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Sample records for 275i major alkaloids

  1. Antibacterial activity of Hydrastis canadensis extract and its major isolated alkaloids.

    Scazzocchio, F; Cometa, M F; Tomassini, L; Palmery, M

    2001-08-01

    The antibacterial activity of extract and isolated major alkaloids (berberine, beta-hydrastine, canadine and canadaline) of Hydrastis canadensis L. (Ranunculaceae) was evaluated against 6 strains of microorganism: Staphylococcus aureus (ATCC 25 993 and ATCC 6538P), Streptococcus sanguis (ATCC 10 556), Escherichia coli (ATCC 25 922), Pseudomonas aeruginosa (ATCC 27 853). Bactericidal activity was evaluated by contact test by measuring the "killing time" on a low density bacterial inoculum, and bacteriostatic activity in liquid medium by M.I.C. values. The results provide a rational basis for the traditional antibacterial use of Hydrastis canadensis. PMID:11509983

  2. IN VITRO EFFECT OF MITRAGYNINE (A MAJOR ALKALOID OF MITRAGYNA SPECIOSA KORTH) ON AMINOPYRINE METABOLISM IN RAT HEPATOCYTES

    Rukhsana Anwar, Abas Hj Hussin , Sabariah Ismail* and Sharif Mahsufi Mansor

    2012-01-01

    Mitragyna speciosa Korth. is a member of the Rubiaceae family. More than 25 alkaloids have been isolated from Mitragyna speciosa. Mitragynine is the major alkaloid of this plant and is responsible for antinociceptive action. No single study is available about the effect of mitragynine on aminopyrine N-demethylase activity in rat hepatocytes. Experiments were undertaken to evaluate the effect of mitragynine in different age groups (adult & old) of Sprague- Dawley (SD) male and female rat hepat...

  3. Relaxant effects of Hydrastis canadensis L. and its major alkaloids on guinea pig isolated trachea.

    Abdel-Haq, H; Cometa, M F; Palmery, M; Leone, M G; Silvestrini, B; Saso, L

    2000-11-01

    Hydrastis or goldenseal, one of the most popular medicinal herbs in the U.S.A., is used in mild pathological conditions like cold and flu, based on the pharmacological properties of its active components, berberine (anticholinergic, antisecretory, and antimicrobial) and beta-hydrastine (astringent). We previously reported the relaxant effect of a total ethanolic extract of hydrastis on carbachol precontracted isolated guinea pig trachea, and with the present study, using the same experimental model, we aimed at evaluating the contribution of its major alkaloids, berberine, beta-hydrastine, canadine and canadaline to the total effect. Furthermore, using specific pharmacological tools, like timolol and xanthine amine congener, we attempted to elucidate its mechanism of action. The EC50 of berberine, beta-hydrastine, canadine and canadaline, were 34.2+/-0.6, 72.8+/-0.6, 11.9+/-1.2 and 2.4+/-0.8 microg/ml, respectively. Timolol effectively antagonized the effect of canadine (EC50 = 19.7+/-3.0 microg/ml) and canadaline (EC50 = 17.1+/-1.2 microg/ml) but not that of berberine and beta-hydrastine, while xanthine amine congener antagonized the effect of beta-hydrastine (EC50 = 149.9+/-35.3 microg/ml) and canadaline (EC50 = 26.1+/-3.0 microg/ml) but not that of berberine and canadine. Besides, the hydrastis extract, at concentrations between 0.01 and 0.1 microg/ml, potentiated the relaxant effect of isoprenaline on carbachol-precontracted isolated guinea pig trachea. These data, which are insufficient to draw definite mechanistic conclusions, indicate that the aforementioned alkaloids may act by interacting with adrenergic and adenosinic receptors. PMID:11129501

  4. Vinca Alkaloids

    Maryam Moudi

    2013-01-01

    Full Text Available Vinca alkaloids are a subset of drugs obtained from the Madagascar periwinkle plant. They are naturally extracted from the pink periwinkle plant, Catharanthus roseus G. Don and have a hypoglycemic as well as cytotoxic effects. They have been used to treat diabetes, high blood pressure and have been used as disinfectants. The vinca alkaloids are also important for being cancer fighters. There are four major vinca alkaloids in clinical use: Vinblastine (VBL, vinorelbine (VRL, vincristine (VCR and vindesine (VDS. VCR, VBL and VRL have been approved for use in the United States. Vinflunine is also a new synthetic vinca alkaloid, which has been approved in Europe for the treatment of second-line transitional cell carcinoma of the urothelium is being developed for other malignancies. Vinca alkaloids are the second-most-used class of cancer drugs and will stay among the original cancer therapies. Different researches and studies for new vinca alkaloid applications will be carried out in this regard.

  5. IN VITRO EFFECT OF MITRAGYNINE (A MAJOR ALKALOID OF MITRAGYNA SPECIOSA KORTH ON AMINOPYRINE METABOLISM IN RAT HEPATOCYTES

    Rukhsana Anwar, Abas Hj Hussin , Sabariah Ismail* and Sharif Mahsufi Mansor

    2012-07-01

    Full Text Available Mitragyna speciosa Korth. is a member of the Rubiaceae family. More than 25 alkaloids have been isolated from Mitragyna speciosa. Mitragynine is the major alkaloid of this plant and is responsible for antinociceptive action. No single study is available about the effect of mitragynine on aminopyrine N-demethylase activity in rat hepatocytes. Experiments were undertaken to evaluate the effect of mitragynine in different age groups (adult & old of Sprague- Dawley (SD male and female rat hepatocytes. In vitro this evaluation was assessed by different concentration of mitragynine (0.0025µM-250µM. Hepatocytes were prepared by collagenase perfusion technique. Aminopyrine N-demethylase activity was determined by measuring the quantity of formaldehyde formed. Results showed that a significant increase in aminopyrine N-demethylase activity was observed in the adult male, female and old female SD rat hepatocytes treated with 250µM mitragynine (p< 0.05. However, the old male rat did not show any significant change at any concentration of mitragynine. In conclusion this study indicates the induction of hepatic drug metabolizing enzymes by mitragynine is affected by the aging process in male but unaffected in female.

  6. A review of the anticancer potential of the antimalarial herbal cryptolepis sanguinolenta and its major alkaloid cryptolepine.

    Ansah, C; Mensah, K B

    2013-09-01

    Cryptolepis sanguinolenta (Lindl.) Schltr (Periplocaceae), has a longstanding traditional use in the treatment of malaria in the West African region. Recent evidence suggests that the aqueous extract from the roots and the major alkaloid from the plant, cryptolepine, have prospects as cancer chemotherapeutic agents on account of their potent cytotoxicity to mammalian cells. Several mechanisms have been proposed to explain the cytotoxic activities of the agents. However, emerging evidence from their anti-inflammatory actions suggest that the mechanism of the cytotoxicity may be closely related to its anti-inflammatory activity. This review looks at the mechanisms of cryptolepis-induced cytotoxicity, its link with inflammation and its potential as anticancer agent. The elucidation of these interwoven mechanisms may be useful in the development of cryptolepine or other analogues as new anticancer agents. PMID:24391229

  7. In vitro genotoxicity of the West African anti-malarial herbal Cryptolepis sanguinolenta and its major alkaloid cryptolepine.

    Ansah, Charles; Khan, Ayesha; Gooderham, Nigel J

    2005-03-01

    Cryptolepine (CLP), the major alkaloid of the West African anti-malarial herbal Cryptolepis sanguinolenta (Periplocaceae) is a DNA intercalator that exhibits potent toxicity to a variety of mammalian cells in vitro. We have hypothesized that the DNA intercalating properties of cryptolepine could trigger genetic damage in mammalian cells. The objective of the present study was therefore to assess the ability of both cryptolepine (CLP) and the traditional anti-malarial formulation, the aqueous extract from the roots (CSE) to induce mutation at the hprt locus and micronuclei (MN) formation in V79, a Chinese hamster fibroblast cell line commonly used in genetic toxicity studies. CSE at a high concentration (50 microg/ml) induced an apparent significant ten fold increase in mutant frequency compared to vehicle control (mean of 38 versus 4 mutant clones/10(6) surviving cells) but, this concentration of CSE was very toxic (<15% cell survival). CLP did not appear to be mutagenic in the dosage range used (up to 2.5 microM, equivalent to 1.1 microg/ml). However, after 24h treatment of V79 cells both CSE and CLP induced a dose-dependent increase in micronuclei of 4.15% and 6.43% (25 microg/ml CSE and 2.5 microM, equivalent to 1.1 microg/ml CLP, respectively) compared to 0.36% in vehicle control. These results show that treatment of mammalian cells with CSE and CLP can lead to DNA damage and we suggest that the routine use of CSE and the potential use of CLP derivatives in malaria chemotherapy could carry a genotoxic risk. PMID:15664441

  8. Analysis of Ergot Alkaloids

    Colin Crews

    2015-06-01

    Full Text Available The principles and application of established and newer methods for the quantitative and semi-quantitative determination of ergot alkaloids in food, feed, plant materials and animal tissues are reviewed. The techniques of sampling, extraction, clean-up, detection, quantification and validation are described. The major procedures for ergot alkaloid analysis comprise liquid chromatography with tandem mass spectrometry (LC-MS/MS and liquid chromatography with fluorescence detection (LC-FLD. Other methods based on immunoassays are under development and variations of these and minor techniques are available for specific purposes.

  9. Biosynthesis of Monoterpenoid Indole Alkaloid Ajmaline Catalyzed by Novel Reductases

    2006-01-01

    @@ Introduction One of the major root alkaloids of the Indian medicinal plant Rauvolfia serpenlina Benth. Ex Kurz is named ajmaline. The enzymatic biosynthesisof this alkaloid has been studied for a long time by our group[1].

  10. RIA for indol alkaloids

    The technique of RIAs for indol alkaloids (ajmaline, ergotamine, ergocristine, ergometrine, and lysergic acid) is described, and applications for this RIA and the RIA for raubasine and serpentine are mentioned. The indol alkaloide RIAs are shown to be suitable both for alkaloid distribution measurements in Catharantus and Rauwolfia plants and C. purpurea sclerotia as well as for the selection of high-efficiency strains and the optimisation of cultures of plant tissues and saprophytic fungi. (orig./MG)

  11. Alkaloids in Marine Algae

    Ekrem Sezik; Aline Percot; Kasım Cemal Güven

    2010-01-01

    This paper presents the alkaloids found in green, brown and red marine algae. Algal chemistry has interested many researchers in order to develop new drugs, as algae include compounds with functional groups which are characteristic from this particular source. Among these compounds, alkaloids present special interest because of their pharmacological activities. Alkaloid chemistry has been widely studied in terrestrial plants, but the number of studies in algae is insignificant. In this review...

  12. Novel Euglenoid Derived Alkaloid

    National Oceanic and Atmospheric Administration, Department of Commerce — Disclosed herein is a purified toxin isolated from Euglena sanguinea. More specifically the toxin, termed euglenophycin, is an alkaloid having herbicidal and...

  13. Occurrence of halogenated alkaloids.

    Gribble, Gordon W

    2012-01-01

    Once considered to be isolation artifacts or chemical "mistakes" of nature, the number of naturally occurring organohalogen compounds has grown from a dozen in 1954 to >5000 today. Of these, at least 25% are halogenated alkaloids. This is not surprising since nitrogen-containing pyrroles, indoles, carbolines, tryptamines, tyrosines, and tyramines are excellent platforms for biohalogenation, particularly in the marine environment where both chloride and bromide are plentiful for biooxidation and subsequent incorporation into these electron-rich substrates. This review presents the occurrence of all halogenated alkaloids, with the exception of marine bromotyrosines where coverage begins where it left off in volume 61 of The Alkaloids. Whereas the biological activity of these extraordinary compounds is briefly cited for some examples, a future volume of The Alkaloids will present full coverage of this topic and will also include selected syntheses of halogenated alkaloids. Natural organohalogens of all types, especially marine and terrestrial halogenated alkaloids, comprise a rapidly expanding class of natural products, in many cases expressing powerful biological activity. This enormous proliferation has several origins: (1) a revitalization of natural product research in a search for new drugs, (2) improved compound characterization methods (multidimensional NMR, high-resolution mass spectrometry), (3) specific enzyme-based and other biological assays, (4) sophisticated collection methods (SCUBA and remote submersibles for deep ocean marine collections), (5) new separation and purification techniques (HPLC and countercurrent separation), (6) a greater appreciation of traditional folk medicine and ethobotany, and (7) marine bacteria and fungi as novel sources of natural products. Halogenated alkaloids are truly omnipresent in the environment. Indeed, one compound, Q1 (234), is ubiquitous in the marine food web and is found in the Inuit from their diet of whale

  14. Marine Indole Alkaloids

    Natalie Netz

    2015-08-01

    Full Text Available Marine indole alkaloids comprise a large and steadily growing group of secondary metabolites. Their diverse biological activities make many compounds of this class attractive starting points for pharmaceutical development. Several marine-derived indoles were found to possess cytotoxic, antineoplastic, antibacterial and antimicrobial activities, in addition to the action on human enzymes and receptors. The newly isolated indole alkaloids of marine origin since the last comprehensive review in 2003 are reported, and biological aspects will be discussed.

  15. Benzylisoquinoline alkaloid biosynthesis in opium poppy.

    Beaudoin, Guillaume A W; Facchini, Peter J

    2014-07-01

    Opium poppy (Papaver somniferum) is one of the world's oldest medicinal plants and remains the only commercial source for the narcotic analgesics morphine, codeine and semi-synthetic derivatives such as oxycodone and naltrexone. The plant also produces several other benzylisoquinoline alkaloids with potent pharmacological properties including the vasodilator papaverine, the cough suppressant and potential anticancer drug noscapine and the antimicrobial agent sanguinarine. Opium poppy has served as a model system to investigate the biosynthesis of benzylisoquinoline alkaloids in plants. The application of biochemical and functional genomics has resulted in a recent surge in the discovery of biosynthetic genes involved in the formation of major benzylisoquinoline alkaloids in opium poppy. The availability of extensive biochemical genetic tools and information pertaining to benzylisoquinoline alkaloid metabolism is facilitating the study of a wide range of phenomena including the structural biology of novel catalysts, the genomic organization of biosynthetic genes, the cellular and sub-cellular localization of biosynthetic enzymes and a variety of biotechnological applications. In this review, we highlight recent developments and summarize the frontiers of knowledge regarding the biochemistry, cellular biology and biotechnology of benzylisoquinoline alkaloid biosynthesis in opium poppy. PMID:24671624

  16. Cytotoxicity of Hymenocallis expansa alkaloids.

    Antoun, M D; Mendoza, N T; Ríos, Y R; Proctor, G R; Wickramaratne, D B; Pezzuto, J M; Kinghorn, A D

    1993-08-01

    From the bulbs and leaves of Hymenocallis expansa (Amaryllidaceae), three alkaloid constituents were identified: (+)-tazettine, (+)-hippeastrine, and (-)-haemanthidine. These alkaloids demonstrated significant cytotoxicity when tested against a panel of human and murine tumor cell lines. PMID:8229020

  17. CRINUM; AN ENDLESS SOURCE OF BIOACTIVE PRINCIPLES: A REVIEW. PART 1- CRINUM ALKALOIDS: LYCORINE-TYPE ALKALOIDS

    John Refaat*, Mohamed S. Kamel , Mahmoud A. Ramadan and Ahmed A. Ali

    2012-07-01

    Full Text Available Crinum is an important Amaryllidaceous plant thanks to the valuable biological and therapeutic activities of its chemical constituents, especially alkaloids. Many Crinum species have been commonly used in traditional medicines worldwide. Long ago, they have been subjected to extensive chemical, cytological and pharmacological investigations. Accordingly, this work comprehensively comprises both the alkaloidal and non-alkaloidal principles of Crinums isolated from 1950 and up to now, together with various biological and toxicological studies conducted on both the total extracts and individual compounds. As being a major common class of Crinum alkaloids, the current part of this review work highlights the lycorine-type alkaloids isolated so far from this plant in addition to their distribution in different Crinum species.

  18. Lycorine alkaloids from Hymenocallis littoralis.

    Lin, L Z; Hu, S F; Chai, H B; Pengsuparp, T; Pezzuto, J M; Cordell, G A; Ruangrungsi, N

    1995-11-01

    From Hymenocallis littoralis, one new alkaloid, named littoraline, together with 13 known lycorine alkaloids and one lignan, were isolated. The structure and NMR assignments of this new alkaloid were determined by 1D and 2D NMR techniques. Littoraline showed inhibitory activity of HIV reverse transcriptase, and lycorine and haemanthamine showed potent in vitro cytotoxicity. PMID:7492374

  19. Histrionicotoxin alkaloids finally detected in an ant

    Jones, Tappey H.; Adams, Rachelle Martha Marie; Spande, Thomas F.; Garraffo, H. Martin; Kaneko, Tetsuo; Schultz, Ted R.

    2012-01-01

    Workers of the ant Carebarella bicolor collected in Panama were found to have two major poison-frog alkaloids, cis- and trans-fused decahydroquinolines (DHQs) of the 269AB type, four minor 269AB isomers, two minor 269B isomers, and three isomers of DHQ 271D. For the first time in an ant, however......, the DHQs were accompanied by six histrionicotoxins (HTXs), viz., 283A, 285A, 285B, 285C, 287A, and 287D. This co-occurrence of the HTX and DHQ alkaloids is the usual pattern seen in dendrobatid frogs. This finding contrasts with our earlier study, where workers of a Brazilian ant, Solenopsis...... (Diplorhoptrum) sp., were found to have a very similar DHQ complex but failed to show HTXs. Several new DHQ alkaloids of MW 271 (named in the frog as 271G) are reported from the above ants that have both m/z 202 and 204 as major fragment ions, unlike the spectrum seen for the poison-frog alkaloid 271D, which has...

  20. Simple Indolizidine and Quinolizidine Alkaloids.

    Michael, Joseph P

    2016-01-01

    This review of simple indolizidine and quinolizidine alkaloids (i.e., those in which the parent bicyclic systems are in general not embedded in polycyclic arrays) is an update of the previous coverage in Volume 55 of this series (2001). The present survey covers the literature from mid-1999 to the end of 2013; and in addition to aspects of the isolation, characterization, and biological activity of the alkaloids, much emphasis is placed on their total synthesis. A brief introduction to the topic is followed by an overview of relevant alkaloids from fungal and microbial sources, among them slaframine, cyclizidine, Steptomyces metabolites, and the pantocins. The important iminosugar alkaloids lentiginosine, steviamine, swainsonine, castanospermine, and related hydroxyindolizidines are dealt with in the subsequent section. The fourth and fifth sections cover metabolites from terrestrial plants. Pertinent plant alkaloids bearing alkyl, functionalized alkyl or alkenyl substituents include dendroprimine, anibamine, simple alkaloids belonging to the genera Prosopis, Elaeocarpus, Lycopodium, and Poranthera, and bicyclic alkaloids of the lupin family. Plant alkaloids bearing aryl or heteroaryl substituents include ipalbidine and analogs, secophenanthroindolizidine and secophenanthroquinolizidine alkaloids (among them septicine, julandine, and analogs), ficuseptine, lasubines, and other simple quinolizidines of the Lythraceae, the simple furyl-substituted Nuphar alkaloids, and a mixed quinolizidine-quinazoline alkaloid. The penultimate section of the review deals with the sizable group of simple indolizidine and quinolizidine alkaloids isolated from, or detected in, ants, mites, and terrestrial amphibians, and includes an overview of the "dietary hypothesis" for the origin of the amphibian metabolites. The final section surveys relevant alkaloids from marine sources, and includes clathryimines and analogs, stellettamides, the clavepictines and pictamine, and bis

  1. Variation and evolution of alkaloid complex in yellow lupine (Lupinus luteus L.) during domestication

    Wiktor Święcicki; Konrad Jach

    2013-01-01

    A colection of 178 primitive and cultivated forms of Lupinus luteus was analysed with respect to composition and level of alkaloids in seeds. A considerable quantitative and qualitative variation in alkaloids was found in the analysed forms. All analysed primitive forms, not cultivated in Central Europe, contained gramine and lupinine; the majority had sparteine as well. Contrary to the common opinion, yellow lupine has three basic alkaloids, i.e. gramine, lupinine and sparteine. Moreover, a ...

  2. Automatic alkaloid removal system.

    Yahaya, Muhammad Rizuwan; Hj Razali, Mohd Hudzari; Abu Bakar, Che Abdullah; Ismail, Wan Ishak Wan; Muda, Wan Musa Wan; Mat, Nashriyah; Zakaria, Abd

    2014-01-01

    This alkaloid automated removal machine was developed at Instrumentation Laboratory, Universiti Sultan Zainal Abidin Malaysia that purposely for removing the alkaloid toxicity from Dioscorea hispida (DH) tuber. It is a poisonous plant where scientific study has shown that its tubers contain toxic alkaloid constituents, dioscorine. The tubers can only be consumed after it poisonous is removed. In this experiment, the tubers are needed to blend as powder form before inserting into machine basket. The user is need to push the START button on machine controller for switching the water pump ON by then creating turbulence wave of water in machine tank. The water will stop automatically by triggering the outlet solenoid valve. The powders of tubers are washed for 10 minutes while 1 liter of contaminated water due toxin mixture is flowing out. At this time, the controller will automatically triggered inlet solenoid valve and the new water will flow in machine tank until achieve the desire level that which determined by ultra sonic sensor. This process will repeated for 7 h and the positive result is achieved and shows it significant according to the several parameters of biological character ofpH, temperature, dissolve oxygen, turbidity, conductivity and fish survival rate or time. From that parameter, it also shows the positive result which is near or same with control water and assuming was made that the toxin is fully removed when the pH of DH powder is near with control water. For control water, the pH is about 5.3 while water from this experiment process is 6.0 and before run the machine the pH of contaminated water is about 3.8 which are too acid. This automated machine can save time for removing toxicity from DH compared with a traditional method while less observation of the user. PMID:24783795

  3. Anticholinesterase inhibitory activity of quaternary alkaloids from Tinospora crispa.

    Yusoff, Mashitah; Hamid, Hazrulrizawati; Houghton, Peter

    2014-01-01

    Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1), along with six known alkaloids-dihydrodiscretamine (2), columbamine (3), magnoflorine (4), N-formylannonaine (5), N-formylnornuciferine (6), and N-trans-feruloyltyramine (7). The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman's method. In the AChE inhibition assay, only columbamine (3) showed strong activity with IC50 48.1 µM. The structure-activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition. PMID:24448061

  4. Variation and evolution of alkaloid complex in yellow lupine (Lupinus luteus L. during domestication

    Wiktor Święcicki

    2013-12-01

    Full Text Available A colection of 178 primitive and cultivated forms of Lupinus luteus was analysed with respect to composition and level of alkaloids in seeds. A considerable quantitative and qualitative variation in alkaloids was found in the analysed forms. All analysed primitive forms, not cultivated in Central Europe, contained gramine and lupinine; the majority had sparteine as well. Contrary to the common opinion, yellow lupine has three basic alkaloids, i.e. gramine, lupinine and sparteine. Moreover, a large number of primitive forms showed traces of unidentified alkaline compounds with alkaloid characteristics. It appears that in the course of introduction of yellow lupine to central Europe, the composition and level of its alkaloids have been gradually changing. Their reproduction and natural selection remarkably decreased the number of forms containing gramine as well as the total level of alkaloids in seeds. Cross breeding and screening for low alkaloid bearing forms significantly decreased the total level of gramine as well as the number of forms containing gramine and almost entirely eliminated traces of unidentified alkaloids. One new form was found to have sparteine and only a little of lupinine (total level of alkaloids 0,04%.

  5. Biosynthesis of tylophora alkaloids

    Using labelled precursors, biosynthesis of the tylophora alkaloids, tylophorine, tylophorinidine and tylophorinide has been investigated in Tylophora asthmatica plants. The radioactive precursors, phenylalanine-2-14C, benzoic acid-1-14C, benzoic acid-ring 14C, acetate-2-14C, ornithine-5-14C, acetate-2-14C, ornithine-5-14C and cinnamic acid-2-14C were administered to the plants individually by wick technique. Tylophorine was isolated in each case and assayed for its radioactivity to find out the incorporation of the label into it. The results indicate that: (1) phenylalanine via cinnamic acid is an important precursor in the biosynthesis of tylophorine (2) orinithine participates in tylophorine biosynthesis via pyrroline and (3) tylophorinidine may be a direct precursor of tylophorine. (M.G.B.)

  6. Anticholinesterase Inhibitory Activity of Quaternary Alkaloids from Tinospora crispa

    Mashitah Yusoff

    2014-01-01

    Full Text Available Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1, along with six known alkaloids—dihydrodiscretamine (2, columbamine (3, magnoflorine (4, N-formylannonaine (5, N-formylnornuciferine (6, and N-trans-feruloyltyramine (7. The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman’s method. In the AChE inhibition assay, only columbamine (3 showed strong activity with IC50 48.1 µM. The structure–activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition.

  7. Genotoxicity of pyrrolizidine alkaloids.

    Chen, Tao; Mei, Nan; Fu, Peter P

    2010-04-01

    Pyrrolizidine alkaloids (PAs) are common constituents of many plant species around the world. PA-containing plants are probably the most common poisonous plants affecting livestock and wildlife. They can inflict harm to humans through contaminated food sources, herbal medicines and dietary supplements. Half of the identified PAs are genotoxic and many of them are tumorigenic. The mutagenicity of PAs has been extensively studied in different biological systems. Upon metabolic activation, PAs produce DNA adducts, DNA cross-linking, DNA breaks, sister chromatid exchange, micronuclei, chromosomal aberrations, gene mutations and chromosome mutations in vivo and in vitro. PAs induced mutations in the cII gene of rat liver and in the p53 and K-ras genes of mouse liver tumors. It has been suggested that all PAs produce a set of (+/-)-6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine-derived DNA adducts and similar types of gene mutations. The signature types of mutations are G : C --> T : A transversion and tandem base substitutions. Overall, PAs are mutagenic in vivo and in vitro and their mutagenicity appears to be responsible for the carcinogenesis of PAs. PMID:20112250

  8. Copper catalysed synthesis of indolylquinazolinone alkaloid bouchardatine

    Mayavan Viji; Rajagopal Nagarajan

    2014-07-01

    We describe the total synthesis of indolylquinazolinone alkaloid bouchardatine and some of the quinazolinone derivatives. The aerobic oxidation induced by copper(I) bromide, followed by Vilsmeier-Haack formylation gives the natural product bouchardatine alkaloid in good yield.

  9. FIVE NEW NORDITERPENOID ALKALOIDS FROM ACONITUM SINOMONTANUM

    FENG-PENG WANG; CHONG-SHENG PENG; XI-XIAN JIAN; DONG-LIN CHEN

    2001-01-01

    From the roots of A conitum sinomontanum, five new norditerpenoid alkaloids, sinomontanitines A (1) and B (2), sinomontanines A (3), B (4) and C (5), were isolated together with the known alkaloids lappaconitine (6) and ranaconitine (7), The structures of the new alkaloids were determined by spectral analysis.

  10. Antimicrobial activity of benzylisoquinoline alkaloids.

    Villar, A; Mares, M; Rios, J L; Canton, E; Gobernado, M

    1987-04-01

    The antimicrobial in vitro activity of 14 benzylisoquinoline alkaloids was investigated by agar diffusion and agar dilution methods against several genera of microorganisms that included Streptococcus, Staphylococcus, Bacillus, Lysteria, Escherichia, Salmonella, Klebsiella, Pseudomonas, Enterobacter, Serratia, Shigella, Mycobacterium and Candida. Anolobine was the most active compound against grampositive bacteria with MIC90 between 12 and 50 mg/l; less active were anonaine, lysicamine and liriodenine. All the alkaloids of the noraporphine and oxoaporphine groups, with the exception of isopiline, showed activity against Mycobacterium phlei (MIC 6-25 mg/l). Candida albicans ATCC26555 was inhibited by anonaine, nornantenine and xylopine (MIC 3-12 mg/l). None of the alkaloids tested had a significant activity against gramnegative rods. The action against susceptible microorganisms was bactericidal. PMID:3615557

  11. Simultaneous determination of the major isosteroidal alkaloids and their glucosides in the bulbs of Fritillaria by high performance liquid chromatography coupled with evaporative light scattering detection%HPLC-ELSD法测定贝母中异甾类生物碱及糖苷类成分的含量

    李萍; 曾令杰; 李松林; 毕志明; 林鸽

    2004-01-01

    目的建立同时测定贝母中5种异甾类生物碱--peimissine, imperialine, sinpeinine A, imperialine-3β-glucoside和yibeinoside A含量的HPLC分析方法.方法 C18柱;流动相:乙腈-水(含0.1%二乙胺);梯度洗脱,流速1.0 mL·min-1;检测器:Alltech 500蒸发光散射检测器(ELSD).结果线性范围为peimissine 13.1~288.2 mg·L-1(r2=0.997 5), imperialine-3β-glucoside 7.7~169.4 mg·L-1 (r2=0.999 3), yibeinoside A 7.3~160.6 mg·L-1 (r2=0.999 7), imperialine 16.5~363.0 mg·L-1 (r2=0.999 2), sinpeinine A 8.7~191.4 mg·L-1 (r2=0.994 2). 5个化合物的精密度和重现性RSD均<5%.结论本方法简便、有效、可行,可用于贝母中5种异甾类生物碱的含量测定.%Aim To establish an HPLC-ELSD method for the simultaneous determination of five major bioactive isosteroidal alkaloids and gluco-alkaloids in the bulbs of Fritillaria namely peimissine, imperialine, sinpeinine A, imperialine-3β-glucoside and yibeinoside A. Methods A Nova-Pak C18 column (150 mm×3.9 mm ID) was used. The chromatography was carried out with a linear gradient programming. The mobile phase was acetonitrile-water (containing 0.1% diethylamine) and the flow rate was 1.0 mL*min-1. Results The linear range of peimissine was 13.1-288.2 mg*L-1 (r2=0.997 5), imperialine-3β-glucoside 7.7-169.4 mg·L-1 (r2=0.999 3), yibeinoside A 7.3-160.6 mg·L-1 (r2=0.999 7), imperialine 16.5-363.0 mg·L-1 (r2=0.999 2), sinpeinine A 8.7-191.4 mg·L-1 (r2=0.994 2). Conclusion The method is accurate with overall intra- and inter-day variation less than 5% and recovery more than 95%. The method was successfully applied to analyze five major bioactive alkaloids and gluco-alkaloids in three Fritillaria bulbs.

  12. Molecular Toxicology of Pyrrolizidine Alkaloids

    Kim, Hea-Young

    1994-01-01

    Pyrrolizidine alkaloids are cytotoxic, carcinogenic, and anti-carcinogenic in vivo and in vitro, and they produce many hazardous effects in humans and animals. Pyrrolizidine alkaloids (PAs) also cross-link with DNA and/or protein. However, whether such cross-linking is important to the toxic action of PAs is not known. In addition, the exact mechanism underlying these DNA cross-links or cytotoxicity is also not clear. In three separate studies, I characterized the nature of PA-induced DNA ...

