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Sample records for secondary metabolite biosynthetic

  1. Distribution of secondary metabolite biosynthetic gene clusters in 343 Fusarium genomes

    Science.gov (United States)

    Fusarium consists of over 200 phylogenetically distinct species, many of which cause important crop diseases and/or produce mycotoxins and other secondary metabolites (SMs). Some fusaria also cause opportunistic infections in humans and other animals. To investigate the distribution of biosynthetic ...

  2. Global analysis of biosynthetic gene clusters reveals vast potential of secondary metabolite production in Penicillium species

    DEFF Research Database (Denmark)

    Nielsen, Jens Christian; Grijseels, Sietske; Prigent, Sylvain

    2017-01-01

    Filamentous fungi produce a wide range of bioactive compounds with important pharmaceutical applications, such as antibiotic penicillins and cholesterol-lowering statins. However, less attention has been paid to fungal secondary metabolites compared to those from bacteria. In this study, we...... sequenced the genomes of 9 Penicillium species and, together with 15 published genomes, we investigated the secondary metabolism of Penicillium and identified an immense, unexploited potential for producing secondary metabolites by this genus. A total of 1,317 putative biosynthetic gene clusters (BGCs) were......-referenced the predicted pathways with published data on the production of secondary metabolites and experimentally validated the production of antibiotic yanuthones in Penicillia and identified a previously undescribed compound from the yanuthone pathway. This study is the first genus-wide analysis of the genomic...

  3. A genomics based discovery of secondary metabolite biosynthetic gene clusters in Aspergillus ustus.

    Directory of Open Access Journals (Sweden)

    Borui Pi

    Full Text Available Secondary metabolites (SMs produced by Aspergillus have been extensively studied for their crucial roles in human health, medicine and industrial production. However, the resulting information is almost exclusively derived from a few model organisms, including A. nidulans and A. fumigatus, but little is known about rare pathogens. In this study, we performed a genomics based discovery of SM biosynthetic gene clusters in Aspergillus ustus, a rare human pathogen. A total of 52 gene clusters were identified in the draft genome of A. ustus 3.3904, such as the sterigmatocystin biosynthesis pathway that was commonly found in Aspergillus species. In addition, several SM biosynthetic gene clusters were firstly identified in Aspergillus that were possibly acquired by horizontal gene transfer, including the vrt cluster that is responsible for viridicatumtoxin production. Comparative genomics revealed that A. ustus shared the largest number of SM biosynthetic gene clusters with A. nidulans, but much fewer with other Aspergilli like A. niger and A. oryzae. These findings would help to understand the diversity and evolution of SM biosynthesis pathways in genus Aspergillus, and we hope they will also promote the development of fungal identification methodology in clinic.

  4. A Genomics Based Discovery of Secondary Metabolite Biosynthetic Gene Clusters in Aspergillus ustus

    Science.gov (United States)

    Pi, Borui; Yu, Dongliang; Dai, Fangwei; Song, Xiaoming; Zhu, Congyi; Li, Hongye; Yu, Yunsong

    2015-01-01

    Secondary metabolites (SMs) produced by Aspergillus have been extensively studied for their crucial roles in human health, medicine and industrial production. However, the resulting information is almost exclusively derived from a few model organisms, including A. nidulans and A. fumigatus, but little is known about rare pathogens. In this study, we performed a genomics based discovery of SM biosynthetic gene clusters in Aspergillus ustus, a rare human pathogen. A total of 52 gene clusters were identified in the draft genome of A. ustus 3.3904, such as the sterigmatocystin biosynthesis pathway that was commonly found in Aspergillus species. In addition, several SM biosynthetic gene clusters were firstly identified in Aspergillus that were possibly acquired by horizontal gene transfer, including the vrt cluster that is responsible for viridicatumtoxin production. Comparative genomics revealed that A. ustus shared the largest number of SM biosynthetic gene clusters with A. nidulans, but much fewer with other Aspergilli like A. niger and A. oryzae. These findings would help to understand the diversity and evolution of SM biosynthesis pathways in genus Aspergillus, and we hope they will also promote the development of fungal identification methodology in clinic. PMID:25706180

  5. IMG-ABC: A Knowledge Base To Fuel Discovery of Biosynthetic Gene Clusters and Novel Secondary Metabolites.

    Science.gov (United States)

    Hadjithomas, Michalis; Chen, I-Min Amy; Chu, Ken; Ratner, Anna; Palaniappan, Krishna; Szeto, Ernest; Huang, Jinghua; Reddy, T B K; Cimermančič, Peter; Fischbach, Michael A; Ivanova, Natalia N; Markowitz, Victor M; Kyrpides, Nikos C; Pati, Amrita

    2015-07-14

    In the discovery of secondary metabolites, analysis of sequence data is a promising exploration path that remains largely underutilized due to the lack of computational platforms that enable such a systematic approach on a large scale. In this work, we present IMG-ABC (https://img.jgi.doe.gov/abc), an atlas of biosynthetic gene clusters within the Integrated Microbial Genomes (IMG) system, which is aimed at harnessing the power of "big" genomic data for discovering small molecules. IMG-ABC relies on IMG's comprehensive integrated structural and functional genomic data for the analysis of biosynthetic gene clusters (BCs) and associated secondary metabolites (SMs). SMs and BCs serve as the two main classes of objects in IMG-ABC, each with a rich collection of attributes. A unique feature of IMG-ABC is the incorporation of both experimentally validated and computationally predicted BCs in genomes as well as metagenomes, thus identifying BCs in uncultured populations and rare taxa. We demonstrate the strength of IMG-ABC's focused integrated analysis tools in enabling the exploration of microbial secondary metabolism on a global scale, through the discovery of phenazine-producing clusters for the first time in Alphaproteobacteria. IMG-ABC strives to fill the long-existent void of resources for computational exploration of the secondary metabolism universe; its underlying scalable framework enables traversal of uncovered phylogenetic and chemical structure space, serving as a doorway to a new era in the discovery of novel molecules. IMG-ABC is the largest publicly available database of predicted and experimental biosynthetic gene clusters and the secondary metabolites they produce. The system also includes powerful search and analysis tools that are integrated with IMG's extensive genomic/metagenomic data and analysis tool kits. As new research on biosynthetic gene clusters and secondary metabolites is published and more genomes are sequenced, IMG-ABC will continue to

  6. IMG-ABC: An Atlas of Biosynthetic Gene Clusters to Fuel the Discovery of Novel Secondary Metabolites

    Energy Technology Data Exchange (ETDEWEB)

    Chen, I-Min; Chu, Ken; Ratner, Anna; Palaniappan, Krishna; Huang, Jinghua; Reddy, T. B.K.; Cimermancic, Peter; Fischbach, Michael; Ivanova, Natalia; Markowitz, Victor; Kyrpides, Nikos; Pati, Amrita

    2014-10-28

    In the discovery of secondary metabolites (SMs), large-scale analysis of sequence data is a promising exploration path that remains largely underutilized due to the lack of relevant computational resources. We present IMG-ABC (https://img.jgi.doe.gov/abc/) -- An Atlas of Biosynthetic gene Clusters within the Integrated Microbial Genomes (IMG) system1. IMG-ABC is a rich repository of both validated and predicted biosynthetic clusters (BCs) in cultured isolates, single-cells and metagenomes linked with the SM chemicals they produce and enhanced with focused analysis tools within IMG. The underlying scalable framework enables traversal of phylogenetic dark matter and chemical structure space -- serving as a doorway to a new era in the discovery of novel molecules.

  7. The antiSMASH database, a comprehensive database of microbial secondary metabolite biosynthetic gene clusters

    DEFF Research Database (Denmark)

    Blin, Kai; Medema, Marnix H.; Kottmann, Renzo

    2017-01-01

    Secondary metabolites produced by microorganisms are the main source of bioactive compounds that are in use as antimicrobial and anticancer drugs, fungicides, herbicides and pesticides. In the last decade, the increasing availability of microbial genomes has established genome mining as a very...

  8. Comprehensive annotation of secondary metabolite biosynthetic genes and gene clusters of Aspergillus nidulans, A. fumigatus, A. niger and A. oryzae

    Science.gov (United States)

    2013-01-01

    Background Secondary metabolite production, a hallmark of filamentous fungi, is an expanding area of research for the Aspergilli. These compounds are potent chemicals, ranging from deadly toxins to therapeutic antibiotics to potential anti-cancer drugs. The genome sequences for multiple Aspergilli have been determined, and provide a wealth of predictive information about secondary metabolite production. Sequence analysis and gene overexpression strategies have enabled the discovery of novel secondary metabolites and the genes involved in their biosynthesis. The Aspergillus Genome Database (AspGD) provides a central repository for gene annotation and protein information for Aspergillus species. These annotations include Gene Ontology (GO) terms, phenotype data, gene names and descriptions and they are crucial for interpreting both small- and large-scale data and for aiding in the design of new experiments that further Aspergillus research. Results We have manually curated Biological Process GO annotations for all genes in AspGD with recorded functions in secondary metabolite production, adding new GO terms that specifically describe each secondary metabolite. We then leveraged these new annotations to predict roles in secondary metabolism for genes lacking experimental characterization. As a starting point for manually annotating Aspergillus secondary metabolite gene clusters, we used antiSMASH (antibiotics and Secondary Metabolite Analysis SHell) and SMURF (Secondary Metabolite Unknown Regions Finder) algorithms to identify potential clusters in A. nidulans, A. fumigatus, A. niger and A. oryzae, which we subsequently refined through manual curation. Conclusions This set of 266 manually curated secondary metabolite gene clusters will facilitate the investigation of novel Aspergillus secondary metabolites. PMID:23617571

  9. Comprehensive annotation of secondary metabolite biosynthetic genes and gene clusters of Aspergillus nidulans, A. fumigatus, A. niger and A. oryzae

    OpenAIRE

    Inglis, Diane O; Binkley, Jonathan; Skrzypek, Marek S; Arnaud, Martha B; Cerqueira, Gustavo C; Shah, Prachi; Wymore, Farrell; Wortman, Jennifer R; Sherlock, Gavin

    2013-01-01

    Background Secondary metabolite production, a hallmark of filamentous fungi, is an expanding area of research for the Aspergilli. These compounds are potent chemicals, ranging from deadly toxins to therapeutic antibiotics to potential anti-cancer drugs. The genome sequences for multiple Aspergilli have been determined, and provide a wealth of predictive information about secondary metabolite production. Sequence analysis and gene overexpression strategies have enabled the discovery of novel s...

  10. Recent development of antiSMASH and other computational approaches to mine secondary metabolite biosynthetic gene clusters

    DEFF Research Database (Denmark)

    Blin, Kai; Kim, Hyun Uk; Medema, Marnix H.

    2017-01-01

    Many drugs are derived from small molecules produced by microorganisms and plants, so-called natural products. Natural products have diverse chemical structures, but the biosynthetic pathways producing those compounds are often organized as biosynthetic gene clusters (BGCs) and follow a highly...... conserved biosynthetic logic. This allows for the identification of core biosynthetic enzymes using genome mining strategies that are based on the sequence similarity of the involved enzymes/genes. However, mining for a variety of BGCs quickly approaches a complexity level where manual analyses...... are no longer possible and require the use of automated genome mining pipelines, such as the antiSMASH software. In this review, we discuss the principles underlying the predictions of antiSMASH and other tools and provide practical advice for their application. Furthermore, we discuss important caveats...

  11. Secondary metabolites from Ganoderma.

    Science.gov (United States)

    Baby, Sabulal; Johnson, Anil John; Govindan, Balaji

    2015-06-01

    Ganoderma is a genus of medicinal mushrooms. This review deals with secondary metabolites isolated from Ganoderma and their biological significance. Phytochemical studies over the last 40years led to the isolation of 431 secondary metabolites from various Ganoderma species. The major secondary compounds isolated are (a) C30 lanostanes (ganoderic acids), (b) C30 lanostanes (aldehydes, alcohols, esters, glycosides, lactones, ketones), (c) C27 lanostanes (lucidenic acids), (d) C27 lanostanes (alcohols, lactones, esters), (e) C24, C25 lanostanes (f) C30 pentacyclic triterpenes, (g) meroterpenoids, (h) farnesyl hydroquinones (meroterpenoids), (i) C15 sesquiterpenoids, (j) steroids, (k) alkaloids, (l) prenyl hydroquinone (m) benzofurans, (n) benzopyran-4-one derivatives and (o) benzenoid derivatives. Ganoderma lucidum is the species extensively studied for its secondary metabolites and biological activities. Ganoderma applanatum, Ganoderma colossum, Ganoderma sinense, Ganoderma cochlear, Ganoderma tsugae, Ganoderma amboinense, Ganoderma orbiforme, Ganoderma resinaceum, Ganoderma hainanense, Ganoderma concinna, Ganoderma pfeifferi, Ganoderma neo-japonicum, Ganoderma tropicum, Ganoderma australe, Ganoderma carnosum, Ganoderma fornicatum, Ganoderma lipsiense (synonym G. applanatum), Ganoderma mastoporum, Ganoderma theaecolum, Ganoderma boninense, Ganoderma capense and Ganoderma annulare are the other Ganoderma species subjected to phytochemical studies. Further phytochemical studies on Ganoderma could lead to the discovery of hitherto unknown biologically active secondary metabolites. Copyright © 2015 Elsevier Ltd. All rights reserved.

  12. Identification of Secondary Metabolite Gene Clusters in the Pseudovibrio Genus Reveals Encouraging Biosynthetic Potential toward the Production of Novel Bioactive Compounds

    Directory of Open Access Journals (Sweden)

    Lynn M. Naughton

    2017-08-01

    Full Text Available Increased incidences of antimicrobial resistance and the emergence of pan-resistant ‘superbugs’ have provoked an extreme sense of urgency amongst researchers focusing on the discovery of potentially novel antimicrobial compounds. A strategic shift in focus from the terrestrial to the marine environment has resulted in the discovery of a wide variety of structurally and functionally diverse bioactive compounds from numerous marine sources, including sponges. Bacteria found in close association with sponges and other marine invertebrates have recently gained much attention as potential sources of many of these novel bioactive compounds. Members of the genus Pseudovibrio are one such group of organisms. In this study, we interrogate the genomes of 21 Pseudovibrio strains isolated from a variety of marine sources, for the presence, diversity and distribution of biosynthetic gene clusters (BGCs. We expand on results obtained from antiSMASH analysis to demonstrate the similarity between the Pseudovibrio-related BGCs and those characterized in other bacteria and corroborate our findings with phylogenetic analysis. We assess how domain organization of the most abundant type of BGCs present among the isolates (Non-ribosomal peptide synthetases and Polyketide synthases may influence the diversity of compounds produced by these organisms and highlight for the first time the potential for novel compound production from this genus of bacteria, using a genome guided approach.

  13. Secondary Metabolites from Higher Fungi: Discovery, Bioactivity, and Bioproduction

    Science.gov (United States)

    Zhong, Jian-Jiang; Xiao, Jian-Hui

    Medicinal higher fungi such as Cordyceps sinensis and Ganoderma lucidum have been used as an alternative medicine remedy to promote health and longevity for people in China and other regions of the world since ancient times. Nowadays there is an increasing public interest in the secondary metabolites of those higher fungi for discovering new drugs or lead compounds. Current research in drug discovery from medicinal higher fungi involves a multifaceted approach combining mycological, biochemical, pharmacological, metabolic, biosynthetic and molecular techniques. In recent years, many new secondary metabolites from higher fungi have been isolated and are more likely to provide lead compounds for new drug discovery, which may include chemopreventive agents possessing the bioactivity of immunomodulatory, anticancer, etc. However, numerous challenges of secondary metabolites from higher fungi are encountered including bioseparation, identification, biosynthetic metabolism, and screening model issues, etc. Commercial production of secondary metabolites from medicinal mushrooms is still limited mainly due to less information about secondary metabolism and its regulation. Strategies for enhancing secondary metabolite production by medicinal mushroom fermentation include two-stage cultivation combining liquid fermentation and static culture, two-stage dissolved oxygen control, etc. Purification of bioactive secondary metabolites, such as ganoderic acids from G. lucidum, is also very important to pharmacological study and future pharmaceutical application. This review outlines typical examples of the discovery, bioactivity, and bioproduction of secondary metabolites of higher fungi origin.

  14. Output ordering and prioritisation system (OOPS): ranking biosynthetic gene clusters to enhance bioactive metabolite discovery.

    Science.gov (United States)

    Peña, Alejandro; Del Carratore, Francesco; Cummings, Matthew; Takano, Eriko; Breitling, Rainer

    2017-12-18

    The rapid increase of publicly available microbial genome sequences has highlighted the presence of hundreds of thousands of biosynthetic gene clusters (BGCs) encoding valuable secondary metabolites. The experimental characterization of new BGCs is extremely laborious and struggles to keep pace with the in silico identification of potential BGCs. Therefore, the prioritisation of promising candidates among computationally predicted BGCs represents a pressing need. Here, we propose an output ordering and prioritisation system (OOPS) which helps sorting identified BGCs by a wide variety of custom-weighted biological and biochemical criteria in a flexible and user-friendly interface. OOPS facilitates a judicious prioritisation of BGCs using G+C content, coding sequence length, gene number, cluster self-similarity and codon bias parameters, as well as enabling the user to rank BGCs based upon BGC type, novelty, and taxonomic distribution. Effective prioritisation of BGCs will help to reduce experimental attrition rates and improve the breadth of bioactive metabolites characterized.

  15. Engineering of secondary metabolite production in streptomycetes

    DEFF Research Database (Denmark)

    Robertsen, Helene Lunde; Gram, Lone

    Streptomycetes are known for their ability to produce a range of different secondary metabolites, including antibiotics, immunosuppressive, anti-fungals, and anti-cancer compounds. Of these compounds, antibiotics play an important role in the clinics for treatment of both mild and severe bacterial...... the computational prediction of suitable 20 bp protospacers for the single guide RNAs and a USER-cloning method for construction of the CRISPR plasmids. Additional improvement to the system was achieved through the development of an optimised USER assembly workflow for cheaper and faster plasmid construction....... The workflow was verified by manual knock-down of two biosynthetic gene clusters in model organism Streptomyces coelicolor A3(2), which confirmed the applicability of the system. A second part of the thesis was devoted to engineering of Streptomyces collinus Tü 365, which is a known producer of the narrow...

  16. Accurate prediction of secondary metabolite gene clusters in filamentous fungi

    DEFF Research Database (Denmark)

    Andersen, Mikael Rørdam; Nielsen, Jakob Blæsbjerg; Klitgaard, Andreas

    2013-01-01

    Biosynthetic pathways of secondary metabolites from fungi are currently subject to an intense effort to elucidate the genetic basis for these compounds due to their large potential within pharmaceutics and synthetic biochemistry. The preferred method is methodical gene deletions to identify...... used A. nidulans for our method development and validation due to the wealth of available biochemical data, but the method can be applied to any fungus with a sequenced and assembled genome, thus supporting further secondary metabolite pathway elucidation in the fungal kingdom....

  17. Primary expectations of secondary metabolites

    Science.gov (United States)

    My program examines the plant secondary metabolites (i.e. phenolics) important for human health, and which impart the organoleptic properties that are quality indicators for fresh and processed foods. Consumer expectations such as appearance, taste, or texture influence their purchasing decisions; a...

  18. Endophytic actinobacteria: Diversity, secondary metabolism and mechanisms to unsilence biosynthetic gene clusters.

    Science.gov (United States)

    Dinesh, Raghavan; Srinivasan, Veeraraghavan; T E, Sheeja; Anandaraj, Muthuswamy; Srambikkal, Hamza

    2017-09-01

    Endophytic actinobacteria, which reside in the inner tissues of host plants, are gaining serious attention due to their capacity to produce a plethora of secondary metabolites (e.g. antibiotics) possessing a wide variety of biological activity with diverse functions. This review encompasses the recent reports on endophytic actinobacterial species diversity, in planta habitats and mechanisms underlying their mode of entry into plants. Besides, their metabolic potential, novel bioactive compounds they produce and mechanisms to unravel their hidden metabolic repertoire by activation of cryptic or silent biosynthetic gene clusters (BGCs) for eliciting novel secondary metabolite production are discussed. The study also reviews the classical conservative techniques (chemical/biological/physical elicitation, co-culturing) as well as modern microbiology tools (e.g. next generation sequencing) that are being gainfully employed to uncover the vast hidden scaffolds for novel secondary metabolites produced by these endophytes, which would subsequently herald a revolution in drug engineering. The potential role of these endophytes in the agro-environment as promising biological candidates for inhibition of phytopathogens and the way forward to thoroughly exploit this unique microbial community by inducing expression of cryptic BGCs for encoding unseen products with novel therapeutic properties are also discussed.

  19. The secondary metabolite bioinformatics portal

    DEFF Research Database (Denmark)

    Weber, Tilmann; Kim, Hyun Uk

    2016-01-01

    . In this context, this review gives a summary of tools and databases that currently are available to mine, identify and characterize natural product biosynthesis pathways and their producers based on ‘omics data. A web portal called Secondary Metabolite Bioinformatics Portal (SMBP at http...... analytical and chemical methods gave access to this group of compounds, nowadays genomics-based methods offer complementary approaches to find, identify and characterize such molecules. This paradigm shift also resulted in a high demand for computational tools to assist researchers in their daily work......Natural products are among the most important sources of lead molecules for drug discovery. With the development of affordable whole-genome sequencing technologies and other ‘omics tools, the field of natural products research is currently undergoing a shift in paradigms. While, for decades, mainly...

  20. Secondary metabolism in Fusarium fujikuroi: strategies to unravel the function of biosynthetic pathways.

    Science.gov (United States)

    Janevska, Slavica; Tudzynski, Bettina

    2018-01-01

    The fungus Fusarium fujikuroi causes bakanae disease of rice due to its ability to produce the plant hormones, the gibberellins. The fungus is also known for producing harmful mycotoxins (e.g., fusaric acid and fusarins) and pigments (e.g., bikaverin and fusarubins). However, for a long time, most of these well-known products could not be linked to biosynthetic gene clusters. Recent genome sequencing has revealed altogether 47 putative gene clusters. Most of them were orphan clusters for which the encoded natural product(s) were unknown. In this review, we describe the current status of our research on identification and functional characterizations of novel secondary metabolite gene clusters. We present several examples where linking known metabolites to the respective biosynthetic genes has been achieved and describe recent strategies and methods to access new natural products, e.g., by genetic manipulation of pathway-specific or global transcritption factors. In addition, we demonstrate that deletion and over-expression of histone-modifying genes is a powerful tool to activate silent gene clusters and to discover their products.

  1. antiSMASH 2.0-a versatile platform for genome mining of secondary metabolite producers

    NARCIS (Netherlands)

    Blin, Kai; Medema, Marnix H.; Kazempour, Daniyal; Fischbach, Michael A.; Breitling, Rainer; Takano, Eriko; Weber, Tilmann

    Microbial secondary metabolites are a potent source of antibiotics and other pharmaceuticals. Genome mining of their biosynthetic gene clusters has become a key method to accelerate their identification and characterization. In 2011, we developed antiSMASH, a web-based analysis platform that

  2. Biochemical and secondary metabolites changes under moisture ...

    African Journals Online (AJOL)

    The study showed the importance of carbohydrate and nitrogen cycle related metabolites in mediating tolerance in cassava by affecting their phenotypic expression in the plant. Keywords: Hydrothermal stress, bio-chemicals, pigments, secondary metabolites, cassava. African Journal of Biotechnology, Vol 13(31) 3173-3186 ...

  3. Secondary metabolites from marine microorganisms.

    Science.gov (United States)

    Kelecom, Alphonse

    2002-03-01

    After 40 years of intensive research, chemistry of marine natural products has become a mature field. Since 1995, there are signals of decreased interest in the search of new metabolites from traditional sources such as macroalgae and octocorals, and the number of annual reports on marine sponges stabilized. On the contrary, metabolites from microorganisms is a rapidly growing field, due, at least in part, to the suspicion that a number of metabolites obtained from algae and invertebrates may be produced by associated microorganisms. Studies are concerned with bacteria and fungi, isolated from seawater, sediments, algae, fish and mainly from marine invertebrates such as sponges, mollusks, tunicates, coelenterates and crustaceans. Although it is still to early to define tendencies, it may be stated that the metabolites from microorganisms are in most cases quite different from those produced by the invertebrate hosts. Nitrogenated metabolites predominate over acetate derivatives, and terpenes are uncommon. Among the latter, sesquiterpenes, diterpenes and carotenes have been isolated; among nitrogenated metabolites, amides, cyclic peptides and indole alkaloids predominate.

  4. Secondary metabolites from marine microorganisms

    Directory of Open Access Journals (Sweden)

    KELECOM ALPHONSE

    2002-01-01

    Full Text Available After 40 years of intensive research, chemistry of marine natural products has become a mature field. Since 1995, there are signals of decreased interest in the search of new metabolites from traditional sources such as macroalgae and octocorals, and the number of annual reports on marine sponges stabilized. On the contrary, metabolites from microorganisms is a rapidly growing field, due, at least in part, to the suspicion that a number of metabolites obtained from algae and invertebrates may be produced by associated microorganisms. Studies are concerned with bacteria and fungi, isolated from seawater, sediments, algae, fish and mainly from marine invertebrates such as sponges, mollusks, tunicates, coelenterates and crustaceans. Although it is still to early to define tendencies, it may be stated that the metabolites from microorganisms are in most cases quite different from those produced by the invertebrate hosts. Nitrogenated metabolites predominate over acetate derivatives, and terpenes are uncommon. Among the latter, sesquiterpenes, diterpenes and carotenes have been isolated; among nitrogenated metabolites, amides, cyclic peptides and indole alkaloids predominate.

  5. Secondary metabolites of cyanobacteria Nostoc sp.

    Science.gov (United States)

    Kobayashi, Akio; Kajiyama, Shin-Ichiro

    1998-03-01

    Cyanobacteria attracted much attention recently because of their secondary metabolites with potent biological activities and unusual structures. This paper reviews some recent studies on the isolation, structural, elucidation and biological activities of the bioactive compounds from cyanobacteria Nostoc species.

  6. Secondary Metabolites Produced during the Germination of Streptomyces coelicolor

    Directory of Open Access Journals (Sweden)

    Matouš Čihák

    2017-12-01

    Full Text Available Spore awakening is a series of actions that starts with purely physical processes and continues via the launching of gene expression and metabolic activities, eventually achieving a vegetative phase of growth. In spore-forming microorganisms, the germination process is controlled by intra- and inter-species communication. However, in the Streptomyces clade, which is capable of developing a plethora of valuable compounds, the chemical signals produced during germination have not been systematically studied before. Our previously published data revealed that several secondary metabolite biosynthetic genes are expressed during germination. Therefore, we focus here on the secondary metabolite production during this developmental stage. Using high-performance liquid chromatography-mass spectrometry, we found that the sesquiterpenoid antibiotic albaflavenone, the polyketide germicidin A, and chalcone are produced during germination of the model streptomycete, S. coelicolor. Interestingly, the last two compounds revealed an inhibitory effect on the germination process. The secondary metabolites originating from the early stage of microbial growth may coordinate the development of the producer (quorum sensing and/or play a role in competitive microflora repression (quorum quenching in their nature environments.

  7. Secondary metabolites from Eremostachys laciniata

    DEFF Research Database (Denmark)

    Calis, Ihsan; Güvenc, Aysegül; Armagan, Metin

    2008-01-01

    ), and forsythoside B (18), and five flavone derivatives, luteolin (19), luteolin 7-O-β-D-glucopyranoside (20), luteolin 7-O-(6''-O-β-D-apiofuranosyl)-β-D-glucopyranoside (21), apigenin 7-O-β-D-glucopyranoside (22), and apigenin 7-O-(6''-O-p-coumaroyl)-β-D-glucopyranoside (23). The structures of the metabolites were...... elucidated from spectroscopic (UV, IR, 1D- and 2D-NMR) and ESI-MS evidence, as well as from their specific optical rotation. The presence of these metabolites of three different classes strongly supports the close relationship of the genera Eremostachys and Phlomis....

  8. Systems biology and biotechnology of Streptomyces species for the production of secondary metabolites

    DEFF Research Database (Denmark)

    Hwang, Kyu-Sang; Kim, Hyun Uk; Charusanti, Pep

    2014-01-01

    Streptomyces species continue to attract attention as a source of novel medicinal compounds. Despite a long history of studies on these microorganisms, they still have many biochemical mysteries to be elucidated. Investigations of novel secondary metabolites and their biosynthetic gene clusters...... collected in the form of databases and knowledgebases, providing predictive information and enabling one to explore experimentally unrecognized biological spaces of secondary metabolism. Herein, we review recent trends in the systems biology and biotechnology of Streptomyces species....

  9. Secondary metabolites in fungus-plant interactions

    Science.gov (United States)

    Pusztahelyi, Tünde; Holb, Imre J.; Pócsi, István

    2015-01-01

    Fungi and plants are rich sources of thousands of secondary metabolites. The genetically coded possibilities for secondary metabolite production, the stimuli of the production, and the special phytotoxins basically determine the microscopic fungi-host plant interactions and the pathogenic lifestyle of fungi. The review introduces plant secondary metabolites usually with antifungal effect as well as the importance of signaling molecules in induced systemic resistance and systemic acquired resistance processes. The review also concerns the mimicking of plant effector molecules like auxins, gibberellins and abscisic acid by fungal secondary metabolites that modulate plant growth or even can subvert the plant defense responses such as programmed cell death to gain nutrients for fungal growth and colonization. It also looks through the special secondary metabolite production and host selective toxins of some significant fungal pathogens and the plant response in form of phytoalexin production. New results coming from genome and transcriptional analyses in context of selected fungal pathogens and their hosts are also discussed. PMID:26300892

  10. Pharmaceutically active secondary metabolites of marine actinobacteria.

    Science.gov (United States)

    Manivasagan, Panchanathan; Venkatesan, Jayachandran; Sivakumar, Kannan; Kim, Se-Kwon

    2014-04-01

    Marine actinobacteria are one of the most efficient groups of secondary metabolite producers and are very important from an industrial point of view. Many representatives of the order Actinomycetales are prolific producers of thousands of biologically active secondary metabolites. Actinobacteria from terrestrial sources have been studied and screened since the 1950s, for many important antibiotics, anticancer, antitumor and immunosuppressive agents. However, frequent rediscovery of the same compounds from the terrestrial actinobacteria has made them less attractive for screening programs in the recent years. At the same time, actinobacteria isolated from the marine environment have currently received considerable attention due to the structural diversity and unique biological activities of their secondary metabolites. They are efficient producers of new secondary metabolites that show a range of biological activities including antibacterial, antifungal, anticancer, antitumor, cytotoxic, cytostatic, anti-inflammatory, anti-parasitic, anti-malaria, antiviral, antioxidant, anti-angiogenesis, etc. In this review, an evaluation is made on the current status of research on marine actinobacteria yielding pharmaceutically active secondary metabolites. Bioactive compounds from marine actinobacteria possess distinct chemical structures that may form the basis for synthesis of new drugs that could be used to combat resistant pathogens. With the increasing advancement in science and technology, there would be a greater demand for new bioactive compounds synthesized by actinobacteria from various marine sources in future. Copyright © 2013 Elsevier GmbH. All rights reserved.

  11. Insights into secondary metabolism from a global analysis of prokaryotic biosynthetic gene clusters

    NARCIS (Netherlands)

    Cimermancic, P.; Medema, Marnix; Claesen, J.; Kurika, K.; Wieland Brown, L.C.; Mavrommatis, K.; Pati, A.; Godfrey, P.A.; Koehrsen, M.; Clardy, J.; Birren, B. W.; Takano, Eriko; Sali, A.; Linington, R.G.; Fischbach, M.A.

    2014-01-01

    Although biosynthetic gene clusters (BGCs) have been discovered for hundreds of bacterial metabolites, our knowledge of their diversity remains limited. Here, we used a novel algorithm to systematically identify BGCs in the extensive extant microbial sequencing data. Network analysis of the

  12. Chemical composition, secondary metabolites, in vitro gas ...

    African Journals Online (AJOL)

    Chemical composition, secondary metabolites, in vitro gas production characteristics and acceptability study of some forage for ruminant feeding in South-Western Nigeria. ... Chemical composition and qualitative analysis of saponins, phenol and steroids of the plants were determined. In vitro gas production (IVGP) was ...

  13. Antibacterial activity of secondary metabolites isolated from ...

    African Journals Online (AJOL)

    Aghomotsegin

    2015-10-28

    Oct 28, 2015 ... Alternaria spp. are cosmopolitan mould fungi and can be found in soils ... the secondary metabolites products from A. alternata and ..... Zone of inhibition (mm) of test bacterial strains to fungal products and standard antibiotics. Fungal ... marine actinomycetes from pulicat, Muttukadu, and Ennore estuaries.

  14. Correlation between Plant Secondary Metabolites and Their Antifungal Mechanisms–A Review

    DEFF Research Database (Denmark)

    Freiesleben, Sara; Jäger, Anna

    2014-01-01

    the biosynthetic group of terpenes and their antifungal mechanisms of action, all of them exhibiting their antifungal action through cell membrane disruption, although some of the terpenes also seemed to work through mitochondrial dysfunction. A clear correlation has not been demonstrated between the two other......The search for new antifungal drugs often involves secondary metabolites from plants because of their pharmacological activity against foreign pathogens. Among the modern drugs in use today about 40% are of natural origin. To distinguish the secondary metabolites they can be divided into groups...... based on their structure or biosynthetic origin. When searching for new antifungal agents it is crucial to search for a mechanism of action for which unwanted side effects can be avoided. This can be done if the mechanism of action only involves fungal cells and not mammalian cells. For that reason...

  15. Biosynthesis of secondary metabolites in sugarcane

    Directory of Open Access Journals (Sweden)

    S.C. França

    2001-12-01

    Full Text Available A set of genes related to secondary metabolism was extracted from the sugarcane expressed sequence tag (SUCEST database and was used to investigate both the gene expression pattern of key enzymes regulating the main biosynthetic secondary metabolism pathways and the major classes of metabolites involved in the response of sugarcane to environmental and developmental cues. The SUCEST database was constructed with tissues in different physiological conditions which had been collected under varied situation of environmental stress. This database allows researchers to identify and characterize the expressed genes of a wide range of putative enzymes able to catalyze steps in the phenylpropanoid, isoprenoid and other pathways of the special metabolic mechanisms involved in the response of sugarcane to environmental changes. Our results show that sugarcane cDNAs encoded putative ultra-violet induced sesquiterpene cyclases (SC; chalcone synthase (CHS, the first enzyme in the pathway branch for flavonoid biosynthesis; isoflavone synthase (IFS, involved in plant defense and root nodulation; isoflavone reductase (IFR, a key enzyme in phenylpropanoid phytoalexin biosynthesis; and caffeic acid-O-methyltransferase, a key enzyme in the biosynthesis of lignin cell wall precursors. High levels of CHS transcripts from plantlets infected with Herbaspirillum rubri or Gluconacetobacter diazotroficans suggests that agents of biotic stress can elicit flavonoid biosynthesis in sugarcane. From this data we have predicted the profile of isoprenoid and phenylpropanoid metabolism in sugarcane and pointed the branches of secondary metabolism activated during tissue-specific stages of development and the adaptive response of sugarcane to agents of biotic and abiotic stress, although our assignment of enzyme function should be confirmed by careful biochemical and genetic supporting evidence.Este trabalho foi realizado com os objetivos de gerar uma coleção de genes

  16. Diverse and Abundant Secondary Metabolism Biosynthetic Gene Clusters in the Genomes of Marine Sponge Derived Streptomyces spp. Isolates

    Directory of Open Access Journals (Sweden)

    Stephen A. Jackson

    2018-02-01

    Full Text Available The genus Streptomyces produces secondary metabolic compounds that are rich in biological activity. Many of these compounds are genetically encoded by large secondary metabolism biosynthetic gene clusters (smBGCs such as polyketide synthases (PKS and non-ribosomal peptide synthetases (NRPS which are modular and can be highly repetitive. Due to the repeats, these gene clusters can be difficult to resolve using short read next generation datasets and are often quite poorly predicted using standard approaches. We have sequenced the genomes of 13 Streptomyces spp. strains isolated from shallow water and deep-sea sponges that display antimicrobial activities against a number of clinically relevant bacterial and yeast species. Draft genomes have been assembled and smBGCs have been identified using the antiSMASH (antibiotics and Secondary Metabolite Analysis Shell web platform. We have compared the smBGCs amongst strains in the search for novel sequences conferring the potential to produce novel bioactive secondary metabolites. The strains in this study recruit to four distinct clades within the genus Streptomyces. The marine strains host abundant smBGCs which encode polyketides, NRPS, siderophores, bacteriocins and lantipeptides. The deep-sea strains appear to be enriched with gene clusters encoding NRPS. Marine adaptations are evident in the sponge-derived strains which are enriched for genes involved in the biosynthesis and transport of compatible solutes and for heat-shock proteins. Streptomyces spp. from marine environments are a promising source of novel bioactive secondary metabolites as the abundance and diversity of smBGCs show high degrees of novelty. Sponge derived Streptomyces spp. isolates appear to display genomic adaptations to marine living when compared to terrestrial strains.

  17. IMG-ABC: new features for bacterial secondary metabolism analysis and targeted biosynthetic gene cluster discovery in thousands of microbial genomes.

    Science.gov (United States)

    Hadjithomas, Michalis; Chen, I-Min A; Chu, Ken; Huang, Jinghua; Ratner, Anna; Palaniappan, Krishna; Andersen, Evan; Markowitz, Victor; Kyrpides, Nikos C; Ivanova, Natalia N

    2017-01-04

    Secondary metabolites produced by microbes have diverse biological functions, which makes them a great potential source of biotechnologically relevant compounds with antimicrobial, anti-cancer and other activities. The proteins needed to synthesize these natural products are often encoded by clusters of co-located genes called biosynthetic gene clusters (BCs). In order to advance the exploration of microbial secondary metabolism, we developed the largest publically available database of experimentally verified and predicted BCs, the Integrated Microbial Genomes Atlas of Biosynthetic gene Clusters (IMG-ABC) (https://img.jgi.doe.gov/abc/). Here, we describe an update of IMG-ABC, which includes ClusterScout, a tool for targeted identification of custom biosynthetic gene clusters across 40 000 isolate microbial genomes, and a new search capability to query more than 700 000 BCs from isolate genomes for clusters with similar Pfam composition. Additional features enable fast exploration and analysis of BCs through two new interactive visualization features, a BC function heatmap and a BC similarity network graph. These new tools and features add to the value of IMG-ABC's vast body of BC data, facilitating their in-depth analysis and accelerating secondary metabolite discovery. © The Author(s) 2016. Published by Oxford University Press on behalf of Nucleic Acids Research.

  18. Novel key metabolites reveal further branching of the roquefortine/meleagrin biosynthetic pathway.

    Science.gov (United States)

    Ries, Marco I; Ali, Hazrat; Lankhorst, Peter P; Hankemeier, Thomas; Bovenberg, Roel A L; Driessen, Arnold J M; Vreeken, Rob J

    2013-12-27

    Metabolic profiling and structural elucidation of novel secondary metabolites obtained from derived deletion strains of the filamentous fungus Penicillium chrysogenum were used to reassign various previously ascribed synthetase genes of the roquefortine/meleagrin pathway to their corresponding products. Next to the structural characterization of roquefortine F and neoxaline, which are for the first time reported for P. chrysogenum, we identified the novel metabolite roquefortine L, including its degradation products, harboring remarkable chemical structures. Their biosynthesis is discussed, questioning the exclusive role of glandicoline A as key intermediate in the pathway. The results reveal that further enzymes of this pathway are rather unspecific and catalyze more than one reaction, leading to excessive branching in the pathway with meleagrin and neoxaline as end products of two branches.

  19. Early Phenylpropanoid Biosynthetic Steps in Cannabis sativa: Link between Genes and Metabolites

    Directory of Open Access Journals (Sweden)

    Immacolata Coraggio

    2013-06-01

    Full Text Available Phenylalanine ammonia-lyase (PAL, Cinnamic acid 4-hydroxylase (C4H and 4-Coumarate: CoA ligase (4CL catalyze the first three steps of the general phenylpropanoid pathway whereas chalcone synthase (CHS catalyzes the first specific step towards flavonoids production. This class of specialized metabolites has a wide range of biological functions in plant development and defence and a broad spectrum of therapeutic activities for human health. In this study, we report the isolation of hemp PAL and 4CL cDNA and genomic clones. Through in silico analysis of their deduced amino acid sequences, more than an 80% identity with homologues genes of other plants was shown and phylogenetic relationships were highlighted. Quantitative expression analysis of the four above mentioned genes, PAL and 4CL enzymatic activities, lignin content and NMR metabolite fingerprinting in different Cannabis sativa tissues were evaluated. Furthermore, the use of different substrates to assay PAL and 4CL enzymatic activities indicated that different isoforms were active in different tissues. The diversity in secondary metabolites content observed in leaves (mainly flavonoids and roots (mainly lignin was discussed in relation to gene expression and enzymatic activities data.

  20. Early phenylpropanoid biosynthetic steps in Cannabis sativa: link between genes and metabolites.

    Science.gov (United States)

    Docimo, Teresa; Consonni, Roberto; Coraggio, Immacolata; Mattana, Monica

    2013-06-28

    Phenylalanine ammonia-lyase (PAL), Cinnamic acid 4-hydroxylase (C4H) and 4-Coumarate: CoA ligase (4CL) catalyze the first three steps of the general phenylpropanoid pathway whereas chalcone synthase (CHS) catalyzes the first specific step towards flavonoids production. This class of specialized metabolites has a wide range of biological functions in plant development and defence and a broad spectrum of therapeutic activities for human health. In this study, we report the isolation of hemp PAL and 4CL cDNA and genomic clones. Through in silico analysis of their deduced amino acid sequences, more than an 80% identity with homologues genes of other plants was shown and phylogenetic relationships were highlighted. Quantitative expression analysis of the four above mentioned genes, PAL and 4CL enzymatic activities, lignin content and NMR metabolite fingerprinting in different Cannabis sativa tissues were evaluated. Furthermore, the use of different substrates to assay PAL and 4CL enzymatic activities indicated that different isoforms were active in different tissues. The diversity in secondary metabolites content observed in leaves (mainly flavonoids) and roots (mainly lignin) was discussed in relation to gene expression and enzymatic activities data.

  1. Cyanobacteria as Cell Factories to Produce Plant Secondary Metabolites

    OpenAIRE

    Xue, Yong; He, Qingfang

    2015-01-01

    Cyanobacteria represent a promising platform for the production of plant secondary metabolites. Their capacity to express plant P450 proteins, which have essential functions in the biosynthesis of many plant secondary metabolites, makes cyanobacteria ideal for this purpose, and their photosynthetic capability allows cyanobacteria to grow with simple nutrient inputs. This review summarizes the advantages of using cyanobacteria to transgenically produce plant secondary metabolites. Some techniq...

  2. Yield improvement strategies for the production of secondary metabolites in plant tissue culture: silymarin from Silybum marianum tissue culture.

    Science.gov (United States)

    AbouZid, S

    2014-01-01

    Plant cell culture can be a potential source for the production of important secondary metabolites. This technology bears many advantages over conventional agricultural methods. The main problem to arrive at a cost-effective process is the low productivity. This is mainly due to lack of differentiation in the cultured cells. Many approaches have been used to maximise the yield of secondary metabolites produced by cultured plant cells. Among these approaches: choosing a plant with a high biosynthetic capacity, obtaining efficient cell line for growth and production of metabolite of interest, manipulating culture conditions, elicitation, metabolic engineering and organ culture. This article gives an overview of the various approaches used to maximise the production of pharmaceutically important secondary metabolites in plant cell cultures. Examples of using these different approaches are shown for the production of silymarin from Silybum marianum tissue culture.

  3. A Proteomic Approach to Investigating Gene Cluster Expression and Secondary Metabolite Functionality in Aspergillus fumigatus

    Science.gov (United States)

    Owens, Rebecca A.; Hammel, Stephen; Sheridan, Kevin J.; Jones, Gary W.; Doyle, Sean

    2014-01-01

    A combined proteomics and metabolomics approach was utilised to advance the identification and characterisation of secondary metabolites in Aspergillus fumigatus. Here, implementation of a shotgun proteomic strategy led to the identification of non-redundant mycelial proteins (n = 414) from A. fumigatus including proteins typically under-represented in 2-D proteome maps: proteins with multiple transmembrane regions, hydrophobic proteins and proteins with extremes of molecular mass and pI. Indirect identification of secondary metabolite cluster expression was also achieved, with proteins (n = 18) from LaeA-regulated clusters detected, including GliT encoded within the gliotoxin biosynthetic cluster. Biochemical analysis then revealed that gliotoxin significantly attenuates H2O2-induced oxidative stress in A. fumigatus (p>0.0001), confirming observations from proteomics data. A complementary 2-D/LC-MS/MS approach further elucidated significantly increased abundance (pproteome and experimental strategies, plus mechanistic data pertaining to gliotoxin functionality in the organism. PMID:25198175

  4. Aspergillus flavus secondary metabolites: more than just aflatoxins

    Science.gov (United States)

    Aspergillus flavus is best known for producing the family of potent carcinogenic secondary metabolites known as aflatoxins. However, this opportunistic plant and animal pathogen also produces numerous other secondary metabolites, many of which have also been shown to be toxic. While about forty of t...

  5. Increasing carbon availability stimulates growth and secondary metabolites via modulation of phytohormones in winter wheat

    Science.gov (United States)

    Reichelt, Michael; Chowdhury, Somak; Hammerbacher, Almuth; Hartmann, Henrik

    2017-01-01

    Abstract Phytohormones play important roles in plant acclimation to changes in environmental conditions. However, their role in whole-plant regulation of growth and secondary metabolite production under increasing atmospheric CO2 concentrations ([CO2]) is uncertain but crucially important for understanding plant responses to abiotic stresses. We grew winter wheat (Triticum aestivum) under three [CO2] (170, 390, and 680 ppm) over 10 weeks, and measured gas exchange, relative growth rate (RGR), soluble sugars, secondary metabolites, and phytohormones including abscisic acid (ABA), auxin (IAA), jasmonic acid (JA), and salicylic acid (SA) at the whole-plant level. Our results show that, at the whole-plant level, RGR positively correlated with IAA but not ABA, and secondary metabolites positively correlated with JA and JA-Ile but not SA. Moreover, soluble sugars positively correlated with IAA and JA but not ABA and SA. We conclude that increasing carbon availability stimulates growth and production of secondary metabolites via up-regulation of auxin and jasmonate levels, probably in response to sugar-mediated signalling. Future low [CO2] studies should address the role of reactive oxygen species (ROS) in leaf ABA and SA biosynthesis, and at the transcriptional level should focus on biosynthetic and, in particular, on responsive genes involved in [CO2]-induced hormonal signalling pathways. PMID:28159987

  6. Rapid generation of recombinant Pseudomonas putida secondary metabolite producers using yTREX

    Directory of Open Access Journals (Sweden)

    Andreas Domröse

    2017-12-01

    Full Text Available Microbial secondary metabolites represent a rich source of valuable compounds with a variety of applications in medicine or agriculture. Effective exploitation of this wealth of chemicals requires the functional expression of the respective biosynthetic genes in amenable heterologous hosts. We have previously established the TREX system which facilitates the transfer, integration and expression of biosynthetic gene clusters in various bacterial hosts. Here, we describe the yTREX system, a new tool adapted for one-step yeast recombinational cloning of gene clusters. We show that with yTREX, Pseudomonas putida secondary metabolite production strains can rapidly be constructed by random targeting of chromosomal promoters by Tn5 transposition. Feasibility of this approach was corroborated by prodigiosin production after yTREX cloning, transfer and expression of the respective biosynthesis genes from Serratia marcescens. Furthermore, the applicability of the system for effective pathway rerouting by gene cluster adaptation was demonstrated using the violacein biosynthesis gene cluster from Chromobacterium violaceum, producing pathway metabolites violacein, deoxyviolacein, prodeoxyviolacein, and deoxychromoviridans. Clones producing both prodigiosin and violaceins could be readily identified among clones obtained after random chromosomal integration by their strong color-phenotype. Finally, the addition of a promoter-less reporter gene enabled facile detection also of phenazine-producing clones after transfer of the respective phenazine-1-carboxylic acid biosynthesis genes from Pseudomonas aeruginosa. All compounds accumulated to substantial titers in the mg range. We thus corroborate here the suitability of P. putida for the biosynthesis of diverse natural products, and demonstrate that the yTREX system effectively enables the rapid generation of secondary metabolite producing bacteria by activation of heterologous gene clusters, applicable for

  7. SECONDARY METABOLITES FROM MARINE PENICILLIUM BREVICOMPACTUM

    OpenAIRE

    ROVIROSA, JUANA; DIAZ-MARRERO, ANA; DARIAS, JOSE; PAINEMAL, KARIN; SAN MARTIN, AURELIO

    2006-01-01

    In a screening of Basidiomycete cultures isolated from marine invertebrates collected along the Chilean coastline for the production of antibiotics we identified a Penicillium brevicompactum strain as a producer of metabolites inhibiting the growth of bacteria and fungi. Bioactivity guided purification resulted in the isolation of four known metabolites. Their structures were elucidated by spectroscopic methods.

  8. Gamma irradiation of medicinally important plants and the enhancement of secondary metabolite production.

    Science.gov (United States)

    Vardhan, P Vivek; Shukla, Lata I

    2017-09-01

    metabolites in response to various biotic and abiotic stresses is compared with ionizing radiation. A ∼5- to 20-fold increase is noted with ∼20 Gy irradiation dose. It increases the yield of secondary metabolites by enhancing the activity of certain key biosynthetic enzymes. Identification of the optimum dose is the important step in the large-scale production of secondary metabolites at industrial level.

  9. Identification, quantification, spatiotemporal distribution and genetic variation of major latex secondary metabolites in the common dandelion (Taraxacum officinale agg.).

    Science.gov (United States)

    Huber, Meret; Triebwasser-Freese, Daniella; Reichelt, Michael; Heiling, Sven; Paetz, Christian; Chandran, Jima N; Bartram, Stefan; Schneider, Bernd; Gershenzon, Jonathan; Erb, Matthias

    2015-07-01

    The secondary metabolites in the roots, leaves and flowers of the common dandelion (Taraxacum officinale agg.) have been studied in detail. However, little is known about the specific constituents of the plant's highly specialized laticifer cells. Using a combination of liquid and gas chromatography, mass spectrometry and nuclear magnetic resonance spectrometry, we identified and quantified the major secondary metabolites in the latex of different organs across different growth stages in three genotypes, and tested the activity of the metabolites against the generalist root herbivore Diabrotica balteata. We found that common dandelion latex is dominated by three classes of secondary metabolites: phenolic inositol esters (PIEs), triterpene acetates (TritAc) and the sesquiterpene lactone taraxinic acid β-D-glucopyranosyl ester (TA-G). Purification and absolute quantification revealed concentrations in the upper mgg(-1) range for all compound classes with up to 6% PIEs, 5% TritAc and 7% TA-G per gram latex fresh weight. Contrary to typical secondary metabolite patterns, concentrations of all three classes increased with plant age. The highest concentrations were measured in the main root. PIE profiles differed both quantitatively and qualitatively between plant genotypes, whereas TritAc and TA-G differed only quantitatively. Metabolite concentrations were positively correlated within and between the different compound classes, indicating tight biosynthetic co-regulation. Latex metabolite extracts strongly repelled D. balteata larvae, suggesting that the latex constituents are biologically active. Copyright © 2015 Elsevier Ltd. All rights reserved.

  10. Prototype of an intertwined secondary-metabolite supercluster

    Science.gov (United States)

    Phillipp Wiemann; Chun-Jun. Guo; Jonathan M. Palmer; Relebohile Sekonyela; Clay C.C. Wang; Nancy P. Keller

    2013-01-01

    The hallmark trait of fungal secondary-metabolite gene clusters is well established, consisting of contiguous enzymatic and often regulatory gene(s) devoted to the production of a metabolite of a specific chemical class. Unexpectedly, we have found a deviation from this motif in a subtelomeric region of Aspergillus fumigatus. This region, under the...

  11. A Review of the Secondary Metabolites and Biological Activities of ...

    African Journals Online (AJOL)

    School of Chemical Sciences, Universiti Sains Malaysia, Penang 11800, Malaysia ... ulcers. A wide range of secondary metabolites such as alkaloids, diterpenes, flavones, phenolics, and triterpenes .... potency than the synthetic antioxidant.

  12. Extraction and applications of cyanotoxins and other cyanobacterial secondary metabolites.

    Science.gov (United States)

    Haque, Fatima; Banayan, Sara; Yee, Josephine; Chiang, Yi Wai

    2017-09-01

    The rapid proliferation of cyanobacteria in bodies of water has caused cyanobacterial blooms, which have become an increasing cause of concern, largely due to the presence of toxic secondary metabolites (or cyanotoxins). Cyanotoxins are the toxins produced by cyanobacteria that may be harmful to surrounding wildlife. They include hepatotoxins, neurotoxins and dermatotoxins, and are classified based on the organs they affect. There are also non-toxic secondary metabolites that include chelators and UV-absorbing compounds. This paper summarizes the optimal techniques for secondary metabolite extraction and the possible useful products that can be obtained from cyanobacteria, with additional focus given to products derived from secondary metabolites. It becomes evident that the potential for their use as biocides, chelators, biofuels, biofertilizers, pharmaceuticals, food and feed, and cosmetics has not yet been comprehensively studied or extensively implemented. Copyright © 2017 Elsevier Ltd. All rights reserved.

  13. Improvement of hairy root cultures and plants by changing biosynthetic pathways leading to pharmaceutical metabolites: strategies and applications.

    Science.gov (United States)

    Ludwig-Müller, Jutta; Jahn, Linda; Lippert, Annemarie; Püschel, Joachim; Walter, Antje

    2014-11-01

    A plethora of bioactive plant metabolites has been explored for pharmaceutical, food chemistry and agricultural applications. The chemical synthesis of these structures is often difficult, so plants are favorably used as producers. While whole plants can serve as a source for secondary metabolites and can be also improved by metabolic engineering, more often cell or organ cultures of relevant plant species are of interest. It should be noted that only in few cases the production for commercial application in such cultures has been achieved. Their genetic manipulation is sometimes faster and the production of a specific metabolite is more reliable, because of less environmental influences. In addition, upscaling in bioreactors is nowadays possible for many of these cultures, so some are already used in industry. There are approaches to alter the profile of metabolites not only by using plant genes, but also by using bacterial genes encoding modifying enzymes. Also, strategies to cope with unwanted or even toxic compounds are available. The need for metabolic engineering of plant secondary metabolite pathways is increasing with the rising demand for (novel) compounds with new bioactive properties. Here, we give some examples of recent developments for the metabolic engineering of plants and organ cultures, which can be used in the production of metabolites with interesting properties. Copyright © 2014 Elsevier Inc. All rights reserved.

  14. Modules of co-regulated metabolites in turmeric (Curcuma longa) rhizome suggest the existence of biosynthetic modules in plant specialized metabolism.

    Science.gov (United States)

    Xie, Zhengzhi; Ma, Xiaoqiang; Gang, David R

    2009-01-01

    Turmeric is an excellent example of a plant that produces large numbers of metabolites from diverse metabolic pathways or networks. It is hypothesized that these metabolic pathways or networks contain biosynthetic modules, which lead to the formation of metabolite modules-groups of metabolites whose production is co-regulated and biosynthetically linked. To test whether such co-regulated metabolite modules do exist in this plant, metabolic profiling analysis was performed on turmeric rhizome samples that were collected from 16 different growth and development treatments, which had significant impacts on the levels of 249 volatile and non-volatile metabolites that were detected. Importantly, one of the many co-regulated metabolite modules that were indeed readily detected in this analysis contained the three major curcuminoids, whereas many other structurally related diarylheptanoids belonged to separate metabolite modules, as did groups of terpenoids. The existence of these co-regulated metabolite modules supported the hypothesis that the 3-methoxyl groups on the aromatic rings of the curcuminoids are formed before the formation of the heptanoid backbone during the biosynthesis of curcumin and also suggested the involvement of multiple polyketide synthases with different substrate selectivities in the formation of the array of diarylheptanoids detected in turmeric. Similar conclusions about terpenoid biosynthesis could also be made. Thus, discovery and analysis of metabolite modules can be a powerful predictive tool in efforts to understand metabolism in plants.

  15. Lichen secondary metabolites affect growth of Physcomitrella patens by allelopathy.

    Science.gov (United States)

    Goga, Michal; Antreich, Sebastian J; Bačkor, Martin; Weckwerth, Wolfram; Lang, Ingeborg

    2017-05-01

    Lichen secondary metabolites can function as allelochemicals and affect the development and growth of neighboring bryophytes, fungi, vascular plants, microorganisms, and even other lichens. Lichen overgrowth on bryophytes is frequently observed in nature even though mosses grow faster than lichens, but there is still little information on the interactions between lichens and bryophytes.In the present study, we used extracts from six lichen thalli containing secondary metabolites like usnic acid, protocetraric acid, atranorin, lecanoric acid, nortistic acid, and thamnolic acid. To observe the influence of these metabolites on bryophytes, the moss Physcomitrella patens was cultivated for 5 weeks under laboratory conditions and treated with lichen extracts. Toxicity of natural mixtures of secondary metabolites was tested at three selected doses (0.001, 0.01, and 0.1 %). When the mixture contained substantial amounts of usnic acid, we observed growth inhibition of protonemata and reduced development of gametophores. Significant differences in cell lengths and widths were also noticed. Furthermore, usnic acid had a strong effect on cell division in protonemata suggesting a strong impact on the early stages of bryophyte development by allelochemicals contained in the lichen secondary metabolites.Biological activities of lichen secondary metabolites were confirmed in several studies such as antiviral, antibacterial, antitumor, antiherbivore, antioxidant, antipyretic, and analgetic action or photoprotection. This work aimed to expand the knowledge on allelopathic effects on bryophyte growth.

  16. Secondary metabolites from Scorzonera latifolia roots

    Czech Academy of Sciences Publication Activity Database

    Acikara, O. B.; Šmejkal, K.; Cvačka, Josef; Buděšínský, Miloš; Dračínský, Martin; Saltan, G.

    2015-01-01

    Roč. 81, č. 16 (2015), PM167 ISSN 0032-0943. [GA 2015. International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research /63./. 23.08.2015-27.08.2015, Budapest] Institutional support: RVO:61388963 Keywords : medical plant * metabolites * Asteraceae Subject RIV: CB - Analytical Chemistry, Separation

  17. Multicomponent Analysis of the Differential Induction of Secondary Metabolite Profiles in Fungal Endophytes

    Directory of Open Access Journals (Sweden)

    Víctor González-Menéndez

    2016-02-01

    Full Text Available Small molecule histone deacetylase (HDAC and DNA methyltransferase (DNMT inhibitors are commonly used to perturb the production of fungal metabolites leading to the induction of the expression of silent biosynthetic pathways. Several reports have described the variable effects observed in natural product profiles in fungi treated with HDAC and DNMT inhibitors, such as enhanced chemical diversity and/or the induction of new molecules previously unknown to be produced by the strain. Fungal endophytes are known to produce a wide variety of secondary metabolites (SMs involved in their adaptation and survival within higher plants. The plant-microbe interaction may influence the expression of some biosynthetic pathways, otherwise cryptic in these fungi when grown in vitro. The aim of this study was to setup a systematic approach to evaluate and identify the possible effects of HDAC and DNMT inhibitors on the metabolic profiles of wild type fungal endophytes, including the chemical identification and characterization of the most significant SMs induced by these epigenetic modifiers.

  18. Metabolomics methods for the synthetic biology of secondary metabolism

    NARCIS (Netherlands)

    Quoc-Thai Nguyen, [No Value; Merlo, Maria E.; Medema, Marnix H.; Jankevics, Andris; Breitling, Rainer; Takano, Eriko; Just, Wilhelm; Reiss, Thomas

    2012-01-01

    Many microbial secondary metabolites are of high biotechnological value for medicine, agriculture, and the food industry. Bacterial genome mining has revealed numerous novel secondary metabolite biosynthetic gene clusters, which encode the potential to synthesize a large diversity of compounds that

  19. Isolation and Biosynthetic Analysis of Haliamide, a New PKS-NRPS Hybrid Metabolite from the Marine Myxobacterium Haliangium ochraceum

    Directory of Open Access Journals (Sweden)

    Yuwei Sun

    2016-01-01

    Full Text Available Myxobacteria of marine origin are rare and hard-to-culture microorganisms, but they genetically harbor high potential to produce novel antibiotics. An extensive investigation on the secondary metabolome of the unique marine myxobacterium Haliangium ochraceum SMP-2 led to the isolation of a new polyketide-nonribosomal peptide hybrid product, haliamide (1. Its structure was elucidated by spectroscopic analyses including NMR and HR-MS. Haliamide (1 showed cytotoxicity against HeLa-S3 cells with IC50 of 12 μM. Feeding experiments were performed to identify the biosynthetic building blocks of 1, revealing one benzoate, one alanine, two propionates, one acetate and one acetate-derived terminal methylene. The biosynthetic gene cluster of haliamide (hla, 21.7 kbp was characterized through the genome mining of the producer, allowing us to establish a model for the haliamide biosynthesis. The sulfotransferase (ST-thioesterase (TE domains encoded in hlaB appears to be responsible for the terminal alkene formation via decarboxylation.

  20. To Stretch the Boundary of Secondary Metabolite Production in Plant Cell-Based Bioprocessing: Anthocyanin as a Case Study

    Directory of Open Access Journals (Sweden)

    Wei Zhang

    2004-01-01

    Full Text Available Plant cells and tissue cultures hold great promise for controlled production of a myriad of useful secondary metabolites on demand. The current yield and productivity cannot fulfill the commercial goal of a plant cell-based bioprocess for the production of most secondary metabolites. In order to stretch the boundary, recent advances, new directions and opportunities in plant cell-based bioprocessing, have been critically examined for the 10 years from 1992 to 2002. A review of the literature indicated that most of the R&D work was devoted predominantly to studies at an empirical level. A rational approach to molecular plant cell bioprocessing based on the fundamental understanding of metabolic pathways and their regulations is urgently required to stimulate further advances; however, the strategies and technical framework are still being developed. It is the aim of this review to take a step forward in framing workable strategies and technologies for molecular plant cell-based bioprocessing. Using anthocyanin biosynthesis as a case study, an integrated postgenomic approach has been proposed. This combines the functional analysis of metabolic pathways for biosynthesis of a particular metabolite from profiling of gene expression and protein expression to metabolic profiling. A global correlation not only can thus be established at the three molecular levels, but also places emphasis on the interactions between primary metabolism and secondary metabolism; between competing and/or complimentary pathways; and between biosynthetic and post-biosynthetic events.

  1. Role of the phosphopantetheinyltransferase enzyme, PswP, in the biosynthesis of antimicrobial secondary metabolites by Serratia marcescens Db10.

    Science.gov (United States)

    Gerc, Amy J; Stanley-Wall, Nicola R; Coulthurst, Sarah J

    2014-08-01

    Phosphopantetheinyltransferase (PPTase) enzymes fulfil essential roles in primary and secondary metabolism in prokaryotes, archaea and eukaryotes. PPTase enzymes catalyse the essential modification of the carrier protein domain of fatty acid synthases, polyketide synthases (PKSs) and non-ribosomal peptide synthetases (NRPSs). In bacteria and fungi, NRPS and PKS enzymes are often responsible for the biosynthesis of secondary metabolites with clinically relevant properties; these secondary metabolites include a variety of antimicrobial peptides. We have previously shown that in the Gram-negative bacterium Serratia marcescens Db10, the PPTase enzyme PswP is essential for the biosynthesis of an NRPS-PKS dependent antibiotic called althiomycin. In this work we utilize bioinformatic analyses to classify PswP as belonging to the F/KES subfamily of Sfp type PPTases and to putatively identify additional NRPS substrates of PswP, in addition to the althiomycin NRPS-PKS, in Ser. marcescens Db10. We show that PswP is required for the production of three diffusible metabolites by this organism, each possessing antimicrobial activity against Staphylococcus aureus. Genetic analyses identify the three metabolites as althiomycin, serrawettin W2 and an as-yet-uncharacterized siderophore, which may be related to enterobactin. Our results highlight the use of an individual PPTase enzyme in multiple biosynthetic pathways, each contributing to the ability of Ser. marcescens to inhibit competitor bacteria by the production of antimicrobial secondary metabolites. © 2014 The Authors.

  2. Bioactive secondary metabolites from marine microbes for drug discovery.

    Science.gov (United States)

    Nikapitiya, Chamilani

    2012-01-01

    The isolation and extraction of novel bioactive secondary metabolites from marine microorganisms have a biomedical potential for future drug discovery as the oceans cover 70% of the planet's surface and life on earth originates from sea. Wide range of novel bioactive secondary metabolites exhibiting pharmacodynamic properties has been isolated from marine microorganisms and many to be discovered. The compounds isolated from marine organisms (macro and micro) are important in their natural form and also as templates for synthetic modifications for the treatments for variety of deadly to minor diseases. Many technical issues are yet to overcome before wide-scale bioprospecting of marine microorganisms becomes a reality. This chapter focuses on some novel secondary metabolites having antitumor, antivirus, enzyme inhibitor, and other bioactive properties identified and isolated from marine microorganisms including bacteria, actinomycetes, fungi, and cyanobacteria, which could serve as potentials for drug discovery after their clinical trials. Copyright © 2012 Elsevier Inc. All rights reserved.

  3. The secondary metabolite bioinformatics portal: Computational tools to facilitate synthetic biology of secondary metabolite production

    Directory of Open Access Journals (Sweden)

    Tilmann Weber

    2016-06-01

    Full Text Available Natural products are among the most important sources of lead molecules for drug discovery. With the development of affordable whole-genome sequencing technologies and other ‘omics tools, the field of natural products research is currently undergoing a shift in paradigms. While, for decades, mainly analytical and chemical methods gave access to this group of compounds, nowadays genomics-based methods offer complementary approaches to find, identify and characterize such molecules. This paradigm shift also resulted in a high demand for computational tools to assist researchers in their daily work. In this context, this review gives a summary of tools and databases that currently are available to mine, identify and characterize natural product biosynthesis pathways and their producers based on ‘omics data. A web portal called Secondary Metabolite Bioinformatics Portal (SMBP at http://www.secondarymetabolites.org is introduced to provide a one-stop catalog and links to these bioinformatics resources. In addition, an outlook is presented how the existing tools and those to be developed will influence synthetic biology approaches in the natural products field.

  4. Diversity of secondary metabolites from Genus Artocarpus (Moraceae

    Directory of Open Access Journals (Sweden)

    ALIEFMAN HAKIM

    2010-11-01

    Full Text Available Hakim A. 2010. The diversity of secondary metabolites from Genus Artocarpus (Moraceae. Nusantara Bioscience 2:146-156. Several species of the Artocarpus genus (Moraceae have been investigated their natural product. The secondary metabolites successfully being isolatad from Artocarpus genus consist of terpenoid, flavonoids, stilbenoid, arylbenzofuran, neolignan, and adduct Diels-Alder. Flavonoid group represent the compound which is the most found from Artocarpus plant. The flavonoids compound which are successfully isolated from Artocarpus plant consist of the varied frameworks like chalcone, flavanone, flavan-3-ol, simple flavone, prenylflavone, oxepinoflavone, pyranoflavone, dihydrobenzoxanthone, furanodihydrobenzoxanthone, pyranodihydrobenzoxanthone, quinonoxanthone, cyclopentenoxanthone, xanthonolide, dihydroxanthone.

  5. Activation of the Silent Secondary Metabolite Production by Introducing Neomycin-Resistance in a Marine-Derived Penicillium purpurogenum G59

    Directory of Open Access Journals (Sweden)

    Chang-Jing Wu

    2015-04-01

    Full Text Available Introduction of neomycin-resistance into a marine-derived, wild-type Penicillium purpurogenum G59 resulted in activation of silent biosynthetic pathways for the secondary metabolite production. Upon treatment of G59 spores with neomycin and dimethyl sulfoxide (DMSO, a total of 56 mutants were obtained by single colony isolation. The acquired resistance of mutants to neomycin was testified by the resistance test. In contrast to the G59 strain, the EtOAc extracts of 28 mutants inhibited the human cancer K562 cells, indicating that the 28 mutants have acquired the capability to produce bioactive metabolites. HPLC-photodiode array detector (PDAD-UV and HPLC-electron spray ionization (ESI-MS analyses further indicated that diverse secondary metabolites have been newly produced in the bioactive mutant extracts. Followed isolation and characterization demonstrated that five bioactive secondary metabolites, curvularin (1, citrinin (2, penicitrinone A (3, erythro-23-O-methylneocyclocitrinol (4 and 22E-7α-methoxy-5α, 6α-epoxyergosta-8(14,22-dien-3β-ol (5, were newly produced by a mutant, 4-30, compared to the G59 strain. All 1–5 were also not yet found in the secondary metabolites of other wild type P. purpurogenum strains. Compounds 1–5 inhibited human cancer K562, HL-60, HeLa and BGC-823 cells to varying extents. Both present bioassays and chemical investigations demonstrated that the introduction of neomycin-resistance into the marine-derived fungal G59 strain could activate silent secondary metabolite production. The present work not only extended the previous DMSO-mediated method for introducing drug-resistance in fungi both in DMSO concentrations and antibiotics, but also additionally exemplified effectiveness of this method for activating silent fungal secondary metabolites. This method could be applied to other fungal isolates to elicit their metabolic potentials to investigate secondary metabolites from silent biosynthetic pathways.

  6. ATNT: an enhanced system for expression of polycistronic secondary metabolite gene clusters in Aspergillus niger.

    Science.gov (United States)

    Geib, Elena; Brock, Matthias

    2017-01-01

    Fungi are treasure chests for yet unexplored natural products. However, exploitation of their real potential remains difficult as a significant proportion of biosynthetic gene clusters appears silent under standard laboratory conditions. Therefore, elucidation of novel products requires gene activation or heterologous expression. For heterologous gene expression, we previously developed an expression platform in Aspergillus niger that is based on the transcriptional regulator TerR and its target promoter P terA . In this study, we extended this system by regulating expression of terR  by the doxycycline inducible Tet-on system. Reporter genes cloned under the control of the target promoter P terA remained silent in the absence of doxycycline, but were strongly expressed when doxycycline was added. Reporter quantification revealed that the coupled system results in about five times higher expression rates compared to gene expression under direct control of the Tet-on system. As production of secondary metabolites generally requires the expression of several biosynthetic genes, the suitability of the self-cleaving viral peptide sequence P2A was tested in this optimised expression system. P2A allowed polycistronic expression of genes required for Asp-melanin formation in combination with the gene coding for the red fluorescent protein tdTomato. Gene expression and Asp-melanin formation was prevented in the absence of doxycycline and strongly induced by addition of doxycycline. Fluorescence studies confirmed the correct subcellular localisation of the respective enzymes. This tightly regulated but strongly inducible expression system enables high level production of secondary metabolites most likely even those with toxic potential. Furthermore, this system is compatible with polycistronic gene expression and, thus, suitable for the discovery of novel natural products.

  7. Role of secondary metabolites/antioxidants in vitro

    Science.gov (United States)

    In literature, secondary metabolites are described as natural products, waste, phytopharmaceuticals, bioactive constituents or by-products of the primary metabolism. They occur in many plant genera and microorganisms in vivo and in vitro, and have complex chemical structures specific to the plants w...

  8. Impact of secondary metabolites and related enzymes in flax ...

    African Journals Online (AJOL)

    Changes in various physiological defenses including secondary metabolites, proline, total soluble protein and antioxidant enzymes were investigated in leaves and stems of 18 flax lines either resistant or susceptible to powdery mildew. The results showed that the total alkaloids content in flax stems was significantly ...

  9. Characterization of primary and secondary metabolites of leaf and ...

    African Journals Online (AJOL)

    This study evaluates the primary and secondary metabolite profiles of Eurycoma longifolia Jack (EL) stems and leaves to determine whether it can be utilized for therapeutic purposes as the roots. A total of six types of extracts were tested. The extracts showed high content of glycosaponins, polysaccharides, proteins and ...

  10. A Review of the Secondary Metabolites and Biological Activities of ...

    African Journals Online (AJOL)

    Tinospora crispa Beumee, a herbaceous climber, has been widely used in traditional medicine for treating various ailments such as contusion, septicaemia, fever, fracture, scabies and other tropical ulcers. A wide range of secondary metabolites such as alkaloids, diterpenes, flavones, phenolics, and triterpenes have been ...

  11. A Review of the Secondary Metabolites and Biological Activities of ...

    African Journals Online (AJOL)

    Review Article. A Review of the Secondary Metabolites and Biological. Activities of Tinospora crispa ... triterpenes have been isolated, some of which have also shown corresponding biological activities. The current review is an update on the .... were found to exhibit higher antioxidative potency than the synthetic antioxidant.

  12. Secondary metabolites from the unique bamboo, Melocanna baccifera.

    Science.gov (United States)

    Govindan, Balaji; Johnson, Anil John; Viswanathan, Gayathri; Ramaswamy, Venkataraman; Koshy, Konnath Chacko; Baby, Sabulal

    2018-02-15

    Phytochemistry of fruits and leaves of the unique bamboo Melocanna baccifera resulted in the isolation of 27 secondary metabolites, including 4-Oxabicyclo[3.2.2]nona-1(7),5,8-triene and Verbacine. Biological activity studies of Verbacine revealed it as an inhibitor of acetylcholinesterase and as cytotoxic against C6 cancer cells.

  13. Extraction of secondary metabolites from plant material: a review

    NARCIS (Netherlands)

    Starmans, D.A.J.; Nijhuis, H.H.

    1996-01-01

    This review article intends to give an overview of the developments in the extraction technology of secondary metabolites from plant material. There are three types of conventional extraction techniques. In order of increasing technological difficulty, these involve the use of solvents, steam or

  14. Towards systems metabolic engineering of streptomycetes for secondary metabolites production

    DEFF Research Database (Denmark)

    Robertsen, Helene Lunde; Weber, Tilmann; Kim, Hyun Uk

    2017-01-01

    Streptomycetes are known for their inherent ability to produce pharmaceutically relevant secondary metabolites. Discovery of medically useful, yet novel compounds has become a great challenge due to frequent rediscovery of known compounds and a consequent decline in the number of relevant clinical...

  15. Role of secondary metabolites biosynthesis in resistance to cotton ...

    African Journals Online (AJOL)

    Secondary metabolites production in healthy and diseased sample of leaves of cotton varieties after the attack of CLCuV found maximum phenolics, carotenoids, chlorophyll a, chlorophyll b and total chlorophyll a and b in healthy sample and minimum contents present in diseased sample. CIM-446 was the best variety to ...

  16. Importance of Secondary Metabolites for Leaf Beetles (Coleoptera: Chrysomelidae

    Directory of Open Access Journals (Sweden)

    A. N. EKİZ

    2014-06-01

    Full Text Available Leaf beetles (Chrysomelidae are one of the most diverse families of herbivorous insects. Many of them are important agricultural pests and cause remarkable loss of crop and money as well. Plant leaves and roots are primary food source of both larva and adults of leaf beetles. Plants produce many secondary metabolites in reaction to herbivore insects. It is a well-known phenomenon that quantity and variety of secondary metabolites in plant leaves may change in response to insect attacks. Herbivore insects have to deal with such defensive secondary chemicals and overcome either by detoxifying or storing them. Accordingly, many specialist herbivores coevolved with their host plant. Certain phenolic glycosides may reduce leaf beetle feeding. Condensed tannins are anti-herbivore defenses against leaf chewing beetles, including leaf beetles. Flavonoid compounds are feeding deterrents for many flea leaf beetles. Cinnamic acid derivatives are other known feeding deterrents for leaf beetles. Secondary metabolites quantity and nutritional quality of host plants are not only important for feeding but also for providing enemy-free space and suitable oviposition sites.

  17. Ecotoxicological effects of selected cyanobacterial secondary metabolites a short review

    International Nuclear Information System (INIS)

    Wiegand, C.; Pflugmacher, S.

    2005-01-01

    Cyanobacteria are one of the most diverse groups of gram-negative photosynthetic prokaryotes. Many of them are able to produce a wide range of toxic secondary metabolites. These cyanobacterial toxins can be classified in five different groups: hepatotoxins, neurotoxins, cytotoxins, dermatotoxins, and irritant toxins (lipopolysaccharides). Cyanobacterial blooms are hazardous due to this production of secondary metabolites and endotoxins, which could be toxic to animals and plants. Many of the freshwater cyanobacterial blooms include species of the toxigenic genera Microcystis, Anabaena, or Plankthotrix. These compounds differ in mechanisms of uptake, affected organs, and molecular mode of action. In this review, the main focus is the aquatic environment and the effects of these toxins to the organisms living there. Some basic toxic mechanisms will be discussed in comparison to the mammalian system

  18. Secondary Metabolites from Inula britannica L. and Their Biological Activities

    Directory of Open Access Journals (Sweden)

    Yoon-Ha Kim

    2010-03-01

    Full Text Available Inula britannica L., family Asteraceae, is used in traditional Chinese and Kampo Medicines for various diseases. Flowers or the aerial parts are a rich source of secondary metabolites. These consist mainly of terpenoids (sesquiterpene lactones and dimmers, diterpenes and triterpenoids and flavonoids. The isolated compounds have shown diverse biological activities: anticancer, antioxidant, anti-inflammatory, neuroprotective and hepatoprotective activities. This review provides information on isolated bioactive phytochemicals and pharmacological potentials of I. britannica.

  19. Antimicrobial efficacy of secondary metabolites from Glomerella cingulata

    OpenAIRE

    Hara Kishore, K.; Misra, Sunil; Ramesh Chandra, D.; Prakash, K.V.V. R.; Suryanarayana Murty, U.

    2007-01-01

    Fungi are known to produce a vast array of secondary metabolites that are gaining importance for their biotechnological applications. Early reports suggest that G. cingulata has the capability to transform many compounds by various enzymatic actions. Therefore, the focus of this study was to determine the antibacterial and antifungal activity of crude ethyl acetate extract of G. cingulata using agar cup bioassay method. Crude extract of G. cingulata exhibited remarkable antifungal activity ag...

  20. [Secondary metabolites accumulating and geoherbs formation under enviromental stress].

    Science.gov (United States)

    Huang, Lu-Qi; Guo, Lan-Ping

    2007-02-01

    This paper analyzed how habitat affected the formation of geoherbs after summarizing the influences of environmental stress on plants growth, especially on theirs secondary metabolites accumulating, and introducing 4 kinds hypothesis about environmental stress affects plants. It was then pointed out that environmental stress may have advantage on the formation of geoherbs. The stress effect hypothesis on forming geoherbs was brought forward, and the ways and methods on study the geoherbs under environmental stress was discussed.

  1. Production of Secondary Metabolites in Extreme Environments: Food- and Airborne Wallemia spp. Produce Toxic Metabolites at Hypersaline Conditions

    DEFF Research Database (Denmark)

    Jančič, Sašo; Frisvad, Jens Christian; Kocev, Dragi

    2016-01-01

    the genome data analysis of W. mellicola (previously W. sebi sensu lato) and W. ichthyophaga revealed a low number of secondary metabolites clusters, a substantial number of secondary metabolites were detected at different conditions. Machine learning analysis of the obtained dataset showed that NaCl has...... of salt or sugar. In relation to food safety, the effect of high salt and sugar concentrations on the production of secondary metabolites by this toxigenic fungus was investigated. The secondary metabolite profiles of 30 strains of the listed species were examined using general growth media, known...... to support the production of secondary metabolites, supplemented with different concentrations of NaCl, glucose and MgCl2. In more than two hundred extracts approximately one hundred different compounds were detected using high-performance liquid chromatography-diode array detection (HPLC-DAD). Although...

  2. Secondary metabolites of Antarctic fungi antagonistic to aquatic pathogenic bacteria

    Directory of Open Access Journals (Sweden)

    Zhao Huibin

    2018-03-01

    Full Text Available Polar microbial derived antibiotics have potential as alternatives to traditional antibiotics in treating fish against pathogenic bacteria. In this paper, 23 strains of polar fungi were fermented to detect bacteriostatic products on three aquatic pathogenic bacteria, subsequently the active fungus was identified. It was indicated that secondary metabolites of 23 strains weredistinct; of these, the extract of strain B-7 (belonging to Bjerkandera according to molecular identification demonstrated a strong antibacterial activity to Streptococcus agalactiae, Vibrio anguillarum and Aeromonas hydrophila ATCC7966 by Kirby-Bauerpaper strip method. During one fermentation cycle, the pH curve of the fermentation liquor became lowest (4.0 on the 4th day and rose back to 7.6 finally after 5 days, The residual sugar curve was decreased before stablising on the 6th day. It is presumed that a large amount of alkaline secondary metabolites might have been produced during fermentation. This study focuses on antagonism between aquatic pathogenic bacteria and fermentation metabolites from Antarctic fungi for the first time, which may provide data on research of antibiotics against aquatic pathogenic bacteria.

  3. Linking fungal secondary metabolites and pathways to their genes in Aspergillus

    DEFF Research Database (Denmark)

    Petersen, Lene Maj

    . oryzae metabolites, however, revealed the chemical link between the two species. In two parallel projects, involving A. niger and A. aculeatus respectively, the polyketide 6-methyl salicylic acid (6-MSA), and corresponding biosynthetic pathways, were investigated. In A. niger, 6-MSA was converted...

  4. A new species of Trichoderma hypoxylon harbours abundant secondary metabolites.

    Science.gov (United States)

    Sun, Jingzu; Pei, Yunfei; Li, Erwei; Li, Wei; Hyde, Kevin D; Yin, Wen-Bing; Liu, Xingzhong

    2016-11-21

    Some species of Trichoderma are fungicolous on fungi and have been extensively studied and commercialized as biocontrol agents. Multigene analyses coupled with morphology, resulted in the discovery of T. hypoxylon sp. nov., which was isolated from surface of the stroma of Hypoxylon anthochroum. The new taxon produces Trichoderma- to Verticillium-like conidiophores and hyaline conidia. Phylogenetic analyses based on combined ITS, TEF1-α and RPB2 sequence data indicated that T. hypoxylon is a well-distinguished species with strong bootstrap support in the polysporum group. Chemical assessment of this species reveals a richness of secondary metabolites with trichothecenes and epipolythiodiketopiperazines as the major compounds. The fungicolous life style of T. hypoxylon and the production of abundant metabolites are indicative of the important ecological roles of this species in nature.

  5. SeMPI: a genome-based secondary metabolite prediction and identification web server.

    Science.gov (United States)

    Zierep, Paul F; Padilla, Natàlia; Yonchev, Dimitar G; Telukunta, Kiran K; Klementz, Dennis; Günther, Stefan

    2017-07-03

    The secondary metabolism of bacteria, fungi and plants yields a vast number of bioactive substances. The constantly increasing amount of published genomic data provides the opportunity for an efficient identification of gene clusters by genome mining. Conversely, for many natural products with resolved structures, the encoding gene clusters have not been identified yet. Even though genome mining tools have become significantly more efficient in the identification of biosynthetic gene clusters, structural elucidation of the actual secondary metabolite is still challenging, especially due to as yet unpredictable post-modifications. Here, we introduce SeMPI, a web server providing a prediction and identification pipeline for natural products synthesized by polyketide synthases of type I modular. In order to limit the possible structures of PKS products and to include putative tailoring reactions, a structural comparison with annotated natural products was introduced. Furthermore, a benchmark was designed based on 40 gene clusters with annotated PKS products. The web server of the pipeline (SeMPI) is freely available at: http://www.pharmaceutical-bioinformatics.de/sempi. © The Author(s) 2017. Published by Oxford University Press on behalf of Nucleic Acids Research.

  6. Secondary metabolites and biological activity of Pentas species: A minireview

    Directory of Open Access Journals (Sweden)

    Heba-tollah M. Sweelam

    2018-03-01

    Full Text Available The genus Pentas belongs to the Rubiaceae family, which contains approximately 40 species. Several Pentas species were reported to be used as a folk treatment by African indigenous people in treating some diseases such as malaria, tapeworms, dysentery, gonorrhea, syphilis and snake poisoning. This article covers the period from 1962 to 2017 and presents an overview of the biological activity of different Pentas species and describes their phytochemical traits. As a conclusion, the main secondary metabolites from Pentas species are quinones, highly oxygenated chromene-based structures, and iridoids. Pentas species are widely used in folk medicine but they have to be more investigated for their medicinal properties.

  7. A proteomic approach to investigating gene cluster expression and secondary metabolite functionality in Aspergillus fumigatus.

    Directory of Open Access Journals (Sweden)

    Rebecca A Owens

    Full Text Available A combined proteomics and metabolomics approach was utilised to advance the identification and characterisation of secondary metabolites in Aspergillus fumigatus. Here, implementation of a shotgun proteomic strategy led to the identification of non-redundant mycelial proteins (n = 414 from A. fumigatus including proteins typically under-represented in 2-D proteome maps: proteins with multiple transmembrane regions, hydrophobic proteins and proteins with extremes of molecular mass and pI. Indirect identification of secondary metabolite cluster expression was also achieved, with proteins (n = 18 from LaeA-regulated clusters detected, including GliT encoded within the gliotoxin biosynthetic cluster. Biochemical analysis then revealed that gliotoxin significantly attenuates H2O2-induced oxidative stress in A. fumigatus (p>0.0001, confirming observations from proteomics data. A complementary 2-D/LC-MS/MS approach further elucidated significantly increased abundance (p<0.05 of proliferating cell nuclear antigen (PCNA, NADH-quinone oxidoreductase and the gliotoxin oxidoreductase GliT, along with significantly attenuated abundance (p<0.05 of a heat shock protein, an oxidative stress protein and an autolysis-associated chitinase, when gliotoxin and H2O2 were present, compared to H2O2 alone. Moreover, gliotoxin exposure significantly reduced the abundance of selected proteins (p<0.05 involved in de novo purine biosynthesis. Significantly elevated abundance (p<0.05 of a key enzyme, xanthine-guanine phosphoribosyl transferase Xpt1, utilised in purine salvage, was observed in the presence of H2O2 and gliotoxin. This work provides new insights into the A. fumigatus proteome and experimental strategies, plus mechanistic data pertaining to gliotoxin functionality in the organism.

  8. Secondary Metabolites and Bioactivity of Hyophila involuta (Hook Jaeg.

    Directory of Open Access Journals (Sweden)

    Amos M. MAKINDE

    2015-12-01

    Full Text Available The phytochemical screening of Hyophila involuta collected from the Biological Garden of the Obafemi Awolowo University, Ile-Ife, Nigeria, was carried out to investigate the presence or absence of some secondary metabolites and its antibiotic potentials, using different extracts (with acetone and ethanol on selected organisms. The extracts obtained were screened for the presence of secondary metabolites like alkaloids, anthraquinones, cardiac glycosides, flavonoids, phlobatanins, saponins, steroids, tannins, triterpenes and xanthoproteins. Antimicrobial activity of the extracts was carried out on Escherichia coli, Staphylococcus aureus, Aspergillus flavus and Candida albicans. Only acetone extract tested positive for the presence of flavonoids, while alkaloids and cardiac glycosides were detected present in both the acetone and ethanolic extracts. Flavonoids were detected present only in the acetone extract. Saponins were detected present only in the ethanolic extract. The extracts (acetone and ethanolic showed significant activity on Staphylococcus aureus and Aspergillus flavus. The results obtained from this study indicated that H. involuta has medicinally important compounds, having therapeutic potential from which effective antimicrobial medicine can be sourced.

  9. Lichen Secondary Metabolite, Physciosporin, Inhibits Lung Cancer Cell Motility

    Science.gov (United States)

    Yang, Yi; Park, So-Yeon; Nguyen, Thanh Thi; Yu, Young Hyun; Nguyen, Tru Van; Sun, Eun Gene; Udeni, Jayalal; Jeong, Min-Hye; Pereira, Iris; Moon, Cheol; Ha, Hyung-Ho; Kim, Kyung Keun; Hur, Jae-Seoun; Kim, Hangun

    2015-01-01

    Lichens produce various unique chemicals that can be used for pharmaceutical purposes. To screen for novel lichen secondary metabolites showing inhibitory activity against lung cancer cell motility, we tested acetone extracts of 13 lichen samples collected in Chile. Physciosporin, isolated from Pseudocyphellaria coriacea (Hook f. & Taylor) D.J. Galloway & P. James, was identified as an effective compound and showed significant inhibitory activity in migration and invasion assays against human lung cancer cells. Physciosporin treatment reduced both protein and mRNA levels of N-cadherin with concomitant decreases in the levels of epithelial-mesenchymal transition markers such as snail and twist. Physciosporin also suppressed KITENIN (KAI1 C-terminal interacting tetraspanin)-mediated AP-1 activity in both the absence and presence of epidermal growth factor stimulation. Quantitative real-time PCR analysis showed that the expression of the metastasis suppressor gene, KAI1, was increased while that of the metastasis enhancer gene, KITENIN, was dramatically decreased by physciosporin. Particularly, the activity of 3’-untranslated region of KITENIN was decreased by physciosporin. Moreover, Cdc42 and Rac1 activities were decreased by physciosporin. These results demonstrated that the lichen secondary metabolite, physciosporin, inhibits lung cancer cell motility through novel mechanisms of action. PMID:26371759

  10. Medicinal Plants: A Source of Anti-Parasitic Secondary Metabolites

    Directory of Open Access Journals (Sweden)

    Michael Wink

    2012-10-01

    Full Text Available This review summarizes human infections caused by endoparasites, including protozoa, nematodes, trematodes, and cestodes, which affect more than 30% of the human population, and medicinal plants of potential use in their treatment. Because vaccinations do not work in most instances and the parasites have sometimes become resistant to the available synthetic therapeutics, it is important to search for alternative sources of anti-parasitic drugs. Plants produce a high diversity of secondary metabolites with interesting biological activities, such as cytotoxic, anti-parasitic and anti-microbial properties. These drugs often interfere with central targets in parasites, such as DNA (intercalation, alkylation, membrane integrity, microtubules and neuronal signal transduction. Plant extracts and isolated secondary metabolites which can inhibit protozoan parasites, such as Plasmodium, Trypanosoma, Leishmania, Trichomonas and intestinal worms are discussed. The identified plants and compounds offer a chance to develop new drugs against parasitic diseases. Most of them need to be tested in more detail, especially in animal models and if successful, in clinical trials.

  11. Secondary Metabolites Production by Solid-State Fermentation

    Directory of Open Access Journals (Sweden)

    Barrios-González, J.

    2005-01-01

    Full Text Available Microbial secondary metabolites are useful high value products with an enormous range of biological activities. Moreover, the past two decades have been a phase of rapid discovery of new activities and development of major compounds for use in different industrial fields, mainly pharmaceuticals, cosmetics, food, agriculture and farming. Many of these metabolites could be produced advantageously in industry by solid–state fermentation (SSF. Two types of SSF can be distinguished, depending on the nature of the solid phase used: 1 Solid cultures of one support-substrate phase in which solid phase is constituted by a material that assumes, simultaneously, the functions of support and of nutrients source; and 2 Solid cultures of two substrate-support phases: solid phase is constituted by an inert support impregnated with a liquid medium. Besides good production performance, two phases systems have provided a convenient model for basic studies. Studies in our laboratory, as well as in others, have shown that physiology of idiophase (production phase in SSF share several similarities with the physiology in liquid medium, so similar strategies must be adapted for efficient production processes. However, our studies indicate the need to develop special strains for SSF since overproducing strains, generated for liquid fermentation, cannot be relied upon to perform well in SSF. On the other hand, there are important parameters, specific for SSF, that have to be optimized (pretreatment, initial moisture content, medium concentration and aeration. Respiration studies of secondary metabolites SSF, performed in our laboratory, have shown more subtle aspects of efficient production in SSF. This indicates that there are certain particularities of physiology in SSF that represent the point that needs a better understanding, and that promise to generate knowledge that will be the basis for efficient processes development and control strategies, as well as for

  12. Does prescribed burning affect leaf secondary metabolites in pine stands?

    Science.gov (United States)

    Lavoir, A V; Ormeño, E; Pasqualini, V; Ferrat, L; Greff, S; Lecareux, C; Vila, B; Mévy, J P; Fernandez, C

    2013-03-01

    Prescribed burning (PB) is gaining popularity as a low-cost forest protection measure that efficiently reduces fuel build-up, but its effects on tree health and growth are poorly understood. Here, we evaluated the impact of PB on plant defenses in Mediterranean pine forests (Pinus halepensis and P. nigra ssp. laricio). These chemical defenses were estimated based on needle secondary metabolites (terpenes and phenolics including flavonoids) and discussed in terms of chlorophyll fluorescence and soil nutrients. Three treatments were applied: absence of burning (control plots); single burns (plots burned once); and repeated burns (plots burned twice). For single burns, we also explored changes over time. In P. laricio, PB tended to trigger only minor modifications consisting exclusively of short-lived increases (observed within 3 months after PB) in flavonoid index, possibly due to the leaf temperature increase during PB. In P. halepensis, PB had detrimental effects on physiological performance, consisting of (i) significant decreases in actual PSII efficiency (ΦPSII) in light-adapted conditions after repeated PB, and (ii) short-lived decreases in variable-to-maximum fluorescence ratio (Fv/Fm) after single PB, indicating that PB actually stressed P. halepensis trees. Repeated PB also promoted terpene-like metabolite production, which increased 2 to 3-fold compared to control trees. Correlations between terpene metabolites and soil chemistry were found. These results suggest that PB impacts needle secondary metabolism both directly (via a temperature impact) and indirectly (via soil nutrients), and that these impacts vary according to species/site location, frequency and time elapsed since last fire. Our findings are discussed with regard to the use of PB as a forest management technique and its consequences on plant investment in chemical defenses.

  13. Dereplication Guided Discovery of Secondary Metabolites of Mixed Biosynthetic Origin from Aspergillus aculeatus

    DEFF Research Database (Denmark)

    Petersen, Lene Maj; Hoeck, Casper; Frisvad, Jens Christian

    2014-01-01

    Investigation of the chemical profile of the industrially important black filamentous fungus Aspergillus aculeatus by UHPLC-DAD-HRMS and subsequent dereplication has led to the discovery of several novel compounds. Isolation and extensive 1D and 2D NMR spectroscopic analyses allowed for structura...

  14. The poplar MYB master switches bind to the SMRE site and activate the secondary wall biosynthetic program during wood formation.

    Directory of Open Access Journals (Sweden)

    Ruiqin Zhong

    Full Text Available Wood is mainly composed of secondary walls, which constitute the most abundant stored carbon produced by vascular plants. Understanding the molecular mechanisms controlling secondary wall deposition during wood formation is not only an important issue in plant biology but also critical for providing molecular tools to custom-design wood composition suited for diverse end uses. Past molecular and genetic studies have revealed a transcriptional network encompassing a group of wood-associated NAC and MYB transcription factors that are involved in the regulation of the secondary wall biosynthetic program during wood formation in poplar trees. Here, we report the functional characterization of poplar orthologs of MYB46 and MYB83 that are known to be master switches of secondary wall biosynthesis in Arabidopsis. In addition to the two previously-described PtrMYB3 and PtrMYB20, two other MYBs, PtrMYB2 and PtrMYB21, were shown to be MYB46/MYB83 orthologs by complementation and overexpression studies in Arabidopsis. The functional roles of these PtrMYBs in regulating secondary wall biosynthesis were further demonstrated in transgenic poplar plants showing an ectopic deposition of secondary walls in PtrMYB overexpressors and a reduction of secondary wall thickening in their dominant repressors. Furthermore, PtrMYB2/3/20/21 together with two other tree MYBs, the Eucalyptus EgMYB2 and the pine PtMYB4, were shown to differentially bind to and activate the eight variants of the 7-bp SMRE consensus sequence, composed of ACC(A/TA(A/C(T/C. Together, our results indicate that the tree MYBs, PtrMYB2/3/20/21, EgMYB2 and PtMYB4, are master transcriptional switches that activate the SMRE sites in the promoters of target genes and thereby regulate secondary wall biosynthesis during wood formation.

  15. Metabolic engineering with systems biology tools to optimize production of prokaryotic secondary metabolites

    DEFF Research Database (Denmark)

    Kim, Hyun Uk; Charusanti, Pep; Lee, Sang Yup

    2016-01-01

    Metabolic engineering using systems biology tools is increasingly applied to overproduce secondary metabolites for their potential industrial production. In this Highlight, recent relevant metabolic engineering studies are analyzed with emphasis on host selection and engineering approaches...... for the optimal production of various prokaryotic secondary metabolites: native versus heterologous hosts (e.g., Escherichia coli) and rational versus random approaches. This comparative analysis is followed by discussions on systems biology tools deployed in optimizing the production of secondary metabolites....... The potential contributions of additional systems biology tools are also discussed in the context of current challenges encountered during optimization of secondary metabolite production....

  16. PECULIARITIES OF SECONDARY METABOLITES BIOSYNTHESIS IN PLANT CELL CULTURES

    Directory of Open Access Journals (Sweden)

    A.M. NOSOV

    2014-06-01

    Full Text Available metabolites formation in plant cell cultures of Panax spp., (ginsenosides; Dioscorea deltoidea (steroid glycosides; Ajuga reptans, Serratula coronata, Rhaponticum carthamoides (ecdisteroids; Polyscias spp., (triterpene glycosides, Taxus spp. (taxoids, Stevia rebaudiana (diterpene steviol-glycosides, Stephania glabra (alkaloids. They are some regular trends of secondary metabolites synthesis in the plant cell culture:It can be noted the stable synthesis of the compound promoting cell proliferation. Indeed, cell cultures of Dioscorea deltoidea were demonstrated to accumulate only furostanol glycosides, which promoted cell division. Furostanol glycoside content of Dioscorea strain DM-0.5 was up to 6 - 12% by dry biomass.Panax ginseng and P. japonicus plant cell cultures synthesize as minimum seven triterpene glycosides (ginsenosides, the productivity of these compounds was up to 6.0 - 8.0% on dry biomass.By contrast, the detectable synthesis of diterpene steviol-glycosides in cultivated cells of Stevia rebaudiana initiated in the mixotrophic cultures during chloroplast formation only.Despite these differences, or mainly due to them, plant cell cultures have become an attractive source of phytochemicals in alternative to collecting wild plants. It provides a guideline to bioreactor-based production of isoprenoids using undifferentiated plant cell cultures. 

  17. Production of Bioactive Secondary Metabolites by Marine Vibrionaceae

    Directory of Open Access Journals (Sweden)

    Lone Gram

    2011-08-01

    Full Text Available Bacteria belonging to the Vibrionaceae family are widespread in the marine environment. Today, 128 species of vibrios are known. Several of them are infamous for their pathogenicity or symbiotic relationships. Despite their ability to interact with eukaryotes, the vibrios are greatly underexplored for their ability to produce bioactive secondary metabolites and studies have been limited to only a few species. Most of the compounds isolated from vibrios so far are non-ribosomal peptides or hybrids thereof, with examples of N-containing compounds produced independent of nonribosomal peptide synthetases (NRPS. Though covering a limited chemical space, vibrios produce compounds with attractive biological activities, including antibacterial, anticancer, and antivirulence activities. This review highlights some of the most interesting structures from this group of bacteria. Many compounds found in vibrios have also been isolated from other distantly related bacteria. This cosmopolitan occurrence of metabolites indicates a high incidence of horizontal gene transfer, which raises interesting questions concerning the ecological function of some of these molecules. This account underlines the pending potential for exploring new bacterial sources of bioactive compounds and the challenges related to their investigation.

  18. Secondary Metabolites of Astragalus cruciatus Link. and Their Chemotaxonomic Significance

    Directory of Open Access Journals (Sweden)

    Wassila Benchadi

    2013-03-01

    Full Text Available In continuation of our chemical studies on the secondary metabolites of Algerian saharan species, we report on the isolation, from the methanol extract of the whole plant Astragalus cruciatus Link. , of seven known compounds including two saponins named azukisaponin V (1 and astragaloside VIII (2, four flavonoids called narcissin (3, nicotiflorin (4, kaempferol 3-O- α -L-rhamnopyranosyl-(1 ¦ 4- α -L-rhamnopyranosyl-(1 ¦ 6-β-D-glucopyranoside (5 and 5,7,2’-trihydroxyflavone (6 and one phytosterol glycoside, daucosterol (7. All the isolated compounds were characterized by using spectroscopic methods especially 1D and 2D NMR and ESI mass spectrometry and comparison with literature data . The chemotaxonomic and systematic characters of the genus Astragalus are summarized in this study to show its interesting chemodiversity throughout the world, as well as to establish the chemotaxonomical classification of this genus.

  19. A characterization NMR of secondary metabolites from lichen Parmotrema praesorediosum

    Science.gov (United States)

    Azman, Anis Asmi; Khalid, Rozida; Bakar, Muntaz Abu

    2018-04-01

    The research study was carried out to extract, isolate and characterize the secondary metabolites of lichen Parmotrema praesorediosum. Most of the lichen samples were obtained from betel nut trees and needle flowers which were collected from 17 different places around UKM Bangi campus. Each lichen sample was dried before being grinded and extracted in methanol for nine days. This process was repeated three times at room temperature. Subsequently, the resulting residues were filtered to obtain the crude extracts and further analysed using Thin Layer Chromatography (TLC) and Vacuum Column Chromatography (VLC). In order to derive the pure compounds, the isolation step was proceeded using Radial Chromatography (RC). These isolated compounds were determined by Nuclear Magnetic Resonances (NMR) and identified as methyl haematomatte (1), methyl chlorohaematomatte (2) and methyl β-orsellinate (3).

  20. Discovery of novel secondary metabolites in Aspergillus aculeatus

    DEFF Research Database (Denmark)

    Petersen, Lene Maj; Holm, Dorte Koefoed; Gotfredsen, Charlotte Held

    2012-01-01

    , whereby several novel secondary metabolites have been discovered. A. aculeatus has recently been genome-sequenced; however no genetic approaches have so far been described to facilitate genetic engineering. We here present a system for non-integrated (AMA1-based) gene expression in A. aculeatus based...... on the USERTM cloning technique. The AMA-1 based gene expression has successfully been applied to express genes in A. aculeatus and by this approach the function of a PKS gene has been established. Furthermore the technique was used to activate a silent cluster by expression of a transcription factor, leading...... of the industrially important black Aspergillus Aspergillus aculeatus by UHPLC-DAD-HRMS has identified several SMs already known from this organism. However, several compounds could not be unambiguously dereplicated wherefore some have been selected, purified and structure elucidated by 1D and 2D NMR spectroscopy...

  1. A combined genetic and multi medium approach revels new secondary metabolites in Aspergillus nidulans

    DEFF Research Database (Denmark)

    Klejnstrup, Marie Louise; Nielsen, Morten Thrane; Frisvad, Jens Christian

    Secondary metabolites are a diverse group of metabolites which serve as important natural sources of drugs for treating diseases. The availability of full genome sequences of several filamentous fungi has revealed a large genetic potential for production of secondary metabolites that are not obse......Secondary metabolites are a diverse group of metabolites which serve as important natural sources of drugs for treating diseases. The availability of full genome sequences of several filamentous fungi has revealed a large genetic potential for production of secondary metabolites...... that are not observed under standard laboratory conditions. Genetic approaches have proven a fruitfull strategy towards the production and identification of these unknown metabolites. Examples include deletion of the cclA1 and laeA2 genes in A. nidulans which affects the expression of secondary metabolites including...... monodictyphenone and terrequinone A respectively. We have deleted the cclA gene in A. nidulans and grown the mutants on several complex media to provoke the production of secondary metabolites. This resulted in the production of several metabolites not previously reported from A. nidulans. Some of these have been...

  2. Nursing protects honeybee larvae from secondary metabolites of pollen.

    Science.gov (United States)

    Lucchetti, Matteo A; Kilchenmann, Verena; Glauser, Gaetan; Praz, Christophe; Kast, Christina

    2018-03-28

    The pollen of many plants contains toxic secondary compounds, sometimes in concentrations higher than those found in the flowers or leaves. The ecological significance of these compounds remains unclear, and their impact on bees is largely unexplored. Here, we studied the impact of pyrrolizidine alkaloids (PAs) found in the pollen of Echium vulgare on honeybee adults and larvae. Echimidine, a PA present in E. vulgare pollen, was isolated and added to the honeybee diets in order to perform toxicity bioassays. While adult bees showed relatively high tolerance to PAs, larvae were much more sensitive. In contrast to other bees, the honeybee larval diet typically contains only traces of pollen and consists predominantly of hypopharyngeal and mandibular secretions produced by nurse bees, which feed on large quantities of pollen-containing bee bread. We quantified the transfer of PAs to nursing secretions produced by bees that had previously consumed bee bread supplemented with PAs. The PA concentration in these secretions was reduced by three orders of magnitude as compared to the PA content in the nurse diet and was well below the toxicity threshold for larvae. Our results suggest that larval nursing protects honeybee larvae from the toxic effect of secondary metabolites of pollen. © 2018 The Authors.

  3. Nursing protects honeybee larvae from secondary metabolites of pollen

    Science.gov (United States)

    Lucchetti, Matteo A.; Kilchenmann, Verena; Glauser, Gaetan; Praz, Christophe

    2018-01-01

    The pollen of many plants contains toxic secondary compounds, sometimes in concentrations higher than those found in the flowers or leaves. The ecological significance of these compounds remains unclear, and their impact on bees is largely unexplored. Here, we studied the impact of pyrrolizidine alkaloids (PAs) found in the pollen of Echium vulgare on honeybee adults and larvae. Echimidine, a PA present in E. vulgare pollen, was isolated and added to the honeybee diets in order to perform toxicity bioassays. While adult bees showed relatively high tolerance to PAs, larvae were much more sensitive. In contrast to other bees, the honeybee larval diet typically contains only traces of pollen and consists predominantly of hypopharyngeal and mandibular secretions produced by nurse bees, which feed on large quantities of pollen-containing bee bread. We quantified the transfer of PAs to nursing secretions produced by bees that had previously consumed bee bread supplemented with PAs. The PA concentration in these secretions was reduced by three orders of magnitude as compared to the PA content in the nurse diet and was well below the toxicity threshold for larvae. Our results suggest that larval nursing protects honeybee larvae from the toxic effect of secondary metabolites of pollen. PMID:29563265

  4. Effect of competition on the production and activity of secondary metabolites in Aspergillus species

    DEFF Research Database (Denmark)

    Losada, L.; Ajayi, O.; Frisvad, Jens Christian

    2009-01-01

    and in the presence of other fungal species. However, it is not known whether secreted secondary metabolites provide a competitive advantage over other fungal species, or whether competition has any effect on the production of those metabolites. Here, we have performed co-cultivation competition assays among......Secondary metabolites are of intense interest to humans due to their pharmaceutical and/or toxic properties. Also, these metabolites are clinically relevant because of their importance in fungal pathogenesis. Aspergillus species secrete secondary metabolites when grown individually...... different species of Aspergillus to determine relative species fitness in culture, and to analyze the presence of possible antifungal activity of secondary metabolites in extracts. The results show that, for the most part, at 30C only one species is able to survive direct competition with a second species...

  5. Antifouling Activity of Secondary Metabolites Isolated from Chinese Marine Organisms

    KAUST Repository

    Li, Yong Xin

    2013-04-25

    Biofouling results in tremendous economic losses to maritime industries around the world. A recent global ban on the use of organotin compounds as antifouling agents has further raised demand for safe and effective antifouling compounds. In this study, 49 secondary metabolites, including diterpenoids, steroids, and polyketides, were isolated from soft corals, gorgonians, brown algae, and fungi collected along the coast of China, and their antifouling activity was tested against cyprids of the barnacle Balanus (Amphibalanus) amphitrite. Twenty of the compounds were found to inhibit larval settlement significantly at a concentration of 25 μg ml-1. Two briarane diterpenoids, juncin O (2) and juncenolide H (3), were the most promising non-toxic antilarval settlement candidates, with EC50 values less than 0.13 μg ml-1 and a safety ratio (LC50/EC50) higher than 400. A preliminary structure-activity relationships study indicated that both furanon and furan moieties are important for antifouling activity. Intriguingly, the presence of hydroxyls enhanced their antisettlement activity. © 2013 Springer Science+Business Media New York.

  6. Antifouling Activity of Secondary Metabolites Isolated from Chinese Marine Organisms

    KAUST Repository

    Li, Yong Xin; Wu, Hui Xian; Xu, Ying; Shao, Chang Lun; Wang, Chang Yun; Qian, Pei Yuan

    2013-01-01

    Biofouling results in tremendous economic losses to maritime industries around the world. A recent global ban on the use of organotin compounds as antifouling agents has further raised demand for safe and effective antifouling compounds. In this study, 49 secondary metabolites, including diterpenoids, steroids, and polyketides, were isolated from soft corals, gorgonians, brown algae, and fungi collected along the coast of China, and their antifouling activity was tested against cyprids of the barnacle Balanus (Amphibalanus) amphitrite. Twenty of the compounds were found to inhibit larval settlement significantly at a concentration of 25 μg ml-1. Two briarane diterpenoids, juncin O (2) and juncenolide H (3), were the most promising non-toxic antilarval settlement candidates, with EC50 values less than 0.13 μg ml-1 and a safety ratio (LC50/EC50) higher than 400. A preliminary structure-activity relationships study indicated that both furanon and furan moieties are important for antifouling activity. Intriguingly, the presence of hydroxyls enhanced their antisettlement activity. © 2013 Springer Science+Business Media New York.

  7. A nitrous acid biosynthetic pathway for diazo group formation in bacteria.

    Science.gov (United States)

    Sugai, Yoshinori; Katsuyama, Yohei; Ohnishi, Yasuo

    2016-02-01

    Although some diazo compounds have bioactivities of medicinal interest, little is known about diazo group formation in nature. Here we describe an unprecedented nitrous acid biosynthetic pathway responsible for the formation of a diazo group in the biosynthesis of the ortho-diazoquinone secondary metabolite cremeomycin in Streptomyces cremeus. This finding provides important insights into the biosynthetic pathways not only for diazo compounds but also for other naturally occurring compounds containing nitrogen-nitrogen bonds.

  8. Differential Retention of Gene Functions in a Secondary Metabolite Cluster.

    Science.gov (United States)

    Reynolds, Hannah T; Slot, Jason C; Divon, Hege H; Lysøe, Erik; Proctor, Robert H; Brown, Daren W

    2017-08-01

    In fungi, distribution of secondary metabolite (SM) gene clusters is often associated with host- or environment-specific benefits provided by SMs. In the plant pathogen Alternaria brassicicola (Dothideomycetes), the DEP cluster confers an ability to synthesize the SM depudecin, a histone deacetylase inhibitor that contributes weakly to virulence. The DEP cluster includes genes encoding enzymes, a transporter, and a transcription regulator. We investigated the distribution and evolution of the DEP cluster in 585 fungal genomes and found a wide but sporadic distribution among Dothideomycetes, Sordariomycetes, and Eurotiomycetes. We confirmed DEP gene expression and depudecin production in one fungus, Fusarium langsethiae. Phylogenetic analyses suggested 6-10 horizontal gene transfers (HGTs) of the cluster, including a transfer that led to the presence of closely related cluster homologs in Alternaria and Fusarium. The analyses also indicated that HGTs were frequently followed by loss/pseudogenization of one or more DEP genes. Independent cluster inactivation was inferred in at least four fungal classes. Analyses of transitions among functional, pseudogenized, and absent states of DEP genes among Fusarium species suggest enzyme-encoding genes are lost at higher rates than the transporter (DEP3) and regulatory (DEP6) genes. The phenotype of an experimentally-induced DEP3 mutant of Fusarium did not support the hypothesis that selective retention of DEP3 and DEP6 protects fungi from exogenous depudecin. Together, the results suggest that HGT and gene loss have contributed significantly to DEP cluster distribution, and that some DEP genes provide a greater fitness benefit possibly due to a differential tendency to form network connections. Published by Oxford University Press on behalf of the Society for Molecular Biology and Evolution 2017. This work is written by US Government employees and is in the public domain in the US.

  9. Secondary Metabolites from Leaves of Manilkara subsericea (Mart.) Dubard.

    Science.gov (United States)

    de Almeida, Fernanda Borges; Fernandes, Caio Pinho; Romao, Wanderson; Vanini, Gabriela; Costa, Helber Barcelos; França, Hildegardo Seibert; Santos, Marcelo Guerra; Carvalho, José Carlos Tavares; Falcão, Deborah Quintanilha; Rocha, Leandro

    2015-10-01

    Manilkara subsericea (Sapotaceae) is a species widely spread in the sandbanks of Restinga de Jurubatiba National Park (Rio de Janeiro, Brazil). It is commonly known as "maçaranduba", "maçarandubinha" and "guracica", being used in this locality as food, and timber. However, M. subsericea remains almost unexplored regarding its chemical constituents, including secondary metabolites from the leaves. Identify the chemical constituents from the leaves of M. subsericea. Leaves were macerated with ethanol (96% v/v), and dried crude ethanolic extract was sequentially washed with the organic solvents in order to obtain an ethyl acetate fraction. Substances from this fraction were identified by different techniques, such as negative-ion electrospray ionization Fourier and (1)H and (13)C nuclear magnetic resonance (NMR). Fresh leaves from M. subsericea were also submitted to hydrodistillation in order to obtain volatile substances, which were identified by gas chromatograph coupled to mass spectrometer. NMR(1)H and (13)C spectra allowed for the identification of the compounds myricetin, quercetin, and kaempferol from the ethyl acetate fraction. The negative-ion electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry mass spectrum also revealed the presence in this fraction of a polyhydroxytriterpene acid (pomolic acid), and some flavonoids, such as quercitrin, and myricitrin. In all 34 volatile compounds were identified by gas chromatography-mass spectrometry, including monoterpenes, sesquiterpenes, and long chain hydrocarbons. This study describes the first reports concerning the phytochemical information about leaves from M. subsericea. Manilkara subsericea fruits proved to be a rich source of triterpenes. However, no phytochemical studies were carried out with leaves. Thus, we described identification of volatile substances from its essential oils, in addition to non-reported triterpene and flavonoids from this species.

  10. Secondary Metabolites from Leaves of Manilkara subsericea (Mart.) Dubard

    Science.gov (United States)

    de Almeida, Fernanda Borges; Fernandes, Caio Pinho; Romao, Wanderson; Vanini, Gabriela; Costa, Helber Barcelos; França, Hildegardo Seibert; Santos, Marcelo Guerra; Carvalho, José Carlos Tavares; Falcão, Deborah Quintanilha; Rocha, Leandro

    2015-01-01

    Background: Manilkara subsericea (Sapotaceae) is a species widely spread in the sandbanks of Restinga de Jurubatiba National Park (Rio de Janeiro, Brazil). It is commonly known as “maçaranduba”, “maçarandubinha” and “guracica”, being used in this locality as food, and timber. However, M. subsericea remains almost unexplored regarding its chemical constituents, including secondary metabolites from the leaves. Objective: Identify the chemical constituents from the leaves of M. subsericea. Materials and Methods: Leaves were macerated with ethanol (96% v/v), and dried crude ethanolic extract was sequentially washed with the organic solvents in order to obtain an ethyl acetate fraction. Substances from this fraction were identified by different techniques, such as negative-ion electrospray ionization Fourier and 1H and 13C nuclear magnetic resonance (NMR). Fresh leaves from M. subsericea were also submitted to hydrodistillation in order to obtain volatile substances, which were identified by gas chromatograph coupled to mass spectrometer. Results: NMR1H and 13C spectra allowed for the identification of the compounds myricetin, quercetin, and kaempferol from the ethyl acetate fraction. The negative-ion electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry mass spectrum also revealed the presence in this fraction of a polyhydroxytriterpene acid (pomolic acid), and some flavonoids, such as quercitrin, and myricitrin. In all 34 volatile compounds were identified by gas chromatography-mass spectrometry, including monoterpenes, sesquiterpenes, and long chain hydrocarbons. Conclusion: This study describes the first reports concerning the phytochemical information about leaves from M. subsericea. SUMMARY Manilkara subsericea fruits proved to be a rich source of triterpenes. However, no phytochemical studies were carried out with leaves. Thus, we described identification of volatile substances from its essential oils, in addition to

  11. The Use of Secondary Metabolites Heracleum Sosnowskyi Manden in Agriculture

    Directory of Open Access Journals (Sweden)

    S. N. BUDARIN

    2014-06-01

    Full Text Available The composition of secondary metabolites Heracleum sosnowskyi include: tannins, essential oils, furanocoumarin and other agent. The greatest interest is the phenolic compounds coumarin furanocoumarin order which is known for their photosensitizing effect. Coumarins are part of hogweed. The greatest number of different kinds of coumarin was found in fruit. Researchers from the Far Eastern Branch of the RAS have been identified series of angelicin furocoumarins (sfondin, angelicin and psoralenum (bergapten, xanthotoxin, oksikumarina umbeliferon furocoumarins. In our research we have identified the influence of active substances hogweed on growth and development of different groups of plants.So experiment with biotest Heracleum sosnowskyi sap (with concentration are 1:1, 1:4, 1:16, and control - H2O stimulates energy germination of pea seeds (Vicia sativa L. - 6%, wheat (Triticum aestivum L. - 1,2%, barley (Hordeum vulgare L. - 5%, and tutsan (Hypéricum perforátum L. - 3,5% at a concentration of 1:16. The same concentration has an inhibitory effect on radish (Raphanus sativus L., chamomile (Matricaria chamomilla L. and oregano (Oríganum vulgáre L..In the experiment on the effect of active substances contained in the soil under hogweed (the control is the soil where wasn’t Heracleum sosnowskyi we observed a stimulatory effect on plant growth and development of wild camomile. So biometric indicators chamomile plants was grown in the A1 horizon (topsoil differ significantly in all indicators of underlying horizons and from controls.So Heracleum sosnowskyi possessing high photosensitizing effect due to content in the bergapten, psoralen, xanthotoxin can be used for medicine along with Ammi majus as the raw material for the preparation of herbal remedies in dermatology. Also in our studies we have shown the use of active substances hogweed in agriculture as regulators growth of some plant species: camomile, wheat, pea, barley, tutsan.

  12. An extensive case study of hairy-root cultures for enhanced secondary-metabolite production through metabolic-pathway engineering.

    Science.gov (United States)

    Mehrotra, Shakti; Rahman, Laiq Ur; Kukreja, Arun Kumar

    2010-08-23

    An intrinsic improvement is taking place in the methodologies for the development of culture systems with first-rate production of plant-based molecules. The blending of HR (hairy root) cultures with ME (metabolic engineering) approaches offers new insights into, and possibilities for, improving the system productivity for known and/or novel high-value plant-derived active compounds. The introduction and expression of foreign genes in plants results in improvement of cellular activities by manipulating enzymatic, regulatory and transport function of the cell. The rational amendments in the rate-limiting steps of a biosynthetic pathway as well as inactivating the inefficient pathway(s) for by-product formation can be accomplished either through single-step engineering or through the multi-step engineering. The hierarchical control of any metabolic process can lead the engineer to apply the ME ideas and principles to any of the strata, including transcriptional, moving on to translational and enzymatic activity. The HR culture systems offer a remarkable potential for commercial production of a number of low-volume, but high-value, secondary metabolites. Taking HR as a model system, in the present review, we discuss engineering principles and perceptions to exploit secondary-metabolite pathways for the production of important bioactive compounds. We also talk about requisites and possible challenges that occur during ME, with emphasis on examples of various HR systems. Furthermore, it also highlights the utilization of global information obtained from '-omic' platforms in order to explore pathway architecture, structural and functional aspects of important enzymes and genes that can support the design of sets of engineering, resulting in the generation of wide-ranging views of DNA sequence-to-metabolite passageway networking and their control to obtain desired results.

  13. Tropical biodiversity: has it been a potential source of secondary metabolites useful for medicinal chemistry?

    Directory of Open Access Journals (Sweden)

    Marilia Valli

    2012-01-01

    Full Text Available The use of natural products has definitely been the most successful strategy in the discovery of novel medicines. Secondary metabolites from terrestrial and marine organisms have found considerable use in the treatment of numerous diseases and have been considered lead molecules both in their natural form and as templates for medicinal chemistry. This paper seeks to show the great value of secondary metabolites and emphasize the rich chemical diversity of Brazilian biodiversity. This natural chemical library remains understudied, but can be a useful source of new secondary metabolites with potential application as templates for drug discovery.

  14. Tropical biodiversity: has it been a potential source of secondary metabolites useful for medicinal chemistry?

    Energy Technology Data Exchange (ETDEWEB)

    Valli, Marilia; Pivatto, Marcos; Danuello, Amanda; Castro-Gamboa, Ian; Silva, Dulce Helena Siqueira; Cavalheiro, Alberto Jose; Araujo, Angela Regina; Furlan, Maysa; Lopes, Marcia Nasser; Bolzani, Vanderlan da Silva, E-mail: bolzaniv@iq.unesp.br [UNESP, Araraquara, SP (Brazil). Inst. de Quimica. Dept. de Quimica Organica

    2012-07-01

    The use of natural products has definitely been the most successful strategy in the discovery of novel medicines. Secondary metabolites from terrestrial and marine organisms have found considerable use in the treatment of numerous diseases and have been considered lead molecules both in their natural form and as templates for medicinal chemistry. This paper seeks to show the great value of secondary metabolites and emphasize the rich chemical diversity of Brazilian biodiversity. This natural chemical library remains understudied, but can be a useful source of new secondary metabolites with potential application as templates for drug discovery. (author)

  15. Tropical biodiversity: has it been a potential source of secondary metabolites useful for medicinal chemistry?

    International Nuclear Information System (INIS)

    Valli, Marilia; Pivatto, Marcos; Danuello, Amanda; Castro-Gamboa, Ian; Silva, Dulce Helena Siqueira; Cavalheiro, Alberto Jose; Araujo, Angela Regina; Furlan, Maysa; Lopes, Marcia Nasser; Bolzani, Vanderlan da Silva

    2012-01-01

    The use of natural products has definitely been the most successful strategy in the discovery of novel medicines. Secondary metabolites from terrestrial and marine organisms have found considerable use in the treatment of numerous diseases and have been considered lead molecules both in their natural form and as templates for medicinal chemistry. This paper seeks to show the great value of secondary metabolites and emphasize the rich chemical diversity of Brazilian biodiversity. This natural chemical library remains understudied, but can be a useful source of new secondary metabolites with potential application as templates for drug discovery. (author)

  16. Metabolomics and bioanalysis of terpenoid derived secondary metabolites : Analysis of Cannabis sativa L. metabolite production and prenylases for cannabinoid production

    NARCIS (Netherlands)

    Muntendam, Remco

    2015-01-01

    Cannabinoid research has gained a renenewed interest by both the public and scientist. Focus is mainly directed to the medicinal activities, as reported for various cannabinoid structures. This thesis focusses on prenyl-derived secondary metabolites with main focus on cannabinoids. Firstly the

  17. Genetically engineering Synechocystis sp. Pasteur Culture Collection 6803 for the sustainable production of the plant secondary metabolite p-coumaric acid.

    Science.gov (United States)

    Xue, Yong; Zhang, Yan; Cheng, Dan; Daddy, Soumana; He, Qingfang

    2014-07-01

    p-Coumaric acid is the precursor of phenylpropanoids, which are plant secondary metabolites that are beneficial to human health. Tyrosine ammonia lyase catalyzes the production of p-coumaric acid from tyrosine. Because of their photosynthetic ability and biosynthetic versatility, cyanobacteria are promising candidates for the production of certain plant metabolites, including phenylpropanoids. Here, we produced p-coumaric acid in a strain of transgenic cyanobacterium Synechocystis sp. Pasteur Culture Collection 6803 (hereafter Synechocystis 6803). Whereas a strain of Synechocystis 6803 genetically engineered to express sam8, a tyrosine ammonia lyase gene from the actinomycete Saccharothrix espanaensis, accumulated little or no p-coumaric acid, a strain that both expressed sam8 and lacked slr1573, a native hypothetical gene shown here to encode a laccase that oxidizes polyphenols, produced ∼82.6 mg/L p-coumaric acid, which was readily purified from the growth medium.

  18. Identification of Volatile Secondary Metabolites from an Endophytic Microfungus Aspergillus Nomius KUB105

    International Nuclear Information System (INIS)

    Lateef Adebola Azeez; Lateef Adebola Azeez; Sepiah Muid; Bolhassan Mohamad Hasnul

    2016-01-01

    Microfungi are a highly diverse group of micro-organisms and important components of the ecosystem with great potential for diverse metabolite production. During a survey of microfungi on leaves in a National Park in Sarawak, an uncommon endophytic microfungus Aspergillus nomius was encountered. The metabolite production of this microfungus was investigated by growing it in a liquid basal medium for 2 weeks. Gas Chromatography - Mass Spectrometry (GC-MS) and Fourier Transform Infrared (FTIR) profiling of the secondary metabolites produced by this microfungus in the liquid medium revealed the presence of 46 different secondary metabolites. The metabolites include saturated hydrocarbons, alkyl halides, alcohols and an unsaturated hydrocarbon. Majority of the metabolites produced were saturated hydrocarbons. Tetracosane, Icosane and 10-Methylicosane were the most abundant metabolites identified while heptadecane and 2,4-dimethylundecane were the least abundant respectively. This study is the first GC-MS and FTIR report of secondary metabolites from A. nomius. The results from this study confirm the ability of microfungi to produce diverse metabolites, including saturated hydrocarbons. (author)

  19. Genomics-guided discovery of secondary metabolites and their regulation in Pseudomonas protegens Pf-5

    Science.gov (United States)

    Pseudomonas protegens strain Pf-5 is a well-characterized rhizosphere bacterium known for its production of a diverse spectrum of secondary metabolites and its capacity to suppress plant diseases caused by soilborne fungal, bacterial and oomycete pathogens. Metabolites produced by Pf-5 include 2,4-...

  20. Secondary metabolites of the argan tree (Morocco) may have ...

    African Journals Online (AJOL)

    Administrator

    knowledge, researchers are screening metabolites of this rare plant to identify bioactive compounds for .... or 29 carbon atoms. ... argan oil does not absorb oxygen to form hydroperoxides ..... dioxide: superiority to alpha-tocopherol. Proc. Nat.

  1. Co-evolution of secondary metabolite gene clusters and their host

    DEFF Research Database (Denmark)

    Kjærbølling, Inge; Vesth, Tammi Camilla; Frisvad, Jens Christian

    Secondary metabolite gene cluster evolution is mainly driven by two events: gene duplication and annexation and horizontal gene transfer. Here we use comparative genomics of Aspergillus species to investigate the evolution of secondary metabolite (SM) gene clusters across a wide spectrum of speci....... We investigate the dynamic evolutionary relationship between the cluster and the host by examining the genes within the cluster and the number of homologous genes found within the host and in closely related species.......Secondary metabolite gene cluster evolution is mainly driven by two events: gene duplication and annexation and horizontal gene transfer. Here we use comparative genomics of Aspergillus species to investigate the evolution of secondary metabolite (SM) gene clusters across a wide spectrum of species...

  2. Linking secondary metabolites to gene clusters through genome sequencing of six diverse Aspergillus species

    DEFF Research Database (Denmark)

    Kjærbølling, Inge; Vesth, Tammi C.; Frisvad, Jens C.

    2018-01-01

    The fungal genus of Aspergillus is highly interesting, containing everything from industrial cell factories, model organisms, and human pathogens. In particular, this group has a prolific production of bioactive secondary metabolites (SMs). In this work, four diverse Aspergillus species (A...

  3. Plant Secondary Metabolites Modulate Insect Behavior-Steps Toward Addiction?

    Directory of Open Access Journals (Sweden)

    Michael Wink

    2018-04-01

    Full Text Available Plants produce a diversity of secondary metabolites (PSMs that serve as defense compounds against herbivores and microorganisms. In addition, some PSMs attract animals for pollination and seed dispersal. In case of pollinating insects, PSMs with colors or terpenoids with fragrant odors attract pollinators in the first place, but when they arrive at a flower, they are rewarded with nectar, so that the pollinators do not feed on flowers. In order to be effective as defense chemicals, PSMs evolved as bioactive substances, that can interfere with a large number of molecular targets in cells, tissues and organs of animals or of microbes. The known functions of PSMs are summarized in this review. A number of PSMs evolved as agonists or antagonists of neuronal signal transduction. Many of these PSMs are alkaloids. Several of them share structural similarities to neurotransmitters. Evidence for neuroactive and psychoactive PSMs in animals will be reviewed. Some of the neuroactive PSMs can cause addiction in humans and other vertrebrates. Why should a defense compound be addictive and thus attract more herbivores? Some insects are food specialists that can feed on plants that are normally toxic to other herbivores. These specialists can tolerate the toxins and many are stored in the insect body as acquired defense chemicals against predators. A special case are pyrrolizidine alkaloids (PAs that are neurotoxic and mutagenic in vertebrates. PAs are actively sequestered by moths of the family Arctiidae and a few other groups of arthropods. In arctiids, PAs are not only used for defense, but also serve as morphogens for the induction of male coremata and as precursors for male pheromones. Caterpillars even feed on filter paper impregnated with pure PAs (that modulate serotonin receptors in vertebrates and maybe even in insects and thus show of behavior with has similarities to addiction in vertebrates. Not only PA specialists, but also many monophagous

  4. The use of secondary metabolite profiling in chemotaxonomy of filamentous fungi

    DEFF Research Database (Denmark)

    Frisvad, Jens Christian; Andersen, Birgitte; Thrane, Ulf

    2008-01-01

    A secondary metabolite is a chemical compound produced by a limited number of fungal species in a genus, an order, or even phylum. A profile of secondary metabolites consists of all the different compounds a fungus can produce on a given substratum and includes toxins, antibiotics and other outwa......, Xylaria and in few basidiomycete genera, but not in Zygomycota and Chytridiomycota. (C) 2007 The British Mycological Society. Published by Elsevier Ltd. All rights reserved....

  5. Estimation of induced secondary metabolites in chickpea tissues in response to elicitor preparation of seaweeds

    International Nuclear Information System (INIS)

    Bi, F.; Iqbal, S.

    2000-01-01

    Disease response of plants in terms of induced browning and phytoalexin (induced secondary metabolites) production were recorded in the tissues of Cicer arietinum (Chick pea) treated with the High Molecular Crude Elicitor Preparations, HMWCEP 'Polysaccharides' of Hypnea musciformis (red algae), Padina tetrastromatica (brown algae) and Ulva lactulus (green algae). A UV-visible spectrophotometric method has been developed for the quantification of induced secondary metabolites with time. (author)

  6. Deciphering the Cryptic Genome: Genome-wide Analyses of the Rice Pathogen Fusarium fujikuroi Reveal Complex Regulation of Secondary Metabolism and Novel Metabolites

    Science.gov (United States)

    Studt, Lena; Niehaus, Eva-Maria; Espino, Jose J.; Huß, Kathleen; Michielse, Caroline B.; Albermann, Sabine; Wagner, Dominik; Bergner, Sonja V.; Connolly, Lanelle R.; Fischer, Andreas; Reuter, Gunter; Kleigrewe, Karin; Bald, Till; Wingfield, Brenda D.; Ophir, Ron; Freeman, Stanley; Hippler, Michael; Smith, Kristina M.; Brown, Daren W.; Proctor, Robert H.; Münsterkötter, Martin; Freitag, Michael; Humpf, Hans-Ulrich; Güldener, Ulrich; Tudzynski, Bettina

    2013-01-01

    The fungus Fusarium fujikuroi causes “bakanae” disease of rice due to its ability to produce gibberellins (GAs), but it is also known for producing harmful mycotoxins. However, the genetic capacity for the whole arsenal of natural compounds and their role in the fungus' interaction with rice remained unknown. Here, we present a high-quality genome sequence of F. fujikuroi that was assembled into 12 scaffolds corresponding to the 12 chromosomes described for the fungus. We used the genome sequence along with ChIP-seq, transcriptome, proteome, and HPLC-FTMS-based metabolome analyses to identify the potential secondary metabolite biosynthetic gene clusters and to examine their regulation in response to nitrogen availability and plant signals. The results indicate that expression of most but not all gene clusters correlate with proteome and ChIP-seq data. Comparison of the F. fujikuroi genome to those of six other fusaria revealed that only a small number of gene clusters are conserved among these species, thus providing new insights into the divergence of secondary metabolism in the genus Fusarium. Noteworthy, GA biosynthetic genes are present in some related species, but GA biosynthesis is limited to F. fujikuroi, suggesting that this provides a selective advantage during infection of the preferred host plant rice. Among the genome sequences analyzed, one cluster that includes a polyketide synthase gene (PKS19) and another that includes a non-ribosomal peptide synthetase gene (NRPS31) are unique to F. fujikuroi. The metabolites derived from these clusters were identified by HPLC-FTMS-based analyses of engineered F. fujikuroi strains overexpressing cluster genes. In planta expression studies suggest a specific role for the PKS19-derived product during rice infection. Thus, our results indicate that combined comparative genomics and genome-wide experimental analyses identified novel genes and secondary metabolites that contribute to the evolutionary success of F

  7. New secondary metabolites of phenylbutyrate in humans and rats.

    Science.gov (United States)

    Kasumov, Takhar; Brunengraber, Laura L; Comte, Blandine; Puchowicz, Michelle A; Jobbins, Kathryn; Thomas, Katherine; David, France; Kinman, Renee; Wehrli, Suzanne; Dahms, William; Kerr, Douglas; Nissim, Itzhak; Brunengraber, Henri

    2004-01-01

    Phenylbutyrate is used to treat inborn errors of ureagenesis, malignancies, cystic fibrosis, and thalassemia. High-dose phenylbutyrate therapy results in toxicity, the mechanism of which is unexplained. The known metabolites of phenylbutyrate are phenylacetate, phenylacetylglutamine, and phenylbutyrylglutamine. These are excreted in urine, accounting for a variable fraction of the dose. We identified new metabolites of phenylbutyrate in urine of normal humans and in perfused rat livers. These metabolites result from interference between the metabolism of phenylbutyrate and that of carbohydrates and lipids. The new metabolites fall into two categories, glucuronides and phenylbutyrate beta-oxidation side products. Two questions are raised by these data. First, is the nitrogen-excreting potential of phenylbutyrate diminished by ingestion of carbohydrates or lipids? Second, does competition between the metabolism of phenylbutyrate, carbohydrates, and lipids alter the profile of phenylbutyrate metabolites? Finally, we synthesized glycerol esters of phenylbutyrate. These are partially bioavailable in rats and could be used to administer large doses of phenylbutyrate in a sodium-free, noncaustic form.

  8. New insights into the organization and regulation of trichothecene biosynthetic genes in Trichoderma

    Science.gov (United States)

    Collectively, species of the genus Trichoderma can produce numerous structurally diverse secondary metabolites (SM). This ability is conferred by the presence of SM biosynthetic gene clusters in their genomes. Species of Trichoderma in the Brevicompactum clade are able to produce trichothecenes, a f...

  9. Physiological and biochemical effect of neem and other Meliaceae plants secondary metabolites against Lepidopteran insects

    Directory of Open Access Journals (Sweden)

    Senthil-Nathan eSengottayan

    2013-12-01

    Full Text Available This review described the physiological and biochemical effects of various secondary metabolites from Meliaceae against major Lepidopteran insect pest including, Noctuidae and Pyralidae. The biochemical effect of major Meliaceae secondary metabolites were discussed more in this review. Several enzymes based on food materials have critical roles in nutritional indices (food utilization of the insect pest population. Several research work has been referred and the effect of Meliaceae secondary metabolites on feeding parameters of insects by demonstrating food consumption, approximate digestibility of consumed food, efficiency of converting the ingested food to body substance, efficiency of converting digested food to body substance and consumption index was reviewed in detail. Further how the digestive enzymes including a-Amylases, α and β- glucosidases (EC 3.2.1.1, lipases (EC 3.1.1 Proteases, serine, cysteine, and aspartic proteinases affected by the Meliaceae secondary metabolites was reviewed. Further effect of Meliaceae secondary metabolites on detoxifying enzymes have been found to react against botanical insecticides including general esterases (EST, glutathione S-transferase (GST and phosphatases was reviewed. Alkaline phosphatase (ALP, E.C.3.1.3.1 and acid phosphatase (ACP, E.C.3.1.3.2 are hydrolytic enzymes, which hydrolyze phosphomonoesters under alkaline or acid conditions, respectively. These enzymes were affected by the secondary metabolites treatment. The detailed mechanism of action was further explained in this review. Acethylcholine esterase (AChE is a key enzyme that terminates nerve impulses by catalyzing the hydrolysis of neurotransmitter, acetylcholine, in the nervous system of various organisms. How the AChE activity was altered by the Meliaceae secondary metabolites reviewed in detail.

  10. Secondary metabolites from the endophytic fungus Talaromyces pinophilus.

    Science.gov (United States)

    Vinale, F; Nicoletti, R; Lacatena, F; Marra, R; Sacco, A; Lombardi, N; d'Errico, G; Digilio, M C; Lorito, M; Woo, S L

    2017-08-01

    Endophytic fungi have a great influence on plant health and growth, and are an important source of bioactive natural compounds. Organic extracts obtained from the culture filtrate of an endophytic strain of Talaromyces pinophilus isolated from strawberry tree (Arbutus unedo) were studied. Metabolomic analysis revealed the presence of three bioactive metabolites, the siderophore ferrirubin, the platelet-aggregation inhibitor herquline B and the antibiotic 3-O-methylfunicone. The latter was the major metabolite produced by this strain and displayed toxic effects against the pea aphid Acyrthosiphon pisum (Homoptera Aphidiidae). This toxicity represents an additional indication that the widespread endophytic occurrence of T. pinophilus may be related to a possible role in defensive mutualism. Moreover, the toxic activity on aphids could promote further study on 3-O-methylfunicone, or its derivatives, as an alternative to synthetic chemicals in agriculture.

  11. [Determination of the profiles of secondary metabolites characteristic of Alternaria strains isolated from tomato].

    Science.gov (United States)

    Benavidez Rozo, Martha Elizabeth; Patriarca, Andrea; Cabrera, Gabriela; Fernández Pinto, Virginia E

    2014-01-01

    Many Alternaria species have been studied for their ability to produce bioactive secondary metabolites, such as tentoxin (TEN), some of which have toxic properties. The main food contaminant toxins are tenuazonic acid, alternariol (AOH), alternariol monomethyl ether (AME), altenuene, and altertoxins i, ii and iii. To determine the profiles of secondary metabolites characteristic of Alternaria strains isolated from tomato for their chemotaxonomic classification. The profiles of secondary metabolites were determined by HPLC MS. The Alternaria isolates obtained from spoiled tomatoes belong, according to their morphological characteristics, to the species groups Alternaria alternata, Alternaria tenuissima and Alternaria arborescens, with A. tenuissima being the most frequent. The most frequent profiles of secondary metabolites belonging to the species groups A. alternata (AOH, AME, TEN), A. tenuissima (AOH, AME, TEN, tenuazonic acid) and A. arborescens (AOH, AME, TEN, tenuazonic acid) were determined, with some isolates of the latter being able to synthesize AAL toxins. Secondary metabolite profiles are a useful tool for the differentiation of small spored Alternaria isolates not easily identifiable by their morphological characteristics. Copyright © 2013 Revista Iberoamericana de Micología. Published by Elsevier Espana. All rights reserved.

  12. Strategies to enhance biologically active-secondary metabolites in cell cultures of Artemisia - current trends.

    Science.gov (United States)

    Ali, Mohammad; Abbasi, Bilal Haider; Ahmad, Nisar; Khan, Haji; Ali, Gul Shad

    2017-11-01

    The genus Artemisia has been utilized worldwide due to its immense potential for protection against various diseases, especially malaria. Artemisia absinthium, previously renowned for its utilization in the popular beverage absinthe, is gaining resurgence due to its extensive pharmacological activities. Like A. annua, this species exhibits strong biological activities like antimalarial, anticancer and antioxidant. Although artemisinin was found to be the major metabolite for its antimalarial effects, several flavonoids and terpenoids are considered to possess biological activities when used alone and also to synergistically boost the bioavailability of artemisinin. However, due to the limited quantities of these metabolites in wild plants, in vitro cultures were established and strategies have been adopted to enhance medicinally important secondary metabolites in these cultures. This review elaborates on the traditional medicinal uses of Artemisia species and explains current trends to establish cell cultures of A. annua and A. absinthium for enhanced production of medicinally important secondary metabolites.

  13. Secondary metabolite profiling of Alternaria dauci, A. porri, A. solani, and A. tomatophila.

    Science.gov (United States)

    Andersen, Birgitte; Dongo, Anita; Pryor, Barry M

    2008-02-01

    Chemotaxonomy (secondary metabolite profiling) has been shown to be of great value in the classification and differentiation in Ascomycota. However, few studies have investigated the use of metabolite production for classification and identification purposes of plant pathogenic Alternaria species. The purpose of the present study was to describe the methodology behind metabolite profiling in chemotaxonomy using A. dauci, A. porri, A. solani, and A. tomatophila strains as examples of the group. The results confirmed that A. dauci, A. solani, and A. tomatophila are three distinct species each with their own specific metabolite profiles, and that A. solani and A. tomatophila both produce altersolanol A, altertoxin I, and macrosporin. By using automated chemical image analysis and other multivariate statistic analyses, three sets of species-specific metabolites could be selected, one each for A. dauci, A. solani, and A. tomatophila.

  14. Patulin and secondary metabolite production by marine-derived Penicillium strains

    DEFF Research Database (Denmark)

    Vansteelandt, Marieke; Kerzaon, Isabelle; Blanchet, Elodie

    2012-01-01

    )–mass spectrometry (MS)/MS. Each strain was grown on six different culture media to enhance the number of observable metabolites.Thirty-two secondary metabolites were detected in crude extracts with twenty first observations for studied species. Patulin, a major mycotoxin, was classically detected in extracts...... of these fungi in shellfish farming areas.Patulin induced acute neurotoxicity on Diptera larvae, indicating the interest of this bioassay as an additional tool for detection of this major mycotoxin in crude extracts....

  15. Secondary metabolite profiling of Alternaria dauci, A. porri, A. solani, and A. tomatophila

    DEFF Research Database (Denmark)

    Andersen, Birgitte; Dongo, Anita; Pryor, Barry M.

    2008-01-01

    Chemotaxonomy (secondary metabolite profiling) has been shown to be of great value in the classification and differentiation in Ascomycota. However, few studies have investigated the use of metabolite production for classification and identification purposes of plant pathogenic Alternaria species....... The purpose of the present study was to describe the methodology behind metabolite profiling in chemotaxonomy using A. dauci, A. porri, A. solani, and A. tomatophila strains as examples of the group. The results confirmed that A. dauci, A. solani, and A. tomatophila are three distinct species each...

  16. Medicinal plants and secondary metabolites for diabetes mellitus control

    Directory of Open Access Journals (Sweden)

    Mahmoud Bahmani

    2014-09-01

    Full Text Available Diabetes mellitus is one of the most common and complex problems of modern societies which has caused many economic and social problems. Because diabetes has no definite treatment, the use of traditional medicine seems to be an appropriate solution to control and manage it. Studies revealed that Vaccinium Arctostaphylos L., Securigera securidaca L., Gymnema sylvestre L., Atriplex halimus L., Camellia sinensis L., Ginkgo biloba L., Mamordica charantia L., Citrullus colocynthis (L. Schrad., Allium cepa L., Allium sativum L., Silybum marianum (L., Gaertn and Trigonella foenum graecum L. are effective against diabetes. Flavonoids, quercin, metformin, quinolizidine, anthocyanin, catechin and flavone, phenylpropanoids, lipoic acid and coumarin metabolites were introduced major impact on diabetes. With regard to the study of plants and their metabolites and the mechanisms of their influence, it is clear that these plants have the potential to reduce blood sugar and diabetes and be considered as candidates for preparing new drugs. Combination of plants extracts or their components may also have synergistic effects to better act on diabetes.

  17. Secondary metabolites from the roots of Astragalus maximus

    Directory of Open Access Journals (Sweden)

    J. Ghasemian-Yadegari

    2017-04-01

    Full Text Available Background and objectives: Astragalus is one of the most abundant genera of flowering plants in Iran. There are a few reports on phytochemical investigation of this valuable genus. Saponins, flavonoids and polysaccharides have been reported as the most important metabolites in Astragalus species. In the present research, we aimed to identify the foremost constituents of Astragalus maximus. Method: Phytochemical analysis of the ethyl acetate (EtOAc fraction of Astragalus maximus roots was performed using different methods of chromatography such as HPLC, SPE and preparative TLC. The structures of the isolated compounds were elucidated on the basis of extensive spectral evidence from 1D and 2D NMR including DQF-COSY, HSQC, HMBC, and DEPT, in comparison with reported values in the literature. Results: Analysis of the extract yielded three flavonoids namely liquiritigenin, formononetin, isoquercitrin and one acylated cycloartane-type saponin, astragaloside I. Conclusion: According to the results of our study, cycloartane-type saponin and flavonoids were the important metabolites in A. maximus.

  18. Antimicrobial properties and the influence of temperature on secondary metabolite production in cold environment soil fungi

    Science.gov (United States)

    Yogabaanu, U.; Weber, Jean-Frederic Faizal; Convey, Peter; Rizman-Idid, Mohammed; Alias, Siti Aisyah

    2017-12-01

    The Arctic and Antarctic share environmental extremes. To survive in such environments, microbes such as soil fungi need to compete with or protect themselves effectively from other soil microbiota and to obtain the often scarce nutrients available, and many use secondary metabolites to facilitate this. We therefore (i) screened for antimicrobial properties of cold-environment Arctic and Antarctic soil fungi, and (ii) identified changes in the secreted secondary metabolite profiles of a subset of these strains in response to temperature variation. A total of 40 polar soil fungal strains from King George Island, maritime Antarctic and Hornsund, Svalbard, High Arctic, were obtained from the Malaysian National Antarctic Research Centre culture collections. The plug assay technique was used to screen for antimicrobial potential against Gram-positive and Gram-negative human pathogenic bacteria (Bacillus subtilis, B. cereus, Pseudomonas aeruginosa, Enterococcus faecalis and Escherichia coli). About 45% of the tested fungal strains showed antimicrobial activity against at least one tested microorganism. Three fungal isolates showed good bioactivity and were subjected to secondary metabolite profiling at different temperatures (4, 10, 15 and 28 °C). We observed a range of responses in fungal metabolite production when incubated at varying temperatures, confirming an influence of environmental conditions such as temperature on the production of secondary metabolites.

  19. A Review on Venom Enzymes Neutralizing Ability of Secondary Metabolites from Medicinal Plants

    Directory of Open Access Journals (Sweden)

    Pushpendra Singh

    2017-09-01

    Full Text Available Objectives: Medicinal plants are vital sources of bioactive compounds that are useful for the treatment of patients with snake bites or are indirectly applicable for boosting the effects of conventional serum therapy. These plants are being used traditionally by local healers and tribes for the treatment of patients with snake bites and therefore can be used as an alternative against snake envenomation. Scientifically, using the secondary metabolites of plants to neutralize venom enzymes has an extra benefit of being based on traditional knowledge; also, the use of such metabolites for the treatment of patients with snake bites is cheaper and the treatment can be started sooner. Methods: All the available information on various secondary metabolites exhibiting venom neutralizing ability were collected via electronic search (using Google books, Pubmed, SciFinder, Scirus, Google Scholar, and Web of Science and articles of peer-reviewed journals. Results: Recent interest in different plant has focused on isolating and identifying of different phytoconstituents that exhibit Phospholipase A2 activity and other venom enzyme neutralizing ability. In this support convincing evidence in experimental animal models are available. Conclusion: Secondary metabolites are naturally present, have no side effect, are stable for a long time, can be easily stored, and can neutralize a wide range of snake enzymes, such as phospholipase A2, hyaluronidase, protease, L-amino acid oxidase, 5’nucleotidase, etc. The current review presents a compilation of important plant secondary metabolites that are effective against snake venom due to enzyme neutralization.

  20. Chemical ecology of insect-plant interactions: ecological significance of plant secondary metabolites.

    Science.gov (United States)

    Nishida, Ritsuo

    2014-01-01

    Plants produce a diverse array of secondary metabolites as chemical barriers against herbivores. Many phytophagous insects are highly adapted to these allelochemicals and use such unique substances as the specific host-finding cues, defensive substances of their own, and even as sex pheromones or their precursors by selectively sensing, incorporating, and/or processing these phytochemicals. Insects also serve as pollinators often effectively guided by specific floral fragrances. This review demonstrates the ecological significance of such plant secondary metabolites in the highly diverse interactions between insects and plants.

  1. Diversity of Secondary Metabolites from Marine Bacillus Species: Chemistry and Biological Activity

    Science.gov (United States)

    Mondol, Muhammad Abdul Mojid; Shin, Hee Jae; Islam, Mohammad Tofazzal

    2013-01-01

    Marine Bacillus species produce versatile secondary metabolites including lipopeptides, polypeptides, macrolactones, fatty acids, polyketides, and isocoumarins. These structurally diverse compounds exhibit a wide range of biological activities, such as antimicrobial, anticancer, and antialgal activities. Some marine Bacillus strains can detoxify heavy metals through reduction processes and have the ability to produce carotenoids. The present article reviews the chemistry and biological activities of secondary metabolites from marine isolates. Side by side, the potential for application of these novel natural products from marine Bacillus strains as drugs, pesticides, carotenoids, and tools for the bioremediation of heavy metal toxicity are also discussed. PMID:23941823

  2. Accumulation of Rutin and Betulinic Acid and Expression of Phenylpropanoid and Triterpenoid Biosynthetic Genes in Mulberry (Morus alba L.).

    Science.gov (United States)

    Zhao, Shicheng; Park, Chang Ha; Li, Xiaohua; Kim, Yeon Bok; Yang, Jingli; Sung, Gyoo Byung; Park, Nam Il; Kim, Soonok; Park, Sang Un

    2015-09-30

    Mulberry (Morus alba L.) is used in traditional Chinese medicine and is the sole food source of the silkworm. Here, 21 cDNAs encoding phenylpropanoid biosynthetic genes and 21 cDNAs encoding triterpene biosynthetic genes were isolated from mulberry. The expression levels of genes involved in these biosynthetic pathways and the accumulation of rutin, betulin, and betulinic acid, important secondary metabolites, were investigated in different plant organs. Most phenylpropanoid and triterpene biosynthetic genes were highly expressed in leaves and/or fruit, and most genes were downregulated during fruit ripening. The accumulation of rutin was more than fivefold higher in leaves than in other organs, and higher levels of betulin and betulinic acid were found in roots and leaves than in fruit. By comparing the contents of these compounds with gene expression levels, we speculate that MaUGT78D1 and MaLUS play important regulatory roles in the rutin and betulin biosynthetic pathways.

  3. Anti-urease Secondary Metabolites from Seriphidium quettense

    Directory of Open Access Journals (Sweden)

    Muhammad Imran Tousif

    2017-03-01

    Full Text Available Ethyl acetate layer of the methanolic extract of Seriphidium quettense was subjected to silica gel column chromatography to isolate one new; seriphiloid (1, and four known compounds; ilicic acid (2, 6 a -hydroxy-8(10-oplopen-14-one (3, 2-(4-hydroxyphenyl-5,6,7-trimethoxy-4H-chromen-4-one (4 and 2-(3,4-dihydroxyphenyl-5,6,7-trimethoxy-4H-chromen-4-one (5. The chemical structure of the new isolate was established with the help of 1D, 2D NMR techniques and high resolution mass spectrometry. Known compounds were identified because of 1D NMR and mass spectrometric analysis and in comparison with the literature values. Compounds 1-5 were evaluated for their acetylcholinesterase, butyrylcholinesterase, a -glucosidase and urease inhibitory activities. Most of the metabolites were found inactive; however, compounds 2 and 3 showed good antiurease activity with IC 50 value 21.5±0.1 and 20.8±0.1 µg/mL, respectively.

  4. Chitosan and grape secondary metabolites: A proteomics and metabolomics approach

    Directory of Open Access Journals (Sweden)

    Bavaresco Luigi

    2017-01-01

    Full Text Available Chitosan is a polysaccharide obtained by deacetylation of chitin, and it is involved in defence mechanisms of plants toward diseases. In the present work, V. vinifera L. cv. Ortrugo, grafted on 420A rootstock was grown in pot and treated, at veraison, by 0.03% chitosan solution at cluster level. Just before the treatment (T0 and 24 hours (T1, 48 hours (T2, 72 hours (T3 and 10 days (T4 later, the concentration of stilbenic compounds was detected, and at T1 proteomics and metabolomics analyses were done. Proteomics relies on the analysis of the complete set of proteins existing in a given substrate, while metabolomics relies on the analyses of the complete set of metabolites in a given substrate. The treatment improved the stilbene concentration over the control at T1. Proteomic analysis showed that superoxide dismutase (SOD and phenylalanine ammonia-lyase (PAL were overexpressed in the treated grapes. SOD is known to be an enzyme active against reactive oxygen species (ROS while PAL is a key enzyme in the phenylpropanoids pathway. Metabolomics analysis highlighted the positive role of the treatment in improving the triperpenoid concentration (betulin, erythrodiol, uvaol, oleanolate; these compounds are known to be effective against microbes, insects and fungi.

  5. Media and growth conditions for induction of secondary metabolite production

    DEFF Research Database (Denmark)

    Frisvad, Jens Christian

    2012-01-01

    -defined media are suited for biochemical studies, but in order to get chemical diversity expressed in filamentous fungi, sources rich in amino acids, vitamins, and trace metals have to be added, such as yeast extract and oatmeal. A battery of solid agar media is recommended for exploration of chemical diversity...... as agar plug samples are easily analyzed to get an optimal representation of the qualitative secondary metabolome. Standard incubation for a week at 25°C in darkness is recommended, but optimal conditions have to be modified depending on the ecology and physiology of different filamentous fungi....

  6. Role of Cereal Secondary Metabolites Involved in Mediating the Outcome of Plant-Pathogen Interactions

    Directory of Open Access Journals (Sweden)

    Lauren A. Du Fall

    2011-12-01

    Full Text Available Cereal crops such as wheat, rice and barley underpin the staple diet for human consumption globally. A multitude of threats to stable and secure yields of these crops exist including from losses caused by pathogens, particularly fungal. Plants have evolved complex mechanisms to resist pathogens including programmed cell death responses, the release of pathogenicity-related proteins and oxidative bursts. Another such mechanism is the synthesis and release of secondary metabolites toxic to potential pathogens. Several classes of these compounds have been identified and their anti-fungal properties demonstrated. However the lack of suitable analytical techniques has hampered the progress of identifying and exploiting more of these novel metabolites. In this review, we summarise the role of the secondary metabolites in cereal crop diseases and briefly touch on the analytical techniques that hold the key to unlocking their potential in reducing yield losses.

  7. The ecology of plant secondary metabolites : from genes to global processes

    NARCIS (Netherlands)

    Iason, G.R.; Dicke, M.; Hartley, S.E.

    2012-01-01

    Plant secondary metabolites (PSM) such as terpenes and phenolic compounds are known to have numerous ecological roles, notably in defence against herbivores, pathogens and abiotic stresses and in interactions with competitors and mutualists. This book reviews recent developments in the field to

  8. Dynamics of plant secondary metabolites and consequences for food chains and community dynamics. Chapter Sixteen.

    NARCIS (Netherlands)

    Dicke, M.; Gols, R.; Poelman, E.H.