  13. Depth-related alkaloid variation in Mediterranean Aplysina sponges.

    Putz, Annika; Kloeppel, Anne; Pfannkuchen, Martin; Brümmer, Franz; Proksch, Peter

    2009-01-01

    Total amounts and patterns of bromoisoxazoline alkaloids of Aplysina sponges from Croatia (Mediterranean Sea) were analyzed along an underwater slope ranging from 1.8 to 38.5 m. Total amounts of alkaloids varied from sample to sample and showed no correlation with depth. In contrast, striking differences of alkaloid patterns were found between sponges from shallow sites (1.8-11.8 m) and those collected from deeper sites (11.8-38.5 m). Sponges from shallow depths consistently exhibited alkaloid patterns typical for Aplysina aerophoba with aerophobin-2 (2) and isofistularin-3 (3) as main constituents. Sponges from deeper sites (below 11.8 m) resembled Aplysina cavernicola with aerothionin (4) and aplysinamisin-1 (1) as major compounds. The typical A. cavernicola pigment 3,4-dihydroxyquinoline-2-carboxylic acid (6), however, could not be detected in A. aerophoba sponges but was replaced by the A. aerophoba pigment uranidine (5) which appeared to be present in all sponge samples analyzed. During transplantation experiments sponges from sites below 30 m featuring the A. cavernicola chemotype of bromoisoxazoline alkaloids were translocated to shallower habitats (10 m). The alkaloid patterns in transplanted sponges were found to be stable over a period of 12 months and unaffected by this change in depth. In a further experiment, clones of Aplysina sponges from shallow depths of 5-6 m resembling the A. aerophoba chemotype were either kept in situ under natural light conditions or artificially shaded by excluding photosynthetically active radiation (PAR). Neither 4 nor 1 were detected in artificially shaded sponges over an observation period of 12 months. In summary, two chemically distinct types of Aplysina sponges were discovered in this study that proved to be remarkably stable with regard to the bromoisoxazoline patterns and unaffected either by changing the light conditions or depth. It is not clear presently whether the Aplysina sponges collected from depths Aplysina

  14. Hypolipidemic Effects of Alkaloids from Rhizoma Coptidis in Diet-Induced Hyperlipidemic Hamsters.

    He, Kai; Kou, Shuming; Zou, Zongyao; Hu, Yinran; Feng, Min; Han, Bing; Li, Xuegang; Ye, Xiaoli

    2016-05-01

    This study was conducted to evaluate the antihyperlipidemic activity of five major alkaloids in Rhizoma Coptidis using high-fat- and high-cholesterol-induced hyperlipidemic hamsters. Hyperlipidemic hamsters were treated with coptisine, berberine, jatrorrhizine, palmatine, epiberberine, and total Rhizoma Coptidis alkaloids with a dose of 46.7 mg/kg × day for 140 days. Serum total cholesterol, triglyceride, high-density lipoprotein cholesterol, low-density lipoprotein cholesterol, and total bile acids were examined after alkaloid treatment. The results showed that all therapy agents prevented body weight gain, reduced the serum total cholesterol, and increased the high-density lipoprotein cholesterol of hamsters. Berberine, jatrorrhizine, and total Rhizoma Coptidis alkaloids decreased the triglyceride level in hyperlipidemic hamsters, while coptisine, jatrorrhizine, palmatine, and total Rhizoma Coptidis alkaloids significantly suppressed the elevation of the low-density lipoprotein cholesterol level. The fecal excretion of bile acids was significantly elevated by berberine, coptisine, jatrorrhizine, palmatine, total Rhizoma Coptidis alkaloids, and orlistat. Notably, total Rhizoma Coptidis alkaloids possess a much stronger lipid-lowering effect than the pure Rhizoma Coptidis alkaloids. Quantitative reverse transcription-polymerase chain reaction analyses revealed that Rhizoma Coptidis alkaloids could retard the synthesis of cholesterol by downregulating the mRNA expression of 3-hydroxy-3-methyl glutaryl coenzyme A reductase and accelerate the clearance of lipids by upregulating the low-density lipoprotein receptor, cholesterol 7α-hydroxylase, and uncoupling protein-2 expression. These findings highlight the critical role of Rhizoma Coptidis alkaloids in hyperlipidemia treatment. Thus, they need to be considered in future therapeutic approaches. PMID:26848702

  15. Determination of Ergot Alkaloids: Purity and Stability Assessment of Standards and Optimization of Extraction Conditions for Cereal Samples

    Krska, R.; Berthiller, F.; Schuhmacher, R.; Nielsen, Kristian Fog; Crews, C.

    2008-01-01

    Results obtained from a purity study on standards of the 6 major ergot alkaloids ergometrine, ergotamine, ergosine, ergocristine, ergocryptine, and ergocornine and their corresponding epimers are discussed. The 6 ergot alkaloids studied have been defined by the European Food Safety Authority as t...

  16. Quaternary alkaloids of tinospora species.

    Bisset, N G; Nwaiwu, J

    1983-08-01

    The occurrence of quaternary alkaloids in TINOSPORA (and PARABAENA) species (Menispermaceae) has been studied. The main components were generally the protoberberine bases berberine and palmatine, with jatrorrhizine an occasional minor constituent, and the aporphine base magnoflorine. Choline was also often present. Only magnoflorine was detected in the PARABAENA material examined. PMID:17404996

  17. Lycopodium alkaloids from Palhinhaea cernua

    Zhao, Fu-Wei [Graduate University of Chinese Academy of Sciences, Beijing (China); Luo, Ji-Feng; Wang, Yue-Hu, E-mail: wangyuehu@mail.kib.ac.cn [Key Laboratory of Economic Plants and Biotechnology, Kunming Institute of Botany, Chinese Academy of Sciences (China); Sun, Qian-Yun; Yang, Fu-Mei [Key Laboratory of Chemistry for Natural Products, Guizhou Province and Chinese Academy of Sciences (China); Liu, Fang [College of Landscape and Horticulture, Yunnan Agricultural University (China); Long, Chun-Lin, E-mail: long@mail.kib.ac.cn [College of Life and Environmental Sciences, Minzu University of China, Beijing, (China)

    2012-07-01

    Two new Lycopodium alkaloids, acetyllycoposerramine M and palcernine A were isolated from whole plant extracts of Palhinhaea cernua L. together with ten previously identified compounds. The structures of the new compounds were elucidated by spectroscopic methods and single-crystal X-ray diffraction analyses using the Flack parameter. (author)

  18. The distribution of inole alkaloids in different organs of Catharanthus roseus G. Don. (Vinca rosea L

    Hassan Ebrahimzadeh

    1996-08-01

    Full Text Available The study of alkaloid extract of the leaf of Vinca rosea by TLC showed the existence of 13 bands, 7 bands of them were: Serpentine, Vincristine, Vinblastine, Ajmaline, Catharantine, Vindoline and Ajmalicine. The existence of these 7 alkaloids was confirmed in the young leaves, old leaves and the roots of the plant by HPLC. Furthermore, two alkaloids with the short retention times and one alkaloid with the medium retention time in the young leaf, three alkaloids with the short retention time and one alkaloid with long retention time in the old leaf, and one alkaioid with the short retention time and two other alkaloids with the long retention times in the root, were observed."nThe study of absorption spectrum of alkaloid extract and its comparison with absorption spectrum of ajmalicine showed that the latter can be used for drawing a standard curve and detecting the amount of total alkaloids. The total alkaloids in fresh root, old leaf and young leaf were 2.1 mg , 1.3 mg and 0.9 mg/g respectively, Vindoline and Catharantine were major alkaloids in all of them. However, their amount were more in the root (1.2 mg/ g of fresh material, 0.85 in the old leaf and 0.38 in the young leaf. Vinblastine existed in all three samples but its amount was more in the root {0.22 mg per gramme of the fresh material in the root, 0.26 in the young leaf and 0.003 in the old leaf."nAjmalicine was detected only in the leaf and its amount was more in young leaf than the old leaf (0.141 mg/g of the fresh material in the young leaf and 0.013 in the old leaf. Serpentine was seen in all of the studied organs but its amount was more in the young leaf than other organs (0.192 mg/ g of the fresh material in the young leaf, 0.11 in the root and 0.07 in the old leaf. Ajmaline existed in all of the organs in minute amount but in the old leaf was more (0 .07 mg/g of the fresh material in the old !eaf,0.044 in the young leaf and 0.04 in the root . The percentage of unknown

  19. Determination of Ephedrine Alkaloids in Botanicals and Dietary Supplements by HPLC-UV: Collaborative Study

    Roman, Mark C.; Gray, D; Luo, G.; McClanahan, R.; Perez, R.; Roper, C; Roscoe, V.; Shevchuk, C.; Suen, E.; Sullivan, D.; Walther, H.J.

    2004-01-01

    An international collaborative study was conducted of a high-performance liquid chromatography (HPLC)-UV method for the determination of the major (ephedrine [EP] and pseudoephedrine [PS]) and minor (norephedrine [NE], norpseudoephedrine [NP], methylephedrine [ME], and methylpseudoephedrine [MP]) alkaloids in selected dietary supplements representative of the commercially available products. Ten collaborating laboratories determined the ephedrine-type alkaloid content in 8 blind replicate sam...

  20. Poisoning of chickens and ducks by pyrrolizidine alkaloids of Heliotropium europaeum.

    Pass, D A; Hogg, G G; Russell, R G; Edgar, J A; Tence, I M; Rikard-Bell, L

    1979-06-01

    The disease produced by feeding chickens and ducks a commercial poultry feed containing heliotrine and lasiocarpine, pyrrolizidine alkaloids of Heliotropium europaeum, is described. Illthrift, ascites and degenerative lesions in the liver were the major findings. Similar lesions occurred in chickens fed a diet containing H. europaeum. The source of the alkaloids in commercial poultry feed was probably the seeds of H. europaeum harvested with wheat. PMID:518422

  1. Alkaloid-Containing Plants Poisonous to Cattle and Horses in Europe

    Cristina Cortinovis; Francesca Caloni

    2015-01-01

    Alkaloids, nitrogen-containing secondary plant metabolites, are of major interest to veterinary toxicology because of their occurrence in plant species commonly involved in animal poisoning. Based on epidemiological data, the poisoning of cattle and horses by alkaloid-containing plants is a relatively common occurrence in Europe. Poisoning may occur when the plants contaminate hay or silage or when forage alternatives are unavailable. Cattle and horses are particularly at risk of poisoning by...

  2. Workers and alate queens of Solenopsis geminata share qualitatively similar but quantitatively different venom alkaloid chemistry

    Qun-Hui eShi

    2015-07-01

    Full Text Available Solenopsis geminata group (Hymenoptera: Formicidae encompasses ant species commonly called fire ants because of their painful sting. The many physiological effects of the venom are caused by 2-methyl-6-alkyl and/or alkenylpiperidine alkaloids. The variation in piperidine alkaloid structures has useful taxonomic characters. The most well studied Solenopsis species is S. invicta, which was accidentally imported into the USA in the 1930s from South America. It quickly spread throughout the southern USA and is now a major invasive pest ant in the USA and in other parts of the world. Interestingly, the invasive S. invicta has largely displaced a native USA fire ant, S. geminata, from the southern USA. We explore the possibility that differences in venom chemistry could be correlated with this displacement. The cis and trans alkaloids from body extracts of workers and alate queens of S. geminata were separated by silica gel chromatography, identified, and quantitated by GC-MS analysis. Both workers and alate queens produce primarily cis- and trans-2-methyl-6-n-undecyl-piperidines, as well as other minor alkaloid components. Imported fire ant, S. invicta, alate queens produce the same alkaloids as S. geminata alate queens, but in contrast S. invicta workers produce piperidine alkaloids with longer side chains, which are purported to be physiologically more effective. These results are discussed in relation to the evolutionary progression of fire ant venom alkaloids and displacement of S. geminata by S. invicta in the USA.

  3. Hepatotoxic pyrrolizidine alkaloids in pollen and drying-related implications for commercial processing of bee pollen.

    Boppré, Michael; Colegate, Steven M; Edgar, John A; Fischer, Ottmar W

    2008-07-23

    Using HPLC-ESI-MS, several saturated and 1,2-dehydropyrrolizidine alkaloids were detected, mainly as their N-oxides, in fresh pollen collected from flowers of the pyrrolizidine alkaloid-producing plants Echium vulgare, E. plantagineum, Senecio jacobaea, S. ovatus, and Eupatorium cannabinum, and/or pollen loads from bees (bee pollen) that foraged on those plants. A major alkaloidal metabolite in S. ovatus was tentatively identified, using its mass spectrometric data and biogenic considerations, as the previously unreported, saturated alkaloid, 2-hydroxysarracine. Heating had very little effect on the 1,2-dehydropyrrolizidine alkaloids and their N-oxides from a variety of sources. Considered in conjunction with international concerns about the adverse effects of these alkaloids, the results strongly indicate a need for monitoring pollen supplies intended for human consumption, at least until conditions for processing and/or selection are clearly defined such as to significantly reduce the hepatotoxic (and potentially carcinogenic and genotoxic) pyrrolizidine alkaloid content of bee pollen. PMID:18553916

  4. Bacterial Alkaloids Prevent Amoebal Predation.

    Klapper, Martin; Götze, Sebastian; Barnett, Robert; Willing, Karsten; Stallforth, Pierre

    2016-07-25

    Bacterial defense mechanisms have evolved to protect bacteria against predation by nematodes, predatory bacteria, or amoebae. We identified novel bacterial alkaloids (pyreudiones A-D) that protect the producer, Pseudomonas fluorescens HKI0770, against amoebal predation. Isolation, structure elucidation, total synthesis, and a proposed biosynthetic pathway for these structures are presented. The generation of P. fluorescens gene-deletion mutants unable to produce pyreudiones rendered the bacterium edible to a variety of soil-dwelling amoebae. PMID:27294402

  5. Pyrrolizidine alkaloids of senecio sp from Peru

    Liliana Ruiz Vásquez and Matías Reina Artiles

    2011-01-01

    Full Text Available Six pyrrolizidine alkaloids (PAs (two saturated macrocyclic, three unsaturated macrocyclic and one unsaturated seco-macrocyclic were isolated from native Peruvian Senecio species. The structures of these alkaloids were established by a complete NMR spectroscopic analysis, chemical transformations and comparison of their NMR data with those published for similar alkaloids. Three PAs were then tested for antifungal activity against Fusarium moniliforme, F. (Sheldon, F. oxysporum fs. lycopersici (Scheldt and F. solani (Mart, no significant activity being observed.

  6. Pyrrolizidine alkaloids of Senecio sp from Peru

    Six pyrrolizidine alkaloids (PAs) (two saturated macrocyclic, three unsaturated macrocyclic and one unsaturated seco-macrocyclic) were isolated from native Peruvian Senecio species. The structures of these alkaloids were established by a complete NMR spectroscopic analysis, chemical transformations and comparison of their NMR data with those published for similar alkaloids. Three PAs were then tested for antifungal activity against Fusarium moniliforme, F. (Sheldon), F. oxysporum fs. lycopersici (Scheldt) and F. solani (Mart), no significant activity being observed. (author)

  7. Pyrrolizidine alkaloids of Senecio sp from Peru

    Ruiz Vasquez, Liliana; Reina Artiles, Matias [Instituto de Productos Naturales y Agrobiologia, CSIC, Tenerife (Spain); Gonzalez Coloma, Azucena [Instituto de Ciencias Agrarias (ICA), CSIC, Madrid (Spain); Cabrera Perez, Raimundo [Universidad de La Laguna (ULL), Tenerife (Spain). Unidad de Fitopatologia, Facultad de Biologia; Ruiz Mesia, Lastenia [Universidad Nacional de la Amazonia Peruana (LIPNAA-UNAP), AA.HH. Nuevo San Lorenzo, San Juan, Iquitos (Peru). Lab. de Investigacion en Productos Naturales Antiparasitarios de la Amazonia

    2011-07-01

    Six pyrrolizidine alkaloids (PAs) (two saturated macrocyclic, three unsaturated macrocyclic and one unsaturated seco-macrocyclic) were isolated from native Peruvian Senecio species. The structures of these alkaloids were established by a complete NMR spectroscopic analysis, chemical transformations and comparison of their NMR data with those published for similar alkaloids. Three PAs were then tested for antifungal activity against Fusarium moniliforme, F. (Sheldon), F. oxysporum fs. lycopersici (Scheldt) and F. solani (Mart), no significant activity being observed. (author)

  8. Halogenated indole alkaloids from marine invertebrates.

    Pauletti, Patrícia Mendonça; Cintra, Lucas Silva; Braguine, Caio Guedes; da Silva Filho, Ademar Alves; Silva, Márcio Luís Andrade E; Cunha, Wilson Roberto; Januário, Ana Helena

    2010-01-01

    This review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates. Meridianins and related compounds (variolins, psammopemmins, and aplicyanins), as well as aplysinopsins and leptoclinidamines, are focused on. A compilation of the (13)C-NMR spectral data of these selected natural indole alkaloids is also provided. PMID:20559487

  9. Halogenated Indole Alkaloids from Marine Invertebrates

    Ana Helena Januário

    2010-04-01

    Full Text Available This review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates. Meridianins and related compounds (variolins, psammopemmins, and aplicyanins, as well as aplysinopsins and leptoclinidamines, are focused on. A compilation of the 13C-NMR spectral data of these selected natural indole alkaloids is also provided.

  10. Halogenated Indole Alkaloids from Marine Invertebrates

    Ana Helena Januário; Wilson Roberto Cunha; Márcio Luís Andrade e Silva; Ademar Alves da Silva Filho; Caio Guedes Braguine; Lucas Silva Cintra; Patrícia Mendonça Pauletti

    2010-01-01

    This review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates. Meridianins and related compounds (variolins, psammopemmins, and aplicyanins), as well as aplysinopsins and leptoclinidamines, are focused on. A compilation of the 13C-NMR spectral data of these selected natural indole alkaloids is also provided.

  11. Iboga-Type Alkaloids from Ervatamia officinalis.

    Tang, Ben-Qin; Wang, Wen-Jing; Huang, Xiao-Jun; Li, Guo-Qiang; Wang, Lei; Jiang, Ren-Wang; Yang, Ting-Ting; Shi, Lei; Zhang, Xiao-Qi; Ye, Wen-Cai

    2014-08-22

    Seven new iboga-type alkaloids, ervaoffines A-D (1-4), (7S)-3-oxoibogaine hydroxyindolenine (5), ibogaine-5,6-dione (6), and 19-epi-5-oxovoacristine (7), and 10 known alkaloids were isolated from Ervatamia officinalis. The absolute configurations of 1-7 were determined through X-ray diffraction and electronic circular dichroism (ECD) analyses. Ervaoffines A and B represent the first iboga-type pseudoindoxyl alkaloids in which the C-2 spiro carbon configuration is opposite to that of other members of this class, such as iboluteine (8). The relationship between the absolute configuration of the spiro carbons and the Cotton effect in the ECD spectrum is established for the first time for iboga-type pseudoindoxyl and oxindole alkaloids. Additionally, a plausible biogenetic pathway for these alkaloids is proposed. PMID:25093992

  12. Aporphine and tetrahydroprotoberberine alkaloids from the leaves of Guatteria friesiana (Annonaceae) and their cytotoxic activities

    Costa, Emmanoel Vilaca; Cruz, Pedro Ernesto O. da, E-mail: emmanoelvc@gmail.com [Universidade Federal de Sergipe (UFSE), Sao Cristovao, SE (Brazil). Departamento de Quimica; Marques, Francisco A.; Barison, Andersson; Maia, Beatriz Helena L.N.S. [Universidade Federal do Parana (UFPR), Curitiba, PR (Brazil). Centro Politecnico. Departamento de Quimica; Pinheiro, Maria Lucia B. [Universidade Federal do Amazonas (UFAM), Manaus, AM (Brazil). Departamento de Quimica; Ruiz, Ana Lucia T.G.; Marchetti, Gabriela M.; Carvalho, Joao Ernesto de [Universidade Estadual de Campinas (UNICAMP), SP (Brazil). Centro Pluridisciplinar de Pesquisas Quimicas, Biologicas e Agricolas. Divisao de Farmacologia e Toxicologia

    2013-05-15

    Phytochemical investigation of the leaves of Guatteria friesiana (Annonaceae) afforded three new isoquinoline alkaloids, 13-hydroxy-discretinine, 6,6a-dehydroguatteriopsiscine and 9-dehydroxy-1-methoxy-dihydroguattouregidine. Eight known alkaloids were also isolated, 13-hydroxy-2,3,9,10-tetramethoxyprotoberberine, guatteriopsiscine, lysicamine, liriodenine, atherospermidine, lanuginosine, 7,8-dihydro-8-hydroxypalmatine and palmatine. 13-Hydroxy- 2,3,9,10-tetramethoxyprotoberberine was only obtained by synthesis and is being reported as a natural product for the first time. The structures of the isolated alkaloids were established by extensive analysis of 1D and 2D nuclear magnetic resonance (NMR) and mass spectrometric (MS) data, as well as by comparison with data reported in the literature. The in vitro cytotoxic activity of the major alkaloids was evaluated against tumor and non-tumor cell lines. All of the alkaloids evaluated were determined to be inactive based on National Cancer Institute (NCI/USA) criteria. However, the alkaloid palmatine exhibited a cytostatic effect on MCF-7 (breast) and U251 (glioma) human tumor cell lines, with GI{sub 50} values lower than 20.0 Greek-Small-Letter-Mu mol L{sup -}1 (10.5and 16.2 Greek-Small-Letter-Mu molL{sup -1}, respectively), suggesting a selective cytotoxic action (author)

  13. Rapid Screening of Ergot Alkaloids in Sclerotia by MALDI-TOF Mass Spectrometry.

    Sivagnanam, Kumaran; Komatsu, Emy; Patrick, Susan; Rampitsch, Christoph; Perreault, Hélène; Gräfenhan, Tom

    2016-07-01

    Ergot is a common disease of wheat and other cereal grains that is predominantly caused by Claviceps purpurea in the field, often affecting crop yield in addition to the environment. Infected grain can be contaminated with dark sclerotia, which contain fungal metabolites such as ergot alkaloids. The occurrence of ergot alkaloids in cereal grain is a major health concern for humans and livestock. Effective and rapid screening of these mycotoxins is crucial for producers, processors, and consumers of cereal-based food and feed grain. Established methods of ergot alkaloid screening based on LC-MS or GC-MS require laborious processes. A novel method using matrix-assisted laser desorption ionization (MALDI)-time-of-flight (TOF) MS was developed to identify four ergot alkaloids. Using dihydroxybenzoic acid as the matrix, ergosine, ergocornine, ergocryptine, and ergocristine were readily detected in individual sclerotia of C. purpurea. The accuracy of the identified ergot alkaloids was further confirmed by tandem MS analysis. MALDI-TOF MS is suitable for high-throughput screening of ergot alkaloids because it permits rapid and accurate identification, simple sample preparation, and no derivatization or chromatographic separation. PMID:27455930

  14. Comparison of Indoie-aikafoids in Vinca major L, V. minor L. and Vinca herbacea L

    Hassan Ebrahimzadeh

    1995-08-01

    Full Text Available Eleven main alkaloids was observed in the leaf of Vinca major, of these, eight is determined: Ajmaline,Vindo[ine, Catharantine, Serpentine, Vincamine, Vincristine, Ajmalicine and Vinblastine. The known main alkaloids formed totally 41.5% and the unknown main alkaloids about 50.6% of the total alkaloid. The amount of the total alkaloid was 2.3 mg per gr of the fresh weight. Vincamine which was not present in V.rosea, was seen in V.major (8.2%."nFurthermore, Vindoline, Catharantine and Serpentine had a lesser amount in V.major, in comparison with V.rosea, respectively 3.7%, 18.1% and 6.3%. The mentioned eight known alkaloids and nine unknown alkaloids was observed in the leaf of V.minor. The known main alkaloids formed totally 37.1% and the unknown main alkaloids about 56.4% of the total alkaloids. The amount of the total alkaloid was 0.5 mg per gr of the fresh weight.All of alkaloids had a lesser amount in V.major, in comparison with alkaloids of similar to itself. Vincamine had the most percent (16.1% and Vindoline (6.6% and Serpentine (7.8% were set after it."nIt was observed, in addition to mentioned eight known alkaloids, eight unknown alkaloids in the leaf of V. herbacea. The known main alkaloids formed totaly 52.5% and the unknown main alkaloids about 41.5% of the total alkaloid."nThe amount of the total alkaloid was 4.7 mg per gr of the fersh weight of the leaf. This amount is more than the amount which was observed in V.rosea (0.75, V.major (2,3, and V.minor (0.5.Vincamine had a high percent (39.8 and Serpentine a low percent (8.7. In short, V.herbacea is a good source for Vincamine and Serpentine, specially the last compound which easily is changed into Ajmalicine. V. rosea and V.major are a good source for Vindoline and Catharantine that can be used for providing Vinblastine and Vincristine.

  15. Widespread Chemical Detoxification of Alkaloid Venom by Formicine Ants.

    LeBrun, Edward G; Diebold, Peter J; Orr, Matthew R; Gilbert, Lawrence E

    2015-10-01

    The ability to detoxify defensive compounds of competitors provides key ecological advantages that can influence community-level processes. Although common in plants and bacteria, this type of detoxification interaction is extremely rare in animals. Here, using laboratory behavioral assays and analyses of videotaped interactions in South America, we report widespread venom detoxification among ants in the subfamily Formicinae. Across both data sets, nine formicine species, representing all major clades, used a stereotyped grooming behavior to self-apply formic acid (acidopore grooming) in response to fire ant (Solenopsis invicta and S. saevissima) venom exposure. In laboratory assays, this behavior increased the survivorship of species following exposure to S. invicta venom. Species expressed the behavior when exposed to additional alkaloid venoms, including both compositionally similar piperidine venom of an additional fire ant species and the pyrrolidine/pyrroline alkaloid venom of a Monomorium species. In addition, species expressed the behavior following exposure to the uncharacterized venom of a Crematogaster species. However, species did not express acidopore grooming when confronted with protein-based ant venoms or when exposed to monoterpenoid-based venom. This pattern, combined with the specific chemistry of the reaction of formic acid with venom alkaloids, indicates that alkaloid venoms are targets of detoxification grooming. Solenopsis thief ants, and Monomorium species stand out as brood-predators of formicine ants that produce piperidine, pyrrolidine, and pyrroline venom, providing an important ecological context for the use of detoxification behavior. Detoxification behavior also represents a mechanism that can influence the order of assemblage dominance hierarchies surrounding food competition. Thus, this behavior likely influences ant-assemblages through a variety of ecological pathways. PMID:26385230

  16. Bioactive acridone alkaloids from Swinglea glutinosa.

    Weniger, B; Um, B H; Valentin, A; Estrada, A; Lobstein, A; Anton, R; Maillé, M; Sauvain, M

    2001-09-01

    A new prenylated acridone alkaloid, 1,3,5-trihydroxy-2,8-bis(3-methylbut-2-enyl)-10-methyl-9-acridone (1), was isolated from the stembark of Swinglea glutinosa, along with three known acridone alkaloids, 5-hydroxynoracronycine (2), 1,3,5-trihydroxy-4-methoxy-2-(3-methylbut-2-enyl)-10-methyl-9-acridone (3), and 1,3,5-trihydroxy-4-methoxy-10-methylacridone (4). The isolated alkaloids were assessed in vitro against chloroquine-sensitive and -resistant Plasmodium falciparum strains and for cytotoxicity using HeLa cells. PMID:11575960

  17. Amount species of halucinogenic mushrooms contain major psychoactive alkaloid psilocybin

    Rambousek, Lukáš; Páleníček, T.; Bubeníková-Valešová, V.; Stuchlík, Aleš; Valeš, Karel

    2008-01-01

    Roč. 12, Suppl.1 (2008), s. 45-45. ISSN 1211-7579. [Česko-slovenská psychofarmakologická konference /50./. 09.01.2008-13.01.2008, Lázně Jeseník] R&D Projects: GA MZd(CZ) NR9178; GA ČR(CZ) GA309/07/0341; GA MŠk(CZ) 1M0517 Institutional research plan: CEZ:AV0Z50110509 Keywords : cpo1 * psilocin * rat * memory Subject RIV: FH - Neurology

  18. Quantitative 1H NMR metabolite profiling as a functional genomics platform to investigate alkaloid biosynthesis in natural mutants of opium poppy

    Opium poppy (Papaver somniferum) produces a diverse array of bioactive benzylisoquinoline alkaloids and has emerged as a versatile model system to study plant alkaloid metabolism. The plant is widely cultivated as the only commercial source of the narcotic analgesics morphine and codeine. Variations in plant secondary metabolism as a result of genetic diversity are often associated with perturbations in other metabolic pathways. As part of a functional genomics platform, we have used 1H NMR metabolite profiling for the analysis of primary and secondary metabolism in opium poppy. Aqueous and chloroform extracts of six different opium poppy cultivars were subjected to chemometric analysis. Principle component analysis of the 1H NMR spectra for latex extracts clearly distinguished two natural mutants, including a low alkaloid variety, and a high-thebaine, low-morphine cultivar. Distinction was also made between pharmaceutical-grade opium poppy cultivars and a condiment variety. Such phenotypic differences were not observed in root extracts. Loadings plots confirmed that morphinan alkaloids contributed predominantly to the variance in latex extracts. Quantification of 34 root and 21 latex metabolites, performed using Chenomx NMR Suite v. 4.6, showed major differences in the accumulation of specific alkaloids in the latex of the low-alkaloid and high-thebaine, low-morphine mutants. However, few significant differences were found in the levels of other metabolites, indicating that the variation was highly specific for alkaloid metabolism. Exceptions included the accumulation of the alkaloid precursor tyramine in the low-alkaloid cultivar, in addition to altered levels of sucrose, select amino acids and malate. Real-time PCR analysis of 42 genes involved in primary and secondary metabolism showed differential gene expression mainly associated with alkaloid biosynthesis. Reduced alkaloid levels in the condiment variety were associated the reduced abundance of transcripts

  19. Sex-related differences in alkaloid chemical defenses of the dendrobatid frog Oophaga pumilio from Cayo Nancy, Bocas del Toro, Panama.

    Saporito, Ralph A; Donnelly, Maureen A; Madden, Anne A; Garraffo, H Martin; Spande, Thomas F

    2010-03-26

    Poison frogs contain an alkaloid-based chemical defense that is sequestered directly from a diet of alkaloid-containing arthropods. Geographic and temporal variation in alkaloid defense is common in poison frogs and is generally attributed to differences in the availability of alkaloid-containing arthropods. Variable chemical defense in poison frogs may have important consequences for predator-prey interactions, requiring a full understanding of the factors involved in explaining such variation. In the present study, we examine alkaloid variation in the dendrobatid poison frog Oophaga pumilio between males and females on Cayo Nancy (Isla Solarte), located in the Bocas del Toro archipelago of Panama. On average, females contained a significantly larger number and quantity of alkaloids when compared to males. Alkaloid composition varied significantly between males and females, illustrating that chemical defense in this population of O. pumilio is sex-dependent. The variation in alkaloids between sexes is attributed to differences in feeding and behavior between males and females. The majority of alkaloids present in the skin of O. pumilio appear to be of oribatid mite origin, supporting the importance of these dietary arthropods in the chemical defense of poison frogs. PMID:20030363

  20. Synthesis of the isoquinoline alkaloid, crispine C

    Blair, A.; Stevenson, L; Sutherland, A

    2012-01-01

    The first total synthesis of the isoquinoline alkaloid, crispine C is described in seven steps using a Henry reaction and the Pictet–Gams variant of the Bischler–Napieralski reaction to effect the key transformations.