    2012-01-01

    Plant secondary metabolites (PSM) such as terpenes and phenolic compounds are known to have numerous ecological roles, notably in defence against herbivores, pathogens and abiotic stresses and in interactions with competitors and mutualists. This book reviews recent developments in the field to

  9. The integrative roles of plant secondary metabolites in natural systems: a synthesis

    NARCIS (Netherlands)

    Iason, G.R.; Dicke, M.; Hartley, S.E.

    2012-01-01

    Plant secondary metabolites (PSM) such as terpenes and phenolic compounds are known to have numerous ecological roles, notably in defence against herbivores, pathogens and abiotic stresses and in interactions with competitors and mutualists. This book reviews recent developments in the field to

  10. Systematics of Penicillium simplicissimum based on rDNA sequences, morphology and secondary metabolites

    DEFF Research Database (Denmark)

    Tuthill, D.E.; Frisvad, Jens Christian; Christensen, M.

    2001-01-01

    supported by differences in micromorphological characters, particularly of the conidia and phialides, and the production of distinct profiles of secondary metabolites by each species. Group-I introns, located in the SSU rDNA, were identified in six of the 21 isolates; their presence was used to test...

  11. Interactions Between a Belowground Herbivore and Primary and Secondary Root Metabolites in Wild Cabbage

    NARCIS (Netherlands)

    Van Geem, Moniek; Harvey, J.A.; Cortesero, A.M.; Raaijmakers, C.E.; Gols, R.

    2015-01-01

    Plants are attacked by both above- and belowground herbivores. Toxic secondary compounds are part of the chemical defense arsenal of plants against a range of antagonists, and are subject to genetic variation. Plants also produce primary metabolites (amino acids, nutrients, sugars) that function as

  12. Plant secondary metabolite-induced shifts in bacterial community structure and degradative ability in contaminated soil

    Czech Academy of Sciences Publication Activity Database

    Uhlík, O.; Musilová, L.; Rídl, Jakub; Hroudová, Miluše; Vlček, Čestmír; Koubek, J.; Holečková, M.; Mackova, M.; Macek, T.

    2013-01-01

    Roč. 97, č. 20 (2013), s. 9245-9256 ISSN 0175-7598 Grant - others:EK(XE) 265946; GA MŠk(CZ) ME10041 Institutional support: RVO:68378050 Keywords : plant secondary metabolites (PSM) * bacterial community * metabolic activity * bioremediation * pyrosequencing Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 3.811, year: 2013

  13. Chemical Diversity and Biological Properties of Secondary Metabolites from Sea Hares of Aplysia Genus

    Directory of Open Access Journals (Sweden)

    Renato B. Pereira

    2016-02-01

    Full Text Available The marine environment is an important source of structurally-diverse and biologically-active secondary metabolites. During the last two decades, thousands of compounds were discovered in marine organisms, several of them having inspired the development of new classes of therapeutic agents. Marine mollusks constitute a successful phyla in the discovery of new marine natural products (MNPs. Over a 50-year period from 1963, 116 genera of mollusks contributed innumerous compounds, Aplysia being the most studied genus by MNP chemists. This genus includes 36 valid species and should be distinguished from all mollusks as it yielded numerous new natural products. Aplysia sea hares are herbivorous mollusks, which have been proven to be a rich source of secondary metabolites, mostly of dietary origin. The majority of secondary metabolites isolated from sea hares of the genus Aplysia are halogenated terpenes; however, these animals are also a source of compounds from other chemical classes, such as macrolides, sterols and alkaloids, often exhibiting cytotoxic, antibacterial, antifungal, antiviral and/or antifeedant activities. This review focuses on the diverse structural classes of secondary metabolites found in Aplysia spp., including several compounds with pronounced biological properties.

  14. Plant protein and secondary metabolites influence diet selection in a mammalian specialist herbivore

    Science.gov (United States)

    Amy C. Ulappa; Rick G. Kelsey; Graham G. Frye; Janet L. Rachlow; LIsa A. Shipley; Laura Bond; Xinzhu Pu; Jennifer Sorensen. Forbey

    2014-01-01

    For herbivores, nutrient intake is limited by the relatively low nutritional quality of plants and high concentrations of potentially toxic defensive compounds (plant secondary metabolites [PSMs]) produced by many plants. In response to phytochemical challenges, some herbivores selectively forage on plants with higher nutrient and lower PSM concentrations relative to...

  15. Exploring plant tissue culture in Withania somnifera (L.) Dunal: in vitro propagation and secondary metabolite production.

    Science.gov (United States)

    Shasmita; Rai, Manoj K; Naik, Soumendra K

    2017-12-26

    Withania somnifera (L.) Dunal (family: Solanaceae), commonly known as "Indian Ginseng", is a medicinally and industrially important plant of the Indian subcontinent and other warmer parts of the world. The plant has multi-use medicinal potential and has been listed among 36 important cultivated medicinal plants of India that are in high demand for trade due to its pharmaceutical uses. The medicinal importance of this plant is mainly due to the presence of different types of steroidal lactones- withanolides in the roots and leaves. Owing to low seed viability and poor germination, the conventional propagation of W. somnifera falls short to cater its commercial demands particularly for secondary metabolite production. Therefore, there is a great need to develop different biotechnological approaches through tissue and organ culture for seasonal independent production of plants in large scale which will provide sufficient raw materials of uniform quality for pharmaceutical purposes. During past years, a number of in vitro plant regeneration protocols via organogenesis and somatic embryogenesis and in vitro conservation through synthetic seed based encapsulation technology have been developed for W. somnifera. Several attempts have also been made to standardize the protocol of secondary metabolite production via tissue/organ cultures, cell suspension cultures, and Agrobacterium rhizogenes-mediated transformed hairy root cultures. Employment of plant tissue culture based techniques would provide means for rapid propagation and conservation of this plant species and also provide scope for enhanced production of different bioactive secondary metabolites. The present review provides a comprehensive report on research activities conducted in the area of tissue culture and secondary metabolite production in W. somnifera during the past years. It also discusses the unexplored areas which might be taken into consideration for future research so that the medicinal properties and

  16. Crop-ecology and nutritional variability influence growth and secondary metabolites of Stevia rebaudiana Bertoni.

    Science.gov (United States)

    Pal, Probir Kumar; Kumar, Rajender; Guleria, Vipan; Mahajan, Mitali; Prasad, Ramdeen; Pathania, Vijaylata; Gill, Baljinder Singh; Singh, Devinder; Chand, Gopi; Singh, Bikram; Singh, Rakesh Deosharan; Ahuja, Paramvir Singh

    2015-02-27

    Plant nutrition and climatic conditions play important roles on the growth and secondary metabolites of stevia (Stevia rebaudiana Bertoni); however, the nutritional dose is strongly governed by the soil properties and climatic conditions of the growing region. In northern India, the interactive effects of crop ecology and plant nutrition on yield and secondary metabolites of stevia are not yet properly understood. Thus, a field experiment comprising three levels of nitrogen, two levels of phosphorus and three levels of potassium was conducted at three locations to ascertain whether the spatial and nutritional variability would dominate the leaf yield and secondary metabolites profile of stevia. Principal component analysis (PCA) indicates that the applications of 90 kg N, 40 kg P2O5 and 40 kg K2O ha-1 are the best nutritional conditions in terms of dry leaf yield for CSIR-IHBT (Council of Scientific and Industrial Research- Institute Himalayan Bioresource Technology) and RHRS (Regional Horticultural Research Station) conditions. The spatial variability also exerted considerable effect on the leaf yield and stevioside content in leaves. Among the three locations, CSIR-IHBT was found most suitable in case of dry leaf yield and secondary metabolites accumulation in leaves. The results suggest that dry leaf yield and accumulation of stevioside are controlled by the environmental factors and agronomic management; however, the accumulation of rebaudioside-A (Reb-A) is not much influenced by these two factors. Thus, leaf yield and secondary metabolite profiles of stevia can be improved through the selection of appropriate growing locations and proper nutrient management.

  17. Comparison of Expression of Secondary Metabolite Biosynthesis Cluster Genes in Aspergillus flavus, A. parasiticus, and A. oryzae

    OpenAIRE

    Ehrlich, Kenneth C.; Mack, Brian M.

    2014-01-01

    Fifty six secondary metabolite biosynthesis gene clusters are predicted to be in the Aspergillus flavus genome. In spite of this, the biosyntheses of only seven metabolites, including the aflatoxins, kojic acid, cyclopiazonic acid and aflatrem, have been assigned to a particular gene cluster. We used RNA-seq to compare expression of secondary metabolite genes in gene clusters for the closely related fungi A. parasiticus, A. oryzae, and A. flavus S and L sclerotial morphotypes. The data help ...

  18. A High-Resolution LC-MS-Based Secondary Metabolite Fingerprint Database of Marine Bacteria

    KAUST Repository

    Lu, Liang

    2014-10-09

    © 2014 Macmillan Publishers Limited. All rights reserved. Marine bacteria are the most widely distributed organisms in the ocean environment and produce a wide variety of secondary metabolites. However, traditional screening for bioactive natural compounds is greatly hindered by the lack of a systematic way of cataloguing the chemical profiles of bacterial strains found in nature. Here we present a chemical fingerprint database of marine bacteria based on their secondary metabolite profiles, acquired by high-resolution LC-MS. Till now, 1,430 bacterial strains spanning 168 known species collected from different marine environments were cultured and profiled. Using this database, we demonstrated that secondary metabolite profile similarity is approximately, but not always, correlated with taxonomical similarity. We also validated the ability of this database to find species-specific metabolites, as well as to discover known bioactive compounds from previously unknown sources. An online interface to this database, as well as the accompanying software, is provided freely for the community to use.

  19. A High-Resolution LC-MS-Based Secondary Metabolite Fingerprint Database of Marine Bacteria

    KAUST Repository

    Lu, Liang; Wang, Jijie; Xu, Ying; Wang, Kailing; Hu, Yingwei; Tian, Renmao; Yang, Bo; Lai, Qiliang; Li, Yongxin; Zhang, Weipeng; Shao, Zongze; Lam, Henry; Qian, Pei-Yuan

    2014-01-01

    © 2014 Macmillan Publishers Limited. All rights reserved. Marine bacteria are the most widely distributed organisms in the ocean environment and produce a wide variety of secondary metabolites. However, traditional screening for bioactive natural compounds is greatly hindered by the lack of a systematic way of cataloguing the chemical profiles of bacterial strains found in nature. Here we present a chemical fingerprint database of marine bacteria based on their secondary metabolite profiles, acquired by high-resolution LC-MS. Till now, 1,430 bacterial strains spanning 168 known species collected from different marine environments were cultured and profiled. Using this database, we demonstrated that secondary metabolite profile similarity is approximately, but not always, correlated with taxonomical similarity. We also validated the ability of this database to find species-specific metabolites, as well as to discover known bioactive compounds from previously unknown sources. An online interface to this database, as well as the accompanying software, is provided freely for the community to use.

  20. [Influence of diethyl sulfate (DES) mutagenesis on growth properties and pigment secondary metabolites of Phellinus igniarius].

    Science.gov (United States)

    Wang, Jing; Wu, Xin-yuan; Ma, Wei; Chen, Jing; Liu, Cheng; Wu, Xiu-li

    2015-06-01

    The diethyl sulfate (DES) mutagenesis was chosen for the mutagenic treatment to Phellinus igniarius, and the relationship of mutagenesis time and death rate was investigated with 0.5% DES. The differences of mycelial growth speed, liquid fermentation mycelia biomass, morphology and pigment classes of secondary metabolites production speed and antioxidant activities of metabolite products were discussed. The study displayed that DES mutagenesis could change mycelial morphology without obvious effect on mycelium growth, and the DES mutagenesis improved antioxidant activities of the active ingredients of P. igniarius and had more antioxidant activity of hypoxia/sugar PC12 nerve cells than that of P. igniarius.

  1. The role of metabolic engineering in the production of secondary metabolites

    DEFF Research Database (Denmark)

    Nielsen, Jens Bredal

    1998-01-01

    In the production of secondary metabolites yield and productivity are the most important design parameters. The focus is therefore to direct the carbon fluxes towards the product of interest, and this can be obtained through metabolic engineering whereby directed genetic changes are introduced...... into the production strain. In this process it is, however, important to analyze the metabolic network through measurement of the intracellular metabolites and the flux distributions. Besides playing an important role in the optimization of existing processes, metabolic engineering also offers the possibility...

  2. Rapid analysis of fungal cultures and dried figs for secondary metabolites by LC/TOF-MS

    Energy Technology Data Exchange (ETDEWEB)

    Senyuva, Hamide Z. [Ankara Test and Analysis Laboratory, Scientific and Technological Research Council of Turkey, Ankara 06330 (Turkey)], E-mail: hamide.senyuva@tubitak.gov.tr; Gilbert, John [Central Science Laboratory, Sand Hutton, York YO41 1LZ (United Kingdom); Oztuerkoglu, Sebnem [Ankara Test and Analysis Laboratory, Scientific and Technological Research Council of Turkey, Ankara 06330 (Turkey)

    2008-06-09

    A liquid chromatography-time-of-flight mass spectrometry (LC/TOF-MS) method has been developed for profiling fungal metabolites. The performance of the procedure in terms of mass accuracy, selectivity (specificity) and repeatability was established by spiking aflatoxins, ochratoxins, trichothecenes and other metabolites into blank growth media. After extracting, and carrying out LC/TOF-MS analysis, the standards were correctly identified by searching a specially constructed database of 465 secondary metabolites. To demonstrate the viability of this approach 11 toxigenic and four non-toxigenic fungi from reference collections were grown on various media, for 7-14 days. The method was also applied to two toxigenic fungi, A. flavus (200-138) and A. parasiticus (2999-465) grown on gamma radiation sterilised dried figs, for 7-14 days. The fungal hyphae plus a portion of growth media or portions of dried figs were solvent extracted and analysed by LC/TOF-MS using a rapid resolution microbore LC column. Data processing based on cluster analysis, showed that electrospray ionization (ESI)-TOF-MS could be used to unequivocally identify metabolites in crude extracts. Using the elemental metabolite database, it was demonstrated that from culture collection isolates, anticipated metabolites. The speed and simplicity of the method has meant that levels of these metabolites could be monitored daily in sterilised figs. Over a 14-day period, levels of aflatoxins and kojic acid maximised at 5-6 days, whilst levels of 5-methoxysterigmatocystin remained relatively constant. In addition to the known metabolites expected to be produced by these fungi, roquefortine A, fumagillin, fumigaclavine B, malformins (peptides), aspergillic acid, nigragillin, terrein, terrestric acid and penicillic acid were also identified.

  3. Towards eco-friendly crop protection: natural deep eutectic solvents and defensive secondary metabolites.

    Science.gov (United States)

    Mouden, Sanae; Klinkhamer, Peter G L; Choi, Young Hae; Leiss, Kirsten A

    2017-01-01

    With mounting concerns over health and environmental effects of pesticides, the search for environmentally acceptable substitutes has amplified. Plant secondary metabolites appear in the horizon as an attractive solution for green crop protection. This paper reviews the need for changes in the techniques and compounds that, until recently, have been the mainstay for dealing with pest insects. Here we describe and discuss main strategies for selecting plant-derived metabolites as candidates for sustainable agriculture. The second part surveys ten important insecticidal compounds, with special emphasis on those involved in human health. Many of these insecticidal metabolites, however, are crystalline solids with limited solubility which might potentially hamper commercial formulation. As such, we introduce the concept of natural deep eutectic solvents for enhancing solubility and stability of such compounds. The concept, principles and examples of green pest control discussed here offer a new suite of environmental-friendly tools designed to promote and adopt sustainable agriculture.

  4. Production of secondary metabolites by some terverticillate penicillia on carbohydrate-rich and meat substrates.

    Science.gov (United States)

    Núñez, Félix; Westphal, Carmen D; Bermúdez, Elena; Asensio, Miguel A

    2007-12-01

    Most terverticillate penicillia isolated from dry-cured meat products are toxigenic, but their ability to produce hazardous metabolites on meat-based substrates is not well known. The production of extrolites by selected terverticillate penicillia isolated from dry-cured ham has been studied on carbohydrate-rich media (malt extract agar, Czapek yeast autolysate agar, rice extract agar, and rice), meat extract triolein salt agar, and ham slices. Chloroform extracts from the selected strains grown on malt extract agar were toxic for the brine shrimp (Artemia salina) larvae and VERO cells at a concentration of 2 mg/ml, but 0.02 mg/ml produced no toxic effect. Analysis by high-pressure liquid chromatography (HPLC) coupled with photodiode array detection (DAD) or with mass spectrometry (MS) and an atmospheric pressure chemical ionization (APCI) source revealed different biologically active metabolites: cyclopiazonic acid and rugulovasine A from Penicillium commune; verrucosidin, anacine, puberuline, verrucofortine, and viridicatols from Penicillium polonicum; arisugacin and viridicatols from Penicillium echinulatum; and compactin and viridicatols from Penicillium solitum. Most of these metabolites, including the amino acid-derived compounds, were produced in the media containing high levels of carbohydrates. High concentrations of nitrogen compounds in the medium does not imply a greater production of the metabolites studied, not even those derived from the amino acids. However, molds growing on dry-cured ham are able to synthesize limited amounts of some secondary metabolites, a fact not previously reported. The combination of HPLC coupled with DAD and MS-APCI was useful for identification of closely related terverticillate Penicillium species from dry-cured ham. These techniques could be used to characterize the risk associated with the potential production of secondary metabolites in cured meats.

  5. Bacillus amyloliquefaciens GA1 as a source of potent antibiotics and other secondary metabolites for biocontrol of plant pathogens

    Directory of Open Access Journals (Sweden)

    Brans Alain

    2009-11-01

    Full Text Available Abstract Background Phytopathogenic fungi affecting crop and post-harvested vegetables are a major threat to food production and food storage. To face these drawbacks, producers have become increasingly dependent on agrochemicals. However, intensive use of these compounds has led to the emergence of pathogen resistance and severe negative environmental impacts. There are also a number of plant diseases for which chemical solutions are ineffective or non-existent as well as an increasing demand by consumers for pesticide-free food. Thus, biological control through the use of natural antagonistic microorganisms has emerged as a promising alternative to chemical pesticides for more rational and safe crop management. Results The genome of the plant-associated B. amyloliquefaciens GA1 was sample sequenced. Several gene clusters involved in the synthesis of biocontrol agents were detected. Four gene clusters were shown to direct the synthesis of the cyclic lipopeptides surfactin, iturin A and fengycin as well as the iron-siderophore bacillibactin. Beside these non-ribosomaly synthetised peptides, three additional gene clusters directing the synthesis of the antibacterial polyketides macrolactin, bacillaene and difficidin were identified. Mass spectrometry analysis of culture supernatants led to the identification of these secondary metabolites, hence demonstrating that the corresponding biosynthetic gene clusters are functional in strain GA1. In addition, genes encoding enzymes involved in synthesis and export of the dipeptide antibiotic bacilysin were highlighted. However, only its chlorinated derivative, chlorotetaine, could be detected in culture supernatants. On the contrary, genes involved in ribosome-dependent synthesis of bacteriocin and other antibiotic peptides were not detected as compared to the reference strain B. amyloliquefaciens FZB42. Conclusion The production of all of these antibiotic compounds highlights B. amyloliquefaciens GA1 as

  6. The cross-pathway control system regulates production of the secondary metabolite toxin, sirodesmin PL, in the ascomycete, Leptosphaeria maculans

    Directory of Open Access Journals (Sweden)

    Fox Ellen M

    2011-07-01

    Full Text Available Abstract Background Sirodesmin PL is a secondary metabolite toxin made by the ascomycetous plant pathogen, Leptosphaeria maculans. The sirodesmin biosynthetic genes are clustered in the genome. The key genes are a non-ribosomal peptide synthetase, sirP, and a pathway-specific transcription factor, sirZ. Little is known about regulation of sirodesmin production. Results Genes involved in regulation of sirodesmin PL in L. maculans have been identified. Two hundred random insertional T-DNA mutants were screened with an antibacterial assay for ones producing low levels of sirodesmin PL. Three such mutants were isolated and each transcribed sirZ at very low levels. One of the affected genes had high sequence similarity to Aspergillus fumigatus cpcA, which regulates the cross-pathway control system in response to amino acid availability. This gene was silenced in L. maculans and the resultant mutant characterised. When amino acid starvation was artificially-induced by addition of 3-aminotriazole for 5 h, transcript levels of sirP and sirZ did not change in the wild type. In contrast, levels of sirP and sirZ transcripts increased in the silenced cpcA mutant. After prolonged amino acid starvation the silenced cpcA mutant produced much higher amounts of sirodesmin PL than the wild type. Conclusions Production of sirodesmin PL in L. maculans is regulated by the cross pathway control gene, cpcA, either directly or indirectly via the pathway-specific transcription factor, sirZ.

  7. Tissue-specific distribution of secondary metabolites in rapeseed (Brassica napus L..

    Directory of Open Access Journals (Sweden)

    Jingjing Fang

    Full Text Available Four different parts, hypocotyl and radicle (HR, inner cotyledon (IC, outer cotyledon (OC, seed coat and endosperm (SE, were sampled from mature rapeseed (Brassica napus L. by laser microdissection. Subsequently, major secondary metabolites, glucosinolates and sinapine, as well as three minor ones, a cyclic spermidine conjugate and two flavonoids, representing different compound categories, were qualified and quantified in dissected samples by high-performance liquid chromatography with diode array detection and mass spectrometry. No qualitative and quantitative difference of glucosinolates and sinapine was detected in embryo tissues (HR, IC and OC. On the other hand, the three minor compounds were observed to be distributed unevenly in different rapeseed tissues. The hypothetic biological functions of the distribution patterns of different secondary metabolites in rapeseed are discussed.

  8. [Effect of different fertilization treatments on yield and secondary metabolites of Codonopsis pilosula].

    Science.gov (United States)

    Hu, Jia-Dong; Mao, Ge; Zhang, Zhi-Wei; Ma, Cun-de; Liang, Zong-Suo; Xia, Guang-Dong; Dong, Juan-E

    2017-08-01

    The research studies the effect of different fertilization treatments on yield and accumulation of secondary metabolites of Codonopsis pilosula by using single factor randomized block design, in order to ensure reasonable harvesting time and fertilization ratio, and provide the basis for standardized cultivation of C. pilosula. According to the clustering results, the nitrogen fertilizer benefitted for the improvement of root diameter and biomass of C. pilosula. The phosphate fertilizer could promote the content of C. pilosula polysaccharide. The organic fertilizers could increase the content of lobetyolin. With the time going on, C. pilosula's yield, polysaccharide and ehanol-soluble extracts increased while the content of lobetyolin decreased. According to various factors, October is a more reasonable harvest period. Organic fertilizers are more helpful to the yield and accumulation of secondary metabolites of C. pilosula. Copyright© by the Chinese Pharmaceutical Association.

  9. In vitro culture of lavenders (Lavandula spp.) and the production of secondary metabolites.

    Science.gov (United States)

    Gonçalves, Sandra; Romano, Anabela

    2013-01-01

    Lavenders (Lavandula spp., Lamiaceae) are aromatic ornamental plants that are used widely in the food, perfume and pharmaceutical industries. The large-scale production of lavenders requires efficient in vitro propagation techniques to avoid the overexploitation of natural populations and to allow the application of biotechnology-based approaches for plant improvement and the production of valuable secondary metabolites. In this review we discuss micropropagation methods that have been developed in several lavender species, mainly based on meristem proliferation and organogenesis. Specific requirements during stages of micropropagation (establishment, shoot multiplication, root induction and acclimatization) and requisites for plant regeneration trough organogenesis, as an important step for the implementation of plant improvement programs, were revised. We also discuss different methods for the in vitro production of valuable secondary metabolites, focusing on the prospects for highly scalable cultures to meet the market demand for lavender-derived products. Copyright © 2012 Elsevier Inc. All rights reserved.

  10. Plant Secondary Metabolite-Derived Polymers: A Potential Approach to Develop Antimicrobial Films

    Directory of Open Access Journals (Sweden)

    Ahmed Al-Jumaili

    2018-05-01

    Full Text Available The persistent issue of bacterial and fungal colonization of artificial implantable materials and the decreasing efficacy of conventional systemic antibiotics used to treat implant-associated infections has led to the development of a wide range of antifouling and antibacterial strategies. This article reviews one such strategy where inherently biologically active renewable resources, i.e., plant secondary metabolites (PSMs and their naturally occurring combinations (i.e., essential oils are used for surface functionalization and synthesis of polymer thin films. With a distinct mode of antibacterial activity, broad spectrum of action, and diversity of available chemistries, plant secondary metabolites present an attractive alternative to conventional antibiotics. However, their conversion from liquid to solid phase without a significant loss of activity is not trivial. Using selected examples, this article shows how plasma techniques provide a sufficiently flexible and chemically reactive environment to enable the synthesis of biologically-active polymer coatings from volatile renewable resources.

  11. Bioactive secondary metabolites from the endophytic fungus Chaetomium sp. isolated from Salvia officinalis growing in Morocco

    Directory of Open Access Journals (Sweden)

    Ebel R.

    2009-01-01

    Full Text Available This study reports the chemical investigation and cytotoxic activity of the secondary metabolites produced by the endophytic fungus Chaetomium sp. isolated from Salvia officinalis growing in Morocco. This plant was collected from the Beni-Mellal Mountain in Morocco and belongs to the Lamiaceae family and is named in Morocco “Salmia”. The endophytic fungus Chaetomium sp. was isolated from the tissues of the stem of this plant. The fungal strain was identified by PCR. The crude organic extract of the fungal strain was proven to be active when tested for cytotoxicity against L5178Y mouse lymphoma cells. Chemical investigation of the secondary metabolites showed that cochliodinol is the main component beside isocochliodinol. The structures of the isolated compounds were determined on the basis of NMR analysis (1H, 13C, COSY and HMBC as well as by mass spectrometry using ESI (Electron Spray Ionisation as source.

  12. Chemical diversity and pharmacological significance of the secondary metabolites of nutmeg (Myristica fragrans Houtt.).

    Science.gov (United States)

    Abourashed, Ehab A; El-Alfy, Abir T

    2016-12-01

    Nutmeg is a valued kitchen spice that has been used for centuries all over the world. In addition to its use in flavoring foods and beverages, nutmeg has been used in traditional remedies for stomach and kidney disorders. The antioxidant, antimicrobial and central nervous system effects of nutmeg have also been reported in literature. Nutmeg is a rich source of fixed and essential oil, triterpenes, and various types of phenolic compounds. Many of the secondary metabolites of nutmeg exhibit biological activities that may support its use in traditional medicine. This article provides an overview of the chemistry of secondary metabolites isolated from nutmeg kernel and mace including common methods for analysis of extracts and pure compounds as well as recent approaches towards total synthesis of some of the major constituents. A summary of the most significant pharmacological investigations of potential drug leads isolated from nutmeg and reported in the last decade is also included.

  13. Genes Linked to Production of Secondary Metabolites in Talaromyces atroroseus Revealed Using CRISPR-Cas9

    DEFF Research Database (Denmark)

    Nielsen, Maria Lund; Petersen, Thomas Isbrandt; Rasmussen, Kasper Bøwig

    2017-01-01

    The full potential of fungal secondary metabolism has until recently been impeded by the lack of universal genetic tools for most species. However, the emergence of several CRISPR-Cas9-based genome editing systems adapted for several genera of filamentous fungi have now opened the doors for future...... efforts in discovery of novel natural products and elucidation and engineering of their biosynthetic pathways in fungi where no genetic tools are in place. So far, most studies have focused on demonstrating the performance of CRISPR-Cas9 in various fungal model species, and recently we presented...... a versatile CRISPR-Cas9 system that can be successfully applied in several diverse Aspergillus species. Here we take it one step further and show that our system can be used also in a phylogenetically distinct and largely unexplored species from the genus of Talaromyces. Specifically, we exploit CRISPR-Cas9...

  14. Antimicrobial and antiproliferative prospective of kosinostatin – a secondary metabolite isolated from Streptomyces sp.

    Directory of Open Access Journals (Sweden)

    Vinayagam Rambabu

    2015-12-01

    Full Text Available Cancer is a communal health hazard worldwide. The present investigation attempts to evaluate antimicrobial and anticancer potential of kosinostatin on mammary carcinoma cell line (MCF-7. The anticancer and antiproliferative activities of kosinostatin were analyzed on MCF cell line by MTT assay and cytotoxicity assays like lactate dehydrogenase (LDH and glutathione (GSH. The secondary metabolite kosinostatin exhibited its apoptotic nature by expressing p53 protein. Collectively, the results acquired from this study promise that kosinostatin shows the potent anticancer activity.

  15. Chemical ecology of insect-plant interactions: ecological significance of plant secondary metabolites.

    OpenAIRE

    Nishida, Ritsuo

    2014-01-01

    Plants produce a diverse array of secondary metabolites as chemical barriers against herbivores. Many phytophagous insects are highly adapted to these allelochemicals and use such unique substances as the specific host-finding cues, defensive substances of their own, and even as sex pheromones or their precursors by selectively sensing, incorporating, and/or processing these phytochemicals. Insects also serve as pollinators often effectively guided by specific floral fragrances. This review d...

  16. Cytoplasmic Acidification and Secondary Metabolite Production in Different Plant Cell Suspensions (A Comparative Study).

    Science.gov (United States)

    Hagendoorn, MJM.; Wagner, A. M.; Segers, G.; Van Der Plas, LHW.; Oostdam, A.; Van Walraven, H. S.

    1994-10-01

    In this study, a correlation is described between low cytoplasmic pH, measured with the fluorescent probes 2[prime],7[prime]-bis-(2-carboxyethyl)-5-(and-6)-carboxyfluorescein (acetoxymethyl ester) and bis- [3-propyl-5-oxoisoxazol-4-yl]pentamethine oxonol, and the production of secondary metabolites for several plant cell-suspension systems. Anthraquinone production in Morinda citrifolia suspensions is negligible in the presence of 2,4-dichlorophenoxyacetic acid (2,4-D), whereas with naphthalene acetic acid (NAA) a significant accumulation is realized. NAA-grown cells showed a lower cytoplasmic pH than did 2,4-D-grown cells. Addition of 2,4-D or parachlorophenoxy acetic acid to NAA-grown cells resulted in an inhibition of anthraquinone production and an increase of the cytoplasmic pH, whereas addition of parachlorophenyl acetic acid had no effect on either parameter. Lignin production in Petunia hybrida cells could be induced by subculturing them in a medium without iron. These cells showed a lower cytoplasmic pH than control cells. Addition of Fe3+ led to a decreased lignin content and an increased cytoplasmic pH. Two cell lines of Linum flavum showed a different level of coniferin and lignin concentration in their cells. Cells that accumulated coniferin and lignin had a lower cytoplasmic pH than cells that did not accumulate these secondary metabolites. Apparently, in different species and after different kinds of treatment there is a correlation between acidification of the cytoplasm and the production of different secondary metabolites. The possible role of this acidification in secondary metabolite production is discussed.

  17. Nectar microbes can reduce secondary metabolites in nectar and alter effects on nectar consumption by pollinators

    OpenAIRE

    Vannette, RL; Fukami, T

    2016-01-01

    © 2016 by the Ecological Society of America. Secondary metabolites that are present in floral nectar have been hypothesized to enhance specificity in plant-pollinator mutualism by reducing larceny by non-pollinators, including microorganisms that colonize nectar. However, few studies have tested this hypothesis. Using synthetic nectar, we conducted laboratory and field experiments to examine the effects of five chemical compounds found in nectar on the growth and metabolism of nectar-colonizi...

  18. A proteomic approach to investigating gene cluster expression and secondary metabolite functionality in Aspergillus fumigatus.

    OpenAIRE

    Owens, RA; Hammel, S; Sheridan, KJ; Jones, GW; Doyle, S

    2014-01-01

    A combined proteomics and metabolomics approach was utilised to advance the identification and characterisation of secondary metabolites in Aspergillus fumigatus. Here, implementation of a shotgun proteomic strategy led to the identification of non-redundant mycelial proteins (n = 414) from A. fumigatus including proteins typically under-represented in 2-D proteome maps: proteins with multiple transmembrane regions, hydrophobic proteins and proteins with extremes of molecular mass and pI. Ind...

  19. Effects of LEDs on chlorophyll fluorescence and secondary metabolites in Phalaenopsis

    DEFF Research Database (Denmark)

    Ouzounis, T.; Fretté, X.; Rosenqvist, Eva

    2015-01-01

    Light emitting diodes (LEDs) are solid-state semiconductor devices that have been integrated in current greenhouse systems the last decades as they provide the opportunity to control light spectrum. Commercial production of potted orchids under LEDs has increased throughout the world the past dec...... was a little higher when compared to the control. Quantitation of secondary metabolites was performed by HPLC. The analysis showed that the treatments with additional blue light had the highest amount of flavonoids and carotenoids....

  20. Taxonomic Characterization and Secondary Metabolite Profiling of Aspergillus Section Aspergillus Contaminating Feeds and Feedstuffs

    OpenAIRE

    Greco, Mariana; Kemppainen, Minna; Pose, Graciela; Pardo, Alejandro

    2015-01-01

    Xerophilic fungal species of the genus Aspergillus are economically highly relevant due to their ability to grow on low water activity substrates causing spoilage of stored goods and animal feeds. These fungi can synthesize a variety of secondary metabolites, many of which show animal toxicity, creating a health risk for food production animals and to humans as final consumers, respectively. Animal feeds used for rabbit, chinchilla and rainbow trout production in Argentina were analysed for t...

  1. Primary and secondary metabolites production in signal grass around the year under nitrogen fertilizer

    OpenAIRE

    Syeda Maryam Hussain

    2016-01-01

    Plants produce a number of substances and products and primary and secondary metabolites (SM) are amongst them with many benefits but limitation as well. Usually, the fodder are not considered toxic to animals or as a source having higher SM. The Brachiaria decumbens has a considerable nutritional value, but it is considered as a toxic grass for causing photosensitization in animals, if the grass is not harvested for more than 30 days or solely. The absence of detailed information in the lite...

  2. Secondary metabolites from Penicillium roqueforti, a starter for the production of Gorgonzola cheese

    Directory of Open Access Journals (Sweden)

    Lisa Vallone

    2014-09-01

    Full Text Available The presence of mold in food, although necessary for production, can involve the presence of secondary metabolites, which are sometimes toxic. Penicillium roqueforti is a common saprophytic fungus but it is also the essential fungus used in the production of Roquefort cheese and other varieties of blue cheese containing internal mold. The study was conducted on industrial batches of Penicillium roqueforti starters used in the production of the Gorgonzola cheese, with the aim to verify the production of secondary metabolites. Nine Penicillium roqueforti strains were tested. The presence of roquefortine C, PR toxin and mycophenolic acid was tested first in vitro, then on bread-like substrate and lastly in vivo in nine cheese samples produced with the same starters and ready to market. In vitro, only Penicillium out of nine produced roquefortine C, four starters showed mycophenolic acid production, while no significant amounts of PR toxin were detected. In the samples grown on bread-like substrate, Penicillium did not produce secondary metabolites, likewise with each cheese samples tested. To protect consumers’ health and safety, the presence of mycotoxins needs to be verified in food which is widely consumed, above all for products protected by the protected denomination of origin (DOP label (i.e. a certificate guaranteeing the geographic origin of the product, such as Gorgonzola cheese.

  3. water stress mediated changes in growth, physiology and secondary metabolites of desi ajwain (trachyspermum ammi l.)

    International Nuclear Information System (INIS)

    Azhar, N.; Hussain, B.; Abbasi, K.Y.

    2011-01-01

    Biotic and abiotic stresses exert a considerable influence on the production of several secondary metabolites in plants; water stress is one of the most important abiotic stress factors. This study was carried out to elucidate the effect of drought stress on growth, physiology and secondary metabolite production in desi ajwain (Trachyspermum ammi L.). Plants were grown in pots and three drought levels (100%, 80% and 60%) of field capacity were created. The experiment was laid out in complete randomized design (CRD) with three replicates. Data on growth, physiological and biochemical parameters were recorded and analyzed statistically. Physiological parameters like transpiration rate and stomatal conductance decreased concentration increased. The photosynthetic rate showed significantly with increasing water stress levels, but internal CO/sub 2/ non-significant reduction from 100% field capacity to 80% field capacity but increased at 60% field capacity. Growth parameters including plant height, herb fresh and dry weights were reduced significantly with increasing stress levels, while total phenolic contents and chlorophyll contents increased under water stress conditions. These results suggest that cultivation of medicinal plants like desi ajwain under drought stress could enhance the production of secondary metabolites. (author)

  4. Secondary metabolites profiles and antioxidant activities of germinated brown and red rice

    Science.gov (United States)

    Nurnaistia, Y.; Aisyah, S.; Munawaroh, H. S. H.; Zackiyah

    2018-05-01

    The research aims to investigate the effect of germination on the secondary metabolite profiles and antioxidant activity of brown and red rice. The germination was performed by using a simple laboratory-scale machine that was designed and optimized to provide conditions that support the germination process. The germination was carried out for 2 days in dark conditions at 26°C and 99% humidity. Analysis of the secondary metabolite profile of ungerminated and germinated rice was performed using LC-MS. The antioxidant activities of ungerminated and germinated rice were done by using DPPH method. The results showed that the profiles of secondary metabolites of brown and red rice changed after germination. Some peaks were found to be induced in the germinated rice. However, some peaks were also loss during germination. The antioxidant activity of brown rice was slightly increased due to the germination, from 11.2% to 22.5%. Meanwhile the antioxidant activity of red rice was decreased after germination, from 73.8% to 60.0%.

  5. Taxonomic Characterization and Secondary Metabolite Profiling of Aspergillus Section Aspergillus Contaminating Feeds and Feedstuffs

    Science.gov (United States)

    Greco, Mariana; Kemppainen, Minna; Pose, Graciela; Pardo, Alejandro

    2015-01-01

    Xerophilic fungal species of the genus Aspergillus are economically highly relevant due to their ability to grow on low water activity substrates causing spoilage of stored goods and animal feeds. These fungi can synthesize a variety of secondary metabolites, many of which show animal toxicity, creating a health risk for food production animals and to humans as final consumers, respectively. Animal feeds used for rabbit, chinchilla and rainbow trout production in Argentina were analysed for the presence of xerophilic Aspergillus section Aspergillus species. High isolation frequencies (>60%) were detected in all the studied rabbit and chinchilla feeds, while the rainbow trout feeds showed lower fungal charge (25%). These section Aspergillus contaminations comprised predominantly five taxa. Twenty isolates were subjected to taxonomic characterization using both ascospore SEM micromorphology and two independent DNA loci sequencing. The secondary metabolite profiles of the isolates were determined qualitatively by HPLC-MS. All the isolates produced neoechinulin A, 17 isolates were positive for cladosporin and echinulin, and 18 were positive for neoechinulin B. Physcion and preechinulin were detected in a minor proportion of the isolates. This is the first report describing the detailed species composition and the secondary metabolite profiles of Aspergillus section Aspergillus contaminating animal feeds. PMID:26364643

  6. Taxonomic Characterization and Secondary Metabolite Profiling of Aspergillus Section Aspergillus Contaminating Feeds and Feedstuffs

    Directory of Open Access Journals (Sweden)

    Mariana Greco

    2015-09-01

    Full Text Available Xerophilic fungal species of the genus Aspergillus are economically highly relevant due to their ability to grow on low water activity substrates causing spoilage of stored goods and animal feeds. These fungi can synthesize a variety of secondary metabolites, many of which show animal toxicity, creating a health risk for food production animals and to humans as final consumers, respectively. Animal feeds used for rabbit, chinchilla and rainbow trout production in Argentina were analysed for the presence of xerophilic Aspergillus section Aspergillus species. High isolation frequencies (>60% were detected in all the studied rabbit and chinchilla feeds, while the rainbow trout feeds showed lower fungal charge (25%. These section Aspergillus contaminations comprised predominantly five taxa. Twenty isolates were subjected to taxonomic characterization using both ascospore SEM micromorphology and two independent DNA loci sequencing. The secondary metabolite profiles of the isolates were determined qualitatively by HPLC-MS. All the isolates produced neoechinulin A, 17 isolates were positive for cladosporin and echinulin, and 18 were positive for neoechinulin B. Physcion and preechinulin were detected in a minor proportion of the isolates. This is the first report describing the detailed species composition and the secondary metabolite profiles of Aspergillus section Aspergillus contaminating animal feeds.

  7. Taxonomic Characterization and Secondary Metabolite Profiling of Aspergillus Section Aspergillus Contaminating Feeds and Feedstuffs.

    Science.gov (United States)

    Greco, Mariana; Kemppainen, Minna; Pose, Graciela; Pardo, Alejandro

    2015-09-02

    Xerophilic fungal species of the genus Aspergillus are economically highly relevant due to their ability to grow on low water activity substrates causing spoilage of stored goods and animal feeds. These fungi can synthesize a variety of secondary metabolites, many of which show animal toxicity, creating a health risk for food production animals and to humans as final consumers, respectively. Animal feeds used for rabbit, chinchilla and rainbow trout production in Argentina were analysed for the presence of xerophilic Aspergillus section Aspergillus species. High isolation frequencies (>60%) were detected in all the studied rabbit and chinchilla feeds, while the rainbow trout feeds showed lower fungal charge (25%). These section Aspergillus contaminations comprised predominantly five taxa. Twenty isolates were subjected to taxonomic characterization using both ascospore SEM micromorphology and two independent DNA loci sequencing. The secondary metabolite profiles of the isolates were determined qualitatively by HPLC-MS. All the isolates produced neoechinulin A, 17 isolates were positive for cladosporin and echinulin, and 18 were positive for neoechinulin B. Physcion and preechinulin were detected in a minor proportion of the isolates. This is the first report describing the detailed species composition and the secondary metabolite profiles of Aspergillus section Aspergillus contaminating animal feeds.

  8. Autophagy-Related Direct Membrane Import from ER/Cytoplasm into the Vacuole or Apoplast: A Hidden Gateway also for Secondary Metabolites and Phytohormones?

    Directory of Open Access Journals (Sweden)

    Ivan Kulich

    2014-04-01

    Full Text Available Transportation of low molecular weight cargoes into the plant vacuole represents an essential plant cell function. Several lines of evidence indicate that autophagy-related direct endoplasmic reticulum (ER to vacuole (and also, apoplast transport plays here a more general role than expected. This route is regulated by autophagy proteins, including recently discovered involvement of the exocyst subcomplex. Traffic from ER into the vacuole bypassing Golgi apparatus (GA acts not only in stress-related cytoplasm recycling or detoxification, but also in developmentally-regulated biopolymer and secondary metabolite import into the vacuole (or apoplast, exemplified by storage proteins and anthocyanins. We propose that this pathway is relevant also for some phytohormones’ (e.g., auxin, abscisic acid (ABA and salicylic acid (SA degradation. We hypothesize that SA is not only an autophagy inducer, but also a cargo for autophagy-related ER to vacuole membrane container delivery and catabolism. ER membrane localized enzymes will potentially enhance the area of biosynthetic reactive surfaces, and also, abundant ER localized membrane importers (e.g., ABC transporters will internalize specific molecular species into the autophagosome biogenesis domain of ER. Such active ER domains may create tubular invaginations of tonoplast into the vacuoles as import intermediates. Packaging of cargos into the ER-derived autophagosome-like containers might be an important mechanism of vacuole and exosome biogenesis and cytoplasm protection against toxic metabolites. A new perspective on metabolic transformations intimately linked to membrane trafficking in plants is emerging.

  9. Bioactive Secondary Metabolites from a Thai Collection of Soil and Marine-Derived Fungi of the Genera Neosartorya and Aspergillus.

    Science.gov (United States)

    Zin, War War May; Prompanya, Chadaporn; Buttachon, Suradet; Kijjoa, Anake

    2016-01-01

    Fungi are microorganisms which can produce interesting secondary metabolites with structural diversity. Although terrestrial fungi have been extensively investigated for their bioactive secondary metabolites such as antibiotics, marine-derived fungi have only recently attracted attention of Natural Products chemists. Our group has been working on the secondary metabolites produced by the cultures of the fungi of the genera Neosartorya and Aspergillus, collected from soil and marine environments from the tropical region for the purpose of finding new leads for anticancer and antibacterial drugs. This review covers only the secondary metabolites of four soil and six marine-derived species of Neosarorya as well as a new species of marine-derived Aspergillus, investigated by our group. In total, we have isolated fifty three secondary metabolites which can be categorized as polyketides (two), isocoumarins (six), terpenoids (two), meroterpenes (fourteen), alkaloids (twenty eight) and cyclic peptide (one). The anticancer and antibacterial activities of these fungal metabolites are also discussed. Among fifty three secondary metabolites isolated, only the alkaloid eurochevalierine and the cadinene sesquiterpene, isolated from the soil fungus N. pseudofisheri, showed relevant in vitro cytostatic activity against glioblastoma (U373) and non-small cell lung cancer (A549) cell lines while the meroditerpene aszonapyrone A exhibited strong antibacterial activity against multidrug-resistant Gram-positive bacteria and also strong antibiofilm activity in these isolates.

  10. Effects of Secondary Metabolites of Permafrost Bacillus sp. on Cytokine Synthesis by Human Peripheral Blood Mononuclear Cells.

    Science.gov (United States)

    Kalenova, L F; Kolyvanova, S S; Bazhin, A S; Besedin, I M; Mel'nikov, V P

    2017-06-01

    We studied the effects of secondary metabolites of Bacillus sp. isolated from late Neogene permafrost on secretion of proinflammatory (TNF-α, IL-1β, IL-8, IL-2, and IFNγ) and antiinflammatory (IL-4 and IL-10) cytokines by human peripheral blood mononuclear cells. It was found that metabolites of Bacillus sp. produced more potent effect on cytokine secretion than mitogen phytohemagglutinin and metabolites of Bacillus cereus, medicinal strain IP5832. Activity of metabolites depended on the temperature of bacteria incubation. "Cold" metabolites of Bacillus sp. (isolated at -5°C) primarily induced Th1-mediated secretion of IFNγ, while "warm" metabolites (obtained at 37°C) induced Th2-mediated secretion of IL-4. The results suggest that Bacillus sp. metabolites are promising material for the development of immunomodulating drugs.

  11. Secondary metabolites from Bacillus amyloliquefaciens isolated from soil can kill Burkholderia pseudomallei.

    Science.gov (United States)

    Boottanun, Patcharaporn; Potisap, Chotima; Hurdle, Julian G; Sermswan, Rasana W

    2017-12-01

    Bacillus species are Gram-positive bacteria found in abundance in nature and their secondary metabolites were found to possess various potential activities, notably antimicrobial. In this study, Bacillus amyloliquefaciens N2-4 and N3-8 were isolated from soil and their metabolites could kill Burkholderia pseudomallei, a Gram-negative pathogenic bacterium also found in soil in its endemic areas. Moreover, the metabolites were able to kill drug resistant isolates of B. pseudomallei and also inhibit other pathogenic bacteria such as Staphylococcus aureus, Escherichia coli and Acinetobacter baumannii but not the non-pathogenic Burkholderia thailandensis, which is closely related to B. pseudomallei. Since the antimicrobial activity of N3-8 was not partially decreased or abolished when treated with proteolytic enzymes or autoclaved, but N2-4 was, these two strains should have produced different compounds. The N3-8 metabolites with antimicrobial activity consisted of both protein and non-protein compounds. The inhibition spectrum of the precipitated proteins compared to the culture supernatant indicated a possible synergistic effect of the non-protein and peptide compounds of N3-8 isolates against other pathogens. When either N2-4 or N3-8 isolates was co-cultured with B. pseudomallei the numbers of the bacteria decreased by 5 log 10 within 72 h. Further purification and characterization of the metabolites is required for future use of the bacteria or their metabolites as biological controls of B. pseudomallei in the environment or for development as new drugs for problematic pathogenic bacteria.

  12. Enhancement of anti-inflammatory activity of Aloe vera adventitious root extracts through the alteration of primary and secondary metabolites via salicylic acid elicitation.

    Directory of Open Access Journals (Sweden)

    Yun Sun Lee

    Full Text Available Aloe vera (Asphodeloideae is a medicinal plant in which useful secondary metabolites are plentiful. Among the representative secondary metabolites of Aloe vera are the anthraquinones including aloe emodin and chrysophanol, which are tricyclic aromatic quinones synthesized via a plant-specific type III polyketide biosynthesis pathway. However, it is not yet clear which cellular responses can induce the pathway, leading to production of tricyclic aromatic quinones. In this study, we examined the effect of endogenous elicitors on the type III polyketide biosynthesis pathway and identified the metabolic changes induced in elicitor-treated Aloe vera adventitious roots. Salicylic acid, methyl jasmonate, and ethephon were used to treat Aloe vera adventitious roots cultured on MS liquid media with 0.3 mg/L IBA for 35 days. Aloe emodin and chrysophanol were remarkably increased by the SA treatment, more than 10-11 and 5-13 fold as compared with untreated control, respectively. Ultra-performance liquid chromatography-electrospray ionization mass spectrometry analysis identified a total of 37 SA-induced compounds, including aloe emodin and chrysophanol, and 3 of the compounds were tentatively identified as tricyclic aromatic quinones. Transcript accumulation analysis of polyketide synthase genes and gas chromatography mass spectrometry showed that these secondary metabolic changes resulted from increased expression of octaketide synthase genes and decreases in malonyl-CoA, which is the precursor for the tricyclic aromatic quinone biosynthesis pathway. In addition, anti-inflammatory activity was enhanced in extracts of SA-treated adventitious roots. Our results suggest that SA has an important role in activation of the plant specific-type III polyketide biosynthetic pathway, and therefore that the efficacy of Aloe vera as medicinal agent can be improved through SA treatment.

  13. Enhancement of anti-inflammatory activity of Aloe vera adventitious root extracts through the alteration of primary and secondary metabolites via salicylic acid elicitation.

    Science.gov (United States)

    Lee, Yun Sun; Ju, Hyun Kyoung; Kim, Yeon Jeong; Lim, Tae-Gyu; Uddin, Md Romij; Kim, Yeon Bok; Baek, Jin Hong; Kwon, Sung Won; Lee, Ki Won; Seo, Hak Soo; Park, Sang Un; Yang, Tae-Jin

    2013-01-01

    Aloe vera (Asphodeloideae) is a medicinal plant in which useful secondary metabolites are plentiful. Among the representative secondary metabolites of Aloe vera are the anthraquinones including aloe emodin and chrysophanol, which are tricyclic aromatic quinones synthesized via a plant-specific type III polyketide biosynthesis pathway. However, it is not yet clear which cellular responses can induce the pathway, leading to production of tricyclic aromatic quinones. In this study, we examined the effect of endogenous elicitors on the type III polyketide biosynthesis pathway and identified the metabolic changes induced in elicitor-treated Aloe vera adventitious roots. Salicylic acid, methyl jasmonate, and ethephon were used to treat Aloe vera adventitious roots cultured on MS liquid media with 0.3 mg/L IBA for 35 days. Aloe emodin and chrysophanol were remarkably increased by the SA treatment, more than 10-11 and 5-13 fold as compared with untreated control, respectively. Ultra-performance liquid chromatography-electrospray ionization mass spectrometry analysis identified a total of 37 SA-induced compounds, including aloe emodin and chrysophanol, and 3 of the compounds were tentatively identified as tricyclic aromatic quinones. Transcript accumulation analysis of polyketide synthase genes and gas chromatography mass spectrometry showed that these secondary metabolic changes resulted from increased expression of octaketide synthase genes and decreases in malonyl-CoA, which is the precursor for the tricyclic aromatic quinone biosynthesis pathway. In addition, anti-inflammatory activity was enhanced in extracts of SA-treated adventitious roots. Our results suggest that SA has an important role in activation of the plant specific-type III polyketide biosynthetic pathway, and therefore that the efficacy of Aloe vera as medicinal agent can be improved through SA treatment.

  14. Plant secondary metabolites in alfalfa, birdsfoot trefoil, reed canarygrass, and tall fescue unaffected by two different nitrogen sources

    Science.gov (United States)

    Plant secondary metabolites (PSM) may increase the sustainability of agriculture systems by reducing inputs, as PSM protect plants against herbivores and pathogens, act as pesticides, insecticides, and anthelmintics, while also attracting pollinators and seed dispersers. Therefore, it is important t...

  15. Secondary Metabolite Profiling of Species of the Genus Usnea by UHPLC-ESI-OT-MS-MS

    Directory of Open Access Journals (Sweden)

    Francisco Salgado

    2017-12-01

    Full Text Available Lichens are symbiotic associations of fungi with microalgae and/or cyanobacteria, which are considered among the slowest growing organisms, with strong tolerance to adverse environmental conditions. There are about 400 genera and 1600 species of lichens and those belonging to the Usnea genus comprise about 360 of these species. Usnea lichens have been used since ancient times as dyes, cosmetics, preservatives, deodorants and folk medicines. The phytochemistry of the Usnea genus includes more than 60 compounds which belong to the following classes: depsides, depsidones, depsones, lactones, quinones, phenolics, polysaccharides, fatty acids and dibenzofurans. Due to scarce knowledge of metabolomic profiles of Usnea species (U. barbata, U. antarctica, U. rubicunda and U. subfloridana, a study based on UHPLC-ESI-OT-MS-MS was performed for a comprehensive characterization of their secondary metabolites. From the methanolic extracts of these species a total of 73 metabolites were identified for the first time using this hyphenated technique, including 34 compounds in U. barbata, 21 in U. antarctica, 38 in U. rubicunda and 37 in U. subfloridana. Besides, a total of 13 metabolites were not identified and reported so far, and could be new according to our data analysis. This study showed that this hyphenated technique is rapid, effective and accurate for phytochemical identification of lichen metabolites and the data collected could be useful for chemotaxonomic studies.

  16. Production of fungal and bacterial growth modulating secondary metabolites is widespread among mycorrhiza-associated streptomycetes

    Science.gov (United States)

    2012-01-01

    Background Studies on mycorrhiza associated bacteria suggest that bacterial-fungal interactions play important roles during mycorrhiza formation and affect plant health. We surveyed Streptomyces Actinobacteria, known as antibiotic producers and antagonists of fungi, from Norway spruce mycorrhizas with predominantly Piloderma species as the fungal partner. Results Fifteen Streptomyces isolates exhibited substantial variation in inhibition of tested mycorrhizal and plant pathogenic fungi (Amanita muscaria, Fusarium oxysporum, Hebeloma cylindrosporum, Heterobasidion abietinum, Heterobasidion annosum, Laccaria bicolor, Piloderma croceum). The growth of the mycorrhiza-forming fungus Laccaria bicolor was stimulated by some of the streptomycetes, and Piloderma croceum was only moderately affected. Bacteria responded to the streptomycetes differently than the fungi. For instance the strain Streptomyces sp. AcM11, which inhibited most tested fungi, was less inhibitory to bacteria than other tested streptomycetes. The determined patterns of Streptomyces-microbe interactions were associated with distinct patterns of secondary metabolite production. Notably, potentially novel metabolites were produced by strains that were less antagonistic to fungi. Most of the identified metabolites were antibiotics (e.g. cycloheximide, actiphenol) and siderophores (e.g. ferulic acid, desferroxiamines). Plant disease resistance was activated by a single streptomycete strain only. Conclusions Mycorrhiza associated streptomycetes appear to have an important role in inhibiting the growth of fungi and bacteria. Additionally, our study indicates that the Streptomyces strains, which are not general antagonists of fungi, may produce still un-described metabolites. PMID:22852578

  17. Production of fungal and bacterial growth modulating secondary metabolites is widespread among mycorrhiza-associated streptomycetes

    Directory of Open Access Journals (Sweden)

    Schrey Silvia D

    2012-08-01

    Full Text Available Abstract Background Studies on mycorrhiza associated bacteria suggest that bacterial-fungal interactions play important roles during mycorrhiza formation and affect plant health. We surveyed Streptomyces Actinobacteria, known as antibiotic producers and antagonists of fungi, from Norway spruce mycorrhizas with predominantly Piloderma species as the fungal partner. Results Fifteen Streptomyces isolates exhibited substantial variation in inhibition of tested mycorrhizal and plant pathogenic fungi (Amanita muscaria, Fusarium oxysporum, Hebeloma cylindrosporum, Heterobasidion abietinum, Heterobasidion annosum, Laccaria bicolor, Piloderma croceum. The growth of the mycorrhiza-forming fungus Laccaria bicolor was stimulated by some of the streptomycetes, and Piloderma croceum was only moderately affected. Bacteria responded to the streptomycetes differently than the fungi. For instance the strain Streptomyces sp. AcM11, which inhibited most tested fungi, was less inhibitory to bacteria than other tested streptomycetes. The determined patterns of Streptomyces-microbe interactions were associated with distinct patterns of secondary metabolite production. Notably, potentially novel metabolites were produced by strains that were less antagonistic to fungi. Most of the identified metabolites were antibiotics (e.g. cycloheximide, actiphenol and siderophores (e.g. ferulic acid, desferroxiamines. Plant disease resistance was activated by a single streptomycete strain only. Conclusions Mycorrhiza associated streptomycetes appear to have an important role in inhibiting the growth of fungi and bacteria. Additionally, our study indicates that the Streptomyces strains, which are not general antagonists of fungi, may produce still un-described metabolites.

  18. Protection by fungal starters against growth and secondary metabolite production of fungal spoilers of cheese.

    Science.gov (United States)

    Nielsen, M S; Frisvad, J C; Nielsen, P V

    1998-06-30

    The influence of fungal starter cultures on growth and secondary metabolite production of fungal contaminants associated with cheese was studied on laboratory media and Camembert cheese. Isolates of the species Penicillium nalgiovense, P. camemberti, P. roqueforti and Geotrichum candidum were used as fungal starters. The species P. commune, P. caseifulvum, P. verrucosum, P. discolor, P. solitum, P. coprophilum and Aspergillus versicolor were selected as contaminants. The fungal starters showed different competitive ability on laboratory media and Camembert cheese. The presence of the Penicillium species, especially P. nalgiovense, showed an inhibitory effect on the growth of the fungal contaminants on laboratory media. G. candidum caused a significant inhibition of the fungal contaminants on Camembert cheese. The results indicate that G. candidum plays an important role in competition with undesirable microorganisms in mould fermented cheeses. Among the starters, P. nalgiovense caused the largest reduction in secondary metabolite production of the fungal contaminants on the laboratory medium. On Camembert cheese no significant changes in metabolite production of the fungal contaminants was observed in the presence of the starters.

  19. Ecosystem, location, and climate effects on foliar secondary metabolites of lodgepole pine populations from central British Columbia.

    Science.gov (United States)

    Wallis, Christopher M; Huber, Dezene P W; Lewis, Kathy J

    2011-06-01

    Lodgepole pines, Pinus contorta Douglas ex Louden var. latifolia Engelm. ex S. Watson, are encountering increased abiotic stress and pest activity due to recent increases in temperature and changes in precipitation throughout their range. This tree species counters these threats by producing secondary metabolites, including phenolics and terpenoids. We examined foliar levels of lignin, soluble phenolics, monoterpenoids, sesquiterpenoids, and diterpenoids in 12 stands in British Columbia, Canada. We used these data to assess associations among foliar secondary metabolite levels and ecosystem, geographic, and climatic variables. Regressions were also performed to observe which combinations of variables best explained secondary metabolite variance. Stands of P. c. latifolia in the Coastal Western Hemlock and Interior Cedar/Hemlock biogeoclimatic zones had consistently greater foliar levels of almost all measured secondary metabolites than did other stands. Lignin was present in greater amounts in Boreal White/Black Spruce ecosystem (i.e., northern) stands than in southern stands, suggesting a role for this metabolite in pine survival in the boreal forest. Attempts to develop regression models with geographic and climatic variables to explain foliar secondary metabolite levels resulted in multiple models with similar predictive capability. Since foliar secondary metabolite levels appeared to vary most between stand ecosystem types and not as much due to geographic and climatic variables, metabolic profiles appeared best matched to the stress levels within local environments. It is unknown if differences in secondary metabolite levels are the result of genetic adaptation or phenotypic plasticity, but results from this and other studies suggest that both are important. These results are interpreted in light of ongoing efforts to assist in the migration of certain populations of P. c. latifolia northward in an effort to counter predicted effects of climate change.

  20. Elicitation Based Enhancement of Secondary Metabolites in Rauwolfia serpentina and Solanum khasianum Hairy Root Cultures.

    Science.gov (United States)

    Srivastava, Mrinalini; Sharma, Swati; Misra, Pratibha

    2016-05-01

    Rauwolfia serpentina and Solanum khasianum are well-known medicinally important plants contained important alkaloids in their different parts. Elicitation of these alkaloids is important because of associated pharmaceutical properties. Targeted metabolites were ajmaline and ajmalicine in R. serpentina; solasodine and α-solanine in S. khasianum. Enhancement of secondary metabolites through biotic and abiotic elicitors in hairy root cultures of R. serpentina and S. khasianum. In this report, hairy root cultures of these two plants were established through Agrobacterium rhizogenes mediated transformation by optimizing various parameters as age of explants, duration of preculture, and co-cultivation period. NaCl was used as abiotic elicitors in these two plants. Cellulase from Aspergillus niger was used as biotic elicitor in S. khasianum and mannan from Saccharomyces cerevisiae was used in R. serpentina. First time we have reported the effect of biotic and abiotic elicitors on the production of important metabolites in hairy root cultures of these two plants. Ajmalicine production was stimulated up to 14.8-fold at 100 mM concentration of NaCl after 1 week of treatment. Ajmaline concentration was also increased 2.9-fold at 100 mg/l dose of mannan after 1 week. Solasodine content was enhanced up to 4.0-fold and 3.6-fold at 100 mM and 200 mM NaCl, respectively, after 6 days of treatments. This study explored the potential of the elicitation strategy in A. rhizogenes transformed cell cultures and this potential further used for commercial production of these pharmaceutically important secondary metabolites. Hairy roots of Rauwolfia serpentina were subjected to salt (abiotic stress) and mannan (biotic stress) treatment for 1 week. Ajmaline and ajmalicine secondary metabolites were quantified before and after stress treatmentAjmalicine yield was enhanced up to 14.8-fold at 100 mM concentration of NaCl. Ajmaline content was also stimulated 2.9-fold at 100 mg/l dose of mannan

  1. Nectar microbes can reduce secondary metabolites in nectar and alter effects on nectar consumption by pollinators.

    Science.gov (United States)

    Vannette, Rachel L; Fukami, Tadashi

    2016-06-01

    Secondary metabolites that are present in floral nectar have been hypothesized to enhance specificity in plant-pollinator mutualism by reducing larceny by non-pollinators, including microorganisms that colonize nectar. However, few studies have tested this hypothesis. Using synthetic nectar, we conducted laboratory and field experiments to examine the effects of five chemical compounds found in nectar on the growth and metabolism of nectar-colonizing yeasts and bacteria, and the interactive effects of these compounds and nectar microbes on the consumption of nectar by pollinators. In most cases, focal compounds inhibited microbial growth, but the extent of these effects depended on compound identity, concentration, and microbial species. Moreover, most compounds did not substantially decrease sugar metabolism by microbes, and microbes reduced the concentration of some compounds in nectar. Using artificial flowers in the field, we also found that the common nectar yeast Metschnikowia reukaufii altered nectar consumption by small floral visitors, but only in nectar containing catalpol. This effect was likely mediated by a mechanism independent of catalpol metabolism. Despite strong compound-specific effects on microbial growth, our results suggest that the secondary metabolites tested here are unlikely to be an effective general defense mechanism for preserving nectar sugars for pollinators. Instead, our results indicate that microbial colonization of nectar could reduce the concentration of secondary compounds in nectar and, in some cases, reduce deterrence to pollinators.

  2. Variability of Secondary Metabolites of the Species Cichorium intybus L. from Different Habitats

    Directory of Open Access Journals (Sweden)

    Nenad M. Zlatić

    2017-09-01

    Full Text Available The principal aim of this paper is to show the influence of soil characteristics on the quantitative variability of secondary metabolites. Analysis of phenolic content, flavonoid concentrations, and the antioxidant activity was performed using the ethanol and ethyl acetate plant extracts of the species Cichorium intybus L. (Asteraceae. The samples were collected from one saline habitat and two non-saline habitats. The values of phenolic content from the samples taken from the saline habitat ranged from 119.83 to 120.83 mg GA/g and from non-saline habitats from 92.44 to 115.10 mg GA/g. The amount of flavonoids in the samples from the saline locality varied between 144.36 and 317.62 mg Ru/g and from non-saline localities between 86.03 and 273.07 mg Ru/g. The IC50 values of antioxidant activity in the samples from the saline habitat ranged from 87.64 to 117.73 μg/mL and from 101.44 to 125.76 μg/mL in the samples from non-saline habitats. The results confirmed that soil types represent a significant influence on the quantitative content of secondary metabolites. The greatest concentrations of phenols and flavonoids and the highest level of antioxidant activity were found in the samples from saline soil. This further corroborates the importance of saline soil as an ecological factor, as it is proven to give rise to increased biosynthesis of secondary metabolites and related antioxidant activity.

  3. The Production of Secondary Metabolites with Flavour Potential during Brewing and Distilling Wort Fermentations

    Directory of Open Access Journals (Sweden)

    Graham G. Stewart

    2017-11-01

    Full Text Available Ethanol, carbon dioxide and glycerol are the major products produced by yeast during wort fermentation but they have little impact on beer and spirit flavour. It is the type and concentration of secondary metabolites that can determine overall beer flavour. These compounds are (but not only primarily: higher alcohols, esters, carbonyls and sulphur compounds—inorganic and organic. There are a number of factors that can modify the balance of these compounds most of which are discussed in this review paper.

  4. Review of secondary metabolites and mycotoxins from the Aspergillus niger group

    DEFF Research Database (Denmark)

    Nielsen, Kristian Fog; Mogensen, Jesper Mølgaard; Johansen, Maria

    2009-01-01

    (excluding A. aculeatus and its close relatives) from which currently 145 different secondary metabolites have been isolated and/or detected. From a human and animal safety point of view, the mycotoxins ochratoxin A (from A. carbonarius and less frequently A. niger) and fumonisin B2 (from A. niger......) are currently the most problematic compounds. Especially in foods and feeds such as coffee, nuts, dried fruits, and grape-based products where fumonisin-producing fusaria are not a problem, fumonisins pose a risk. Moreover, compounds such as malformins, naptho-γ-pyrones, and bicoumarins (kotanins) call...

  5. Antifouling activity exhibited by secondary metabolites of the marine sponge, Haliclona exigua (Kirkpatrick)

    Digital Repository Service at National Institute of Oceanography (India)

    LimnaMol, V.P.; Raveendran, T.V.; Parameswaran, P.S.

    stream_size 29406 stream_content_type text/plain stream_name Int_Biodeterior_Biodegrad_63_67.pdf.txt stream_source_info Int_Biodeterior_Biodegrad_63_67.pdf.txt Content-Encoding UTF-8 Content-Type text/plain; charset=UTF-8... 1    Author version: Int. Biodeterior. Biodegrad.: 63(1); 2009; 67-72 Antifouling activity exhibited by secondary metabolites of the marine sponge, Haliclona exigua (Kirkpatrick) VP LIMNA MOL a , TV RAVEENDRAN a, * & PS PARAMESWARAN b a...

  6. New Antioxidative Secondary Metabolites from the Fruits of a Beibu Gulf Mangrove, Avicennia marina

    Directory of Open Access Journals (Sweden)

    Cheng-Hai Gao

    2014-07-01

    Full Text Available Further chemical investigation of the fruits of the mangrove, Avicennia marina, afforded three new phenylethyl glycosides, marinoids J–L (1–3, and a new cinnamoyl glycoside, marinoid M (4. The structures of isolates were elucidated on the basis of extensive spectroscopic analysis and by comparison of the data with those of related secondary metabolites. The antioxidant activity of the isolates was evaluated using the cellular antioxidant assay (CAA, and compounds 1–4 showed antioxidant activities, with EC50 values ranging from 23.0 ± 0.71 μM to 247.8 ± 2.47 μM.

  7. Isolation and characterisation of three new anthraquinone secondary metabolites from Symplocos racemosa.

    Science.gov (United States)

    Farooq, Umar; Naz, Sadia; Khan, Ajmal; Khan, Sara; Khan, Afsar; Ali, Mumtaz; Khan, Saleha Suleman

    2016-01-01

    Three new anthraquinone secondary metabolites were isolated from Symplocos racemosa, a small tree of family symplocaceae. The structures of compounds (1-3) were elucidated to be 1,4-dihydroxy-6-(ethoxymethyl)-8-propylanthracene-9,10-dione (1), 1,4-dihydroxy-6-(hydroxymethyl)-8-butylanthracene-9,10-dione (2) and 1,4-dihydroxy-6-(hydroxymethyl)-8-propyl anthracene-9,10-dione (3) using their spectral data, i.e. through IR, UV, (1)H NMR, (13)C NMR and two-dimensional (2D) NMR techniques including heteronuclear multiple quantum coherence, heteronuclear multiple bond correlation and correlation spectroscopy.

  8. In vitro erythrocytic membrane effects of dibenzyl trisulfide, a secondary metabolite of Petiveria alliacea.

    Science.gov (United States)

    Pepple, D J; Richards, A A; Lowe, D A; Reid, W A; Younger, N O; Williams, L A D

    2010-12-01

    We investigated the in vitro effect of dibenzyl trisulfide (DTS), a secondary metabolite of Petiveria alliacea, on erythrocyte elasticity, relaxation time and membrane morphology. Blood samples from 8 volunteers with hemoglobin AA were exposed to 100, 200, 400, 800 and 1000 ng/ml of DTS respectively and the elasticity and relaxation time measured. There were statistically significant, dose-dependent increases in elasticity and relaxation times. The changes in membrane morphology observed also increased with increased concentration of DTS. This suggests that DTS interaction with membrane protein resulted in increased elasticity, relaxation time and deformation of the erythrocyte membrane. Copyright © 2010 Elsevier B.V. All rights reserved.

  9. [Effective productions of plant secondary metabolites having antitumor activity by plant cell and tissue cultures].

    Science.gov (United States)

    Taniguchi, Shoko

    2005-06-01

    Methods for the effective production of plant secondary metabolites with antitumor activity using plant cell and tissue cultures were developed. The factors in tannin productivity were investigated using culture strains producing different types of hydrolyzable tannins, i.e., gallotannins (mixture of galloylglucoses), ellagi-, and dehydroellagitannins. Production of ellagi- and dehydroellagitannins was affected by the concentrations and ratio of nitrogen sources in the medium. The formation of oligomeric ellagitannins in shoots of Oenothera tetraptera was correlated with the differentiation of tissues. Cultured cells of Eriobotrya japonica producing ursane- and oleanane-type triterpenes with antitumor activities were also established.

  10. Quantification of a bacterial secondary metabolite by SERS combined with SLM extraction for bioprocess monitoring

    DEFF Research Database (Denmark)

    Morelli, Lidia; Andreasen, Sune Zoëga; Jendresen, Christian Bille

    2017-01-01

    and combined it with surface enhanced Raman scattering (SERS) sensing for the screening of a biological process, namely for the quantification of a bacterial secondary metabolite, p-coumaric acid (pHCA), produced by Escherichia coli. The microfluidic device proved to be robust and reusable, enabling efficient...... removal of interfering compounds from the real samples, reaching more than 13-fold up-concentration of the donor at 10 μL min-1 flow rate. With this method, we quantified pHCA directly from the bacterial supernatant, distinguishing between various culture conditions based on the pHCA production yield...

  11. Subcellular localization of secondary lipid metabolites including fragrance volatiles in carnation petals

    International Nuclear Information System (INIS)

    Hudak, K.A.; Thompson, J.E.

    1997-01-01

    Pulse-chase labeling of carnation (Dianthus caryophyllus L. cv Improved White Sim) petals with [14C]acetate has provided evidence for a hydrophobic subcompartment of lipid-protein particles within the cytosol that resemble oil bodies, are formed by blebbing from membranes, and are enriched in lipid metabolites (including fragrance volatiles) derived from membrane fatty acids. Fractionation of the petals during pulse-chase labeling revealed that radiolabeled fatty acids appear first in microsomal membranes and subsequently in cytosolic lipid-protein particles, indicating that the particles originate from membranes. This interpretation is supported by the finding that the cytosolic lipid-protein particles contain phospholipid as well as the same fatty acids found in microsomal membranes. Radiolabeled polar lipid metabolites (methanol/ water-soluble) were detectable in both in situ lipid-protein particles isolated from the cytosol and those generated in vitro from isolated radiolabeled microsomal membranes. The lipid-protein particles were also enriched in hexanal, trans-2-hexenal, 1-hexanol, 3-hexen-1-ol, and 2-hexanol, volatiles of carnation flower fragrance that are derived from membrane fatty acids through the lipoxygenase pathway. Therefore, secondary lipid metabolites, including components of fragrance, appear to be formed within membranes of petal tissue and are subsequently released from the membrane bilayers into the cytosol by blebbing of lipid-protein particles

  12. Protozoan growth rates on secondary-metabolite-producing Pseudomonas spp. correlate with high-level protozoan taxonomy

    DEFF Research Database (Denmark)

    Pedersen, Annette L.; Winding, Anne; Altenburger, Andreas

    2011-01-01

    Different features can protect bacteria against protozoan grazing, for example large size, rapid movement, and production of secondary metabolites. Most papers dealing with these matters focus on bacteria. Here, we describe protozoan features that affect their ability to grow on secondary-metabol...

  13. Influence of natural substrates and co-occurring marine bacteria on the production of secondary metabolites by Photobacterium halotolerans

    DEFF Research Database (Denmark)

    Månsson, Maria; Giobergia, Sonia; Møller, Kirsten A.

    Genome sequences reveal that our current standard laboratory conditions only support a fraction of the potential secondary metabolism in bacteria. Thus, we must rethink cultivation, detection, and isolation strategies for bacterial secondary metabolites in order to explore the huge, so far...

  14. Production of secondary metabolites trimethyl xanthina by Camellia sinensis L suspension culture

    Science.gov (United States)

    Sutini, Sodiq, Mochamad; Muslihatin, Wirdhatul; Indra, Mochamad Rasjad

    2017-06-01

    Bioactive trimethyl xanthina can be obtained from the plant Camellia sinensis L. To obtain bioactive plant of which there are several hurdles for instance to wait up to five years to be harvested, also it needs land at a certain height from the sea level. Therefore, the production of secondary metabolites trimethyl xanthina need to be developed with suspense culture techniques. The purpose of this study obtained the production of bioactive trimethyl xanthina way culturally suspense in large scale with a relatively short time, potentially as anti-oxidants. Research methods include: (1) initiation of callus from pieces of leaves, shoots the youngest of the plant Camellia sinensis L in the media MS with the optimization of the addition of growth regulators, (2) the subculture of callus on media and plant growth regulator that is equal to the stage of initiation, (3) initiation of suspension culture using explants of callus Camellia sinensis L, (4) Analysis of secondary metabolites trimethyl xanthina growth in suspension culture, (5) the isolation and identification of trimethyl xanthina qualitatively and quantitatively using thin layer chromatography/high performance chromatography column. The results of the study suspension cultures containing bioactive trimethyl xanthina candidates that can be used as an antioxidant.

  15. Effects of space flight on DNA mutation and secondary metabolites of licorice (Glycyrrhiza uralensis Fisch.)

    Institute of Scientific and Technical Information of China (English)

    GAO WenYuan; LI KeFeng; YAN Shuo; GAO XiuMei; HU LiMin

    2009-01-01

    Licorice (Glycyrrhiza uralensis Fisch.) seeds were flown on a recoverable satellite for 18 days(the average radiation dose in the flight recovery module was 0.102 mGy/d, the distance from flight apogee to earth was 350 km, gravity 10~(-6)). After returning to earth, the seeds were germinated and grown to maturity. The parallel ground-based seeds were also planted under the same conditions. The leaves of licorice were used for inter-simple sequence repeat (ISSR) analysis and the two main secondary metabolites in one-year-old roots were analyzed by high performance liquid chromatography (HPLC).Among 22 random primers used in this experiment, 6 primers generated different DNA band types. Analysis of HPLC showed that the content of glycyrrhizic acid (GA) and liquiritin (LQ) in the roots from seeds flown in space was respectively 2.19, 1.18 times higher than that of the control group. The results demonstrated that the extraterrestrial environment induced mutagenic effects on licorice and affected its secondary metabolites. These changes indicated that extraterrestrial orbit is possible means of breeding of licorice so as to preserve this endangered medicinal plant.

  16. Effects of space flight on DNA mutation and secondary metabolites of licorice (Glycyrrhiza uralensis Fisch.)

    Institute of Scientific and Technical Information of China (English)

    2009-01-01

    Licorice (Glycyrrhiza uralensis Fisch.) seeds were flown on a recoverable satellite for 18 days(the average radiation dose in the flight recovery module was 0.102 mGy/d, the distance from flight apogee to earth was 350 km, gravity 10-6). After returning to earth, the seeds were germinated and grown to maturity. The parallel ground-based seeds were also planted under the same conditions. The leaves of licorice were used for inter-simple sequence repeat (ISSR) analysis and the two main secondary me-tabolites in one-year-old roots were analyzed by high performance liquid chromatography (HPLC). Among 22 random primers used in this experiment, 6 primers generated different DNA band types. Analysis of HPLC showed that the content of glycyrrhizic acid (GA) and liquiritin (LQ) in the roots from seeds flown in space was respectively 2.19, 1.18 times higher than that of the control group. The results demonstrated that the extraterrestrial environment induced mutagenic effects on licorice and affected its secondary metabolites. These changes indicated that extraterrestrial orbit is possible means of breeding of licorice so as to preserve this endangered medicinal plant.