  1. A novel approach to quinazoline alkaloids

    Chmela, Václav; Amatov, Tynchtyk; Jahn, Ullrich

    Praha: Czech Chemical Society, 2015. s. 82. [Liblice 2015. Advances in Organic , Bioorganic and Pharmaceutical Chemistry /50./. 06.11.2015-08.11.2015, Olomouc] Institutional support: RVO:61388963 Keywords : quinazoline * alkaloids Subject RIV: CC - Organic Chemistry

  2. In vitro anticholinesterase activity of various alkaloids.

    Orhan, Ilkay; Naz, Qamar; Kartal, Murat; Tosun, Fatma; Sener, Bilge; Choudhary, M Iqbal

    2007-01-01

    In the current study, a number of alkaloids including retamine, cytisine, and sparteine (quinolizidine-type), yohimbine and vincamine (indole-type), scopolamine and atropine (tropane-type), colchicine (tropolone-type), allantoin (imidazolidine-type), trigonelline (pyridine-type) as well as octopamine, synephrine, and capsaicin (exocyclic amine-type) were tested in vitro for their inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) at 1 mg/ml concentration by the Ellman method using an ELISA microplate reader. Among the alkaloids tested, only capsaicin exerted a remarkable inhibitory effect towards both AChE and BChE [(62.7 +/- 0.79)% and (75.3 +/- 0.98)%, respectively]. While the rest of the alkaloids did not show any significant inhibition against AChE, three of the alkaloids, namely retamine, sparteine, and yohimbine, exerted a noteworthy anti-BChE effect as compared to galanthamine, the reference drug. PMID:18069241

  3. A novel alkaloid from Gaultheria nummularioides.

    Yang, M-F; Li, Y-Y; Li, B-G; Zhang, G-L

    2007-03-01

    A novel alkaloid, gaultherialine A (1), along with twenty-seven known compounds were isolated from the whole plants of Gaultheria nummularioides D. Don. The structure of the new alkaloid was elucidated as 7,8-dimethoxy-1-(4-methoxyphenyl)-4,5-dihydro-2H-benzo[e]indole-2-one N-oxide (1) on the basis of spectral evidence. PMID:17454316

  4. Alkaloids from Fissistigma latifolium (Dunal) Merr.

    Asmah Alias; Hazrina Hazni; Faridahanim Mohd Jaafar; Khalijah Awang; Nor Hadiani Ismail

    2010-01-01

    A phytochemical study of the bark of Fissistigma latifolium (Annonaceae) yielded a new aporphine alkaloid, (-)-N-methylguattescidine (1), and eight known alkaloids: liriodenine (2), oxoxylopine (3), (-)-asimilobine (4), dimethyltryptamine (5), (-)-remerine (6), (-)-anonaine (7), columbamine (8) and lysicamine (9). The compounds were isolated using various chromatographic methods and structural elucidation was accomplished by means of spectroscopic methods, notably 1D-NMR (1H, 13C, DEPT), 2D-N...

  5. Alkaloids from Fissistigma latifolium (Dunal Merr.

    Asmah Alias

    2010-06-01

    Full Text Available A phytochemical study of the bark of Fissistigma latifolium (Annonaceae yielded a new aporphine alkaloid, (--N-methylguattescidine (1, and eight known alkaloids: liriodenine (2, oxoxylopine (3, (--asimilobine (4, dimethyltryptamine (5, (--remerine (6, (--anonaine (7, columbamine (8 and lysicamine (9. The compounds were isolated using various chromatographic methods and structural elucidation was accomplished by means of spectroscopic methods, notably 1D-NMR (1H, 13C, DEPT, 2D-NMR (COSY, HMQC, HMBC, UV, IR and MS.

  6. Ether bridge formation in loline alkaloid biosynthesis

    Pan, Juan; Bhardwaj, Minakshi; Faulkner, Jerome R.; Nagabhyru, Padmaja; Charlton, Nikki D.; Higashi, Richard M.; Miller, Anne-Frances; Young, Carolyn A; Grossman, Robert B.; Schardl, Christopher L

    2013-01-01

    Lolines are potent insecticidal agents produced by endophytic fungi of cool-season grasses. These alkaloids are composed of a pyrrolizidine ring system and an uncommon ether bridge linking carbons 2 and 7. Previous results indicated that 1-aminopyrrolizidine was a pathway intermediate. We used RNA interference to knock down expression of lolO, resulting in the accumulation of a novel alkaloid identified as exo-1-acetamidopyrrolizidine based on high-resolution MS and NMR. Genomes of endophytes...

  7. Seco-tabersonine alkaloids from Tabernaemontana corymbosa.

    Lim, Kuan-Hon; Thomas, Noel F; Abdullah, Zanariah; Kam, Toh-Seok

    2009-02-01

    Two seco-tabersonine alkaloids, jerantiphyllines A and B, in addition to a tabersonine hydroxyindolenine, jerantinine H, and a recently reported vincamine alkaloid 7, were isolated from the leaf extract of the Malayan Tabernaemontana corymbosa and the structures were established using NMR and MS analysis. Biomimetic conversion of jerantinines A and E to their respective vincamine and 16-epivincamine derivatives were also carried out. PMID:19217125

  8. Identification and Quantification of the Main Active Anticancer Alkaloids from the Root of Glaucium flavum

    Lamine Bournine

    2013-12-01

    Full Text Available Glaucium flavum is used in Algerian folk medicine to remove warts (benign tumors. Its local appellations are Cheqiq el-asfar and Qarn el-djedyane. We have recently reported the anti-tumoral activity of Glaucium flavum root alkaloid extract against human cancer cells, in vitro and in vivo. The principal identified alkaloid in the extract was protopine. This study aims to determine which component(s of Glaucium flavum root extract might possess potent antitumor activity on human cancer cells. Quantitative estimation of Glaucium flavum alkaloids was realized by HPLC-DAD. Glaucium flavum effect on human normal and cancer cell viability was determined using WST-1 assay. Quantification of alkaloids in Glaucium flavum revealed that the dried root part contained 0.84% of protopine and 0.07% of bocconoline (w/w, while the dried aerial part contained only 0.08% of protopine, glaucine as the main alkaloid, and no bocconoline. In vitro evaluation of the growth inhibitory activity on breast cancer and normal cells demonstrated that purified protopine did not reproduce the full cytotoxic activity of the alkaloid root extract on cancer cell lines. On the other hand, bocconoline inhibited strongly the viability of cancer cells with an IC50 of 7.8 µM and only a low cytotoxic effect was observed against normal human cells. Our results showed for the first time that protopine is the major root alkaloid of Glaucium flavum. Finally, we are the first to demonstrate a specific anticancer effect of Glaucium flavum root extract against breast cancer cells, which can be attributed, at least in part, to bocconoline.

  9. Differences in tolerance to host cactus alkaloids in Drosophila koepferae and D. buzzatii.

    Soto, Ignacio M; Carreira, Valeria P; Corio, Cristian; Padró, Julián; Soto, Eduardo M; Hasson, Esteban

    2014-01-01

    The evolution of cactophily in the genus Drosophila was a major ecological transition involving over a hundred species in the Americas that acquired the capacity to cope with a variety of toxic metabolites evolved as feeding deterrents in Cactaceae. D. buzzatii and D. koepferae are sibling cactophilic species in the D. repleta group. The former is mainly associated with the relatively toxic-free habitat offered by prickly pears (Opuntia sulphurea) and the latter has evolved the ability to use columnar cacti of the genera Trichocereus and Cereus that contain an array of alkaloid secondary compounds. We assessed the effects of cactus alkaloids on fitness-related traits and evaluated the ability of D. buzzatii and D. koepferae to exploit an artificial novel toxic host. Larvae of both species were raised in laboratory culture media to which we added increasing doses of an alkaloid fraction extracted from the columnar cactus T. terschekii. In addition, we evaluated performance on an artificial novel host by rearing larvae in a seminatural medium that combined the nutritional quality of O. sulphurea plus amounts of alkaloids found in fresh T. terschekii. Performance scores in each rearing treatment were calculated using an index that took into account viability, developmental time, and adult body size. Only D. buzzatii suffered the effects of increasing doses of alkaloids and the artificial host impaired viability in D. koepferae, but did not affect performance in D. buzzatii. These results provide the first direct evidence that alkaloids are key determinants of host plant use in these species. However, the results regarding the artificial novel host suggest that the effects of alkaloids on performance are not straightforward as D. koepferae was heavily affected. We discuss these results in the light of patterns of host plan evolution in the Drosophila repleta group. PMID:24520377

  10. Identification of cellular and molecular factors determining the response of cancer cells to six ergot alkaloids.

    Mrusek, Marco; Seo, Ean-Jeong; Greten, Henry Johannes; Simon, Michael; Efferth, Thomas

    2015-02-01

    Ergot alkaloids are psychoactive and vasoconstricting agents of the fungus Claviceps purpurea causing poisoning such as ergotism in medieval times (St. Anthony's Fire). This class of substances also inhibits tumor growth in vitro and in vivo, though the underlying mechanisms are unclear as yet. We investigated six ergot alkaloids (agroclavine, ergosterol, ergocornin E, ergotamine, dihydroergocristine, and 1-propylagroclavine tartrate) for their cytotoxicity towards tumor cell lines of the National Cancer Institute, USA. 1-Propylagroclavine tartrate (1-PAT) revealed the strongest cytotoxicity. Out of 76 clinically established anticancer drugs, cross-resistance was found between the ergot alkaloids and 6/7 anti-hormonal drugs (=85.7 %) and 5/15 DNA-alkylating drugs (=33.3 %). The IC50 values for the six alkaloids were not correlated to well-known determinants of drug resistance, such as proliferative activity (as measured by cell doubling times, PCNA expression, and cell cycle distribution), the multidrug resistance-mediating P-glycoprotein/MDR1 and expression or mutations of oncogenes and tumor suppressor genes (EGFR, RAS, TP53). While resistance of control drugs (daunorubicin, cisplatin, erlotinib) correlated with these classical resistance mechanisms, ergot alkaloids did not. Furthermore, COMPARE and hierarchical cluster analyses were performed of mRNA microarray data to identify genes correlating with sensitivity or resistance to 1-PAT. Twenty-three genes were found with different biological functions (signal transducers, RNA metabolism, ribosome constituents, cell cycle and apoptosis regulators etc.). The expression of only 3/66 neuroreceptor genes correlated with the IC50 values for 1-PAT, suggesting that the psychoactive effects of ergot alkaloids may not play a major role for the cytotoxic activity against cancer cells. In conclusion, the cytotoxicity of ergot alkaloids is not involved in classical mechanisms of drug resistance opening the possibility to

  11. Visual identification of alkaloids in some medicinal plants: common alkaloid reagents versus bromocresol green

    Shamsa F, Esfahani HR, Gamooshi RA

    2008-07-01

    Full Text Available "n Normal 0 false false false MicrosoftInternetExplorer4 /* Style Definitions */ table.MsoNormalTable {mso-style-name:"Table Normal"; mso-tstyle-rowband-size:0; mso-tstyle-colband-size:0; mso-style-noshow:yes; mso-style-parent:""; mso-padding-alt:0cm 5.4pt 0cm 5.4pt; mso-para-margin:0cm; mso-para-margin-bottom:.0001pt; mso-pagination:widow-orphan; font-size:10.0pt; font-family:"Times New Roman"; mso-ansi-language:#0400; mso-fareast-language:#0400; mso-bidi-language:#0400;} Background: Alkaloids are a group of nitrogenous compounds with potential effects on the physiological behavior of human and animals. Some of these compounds are considered important drugs in modern medicine, such as atropine and morphine. Plants are considered the most important source of alkaloids. Therefore, investigating the presence of alkaloids in different plants is very important. Usually, alkaloids in plants are identified by methods such as those of Dragendorf, Wagner and Meyer, among others, which require milligrams of alkaloids for identification. In the present study, a fast and sensitive procedure for detecting of alkaloids in plants is presented.   "n"nMethods: Twelve dried plants samples were investigated for the presence alkaloids. After extracting the total alkaloid into methanol using a Soxhlet extractor, a few milligrams of the extract was transferred to a separatory funnel, buffered to pH 4.7, the bromocresol green (BCG solution (10-4 M was added, mixed and extracted with CHCl3 until a yellow color was observed in the CHCl3 layer, indicating the presence of the alkaloid. The crude extracts were also investigated by the standard methods of Dragendorf, Wagner and Meyer for the presence of alkaloids.   "n"nResults: Investigation of the 12 plant samples for the presence of alkaloids by the standard reagents of Dragendorf, Wagner, and Meyer showed that only Camelia sinensis (flowers, Echium amoenum Fisch & Mey (flowers, and Stachys (aerial parts are devoid

  12. Integration of transcriptome, proteome and metabolism data reveals the alkaloids biosynthesis in Macleaya cordata and Macleaya microcarpa.

    Jianguo Zeng

    Full Text Available BACKGROUND: The Macleaya spp., including Macleaya cordata and Macleaya microcarpa, are traditional anti-virus, inflammation eliminating, and insecticide herb medicines for their isoquinoline alkaloids. They are also known as the basis of the popular natural animal food addictive in Europe. However, few studies especially at genomics level were conducted on them. Hence, we performed the Macleaya spp. transcriptome and integrated it with iTRAQ proteome analysis in order to identify potential genes involved in alkaloids biosynthesis. METHODOLOGY AND PRINCIPAL FINDINGS: We elaborately designed the transcriptome, proteome and metabolism profiling for 10 samples of both species to explore their alkaloids biosynthesis. From the transcriptome data, we obtained 69367 and 78255 unigenes for M. cordata and M. microcarpa, in which about two thirds of them were similar to sequences in public databases. By metabolism profiling, reverse patterns for alkaloids sanguinarine, chelerythrine, protopine, and allocryptopine were observed in different organs of two species. We characterized the expressions of enzymes in alkaloid biosynthesis pathways. We also identified more than 1000 proteins from iTRAQ proteome data. Our results strongly suggest that the root maybe the organ for major alkaloids biosynthesis of Macleaya spp. Except for biosynthesis, the alkaloids storage and transport were also important for their accumulation. The ultrastructure of laticifers by SEM helps us to prove the alkaloids maybe accumulated in the mature roots. CONCLUSIONS/SIGNIFICANCE: To our knowledge this is the first study to elucidate the genetic makeup of Macleaya spp. This work provides clues to the identification of the potential modulate genes involved in alkaloids biosynthesis in Macleaya spp., and sheds light on researches for non-model medicinal plants by integrating different high-throughput technologies.

  13. Interactions between {beta}-carboline alkaloids and bovine serum albumin: Investigation by spectroscopic approach

    Nafisi, Shohreh, E-mail: drshnafisi@gmail.com [Department of Chemistry, Islamic Azad University, Central Tehran Branch (IAUCTB), Tehran (Iran, Islamic Republic of); Panahyab, Ataollah [Department of Chemistry, Islamic Azad University, Central Tehran Branch (IAUCTB), Tehran (Iran, Islamic Republic of); Bagheri Sadeghi, Golshan [Department of Biology, Islamic Azad University, Science and Research Branch, Tehran (Iran, Islamic Republic of)

    2012-09-15

    {beta}-Carboline alkaloids are present in medicinal plants such as Peganum harmala L. that have been used as folk medicine in anticancer therapy. BSA is the major soluble protein constituent of the circulatory system, and has many physiological functions including the transport of a variety of compounds. This study is the first attempt to investigate the binding of {beta}-carboline alkaloids to BSA by using a constant protein concentration and varying drug concentrations at pH 7.2. FTIR and UV-Vis spectroscopic methods were used to analyze the binding modes of {beta}-carboline alkaloids, the binding constants and the effects of drug complexation on BSA stability and conformation. Spectroscopic evidence showed that {beta}-carboline alkaloids bind BSA via hydrophobic interaction and van der Waals contacts along with H-bonding with the -NH groups, with overall binding constants of K{sub harmine-BSA}=2.04 Multiplication-Sign 10{sup 4} M{sup -1}, K{sub tryptoline-BSA}=1.2 Multiplication-Sign 10{sup 4} M{sup -1}, K{sub harmaline-BSA}=5.04 Multiplication-Sign 10{sup 3} M{sup -1}, K{sub harmane-BSA}=1.41 Multiplication-Sign 10{sup 3} M{sup -1} and K{sub harmalol-BSA}=1.01 Multiplication-Sign 10{sup 3} M{sup -1}, assuming that there is one drug molecule per protein. The BSA secondary structure was altered with a major decrease of {alpha}-helix from 64% (free protein) to 59% (BSA-harmane), 56% (BSA-harmaline and BSA-harmine), 55% (BSA-tryptoline), 54% (BSA-harmalol) and {beta}-sheet from 15% (free protein) to 6-8% upon {beta}-carboline alkaloids complexation, inducing a partial protein destabilization. - Highlights: Black-Right-Pointing-Pointer We model the binding of {beta}-carboline alkaloids to BSA by using the spectroscopic methods. Black-Right-Pointing-Pointer We investigate the effects of drug complexation on BSA stability and conformation. Black-Right-Pointing-Pointer A partial protein destabilization occurred at high alkaloids concentration. Black

  14. Fighting against Leishmaniasis: search of alkaloids as future true potential anti-Leishmanial agents.

    Mishra, Bhuwan B; Singh, Rakesh K; Srivastava, A; Tripathi, V J; Tiwari, Vinod K

    2009-01-01

    Leishmaniasis, a group of tropical diseases caused by protozoan parasites of genus Leishmania, is a major health problem worldwide that affects millions of people especially in the developing nations. Generic pentavalent antimonials have been the mainstay for therapy in the endemic regions due to efficacy and cost effectiveness, but the growing incidence of their resistance has seriously hampered their use. In many cases the drugs employed for the treatment are toxic, marginally effective, given by injection and, compromised by the development of resistance. Therefore, the development of new mechanism based safe, effective and affordable chemotherapeutic agents to fight leishmaniasis would be an urgent priority research. The recent researches focused on natural products have shown a wise way to get a true and potentially rich source of drug candidates against leishmaniasis, where alkaloids have been found more effective. The present review briefly illustrates an account on current status of leishmaniasis, life cycle of parasites and biology, synergy of the disease with HIV, therapeutic options available to cure this disease and, highlights why natural products especially alkaloids as folk medicines are so important? Additionally, the outlines for the leishmanicidal activities of various alkaloids including indole, quinoline, isoquinoline, pyrimidine-beta-carboline, steroidal and diterpene alkaloids from various plants as well as alkaloids from marine sources have been provided with their mechanistic studies. PMID:19149664

  15. Leishmanicidal, antiplasmodial and cytotoxic activity of indole alkaloids from Corynanthe pachyceras

    Staerk, D; Lemmich, E; Christensen, J;

    2000-01-01

    -NMR resonances by COSY and NOESY experiments. These and related alkaloids showed pronounced activity against Leishmania major promastigotes (IC50 at the micromolar level) but no significant in vitro antiplasmodial activity (against chloroquine-sensitive Plasmodium falciparum). Cytotoxicity assessed with drug...

  16. Alkaloid-Containing Plants Poisonous to Cattle and Horses in Europe.

    Cortinovis, Cristina; Caloni, Francesca

    2015-12-01

    Alkaloids, nitrogen-containing secondary plant metabolites, are of major interest to veterinary toxicology because of their occurrence in plant species commonly involved in animal poisoning. Based on epidemiological data, the poisoning of cattle and horses by alkaloid-containing plants is a relatively common occurrence in Europe. Poisoning may occur when the plants contaminate hay or silage or when forage alternatives are unavailable. Cattle and horses are particularly at risk of poisoning by Colchicum autumnale (meadow saffron), Conium maculatum (poison hemlock), Datura stramonium (jimson weed), Equisetum palustre (marsh horsetail), Senecio spp. (ragwort and groundsel) and Taxus baccata (European yew). This review of poisonous alkaloid-containing plants describes the distribution of these plants, conditions under which poisoning occurs, active toxic principles involved and subsequent clinical signs observed. PMID:26670251

  17. Two New C19-Diterpenoid Alkaloids from Delphinium davidii Franch.

    Xiao Xia LIANG; Dong Lin CHEN; Feng Peng WANG

    2006-01-01

    Two new C19-diterpenoid alkaloids, davidisines A (1) and B (2) along with thirteen known alkaloids were isolated from the whole herb of Delphinium davidii Franch. Their structures were established by spectral methods, especially 2D NMR techniques.

  18. Actions of Piperidine Alkaloid Teratogens at Fetal Nicotinic Acetylcholine Receptors.

    Teratogenic alkaloids are found in many species of plants including Conium maculatum L., Nicotiana glauca, Nicotiana tabaccum, and multiple Lupinus spp. Fetal musculoskeletal defects produced by alkaloids from these plants include arthrogyropisis, scoliosis, torticollis, kyposis, lordosis, and clef...

  19. Monoterpenoid Indole Alkaloids from Catharanthus roseus Cultivated in Yunnan.

    Wang, Bei; Liu, Lu; Chen, Ying-ying; Li, Qiong; Li, Dan; Liu, Va-ping; Luo, Xiao-dong

    2015-12-01

    A new monoterpenoid indole alkaloid, 15,20-dehydro-3α-(2-oxopropyl) coronaridine (1), along with sixteen analogues (2-17) were isolated from the leaves of Catharanthus roseus cultivated in Yunnan. The new alkaloid was elucidated on the basis of extensive spectroscopic analysis, and the known alkaloids were identified by comparison with the reported spectroscopic data. Among them, alkaloid 16 was isolated from Catharanthus for the first time. PMID:26882670

  20. Antibacterial and antifungal activity of liriodenine and related oxoaporphine alkaloids.

    Hufford, C D; Sharma, A S; Oguntimein, B O

    1980-10-01

    Liriodenine was evaluated for its antibacterial and antifungal activity against several microorganisms. Other related oxoaporphine alkaloids also were evaluated. Attempts to prepare oxoaporphine alkaloids from N-acetylnoraporphines were unsuccessful, but an unexpected phenanthrene alkaloid was obtained. A novel N-demethylation reaction was noted when oxogaucine methiodide and liriodenine methiodide were treated with alumina. PMID:7420287

  1. An efficient synthesis of loline alkaloids

    Cakmak, Mesut; Mayer, Peter; Trauner, Dirk

    2011-07-01

    Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. It has been known for more than a century and has been the subject of extensive biological investigations, but only two total syntheses have been achieved to date. Here, we report an asymmetric total synthesis of loline that, with less then ten steps, is remarkably short. Our synthesis incorporates a Sharpless epoxidation, a Grubbs olefin metathesis and an unprecedented transannular aminobromination, which converts an eight-membered cyclic carbamate into a bromopyrrolizidine. The synthesis is marked by a high degree of chemo- and stereoselectivity and gives access to several members of the loline alkaloid family. It delivers sufficient material to support a programme aimed at studying the complex interactions between plants, fungi, insects and bacteria brokered by loline alkaloids.

  2. Analysis of toxic alkaloids in body samples.

    Beyer, Jochen; Drummer, Olaf H; Maurer, Hans H

    2009-03-10

    Many plants contain toxic alkaloids which may be dangerous to humans. Despite the large number of poisonous plants, cases of fatal plant poisonings are relatively rare. The frequencies of poisonings and the plants involved are often regionally specific. Plant poisonings can be aggregated into three categories: unintended ingestions, intended ingestions, and poisoning due to abuse of plant material. Unintended ingestions often occur in children or from a mix-up of plants and mushrooms in adults. Intended ingestions are common in homicides and suicides. Increasingly common is the abuse of plants for hallucinogenic reasons. Toxicological analysis of such alkaloids may help in diagnosis of poisoning or abuse cases. This review describes the toxic alkaloids aconitine, atropine, coniine, colchicine, cytisine, dimethyltryptamine, harmine, harmaline, ibogaine, kawain, mescaline, scopolamine, and taxine, which are often involved in fatal and non-fatal poisonings. The paper summarizes the symptoms of the intoxications and reviews the methods of detection of their toxic constituents in biological fluids. PMID:19147309

  3. Two New Alkaloids from Narcissus serotinus L.

    Francesc Viladomat

    2010-10-01

    Full Text Available The Amaryllidaceae family is well known for the presence of an exclusive group of alkaloids with a wide range of biological activities. Narcissus serotinus L. is a plant belonging to this family and its geographical distribution is mainly located along the Mediterranean coast. In the present work, specimens collected near Casablanca (Morocco were used to study the alkaloid content of this species. Starting with 350 g of the whole plant we used standard extraction and purification procedures to obtain fractions and compounds for GC-MS and NMR analysis. As well as five known alkaloids, we isolated two new compounds: 1-O-(3´-acetoxybutanoyllycorine and narseronine. The latter has been previously published, but with an erroneous structure.

  4. Decontamination of alkaloid drugs with ionizing radiation

    The investigation of the effect of ionizing radiation (doses of 5, 10 and 25 kGy) on selected kinds of alkaloid drugs revealed a statistically significant decrease in the number of microorganisms (bacteria, moulds) in dependence on the dose. The largest decrease in the alkaloid content due to ionizing radiation took place in Radix veratri. in other drugs the differences are statistically insignificant. The alkaloid content never decreased to below the limit required by the pharmacopoeia. Infusions prepared from the parent material complied with the requirements of PhBs 4 for microbiological purity except for Folium belladonnae; in infusions from the irradiated drugs the decrease in the number of microorganisms correlated with the decrease found after the irradiation of the drug. (author). 7 tabs., 14 refs

  5. Aporphine alkaloids from Ocotea macrophylla (Lauraceae

    Ludy Cristina Pabon

    2010-01-01

    Full Text Available Four aporphine alkaloids from the wood of Ocotea macrophylla (Lauraceae were isolated and characterized as (S-3-methoxy-nordomesticine (1, (S-N-ethoxycarbonyl-3-methoxy-nordomesticine (2, (S-N-formyl-3-methoxy-nordomesticine (3 and (S-N-methoxycarbonyl-3-methoxy-nordomesticine (4; alkaloids 2-4 are being report for the first time. The structure the isolated compounds were determined based on their spectral data and by comparison of their spectral data with values described in literature. The alkaloid fraction and compound 1 showed antifungal activity against Fusarium oxysporum f. sp. lycopersici and also compound 1 showed antimicrobial activity towards Staphylococcus aureus, Enterococcus faecalis as well.

  6. Aporphine alkaloids from Ocotea macrophylla (Lauraceae)

    Pabon, Ludy Cristina; Cuca, Luis Enrique, E-mail: lcpabonb@unal.edu.c [Universidad Nacional de Bogota (Colombia). Facultad de Ciencias. Dept. de Quimica

    2010-07-01

    Four aporphine alkaloids from the wood of Ocotea macrophylla (Lauraceae) were isolated and characterized as (S)-3-methoxy-nordomesticine (1), (S)-N-ethoxycarbonyl-3-methoxy-nordomesticine (2), (S)-N-formyl-3-methoxy-nordomesticine (3) and (S)-N-methoxycarbonyl-3-methoxy-nordomesticine (4); alkaloids 2-4 are being report for the first time. The structure the isolated compounds were determined based on their spectral data and by comparison of their spectral data with values described in literature. The alkaloid fraction and compound 1 showed antifungal activity against Fusarium oxysporum f. sp. lycopersici and also compound 1 showed antimicrobial activity towards Staphylococcus aureus, Enterococcus faecalis as well. (author)

  7. Antimicrobial hasubanalactam alkaloid from Stephania glabra.

    Semwal, Deepak Kumar; Rawat, Usha

    2009-03-01

    A novel hasubanalactam alkaloid, named glabradine, has been isolated from the tubers of Stephania glabra, together with three known quaternary protoberberine alkaloids, palmatine, dehydrocorydalmine and stepharanine. The structure of glabradine was assigned as 7-O-demethyl-N,O-dimethyloxostephinine, by means of rigorous spectroscopic analysis including 2 D NMR measurements. It was evaluated for antimicrobial activity against Staphylococcus aureus, S. mutans, Microsporum gypseum, M. canis and Trichophyton rubrum and displayed potent antimicrobial activity superior to those of novobiocin and erythromycin used as positive controls. PMID:19148860

  8. Antiprotozoal alkaloids from Psychotria prunifolia (Kunth) Steyerm

    Kato, Lucilia; Oliveira, Cecilia M.A. de; Faria, Emiret O.; Ribeiro, Laryssa C.; Carvalho, Brenda G., E-mail: lucilia@quimica.ufg.br [Instituto de Quimica, Universidade Federal de Goias, Campus II, Samambaia, Goiania, GO (Brazil); Silva, Cleuza C. da; Santin, Silvana M.O. [Departamento de Quimica, Universidade Estadual de Maringa, Maringa, PR (Brazil); Schuque, Ivania T.A.; Nakamura, Celso V.; Britta, Elisandra A.; Miranda, Nathielle [Departamento de Farmacia e Farmacologia, Universidade Estadual de Maringa, PR (Brazil); Iglesias, Amadeu H. [Waters Technologies do Brasil LTDA, Barueri, SP (Brazil); Delprete, Piero G. [VHerbier de Guyane, Institut de Recherche pour le Developpement (IRD), UMR AMAP, French Guiana (France)

    2012-07-01

    The continuity of the phyto chemical study of crude extracts of P. prunifolia's roots and branches led to the isolation of five indole-{beta}-carboline alkaloids. Among them, the 10-hydroxy-iso-deppeaninol and N-oxide-10-hydroxy-antirhine derivatives are described here for the first time. The structures were achieved through 1D and 2D NMR, IR and HRMS analyses. The branches and roots crude extracts and the alkaloids 14-oxoprunifoleine and strictosamide showed selective activity against L. amazonensis, with IC{sub 50} values of 16.0 and 40.7 {mu}g per mL, respectively. (author)

  9. Thin-Layer Chromatography/Desorption Electrospray Ionization Mass Spectrometry: Investigation of Goldenseal Alkaloids

    Van Berkel, Gary J [ORNL; Tomkins, Bruce A [ORNL; Kertesz, Vilmos [ORNL

    2007-01-01

    Desorption electrospray ionization mass spectrometry was investigated as a means to qualitatively identify and to quantify analytes directly from developed normal-phase thin layer chromatography plates. The atmospheric sampling capillary of a commercial ion trap mass spectrometer was extended to permit sampling and ionization of analytes in bands separated on intact TLC plates (up to 10 cm x 10 cm). A surface positioning software package and the appropriate hardware enabled computer-controlled surface scanning along the length of development lanes or at fixed RF value across the plates versus the stationary desorption electrospray emitter. Goldenseal (Hydrastis canadensis) and related alkaloids and commercial dietary supplements were used as standards and samples. Alkaloid standards and samples were spotted and separated on aluminum- or glass-backed plates using established literature methods. The mass spectral signal levels as a function of desorption spray solvent were investigated with acetonitrile proving superior to methanol. The detection levels (ca. 5 ng each or 14 -28 pmol) in mass spectral full scan mode were determined statistically from the calibration curves (2.5 - 100 pmol) for the standards berberine, palmatine and hydrastinine spotted as a mixture and separated on the plates. Qualitative screening of the major alkaloids present in six different over-the-counter "goldenseal" dietary supplements was accomplished by obtaining full scan mass spectra during surface scans along the development lane in the direction of increasing RF value. In one sample, alkaloids were detected that strongly suggested the presence of at least one additional herb undeclared on the product label. These same data indicated the misidentification of one of the alkaloids in the TLC literature. Quantities of the alkaloids present in two of the samples determined using the mass spectral data were in reasonable agreement with the label values indicating the quantitative ability of

  10. Hydrofocusing Bioreactor Produces Anti-Cancer Alkaloids

    Gonda, Steve R.; Valluri, Jagan V.

    2011-01-01

    A methodology for growing three-dimensional plant tissue models in a hydrodynamic focusing bioreactor (HFB) has been developed. The methodology is expected to be widely applicable, both on Earth and in outer space, as a means of growing plant cells and aggregates thereof under controlled conditions for diverse purposes, including research on effects of gravitation and other environmental factors upon plant growth and utilization of plant tissue cultures to produce drugs in quantities greater and at costs lower than those of conventional methodologies. The HFB was described in Hydro focus - ing Bioreactor for Three-Dimensional Cell Culture (MSC-22358), NASA Tech Briefs, Vol. 27, No. 3 (March 2003), page 66. To recapitulate: The HFB offers a unique hydrofocusing capability that enables the creation of a low-shear liquid culture environment simultaneously with the herding of suspended cells and tissue assemblies and removal of unwanted air bubbles. The HFB includes a rotating cell-culture vessel with a centrally located sampling port and an internal rotating viscous spinner attached to a rotating base. The vessel and viscous spinner can be made to rotate at the same speed and direction or different speeds and directions to tailor the flow field and the associated hydrodynamic forces in the vessel in order to obtain low-shear suspension of cells and control of the locations of cells and air bubbles. For research and pharmaceutical-production applications, the HFB offers two major benefits: low shear stress, which promotes the assembly of cells into tissue-like three-dimensional constructs; and randomization of gravitational vectors relative to cells, which affects production of medicinal compounds. Presumably, apposition of plant cells in the absence of shear forces promotes cell-cell contacts, cell aggregation, and cell differentiation. Only gentle mixing is necessary for distributing nutrients and oxygen. It has been postulated that inasmuch as cells in the simulated

  11. Pharmacokinetics of Hoasca alkaloids in healthy humans.

    Callaway, J C; McKenna, D J; Grob, C S; Brito, G S; Raymon, L P; Poland, R E; Andrade, E N; Andrade, E O; Mash, D C

    1999-06-01

    N,N-Dimethyltryptamine (DMT), harmine, harmaline and tetrahydroharmine (THH) are the characteristic alkaloids found in Amazonian sacraments known as hoasca, ayahuasca, and yajè. Such beverages are characterized by the presence of these three harmala alkaloids, where harmine and harmaline reversibly inhibit monoamine oxidase A (MAO-A) while tetrahydroharmine weakly inhibits the uptake of serotonin. Together, both actions increase central and peripheral serotonergic activity while facilitating the psychoactivity of DMT. Though the use of such 'teas' has be known to western science for over 100 years, little is known of their pharmacokinetics. In this study, hoasca was prepared and administered in a ceremonial context. All four alkaloids were measured in the tea and in the plasma of 15 volunteers, subsequent to the ingestion of 2 ml hoasca/kg body weight, using gas (GC) and high pressure liquid chromatographic (HPLC) methods. Pharmacokinetic parameters were calculated and peak times of psychoactivity coincided with high alkaloid concentrations, particularly DMT which had an average Tmax of 107.5 +/- 32.5 min. While DMT parameters correlated with those of harmine, THH showed a pharmacokinetic profile relatively independent of harmine's. PMID:10404423

  12. Acetylcholinesterase-inhibiting Alkaloids from Zephyranthes concolor

    Sebastien Arseneau

    2011-11-01

    Full Text Available The bulbs and aerial parts of Zephyranthes concolor (Lindl. Benth. & Hook. f. (Amaryllidaceae, an endemic species to Mexico, were found to contain the alkaloids chlidanthine, galanthamine, galanthamine N-oxide, lycorine, galwesine, and epinorgalanthamine. Since currently only partial and low resolution 1H-NMR data for chlidanthine acetate are available, and none for chlidanthine, its 1D and 2D high resolution 1H- and 13C-NMR spectra were recorded. Unambiguous assignations were achieved with HMBC, and HSQC experiments, and its structure was corroborated by X-ray diffraction. Minimum energy conformation for structures of chlidanthine, and its positional isomer galanthamine, were calculated by molecular modelling. Galanthamine is a well known acetylcholinesterase inhibitor; therefore, the isolated alkaloids were tested for this activity. Chlidanthine and galanthamine N-oxide inhibited electric eel acetylcholinesterase (2.4 and 2.6 × 10−5 M, respectively, indicating they are about five times less potent than galanthamine, while galwesine was inactive at 10−3 M. Inhibitory activity of HIV-1 replication, and cytotoxicity of the isolated alkaloids were evaluated in human MT-4 cells; however, the alkaloids showed poor activity as compared with standard anti-HIV drugs, but most of them were not cytotoxic.

  13. Saponins and alkaloids from Abuta grandifolia

    Sayagh, C.; Long, C; Moretti, Christian; Lavaud, C.

    2012-01-01

    Five new bidesmosidic saponins (1-5), along with six known triterpenoid saponins, were isolated from the methanolic extracts of the leaves and twigs of Abuta grandifolia. The ethyl acetate extracts allowed the isolation of three tropoloisoquinolines and of one isoquinoline; all were known alkaloids. The structures of all compounds were elucidated on the basis of extensive spectroscopic data analysis.

  14. A new indole alkaloid from Ervatamia yunnanensis.

    Jin, Yong-Sheng; Du, Jing-Ling; Chen, Hai-Sheng; Jin, Li; Liang, Shuang

    2010-01-01

    The stems of Ervatamia yunnanensis have afforded a new indole alkaloid, ervataine (1), whose structure was determined by spectroscopic analysis. Five known compounds, ibogaine (2) coronaridine (3), heyneanine (4), voacangine hydroxyindolenine (5) and coronaridine hydroxyindolenine (6), were also isolated. PMID:19647051

  15. Semisynthetic dimers of antiparkinsonic ergot alkaloids

    Křen, Vladimír; Weignerová, Lenka; Kuzma, Marek; Jegorov, A.; Sedmera, Petr

    2001-01-01

    Roč. 55, č. 6 (2001), s. 1045-1056. ISSN 0385-5414 R&D Projects: GA AV ČR IAA4020901 Institutional research plan: CEZ:AV0Z5020903 Keywords : ergot alkaloids * antiparkinsonic activity Subject RIV: EE - Microbiology, Virology Impact factor: 0.970, year: 2001

  16. A New Alkaloid from Sinomenium acutum

    Wei Ming CHENG; Feng QIU; Li Jun WU; Xin Sheng YAO

    2005-01-01

    Sinomenium acutum is widely used in East and South Asia for the treatment of many diseases, especially rheumatoid arthritis (RA). The chemical research on Sinomenium acutum led to the isolation of a new alkaloid compound (1). On the basis of chemical evidences and spectral analysis, 1 was identified as N-(1, 7-dimethoxylphenanthren-2-yl)acetamide.

  17. Alkaloids in the pharmaceutical industry: Structure, isolation and application

    Nikolić Milan

    2003-01-01

    Full Text Available By the end of the 18th and the beginning of the 19th century a new era began in medicine, pharmaceutics and chemistry that was strongly connected with alkaloids and alkaloid drugs. Even before that it was known that certain drugs administered in limited doses were medicines, and toxic if taken in larger doses (opium, coke leaves, belladonna roots, monkshood tubers crocus or hemlock seeds. However, the identification, isolation and structural characterization of the active ingredients of the alkaloid drugs was only possible in the mid 20th century by the use of modern extraction equipment and instrumental methods (NMR, X-ray diffraction and others.In spite of continuing use over a long time, there is still great interest in investigating new drugs, potential raw materials for the pharmaceutical industry, as well as the more detailed investigation and definition of bio-active components and the indication of their activity range, and the partial synthesis of new alkaloid molecules based on natural alkaloids. The scope of these investigations, especially in the field of semi-synthesis is to make better use of the bio-active ingredients of alkaloid drugs, i.e. to improve the pharmacological effect (stronger and prolonged effect of the medicine, decreased toxicity and side effects, or to extend or change the applications. A combined classification of alkaloids was used, based on the chemical structure and origin, i.e. the source of their isolation to study alkaloid structure. For practical reasons, the following classification of alkaloids was used: ergot alkaloids, poppy alkaloids, tropanic alkaloids purine derivative alkaloids, carbon-cyclic alkaloids, and other alkaloids. The second part of this report presents a table of general procedures for alkaloid isolation from plant drugs (extraction by water non-miscible solvents, extraction by water-miscible solvents and extraction by diluted acid solutions. Also, methods for obtaining chelidonine and

  18. Alkaloids Isolated from Natural Herbs as the Anticancer Agents

    Jin-Jian Lu

    2012-01-01

    Full Text Available Alkaloids are important chemical compounds that serve as a rich reservoir for drug discovery. Several alkaloids isolated from natural herbs exhibit antiproliferation and antimetastasis effects on various types of cancers both in vitro and in vivo. Alkaloids, such as camptothecin and vinblastine, have already been successfully developed into anticancer drugs. This paper focuses on the naturally derived alkaloids with prospective anticancer properties, such as berberine, evodiamine, matrine, piperine, sanguinarine, and tetrandrine, and summarizes the mechanisms of action of these compounds. Based on the information in the literature that is summarized in this paper, the use of alkaloids as anticancer agents is very promising, but more research and clinical trials are necessary before final recommendations on specific alkaloids can be made.

  19. Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins

    Yasufumi Wada

    2010-04-01

    Full Text Available Manynatural products with biologically interesting structures have been isolated from marine animals and plants such as sponges, corals, worms, etc. Some of them are discorhabdin alkaloids. The discorhabdin alkaloids (discorhabdin A-X, isolated from marine sponges, have a unique structure with azacarbocyclic spirocyclohexanone and pyrroloiminoquinone units. Due to their prominent potent antitumor activity, discorhabdins have attracted considerable attention. Many studies have been reported toward the synthesis of discorhabdins. We have accomplished the first total synthesis of discorhabdin A (1, having the strongest activity in vitro among discorhabdins in 2003. In 2009, we have also accomplished the first total synthesis of prianosin B (2, having the 16,17-dehydropyrroloiminoquinone moiety, by a novel dehydrogenation reaction with a catalytic amount of NaN3. These synthetic studies, as well as syntheses of the discorhabdins by various chemists to-date, are reviewed here.

  20. Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum.

    Nissanka, A P; Karunaratne, V; Bandara, B M; Kumar, V; Nakanishi, T; Nishi, M; Inada, A; Tillekeratne, L M; Wijesundara, D S; Gunatilaka, A A

    2001-04-01

    Two benzophenanthrene alkaloids, 8-acetonyldihydronitidine and 8-acetonyldihydroavicine were isolated from Zanthoxylum tetraspermum stem bark along with liriodenine, sesamin, lichexanthone and (+)-piperitol-gamma,gamma-dimethylallylether. The species endemic to Sri Lanka, Z. caudatum, contained sesamin, savinin, liriodenine, decarine and 8-O-desmethyl-N-nornitidine. 8-Acetonyldihydronitidine and 8-acetonyldihydroavicine showed significant antibacterial activity while the former along with liriodenine was strongly antifungal. Savinin exhibited potent spermicidal activity. Both savinin and sesamin exhibited significant insecticidal activity. PMID:11324918

  1. Pyrrolizidine alkaloids and diterpenes from Villasenoria orcuttii

    Arciniegas, Amira; Perez-Castorena, Ana L.; Gonzalez, Karina; Vivar, Alfonso Romo de, E-mail: alperezc@unam.mx [Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Circuito Exterior, Ciudad Universitaria, Coyoacan, DF (Mexico); Reyes-Lezama, Marisol [Centro Conjunto de Investigacion en Quimica Sustentable, Universidad Autonoma del Estado de Mexico-Universidad Nacional Autonoma de Mexico (UAEM-UNAM), Carretera Toluca-Atlacomulco, Estado de Mexico (Mexico); Villasenor, Jose Luis [Instituto de Biologia, Universidad Nacional Autonoma de Mexico, Circuito Exterior, Ciudad Universitaria, Coyoacan, DF, (Mexico)

    2013-07-15

    The chemical study of Villasenoria orcuttii, the only species of the genus Villasenoria, afforded three acyclic diterpenes, two of them described for the first time. Two pyrrolizidine alkaloids, florosenine and floridanine, among other known compounds were also isolated. The absolute configuration of floridanine was determined by X-ray analysis using anomalous dispersion with Cu K{sub {alpha}} radiation, and its {sup 1}H and {sup 13}C nuclear magnetic resonance (NMR) data were corrected. (author)

  2. Radioactive labelling of alkaloids with morphine skeleton

    Results achieved by the sup(14)C, sup(125)I and sup(3)H labelling of alkaloids with morphine skeleton for kinetic, receptor, metabolims and pharmacological investigations are summarized and evaluated. The methods for the preparation of sup(3)H labelled dihydromorphine, dihydroethylmorphine, dihydrocodeine, naloxone and naloxazone are described. The compounds have higher specific molar activity than those referred to in literature which makes them suitable for a number of investigations. (author)

  3. Synthesis studies on the Melodinus alkaloid meloscine

    Feldman, Ken S.; Antoline, Joshua F.

    2013-01-01

    The pentacyclic Melodinus alkaloid (±)-meloscine was synthesized in 19 chemical steps from 2-bromobenzaldehyde through a route featuring an allenyl azide cyclization cascade to deliver the core azabicyclo[3.3.0]octane substructure. Peripheral functionalization of this core included a Tollens-type aldol condensation to set the quaternary center at C(20) and a diastereoselective ring closing metathesis to forge the tetrahydropyridine ring.

  4. A new alkaloid from Solanum cathayanum

    Fan Cheng; Xiang Li; Jun Zhi Wang

    2008-01-01

    A new alkaloid compound I was obtained from Solanum cathayanum, a folk medicine of Hubei Province, together with a knownalkaloid, orotic acid ethyl ester. On the basis of spectroscopic data and chemical methods, I was identified as 8-hydroxy-3-methoxy-5H-pyrido[2,1-c]pyrazin-5-one. Compound 1 can inhibit the production of NO in peritoneal macrophage of mice induced with LPS.The content of NO was determined by enzyme methods.

  5. Potential antimalarial activity of indole alkaloids

    Frederich, Michel; Tits, Monique; Angenot, Luc

    2008-01-01

    New antimalarial treatments are now urgently required, following the emergence of resistance to the most used drugs. Natural products contribute greatly to the therapeutic arsenal in this area, including artemisinin and quinine (and atovaquone, semi-synthetic). Among the natural products, indole alkaloids represent an interesting class of compounds. Screening carried out to date has revealed several substances active in vitro under the micromolar range and with a good selectivity index. This ...

  6. Potential of solid state fermentation for production of ergot alkaloids

    Trejo Hernandez, M.R.; Raimbault, Maurice; Roussos, Sevastianos; Lonsane, B. K.

    1992-01-01

    Production of total ergot alkaloids by #Claviceps fusiformis$ in solid state fermentation was 3.9 times higher compared to that in submerged fermentation. Production was equal in the case of #Claviceps purpurea$ but the spectra of alkaloids were advantageous with the use of solid state fermentation. The data establish potential of solid state fermentation which was not explored earlier for production of ergot alkaloids. (Résumé d'auteur)

  7. Initial Studies on Alkaloids from Lombok Medicinal Plants

    John B. Bremner

    2001-01-01

    Full Text Available Initial investigation of medicinal plants from Lombok has resulted in the collection of 100 plant species predicted to have antimicrobial, including antimalarial, properties according to local medicinal uses. These plants represent 49 families and 80 genera; 23% of the plants tested positively for alkaloids. Among the plants testing positive, five have been selected for further investigation involving structure elucidation and antimicrobial testing on the extracted alkaloids. Initial work on structural elucidation of some of the alkaloids is reported briefly.

  8. New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

    Alois Plodek; Franz Bracher

    2016-01-01

    Secondary metabolites from marine organisms are a rich source of novel leads for drug development. Among these natural products, polycyclic aromatic alkaloids of the pyridoacridine type have attracted the highest attention as lead compounds for the development of novel anti-cancer and anti-infective drugs. Numerous sophisticated total syntheses of pyridoacridine alkaloids have been worked out, and many of them have also been extended to the synthesis of libraries of analogues of the alkaloids...

  9. A new monoterpenoid oxindole alkaloid from Hamelia patens micropropagated plantlets.

    Paniagua-Vega, David; Cerda-García-Rojas, Carlos M; Ponce-Noyola, Teresa; Ramos-Valdivia, Ana C

    2012-11-01

    Chemical studies on Hamelia patens (Rubiaceae) micropropagated plantlets allowed production of a new monoterpenoid oxindole alkaloid, named (-)-hameline (7), together with eight known alkaloids, tetrahydroalstonine (1), aricine (2), pteropodine (3), isopteropodine (4), uncarine F (5), speciophylline (6), palmirine (8), and rumberine (9). The structure of the new alkaloid was assigned on the basis of 1D and 2D NMR spectroscopy, mass spectrometry, and molecular modeling. PMID:23285803

  10. Determination of ephedrine alkaloids in botanicals and dietary supplements by HPLC-UV: collaborative study.

    Roman, Mark C

    2004-01-01

    An international collaborative study was conducted of a high-performance liquid chromatography (HPLC)-UV method for the determination of the major (ephedrine [EP] and pseudoephedrine [PS]) and minor (norephedrine [NE], norpseudoephedrine [NP], methylephedrine [ME], and methylpseudoephedrine [MP]) alkaloids in selected dietary supplements representative of the commercially available products. Ten collaborating laboratories determined the ephedrine-type alkaloid content in 8 blind replicate samples. Five products contained ephedra ground herb or ephedra extract. These 5 products included ground botanical raw material of Ephedra sinica, a common powdered extract of Ephedra sinica, a finished product containing only Ephedra sinica ground botanical raw material, a complex multicomponent dietary supplement containing Ma Huang, and a high-protein chocolate flavored drink mix containing Ma Huang extract. In addition, collaborating laboratories received a negative control and negative control spiked with ephedrine alkaloids at high and low levels for recovery studies. Test extracts were treated to solid-phase extraction using a strong-cation exchange column to help remove interferences. The HPLC analyses were performed on a polar-embedded phenyl column using UV detection at 210 nm. Repeatability relative standard deviations (RSDr) ranged from 0.64-3.0% for EP and 2.0-6.6% for PS, excluding the high protein drink mix. Reproducibility relative standard deviations (RSDR) ranged from 2.1-6.6% for EP and 9.0-11.4% for PS, excluding the high protein drink mix. Recoveries ranged from 84.7-87.2% for EP and 84.6-98.2% for PS. The data developed for the minor alkaloids are more variable with generally unsatisfactory HORRATS (i.e., >2). However, since these alkaloids generally add little to the total alkaloid content of the products, the method gives satisfactory results in measuring total alkaloid content (RSDr 0.85-3.13%; RSDR 2.03-10.97%, HORRAT 0.69-3.23, exclusive of the results

  11. Antidiabetic and Antioxidant Properties of Alkaloids from Catharanthus roseus (L.) G. Don

    Won Fen Wong; Shiau-Chuen Cheah; Mohd Rais Mustafa; Mohammadjavad Paydar; Aditya Arya; Soon Huat Tiong; Chung Yeng Looi; Khalijah Awang; Hazrina Hazni

    2013-01-01

    Catharanthus roseus (L.) G. Don is a herbal plant traditionally used by local populations in India, South Africa, China and Malaysia to treat diabetes. The present study reports the in vitro antioxidant and antidiabetic activities of the major alkaloids isolated from Catharanthus roseus (L.) G. Don leaves extract. Four alkaloids—vindoline I, vindolidine II, vindolicine III and vindolinine IV—were isolated and identified from the dichloromethane extract (DE) of this plant’s leaves. DE and comp...

  12. Binding Parameters of Alkaloids Berberine and Sanguinarine with DNA

    Gumenyuk, V G; Kutovyy, S Yu; Yashchuk, V M; Zaika, L A

    2012-01-01

    We study the interaction of berberine and sanguinarine (plant alkaloids) with DNA in aqueous solutions, by using optical spectroscopy methods (absorption and fluorescence). The dependencies of alkaloid spectral characteristics on the concentration ratio N/c between the DNA base pairs and alkaloid molecules in the solutions are considered, and the manifestations of the alkaloid-DNA binding are revealed. The character of binding is found to depend on N/c. The parameters of the binding of berberine and sanguinarine with DNA are determined, by using the modified Scatchard and McGhee-von Hippel equations

  13. New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

    Plodek, Alois; Bracher, Franz

    2016-01-01

    Secondary metabolites from marine organisms are a rich source of novel leads for drug development. Among these natural products, polycyclic aromatic alkaloids of the pyridoacridine type have attracted the highest attention as lead compounds for the development of novel anti-cancer and anti-infective drugs. Numerous sophisticated total syntheses of pyridoacridine alkaloids have been worked out, and many of them have also been extended to the synthesis of libraries of analogues of the alkaloids. This review summarizes the progress in the chemistry of pyridoacridine alkaloids that was made in the last one-and-a-half decades. PMID:26821033

  14. Analytical methods for determination of alkaloids and saponins from roots of Caulophyllum thalictroids (L) Michx using UPLC HPLC and HPTLC

    A comparison study of analytical methods including HPLC, UPLC and HPTLC are presented in this paper for the determination of major alkaloid and triterpene saponins from the roots of Caulophyllum thalictroides (L.) Michx. (blue cohosh) and dietary supplements claiming to contain blue cohosh. The meth...

  15. The comparative toxicity of a reduced, crude comfrey (Symphytum officinale) alkaloid extract and the pure, comfrey-derived pyrrolizidine alkaloids, lycopsamine and intermedine in chicks (Gallus gallus domesticus).

    Brown, Ammon W; Stegelmeier, Bryan L; Colegate, Steven M; Gardner, Dale R; Panter, Kip E; Knoppel, Edward L; Hall, Jeffery O

    2016-05-01

    Comfrey (Symphytum officinale), a commonly used herb, contains dehydropyrrolizidine alkaloids that, as a group of bioactive metabolites, are potentially hepatotoxic, pneumotoxic, genotoxic and carcinogenic. Consequently, regulatory agencies and international health organizations have recommended comfrey be used for external use only. However, in many locations comfrey continues to be ingested as a tisane or as a leafy vegetable. The objective of this work was to compare the toxicity of a crude, reduced comfrey alkaloid extract to purified lycopsamine and intermedine that are major constituents of S. officinale. Male, California White chicks were orally exposed to daily doses of 0.04, 0.13, 0.26, 0.52 and 1.04 mmol lycopsamine, intermedine or reduced comfrey extract per kg bodyweight (BW) for 10 days. After another 7 days chicks were euthanized. Based on clinical signs of poisoning, serum biochemistry, and histopathological analysis the reduced comfrey extract was more toxic than lycopsamine and intermedine. This work suggests a greater than additive effect of the individual alkaloids and/or a more potent toxicity of the acetylated derivatives in the reduced comfrey extract. It also suggests that safety recommendations based on purified compounds may underestimate the potential toxicity of comfrey. PMID:26177929

  16. New monoterpenoid alkaloids from the aerial parts of Uncaria hirsuta.

    Jia, Jun-Feng; Zhang, Yuan; Huang, Xiao-Jun; Zhang, Sheng-Yuan; Tian, Hai-Yan; Wang, Lei; Ye, Wen-Cai

    2014-01-01

    To investigate the chemical constituents of medicinal plant Uncaria hirsuta, three new monoterpenoid alkaloids, named hirsutanines A-C (1-3), were isolated. Their structures with absolute configurations were elucidated by means of NMR, X-ray diffraction and CD analysis. Compound 3 was the first dimeric monoterpenoid alkaloid obtained from genus Uncaria. PMID:24684175

  17. Effects of Ergot Alkaloids on Bovine Sperm Motility In Vitro

    Ergot alkaloids are synthesized by endophyte-infected (Neotyphodium coenophialum) tall fescue (Lolium arundinaceum (Schreb.) S.J. Darbyshire). Our objective was to determine direct effects of ergot alkaloids (ergotamine, dihydroergotamine and ergonovine) on the motility of bovine spermatozoa in vit...

  18. Studies of interaction between two alkaloids and double helix DNA

    This article presents the study on the interaction of two alkaloids (matrine and evodiamine) and hs-DNA by absorption, fluorescence, circular dichroism (CD), DNA melting and viscosity experiments. The spectroscopic studies suggested that two alkaloids can bind to DNA through an intercalative mode. The viscosity measurement and thermal denaturation also indicated that two alkaloids can intercalate to DNA. The binding constants (KA) and the number of binding sites (n) were determined. At the same time, some significant thermodynamic parameters of the binding of the alkaloids to DNA were obtained. Competitive binding studies revealed that alkaloids had an effect on ethidium bromide (EB) bound DNA. In addition, it was also proved that the fluorescence quenching was influenced by ionic strength. - Highlights: • Interaction between two alkaloids and DNA is studied by spectral methods. • The binding constant and the binding sites between two alkaloids and DNA are obtained. • There are a classical intercalative mode between alkaloids and DNA. • The binding of matrine with DNA is weaker than that of evodiamine. • It is important for us to understand the alkaloids–DNA interactions at a molecular level

  19. Pyrrolizidine alkaloids from Bulgarian species of the genus Senecio

    NADEZHDA KOSTOVA

    2006-12-01

    Full Text Available Nine Bulgarian species from the genus Senecio were studied phytochemically and/or by GC-MS analysis. Senecivernine-N-oxide was isolated and identified by spectral data for the first time. Different types of pyrrolizidine alkaloids were tested for cytotoxicity on murine lymphocytes. At a concentration of 100 µg/ml, the alkaloid retroisosenine showed immunosuppressive effect.

  20. In vitro antibacterial screening of Cryptolepis sanguinolenta alkaloids.

    Paulo, A; Duarte, A; Gomes, E T

    1994-10-01

    The ethanol and aqueous crude extracts and five alkaloids isolated from the roots of Crytolepis sanguinolenta (Lindl.) Schlechter were screened for antibacterial activity against 7 reference strains by the twofold serial broth microdilution assay. The ethanol extract and the alkaloids cryptolepine and cryptoheptine inhibited the growth of all strains tested except that of Pseudomonas aeruginosa. PMID:7853864

  1. Volatiles, A Glutarimide Alkaloid and Antimicrobial Effects of Croton pullei (Euphorbiaceae

    Lourivaldo S. Santos

    2013-03-01

    Full Text Available Chemical investigation of Croton pullei (Euphorbiaceae collected in the Brazilian Amazon region was revisited. The chemical composition of the essential oils of leaves and stems was analyzed by GC/MS. It was found that both the oils comprise mainly terpenes, among which linalool was the major one (24.90 and 39.72%, respectively. Phytochemical investigation of the stem methanol extract led to the isolation of a new natural product from the glutarimide alkaloid group named N-[2,6-dioxo-1-(2-phenylethyl-3-piperidinyl]-acetamide, confirming that C. pullei is a rich source of this class of alkaloids. The hexane and methanol extracts of the stems of C. pullei showed moderate antibacterial and antifungal activity and the highest inhibition was observed when the methanol extract was tested against Staphylococcus aureus CCMB 262 and CCMB 263.

  2. hERG Blockade by Iboga Alkaloids.

    Alper, Kenneth; Bai, Rong; Liu, Nian; Fowler, Steven J; Huang, Xi-Ping; Priori, Silvia G; Ruan, Yanfei

    2016-01-01

    The iboga alkaloids are a class of naturally occurring and synthetic compounds, some of which modify drug self-administration and withdrawal in humans and preclinical models. Ibogaine, the prototypic iboga alkaloid that is utilized clinically to treat addictions, has been associated with QT prolongation, torsades de pointes and fatalities. hERG blockade as IKr was measured using the whole-cell patch clamp technique in HEK 293 cells. This yielded the following IC50 values: ibogaine manufactured by semisynthesis via voacangine (4.09 ± 0.69 µM) or by extraction from T. iboga (3.53 ± 0.16 µM); ibogaine's principal metabolite noribogaine (2.86 ± 0.68 µM); and voacangine (2.25 ± 0.34 µM). In contrast, the IC50 of 18-methoxycoronaridine, a product of rational synthesis and current focus of drug development was >50 µM. hERG blockade was voltage dependent for all of the compounds, consistent with low-affinity blockade. hERG channel binding affinities (K i) for the entire set of compounds, including 18-MC, ranged from 0.71 to 3.89 µM, suggesting that 18-MC binds to the hERG channel with affinity similar to the other compounds, but the interaction produces substantially less hERG blockade. In view of the extended half-life of noribogaine, these results may relate to observations of persistent QT prolongation and cardiac arrhythmia at delayed intervals of days following ibogaine ingestion. The apparent structure-activity relationships regarding positions of substitutions on the ibogamine skeleton suggest that the iboga alkaloids might provide an informative paradigm for investigation of the structural biology of the hERG channel. PMID:25636206

  3. Identification and Characterization of Indole and Oxindole Alkaloids from Leaves of Mitragyna speciosa Korth Using Liquid Chromatography-Accurate QToF Mass Spectrometry.