  17. Ecological functions of Trichoderma spp. and their secondary metabolites in the rhizosphere: interactions with plants.

    Science.gov (United States)

    Contreras-Cornejo, Hexon Angel; Macías-Rodríguez, Lourdes; del-Val, Ek; Larsen, John

    2016-04-01

    Trichodermaspp. are common soil and root inhabitants that have been widely studied due to their capacity to produce antibiotics, parasitize other fungi and compete with deleterious plant microorganisms. These fungi produce a number of secondary metabolites such as non-ribosomal peptides, terpenoids, pyrones and indolic-derived compounds. In the rhizosphere, the exchange and recognition of signaling molecules byTrichodermaand plants may alter physiological and biochemical aspects in both. For example, severalTrichodermastrains induce root branching and increase shoot biomass as a consequence of cell division, expansion and differentiation by the presence of fungal auxin-like compounds. Furthermore,Trichoderma, in association with plant roots, can trigger systemic resistance and improve plant nutrient uptake. The present review describes the most recent advances in understanding the ecological functions ofTrichodermaspp. in the rhizosphere at biochemical and molecular levels with special emphasis on their associations with plants. Finally, through a synthesis of the current body of work, we present potential future research directions on studies related toTrichodermaspp. and their secondary metabolites in agroecosystems. © FEMS 2016. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.

  18. Direct Analyses of Secondary Metabolites by Mass Spectrometry Imaging (MSI) from Sunflower (Helianthus annuus L.) Trichomes.

    Science.gov (United States)

    Brentan Silva, Denise; Aschenbrenner, Anna-Katharina; Lopes, Norberto Peporine; Spring, Otmar

    2017-05-10

    Helianthus annuus (sunflower) displays non-glandular trichomes (NGT), capitate glandular trichomes (CGT), and linear glandular trichomes (LGT), which reveal different chemical compositions and locations in different plant tissues. With matrix-assisted laser desorption/ionization (MALDI) and laser desorption/ionization (LDI) mass spectrometry imaging (MSI) techniques, efficient methods were developed to analyze the tissue distribution of secondary metabolites (flavonoids and sesquiterpenes) and proteins inside of trichomes. Herein, we analyzed sesquiterpene lactones, present in CGT, from leaf transversal sections using the matrix 2,5-dihydroxybenzoic acid (DHB) and α-cyano-4-hydroxycinnamic acid (CHCA) (mixture 1:1) with sodium ions added to increase the ionization in positive ion mode. The results observed for sesquiterpenes and polymethoxylated flavones from LGT were similar. However, upon desiccation, LGT changed their shape in the ionization source, complicating analyses by MSI mainly after matrix application. An alternative method could be applied to LGT regions by employing LDI (without matrix) in negative ion mode. The polymethoxylated flavones were easily ionized by LDI, producing images with higher resolution, but the sesquiterpenes were not observed in spectra. Thus, the application and viability of MALDI imaging for the analyses of protein and secondary metabolites inside trichomes were confirmed, highlighting the importance of optimization parameters.

  19. Optimized Jasmonic Acid Production by Lasiodiplodia theobromae Reveals Formation of Valuable Plant Secondary Metabolites.

    Directory of Open Access Journals (Sweden)

    Felipe Eng

    Full Text Available Jasmonic acid is a plant hormone that can be produced by the fungus Lasiodiplodia theobromae via submerged fermentation. From a biotechnological perspective jasmonic acid is a valuable feedstock as its derivatives serve as important ingredients in different cosmetic products and in the future it may be used for pharmaceutical applications. The objective of this work was to improve the production of jasmonic acid by L. theobromae strain 2334. We observed that jasmonic acid formation is dependent on the culture volume. Moreover, cultures grown in medium containing potassium nitrate as nitrogen source produced higher amounts of jasmonic acid than analogous cultures supplemented with ammonium nitrate. When cultivated under optimal conditions for jasmonic acid production, L. theobromae secreted several secondary metabolites known from plants into the medium. Among those we found 3-oxo-2-(pent-2-enyl-cyclopentane-1-butanoic acid (OPC-4 and hydroxy-jasmonic acid derivatives, respectively, suggesting that fungal jasmonate metabolism may involve similar reaction steps as that of plants. To characterize fungal growth and jasmonic acid-formation, we established a mathematical model describing both processes. This model may form the basis of industrial upscaling attempts. Importantly, it showed that jasmonic acid-formation is not associated to fungal growth. Therefore, this finding suggests that jasmonic acid, despite its enormous amount being produced upon fungal development, serves merely as secondary metabolite.

  20. Herbal extracts and phytochemicals: plant secondary metabolites and the enhancement of human brain function.

    Science.gov (United States)

    Kennedy, David O; Wightman, Emma L

    2011-01-01

    Humans consume a wide range of foods, drugs, and dietary supplements that are derived from plants and which modify the functioning of the central nervous sytem (CNS). The psychoactive properties of these substances are attributable to the presence of plant secondary metabolites, chemicals that are not required for the immediate survival of the plant but which are synthesized to increase the fitness of the plant to survive by allowing it to interact with its environment, including pathogens and herbivorous and symbiotic insects. In many cases, the effects of these phytochemicals on the human CNS might be linked either to their ecological roles in the life of the plant or to molecular and biochemical similarities in the biology of plants and higher animals. This review assesses the current evidence for the efficacy of a range of readily available plant-based extracts and chemicals that may improve brain function and which have attracted sufficient research in this regard to reach a conclusion as to their potential effectiveness as nootropics. Many of these candidate phytochemicals/extracts can be grouped by the chemical nature of their potentially active secondary metabolite constituents into alkaloids (caffeine, nicotine), terpenes (ginkgo, ginseng, valerian, Melissa officinalis, sage), and phenolic compounds (curcumin, resveratrol, epigallocatechin-3-gallate, Hypericum perforatum, soy isoflavones). They are discussed in terms of how an increased understanding of the relationship between their ecological roles and CNS effects might further the field of natural, phytochemical drug discovery.

  1. Herbal Extracts and Phytochemicals: Plant Secondary Metabolites and the Enhancement of Human Brain Function1

    Science.gov (United States)

    Kennedy, David O.; Wightman, Emma L.

    2011-01-01

    Humans consume a wide range of foods, drugs, and dietary supplements that are derived from plants and which modify the functioning of the central nervous sytem (CNS). The psychoactive properties of these substances are attributable to the presence of plant secondary metabolites, chemicals that are not required for the immediate survival of the plant but which are synthesized to increase the fitness of the plant to survive by allowing it to interact with its environment, including pathogens and herbivorous and symbiotic insects. In many cases, the effects of these phytochemicals on the human CNS might be linked either to their ecological roles in the life of the plant or to molecular and biochemical similarities in the biology of plants and higher animals. This review assesses the current evidence for the efficacy of a range of readily available plant-based extracts and chemicals that may improve brain function and which have attracted sufficient research in this regard to reach a conclusion as to their potential effectiveness as nootropics. Many of these candidate phytochemicals/extracts can be grouped by the chemical nature of their potentially active secondary metabolite constituents into alkaloids (caffeine, nicotine), terpenes (ginkgo, ginseng, valerian, Melissa officinalis, sage), and phenolic compounds (curcumin, resveratrol, epigallocatechin-3-gallate, Hypericum perforatum, soy isoflavones). They are discussed in terms of how an increased understanding of the relationship between their ecological roles and CNS effects might further the field of natural, phytochemical drug discovery. PMID:22211188

  2. Optimization of adventitious root culture for production of biomass and secondary metabolites in Prunella vulgaris L.

    Science.gov (United States)

    Fazal, Hina; Abbasi, Bilal Haider; Ahmad, Nisar

    2014-11-01

    Adventitious root cultures of Prunella vulgaris L. were established in shaking flask system for the production of biomass and secondary metabolites. Adventitious root cultures were induced from callus cultures obtained from leaf explants on solid Murashige and Skoog (MS) medium containing combination of 6-benzyladenine (BA; 1.0 mg l(-1)) and naphthalene acetic acid (NAA; 1.5 mg l(-1)). Thereafter, 0.49 g inoculum was transferred to liquid MS medium supplemented with different concentrations of NAA (0.5-2.0 mg l(-1)). Growth kinetics of adventitious roots was recorded with an interval of 7 days for 49 days period. Highest biomass accumulation (2.13 g/l) was observed in liquid medium containing 1.0 mg l(-1) NAA after 21 days of inoculation. However, other concentrations of NAA also showed similar accumulation pattern but the biomass gradually decreases after 49 days of inoculation. Adventitious roots were collected and dried for investigation of total phenolics (TP), total flavonoids (TF), and antioxidant activities. Higher TPC (0.995 GAE mg/g-DRB) and TFC (6.615 RE mg/g-DRB) were observed in 0.5 mg l(-1) NAA treated cultures. In contrast, higher antioxidant activity (83.53 %) was observed 1.5 mg l(-1) NAA treated cultures. These results are helpful in up scaling of root cultures into bioreactor for secondary metabolites production.

  3. Synthesis and Bioactivity of Secondary Metabolites from Marine Sponges Containing Dibrominated Indolic Systems

    Directory of Open Access Journals (Sweden)

    Azzurra Stefanucci

    2012-05-01

    Full Text Available Marine sponges. (e.g., Hyrtios sp., Dragmacidin sp., Aglophenia pleuma, Aplidium cyaneum, Aplidium meridianum. produce bioactive secondary metabolites involved in their defence mechanisms. Recently it was demonstrated that several of those compounds show a large variety of biological activities against different human diseases with possible applications in medicinal chemistry and in pharmaceutical fields, especially related to the new drug development process. Researchers have focused their attention principally on secondary metabolites with anti-cancer and cytotoxic activities. A common target for these molecules is the cytoskeleton, which has a central role in cellular proliferation, motility, and profusion involved in the metastatic process associate with tumors. In particular, many substances containing brominated indolic rings such as 5,6-dibromotryptamine, 5,6-dibromo-N-methyltryptamine, 5,6-dibromo-N-methyltryptophan (dibromoabrine, 5,6-dibromo-N,N-dimethyltryptamine and 5,6-dibromo-L-hypaphorine isolated from different marine sources, have shown anti-cancer activity, as well as antibiotic and anti-inflammatory properties. Considering the structural correlation between endogenous monoamine serotonin with marine indolic alkaloids 5,6-dibromoabrine and 5,6-dibromotryptamine, a potential use of some dibrominated indolic metabolites in the treatment of depression-related pathologies has also been hypothesized. Due to the potential applications in the treatment of various diseases and the increasing demand of these compounds for biological assays and the difficult of their isolation from marine sources, we report in this review a series of recent syntheses of marine dibrominated indole-containing products.

  4. Accessing biological actions of Ganoderma secondary metabolites by in silico profiling

    Science.gov (United States)

    Grienke, Ulrike; Kaserer, Teresa; Pfluger, Florian; Mair, Christina E.; Langer, Thierry; Schuster, Daniela; Rollinger, Judith M.

    2016-01-01

    The species complex around the medicinal fungus Ganoderma lucidum Karst. (Ganodermataceae) is widely known in traditional medicines as well as in modern applications such as functional food or nutraceuticals. A considerable number of publications reflects its abundance and variety in biological actions either provoked by primary metabolites such as polysaccharides or secondary metabolites such as lanostane-type triterpenes. However, due to this remarkable amount of information, a rationalization of the individual Ganoderma constituents to biological actions on a molecular level is quite challenging. To overcome this issue, a database was generated containing meta-information, i.e. chemical structures and biological actions of hitherto identified Ganoderma constituents (279). This was followed by a computational approach subjecting this 3D multi-conformational molecular dataset to in silico parallel screening against an in-house collection of validated structure- and ligand-based 3D pharmacophore models. The predictive power of the evaluated in silico tools and hints from traditional application fields served as criteria for the model selection. Thus, we focused on representative druggable targets in the field of viral infections (5) and diseases related to the metabolic syndrome (22). The results obtained from this in silico approach were compared to bioactivity data available from the literature to distinguish between true and false positives or negatives. 89 and 197 Ganoderma compounds were predicted as ligands of at least one of the selected pharmacological targets in the antiviral and the metabolic syndrome screening, respectively. Among them only a minority of individual compounds (around 10%) has ever been investigated on these targets or for the associated biological activity. Accordingly, this study discloses putative ligand target interactions for a plethora of Ganoderma constituents in the empirically manifested field of viral diseases and metabolic

  5. Comparison of expression of secondary metabolite biosynthesis cluster genes in Aspergillus flavus, A. parasiticus, and A. oryzae.

    Science.gov (United States)

    Ehrlich, Kenneth C; Mack, Brian M

    2014-06-23

    Fifty six secondary metabolite biosynthesis gene clusters are predicted to be in the Aspergillus flavus genome. In spite of this, the biosyntheses of only seven metabolites, including the aflatoxins, kojic acid, cyclopiazonic acid and aflatrem, have been assigned to a particular gene cluster. We used RNA-seq to compare expression of secondary metabolite genes in gene clusters for the closely related fungi A. parasiticus, A. oryzae, and A. flavus S and L sclerotial morphotypes. The data help to refine the identification of probable functional gene clusters within these species. Our results suggest that A. flavus, a prevalent contaminant of maize, cottonseed, peanuts and tree nuts, is capable of producing metabolites which, besides aflatoxin, could be an underappreciated contributor to its toxicity.

  6. Biosynthesis and Total Synthesis of Pyrronazol B: a Secondary Metabolite from Nannocystis pusilla.

    Science.gov (United States)

    Witte, Swjatoslaw N R; Hug, Joachim J; Géraldy, Magalie N E; Müller, Rolf; Kalesse, Markus

    2017-11-13

    The first stereoselective total synthesis of the natural product pyrronazol B, which contains a chlorinated pyrrole-oxazole-pyrone framework, has been achieved. Genome sequencing of the myxobacterial producer strain Nannocystis pusilla Ari7 led to the identification of the putative biosynthetic gene cluster. The proposed biosynthetic pathway was supported by feeding experiments with stable isotopes of three biosynthetic building blocks, namely l-proline, l-serine, and l-methionine. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  7. Ecotype variability in growth and secondary metabolite profile in Moringa oleifera: impact of sulfur and water availability.

    Science.gov (United States)

    Förster, Nadja; Ulrichs, Christian; Schreiner, Monika; Arndt, Nick; Schmidt, Reinhard; Mewis, Inga

    2015-03-25

    Moringa oleifera is widely cultivated in plantations in the tropics and subtropics. Previous cultivation studies with M. oleifera focused primarily only on leaf yield. In the present study, the content of potentially health-promoting secondary metabolites (glucosinolates, phenolic acids, and flavonoids) were also investigated. Six different ecotypes were grown under similar environmental conditions to identify phenotypic differences that can be traced back to the genotype. The ecotypes TOT4880 (origin USA) and TOT7267 (origin India) were identified as having the best growth performance and highest secondary metabolite production, making them an ideal health-promoting food crop. Furthermore, optimal cultivation conditions-exemplarily on sulfur fertilization and water availability-for achieving high leaf and secondary metabolite yields were investigated for M. oleifera. In general, plant biomass and height decreased under water deficiency compared to normal cultivation conditions, whereas the glucosinolate content increased. The effects depended to a great extent on the ecotype.

  8. Cellular Immune Reactions of the Sunn Pest, Eurygaster integriceps, to the Entomopathogenic Fungus, Beauveria bassiana and Its Secondary Metabolites

    Science.gov (United States)

    Zibaee, Arash; Bandani, Ali Reza; Talaei-Hassanlouei, Reza; Malagoli, Davide

    2011-01-01

    In this study, five morphological types of circulating hemocytes were recognized in the hemolymph of the adult sunn pest, Eurygaster integriceps Puton (Hemiptera: Scutelleridae), namely prohemocytes, plasmatocytes, granulocytes, adipohemocytes, and oenocytoids. The effects of the secondary metabolites of the entomopathogenic fungus Beauveria bassiana on cellular immune defenses of Eurygaster integriceps were investigated. The results showed that the fungal secondary metabolites inhibited phagocytic activity of E. integriceps hemocytes and hampered nodule formation. A reduction of phenoloxidase activity was also observed. The data suggest that B. bassiana produce secondary metabolites that disable several immune mechanisms allowing the fungus to overcome and then kill its host. This characteristic makes B. bassiana a promising model for biological control of insect pests such as E. integriceps. PMID:22233481

  9. SistematX, an Online Web-Based Cheminformatics Tool for Data Management of Secondary Metabolites.

    Science.gov (United States)

    Scotti, Marcus Tullius; Herrera-Acevedo, Chonny; Oliveira, Tiago Branquinho; Costa, Renan Paiva Oliveira; Santos, Silas Yudi Konno de Oliveira; Rodrigues, Ricardo Pereira; Scotti, Luciana; Da-Costa, Fernando Batista

    2018-01-03

    The traditional work of a natural products researcher consists in large part of time-consuming experimental work, collecting biota to prepare and analyze extracts and to identify innovative metabolites. However, along this long scientific path, much information is lost or restricted to a specific niche. The large amounts of data already produced and the science of metabolomics reveal new questions: Are these compounds known or new? How fast can this information be obtained? To answer these and other relevant questions, an appropriate procedure to correctly store information on the data retrieved from the discovered metabolites is necessary. The SistematX (http://sistematx.ufpb.br) interface is implemented considering the following aspects: (a) the ability to search by structure, SMILES (Simplified Molecular-Input Line-Entry System) code, compound name and species; (b) the ability to save chemical structures found by searching; (c) compound data results include important characteristics for natural products chemistry; and (d) the user can find specific information for taxonomic rank (from family to species) of the plant from which the compound was isolated, the searched-for molecule, and the bibliographic reference and Global Positioning System (GPS) coordinates. The SistematX homepage allows the user to log into the data management area using a login name and password and gain access to administration pages. In this article, we introduced a modern and innovative web interface for the management of a secondary metabolite database. With its multiplatform design, it is able to be properly consulted via the internet and managed from any accredited computer. The interface provided by SistematX contains a wealth of useful information for the scientific community about natural products, highlighting the locations of species from which compounds are isolated.

  10. An invasive plant promotes its arbuscular mycorrhizal symbioses and competitiveness through its secondary metabolites: indirect evidence from activated carbon.

    Directory of Open Access Journals (Sweden)

    Yongge Yuan

    Full Text Available Secondary metabolites released by invasive plants can increase their competitive ability by affecting native plants, herbivores, and pathogens at the invaded land. Whether these secondary metabolites affect the invasive plant itself, directly or indirectly through microorganisms, however, has not been well documented. Here we tested whether activated carbon (AC, a well-known absorbent for secondary metabolites, affect arbuscular mycorrhizal (AM symbioses and competitive ability in an invasive plant. We conducted three experiments (experiments 1-3 with the invasive forb Solidago canadensis and the native Kummerowia striata. Experiment 1 determined whether AC altered soil properties, levels of the main secondary metabolites in the soil, plant growth, and AMF communities associated with S. canadensis and K. striata. Experiment 2 determined whether AC affected colonization of S. canadensis by five AMF, which were added to sterilized soil. Experiment 3 determined the competitive ability of S. canadensis in the presence and absence of AMF and AC. In experiment 1, AC greatly decreased the concentrations of the main secondary metabolites in soil, and the changes in concentrations were closely related with the changes of AMF in S. canadensis roots. In experiment 2, AC inhibited the AMF Glomus versiforme and G. geosporum but promoted G. mosseae and G. diaphanum in the soil and also in S. canadensis roots. In experiment 3, AC reduced S. canadensis competitive ability in the presence but not in the absence of AMF. Our results provided indirect evidence that the secondary metabolites (which can be absorbed by AC of the invasive plant S. canadensis may promote S. canadensis competitiveness by enhancing its own AMF symbionts.

  11. An invasive plant promotes its arbuscular mycorrhizal symbioses and competitiveness through its secondary metabolites: indirect evidence from activated carbon.

    Science.gov (United States)

    Yuan, Yongge; Tang, Jianjun; Leng, Dong; Hu, Shuijin; Yong, Jean W H; Chen, Xin

    2014-01-01

    Secondary metabolites released by invasive plants can increase their competitive ability by affecting native plants, herbivores, and pathogens at the invaded land. Whether these secondary metabolites affect the invasive plant itself, directly or indirectly through microorganisms, however, has not been well documented. Here we tested whether activated carbon (AC), a well-known absorbent for secondary metabolites, affect arbuscular mycorrhizal (AM) symbioses and competitive ability in an invasive plant. We conducted three experiments (experiments 1-3) with the invasive forb Solidago canadensis and the native Kummerowia striata. Experiment 1 determined whether AC altered soil properties, levels of the main secondary metabolites in the soil, plant growth, and AMF communities associated with S. canadensis and K. striata. Experiment 2 determined whether AC affected colonization of S. canadensis by five AMF, which were added to sterilized soil. Experiment 3 determined the competitive ability of S. canadensis in the presence and absence of AMF and AC. In experiment 1, AC greatly decreased the concentrations of the main secondary metabolites in soil, and the changes in concentrations were closely related with the changes of AMF in S. canadensis roots. In experiment 2, AC inhibited the AMF Glomus versiforme and G. geosporum but promoted G. mosseae and G. diaphanum in the soil and also in S. canadensis roots. In experiment 3, AC reduced S. canadensis competitive ability in the presence but not in the absence of AMF. Our results provided indirect evidence that the secondary metabolites (which can be absorbed by AC) of the invasive plant S. canadensis may promote S. canadensis competitiveness by enhancing its own AMF symbionts.

  12. Comparative evaluation of two Trichoderma harzianum strains for major secondary metabolite production and antifungal activity.

    Science.gov (United States)

    Ahluwalia, Vivek; Kumar, Jitendra; Rana, Virendra S; Sati, Om P; Walia, S

    2015-01-01

    This investigation was undertaken to identify the major secondary metabolite, produced by two Trichoderma harzianum strains (T-4 and T-5) with their antifungal activity against phytopathogenic fungi using poison food technique. The ethyl acetate extract was subjected to column chromatography using n-hexane, ethyl acetate and methanol gradually. Chromatographic separation of ethyl acetate extract of T. harzianum (T-4) resulted in the isolation and identification of palmitic acid (1), 1,8-dihydroxy-3-methylanthraquinone (2), 6-pentyl-2H-pyran-2-one (3), 2(5H)-furanone (4), stigmasterol (5) and β-sitosterol (6), while T. harzianum (T-5) gave palmitic acid (1), 1-hydroxy-3-methylanthraquinone (7), δ-decanolactone (8), 6-pentyl-2H-pyran-2-one (3), ergosterol (9), harzianopyridone (10) and 6-methyl-1,3,8-trihydroxyanthraquinone (11) as major metabolites. Among compounds screened for antifungal activity, compound 10 was found to be most active (EC50 35.9-50.2 μg mL(-1)). In conclusion, the present investigation provided significant information about antifungal activity and compounds isolated from two different strains of T. harzianum obtained from two different Himalayan locations.

  13. Antioxidant potential of lichen species and their secondary metabolites. A systematic review.

    Science.gov (United States)

    Fernández-Moriano, Carlos; Gómez-Serranillos, María Pilar; Crespo, Ana

    2016-01-01

    Pharmacological interest of lichens lies in their capacity to produce bioactive secondary metabolites, being most of them phenolic compounds with reactive hydroxyl groups that confer antioxidant potential through various mechanisms. Increasing incidence and impact of oxidative stress-related diseases (i.e., neurodegenerative disorders) has encouraged the search of new pharmacological strategies to face them. Lichens appear to be a promising source of phenolic compounds in the discovery of natural products exerting antioxidant activity. The present review thoroughly discusses the available knowledge on antioxidant properties of lichens, including both in vitro and in vivo studies and the parameters assessed so far on lichen constituents. Literature survey was performed by using as main databases PubMed, Google Scholar, Scopus, Science Direct, and Recent Literature on Lichens. We reviewed 98 highlighted research articles without date restriction. Current report collects data related to antioxidant activities of more than 75 lichen species (from 18 botanical families) and 65 isolated metabolites. Much information comes from in vitro investigations, such as chemical assays evaluating radical scavenging properties, lipid peroxidation inhibition, and reducing power of lichen species and compounds; similarly, research on cellular substrates and animal models generally measures antioxidant enzymes levels and other antioxidant markers, such as glutathione levels or tissue peroxidation. Since consistent evidence demonstrated the contribution of oxidative stress on the development and progression of several human diseases, reviewed data suggest that some lichen compounds are worthy of further investigation and better understanding of their antioxidant and neuroprotective potentials.

  14. SECONDARY METABOLITE FROM ENDOPHYTIC FUNGI Aspergillus niger OF THE STEM BARK OF KANDIS GAJAH (Garcinia griffithii

    Directory of Open Access Journals (Sweden)

    Elfita Elfita

    2012-06-01

    Full Text Available Garcinia griffithii are known as kandis gajah including the Garcinia genus. This plant has been traditionally used by local communities Sarasah Bonta, Lembah Arau, West Sumatra, to treat various diseases including gout. Aspergillus niger was isolated from the tissues of the stem bark of Garcinia griffithii. The fungi strain was identified base on colony and cell morphology characteristic. Aspergillus niger cultured in media 5L Potatos Dextose Broth (PDB for 8 weeks and filtered. Media that already contains secondary metabolites are partitioned using ethyl acetate solvent in 5 L (twice, followed by evaporation. Furthermore, the extract is separated by chromatographic techniques to obtain a pure compound of white crystal. The molecular structures of isolated compounds are determined by spectroscopic methods including IR, 1H-NMR, 13C-NMR, HMQC, HMBC, and COSY. The compound was determined as phenolic (1.

  15. [Secondary metabolites from a deep-sea-derived actinomycete Micrococcus sp. R21].

    Science.gov (United States)

    Peng, Kun; Su, Rui-qiang; Zhang, Gai-yun; Cheng, Xuan-xuan; Yang, Quan; Liu, Yong-hong; Yang, Xian-wen

    2015-06-01

    To investigate cytotoxic secondary metabolites of Micrococcus sp. R21, an actinomycete isolated from a deep-sea sediment (-6 310 m; 142 degrees 19. 9' E, 10 degrees 54. 6' N) of the Western Pacific Ocean, column chromatography was introduced over silica gel, ODS, and Sephadex LH-20. As a result, eight compounds were obtained. By mainly detailed analysis of the NMR data, their structures were elucidated as cyclo(4-hydroxy-L-Pro-L-leu) (1), cyclo(L-Pro-L-Gly) (2), cyclo( L-Pro-L-Ala) (3), cyclo( D-Pro-L-Leu) (4), N-β-acetyltryptamine (5), 2-hydroxybenzoic acid (6), and phenylacetic acid (7). Compound 1 exhibited weak cytotoxic activity against RAW264. 7 cells with IC50 value of 9.1 μmol x L(-1).

  16. Secondary metabolites from Sida rhombifolia L. (Malvaceae) and the vasorelaxant activity of cryptolepinone.

    Science.gov (United States)

    Chaves, Otemberg Souza; Gomes, Roosevelt Albuquerque; Tomaz, Anna Cláudia de Andrade; Fernandes, Marianne Guedes; das Graças Mendes, Leônidas; de Fátima Agra, Maria; Braga, Valdir Andrade; de Fátima Vanderlei de Souza, Maria

    2013-03-01

    The phytochemical study of Sida rhombifolia L. (Malvaceae) led to the isolation through chromatographic techniques of eleven secondary metabolites: sitosterol (1a) and stigmasterol (1b), sitosterol-3-O-b-D-glucopyranoside (2a) and stigmasterol-3-O-b-D-glucopyranoside (2b), phaeophytin A (3), 17³-ethoxypheophorbide A (4), 13²-hydroxy phaeophytin B (5), 17³-ethoxypheophorbide B (6), 5,7-dihydroxy-4'-methoxyflavone (7), cryptolepinone (8) and a salt of cryptolepine (9). Their structures were identified by ¹H- and ¹³C-NMR using one- and two-dimensional techniques. In addition, the vasorelaxant activity of cryptolepinone in rat mesenteric artery rings is reported herein for the first time.

  17. Secondary Metabolites from Sida rhombifolia L. (Malvaceae and the Vasorelaxant Activity of Cryptolepinone

    Directory of Open Access Journals (Sweden)

    Maria de Fátima Vanderlei de Souza

    2013-03-01

    Full Text Available The phytochemical study of Sida rhombifolia L. (Malvaceae led to the isolation through chromatographic techniques of eleven secondary metabolites: sitosterol (1a and stigmasterol (1b, sitosterol-3-O-b-D-glucopyranoside (2a and stigmasterol-3-O-b-D-glucopyranoside (2b, phaeophytin A (3, 173-ethoxypheophorbide A (4, 132-hydroxy phaeophytin B (5, 173-ethoxypheophorbide B (6, 5,7-dihydroxy-4'-methoxyflavone (7, cryptolepinone (8 and a salt of cryptolepine (9. Their structures were identified by 1H- and 13C-NMR using one- and two-dimensional techniques. In addition, the vasorelaxant activity of cryptolepinone in rat mesenteric artery rings is reported herein for the first time.

  18. Therapeutic potential of secondary metabolites produced in the hairy roots cultures

    Directory of Open Access Journals (Sweden)

    Tomasz Kowalczyk

    2015-05-01

    Full Text Available Plants have always been a source of many valuable substances for humans. Growing advancement of methods of modern biotechnology, combined with genetic engineering techniques, gradually increase the variety of compounds obtained, the number of plant species used and the production efficiency. Consequently, there is an undebatable interest in biotechnological production of such compounds, especially those pharmacologically active, that can be used in treatment of neoplastic, viral, and many other types of diseases. Most of these compounds represent a diverse group of secondary metabolites. One of the effective ways of obtaining such molecules is the utilization of hairy roots cultures. The advantages of such systems make them an attractive method of obtaining important plant-derived compounds, creating an interesting alternative to other methods, including the cell suspension cultures or expensive chemical syntheses.

  19. Development of a yeast cell factory for production of aromatic secondary metabolites

    DEFF Research Database (Denmark)

    Rodriguez Prado, Edith Angelica

    Aromatic secondary metabolites are compounds mainly synthesized by plants and fungi as a response to predators and environmental stresses. These compounds have a broad range of natural properties such as reduction of oxidative damage in cells, antibacterial effects and UV protection. Many...... of these properties can be useful for the treatment of different diseases and development of pharmaceutical products. The low abundance of these compounds in natural sources together with technical challenges for the extraction of these compounds from plants, open up the possibility for synthesizing aromatic....... The systems biology analysis of the platform strain suggests that the strain has transcriptional downregulations in genes involved in the transport of amino acids and sugars, which could be a response to the stress triggered by the production of p-coumaric acid. The platform strain was capable of synthesizing...

  20. Secondary Metabolites from the Marine-Derived Fungus Dichotomomyces sp. L-8 and Their Cytotoxic Activity

    Directory of Open Access Journals (Sweden)

    Li-Hong Huang

    2017-03-01

    Full Text Available Bioassay-guided isolation of the secondary metabolites from the fungus Dichotomomyces sp. L-8 associated with the soft coral Lobophytum crassum led to the discovery of two new compounds, dichotones A and B (1 and 2, together with four known compounds including dichotocejpin C (3, bis-N-norgliovictin (4, bassiatin (5 and (3R,6R-bassiatin (6. The structures of these compounds were determined by 1D, 2D NMR and mass spectrometry. (3R,6R-bassiatin (6 displayed significant cytotoxic activities against the human breast cancer cell line MDA-MB-435 and the human lung cancer cell line Calu3 with IC50 values of 7.34 ± 0.20 and 14.54 ± 0.01 μM, respectively, while bassiatin (5, the diastereomer of compound 6, was not cytotoxic.

  1. Molecular and crystal structure of the antibiotic enniatin B, a secondary microbial metabolite

    International Nuclear Information System (INIS)

    Zhukhlistova, N.E.; Tishchenko, G.N.; Tolstykh, I.V.; Zenkova, V.A.

    1999-01-01

    Single crystals of the secondary microbial metabolite C 33 H 57 N 3 O 9 ·1(2/3)H 2 O with the known molecular weight were studied by the method of X-ray diffraction analysis, where a=b=15.102(3) A, c=14.548(3) A, sp. gr.R3, R=0.057. In the course of the structure determination, it was established that the substance is a natural antibiotic, namely, enniatin B. The conformation of its molecule is similar to that of the known synthetic antibiotic. The main difference between the natural and synthesized forms reduces to the different numbers of water molecules and their arrangement in the cavity of the antibiotic molecule

  2. Various extraction and analytical techniques for isolation and identification of secondary metabolites from Nigella sativa seeds.

    Science.gov (United States)

    Liu, X; Abd El-Aty, A M; Shim, J-H

    2011-10-01

    Nigella sativa L. (black cumin), commonly known as black seed, is a member of the Ranunculaceae family. This seed is used as a natural remedy in many Middle Eastern and Far Eastern countries. Extracts prepared from N. sativa have, for centuries, been used for medical purposes. Thus far, the organic compounds in N. sativa, including alkaloids, steroids, carbohydrates, flavonoids, fatty acids, etc. have been fairly well characterized. Herein, we summarize some new extraction techniques, including microwave assisted extraction (MAE) and supercritical extraction techniques (SFE), in addition to the classical method of hydrodistillation (HD), which have been employed for isolation and various analytical techniques used for the identification of secondary metabolites in black seed. We believe that some compounds contained in N. sativa remain to be identified, and that high-throughput screening could help to identify new compounds. A study addressing environmentally-friendly techniques that have minimal or no environmental effects is currently underway in our laboratory.

  3. An Overview of Herbal Products and Secondary Metabolites Used for Management of Type Two Diabetes.

    Science.gov (United States)

    Ota, Ajda; Ulrih, Nataša P

    2017-01-01

    Diabetes mellitus is a common effect of uncontrolled high blood sugar and it is associated with long-term damage, dysfunction, and failure of various organs. In the adult population, the global prevalence of diabetes has nearly doubled since 1980. Without effective prevention and management programs, the continuing significant rise in diabetes will have grave consequences on the health and lifespan of the world population, and also on the world economy. Supplements can be used to correct nutritional deficiencies or to maintain an adequate intake of certain nutrients. These are often used as treatments for diabetes, sometimes because they have lower costs, or are more accessible or "natural" compared to prescribed medications. Several vitamins, minerals, botanicals, and secondary metabolites have been reported to elicit beneficial effects in hypoglycemic actions in vivo and in vitro ; however, the data remain conflicting. Many pharmaceuticals commonly used today are structurally derived from natural compounds from traditional medicinal plants. Botanicals that are most frequently used to help manage blood glucose include: bitter melon ( Momordica charantia ), fenugreek ( Trigonella foenum graecum ), gurmar ( Gymnema sylvestre ), ivy gourd ( Coccinia indica ), nopal ( Opuntia spp.), ginseng, Russian tarragon ( Artemisia dracunculus ), cinnamon ( Cinnamomum cassia ), psyllium ( Plantago ovata ), and garlic ( Allium sativum ). In majority of the herbal products and secondary metabolites used in treating diabetes, the mechanisms of action involve regulation of insulin signaling pathways, translocation of GLUT-4 receptor and/or activation the PPARγ. Several flavonoids inhibit glucose absorption by inhibiting intestinal α-amylase and α-glucosidase. In-depth studies to validate the efficacies and safeties of extracts of these traditional medicinal plants are needed, and large, well designed, clinical studies need to be carried out before the use of such preparations can

  4. Antitumor activity of hierridin B, a cyanobacterial secondary metabolite found in both filamentous and unicellular marine strains.

    Directory of Open Access Journals (Sweden)

    Pedro N Leão

    Full Text Available Cyanobacteria are widely recognized as a valuable source of bioactive metabolites. The majority of such compounds have been isolated from so-called complex cyanobacteria, such as filamentous or colonial forms, which usually display a larger number of biosynthetic gene clusters in their genomes, when compared to free-living unicellular forms. Nevertheless, picocyanobacteria are also known to have potential to produce bioactive natural products. Here, we report the isolation of hierridin B from the marine picocyanobacterium Cyanobium sp. LEGE 06113. This compound had previously been isolated from the filamentous epiphytic cyanobacterium Phormidium ectocarpi SAG 60.90, and had been shown to possess antiplasmodial activity. A phylogenetic analysis of the 16S rRNA gene from both strains confirmed that these cyanobacteria derive from different evolutionary lineages. We further investigated the biological activity of hierridin B, and tested its cytotoxicity towards a panel of human cancer cell lines; it showed selective cytotoxicity towards HT-29 colon adenocarcinoma cells.

  5. Changes of main secondary metabolites in leaves of Ginkgo biloba in response to ozone fumigation

    Institute of Scientific and Technical Information of China (English)

    HE Xingyuan; HUANG Wei; CHEN Wei; DONG Tian; LIU Changbing; CHEN Zhenju; XU Sheng; RUAN Yanan

    2009-01-01

    To investigate the effect of elevated O3 on the accumulation of main secondary metabolites in leaves of Ginkgo biloba L., four-year-old trees were exposed in open-top chambers with ambient air and the air with twice ambient O3 concentration in Shenyang in 2006.Elevated O3 increased the concentrations of terpenes, but decreased the concentrations of phenolics in G.biloba leaves.The results showed that secondary compounds from G.biloba leaves responded to the elevated O3 exposure in a different way when compared to previous studies which showed elevated O3 increased the concentrations of phenolics but had no effect on the terpenes in leaves of other deciduous trees.Furthermore, reduced synthesis of phenolics may decrease the resistance of G.biloba to O3 and other environmental factors.On the other hand, the induced synthesis of terpenes may enhance the antioxidant abilities in G.biloba leaves at the end of O3 fumigation.

  6. Chemical transformations of characteristic hop secondary metabolites in relation to beer properties and the brewing process: a review.

    Science.gov (United States)

    Steenackers, Bart; De Cooman, Luc; De Vos, Dirk

    2015-04-01

    The annual production of hops (Humulus lupulus L.) exceeds 100,000 mt and is almost exclusively consumed by the brewing industry. The value of hops is attributed to their characteristic secondary metabolites; these metabolites are precursors which are transformed during the brewing process into important bittering, aromatising and preservative components with rather low efficiency. By selectively transforming these components off-line, both their utilisation efficiency and functionality can be significantly improved. Therefore, the chemical transformations of these secondary metabolites will be considered with special attention to recent advances in the field. The considered components are the hop alpha-acids, hop beta-acids and xanthohumol, which are components unique to hops, and alpha-humulene and beta-caryophyllene, sesquiterpenes which are highly characteristic of hops. Copyright © 2014 Elsevier Ltd. All rights reserved.

  7. Bacterial natural product biosynthetic domain composition in soil correlates with changes in latitude on a continent-wide scale.

    Science.gov (United States)

    Lemetre, Christophe; Maniko, Jeffrey; Charlop-Powers, Zachary; Sparrow, Ben; Lowe, Andrew J; Brady, Sean F

    2017-10-31

    Although bacterial bioactive metabolites have been one of the most prolific sources of lead structures for the development of small-molecule therapeutics, very little is known about the environmental factors associated with changes in secondary metabolism across natural environments. Large-scale sequencing of environmental microbiomes has the potential to shed light on the richness of bacterial biosynthetic diversity hidden in the environment, how it varies from one environment to the next, and what environmental factors correlate with changes in biosynthetic diversity. In this study, the sequencing of PCR amplicons generated using primers targeting either ketosynthase domains from polyketide biosynthesis or adenylation domains from nonribosomal peptide biosynthesis was used to assess biosynthetic domain composition and richness in soils collected across the Australian continent. Using environmental variables collected at each soil site, we looked for environmental factors that correlated with either high overall domain richness or changes in the domain composition. Among the environmental variables we measured, changes in biosynthetic domain composition correlate most closely with changes in latitude and to a lesser extent changes in pH. Although it is unclear at this time the exact mix of factors that may drive the relationship between biosynthetic domain composition and latitude, from a practical perspective the identification of a latitudinal basis for differences in soil metagenome biosynthetic domain compositions should help guide future natural product discovery efforts. Published under the PNAS license.

  8. Growth and Accumulation of Secondary Metabolites in Perilla as Affected by Photosynthetic Photon Flux Density and Electrical Conductivity of the Nutrient Solution

    Directory of Open Access Journals (Sweden)

    Na Lu

    2017-05-01

    Full Text Available The global demand for medicinal plants is increasing. The quality of plants grown outdoors, however, is difficult to control. Myriad environmental factors influence plant growth and directly impact biosynthetic pathways, thus affecting the secondary metabolism of bioactive compounds. Plant factories use artificial lighting to increase the quality of medicinal plants and stabilize production. Photosynthetic photon flux density (PPFD and electrical conductivity (EC of nutrient solutions are two important factors that substantially influence perilla (Perilla frutescens, Labiatae plant growth and quality. To identify suitable levels of PPFD and EC for perilla plants grown in a plant factory, the growth, photosynthesis, and accumulation of secondary metabolites in red and green perilla plants were measured at PPFD values of 100, 200, and 300 μmol m-2 s-1 in nutrient solutions with EC values of 1.0, 2.0, and 3.0 dS m-1. The results showed significant interactive effects between PPFD and EC for both the fresh and dry weights of green perilla, but not for red perilla. The fresh and dry weights of shoots and leafy areas were affected more by EC than by PPFD in green perilla, whereas they were affected more by PPFD than by EC in red perilla. Leaf net photosynthetic rates were increased as PPFD increased in both perilla varieties, regardless of EC. The perillaldehyde concentration (mg g-1 in red perilla was unaffected by the treatments, but accumulation in plants (mg per plant was significantly enhanced as the weight of dry leaves increased. Perillaldehyde concentrations in green perilla showed significant differences between combinations of the highest PPFD with the highest EC and the lowest PPFD with the lowest EC. Rosmarinic acid concentration (mg g-1 was increased in a combination of low EC and high PPFD conditions. Optimal cultivation conditions of red and green perilla in plant factory will be discussed in terms of plant growth and contents of

  9. Insights into the mechanisms of Promysalin, a secondary metabolite with genus-specific antibacterial activity against Pseudomonas

    Science.gov (United States)

    Promysalin, a secondary metabolite produced by Pseudomonas putida RW10S1, has antibacterial activity against a wide variety of Pseudomonas sp., including both human and plant pathogens. Promysalin induces swarming and biofilm formation in the producing species, and inhibits growth of susceptible sp...

  10. Impact of metal stress on the production of secondary metabolites in Pteris vittata L. and associated rhizosphere bacterial communities.

    Science.gov (United States)

    Pham, Hoang Nam; Michalet, Serge; Bodillis, Josselin; Nguyen, Tien Dat; Nguyen, Thi Kieu Oanh; Le, Thi Phuong Quynh; Haddad, Mohamed; Nazaret, Sylvie; Dijoux-Franca, Marie-Geneviève

    2017-07-01

    Plants adapt to metal stress by modifying their metabolism including the production of secondary metabolites in plant tissues. Such changes may impact the diversity and functions of plant associated microbial communities. Our study aimed to evaluate the influence of metals on the secondary metabolism of plants and the indirect impact on rhizosphere bacterial communities. We then compared the secondary metabolites of the hyperaccumulator Pteris vittata L. collected from a contaminated mining site to a non-contaminated site in Vietnam and identified the discriminant metabolites. Our data showed a significant increase in chlorogenic acid derivatives and A-type procyanidin in plant roots at the contaminated site. We hypothesized that the intensive production of these compounds could be part of the antioxidant defense mechanism in response to metals. In parallel, the structure and diversity of bulk soil and rhizosphere communities was studied using high-throughput sequencing. The results showed strong differences in bacterial composition, characterized by the dominance of Proteobacteria and Nitrospira in the contaminated bulk soil, and the enrichment of some potential human pathogens, i.e., Acinetobacter, Mycobacterium, and Cupriavidus in P. vittata's rhizosphere at the mining site. Overall, metal pollution modified the production of P. vittata secondary metabolites and altered the diversity and structure of bacterial communities. Further investigations are needed to understand whether the plant recruits specific bacteria to adapt to metal stress.

  11. A comparative study of conventional and supercritical fluid extraction methods for the recovery of secondary metabolites from Syzygium campanulatum Korth#

    Science.gov (United States)

    Memon, Abdul Hakeem; Hamil, Mohammad Shahrul Ridzuan; Laghari, Madeeha; Rithwan, Fahim; Zhari, Salman; Saeed, Mohammed Ali Ahmed; Ismail, Zhari; Majid, Amin Malik Shah Abdul

    2016-01-01

    Syzygium campanulatum Korth is a plant, which is a rich source of secondary metabolites (especially flavanones, chalcone, and triterpenoids). In our present study, three conventional solvent extraction (CSE) techniques and supercritical fluid extraction (SFE) techniques were performed to achieve a maximum recovery of two flavanones, chalcone, and two triterpenoids from S. campanulatum leaves. Furthermore, a Box-Behnken design was constructed for the SFE technique using pressure, temperature, and particle size as independent variables, and yields of crude extract, individual and total secondary metabolites as the dependent variables. In the CSE procedure, twenty extracts were produced using ten different solvents and three techniques (maceration, soxhletion, and reflux). An enriched extract of five secondary metabolites was collected using n-hexane:methanol (1:1) soxhletion. Using food-grade ethanol as a modifier, the SFE methods produced a higher recovery (25.5%‒84.9%) of selected secondary metabolites as compared to the CSE techniques (0.92%‒66.00%). PMID:27604860

  12. A comparative study of conventional and supercritical fluid extraction methods for the recovery of secondary metabolites from Syzygium campanulatum Korth.

    Science.gov (United States)

    Memon, Abdul Hakeem; Hamil, Mohammad Shahrul Ridzuan; Laghari, Madeeha; Rithwan, Fahim; Zhari, Salman; Saeed, Mohammed Ali Ahmed; Ismail, Zhari; Majid, Amin Malik Shah Abdul

    2016-09-01

    Syzygium campanulatum Korth is a plant, which is a rich source of secondary metabolites (especially flavanones, chalcone, and triterpenoids). In our present study, three conventional solvent extraction (CSE) techniques and supercritical fluid extraction (SFE) techniques were performed to achieve a maximum recovery of two flavanones, chalcone, and two triterpenoids from S. campanulatum leaves. Furthermore, a Box-Behnken design was constructed for the SFE technique using pressure, temperature, and particle size as independent variables, and yields of crude extract, individual and total secondary metabolites as the dependent variables. In the CSE procedure, twenty extracts were produced using ten different solvents and three techniques (maceration, soxhletion, and reflux). An enriched extract of five secondary metabolites was collected using n-hexane:methanol (1:1) soxhletion. Using food-grade ethanol as a modifier, the SFE methods produced a higher recovery (25.5%‒84.9%) of selected secondary metabolites as compared to the CSE techniques (0.92%‒66.00%).

  13. Nutrient and secondary metabolite concentrations in a savanna are independently affected by large herbivores and shoot growth rate

    CSIR Research Space (South Africa)

    Scogings, PF

    2014-01-01

    Full Text Available Carbon-based secondary metabolites (CBSMs) such as tannins are assumed to function as plant defences against herbivores. CBSMs are thought to be inversely related to growth rate and nutrient concentrations because a physiological trade-off exists...

  14. Transcriptome of Aspergillus flavus aswA (AFLA_085170) deletion strain related to sclerotial development and production of secondary metabolites

    Science.gov (United States)

    Aspergillus flavus produces many secondary metabolites including aflatoxins. Besides conidia, the fungus uses sclerotia as another type of propagule. We obtained transcriptomes from four growth conditions of the aswA mutant, a strain impaired in sclerotial development and production of sclerotium-sp...

  15. Antioxidant Secondary Metabolites in Cereals: Potential Involvement in Resistance to Fusarium and Mycotoxin Accumulation

    Directory of Open Access Journals (Sweden)

    Vessela eATANASOVA-PENICHON

    2016-04-01

    Full Text Available Gibberella and Fusarium Ear Rot and Fusarium Head Blight are major diseases affecting European cereals. These diseases are mainly caused by fungi of the Fusarium genus, primarily Fusarium graminearum and Fusarium verticillioides. These Fusarium species pose a serious threat to food safety because of their ability to produce a wide range of mycotoxins, including type B trichothecenes and fumonisins. Many factors such as environmental, agronomic or genetic ones may contribute to high levels of accumulation of mycotoxins in the grain and there is an urgent need to implement efficient and sustainable management strategies to reduce mycotoxin contamination. Actually, fungicides are not fully efficient to control the mycotoxin risk. In addition, because of harmful effects on human health and environment, their use should be seriously restricted in the near future. To durably solve the problem of mycotoxin accumulation, the breeding of tolerant genotypes is one of the most promising strategies for cereals. A deeper understanding of the molecular mechanisms of plant resistance to both Fusarium and mycotoxin contamination will shed light on plant-pathogen interactions and provide relevant information for improving breeding programs. Resistance to Fusarium depends on the plant ability in preventing initial infection and containing the development of the toxigenic fungi while resistance to mycotoxin contamination is also related to the capacity of plant tissues in reducing mycotoxin accumulation. This capacity can result from two mechanisms: metabolic transformation of the toxin into less toxic compounds and inhibition of toxin biosynthesis. This last mechanism involves host metabolites able to interfere with mycotoxin biosynthesis. This review aims at gathering the latest scientific advances that support the contribution of grain antioxidant secondary metabolites to the mechanisms of plant resistance to Fusarium and mycotoxin accumulation.

  16. Cultivar and Year Rather than Agricultural Practices Affect Primary and Secondary Metabolites in Apple Fruit

    Science.gov (United States)

    Renard, Catherine M. G. C.; Plenet, Daniel; Gautier, Hélène; Touloumet, Line; Girard, Thierry; Simon, Sylvaine

    2015-01-01

    Many biotic and abiotic parameters affect the metabolites involved in the organoleptic and health value of fruits. It is therefore important to understand how the growers' decisions for cultivar and orchard management can affect the fruit composition. Practices, cultivars and/or year all might participate to determine fruit composition. To hierarchize these factors, fruit weight, dry matter, soluble solids contents, titratable acidity, individual sugars and organics acids, and phenolics were measured in three apple cultivars (‘Ariane’, ‘Melrose’ and ‘Smoothee’) managed under organic, low-input and conventional management. Apples were harvested at commercial maturity in the orchards of the cropping system experiment BioREco at INRA Gotheron (Drôme, 26) over the course of three years (2011, 2012 and 2013). The main factors affecting primary and secondary metabolites, in both apple skin and flesh, were by far the cultivar and the yearly conditions, while the management system had a very limited effect. When considering the three cultivars and the year 2011 to investigate the effect of the management system per se, only few compounds differed significantly between the three systems and in particular the total phenolic content did not differ significantly between systems. Finally, when considering orchards grown in the same pedoclimatic conditions and of the same age, instead of the usual organic vs. conventional comparison, the effect of the management system on the apple fruit quality (Fruit weight, dry matter, soluble solids content, titratable acidity, individual sugars, organic acids, and phenolics) was very limited to non-significant. The main factors of variation were the cultivar and the year of cropping rather than the cropping system. More generally, as each management system (e.g. conventional, organic…) encompasses a great variability of practices, this highlights the importance of accurately documenting orchard practices and design beside the

  17. Cultivar and Year Rather than Agricultural Practices Affect Primary and Secondary Metabolites in Apple Fruit.

    Directory of Open Access Journals (Sweden)

    Carine Le Bourvellec

    Full Text Available Many biotic and abiotic parameters affect the metabolites involved in the organoleptic and health value of fruits. It is therefore important to understand how the growers' decisions for cultivar and orchard management can affect the fruit composition. Practices, cultivars and/or year all might participate to determine fruit composition. To hierarchize these factors, fruit weight, dry matter, soluble solids contents, titratable acidity, individual sugars and organics acids, and phenolics were measured in three apple cultivars ('Ariane', 'Melrose' and 'Smoothee' managed under organic, low-input and conventional management. Apples were harvested at commercial maturity in the orchards of the cropping system experiment BioREco at INRA Gotheron (Drôme, 26 over the course of three years (2011, 2012 and 2013. The main factors affecting primary and secondary metabolites, in both apple skin and flesh, were by far the cultivar and the yearly conditions, while the management system had a very limited effect. When considering the three cultivars and the year 2011 to investigate the effect of the management system per se, only few compounds differed significantly between the three systems and in particular the total phenolic content did not differ significantly between systems. Finally, when considering orchards grown in the same pedoclimatic conditions and of the same age, instead of the usual organic vs. conventional comparison, the effect of the management system on the apple fruit quality (Fruit weight, dry matter, soluble solids content, titratable acidity, individual sugars, organic acids, and phenolics was very limited to non-significant. The main factors of variation were the cultivar and the year of cropping rather than the cropping system. More generally, as each management system (e.g. conventional, organic… encompasses a great variability of practices, this highlights the importance of accurately documenting orchard practices and design beside

  18. Antibacterial Secondary Metabolites from the Cave Sponge Xestospongia sp.

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    Sridevi Ankisetty

    2012-05-01

    Full Text Available Chemical investigation of the cave sponge Xestospongia sp. resulted in the isolation of three new polyacetylenic long chain compounds along with two known metabolites. The structures of the new metabolites were established by NMR and MS analyses. The antibacterial activity of the new metabolites was also evaluated.

  19. An Overview of Herbal Products and Secondary Metabolites Used for Management of Type Two Diabetes

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    Ajda Ota

    2017-07-01

    Full Text Available Diabetes mellitus is a common effect of uncontrolled high blood sugar and it is associated with long-term damage, dysfunction, and failure of various organs. In the adult population, the global prevalence of diabetes has nearly doubled since 1980. Without effective prevention and management programs, the continuing significant rise in diabetes will have grave consequences on the health and lifespan of the world population, and also on the world economy. Supplements can be used to correct nutritional deficiencies or to maintain an adequate intake of certain nutrients. These are often used as treatments for diabetes, sometimes because they have lower costs, or are more accessible or “natural” compared to prescribed medications. Several vitamins, minerals, botanicals, and secondary metabolites have been reported to elicit beneficial effects in hypoglycemic actions in vivo and in vitro; however, the data remain conflicting. Many pharmaceuticals commonly used today are structurally derived from natural compounds from traditional medicinal plants. Botanicals that are most frequently used to help manage blood glucose include: bitter melon (Momordica charantia, fenugreek (Trigonella foenum graecum, gurmar (Gymnema sylvestre, ivy gourd (Coccinia indica, nopal (Opuntia spp., ginseng, Russian tarragon (Artemisia dracunculus, cinnamon (Cinnamomum cassia, psyllium (Plantago ovata, and garlic (Allium sativum. In majority of the herbal products and secondary metabolites used in treating diabetes, the mechanisms of action involve regulation of insulin signaling pathways, translocation of GLUT-4 receptor and/or activation the PPARγ. Several flavonoids inhibit glucose absorption by inhibiting intestinal α-amylase and α-glucosidase. In-depth studies to validate the efficacies and safeties of extracts of these traditional medicinal plants are needed, and large, well designed, clinical studies need to be carried out before the use of such preparations can be

  20. Effects of Plant Secondary Metabolites on Methane Production and Fermentation Parameters in In vitro Ruminal Cultures

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    Mihaela Giuburunca

    2014-10-01

    Full Text Available Enteric fermentation process is of concern worldwide for its contribution to global warming. It is known that ruminant animals, due to natural fermentation process contribute substantially to the increase in methane production. Methanogenesis process represents besides its contribution to greenhouse gases emissions an energy loss to the animal. To reduce ruminal methane productions in an ecologically and sustainable way, many attempts have been initiated, such as: uses of chemicals additives or ionophore antibiotics, defaunation process or immunization against ruminal methanogenesis. In the last years, a new strategy has been evaluated whether plant secondary metabolites can be used as natural additives to reduce ruminal methane emissions. The present study has been conducted to investigate the effects of trans-cinnamic, caffeic, p-coumaric acids and catechin hydrate, four plant secondary metabolites (PSMs on methane production and fermentation in in vitro ruminal cultures. The four PSMs were added anaerobically in a 6 mM concentration to 100 ml serum bottles containing 500 mg grass hay as a substrate, 10 ml rumen fluid collected from a fistulated sheep before morning feeding and 40 ml 141 DSM culture medium. The bottles were incubated at 39 ̊C. After 24 h, the following variables were measured: total gas volume, pH, methane and volatile fatty acids (VFAs production. The results showed that caffeic (p = 0.058 and p-coumaric (p = 0.052 acids tended to decrease methane production in comparison to control but the decrease was not statistic significantly at α= 0.05. The other two PSMs had no significant effect on methane production. Addition of PSMs did not affected the total gas volume, the pH and VFAs profile (P>0.05 in relation to the control (no PSM added. In conclusion, caffeic and p-coumaric acids in 6 mM concentration showed some promising effects for decreasing ruminal methane emissions without affecting ruminal fermentation parameters but

  1. Dung-inhabiting fungi: a potential reservoir of novel secondary metabolites for the control of plant pathogens.

    Science.gov (United States)

    Sarrocco, Sabrina

    2016-04-01

    Coprophilous fungi are a large group of saprotrophic fungi mostly found in herbivore dung. The number of these fungi undergoing investigation is continually increasing, and new species and genera continue to be described. Dung-inhabiting fungi play an important ecological role in decomposing and recycling nutrients from animal dung. They produce a large array of bioactive secondary metabolites and have a potent enzymatic arsenal able to utilise even complex molecules. Bioactive secondary metabolites are actively involved in interaction with and defence against other organisms whose growth can be inhibited, resulting in an enhanced ecological fitness of producer strains. Currently, these antibiotics and bioactive secondary metabolites are of interest in medicine in particular, while very little information is available concerning their potential use in agriculture. This review introduces the ecology of dung-inhabiting fungi, with particular emphasis on the production of antibiotic compounds as a means to compete with other microorganisms. Owing to the fast pace of technological progress, new approaches to predicting the biosynthesis of bioactive metabolites are proposed. Coprophilous fungi should be considered as elite candidate organisms for the discovery of novel antifungal compounds, above all in view of their exploitation for crop protection. © 2015 Society of Chemical Industry.

  2. Profiling of secondary metabolite gene clusters regulated by LaeA in Aspergillus niger FGSC A1279 based on genome sequencing and transcriptome analysis.

    Science.gov (United States)

    Wang, Bin; Lv, Yangyong; Li, Xuejie; Lin, Yiying; Deng, Hai; Pan, Li

    The global regulator LaeA controls the production of many fungal secondary metabolites, possibly via chromatin remodeling. Here we aimed to survey the secondary metabolite profile regulated by LaeA in Aspergillus niger FGSC A1279 by genome sequencing and comparative transcriptomics between the laeA deletion (ΔlaeA) and overexpressing (OE-laeA) mutants. Genome sequencing revealed four putative polyketide synthase genes specific to FGSC A1279, suggesting that the corresponding polyketide compounds might be unique to FGSC A1279. RNA-seq data revealed 281 putative secondary metabolite genes upregulated in the OE-laeA mutants, including 22 secondary metabolite backbone genes. LC-MS chemical profiling illustrated that many secondary metabolites were produced in OE-laeA mutants compared to wild type and ΔlaeA mutants, providing potential resources for drug discovery. KEGG analysis annotated 16 secondary metabolite clusters putatively linked to metabolic pathways. Furthermore, 34 of 61 Zn 2 Cys 6 transcription factors located in secondary metabolite clusters were differentially expressed between ΔlaeA and OE-laeA mutants. Three secondary metabolite clusters (cluster 18, 30 and 33) containing Zn 2 Cys 6 transcription factors that were upregulated in OE-laeA mutants were putatively linked to KEGG pathways, suggesting that Zn 2 Cys 6 transcription factors might play an important role in synthesizing secondary metabolites regulated by LaeA. Taken together, LaeA dramatically influences the secondary metabolite profile in FGSC A1279. Copyright © 2017 Institut Pasteur. Published by Elsevier Masson SAS. All rights reserved.

  3. Jasmonate-responsive transcription factors regulating plant secondary metabolism.

    Science.gov (United States)

    Zhou, Meiliang; Memelink, Johan

    2016-01-01

    Plants produce a large variety of secondary metabolites including alkaloids, glucosinolates, terpenoids and phenylpropanoids. These compounds play key roles in plant-environment interactions and many of them have pharmacological activity in humans. Jasmonates (JAs) are plant hormones which induce biosynthesis of many secondary metabolites. JAs-responsive transcription factors (TFs) that regulate the JAs-induced accumulation of secondary metabolites belong to different families including AP2/ERF, bHLH, MYB and WRKY. Here, we give an overview of the types and functions of TFs that have been identified in JAs-induced secondary metabolite biosynthesis, and highlight their similarities and differences in regulating various biosynthetic pathways. We review major recent developments regarding JAs-responsive TFs mediating secondary metabolite biosynthesis, and provide suggestions for further studies. Copyright © 2016 Elsevier Inc. All rights reserved.

  4. Plant protein and secondary metabolites influence diet selection in a mammalian specialist herbivore

    Science.gov (United States)

    Ulappa, Amy C.; Kelsey, Rick G.; Frye, Graham G.; Rachlow, Janet L.; Shipley, Lisa A.; Bond, Laura; Pu, Xinzhu; Forbey, Jennifer Sorensen

    2015-01-01

    For herbivores, nutrient intake is limited by the relatively low nutritional quality of plants and high concentrations of potentially toxic defensive compounds (plant secondary metabolites, PSMs) produced by many plants. In response to phytochemical challenges, some herbivores selectively forage on plants with higher nutrient and lower PSM concentrations relative to other plants. Pygmy rabbits (Brachylagus idahoensis) are dietary specialists that feed on sagebrush (Artemisia spp.) and forage on specific plants more than others within a foraging patch. We predicted that the plants with evidence of heavy foraging (browsed plants) would be of higher dietary quality than plants that were not browsed (unbrowsed). We used model selection to determine which phytochemical variables best explained the difference between browsed and unbrowsed plants. Higher crude protein increased the odds that plants would be browsed by pygmy rabbits and the opposite was the case for certain PSMs. Additionally, because pygmy rabbits can occupy foraging patches (burrows) for consecutive years, their browsing may influence the nutritional and PSM constituents of plants at the burrows. In a post hoc analysis, we did not find a significant relationship between phytochemical concentrations, browse status and burrow occupancy length. We concluded that pygmy rabbits use nutritional and chemical cues while making foraging decisions. PMID:26366011

  5. Microbial communication leading to the activation of silent fungal secondary metabolite gene clusters

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    Tina eNetzker

    2015-04-01

    Full Text Available Microorganisms form diverse multispecies communities in various ecosystems. The high abundance of fungal and bacterial species in these consortia results in specific communication between the microorganisms. A key role in this communication is played by secondary metabolites (SMs, which are also called natural products. Recently, it was shown that interspecies ‘talk’ between microorganisms represents a physiological trigger to activate silent gene clusters leading to the formation of novel SMs by the involved species. This review focuses on mixed microbial cultivation, mainly between bacteria and fungi, with a special emphasis on the induced formation of fungal SMs in co-cultures. In addition, the role of chromatin remodeling in the induction is examined, and methodical perspectives for the analysis of natural products are presented. As an example for an intermicrobial interaction elucidated at the molecular level, we discuss the specific interaction between the filamentous fungi Aspergillus nidulans and Aspergillus fumigatus with the soil bacterium Streptomyces rapamycinicus, which provides an excellent model system to enlighten molecular concepts behind regulatory mechanisms and will pave the way to a novel avenue of drug discovery through targeted activation of silent SM gene clusters through co-cultivations of microorganisms.

  6. Old meets new: using interspecies interactions to detect secondary metabolite production in actinomycetes.

    Science.gov (United States)

    Seyedsayamdost, Mohammad R; Traxler, Matthew F; Clardy, Jon; Kolter, Roberto

    2012-01-01

    Actinomycetes, a group of filamentous, Gram-positive bacteria, have long been a remarkable source of useful therapeutics. Recent genome sequencing and transcriptomic studies have shown that these bacteria, responsible for half of the clinically used antibiotics, also harbor a large reservoir of gene clusters, which have the potential to produce novel secreted small molecules. Yet, many of these clusters are not expressed under common culture conditions. One reason why these clusters have not been linked to a secreted small molecule lies in the way that actinomycetes have typically been studied: as pure cultures in nutrient-rich media that do not mimic the complex environments in which these bacteria evolved. New methods based on multispecies culture conditions provide an alternative approach to investigating the products of these gene clusters. We have recently implemented binary interspecies interaction assays to mine for new secondary metabolites and to study the underlying biology of interactinomycete interactions. Here, we describe the detailed biological and chemical methods comprising these studies. Copyright © 2012 Elsevier Inc. All rights reserved.

  7. Secondary metabolite from Nostoc XPORK14A inhibits photosynthesis and growth of Synechocystis PCC 6803.

    Science.gov (United States)

    Shunmugam, Sumathy; Jokela, Jouni; Wahlsten, Matti; Battchikova, Natalia; Ateeq ur Rehman; Vass, Imre; Karonen, Maarit; Sinkkonen, Jari; Permi, Perttu; Sivonen, Kaarina; Aro, Eva-Mari; Allahverdiyeva, Yagut

    2014-06-01

    Screening of 55 different cyanobacterial strains revealed that an extract from Nostoc XPORK14A drastically modifies the amplitude and kinetics of chlorophyll a fluorescence induction of Synechocystis PCC6803 cells.After 2 d exposure to the Nostoc XPORK14A extract, Synechocystis PCC 6803 cells displayed reduced net photosynthetic activity and significantly modified electron transport properties of photosystem II under both light and dark conditions. However, the maximum oxidizable amount of P700 was not strongly affected. The extract also induced strong oxidative stress in Synechocystis PCC 6803 cells in both light and darkness. We identified the secondary metabolite of Nostoc XPORK14A causing these pronounced effects on Synechocystis cells. Mass spectrometry and nuclear magnetic resonance analyses revealed that this compound, designated as M22, has a non-peptide structure. We propose that M22 possesses a dualaction mechanism: firstly, by photogeneration of reactive oxygen species in the presence of light, which in turn affects the photosynthetic machinery of Synechocystis PCC 6803; and secondly, by altering the in vivo redox status of cells, possibly through inhibition of protein kinases.

  8. Antiproliferative, Antibacterial and Antifungal Activity of the Lichen Xanthoria parietina and Its Secondary Metabolite Parietin

    Directory of Open Access Journals (Sweden)

    Adriana Basile

    2015-04-01

    Full Text Available Lichens are valuable natural resources used for centuries throughout the world as medicine, food, fodder, perfume, spices and dyes, as well as for other miscellaneous purposes. This study investigates the antiproliferative, antibacterial and antifungal activity of the acetone extract of the lichen Xanthoria parietina (Linnaeus Theodor Fries and its major secondary metabolite, parietin. The extract and parietin were tested for antimicrobial activity against nine American Type Culture Collection standard and clinically isolated bacterial strains, and three fungal strains. Both showed strong antibacterial activity against all bacterial strains and matched clinical isolates, particularly against Staphylococcus aureus from standard and clinical sources. Among the fungi tested, Rhizoctonia solani was the most sensitive. The antiproliferative effects of the extract and parietin were also investigated in human breast cancer cells. The extract inhibited proliferation and induced apoptosis, both effects being accompanied by modulation of expression of cell cycle regulating genes such as p16, p27, cyclin D1 and cyclin A. It also mediated apoptosis by activating extrinsic and intrinsic cell death pathways, modulating Tumor Necrosis Factor-related apoptosis-inducing ligand (TRAIL and B-cell lymphoma 2 (Bcl-2, and inducing Bcl-2-associated agonist of cell death (BAD phosphorylation. Our results indicate that Xanthoria parietina is a major potential source of antimicrobial and anticancer substances.

  9. [Study on secondary metabolites of marine fungus Penicillium sp. FS60 from the South China Sea].

    Science.gov (United States)

    Zhang, Ling; Li, Dong-Li; Chen, Yu-Chan; Tao, Mei-Hua; Zhang, Wei-Min

    2012-07-01

    To study the secondary metabolites of the marine fungus Penicillium sp. FS60 from the South China Sea and their cytotoxicities. The compounds were isolated from the culture of strain FS60 by various chromatographic methods (silica gel, reverse silica gel, Sephadex-LH20, preparative TLC, HPLC and PTLC) and recrystallization. Their structures were identified by extensive analysis of their spectroscopic data. Compounds were tested for their cytotoxicities against SF-268, MCF-7, and NCI-H460 cell lines by SRB method. While, Compounds were tested for their antibacterial activities against S. aureus, E. coli and P. aeruginosa. Seven compounds were isolated from the culture and identified as methyl 2,4-dihydroxy-3,5,6-trimethylbenzoate (1), 4-hydroxyacetophenone (2), 5-hydroxymethyl-furoic acid (3), isochromophilones VIII (4), ergosterol (5), ergosterol peroxide (6), and cerevisterol (7). Compound 1 is isolated from the genus Penicillium for the first time. Compound 3 is demonstrated to have significant inhibition against S. aureus and P. aeruginosa. Compound 4 is demonstrated to have significant inhibition against the three cell lines.

  10. Secondary metabolites of Mirabilis jalapa structurally inhibit Lactate Dehydrogenase A in silico: a potential cancer treatment

    Science.gov (United States)

    Kusumawati, R.; Nasrullah, A. H.; Pesik, R. N.; Muthmainah; Indarto, D.

    2018-03-01

    Altered energy metabolism from phosphorylated oxidation to aerobic glycolysis is one of the cancer hallmarks. Lactate dehydrogenase A (LDHA) is a major enzyme that catalyses pyruvate to lactate in such condition. The aim of this study was to explore LDHA inhibitors derived from Indonesian herbal plants. In this study, LDHA and oxamate molecular structures were obtained from protein data bank. As a standard ligand inhibitor, oxamate was molecularly re-validated using Autodock Vina 1.1.2 software and showed binding energy -4.26 ± 0.006 kcal/mol and interacted with LDHA at Gln99, Arg105, Asn137, Arg168, His192, and Thr247 residues. Molecular docking was used to visualize interaction between Indonesian phytochemicals and LDHA. Indonesian phytochemicals with the lowest binding energy and similar residues with standard ligand was Miraxanthin-III (-8.53 ± 0.006 kcal/mol), Vulgaxanthin-I (-8.46 ± 0.006 kcal/mol), Miraxanthin-II (-7.9 ± 0.2 kcal/mol) and Miraxanthin-V (-7.96 ± kcal/mol). Lower energy binding to LDHA and binding site at these residues was predicted to inhibit LDHA activity better than standard ligand. All phytochemicals were found in Mirabilis jalapa plant. Secondary metabolites in Mirabilis jalapa have LDHA inhibitor property in silico. Further in vitro study should be performed to confirm this result.

  11. Yellow-Cedar, Callitropsis (Chamaecyparis) nootkatensis, Secondary Metabolites, Biological Activities, and Chemical Ecology.

    Science.gov (United States)

    Karchesy, Joseph J; Kelsey, Rick G; González-Hernández, M P

    2018-05-01

    Yellow-cedar, Callitropsis nootkatensis, is prevalent in coastal forests of southeast Alaska, western Canada, and inland forests along the Cascades to northern California, USA. These trees have few microbial or animal pests, attributable in part to the distinct groups of biologically active secondary metabolites their tissues store for chemical defense. Here we summarize the new yellow-cedar compounds identified and their biological activities, plus new or expanded activities for tissues, extracts, essential oils and previously known compounds since the last review more than 40 years ago. Monoterpene hydrocarbons are the most abundant compounds in foliage, while heartwood contains substantial quantities of oxygenated monoterpenes and oxygenated sesquiterpenes, with one or more tropolones. Diterpenes occur in foliage and bark, whereas condensed tannins have been isolated from inner bark. Biological activities expressed by one or more compounds in these groups include fungicide, bactericide, sporicide, acaricide, insecticide, general cytotoxicity, antioxidant and human anticancer. The diversity of organisms impacted by whole tissues, essential oils, extracts, or individual compounds now encompasses ticks, fleas, termites, ants, mosquitoes, bacteria, a water mold, fungi and browsing animals. Nootkatone, is a heartwood component with sufficient activity against arthropods to warrant research focused toward potential development as a commercial repellent and biopesticide for ticks, mosquitoes and possibly other arthropods that vector human and animal pathogens.

  12. Salicornia ramosissima: Secondary metabolites and protective effect against acute testicular toxicity

    Directory of Open Access Journals (Sweden)

    Daniela Ferreira

    2018-01-01

    Full Text Available Salicornia ramosissima J. Woods is a salt tolerant plant currently used in the human diet, whose genus not only displays great potential as a crop plant in deserts and highly saline soils, but also has value in traditional medicine and exhibits promising biological activities. The present study was designed to evaluate the effect of S. ramosissima ethanolic extract on carbon tetrachloride (CCl4-induced testicular damage in a mouse model and identify secondary metabolites present in the tested extract. The histopathological analysis showed that the treatment with the ethanolic extract prior to CCl4 administration prevented significantly the architectural disorder of seminiferous epithelium and germ cell exfoliation. The phytochemical study allowed the identification of known phenolic and aliphatic compounds [ethyl linolenoate (1, sitostanol (2, octadecyl (3 and eicosanyl (4 (E-ferulates, ethyl (E-2-hydroxycinnamate (5, scopoletin (6, a triacylglycerol of tetracosanoic acid (7], and three new compounds: saliramoester, a long chain triester (8, saliramophenone, a propiophenone derivative (9 and saliramopyrrole a pyrrole-3-carbaldehyde derivative (10. Their chemical structures were elucidated using detailed spectroscopic studies (1D and 2D NMR and MS. These results enhance the value of S. ramosissima as an excellent source of structurally interesting phytochemicals and as protective agent against testicular toxicity.

  13. Enzyme-linked immunosorbent assay for the quantitative/qualitative analysis of plant secondary metabolites.

    Science.gov (United States)

    Sakamoto, Seiichi; Putalun, Waraporn; Vimolmangkang, Sornkanok; Phoolcharoen, Waranyoo; Shoyama, Yukihiro; Tanaka, Hiroyuki; Morimoto, Satoshi

    2018-01-01

    Immunoassays are antibody-based analytical methods for quantitative/qualitative analysis. Since the principle of immunoassays is based on specific antigen-antibody reaction, the assays have been utilized worldwide for diagnosis, pharmacokinetic studies by drug monitoring, and the quality control of commercially available products. Berson and Yalow were the first to develop an immunoassay, known as radioimmunoassay (RIA), for detecting endogenous plasma insulin [1], a development for which Yalow was awarded the Nobel Prize in Physiology or Medicine in 1977. Even today, after half a century, immunoassays are widely utilized with some modifications from the originally proposed system, e.g., radioisotopes have been replaced with enzymes because of safety concerns regarding the use of radioactivity, which is referred to as enzyme immunoassay/enzyme-linked immunosorbent assay (ELISA). In addition, progress has been made in ELISA with the recent advances in recombinant DNA technology, leading to increase in the range of antibodies, probes, and even systems. This review article describes ELISA and its applications for the detection of plant secondary metabolites.

  14. Fermentation conditions optimization of secondary metabolites of crocus sativus L in endophytic fungi

    Directory of Open Access Journals (Sweden)

    DU Yan

    2012-08-01

    Full Text Available In this paper,Endophytic fungi,isolated from corm of saffron,were selected.Strains Q31 fermentation conditions on production of carotenoids were studied.Three kinds of carbon sources were selected.Study found that sucrose could promote cell growth and carotenoid accumulation,and amount of mycelium had an increase of 50.83% in the experimental group than the control group.Carotenoid yield was 23.15 times of the control group.Select three kinds of nitrogen and crosscombinations between them,found that add ammonium sulfate,Mycelium of experimental group had an increased of 86.43% than the control group and carotenoid yield was 5.91 times of the control group.the optimal conditions was found by orthogonal test:sucrose 40 g/L,ammonium sulfate 1.0 g/L,bottling amout 100 mL/250 mL,Inoculum size 5%.By using LC-MS to analyze secondary metabolites of endophytic fungi Q31 from saffron,we found it could steady metabolize one kind of carotinoid,its peak time was 22.447min,maximum absorption peaks were 414.4 and 438.3nm,MW was 738.

  15. Impact of shelf life on content of primary and secondary metabolites in apple (Malus domestica Borkh.).

    Science.gov (United States)

    Veberic, Robert; Schmitzer, Valentina; Petkovsek, Maja M; Stampar, Franci

    2010-01-01

    In this study, we evaluated the changes in apple fruit quality during shelf life. After a month of cold storage, apples of cultivars "Jonagold" and "Golden Delicious" were exposed to ambient temperatures for 21 d, with subsequent sampling every 3 or 4 d. Fruit firmness, changes in amounts of sugars, malic acid, and phenolics were observed during shelf life. Chemical analyses were done with HPLC-PDA system. An interchange between various sugars was noticed, but in general, the sum of sugars remained at the same level. The content of malic acid remained stable or dropped, resulting in sweeter fruit. Levels of phenolics were more constant in the pulp of both cultivars analyzed, while in the peel, the changes were more pronounced. In the pulp, a peak in the content of hydroxycinnamic acids and flavanols was noticed on the 2nd or 3rd sampling and afterwards, the amounts remained constant. In the peel an initial decrease of all analyzed phenolic groups was observed in both cultivars, however it was more pronounced in "Jonagold." It can be concluded that changes in primary and secondary metabolites are not the main reason for the lower quality of fruit exposed to ambient temperatures. On the other hand, fruit firmness might be the limiting factor for shelf life duration. © 2010 Institute of Food Technologists®

  16. Erinacine C: A novel approach to produce the secondary metabolite by submerged cultivation of Hericium erinaceus.

    Science.gov (United States)

    Wolters, Niklas; Schembecker, Gerhard; Merz, Juliane

    2015-12-01

    Erinacine C is a cyathane scaffold-based secondary metabolite, which is naturally produced by the filamentous fungus Hericium erinaceus and has a high potential to treat nervous diseases such as Alzheimer's disease. The investigated approach consists of combining an optimised precultivation of H. erinaceus with an enhanced erinacine C production by developing a suitable main cultivation medium enabling the utilisation of high biomass contents. The final erinacine C production medium is buffered by 100 mM HEPES to ensure a stable pH value of 7.5 during main cultivation at inoculation ratios of up to 5:10 (v/v). The medium components, such as 5.0 g L(-1) oatmeal, 1.5 g L(-1) calcium carbonate, and 0.5 g L(-1) Edamin(®) K are crucial for an increased erinacine C production. Besides, different carbon to nitrogen ratios of 25, 64, and 103 do not affect the erinacine C synthesis. The investigated approach enables the production of 2.73 g erinacine C per litre main cultivation broth, which is tenfold higher than published data. In addition, erinacine C biosynthesis is determined to occur mainly in the first six days of main cultivation. Copyright © 2015 The British Mycological Society. Published by Elsevier Ltd. All rights reserved.