    Avula, Bharathi; Sagi, Satyanarayanaraju; Wang, Yan-Hong; Wang, Mei; Ali, Zulfiqar; Smillie, Troy J; Zweigenbaum, Jerry; Khan, Ikhlas A

    2015-01-01

    Alkaloids have been reported to be the major physiologically active constituents in Mitragyna. An analytical method was developed to provide an alternative, fast method for characterization of alkaloids from various M. speciosa samples. The separation was achieved using an RP octylsilyl (C8) column, MS detection, and a water-acetonitrile with formic acid gradient as the mobile phase. Ultra-HPLC/quadrupole time-of-flight MS analysis and characterization were performed on 12 corynanthe-type indole/oxindole alkaloids obtained from the leaves of M. speciosa Korth. The indoles and oxindoles had an open E ring with or without substitution occurring at the C9 position. The full single mass spectrum of alkaloids showed a strong signal for the protonated molecule [M+H]+. The product ion spectrum of mitragynine type of alkaloids showed strong response at m/z=174.0901 suggestive of an ion containing an odd number of nitrogen atoms corresponding to formula C11H12NO, which is characteristic of indole alkaloids. A multivariate statistical analysis technique, principal component analysis, was used to show discrimination between the M. speciosa samples. The results indicated that the analytical method is suitable for QC testing of various Mitragyna commercial samples and can be used to evaluate market products purported to contain M. speciosa. PMID:25857873

  4. Significance of saguaro cactus alkaloids in ecology ofDrosophila mettleri, a soil-breeding, cactophilic drosophilid.

    Meyer, J M; Fogleman, J C

    1987-11-01

    Drosophila mettleri is a soil-breeding, cactophilic drosophilid which lives in the Sonoran Desert. Several chemical constituents of cacti in this region have been identified as having major roles in insect-host plant relationships involvingDrosophila. For example, isoquinoline alkaloids, which are present in senita cactus, have been shown to be toxic to seven of the nine species tested. The two tolerant species areD. pachea, the normal resident, andD. mettleri. Necroses of senita cacti are often used as feeding substrates byD. mettleri adults, but this species has never been reared from senita rots. Soil, which have been soaked by juice from saguaro and cardón rots, are the typical breeding substrates of this species. The tissues of both of these cacti also contain alkaloids, chemically related to those in senita, but at much lower concentrations. Alkaloid concentration in saguaro-soaked soil was found to be 1.4-27 times the average concentration in fresh tissue. Alkaloids were extracted from saguaro tissue and used in tests of larva-to-adult viability, developmental rate, and adult longevity. Elevated concentrations of saguaro alkaloids had no significant effect on the longevity ofD. mettleri, but significantly reduced the longevity ofD. nigrospiracula andD. mojavensis, two nonsoil breeding cactophilic species. Viability and developmental rates of all three species were affected, but the effect onD. nigrospiracula was comparatively greater. It is argued that the adaptations that allowD. mettleri to utilize the saguaro soil niche also convey tolerance to alkaloids present in senita tissue. The ability to utilize senita necroses as feeding substrates represents an ecological advantage to D. mettleri, in that the density of potential feeding sites is increased as compared to species which are more specific in their host-plant relationships. PMID:24301541

  5. Antifungal Indole Alkaloids from Winchia calophylla.

    Yang, Mei-Li; Chen, Jia; Sun, Meng; Zhang, Dong-Bo; Gao, Kun

    2016-05-01

    Ten indole alkaloids (1-10) were obtained from an antifungal extract of Winchia calophylla, of which two (2 and 4) were new. N(4)-Methyl-10-hydroxyl-desacetylakuammilin (2) was an akuammiline-type indole alkaloid. N(1)-Methyl-echitaminic acid (4) was an unusual zwitterion with a basic vincorine-type skeleton. This is the first report of 10 in W. calophylla. The structures of all of the compounds were determined based on spectroscopic data, and their bioactivities were assessed. Compound 1 showed potent activity against the plant pathogenic fungi of Penicillium italicum and Fusarium oxysporum f.sp cubens with IC50 s of 10.4 and 11.5 µM, respectively, and 3 inhibited Rhizoctonia solani with an IC50 of 11.7 µM. Compounds 2 and 4 showed weak cytotoxicity against the human leukemic cell line HL-60 in vitro with IC50 s of 51.4 and 75.3 µM, respectively. Compounds 1 and 2 displayed weak activity against acetylcholinesterase with IC50 s around 61.3 and 52.6 µM, respectively. PMID:27002397

  6. Neurotoxic Alkaloids: Saxitoxin and Its Analogs

    Troco K. Mihali

    2010-07-01

    Full Text Available Saxitoxin (STX and its 57 analogs are a broad group of natural neurotoxic alkaloids, commonly known as the paralytic shellfish toxins (PSTs. PSTs are the causative agents of paralytic shellfish poisoning (PSP and are mostly associated with marine dinoflagellates (eukaryotes and freshwater cyanobacteria (prokaryotes, which form extensive blooms around the world. PST producing dinoflagellates belong to the genera Alexandrium, Gymnodinium and Pyrodinium whilst production has been identified in several cyanobacterial genera including Anabaena, Cylindrospermopsis, Aphanizomenon Planktothrix and Lyngbya. STX and its analogs can be structurally classified into several classes such as non-sulfated, mono-sulfated, di-sulfated, decarbamoylated and the recently discovered hydrophobic analogs—each with varying levels of toxicity. Biotransformation of the PSTs into other PST analogs has been identified within marine invertebrates, humans and bacteria. An improved understanding of PST transformation into less toxic analogs and degradation, both chemically or enzymatically, will be important for the development of methods for the detoxification of contaminated water supplies and of shellfish destined for consumption. Some PSTs also have demonstrated pharmaceutical potential as a long-term anesthetic in the treatment of anal fissures and for chronic tension-type headache. The recent elucidation of the saxitoxin biosynthetic gene cluster in cyanobacteria and the identification of new PST analogs will present opportunities to further explore the pharmaceutical potential of these intriguing alkaloids.

  7. Chirality and Numbering of Substituted Tropane Alkaloids

    Philippe Christen

    2011-08-01

    Full Text Available The strict application of IUPAC rules for the numbering of tropane alkaloids is not always applied by authors and there is hence a lot of confusion in the literature. In most cases, the notation of 3, 6/7-disubstituted derivatives has been chosen arbitrarily, based on NMR and MS data, without taking into account the absolute configuration of these two carbons. This paper discusses the problem and the relevance of CD and NMR to determine molecular configurations. We report on the use of 1H-NMR anisochrony (Δd induced by the Mosher’s chiral auxiliary reagents (R-(-- and (S-(+-α-methoxy-α-trifluoromethyl-phenylacetyl chlorides (MTPA-Cl, to determine the absolute configuration of (3R,6R-3α-hydroxy-6b-senecioyloxytropane, a disubstituted tropane alkaloid isolated from the aerial parts of Schizanthus grahamii (Solanaceae. These analytical tools should help future works in correctly assigning the configuration of additional 3, 6/7 disubstituted tropane derivatives.

  8. Improving field production of ergot alkaloids by application of gametocide on rye host plants.

    Hanosová, Helena; Koprna, Radoslav; Valík, Josef; Knoppová, Lucie; Frébort, Ivo; Dzurová, Lenka; Galuszka, Petr

    2015-12-25

    Ergot alkaloids are widely used in the pharmaceutical industry in drug preparations for treating migraines and Parkinson's disease, inducing uterine contraction, and other purposes. Phytopathogenic fungi of the genus Claviceps (e.g. C. purpurea) comprise a major biological source of ergot alkaloids. Worldwide industrial production of these alkaloids derives almost equally from two biotechnological procedures: submerged culture of the fungus in fermenters and field parasitic production in dormant fungal organs known as sclerotia (also termed ergot). Ergot yields from field cultivation are greatly affected by weather and also can be much reduced by pollen contamination from imperfectly male-sterile rye, as only unfertilized ovaries can be infected by C. purpurea spores. Two substances with gametocidal effect - maleic hydrazide and 2-chloroethylphosphonic acid - were tested during three consecutive seasons in small field experiments for the ability to induce or amplify the male sterility of rye as well as the impacts on germination of C. purpurea spores and general vitality of rye host plants. Maleic hydrazide was proven to be a highly effective gametocide on both a fertile rye variety and a variety with imperfectly induced cytoplasmic male sterility. It showed negligible effect on germination of C. purpurea spores. Both accurate dosaging of the active gametocidal compound and timing of the application just 2-3 weeks before onset of anthesis proved crucial to achieving high ergot yield with minimum grain impurities. PMID:25639197

  9. Antidiabetic and antioxidant properties of alkaloids from Catharanthus roseus (L.) G. Don.

    Tiong, Soon Huat; Looi, Chung Yeng; Hazni, Hazrina; Arya, Aditya; Paydar, Mohammadjavad; Wong, Won Fen; Cheah, Shiau-Chuen; Mustafa, Mohd Rais; Awang, Khalijah

    2013-01-01

    Catharanthus roseus (L.) G. Don is a herbal plant traditionally used by local populations in India, South Africa, China and Malaysia to treat diabetes. The present study reports the in vitro antioxidant and antidiabetic activities of the major alkaloids isolated from Catharanthus roseus (L.) G. Don leaves extract. Four alkaloids--vindoline I, vindolidine II, vindolicine III and vindolinine IV--were isolated and identified from the dichloromethane extract (DE) of this plant's leaves. DE and compounds I-III were not cytotoxic towards pancreatic β-TC6 cells at the highest dosage tested (25.0 µg/mL). All four alkaloids induced relatively high glucose uptake in pancreatic β-TC6 or myoblast C2C12 cells, with III showing the highest activity. In addition, compounds II-IV demonstrated good protein tyrosine phosphatase-1B (PTP-1B) inhibition activity, implying their therapeutic potential against type 2 diabetes. III showed the highest antioxidant potential in ORAC and DPPH assays and it also alleviated H₂O₂-induced oxidative damage in β-TC6 cells at 12.5 µg/mL and 25.0 µg/mL. PMID:23955322

  10. Effects of Microdesmis keayana alkaloids on vascular parameters of erectile dysfunction.

    Zamblé, Alexis; Martin-Nizard, Françoise; Sahpaz, Sevser; Reynaert, Marie-Line; Staels, Bart; Bordet, Régis; Duriez, Patrick; Gressier, Bernard; Bailleul, François

    2009-06-01

    Microdesmis keayana (Pandaceae) is an African tropical plant whose roots are used in traditional medicine for erection impairment but the compounds responsible for its action are unknown. Two major alkaloids recently isolated from the roots of M. keayana, keayanidine B and keayanine, were tested for vasorelaxing properties using isolated rat aortic rings precontracted by phenylephrine to confirm its traditional use. Influence of the alkaloids on the endothelial production of endothelial nitric oxide synthase (eNOS) was measured by quantitative polymerase chain reaction (QPCR) analysis. Scavenging activities were assessed versus 1,1-diphenyl-2-picrylhydrazyle (DPPH) and reactive oxygen species (ROS) such as superoxide anion (O(2)(*-) and hydrogen peroxide (H(2)O(2)) in cell-free and cellular systems. The results showed that keayanidine B and keayanine had significant vasorelaxing properties. This effect could be due to their strong antioxidant activity versus O(2)(*-) and H(2)O(2) and to their stimulation of eNOS mRNA expression. Therefore these alkaloids could indirectly stimulate NO production in the vascular bed and would explain the traditional use of M. keayana in erectile dysfunction. PMID:19107738

  11. Antiplasmodial activity of Cryptolepis sanguinolenta alkaloids from leaves and roots.

    Paulo, A; Gomes, E T; Steele, J; Warhurst, D C; Houghton, P J

    2000-02-01

    The roots of Cryptolepis sanguinolenta have been investigated for their chemical composition since 1931 but so far no studies on the leaves have been reported although they are used in traditional medicine in Guinea-Bissau. Two new alkaloids identified as cryptolepinoic acid (1) and methyl cryptolepinoate (2) and the known alkaloids cryptolepine (4), hydroxycryptolepine (5/5a) and quindoline (6), were isolated from the ethanolic and chlorophormic leaf extracts. Aqueous and ethanolic extracts of the leaves and roots and seven alkaloids isolated from those extracts were tested in vitro against Plasmodium falciparum K1 (multidrug-resistant strain) and T996 (chloroquine-sensitive clone). All the extracts were shown to give 90% inhibition of P. falciparum K1 growth at concentrations < 23 micrograms/ml. Cryptolepine (4) was the most active alkaloid tested with IC50 values (0.23 microM to K1; 0.059 microM to T996) comparable with chloroquine (0.26 microM to K1; 0.019 microM to T996). The indolobenzazepine alkaloid cryptoheptine (7) was the second most active with IC50 values of 0.8 microM (K1) and 1.2 microM (T996). Cryptolepinoic acid (1) showed no significant activity while its ethyl ester derivative 3 was active against P. falciparum K1 (IC50 = 3.7 microM). All the indoloquinoline alkaloids showed cross-resistance with chloroquine but not the indolobenzazepine alkaloid 7. It was noticed that alkaloids with weakly basic characteristics were active whereas other structurally related alkaloids with different acid-base profiles were inactive. These observations are in agreement with the antimalarial mechanism of action for quinolines. PMID:10705730

  12. Analytical chemical study of alkaloid fraction of methanolic extract of Croton baillonianus (AUBL) leaves

    The objective of the present study has been to extract and isolate the alkaloids from leaves of Croton baillonianus, corresponding to the methanolic extract by exclusion chromatography with Sephadex LH-20 followed by a purification by high performance liquid chromatography, obtaining six alkaloids. Two low polarity alkaloid and two glycoside alkaloids were analyzed by Electronic System impact mass spectrometry; these alkaloids belong to bencylisoquinolinic type; the study has connection to the determination of its antioxidant, antiulcerose and cytotoxic properties. (author).

  13. The distribution of inole alkaloids in different organs of Catharanthus roseus G. Don. (Vinca rosea L)

    Hassan Ebrahimzadeh; Azra Ataei -Azimi4 Mohammad-Reza Noori-Dafoi

    1996-01-01

    The study of alkaloid extract of the leaf of Vinca rosea by TLC showed the existence of 13 bands, 7 bands of them were: Serpentine, Vincristine, Vinblastine, Ajmaline, Catharantine, Vindoline and Ajmalicine. The existence of these 7 alkaloids was confirmed in the young leaves, old leaves and the roots of the plant by HPLC. Furthermore, two alkaloids with the short retention times and one alkaloid with the medium retention time in the young leaf, three alkaloids with the short retention time a...

  14. Qualitative determination of indole alkaloids of Tabernaemontana fuchsiaefolia (Apocynaceae)

    This paper describes a fast and efficient procedure to separate and identify indole alkaloids from the ethanolic extract of Tabernaemontana fuchsiaefolia (Apocynaceae). The alkaloidal fractions obtained from ethanolic extracts of leaves and stem barks and root barks were fractioned and analyzed by Thin-Layer Chromatography (TLC) and by Gas Chromatography coupled to Mass Spectrometry (GC-MS). The following indole alkaloids were identified: ibogamine, coronaridine, ibogaine pseudoindoxyl, voacangine hydroxyindolenine, voacangine pseudoindoxyl, tabernanthine, catharanthine, voacangine, 19-oxovoacangine, 10-hydroxycoronaridine, affinisine, 16-epi-affinine, voachalotine, ibogaline, and conopharyngine. (author)

  15. Qualitative determination of indole alkaloids of Tabernaemontana fuchsiaefolia (Apocynaceae)

    Zocoler, Marcos A. [Universidade do Oeste Paulista, Presidente Prudente, SP (Brazil). Dept. de Farmacos e Medicamentos; Oliveira, Arildo J.B. de [Universidade Estadual de Maringa, PR (Brazil). Dept. de Farmacia e Farmacologia; Sarragiotto, Maria H.; Grzesiuk, Viviane L.; Vidotti, Gentil J. [Universidade Estadual de Maringa, PR (Brazil). Dept. de Quimica]. E-mail: gjvidotti@uem.br

    2005-11-15

    This p describes a fast and efficient procedure to separate and identify indole alkaloids from the ethanolic extract of Tabernaemontana fuchsiaefolia (Apocynaceae). The alkaloidal fractions obtained from ethanolic extracts of leaves and stem barks and root barks were fractioned and analyzed by Thin-Layer Chromatography (TLC) and by Gas Chromatography coupled to Mass Spectrometry (GC-MS). The following indole alkaloids were identified: ibogamine, coronaridine, ibogaine pseudoindoxyl, voacangine hydroxyindolenine, voacangine pseudoindoxyl, tabernanthine, catharanthine, voacangine, 19-oxovoacangine, 10-hydroxycoronaridine, affinisine, 16-epi-affinine, voachalotine, ibogaline, and conopharyngine. (author)

  16. Two New N-Oxide Alkaloids from Stemona cochinchinensis

    Ligen Lin

    2014-12-01

    Full Text Available Two new N-oxide alkaloids with pyrrolo[1,2-α]azepine skeleton, namely isoneostemocochinine-N-oxide (1 and neostemocochinine-N-oxide (2, as well as three known alkaloids with pyrido[1,2-α]azepine skeletons, were isolated and identified from the roots of Stemona cochinchinensis (Stemonaceae. The structures of these compounds were elucidated by 1D- and 2D-NMR spectra and other spectroscopic studies. Additionally, the 1H- and 13C-NMR characteristic of N-oxide Stemona alkaloids was summarized. Stemokerrin showed potent anti-tussive activity on citric acid-induced guinea pig model.

  17. Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution.

    Nge, Choy-Eng; Chong, Kam-Weng; Thomas, Noel F; Lim, Siew-Huah; Low, Yun-Yee; Kam, Toh-Seok

    2016-05-27

    Ten new indole alkaloids (1-10) comprising five ibogan, two aspidosperman, one vincamine, and two bisindole alkaloids, in addition to 32 known alkaloids, were isolated from the stem-bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the NMR and MS data and, in five instances (1, 3, 5, 6, 8), confirmed by X-ray diffraction analysis. Two of the iboga alkaloids, conodusines B (2) and C (3), and the iboga-containing bisindole tabernamidine B (10) are notable for the presence of an α-substituted acetyl group at C-20 of the iboga carbon skeleton. The iboga alkaloid (+)-conodusine E (5) had MS and NMR data that were identical to those of (-)-ervatamine I, recently isolated from Ervatamia hainanensis. Establishment of the absolute configuration of (+)-conodusine E (5) was based on analysis of the ECD data, correlation with (-)-heyneanine, and X-ray analysis, which showed that (+)-5 belongs to the same enantiomeric series as exemplified by (-)-coronaridine. The configuration at C-20' of the previously reported Tabernaemontana bisindole alkaloid 19'-oxotabernamine (renamed tabernamidine B) required revision based on the present results. Several of the bisindoles showed pronounced in vitro growth inhibitory activity against drug-sensitive and vincristine-resistant KB cells. PMID:27077800

  18. Antifouling Alkaloids from Crinum augustum (Amaryllidaceae

    John Refaat

    2009-01-01

    Full Text Available Fractionation and purification of the ethanolic extract of the bulbs of Crinum augustum Rox. (Amaryllidaceae cultivated in Egypt yielded five alkaloids 6-methoxy-crinamine (1 , crinamine (2 , buphanisine (3 , ungeremine (4 , and hippadine (5 ; two fatty acid derivatives: myristic acid ethyl ester (6 and palmitic acid ethyl ester (7 ; four terpenoidal and steroidal compounds: ursolic acid (8 , β-sitosterol-O- β glucopyranoside (9 and mixture of β--sitosterol (10 and stigmasterol (11 . The structures of all compounds were determined by interpretation of their spectroscopic data; 1D ( 1 H and 13 C, 2D (HSQC, COSY, DQF, NOE and HMBC NMR; MS and UV analyses. The compounds (1 -4 and (6-8 were tested towards biofouling activity using larvae of barnacle Balance amphitrie. Significant activities of 1, 2 and 3 with EC 50 1.8, 1.2 and 0.75 μg/mL respectively, were observed.

  19. Investigation of Aconitine-type Alkaloids from Processed Tuber of Aconitum carmiechaeli by HPLC-ESI-MS/MSn

    YUE Hao; PI Zi-feng; ZHAO Yu-feng; SONG Feng-rui; LIU Zhi-qiang; LIU Shu-ying

    2007-01-01

    @@ Introduction Aconitine-type alkaloids isolated from the roots of Aconitum carmiechaeli show a potential toxicity and a broad spectrum of bioactivity[1-4]. On the basis of the C8-substituent of C19-diterpenoid skeleton, aconitinetype alkaloids can be divided into diester-diterpenoid alkaloids( DDAs), monoester-diterpenoid alkaloids(MDAs), and lipo-alkaloids( Fig. 1 ).

  20. Two bromotyrosine alkaloids from the sponge Psammaplysilla purpurea

    Tilvi, S.; Parameswaran, P.S.; Naik, C.G.

    The sponge Psammaplysilla purpurea (Order: Verongidae, Family: Aplysinellidae) is a well known source for several bromotyrosine alkaloids of unique structural features and exhibiting promising biological activities such as cytotoxicity...

  1. A New Binary Carbazole Alkaloid from Murraya koenigii

    2002-01-01

    A new binary carbazole alkaloid, 8, 8"-biskoenigine (1), along with its monomer,kocnigine, was isolated from the dried leaves of Murraya koenigii collected in Xishuangbanna,Yunnan province. The structure of 1 was established by spectroscopic methods.

  2. Total synthesis, biosynthesis and biological profiles of clavine alkaloids.

    McCabe, Stephanie R; Wipf, Peter

    2016-07-01

    This review highlights noteworthy synthetic and biological aspects of the clavine subfamily of ergot alkaloids. Recent biosynthetic insights have laid the groundwork for a better understanding of the diverse biological pathways leading to these indole derivatives. Ergot alkaloids were among the first fungal-derived natural products identified, inspiring pharmaceutical applications in CNS disorders, migraine, infective diseases, and cancer. Pergolide, for example, is a semi-synthetic clavine alkaloid that has been used to treat Parkinson's disease. Synthetic activities have been particularly valuable to facilitate access to rare members of the Clavine family and empower medicinal chemistry research. Improved molecular target identification tools and a better understanding of signaling pathways can now be deployed to further extend the biological and medical utility of Clavine alkaloids. PMID:27215547

  3. Leishmanicidal Evaluation of Tetrahydroprotoberberine and Spirocyclic Erythrina-Alkaloids

    Daniel R. Callejon

    2014-05-01

    Full Text Available Leishmaniasis is one of the World’s most problematic diseases in developing countries. Traditional medicines to treat leishmaniasis have serious side effects, as well as significant parasite resistance problems. In this work, two alkaloids 1 and 2 were obtained from Corydalis govaniana Wall and seven alkaloids 3–9, were obtained from Erythrina verna. The structures of the compounds were confirmed by mass spectrometry and 1D- and 2D-NMR spectroscopy. The leishmanicidal activity of compounds 1–9 against Leishmania amazonensis was tested on promastigote forms and cytotoxicity against J774 (macrophage cell line was assessed in vitro. Compound 1 showed potent activity (IC50 = 0.18 µg/mL, compared with the standard amphotericin B (IC50 = 0.20 µg/mL. The spirocyclic erythrina-alkaloids showed lower leishmanicidal activity than dibenzoquinolizine type alkaloids.

  4. A new phenanthridine alkaloid from Hymenocallis x festalis.

    Hohmann, J; Forgo, P; Szabó, P

    2002-12-01

    Investigation of the alkaloid fraction of the bulbs of Hymenocallis x festalis yielded a new natural product, 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (1). The structure was elucidated on the basis of spectroscopic data. PMID:12490249

  5. Ergot alkaloids induce vasoconstriction of bovine foregut vasculature

    Alkaloids produced by the Neotyphodium coenophialum endophyte in association with tall fescue (Lolium arundinaceum) are imputed to cause peripheral symptoms of fescue toxicosis. We hypothesized that theses compounds could correspondingly affect foregut vasculature. The objective of this study was to...

  6. New bromotyrosine alkaloids from the marine sponge Psammaplysilla purpurea

    Tilvi, S.; Rodrigues, C.; Naik, C.G.; Parameswaran, P.S.; Wahidullah, S.

    Seven new bromotyrosine alkaloids Purpurealidin A, B, C, D, F, G, H and the known compounds Purealidin Q, Purpurealidin E, 16-Debromoaplysamine-4 and Purpuramine I have been isolated from the marine sponge Psammaplysilla purpurea. Their structure...

  7. Quinolizidines alkaloids: Petrosin and xestospongins from the sponge Oceanapia sp.

    Singh, K.S.; Das, B.; Naik, C.G.

    having di-hetro atom rings, from the ethyl acetate extract of the sponge. The compounds exhibited moderate to high activities against some microorganisms and clinical isolates. The structures of the alkaloids were elucidated by NMR and ESIMS spectroscopic...

  8. Reviewing colchicaceae alkaloids – perspectives of evolution on medicinal chemistry

    Larsson, Sonny; Rønsted, Nina

    2014-01-01

    . In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Following on the trends of utilizing evolutionary reasoning in inferring mechanisms in eg. drug resistance...

  9. Microcalorimetry studies of the antimicrobial actions of Aconitum alkaloids.

    Shi, Yan-bin; Liu, Lian; Shao, Wei; Wei, Ting; Lin, Gui-mei

    2015-08-01

    The metabolic activity of organisms can be measured by recording the heat output using microcalorimetry. In this paper, the total alkaloids in the traditional Chinese medicine Radix Aconiti Lateralis were extracted and applied to Escherichia coli and Staphylococcus aureus. The effect of alkaloids on bacteria growth was studied by microcalorimetry. The power-time curves were plotted with a thermal activity monitor (TAM) air isothermal microcalorimeter and parameters such as growth rate constant (μ), peak-time (Tm), inhibitory ratio (I), and enhancement ratio (E) were calculated. The relationships between the concentration of Aconitum alkaloids and μ of E. coli or S. aureus were discussed. The results showed that Aconitum alkaloids had little effect on E. coli and had a potentially inhibitory effect on the growth of S. aureus. PMID:26238544

  10. Gastric and Duodenal Antiulcer Activity of Alkaloids: A Review

    José Maria Barbosa-Filho

    2008-12-01

    Full Text Available Peptic ulcer disease is a deep gastrointestinal erosion disorder that involves the entire mucosal thickness and can even penetrate the muscular mucosa. Numerous natural products have been evaluated as therapeutics for the treatment of a variety of diseases, including this one. These products usually derive from plant and animal sources that contain active constituents such as alkaloids, flavonoids, terpenoids, tannins and others. The alkaloids are natural nitrogen-containing secondary metabolites mostly derived from amino acids and found in about 20% of plants. There has been considerable pharmacological research into the antiulcer activity of these compounds. In this work we review the literature on alkaloids with antiulcer activity, which covers about sixty-one alkaloids, fifty-five of which have activity against this disease when induced in animals.

  11. NEW NORDITERPENOID ALKALOIDS FROM THE ROOTS OF ACONITUM GENICULATUM

    ZHENG-BANG LI; LIANG XU; XI-XIAN JIAN; FENG-PENG WANG

    2001-01-01

    Four new norditerpenoid alkaloids, geniculatines A (1), B (4), C (7) and D (8), were isolated from the roots of Aconitum geniculatum Fletcher, and their structures were elucidated by spectral methods.

  12. 3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens.

    S. C. Liu; Oguntimein, B; Hufford, C D; Clark, A M

    1990-01-01

    Further examination of the active ethanolic extract of the root bark of Cleistopholis patens by using bioassay-directed fractionation resulted in the isolation of a new alkaloid, 3-methoxysampangine (compound I), together with three known alkaloids, eupolauridine (compound II), liriodenine (compound III), and eupolauridine N-oxide (compound IV). The proposed structure of compound I was based on its physicochemical properties and spectral data. 3-Methoxysampangine exhibited significant antifun...

  13. Initial Studies on Alkaloids from Lombok Medicinal Plants

    John B. Bremner; Surya Hadi

    2001-01-01

    Initial investigation of medicinal plants from Lombok has resulted in the collection of 100 plant species predicted to have antimicrobial, including antimalarial, properties according to local medicinal uses. These plants represent 49 families and 80 genera; 23% of the plants tested positively for alkaloids. Among the plants testing positive, five have been selected for further investigation involving structure elucidation and antimicrobial testing on the extracted alkaloids. Initial work on ...

  14. Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids.

    Zhao, Gaoyuan; Xie, Xingang; Sun, Haiyu; Yuan, Ziyun; Zhong, Zhuliang; Tang, Shouchu; She, Xuegong

    2016-05-20

    We present the application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids: (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D. In particular, tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic transformations into other iboga-type alkaloids. PMID:27160167

  15. Pyrrolizidine alkaloid poisoning of sheep in New South Wales.

    Seaman, J T

    1987-06-01

    Pyrrolizidine alkaloid poisoning of sheep in New South Wales was reviewed, based on the records of the New South Wales Department of Agriculture's Regional Veterinary Laboratories. The plant species causing significant mortalities were Echium plantagineum and Heliotropium europaeum. The syndrome of hepatogenous chronic copper poisoning was more frequently diagnosed than primary pyrrolizidine alkaloid poisoning, particularly when grazing E. plantagineum. The data indicated that adult crossbred ewes were the most commonly affected class of sheep. PMID:3632498

  16. Genetics, Genomics and Evolution of Ergot Alkaloid Diversity

    Carolyn A. Young

    2015-04-01

    Full Text Available The ergot alkaloid biosynthesis system has become an excellent model to study evolutionary diversification of specialized (secondary metabolites. This is a very diverse class of alkaloids with various neurotropic activities, produced by fungi in several orders of the phylum Ascomycota, including plant pathogens and protective plant symbionts in the family Clavicipitaceae. Results of comparative genomics and phylogenomic analyses reveal multiple examples of three evolutionary processes that have generated ergot-alkaloid diversity: gene gains, gene losses, and gene sequence changes that have led to altered substrates or product specificities of the enzymes that they encode (neofunctionalization. The chromosome ends appear to be particularly effective engines for gene gains, losses and rearrangements, but not necessarily for neofunctionalization. Changes in gene expression could lead to accumulation of various pathway intermediates and affect levels of different ergot alkaloids. Genetic alterations associated with interspecific hybrids of Epichloë species suggest that such variation is also selectively favored. The huge structural diversity of ergot alkaloids probably represents adaptations to a wide variety of ecological situations by affecting the biological spectra and mechanisms of defense against herbivores, as evidenced by the diverse pharmacological effects of ergot alkaloids used in medicine.