  17. Genome-Wide Analysis of Secondary Metabolite Gene Clusters in Ophiostoma ulmi and Ophiostoma novo-ulmi Reveals a Fujikurin-Like Gene Cluster with a Putative Role in Infection

    Directory of Open Access Journals (Sweden)

    Nicolau Sbaraini

    2017-06-01

    Full Text Available The emergence of new microbial pathogens can result in destructive outbreaks, since their hosts have limited resistance and pathogens may be excessively aggressive. Described as the major ecological incident of the twentieth century, Dutch elm disease, caused by ascomycete fungi from the Ophiostoma genus, has caused a significant decline in elm tree populations (Ulmus sp. in North America and Europe. Genome sequencing of the two main causative agents of Dutch elm disease (Ophiostoma ulmi and Ophiostoma novo-ulmi, along with closely related species with different lifestyles, allows for unique comparisons to be made to identify how pathogens and virulence determinants have emerged. Among several established virulence determinants, secondary metabolites (SMs have been suggested to play significant roles during phytopathogen infection. Interestingly, the secondary metabolism of Dutch elm pathogens remains almost unexplored, and little is known about how SM biosynthetic genes are organized in these species. To better understand the metabolic potential of O. ulmi and O. novo-ulmi, we performed a deep survey and description of SM biosynthetic gene clusters (BGCs in these species and assessed their conservation among eight species from the Ophiostomataceae family. Among 19 identified BGCs, a fujikurin-like gene cluster (OpPKS8 was unique to Dutch elm pathogens. Phylogenetic analysis revealed that orthologs for this gene cluster are widespread among phytopathogens and plant-associated fungi, suggesting that OpPKS8 may have been horizontally acquired by the Ophiostoma genus. Moreover, the detailed identification of several BGCs paves the way for future in-depth research and supports the potential impact of secondary metabolism on Ophiostoma genus’ lifestyle.

  18. Primary, Secondary Metabolites, H2O2, Malondialdehyde and Photosynthetic Responses of Orthosiphon stimaneus Benth. to Different Irradiance Levels

    Directory of Open Access Journals (Sweden)

    Mohd Hafiz Ibrahim

    2012-01-01

    Full Text Available The resource availability hypothesis predicts an increase in the allocation to secondary metabolites when carbon gain is improved relative to nutrient availability, which normally occurs during periods of low irradiance. The present work was carried out to confirm this hypothesis by investigating the effects of decreasing irradiance on the production of plant secondary metabolites (flavonoids and phenolics in the herbal plant Orthosiphon stamineus, and to characterize this production by carbohydrate, H2O2, and malondialdehyde (MDA levels, net photosynthesis, leaf chlorophyll content and carbon to nitrogen ratio (C/N. Four levels of irradiance (225, 500, 625 and 900 µmol/m2/s were imposed onto two-week old seedlings for 12 weeks in a randomized complete block design experiment. Peak production of total flavonoids, phenolics, soluble sugar, starch and total non-structural carbohydrate ocurred under low irradiance of 225 µmol/m2/s, and decreased with increasing irradiance. The up-regulation of secondary metabolites could be explained by the concomitant increases in H2O2 and MDA activities under low irradiance. This condition also resulted in enhanced C/N ratio signifying a reduction in nitrogen levels, which had established significant negative correlations with net photosynthesis, total biomass and total chlorophyll content, indicating the possible existence of a trade-off between growth and secondary metabolism under low irradiance with reduced nitrogen content. The competition between total chlorophyll and secondary metabolites production, as exhibited by the negative correlation coefficient under low irradiance, also suggests a sign of gradual switch of investment from chlorophyll to polyphenols production.

  19. Anti-rheumatoid Activity of Secondary Metabolites Produced by Endophytic Chaetomium globosum

    Science.gov (United States)

    Abdel-Azeem, Ahmed M.; Zaki, Sherif M.; Khalil, Waleed F.; Makhlouf, Noha A.; Farghaly, Lamiaa M.

    2016-01-01

    The aim of the present study was to investigate the anti-rheumatoid activity of secondary metabolites produced by endophytic mycobiota in Egypt. A total of 27 endophytic fungi were isolated from 10 dominant medicinal plant host species in Wadi Tala, Saint Katherine Protectorate, arid Sinai, Egypt. Of those taxa, seven isolates of Chaetomium globosum (CG1–CG7), being the most frequent taxon, were recovered from seven different host plants and screened for production of active anti-inflammatory metabolites. Isolates were cultivated on half – strength potato dextrose broth for 21 days at 28°C on a rotatory shaker at 180 rpm, and extracted in ethyl acetate and methanol, respectively. The probable inhibitory effects of both extracts against an adjuvant induced arthritis (AIA) rat model were examined and compared with the effects of methotrexate (MTX) as a standard disease-modifying anti-rheumatoid drug. Disease activity and mobility scoring of AIA, histopathology and transmission electron microscopy (TEM) were used to evaluate probable inhibitory roles. A significant reduction (P < 0.05) in the severity of arthritis was observed in both the methanolic extract of CG6 (MCG6) and MTX treatment groups 6 days after treatment commenced. The average arthritis score of the MCG6 treatment group was (10.7 ± 0.82) compared to (13.8 ± 0.98) in the positive control group. The mobility score of the MCG6 treatment group (1.50 ± 0.55) was significantly lower than that of the positive control group (3.33 ± 0.82). In contrast, the ethyl acetate extract of CG6 (EACG6) treatment group showed no improvements in arthritis and mobility scores in AIA model rats. Histopathology and TEM findings confirmed the observation. Isolate CG6 was subjected to sequencing for confirmation of phenotypic identification. The internal transcribed spacer (ITS) 1–5.8 s – ITS2 rDNA sequences obtained were compared with those deposited in the GenBank Database and registered with accession number KC

  20. Sucrose-enhanced biosynthesis of medicinally important antioxidant secondary metabolites in cell suspension cultures of Artemisia absinthium L.

    Science.gov (United States)

    Ali, Mohammad; Abbasi, Bilal Haider; Ahmad, Nisar; Ali, Syed Shujait; Ali, Shahid; Ali, Gul Shad

    2016-12-01

    Natural products are gaining tremendous importance in pharmaceutical industry and attention has been focused on the applications of in vitro technologies to enhance yield and productivity of such products. In this study, we investigated the accumulation of biomass and antioxidant secondary metabolites in response to different carbohydrate sources (sucrose, maltose, fructose and glucose) and sucrose concentrations (1, 3, 5, 7 and 9 %). Moreover, the effects of 3 % repeated sucrose feeding (day-12, -18 and -24) were also investigated. The results showed the superiority of disaccharides over monosaccharides for maximum biomass and secondary metabolites accumulation. Comparable profiles for maximum biomass were observed in response to sucrose and maltose and initial sucrose concentrations of 3 and 5 %. Maximum total phenolic and total flavonoid contents were displayed by cultures treated with sucrose and maltose; however, initial sucrose concentrations of 5 and 7 % were optimum for both classes of metabolites, respectively. Following 3 % extra sucrose feeding, cultures fed on day-24 (late-log phase) showed higher biomass, total phenolic and total flavonoid contents as compared to control cultures. Highest antioxidant activity was exhibited by maltose-treated cultures. Moreover, sucrose-treated cultures displayed positive correlation of antioxidant activity with total phenolics and total flavonoids production. This work describes the stimulatory role of disaccharides and sucrose feeding strategy for higher accumulation of phenolics and flavonoids, which could be potentially scaled up to bioreactor level for the bulk production of these metabolites in suspension cultures of A. absinthium.

  1. A fish-feeding laboratory bioassay to assess the antipredatory activity of secondary metabolites from the tissues of marine organisms.

    Science.gov (United States)

    Marty, Micah J; Pawlik, Joseph R

    2015-01-11

    Marine chemical ecology is a young discipline, having emerged from the collaboration of natural products chemists and marine ecologists in the 1980s with the goal of examining the ecological functions of secondary metabolites from the tissues of marine organisms. The result has been a progression of protocols that have increasingly refined the ecological relevance of the experimental approach. Here we present the most up-to-date version of a fish-feeding laboratory bioassay that enables investigators to assess the antipredatory activity of secondary metabolites from the tissues of marine organisms. Organic metabolites of all polarities are exhaustively extracted from the tissue of the target organism and reconstituted at natural concentrations in a nutritionally appropriate food matrix. Experimental food pellets are presented to a generalist predator in laboratory feeding assays to assess the antipredatory activity of the extract. The procedure described herein uses the bluehead, Thalassoma bifasciatum, to test the palatability of Caribbean marine invertebrates; however, the design may be readily adapted to other systems. Results obtained using this laboratory assay are an important prelude to field experiments that rely on the feeding responses of a full complement of potential predators. Additionally, this bioassay can be used to direct the isolation of feeding-deterrent metabolites through bioassay-guided fractionation. This feeding bioassay has advanced our understanding of the factors that control the distribution and abundance of marine invertebrates on Caribbean coral reefs and may inform investigations in diverse fields of inquiry, including pharmacology, biotechnology, and evolutionary ecology.

  2. Comprehensive Secondary Metabolite Profiling Toward Delineating the Solid and Submerged-State Fermentation of Aspergillus oryzae KCCM 12698

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    Su Y. Son

    2018-05-01

    Full Text Available Aspergillus oryzae has been commonly used to make koji, meju, and soy sauce in traditional food fermentation industries. However, the metabolic behaviors of A. oryzae during fermentation in various culture environments are largely uncharacterized. Thus, we performed time resolved (0, 4, 8, 12, 16 day secondary metabolite profiling for A. oryzae KCCM 12698 cultivated on malt extract agar and broth (MEA and MEB under solid-state fermentation (SSF and submerged fermentation (SmF conditions using the ultrahigh performance liquid chromatography-linear trap quadrupole-ion trap-mass spectrometry (UHPLC-LTQ-IT-MS/MS followed by multivariate analyses. We observed the relatively higher proportions of coumarins and oxylipins in SSF, whereas the terpenoids were abundant in SmF. Moreover, we investigated the antimicrobial efficacy of metabolites that were extracted from SSF and SmF. The SSF extracts showed higher antimicrobial activities as compared to SmF, with higher production rates of bioactive secondary metabolites viz., ketone-citreoisocoumarin, pentahydroxy-anthraquinone, hexylitaconic acid, oxylipins, and saturated fatty acids. The current study provides the underpinnings of a metabolomic framework regarding the growth and bioactive compound production for A. oryzae under the primarily employed industrial cultivation states. Furthermore, the study holds the potentials for rapid screening and MS-characterization of metabolites helpful in determining the consumer safety implications of fermented foods involving Koji mold.

  3. Secondary metabolite profiling of Curcuma species grown at different locations using GC/TOF and UPLC/Q-TOF MS.

    Science.gov (United States)

    Lee, Jueun; Jung, Youngae; Shin, Jeoung-Hwa; Kim, Ho Kyoung; Moon, Byeong Cheol; Ryu, Do Hyun; Hwang, Geum-Sook

    2014-07-04

    Curcuma, a genus of rhizomatous herbaceous species, has been used as a spice, traditional medicine, and natural dye. In this study, the metabolite profile of Curcuma extracts was determined using gas chromatography-time of flight mass spectrometry (GC/TOF MS) and ultrahigh-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF MS) to characterize differences between Curcuma aromatica and Curcuma longa grown on the Jeju-do or Jin-do islands, South Korea. Previous studies have performed primary metabolite profiling of Curcuma species grown in different regions using NMR-based metabolomics. This study focused on profiling of secondary metabolites from the hexane extract of Curcuma species. Principal component analysis (PCA) and partial least-squares discriminant analysis (PLS-DA) plots showed significant differences between the C. aromatica and C. longa metabolite profiles, whereas geographical location had little effect. A t-test was performed to identify statistically significant metabolites, such as terpenoids. Additionally, targeted profiling using UPLC/Q-TOF MS showed that the concentration of curcuminoids differed depending on the plant origin. Based on these results, a combination of GC- and LC-MS allowed us to analyze curcuminoids and terpenoids, the typical bioactive compounds of Curcuma, which can be used to discriminate Curcuma samples according to species or geographical origin.

  4. Cultivar-Specific Changes in Primary and Secondary Metabolites in Pak Choi (Brassica Rapa, Chinensis Group by Methyl Jasmonate

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    Moo Jung Kim

    2017-05-01

    Full Text Available Glucosinolates, their hydrolysis products and primary metabolites were analyzed in five pak choi cultivars to determine the effect of methyl jasmonate (MeJA on metabolite flux from primary metabolites to glucosinolates and their hydrolysis products. Among detected glucosinolates (total 14 glucosinolates; 9 aliphatic, 4 indole and 1 aromatic glucosinolates, indole glucosinolate concentrations (153–229% and their hydrolysis products increased with MeJA treatment. Changes in the total isothiocyanates by MeJA were associated with epithiospecifier protein activity estimated as nitrile formation. Goitrin, a goitrogenic compound, significantly decreased by MeJA treatment in all cultivars. Changes in glucosinolates, especially aliphatic, significantly differed among cultivars. Primary metabolites including amino acids, organic acids and sugars also changed with MeJA treatment in a cultivar-specific manner. A decreased sugar level suggests that they might be a carbon source for secondary metabolite biosynthesis in MeJA-treated pak choi. The result of the present study suggests that MeJA can be an effective agent to elevate indole glucosinolates and their hydrolysis products and to reduce a goitrogenic compound in pak choi. The total glucosinolate concentration was the highest in “Chinese cabbage” in the control group (32.5 µmol/g DW, but indole glucosinolates increased the greatest in “Asian” when treated with MeJA.

  5. Secondary Metabolite Profiling of Curcuma Species Grown at Different Locations Using GC/TOF and UPLC/Q-TOF MS

    Directory of Open Access Journals (Sweden)

    Jueun Lee

    2014-07-01

    Full Text Available Curcuma, a genus of rhizomatous herbaceous species, has been used as a spice, traditional medicine, and natural dye. In this study, the metabolite profile of Curcuma extracts was determined using gas chromatography-time of flight mass spectrometry (GC/TOF MS and ultrahigh-performance liquid chromatography–quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF MS to characterize differences between Curcuma aromatica and Curcuma longa grown on the Jeju-do or Jin-do islands, South Korea. Previous studies have performed primary metabolite profiling of Curcuma species grown in different regions using NMR-based metabolomics. This study focused on profiling of secondary metabolites from the hexane extract of Curcuma species. Principal component analysis (PCA and partial least-squares discriminant analysis (PLS-DA plots showed significant differences between the C. aromatica and C. longa metabolite profiles, whereas geographical location had little effect. A t-test was performed to identify statistically significant metabolites, such as terpenoids. Additionally, targeted profiling using UPLC/Q-TOF MS showed that the concentration of curcuminoids differed depending on the plant origin. Based on these results, a combination of GC- and LC-MS allowed us to analyze curcuminoids and terpenoids, the typical bioactive compounds of Curcuma, which can be used to discriminate Curcuma samples according to species or geographical origin.

  6. Introduction to metabolic genetic engineering for the production of valuable secondary metabolites in in vivo and in vitro plant systems.

    Science.gov (United States)

    Benedito, Vagner A; Modolo, Luzia V

    2014-01-01

    Plants are capable of producing a myriad of chemical compounds. While these compounds serve specific functions in the plant, many have surprising effects on the human body, often with positive action against diseases. These compounds are often difficult to synthesize ex vivo and require the coordinated and compartmentalized action of enzymes in living organisms. However, the amounts produced in whole plants are often small and restricted to single tissues of the plant or even cellular organelles, making their extraction an expensive process. Since most natural products used in therapeutics are specialized, secondary plant metabolites, we provide here an overview of the classification of the main classes of these compounds, with its biochemical pathways and how this information can be used to create efficient in and ex planta production pipelines to generate highly valuable compounds. Metabolic genetic engineering is introduced in light of physiological and genetic methods to enhance production of high-value plant secondary metabolites.

  7. NUTRITIVE VALUE, In Vitro FERMENTATION AND SECONDARY METABOLITES OF WEEDS AND MAIZE STRAW USED FOR FEEDING DAIRY CATTLE

    Directory of Open Access Journals (Sweden)

    Raquel Martínez-Loperena

    2011-03-01

    Full Text Available In the highlands of Central Mexico a surplus of different forages is observed during the rainy season particularly weeds, which grow in maize fields. Weeds are widely used by farmers to feed dairy cattle. The objective of the present work was to determine the nutritive value of weeds, their content of secondary metabolites, and their effect on in vitro fermentation kinetics when included (at different levels of inclusion in a diet based on maize straw. The present study was carried out in two regions of the Toluca valley from August to October 2007. A split plot design was used to evaluate the variables associated with the nutritive value and a randomized design was employed to evaluate the content of secondary metabolites in the different weed species. Significant differences (P

  8. Antimicrobial efficacy of secondary metabolites from Glomerella cingulata Eficiência antimicrobiana do extrato bruto de Glomerella cingulata

    OpenAIRE

    K. Hara Kishore; Sunil Misra; D. Ramesh Chandra; K.V.V. R. Prakash; U. Suryanarayana Murty

    2007-01-01

    Fungi are known to produce a vast array of secondary metabolites that are gaining importance for their biotechnological applications. Early reports suggest that G. cingulata has the capability to transform many compounds by various enzymatic actions. Therefore, the focus of this study was to determine the antibacterial and antifungal activity of crude ethyl acetate extract of G. cingulata using agar cup bioassay method. Crude extract of G. cingulata exhibited remarkable antifungal activity ag...

  9. Selective and Specific Inhibition of the Plasmodium falciparum Lysyl-tRNA Synthetase by the Fungal Secondary Metabolite Cladosporin

    OpenAIRE

    Hoepfner, Dominic; McNamara, Case W.; Lim, Chek Shik; Studer, Christian; Riedl, Ralph; Aust, Thomas; McCormack, Susan L.; Plouffe, David M.; Meister, Stephan; Schuierer, Sven; Plikat, Uwe; Hartmann, Nicole; Staedtler, Frank; Cotesta, Simona; Schmitt, Esther K.

    2012-01-01

    Summary With renewed calls for malaria eradication, next-generation antimalarials need be active against drug-resistant parasites and efficacious against both liver- and blood-stage infections. We screened a natural product library to identify inhibitors of Plasmodium falciparum blood- and liver-stage proliferation. Cladosporin, a fungal secondary metabolite whose target and mechanism of action are not known for any species, was identified as having potent, nanomolar, antiparasitic activity a...

  10. Secondary Metabolite Content in Roots and Callus of Paeonia Anomala L.

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    A.A. ZARIPOVA

    2014-06-01

    Full Text Available Taking into account the fact that in the process of introduction in vitro culture the change of secondary metabolite content may take place we compared the chemical composition of plant material of wild-growing plants of Paeonia anomala introduced and produced using the methods of clonal micropropagation, callus tissue.The content of phenolic compounds, that is catechins and gallatos was compared. Paeoniflorin content was estimated by direct spectrophotometry of methanol extracts (λ = 231,7 nm, ε 1% 1 sm = 265.4. Integral characteristic of the obtained extracts was received by comparison of absorption spectra using spectrophotometer SP - 121 within wave diapason 300 - 460 nm.Light absorption curves of methanol extracts had two distinct peaks at λ = 232 nm and λ = 275 nm typical of paeoniflorin. Paeoniflorin content was 80 % higher in young peony roots than in control plant. This glycoside content in callus culture was 44 % higher than in wild-growing plant roots and 26 % lower than in plantlet roots.The use of ethanol as extragent showed a higher content of extracted substances in callus tissue. The comparison of the obtained spectra in the region corresponding to phenolic compound absorption shows the highest phenolic compound content in callus tissue and young plant roots. Judging by light absorption maximum it may be phenolic acids. The lowest phenolic compound content was determined in adult wild-growing plant roots, where a high phlobaphene content was visually observed.The conducted research confirms the fact that callus culture of Paeonia anomala L. is a perspective producer of monoterpene glycosides and phenolic compounds. Extracts from plantlets and callus culture exceed in biological active substance content rootstock extracts of open air plants.

  11. Comparative analysis of secondary metabolites contents in[i] Fragaria vesca[/i] L. fruits

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    Agnieszka Najda

    2014-06-01

    Full Text Available [i]Fragaria vesca[/i] (wild strawberry belongs to the Rosaceae family. Besides the leaves ([i]Fragariae folium[/i] and roots ([i]Fragariae radix[/i], the aromatic fruits ([i]Fragariae fructus[/i] of wild strawberry are also herbal materials used in medicine. The aim of this study was to compare the value of phytochemical and antioxidant activity of wild strawberry fruits ([i]Fragaria vesca L[/i].. The fruits were analyzed regarding their secondary metabolites contents (flavonoids, sum of phenolic acids, tannins, anthocyanins, DPPH, depending on the origin of the raw material (from natural habitats vs. cultivation. According to the obtained results, raw material originating from natural habitats contained significantly more flavonoids (0.559 mg∙g [sup]-1[/sup] , compared to fruits harvested from cultivation (0.472 mg∙g [sup]-1[/sup] , on average. Mean concentration of phenolic acids ranged from 1.648 mg∙g[sup] -1[/sup] – 2.348 mg∙g [sup]-1[/sup] , although the wild form was characterized by higher levels of examined substances. Tannins are an important fraction of phenolic compounds; their content in studied fruits ranged from 2.2% (from cultivation – 3.0% (from natural habitats. When comparing the average contents of anthocyanins in the studied materials, it was revealed that remarkably more of these compounds were recorded in wild strawberry fruits harvested from natural habitats vs. those from cultivations: 132 mg∙100 g [sup]-1[/sup] vs. 90 mg∙100 g [sup]-1[/sup] . A difference was indicated with respect to the ability of DPPH radical reduction to diphenylpicrylhydrazine by extracts made of examined fruits.

  12. Spongionella secondary metabolites, promising modulators of immune response through CD147 receptor modulation

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    Jon Andoni Sánchez

    2016-10-01

    Full Text Available The modulation of the immune system can have multiple applications such as cancer treatment, and a wide type of processes involving inflammation where the potent chemotactic agent cyclophilin A (Cyp A is implicated. The Porifera phylum, in which Spongionella is encompassed, is the main producer of marine bioactive compounds. Four secondary metabolites obtained from Spongionella (Gracilin H, A, L and Tetrahydroaplysulphurin-1 were described to hit Cyp A and to block the release of inflammation mediators. Based on these results some role of Spongionella compounds on other steps of the signalling pathway mediated by this chemotactic agent can be hypothesised. In the present paper we studied the effect of these four compounds on the surface membrane CD147 receptor expression, on the extracellular levels of Cyp A and on the ability to migrate of concanavalin (Con A-activated T lymphocytes. Similarly to a well-known immunosuppressive agent cyclosporine A (CsA, Gracilin H, A, L and tetrahydroaplysulphurin-1 were able to reduce the CD147 membrane expression and to block the release of Cyp A to the medium. Besides, by using Cyp A as chemotactic agent, T cell migration was inhibited when cells were previously incubated with Gracilin A and Gracilin L. These positive results lead us to test the in vivo effect of Gracilin H and L in a mouse ear delayed hypersensitive reaction. Thus, both compounds efficiently reduce the ear swelling as well as the inflammatory cell infiltration. These results provide more evidences for their potential therapeutic application in immune related diseases of Spongionella compounds.

  13. Toxicity of Secondary Metabolites from Meliaceae Against Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae).

    Science.gov (United States)

    Giongo, A M M; Vendramim, J D; Freitas, S D L; Silva, M F G F

    2016-12-01

    The study was carried out to evaluate the bioactivity of secondary metabolites from Trichilia pallida, Trichilia pallens, and Toona ciliata against fall armyworm Spodoptera frugiperda (J. E. Smith) larvae. The studied compounds included (+/-)-catechins, a triglyceride, and cedrelone isolated from T. ciliata branches, fruits, and stems, respectively; dammaradienol isolated from T. pallida leaves; and scopoletin isolated from T. pallens branches. The compounds' activity was evaluated through ingestion and topic treatment. Treated artificial diet was offered to first instar larvae to evaluate ingestion effect, while an application on the dorsal thoracic region of third instar larvae was used to evaluate the topic effect. Mortality was assessed daily, and larval weight was recorded after 7 days for ingestion and 5 days for topic application. Scopoletin and triglyceride caused low mortality rates and reduction in larval weight by ingestion, (+/-)-catechins caused larval weight reduction by ingestion, and scopoletin reduced survival by topic treatment. The most effective compound was cedrelone that affected larval survival and development mainly by ingestion. The estimated LC 50 , LC 90 , and EC 50 for cedrelone were 0.0365, 0.0659, and 0.0095%, respectively. Further, cedrelone-treated corn leaf discs were offered to fourth instar larvae during 16 h in choice and no-choice tests. The deterrence indexes obtained in the choice tests were 23.5 and 36.3% at concentrations of 0.0365 and 0.0659, respectively. Consumption of cedrelone-treated leaf discs at the concentration of 0.0659% was lower compared to the control in the no-choice test. Thus, cedrelone caused lethal and sublethal effects and phagodeterrence on S. frugiperda and should be further studied.

  14. Effects of bacterial inoculants on the indigenous microbiome and secondary metabolites of chamomile plants

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    Ruth eSchmidt

    2014-02-01

    Full Text Available Plant-associated bacteria fulfil important functions for plant growth and health of their host. However, our knowledge about the impact of bacterial treatments on the host’s microbiome and physiology is limited. The present study was conducted to assess the impact of bacterial inoculants on the microbiome of chamomile plants Chamomilla recutita (L. Rauschert grown in a field under organic management in Egypt. Chamomile seedlings were inoculated with three indigenous Gram-positive strains (Streptomyces subrutilus Wbn2-11, Bacillus subtilis Co1-6, Paenibacillus polymyxa Mc5Re-14 from Egypt and three European Gram-negative strains (Pseudomonas fluorescens L13-6-12, Stenotrophomonas rhizophila P69, Serratia plymuthica 3Re4-18 already known for their beneficial plant-microbe interaction. Molecular fingerprints of 16S rRNA gene as well as real-time PCR analyses did not show statistically significant differences for all applied bacterial antagonists compared to the control. In contrast, a pyrosequencing analysis of the 16S rRNA gene libraries revealed significant differences in the community structure of bacteria between the treatments. These differences could be clearly shown by a shift within the community structure and corresponding beta-diversity indices. Moreover, B. subtilis Co1-6 and P. polymyxa Mc5Re-14 showed an enhancement of the bioactive secondary metabolite apigenin-7-O-glucoside. This indicates a possible new function of bacterial inoculants: to interact with the plant microbiome as well as with the plant metabolome.

  15. Antibacterial activity and characterization of secondary metabolites isolated from mangrove plant Avicennia officinalis

    Institute of Scientific and Technical Information of China (English)

    Valentin Bhimba B; J Meenupriya; Elsa Lycias Joel; D Edaya Naveena; Suman kumar; M Thangaraj

    2010-01-01

    Objective:To explore antibacterial activity and characterization of secondary metabolites isolated from mangrove plant Avicennia officinalis (A. officinalis). Methods:In the present study the leaf extracts of A. officinalis were examined for its antibacterial potential using five different solvents against some reference strains of human pathogenic bacteria for the crude extract. Maximum activity was observed for ethyl acetate and hence different concentrations like 15μL, 25μL, and 50μL of ethyl extracts was checked for its antibacterial activity. Partial purification of crude extract was carried by column chromatography and fractions were analyzed using gas chromatography-mass spectrometry (GC-MS) to identify compounds. Results:The crude ethyl acetate extracts of A. officinalis showed remarkable antibacterial activity with zones of inhibition of 13 mm against Eschericia coli (E. coli) and 11 mm against Staphylococcus aureus (S. aureus). Fraction 13 (ethyl acetate÷methanol=8÷2) as the most potent one against with the minimal inhibitory concentration of 30 mm against E. coli and 25 mm against S. aureus. The GC-MS resultsof active column fraction (F13) revealed that the active principals were a mixture of hydroxy-4 methoxybenzoic acid, diethyl phthalate, oleic acid. Conclusions:The leaf extracts with proven antibacterial effects can clearly be directed towards cancer treatment as to inhibiting cancer cell growth. The limited number of test organisms owes to a constraint of resource. So, the effect of strong bursts of leaf extracts on human pathogenic bacteria should further be tested on a wide range of test organisms.

  16. Evaluation of primary and secondary metabolites in selected varieties of potatoes.

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    Ján Mareček

    2016-01-01

    Full Text Available The aim of study was to determine primary and secondary metabolites in selected varieties of potatoes. Potatoes (Solanum tuberosum L. are good source of bioactive compounds, mainly phenols as one of the most important components. The chemical composition with reducing sugar, starch, ascorbic acid, total polyphenol and flavonoid content were analyzed in five potato varieties (Agria, Marabel, Red Anna, Picasso, Princess. Values of dry matter content ranged from 20.34 to 23.64%. In terms of tubers storage, its content above 20% is required. The highest level of starch was detected in variety Princess (16.82%. The lowest reducing sugar content was recorded by variety Marabel (0.08%. Similarly, low values reached varieties Princess (0.12%, Agria (0.14 and Red Anna (0.16%. These would be appropriate to use for food processing and for production of fried potato chips or fries. Variety Red Anna reached the highest amount of vitamin C (73.72 mg.kg-1. The lower levels of this vitamin showed tubers of varieties Picasso (35.02 mg.kg-1 and Princess (36.89 mg.kg-1. The antioxidant activity was measured with radical scavenging assays using 1,1-diphenyl-2-picrylhydrazyl (DPPH radical as well as phosphomolybdenic assay. Potato varieties contained high levels of total polyphenols (0.474 – 1.550 mg GAE per dry weight and flavonoids (1.407 – 15.933 μg QE per dry weight. The consumption of potatoes can provide nutritional value along with antioxidant potential that can be helpful for proper functioning of the body physiological systems. Statistical evaluation by the single factor analysis of variance detected high significant impact of variety on the content of all the analytical parameters in evaluated varieties of potato tubers. Normal 0 21 false false false SK X-NONE X-NONE

  17. Extraction and Identification of Secondary Metabolites Produced by Trichoderma atroviridae (6022 and Evaluating of their Antifungal Effects

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    M. Shahiri Tabarestani

    2017-08-01

    Full Text Available Introduction: Fungi release wide spectrum of secondary metabolites that belong to several chemical groups with different biochemical origins. These materials produce as intermediate and end products of diverse metabolic pathways. The profile of the secondary metabolites for a known species or strain will vary depending on the substrate, the duration of incubation, the type of nutrients, temperature and other environmental parameters. Trichoderma spp. are well-known producers of secondary metabolites with different biological activities. The secondary metabolites with antibiotic activity can be classified into two main types. Low molecular weight and volatile metabolites which are involved in complex Trichoderma plant-pathogen interactions. They belong to various structure classes such as alcohols, ketones, alkanes, furans, simple aromatic compounds, isocyanate compounds, volatile terpenes, some polyketides, butenolides, and pyrones. All of them are relatively nonpolar compounds with a significant vapor pressure. These volatile organic compounds (VOCs in the soil environment could be traveled over distance and affect the physiology of the pathogens. They also enhance growth and systemic resistance in plants. These VOCs have been evaluated for T. atroviride, T. harzianum, T. viride, T. longibrachiatum, T. pseudokoningii and T. aureoviride. High molecular weight metabolites (like peptaibols are polar metabolites which act directly by contact between Trichoderma species and competitor organisms. Due to potent separation and highly sensitive detection, gas chromatography-mass spectrometry (GC-MS is the main method for detection of the fungal VOCs. Mass spectrometric detection offers the possibility to identify individual volatiles from complex mixtures. Structure characterization and confirmation of identity are usually achieved by comparison of mass spectra with library spectra and the determination of chromatographic retention indices. Due to the

  18. Minimum Information about a Biosynthetic Gene cluster : commentary

    NARCIS (Netherlands)

    Medema, Marnix H; Kottmann, Renzo; Yilmaz, Pelin; Cummings, Matthew; Biggins, John B; Blin, Kai; de Bruijn, Irene; Chooi, Yit Heng; Claesen, Jan; Coates, R Cameron; Cruz-Morales, Pablo; Duddela, Srikanth; Dusterhus, Stephanie; Edwards, Daniel J; Fewer, David P; Garg, Neha; Geiger, Christoph; Gomez-Escribano, Juan Pablo; Greule, Anja; Hadjithomas, Michalis; Haines, Anthony S; Helfrich, Eric J N; Hillwig, Matthew L; Ishida, Keishi; Jones, Adam C; Jones, Carla S; Jungmann, Katrin; Kegler, Carsten; Kim, Hyun Uk; Kotter, Peter; Krug, Daniel; Masschelein, Joleen; Melnik, Alexey V; Mantovani, Simone M; Monroe, Emily A; Moore, Marcus; Moss, Nathan; Nutzmann, Hans-Wilhelm; Pan, Guohui; Pati, Amrita; Petras, Daniel; Reen, F Jerry; Rosconi, Federico; Rui, Zhe; Tian, Zhenhua; Tobias, Nicholas J; Tsunematsu, Yuta; Wiemann, Philipp; Wyckoff, Elizabeth; Yan, Xiaohui; Yim, Grace; Yu, Fengan; Xie, Yunchang; Aigle, Bertrand; Apel, Alexander K; Balibar, Carl J; Balskus, Emily P; Barona-Gomez, Francisco; Bechthold, Andreas; Bode, Helge B; Borriss, Rainer; Brady, Sean F; Brakhage, Axel A; Caffrey, Patrick; Cheng, Yi-Qiang; Clardy, Jon; Cox, Russell J; De Mot, Rene; Donadio, Stefano; Donia, Mohamed S; van der Donk, Wilfred A; Dorrestein, Pieter C; Doyle, Sean; Driessen, Arnold J M; Ehling-Schulz, Monika; Entian, Karl-Dieter; Fischbach, Michael A; Gerwick, Lena; Gerwick, William H; Gross, Harald; Gust, Bertolt; Hertweck, Christian; Hofte, Monica; Jensen, Susan E; Ju, Jianhua; Katz, Leonard; Kaysser, Leonard; Klassen, Jonathan L; Keller, Nancy P; Kormanec, Jan; Kuipers, Oscar P; Kuzuyama, Tomohisa; Kyrpides, Nikos C; Kwon, Hyung-Jin; Lautru, Sylvie; Lavigne, Rob; Lee, Chia Y; Linquan, Bai; Liu, Xinyu; Liu, Wen; Luzhetskyy, Andriy; Mahmud, Taifo; Mast, Yvonne; Mendez, Carmen; Metsa-Ketela, Mikko; Micklefield, Jason; Mitchell, Douglas A; Moore, Bradley S; Moreira, Leonilde M; Muller, Rolf; Neilan, Brett A; Nett, Markus; Nielsen, Jens; O'Gara, Fergal; Oikawa, Hideaki; Osbourn, Anne; Osburne, Marcia S; Ostash, Bohdan; Payne, Shelley M; Pernodet, Jean-Luc; Petricek, Miroslav; Piel, Jorn; Ploux, Olivier; Raaijmakers, Jos M; Salas, Jose A; Schmitt, Esther K; Scott, Barry; Seipke, Ryan F; Shen, Ben; Sherman, David H; Sivonen, Kaarina; Smanski, Michael J; Sosio, Margherita; Stegmann, Evi; Sussmuth, Roderich D; Tahlan, Kapil; Thomas, Christopher M; Tang, Yi; Truman, Andrew W; Viaud, Muriel; Walton, Jonathan D; Walsh, Christopher T; Weber, Tilmann; van Wezel, Gilles P; Wilkinson, Barrie; Willey, Joanne M; Wohlleben, Wolfgang; Wright, Gerard D; Ziemert, Nadine; Zhang, Changsheng; Zotchev, Sergey B; Breitling, Rainer; Takano, Eriko; Glockner, Frank Oliver

    A wide variety of enzymatic pathways that produce specialized metabolites in bacteria, fungi and plants are known to be encoded in biosynthetic gene clusters. Information about these clusters, pathways and metabolites is currently dispersed throughout the literature, making it difficult to exploit.

  19. Antifungal activity of secondary plant metabolites from potatoes (Solanum tuberosum L.): Glycoalkaloids and phenolic acids show synergistic effects.

    Science.gov (United States)

    Sánchez-Maldonado, A F; Schieber, A; Gänzle, M G

    2016-04-01

    To study the antifungal effects of the potato secondary metabolites α-solanine, α-chaconine, solanidine and caffeic acid, alone or combined. Resistance to glycoalkaloids varied among the fungal species tested, as derived from minimum inhibitory concentrations assays. Synergistic antifungal activity between glycoalkaloids and phenolic compounds was found. Changes in the fluidity of fungal membranes caused by potato secondary plant metabolites were determined by calculation of the generalized polarization values. The results partially explained the synergistic effect between caffeic acid and α-chaconine and supported findings on membrane disruption mechanisms from previous studies on artificial membranes. LC/MS analysis was used to determine variability and relative amounts of sterols in the different fungal species. Results suggested that the sterol pattern of fungi is related to their resistance to potato glycoalkaloids and to their taxonomy. Fungal resistance to α-chaconine and possibly other glycoalkaloids is species dependent. α-Chaconine and caffeic acid show synergistic antifungal activity. The taxonomic classification and the sterol pattern play a role in fungal resistance to glycoalkaloids. Results improve the understanding of the antifungal mode of action of potato secondary metabolites, which is essential for their potential utilization as antifungal agents in nonfood systems. © 2016 The Society for Applied Microbiology.

  20. Lichen secondary metabolites are responsible for induction of apoptosis in HT-29 and A2780 human cancer cell lines.

    Science.gov (United States)

    Bačkorová, M; Jendželovský, R; Kello, M; Bačkor, M; Mikeš, J; Fedoročko, P

    2012-04-01

    Lichens are a known source of approximately 800 unique secondary metabolites, many of which play important ecological roles, including regulating the equilibrium between symbionts. However, only a few of these compounds have been assessed for their effectiveness against various in vitro cancer models. Moreover, the mechanisms of biological activity of lichen secondary metabolites on living cells (including cancer cells) are still almost entirely unknown. In the present study, we investigated the mechanisms of cytotoxicity of four lichen secondary metabolites (parietin, atranorin, usnic acid and gyrophoric acid) on A2780 and HT-29 cancer cell lines. We found that usnic acid and atranorin were more effective anti-cancer compounds when compared to parietin and gyrophoric acid. Usnic acid and atranorin were capable of inducing a massive loss in the mitochondrial membrane potential, along with caspase-3 activation (only in HT-29 cells) and phosphatidylserine externalization in both tested cell lines. Induction of both ROS and especially RNS may be responsible, at least in part, for the cytotoxic effects of the tested compounds. Based on the detection of protein expression (PARP, p53, Bcl-2/Bcl-xL, Bax, p38, pp38) we found that usnic acid and atranorin are activators of programmed cell death in A2780 and HT-29, probably through the mitochondrial pathway. Copyright © 2012 Elsevier Ltd. All rights reserved.

  1. Activation of dormant secondary metabolite production by introducing neomycin resistance into the deep-sea fungus, Aspergillus versicolor ZBY-3.

    Science.gov (United States)

    Dong, Yuan; Cui, Cheng-Bin; Li, Chang-Wei; Hua, Wei; Wu, Chang-Jing; Zhu, Tian-Jiao; Gu, Qian-Qun

    2014-07-29

    A new ultrasound-mediated approach has been developed to introduce neomycin-resistance to activate silent pathways for secondary metabolite production in a bio-inactive, deep-sea fungus, Aspergillus versicolor ZBY-3. Upon treatment of the ZBY-3 spores with a high concentration of neomycin by proper ultrasound irradiation, a total of 30 mutants were obtained by single colony isolation. The acquired resistance of the mutants to neomycin was confirmed by a resistance test. In contrast to the ZBY-3 strain, the EtOAc extracts of 22 of the 30 mutants inhibited the human cancer K562 cells, indicating that these mutants acquired a capability to produce antitumor metabolites. HPLC-photodiode array detector (PDAD)-UV and HPLC-electron spray ionization (ESI)-MS analyses of the EtOAc extracts of seven bioactive mutants and the ZBY-3 strain indicated that diverse secondary metabolites have been newly produced in the mutant extracts in contrast to the ZBY-3 extract. The followed isolation and characterization demonstrated that six metabolites, cyclo(D-Pro-D-Phe) (1), cyclo(D-Tyr-D-Pro) (2), phenethyl 5-oxo-L-prolinate (3), cyclo(L-Ile-L-Pro) (4), cyclo(L-Leu-L-Pro) (5) and 3β,5α,9α-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (6), were newly produced by the mutant u2n2h3-3 compared to the parent ZBY-3 strain. Compound 3 was a new compound; 2 was isolated from a natural source for the first time, and all of these compounds were also not yet found in the metabolites of other A. versicolor strains. Compounds 1-6 inhibited the K562 cells, with inhibition rates of 54.6% (1), 72.9% (2), 23.5% (3), 29.6% (4), 30.9% (5) and 51.1% (6) at 100 μg/mL, and inhibited also other human cancer HL-60, BGC-823 and HeLa cells, to some extent. The present study demonstrated the effectiveness of the ultrasound-mediated approach to activate silent metabolite production in fungi by introducing acquired resistance to aminoglycosides and its potential for discovering new compounds from silent fungal

  2. Dual biosynthetic pathways to phytosterol via cycloartenol and lanosterol in Arabidopsis.

    Science.gov (United States)

    Ohyama, Kiyoshi; Suzuki, Masashi; Kikuchi, Jun; Saito, Kazuki; Muranaka, Toshiya

    2009-01-20

    The differences between the biosynthesis of sterols in higher plants and yeast/mammals are believed to originate at the cyclization step of oxidosqualene, which is cyclized to cycloartenol in higher plants and lanosterol in yeast/mammals. Recently, lanosterol synthase genes were identified from dicotyledonous plant species including Arabidopsis, suggesting that higher plants possess dual biosynthetic pathways to phytosterols via lanosterol, and through cycloartenol. To identify the biosynthetic pathway to phytosterol via lanosterol, and to reveal the contributions to phytosterol biosynthesis via each cycloartenol and lanosterol, we performed feeding experiments by using [6-(13)C(2)H(3)]mevalonate with Arabidopsis seedlings. Applying (13)C-{(1)H}{(2)H} nuclear magnetic resonance (NMR) techniques, the elucidation of deuterium on C-19 behavior of phytosterol provided evidence that small amounts of phytosterol were biosynthesized via lanosterol. The levels of phytosterol increased on overexpression of LAS1, and phytosterols derived from lanosterol were not observed in a LAS1-knockout plant. This is direct evidence to indicate that the biosynthetic pathway for phytosterol via lanosterol exists in plant cells. We designate the biosynthetic pathway to phytosterols via lanosterol "the lanosterol pathway." LAS1 expression is reported to be induced by the application of jasmonate and is thought to have evolved from an ancestral cycloartenol synthase to a triterpenoid synthase, such as beta-amyrin synthase and lupeol synthase. Considering this background, the lanosterol pathway may contribute to the biosynthesis of not only phytosterols, but also steroids as secondary metabolites.

  3. Fungal community, Fusarium head blight complex and secondary metabolites associated with malting barley grains harvested in Umbria, central Italy.

    Science.gov (United States)

    Beccari, Giovanni; Senatore, Maria Teresa; Tini, Francesco; Sulyok, Michael; Covarelli, Lorenzo

    2018-05-20

    In recent years, due to the negative impact of toxigenic mycobiota and of the accumulation of their secondary metabolites in malting barley grains, monitoring the evolution of fungal communities in a certain cultivation area as well as detecting the different mycotoxins present in the raw material prior to malting and brewing processes have become increasingly important. In this study, a survey was carried out on malting barley samples collected after their harvest in the Umbria region (central Italy). Samples were analyzed to determine the composition of the fungal community, to identify the isolated Fusarium species, to quantify fungal secondary metabolites in the grains and to characterize the in vitro mycotoxigenic profile of a subset of the isolated Fusarium strains. The fungal community of barley grains was mainly composed of microorganisms belonging to the genus Alternaria (77%), followed by those belonging to the genus Fusarium (27%). The Fusarium head blight (FHB) complex was represented by nine species with the predominance of Fusarium poae (37%), followed by Fusarium avenaceum (23%), Fusarium graminearum (22%) and Fusarium tricinctum (7%). Secondary metabolites biosynthesized by Alternaria and Fusarium species were present in the analyzed grains. Among those biosynthesized by Fusarium species, nivalenol and enniatins were the most prevalent ones. Type A trichothecenes (T-2 and HT-2 toxins) as well as beauvericin were also present with a high incidence. Conversely, the number of samples contaminated with deoxynivalenol was low. Conjugated forms, such as deoxynivalenol-3-glucoside and HT-2-glucoside, were detected for the first time in malting barley grains cultivated in the surveyed area. In addition, strains of F. avenaceum and F. tricinctum showed the ability to biosynthesize in vitro high concentrations of enniatins. The analysis of fungal secondary metabolites, both in the grains and in vitro, revealed also the presence of other compounds, for which

  4. The importance of mass spectrometric dereplication in fungal secondary metabolite analysis

    DEFF Research Database (Denmark)

    Nielsen, Kristian Fog; Larsen, Thomas Ostenfeld

    2015-01-01

    Having entered the Genomic Era, it is now evident that the biosynthetic potential of filamentous fungi is much larger than was thought even a decade ago. Fungi harbor many cryptic gene clusters encoding for the biosynthesis of polyketides, non-ribosomal peptides, and terpenoids - which can all...... the importance of each stage of the process from sample preparation to chromatographic separation and finally toward both manual and more targeted methods for automated dereplication of fungal natural products using state-of-the art MS instrumentation....

  5. Rewiring a secondary metabolite pathway towards itaconic acid production in Aspergillus niger.

    Science.gov (United States)

    Hossain, Abeer H; Li, An; Brickwedde, Anja; Wilms, Lars; Caspers, Martien; Overkamp, Karin; Punt, Peter J

    2016-07-28

    The industrially relevant filamentous fungus Aspergillus niger is widely used in industry for its secretion capabilities of enzymes and organic acids. Biotechnologically produced organic acids promise to be an attractive alternative for the chemical industry to replace petrochemicals. Itaconic acid (IA) has been identified as one of the top twelve building block chemicals which have high potential to be produced by biotechnological means. The IA biosynthesis cluster (cadA, mttA and mfsA) has been elucidated in its natural producer Aspergillus terreus and transferred to A. niger to enable IA production. Here we report the rewiring of a secondary metabolite pathway towards further improved IA production through the overexpression of a putative cytosolic citrate synthase citB in a A. niger strain carrying the IA biosynthesis cluster. We have previously shown that expression of cadA from A. terreus results in itaconic acid production in A. niger AB1.13, albeit at low levels. This low-level production is boosted fivefold by the overexpression of mttA and mfsA in itaconic acid producing AB1.13 CAD background strains. Controlled batch cultivations with AB1.13 CAD + MFS + MTT strains showed increased production of itaconic acid compared with AB1.13 CAD strain. Moreover, preliminary RNA-Seq analysis of an itaconic acid producing AB1.13 CAD strain has led to the identification of the putative cytosolic citrate synthase citB which was induced in an IA producing strain. We have overexpressed citB in a AB1.13 CAD + MFS + MTT strain and by doing so hypothesize to have targeted itaconic acid production to the cytosolic compartment. By overexpressing citB in AB1.13 CAD + MFS + MTT strains in controlled batch cultivations we have achieved highly increased titers of up to 26.2 g/L IA with a productivity of 0.35 g/L/h while no CA was produced. Expression of the IA biosynthesis cluster in Aspergillus niger AB1.13 strain enables IA production. Moreover, in the AB1.13 CAD

  6. Capacity for absorption of water-soluble secondary metabolites greater in birds than in rodents.

    Science.gov (United States)

    Karasov, William H; Caviedes-Vidal, Enrique; Bakken, Bradley Hartman; Izhaki, Ido; Samuni-Blank, Michal; Arad, Zeev

    2012-01-01

    Plant secondary metabolites (SMs) are pervasive in animal foods and potentially influence feeding behavior, interspecies interactions, and the distribution and abundance of animals. Some of the major classes of naturally occurring SMs in plants include many water-soluble compounds in the molecular size range that could cross the intestinal epithelium via the paracellular space by diffusion or solvent drag. There are differences among species in paracellular permeability. Using Middle Eastern rodent and avian consumers of fruits containing SMs, we tested the hypothesis that avian species would have significantly higher paracellular permeability than rodent species. Permeability in intact animals was assessed using standard pharmacological methodology to measure absorption of two radiolabeled, inert, neutral water-soluble probes that do not interact with intestinal nutrient transporters, L-arabinose (M(r) = 150.1 Da) and lactulose (M(r) = 342.3 Da). We also measured absorption of labeled 3-O-methyl-D-glucose (3OMD-glucose; M(r) = 194.2 Da), which is a nonmetabolized analogue of D-glucose that is passively absorbed through the paracellular space but also transported across the enterocyte membranes. Most glucose was absorbed by all species, but arabinose fractional absorption (f) was nearly three times higher in birds (1.03±0.17, n = 15 in two species) compared to rodents (0.37±0.06, n = 10 in two species) (Pbirds of arabinose exceeded those of 3OMD-glucose. Our findings are in agreement with previous work showing that the paracellular pathway is more prominent in birds relative to nonflying mammals, and suggests that birds may be challenged by greater absorption of water-soluble, dietary SMs. The increased expression of the paracellular pathway in birds hints at a tradeoff: the free energy birds gain by absorbing water-soluble nutrients passively may be offset by the metabolic demands placed on them to eliminate concomitantly absorbed SMs.

  7. Secondary metabolites as anti-nutritional factors in locally used halophytic forage/fodder

    International Nuclear Information System (INIS)

    Ehsen, S.; Qasim, M.; Abideen, Z.; Rizve, R. F.; Gul, B.; Ansari, R.

    2016-01-01

    Rampant salinity coupled with population explosion necessitates search for suitable alternatives to conventional sources of food both for human and animal consumption. While it may be difficult to change our culinary preferences, training animals to adopt a changed diet of nonconventional salt tolerant plants is easier. Using these wild plants however, requires estimation of undesirable secondary metabolites (SMs) produced during stressful conditions, which may be harmful for health of animals. Some of these anti-nutritional components (total phenols, flavonoids, tannins, nitrates, saponins and oxalates) were determined in 22 halophytes locally used as fodder/forage. Most of the species were perennial shrubs and herbs of an area where environmental conditions like high mean annual temperature (∼35 degree C), low rainfall (< 250mm) with soil mostly dry (average 2 percent moisture) and saline (average EC 13 dSm/sup -1/) supported the growth of halophytes and xerophytes. Values of SMs in the studied plants ranged from 0.13-4.05 percent for total phenols, 0.38-6.99 percent for tannins, 0.15-1.50 percent for flavonoids, 0.10-1.15 percent for nitrates, 0.45-8.68 percent for saponins and 0.36-2.34 percent for oxalates. Most of the species (19) contained low to moderate amount of individual as well as total SMs which were within the non-toxic ranges. However, three species distributed in coastal habitats where average soil salinity (27.67 dSm-1) was considerably higher than inland ones (7.09 dSm-1) had SMs contents above the safe limits. It is evident from these Results that most of these plants contained moderate to low levels of anti-nutritional factors, which lies under the safe limits and hence, could be used as a potential feed source to raise animals, particularly in arid/semiarid areas. Additionally, these plants represents a viable choice as they can be grown without encroaching on agricultural lands and fresh water resources and could promote livestock

  8. Secondary metabolites from Tetracera potatoria stem bark with anti-mycobacterial activity.

    Science.gov (United States)

    Fomogne-Fodjo, M C Y; Ndinteh, D T; Olivier, D K; Kempgens, P; van Vuuren, S; Krause, R W M

    2017-01-04

    Tetracera potatoria Afzel. Exg. Don (Dilleniaceae) is a medicinal plant used traditionally in Africa for the treatment of tuberculosis related ailments and respiratory infections. The antibacterial activity of the medium polar extracts of T. potatoria leaves and stem bark was recently reported against Mycobacterium smegmatis (MIC 25µg/mL) and M. aurum (65µg/mL), two fast-growing Mycobacterium strains used as model micro-organisms for the more pathogenic strain Mycobacterium tuberculosis (Fomogne-Fodjo et al., 2014). The aim of this study was consequently to isolate the compounds possibly contributing to this activity, and which may therefore be promising precursors to be used for the development of novel anti-TB drugs. T. potatoria medium polar extract [MeOH/DCM (1:1, v/v)] was fractionated sequentially with petroleum ether to which EtOAC and MeOH were gradually added to increase the polarity. The examination of T. potatoria extract and its fractions was guided by bioassays for anti-mycobacterial activity against M. smegmatis (ATCC 23246) and M. aurum (NCTC 10437) using the minimum inhibitory concentration (MIC) method. All the isolated compounds were structurally elucidated using spectroscopic techniques and evaluated for their anti-mycobacterial activity. Two novel secondary metabolites (1, 2) named tetraceranoate and N-hydroxy imidate-tetracerane, together with five known compounds [β-stigmasterol (3), stigmast-5-en-3β-yl acetate (4), betulinic acid (5), betulin (6) and lupeol (7)] were isolated and identified. Tetraceranoate exhibited the best activity against M. smegmatis with a minimum inhibitory concentration (MIC) of 7.8µg/mL, while β-stigmasterol, betulinic acid and betulin showed appreciable anti-mycobacterial activity against both strains (MIC 15µg/mL). Seven compounds were isolated from the medium polar extract [MeOH/DCM (1:1, v/v)] of T. potatoria stem bark. Only tetraceranoate one of the isolated compounds showed antibacterial activity against

  9. Metabolite profiling approach reveals the interface of primary and secondary metabolism in colored cauliflowers (Brassica oleracea L. ssp. botrytis).

    Science.gov (United States)

    Park, Soo-Yun; Lim, Sun-Hyung; Ha, Sun-Hwa; Yeo, Yunsoo; Park, Woo Tae; Kwon, Do Yeon; Park, Sang Un; Kim, Jae Kwang

    2013-07-17

    In the present study, carotenoids, anthocyanins, and phenolic acids of cauliflowers ( Brassica oleracea L. ssp. botrytis) with various colored florets (white, yellow, green, and purple) were characterized to determine their phytochemical diversity. Additionally, 48 metabolites comprising amino acids, organic acids, sugars, and sugar alcohols were identified using gas chromatography-time-of-flight mass spectrometry (GC-TOFMS). Carotenoid content was considerably higher in green cauliflower; anthocyanins were detected only in purple cauliflower. Phenolic acids were higher in both green and purple cauliflower. Results of partial least-squares discriminant, Pearson correlation, and hierarchical clustering analyses showed that green cauliflower is distinct on the basis of the high levels of amino acids and clusters derived from common or closely related biochemical pathways. These results suggest that GC-TOFMS-based metabolite profiling, combined with chemometrics, is a useful tool for determining phenotypic variation and identifying metabolic networks connecting primary and secondary metabolism.

  10. Potentially harmful secondary metabolites produced by indoor Chaetomium species on artificially and naturally contaminated building materials

    DEFF Research Database (Denmark)

    Dosen, Ina; Nielsen, Kristian Fog; Clausen, Geo

    2017-01-01

    , have been screened for, and thus detected in buildings. In this study, we used a liquid chromatography-high resolution mass spectrometry approach to screen both artificially and naturally infected building materials for all the Chaetomium metabolites described in the literature. Pure agar cultures were...... also investigated in order to establish differences between metabolite production in vitro and on building materials as well as comparison to non-indoor reference strains. On building materials six different chaetoglobosins were detected in total concentrations of up to 950 mg/m2 from C. globosum along...... with three different chaetoviridins/chaetomugilins in concentrations up to 200 mg/m2. Indoor Chaetomium spp. preferred wood-based materials over gypsum, both in terms of growth rate and metabolite production. Cochliodones were detected for the first time on all building materials infected by both C. globosum...

  11. LC-MS based analysis of secondary metabolites from Chaetomium and Stachybotrys growth in indoor environments

    DEFF Research Database (Denmark)

    Dosen, Ina

    of causing negative health impact. With this in mind, a prime goal of this PhD study was to develop and optimize methods for qualitative and semi-quantitative analysis of secondary metabolites and bioactive compounds produced by Stachybotrys spp. and Chaetomium spp. The main analytical technique used...... and not included in the library, as well as tentatively identified compounds. Metabolite profiling of Stachybotrys spp. and Chaetomium spp. was performed in pure agar cultures. Thereafter, mapped secondary metabolites were screened for in extracts of artificially inoculated building materials and materials from...... analytical tools were applied to the analysis of naturally contaminated building materials, where presence of all previously mapped metabolites was confirmed. Work done on Stachybotrys spp showed no significant difference in metabolite profiles obtained in vitro and in vivo. Concurrently the study...

  12. Functional Genome Mining for Metabolites Encoded by Large Gene Clusters through Heterologous Expression of a Whole-Genome Bacterial Artificial Chromosome Library in Streptomyces spp.

    Science.gov (United States)

    Xu, Min; Wang, Yemin; Zhao, Zhilong; Gao, Guixi; Huang, Sheng-Xiong; Kang, Qianjin; He, Xinyi; Lin, Shuangjun; Pang, Xiuhua; Deng, Zixin

    2016-01-01

    ABSTRACT Genome sequencing projects in the last decade revealed numerous cryptic biosynthetic pathways for unknown secondary metabolites in microbes, revitalizing drug discovery from microbial metabolites by approaches called genome mining. In this work, we developed a heterologous expression and functional screening approach for genome mining from genomic bacterial artificial chromosome (BAC) libraries in Streptomyces spp. We demonstrate mining from a strain of Streptomyces rochei, which is known to produce streptothricins and borrelidin, by expressing its BAC library in the surrogate host Streptomyces lividans SBT5, and screening for antimicrobial activity. In addition to the successful capture of the streptothricin and borrelidin biosynthetic gene clusters, we discovered two novel linear lipopeptides and their corresponding biosynthetic gene cluster, as well as a novel cryptic gene cluster for an unknown antibiotic from S. rochei. This high-throughput functional genome mining approach can be easily applied to other streptomycetes, and it is very suitable for the large-scale screening of genomic BAC libraries for bioactive natural products and the corresponding biosynthetic pathways. IMPORTANCE Microbial genomes encode numerous cryptic biosynthetic gene clusters for unknown small metabolites with potential biological activities. Several genome mining approaches have been developed to activate and bring these cryptic metabolites to biological tests for future drug discovery. Previous sequence-guided procedures relied on bioinformatic analysis to predict potentially interesting biosynthetic gene clusters. In this study, we describe an efficient approach based on heterologous expression and functional screening of a whole-genome library for the mining of bioactive metabolites from Streptomyces. The usefulness of this function-driven approach was demonstrated by the capture of four large biosynthetic gene clusters for metabolites of various chemical types, including

  13. Secondary metabolites produced by marine streptomyces as antibiofilm and quorum-sensing inhibitor of uropathogen Proteus mirabilis.

    Science.gov (United States)

    Younis, Khansa Mohammed; Usup, Gires; Ahmad, Asmat

    2016-03-01

    Quorum-sensing regulates bacterial biofilm formation and virulence factors, thereby making it an interesting target for attenuating pathogens. In this study, we investigated anti-biofilm and anti-quorum-sensing compounds from secondary metabolites of halophiles marine streptomyces against urinary catheter biofilm forming Proteus mirabilis without effect on growth viability. A total of 40 actinomycetes were isolated from samples collected from different places in Iraq including marine sediments and soil samples. Fifteen isolates identified as streptomyces and their supernatant screened as anti-quorum-sensing by inhibiting quorum-sensing regulated prodigiosin biosynthesis of Serratia marcescens strain Smj-11 as a reporter strain. Isolate Sediment Lake Iraq (sdLi) showed potential anti-quorum-sensing activity. Out of 35 clinical isolates obtained from Urinary catheter used by patient at the Universiti Kebangsaan Malaysia Medical Center, 22 isolates were characterized and identified as Proteus mirabilis. Isolate Urinary Catheter B4 (UCB4) showed the highest biofilm formation with highest resistance to used antibiotic and was chosen for further studies. Ethyl acetate secondary metabolites extract was produced from sdLi isolate. First, we determined the Minimum Inhibitory Concentration (MIC) of sdLi crude extract against UCB4 isolate, and all further experiments used concentrations below the MIC. Tests of subinhibitory concentrations of sdLi crude extract showed good inhibition against UCB4 isolate biofilm formation on urinary catheter and cover glass using Scanning electron microscopy and light microscopy respectively. The influence of sub-MIC of sdLi crude extract was also found to attenuate the quorum sensing (QS)-dependent factors such as hemolysin activity, urease activity, pH value, and motility of UCB4 isolate. Evidence is presented that these nontoxic secondary metabolites may act as antagonists of bacterial quorum sensing by competing with quorum-sensing signals

  14. Secondary metabolites from Pinus mugo Turra subsp. mugo growing in the Majella National Park (Central Apennines, Italy).

    Science.gov (United States)

    Venditti, Alessandro; Serrilli, Anna Maria; Vittori, Sauro; Papa, Fabrizio; Maggi, Filippo; Di Cecco, Mirella; Ciaschetti, Gianpiero; Bruno, Maurizio; Rosselli, Sergio; Bianco, Amandodoriano

    2013-11-01

    In this study, we examined the composition regarding secondary metabolites of P. mugo Turra ssp. mugo growing in the protected area of Majella National Park, which is the southernmost station of the habitat of this species. Both the nonpolar and polar fractions were considered. In particular, the essential-oil composition showed a high variety of compounds, and 109 compounds were detected, and 101 were identified, among which abietane-type compounds have a taxonomic relevance. Abietanes were also isolated from the polar fraction, together with an acylated flavonol and a remarkably high amount of shikimic acid. Copyright © 2013 Verlag Helvetica Chimica Acta AG, Zürich.

  15. Quorum quenchers and sensors as possible roles for mycotoxins and other secondary metabolites of fungi

    Science.gov (United States)

    The assumed role for mycotoxins is to act as defensive metabolites thus serving as protection for fungi from biotic antagonisms and as such do not interact with the daily metabolic requirements of the producing fungus. Preventive strategies are devoted to reducing the accumulation of mycotoxins bas...

  16. Biosynthesis, localization and ecological role of pyrethrins and linked secondary metabolites in pyrethrum

    NARCIS (Netherlands)

    Jongsma, M.A.; Ramirez, A.

    2017-01-01

    The perennial herbaceous plant Tanacetum cinerariifolium, also known as pyrethrum, is a daisy-like flower with an inherent ability to produce considerable amounts of biologically active metabolites, especially pyrethrins, probably intended for self-defence. The discovery of pyrethrin toxicity

  17. Secondary metabolite gene clusters in the entomopathogen fungus Metarhizium anisopliae: genome identification and patterns of expression in a cuticle infection model

    Directory of Open Access Journals (Sweden)

    Nicolau Sbaraini

    2016-10-01

    Full Text Available Abstract Background The described species from the Metarhizium genus are cosmopolitan fungi that infect arthropod hosts. Interestingly, while some species infect a wide range of hosts (host-generalists, other species infect only a few arthropods (host-specialists. This singular evolutionary trait permits unique comparisons to determine how pathogens and virulence determinants emerge. Among the several virulence determinants that have been described, secondary metabolites (SMs are suggested to play essential roles during fungal infection. Despite progress in the study of pathogen-host relationships, the majority of genes related to SM production in Metarhizium spp. are uncharacterized, and little is known about their genomic organization, expression and regulation. To better understand how infection conditions may affect SM production in Metarhizium anisopliae, we have performed a deep survey and description of SM biosynthetic gene clusters (BGCs in M. anisopliae, analyzed RNA-seq data from fungi grown on cattle-tick cuticles, evaluated the differential expression of BGCs, and assessed conservation among the Metarhizium genus. Furthermore, our analysis extended to the construction of a phylogeny for the following three BGCs: a tropolone/citrinin-related compound (MaPKS1, a pseurotin-related compound (MaNRPS-PKS2, and a putative helvolic acid (MaTERP1. Results Among 73 BGCs identified in M. anisopliae, 20 % were up-regulated during initial tick cuticle infection and presumably possess virulence-related roles. These up-regulated BGCs include known clusters, such as destruxin, NG39x and ferricrocin, together with putative helvolic acid and, pseurotin and tropolone/citrinin-related compound clusters as well as uncharacterized clusters. Furthermore, several previously characterized and putative BGCs were silent or down-regulated in initial infection conditions, indicating minor participation over the course of infection. Interestingly, several up

  18. [Secondary metabolites of a marine mangrove fungus (Penicillium sp. no. 2556) from South China Sea].

    Science.gov (United States)

    Li, Chun-Yuan; Ding, Wei-Jia; Shao, Chang-Lun; She, Zhi-Gang; Lin, Yong-Cheng

    2008-07-01

    The metabolites of a marine mangrove fungus (Penicillium sp. No. 2556) were studied in this paper and six compounds were isolated from the fermentation liquid. Their structures were elucidated by spectroscopy methods as Sch54796 (1), Sch54794 (2), 4-hydroxybenzoic acid (3), urail (4), succinic acid (5), Vermopyrone (6). Among them, compounds 1, 2 and 6 were firstly isolated from Penicillium sp., Coumpounds 1 and 2 remarkably inhibited the growth of cancer cell lines hep2 and hepG2.

  19. Effects of Secondary Plant Metabolites on Microbial Populations: Changes in Community Structure and Metabolic Activity in Contaminated Environments

    Directory of Open Access Journals (Sweden)

    Lucie Musilova

    2016-07-01

    Full Text Available Secondary plant metabolites (SPMEs play an important role in plant survival in the environment and serve to establish ecological relationships between plants and other organisms. Communication between plants and microorganisms via SPMEs contained in root exudates or derived from litter decomposition is an example of this phenomenon. In this review, the general aspects of rhizodeposition together with the significance of terpenes and phenolic compounds are discussed in detail. We focus specifically on the effect of SPMEs on microbial community structure and metabolic activity in environments contaminated by polychlorinated biphenyls (PCBs and polyaromatic hydrocarbons (PAHs. Furthermore, a section is devoted to a complex effect of plants and/or their metabolites contained in litter on bioremediation of contaminated sites. New insights are introduced from a study evaluating the effects of SPMEs derived during decomposition of grapefruit peel, lemon peel, and pears on bacterial communities and their ability to degrade PCBs in a long-term contaminated soil. The presented review supports the “secondary compound hypothesis” and demonstrates the potential of SPMEs for increasing the effectiveness of bioremediation processes.

  20. Secondary Metabolite Profiles and Mating Populations of Fusarium species in Section Liseola Associated with Bakanae Disease of Rice

    Directory of Open Access Journals (Sweden)

    Nur Ain Izzati, M. Z.

    2008-01-01

    Full Text Available A total of 25 strains of Fusarium species that belong to F. fujikuroi (a pathogen of bakanae disease, F. proliferatum, F. sacchari, F. subglutinans and F. verticillioides were isolated from rice plants showing typical bakanae symptoms in Malaysia and Indonesia and screened for their secondary metabolites. The objectives of the studies were to determine the physiological variability based on production of moniliformin (MON, fumonisin (FB1, gibberellic acid (GA3 and fusaric acid (FA as well as to ascertain the mating populations (MPs within the Gibberella fujikuroi species complex based on their ability to produce perithecia and viable ascospores. Production of GA3 could be used to separate F. fujikuroi that belongs to MP-C from other species. In crosses with seven standard testers of MPs, 76% of strains could be assigned to at least one of the G. fujikuroi species complex namely MP-A (G. moniliformis, MP-B (G. sacchari, MP-C (G. fujikuroi and MP-D (G. intermedia. Single strain (M3237P that was assigned as MP-C, and has also been identified morphologically as F. fujikuroi was also crossed-fertile with MP-D tester. The secondary metabolites profiles and the presence of MP-A, MP-B, MP-C and MP-D strains on samples of bakanae-infected rice plants are new records in Malaysia.

  1. Light-induced biochemical variations in secondary metabolite production and antioxidant activity in callus cultures of Stevia rebaudiana (Bert).

    Science.gov (United States)

    Ahmad, Naveed; Rab, Abdur; Ahmad, Nisar

    2016-01-01

    Stevia rebaudiana (S. rebaudiana) is a very important species with worldwide medicinal and commercial uses. Light is one of the major elicitors that fluctuate morphogenic potential and biochemical responses. In the present study, we investigated the effect of various spectral lights on biomass accumulation and secondary metabolite production in callus cultures of S. rebaudiana. Leaf explants were placed on Murashige and Skoog (MS) medium and exposed to various spectral lights. 6-Benzyle adenine (BA) and 2, 4-dichlorophenoxy acetic acid (2, 4-D; 2.0 mgl(-1)) were used for callus induction. The control light (16/8h) produced optimum callogenic response (92.73%) than other colored lights. Compared to other colored lights, control grown cultures displayed maximum biomass accumulation (5.78 gl(-1)) during a prolonged log phase at the 18th day of growth kinetics. Cultures grown under blue light enhanced total phenolic content (TPC; 102.32 μg/g DW), total flavonoid content (TFC; 22.07 μg/g DW) and total antioxidant capacity (TAC; 11.63 μg/g DW). On the contrary, green and red lights improved reducing power assay (RPA; 0.71Fe(II)g(-1) DW) and DPPH-radical scavenging activity (DRSA; 80%). Herein, we concluded that the utilization of colored lights is a promising strategy for enhanced production of antioxidant secondary metabolites in callus cultures of S. rebaudiana. Copyright © 2015 Elsevier B.V. All rights reserved.

  2. [Effects of elicitors on growth of adventitious roots and contents of secondary metabolites in Tripterygium wilfordii Hook. f].

    Science.gov (United States)

    Li, Yan; Zhao, Lei; Cui, Lei; Lei, Jiamin; Zhang, Xing

    2015-05-01

    To study the effects of the extract of fungal elicitor, AgNO3, MeJA and yeast on the growth and content of secondary metabolites of adventitious roots in Tripterygium wilfordii. The above elicitors were supplemented to the medium, the growth and the content of secondary metabolites were measured. When the medium was supplemented with the elicitor Glomerella cingulata or Collectotrichum gloeosporioides, the content of triptolide was increased by 2.24 and 1.93-fold, the alkaloids content was increased by 2.02 and 2.07-fold, respectively. The optimal concentration of G. cingulata was 50 μg/mL for accumulation of triptolide, alkaloids and for the growth of adventitious roots. AgNO3 inhibited the growth of adventitious roots and the accumulation of the alkaloids, whereas it (at 25 μmol/L) increased the accumulation of triptolide by 1.71-fold compared to the control. The growth of adventitious roots, the contents of triptolide and alkaloids were increased 1.04, 1.64 and 2.12-folds, respectively when MeJA was at 50 μmol/L. When the concentration of yeast reached 2 g/L, the content of triptolide increased 1.48-folds. This research demonstrated that supplementation of AgNO3 and yeast enhanced the biosynthesis of triptolide in adventitious roots and the synergism of G. cingulata and MeJA could promote the biosynthesis of both triptolide and alkaloids.

  3. Heavy metals in contaminated environment: Destiny of secondary metabolite biosynthesis, oxidative status and phytoextraction in medicinal plants.

    Science.gov (United States)

    Asgari Lajayer, Behnam; Ghorbanpour, Mansour; Nikabadi, Shahab

    2017-11-01

    Contamination of soils, water and air with toxic heavy metals by various human activities is a crucial environmental problem in both developing and developed countries. Heavy metals could be introduced into medicinal plant products through contaminated environment (soil, water and air resources) and/or poor production practices. Growing of medicinal plants in heavy metal polluted environments may eventually affect the biosynthesis of secondary metabolites, causing significant changes in the quantity and quality of these compounds. Certain medicinal and aromatic plants can absorb and accumulate metal contaminants in the harvestable foliage and, therefore, considered to be a feasible alternative for remediation of polluted sites without any contamination of essential oils. Plants use different strategies and complex arrays of enzymatic and non-enzymatic anti-oxidative defense systems to cope with overproduction of ROS causes from the heavy metals entered their cells through foliar and/or root systems. This review summarizes the reports of recent investigations involving heavy metal accumulation by medicinal plants and its effects on elicitation of secondary metabolites, toxicity and detoxification pathways, international standards regarding in plants and plant-based products, and human health risk assessment of heavy metals in soil-medicinal plants systems. Copyright © 2017 Elsevier Inc. All rights reserved.

  4. Genomic and transcriptomic analyses reveal differential regulation of diverse terpenoid and polyketides secondary metabolites in Hericium erinaceus.

    Science.gov (United States)

    Chen, Juan; Zeng, Xu; Yang, Yan Long; Xing, Yong Mei; Zhang, Qi; Li, Jia Mei; Ma, Ke; Liu, Hong Wei; Guo, Shun Xing

    2017-08-31

    The lion's mane mushroom Hericium erinaceus is a famous traditional medicinal fungus credited with anti-dementia activity and a producer of cyathane diterpenoid natural products (erinacines) useful against nervous system diseases. To date, few studies have explored the biosynthesis of these compounds, although their chemical synthesis is known. Here, we report the first genome and tanscriptome sequence of the medicinal fungus H. erinaceus. The size of the genome is 39.35 Mb, containing 9895 gene models. The genome of H. erinaceus reveals diverse enzymes and a large family of cytochrome P450 (CYP) proteins involved in the biosynthesis of terpenoid backbones, diterpenoids, sesquiterpenes and polyketides. Three gene clusters related to terpene biosynthesis and one gene cluster for polyketides biosynthesis (PKS) were predicted. Genes involved in terpenoid biosynthesis were generally upregulated in mycelia, while the PKS gene was upregulated in the fruiting body. Comparative genome analysis of 42 fungal species of Basidiomycota revealed that most edible and medicinal mushroom show many more gene clusters involved in terpenoid and polyketide biosynthesis compared to the pathogenic fungi. None of the gene clusters for terpenoid or polyketide biosynthesis were predicted in the poisonous mushroom Amanita muscaria. Our findings may facilitate future discovery and biosynthesis of bioactive secondary metabolites from H. erinaceus and provide fundamental information for exploring the secondary metabolites in other Basidiomycetes.

  5. Microbial secondary metabolites are an alternative approaches against insect vector to prevent zoonotic diseases

    Directory of Open Access Journals (Sweden)

    Dharumadurai Dhanasekaran

    2014-08-01

    Full Text Available Approximately 1500 naturally occurring microorganisms have been identified as potentially insecticidal agents. Metabolites from 942 microbial isolates were screened for insecticidal and properties. The isolates included 302 streptomycetes, 502 novel actinobacteria including representatives of 18 genera, 28 unidentified aerobic actinobacteria, 70 fungi and 40 bacteria other than actinobacteria showed the insecticidal activity. Most spore-forming bacteria pathogenic to insects belong to the family Bacillaceae. Only four Bacillus species namely Bacillus thuringiensis, Bacillus popilliae, Bacillus lentimorbus, Bacillus sphaericus have been closely examined as insect control agents. Fungi are applied directly in the form of spores, mycelia or blastospores or by their metabolites. Many viruses that belong to the family Baculoviridae are pathogenic in insects. The microbial insecticides are generally pest-specific, readily biodegradable and usually lack toxicity to higher animals. This review paper communicates the insect problem in the transmission of diseases in human, animals, plants and problem of chemical insecticides control of insects using microbial metabolites from actinobacteria, bacteria, fungi and viruses.

  6. Turmeric (Curcuma longa): miRNAs and their regulating targets are involved in development and secondary metabolite pathways.

    Science.gov (United States)

    Singh, Noopur; Sharma, Ashok

    Turmeric has been used as a therapeutic herb over centuries in traditional medicinal systems due to the presence of several secondary metabolite compounds. microRNAs are known to regulate gene expression at the post-transcriptional level by transcriptional cleavage or translation repression. miRNAs have been demonstrated to play an active role in secondary metabolism regulation. The present work was focused on the identification of the miRNAs involved in the regulation of secondary metabolite and development process of turmeric. Eighteen miRNA families were identified for turmeric. Sixteen miRNA families were observed to regulate 238 target transcripts. LncRNAs targets of the putative miRNA candidates were also predicted. Our results indicated their role in binding, reproduction, stress, and other developmental processes. Gene annotation and pathway analysis illustrated the biological function of the targets regulated by the putative miRNAs. The miRNA-mediated gene regulatory network also revealed co-regulated targets that were regulated by two or more miRNA families. miR156 and miR5015 were observed to be involved in rhizome development. miR5021 showed regulation for terpenoid backbone biosynthesis and isoquinoline alkaloid biosynthesis pathways. The flavonoid biosynthesis pathway was observed to be regulated by miR2919. The analysis revealed the probable involvement of three miRNAs (miR1168.2, miR156b and miR1858) in curcumin biosynthesis. Other miRNAs were found to be involved in the growth and developmental process of turmeric. Phylogenetic analysis of selective miRNAs was also performed. Copyright © 2017 Académie des sciences. Published by Elsevier Masson SAS. All rights reserved.