  17. Genetics, Genomics and Evolution of Ergot Alkaloid Diversity

    Young, Carolyn A.; Schardl, Christopher L.; Panaccione, Daniel G.; Florea, Simona; Takach, Johanna E.; Charlton, Nikki D.; Moore, Neil; Webb, Jennifer S.; Jaromczyk, Jolanta

    2015-01-01

    The ergot alkaloid biosynthesis system has become an excellent model to study evolutionary diversification of specialized (secondary) metabolites. This is a very diverse class of alkaloids with various neurotropic activities, produced by fungi in several orders of the phylum Ascomycota, including plant pathogens and protective plant symbionts in the family Clavicipitaceae. Results of comparative genomics and phylogenomic analyses reveal multiple examples of three evolutionary processes that have generated ergot-alkaloid diversity: gene gains, gene losses, and gene sequence changes that have led to altered substrates or product specificities of the enzymes that they encode (neofunctionalization). The chromosome ends appear to be particularly effective engines for gene gains, losses and rearrangements, but not necessarily for neofunctionalization. Changes in gene expression could lead to accumulation of various pathway intermediates and affect levels of different ergot alkaloids. Genetic alterations associated with interspecific hybrids of Epichloë species suggest that such variation is also selectively favored. The huge structural diversity of ergot alkaloids probably represents adaptations to a wide variety of ecological situations by affecting the biological spectra and mechanisms of defense against herbivores, as evidenced by the diverse pharmacological effects of ergot alkaloids used in medicine. PMID:25875294

  18. Coptis chinensis alkaloids exert anti-adipogenic activity on 3T3-L1 adipocytes by downregulating C/EBP-α and PPAR-γ.

    Choi, Jae Sue; Kim, Ji-Hye; Ali, Md Yousof; Min, Byung-Sun; Kim, Gun-Do; Jung, Hyun Ah

    2014-10-01

    Obesity is a complex, multifactorial, and chronic disease that increases the risk for type 2 diabetes, coronary heart disease and hypertension, and has become a major worldwide health problem. Developing novel anti-obesity drugs from natural products is a promising solution to the global health problem of obesity. While screening anti-obesity potentials of natural products, the methanol extract of the rhizome of Coptis chinensis (Coptidis Rhizoma) was found to significantly inhibit adipocyte differentiation and lipid contents in 3T3-L1 cells, as assessed by Oil-Red O staining. Five known alkaloids, berberine, epiberberine, coptisine, palmatine, and magnoflorine, were isolated from the n-BuOH fraction of the methanol extract of Coptidis Rhizoma. We determined the chemical structure of these alkaloids through comparisons of published nuclear magnetic resonance (NMR) spectral data. Furthermore, we screened these alkaloids for their ability to inhibit adipogenesis over a range of concentrations (12.5-50 μM). All five Coptidis Rhizoma alkaloids significantly inhibited lipid accumulation in 3T3-L1 cells without affecting cell viability in a concentration dependent manner. In addition, the five alkaloids significantly reduced the expression levels of several adipocyte marker genes including proliferator activated receptor-γ (PPAR-γ) and CCAAT/enhancer-binding protein-α (C/EBP-α). In the present study, we found that the isolated alkaloids inhibited adipogenesis in a dose-dependent manner in 3T3-L1 cells; this inhibition was attributed to their abilities to downregulate the protein levels of the adipocyte marker proteins PPAR-γ and C/EBP-α. Thus, these results suggest that Coptidis Rhizoma extract and its isolated alkaloids may be of therapeutic interest with respect to the treatment of obesity. PMID:25128422

  19. Effect of Iboga alkaloids on µ-opioid receptor-coupled G protein activation.

    Tamara Antonio

    Full Text Available OBJECTIVE: The iboga alkaloids are a class of small molecules defined structurally on the basis of a common ibogamine skeleton, some of which modify opioid withdrawal and drug self-administration in humans and preclinical models. These compounds may represent an innovative approach to neurobiological investigation and development of addiction pharmacotherapy. In particular, the use of the prototypic iboga alkaloid ibogaine for opioid detoxification in humans raises the question of whether its effect is mediated by an opioid agonist action, or if it represents alternative and possibly novel mechanism of action. The aim of this study was to independently replicate and extend evidence regarding the activation of μ-opioid receptor (MOR-related G proteins by iboga alkaloids. METHODS: Ibogaine, its major metabolite noribogaine, and 18-methoxycoronaridine (18-MC, a synthetic congener, were evaluated by agonist-stimulated guanosine-5´-O-(γ-thio-triphosphate ([(35S]GTPγS binding in cells overexpressing the recombinant MOR, in rat thalamic membranes, and autoradiography in rat brain slices. RESULTS AND SIGNIFICANCE: In rat thalamic membranes ibogaine, noribogaine and 18-MC were MOR antagonists with functional Ke values ranging from 3 uM (ibogaine to 13 uM (noribogaine and 18MC. Noribogaine and 18-MC did not stimulate [(35S]GTPγS binding in Chinese hamster ovary cells expressing human or rat MORs, and had only limited partial agonist effects in human embryonic kidney cells expressing mouse MORs. Ibogaine did not did not stimulate [(35S]GTPγS binding in any MOR expressing cells. Noribogaine did not stimulate [(35S]GTPγS binding in brain slices using autoradiography. An MOR agonist action does not appear to account for the effect of these iboga alkaloids on opioid withdrawal. Taken together with existing evidence that their mechanism of action also differs from that of other non-opioids with clinical effects on opioid tolerance and withdrawal, these

  20. Volatiles, A Glutarimide Alkaloid and Antimicrobial Effects of Croton pullei (Euphorbiaceae)

    Lourivaldo S. Santos; Ana Paula T. Uetanabaro; Isabella S. Araújo; Zoghbi, Maria das Graças B.; Giselle M. S. P. Guilhon; Peixoto, Rosana N.S.; Brasil, Davi do S.B.

    2013-01-01

    Chemical investigation of Croton pullei (Euphorbiaceae) collected in the Brazilian Amazon region was revisited. The chemical composition of the essential oils of leaves and stems was analyzed by GC/MS. It was found that both the oils comprise mainly terpenes, among which linalool was the major one (24.90 and 39.72%, respectively). Phytochemical investigation of the stem methanol extract led to the isolation of a new natural product from the glutarimide alkaloid group named N-[2,6-dioxo-1-(2-p...

  1. Analysis of Norditerpenoid Alkaloids Extracted from Aconitum sinomantanum Nakai by Electrospray Ionization Tandem Mass Spectrometry

    2006-01-01

    Electrospray ionization mass spectrometry(ESI-MS) was applied simultaneously in determining norditerpenoid alkaloids from the roots of Aconitum sinomantanum Nakai (RAS) based on molecular mass information. The tandem mass spectra(ESI-MSn) provided the alkaloidal structural information, through which the existence of these alkaloids was further confirmed. Accordingly, six known norditerpenoid alkaloids were simultaneously determined on the basis of their ESI-MSn spectra. Furthermore, based on the diagnostic fragmentation pathways of alkaloidal MSn, a rapid method for direct detection and characterization of alkaloids from an ethanolic extract of RAS was described.

  2. Astonishing diversity of natural surfactants: 6. Biologically active marine and terrestrial alkaloid glycosides.

    Dembitsky, Valery M

    2005-11-01

    This review article presents 209 alkaloid glycosides isolated and identified from plants, microorganisms, and marine invertebrates that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active glycosides have good potential for future chemical preparation of compounds useful as antioxidants, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been subdivided into several groups, including: acridone; aporphine; benzoxazinoid; ergot; indole; enediyne alkaloidal antibiotics; glycosidic lupine alkaloids; piperidine, pyridine, pyrrolidine, and pyrrolizidine alkaloid glycosides; glycosidic quinoline and isoquinoline alkaloids; steroidal glycoalkaloids; and miscellaneous alkaloid glycosides. PMID:16459921

  3. Evaluation of tobacco (Nicotiana tabacum L. cv. Petit Havana SR1) hairy roots for the production of geraniol, the first committed step in terpenoid indole alkaloid pathway

    Ritala, A.; Dong, L.; Imseng, N.; Seppanen-Laakso, T.; Vasilev, N.; Krol, van der A.R.; Rischer, H.; Maaheimo, H.; Virkki, A.; Brandli, J.; Schillberg, S.; Eibl, R.; Bouwmeester, H.J.; Oksman-Caldentey, K.M.

    2014-01-01

    The terpenoid indole alkaloids are one of the major classes of plant-derived natural products and are well known for their many applications in the pharmaceutical, fragrance and cosmetics industries. Hairy root cultures are useful for the production of plant secondary metabolites because of their ge

  4. Toward the ABCD Core of the Calyciphylline A-Type Daphniphyllum Alkaloids: Solvent non-Innocence in Neutral Aminyl Radical Cyclizations

    Stockdill, Jennifer L.; Lopez, Alberto M.; Ibrahim, Ahmad A.

    2015-01-01

    The Daphniphyllum alkaloids remain an attractive target in the synthetic community because of their unique framework and promising biological activities. We have shown that the ABC core of the calyciphylline A-type alkaloids can be rapidly accessed via the tandem cyclization of a neutral aminyl radical with a polarized cyclic olefin. Deuterium labeling experiments and reactions omitting a tin hydride reagent suggest that the solvent is the major source of the terminating hydrogen atom in the cyclization cascade. Incorporation of an internal alkyne in the radical pathway was tolerated in the reaction, and it provided the necessary atoms to enable completion of the D ring of the calyciphylline A-type alkaloids. PMID:26028785

  5. Alkaloids and athlete immune function: caffeine, theophylline, gingerol, ephedrine, and their congeners.

    Senchina, David S; Hallam, Justus E; Kohut, Marian L; Nguyen, Norah A; Perera, M Ann d N

    2014-01-01

    Plant alkaloids are found in foods, beverages, and supplements consumed by athletes for daily nutrition, performance enhancement, and immune function improvement. This paper examined possible immunomodulatory roles of alkaloids in exercise contexts, with a focus on human studies. Four representative groups were scrutinized: (a) caffeine (guaranine, mateine); (b) theophylline and its isomers, theobromine and paraxanthine; (c) ginger alkaloids including gingerols and shogaol; and (d) ephedra alkaloids such as ephedrine and pseudoephedrine. Emerging or prospective alkaloid sources (Goji berry, Noni berry, and bloodroot) were also considered. Human in vitro and in vivo studies on alkaloids and immune function were often conflicting. Caffeine may be immunomodulatory in vivo depending on subject characteristics, exercise characteristics, and immune parameters measured. Caffeine may exhibit antioxidant capacities. Ginger may exert in vivo anti-inflammatory effects in certain populations, but it is unclear whether these effects are due to alkaloids or other biochemicals. Evidence for an immunomodulatory role of alkaloids in energy drinks, cocoa, or ephedra products in vivo is weak to nonexistent. For alkaloid sources derived from plants, variability in the reviewed studies may be due to the presence of unrecognized alkaloids or non-alkaloid compounds (which may themselves be immunomodulatory), and pre-experimental factors such as agricultural or manufacturing differences. Athletes should not look to alkaloids or alkaloid-rich sources as a means of improving immune function given their inconsistent activities, safety concerns, and lack of commercial regulation. PMID:24974722

  6. Major depression

    Depression - major; Depression - clinical; Clinical depression; Unipolar depression; Major depressive disorder ... Doctors do not know the exact causes of depression. It is believed that chemical changes in the ...

  7. Alkaloids of the Annonaceae: occurrence and a compilation of their biological activities.

    Lúcio, Ana Silvia Suassuna Carneiro; Almeida, Jackson Roberto Guedes da Silva; Da-Cunha, Emídio Vasconcelos Leitão; Tavares, Josean Fechine; Barbosa Filho, Jos Maria

    2015-01-01

    This chapter presents an overview of the chemistry and pharmacology of the alkaloids found in species of the Annonaceae family. The occurrence of alkaloids from Annonaceae species, as well as their chemical structures and pharmacological activities are summarized in informative and easy-to-understand tables. Within the Annonaceae family, the genera Annona, Duguetia, and Guatteria have led to many important publications. Valuable and comprehensive information about the structure of these alkaloids is provided. The alkaloids of the aporphine type represent the predominant group in this family. Many of the isolated alkaloids exhibit unique structures. In addition to the chemical structures, the pharmacological activities of some alkaloids are also presented in this chapter. Thus, the leishmanicidal, antimicrobial, antitumor, cytotoxic, and antimalarial activities observed for these alkaloids are highlighted. The chapter is presented as a contribution for the scientific community, mainly to enable the search for alkaloids in species belonging to the Annonaceae family. PMID:25845063

  8. Antiparasitic activities of acridone alkaloids from Swinglea glutinosa (Bl.) Merr

    Eleven acridone alkaloids isolated from Swinglea glutinosa (Bl.) Merr. were examined for in vitro activity against chloroquine-sensitive Plasmodium falciparum 3D7, Trypanosoma brucei rhodesiense STIB900 and Leishmania donovani L82. An assay with KB cells was developed in order to compare in vitro toxicity of alkaloids with the selective action on the parasites. Nine of the compounds had IC50 values ranging from 0.3 to 11.6 μM against P. falciparum. In contrast, a small number of compounds showed significant activity against T. brucei rhodesiense and none had activity against L. donovani. Among the alkaloids three had IC50 50 < 10 μM. The characterization of the acridone alkaloids, 1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9 (10H)-one (1), 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-methoxy-10-methylfuro [3,2-b] acridin-5(10H)-one (2) and 3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2Hpyrano[ 2,3-a]acridin-12(7H)-one (3), is discussed, as well as the structure-activity relationship of all compounds assayed. Isolation and spectral data of alkaloids 1-3 are described for the first time although their cytotoxicities to cancer cells have been described before. (author)

  9. Ornithine Decarboxylase, Polyamines, and Pyrrolizidine Alkaloids in Senecio and Crotalaria

    Birecka, Helena; Birecki, Mieczyslaw; Cohen, Eric J.; Bitonti, Alan J.; McCann, Peter P.

    1988-01-01

    When tested for ornithine and arginine decarboxylases, pyrrolizidine alkaloid-bearing Senecio riddellii, S. longilobus (Compositae), and Crotalaria retusa (Leguminosae) plants exhibited only ornithine decarboxylase activity. This contrasts with previous studies of four species of pyrrolizidine alkaloid-bearing Heliotropium (Boraginaceae) in which arginine decarboxylase activity was very high relative to that of ornithine decarboxylase. Unlike Heliotropium angiospermum and Heliotropium indicum, in which endogenous arginine was the only detectable precursor of putrescine channeled into pyrrolizidines, in the species studied here—using difluoromethylornithine and difluoromethylarginine as the enzyme inhibitors—endogenous ornithine was the main if not the only precursor of putrescine converted into the alkaloid aminoalcohol moiety. In S. riddellii and C. retusa at flowering, ornithine decarboxylase activity was present mainly in leaves, especially the young ones. However, other very young organs such as inflorescence and growing roots exhibited much lower or very low activities; the enzyme activity in stems was negligible. There was no correlation between the enzyme activity and polyamine or alkaloid content in either species. In both species only free polyamines were detected except for C. retusa roots and inflorescence—with relatively very high levels of these compounds—in which conjugated putrescine, spermidine, and spermine were also found; agmatine was not identified by HPLC in any plant organ except for C. retusa roots with rhizobial nodules. Organ- or age-dependent differences in the polyamine levels were small or insignificant. The highest alkaloid contents were found in young leaves and inflorescence. PMID:16665870

  10. Phylogenetic Analyses Reveal Monophyletic Origin of the Ergot Alkaloid Gene dmaW in Fungi

    Miao Liu; Panaccione, Daniel G.; Schardl, Christopher L.

    2009-01-01

    Ergot alkaloids are indole-derived mycotoxins that are important in agriculture and medicine. Ergot alkaloids are produced by a few representatives of two distantly related fungal lineages, the Clavicipitaceae and the Trichocomaceae. Comparison of the ergot alkaloid gene clusters from these two lineages revealed differences in the relative positions and orientations of several genes. The question arose: is ergot alkaloid biosynthetic capability from a common origin? We used a molecular phylog...

  11. Effect of biotin on alkaloid production during submerged cultivation of Claviceps sp. strain SD-58.

    Desai, J. D.; Desai, A J; Patel, H C

    1983-01-01

    Addition of biotin to culture medium NL-406 significantly increased alkaloid yield during submerged cultivation of Claviceps sp. strain SD-58. Alkaloid yield was further enhanced by incorporating leucine in biotin-supplemented culture medium. Increased alkaloid production was associated with an increase in the lipid content of cells and in the number of chlamydospores. Biotin deficiency caused a reduction in alkaloid yield and a parallel decrease in lipid content and chlamydospore numbers.

  12. Solid substrate mediated changes in ergot alkaloid spectra in solid state fermentation system

    Trejo Hernandez, M.R.; Lonsane, B.K.; Raimbault, Maurice; Roussos, Sevastianos

    1993-01-01

    Use of different solid substrates resulted in minor alterations in total alkaloid production by #Claviceps purpurea$ 1029c in solid state fermentation system but the changes in the spectra of ergot alkaloids were of significantly higher magnitudes. Ergonovine accounted for 93% of the total alkaloid production in wheat grain medium while lysergic acid derivatives and ergonovine comprised of 66% and 32% of total alkaloids in rye grain medium. In contrast, ergonovine, ergotamine, and lysergic ac...

  13. THE ALKALOID CYTISINE IN THE CELL CULTURE

    Gazaliev A.M.

    2012-08-01

    Full Text Available Alkaloids are vegetative establishments of complex and original structure with nitrous heterocycles in the basis. For a long time they drew researchers’ attention because of their unique and specific physiological effect on alive organisms. Not all the representatives of the globe’s flora contain these unique substances. Alkaloid cytisine is to be found mainly in the plants of the fabaceous family - Fabaceae. For the cytisine production the seeds of Thermopsis lanceolata R.Br (T. lanceolata R.Br and Cytisus laburnum (C. laburnum are used as a raw material. The object of the research is T. lanceolata cell culture. Sterile sprouts are used at the first stage of the experiment. Callus genesis is accompanied with dedifferentiation. It leads to the cellular organization simplification. Based on an important property of a plant cell, such as totipotency, there appears the formation of the “de novo” biosynthetic device. The cultivation algorithm consists of two basic stages: (i the cultivation conditions optimization of callus with a high level of the primary metabolites biosynthesis (Aspartat – lysine; (ii the research of cultivation chemical and physical factors influence on the secondary metabolite (cytisine biosynthesis and accumulation. During the cultivation the Murashige and Skoog classical recipe of nutrient medium will be used. Optimization of the cultivation conditions will concern the phytohormones, macro- and micronutrients content, as the purpose of optimization is the production of the determined high-level competence embriogenical callus. The main problem is genetic heterogeneity of a cellular population and instability of morpho-physiological processes. The correct management of higher plants cells population is possible at the synchronization of a cellular cycle phases. The references analysis has shown that it is almost impossible to synchronize cellular cycles in the culture of plant tissue. The application of chemical

  14. Three new C20-diterpenoid alkaloids from Delphinium anthriscifolium var. savatieri

    Xiao Yu Liu; Qiao Hong Chen; Feng Peng Wang

    2009-01-01

    Three new C20-diterpenoid alkaloids, designated as anthriscifolmines A-C (1-3), together with two known alkaloids denudatine and delgramine, were isolated from the whole herb of Delphinium anthriscifolium var. savatieri. The structures of these new alkaloids were elucidated on the basis of spectral data.

  15. Two new C19-diterpenoid alkaloids from roots Aconitum hemsleyanium var. atropurpureum

    Pei Tang; Dong Lin Chen; Xi Xian Jian; Feng Peng Wang

    2007-01-01

    A new franchetine-type C19-diterpenoid alkaloid 3-hydroxyfranchetine 1 and a new aconitine-type C19-diterpenoid alkaloid atropurpursine 2 have been isolated from the roots of Aconitum hemsleyanium var.atropurpureum.The structures of these new alkaloids were established on the basis of spectral data.

  16. Steroidal glyco alkaloids and molluscicidal activity of Solanum asperum Rich. fruits

    Silva, Tania M.S. [Instituto Multidisciplinar em Saude, Vitoria da Conquista, BA (Brazil). Campus Avancado Anisio Teixeira]. E-mail: sarmento@pesquisador.cnpq.br; Camara, Celso A. [Universidade Federal Rural de Pernambuco, Recife, PE (Brazil). Dept. de Quimica; Freire, Kristerson R.L.; Silva, Thiago G. da; Agra, Maria de F.; Bhattacharyya, Jnanabrata [Universidade Federal da Paraiba (UFPB), Joao Pessoa, PB (Brazil). Lab. de Tecnologia Farmaceutica

    2008-07-01

    Bioassay-guided fractionation of the alkaloidal extract of the green fruits of Solanum asperum afforded a new compound, solanandaine along with solasonine and solamargine. The total crude alkaloids as well as the isolated pure alkaloids exhibited significant molluscicidal activity. (author)

  17. Alkaloid analysis by high-performance liquid chromatography-solid phase extraction-nuclear magnetic resonance

    Johansen, Kenneth; Ebild, S.J.; Christensen, S.B.;

    2012-01-01

    cartridge limiting the general application of the procedure. In this work, two new approaches for efficient SPE trapping of alkaloids and elution efficiencies were evaluated using 24 model alkaloids. Use of a 0.1M NaOH solution as the post-column dilution greatly enhanced trapping of alkaloids...

  18. Activity of Alkaloids on Peptic Ulcer: What’s New?

    Raphaela Francelino do Nascimento

    2015-01-01

    Full Text Available Peptic ulcer is a common disease characterized by lesions that affect the mucosa of the esophagus, stomach and/or duodenum, and may extend into the muscular layer of the mucosa. Natural products have played an important role in the process of development and discovery of new drugs, due to their wide structural diversity and present, mostly specific and selective biological activities. Among natural products the alkaloids, biologically active secondary metabolites, that can be found in plants, animals or microorganisms stand out. The alkaloids are compounds consisting of a basic nitrogen atom that may or may not be part of a heterocyclic ring. This review will describe 15 alkaloids with antiulcer activity in animal models and in vitro studies.

  19. Terpenoid Indole Alkaloids Biosynthesis and Metabolic Engineering in Catharanthus roseus

    2007-01-01

    Catharanthus roseus L. (Madagascar periwinkle) biosynthesizes a diverse array of secondary metabolites including anticancer dimeric alkaloids (vinblastine and vincristine) and antihypertensive alkaloids (ajmalicine and serpentine). The multi-step terpenoid indole alkaloids (TIAs) biosynthetic pathway in C. roseus is complex and is under strict molecular regulation. Many enzymes and genes involved in the TIAs biosynthesis have been studied in recent decades. Moreover,some regulatory proteins were found recently to control the production of TIAs in C. roseus. Based on mastering the rough scheme of the pathway and cloning the related genes, metabolic engineering of TIAs biosynthesis has been studied in C.roseus aiming at increasing the desired secondary metabolites in the past few years. The present article summarizes recent advances in isolation and characterization of TIAs biosynthesis genes and transcriptional regulators involved in the second metabolic control in C. roseus. Metabolic engineering applications in TIAs pathway via overexpression of these genes and regulators in C. roseus are also discussed.

  20. A look inside an alkaloid multisite plant: the Catharanthus logistics.

    Courdavault, Vincent; Papon, Nicolas; Clastre, Marc; Giglioli-Guivarc'h, Nathalie; St-Pierre, Benoit; Burlat, Vincent

    2014-06-01

    Environmental pressures forced plants to diversify specialized metabolisms to accumulate noxious molecules such as alkaloids constituting one of the largest classes of defense metabolites. Catharanthus roseus produces monoterpene indole alkaloids via a highly elaborated biosynthetic pathway whose characterization greatly progressed with the recent expansion of transcriptomic resources. The complex architecture of this pathway, sequentially distributed in at least four cell types and further compartmentalized into several organelles, involves partially identified inter-cellular and intra-cellular translocation events acting as potential key-regulators of metabolic fluxes. The description of this spatial organization and the inherent secretion and sequestration of metabolites not only provide new insight into alkaloid cell biology and its involvement in plant defense processes but also present new biotechnological challenges for synthetic biology. PMID:24727073

  1. Chemotaxonomic value of alkaloids in solanum nigrum complex

    The comparison of alkaloidal profile of delimited species in the 5 locally available taxa of S. nigrum complex were used to establish the boundaries among close taxonomic groups. Several glyco alkaloids (Solasonine, alpha-Solamargine, alpha-Solamargine and alpha-Solanine) and their aglycones (Solasodine and Solanidine) were analyzed that were shown to be a valuable tool to resolve the international taxonomic controversy based on morphological characters. HPLC and GC-MS were used for the first time for the analysis of alkaloids in S. nigrum complex. Qualitative and quantitative comparison by cluster analysis demonstrated significant distances among S. chenopodioides and S. villosum as well as in S. americanum and S. nigrum, in their respective clusters, indicated them as distinct species. But S. retroflexum did not show such a marked difference and hence might be regarded as a variety or subspecies of S. nigrum. (author)

  2. Comparative Analysis of Amaryllidaceae Alkaloids from Three Lycoris Species

    Yongqiang Tian

    2015-12-01

    Full Text Available The major active constituents from Amaryllidaceae family were reported to be Amaryllidaceae alkaloids (AAs, which exhibited a wide spectrum of biological activities, such as anti-tumor, anti-viral, and acetyl-cholinesterase-inhibitory activities. In order to better understand their potential as a source of bioactive AAs and the phytochemical variations among three different species of Lycoris herbs, the HPLC fingerprint profiles of Lycoris aurea (L. aurea, L. radiata, and L. guangxiensis were firstly determined and compared using LC-UV and LC-MS/MS. As a result, 39 peaks were resolved and identified as AAs, of which nine peaks were found in common for all these three species, while the other 30 peaks could be revealed as characteristic AAs for L. aurea, L. radiata and L. guangxiensis, respectively. Thus, these AAs can be used as chemical markers for the identification and quality control of these plant species. To further reveal correlations between chemical components and their pharmaceutical activities of these species at the molecular level, the bioactivities of the total AAs from the three plant species were also tested against HepG2 cells with the inhibitory rate at 78.02%, 84.91% and 66.81% for L. aurea, L. radiata and L. guangxiensis, respectively. This study firstly revealed that the three species under investigation were different not only in the types of AAs, but also in their contents, and both contributed to their pharmacological distinctions. To the best of our knowledge, the current research provides the most detailed phytochemical profiles of AAs in these species, and offers valuable information for future valuation and exploitation of these medicinal plants.

  3. 3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens.

    Liu, S C; Oguntimein, B; Hufford, C D; Clark, A M

    1990-04-01

    Further examination of the active ethanolic extract of the root bark of Cleistopholis patens by using bioassay-directed fractionation resulted in the isolation of a new alkaloid, 3-methoxysampangine (compound I), together with three known alkaloids, eupolauridine (compound II), liriodenine (compound III), and eupolauridine N-oxide (compound IV). The proposed structure of compound I was based on its physicochemical properties and spectral data. 3-Methoxysampangine exhibited significant antifungal activity against Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans. This is the first report of the isolation of liriodenine (compound III) from the root bark of C. patens. PMID:2188584

  4. New cyclopeptide alkaloid and lignan glycoside from Justicia procumbens.

    Jin, Hong; Chen, Li; Tian, Ying; Li, Bin; Dong, Jun-Xing

    2015-01-01

    This study reported a new cyclopeptide alkaloid, justicianene A (1), and a new lignan glycoside, procumbenoside H (2), isolated from Justicia procumbens. The structures of the new compounds were elucidated by means of spectroscopic analysis, including extensive 2D NMR studies and mass spectrometry. Cyclopeptide alkaloids were first observed from the genus Justicia. Compound 2 was cytotoxic against human LoVo colon carcinoma cells with an IC50 value of 17.908 ± 1.949 μM. PMID:25367562

  5. Quinolizidines alkaloids: Petrosin and xestospongins from the sponge Oceanapia sp.

    Keisham Sarjit Singh; Babulal Das; Chandrakant G Naik

    2011-09-01

    A bisquinolizidine alkaloid, petrosin (1) and a series of bis-1-oxaquinolizidine, xestospongins (2-9), were obtained from the ethyl acetate extract of the sponge Oceanapia sp. Petrosin was obtained along with xestospongin- C, D, E, F, G, H, I and J having di-hetroatom rings, from the ethyl acetate extract of the sponge. The compounds exhibited moderate to high activities against some microorganisms and clinical isolates. The structures of the alkaloids were elucidated by NMR and ESIMS spectroscopic data. The structure of petrosin was confirmed by an X-ray diffraction study.

  6. Antioxidant Potential of Cyclopeptyide Alkaloids Isolated from Zizyphus Oxphylla

    The present study reports on the antioxidant potential of five cyclopeptide alkaloids isolated from Zizyphus oxyphylla including Oxyphylline-D 1, Nummularin-C 2, Nummularin-R 3, Oxyphylline-B 4, Oxyphylline C 5 using DPPH free radical assay, nitric oxide radical assay and reducing power assay. The isolated alkaloids demonstrated marked antioxidant potential in a concentration dependent manner. Among the tested molecules, the compounds, 2 was most potent with IC50 values of 27.23, 32.03 and 22.45 μg/ml in DPPH free radical assay, nitric oxide radical assay and reducing power assay respectively. (author)

  7. Characterization of chemical constituents and rats metabolites of an alkaloidal extract of Alstonia scholaris leaves by liquid chromatography coupled with mass spectrometry.

    Cao, Jing; Shen, Hong-Mei; Wang, Qi; Qian, Yi; Guo, Hong-Cheng; Li, Kai; Qiao, Xue; Guo, De-An; Luo, Xiao-Dong; Ye, Min

    2016-07-15

    Alstonia scholaris has been used in "Dai" ethnic medicine to treat chronic respiratory diseases for a long history, and the major bioactive constituents are alkaloids. An alkaloidal extract of A. scholaris leaves (AAS) has been developed into an investigational new drug, and has been approved for phase I/II clinical trials by China Food and Drug Administration. However, little is known on the chemical composition and in vivo metabolism of AAS, thus far. In this study, an ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UHPLC/qTOF-MS) method was established to characterize the chemical constituents of AAS. Samples were separated on an ACQUITY UPLC CSH column (2.1×100mm, 1.7μm) with acetonitrile and water containing 0.3% formic acid as the mobile phase. On the basis of high-accuracy mass spectral analysis, a total of 35 alkaloids were characterized from AAS, including 11 scholaricine-type, 9 vallesamine-type, 12 picrinine-type, and 3 tubotaiwine-type alkaloids. Furthermore, the metabolic pathways of 4 representative alkaloids in rats were studied. They mainly undertook hydroxylation and glucuronidation reactions. Based on the above metabolic pathways, the metabolism of AAS (10mg/kg) in rats after oral administration was studied by LC/MS. A total of 33 compounds in plasma, 40 compounds in urine, and 38 compounds in feces were characterized. The results indicated that scholaricine-type alkaloids could get into circulation more readily than the other types. This is the first systematic study on chemical profiling and metabolites identification of AAS. PMID:26275898

  8. Comparison of three chromatographic techniques for the detection of mitragynine and other indole and oxindole alkaloids in Mitragyna speciosa (kratom) plants.

    Wang, Mei; Carrell, Emily J; Ali, Zulfiqar; Avula, Bharathi; Avonto, Cristina; Parcher, Jon F; Khan, Ikhlas A

    2014-06-01

    Leaves of the Southeast Asian plant Mitragyna speciosa are used to suppress pain and mitigate opioid withdrawal syndromes. The potential threat of abuse and ready availability of this uncontrolled psychoactive plant have led to the need for improved analytical techniques for the detection of the major active components, mitragynine and 7-hydroxymitragynine. Three independent chromatographic methods coupled to two detection systems, GC with MS, supercritical fluid chromatography with diode array detection, and HPLC with MS and diode array detection, were compared for the analysis of mitragynine and other indole and oxindole alkaloids in M. speciosa plants. The indole alkaloids included two sets of diastereoisomers: (i) paynantheine and 3-isopaynantheine and (ii) mitragynine, speciogynine, and speciociliatine. Two oxindole alkaloid diastereoisomers, corynoxine and corynoxine B, were also studied. The HPLC and supercritical fluid chromatography methods successfully resolved the major components with slightly different elution orders. The GC method was less satisfactory because it was unable to resolve mitragynine and speciociliatine. This separation was difficult by GC with a liquid stationary phase because these diastereoisomers differ only in the orientation of an interior hydrogen atom. The observed lack of resolution of the indole alkaloid diastereoisomers coupled with the likeness of the mass and tandem mass spectra, calls into question proposed GC methods for the analysis of mitragynine based on solely GC with MS separation and identification. PMID:24659356

  9. Histochemical Investigation and Kinds of Alkaloids in Leaves of Different Developmental Stages in Thymus quinquecostatus

    Haiting Jing

    2014-01-01

    Full Text Available Thymus quinquecostatus, with more medical value, is a kind of wild plants. In order to exploit and utilize this plant, we studied the species and locations of alkaloids in its leaves. In this paper, histochemical study of leaves at different developing stages was taken to localize the alkaloids. Meanwhile, the kinds and content of alkaloids in leaves were identified using GC-MS technique. It was found that there were two kinds of glandular trichomes, namely, peltate trichomes and capitate trichomes, on the surface of leaves, and their secretory cells could secrete alkaloids. Results showed that trichomes could secrete alkaloids as soon as the first pair of leaves formed, and there were altogether 18 kinds of alkaloids identified by GC-MS. Nearly all of these alkaloids of leaves at different developing stages were distinct from each other, except one, 3-methoxy-a-methyl-benzeneethanamine, persists at different developing stages with high concentration.