  7. Changes of primary and secondary metabolites in barley plants exposed to CdO nanoparticles

    Czech Academy of Sciences Publication Activity Database

    Večeřová, Kristýna; Večeřa, Zbyněk; Dočekal, Bohumil; Oravec, Michal; Pompeiano, Antonio; Tříska, Jan; Urban, Otmar

    2016-01-01

    Roč. 218, NOV (2016), s. 207-218 ISSN 0269-7491 R&D Projects: GA MŠk(CZ) LO1415; GA ČR(CZ) GAP503/11/2315; GA ČR(CZ) GBP503/12/G147; GA MŠk(CZ) LD15039 Institutional support: RVO:67179843 ; RVO:68081715 Keywords : Barley * CdO nanoparticles * Gas chromatography * High performance liquid chromatography * Mass spectrometry * Plant metabolites Subject RIV: EH - Ecology, Behaviour; CB - Analytical Chemistry, Separation (UIACH-O) Impact factor: 5.099, year: 2016

  8. antiSMASH 3.0—a comprehensive resource for the genome mining of biosynthetic gene clusters

    DEFF Research Database (Denmark)

    Weber, Tilmann; Blin, Kai; Duddela, Srikanth

    2015-01-01

    Microbial secondary metabolism constitutes a rich source of antibiotics, chemotherapeutics, insecticides and other high-value chemicals. Genome mining of gene clusters that encode the biosynthetic pathways for these metabolites has become a key methodology for novel compound discovery. In 2011, we...... introduced antiSMASH, a web server and stand-alone tool for the automatic genomic identification and analysis of biosynthetic gene clusters, available at http://antismash.secondarymetabolites.org. Here, we present version 3.0 of antiSMASH, which has undergone major improvements. A full integration...... of the recently published ClusterFinder algorithm now allows using this probabilistic algorithm to detect putative gene clusters of unknown types. Also, a new dereplication variant of the ClusterBlast module now identifies similarities of identified clusters to any of 1172 clusters with known end products...

  9. Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices.

    Science.gov (United States)

    Park, J-H; Sulyok, M; Lemons, A R; Green, B J; Cox-Ganser, J M

    2018-05-04

    Recent developments in molecular and chemical methods have enabled the analysis of fungal DNA and secondary metabolites, often produced during fungal growth, in environmental samples. We compared 3 fungal analytical methods by analysing floor dust samples collected from an office building for fungi using viable culture, internal transcribed spacer (ITS) sequencing and secondary metabolites using liquid chromatography-tandem mass spectrometry. Of the 32 metabolites identified, 29 had a potential link to fungi with levels ranging from 0.04 (minimum for alternariol monomethylether) to 5700 ng/g (maximum for neoechinulin A). The number of fungal metabolites quantified per sample ranged from 8 to 16 (average = 13/sample). We identified 216 fungal operational taxonomic units (OTUs) with the number per sample ranging from 6 to 29 (average = 18/sample). We identified 37 fungal species using culture, and the number per sample ranged from 2 to 13 (average = 8/sample). Agreement in identification between ITS sequencing and culturing was weak (kappa = -0.12 to 0.27). The number of cultured fungal species poorly correlated with OTUs, which did not correlate with the number of metabolites. These suggest that using multiple measurement methods may provide an improved understanding of fungal exposures in indoor environments and that secondary metabolites may be considered as an additional source of exposure. © 2018 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.

  10. [Microscopic anatomy and volatile secondary metabolites at three stages of development of the inflorescences of Lantana camara (Verbenaceae)].

    Science.gov (United States)

    Caroprese Araque, José Fernando; Parra Garcés, María Isabel; Arrieta Prieto, Dagoberto; Stashenko, Elena

    2011-03-01

    Plants of the Verbenaceae family, like L. camara, have called the attention of researchers, not only because of its high diversity and its distribution around the world, but also for its variable use as popular medicine to treat diseases like tetanus, rheumatism and malaria, and as bactericide and insecticide. To assess this, the morphology and ontogeny of the inflorescences of Lantana camara and the chemical composition of volatile secondary metabolites were analyzed at three different ontogeny stages. Plants were collected from the experimental crop area in CENIVAM, Bucaramanga, Colombia. Fresh inflorescence stages were established and analyzed using a stereoscopic microscope, fixed in FAA and included in parafine. Transversal and longitudinal 10 microm thick sections were prepared using a rotative microtome, safranine-fastgreen stained and were observed and photographed using a light microscope. The chemical composition of volatile secondary metabolites were analyzed for each stage. The analytes, obtained from 0.7 g of plant, were isolated by solid phase micro-extraction in the headspace mode (HS-SPME) and were placed in 20 ml vials. The components were analyzed by gas chromatography coupled to mass spectrometry (GC-MS). Stage I was microscopically characterized by an immature development in which the meristematic differentiation begins with a mass of cells. In Stage II, the morphogenetic movement gives way to the formation of the respective floral sexual structures, calyx and corolla. In Stage III, the different organs are conspicuous: four stamens epipetals and didynamous, monocarpelar, biloculate and globose gynoecium, upper ovary and lateral stigma; the flowers are hermaphroditic. The main secondary metabolites detected by GC-MS were bicyclosesquiphellandrene, E-beta-farnesene, E-beta-caryophyllene, gamma-muurolene + gamma-curcumene and alpha-zingiberene. Nevertheless, this study reports for the first time in plant species alpha-gurjunene, gamma

  11. Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli.

    Science.gov (United States)

    Stahlhut, Steen G; Siedler, Solvej; Malla, Sailesh; Harrison, Scott J; Maury, Jérôme; Neves, Ana Rute; Forster, Jochen

    2015-09-01

    Plant secondary metabolites are an underutilized pool of bioactive molecules for applications in the food, pharma and nutritional industries. One such molecule is fisetin, which is present in many fruits and vegetables and has several potential health benefits, including anti-cancer, anti-viral and anti-aging activity. Moreover, fisetin has recently been shown to prevent Alzheimer's disease in mice and to prevent complications associated with diabetes type I. Thus far the biosynthetic pathway of fisetin in plants remains elusive. Here, we present the heterologous assembly of a novel fisetin pathway in Escherichia coli. We propose a novel biosynthetic pathway from the amino acid, tyrosine, utilizing nine heterologous enzymes. The pathway proceeds via the synthesis of two flavanones never produced in microorganisms before--garbanzol and resokaempferol. We show for the first time a functional biosynthetic pathway and establish E. coli as a microbial platform strain for the production of fisetin and related flavonols. Copyright © 2015 International Metabolic Engineering Society. Published by Elsevier Inc. All rights reserved.

  12. Linking secondary metabolites to biosynthesis genes in the fungal endophyte Cyanodermella asteris: The anti-cancer bisanthraquinone skyrin

    DEFF Research Database (Denmark)

    Jahn, Linda; Schafhauser, Thomas; Wibberg, Daniel

    2017-01-01

    Fungal aromatic polyketides display a very diverse and widespread group of natural products. Due to their excellent light absorption properties and widely studied biological activities, they offer numerous application for food, textile and pharmaceutical industry. The biosynthetic pathways...... far and further elucidation of the individual biosynthetic steps is needed to fully exploit the biotechnological and medicinal potential of these compounds. Here, we identified the bisanthraquinone skyrin as the main pigment of the fungus Cyanodermella asteris, an endophyte that has recently been...

  13. Bacillus velezensis RC 218 as a biocontrol agent to reduce Fusarium head blight and deoxynivalenol accumulation: Genome sequencing and secondary metabolite cluster profiles.

    Science.gov (United States)

    Palazzini, Juan M; Dunlap, Christopher A; Bowman, Michael J; Chulze, Sofía N

    2016-11-01

    Bacillus subtilis RC 218 was originally isolated from wheat anthers as a potential antagonist of Fusarium graminearum, the causal agent of Fusarium head blight (FHB). It was demonstrated to have antagonist activity against the plant pathogen under in vitro and greenhouse assays. The current study extends characterizing B. subtilis RC 218 with a field study and genome sequencing. The field study demonstrated that B. subtilis RC 218 could reduce disease severity and the associated mycotoxin (deoxynivalenol) accumulation, under field conditions. The genome sequencing allowed us to accurately determine the taxonomy of the strain using a phylogenomic approach, which places it in the Bacillus velezensis clade. In addition, the draft genome allowed us to use bioinformatics to mine the genome for potential metabolites. The genome mining allowed us to identify 9 active secondary metabolites conserved by all B. velezensis strains and one additional secondary metabolite, the lantibiotic ericin, which is unique to this strain. This study represents the first confirmed production of ericin by a B. velezensis strain. The genome also allowed us to do a comparative genomics with its closest relatives and compare the secondary metabolite production of the publically available B. velezensis genomes. The results showed that the diversity in secondary metabolites of strains in the B. velezensis clade is driven by strains making different antibacterials. Copyright © 2016 Elsevier GmbH. All rights reserved.

  14. Anti-inflammatory effects of secondary metabolites isolated from the marine-derived fungal strain Penicillium sp. SF-5629.

    Science.gov (United States)

    Ngan, Nguyen Thi Thanh; Quang, Tran Hong; Kim, Kwan-Woo; Kim, Hye Jin; Sohn, Jae Hak; Kang, Dae Gill; Lee, Ho Sub; Kim, Youn-Chul; Oh, Hyuncheol

    2017-03-01

    After the chemical investigation of the ethyl acetate extract of the marine-derived fungal strain Penicillium sp. SF-5629, the isolation and structural elucidation of eight secondary metabolites, including (3R,4S)-6,8-dihydroxy-3,4,7-trimethylisocoumarin (1), (3S,4S)-sclerotinin A (2), penicitrinone A (3), citrinin H1 (4), emodin (5), ω-hydroxyemodin (6), 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (7), and 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (8) were carried out. Evaluation of the anti-inflammatory activity of these metabolites showed that 4 inhibited nitric oxide and prostaglandin E2 production in lipopolysaccharide-stimulated BV2 microglia, with IC 50 values of 8.1 ± 1.9 and 8.0 ± 2.8 μM, respectively. The inhibitory function of 4 was confirmed based on decreases in inducible nitric oxide synthesis and cyclooxygenase-2 gene expression. In addition, 4 was found to suppress the phosphorylation of inhibitor kappa B-α, interrupt the nuclear translocation of nuclear factor kappa B, and decrease the activation of p38 mitogen-activated protein kinase.

  15. Antimicrobial activities of secondary metabolites and phylogenetic study of sponge endosymbiotic bacteria, Bacillus sp. at Agatti Island, Lakshadweep Archipelago

    Directory of Open Access Journals (Sweden)

    Gopi Mohan

    2016-09-01

    Full Text Available Twenty-one species of sponges were recorded under the class of Demospongiae and Calcareous sponges of which 19 species were new to Agatti reef. A total of 113 Sponge endosymbiotic bacterial strains were isolated from twenty-one species of sponges and screened for antimicrobial activity. Five bacterial strains of sponge endosymbiotic bacteria (SEB namely SEB32, SEB33, SEB36, SEB43 and SEB51 showed antimicrobial activity against virulent marine fish pathogens such as Vibrio alginolyticus, Vibrio vulnificus, Vibrio parahaemolyticus, Aeromonas salmonicida, Flavobacterium sp., Edwardsiella sp., Proteus mirabilis and Citrobacter brackii. The secondary metabolites produced by SEB32 from sponge Dysidea fragilis (Montagu, 1818 [48] was selected with broad range of antibacterial activity and subjected for production, characterization by series of chromatography techniques and spectroscopic methods. Based on the results of FT-IR and mass spectrometry, the active molecule was tentatively predicted as “Pyrrol” and the structure is Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro- with molecular formula of C7H10N2O2. The LC50 of active molecule was 31 μg/ml and molecular weight of the metabolites was 154. The potential strain SEB32 was identified by gene sequence (GenBank Accession number JX985748 and identified as Bacillus sp. from GenBank database.

  16. Mycosporine-Like Amino Acids: Relevant Secondary Metabolites. Chemical and Ecological Aspects

    Directory of Open Access Journals (Sweden)

    Mario O. Carignan

    2011-03-01

    Full Text Available Taxonomically diverse marine, freshwater and terrestrial organisms have evolved the capacity to synthesize, accumulate and metabolize a variety of UV-absorbing substances called mycosporine-like amino acids (MAAs as part of an overall strategy to diminish the direct and indirect damaging effects of environmental ultraviolet radiation (UVR. Whereas the enzymatic machinery to synthesize MAAs was probably inherited from cyanobacteria ancestors via the endosymbionts hypothesis, metazoans lack this biochemical pathway, but can acquire and metabolize these compounds by trophic transference, symbiotic or bacterial association. In this review we describe the structure and physicochemical properties of MAAs, including the recently discovered compounds and the modern methods used for their isolation and identification, updating previous reviews. On this basis, we review the metabolism and distribution of this unique class of metabolites among marine organism.

  17. Mycosporine-Like Amino Acids: Relevant Secondary Metabolites. Chemical and Ecological Aspects

    Science.gov (United States)

    Carreto, Jose I.; Carignan, Mario O.

    2011-01-01

    Taxonomically diverse marine, freshwater and terrestrial organisms have evolved the capacity to synthesize, accumulate and metabolize a variety of UV-absorbing substances called mycosporine-like amino acids (MAAs) as part of an overall strategy to diminish the direct and indirect damaging effects of environmental ultraviolet radiation (UVR). Whereas the enzymatic machinery to synthesize MAAs was probably inherited from cyanobacteria ancestors via the endosymbionts hypothesis, metazoans lack this biochemical pathway, but can acquire and metabolize these compounds by trophic transference, symbiotic or bacterial association. In this review we describe the structure and physicochemical properties of MAAs, including the recently discovered compounds and the modern methods used for their isolation and identification, updating previous reviews. On this basis, we review the metabolism and distribution of this unique class of metabolites among marine organism. PMID:21556168

  18. Chemical mediation of bacterial surface colonisation by secondary metabolites from the red alga Delisea pulchra

    DEFF Research Database (Denmark)

    Maximilien, Ria; de Nys, Rocky; Holmström, Carola

    1998-01-01

    -occurring algal species, all of which lack furanones. There was also a strong inverse correlation between bacterial abundance and furanone content (previously determined) for different sections of the thallus of D. pulchra, consistent with inhibition of bacteria by furanones. Based on these observations we....... pulchra the most. As inhibition of growth did not provide an adequate explanation for the inverse relationship between levels of furanones and bacteria abundance on D. pulchra, we proceeded to investigate the effects of these metabolites on other bacterial characteristics relevant to colonisation...... of different bacterial isolates or phenotypes by furanones, as well as affecting overall bacterial abundance on the alga, should have strong effects on the species composition of the bacterial community on the alga's surface. The effects of furanones on specific bacterial colonisation traits are discussed...

  19. Accumulation of primary and secondary metabolites in edible jackfruit seed tissues and scavenging of reactive nitrogen species.

    Science.gov (United States)

    Fernandes, Fátima; Ferreres, Federico; Gil-Izquierdo, Angel; Oliveira, Andreia P; Valentão, Patrícia; Andrade, Paula B

    2017-10-15

    Studies involving jackfruit tree (Artocarpus heterophyllus Lam.) focus on its fruit. Nevertheless a considerable part of jackfruit weight is represented by its seeds. Despite being consumed in several countries, knowledge about the chemical composition of these seeds is scarce. In this work, the accumulation of primary and secondary metabolites in jackfruit seed kernel and seed coating membrane was studied. Sixty-seven compounds were identified, sixty of them being reported for the first time in jackfruit seed. Both tissues had a similar qualitative profile, but significant quantitative differences were found. The capacity of aqueous extracts from jackfruit seed kernel and seed coating membranes to scavenge nitric oxide radical was also evaluated for the first time, the extract prepared from the seed coating membrane being the most potent. This work increases the potential revenue from a food that is still largely wasted. Copyright © 2017 Elsevier Ltd. All rights reserved.

  20. Using secondary metabolites in the monitoring of the condition of tree stands under industrial pollution

    Science.gov (United States)

    L. L. Fuksman

    2000-01-01

    The aim of this paper is to determine tile optimal physiological indicator in diagnosing the condition of tree stands under the stress of industrial pollution. Based on experimental results of the fumigation on pine seedlings with sulphur dioxide, acid rain treatment, and the effect of heavy metals on the seedlings, it is reasonable to use the secondary substances or...

  1. Changes of Enzymes Activity and Production of Secondary Metabolites of Artemisia aucheri in Different Altitudes and Its Relation to Adaptation

    Directory of Open Access Journals (Sweden)

    Hassan Zare-maivan

    2014-08-01

    Full Text Available Artemisia plants are the most abundant plants species in Iran which contain strong antioxidant properties and as such, have medicinal and economic value. Despite wide distribution of Artemisisa species, ecophysiology of its adaptation to changes in altitude and soil property had not been investigated. In this study, the relationships between ecophysiological and adaptation capabilities of A. aucheri to altitude changes through measuring changes in the activity of its antioxidant enzymes and secondary metabolites in situ was investigated based on a completely randomized experiment. The enzyme activities of superoxide dismutase, catalase, peroxidase, and the amount of total phenolics, flavonoids, anthocyanins, malondialdehyde and chlorophylls A and B were measured in A. aucheri plants growing in three different altitudes at and above the 36° latitude on the southern slopes of Eastern Alborz Mountain ranges in triplicate 10*10 m quadrates. Statistical analysis of data showed that soil type was loamy significantly becoming more sandy- loam with lowering in altitude and the soil contained greater amounts of oxides of silicone, aluminum, magnesium, sodium, potassium and phosphorus in upper altitude except calcium which was present in greater quantity in lower altitude. With increasing altitude, activity of superoxide dismutase and quantities of chlorophylls and total phenols in leaves increased. Some biochemical factors in A. aucheri showed significant positive correlation(P ≤ 0.05 between them. Adaptation of A. aucheri to changes in altitude occurred through changing its antioxidant enzymes activity and production of secondary metabolites in response to factors related to the altitude including soil type and texture, moisture level, temperature and most importantly radiation

  2. Simultaneous determination of secondary metabolites from Vinca rosea plant extractives by reverse phase high performance liquid chromatography

    Science.gov (United States)

    Siddiqui, Mohammad Jamshed Ahmad; Ismail, Zhari; Saidan, Noor Hafizoh

    2011-01-01

    Background: Vinca rosea (Apocynaceae) is one of the most important and high value medicinal plants known for its anticancer alkaloids. It is the iota of the isolated secondary metabolites used in chemotherapy to treat diverse cancers. Several high performance liquid chromatography (HPLC) methods have been developed to quantify the active alkaloids in the plant. However, this method may serve the purpose in quantification of V. rosea plant extracts in totality. Objective: To develop and validate the reverse phase (RP)-HPLC method for simultaneous determination of secondary metabolites, namely alkaloids from V. rosea plant extracts. Materials and Methods: The quantitative determination was conducted by RP-HPLC equipped with ultraviolet detector. Optimal separation was achieved by isocratic elution with mobile phase consisting of methanol:acetonitrile:ammonium acetate buffer (25 mM) with 0.1% triethylamine (15:45:40 v/v) on a column (Zorbax Eclipse plus C18, 250 mm % 4.6 mm; 5 μm). The standard markers (vindoline, vincristine, catharanthine, and vinblastine) were identified by retention time and co-injected with reference standard and quantified by external standard method at 297 nm. Results: The precision of the method was confirmed by the relative standard deviation (R.S.D.), which was lower than 2.68%. The recoveries were in the range of 98.09%-108%. The limits of detection (LOD) for each marker alkaloids were lower than 0.20 μg. Different parts of the V. rosea extracts shows different concentrations of markers, flower samples were high in vinblastine content, while methanol extract from the leaves contains all the four alkaloids in good yield, and there is no significant presence of markers in water extracts. Conclusion: HPLC method established is appropriate for the standardization and quality assurance of V. rosea plant extracts. PMID:21716929

  3. Peptaibol, secondary-metabolite, and hydrophobin pattern of commercial biocontrol agents formulated with species of the Trichoderma harzianum complex.

    Science.gov (United States)

    Degenkolb, Thomas; Fog Nielsen, Kristian; Dieckmann, Ralf; Branco-Rocha, Fabiano; Chaverri, Priscila; Samuels, Gary J; Thrane, Ulf; von Döhren, Hans; Vilcinskas, Andreas; Brückner, Hans

    2015-04-01

    The production of bioactive polypeptides (peptaibiotics) in vivo is a sophisticated adaptation strategy of both mycoparasitic and saprotrophic Trichoderma species for colonizing and defending their natural habitats. This feature is of major practical importance, as the detection of peptaibiotics in plant-protective Trichoderma species, which are successfully used against economically relevant bacterial and fungal plant pathogens, certainly contributes to a better understanding of these complex antagonistic interactions. We analyzed five commercial biocontrol agents (BCAs), namely Canna(®) , Trichosan(®) , Vitalin(®) , Promot(®) WP, and TrichoMax(®) , formulated with recently described species of the Trichoderma harzianum complex, viz. T. afroharzianum, T. simmonsii, and T. guizhouense. By using the well-established, HPLC/MS-based peptaibiomics approach, it could unequivocally be demonstrated that all of these formulations contained new and recurrent peptaibols, i.e., peptaibiotics carrying an acetylated N-terminus, the C-terminus of which is reduced to a 1,2-amino alcohol. Their chain lengths, including the amino alcohol, were 11, 14, and 18 residues, respectively. Peptaibols were also to be the dominating secondary metabolites in plate cultures of the four strains obtained from four of the Trichoderma- based BCAs, contributing 95% of the UHPLC-UV/VIS peak areas and 99% of the total ion count MS peak area from solid media. Furthermore, species-specific hydrophobins, as well as non-peptaibiotic secondary metabolites, were detected, the latter being known for their antifungal, siderophore, or plant-growth-promoting activities. Notably, none of the isolates produced low-molecular weight mycotoxins. Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.

  4. Combined effects of O3 and UV radiation on secondary metabolites and endogenous hormones of soybean leaves.

    Directory of Open Access Journals (Sweden)

    Bing Mao

    Full Text Available Enhanced ultraviolet radiation (UV and elevated tropospheric ozone (O3 may individually cause reductions in the growth and productivity of important agricultural crops. However, research regarding their combined effects on important agricultural crops is still scarce, especially on changes in secondary metabolites and endogenous hormones, which are important protective substances and signal components that control plant responses to environment stresses. In this study, using an experimental setup of open top chambers, we monitored the responses of seed yield per plant, leaf secondary metabolites and leaf endogenous hormones under the stress of elevated O3 and enhanced UV radiation individually, as well as their combined stress. The results indicated that elevated O3 (110 ± 10 nmol mol-1 for 8 hours per day and enhanced UV radiation (1.73 kJ h-1 m-2 significantly decreased seed yield per plant. Concentrations of rutin, queretin and total flavonoids were significantly increased under the elevated O3 treatment or the enhanced UV radiation treatment or the combination treatment at flowering and podding stages, and concentrations of rutin, queretin and total flavonoids showed significant correlations with seed yield per plant. Concentrations of ABA and IAA decreased under the three treatments. There was a significant positive correlation between the ABA concentration and seed yield and a negative correlation between the IAA concentration and seed yield. We concluded that the combined stress of elevated O3 and UV radiation significantly decreased seed yield per plant. Yield reduction was associated with changes in the concentrations of flavonoids, ABA and IAA in soybean leaves. The effects of the combined O3 and UV stress were always greater than those of the individual stresses alone.

  5. Metabolic Profiling of Primary and Secondary Biosynthetic Pathways in Angiosperms: Comparative Metabonomics and Applications of Hyphenated LC-NMR and LC-MS

    OpenAIRE

    Kaiser, Kayla Anne

    2012-01-01

    The goal of this dissertation was to advance plant metabolomics through optimization of biological experimental design, sampling and sample preparation, data acquisition and pre-processing, and multivariable data analysis. The analytical platform most employed for comparative metabonomics was nuclear magnetic resonance (NMR). Liquid-chromatography (LC) coupled to NMR and mass spectrometry (MS) extended metabolic profile coverage from primary into secondary metabolic pathways. Comparative p...

  6. Imprint Desorption Electrospray Ionization Mass Spectrometry Imaging for Monitoring Secondary Metabolites Production during Antagonistic Interaction of Fungi.

    Science.gov (United States)

    Tata, Alessandra; Perez, Consuelo; Campos, Michel L; Bayfield, Mark A; Eberlin, Marcos N; Ifa, Demian R

    2015-12-15

    Direct analysis of microbial cocultures grown on agar media by desorption electrospray ionization mass spectrometry (DESI-MS) is quite challenging. Due to the high gas pressure upon impact with the surface, the desorption mechanism does not allow direct imaging of soft or irregular surfaces. The divots in the agar, created by the high-pressure gas and spray, dramatically change the geometry of the system decreasing the intensity of the signal. In order to overcome this limitation, an imprinting step, in which the chemicals are initially transferred to flat hard surfaces, was coupled to DESI-MS and applied for the first time to fungal cocultures. Note that fungal cocultures are often disadvantageous in direct imaging mass spectrometry. Agar plates of fungi present a complex topography due to the simultaneous presence of dynamic mycelia and spores. One of the most devastating diseases of cocoa trees is caused by fungal phytopathogen Moniliophthora roreri. Strategies for pest management include the application of endophytic fungi, such as Trichoderma harzianum, that act as biocontrol agents by antagonizing M. roreri. However, the complex chemical communication underlying the basis for this phytopathogen-dependent biocontrol is still unknown. In this study, we investigated the metabolic exchange that takes place during the antagonistic interaction between M. roreri and T. harzianum. Using imprint-DESI-MS imaging we annotated the secondary metabolites released when T. harzianum and M. roreri were cultured in isolation and compared these to those produced after 3 weeks of coculture. We identified and localized four phytopathogen-dependent secondary metabolites, including T39 butenolide, harzianolide, and sorbicillinol. In order to verify the reliability of the imprint-DESI-MS imaging data and evaluate the capability of tape imprints to extract fungal metabolites while maintaining their localization, six representative plugs along the entire M. roreri/T. harzianum

  7. Bioactive Metabolites from Pathogenic and Endophytic Fungi of Forest Trees.

    Science.gov (United States)

    Masi, Marco; Maddau, Lucia; Linaldeddu, Benedetto Teodoro; Scanu, Bruno; Evidente, Antonio; Cimmino, Alessio

    2018-01-01

    Fungi play an important role in terrestrial ecosystems interacting positively or negatively with plants. These interactions are complex and the outcomes are different depending on the fungal lifestyles, saprotrophic, mutualistic or pathogenic. Furthermore, fungi are well known for producing secondary metabolites, originating from different biosynthetic pathways, which possess biological properties of considerable biotechnological interest. Among the terrestrial ecosystems, temperate forests represent an enormous reservoir of fungal diversity. This review will highlight the goldmine of secondary metabolites produced by pathogenic and endophytic fungi of forest trees with focus on their biological activities. A structured search of bibliographic databases for peer-reviewed research literature was undertaken using a research discovery application providing access to a large and authoritative source of references. The papers selected were examined and the main results were reported and discussed. Two hundred forthy-one papers were included in the review, outlined a large number of secondary metabolites produced by pathogenic and endophiltic fungi and their biological activities, including phytotoxic, antifungal, antioomycetes, antibacterial, brine shrimp lethality, mosquito biting deterrence and larvicidal, cytotoxic, antiproliferative and many other bioactivities. The findings of this review confirm the importance of secondary metabolites produced by pathogenic and endophytic fungi from forest plants growing in temperate regions as an excellent prospects to discover compounds with new bioactivities and mode of actions. In addition, the potential of some metabolites as a source of new drugs and biopesticides is underlined. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  8. Effect of Glomus mosseae and plant growth promoting rhizomicroorganisms (PGPR's on growth, nutrients and content of secondary metabolites in Begonia malabarica Lam.

    Directory of Open Access Journals (Sweden)

    Thangavel Selvaraj

    2008-10-01

    Full Text Available Begonia malabarica Lam. (Begoniaceae is one of the important medicinal plants whose main secondary metabolites are luteolin, quercetin and β-sitosterol. The leaves are used for the treatment of respiratory tract infections, diarrhoea, blood cancer and skin diseases. A study was undertaken to determine the effect of arbuscular mycorrhizal (AM fungus, Glomus mosseae, and some plant growth promoting rhizomicro-organisms (PGPR's on the growth, biomass, nutrients, and content of secondary metabolites of B. malabarica plant under green house conditions. Various plant growth parameters (total plant biomass, mycorrhizal parameter, shoot and root phosphorus, mineral content (potassium, iron, zinc, and copper, and secondary metabolites (total phenols, ortho-dihydroxy phenols, tannins, flavonoids, and alkaloids were determined and found to vary with different treatments. Among all the treatments, plants inoculated with 'microbial consortium' consisting of Glomus mosseae + Bacillus coagulans + Trichoderma viride performed better than with other treatments or uninoculated control plants. The results of this experiment clearly indicated that inoculation of B. malabarica with G. mosseae along with PGPR's enhanced its growth, biomass yield, nutrients and secondary metabolites.

  9. Sequential metabolism of secondary alkyl amines to metabolic-intermediate complexes: opposing roles for the secondary hydroxylamine and primary amine metabolites of desipramine, (s)-fluoxetine, and N-desmethyldiltiazem.

    Science.gov (United States)

    Hanson, Kelsey L; VandenBrink, Brooke M; Babu, Kantipudi N; Allen, Kyle E; Nelson, Wendel L; Kunze, Kent L

    2010-06-01

    Three secondary amines desipramine (DES), (S)-fluoxetine [(S)-FLX], and N-desmethyldiltiazem (MA) undergo N-hydroxylation to the corresponding secondary hydroxylamines [N-hydroxydesipramine, (S)-N-hydroxyfluoxetine, and N-hydroxy-N-desmethyldiltiazem] by cytochromes P450 2C11, 2C19, and 3A4, respectively. The expected primary amine products, N-desmethyldesipramine, (S)-norfluoxetine, and N,N-didesmethyldiltiazem, are also observed. The formation of metabolic-intermediate (MI) complexes from these substrates and metabolites was examined. In each example, the initial rates of MI complex accumulation followed the order secondary hydroxylamine > secondary amine > primary amine, suggesting that the primary amine metabolites do not contribute to formation of MI complexes from these secondary amines. Furthermore, the primary amine metabolites, which accumulate in incubations of the secondary amines, inhibit MI complex formation. Mass balance studies provided estimates of the product ratios of N-dealkylation to N-hydroxylation. The ratios were 2.9 (DES-CYP2C11), 3.6 [(S)-FLX-CYP2C19], and 0.8 (MA-CYP3A4), indicating that secondary hydroxylamines are significant metabolites of the P450-mediated metabolism of secondary alkyl amines. Parallel studies with N-methyl-d(3)-desipramine and CYP2C11 demonstrated significant isotopically sensitive switching from N-demethylation to N-hydroxylation. These findings demonstrate that the major pathway to MI complex formation from these secondary amines arises from N-hydroxylation rather than N-dealkylation and that the primary amines are significant competitive inhibitors of MI complex formation.

  10. Secondary metabolites from the phloem of Piper solmsianum (Piperaceae) in the honeydew of Edessa meditabunda.

    Science.gov (United States)

    Ramos, Clécio S; Kato, Massuo J

    2012-01-01

    The phytochemistry of species of the genus Piper has been studied extensively, including Piper solmsianum. However, no studies have addressed the phytochemistry of the sap content of Piper species. To evaluate the transferring of secondary compounds from the saps of P. solmsianum to the honeydew of Edessa meditabunda. The honeydew of E. meditabunda and saps of P. solmsianum were analysed by GC-MS, (1) H-NMR and LC-MS. The lignan (-)-grandisin and the phenylpropanoid (E)-isoelemicin were detected in both saps of P. solmsianum and honeydew of E. meditabunda. Analysis of honeydew secreted by the sap-sucking insect E. meditabunda indicated that (-)-grandisin and (E)-isoelemicin are absorbed from the phloem of Piper solmsianum. Copyright © 2012 John Wiley & Sons, Ltd.

  11. Pharmacological synergism of bee venom and melittin with antibiotics and plant secondary metabolites against multi-drug resistant microbial pathogens.

    Science.gov (United States)

    Al-Ani, Issam; Zimmermann, Stefan; Reichling, Jürgen; Wink, Michael

    2015-02-15

    The goal of this study was to investigate the antimicrobial activity of bee venom and its main component, melittin, alone or in two-drug and three-drug combinations with antibiotics (vancomycin, oxacillin, and amikacin) or antimicrobial plant secondary metabolites (carvacrol, benzyl isothiocyanate, the alkaloids sanguinarine and berberine) against drug-sensitive and antibiotic-resistant microbial pathogens. The secondary metabolites were selected corresponding to the molecular targets to which they are directed, being different from those of melittin and the antibiotics. The minimal inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) were evaluated by the standard broth microdilution method, while synergistic or additive interactions were assessed by checkerboard dilution and time-kill curve assays. Bee venom and melittin exhibited a broad spectrum of antibacterial activity against 51 strains of both Gram-positive and Gram-negative bacteria with strong anti-MRSA and anti-VRE activity (MIC values between 6 and 800 µg/ml). Moreover, bee venom and melittin showed significant antifungal activity (MIC values between 30 and 100 µg/ml). Carvacrol displayed bactericidal activity, while BITC exhibited bacteriostatic activity against all MRSA and VRE strains tested (reference strains and clinical isolates), both compounds showed a remarkable fungicidal activity with minimum fungicidal concentration (MFC) values between 30 and 200 µg/ml. The DNA intercalating alkaloid sanguinarine showed bactericidal activity against MRSA NCTC 10442 (MBC 20 µg/ml), while berberine exhibited bacteriostatic activity against MRSA NCTC 10442 (MIC 40 µg/ml). Checkerboard dilution tests mostly revealed synergism of two-drug combinations against all the tested microorganisms with FIC indexes between 0.24 and 0.50, except for rapidly growing mycobacteria in which combinations exerted an additive effect (FICI = 0.75-1). In time-kill assays all three

  12. Spectral lights trigger biomass accumulation and production of antioxidant secondary metabolites in adventitious root cultures of Stevia rebaudiana (Bert.).

    Science.gov (United States)

    Idrees, Muhammad; Sania, Bibi; Hafsa, Bibi; Kumari, Sana; Khan, Haji; Fazal, Hina; Ahmad, Ishfaq; Akbar, Fazal; Ahmad, Naveed; Ali, Sadeeq; Ahmad, Nisar

    2018-05-30

    Stevia rebaudiana (S. rebaudiana) is the most important therapeutic plant species and has been accepted as such worldwide. It has a tendency to accumulate steviol glycosides, which are 300 times sweeter than marketable sugar. Recently, diabetic patients commonly use this plant as a sugar substitute for sweet taste. In the present study, the effects of different spectral lights were investigated on biomass accumulation and production of secondary metabolites in adventitious root cultures of S. rebaudiana. For callus development, leaf explants were excised from seed-derived plantlets and inoculated on a Murashige and Skoog (MS) medium containing the combination of 2,4-dichlorophenoxy acetic acid (2, 4-D, 2.0mg/l) and 6-benzyladenine (BA, 2.0mg/l), while 0.5mg/l naphthalene acetic acid (NAA) was used for adventitious root culture. Adventitious root cultures were exposed to different spectral lights (blue, green, violet, red and yellow) for a 30-day period. White light was used as control. The growth kinetics was studied for 30days with 3-day intervals. In this study, the violet light showed the maximum accumulation of fresh biomass (2.495g/flask) as compared to control (1.63g/flask), while red light showed growth inhibition (1.025g/flask) as compared to control. The blue light enhanced the highest accumulation of phenolic content (TPC; 6.56mg GAE/g DW), total phenolic production (TPP; 101mg/flask) as compared to control (5.44mg GAE/g DW; 82.2mg GAE/g DW), and exhibited a strong correlation with dry biomass. Blue light also improved the accumulation of total flavonoid content (TFC; 4.33mg RE/g DW) and total flavonoid production (TFP; 65mg/flask) as compared to control. The violet light showed the highest DPPH inhibition (79.72%), while the lowest antioxidant activity was observed for control roots (73.81%). Hence, we concluded that the application of spectral lights is an auspicious strategy for the enhancement of the required antioxidant secondary metabolites in

  13. Radioprotection offered by bacterial secondary metabolite RK-IP-006.G to the mice by oral route of administration

    International Nuclear Information System (INIS)

    Gupta, Ashutosh K.; Malhotra, Poonam; Singh, Praveen K.; Chhachhia, Neha; Singh, Shravan K.; Kumar, Raj

    2014-01-01

    Ionizing radiation is known to cause oxidative damage in biological system primarily by generating reactive oxygen species (ROS). Gastrointestinal system is considered one of the most radiosensitive biological systems. The most radiosensitive cells type found in the intestine are continuously proliferative crypt cells. Damage to intestinal crypt cells lead to gastrointestinal functions impairment that contribute to mortality. In the present study, whole body radioprotective efficacy of bacterial secondary metabolite RK-IP-006.G was evaluated in C57BL/6 male mice. To determine free radical scavenging properties of RK-IP-006.G 2',7'-dichlorodihydrofluorescein diacetate (DCFDA) assay was performed. Radiation induced lipid peroxidation and its inhibition by RK-IP-006.G pretreatment was assessed in intestinal tissue homogenate. To find out cellular antioxidant status of the irradiated and RK-IP- 006.G treated mice, SOD, Catalase, and Glutathion-S-Transferase activity were estimated in intestinal tissue homogenate. Anti-apoptotic and mitochondrial membrane hypopolarization effect of the RK-IP-006.G was also analyzed using fluorescent probes Acridine Orange and Rhodamine123 respectively. Results of the study demonstrated that, RK-IP-006.G pretreatment (∼2h; 150 mg/kg.b.wt. oral administration) to the lethally irradiated (9 Gy) C57BL/6 male mice contributes to >83% whole body radioprotection in mice. Significant (P>0.05%) inhibition in lipid peroxidation was observed in intestinal tissue of irradiated mice pretreated with RK-IP-006.G compared to only irradiated controls. Significant (P>0.05%) increase in antioxidant enzyme i.e. Catalase, SOD and GST activities was reported in irradiated mice pretreated with RK-IP-006.G compared to irradiated control groups. RK-IP-006.G pretreatment also found to be instrumental in inhibiting radiation induced apoptosis and mitochondrial membrane hyperpolarization. In conclusion, present study revealed that bacterial secondary

  14. Motif-Independent De Novo Detection of Secondary Metabolite Gene Clusters – Towards Identification of Novel Secondary Metabolisms from Filamentous Fungi -

    Directory of Open Access Journals (Sweden)

    Myco eUmemura

    2015-05-01

    Full Text Available Secondary metabolites are produced mostly by clustered genes that are essential to their biosynthesis. The transcriptional expression of these genes is often cooperatively regulated by a transcription factor located inside or close to a cluster. Most of the secondary metabolism biosynthesis (SMB gene clusters identified to date contain so-called core genes with distinctive sequence features, such as polyketide synthase (PKS and non-ribosomal peptide synthetase (NRPS. Recent efforts in sequencing fungal genomes have revealed far more SMB gene clusters than expected based on the number of core genes in the genomes. Several bioinformatics tools have been developed to survey SMB gene clusters using the sequence motif information of the core genes, including SMURF and antiSMASH.More recently, accompanied by the development of sequencing techniques allowing to obtain large-scale genomic and transcriptomic data, motif-independent prediction methods of SMB gene clusters, including MIDDAS-M, have been developed. Most these methods detect the clusters in which the genes are cooperatively regulated at transcriptional levels, thus allowing the identification of novel SMB gene clusters regardless of the presence of the core genes. Another type of the method, MIPS-CG, uses the characteristics of SMB genes, which are highly enriched in non-syntenic blocks (NSBs, enabling the prediction even without transcriptome data although the results have not been evaluated in detail. Considering that large portion of SMB gene clusters might be sufficiently expressed only in limited uncommon conditions, it seems that prediction of SMB gene clusters by bioinformatics and successive experimental validation is an only way to efficiently uncover hidden SMB gene clusters. Here, we describe and discuss possible novel approaches for the determination of SMB gene clusters that have not been identified using conventional methods.

  15. Comparative Genome Structure, Secondary Metabolite, and Effector Coding Capacity across Cochliobolus Pathogens

    Energy Technology Data Exchange (ETDEWEB)

    Condon, Bradford J.; Leng, Yueqiang; Wu, Dongliang; Bushley, Kathryn E.; Ohm, Robin A.; Otillar, Robert; Martin, Joel; Schackwitz, Wendy; Grimwood, Jane; MohdZainudin, NurAinlzzati; Xue, Chunsheng; Wang, Rui; Manning, Viola A.; Dhillon, Braham; Tu, Zheng Jin; Steffenson, Brian J.; Salamov, Asaf; Sun, Hui; Lowry, Steve; LaButti, Kurt; Han, James; Copeland, Alex; Lindquist, Erika; Barry, Kerrie; Schmutz, Jeremy; Baker, Scott E.; Ciuffetti, Lynda M.; Grigoriev, Igor V.; Zhong, Shaobin; Turgeon, B. Gillian

    2013-01-24

    The genomes of five Cochliobolus heterostrophus strains, two Cochliobolus sativus strains, three additional Cochliobolus species (Cochliobolus victoriae, Cochliobolus carbonum, Cochliobolus miyabeanus), and closely related Setosphaeria turcica were sequenced at the Joint Genome Institute (JGI). The datasets were used to identify SNPs between strains and species, unique genomic regions, core secondary metabolism genes, and small secreted protein (SSP) candidate effector encoding genes with a view towards pinpointing structural elements and gene content associated with specificity of these closely related fungi to different cereal hosts. Whole-genome alignment shows that three to five of each genome differs between strains of the same species, while a quarter of each genome differs between species. On average, SNP counts among field isolates of the same C. heterostrophus species are more than 25 higher than those between inbred lines and 50 lower than SNPs between Cochliobolus species. The suites of nonribosomal peptide synthetase (NRPS), polyketide synthase (PKS), and SSP encoding genes are astoundingly diverse among species but remarkably conserved among isolates of the same species, whether inbred or field strains, except for defining examples that map to unique genomic regions. Functional analysis of several strain-unique PKSs and NRPSs reveal a strong correlation with a role in virulence.

  16. Silencing onion lachrymatory factor synthase causes a significant change in the sulfur secondary metabolite profile.

    Science.gov (United States)

    Eady, Colin C; Kamoi, Takahiro; Kato, Masahiro; Porter, Noel G; Davis, Sheree; Shaw, Martin; Kamoi, Akiko; Imai, Shinsuke

    2008-08-01

    Through a single genetic transformation in onion (Allium cepa), a crop recalcitrant to genetic transformation, we suppressed the lachrymatory factor synthase gene using RNA interference silencing in six plants. This reduced lachrymatory synthase activity by up to 1,544-fold, so that when wounded the onions produced significantly reduced levels of tear-inducing lachrymatory factor. We then confirmed, through a novel colorimetric assay, that this silencing had shifted the trans-S-1-propenyl-l-cysteine sulfoxide breakdown pathway so that more 1-propenyl sulfenic acid was converted into di-1-propenyl thiosulfinate. A consequence of this raised thiosulfinate level was a marked increase in the downstream production of a nonenzymatically produced zwiebelane isomer and other volatile sulfur compounds, di-1-propenyl disulfide and 2-mercapto-3,4-dimethyl-2,3-dihydrothiophene, which had previously been reported in trace amounts or had not been detected in onion. The consequences of this dramatic simultaneous down- and up-regulation of secondary sulfur products on the health and flavor attributes of the onion are discussed.

  17. Emergent biosynthetic capacity in simple microbial communities.

    Directory of Open Access Journals (Sweden)

    Hsuan-Chao Chiu

    2014-07-01

    Full Text Available Microbes have an astonishing capacity to transform their environments. Yet, the metabolic capacity of a single species is limited and the vast majority of microorganisms form complex communities and join forces to exhibit capabilities far exceeding those achieved by any single species. Such enhanced metabolic capacities represent a promising route to many medical, environmental, and industrial applications and call for the development of a predictive, systems-level understanding of synergistic microbial capacity. Here we present a comprehensive computational framework, integrating high-quality metabolic models of multiple species, temporal dynamics, and flux variability analysis, to study the metabolic capacity and dynamics of simple two-species microbial ecosystems. We specifically focus on detecting emergent biosynthetic capacity--instances in which a community growing on some medium produces and secretes metabolites that are not secreted by any member species when growing in isolation on that same medium. Using this framework to model a large collection of two-species communities on multiple media, we demonstrate that emergent biosynthetic capacity is highly prevalent. We identify commonly observed emergent metabolites and metabolic reprogramming patterns, characterizing typical mechanisms of emergent capacity. We further find that emergent secretion tends to occur in two waves, the first as soon as the two organisms are introduced, and the second when the medium is depleted and nutrients become limited. Finally, aiming to identify global community determinants of emergent capacity, we find a marked association between the level of emergent biosynthetic capacity and the functional/phylogenetic distance between community members. Specifically, we demonstrate a "Goldilocks" principle, where high levels of emergent capacity are observed when the species comprising the community are functionally neither too close, nor too distant. Taken together

  18. Adaptive changes in photosynthetic performance and secondary metabolites during white dead nettle micropropagation.

    Science.gov (United States)

    Kapchina-Toteva, V; Dimitrova, M A; Stefanova, M; Koleva, D; Kostov, K; Yordanova, Zh P; Stefanov, D; Zhiponova, M K

    2014-09-15

    The white dead nettle, Lamium album L., is an herb that has been successfully cultivated under in vitro conditions. The L. album micropropagation system offers a combination of factors (light intensity, temperature, carbon dioxide (CO2) level, humidity) that are limiting for plant growth and bioactive capacity. To get a better understanding of the mechanism of plant acclimation towards environmental changes, we performed a comparative investigation on primary and secondary metabolism in fully expanded L. album leaves during the consecutive growth in in situ, in vitro, and ex vitro conditions. Although the genetic identity was not affected, structural and physiological deviations were observed, and the level of bioactive compounds was modified. During in vitro cultivation, the L. album leaves became thinner with unaffected overall leaf organization, but with a reduced number of palisade mesophyll layers. Structural deviation of the thylakoid membrane system was detected. In addition, the photosystem 2 (PS2) electron transport was retarded, and the plants were more vulnerable to light damage as indicated by the decreased photoprotection ability estimated by fluorescence parameters. The related CO2 assimilation and transpiration rates were subsequently reduced, as were the content of essential oils and phenolics. Transfer of the plants ex vitro did not increase the number of palisade numbers, but the chloroplast structure and PS2 functionality were recovered. Strikingly, the rates of CO2 assimilation and transpiration were increased compared to in situ control plants. While the phenolics content reached normal levels during ex vitro growth, the essential oils remained low. Overall, our study broadens the understanding about the nature of plant responses towards environmental conditions. Copyright © 2014 Elsevier GmbH. All rights reserved.

  19. ABA and GA3 regulate the synthesis of primary and secondary metabolites related to alleviation from biotic and abiotic stresses in grapevine.

    Science.gov (United States)

    Murcia, Germán; Fontana, Ariel; Pontin, Mariela; Baraldi, Rita; Bertazza, Gianpaolo; Piccoli, Patricia N

    2017-03-01

    Plants are able to synthesize a large number of organic compounds. Among them, primary metabolites are known to participate in plant growth and development, whereas secondary metabolites are mostly involved in defense and other facultative processes. In grapevine, one of the major fruit crops in the world, secondary metabolites, mainly polyphenols, are of great interest for the wine industry. Even though there is an extensive literature on the content and profile of those compounds in berries, scarce or no information is available regarding polyphenols in other organs. In addition, little is known about the effect of plant growth regulators (PGRs), ABA and GA 3 (extensively used in table grapes) on the synthesis of primary and secondary metabolites in wine grapes. In table grapes, cultural practices include the use of GA 3 sprays shortly before veraison, to increase berry and bunch size, and sugar content in fruits. Meanwhile, ABA applications to the berries on pre-veraison improve the skin coloring and sugar accumulation, anticipating the onset of veraison. Accordingly, the aim of this study was to assess and characterize primary and secondary metabolites in leaves, berries and roots of grapevine plants cv. Malbec at veraison, and changes in compositions after ABA and GA 3 aerial sprayings. Metabolic profiling was conducted using GC-MS, GC-FID and HPLC-MWD. A large set of metabolites was identified: sugars, alditols, organic acids, amino acids, polyphenols (flavonoids and non-flavonoids) and terpenes (mono-, sesqui-, di- and triterpenes). The obtained results showed that ABA applications elicited synthesis of mono- and sesquiterpenes in all assessed tissues, as well as L-proline, acidic amino acids and anthocyanins in leaves. Additionally, applications with GA 3 elicited synthesis of L-proline in berries, and mono- and sesquiterpenes in all the tissues. However, treatment with GA 3 seemed to block polyphenol synthesis, mainly in berries. In conclusion, ABA and GA

  20. In silico profiling for secondary metabolites from Lepidium meyenii (maca) by the pharmacophore and ligand-shape-based joint approach.

    Science.gov (United States)

    Yi, Fan; Tan, Xiao-Lei; Yan, Xin; Liu, Hai-Bo

    2016-01-01

    Lepidium meyenii Walpers (maca) is an herb known as a traditional nutritional supplement and widely used in Peru, North America, and Europe to enhance human fertility and treat osteoporosis. The secondary metabolites of maca, namely, maca alkaloids, macaenes, and macamides, are bioactive compounds, but their targets are undefined. The pharmacophore-based PharmaDB targets database screening joint the ligand shape similarity-based WEGA validation approach is proposed to predict the targets of these unique constituents and was performed using Discovery Studio 4.5 and PharmaDB. A compounds-targets-diseases network was established using Cytoscape 3.2. These suitable targets and their genes were calculated and analyzed using ingenuity pathway analysis and GeneMANIA. Certain targets were identified in osteoporosis (8 targets), prostate cancer (9 targets), and kidney diseases (11 targets). This was the first study to identify the targets of these bioactive compounds in maca for cardiovascular diseases (29 targets). The compound with the most targets (46) was an amide alkaloid (MA-24). In silico target fishing identified maca's traditional effects on treatment and prevention of osteoporosis, prostate cancer, and kidney diseases, and its potential function of treating cardiovascular diseases, as the most important of this herb's possible activities.

  1. Responses to mild water deficit and rewatering differ among secondary metabolites but are similar among provenances within Eucalyptus species.

    Science.gov (United States)

    McKiernan, Adam B; Potts, Brad M; Brodribb, Timothy J; Hovenden, Mark J; Davies, Noel W; McAdam, Scott A M; Ross, John J; Rodemann, Thomas; O'Reilly-Wapstra, Julianne M

    2016-02-01

    Water deficit associated with drought can severely affect plants and influence ecological interactions involving plant secondary metabolites. We tested the effect of mild water deficit and rewatering on physiological, morphological and chemical traits of juvenile Eucalyptus globulus Labill. and Eucalyptus viminalis Labill. We also tested if responses of juvenile eucalypts to water deficit and rewatering varied within species using provenances across a rainfall gradient. Both species and all provenances were similarly affected by mild water deficit and rewatering, as only foliar abscisic acid levels differed among provenances during water deficit. Across species and provenances, water deficit decreased leaf water potential, above-ground biomass and formylated phloroglucinol compound concentrations, and increased condensed tannin concentrations. Rewatering reduced leaf carbon : nitrogen, and total phenolic and chlorogenic acid concentrations. Water deficit and rewatering had no effect on total oil or individual terpene concentrations. Levels of trait plasticity due to water deficit and rewatering were less than levels of constitutive trait variation among provenances. The overall uniformity of responses to the treatments regardless of native provenance indicates limited diversification of plastic responses when compared with the larger quantitative variation of constitutive traits within these species. These responses to mild water deficit may differ from responses to more extreme water deficit or to responses of juvenile/mature eucalypts growing at each locality. © The Author 2015. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

  2. Identification of Minor Secondary Metabolites from the Latex of Croton lechleri (Muell-Arg and Evaluation of Their Antioxidant Activity

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    Maria Iorizzi

    2008-06-01

    Full Text Available Dragon’s blood (Sangre de drago, a viscous red sap derived from Croton lechleri Muell-Arg (Euphorbiaceae, is extensively used by indigenous cultures of the Amazonian basin for its wound healing properties. The aim of this study was to identify the minor secondary metabolites and test the antioxidant activity of this sustance. A bioguided fractionation of the n-hexane, chloroform, n-butanol, and aqueous extracts led to the isolation of 15 compounds: three megastigmanes, four flavan-3-ols, three phenylpropanoids, three lignans, a clerodane, and the alkaloid taspine. In addition to these known molecules, six compounds were isolated and identified for the first time in the latex: blumenol B, blumenol C, 4,5-dihydroblumenol A, erythro-guaiacyl-glyceryl-β-O-4’- dihydroconiferyl ether, 2-[4-(3-hydroxypropyl-2-methoxyphenoxy]-propane-1,3-diol and floribundic acid glucoside. Combinations of spectroscopic methods (1H-, 13C- NMR and 2D-NMR experiments, ESI-MS, and literature comparisons were used for compound identification. In vitro antioxidant activities were assessed by DPPH, total antioxidant capacity and lipid peroxidation assays. Flavan-3-ols derivatives (as major phenolic compounds in the latex exhibited the highest antioxidant activity.

  3. Push-Pull Effects of Three Plant Secondary Metabolites on Oviposition of the Potato Tuber Moth, Phthorimaea operculella

    Science.gov (United States)

    Ma, Y.F.; Xiao, C.

    2013-01-01

    The push-pull effects of three plant secondary metabolites, azadirachtin, eucalyptol, and heptanal, on the oviposition choices of potato tubers by the potato tuber moth, Phthorimaea operculella (Zeller) (Lepidoptera: Gelechiidae) were tested in the laboratory. Azadirachtin at concentrations from 1.5 to 12 mg/L had a significant repellent effect on oviposition. Eucalyptol at concentrations from 3 to 12 mg/L promoted oviposition. Heptanal promoted oviposition at low concentrations from 0.1875 to 3.0 mg/L but repelled it at higher concentrations from 12 to 24 mg/L. The combination of azadirachtin (12 mg/L) with eucalyptol (3.0 mg/L) resulted in a significant pushpull effect of 56.3% on oviposition. The average maximum push-pull effects occurred with the combinations of azadirachtin with heptanal (12 and 0.375 mg/L, respectively; 38.7% push-pull effect), heptanal with eucalyptol (12 and 6 mg/L, respectively; 31.4% push-pull effect), and heptanal (high concentration) with heptanal (low concentration) (12.0 and 0.375 mg/L, respectively; 25% push-pull effect). PMID:24786822

  4. Effects of hybridization and evolutionary constraints on secondary metabolites: the genetic architecture of phenylpropanoids in European populus species.

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    Caseys, Celine; Stritt, Christoph; Glauser, Gaetan; Blanchard, Thierry; Lexer, Christian

    2015-01-01

    The mechanisms responsible for the origin, maintenance and evolution of plant secondary metabolite diversity remain largely unknown. Decades of phenotypic studies suggest hybridization as a key player in generating chemical diversity in plants. Knowledge of the genetic architecture and selective constraints of phytochemical traits is key to understanding the effects of hybridization on plant chemical diversity and ecological interactions. Using the European Populus species P. alba (White poplar) and P. tremula (European aspen) and their hybrids as a model, we examined levels of inter- and intraspecific variation, heritabilities, phenotypic correlations, and the genetic architecture of 38 compounds of the phenylpropanoid pathway measured by liquid chromatography and mass spectrometry (UHPLC-MS). We detected 41 quantitative trait loci (QTL) for chlorogenic acids, salicinoids and flavonoids by genetic mapping in natural hybrid crosses. We show that these three branches of the phenylpropanoid pathway exhibit different geographic patterns of variation, heritabilities, and genetic architectures, and that they are affected differently by hybridization and evolutionary constraints. Flavonoid abundances present high species specificity, clear geographic structure, and strong genetic determination, contrary to salicinoids and chlorogenic acids. Salicinoids, which represent important defence compounds in Salicaceae, exhibited pronounced genetic correlations on the QTL map. Our results suggest that interspecific phytochemical differentiation is concentrated in downstream sections of the phenylpropanoid pathway. In particular, our data point to glycosyltransferase enzymes as likely targets of rapid evolution and interspecific differentiation in the 'model forest tree' Populus.

  5. Effects of hybridization and evolutionary constraints on secondary metabolites: the genetic architecture of phenylpropanoids in European populus species.

    Directory of Open Access Journals (Sweden)

    Celine Caseys

    Full Text Available The mechanisms responsible for the origin, maintenance and evolution of plant secondary metabolite diversity remain largely unknown. Decades of phenotypic studies suggest hybridization as a key player in generating chemical diversity in plants. Knowledge of the genetic architecture and selective constraints of phytochemical traits is key to understanding the effects of hybridization on plant chemical diversity and ecological interactions. Using the European Populus species P. alba (White poplar and P. tremula (European aspen and their hybrids as a model, we examined levels of inter- and intraspecific variation, heritabilities, phenotypic correlations, and the genetic architecture of 38 compounds of the phenylpropanoid pathway measured by liquid chromatography and mass spectrometry (UHPLC-MS. We detected 41 quantitative trait loci (QTL for chlorogenic acids, salicinoids and flavonoids by genetic mapping in natural hybrid crosses. We show that these three branches of the phenylpropanoid pathway exhibit different geographic patterns of variation, heritabilities, and genetic architectures, and that they are affected differently by hybridization and evolutionary constraints. Flavonoid abundances present high species specificity, clear geographic structure, and strong genetic determination, contrary to salicinoids and chlorogenic acids. Salicinoids, which represent important defence compounds in Salicaceae, exhibited pronounced genetic correlations on the QTL map. Our results suggest that interspecific phytochemical differentiation is concentrated in downstream sections of the phenylpropanoid pathway. In particular, our data point to glycosyltransferase enzymes as likely targets of rapid evolution and interspecific differentiation in the 'model forest tree' Populus.

  6. Anticancer Activity of Ramalin, a Secondary Metabolite from the Antarctic Lichen Ramalina terebrata, against Colorectal Cancer Cells

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    Sung-Suk Suh

    2017-08-01

    Full Text Available Colorectal cancer is a leading cause of death worldwide and occurs through the highly complex coordination of multiple cellular pathways, resulting in carcinogenesis. Recent studies have increasingly revealed that constituents of lichen extracts exhibit potent pharmaceutical activities, including anticancer activity against various cancer cells, making them promising candidates for new anticancer therapeutic drugs. The main objective of this study was to evaluate the anticancer capacities of ramalin, a secondary metabolite from the Antarctic lichen Ramalina terebrata, in the human colorectal cancer cell line HCT116. In this study, ramalin displayed concentration-dependent anticancer activity against HCT116 cells, significantly suppressing proliferation and inducing apoptosis. Furthermore, ramalin induced cell cycle arrest in the gap 2/mitosis (G2/M phase through the modulation of hallmark genes involved in the G2/M phase transition, such as tumour protein p53 (TP53, cyclin-dependent kinase inhibitor 1A (CDKN1A, cyclin-dependent kinase 1 (CDK1 and cyclin B1 (CCNB1. At both the transcriptional and translational level, ramalin caused a gradual increase in the expression of TP53 and its downstream gene CDKN1A, while decreasing the expression of CDK1 and CCNB1 in a concentration-dependent manner. In addition, ramalin significantly inhibited the migration and invasion of colorectal cancer cells in a concentration-dependent manner. Taken together, these data suggest that ramalin may be a therapeutic candidate for the targeted therapy of colorectal cancer.

  7. Selective and specific inhibition of the plasmodium falciparum lysyl-tRNA synthetase by the fungal secondary metabolite cladosporin.

    Science.gov (United States)

    Hoepfner, Dominic; McNamara, Case W; Lim, Chek Shik; Studer, Christian; Riedl, Ralph; Aust, Thomas; McCormack, Susan L; Plouffe, David M; Meister, Stephan; Schuierer, Sven; Plikat, Uwe; Hartmann, Nicole; Staedtler, Frank; Cotesta, Simona; Schmitt, Esther K; Petersen, Frank; Supek, Frantisek; Glynne, Richard J; Tallarico, John A; Porter, Jeffrey A; Fishman, Mark C; Bodenreider, Christophe; Diagana, Thierry T; Movva, N Rao; Winzeler, Elizabeth A

    2012-06-14

    With renewed calls for malaria eradication, next-generation antimalarials need be active against drug-resistant parasites and efficacious against both liver- and blood-stage infections. We screened a natural product library to identify inhibitors of Plasmodium falciparum blood- and liver-stage proliferation. Cladosporin, a fungal secondary metabolite whose target and mechanism of action are not known for any species, was identified as having potent, nanomolar, antiparasitic activity against both blood and liver stages. Using postgenomic methods, including a yeast deletion strains collection, we show that cladosporin specifically inhibits protein synthesis by directly targeting P. falciparum cytosolic lysyl-tRNA synthetase. Further, cladosporin is >100-fold more potent against parasite lysyl-tRNA synthetase relative to the human enzyme, which is conferred by the identity of two amino acids within the enzyme active site. Our data indicate that lysyl-tRNA synthetase is an attractive, druggable, antimalarial target that can be selectively inhibited. Copyright © 2012 Elsevier Inc. All rights reserved.

  8. Endophytic Actinobacteria from the Brazilian Medicinal Plant Lychnophora ericoides Mart. and the Biological Potential of Their Secondary Metabolites.

    Science.gov (United States)

    Conti, Raphael; Chagas, Fernanda Oliveira; Caraballo-Rodriguez, Andrés Mauricio; Melo, Weilan Gomes da Paixão; do Nascimento, Andréa Mendes; Cavalcanti, Bruno Coêlho; de Moraes, Manoel Odorico; Pessoa, Cláudia; Costa-Lotufo, Letícia Veras; Krogh, Renata; Andricopulo, Adriano Defini; Lopes, Norberto Peporine; Pupo, Mônica Tallarico

    2016-06-01

    Endophytic actinobacteria from the Brazilian medicinal plant Lychnophora ericoides were isolated for the first time, and the biological potential of their secondary metabolites was evaluated. A phylogenic analysis of isolated actinobacteria was accomplished with 16S rRNA gene sequencing, and the predominance of the genus Streptomyces was observed. All strains were cultured on solid rice medium, and ethanol extracts were evaluated with antimicrobial and cytotoxic assays against cancer cell lines. As a result, 92% of the extracts showed a high or moderate activity against at least one pathogenic microbial strain or cancer cell line. Based on the biological and chemical analyses of crude extracts, three endophytic strains were selected for further investigation of their chemical profiles. Sixteen compounds were isolated, and 3-hydroxy-4-methoxybenzamide (9) and 2,3-dihydro-2,2-dimethyl-4(1H)-quinazolinone (15) are reported as natural products for the first time in this study. The biological activity of the pure compounds was also assessed. Compound 15 displayed potent cytotoxic activity against all four tested cancer cell lines. Nocardamine (2) was only moderately active against two cancer cell lines but showed strong activity against Trypanosoma cruzi. Our results show that endophytic actinobacteria from L. ericoides are a promising source of bioactive compounds. © 2016 Verlag Helvetica Chimica Acta AG, Zürich.

  9. Salt Stress Effects on Secondary Metabolites of Cotton in Relation to Gene Expression Responsible for Aphid Development.

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    Qi Wang

    Full Text Available Many secondary metabolites have insecticidal efficacy against pests and may be affected by abiotic stress. However, little is known of how plants may respond to such stress as pertains the growth and development of pests. The objective of this study was to determine if and how salt stress on cotton plants affects the population dynamics of aphids. The NaCl treatment (50 mM, 100 mM, 150 mM and 200 mM increased contents of gossypol in cotton by 26.8-51.4%, flavonoids by 22.5-37.6% and tannic by 15.1-24.3% at 7-28 d after salt stress. Compared with non-stressed plants, the population of aphids on 150 and 200 mM NaCl stressed plants was reduced by 46.4 and 65.4% at 7d and by 97.3 and 100% at 14 days after infestation. Reductions in aphid population were possibly attributed to the elevated secondary metabolism under salt stress. A total of 796 clones for aphids transcriptome, 412 clones in the positive- library (TEST and 384 clones in the reverse-library (Ck, were obtained from subtracted cDNA libraries and sequenced. Gene ontology (GO functional classification and KEGG pathway analysis showed more genes related to fatty acid and lipid biosynthesis, and fewer genes related to carbohydrate metabolism, amino acid metabolism, energy metabolism and cell motility pathways in TEST than in Ck library, which might be the reason of aphids population reduction. A comparative analysis with qRT-PCR indicated high expression of transcripts CYP6A14, CYP6A13, CYP303A1, NADH dehydrogenase and fatty acid synthase in the TEST group. However, CYP307A1 and two ecdysone-induced protein genes were down regulated. The results indicate that genes of aphids related to growth and development can express at a higher level in reaction to the enhanced secondary metabolism in cotton under salinity stress. The expression of CYP307A1 was positively correlated with the population dynamics of aphids since it was involved in ecdysone synthesis.

  10. Seasonal variation of the major secondary metabolites present in the extract of Eremanthus mattogrossensis Less (Asteraceae: Vernonieae leaves

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    Dayana Rubio Gouvea

    2012-01-01

    Full Text Available The species Eremanthus mattogrossensis, known as "veludo do cerrado" (cerrado velvet, is native to the Brazilian Cerrado. Because the amount of metabolites present in plants may be influenced by biological and environmental factors, here we conducted an HPLC-DAD-MS/MS investigation of the metabolite concentrations found in the MeOH/H2O extract of the leaves of this species. The main compounds were identified and quantified, and the metabolites were grouped by chemical class (caffeoylquinic acids, flavonoids, and sesquiterpene lactone. Statistical analysis indicated a straight correlation between the quantity of metabolites and seasonality, suggesting that environmental properties elicit important metabolic responses.

  11. Metabolomics by Proton High-Resolution Magic-Angle-Spinning Nuclear Magnetic Resonance of Tomato Plants Treated with Two Secondary Metabolites Isolated from Trichoderma.

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    Mazzei, Pierluigi; Vinale, Francesco; Woo, Sheridan Lois; Pascale, Alberto; Lorito, Matteo; Piccolo, Alessandro

    2016-05-11

    Trichoderma fungi release 6-pentyl-2H-pyran-2-one (1) and harzianic acid (2) secondary metabolites to improve plant growth and health protection. We isolated metabolites 1 and 2 from Trichoderma strains, whose different concentrations were used to treat seeds of Solanum lycopersicum. The metabolic profile in the resulting 15 day old tomato leaves was studied by high-resolution magic-angle-spinning nuclear magnetic resonance (HRMAS NMR) spectroscopy directly on the whole samples without any preliminary extraction. Principal component analysis (PCA) of HRMAS NMR showed significantly enhanced acetylcholine and γ-aminobutyric acid (GABA) content accompanied by variable amount of amino acids in samples treated with both Trichoderma secondary metabolites. Seed germination rates, seedling fresh weight, and the metabolome of tomato leaves were also dependent upon doses of metabolites 1 and 2 treatments. HRMAS NMR spectroscopy was proven to represent a rapid and reliable technique for evaluating specific changes in the metabolome of plant leaves and calibrating the best concentration of bioactive compounds required to stimulate plant growth.

  12. Secondary metabolite profiles and antifungal drug susceptibility of Aspergillus fumigatus and closely related species, Aspergillus lentulus, Aspergillus udagawae, and Aspergillus viridinutans.

    Science.gov (United States)

    Tamiya, Hiroyuki; Ochiai, Eri; Kikuchi, Kazuyo; Yahiro, Maki; Toyotome, Takahito; Watanabe, Akira; Yaguchi, Takashi; Kamei, Katsuhiko

    2015-05-01

    The incidence of Aspergillus infection has been increasing in the past few years. Also, new Aspergillus fumigatus-related species, namely Aspergillus lentulus, Aspergillus udagawae, and Aspergillus viridinutans, were shown to infect humans. These fungi exhibit marked morphological similarities to A. fumigatus, albeit with different clinical courses and antifungal drug susceptibilities. The present study used liquid chromatography/time-of-flight mass spectrometry to identify the secondary metabolites secreted as virulence factors by these Aspergillus species and compared their antifungal susceptibility. The metabolite profiles varied widely among A. fumigatus, A. lentulus, A. udagawae, and A. viridinutans, producing 27, 13, 8, and 11 substances, respectively. Among the mycotoxins, fumifungin, fumiquinazoline A/B and D, fumitremorgin B, gliotoxin, sphingofungins, pseurotins, and verruculogen were only found in A. fumigatus, whereas auranthine was only found in A. lentulus. The amount of gliotoxin, one of the most abundant mycotoxins in A. fumigatus, was negligible in these related species. In addition, they had decreased susceptibility to antifungal agents such as itraconazole and voriconazole, even though metabolites that were shared in the isolates showing higher minimum inhibitory concentrations than epidemiological cutoff values were not detected. These strikingly different secondary metabolite profiles may lead to the development of more discriminative identification protocols for such closely related Aspergillus species as well as improved treatment outcomes. Copyright © 2015 Japanese Society of Chemotherapy and The Japanese Association for Infectious Diseases. Published by Elsevier Ltd. All rights reserved.

  13. antiSMASH 3.0-a comprehensive resource for the genome mining of biosynthetic gene clusters.

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    Weber, Tilmann; Blin, Kai; Duddela, Srikanth; Krug, Daniel; Kim, Hyun Uk; Bruccoleri, Robert; Lee, Sang Yup; Fischbach, Michael A; Müller, Rolf; Wohlleben, Wolfgang; Breitling, Rainer; Takano, Eriko; Medema, Marnix H

    2015-07-01

    Microbial secondary metabolism constitutes a rich source of antibiotics, chemotherapeutics, insecticides and other high-value chemicals. Genome mining of gene clusters that encode the biosynthetic pathways for these metabolites has become a key methodology for novel compound discovery. In 2011, we introduced antiSMASH, a web server and stand-alone tool for the automatic genomic identification and analysis of biosynthetic gene clusters, available at http://antismash.secondarymetabolites.org. Here, we present version 3.0 of antiSMASH, which has undergone major improvements. A full integration of the recently published ClusterFinder algorithm now allows using this probabilistic algorithm to detect putative gene clusters of unknown types. Also, a new dereplication variant of the ClusterBlast module now identifies similarities of identified clusters to any of 1172 clusters with known end products. At the enzyme level, active sites of key biosynthetic enzymes are now pinpointed through a curated pattern-matching procedure and Enzyme Commission numbers are assigned to functionally classify all enzyme-coding genes. Additionally, chemical structure prediction has been improved by incorporating polyketide reduction states. Finally, in order for users to be able to organize and analyze multiple antiSMASH outputs in a private setting, a new XML output module allows offline editing of antiSMASH annotations within the Geneious software. © The Author(s) 2015. Published by Oxford University Press on behalf of Nucleic Acids Research.

  14. Effect of secondary metabolite of Actinidia deliciosa on the biofilm and extra-cellular matrix components of Acinetobacter baumannii.

    Science.gov (United States)

    Tiwari, Vishvanath; Tiwari, Deepika; Patel, Varsha; Tiwari, Monalisa

    2017-09-01

    Acinetobacter baumannii, opportunistic nosocomial pathogen, increases gradually in the clinical setup. The high level of resistance mechanisms acquired by these bacteria makes their eradication difficult and biofilm formation is one of them. Biofilm comprises of closely packed bacterial population crowded together by extra-cellular matrix (ECM). ECM contains bacterial secreted polymers such as exopolysaccharides (EPS), proteins and extracellular-DNA (e-DNA) and rarely amyloidogenic proteins. Biofilm offers protection of underlying bacterial population against chemotherapeutic agents and host immune system. Therefore, present efforts are focused to find a novel therapeutic that targets biofilm-associated infections. Plants are used as a natural therapeutic for numerous ailments. In order to find an alternative of the available antibacterial drugs, we have focused on the natural herbal active compounds. In this study, we have extracted active compounds from various medicinal plants and screened its anti-biofilm activity against carbapenem resistant strain of A. baumannii. Results showed that polar extract of kiwi (Actinidia deliciosa) and clove (Syzygium aromaticum) exhibit effective anti-biofilm activity. These two plants were also used for their phytochemical screening and TLC profiling to find out the constituting secondary metabolites. Actinidia deliciosa extract contains an alkaloid (sanquinarine) as well as a flavonoid (hydroxyflavone). Anti-biofilm effect of this extract on the ECM of A. baumannii showed that it reduces EPS, protein and eDNA contents in the ECM. Proteins of ECM have also shown to form amyloid like structure, which was evident from its interaction with the Congo Red. CFU counting after Actinidia deliciosa extract treatment also supported the results. Therefore, it can be concluded that polar extract of A. deliciosa can be used to find suitable alternative therapeutic to control biofilm formation by carbapenem resistant strain of

  15. Current concepts on selected plant secondary metabolites with promising inhibitory effects against enzymes linked to Alzheimer's disease.

    Science.gov (United States)

    Orhan, I Erdogan

    2012-01-01

    Alzheimer's disease (AD) has become one of the deadliest diseases for human beings with special incidence in elderly population. It is a progressive neurodegenerative disease and the most prevalent cause of dementia. The neuropathology of AD has not been fully elucidated yet, however, cholinergic hypothesis is the most accepted theory nowadays, resulting from the cholinergic deficit emerging in the brains of AD patients. Shortage of the neurotransmitters, acetylcholine and butyrylcholine has been demonstrated, and therefore, inhibition of the enzymes; acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) that break down acetylcholine and butyrylcholine has become a standard approach for AD treatment. However, cholinesterase inhibitors are only effective in symptomatic treatment and have no ability to impede the disease. The pathogenesis of AD is highly complex and another hypothesis is the formation of amyloid plaques containing beta-amyloid peptide, which causes neurolesions in the brains of AD patients. Beta-amyloid peptide is generated after the sequential cleavage of amyloid precursor protein, especially by the beta- and gamma-secretase in the amyloidogenic pathway. The secretases involved in the processing of amyloid precursor protein are of particular interest and, consequently, the inhibition of secretase enzyme family of protease type has become another desired treatment strategy for AD. On the other hand, medicinal plants are attractive sources for drug research and development as they produce chemically-varying molecules with preferred biological activities. The aim of this article is to review the available data on selected inhibitors from plant secondary metabolites with emphasis on cholinesterase, prolyl endopeptidase, and secretase enzyme families as being the current treatments of AD.

  16. Antimicrobial efficacy of secondary metabolites from Glomerella cingulata Eficiência antimicrobiana do extrato bruto de Glomerella cingulata

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    K. Hara Kishore

    2007-03-01

    Full Text Available Fungi are known to produce a vast array of secondary metabolites that are gaining importance for their biotechnological applications. Early reports suggest that G. cingulata has the capability to transform many compounds by various enzymatic actions. Therefore, the focus of this study was to determine the antibacterial and antifungal activity of crude ethyl acetate extract of G. cingulata using agar cup bioassay method. Crude extract of G. cingulata exhibited remarkable antifungal activity against Rhizopus oryzae, Chrysoporium tropicum and Beauveria bassiana but no antifungal activity was found against Alternaria tenuissima and Aspergillus niger at any concentrations. The crude extract presented no antibacterial activity against Gram positive and Gram negative bacteria at any concentration.Fungos são conhecidos produtores de uma vasta coleção de metabólitos secundários que vem mostrando importância crescente na sua aplicação biotecnológica. Publicações anteriores sugerem que G. cingulata tem a capacidade de transformar vários componentes por diferentes ações enzimáticas. Logo, o foco deste estudo foi determinar a atividade antibacteriana e antifúngica do extrato bruto de G. cingulata obtido por acetato de etila utilizando-se um método envolvendo bloco de agar. O extrato bruto de G. cingulata demonstrou marcante atividade antifungica contra Rhizopus oryzae, Chrysoporium tropicum e Beauveria bassiana entretanto, não foi possível detectar, em nenhuma concentração, atividade antifungica contra Alternaria tenuissima e Aspergillus niger. O mesmo extrato não apresentou atividade antibacteriana, em nenhuma concentração, contra bactérias Gram negativa e positiva.

  17. Supplementing Blends of Sugars, Amino Acids, and Secondary Metabolites to the Diet of Termites (Reticulitermes flavipes) Drive Distinct Gut Bacterial Communities.

    Science.gov (United States)

    Huang, Xing-Feng; Chaparro, Jacqueline M; Reardon, Kenneth F; Judd, Timothy M; Vivanco, Jorge M

    2016-10-01

    Although it is well known that diet is one of the major modulators of the gut microbiome, how the major components of diet shape the gut microbial community is not well understood. Here, we developed a simple system that allows the investigation of the impact of given compounds as supplements of the diet on the termite gut microbiome. The 16S rRNA pyrosequencing analysis revealed that feeding termites different blends of sugars and amino acids did not majorly impact gut community composition; however, ingestion of blends of secondary metabolites caused shifts in gut bacterial community composition. The supplementation of sugars and amino acids reduced the richness significantly, and sugars alone increased the evenness of the gut bacterial community significantly. Secondary metabolites created the most dramatic effects on the microbial community, potentially overriding the effect of other types of compounds. Furthermore, some microbial groups were stimulated specifically by particular groups of compounds. For instance, termites fed with secondary metabolites contained more Firmicutes and Spirochaetes compared to the other treatments. In conclusion, our results suggest that the termite (Reticulitermes flavipes) can be used as a simple and effective system to test the effects of particular chemical compounds in modulating the gut microbiome.

  18. Genomic characterization of a new endophytic Streptomyces kebangsaanensis identifies biosynthetic pathway gene clusters for novel phenazine antibiotic production

    Directory of Open Access Journals (Sweden)

    Juwairiah Remali

    2017-11-01

    Full Text Available Background Streptomyces are well known for their capability to produce many bioactive secondary metabolites with medical and industrial importance. Here we report a novel bioactive phenazine compound, 6-((2-hydroxy-4-methoxyphenoxy carbonyl phenazine-1-carboxylic acid (HCPCA extracted from Streptomyces kebangsaanensis, an endophyte isolated from the ethnomedicinal Portulaca oleracea. Methods The HCPCA chemical structure was determined using nuclear magnetic resonance spectroscopy. We conducted whole genome sequencing for the identification of the gene cluster(s believed to be responsible for phenazine biosynthesis in order to map its corresponding pathway, in addition to bioinformatics analysis to assess the potential of S. kebangsaanensis in producing other useful secondary metabolites. Results The S. kebangsaanensis genome comprises an 8,328,719 bp linear chromosome with high GC content (71.35% consisting of 12 rRNA operons, 81 tRNA, and 7,558 protein coding genes. We identified 24 gene clusters involved in polyketide, nonribosomal peptide, terpene, bacteriocin, and siderophore biosynthesis, as well as a gene cluster predicted to be responsible for phenazine biosynthesis. Discussion The HCPCA phenazine structure was hypothesized to derive from the combination of two biosynthetic pathways, phenazine-1,6-dicarboxylic acid and 4-methoxybenzene-1,2-diol, originated from the shikimic acid pathway. The identification of a biosynthesis pathway gene cluster for phenazine antibiotics might facilitate future genetic engineering design of new synthetic phenazine antibiotics. Additionally, these findings confirm the potential of S. kebangsaanensis for producing various antibiotics and secondary metabolites.

  19. Occurrence of Ochratoxins, Fumonisin B2 , Aflatoxins (B1 and B2 ), and Other Secondary Fungal Metabolites in Dried Date Palm Fruits from Egypt: A Mini-Survey.

    Science.gov (United States)

    Abdallah, Mohamed F; Krska, Rudolf; Sulyok, Michael

    2018-02-01

    This study was conducted to investigate the natural co-occurrence of 295 fungal and bacterial metabolites in 28 samples of dried date palm fruits collected from different shops distributed in Assiut Governorate, Upper Egypt in 2016. Extraction and quantification of the target analytes were done using the "dilute and shoot" approach followed by liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis. In total, 30 toxic fungal metabolites were detected. Among these metabolites, 4 types of ochratoxins including ochratoxin type A and B were quantified in 3 samples (11%) with a contamination range from 1.48 to 6070 μg/kg for ochratoxin A and from 0.28 to 692 μg/kg for ochratoxin B. In addition, fumonisin B 2 was observed in 2 (7%) samples with contamination levels ranging from 4.99 to 16.2 μg/kg. The simultaneous detection of fumonisin B 2 in the same contaminated samples with ochratoxins indicates the fungal attack by Aspergillus niger species during storage. Only 1 sample was contaminated with aflatoxin B 1 (14.4 μg/kg) and B 2 (2.44 μg/kg). The highest maximum concentration (90400 μg/kg) was for kojic acid that contaminated 43% of the samples. To the best of the authors' knowledge, this is the first report of the natural co-occurrence of fumonisin B 2 and ochratoxin A and B in addition to a wide range of other fungal metabolites in date palm fruits. Mycotoxins are secondary metabolites produced by different fungi. These metabolites pose a potential risk on human health since they contaminate many food commodities. Among these, date palm fruits which are an integral part of diet in several countries. Therefore, detection of mycotoxins is a prerequisite to insure the safety of food. Here, different types of mycotoxins have been detected in levels that may have health hazard. © 2018 Institute of Food Technologists®.

  20. The Arabidopsis histone chaperone FACT is required for stress-induced expression of anthocyanin biosynthetic genes.

    Science.gov (United States)

    Pfab, Alexander; Breindl, Matthias; Grasser, Klaus D

    2018-03-01

    The histone chaperone FACT is involved in the expression of genes encoding anthocyanin biosynthetic enzymes also upon induction by moderate high-light and therefore contributes to the stress-induced plant pigmentation. The histone chaperone FACT consists of the SSRP1 and SPT16 proteins and associates with transcribing RNAPII (RNAPII) along the transcribed region of genes. FACT can promote transcriptional elongation by destabilising nucleosomes in the path of RNA polymerase II, thereby facilitating efficient transcription of chromatin templates. Transcript profiling of Arabidopsis plants depleted in SSRP1 or SPT16 demonstrates that only a small subset of genes is differentially expressed relative to wild type. The majority of these genes is either up- or down-regulated in both the ssrp1 and spt16 plants. Among the down-regulated genes, those encoding enzymes of the biosynthetic pathway of the plant secondary metabolites termed anthocyanins (but not regulators of the pathway) are overrepresented. Upon exposure to moderate high-light stress several of these genes are up-regulated to a lesser extent in ssrp1/spt16 compared to wild type plants, and accordingly the mutant plants accumulate lower amounts of anthocyanin pigments. Moreover, the expression of SSRP1 and SPT16 is induced under these conditions. Therefore, our findings indicate that FACT is a novel factor required for the accumulation of anthocyanins in response to light-induction.

  1. Antioxidant Enzyme Activities and Secondary Metabolite Profiling of Oil Palm Seedlings Treated with Combination of NPK Fertilizers Infected with Ganoderma boninense

    Science.gov (United States)

    Mohidin, Hasmah; Idris, Abu Seman; Fariz, A.; Abiri, Rambod; Taheri, Sima; Moradpoor, Mehdi

    2018-01-01

    Oil palm (Elaeis guineensis Jacq) is one of the major sources of edible oil. Reducing the effect of Ganoderma, main cause of basal stem rot (BSR) on oil palm, is the main propose of this study. Understanding the oil palm defense mechanism against Ganoderma infection through monitoring changes in the secondary metabolite compounds levels before/after infection by Ganoderma under different fertilizing treatment is required. Oil palm requires macro- and microelements for growth and yield. Manipulating the nutrient for oil palm is a method to control the disease. The 3-4-month-old oil palm seedlings were given different macronutrient treatments to evaluate induction of defense related enzymes and production of secondary metabolite compounds in response to G. boninense inoculation. The observed trend of changes in the infected and uninfected seedlings was a slightly higher activity for β-1,3-glucanases, chitinase, peroxidase, and phenylalanine ammonia-lyase during the process of pathogenesis. It was found that PR proteins gave positive response to the interaction between oil palm seedlings and Ganoderma infection. Although the responses were activated systematically, they were short-lasting as the changes in enzymes activities appeared before the occurrence of visible symptoms. Effect of different nutrients doses was obviously observed among the results of the secondary metabolite compounds. Many identified/unidentified metabolite compounds were presented, of which some were involved in plant cell defense mechanism against pathogens, mostly belonging to alkaloids with bitter-tasting nitrogenous-compounds, and some had the potential to be used as new markers to detect basal stem rot at the initial step of disease. PMID:29721500

  2. Antioxidant Enzyme Activities and Secondary Metabolite Profiling of Oil Palm Seedlings Treated with Combination of NPK Fertilizers Infected with Ganoderma boninense.

    Science.gov (United States)

    Sahebi, Mahbod; Hanafi, Mohamed M; Mohidin, Hasmah; Rafii, M Y; Azizi, Parisa; Idris, Abu Seman; Fariz, A; Abiri, Rambod; Taheri, Sima; Moradpoor, Mehdi

    2018-01-01

    Oil palm ( Elaeis guineensis Jacq) is one of the major sources of edible oil. Reducing the effect of Ganoderma, main cause of basal stem rot (BSR) on oil palm, is the main propose of this study. Understanding the oil palm defense mechanism against Ganoderma infection through monitoring changes in the secondary metabolite compounds levels before/after infection by Ganoderma under different fertilizing treatment is required. Oil palm requires macro- and microelements for growth and yield. Manipulating the nutrient for oil palm is a method to control the disease. The 3-4-month-old oil palm seedlings were given different macronutrient treatments to evaluate induction of defense related enzymes and production of secondary metabolite compounds in response to G. boninense inoculation. The observed trend of changes in the infected and uninfected seedlings was a slightly higher activity for β -1,3-glucanases, chitinase, peroxidase, and phenylalanine ammonia-lyase during the process of pathogenesis. It was found that PR proteins gave positive response to the interaction between oil palm seedlings and Ganoderma infection. Although the responses were activated systematically, they were short-lasting as the changes in enzymes activities appeared before the occurrence of visible symptoms. Effect of different nutrients doses was obviously observed among the results of the secondary metabolite compounds. Many identified/unidentified metabolite compounds were presented, of which some were involved in plant cell defense mechanism against pathogens, mostly belonging to alkaloids with bitter-tasting nitrogenous-compounds, and some had the potential to be used as new markers to detect basal stem rot at the initial step of disease.

  3. Antioxidant Enzyme Activities and Secondary Metabolite Profiling of Oil Palm Seedlings Treated with Combination of NPK Fertilizers Infected with Ganoderma boninense

    Directory of Open Access Journals (Sweden)

    Mahbod Sahebi

    2018-01-01

    Full Text Available Oil palm (Elaeis guineensis Jacq is one of the major sources of edible oil. Reducing the effect of Ganoderma, main cause of basal stem rot (BSR on oil palm, is the main propose of this study. Understanding the oil palm defense mechanism against Ganoderma infection through monitoring changes in the secondary metabolite compounds levels before/after infection by Ganoderma under different fertilizing treatment is required. Oil palm requires macro- and microelements for growth and yield. Manipulating the nutrient for oil palm is a method to control the disease. The 3-4-month-old oil palm seedlings were given different macronutrient treatments to evaluate induction of defense related enzymes and production of secondary metabolite compounds in response to G. boninense inoculation. The observed trend of changes in the infected and uninfected seedlings was a slightly higher activity for β-1,3-glucanases, chitinase, peroxidase, and phenylalanine ammonia-lyase during the process of pathogenesis. It was found that PR proteins gave positive response to the interaction between oil palm seedlings and Ganoderma infection. Although the responses were activated systematically, they were short-lasting as the changes in enzymes activities appeared before the occurrence of visible symptoms. Effect of different nutrients doses was obviously observed among the results of the secondary metabolite compounds. Many identified/unidentified metabolite compounds were presented, of which some were involved in plant cell defense mechanism against pathogens, mostly belonging to alkaloids with bitter-tasting nitrogenous-compounds, and some had the potential to be used as new markers to detect basal stem rot at the initial step of disease.

  4. Identification of a Classical Mutant in the Industrial Host Aspergillus niger by Systems Genetics: LaeA Is Required for Citric Acid Production and Regulates the Formation of Some Secondary Metabolites

    DEFF Research Database (Denmark)

    Niu, Jing; Arentshorst, Mark; Nair, P. Deepa S.

    2015-01-01

    could provide new insights into the transcriptional control mechanisms related to citric acid production in A. niger. Interestingly, the secondary metabolite profile of a ΔlaeA strain differed from the wild-type strain, showing both decreased and increased metabolite levels, indicating that LaeA is also...

  5. Phenylpropanoids accumulation in eggplant fruit: characterization of biosynthetic genes and regulation by a MYB transcription factor

    Directory of Open Access Journals (Sweden)

    Teresa eDocimo

    2016-01-01

    Full Text Available Phenylpropanoids are major secondary metabolites in eggplant (Solanum melongena fruits. Chlorogenic acid (CGA accounts for 70 to 90% of total phenolics in flesh tissues, while anthocyanins are mainly present in the fruit skin. As a contribution to the understanding of the peculiar accumulation of these health-promoting metabolites in eggplant, we report on metabolite abundance, regulation of CGA and anthocyanin biosynthesis, and characterization of candidate CGA biosynthetic genes in S. melongena.Higher contents of CGA, Delphinidin 3-rutinoside and rutin were found in eggplant fruits compared to other tissues, associated to an elevated transcript abundance of structural genes such as PAL, HQT, DFR and ANS, suggesting that active in situ biosynthesis contributes to anthocyanin and CGA accumulation in fruit tissues. Putative orthologs of the two CGA biosynthetic genes PAL and HQT, as well as a variant of a MYB1 transcription factor showing identity with group 6 MYBs, were isolated from an Occidental S. melongena traditional variety and demonstrated to differ from published sequences from Asiatic varieties.In silico analysis of the isolated SmPAL1, SmHQT1, SmANS, and SmMyb1 promoters revealed the presence of several Myb regulatory elements for the biosynthetic genes and unique elements for the TF, suggesting its involvement in other physiological roles beside phenylpropanoid biosynthesis regulation.Transient overexpression in Nicotiana benthamiana leaves of SmMyb1 and of a C-terminal SmMyb1 truncated form (SmMyb1Δ9 resulted in anthocyanin accumulation only of SmMyb1 agro-infiltrated leaves. A yeast two-hybrid assay confirmed the interaction of both SmMyb1 and SmMyb1Δ9 with an anthocyanin-related potato bHLH1 TF. Interestingly, a doubled amount of CGA was detected in both SmMyb1 and SmMyb1Δ9 agro-infiltrated leaves, thus suggesting that the N-terminal region of SmMyb1 is sufficient to activate its synthesis. These data suggest that a deletion of

  6. SOS response in bacteria: Inhibitory activity of lichen secondary metabolites against Escherichia coli RecA protein.

    Science.gov (United States)

    Bellio, Pierangelo; Di Pietro, Letizia; Mancini, Alisia; Piovano, Marisa; Nicoletti, Marcello; Brisdelli, Fabrizia; Tondi, Donatella; Cendron, Laura; Franceschini, Nicola; Amicosante, Gianfranco; Perilli, Mariagrazia; Celenza, Giuseppe

    2017-06-15

    RecA is a bacterial multifunctional protein essential to genetic recombination, error-prone replicative bypass of DNA damages and regulation of SOS response. The activation of bacterial SOS response is directly related to the development of intrinsic and/or acquired resistance to antimicrobials. Although recent studies directed towards RecA inactivation via ATP binding inhibition described a variety of micromolar affinity ligands, inhibitors of the DNA binding site are still unknown. Twenty-seven secondary metabolites classified as anthraquinones, depsides, depsidones, dibenzofurans, diphenyl-butenolides, paraconic acids, pseudo-depsidones, triterpenes and xanthones, were investigated for their ability to inhibit RecA from Escherichia coli. They were isolated in various Chilean regions from 14 families and 19 genera of lichens. The ATP hydrolytic activity of RecA was quantified detecting the generation of free phosphate in solution. The percentage of inhibition was calculated fixing at 100µM the concentration of the compounds. Deeper investigations were reserved to those compounds showing an inhibition higher than 80%. To clarify the mechanism of inhibition, the semi-log plot of the percentage of inhibition vs. ATP and vs. ssDNA, was evaluated. Only nine compounds showed a percentage of RecA inhibition higher than 80% (divaricatic, perlatolic, alpha-collatolic, lobaric, lichesterinic, protolichesterinic, epiphorellic acids, sphaerophorin and tumidulin). The half-inhibitory concentrations (IC 50 ) calculated for these compounds were ranging from 14.2µM for protolichesterinic acid to 42.6µM for sphaerophorin. Investigations on the mechanism of inhibition showed that all compounds behaved as uncompetitive inhibitors for ATP binding site, with the exception of epiphorellic acid which clearly acted as non-competitive inhibitor of the ATP site. Further investigations demonstrated that epiphorellic acid competitively binds the ssDNA binding site. Kinetic data were

  7. Screening of the in vitro antileishmanial activities of compounds and secondary metabolites isolated from Maytenus guianensis Klotzsch ex Reissek (Celastraceae chichuá Amazon

    Directory of Open Access Journals (Sweden)

    Dionatas Ulises de Oliveira Meneguetti

    Full Text Available Abstract INTRODUCTION Maytenus guianensis is a member of the Celastraceae family that is used in traditional medicine, particularly for its anti-parasitic and anti-cancer effects. To explore the ethnopharmacological potential of this plant, the present study was designed to screen the in vitro antileishmanial activities of extracts and compounds isolated from M. guianensis. METHODS Maytenus guianensis stems and leaves were extracted in acetone, followed by the preparation of eluates and isolation of secondary metabolites using chromatography on a glass column with silica gel as the fixed phase. The chemical components were identified using spectroscopic methods, including one- and two-dimensional nuclear magnetic resonance of hydrogen-1 and carbon-13, mass spectroscopy, and infrared spectroscopy. The anti-Leishmania amazonensis activities of these eluates and compounds were evaluated by direct promastigote counting and viability assays. RESULTS It was found that the hexane bark eluate produced the strongest anti-L. amazonensis effect, with 90-100% inhibition of the promastigote form. The isolated metabolite that produced the best result was tingenone B, followed by a compound formed by the union of tingenone and tingenone B (80-90% inhibition. CONCLUSIONS Maytenus guianensis shows anti-parasite activity that warrants further investigation to determine the mechanisms underlying this antileishmanial effect and to evaluate the pharmacological potential of these eluates and isolated secondary metabolites, while minimizing any adverse effects.

  8. Screening of the in vitro antileishmanial activities of compounds and secondary metabolites isolated from Maytenus guianensis Klotzsch ex Reissek (Celastraceae) chichuá Amazon.

    Science.gov (United States)

    Meneguetti, Dionatas Ulises de Oliveira; Lima, Renato Abreu; Hurtado, Fernanda Bay; Passarini, Guilherme Matos; Macedo, Sharon Rose Aragão; Barros, Neuza Biguinati de; Oliveira, Flávio Augusto de Souza; Medeiros, Patrícia Soares de Maria de; Militão, Júlio Sancho Linhares Teixeira; Nicolete, Roberto; Facundo, Valdir Alves

    2016-01-01

    Maytenus guianensis is a member of the Celastraceae family that is used in traditional medicine, particularly for its anti-parasitic and anti-cancer effects. To explore the ethnopharmacological potential of this plant, the present study was designed to screen the in vitro antileishmanial activities of extracts and compounds isolated from M. guianensis. Maytenus guianensis stems and leaves were extracted in acetone, followed by the preparation of eluates and isolation of secondary metabolites using chromatography on a glass column with silica gel as the fixed phase. The chemical components were identified using spectroscopic methods, including one- and two-dimensional nuclear magnetic resonance of hydrogen-1 and carbon-13, mass spectroscopy, and infrared spectroscopy. The anti-Leishmania amazonensis activities of these eluates and compounds were evaluated by direct promastigote counting and viability assays. It was found that the hexane bark eluate produced the strongest anti-L. amazonensis effect, with 90-100% inhibition of the promastigote form. The isolated metabolite that produced the best result was tingenone B, followed by a compound formed by the union of tingenone and tingenone B (80-90% inhibition). Maytenus guianensis shows anti-parasite activity that warrants further investigation to determine the mechanisms underlying this antileishmanial effect and to evaluate the pharmacological potential of these eluates and isolated secondary metabolites, while minimizing any adverse effects.

  9. Penicillium arizonense, a new, genome sequenced fungal species, reveals a high chemical diversity in secreted metabolites

    Science.gov (United States)

    Grijseels, Sietske; Nielsen, Jens Christian; Randelovic, Milica; Nielsen, Jens; Nielsen, Kristian Fog; Workman, Mhairi; Frisvad, Jens Christian

    2016-01-01

    A new soil-borne species belonging to the Penicillium section Canescentia is described, Penicillium arizonense sp. nov. (type strain CBS 141311T = IBT 12289T). The genome was sequenced and assembled into 33.7 Mb containing 12,502 predicted genes. A phylogenetic assessment based on marker genes confirmed the grouping of P. arizonense within section Canescentia. Compared to related species, P. arizonense proved to encode a high number of proteins involved in carbohydrate metabolism, in particular hemicellulases. Mining the genome for genes involved in secondary metabolite biosynthesis resulted in the identification of 62 putative biosynthetic gene clusters. Extracts of P. arizonense were analysed for secondary metabolites and austalides, pyripyropenes, tryptoquivalines, fumagillin, pseurotin A, curvulinic acid and xanthoepocin were detected. A comparative analysis against known pathways enabled the proposal of biosynthetic gene clusters in P. arizonense responsible for the synthesis of all detected compounds except curvulinic acid. The capacity to produce biomass degrading enzymes and the identification of a high chemical diversity in secreted bioactive secondary metabolites, offers a broad range of potential industrial applications for the new species P. arizonense. The description and availability of the genome sequence of P. arizonense, further provides the basis for biotechnological exploitation of this species. PMID:27739446

  10. Targeting fumonisin biosynthetic genes

    Science.gov (United States)

    The fungus Fusarium is an agricultural problem because it can cause disease on most crop plants and can contaminate crops with mycotoxins. There is considerable variation in the presence/absence and genomic location of gene clusters responsible for synthesis of mycotoxins and other secondary metabol...

  11. Correlation of different spectral lights with biomass accumulation and production of antioxidant secondary metabolites in callus cultures of medicinally important Prunella vulgaris L.

    Science.gov (United States)

    Fazal, Hina; Abbasi, Bilal Haider; Ahmad, Nisar; Ali, Syed Shujait; Akbar, Fazal; Kanwal, Farina

    2016-06-01

    Light is one of the key elicitors that directly fluctuates plant developmental processes and biosynthesis of secondary metabolites. In this study, the effects of various spectral lights on biomass accumulation and production of antioxidant secondary metabolites in callus cultures of Prunella vulgaris were investigated. Among different spectral lights, green light induced the maximum callogenic response (95%). Enhanced fresh biomass accumulation was observed in log phases on day-35, when callus cultures were exposed to yellow and violet lights. Yellow light induced maximum biomass accumulation (3.67g/100ml) from leaf explants as compared to control (1.27g/100ml). In contrast, violet lights enhanced biomass accumulation (3.49g/100ml) from petiole explant. Maximum total phenolics content (TPC; 23.9mg/g-DW) and total flavonoids content (TFC; 1.65mg/g-DW) were observed when cultures were grown under blue lights. In contrast, green and yellow lights enhanced total phenolics production (TPP; 112.52g/100ml) and total flavonoids production (TFP; 9.64g/100ml) as compared to control. The calli grown under green, red and blue lights enhanced DPPH-free radical scavenging activity (DFRSA; 91.3%, 93.1% and 93%) than control (56.44%) respectively. The DFRSA was correlated either with TPC and TFC or TPP and TFP. Furthermore, yellow lights enhanced superoxide dismutase (SOD), peroxidase (POD) and protease activities, however, the content of total protein (CTP) was higher in control cultures (186μg BSAE/mg FW) as compared to spectral lights. These results suggest that the exposure of callus cultures to various spectral lights have shown a key role in biomass accumulation and production of antioxidant secondary metabolites. Copyright © 2016 Elsevier B.V. All rights reserved.

  12. Production of cyathane type secondary metabolites by submerged cultures of Hericium erinaceus and evaluation of their antibacterial activity by direct bioautography.

    Science.gov (United States)

    Shen, T; Morlock, G; Zorn, H

    2015-01-01

    Fungi of the phylum Basidiomycota are well-known to form a broad spectrum of biologically active secondary metabolites, especially low molecular weight compounds such as terpenoids. Hericium erinaceus produces various cyathane type diterpenoids including erinacines. However, no quantitative data and production kinetics have been reported on the biosynthesis of the erinacines C and P in submerged cultures. In the present study, the production of erinacine C was optimized, and the product formation kinetics as well as the antimicrobial activity were studied by high-performance liquid chromatography (HPLC), high-performance thin-layer chromatography (HPTLC) and direct bioautography. Oatmeal and Edamin ® K were identified to be crucial media components for an efficient production of erinacine C. The highest concentrations of erinacine C were obtained in the optimized culture medium on the 9 th culture day (approximately 260 mg L -1 ). The production of erinacine P was strongly time dependent. The maximum concentration of erinacine P of 184 mg L -1 was observed on the third culture day. Afterwards, the concentrations of erinacine P decreased while the concentrations of erinacine C steadily increased. Comparable results were obtained by HPTLC with UV detection and HPLC with diode-array detection (DAD) analyses. Direct bioautography allowed for an additional analysis of the antimicrobial activity of the secondary metabolites. The C and N sources oatmeal and Edamin ® K induced the formation of erinacine C. Detailed product formation kinetics of the erinacines C and P have been reported for the first time. HPTLC combined with the Aliivibrio fischeri bioassay allowed for an instant detection of cyathane diterpenoids in crude extracts and for an evaluation of the antimicrobial activity of the secondary metabolites directly on the plate.

  13. Vanillin biosynthetic pathways in plants.

    Science.gov (United States)

    Kundu, Anish

    2017-06-01

    The present review compiles the up-to-date knowledge on vanillin biosynthesis in plant systems to focus principally on the enzymatic reactions of in planta vanillin biosynthetic pathway and to find out its impact and prospect in future research in this field. Vanillin, a very popular flavouring compound, is widely used throughout the world. The principal natural resource of vanillin is the cured vanilla pods. Due to the high demand of vanillin as a flavouring agent, it is necessary to explore its biosynthetic enzymes and genes, so that improvement in its commercial production can be achieved through metabolic engineering. In spite of significant advancement in elucidating vanillin biosynthetic pathway in the last two decades, no conclusive demonstration had been reported yet for plant system. Several biosynthetic enzymes have been worked upon but divergences in published reports, particularly in characterizing the crucial biochemical steps of vanillin biosynthesis, such as side-chain shortening, methylation, and glucoside formation and have created a space for discussion. Recently, published reviews on vanillin biosynthesis have focused mainly on the biotechnological approaches and bioconversion in microbial systems. This review, however, aims to compile in brief the overall vanillin biosynthetic route and present a comparative as well as comprehensive description of enzymes involved in the pathway in Vanilla planifolia and other plants. Special emphasis has been given on the key enzymatic biochemical reactions that have been investigated extensively. Finally, the present standpoint and future prospects have been highlighted.

  14. Polyphasic characterization of Dolichospermum spp. and Sphaerospermopsis spp. (Nostocales, cyanobacteria): morphology, 16S rRNA gene sequences and fatty acid and secondary metabolite profiles

    Czech Academy of Sciences Publication Activity Database

    Zapomělová, Eliška; Hrouzek, Pavel; Řezanka, Tomáš; Jezberová, Jitka; Řeháková, Klára; Hisem, D.; Komárková, Jaroslava

    2011-01-01

    Roč. 47, č. 5 (2011), s. 1152-1163 ISSN 0022-3646 R&D Projects: GA AV ČR(CZ) KJB600960703; GA ČR(CZ) GAP504/10/1501; GA ČR(CZ) GA206/09/0309 Institutional research plan: CEZ:AV0Z60170517; CEZ:AV0Z50200510; CEZ:AV0Z60050516 Keywords : taxonomy * cyanobacteria * Anabaena * Dolichospermum * Sphaerospermopsis * phylogeny * 16S rRNA gene * fatty acids * secondary metabolites Subject RIV: EE - Microbiology, Virology Impact factor: 2.071, year: 2011

  15. Production of trichothecenes and other secondary metabolites by Fusarium culmorum and Fusarium equiseti on common laboratory media and a soil organic matter agar: An ecological interpretation

    DEFF Research Database (Denmark)

    Hestbjerg, H.; Nielsen, Kristian Fog; Thrane, Ulf

    2002-01-01

    trichothecene production was detected for 94 of 102 F culmorum isolates, only 8 of 57 F equiseti isolates were positive. Profiles of secondary metabolites were compared by following growth on yeast extract sucrose agar (YES), potato sucrose agar (PSA), and an agar medium, prepared from soil organic matter (SOM......), which was included to simulate growth, conditions in soil. SOM supported the production of chrysogine by F culmorum. The two species utilized the media differently. F culmorum produced zearalenone (ZEA) on YES, whereas some F. equiseti isolates produced ZEA on PSA. Other F. equiseti isolates produced...

  16. Secondary metabolite comparison of the species within the Heterobasidion annosum s.l. complex

    DEFF Research Database (Denmark)

    Hansson, David; Wubshet, Sileshi Gizachew; Olson, Åke

    2014-01-01

    The metabolite production of the five members of the fungal species complex Heterobasidion annosum s.l., i.e. H. annosum s.s., H. abietinum, H. parviporum, H. occidentale and H. irregulare, was analyzed by LC–HRMS. The five members are described to have differences in host preferences: H. annosum...

  17. Changing trends in biotechnology of secondary metabolism in medicinal and aromatic plants.

    Science.gov (United States)

    Gandhi, Sumit G; Mahajan, Vidushi; Bedi, Yashbir S

    2015-02-01

    Medicinal and aromatic plants are known to produce secondary metabolites that find uses as flavoring agents, fragrances, insecticides, dyes and drugs. Biotechnology offers several choices through which secondary metabolism in medicinal plants can be altered in innovative ways, to overproduce phytochemicals of interest, to reduce the content of toxic compounds or even to produce novel chemicals. Detailed investigation of chromatin organization and microRNAs affecting biosynthesis of secondary metabolites as well as exploring cryptic biosynthetic clusters and synthetic biology options, may provide additional ways to harness this resource. Plant secondary metabolites are a fascinating class of phytochemicals exhibiting immense chemical diversity. Considerable enigma regarding their natural biological functions and the vast array of pharmacological activities, amongst other uses, make secondary metabolites interesting and important candidates for research. Here, we present an update on changing trends in the biotechnological approaches that are used to understand and exploit the secondary metabolism in medicinal and aromatic plants. Bioprocessing in the form of suspension culture, organ culture or transformed hairy roots has been successful in scaling up secondary metabolite production in many cases. Pathway elucidation and metabolic engineering have been useful to get enhanced yield of the metabolite of interest; or, for producing novel metabolites. Heterologous expression of putative plant secondary metabolite biosynthesis genes in a microbe is useful to validate their functions, and in some cases, also, to produce plant metabolites in microbes. Endophytes, the microbes that normally colonize plant tissues, may also produce the phytochemicals produced by the host plant. The review also provides perspectives on future research in the field.

  18. Pectin Enhances Bio-Control Efficacy by Inducing Colonization and Secretion of Secondary Metabolites by Bacillus amyloliquefaciens SQY 162 in the Rhizosphere of Tobacco.

    Directory of Open Access Journals (Sweden)

    Kai Wu

    Full Text Available Bacillus amyloliquefaciens is a plant-beneficial Gram-positive bacterium involved in suppressing soil-borne pathogens through the secretion of secondary metabolites and high rhizosphere competence. Biofilm formation is regarded as a prerequisite for high rhizosphere competence. In this work, we show that plant extracts affect the chemotaxis and biofilm formation of B. amyloliquefaciens SQY 162 (SQY 162. All carbohydrates tested induced the chemotaxis and biofilm formation of the SQY 162 strain; however, the bacterial growth rate was not influenced by the addition of carbohydrates. A strong chemotactic response and biofilm formation of SQY 162 were both induced by pectin through stimulation of surfactin synthesis and transcriptional expression of biofilm formation related matrix genes. These results suggested that pectin might serve as an environmental factor in the stimulation of the biofilm formation of SQY 162. Furthermore, in pot experiments the surfactin production and the population of SQY 162 in the rhizosphere significantly increased with the addition of sucrose or pectin, whereas the abundance of the bacterial pathogen Ralstonia decreased. With increased production of secondary metabolites in the rhizosphere of tobacco by SQY 162 and improved colonization density of SQY 162 in the pectin treatment, the disease incidences of bacterial wilt were efficiently suppressed. The present study revealed that certain plant extracts might serve as energy sources or environmental cues for SQY 162 to enhance the population density on tobacco root and bio-control efficacy of tobacco bacterial wilt.

  19. Causal agents of Fusarium head blight of durum wheat (Triticum durum Desf.) in central Italy and their in vitro biosynthesis of secondary metabolites.

    Science.gov (United States)

    Beccari, G; Colasante, V; Tini, F; Senatore, M T; Prodi, A; Sulyok, M; Covarelli, L

    2018-04-01

    Durum wheat samples harvested in central Italy (Umbria) were analyzed to: evaluate the occurrence of the fungal community in the grains, molecularly identify the Fusarium spp. which are part of the Fusarium head blight (FHB) complex and characterize the in vitro secondary metabolite profiles of a subset of Fusarium strains. The Fusarium genus was one of the main components of the durum wheat fungal community. The FHB complex was composed of eight species: Fusarium avenaceum (61%), F. graminearum (22%), F. poae (9%), F. culmorum (4%), F. proliferatum (2%), F. sporotrichioides (1%), F. sambucinum (0.5%) and F. langsethiae (0.5%). F. graminearum population was mainly composed of the 15-acetyldeoxynivalenol chemotype, while, F. culmorum population was composed of the 3-acetyldeoxynivalenol chemotype. In vitro characterization of secondary metabolite biosynthesis was conducted for a wide spectrum of substances, showing the mycotoxigenic potential of the species complex. F. avenaceum strains were characterized by high enniantin and moniliformin production. F. graminearum strains were in prevalence deoxynivalenol producers. F. poae strains were characterized by a high biosynthesis of beauvericin like the F. sporotrichioides strain which was also found to be a high T-2/HT-2 toxins producer. Production of aurofusarin, butenolide, gibepyrone D, fusarin C, apicidin was also reported for the analyzed strains. Copyright © 2017 Elsevier Ltd. All rights reserved.

  20. The Application of Ultra-High-Performance Liquid Chromatography Coupled with a LTQ-Orbitrap Mass Technique to Reveal the Dynamic Accumulation of Secondary Metabolites in Licorice under ABA Stress.

    Science.gov (United States)

    Li, Da; Xu, Guojie; Ren, Guangxi; Sun, Yufeng; Huang, Ying; Liu, Chunsheng

    2017-10-20

    The traditional medicine licorice is the most widely consumed herbal product in the world. Although much research work on studying the changes in the active compounds of licorice has been reported, there are still many areas, such as the dynamic accumulation of secondary metabolites in licorice, that need to be further studied. In this study, the secondary metabolites from licorice under two different methods of stress were investigated by ultra-high-performance liquid chromatography coupled with hybrid linear ion trap-Orbitrap mass spectrometry (UHPLC-LTQ-Orbitrap-MS). A complex continuous coordination of flavonoids and triterpenoids in a network was modulated by different methods of stress during growth. The results showed that a total of 51 secondary metabolites were identified in licorice under ABA stress. The partial least squares-discriminate analysis (PLS-DA) revealed the distinction of obvious compounds among stress-specific districts relative to ABA stress. The targeted results showed that there were significant differences in the accumulation patterns of the deeply targeted 41 flavonoids and 10 triterpenoids compounds by PCA and PLS-DA analyses. To survey the effects of flavonoid and triterpenoid metabolism under ABA stress, we inspected the stress-specific metabolic changes. Our study testified that the majority of flavonoids and triterpenoids were elevated in licorice under ABA stress, while the signature metabolite affecting the dynamic accumulation of secondary metabolites was detected. Taken together, our results suggest that ABA-specific metabolite profiling dynamically changed in terms of the biosynthesis of flavonoids and triterpenoids, which may offer new trains of thought on the regular pattern of dynamic accumulation of secondary metabolites in licorice at the metabolite level. Our results also provide a reference for clinical applications and directional planting and licorice breeding.

  1. The Application of Ultra-High-Performance Liquid Chromatography Coupled with a LTQ-Orbitrap Mass Technique to Reveal the Dynamic Accumulation of Secondary Metabolites in Licorice under ABA Stress

    Directory of Open Access Journals (Sweden)

    Da Li

    2017-10-01

    Full Text Available The traditional medicine licorice is the most widely consumed herbal product in the world. Although much research work on studying the changes in the active compounds of licorice has been reported, there are still many areas, such as the dynamic accumulation of secondary metabolites in licorice, that need to be further studied. In this study, the secondary metabolites from licorice under two different methods of stress were investigated by ultra-high-performance liquid chromatography coupled with hybrid linear ion trap–Orbitrap mass spectrometry (UHPLC-LTQ-Orbitrap-MS. A complex continuous coordination of flavonoids and triterpenoids in a network was modulated by different methods of stress during growth. The results showed that a total of 51 secondary metabolites were identified in licorice under ABA stress. The partial least squares–discriminate analysis (PLS-DA revealed the distinction of obvious compounds among stress-specific districts relative to ABA stress. The targeted results showed that there were significant differences in the accumulation patterns of the deeply targeted 41 flavonoids and 10 triterpenoids compounds by PCA and PLS-DA analyses. To survey the effects of flavonoid and triterpenoid metabolism under ABA stress, we inspected the stress-specific metabolic changes. Our study testified that the majority of flavonoids and triterpenoids were elevated in licorice under ABA stress, while the signature metabolite affecting the dynamic accumulation of secondary metabolites was detected. Taken together, our results suggest that ABA-specific metabolite profiling dynamically changed in terms of the biosynthesis of flavonoids and triterpenoids, which may offer new trains of thought on the regular pattern of dynamic accumulation of secondary metabolites in licorice at the metabolite level. Our results also provide a reference for clinical applications and directional planting and licorice breeding.

  2. Biogenic synthesis of silver nanoparticle by using secondary metabolites from Pseudomonas aeruginosa DM1 and its anti-algal effect on Chlorella vulgaris and Chlorella pyrenoidosa.

    Science.gov (United States)

    Kumari, Rima; Barsainya, Manjari; Singh, Devendra Pratap

    2017-02-01

    Biogenic synthesis of silver nanoparticles (AgNPs) using extracellular metabolites from the bacterium Pseudomonas aeruginosa DM1 offers an eco-friendly and sustainable way of metal nanoparticle synthesis. The present work highlights the biotransformation of silver nitrate solution into AgNP, mediated by extracellular secondary metabolite pyoverdine, a siderophore produced by P. aeruginosa. The bioreduction of silver ions into AgNPs by using pyoverdine was recorded in terms of Fourier transform infrared spectroscopy (FTIR) analysis and color change in the reaction mixture (AgNO 3 + pyoverdine) from pale yellow to dark brown with absorption maxima at 415 nm. The results of X-ray diffraction (XRD) analysis of AgNPs showed its crystalline face-centered cubic structure. The scanning electron microscopy (SEM) and transmission electron microscopy (TEM) pictures of AgNPs showed spherical morphology of AgNP in the range of 45-100 nm, with tendency of agglomerations. The energy-dispersive X-ray (EDX) analysis of particles provided strong signal of elemental silver with few minor peaks of other impurities. The present approach offers a unique in vitro method of metal nanoparticle synthesis by exogenously produced bacterial secondary metabolites, where direct contact between the toxic metal and biological resource material can be avoided. The biologically synthesized AgNPs are found to have anti-algal effects against two species of Chlorella (Chlorella vulgaris and Chlorella pyenoidosa), as indicated by zone of growth inhibition on algal culture plates. Further results exhibit concentration-dependent progressive inhibition of chlorophyll content in the algal cells by AgNPs, confirming the algicidal effect of AgNPs.

  3. Secondary metabolites of Cynodon dactylon as an antagonist to angiotensin II type1 receptor: Novel in silico drug targeting approach for diabetic retinopathy

    Science.gov (United States)

    Jananie, R. K.; Priya, V.; Vijayalakshmi, K.

    2012-01-01

    Objectives: To study the ability of the secondary metabolites of Cynodon dactylon to serve as an antagonist to angiotensin II type 1 receptor (AT1); activation of this receptor plays a vital role in diabetic retinopathy (DR). Materials and Methods: In silico methods are mainly harnessed to reduce time, cost and risk associated with drug discovery. Twenty-four compounds were identified as the secondary metabolites of hydroalcoholic extract of C. dactylon using the GCMS technique. These were considered as the ligands or inhibitors that would serve as an antagonist to the AT1. The ACD/Chemsketch tool was used to generate 3D structures of the ligands. A molecular file format converter tool was used to convert the generated data to the PDB format (Protein Data Bank) and was used for docking studies. The AT1 structure was retrieved from the Swissprot data base and PDB and visualized using the Rasmol tool. Domain analysis was carried from the Pfam data base; following this, the active site of the target protein was identified using a Q-site finder tool. The ability of the ligands to bind with the active site of AT1 was studied using the Autodocking tool. The docking results were analyzed using the WebLab viewer tool. Results: Sixteen ligands showed effective binding with the target protein; diazoprogesteron, didodecyl phthalate, and 9,12-octadecadienoyl chloride (z,z) may be considered as compounds that could be used to bind with the active site sequence of AT1. Conclusions: The present study shows that the metabolites of C. dactylon could serve as a natural antagonist to AT1 that could be used to treat diabetic retinopathy. PMID:22368412

  4. Secondary metabolites of vertebrate-dispersed fruits: evidence for adaptive functions Metabolitos secundarios de frutos dispersados por aves: evidencia de funciones adaptativas

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    MARTIN L. CIPOLLINI

    2000-09-01

    Full Text Available In this paper, I discuss recent evidence concerning the adaptive significance of secondary metabolites in ripe fleshy fruits, and implications for seed dispersal by birds and other vertebrates. Specifically, I revisit a number of adaptive hypotheses originally presented and discussed by Cipollini & Levey in 1997, including the Attraction/Association, Seed Germination Effects, Attraction/Repulsion, Protein Assimilation, Gut Retention Time, Directed and General Toxicity, and Defense Tradeoffs hypotheses. I also present and discuss a new adaptive hypothesis, the Direct Nutritional Benefits hypothesis, posed to reflect recent discoveries concerning the positive dietary effects of some secondary metabolites. From this review, I conclude that focused studies are much needed to provide direct tests of these hypotheses. Evidence addressing many of the hypotheses is either observational or indirect, and gleaned from studies not directly designed to address these hypotheses. Despite this, most hypotheses find at least some level of support - even when the same metabolite is being considered (e.g., anthocyanins and carotenoids having functions as pigments as well as nutritional antioxidants. I conclude with a discussion of the nature of multiple molecular targets of plant secondary chemicals. In doing so, I reinforce the notion that synergistic interactions and multifunctionality of secondary metabolites may provide economical evolutionary solutions for plants facing the disparate and temporally variable selective pressures that impinge upon fruits and seeds. As such, it may not be surprising that specific secondary metabolites serve more than one adaptive function in ripe fleshy fruits; finding support for several non-mutually exclusive hypotheses is likely. Comparative studies designed to address these hypotheses should be undertaken with a careful consideration of the potential underlying effects of phylogeny and physiological constraints on such

  5. Genomic and secondary metabolite analyses of Streptomyces sp. 2AW provide insight into the evolution of the cycloheximide pathway

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    Elizabeth eStulberg

    2016-05-01

    Full Text Available The dearth of new antibiotics in the face of widespread antimicrobial resistance makes developing innovative strategies for discovering new antibiotics critical for the future management of infectious disease. Understanding the genetics and evolution of antibiotic producers will help guide the discovery and bioengineering of novel antibiotics. We discovered an isolate in Alaskan boreal forest soil that had broad antimicrobial activity. We elucidated the corresponding antimicrobial natural products and sequenced the genome of this isolate, designated Streptomyces sp. 2AW. This strain illustrates the chemical virtuosity typical of the Streptomyces genus, producing cycloheximide as well as two other biosynthetically unrelated antibiotics, neutramycin and hygromycin A. Combining bioinformatic and chemical analyses, we identified the gene clusters responsible for antibiotic production. Interestingly, 2AW appears dissimilar from other cycloheximide producers in that the gene encoding the polyketide synthase resides on a separate part of the chromosome from the genes responsible for tailoring cycloheximide-specific modifications. This gene arrangement and our phylogenetic analyses of the gene products suggest that 2AW holds an evolutionarily ancestral lineage of the cycloheximide pathway. Our analyses support the hypothesis that the 2AW glutaramide gene cluster is basal to the lineage wherein cycloheximide production diverged from other glutarimide antibiotics. This study illustrates the power of combining modern biochemical and genomic analyses to gain insight into the evolution of antibiotic-producing microorganisms.

  6. Transcriptome sequencing and de novo assembly in arecanut, Areca catechu L elucidates the secondary metabolite pathway genes

    Directory of Open Access Journals (Sweden)

    Ramaswamy Manimekalai

    2018-03-01

    Full Text Available Areca catechu L. belongs to the Arecaceae family which comprises many economically important palms. The palm is a source of alkaloids and carotenoids. The lack of ample genetic information in public databases has been a constraint for the genetic improvement of arecanut. To gain molecular insight into the palm, high throughput RNA sequencing and de novo assembly of arecanut leaf transcriptome was undertaken in the present study. A total 56,321,907 paired end reads of 101 bp length consisting of 11.343 Gb nucleotides were generated. De novo assembly resulted in 48,783 good quality transcripts, of which 67% of transcripts could be annotated against NCBI non – redundant database. The Gene Ontology (GO analysis with UniProt database identified 9222 biological process, 11268 molecular function and 7574 cellular components GO terms. Large scale expression profiling through Fragments per Kilobase per Million mapped reads (FPKM showed major genes involved in different metabolic pathways of the plant. Metabolic pathway analysis of the assembled transcripts identified 124 plant related pathways. The transcripts related to carotenoid and alkaloid biosynthetic pathways had more number of reads and FPKM values suggesting higher expression of these genes. The arecanut transcript sequences generated in the study showed high similarity with coconut, oil palm and date palm sequences retrieved from public domains. We also identified 6853 genic SSR regions in the arecanut. The possible primers were designed for SSR detection and this would simplify the future efforts in genetic characterization of arecanut.

  7. Penicillium arizonense, a new, genome sequenced fungal species, reveals a high chemical diversity in secreted metabolites

    DEFF Research Database (Denmark)

    Grijseels, Sietske; Nielsen, Jens Christian; Randelovic, Milica

    2016-01-01

    A new soil-borne species belonging to the Penicillium section Canescentia is described, Penicillium arizonense sp. nov. (type strain CBS 141311T = IBT 12289T). The genome was sequenced and assembled into 33.7 Mb containing 12,502 predicted genes. A phylogenetic assessment based on marker genes...... confirmed the grouping of P. arizonense within section Canescentia. Compared to related species, P. arizonense proved to encode a high number of proteins involved in carbohydrate metabolism, in particular hemicellulases. Mining the genome for genes involved in secondary metabolite biosynthesis resulted...... of biosynthetic gene clusters in P. arizonense responsible for the synthesis of all detected compounds except curvulinic acid. The capacity to produce biomass degrading enzymes and the identification of a high chemical diversity in secreted bioactive secondary metabolites, offers a broad range of potential...

  8. Tilting Plant Metabolism for Improved Metabolite Biosynthesis and Enhanced Human Benefit

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    Bhekumthetho Ncube

    2015-07-01

    Full Text Available The immense chemical diversity of plant-derived secondary metabolites coupled with their vast array of biological functions has seen this group of compounds attract considerable research interest across a range of research disciplines. Medicinal and aromatic plants, in particular, have been exploited for this biogenic pool of phytochemicals for products such as pharmaceuticals, fragrances, dyes, and insecticides, among others. With consumers showing increasing interests in these products, innovative biotechnological techniques are being developed and employed to alter plant secondary metabolism in efforts to improve on the quality and quantity of specific metabolites of interest. This review provides an overview of the biosynthesis for phytochemical compounds with medicinal and other related properties and their associated biological activities. It also provides an insight into how their biosynthesis/biosynthetic pathways have been modified/altered to enhance production.

  9. Biosynthetic Pathway and Metabolic Engineering of Plant Dihydrochalcones.

    Science.gov (United States)

    Ibdah, Mwafaq; Martens, Stefan; Gang, David R

    2018-03-14

    Dihydrochalcones are plant natural products containing the phenylpropanoid backbone and derived from the plant-specific phenylpropanoid pathway. Dihydrochalcone compounds are important in plant growth and response to stresses and, thus, can have large impacts on agricultural activity. In recent years, these compounds have also received increased attention from the biomedical community for their potential as anticancer treatments and other benefits for human health. However, they are typically produced at relatively low levels in plants. Therefore, an attractive alternative is to express the plant biosynthetic pathway genes in microbial hosts and to engineer the metabolic pathway/host to improve the production of these metabolites. In the present review, we discuss in detail the functions of genes and enzymes involved in the biosynthetic pathway of the dihydrochalcones and the recent strategies and achievements used in the reconstruction of multi-enzyme pathways in microorganisms in efforts to be able to attain higher amounts of desired dihydrochalcones.

  10. Proteomic and Metabolomic Analyses Reveal Contrasting Anti-Inflammatory Effects of an Extract of Mucor Racemosus Secondary Metabolites Compared to Dexamethasone.

    Science.gov (United States)

    Meier, Samuel M; Muqaku, Besnik; Ullmann, Ronald; Bileck, Andrea; Kreutz, Dominique; Mader, Johanna C; Knasmüller, Siegfried; Gerner, Christopher

    2015-01-01

    Classical drug assays are often confined to single molecules and targeting single pathways. However, it is also desirable to investigate the effects of complex mixtures on complex systems such as living cells including the natural multitude of signalling pathways. Evidence based on herbal medicine has motivated us to investigate potential beneficial health effects of Mucor racemosus (M rac) extracts. Secondary metabolites of M rac were collected using a good-manufacturing process (GMP) approved production line and a validated manufacturing process, in order to obtain a stable product termed SyCircue (National Drug Code USA: 10424-102). Toxicological studies confirmed that this product does not contain mycotoxins and is non-genotoxic. Potential effects on inflammatory processes were investigated by treating stimulated cells with M rac extracts and the effects were compared to the standard anti-inflammatory drug dexamethasone on the levels of the proteome and metabolome. Using 2D-PAGE, slight anti-inflammatory effects were observed in primary white blood mononuclear cells, which were more pronounced in primary human umbilical vein endothelial cells (HUVECs). Proteome profiling based on nLC-MS/MS analysis of tryptic digests revealed inhibitory effects of M rac extracts on pro-inflammatory cytoplasmic mediators and secreted cytokines and chemokines in these endothelial cells. This finding was confirmed using targeted proteomics, here treatment of stimulated cells with M rac extracts down-regulated the secretion of IL-6, IL-8, CXCL5 and GROA significantly. Finally, the modulating effects of M rac on HUVECs were also confirmed on the level of the metabolome. Several metabolites displayed significant concentration changes upon treatment of inflammatory activated HUVECs with the M rac extract, including spermine and lysophosphatidylcholine acyl C18:0 and sphingomyelin C26:1, while the bulk of measured metabolites remained unaffected. Interestingly, the effects of M rac

  11. Biosynthetic Pathways of Ergot Alkaloids

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    Nina Gerhards

    2014-12-01

    Full Text Available Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines. All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine. Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes.

  12. Cloning, reassembling and integration of the entire nikkomycin biosynthetic gene cluster into Streptomyces ansochromogenes lead to an improved nikkomycin production

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    Yang Haihua

    2010-01-01

    Full Text Available Abstract Background Nikkomycins are a group of peptidyl nucleoside antibiotics produced by Streptomyces ansochromogenes. They are competitive inhibitors of chitin synthase and show potent fungicidal, insecticidal, and acaricidal activities. Nikkomycin X and Z are the main components produced by S. ansochromogenes. Generation of a high-producing strain is crucial to scale up nikkomycins production for further clinical trials. Results To increase the yields of nikkomycins, an additional copy of nikkomycin biosynthetic gene cluster (35 kb was introduced into nikkomycin producing strain, S. ansochromogenes 7100. The gene cluster was first reassembled into an integrative plasmid by Red/ET technology combining with classic cloning methods and then the resulting plasmid(pNIKwas introduced into S. ansochromogenes by conjugal transfer. Introduction of pNIK led to enhanced production of nikkomycins (880 mg L-1, 4 -fold nikkomycin X and 210 mg L-1, 1.8-fold nikkomycin Z in the resulting exconjugants comparing with the parent strain (220 mg L-1 nikkomycin X and 120 mg L-1 nikkomycin Z. The exconjugants are genetically stable in the absence of antibiotic resistance selection pressure. Conclusion A high nikkomycins producing strain (1100 mg L-1 nikkomycins was obtained by introduction of an extra nikkomycin biosynthetic gene cluster into the genome of S. ansochromogenes. The strategies presented here could be applicable to other bacteria to improve the yields of secondary metabolites.

  13. Anticancer and antibacterial secondary metabolites from the endophytic fungus Penicillium sp. CAM64 against multi-drug resistant Gram-negative bacteria.

    Science.gov (United States)

    Jouda, Jean-Bosco; Tamokou, Jean-de-Dieu; Mbazoa, Céline Djama; Sarkar, Prodipta; Bag, Prasanta Kumar; Wandji, Jean

    2016-09-01

    The emergence of multiple-drug resistance bacteria has become a major threat and thus calls for an urgent need to search for new effective and safe anti-bacterial agents. This study aims to evaluate the anticancer and antibacterial activities of secondary metabolites from Penicillium sp., an endophytic fungus associated with leaves of Garcinia nobilis. The culture filtrate from the fermentation of Penicillium sp. was extracted and analyzed by liquid chromatography-mass spectrometry, and the major metabolites were isolated and identified by spectroscopic analyses and by comparison with published data. The antibacterial activity of the compounds was assessed by broth microdilution method while the anticancer activity was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The fractionation of the crude extract afforded penialidin A-C (1-3), citromycetin (4), p-hydroxyphenylglyoxalaldoxime (5) and brefelfin A (6). All of the compounds tested here showed antibacterial activity (MIC = 0.50 - 128 µg/mL) against Gramnegative multi-drug resistance bacteria, Vibrio cholerae (causative agent of dreadful disease cholera) and Shigella flexneri (causative agent of shigellosis), as well as the significant anticancer activity (LC 50 = 0.88 - 9.21 µg/mL) against HeLa cells. The results obtained indicate that compounds 1-6 showed good antibacterial and anticancer activities with no toxicity to human red blood cells and normal Vero cells.

  14. HPLC-ElCD: an useful tool for the pursuit of novel analytical strategies for the detection of antioxidant secondary metabolites

    Directory of Open Access Journals (Sweden)

    Castro-Gamboa Ian

    2003-01-01

    Full Text Available Living cells are continuously exposed to a variety of challenges that exert oxidative stress and are directly related with senescence and the onset of various pathological conditions such as coronary heart disease, rheumatoid arthritis and cancer. Nevertheless, living organisms have developed a complex antioxidant network to counteract reactive species that are detrimental to life. With the aim of bio-prospecting plant species from the Brazilian Cerrado and Atlantic Forest, we have established a methodology to detect secondary antioxidant metabolites in crude extracts and fractions obtained from plant species. Combining HPLC with an electrochemical detector allowed us to detect micromolecules that showed antioxidant activities in Chimarrhis turbinata (DC leaf extracts. Comparison with purified flavonoid standards led us to identify the compounds in their natural matrices giving valuable information on their antioxidant capacity.

  15. Productivity of the study of secondary metabolites of Cassia alata L. (Caesalpinaceae) by the techniques of in vitro culture was associated gamma-irradiation

    International Nuclear Information System (INIS)

    Luyindula, N.; Mbaya, N.; Ekalakala, T.; Kikakedimau, N.; Bulubulu, O.; Diamuini, N.; Nyembo, K.; Mwambi, N.; Mulwele, N.

    2005-01-01

    The leaves explants of Cassia alata L. has been radiated to the gamma radiance to the doses of 1; 2.5; 5; 7.5 and 10 Gy and cultivated on the Middle MS. The gotten results revealed that the callogenesis of Cassia alata decreases with the increase of the irradiation dose. The yield of secondary metabolites is superior at the calli of explants radiated to 5 Gy (25.37% for the chloroformics extracts and 35.9% for the aqueous extracts) in relation to the yield gotten at the calli of explants radiated to other doses however no and at the original plant. An antibacterial activity (on Shigella flexneri, Staphylococcus aureus and Escherichia coli); and antifongic (on Candida albicans) has been observed.

  16. High GC Content Cas9-Mediated Genome-Editing and Biosynthetic Gene Cluster Activation in Saccharopolyspora erythraea.

    Science.gov (United States)

    Liu, Yong; Wei, Wen-Ping; Ye, Bang-Ce

    2018-05-18

    The overexpression of bacterial secondary metabolite biosynthetic enzymes is the basis for industrial overproducing strains. Genome editing tools can be used to further improve gene expression and yield. Saccharopolyspora erythraea produces erythromycin, which has extensive clinical applications. In this study, the CRISPR-Cas9 system was used to edit genes in the S. erythraea genome. A temperature-sensitive plasmid containing the PermE promoter, to drive Cas9 expression, and the Pj23119 and PkasO promoters, to drive sgRNAs, was designed. Erythromycin esterase, encoded by S. erythraea SACE_1765, inactivates erythromycin by hydrolyzing the macrolactone ring. Sequencing and qRT-PCR confirmed that reporter genes were successfully inserted into the SACE_1765 gene. Deletion of SACE_1765 in a high-producing strain resulted in a 12.7% increase in erythromycin levels. Subsequent PermE- egfp knock-in at the SACE_0712 locus resulted in an 80.3% increase in erythromycin production compared with that of wild type. Further investigation showed that PermE promoter knock-in activated the erythromycin biosynthetic gene clusters at the SACE_0712 locus. Additionally, deletion of indA (SACE_1229) using dual sgRNA targeting without markers increased the editing efficiency to 65%. In summary, we have successfully applied Cas9-based genome editing to a bacterial strain, S. erythraea, with a high GC content. This system has potential application for both genome-editing and biosynthetic gene cluster activation in Actinobacteria.

  17. Abscisic Acid Induced Changes in Production of Primary and Secondary Metabolites, Photosynthetic Capacity, Antioxidant Capability, Antioxidant Enzymes and Lipoxygenase Inhibitory Activity of Orthosiphon stamineus Benth.

    Directory of Open Access Journals (Sweden)

    Mohd Hafiz Ibrahim

    2013-07-01

    Full Text Available An experiment was conducted to investigate and distinguish the relationships in the production of total phenolics, total flavonoids, soluble sugars, H2O2, O2−, phenylalanine ammonia lyase (PAL activity, leaf gas exchange, antioxidant activity, antioxidant enzyme activity [ascorbate peroxidase (APX, catalase (CAT, superoxide dismutase (SOD and Lipoxygenase inhibitory activity (LOX] under four levels of foliar abscisic acid (ABA application (0, 2, 4, 6 µM for 15 weeks in Orthosiphon stamineus Benth. It was found that the production of plant secondary metabolites, soluble sugars, antioxidant activity, PAL activity and LOX inhibitory activity was influenced by foliar application of ABA. As the concentration of ABA was increased from 0 to 6 µM the production of total phenolics, flavonoids, sucrose, H2O2, O2−, PAL activity and LOX inhibitory activity was enhanced. It was also observed that the antioxidant capabilities (DPPH and ORAC were increased. This was followed by increases in production of antioxidant enzymes APX, CAT and SOD. Under high application rates of ABA the net photosynthesis and stomatal conductance was found to be reduced. The production of primary and secondary metabolites displayed a significant positive relationship with H2O2 (total phenolics, r2 = 0.877; total flavonoids, r2 = 0.812; p ≤ 0.05 and O2− (total phenolics, r2 = 0.778; total flavonoids, r2 = 0.912; p ≤ 0.05. This indicated that increased oxidative stress at high application rates of ABA, improved the production of phytochemicals.

  18. The rate of aucubin, a secondary metabolite in Plantago lanceolata and potential nitrification inhibitor, needed to reduce ruminant urine patch nitrous oxide emissions

    Science.gov (United States)

    Gardiner, C. A.; Clough, T.; Cameron, K.; Di, H.; Edwards, G. R.

    2017-12-01

    Nitrous oxide (N2O) losses derived from grazing ruminant livestock urine patches account for 40% of global N2O emissions. It has been shown that Plantago lanceolata, an herb species used in grazed pastures, contains an active secondary metabolite (aucubin) that has the potential to be excreted by grazing ruminants and inhibit nitrification in the urine patch, a key step in soil N2O production. However, the urinary excretion rate of aucubin needed to significantly reduce urine patch N2O emissions remains unknown. Aucubin was dissolved in bovine urine at three rates (47, 243, and 486 kg ha-1), based on rates used in Dietz et al. (2013) and the calculated highest potential aucubin application rate, from Gardiner et al. (2017). A control, along with a urine treatment and the three aucubin treatments (all urine applied at 700 kg N ha-1), was applied to 20 g soil and incubated in the laboratory for 35 d. Soils were monitored for surface pH, inorganic N concentration (NH4+/NO3-), and gas (N2O and CO2) fluxes. This experiment is currently underway and the results will be presented at the conference. Dietz M, Machill S, Hoffmann H, Schmidtke K 2013. Inhibitory effects of Plantago lanceolata L. on soil N mineralization. Plant and Soil 368: 445-458. Gardiner CA, Clough TJ, Cameron KC, Di HJ, Edwards GR, de Klein CAM 2017. The potential inhibitory effects of Plantago lanceolata and its active secondary metabolite aucubin on soil nitrification and nitrous oxide emissions under ruminant urine patch conditions. Manuscript submitted for publication.

  19. New Insights on Wood Dimensional Stability Influenced by Secondary Metabolites: The Case of a Fast-Growing Tropical Species Bagassa guianensis Aubl.

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    Julie Bossu

    Full Text Available Challenging evaluation of tropical forest biodiversity requires the reporting of taxonomic diversity but also the systematic characterization of wood properties in order to discover new promising species for timber industry. Among wood properties, the dimensional stability is regarded as a major technological characteristic to validate whether a wood species is adapted to commercial uses. Cell structure and organization are known to influence the drying shrinkage making wood density and microfibrils angle markers of choice to predict wood dimensional stability. On the contrary the role of wood extractive content remains unclear. This work focuses on the fast-growing tropical species Bagassa guianensis and we report herein a correlation between heartwood drying shrinkage and extractive content. Chemical extractions and shrinkage experiments were performed on separate wood twin samples to better evaluate correctly how secondary metabolites influence the wood shrinkage behaviour. Extractive content were qualitatively and quantitatively analysed using HPLC and NMR spectroscopy. We found that B guianensis heartwood has a homogeneous low shrinkage along its radius that could not be explained only by its basic density. In fact the low drying shrinkage is correlated to the high extractive content and a corrected model to improve the prediction of wood dimensional stability is presented. Additionally NMR experiments conducted on sapwood and heartwood extracts demonstrate that secondary metabolites biosynthesis occurs in sapwood thus revealing B. guianensis as a Juglans-Type heartwood formation. This work demonstrates that B. guianensis, a fast-growing species associated with high durability and high dimensional stability, is a good candidate for lumber production and commercial purposes.

  20. Intercropping Induces Changes in Specific Secondary Metabolite Concentration in Ethiopian Kale (Brassica carinata) and African Nightshade (Solanum scabrum) under Controlled Conditions.

    Science.gov (United States)

    Ngwene, Benard; Neugart, Susanne; Baldermann, Susanne; Ravi, Beena; Schreiner, Monika

    2017-01-01

    Intercropping is widespread in small-holder farming systems in tropical regions and is also practiced in the cultivation of indigenous vegetables, to alleviate the multiple burdens of malnutrition. Due to interspecific competition and/or complementation between intercrops, intercropping may lead to changes in plants accumulation of minerals and secondary metabolites and hence, alter nutritional quality for consumers. Intercropping aims to intensify land productivity, while ensuring that nutritional quality is not compromised. This study aimed to investigate changes in minerals and secondary plant metabolites in intercropped Brassica carinata and Solanum scabrum , two important African indigenous vegetables, and evaluated the suitability of this combination for dryer areas. B. carinata and S. scabrum were grown for 6 weeks under controlled conditions in a greenhouse trial. Large rootboxes (8000 cm 3 volume) were specifically designed for this experiment. Each rootbox was planted with two plants, either of the same plant species (mono) or one of each plant species (mixed). A quartz sand/soil substrate was used and fertilized adequately for optimal plant growth. During the last 4 weeks of the experiment, the plants were either supplied with optimal (65% WHC) or low (30% WHC) irrigation, to test the effect of a late-season drought. Intercropping increased total glucosinolate content in B. carinata , while maintaining biomass production and the contents of other health related minerals in both B. carinata and S. scabrum . Moreover, low irrigation led to an increase in carotene accumulation in both mono and intercropped S. scabrum , but not in B. carinata , while the majority of kaempferol glycosides and hydroxycinnamic acid derivatives of both species were decreased by intercropping and drought treatment. This study indicates that some health-related phytochemicals can be modified by intercropping or late-season drought, but field validation of these results is

  1. Intercropping Induces Changes in Specific Secondary Metabolite Concentration in Ethiopian Kale (Brassica carinata and African Nightshade (Solanum scabrum under Controlled Conditions

    Directory of Open Access Journals (Sweden)

    Benard Ngwene

    2017-09-01

    Full Text Available Intercropping is widespread in small-holder farming systems in tropical regions and is also practiced in the cultivation of indigenous vegetables, to alleviate the multiple burdens of malnutrition. Due to interspecific competition and/or complementation between intercrops, intercropping may lead to changes in plants accumulation of minerals and secondary metabolites and hence, alter nutritional quality for consumers. Intercropping aims to intensify land productivity, while ensuring that nutritional quality is not compromised. This study aimed to investigate changes in minerals and secondary plant metabolites in intercropped Brassica carinata and Solanum scabrum, two important African indigenous vegetables, and evaluated the suitability of this combination for dryer areas. B. carinata and S. scabrum were grown for 6 weeks under controlled conditions in a greenhouse trial. Large rootboxes (8000 cm3 volume were specifically designed for this experiment. Each rootbox was planted with two plants, either of the same plant species (mono or one of each plant species (mixed. A quartz sand/soil substrate was used and fertilized adequately for optimal plant growth. During the last 4 weeks of the experiment, the plants were either supplied with optimal (65% WHC or low (30% WHC irrigation, to test the effect of a late-season drought. Intercropping increased total glucosinolate content in B. carinata, while maintaining biomass production and the contents of other health related minerals in both B. carinata and S. scabrum. Moreover, low irrigation led to an increase in carotene accumulation in both mono and intercropped S. scabrum, but not in B. carinata, while the majority of kaempferol glycosides and hydroxycinnamic acid derivatives of both species were decreased by intercropping and drought treatment. This study indicates that some health-related phytochemicals can be modified by intercropping or late-season drought, but field validation of these results is

  2. Widespread occurrence of secondary lipid biosynthesis potential in microbial lineages.

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    Christine N Shulse

    Full Text Available Bacterial production of long-chain omega-3 polyunsaturated fatty acids (PUFAs, such as eicosapentaenoic acid (EPA, 20:5n-3 and docosahexaenoic acid (DHA, 22:6n-3, is constrained to a narrow subset of marine γ-proteobacteria. The genes responsible for de novo bacterial PUFA biosynthesis, designated pfaEABCD, encode large, multi-domain protein complexes akin to type I iterative fatty acid and polyketide synthases, herein referred to as "Pfa synthases". In addition to the archetypal Pfa synthase gene products from marine bacteria, we have identified homologous type I FAS/PKS gene clusters in diverse microbial lineages spanning 45 genera representing 10 phyla, presumed to be involved in long-chain fatty acid biosynthesis. In total, 20 distinct types of gene clusters were identified. Collectively, we propose the designation of "secondary lipids" to describe these biosynthetic pathways and products, a proposition consistent with the "secondary metabolite" vernacular. Phylogenomic analysis reveals a high degree of functional conservation within distinct biosynthetic pathways. Incongruence between secondary lipid synthase functional clades and taxonomic group membership combined with the lack of orthologous gene clusters in closely related strains suggests horizontal gene transfer has contributed to the dissemination of specialized lipid biosynthetic activities across disparate microbial lineages.

  3. PTP1B inhibitory secondary metabolites from marine-derived fungal strains Penicillium spp. and Eurotium sp.

    Science.gov (United States)

    Sohn, Jae Hak; Lee, Yu-Ri; Lee, Dong-Sung; Kim, Youn-Chul; Oh, Hyuncheol

    2013-09-28

    The selective inhibition of PTP1B has been widely recognized as a potential drug target for the treatment of type 2 diabetes and obesity. In the course of screening for PTP1B inhibitory fungal metabolites, the organic extracts of several fungal species isolated from marine environments were found to exhibit significant inhibitory effects, and the bioassay-guided investigation of these extracts resulted in the isolation of fructigenine A (1), cyclopenol (2), echinulin (3), flavoglaucin (4), and viridicatol (5). The structures of these compounds were determined mainly by analysis of NMR and MS data. These compounds inhibited PTP1B activity with 50% inhibitory concentration values of 10.7, 30.0, 29.4, 13.4, and 64.0 micrometer, respectively. Furthermore, the kinetic analysis of PTP1B inhibition by compounds 1 and 5 suggested that compound 1 inhibited PTP1B activity in a noncompetitive manner, whereas compound 5 inhibited PTP1B activity in a competitive manner.

  4. Effects of Selected Dietary Secondary Metabolites on Reactive Oxygen Species Production Caused by Iron(II Autoxidation

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    Vladimir Chobot

    2014-12-01

    Full Text Available Iron is an essential co-factor for many enzymes that catalyze electron transfer reactions. It is well known that so-called “poorly liganded” iron can increase ROS concentrations and trigger oxidative stress that is capable of initiating apoptosis. Conversely, controlled ROS production has been recognized as an integral part of cellular signaling. Elevated ROS concentrations are associated with aging, inflammatory and degenerative diseases. Anti-aging properties have been attributed especially to antioxidant phenolic plant metabolites that represent food additives in our diet. Consequently, this study explores the effects of flavonoids (quercetin and rutin, several phenolic acids (caffeic, chlorogenic, and protocatechuic acid, and the alkaloid caffeine on iron(II autoxidation and ROS production in comparison to the standard antioxidants ascorbic acid and Trolox. The iron(II autoxidation assay was carried out in pH 6.0 (plant apoplast and inflamed human tissue and 7.4 (cell cytoplasm and human blood plasma. The obtained results accentuate phenolic acids as the more specific antioxidants compared to ascorbic acid and Trolox. Flavonoid redox chemistry depends more on the chemical milieu, specifically on pH. In vivo, the presence of iron cannot be ruled out and “wrongly” or “poorly” complexed iron has been pointed out as causative agent of various age-related diseases.

  5. In vitro production of secondary metabolite using Atropa komarovii Bline&Shal (Solanaceae hairy root culture via Agrobacterium rhizogenes ATCC15834

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    Ofelia Banihashemi

    2017-07-01

    Full Text Available Background & Aim:A new sustainable tissue-based system is presented by plant hairy roots, preserving all of the several specialized types of cell with critical roles in allowing bioactive secondary molecules to be synthesized more consistently as usual. The system is also essential for studying the production of alkaloid in culture. Experimental: The Atropa komarovii leaves were wounded and infected with soil gram-negative bacterium Agrobacterium rhizogenes ATCC15834. After three weeks, the transformation roots and control roots without infection, appeared, and for confirming that T-DNA Ri plasmid fragments were transformed and integrated to plant genome, the rolB gene region, was amplified using PCR. HPLC method was then used for assaying how two tropane alkaloids such as atropine (hyosciamine and scopolamine (hyoscine were produced in hairy roots,control roots, leaves and roots of plantlet. Results: The data indicated that diagnostic 500bp rol B product amplification was exhibited to be present by all the transformed hairy roots. Scopolamine content in hairy roots was considerably greater than that in control roots but greatest (Hyoscyamine atropine content was observed in control roots. Analysis of DW, FW and root length showed that fresh and dry root weight increased in hairy roots compared with that in non transformed root. Recommended applications/industries: The present study demonstrated that secondary metabolite production using medicinal plants concerns many researchers worldwide today and hairy root culture is a useful method for producing tropane alkaloids in solanaceae.

  6. Chronic ozone exposure alters the secondary metabolite profile, antioxidant potential, anti-inflammatory property, and quality of red pepper fruit from Capsicum baccatum.

    Science.gov (United States)

    Bortolin, Rafael Calixto; Caregnato, Fernanda Freitas; Divan Junior, Armando Molina; Zanotto-Filho, Alfeu; Moresco, Karla Suzana; Rios, Alessandro de Oliveira; Salvi, Aguisson de Oliveira; Ortmann, Caroline Flach; de Carvalho, Pâmela; Reginatto, Flávio Henrique; Gelain, Daniel Pens; Moreira, José Cláudio Fonseca

    2016-07-01

    Tropospheric ozone (O3) background concentrations have increased since pre-industrial times, reaching phytotoxic concentrations in many regions globally. However, the effect of high O3 concentrations on quality of fruit and vegetables remains unknown. Here, we evaluated whether O3 pollution alters the quality of Capsicum baccatum peppers by changing the secondary compound profiles and biological activity of the fruit. C. baccatum pepper plants were exposed to ozone for 62 days in an open-top chamber at a mean O3 concentration of 171.6µg/m(3). Capsaicin levels decreased by 50% in the pericarp, but remained unchanged in the seeds. In contrast, the total carotenoid content increased by 52.8% in the pericarp. The content of total phenolic compounds increased by 17% in the pericarp. The total antioxidant potential decreased by 87% in seeds of O3-treated plants. The seeds contributed more than the pericarp to the total radical-trapping antioxidant potential and total antioxidant reactivity. O3 treatment impaired the ferric-reducing antioxidant power of the seeds and reduced NO(•)-scavenging activity in the pericarp. However, O3 treatment increased ferrous ion-chelating activity and hydroxyl radical-scavenging activity in the pericarp. Our results confirm that O3 alters the secondary metabolite profile of C. baccatum pepper fruits and, consequently, their biological activity profile. Copyright © 2016 Elsevier Inc. All rights reserved.

  7. In silico analysis and expression profiling of miRNAs targeting genes of steviol glycosides biosynthetic pathway and their relationship with steviol glycosides content in different tissues of Stevia rebaudiana.

    Science.gov (United States)

    Saifi, Monica; Nasrullah, Nazima; Ahmad, Malik Mobeen; Ali, Athar; Khan, Jawaid A; Abdin, M Z

    2015-09-01

    miRNAs are emerging as potential regulators of the gene expression. Their proven promising role in regulating biosynthetic pathways related gene networks may hold the key to understand the genetic regulation of these pathways which may assist in selection and manipulation to get high performing plant genotypes with better secondary metabolites yields and increased biomass. miRNAs associated with genes of steviol glycosides biosynthetic pathway, however, have not been identified so far. In this study miRNAs targeting genes of steviol glycosides biosynthetic pathway were identified for the first time whose precursors were potentially generated from ESTs and nucleotide sequences of Stevia rebaudiana. Thereafter, stem-loop coupled real time PCR based expressions of these miRNAs in different tissues of Stevia rebaudiana were investigated and their relationship pattern was analysed with the expression levels of their target mRNAs as well as steviol glycoside contents. All the miRNAs investigated showed differential expressions in all the three tissues studied, viz. leaves, flowers and stems. Out of the eleven miRNAs validated, the expression levels of nine miRNAs (miR319a, miR319b, miR319c, miR319d, miR319e, miR319f, miR319h, miRstv_7, miRstv_9) were found to be inversely related, while expression levels of the two, i.e. miR319g and miRstv_11 on the contrary, showed direct relation with the expression levels of their target mRNAs and steviol glycoside contents in the leaves, flowers and stems. This study provides a platform for better understanding of the steviol glycosides biosynthetic pathway and these miRNAs can further be employed to manipulate the biosynthesis of these metabolites to enhance their contents and yield in S. rebaudiana. Copyright © 2015 Elsevier Masson SAS. All rights reserved.

  8. α-Glucosidase Inhibition and Antibacterial Activity of Secondary Metabolites from the Ecuadorian Species Clinopodium taxifolium (Kunth Govaerts

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    Vladimir Morocho

    2018-01-01

    Full Text Available The phytochemical investigation of both volatile and fixed metabolites of Clinopodium taxifolium (Kunth Govaerts (Lamiaceae was performed for the first time. It allowed the isolation and characterization of the essential oil and six known compounds: carvacrol (1, squalane (2, uvaol (3, erythrodiol (4, ursolic acid (5, and salvigenin (6. Their structures were identified and characterized by Nuclear Magnetic Resonance (NMR and Gas Chromatography coupled to Mass Spectroscopy (GC-MS, and corroborated by literature. The essential oil of the leaves was obtained by hydrodistillation in two different periods and analyzed by GC-MS and GC coupled to Flame Ionization Detector (GC-FID. A total of 54 compounds were detected, of which 42 were identified (including trace constituents. The major constituents were carvacrol methyl ether (18.9–23.2%, carvacrol (13.8–16.3% and, carvacryl acetate (11.4–4.8%. The antibacterial activities were determined as Minimum Inhibition Concentration (MIC against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Pseudomonas aeruginosa and Micrococcus luteus. The hexane and methanol extracts exhibited activity only against Klebsiella pneumoniae (250 and 500 μg/mL respectively, while the ethyl acetate extract was inactive. The hypoglycemic activity was evaluated by the in vitro inhibition of α-glucosidase. The ethyl acetate (EtOAc extract showed strong inhibitory activity with IC50 = 24.88 µg/mL, however methanolic and hexanic extracts showed weak activity. As a pure compound, only ursolic acid showed a strong inhibitory activity, with IC50 = 72.71 μM.

  9. Deletion of the signalling molecule synthase ScbA has pleiotropic effects on secondary metabolite biosynthesis, morphological differentiation and primary metabolism in Streptomyces coelicolor A3(2)

    NARCIS (Netherlands)

    D'Alia, Davide; Eggle, D.; Nieselt, K.; Hu, W.-S.; Breitling, R.; Takano, E.