  10. New Diterpenoid Alkaloids from Spiraea japonica var. ovalifolia

    2001-01-01

    Five new diterpenoid alkaloids, 19-O-deethylspiramine N (1), deacetylspiramine S (2), spiramidine A (3), spiramidine B (4) and deacetylspiramine F (5) were isolated from the aerial parts of Spireae japonica L. f. var. ovalifolia. Their structures were charaterized mainly based on spectral analysis.

  11. Dendrimery námelových alkaloidů

    Trnka, Jan; Sedmera, Petr; Halada, Petr; Přikrylová, Věra; Jegorov, A.; Křen, Vladimír

    1999-01-01

    Roč. 93, č. 11 (1999), s. 751-752. ISSN 0009-2770. [Konference Pokroky v organické, bioorganické a farmaceutické chemii /34./. 15.11.1999-17.11.1999, Liblice] R&D Projects: GA AV ČR IAA4020901 Keywords : alkaloids * enzymes * microbial Subject RIV: EE - Microbiology, Virology

  12. Metabolic Engineering of Tropane Alkaloid Biosynthesis in Plants

    Lei ZHANG; Guo-Yin KAI; Bei-Bei LU; Han-Ming ZHANG; Ke-Xuan TANG; Ji-Hong JIANG; Wan-Sheng CHEN

    2005-01-01

    Over the past decade, the evolving commercial importance of so-called plant secondary metabolites has resulted in a great interest in secondary metabolism and, particularly, in the possibilities to enhance the yield of fine metabolites by means of genetic engineering. Plant alkaloids, which constitute one of the largest groups of natural products, provide many pharmacologically active compounds. Several genes in the tropane alkaloids biosynthesis pathways have been cloned, making the metabolic engineering of these alkaloids possible. The content of the target chemical scopolamine could be significantly increased by various approaches, such as introducing genes encoding the key biosynthetic enzymes or genes encoding regulatory proteins to overcome the specific rate-limiting steps. In addition, antisense genes have been used to block competitive pathways. These investigations have opened up new, promising perspectives for increased production in plants or plant cell culture. Recent achievements have been made in the metabolic engineering of plant tropane alkaloids and some new powerful strategies are reviewed in the present paper.

  13. Clustered Ergot Alkaloids Modulate Cell-mediated Cytotoxicity

    Křen, Vladimír; Fišerová, Anna; Weignerová, Lenka; Stibor, I.; Halada, Petr; Přikrylová, Věra; Sedmera, Petr; Pospíšil, Miloslav

    2002-01-01

    Roč. 10, - (2002), s. 415-424. ISSN 0968-0896 R&D Projects: GA AV ČR IAA4020901; GA ČR GA310/98/0347 Institutional research plan: CEZ:AV0Z5020903 Keywords : clustered * ergot * alkaloids Subject RIV: EE - Microbiology, Virology Impact factor: 2.043, year: 2002

  14. Mechanistic Insights to the Cytotoxicity of Amaryllidaceae Alkaloids

    Nair, J. J.; Rárová, L.; Strnad, Miroslav; Bastida, J.; van Staden, J.

    2015-01-01

    Roč. 10, č. 1 (2015), s. 171-182. ISSN 1934-578X Grant ostatní: GA MŠk(CZ) ED0007/01/01 Institutional support: RVO:61389030 Keywords : Alkaloid * Amaryllidaceae * Apoptosis Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 0.906, year: 2014 http://www.ncbi.nlm.nih.gov/pubmed/25920242

  15. New cholinesterase inhibiting bisbenzylisoquinoline alkaloids from Abuta grandifolia.

    Cometa, Maria Francesca; Fortuna, Stefano; Palazzino, Giovanna; Volpe, Maria Teresa; Rengifo Salgado, Elsa; Nicoletti, Marcello; Tomassini, Lamberto

    2012-04-01

    The phytochemical study of the stem bark and wood of Abuta grandifolia (Mart.) Sandwith led to the identification of four bisbenzylisoquinoline alkaloids (BBIQs), namely (R,S)-2 N-norberbamunine (1), (R,R)-isochondodendrine (2), (S-S)-O4″-methyl, Nb-nor-O6'-demethyl-(+)-curine (3), and (S-S)-O4″-methyl, O6'-demethyl-(+)-curine (4), together with the aporphine alkaloid R-nornuciferine (5), all obtained by countercurrent distribution separation (CCD) and identified on the basis of their spectroscopic data. Alkaloids 3 and 4 were new. All the isolated compounds were tested for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. 1 was the most active against AChE, whereas 3 and 4 were the most potent against BChE. Interestingly, all tested alkaloids are more potent against BChE than against AChE. This selectivity of cholinesterase (ChE) inhibition could be important in order to speculate on their potential therapeutic relevance. PMID:22230193

  16. Pyrrolizidine alkaloid toxicity in livestock: A paradigm for human poisoning

    Livestock poisoning, primarily liver damage, caused by consumption of plants containing 1,2-dehydropyrro-lizidine ester alkaloids (dehydroPAs), and the corresponding N-oxides, is a relatively common occurrence worldwide. Because of the economic impact, extensive investigations...

  17. ALKALOIDS OF THE SEDUM ACRE-GROUP (CRASSULACEAE)

    STEVENS, JF; THART, H; HENDRIKS, H; MALINGRE, TM

    1993-01-01

    The 16 species of the Sedum acre-group were investigated for the presence of alkaloids. They are S. acre of S. ser. Acria, S. alpestre, S. annuum, S. apoleipon, S. borissovae, S. euxinum, S. grisebachii, S. laconicum, S. multiceps, S. sexangulare, S. tuberiferum, S. tuberosum, S. ursi, and S. urvill

  18. 21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.

    2010-04-01

    ... 21 Food and Drugs 2 2010-04-01 2010-04-01 false Dietary supplements containing ephedrine alkaloids. 119.1 Section 119.1 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION DIETARY SUPPLEMENTS THAT PRESENT A SIGNIFICANT...

  19. Repellence and attraction of Apis mellifera foragers by nectar alkaloids

    Hroncová Z.

    2016-03-01

    Full Text Available Plant secondary metabolites present naturally in nectar, such as alkaloids, may change the behavioural responses of floral visitors and affect pollination. Some studies have shown that nectar containing low concentrations of these secondary metabolites is preferred by honey bee foragers over pure nectar. However, it remains unclear whether this is caused by dependence or addictive behaviour, a simple taste preference, or by other conditions such as self-medication. In our choice experiment, free-flying bees were presented with artificial flowers holding 20% sucrose containing 0.5−50 μg ml−1 of one of the naturally occurring nectar alkaloids - caffeine, nicotine, senecionine, and gelsemine. Nectar uptake was determined by weighing each flower and comparing the weight to that of the control flower. Our experimental design minimized memorizing and marking; despite this, caffeine was significantly preferred at concentrations 0.5−2 μg ml−1 over control nectar; this preference was not observed for other alkaloids. All of the compounds tested were repellent at concentrations above 5 μg ml−1. We confirmed previous reports that bees exhibit a preference for caffeine, and hypothesize that this is not due only to addictive behaviour but is at least partially mediated by taste preference. We observed no significant preference for nicotine or any other alkaloid.

  20. The alkaloid profiles of Sophora nuttalliana and Sophora stenophylla

    Sophora is a diverse genus in the family Fabaceae, comprised of herbs, shrubs, and trees that occurs throughout the world, primarily in the northern hemisphere. Species of Sophora are known to contain quinolizidine alkaloids that are toxic and potentially teratogenic. Two perennial herbaceous spec...

  1. The ergot alkaloid gene cluster: Functional analyses and evolutionary aspects

    Lorenz, N.; Haarmann, T.; Pažoutová, Sylvie; Jung, M.; Tudzynski, P.

    2009-01-01

    Roč. 70, 15-16 (2009), s. 1822-1832. ISSN 0031-9422 Institutional research plan: CEZ:AV0Z50200510 Keywords : Claviceps purpurea * Ergot fungus * Ergot alkaloid gene cluster Subject RIV: EE - Microbiology, Virology Impact factor: 3.104, year: 2009

  2. Alkaloid profiling and anticholinesterase activity of South American Lycopodiaceae species.

    Konrath, Eduardo Luis; Ortega, María Gabriela; de Loreto Bordignon, Sérgio; Apel, Miriam Anders; Henriques, Amélia Teresinha; Cabrera, José Luis

    2013-02-01

    The alkaloid extracts of four Huperzia and one Lycopodiella species, from Brazilian habitats, were tested for their in vitro anticholinesterase activities. IC(50) values showed a potent acetylcholinesterase inhibition for H. reflexa (0.11 ± 0.05 μg/mL), followed by H. quadrifariata (2.0 ± 0.3 μg/mL), H. acerosa (5.5 ± 0.9 μg/mL), H. heterocarpon (25.6 ± 2.7 μg/mL) and L. cernua (42.6 ± 1.5 μg/mL). A lower inhibition of butyrylcholinesterase was observed for all species with the exception of H. heterocarpon (8.3 ± 0.9 μg/mL), whose alkaloid extract presented a selectivity for pseudocholinesterase. Moreover, the chemical study of the bioactive extracts performed by GC-MS, revealed the presence of a number of Lycopodium alkaloids belonging to the lycopodane, flabellidane and cernuane groups. Surprisingly, the potent acetylcholinesterase inhibitors huperzines A and B were not detected in the extracts, suggesting that other alkaloids may be responsible for such an effect. PMID:22117191

  3. Effect of Ergot Alkaloids on Bovine Foregut Vasculature

    Ergot alkaloids induce vasoconstriction of bovine foregut vasculature. Ergovaline induced the greatest response in ruminal artery while ergovaline and ergotamine induced the greatest response in ruminal vein. Lysergic acid did not stimulate a contractile response in either the ruminal artery or vein...

  4. Scientific Opinion on Ergot alkaloids in food and feed

    Beuerle, T.; Benford, D.; Brimer, L.; Cottrill, B.; Doerge, D.; Dusemund, B.; Farmer, P.; Fürst, P.; Humpf, H.; Mulder, P.P.J.

    2012-01-01

    The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs) in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread C

  5. Scientific Opinion on Tropane alkaloids in food and feed

    Beuerle, T.; Benford, D.; Brimer, L.; Cottrill, B.; Doerge, D.; Dusemund, B.; Farmer, P.; Fürst, P.; Humpf, H.; Mulder, P.P.J.

    2013-01-01

    The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs) in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread C

  6. Scientific Opinion on Pyrrolizidine alkaloids in food and feed

    Beuerle, T.; Benford, D.; Brimer, L.; Cottrill, B.; Doerge, D.; Dusemund, B.; Farmer, P.; Fürst, P.; Humpf, H.; Mulder, P.P.J.

    2013-01-01

    The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs) in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread C

  7. In vitro cytotoxicity of various dehydropyrrolizidine ester alkaloids

    Dehydropyrrolizidine alkaloids (DHPAs) are plant-derived hepato-, pneumo- and geno-toxins that are carcinogenic in several species. Because of the difficulty in isolating sufficient DHPA for toxicological studies, there are few direct comparisons of toxicity. The objectives of this study was to de...

  8. Investigation of a betainic alkaloid from Punica granatum.

    Schmidt, Andreas; Mordhorst, Thorsten; Nieger, Martin

    2005-07-01

    Spectroscopic investigations reveal that a hydroquinone pyridinium alkaloid isolated from the leaves of pomegranates Punica granatum L. (X-ray) exists as a mixture of a conjugated and a cross-conjugated heterocyclic mesomeric betaine in aqueous and DMSO-d6 solution. Twofold deprotonation yields an anionic tripole. PMID:15938201

  9. The mutagenicities of alkaloids and N-nitrosoguvacoline from betel quid.

    Wang, C K; Peng, C H

    1996-08-01

    In Taiwan, betel quid is a natural masticatory, which is composed of fresh green areca fruit, Piper betle and slaked lime paste. Areca fruit contains some alkaloids, of which arecoline is the major one. N-Nitrosoguvacoline (NG), one of the N-nitrosation products of arecoline, is the only one N-nitrosamine found in Taiwanese betel quid chewing saliva. The mutagenic studies in Ames Salmonella microsome test showed that crude alkaloid extracts of areca fruit and arecoline were active in Salmonella typhimurium TA100, and NG was weakly active in TA98 and TA100. The activities in both arecoline and NG decreased further in the presence of rat liver S9 mix. Nitrite was significantly consumed during the N-nitrosation of arecoline and sodium nitrite at acidic condition (pH 3), whereas the formation of NG was favored at neutral condition (pH 7). Crude phenolic extracts of leaf and inflorescence of Piper betle inhibited the formation of NG by blocking the nitrite. However, a high amount of crude phenolic extracts of areca fruit enhanced the formation of NG. PMID:8692215

  10. Analysis of pyrrolizidine alkaloids and evaluation of some biological activities of Algerian Senecio delphinifolius (Asteraceae).

    Tidjani, Soukaina; Okusa, Philippe N; Zellagui, Amar; Banuls, Laetitia Moreno Y; Stévigny, Caroline; Duez, Pierre; Rhouati, Salah

    2013-04-01

    Although Senecio species are known as sources of potentially toxic pyrrolizidine alkaloids (PAs), some species of this genus are traditionally used as remedies, notably in Algeria. In this paper, the evaluation of biological activities and the analysis of PAs of Algerian specimens of Senecio delphinifolius Vahl are reported. The n-butanolic extract of the herb showed a weak antibacterial effect against Escherichia coli with a MIC of 1 mg/mL, but was inactive against Staphylococcus aureus and Pseudomonas aeruginosa. The n-butanolic extracts of the roots, stems and herb showed a modest antioxidant activity, scavenging the free radical DPPH with respective IC50 values of 55.3, 50.2 and 13.3 microg/mL. A cytotoxic effect against a series of human tumor cell lines was observed with the n-butanolic extract from stems (IC50 ranging between 34 and 88 microg/mL). The herb of the evaluated sample contains 140 ppm of PAs (senecionine, seneciphylline, integerrimine, senkirkine) and PA-related alkaloids (dehydrosenkirkine and neosenkirkine). As the major PAs belong to the toxic series (1,2-unsaturation in the pyrrolizidine cycle and macrocyclic diester), the use of S. delphinifolius should be discouraged in traditional medicine. PMID:23738446

  11. Multicellular compartmentation of catharanthus roseus alkaloid biosynthesis predicts intercellular translocation of a pathway intermediate

    St-Pierre, B; Vazquez-Flota, FA; De Luca V

    1999-01-01

    In situ RNA hybridization and immunocytochemistry were used to establish the cellular distribution of monoterpenoid indole alkaloid biosynthesis in Madagascar periwinkle (Catharanthus roseus). Tryptophan decarboxylase (TDC) and strictosidine synthase (STR1), which are involved in the biosynthesis of the central intermediate strictosidine, and desacetoxyvindoline 4-hydroxylase (D4H) and deacetylvindoline 4-O-acetyltransferase (DAT), which are involved in the terminal steps of vindoline biosynthesis, were localized. tdc and str1 mRNAs were present in the epidermis of stems, leaves, and flower buds, whereas they appeared in most protoderm and cortical cells around the apical meristem of root tips. In marked contrast, d4h and dat mRNAs were associated with the laticifer and idioblast cells of leaves, stems, and flower buds. Immunocytochemical localization for TDC, D4H, and DAT proteins confirmed the differential localization of early and late stages of vindoline biosynthesis. Therefore, we concluded that the elaboration of the major leaf alkaloids involves the participation of at least two cell types and requires the intercellular translocation of a pathway intermediate. A basipetal gradient of expression in maturing leaves also was shown for all four genes by in situ RNA hybridization studies and by complementary studies with dissected leaves, suggesting that expression of the vindoline pathway occurs transiently during early leaf development. These results partially explain why attempts to produce vindoline by cell culture technology have failed. PMID:10330473

  12. Antidiabetic and Antioxidant Properties of Alkaloids from Catharanthus roseus (L. G. Don

    Won Fen Wong

    2013-08-01

    Full Text Available Catharanthus roseus (L. G. Don is a herbal plant traditionally used by local populations in India, South Africa, China and Malaysia to treat diabetes. The present study reports the in vitro antioxidant and antidiabetic activities of the major alkaloids isolated from Catharanthus roseus (L. G. Don leaves extract. Four alkaloids—vindoline I, vindolidine II, vindolicine III and vindolinine IV—were isolated and identified from the dichloromethane extract (DE of this plant’s leaves. DE and compounds I–III were not cytotoxic towards pancreatic β-TC6 cells at the highest dosage tested (25.0 µg/mL. All four alkaloids induced relatively high glucose uptake in pancreatic β-TC6 or myoblast C2C12 cells, with III showing the highest activity. In addition, compounds II–IV demonstrated good protein tyrosine phosphatase-1B (PTP-1B inhibition activity, implying their therapeutic potential against type 2 diabetes. III showed the highest antioxidant potential in ORAC and DPPH assays and it also alleviated H2O2-induced oxidative damage in β-TC6 cells at 12.5 µg/mL and 25.0 µg/mL.

  13. Antiparasitic activities of acridone alkaloids from Swinglea glutinosa (Bl.) Merr

    Santos, Djalma A.P. dos; Vieira, Paulo C.; Silva, M. Fatima das G.F. da; Fernandes, Joao B. [Universidade Federal de Sao Carlos, SP (Brazil). Dept. de Quimica; Rattray, Lauren; Croft, Simon L. [London School of Hygiene and Tropical Medicine, London (United Kingdom). Dept. of Infectious and Tropical Diseases

    2009-07-01

    Eleven acridone alkaloids isolated from Swinglea glutinosa (Bl.) Merr. were examined for in vitro activity against chloroquine-sensitive Plasmodium falciparum 3D7, Trypanosoma brucei rhodesiense STIB900 and Leishmania donovani L82. An assay with KB cells was developed in order to compare in vitro toxicity of alkaloids with the selective action on the parasites. Nine of the compounds had IC{sub 50} values ranging from 0.3 to 11.6 {mu}M against P. falciparum. In contrast, a small number of compounds showed significant activity against T. brucei rhodesiense and none had activity against L. donovani. Among the alkaloids three had IC{sub 50} < 1.0 {mu}M against P. falciparum, whereas against T. b. rhodesiense five had IC{sub 50} < 10 {mu}M. The characterization of the acridone alkaloids, 1,3,5-trihydroxy-4-methoxy-10-methyl-2,8-bis(3-methylbut-2-enyl)acridin-9 (10H)-one (1), 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxypropan-2-yl)-11-methoxy-10-methylfuro [3,2-b] acridin-5(10H)-one (2) and 3,4-dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2Hpyrano[ 2,3-a]acridin-12(7H)-one (3), is discussed, as well as the structure-activity relationship of all compounds assayed. Isolation and spectral data of alkaloids 1-3 are described for the first time although their cytotoxicities to cancer cells have been described before. (author)

  14. Major Roads

    Minnesota Department of Natural Resources — This data set contains roadway centerlines for major roads (interstates and trunk highways) found on the USGS 1:24,000 mapping series. These roadways are current...

  15. Molecular Cloning and Characterization of a Vacuolar Class III Peroxidase Involved in the Metabolism of Anticancer Alkaloids in Catharanthus roseus1[C

    Costa, Maria Manuela R.; Hilliou, Frederique; Duarte, Patrícia; Pereira, Luís Gustavo; Almeida, Iolanda; Leech, Mark; Memelink, Johan; Barceló, Alfonso Ros; Sottomayor, Mariana

    2008-01-01

    Catharanthus roseus produces low levels of two dimeric terpenoid indole alkaloids, vinblastine and vincristine, which are widely used in cancer chemotherapy. The dimerization reaction leading to α-3′,4′-anhydrovinblastine is a key regulatory step for the production of the anticancer alkaloids in planta and has potential application in the industrial production of two semisynthetic derivatives also used as anticancer drugs. In this work, we report the cloning, characterization, and subcellular localization of an enzyme with anhydrovinblastine synthase activity identified as the major class III peroxidase present in C. roseus leaves and named CrPrx1. The deduced amino acid sequence corresponds to a polypeptide of 363 amino acids including an N-terminal signal peptide showing the secretory nature of CrPrx1. CrPrx1 has a two-intron structure and is present as a single gene copy. Phylogenetic analysis indicates that CrPrx1 belongs to an evolutionary branch of vacuolar class III peroxidases whose members seem to have been recruited for different functions during evolution. Expression of a green fluorescent protein-CrPrx1 fusion confirmed the vacuolar localization of this peroxidase, the exact subcellular localization of the alkaloid monomeric precursors and dimeric products. Expression data further supports the role of CrPrx1 in α-3′,4′-anhydrovinblastine biosynthesis, indicating the potential of CrPrx1 as a target to increase alkaloid levels in the plant. PMID:18065566

  16. Application of pH-zone refining hydrostatic countercurrent chromatography (hCCC) for the recovery of antioxidant phenolics and the isolation of alkaloids from Siberian barberry herb.

    Kukula-Koch, Wirginia; Koch, Wojciech; Angelis, Apostolis; Halabalaki, Maria; Aligiannis, Nektarios

    2016-07-15

    The development of a fast hCCC method tailored to recover phenolics of Siberian barberry (Berberis sibirica, Berberidaceae) responsible for the observed strong antioxidant activity was performed. Initially, the optimization of extraction procedure was evaluated based on the antiradical potential assessment (DPPH and Folin-Ciocalteu assays). 100 °C methanol ASE extract exhibited the highest antiradical activity (IC50=60 ± 4 μg/mL), and a significant TPC (159 ± 2 mgGAE/g). Thorough determination of phenolic content by UHPLC-DAD-ESI(-)HRMS revealed the presence of 10 phenolics as major constituents, and several groups of alkaloids. pH-zone refining hCCC was chosen as the most promising method for the extract's fractionation due to the ionizable character of its constituents. For this purpose a MtBE-H2O (1:1) system with 10mM TEA and HCl was applied leading to a phenolic fraction, free of alkaloids, with higher antioxidant capacity (IC50=25 μg/mL, TPC=178 mg GAE/g). Additionally, fractionation of alkaloids was achieved resulting isolation of pharmacologically important alkaloids: magnoflorine and berberine. PMID:26948630

  17. Solid-phase extraction and LC-MS analysis of pyrrolizidine alkaloids in honeys.

    Beales, Kerrie A; Betteridge, Keith; Colegate, Steven M; Edgar, John A

    2004-10-20

    Strong-cation-exchange, solid-phase extraction of pyrrolizidine alkaloids and their N-oxides from honey samples was followed by reduction of the N-oxides and subsequent analysis of total pyrrolizidine alkaloids using high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. A limited survey of 63 preprocessing samples of honey, purposefully biased toward honeys attributed to floral sources known to produce pyrrolizidine alkaloids, demonstrated levels of pyrrolizidine alkaloids up to approximately 2000 parts per billion (ppb) in a sample attributed to Echium plantagineum. Up to 800 ppb pyrrolizidine alkaloids was detected in some honeys not attributed by the collector to any pyrrolizidine alkaloid-producing floral source. No pyrrolizidine alkaloids were detected in approximately 30% of the samples in this limited study, while some honeys showed the copresence of pyrrolizidine alkaloids from multiple floral sources such as E. plantagineum and Heliotropium europaeum. In addition, retail samples of blended honeys (with no labeling to suggest that pyrrolizidine alkaloid-producing floral sources were used in the blends) have been shown to contain up to approximately 250 ppb pyrrolizidine alkaloids. PMID:15479038

  18. Ergot Alkaloids Produced by Endophytic Fungi of the Genus Epichloë

    Philippe Guerre

    2015-03-01

    Full Text Available The development of fungal endophytes of the genus Epichloë in grasses results in the production of different groups of alkaloids, whose mechanism and biological spectrum of toxicity can differ considerably. Ergot alkaloids, when present in endophyte-infected tall fescue, are responsible for “fescue toxicosis” in livestock, whereas indole-diterpene alkaloids, when present in endophyte-infected ryegrass, are responsible for “ryegrass staggers”. In contrast, peramine and loline alkaloids are deterrent and/or toxic to insects. Other toxic effects in livestock associated with the consumption of endophyte-infected grass that contain ergot alkaloids include the “sleepy grass” and “drunken horse grass” diseases. Although ergovaline is the main ergopeptine alkaloid produced in endophyte-infected tall fescue and is recognized as responsible for fescue toxicosis, a number of questions still exist concerning the profile of alkaloid production in tall fescue and the worldwide distribution of tall fescue toxicosis. The purpose of this review is to present ergot alkaloids produced in endophyte-infected grass, the factors of variation of their level in plants, and the diseases observed in the mammalian species as relate to the profiles of alkaloid production. In the final section, interactions between ergot alkaloids and drug-metabolizing enzymes are presented as mechanisms that could contribute to toxicity.

  19. Pyrrolizidine alkaloids from seven wild-growing Senecio species in Serbia and Montenegro

    BORIS M. MANDIC

    2009-01-01

    Full Text Available The genus Senecio (family Asteraceae is one of the largest in the world. It comprises about 1100 species which are the rich source of pyrrolizidine alkaloids. Plants containing pyrrolizidine alkaloids are among the most important sources of human and animal exposure to plant toxins and carcinogens. The pyrrolizidine alkaloids of seven Senecio species (S. erucifolius, S. othonnae, S. wagneri, S. subalpinus, S. carpathicus, S. paludosus and S. rupestris were studied. Fourteen alkaloids were isolated and their structures determined from spectroscopic data (1H- and 13C-NMR, IR and MS. Five of them were identified in S. erucifolius, four in S. othonnae, two in S. wagneri, four in S. subalpinus, two in S. carpathicus, three in S. paludosus and three in S. rupestris. Seven pyrrolizidine alkaloids were found for the first time in particular species. The results have chemotaxonomic importance. The cytotoxic activity and antimicrobial activity of some alkaloids were also studied.

  20. Gas Chromatographic Determination of Quinolizidine Alkaloids in Genista sandrasica and Their Antimicrobial Activity

    Nurgün Küçükboyacı

    2012-01-01

    Full Text Available Alkaloid profile of the aerial parts of Genista sandrasica Hartvig & Strid. (Fabaceae growing in Turkey was studied by capillary gas chromatography-mass spectrometry (GC-MS. Ten quinolizidine alkaloids were identified in the alkaloid extract of G. sandrasica . The main alkaloids were: sparteine (13.68%, N-acetylcytisine (6.48%, 13-methoxylupanine (13.12%, anagyrine (40.49% and baptifoline (10.76%. In addition, antibacterial and antifungal activities of the alkaloid extract of G. sandrasica were tested against standard strains of the bacteria (Escherichia coli , Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus as well as the fungi (Candida albicans and Candida krusei. The alkaloid extract of G. sandrasica showed significant activity against B. subtilis and S. aureus with minimum inhibitory concentrations (MIC of 31.25 and 62.5 µg/mL.

  1. Various alkaloid profiles in decoctions of Banisteriopsis caapi.

    Callaway, J C

    2005-06-01

    Twenty nine decoctions of Banisteriopsis caapi from four different sources and one specimen of B. caapi paste were analyzed for N,N-dimethyltryptamine (DMT), tetrahydroharmine (THH), harmaline and harmine. Other plants were also used in the preparation of these products, typically Psychotria viridis, which provides DMT. There were considerable variations in alkaloid profiles, both within and between sample sources. DMT was not detected in all samples. Additional THH may be formed from both harmine and harmaline during the preparation of these products. The alkaloid composition of one decoction sample did not change significantly after standing at room temperature for 80 days, but the initial acidic pH was neutralized by natural fermentation after 50 days. PMID:16149328

  2. Synthesis of bicyclic alkaloids from the iridoid antirrhinoside

    Frederiksen, Signe Maria

    The present thesis describes the isolation of the iridoid glucoside antirrhinoside from Antirrhinum majus, and the approaches made towards its transformation into analogues of biologically active compounds, with special interest in syntheses of bicyclic alkaloids.A synthetic piperidine monoterpene...... alkaloids. The corresponding ditosyl derivative was treated with benzylamine to afford a bicyclic N-benzylated pyrrolidine. An alternative starting material was prepared from 5,6:4',6'-di-O-isopropylidene antirrhinoside by reduction with lithium aluminum hydride. Subsequent ozonolysis and sodium borohydride...... gave the expected triol. The corresponding ditosyl derivative was treated with benzylamine or 2-methoxy-benzylamine to afford bicyclic pyrrolidines in 54-66% yield. The isopropylidene protection was removed and the unprotected pyrrolidine was acylated with benzoyl chloride to afford a potential...

  3. Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound.

    Van Miert, Sabine; Hostyn, Steven; Maes, Bert U W; Cimanga, Kanyanga; Brun, Reto; Kaiser, Marcel; Mátyus, Péter; Dommisse, Roger; Lemière, Guy; Vlietinck, Arnold; Pieters, Luc

    2005-05-01

    The antiprotozoal activities of three naturally occurring isomeric indoloquinoline alkaloids, i.e., cryptolepine (1), neocryptolepine (2), and isocryptolepine (3), and two dimeric indoloquinoline alkaloids, cryptoquindoline (6) and biscryptolepine (7), originally obtained from the plant Cryptolepis sanguinolenta, were compared with those of a new synthetic indoloquinoline isomer, isoneocryptolepine (4), and a quaternary derivative, N-methyl-isocryptolepinium iodide (5). The latter compounds showed a high antiplasmodial activity against the chloroquine-resistant Plasmodium falciparum strain K1 (IC50 of 0.23 +/- 0.04 and 0.017 +/- 0.004 microM, respectively), while the cytotoxicity (L6 cells) was 4.32 +/- 0.04 and 12.7 +/- 2.0 microM, respectively. Isoneocryptolepine (4) was found to act as an inhibitor of beta-hematin formation and as a DNA-intercalating agent. PMID:15921407

  4. Antiplasmodial activities of furoquinoline alkaloids from Teclea afzelii.

    Wansi, Jean Duplex; Hussain, Hidayat; Tcho, Alain Tadjong; Kouam, Simeon F; Specht, Sabine; Sarite, Salem Ramadan; Hoerauf, Achim; Krohn, Karsten

    2010-05-01

    The study of the chemical constituents of the stem bark of Teclea afzelii (Rutaceae) has resulted in the isolation and characterization of four furoquinoline alkaloids, namely kokusaginine (1), tecleaverdoornine (2), maculine (3) and montrifoline (4) together with lupeol (5) and beta-sitosterol glucopyranoside (6). The structures of the isolated compounds were elucidated based on spectroscopic studies. The antimalarial activity of compounds 1-4 against Plasmodium falciparum in vitro shows partial suppression of parasitic growth. PMID:19496062

  5. Bis(indolyl)methane alkaloids: Isolation, bioactivity, and syntheses

    Praveen, P.; Parameswaran, P.S.; Majik, M.S.