    2011-01-01

    Streptomycetes have high biotechnological relevance as producers of diverse metabolites widely used in medical and agricultural applications. The biosynthesis of these metabolites is controlled by signalling molecules, gamma-butyrolactones, that act as bacterial hormones. In Streptomyces coelicolor,

  10. UV-B Irradiation Changes Specifically the Secondary Metabolite Profile in Broccoli Sprouts: Induced Signaling Overlaps with Defense Response to Biotic Stressors

    Science.gov (United States)

    Mewis, Inga; Schreiner, Monika; Nguyen, Chau Nhi; Krumbein, Angelika; Ulrichs, Christian; Lohse, Marc; Zrenner, Rita

    2012-01-01

    Only a few environmental factors have such a pronounced effect on plant growth and development as ultraviolet light (UV). Concerns have arisen due to increased UV-B radiation reaching the Earth’s surface as a result of stratospheric ozone depletion. Ecologically relevant low to moderate UV-B doses (0.3–1 kJ m–2 d–1) were applied to sprouts of the important vegetable crop Brassica oleracea var. italica (broccoli), and eco-physiological responses such as accumulation of non-volatile secondary metabolites were related to transcriptional responses with Agilent One-Color Gene Expression Microarray analysis using the 2×204 k format Brassica microarray. UV-B radiation effects have usually been linked to increases in phenolic compounds. As expected, the flavonoids kaempferol and quercetin accumulated in broccoli sprouts (the aerial part of the seedlings) 24 h after UV-B treatment. A new finding is the specific UV-B-mediated induction of glucosinolates (GS), especially of 4-methylsulfinylbutyl GS and 4-methoxy-indol-3-ylmethyl GS, while carotenoids and Chl levels remained unaffected. Accumulation of defensive GS metabolites was accompanied by increased expression of genes associated with salicylate and jasmonic acid signaling defense pathways and up-regulation of genes responsive to fungal and bacterial pathogens. Concomitantly, plant pre-exposure to moderate UV-B doses had negative effects on the performance of the caterpillar Pieris brassicae (L.) and on the population growth of the aphid Myzus persicae (Sulzer). Moreover, insect-specific induction of GS in broccoli sprouts was affected by UV-B pre-treatment. PMID:22773681

  11. Metabolitos secundários como fontes de bioherbicidas: situação actual e perspectivas Secondary metabolites as sources of bioherbicides: present situation and perspectives

    Directory of Open Access Journals (Sweden)

    L.S. Dias

    2007-01-01

    Full Text Available Metabolitos secundários produzidos e libertados por plantas, bactérias e fungos estão envolvidos numa variedade de processos ecológicos, nomeadamente como semioquímicos e alelopatinos. Adicionalmente, e para além das suas possíveis funções ecológicas, muitos dos metabolitos secundários são fitotóxicos, constituindo uma fonte relativamente inexplorada de novos herbicidas. Solanum nigrum (erva-moira é uma infestante importante e muito bem sucedida num grande número de culturas, nomeadamente hortícolas e será usada como exemplo principal das utilizações actuais de aleloquímicos vegetais bem como das perspectivas de utilização deste tipo de compostos como bioherbicidas. Nesse âmbito revêem-se as principais estratégias de pesquisa de bioherbicidas e apresenta-se o estado da arte dos modos de acção de aleloquímicos já comercializados como herbicidas (Bialaphos e PPT, patenteados (AAL-toxina e em investigação, quer produzidos por plantas superiores (sorgoleona e derivados do cineol quer de origem bacteriana (hidantocidina e fúngica (fumonisinas, coletotriquina.Secondary metabolites produced and released by plants, bacteria, and fungi are involved in a number of ecological processes, namely as semiochemicals and allelopathins. In addition, and beside their possible ecological roles, a greater number of secondary metabolites are phytotoxic and represent a relatively unexplored source of new herbicides. Solanum nigrum (black nightshade is an important and successful weed in many crops, namely in horticulture, and will be used as a major example of actual and prospective uses of phytoallelochemicals as bioherbicides. Therefore, the main strategies for bioherbicides search are reviewed and the state of art of the modes of action of allelochemicals is presented, including those already in use as herbicides (Bialaphos and PPT, patented (AAL-toxin, and under investigation, whether produced by plants (sorgoleone and cineol

  12. Calcium and potassium supplementation enhanced growth, osmolytes, secondary metabolite production, and enzymatic antioxidant machinery in cadmium-exposed chickpea (Cicer arietinum L.

    Directory of Open Access Journals (Sweden)

    Parvaiz eAhmad

    2016-04-01

    Full Text Available The present work was conducted to examine the role of exogenously applied calcium (Ca; 50 mM and potassium (K; 10 mM (alone and in combination in alleviating the negative effects of cadmium (Cd; 200 μM on growth, biochemical attributes, secondary metabolites and yield of chickpea (Cicer arietinum L.. Cd stress significantly decreased length and fresh and dry weight of shoot and root, and number of pods and seed yield (vs. control. Exhibition of decreases in chlorophyll (Chl a, Chl b, and total Chl was also observed with Cd-exposure when compared to control. However, Cd-exposure led to an increase in the content of carotenoid. In contrast, the exogenous application of Ca and K individually as well as in combination minimized the extent of Cd-impact on previous traits. C. arietinum seedlings subjected to Cd treatment exhibited increased contents of organic solute (proline, Pro and total protein; whereas, Ca and K-supplementation further enhanced the Pro and total protein content. Additionally, compared to control, Cd-exposure also caused elevation in the contents of oxidative stress markers (hydrogen peroxidase, H2O2; malondialdehyde, MDA and in the activity of antioxidant defense enzymes (superoxide dismutase, SOD; catalase, CAT; ascorbate peroxidase, APX; glutathione reductase, GR. Ca, K and Ca + K supplementation caused further enhancements in the activity of these enzymes but significantly decreased contents of H2O2 and MDA, also that of Cd in shoot and root. The contents of total phenol, flavonoid and mineral elements (S, Mn, Mg, Ca and K that were also suppressed in Cd stressed plants in both shoot and root were restored to appreciable levels with Ca- and K-supplementation. However, the combination of Ca + K supplementation was more effective in bringing the positive response as compared to individual effect of Ca and K on Cd-exposed C. arietinum. Overall, this investigation suggests that application of Ca and/or K can efficiently minimize

  13. Discovering potential Streptomyces hormone producers by using disruptants of essential biosynthetic genes as indicator strains.

    Science.gov (United States)

    Thao, Nguyen B; Kitani, Shigeru; Nitta, Hiroko; Tomioka, Toshiya; Nihira, Takuya

    2017-10-01

    Autoregulators are low-molecular-weight signaling compounds that control the production of many secondary metabolites in actinomycetes and have been referred to as 'Streptomyces hormones'. Here, potential producers of Streptomyces hormones were investigated in 40 Streptomyces and 11 endophytic actinomycetes. Production of γ-butyrolactone-type (IM-2, VB) and butenolide-type (avenolide) Streptomyces hormones was screened using Streptomyces lavendulae FRI-5 (ΔfarX), Streptomyces virginiae (ΔbarX) and Streptomyces avermitilis (Δaco), respectively. In these strains, essential biosynthetic genes for Streptomyces hormones were disrupted, enabling them to respond solely to the externally added hormones. The results showed that 20% of each of the investigated strains produced IM-2 and VB, confirming that γ-butyrolactone-type Streptomyces hormones are the most common in actinomycetes. Unlike the γ-butyrolactone type, butenolide-type Streptomyces hormones have been discovered in recent years, but their distribution has been unclear. Our finding that 24% of actinomycetes (12 of 51 strains) showed avenolide activity revealed for the first time that the butenolide-type Streptomyces hormone is also common in actinomycetes.

  14. Screening of metabolites secondary compounds in extract of moringa fruit and determination of inhibitory effect on growth of the fungus Candida albicans

    Science.gov (United States)

    Nuryanti, Siti; Puspitasari, Dwi Juli

    2017-08-01

    Moringa (Moringa oleifera Lamk) is a nutritious plant that can cure various diseases. Parts of this plant like leave, root, flower, and fruit can be used as a traditional medicine. The research about screening of secondary metabolites in moringa extracts and the determination of their inhibitory effect on growth of the fungus Candida albicans have been done. This research was conducted by extracting the moringa fruit with various solvent with different polarity namely hexane, distilled water and ethanol. The fungal inhibition test was done by well-difuse method. Suspensions of Candida albicans was standardized by 0.5 Mc Farland standard. The results showed that the extracts of Moringa with distilled water provided the greatest inhibition on the growth of the fungus Candida albicans compared to moringa fruit extracted by ethanol and hexane. The percentages inhibition of Moringa extracts on the growth of the Candida albicans with distilled water, ethanol and hexane solvents were 89.90%, 57.90% and 8.97% respectively. Phytochemical screening test showed that the moringa fruit contain alkaloids, flavonoids and steroids.

  15. Characterization of main primary and secondary metabolites and in vitro antioxidant and antihyperglycemic properties in the mesocarp of three biotypes of Pouteria lucuma.

    Science.gov (United States)

    Fuentealba, Claudia; Gálvez, Lena; Cobos, Ariel; Olaeta, José Antonio; Defilippi, Bruno G; Chirinos, Rosana; Campos, David; Pedreschi, Romina

    2016-01-01

    Pouteria lucuma is an Andean fruit from pre-Incas' times highly appreciated due to its characteristic flavor and taste in its homeland. We characterized the primary (e.g., sugars and organic acids), and secondary (e.g., phenolics and carotenoids) and in vitro antioxidant and antihyperglycemic properties of Rosalia, Montero and Leiva 1 lucuma biotypes. Significant differences were found in these metabolites and functional properties related to biotype and ripeness stage. Results showed significant amounts of sugars (119.4-344 mg total sugars g(-1)DW) and organic acids (44.4-30.0 mg g(-1)DW) and functional associated compounds such as ascorbic acid (0.35-1.07 mg g(-1)DW), total phenolics (0.7-61.6 mg GAE g(-1)DW) and total carotenoids (0.22-0.50 mg β-carotene g(-1)DW). Important in vitro antioxidant and antihyperglycemic properties were found and provide the base for the standardization of lucuma harvest and postharvest focused not only on the enhancement of sensory but functional properties. Copyright © 2015 Elsevier Ltd. All rights reserved.

  16. Fast and comprehensive analysis of secondary metabolites in cocoa products using ultra high-performance liquid chromatography directly after pressurized liquid extraction.

    Science.gov (United States)

    Damm, Irina; Enger, Eileen; Chrubasik-Hausmann, Sigrun; Schieber, Andreas; Zimmermann, Benno F

    2016-08-01

    Fast methods for the extraction and analysis of various secondary metabolites from cocoa products were developed and optimized regarding speed and separation efficiency. Extraction by pressurized liquid extraction is automated and the extracts are analyzed by rapid reversed-phase ultra high-performance liquid chromatography and normal-phase high-performance liquid chromatography methods. After extraction, no further sample treatment is required before chromatographic analysis. The analytes comprise monomeric and oligomeric flavanols, flavonols, methylxanthins, N-phenylpropenoyl amino acids, and phenolic acids. Polyphenols and N-phenylpropenoyl amino acids are separated in a single run of 33 min, procyanidins are analyzed by normal-phase high-performance liquid chromatography within 16 min, and methylxanthins require only 6 min total run time. A fourth method is suitable for phenolic acids, but only protocatechuic acid was found in relevant quantities. The optimized methods were validated and applied to 27 dark chocolates, one milk chocolate, two cocoa powders and two food supplements based on cocoa extract. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  17. Profiling secondary metabolites of needles of ozone-fumigated white pine (Pinus strobus) clones by thermally assisted hydrolysis/methylation GC/MS.

    Science.gov (United States)

    Shadkami, F; Helleur, R J; Cox, R M

    2007-07-01

    Plant secondary metabolites have an important role in defense responses against herbivores and pathogens, and as a chemical barrier to elevated levels of harmful air pollutants. This study involves the rapid chemical profiling of phenolic and diterpene resin acids in needles of two (ozone-tolerant and ozone-sensitive) white pine (Pinus strobus) clones, fumigated with different ozone levels (control, and daily events peaking at 80 and 200 ppb) for 40 days. The phenolic and resin acids were measured using thermally assisted hydrolysis and methylation (THM) gas chromatography/mass spectrometry. Short-term fumigation affected the levels of two phenolic acids, i.e., 3-hydroxybenzoic and 3,4-dihydroxybenzoic acids, in that both showed a substantial decrease in concentration with increased ozone dose. The decrease in concentration of these THM products may be caused by inhibition of the plant's shikimate biochemical pathway caused by ozone exposure. The combined occurrence of these two ozone-sensitive indicators has a role in biomonitoring of ozone levels and its impact on forest productivity. In addition, chromatographic profile differences in the major diterpene resin acid components were observed between ozone-tolerant and ozone-sensitive clones. The resin acids anticopalic, 3-oxoanticopalic, 3beta-hydroxyanticopalic, and 3,4-cycloanticopalic acids were present in the ozone-sensitive pine; however, only anticopalic acid was present in the ozone-tolerant clone. This phenotypic variation in resin acid composition may be useful in distinguishing populations that are differentially adapted to air pollutants.

  18. Genomics of Sponge-Associated Streptomyces spp. Closely Related to Streptomyces albus J1074: Insights into Marine Adaptation and Secondary Metabolite Biosynthesis Potential

    Science.gov (United States)

    Ian, Elena; Malko, Dmitry B.; Sekurova, Olga N.; Bredholt, Harald; Rückert, Christian; Borisova, Marina E.; Albersmeier, Andreas; Kalinowski, Jörn; Gelfand, Mikhail S.; Zotchev, Sergey B.

    2014-01-01

    A total of 74 actinomycete isolates were cultivated from two marine sponges, Geodia barretti and Phakellia ventilabrum collected at the same spot at the bottom of the Trondheim fjord (Norway). Phylogenetic analyses of sponge-associated actinomycetes based on the 16S rRNA gene sequences demonstrated the presence of species belonging to the genera Streptomyces, Nocardiopsis, Rhodococcus, Pseudonocardia and Micromonospora. Most isolates required sea water for growth, suggesting them being adapted to the marine environment. Phylogenetic analysis of Streptomyces spp. revealed two isolates that originated from different sponges and had 99.7% identity in their 16S rRNA gene sequences, indicating that they represent very closely related strains. Sequencing, annotation, and analyses of the genomes of these Streptomyces isolates demonstrated that they are sister organisms closely related to terrestrial Streptomyces albus J1074. Unlike S. albus J1074, the two sponge streptomycetes grew and differentiated faster on the medium containing sea water. Comparative genomics revealed several genes presumably responsible for partial marine adaptation of these isolates. Genome mining targeted to secondary metabolite biosynthesis gene clusters identified several of those, which were not present in S. albus J1074, and likely to have been retained from a common ancestor, or acquired from other actinomycetes. Certain genes and gene clusters were shown to be differentially acquired or lost, supporting the hypothesis of divergent evolution of the two Streptomyces species in different sponge hosts. PMID:24819608

  19. Hepatoprotective evaluation and isolation of the major secondary metabolites from the ethyl acetate extract of liquid culture filtrate of Chaetomium globosum.

    Science.gov (United States)

    Awad, Nagwa E; Kassem, Hanaa A; Hamed, Manal A; El-Feky, Amal M; El-Naggar, Mohamed A A

    2018-01-01

    The aim of the present study was to evaluate the hepatoprotective activity of ethyl acetate extract of the liquid culture filtrate of Chaetomium globosum fungus (family Chaetomiaceae). Rats were intraperitoneally injected by CCl4 (0.5ml/kg) twice a week for six consecutive weeks. Treatment tacks (250mg/kg) place at the same time of CCl4 induction and with the same duration. The evaluation was done through determination of liver function indices; aspartate aminotransferase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP), and total serum protein content. In addition, the oxidative stress markers; hepatic glutathione content (GSH), hepatic malondialdehyde (MDA), hepatic superoxide dismutase (SOD), and hepatic total protein were estimated. Moreover, the liver architectures were also examined. Isolation and identification of the main secondary metabolites were identified. Seven volatile compounds were identified from the plain chloroform fraction where, 1-Cyclopentyl-2,2-dimethyl-1-propanol (54.63%) was presented as the major compound. Eleven compounds were also identified from the fraction eluted by chloroform: methanol (85:15). 1,5,5-Trimethyl-6-methylene-1-cyclohexene (25.79%) and Norbornan-2-one (26.84%) are presented as the major compounds of this fraction. In conclusion, the extract recorded hepatoprotective effect by ameliorating the biochemical parameters under investigation. The liver histopathological pictures confirmed our results. Copyright © 2017. Published by Elsevier Masson SAS.

  20. The PacC transcription factor regulates secondary metabolite production and stress response, but has only minor effects on virulence in the insect pathogenic fungus Beauveria bassiana.

    Science.gov (United States)

    Luo, Zhibing; Ren, Hui; Mousa, Jarrod J; Rangel, Drauzio E N; Zhang, Yongjun; Bruner, Steven D; Keyhani, Nemat O

    2017-02-01

    The PacC transcription factor is an important component of the fungal ambient pH-responsive regulatory system. Loss of pacC in the insect pathogenic fungus Beauveria bassiana resulted in an alkaline pH-dependent decrease in growth and pH-dependent increased susceptibility to osmotic (salt, sorbitol) stress and SDS. Extreme susceptibility to Congo Red was noted irrespective of pH, and ΔBbpacC conidia showed subtle increases in UV susceptibility. The ΔBbPacC mutant showed a reduced ability to acidify media during growth due to failure to produce oxalic acid. The ΔBbPacC mutant also did not produce the insecticidal compound dipicolinic acid, however, production of a yellow-colored compound was noted. The compound, named bassianolone B, was purified and its structure determined. Despite defects in growth, stress resistance, and oxalate/insecticidal compound production, only a small decrease in virulence was seen for the ΔBbpacC strain in topical insect bioassays using larvae from the greater waxmoth, Galleria mellonella or adults of the beetle, Tenebrio molitor. However, slightly more pronounced decreases were seen in virulence via intrahemcoel injection assays (G. mellonella) and in assays using T. molitor larvae. These data suggest important roles for BbpacC in mediating growth at alkaline pH, regulating secondary metabolite production, and in targeting specific insect stages. © 2017 Society for Applied Microbiology and John Wiley & Sons Ltd.

  1. The AreA transcription factor in Fusarium graminearum regulates the use of some nonpreferred nitrogen sources and secondary metabolite production.

    Science.gov (United States)

    Giese, Henriette; Sondergaard, Teis Esben; Sørensen, Jens Laurids

    2013-01-01

    Growth conditions are known to affect the production of secondary metabolites in filamentous fungi. The influence of different nitrogen sources and the transcription factor AreA on the production of mycotoxins in Fusarium graminearum was examined. Growth on glutamine or NH4-sources was poor and asparagine was found to be a preferential nitrogen source for F. graminearum. Deletion of areA led to poor growth on NaNO₃ suggesting its involvement in regulation of the nitrate reduction process. In addition utilization of aspartic acid, histidine, isoleucine, leucine, threonine, tyrosine, and valine as nitrogen sources was shown to depend of a functional AreA. AreA was shown to be required for the production of the mycotoxins deoxynivalenol (DON), zearalenone, and fusarielin H regardless of the nutrient medium. Deletion of nmr, the repressor of AreA under nitrogen sufficient conditions, had little effect on either growth or toxin production. AreA appears to regulate production of some mycotoxins directly or indirectly independent on nitrogen status and plays a role in utilization of certain amino acids. Copyright © 2013 The British Mycological Society. All rights reserved.

  2. Marine metabolites: The sterols of soft coral

    Digital Repository Service at National Institute of Oceanography (India)

    Sarma, N.S.; Krishna, M.S.; Pasha, Sk.G.; Rao, T.S.P.; Venkateswarlu, Y.; Parameswaran, P.S.

    Sterols constitute a major group of secondary metabolites of soft corals. Several of these compounds have the 'usual' 3 beta-hydroxy, delta sup(5) (or delta sup(0)) cholestane skeleton, a large number of these metabolites are polar sterols...

  3. Secondary metabolites from Eurotium species, Aspergillus calidoustus and A. insuetus common in Canadian homes with a review of their chemistry and biological activities

    DEFF Research Database (Denmark)

    Slack, G. J.; Puniani, E.; Frisvad, Jens Christian

    2009-01-01

    As part of studies of metabolites from fungi common in the built environment in Canadian homes, we investigated metabolites from strains of three Eurotium species, namely E. herbariorum, E. amstelodami, and E. rubrum as well as a number of isolates provisionally identified as Aspergillus ustus. T...

  4. Secondary metabolites from Eurotium species, Aspergillus calidoustus and A. insuetus common in Canadian homes with a review of their chemistry and biological activities

    NARCIS (Netherlands)

    Slack, G.J.; Puniani, E.; Frisvad, J.C.; Samson, R.A.; Miller, J.D.

    2009-01-01

    As part of studies of metabolites from fungi common in the built environment in Canadian homes, we investigated metabolites from strains of three Eurotium species, namely E. herbariorum, E. amstelodami, and E. rubrum as well as a number of isolates provisionally identified as Aspergillus ustus. The

  5. Secondary metabolites from Eurotium species, Aspergillus calidoustus and A. insuetus common in Canadian homes with a review of their chemistry and biological activities.

    Science.gov (United States)

    Slack, Gregory J; Puniani, Eva; Frisvad, Jens C; Samson, Robert A; Miller, J David

    2009-04-01

    As part of studies of metabolites from fungi common in the built environment in Canadian homes, we investigated metabolites from strains of three Eurotium species, namely E. herbariorum, E. amstelodami, and E. rubrum as well as a number of isolates provisionally identified as Aspergillus ustus. The latter have been recently assigned as the new species A. insuetus and A. calidoustus. E. amstelodami produced neoechinulin A and neoechinulin B, epiheveadride, flavoglaucin, auroglaucin, and isotetrahydroauroglaucin as major metabolites. Minor metabolites included echinulin, preechinulin and neoechinulin E. E. rubrum produced all of these metabolites, but epiheveadride was detected as a minor metabolite. E. herbariorum produced cladosporin as a major metabolite, in addition to those found in E. amstelodami. This species also produced questin and neoechinulin E as minor metabolites. This is the first report of epiheveadride occurring as a natural product, and the first nonadride isolated from Eurotium species. Unlike strains from mainly infection-related samples, largely from Europe, neither ophiobolins G and H nor austins were detected in the Canadian strains of A. insuetus and A. calidoustus tested, all of which had been reported from the latter species. TMC-120 A, B, C and a sesquiterpene drimane are reported with certainty for the first time from indoor isolates, as well as two novel related methyl isoquinoline alkaloids.

  6. Linking metabolic QTLs with network and cis-eQTLs controlling biosynthetic pathways.

    Directory of Open Access Journals (Sweden)

    Adam M Wentzell

    2007-09-01

    Full Text Available Phenotypic variation between individuals of a species is often under quantitative genetic control. Genomic analysis of gene expression polymorphisms between individuals is rapidly gaining popularity as a way to query the underlying mechanistic causes of variation between individuals. However, there is little direct evidence of a linkage between global gene expression polymorphisms and phenotypic consequences. In this report, we have mapped quantitative trait loci (QTLs-controlling glucosinolate content in a population of 403 Arabidopsis Bay x Sha recombinant inbred lines, 211 of which were previously used to identify expression QTLs controlling the transcript levels of biosynthetic genes. In a comparative study, we have directly tested two plant biosynthetic pathways for association between polymorphisms controlling biosynthetic gene transcripts and the resulting metabolites within the Arabidopsis Bay x Sha recombinant inbred line population. In this analysis, all loci controlling expression variation also affected the accumulation of the resulting metabolites. In addition, epistasis was detected more frequently for metabolic traits compared to transcript traits, even when both traits showed similar distributions. An analysis of candidate genes for QTL-controlling networks of transcripts and metabolites suggested that the controlling factors are a mix of enzymes and regulatory factors. This analysis showed that regulatory connections can feedback from metabolism to transcripts. Surprisingly, the most likely major regulator of both transcript level for nearly the entire pathway and aliphatic glucosinolate accumulation is variation in the last enzyme in the biosynthetic pathway, AOP2. This suggests that natural variation in transcripts may significantly impact phenotypic variation, but that natural variation in metabolites or their enzymatic loci can feed back to affect the transcripts.

  7. Effect of phytotoxic secondary metabolites and semisynthetic compounds from endophytic fungus Xylaria feejeensis strain SM3e-1b on spinach chloroplast photosynthesis.

    Science.gov (United States)

    Macías-Rubalcava, Martha Lydia; García-Méndez, Marbella Claudia; King-Díaz, Beatriz; Macías-Ruvalcaba, Norma Angélica

    2017-01-01

    We investigated the mechanism of action on the photosynthesis light reactions of three major secondary metabolites produced by the endophytic fungus Xylaria feejeensis strain SM3e-1b, isolated from Sapium macrocarpum; and four novel derivatives of coriloxine, a major compound produced by X. feejeensis. The natural phytotoxins include one epoxycyclohexenone derivative, coriloxine (1), and two quinone derivatives (2-3). The semisynthetic derivatives of coriloxine are two cyclohexenone (4-6) and two quinone compounds (5-7). Cyclohexenone (4), (4R,5S,6R)-6-chloro-4,5-dihydroxy-3-methoxy-5-methylcyclohex-2-enone, inhibited ATP synthesis in freshly lysed spinach chloroplasts from water to MV; it also partly inhibited the basal and uncoupled photosynthetic electron transport, and significantly enhanced the phosphorylating electron transport and Mg 2+ -ATPase activity, thus demonstrating its action as an uncoupler agent. On the other hand, quinone (7), 2-((4-butylphenyl)amino)-5-methoxy-3-methylcyclohexa-2,5-diene-1,4-dione, inhibited ATP synthesis, and non-cyclic electron transport from water to MV in basal, phosphorylating and uncoupled conditions in a concentration-dependent manner. Hence, (7) behaves as a Hill reaction inhibitor at the PSII electron transport on the water splitting enzyme (OEC), and on the acceptor side between P 680 and Q A . This mechanism of action was confirmed by chlorophyll a fluorescence measurements. These results indicate that coriloxine derivatives 4 and 7 could work as prototype structures for the development of new herbicides. Contrastingly, natural products 1-3, and derivatives 5 and 6 did not show a significant inhibitory effect on ATP synthesis. Copyright © 2016 Elsevier B.V. All rights reserved.

  8. Identification and characterization of lbpA, an indigoidine biosynthetic gene in the γ-butyrolactone signaling system of Streptomyces lavendulae FRI-5.

    Science.gov (United States)

    Pait, Ivy Grace Umadhay; Kitani, Shigeru; Kurniawan, Yohanes Novi; Asa, Maeda; Iwai, Takashi; Ikeda, Haruo; Nihira, Takuya

    2017-10-01

    Streptomyces lavendulae FRI-5 produces the blue pigment indigoidine and other secondary metabolites (d-cycloserine and nucleoside antibiotics). The production of these useful compounds is controlled by a signaling cascade mediated by the γ-butyrolactone autoregulator IM-2. Previously we revealed that the far regulatory island includes the IM-2 receptor, the IM-2 biosynthetic enzyme, and several transcriptional regulators, and that it contributes to the regulation of indigoidine production in response to the signaling molecule. Here, we found that the vicinity of the far regulatory island includes the putative gene cluster for the biosynthesis of indigoidine and unidentified compounds, and demonstrated that the expression of the gene cluster is under the control of the IM-2 regulatory system. Heterologous expression of lbpA, encoding a plausible nonribosomal peptide synthetase, in the versatile model host Streptomyces avermitilis SUKA22 led to indigoidine production, which was enhanced dramatically by feeding of the indigoidine precursor l-glutamine. These results confirmed that LbpA is an indigoidine biosynthetic enzyme in the IM-2 signaling cascade. Copyright © 2017 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

  9. Detection of biosynthetic gene and phytohormone production by endophytic actinobacteria associated with Solanum lycopersicum and their plant-growth-promoting effect.

    Science.gov (United States)

    Passari, Ajit Kumar; Chandra, Preeti; Zothanpuia; Mishra, Vineet Kumar; Leo, Vincent Vineeth; Gupta, Vijai Kumar; Kumar, Brijesh; Singh, Bhim Pratap

    2016-10-01

    In the present study, fifteen endophytic actinobacterial isolates recovered from Solanum lycopersicum were studied for their antagonistic potential and plant-growth-promoting (PGP) traits. Among them, eight isolates showed significant antagonistic and PGP traits, identified by amplification of the 16S rRNA gene. Isolate number DBT204, identified as Streptomyces sp., showed multiple PGP traits tested in planta and improved a range of growth parameters in seedlings of chili (Capsicum annuum L.) and tomato (S. lycopersicum L.). Further, genes of indole acetic acid (iaaM) and 1-aminocyclopropane-1-carboxylate (ACC) deaminase (acdS) were successively amplified from five strains. Six antibiotics (trimethoprim, fluconazole, chloramphenicol, nalidixic acid, rifampicin and streptomycin) and two phytohormones [indole acetic acid (IAA) and kinetin (KI)] were detected and quantified in Streptomyces sp. strain DBT204 using UPLC-ESI-MS/MS. The study indicates the potential of these PGP strains for production of phytohormones and shows the presence of biosynthetic genes responsible for production of secondary metabolites. It is the first report showing production of phytohormones (IAA and KI) by endophytic actinobacteria having PGP and biosynthetic potential. We propose Streptomyces sp. strain DBT204 for inoculums production and development of biofertilizers for enhancing growth of chili and tomato seedlings. Copyright © 2016 Institut Pasteur. Published by Elsevier Masson SAS. All rights reserved.

  10. Qualitative and quantitative characterization of secondary metabolites and carbohydrates in Bai-Hu-Tang using ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry and ultraperformance liquid chromatography coupled with photodiode array detector.

    Science.gov (United States)

    Zhong, Wei-Fang; Tong, Wing-Sum; Zhou, Shan-Shan; Yip, Ka-Man; Li, Song-Lin; Zhao, Zhong-Zhen; Xu, Jun; Chen, Hu-Biao

    2017-10-01

    Bai-Hu-Tang (BHT), a classic traditional Chinese medicine (TCM) formula used for clearing heat and promoting body fluid, consists of four traditional Chinese medicines, i.e., Gypsum Fibrosum (Shigao), Anemarrhenae Rhizoma (Zhimu), Glycyrrhizae Radix et Rhizoma Praeparata cum Melle (Zhigancao), and nonglutinous rice (Jingmi). The chemical composition of BHT still remains largely elusive thus far. To qualitatively and quantitatively characterize secondary metabolites and carbohydrates in BHT, here a combination of analytical approaches using ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry and ultraperformance liquid chromatography coupled with photodiode array detector was developed and validated. A total of 42 secondary metabolites in BHT were tentatively or definitely identified, of which 10 major chemicals were quantified by the extracting ion mode of quadrupole time-of-flight mass spectrometry. Meanwhile, polysaccharides, oligosaccharides, and monosaccharides in BHT were also characterized via sample pretreatment followed by sugar composition analysis. The quantitative results indicated that the determined chemicals accounted for 35.76% of the total extract of BHT, which demonstrated that the study could be instrumental in chemical dissection and quality control of BHT. The research deliverables not only laid the root for further chemical and biological evaluation of BHT, but also provided a comprehensive analytical strategy for chemical characterization of secondary metabolites and carbohydrates in traditional Chinese medicine formulas. Copyright © 2017. Published by Elsevier B.V.

  11. Qualitative and quantitative characterization of secondary metabolites and carbohydrates in Bai-Hu-Tang using ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry and ultraperformance liquid chromatography coupled with photodiode array detector

    Directory of Open Access Journals (Sweden)

    Wei-Fang Zhong

    2017-10-01

    Full Text Available Bai-Hu-Tang (BHT, a classic traditional Chinese medicine (TCM formula used for clearing heat and promoting body fluid, consists of four traditional Chinese medicines, i.e., Gypsum Fibrosum (Shigao, Anemarrhenae Rhizoma (Zhimu, Glycyrrhizae Radix et Rhizoma Praeparata cum Melle (Zhigancao, and nonglutinous rice (Jingmi. The chemical composition of BHT still remains largely elusive thus far. To qualitatively and quantitatively characterize secondary metabolites and carbohydrates in BHT, here a combination of analytical approaches using ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry and ultraperformance liquid chromatography coupled with photodiode array detector was developed and validated. A total of 42 secondary metabolites in BHT were tentatively or definitely identified, of which 10 major chemicals were quantified by the extracting ion mode of quadrupole time-of-flight mass spectrometry. Meanwhile, polysaccharides, oligosaccharides, and monosaccharides in BHT were also characterized via sample pretreatment followed by sugar composition analysis. The quantitative results indicated that the determined chemicals accounted for 35.76% of the total extract of BHT, which demonstrated that the study could be instrumental in chemical dissection and quality control of BHT. The research deliverables not only laid the root for further chemical and biological evaluation of BHT, but also provided a comprehensive analytical strategy for chemical characterization of secondary metabolites and carbohydrates in traditional Chinese medicine formulas.

  12. Heterologous expression of oxytetracycline biosynthetic gene cluster in Streptomyces venezuelae WVR2006 to improve production level and to alter fermentation process.

    Science.gov (United States)

    Yin, Shouliang; Li, Zilong; Wang, Xuefeng; Wang, Huizhuan; Jia, Xiaole; Ai, Guomin; Bai, Zishang; Shi, Mingxin; Yuan, Fang; Liu, Tiejun; Wang, Weishan; Yang, Keqian

    2016-12-01

    Heterologous expression is an important strategy to activate biosynthetic gene clusters of secondary metabolites. Here, it is employed to activate and manipulate the oxytetracycline (OTC) gene cluster and to alter OTC fermentation process. To achieve these goals, a fast-growing heterologous host Streptomyces venezuelae WVR2006 was rationally selected among several potential hosts. It shows rapid and dispersed growth and intrinsic high resistance to OTC. By manipulating the expression of two cluster-situated regulators (CSR) OtcR and OtrR and precursor supply, the OTC production level was significantly increased in this heterologous host from 75 to 431 mg/l only in 48 h, a level comparable to the native producer Streptomyces rimosus M4018 in 8 days. This work shows that S. venezuelae WVR2006 is a promising chassis for the production of secondary metabolites, and the engineered heterologous OTC producer has the potential to completely alter the fermentation process of OTC production.

  13. Evolution and Diversity of Biosynthetic Gene Clusters in Fusarium

    Directory of Open Access Journals (Sweden)

    Koen Hoogendoorn

    2018-06-01

    Full Text Available Plant pathogenic fungi in the Fusarium genus cause severe damage to crops, resulting in great financial losses and health hazards. Specialized metabolites synthesized by these fungi are known to play key roles in the infection process, and to provide survival advantages inside and outside the host. However, systematic studies of the evolution of specialized metabolite-coding potential across Fusarium have been scarce. Here, we apply a combination of bioinformatic approaches to identify biosynthetic gene clusters (BGCs across publicly available genomes from Fusarium, to group them into annotated families and to study gain/loss events of BGC families throughout the history of the genus. Comparison with MIBiG reference BGCs allowed assignment of 29 gene cluster families (GCFs to pathways responsible for the production of known compounds, while for 57 GCFs, the molecular products remain unknown. Comparative analysis of BGC repertoires using ancestral state reconstruction raised several new hypotheses on how BGCs contribute to Fusarium pathogenicity or host specificity, sometimes surprisingly so: for example, a gene cluster for the biosynthesis of hexadehydro-astechrome was identified in the genome of the biocontrol strain Fusarium oxysporum Fo47, while being absent in that of the tomato pathogen F. oxysporum f.sp. lycopersici. Several BGCs were also identified on supernumerary chromosomes; heterologous expression of genes for three terpene synthases encoded on the Fusarium poae supernumerary chromosome and subsequent GC/MS analysis showed that these genes are functional and encode enzymes that each are able to synthesize koraiol; this observed functional redundancy supports the hypothesis that localization of copies of BGCs on supernumerary chromosomes provides freedom for evolutionary innovations to occur, while the original function remains conserved. Altogether, this systematic overview of biosynthetic diversity in Fusarium paves the way for

  14. Targeting the GPI biosynthetic pathway.

    Science.gov (United States)

    Yadav, Usha; Khan, Mohd Ashraf

    2018-02-27

    The GPI (Glycosylphosphatidylinositol) biosynthetic pathway is a multistep conserved pathway in eukaryotes that culminates in the generation of GPI glycolipid which in turn anchors many proteins (GPI-APs) to the cell surface. In spite of the overall conservation of the pathway, there still exist subtle differences in the GPI pathway of mammals and other eukaryotes which holds a great promise so far as the development of drugs/inhibitors against specific targets in the GPI pathway of pathogens is concerned. Many of the GPI structures and their anchored proteins in pathogenic protozoans and fungi act as pathogenicity factors. Notable examples include GPI-anchored variant surface glycoprotein (VSG) in Trypanosoma brucei, GPI-anchored merozoite surface protein 1 (MSP1) and MSP2 in Plasmodium falciparum, protein-free GPI related molecules like lipophosphoglycans (LPGs) and glycoinositolphospholipids (GIPLs) in Leishmania spp., GPI-anchored Gal/GalNAc lectin and proteophosphoglycans in Entamoeba histolytica or the GPI-anchored mannoproteins in pathogenic fungi like Candida albicans. Research in this active area has already yielded encouraging results in Trypanosoma brucei by the development of parasite-specific inhibitors of GlcNCONH 2 -β-PI, GlcNCONH 2 -(2-O-octyl)-PI and salicylic hydroxamic acid (SHAM) targeting trypanosomal GlcNAc-PI de-N-acetylase as well as the development of antifungal inhibitors like BIQ/E1210/gepinacin/G365/G884 and YW3548/M743/M720 targeting the GPI specific fungal inositol acyltransferase (Gwt1) and the phosphoethanolamine transferase-I (Mcd4), respectively. These confirm the fact that the GPI pathway continues to be the focus of researchers, given its implications for the betterment of human life.

  15. Aspergillus hancockii sp. Nov., a biosynthetically talented fungus endemic to southeastern Australian soils

    DEFF Research Database (Denmark)

    Pitt, John I.; Lange, Lene; Lacey, Alastair E.

    2017-01-01

    secondary metabolites. Eleven of the 15 most abundant secondary metabolites, constituting 90% of the total area under the curve of the HPLC trace of the crude extract, were novel. The genome of A. hancockii, approximately 40 Mbp, was sequenced and mined for genes encoding carbohydrate degrading enzymes...

  16. Assessing biosynthetic potential of agricultural groundwater through metagenomic sequencing: A diverse anammox community dominates nitrate-rich groundwater.

    Directory of Open Access Journals (Sweden)

    William B Ludington

    Full Text Available Climate change produces extremes in both temperature and precipitation causing increased drought severity and increased reliance on groundwater resources. Agricultural practices, which rely on groundwater, are sensitive to but also sources of contaminants, including nitrate. How agricultural contamination drives groundwater geochemistry through microbial metabolism is poorly understood.On an active cow dairy in the Central Valley of California, we sampled groundwater from three wells at depths of 4.3 m (two wells and 100 m (one well below ground surface (bgs as well as an effluent surface water lagoon that fertilizes surrounding corn fields. We analyzed the samples for concentrations of solutes, heavy metals, and USDA pathogenic bacteria of the Escherichia coli and Enterococcus groups as part of a long term groundwater monitoring study. Whole metagenome shotgun sequencing and assembly revealed taxonomic composition and metabolic potential of the community.Elevated nitrate and dissolved organic carbon occurred at 4.3m but not at 100m bgs. Metagenomics confirmed chemical observations and revealed several Planctomycete genomes, including a new Brocadiaceae lineage and a likely Planctomycetes OM190, as well novel diversity and high abundance of nano-prokaryotes from the Candidate Phyla Radiation (CPR, the Diapherotrites, Parvarchaeota, Aenigmarchaeota, Nanoarchaeota, Nanohaloarchaea (DPANN and the Thaumarchaeota, Aigarchaeota, Crenarchaeota, Korarchaeota (TACK superphyla. Pathway analysis suggests community interactions based on complimentary primary metabolic pathways and abundant secondary metabolite operons encoding antimicrobials and quorum sensing systems.The metagenomes show strong resemblance to activated sludge communities from a nitrogen removal reactor at a wastewater treatment plant, suggesting that natural bioremediation occurs through microbial metabolism. Elevated nitrate and rich secondary metabolite biosynthetic capacity suggest

  17. Distribution of mycotoxin biosynthetic genes in 200 Fusarium genomes

    Science.gov (United States)

    Fusarium is a species-rich genus of fungi that causes disease on most crop plants and produces diverse secondary metabolites (SMs), including some of the mycotoxins of greatest concern to food and feed safety. To determine the potential SM diversity within Fusarium as well as the distribution and ev...

  18. Secondary metabolites constituents and antioxidant, anticancer and antibacterial activities of Etlingera elatior (Jack) R.M.Sm grown in different locations of Malaysia.

    Science.gov (United States)

    Ghasemzadeh, Ali; Jaafar, Hawa Z E; Rahmat, Asmah; Ashkani, Sadegh

    2015-09-23

    Etlingera elatior is a well-known herb in Malaysia with various pharmaceutical properties. E. elatior flowers grown in three different locations of Malaysia (Kelantan, Pahang and Johor), were investigated for differences in their content of secondary metabolites (total phenolics [TPC], total flavonoids [TFC], and total tannin content [TTC]) as well as for their antioxidant, anticancer, and antibacterial properties. Phenolic acids and flavonoids were isolated and identified using ultra-high performance liquid chromatography (UHPLC). Ferric reducing antioxidant potential (FRAP) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) assays were used to evaluate the antioxidant activities. The anticancer activity of extracts was evaluated using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. When extracted with various solvents (aqueous and ethanolic), samples from the different locations yielded significantly different results for TPC, TFC, and TTC as well as antioxidant activity. Aqueous extracts of E. elatior flowers collected from Kelantan exhibited the highest values: TPC (618.9 mg/100 g DM), TFC (354.2 mg/100 g DM), TTC (129.5 mg/100 g DM), DPPH (76.4 %), and FRAP (6.88 mM of Fe (II)/g) activity with a half-maximal inhibitory concentration (IC50) of 34.5 μg/mL compared with extracts of flowers collected from the other two locations. The most important phenolic compounds isolated in this study, based on concentration, were: gallic acid > caffeic acid > tannic acid > chlorogenic acid; and the most important flavonoids were: quercetin > apigenin > kaempferol > luteolin > myricetin. Extracts of flowers from Kelantan exhibited potent anticancer activity with a IC50of 173.1 and 196.2 μg/mL against the tumor cell lines MCF-7 and MDA-MB-231 respectively, compared with extracts from Pahang (IC50 = 204.5 and 246.2 μg/mL) and Johor samples (IC50 = 277.1 and 296.7 μg/mL). Extracts of E. elatior flowers also showed

  19. Gamma radiation induced oxidative stress and apoptosis inhibiting properties of bacterial secondary metabolite RK-IP-006.G in J774A.1 murine cell line

    International Nuclear Information System (INIS)

    Malhotra, Poonam; Gupta, Ashutosh K.; Singh, Praveen K.; Chhachhia, Neha; Singh, Shravan K.; Raj Kumar

    2014-01-01

    Redox imbalance due to radiation induced oxidation of vital bio-macromolecules activates inflammatory response cascade leading to cell death. In present study, bacterial secondary metabolite, RK-IP-006.G, was evaluated for its oxidative stress and apoptosis inhibiting activities in irradiated J774A.1 murine macrophage cell line. Radiation induced intracellular ROS generation and its inhibition upon RK-IP-006.G pretreatment was estimated using 2',7'dichlorodihydroflurescein diacetate (DCFDA). Modulation in mitochondrial membrane potential (MMP) in irradiated cells and its protection by RK-IP-006.G pretreatment was evaluated using Rhodamine-123. Modulation in protein expression in irradiated and RK-IP-006.G treated J774A.1 cells was assessed by SDS-PAGE. Compensatory effect of RK-IP-006.G treatment on TNF-α expression in irradiated cells was estimated using ELISA assay. APO-BrDU assay was performed to evaluate radiation-induced apoptosis in irradiated cells. Radiation-induced cell damage and protective ability of RK-IP-006.G was also evaluated using Differential Interference Contrast Microscopy. Results of the study indicated significant (p< 0.05) decrease in DCFDA fluorescence in irradiated cells that were pretreated (∼2h) with RK-IP-006.G (0.25 μg/ml) as compared to irradiated cells. Similarly, significant (p<0.05) decrease in MMP was observed in irradiated cells pretreated with RK-IP-006.G (0.25 μg/ml) as compared to only irradiated cells at 1 h time point. SDS-PAGE analysis clearly demonstrated up-regulation of some prominent proteins in irradiated cells pretreated with RK-IP-006.G at 2-4h after treatment as compared to irradiated control. Significant (p<0.05) down regulation in TNF-α expression was observed in irradiated cells that pretreated with RK-IP-006.G compared to irradiated controls. APO-BrDU assay revealed significant reduction in apoptosis in irradiated cells pretreated with RK-IP-006.G when compared to irradiated control. The findings

  20. Strain-Level Diversity of Secondary Metabolism in Streptomyces albus

    Science.gov (United States)

    Seipke, Ryan F.

    2015-01-01

    Streptomyces spp. are robust producers of medicinally-, industrially- and agriculturally-important small molecules. Increased resistance to antibacterial agents and the lack of new antibiotics in the pipeline have led to a renaissance in natural product discovery. This endeavor has benefited from inexpensive high quality DNA sequencing technology, which has generated more than 140 genome sequences for taxonomic type strains and environmental Streptomyces spp. isolates. Many of the sequenced streptomycetes belong to the same species. For instance, Streptomyces albus has been isolated from diverse environmental niches and seven strains have been sequenced, consequently this species has been sequenced more than any other streptomycete, allowing valuable analyses of strain-level diversity in secondary metabolism. Bioinformatics analyses identified a total of 48 unique biosynthetic gene clusters harboured by Streptomyces albus strains. Eighteen of these gene clusters specify the core secondary metabolome of the species. Fourteen of the gene clusters are contained by one or more strain and are considered auxiliary, while 16 of the gene clusters encode the production of putative strain-specific secondary metabolites. Analysis of Streptomyces albus strains suggests that each strain of a Streptomyces species likely harbours at least one strain-specific biosynthetic gene cluster. Importantly, this implies that deep sequencing of a species will not exhaust gene cluster diversity and will continue to yield novelty. PMID:25635820

  1. Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes

    Science.gov (United States)

    Horsman, Geoff P.; Chen, Yihua; Thorson, Jon S.; Shen, Ben

    2010-01-01

    Enediynes are potent antitumor antibiotics that are classified as 9- or 10-membered according to the size of the enediyne core structure. However, almost nothing is known about enediyne core biosynthesis, and the determinants of 9- versus 10-membered enediyne core biosynthetic divergence remain elusive. Previous work identified enediyne-specific polyketide synthases (PKSEs) that can be phylogenetically distinguished as being involved in 9- versus 10-membered enediyne biosynthesis, suggesting that biosynthetic divergence might originate from differing PKSE chemistries. Recent in vitro studies have identified several compounds produced by the PKSE and associated thioesterase (TE), but condition-dependent product profiles make it difficult to ascertain a true catalytic difference between 9- and 10-membered PKSE-TE systems. Here we report that PKSE chemistry does not direct 9- versus 10-membered enediyne core biosynthetic divergence as revealed by comparing the products from three 9-membered and two 10-membered PKSE-TE systems under identical conditions using robust in vivo assays. Three independent experiments support a common catalytic function for 9- and 10-membered PKSEs by the production of a heptaene metabolite from: (i) all five cognate PKSE-TE pairs in Escherichia coli; (ii) the C-1027 and calicheamicin cognate PKSE-TEs in Streptomyces lividans K4-114; and (iii) selected native producers of both 9- and 10-membered enediynes. Furthermore, PKSEs and TEs from different 9- and 10-membered enediyne biosynthetic machineries are freely interchangeable, revealing that 9- versus 10-membered enediyne core biosynthetic divergence occurs beyond the PKSE-TE level. These findings establish a starting point for determining the origins of this biosynthetic divergence. PMID:20534556

  2. Characterization of the biosynthetic gene cluster for cryptic phthoxazolin A in Streptomyces avermitilis.

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    Dian Anggraini Suroto

    Full Text Available Phthoxazolin A, an oxazole-containing polyketide, has a broad spectrum of anti-oomycete activity and herbicidal activity. We recently identified phthoxazolin A as a cryptic metabolite of Streptomyces avermitilis that produces the important anthelmintic agent avermectin. Even though genome data of S. avermitilis is publicly available, no plausible biosynthetic gene cluster for phthoxazolin A is apparent in the sequence data. Here, we identified and characterized the phthoxazolin A (ptx biosynthetic gene cluster through genome sequencing, comparative genomic analysis, and gene disruption. Sequence analysis uncovered that the putative ptx biosynthetic genes are laid on an extra genomic region that is not found in the public database, and 8 open reading frames in the extra genomic region could be assigned roles in the biosynthesis of the oxazole ring, triene polyketide and carbamoyl moieties. Disruption of the ptxA gene encoding a discrete acyltransferase resulted in a complete loss of phthoxazolin A production, confirming that the trans-AT type I PKS system is responsible for the phthoxazolin A biosynthesis. Based on the predicted functional domains in the ptx assembly line, we propose the biosynthetic pathway of phthoxazolin A.

  3. On the biosynthetic origin of carminic acid

    DEFF Research Database (Denmark)

    Rasmussen, Silas A.; Kongstad, Kenneth T; Khorsand-Jamal, Paiman

    2018-01-01

    provides solid evidence of a polyketide, rather than a shikimate, origin of coccid pigments. Based on the newly identified compounds, we present a detailed biosynthetic scheme that accounts for the formation of carminic acid (CA) in D. coccus and all described coccid pigments which share a flavokermesic...... distribution suggests a common evolutionary origin for the trait in all coccid dye producing insect species....

  4. New opportunities for the regulation of secondary metabolism in plants: focus on microRNAs.

    Science.gov (United States)

    Bulgakov, Victor P; Avramenko, Tatiana V

    2015-09-01

    Plant cell cultures are of particular interest in industrial applications as a source of biologically active substances. It is difficult, however, to achieve stable production of secondary metabolites for many plant cell cultures using classical techniques. Novel approaches should be developed for removal of the inhibitor blocks that prevent pathway activation and shift the regulatory balance to the activation of entire biosynthetic pathways. MicroRNAs (miRNAs) are small RNAs that play important regulatory roles in various biological processes. Only recently miRNAs have been demonstrated as active in secondary metabolism regulation. In this work, we summarize recent data on the emerging approaches based on regulation of secondary metabolism by miRNAs.

  5. Chemical fingerprint and simultaneous determination of alkaloids and flavonoids in aerial parts of genus Peganum indigenous to China based on HPLC-UV: application of analysis on secondary metabolites accumulation.

    Science.gov (United States)

    Wen, Fangfang; Cheng, Xuemei; Liu, Wei; Xuan, Min; Zhang, Lei; Zhao, Xin; Shan, Meng; Li, Yan; Teng, Liang; Wang, Zhengtao; Wang, Changhong

    2014-12-01

    The aerial parts of genus Peganum are officially used in traditional Chinese medicine. The paper aims to establish a high-performance liquid chromatography (HPLC) method for fingerprint analysis and simultaneous determination of three alkaloids and two flavonoids in aerial parts of genus Peganum, and to analyze accumulative difference of secondary metabolites in inter-species, individuals of plants, inter-/intra-population and from different growing seasons. HPLC analysis was performed on a C18 column with gradient elution using 0.1% trifloroacetic acid and acetonitrile as mobile phase and detected at 265 nm, by conventional methodology validation. For fingerprint analysis, the RSDs of relative retention time and relative peak area of the characteristic peaks were within 0.07-0.78 and 0.94-9.09%, respectively. For simultaneous determination of vasicine, harmaline, harmine, deacetylpeganetin and peganetin, all calibration curves showed good linearity (r > 0.9990) within the test range. The relative standard deviations of precision, repeatability and stability test did not exceed 2.37, 2.68 and 2.67%, respectively. The average recoveries for the five analytes were between 96.47 and 101.20%. HPLC fingerprints play a minor role in authenticating and differentiating the herbs of different species of genus Peganum. However, the secondary metabolites levels of alkaloids and flavonoids in aerial parts of genus Peganum rely on species-, habitat-, and growth season-dependent accumulation. Copyright © 2014 John Wiley & Sons, Ltd.

  6. Identification of a Classical Mutant in the Industrial Host Aspergillus niger by Systems Genetics: LaeA Is Required for Citric Acid Production and Regulates the Formation of Some Secondary Metabolites

    Directory of Open Access Journals (Sweden)

    Jing Niu

    2016-01-01

    Full Text Available The asexual filamentous fungus Aspergillus niger is an important industrial cell factory for citric acid production. In this study, we genetically characterized a UV-generated A. niger mutant that was originally isolated as a nonacidifying mutant, which is a desirable trait for industrial enzyme production. Physiological analysis showed that this mutant did not secrete large amounts of citric acid and oxalic acid, thus explaining the nonacidifying phenotype. As traditional complementation approaches to characterize the mutant genotype were unsuccessful, we used bulk segregant analysis in combination with high-throughput genome sequencing to identify the mutation responsible for the nonacidifying phenotype. Since A. niger has no sexual cycle, parasexual genetics was used to generate haploid segregants derived from diploids by loss of whole chromosomes. We found that the nonacidifying phenotype was caused by a point mutation in the laeA gene. LaeA encodes a putative methyltransferase-domain protein, which we show here to be required for citric acid production in an A. niger lab strain (N402 and in other citric acid production strains. The unexpected link between LaeA and citric acid production could provide new insights into the transcriptional control mechanisms related to citric acid production in A. niger. Interestingly, the secondary metabolite profile of a ΔlaeA strain differed from the wild-type strain, showing both decreased and increased metabolite levels, indicating that LaeA is also involved in regulating the production of secondary metabolites. Finally, we show that our systems genetics approach is a powerful tool to identify trait mutations.

  7. Identification of a Classical Mutant in the Industrial Host Aspergillus niger by Systems Genetics: LaeA Is Required for Citric Acid Production and Regulates the Formation of Some Secondary Metabolites.

    Science.gov (United States)

    Niu, Jing; Arentshorst, Mark; Nair, P Deepa S; Dai, Ziyu; Baker, Scott E; Frisvad, Jens C; Nielsen, Kristian F; Punt, Peter J; Ram, Arthur F J

    2015-11-13

    The asexual filamentous fungus Aspergillus niger is an important industrial cell factory for citric acid production. In this study, we genetically characterized a UV-generated A. niger mutant that was originally isolated as a nonacidifying mutant, which is a desirable trait for industrial enzyme production. Physiological analysis showed that this mutant did not secrete large amounts of citric acid and oxalic acid, thus explaining the nonacidifying phenotype. As traditional complementation approaches to characterize the mutant genotype were unsuccessful, we used bulk segregant analysis in combination with high-throughput genome sequencing to identify the mutation responsible for the nonacidifying phenotype. Since A. niger has no sexual cycle, parasexual genetics was used to generate haploid segregants derived from diploids by loss of whole chromosomes. We found that the nonacidifying phenotype was caused by a point mutation in the laeA gene. LaeA encodes a putative methyltransferase-domain protein, which we show here to be required for citric acid production in an A. niger lab strain (N402) and in other citric acid production strains. The unexpected link between LaeA and citric acid production could provide new insights into the transcriptional control mechanisms related to citric acid production in A. niger. Interestingly, the secondary metabolite profile of a ΔlaeA strain differed from the wild-type strain, showing both decreased and increased metabolite levels, indicating that LaeA is also involved in regulating the production of secondary metabolites. Finally, we show that our systems genetics approach is a powerful tool to identify trait mutations. Copyright © 2016 Niu et al.

  8. Lipopolysaccharide (LPS) stimulation of fungal secondary metabolism

    Science.gov (United States)

    Khalil, Zeinab G.; Kalansuriya, Pabasara; Capon, Robert J.

    2014-01-01

    We report on a preliminary investigation of the use the Gram-negative bacterial cell wall constituent lipopolysaccharide (LPS) as a natural chemical cue to stimulate and alter the expression of fungal secondary metabolism. Integrated high-throughput micro-cultivation and micro-analysis methods determined that 6 of 40 (15%) of fungi tested responded to an optimal exposure to LPS (0.6 ng/mL) by activating, enhancing or accelerating secondary metabolite production. To explore the possible mechanisms behind this effect, we employed light and fluorescent microscopy in conjunction with a nitric oxide (NO)-sensitive fluorescent dye and an NO scavenger to provide evidence that LPS stimulation of fungal secondary metabolism coincided with LPS activation of NO. Several case studies demonstrated that LPS stimulation can be scaled from single microplate well (1.5 mL) to preparative (>400 mL) scale cultures. For example, LPS treatment of Penicillium sp. (ACM-4616) enhanced pseurotin A and activated pseurotin A1 and pseurotin A2 biosynthesis, whereas LPS treatment of Aspergillus sp. (CMB-M81F) substantially accelerated and enhanced the biosynthesis of shornephine A and a series of biosynthetically related ardeemins and activated production of neoasterriquinone. As an indication of broader potential, we provide evidence that cultures of Penicillium sp. (CMB-TF0411), Aspergillus niger (ACM-4993F), Rhizopus oryzae (ACM-165F) and Thanatephorus cucumeris (ACM-194F) were responsive to LPS stimulation, the latter two examples being particular noteworthy as neither are known to produce secondary metabolites. Our results encourage the view that LPS stimulation can be used as a valuable tool to expand the molecular discovery potential of fungal strains that either have been exhaustively studied by or are unresponsive to traditional culture methodology. PMID:25379339

  9. Co-Occurrence of Regulated, Masked and Emerging Mycotoxins and Secondary Metabolites in Finished Feed and Maize—An Extensive Survey

    Directory of Open Access Journals (Sweden)

    Paula Kovalsky

    2016-12-01

    Full Text Available Global trade of agricultural commodities (e.g., animal feed requires monitoring for fungal toxins. Also, little is known about masked and emerging toxins and metabolites. 1926 samples from 52 countries were analysed for toxins and metabolites. Of 162 compounds detected, up to 68 metabolites were found in a single sample. A subset of 1113 finished feed, maize and maize silage samples containing 57 compounds from 2012 to 2015 from 44 countries was investigated using liquid chromatography and mass spectrometry. Deoxynivalenol (DON, zearalenone (ZEN and fumonisins showed large increases of annual medians in Europe. Within a region, distinct trends were observed, suggesting importance of local meteorology and cultivars. In 2015, median DON concentrations increased to 1400 μ g·kg − 1 in Austria, but were stable in Germany at 350 μ g·kg − 1 . In 2014, enniatins occurred at median concentrations of 250 μ g·kg − 1 in Europe, at levels similar to DON and ZEN. The latter were frequently correlated with DON-3-glucoside and ZEN-14-sulfate. Co-occurrence of regulated toxins was frequent with e.g., enniatins, and moniliformin. Correlation was observed between DON and DON-3-glucoside and with beauvericin. Results indicate that considerably more than 25% of agricultural commodities could be contaminated with mycotoxins as suggested by FAO, although this is at least partly due to the lower limits of detection in the current survey. Observed contamination percentages ranged from 7.1 to 79% for B trichothecenes and 88% for ZEN.

  10. Giant linear plasmids in Streptomyces: a treasure trove of antibiotic biosynthetic clusters.

    Science.gov (United States)

    Kinashi, Haruyasu

    2011-01-01

    Many giant linear plasmids have been isolated from Streptomyces by using pulsed-field gel electrophoresis and some of them were found to carry an antibiotic biosynthetic cluster(s); SCP1 carries biosynthetic genes for methylenomycin, pSLA2-L for lankacidin and lankamycin, and pKSL for lasalocid and echinomycin. Accumulated data suggest that giant linear plasmids have played critical roles in genome evolution and horizontal transfer of secondary metabolism. In this review, I summarize typical examples of giant linear plasmids whose involvement in antibiotic production has been studied in some detail, emphasizing their finding processes and interaction with the host chromosomes. A hypothesis on horizontal transfer of secondary metabolism involving giant linear plasmids is proposed at the end.

  11. Serotonin syndrome following sibutramine poisoning in a child, with sequential quantification of sibutramine and its primary and secondary amine metabolites in plasma.

    Science.gov (United States)

    Bucaretchi, Fábio; de Capitani, Eduardo Mello; Mello, Sueli Moreira; Lanaro, Rafael; Barros, Roberta F; Fernandes, Luciane C R; da Costa, José Luiz; Hyslop, Stephen

    2009-07-01

    To report a case of serotonin syndrome (SS) after sibutramine overdose in a child. A 4-year-old girl was admitted 25 h after accidentally ingesting approximately 27 pills of sibutramine (15 mg, approximately 23 mg/kg). The child developed clinical features suggestive of SS, including diaphoresis, tachycardia, hypertension, agitation, insomnia, incoordination, hypertonia (lower limbs > upper limbs), and hallucinations. Serum creatine phosphokinase levels reached a peak on day 3 (2,577 U/L, reference value sibutramine and the active metabolites, M1 (mono-desmethyl sibutramine) and M2 (di-desmethyl sibutramine), by liquid chromatography/electrospray ionization tandem mass spectrometry in six sequential samples collected from 25 to 147 h post-ingestion revealed a nonlinear decrease in the log-scale plasma concentrations. Treatment was only supportive and involved prolonged sedation to control the agitation, sleeplessness, and hypertension; no cyproheptadine was used. The patient was discharged on day 6 and follow-up revealed no sequelae. To our knowledge, this is the first report of SS after sibutramine overdose in a child, with sequential monitoring of the plasma levels of the drug and its two active metabolites. The growing consumption of weight reducing pills may increase the risk of unintentional acute toxic exposures in children.

  12. Secondary metabolism in the lichen symbiosis.

    Science.gov (United States)

    Calcott, Mark J; Ackerley, David F; Knight, Allison; Keyzers, Robert A; Owen, Jeremy G

    2018-03-05

    Lichens, which are defined by a core symbiosis between a mycobiont (fungal partner) and a photobiont (photoautotrophic partner), are in fact complex assemblages of microorganisms that constitute a largely untapped source of bioactive secondary metabolites. Historically, compounds isolated from lichens have predominantly been those produced by the dominant fungal partner, and these continue to be of great interest for their unique chemistry and biotechnological potential. In recent years it has become apparent that many photobionts and lichen-associated bacteria also produce a range of potentially valuable molecules. There is evidence to suggest that the unique nature of the symbiosis has played a substantial role in shaping many aspects of lichen chemistry, for example driving bacteria to produce metabolites that do not bring them direct benefit but are useful to the lichen as a whole. This is most evident in studies of cyanobacterial photobionts, which produce compounds that differ from free living cyanobacteria and are unique to symbiotic organisms. The roles that these and other lichen-derived molecules may play in communication and maintaining the symbiosis are poorly understood at present. Nonetheless, advances in genomics, mass spectrometry and other analytical technologies are continuing to illuminate the wealth of biological and chemical diversity present within the lichen holobiome. Implementation of novel biodiscovery strategies such as metagenomic screening, coupled with synthetic biology approaches to reconstitute, re-engineer and heterologously express lichen-derived biosynthetic gene clusters in a cultivable host, offer a promising means for tapping into this hitherto inaccessible wealth of natural products.

  13. Production and purification of anti-bacterial biometabolite from wild-type Lactobacillus, isolated from fermented bamboo shoot: future suggestions and a proposed system for secondary metabolite onsite recovery during continuous fermentation.

    Science.gov (United States)

    Badwaik, Laxmikant S; Borah, Pallab Kumar; Deka, Sankar C

    2015-02-01

    Wild-type lactobacillus isolated form Khorisa, a fermented bamboo shoot product of Assam, India were evaluated for production anti-bacterial secondary biometabolites, against Staphylococcus aureus. Submerged fermentation technique was used for the production of secondary anti-microbial biometabolite by a single wild-type lactobacillus strain, which tested positive for the release of anti-bacterial factor(s). Crude cell-free supernatant was obtained, followed by extraction in water-immiscible solvents viz., chloroform, hexane, petroleum ether. Chloroform extract of cell-free crude supernatant showed maximum yield (0.054 g/ml) and inhibited all indicator bacterial strains viz., Escherichia coli, Staphylococcus aureus, and Bacillus cereus. Yields of hexane and petroleum ether extract were 0.052 and 0.026 g/ml, respectively. Minimum lethal dose concentration assay of the chloroform extract showed LDmin values at 27, 1.68, and 1.68 mg/ml for E. coli, S. aureus, and B. cereus, respectively. Kill time for all the indicator bacterial strains were less than 12 h. The efficacy of the anti-bacterial substance seemed to depend on the presence of organic acids, particularly lactic acid. Conceptual-based suggestion for the development of an onsite secondary metabolites recovery system during continuous fermentation has also been attempted.

  14. Proteomics Coupled with Metabolite and Cell Wall Profiling Reveal Metabolic Processes of a Developing Rice Stem Internode

    Energy Technology Data Exchange (ETDEWEB)

    Lin, Fan; Williams, Brad J.; Thangella, Padmavathi A. V.; Ladak, Adam; Schepmoes, Athena A.; Olivos, Hernando J.; Zhao, Kangmei; Callister, Stephen J.; Bartley, Laura E.

    2017-07-13

    Internodes of grass stems function in mechanical support, transport, and, in some species, are a major sink organ for carbon in the form of cell wall polymers. This study reports cell wall composition, proteomic and metabolite analyses of the rice elongating internode. Along eight segments of the second rice internode (internode II) at booting stage, cellulose, lignin, and xylose increase as a percentage of cell wall material from the younger to the older internode segments, indicating active cell wall synthesis. Liquid-chromatography tandem mass spectrometry (LC-MS/MS) of trypsin-digested peptides of size-fractionated proteins extracted from this internode at booting reveals 2547proteins with at least two unique peptides. The dataset includes many glycosyltransferases, acyltransferases, glycosyl hydrolases, cell wall-localized proteins, and protein kinases that have or may have functions in cell wall biosynthesis or remodeling. Phospho-enrichment of the internode II peptides identified 21 unique phosphopeptides belonging to 20 phosphoproteins including an LRR-III family receptor like kinase. GO over-representation and KEGG pathway analyses highlight the abundances of internode proteins involved in biosynthetic processes, especially the synthesis of secondary metabolites such as phenylpropanoids and flavonoids. LC-MS of hot methanol-extracted secondary metabolites from internode II at four stages (elongation, early mature, mature and post mature) indicates that secondary metabolites in stems are distinct from those of roots and leaves, and differ during stem maturation. This work fills a void of knowledge of proteomics and metabolomics data for grass stems, specifically for rice, and provides baseline knowledge for more detailed studies of cell wall synthesis and other biological processes during internode development, toward improving grass agronomic properties.

  15. Phytotoxic activity against Bromus tectorum for secondary metabolites of a seed-pathogenic Fusarium strain belonging to the F. tricinctum species complex.

    Science.gov (United States)

    Masi, Marco; Meyer, Susan; Pescitelli, Gennaro; Cimmino, Alessio; Clement, Suzette; Peacock, Beth; Evidente, Antonio

    2017-12-01

    The winter annual grass Bromus tectorum (cheatgrass) has become highly invasive in semiarid ecosystems of western North America. In these areas, a natural phenomenon, complete cheatgrass stand failure ('die-off'), is apparently caused by a complex interaction among soilborne fungal pathogens. Several Fusarium strains belonging to the Fusarium tricinctum species complex were isolated from these soils and found to be pathogenic on B. tectorum seeds. One of these strains was produced in cheatgrass seed culture to evaluate its ability to produce phytotoxins. Six metabolites were isolated and identified by spectroscopic methods (essentially 1D and 2D NMR and ESIMS) as acuminatopyrone (1), blumenol A (2), chlamydosporol (3), isochlamydosporol (4), ergosterol (5) and 4-hydroxybenzaldehyde (6). Upon testing against B. tectorum in a seedling bioassay, (6) the coleoptile and radicle length of cheatgrass seedlings were significantly reduced. Compounds 1 and 2 showed moderate activity, while 3-5 were not significantly different from the control.

  16. PTP1B Inhibitory and Anti-Inflammatory Effects of Secondary Metabolites Isolated from the Marine-Derived Fungus Penicillium sp. JF-55

    Directory of Open Access Journals (Sweden)

    Youn-Chul Kim

    2013-04-01

    Full Text Available Protein tyrosine phosphatase 1B (PTP1B plays a major role in the negative regulation of insulin signaling, and is thus considered as an attractive therapeutic target for the treatment of diabetes. Bioassay-guided investigation of the methylethylketone extract of marine-derived fungus Penicillium sp. JF-55 cultures afforded a new PTP1B inhibitory styrylpyrone-type metabolite named penstyrylpyrone (1, and two known metabolites, anhydrofulvic acid (2 and citromycetin (3. Compounds 1 and 2 inhibited PTP1B activity in a dose-dependent manner, and kinetic analyses of PTP1B inhibition suggested that these compounds inhibited PTP1B activity in a competitive manner. In an effort to gain more biological potential of the isolated compounds, the anti-inflammatory effects of compounds 1–3 were also evaluated. Among the tested compounds, only compound 1 inhibited the production of NO and PGE2, due to the inhibition of the expression of iNOS and COX-2. Penstyrylpyrone (1 also reduced TNF-α and IL-1β production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of IκB-α, NF-κB nuclear translocation, and NF-κB DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP, an inhibitor of HO-1, it was verified that the inhibitory effects of penstyrylpyrone (1 on the pro-inflammatory mediators and NF-κB DNA binding activity were associated with the HO-1 expression. Therefore, these results suggest that penstyrylpyrone (1 suppresses PTP1B activity, as well as the production of pro-inflammatory mediators via NF-κB pathway, through expression of anti-inflammatory HO-1.

  17. PTP1B Inhibitory and Anti-Inflammatory Effects of Secondary Metabolites Isolated from the Marine-Derived Fungus Penicillium sp. JF-55

    Science.gov (United States)

    Lee, Dong-Sung; Jang, Jae-Hyuk; Ko, Wonmin; Kim, Kyoung-Su; Sohn, Jae Hak; Kang, Myeong-Suk; Ahn, Jong Seog; Kim, Youn-Chul; Oh, Hyuncheol

    2013-01-01

    Protein tyrosine phosphatase 1B (PTP1B) plays a major role in the negative regulation of insulin signaling, and is thus considered as an attractive therapeutic target for the treatment of diabetes. Bioassay-guided investigation of the methylethylketone extract of marine-derived fungus Penicillium sp. JF-55 cultures afforded a new PTP1B inhibitory styrylpyrone-type metabolite named penstyrylpyrone (1), and two known metabolites, anhydrofulvic acid (2) and citromycetin (3). Compounds 1 and 2 inhibited PTP1B activity in a dose-dependent manner, and kinetic analyses of PTP1B inhibition suggested that these compounds inhibited PTP1B activity in a competitive manner. In an effort to gain more biological potential of the isolated compounds, the anti-inflammatory effects of compounds 1–3 were also evaluated. Among the tested compounds, only compound 1 inhibited the production of NO and PGE2, due to the inhibition of the expression of iNOS and COX-2. Penstyrylpyrone (1) also reduced TNF-α and IL-1β production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of IκB-α, NF-κB nuclear translocation, and NF-κB DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP), an inhibitor of HO-1, it was verified that the inhibitory effects of penstyrylpyrone (1) on the pro-inflammatory mediators and NF-κB DNA binding activity were associated with the HO-1 expression. Therefore, these results suggest that penstyrylpyrone (1) suppresses PTP1B activity, as well as the production of pro-inflammatory mediators via NF-κB pathway, through expression of anti-inflammatory HO-1. PMID:23612372

  18. The Cremeomycin Biosynthetic Gene Cluster Encodes a Pathway for Diazo Formation.

    Science.gov (United States)

    Waldman, Abraham J; Pechersky, Yakov; Wang, Peng; Wang, Jennifer X; Balskus, Emily P

    2015-10-12

    Diazo groups are found in a range of natural products that possess potent biological activities. Despite longstanding interest in these metabolites, diazo group biosynthesis is not well understood, in part because of difficulties in identifying specific genes linked to diazo formation. Here we describe the discovery of the gene cluster that produces the o-diazoquinone natural product cremeomycin and its heterologous expression in Streptomyces lividans. We used stable isotope feeding experiments and in vitro characterization of biosynthetic enzymes to decipher the order of events in this pathway and establish that diazo construction involves late-stage N-N bond formation. This work represents the first successful production of a diazo-containing metabolite in a heterologous host, experimentally linking a set of genes with diazo formation. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  19. Efecto del Tostado Sobre los Metabolitos Secundarios y la Actividad Antioxidante de Clones de Cacao Colombiano / Effect of Roasting on the Secondary Metabolites and Antioxidant Activity of Colombian Cocoa Clones

    Directory of Open Access Journals (Sweden)

    Sandra Zapata Bustamante

    2014-12-01

    Full Text Available Resumen. El tostado es una de las operaciones tecnológicas másimportantes en el procesamiento de los granos de cacao; esteproceso conduce a la formación de los productos de la reacciónde Maillard (RM los cuales son cruciales para el desarrollo dela calidad organoléptica de los granos de cacao y sus productosasociados. En el presente estudio se evaluó el efecto del tostadosobre el contenido de metabolitos secundarios y la actividadantioxidante en cinco clones de cacao cultivados en Colombia.En los extractos metanólicos de los diferentes clones de cacao sedeterminó el contenido de fenoles totales, taninos condensados,antocianinas totales, catequina y epicatequina, teobromina ycafeína. Además, se determinó la actividad antioxidante pormedio de la actividad atrapadora del radical ABTS•+, el métodoORAC y la capacidad atrapadora de radicales superóxido. Enconclusión, el efecto del tostado en los clones de cacao no tuvo uncomportamiento uniforme sobre los cambios en los contenidos delos diversos metabolitos secundarios y la actividad antioxidante. /  Abstract. Roasting is one of the most important technologicaloperations in the processing of cocoa beans; this process leads tothe formation of products of the Maillard reaction (RM, which arecrucial for the development of organoleptic quality of cocoa beansand its associated products. The aim of this study was to evaluatethe effect of roasting on the content of secondary metabolites andantioxidant activity in five Colombian cocoa clones, by differentmethodologies. The methanolic extracts of the cocoa beans wereanalyzed for total phenols content, condensed tannins, totalantiocianins, catechin and epicatechin, theobromine and caffeine.The antioxidant activity was determined by ABTS assay, ORACmethod and superoxide radical scavenging method. The effect ofroasting on cocoa clones did not have an unspecified behavior. Inconclusion, the effect of roasting of cacao clones was not uniformon the

  20. Isolation and structural elucidation of secondary metabolites from plants of the family Flacourtiaceae and Asclepiadaceae, and evaluation of biological activity of the sesquiterpene lactones and the diterpenes of Casearia sp

    International Nuclear Information System (INIS)

    Binns Quiros, Franklin

    2012-01-01

    A phytochemical study was realized of the plants Casearia aculeata, Casearia nitida and Asclepias verticillata, using experiments of nuclear magnetic resonance (NMR) of one and two dimensions. Ten secondary metabolites are isolated from C. aculeata and C. nitida. Three of the secondary metabolites have presented a structure known: a diterpene type kaurane: ent-kaurenic acid, a diterpene type pimarane: oxide of 3β-hydroximanoil and a steroid: 4-stigmastene-3-ona. Seven remaining compounds have corresponded to diterpene type clerodane of novel structure. Eight glycosides of poly oxidized pregnanes of novel structure are isolated from A. verticillata. In vitro tests of cytotoxicity and induction of caspase-3 are performed on leukemia cells type Jurkat T. These tests were performed at fifteen sesquiterpene lactones and at four diterpenes. The tests developed have had the purpose to describe structure-activity relationships that can be linked with the capacity to inhibit the factor NF-κB (sesquiterpene lactones) described in the literature and with the known mechanism of action induction of apoptosis in diterpenes type clerodane. A clear relationship between the capacity (high, intermediate or low) to inhibit the factor NF-κB and the capacity to induce to the caspase-3 has remained without observation in the sesquiterpene lactones. Some structural comparisons related with the cytotoxic capacity and the induction of the caspase-3 have been described for the series of LSs with carbon structure of pseudoguianolides. Diterpenes with carbon structure of diterpenes type clerodane have had greater cytotoxic activity with respect to without carbon structure. Diterpenes type clerodane isolated from the family Flacourtiaceae have been cytotoxics, their capacity to induce to the caspase-3 has remained without be nearby to induction realized by the actinomycin D (pure inducer of the caspase-3). (author) [es

  1. Morphine metabolites

    DEFF Research Database (Denmark)

    Christrup, Lona Louring

    1997-01-01

    , morphine-3-glucuronide (M3G) and morphine-6-glucuronide (M6G) are the major metabolites of morphine. The metabolism of morphine occurs not only in the liver, but may also take place in the brain and the kidneys. The glucuronides are mainly eliminated via bile and urine. Glucuronides as a rule...... are considered as highly polar metabolites unable to cross the blood-brain barrier. Although morphine glucuronidation has been demonstrated in human brain tissue, the capacity is very low compared to that of the liver, indicating that the M3G and M6G concentrations observed in the cerebrospinal fluid (CSF) after...... systemic administration reflect hepatic metabolism of morphine and that the morphine glucuronides, despite their high polarity, can penetrate into the brain. Like morphine, M6G has been shown to be relatively more selective for mu-receptors than for delta- and kappa-receptors while M3G does not appear...

  2. ESTRATEGIAS PARA INCREMENTAR LA PRODUCCIÓN DE METABOLITOS SECUNDARIOS EN CULTIVOS DE CÉLULAS VEGETALES STRATEGIES FOR THE IMPROVEMENT OF SECONDARY METABOLITES PRODUCTION IN PLAN CELL CULTURES

    Directory of Open Access Journals (Sweden)

    Mario Arias Zabala

    2009-06-01

    Full Text Available El cultivo de células vegetales ha surgido como una alternativa para la obtención de metabolitos de alto valor agregado, producidos en las plantas en bajas concentraciones y para los cuales, no existen procesos de síntesis química conocidos; sin embargo, para la implementación de esta tecnología es necesario el desarrollo de estrategias que permitan incrementar la productividad de los cultivos in vitro. En este trabajo se discuten diferentes alternativas planteadas para lograr este objetivo: en la p