    Author version: Synthesis - Stuttgart, vol.47; 2015; 1827-1837 Bisindolyl Methane Alkaloids: Isolation, Bioactivity and Syntheses P. J. Praveen,a,b P. S. Parameswaran*b, M. S. Majik*c aCSIR-National Institute of Oceanography, Bioorganic Chemistry... Laboratory, Dona Paula Goa- India; bCSIR-National Institute of Oceanography Regional centre, Kochi, India, Email:param@nio.org; cDepartment of Chemistry, Goa University, Goa 403 206, India, Email:majikms@gmail.com Abstract Bis...

  6. Alkaloid and other chemical constituents from Psychotria stachyoides Benth

    Pimenta, Antonia T.A.; Uchoa, Daniel E.A.; Silveira, Edilberto R.; Lima, Mary Anne S. [Departamento de Quimica Organica e Inorganica, Universidade Federal do Ceara, Fortaleza, CE (Brazil); Braz-Filho, Raimundo, E-mail: mary@dqoi.ufc.br [Centro de Ciencias, Universidade Estadual do Norte Fluminense and Universidade Federal Rural do Rio de Janeiro, Campos dos Goytacazes-RJ (Brazil)

    2011-09-15

    The organic extracts of leaves and roots of Psychotria stachyoides provided the new glucoside monoterpenoid indole alkaloid N-demethylcorreantoside, besides bizantionoside B, a-amyrin, alizarine methyl-ether, rubiadine, scopoletin, barbinevic acid and a mixture of b-sitosterol and stigmasterol glucosides. The structural characterization of the isolates was established based on infrared spectroscopy (IR), mass spectrometry (MS) and, particularly, 1D and 2D nuclear magnetic resonance (NMR). (author)

  7. Alkaloids of in vitro cultures of Rhazya stricta

    Akhgari, Amir

    2015-01-01

    Rhazya stricta Decne. (Apocynaceae) is a traditional medicinal plant in the Middle East and South Asia. It produces a large number of terpenoid indole alkaloids(TIAs), some of which possess important pharmacological properties. This study focused on the establishment of biotechnological production tools of R. stricta, namely undifferentiated cell cultures, and an Agrobacterium rhizogenes-mediated transformation method to obtain hairy roots expressing heterologous genes from the early TIA path...

  8. Alkaloid and other chemical constituents from Psychotria stachyoides Benth

    The organic extracts of leaves and roots of Psychotria stachyoides provided the new glucoside monoterpenoid indole alkaloid N-demethylcorreantoside, besides bizantionoside B, a-amyrin, alizarine methyl-ether, rubiadine, scopoletin, barbinevic acid and a mixture of b-sitosterol and stigmasterol glucosides. The structural characterization of the isolates was established based on infrared spectroscopy (IR), mass spectrometry (MS) and, particularly, 1D and 2D nuclear magnetic resonance (NMR). (author)

  9. Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives

    Gaziano, Roberta; Moroni, Gabriella; Buè, Cristina; Miele, Martino Tony; Sinibaldi-Vallebona, Paola; Pica, Francesca

    2016-01-01

    Historically, natural products have represented a significant source of anticancer agents, with plant-derived drugs becoming increasingly explored. In particular, sanguinarine is a benzophenanthridine alkaloid obtained from the root of Sanguinaria canadensis, and from other poppy Fumaria species, with recognized anti-microbial, anti-oxidant and anti-inflammatory properties. Recently, increasing evidence that sanguinarine exibits anticancer potential through its capability of inducing apoptosi...

  10. Activity of Alkaloids on Peptic Ulcer: What’s New?

    Raphaela Francelino do Nascimento; Igor Rafael Praxedes de Sales; Rodrigo de Oliveira Formiga; José Maria Barbosa-Filho; Marianna Vieira Sobral; Josean Fechine Tavares; Margareth de Fátima Formiga de Melo Diniz; Leônia Maria Batista

    2015-01-01

    Peptic ulcer is a common disease characterized by lesions that affect the mucosa of the esophagus, stomach and/or duodenum, and may extend into the muscular layer of the mucosa. Natural products have played an important role in the process of development and discovery of new drugs, due to their wide structural diversity and present, mostly specific and selective biological activities. Among natural products the alkaloids, biologically active secondary metabolites, that can be found in plants,...

  11. Claviceps nigricans and Claviceps grohii: their alkaloids and phylogenetic placement

    Pažoutová, Sylvie; Olšovská, Jana; Šulc, Miroslav; Chudíčková, Milada; Flieger, Miroslav

    2008-01-01

    Roč. 71, č. 6 (2008), s. 1085-1088. ISSN 0021-8995 R&D Projects: GA MŠk LC07017 Grant ostatní: US(US) Sorghum, Millet and Other Grains CRSP (USAID) Institutional research plan: CEZ:AV0Z50200510 Keywords : ergot fungi * alkaloid * uplc Subject RIV: EE - Microbiology, Virology Impact factor: 1.187, year: 2008

  12. Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

    Larsson, Sonny; Rønsted, Nina

    2014-01-01

    The subject of chemosystematics has provided insight to both botanical classification and drug development. However, degrees of subjectivity in botanical classifications and limited understanding of the evolution of chemical characters and their biosynthetic pathways has often hampered such studies. In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Fol...

  13. Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus

    Jianhua Zhu; Mingxuan Wang; Wei Wen; Rongmin Yu

    2015-01-01

    Catharanthus roseus produces a wide range of terpenoid indole alkaloids (TIA). Many of them, such as vinblastine and vincristine, have significant bioactivity. They are valuable chemotherapy drugs used in combination with other drugs to treat lymphoma and leukemia. The TIA biosynthetic pathway has been investigated for many years, for scientific interest and for their potential in manufacturing applications, to fulfill the market demand. In this review, the progress and perspective of C. rose...

  14. Anxiolytic-like effects of erythrinian alkaloids from Erythrina suberosa

    Serrano, Maria Amelia R.; Batista, Andrea N. de L.; Bolzani, Vanderlan da S.; Santos, Luciana de A. [UNESP, Araraquara, SP (Brazil). Inst. de Quimica; Nogueira, Paulo J. de C.; Nunes-de-Souza, Ricardo L. [UNESP, Araraquara, SP (Brazil). Faculdade de Ciencias Farmaceuticas; Latif, Abdul; Arfan, Mohammad [University of Peshawar, Peshawar (Pakistan). Inst. of Chemical Sciences

    2011-07-01

    Two alkaloids, erysodine (1) and erysothrine (2) were isolated from the flowers of a Pakistani medicinal plant, Erythrina suberosa. These compounds were investigated for anxiolytic properties, and the results showed significant effect, in an acute oral treatment with 1-2, which were suspended in saline (NaCl 0.9%) plus DMSO 1%, and evaluated in 122 Swiss male mice exposed to two tests of anxiety - the elevated plus-maze (EPM) and the light/dark transition model (LDTM). (author)

  15. Enantioselective Nazarov Cyclization Catalyzed by a Cinchona Alkaloid Derivative

    Huang, Yu-Wen; Frontier, Alison J.

    2015-01-01

    Nucleophilic catalysts for a 1,6 addition/Nazarov cyclization/elimination sequence were evaluated for their ability to induce enantioselectivity in the electrocyclization step. Of the tertiary amines examined, it was found that a cinchona alkaloid derivative was able to generate substituted 5-hydroxy γ-methylene cyclopentenones with excellent enantioselectivity. The study results suggest that successful cyclization depends upon the ability of the dienyl diketone substrate to readily adopt an s-cis conformation. PMID:26085696

  16. Wild Argentinian Amaryllidaceae, a New Renewable Source of the Acetylcholinesterase Inhibitor Galanthamine and Other Alkaloids

    Feresin, Gabriela E.; Jaume Bastida; Alejandro Tapia; German Roitman; Cristina Theoduloz; Strahil Berkov; Natalia B. Pigni; Javier E. Ortiz

    2012-01-01

    The Amaryllidaceae family is well known for its pharmacologically active alkaloids. An important approach to treat Alzheimer’s disease involves the inhibition of the enzyme acetylcholinesterase (AChE). Galanthamine, an Amaryllidaceae alkaloid, is an effective, selective, reversible, and competitive AchE inhibitor. This work was aimed at studying the alkaloid composition of four wild Argentinian Amarillydaceae species for the first time, as well as analyzing their inhibitory activity...

  17. Radiation Processed Carrageenan Improves Plant Growth, Physiological Activities, and Alkaloids Production in Catharanthus roseus L.

    Naeem, M.; Mohd Idrees; Tariq Aftab; M. Masidur Alam; Khan, M. Masroor A.; Moin Uddin; Lalit Varshney

    2015-01-01

    Catharanthus roseus (L.) G. Don (Apocynaceae) is a medicinal plant that produces indole alkaloids used in cancer chemotherapy. Commercially important antineoplastic alkaloids, namely, vinblastine and vincristine, are mainly present in the leaves of C. roseus. Gamma-rays irradiated carrageenan (ICR) has been proven as plant growth promoting substance for a number of medicinal and agricultural plants. Considering the importance of ICR as a promoter of plant growth and alkaloids production in C....

  18. Main Alkaloids of Peganum harmala L. and Their Different Effects on Dicot and Monocot Crops

    Chi Zhang; Yuanming Zhang; Hua Shao; Xiaoli Huang

    2013-01-01

    Alkaloids with allelopathic activity are not as well-known as other allelochemicals. Our study revealed that total alkaloids from seeds of the medicinal plant Peganum harmala L. possessed significant growth inhibitory effect on four treated plants, with dicot plants (lettuce and amaranth) being more sensitive than the tested monocot plants (wheat and ryegrass). Further investigation led to the isolation of harmaline and harmine as the main active ingredients in the total alkaloids of P. harma...

  19. Alkaloids Induce Programmed Cell Death in Bloodstream Forms of Trypanosomes (Trypanosoma b. brucei)

    Michael Wink; Vera Rosenkranz

    2008-01-01

    The potential induction of a programmed cell death (PCD) in Trypanosoma b. brucei by 55 alkaloids of the quinoline, quinolizidine, isoquinoline, indole, terpene, tropane, steroid, and piperidine type was studied by measuring DNA fragmentation and changes in mitochondrial membrane potential. For comparison, the induction of apoptosis by the same alkaloids in human leukemia cells (Jurkat APO-S) was tested. Several alkaloids of the isoquinoline, quinoline, indole and steroidal type (berberine, c...

  20. Radiolytically degraded sodium alginate enhances plant growth, physiological activities and alkaloids production in Catharanthus roseus L.

    Naeem, M.; Tariq Aftab; Abid A. Ansari; Mohd Idrees; Akbar Ali; Khan, M. Masroor A.; Moin Uddin; Lalit Varshney

    2015-01-01

    Catharanthus roseus (L.) G. Don (Family Apocynaceae) is a medicinal plant that produces indole alkaloids used in cancer chemotherapy. The anticancerous alkaloids, viz. vinblastine and vincristine, are mainly present in the leaves of C. roseus. High demand and low yield of these alkaloids in the plant has led to explore the alternative means for their production. Gamma irradiated sodium alginate (ISA) has proved as a plant growth promoting substance for various medicinal and agricultural crops...

  1. Binary stress induces an increase in indole alkaloid biosynthesis in Catharanthus roseus

    Wei ZHU; Yang, Bingxian; Komatsu, Setsuko; Lu, Xiaoping; Li, Ximin; Tian, Jingkui

    2015-01-01

    Catharanthus roseus is an important medicinal plant, which produces a variety of indole alkaloids of significant pharmaceutical relevance. In the present study, we aimed to investigate the potential stress-induced increase of indole alkaloid biosynthesis in C. roseus using proteomic technique. The contents of the detectable alkaloids ajmalicine, vindoline, catharanthine, and strictosidine in C. roseus were significantly increased under binary stress. Proteomic analysis revealed that the abund...

  2. Binary Stress Induces an Increase in Indole Alkaloid Biosynthesis in Catharanthus roseus

    Wei eZhu; Bingxian eYang; Setsuko eKomatsu; Xiaoping eLu; Ximin eLi; Jingkui eTian

    2015-01-01

    Catharanthus roseus is an important medicinal plant, which produces a variety of indole alkaloids of significant pharmaceutical relevance. In the present study, we aimed to investigate the potential stress-induced increase of indole alkaloid biosynthesis in C. roseus using proteomic technique. The contents of the detectable alkaloids ajmalicine, vindoline, catharanthine, and strictosidine in C. roseus were significantly increased under binary stress. Proteomic analysis revealed that the abund...

  3. A virus-induced gene silencing approach to understanding alkaloid metabolism in Catharanthus roseus

    Liscombe, David K.; O’Connor, Sarah E.

    2011-01-01

    The anticancer agents vinblastine and vincristine are bisindole alkaloids derived from coupling vindoline and catharanthine, monoterpenoid indole alkaloids produced exclusively by Madagascar periwinkle (Catharanthus roseus) plants. Industrial production of vinblastine and vincristine currently relies on isolation from C. roseus leaves, a process that affords these compounds in 0.0003–0.01% yields. Metabolic engineering efforts to improve alkaloid content or provide alternative sources of the ...

  4. Penentuan Sifat Kimia Fisika Senyawa Alkaloid Hasil Isolasi Dari Daun Bandotan (Ageratum Conyzoides Linn.)

    Hasibuan, Poppy Anjelisa Z.; Nainggolan, Marline

    2010-01-01

    Extraction, isolation and identification of alkaloid from bandotan’s leaf (Ageratum conyzoides Linn.) has been carried out. Extraction was done by maceration method by using methanol. Isolation has been carried out by adding acid base to give crude alkaloid. The isolation followed by column chromatography by using chloroform-methanol-amonia as mobile phase (85-15-1) and silica gel 60 (mesh 70-230 ASTM) as statis phase. The result of column chromatography has get one white crystal alkaloid...

  5. Alkaloids and acetogenins in Annonaceae development: biological considerations

    Alma Rosa González-Esquinca

    2014-01-01

    Full Text Available Chemical studies of the plant family Annonaceae have intensified in the last several decades due to the discovery of annonaceous molecules with medicinal potential (e.g., benzylisoquinoline alkaloids and acetogenins. Approximately 500 alkaloids have been identified in 138 Annonaceae species in 43 genera. In addition, until 2004, 593 annonaceous acetogenins (ACGs had been identified, from 51 species in 13 genera.This suggests that plants from this family allocate important resources to the biosynthesis of these compounds. Despite the diversity of these molecules, their biological roles, including their physiological and/or ecological functions, are not well understood. In this study, it was provided new data describing the variety and distribution of certain alkaloids and ACGs in annonaceous plants in distinct stages of development. The potential relationships among some of these compounds and the seasonally climatic changes occurring in the plant habitat are also discussed. These data will improve our understanding of the secondary metabolism of these pharmacologically important molecules and their expression patterns during development, which will help to determine the optimal growth conditions and harvest times for their production.

  6. Absence of alkaloids in Psychotria carthagenensis Jacq. (Rubiaceae).

    Leal, M B; Elisabetsky, E

    1996-10-01

    Psychotria viridis and P. carthagenensis are often discussed in relation to the hallucinogenic beverage Ayahuasca, used for religious, medicinal and social purposes. The significance of including Psychotria species in this beverage has been understood on the basis of substantial amounts of tryptamine alkaloids detected on leaves of both P. viridis and P. carthagenensis. Nevertheless, there is a long lasting debate over the identification of which Psychotria species are actually traditionally employed. We here report that a P. carthagenensis leaf ethanol extract was found to be devoid of alkaloids. The extract significantly decreased mice body temperature (350 and 500 mg/kg). Toxicity assessment revealed that the extract induced sedation and slight ptoses (75% of animals treated with 1000 mg/kg). Lethality was not observed within 48 h. The data indicate that P. carthagenensis does have bioactive compound(s), possibly active at the central nervous system, but unlikely to be tryptamine alkaloids as in the case of P. viridis. Therefore, if P. carthagenensis is indeed used by ayahuasqueros, its chemical and pharmacological significance have yet to be elucidated. PMID:8941866

  7. Metabolic engineering for the production of plant isoquinoline alkaloids.

    Diamond, Andrew; Desgagné-Penix, Isabel

    2016-06-01

    Several plant isoquinoline alkaloids (PIAs) possess powerful pharmaceutical and biotechnological properties. Thus, PIA metabolism and its fascinating molecules, including morphine, colchicine and galanthamine, have attracted the attention of both the industry and researchers involved in plant science, biochemistry, chemical bioengineering and medicine. Currently, access and availability of high-value PIAs [commercialized (e.g. galanthamine) or not (e.g. narciclasine)] is limited by low concentration in nature, lack of cultivation or geographic access, seasonal production and risk of overharvesting wild plant species. Nevertheless, most commercial PIAs are still extracted from plant sources. Efforts to improve the production of PIA have largely been impaired by the lack of knowledge on PIA metabolism. With the development and integration of next-generation sequencing technologies, high-throughput proteomics and metabolomics analyses and bioinformatics, systems biology was used to unravel metabolic pathways allowing the use of metabolic engineering and synthetic biology approaches to increase production of valuable PIAs. Metabolic engineering provides opportunity to overcome issues related to restricted availability, diversification and productivity of plant alkaloids. Engineered plant, plant cells and microbial cell cultures can act as biofactories by offering their metabolic machinery for the purpose of optimizing the conditions and increasing the productivity of a specific alkaloid. In this article, is presented an update on the production of PIA in engineered plant, plant cell cultures and heterologous micro-organisms. PMID:26503307

  8. Short-term toxicity studies of loline alkaloids in mice.

    Finch, S C; Munday, J S; Munday, R; Kerby, J W F

    2016-08-01

    Epichloë endophytes have been used successfully in pastoral systems to reduce the impact of insect pests through the expression of secondary metabolites. The use of endophytes could be extended to other plant species, such as cereal crops, where the production of bioactive secondary metabolites would reduce the reliance on pesticides for insect control. The success of this approach is dependent on the selection of an appropriate secondary metabolite target which must not only be effective against insect pests but also be safe for grazing and monogastric animals. The loline alkaloids have been identified as possible target metabolites as they are associated with potent effects on insects and low toxicity to grazing animals. The purpose of the current study was to generate toxicological data on the loline alkaloids in a monogastric system using mice. Male and female mice were fed 415 mg/kg/day total lolines for a 3-week period. The loline treatment caused no statistically significant effect on gross pathology, histology, haematology, blood chemistry, heart rate, blood pressure or motor coordination. Reduced weight gain and food consumption were noted in the loline groups during the initial stages of the experiment. This experiment raises no food safety concerns for the loline alkaloids. PMID:27276360

  9. Ultrasonic extraction of steroidal alkaloids from potato peel waste.

    Hossain, Mohammad B; Tiwari, Brijesh K; Gangopadhyay, Nirupama; O'Donnell, Colm P; Brunton, Nigel P; Rai, Dilip K

    2014-07-01

    Potato processors produce large volumes of waste in the form of potato peel which is either discarded or sold at a low price. Potato peel waste is a potential source of steroidal alkaloids which are biologically active secondary metabolites which could serve as precursors to agents with apoptotic, chemopreventive and anti-inflammatory properties. The present study investigated the relative efficacy of ultrasound assisted extraction (UAE) and solid liquid extraction (SLE) both using methanol, to extract steroidal alkaloids from potato peel waste and identified optimal conditions for UAE of α-solanine, α-chaconine, solanidine and demissidine. Using response surface methodology optimal UAE conditions were identified as an amplitude of 61 μm and an extraction time of 17 min which resulted the recovery of 1102 μg steroidal alkaloids/g dried potato peel (DPP). In contrast, SLE yielded 710.51 glycoalkaloid μg/g DPP. Recoveries of individual glycoalkoids using UAE yielded 273, 542.7, 231 and 55.3 μg/g DPP for α-solanine, α-chaconine, solanidine and demissidine respectively. Whereas for SLE yields were 180.3, 337.6, 160.2 and 32.4 μg/g DPP for α-solanine, α-chaconine, solanidine and demissidine respectively. The predicted values from the developed second order quadratic polynomial equation were in close agreement with the experimental values with low average mean deviation (Epotato peel waste. PMID:24582305

  10. Naturally occurring bioactive Cyclobutane-containing (CBC) alkaloids in fungi, fungal endophytes, and plants.

    Dembitsky, Valery M

    2014-10-15

    This article focuses on the occurrence and biological activities of cyclobutane-containing (CBC) alkaloids obtained from fungi, fungal endophytes, and plants. Naturally occurring CBC alkaloids are of particular interest because many of these compounds display important biological activities and possess antitumour, antibacterial, antimicrobial, antifungal, and immunosuppressive properties. Therefore, these compounds are of great interest in the fields of medicine, pharmacology, medicinal chemistry, and the pharmaceutical industry. Fermentation and production of CBC alkaloids by fungi and/or fungal endophytes is also discussed. This review presents the structures and describes the activities of 98 CBC alkaloids. PMID:25442265

  11. Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

    Assem El-Shazly

    2014-04-01

    Full Text Available Among the diversity of secondary metabolites which are produced by plants as means of defence against herbivores and microbes, pyrrolizidine alkaloids (PAs are common in Boraginaceae, Asteraceae and some other plant families. Pyrrolizidine alkaloids are infamous as toxic compounds which can alkylate DNA und thus cause mutations and even cancer in herbivores and humans. Almost all genera of the family Boraginaceae synthesize and store this type of alkaloids. This review reports the available information on the present status (literature up to early 2014 of the pyrrolizidine alkaloids in the Boraginaceae and summarizes the topics structure, distribution, chemistry, chemotaxonomic significance, and biological properties.

  12. Determination of N,N-dimethyltryptamine and beta-carboline alkaloids in human plasma following oral administration of Ayahuasca.

    Yritia, Mercedes; Riba, Jordi; Ortuño, Jordi; Ramirez, Ariel; Castillo, Araceli; Alfaro, Yolanda; de la Torre, Rafael; Barbanoj, Manel J

    2002-11-01

    Ayahuasca is a South American psychotropic beverage prepared from plants native to the Amazon River Basin. It combines the hallucinogenic agent and 5-HT(2A/2C) agonist N,N-dimethyltryptamine (DMT) with beta-carboline alkaloids showing monoamine oxidase-inhibiting properties. In the present paper, an analytical methodology for the plasma quantification of the four main alkaloids present in ayahuasca plus two major metabolites is described. DMT was extracted by liquid-liquid extraction with n-pentane and quantified by gas chromatography with nitrogen-phosphorus detection. Recovery was 74%, and precision and accuracy were better than 9.9%. The limit of quantification (LOQ) was 1.6 ng/ml. Harmine, harmaline, and tetrahydroharmine (THH), the three main beta-carbolines present in ayahuasca, and harmol and harmalol (O-demethylation metabolites of harmine and harmaline, respectively) were measured in plasma by means of high-performance liquid chromatography (HPLC) with fluorescence detection. Sample preparation was accomplished by solid-phase extraction, which facilitated the automation of the process. All five beta-carbolines were measured using a single detector by switching wavelengths. Separation of harmol and harmalol required only slight changes in the chromatographic conditions. Method validation demonstrated good recoveries, above 87%, and accuracy and precision better than 13.4%. The LOQ was 0.5 ng/ml for harmine, 0.3 ng/ml for harmaline, 1.0 ng/ml for THH, and 0.3 ng/ml for harmol and harmalol. Good linearity was observed in the concentration ranges evaluated for DMT (2.5-50 ng/ml) and the beta-carbolines (0.3-100 ng/ml). The gas chromatography and HPLC methods described allowed adequate characterization of the pharmacokinetics of the four main alkaloids present in ayahuasca, and also of two major beta-carboline metabolites not previously described in the literature. PMID:12361741

  13. Atropurpuran – Missing Biosynthetic Link Leading to the Hetidine and Arcutine C20-Diterpenoid Alkaloids or an Oxidative Degradation Product?

    Weber, Manuel; Owens, Kyle; Sarpong, Richmond

    2015-01-01

    A possible biosynthetic link between atropurpuran, the hetidine diterpenoid alkaloids and the alkaloid arcutine and congeners is proposed. The feasibility of aspects of this biosynthesis, especially key 1,2-rearrangements, have been examined computationally. PMID:26028789

  14. Fos-like immunoreactivity in rat dorsal raphe nuclei induced by alkaloid extract of Mitragyna speciosa.

    Kumarnsit, Ekkasit; Vongvatcharanon, Uraporn; Keawpradub, Niwat; Intasaro, Pranom

    2007-04-12

    Mitragyna speciosa (MS) has been traditionally used for medicinal purposes especially in southern Thailand. Previously, an alkaloid extract of this plant was demonstrated to mediate antinociception, partly, through the descending serotonergic system. The present study investigated the stimulatory effect of the MS extract on the dorsal raphe nucleus and its antidepressant-like activity. The MS extract containing approximately 60% mitragynine as a major indole alkaloid was used to treat the animals. The stimulatory effect of the MS extract was determined by detecting the expression of the immediate early gene, cfos, in the dorsal raphe nucleus of male Wistar rats. The immunohistochemistry was used to detect Fos protein, the protein product of cfos gene. The present data show that a significant increase in Fos expression was observed following long-term administration of the MS extract (40 mg/kg) for 60 consecutive days. In addition, the antidepressant-like activity of the MS extract was determined by using the forced swimming test (FST) in male mice. The results show that a single injection (either 60 or 90 mg/kg doses) significantly decreased immobility time in the FST. These findings indicate that the MS extract has a stimulatory effect on the dorsal raphe nucleus and an antidepressant-like activity. Stimulation of this brain area has been known to cause antinociception. These findings suggest that the MS extract might produce antinociceptive and/or antidepressive actions partly through activation of the dorsal raphe nucleus. Moreover, the dorsal raphe nucleus may be one of site of MS action in the central nervous system. PMID:17316993

  15. Analysis of Alkaloids from Physalis peruviana by Capillary GC, Capillary GC-MS, and GC-FTIR.

    Kubwabo, C; Rollmann, B; Tilquin, B

    1993-04-01

    The alkaloid composition of the aerial parts and roots of PHYSALIS PERUVIANA was analysed by capillary GC (GC (2)), GC (2)-MS and GC (2)-FTIR. Eight alkaloids were identified, three of those alkaloids are 3beta-acetoxytropane and two N-methylpyrrolidinylhygrine isomers, which were not previously found in the genus PHYSALIS. A reproduction of the identification of alkaloids detected in the plant by the use of retention indices has been proposed. PMID:17230349

  16. A divergent approach to benzylisoquinoline-type and oxoaporphine alkaloids via regioselective direct ring metalation of alkoxy isoquinolines.

    Melzer, Benedikt; Bracher, Franz

    2015-07-28

    Methoxy- and benzyloxy-substituted isoquinolines are regioselectively metalated at C-1 with the Knochel-Hauser base, subsequent trapping with aromatic aldehydes gives aryl(isoquinolin-1-yl)carbinols as building blocks for divergent syntheses of different types of benzylisoquinoline alkaloids. Photochemical cyclization of ortho-bromo analogues under reductive conditions gives oxoaporphine alkaloids. Nine benzylisoquinoline alkaloids and two oxoaporphine alkaloids were obtained in two or three steps from appropriate isoquinolines. PMID:26081123

  17. New C19-Diterpenoid Alkaloids from the Roots of Delphinium Giraldii

    周先礼; 陈巧鸿; 陈东林; 王锋鹏

    2003-01-01

    Three new C19-diterpenoid alkaloids, giraldines A (1), B (3) and C (4), were isolated from the roots of Delphinium giraldii Diels, together with three known C19-diterpenoid alkaloids, dihydrogadesine (5), tatsiensine (6) and siwanine A (7), as well as their structures were elucidated by chemical evidence and spectral analyses, including IR, MS, 1D NMR and 2D NMR.

  18. Conformational, IR spectroscopic and electronic properties of conium alkaloids and their adducts with C60 fullerene

    Zabolotnyi, M. A.; Prylutskyy, Yu I.; Poluyan, N. A.; Evstigneev, M. P.; Dovbeshko, G. I.

    2016-08-01

    Conformational, IR spectroscopic and electronic properties of the components of Conium alkaloids (Conium maculatum) in aqueous environment were determined by model calculations and experiment. With the help of FT-IR spectroscopy the possibility of formation of an adduct between γ-coniceine alkaloid and C60 fullerene was demonstrated, which is important for further application of conium analogues in biomedical purposes.

  19. The toxicity of Poison Dart Frog alkaloids against the Fire Ant (Solenopsis invicta)

    Hundreds of alkaloids, representing over 20 structural classes, have been identified from the skin of neotropical poison frogs (Dendrobatidae). These alkaloids are derived from arthropod prey of the frogs, and are generally are believed to deter vertebrate predators. We developed a method to put ind...

  20. Antimicrobial activity of benzylisoquinoline alkaloids from Annona salzmanii D.C.

    Paulo, M de Q; Barbosa-Filho, J M; Lima, E O; Maia, R F; Barbosa, R de C; Kaplan, M A

    1992-02-01

    Bark of Annona salzmanii D.C. (Annonaceae), used in Brazilian folk medicine, was found to contain four benzylisoquinoline alkaloids, namely reticuline, anonaine, laurelliptine and isoboldine. Only anonaine possesses some antibacterial property while all four alkaloids show some antifungal activity. PMID:1501491

  1. Heterozygous P53 knockout mouse model for dehydropyrrolizidine alkaloid-induced carcinogenesis

    Dehydropyrrolizidine alkaloids are a large, structurally diverse group of plant-derived protoxins that are potentially carcinogenic. With worldwide significance, these alkaloids can contaminate or be naturally present in the human food supply. To develop a small animal model that may be used to com...

  2. Renieramycins H and I, two novel alkaloids from the sponge Haliclona cribricutis Dendy

    Parameswaran, P.S.; Naik, C.G.; Kamat, S.Y.; Pramanik, B.N.

    The known alkaloid, mimosamycin 1, along with its moon- and di hydroxy derivaties, 4-hydroxy mimosamycin 2 and 1, 4-dihydroxymimosamycin 3 and two new dimeric alkaloids: namely renieramycins H and I 4 and 5 have been isolated from the MeOH extract...

  3. Livestock Poisoning with Pyrrolizidine Alkaloid Containing Plants (Senecio, Crotalaria, Cynoglossum, Amsinckia, Heliotropium and Echium spp.)

    Pyrrolizidine alkaloids (PAs) are potent liver toxins that have been identified in over 6,000 plants throughout the world. Alkaloids are nitrogen-based compounds with potent biological activity. About half of the identified PAs are toxic and several cause cancer (carcinogenic). PA-containing plants...

  4. 11-Isopropylcryptolepine: A novel alkaloid isolated from cryptolepis sanguinolenta characterized using submicro NMR techniques

    Hadden; Sharaf; Guido; Robins; Tackie; Phoebe; Schiff; Martin

    1999-02-01

    A new alkaloid has been isolated from extracts of the West African plant Cryptolepis sanguinolenta and identified by submicro NMR techniques as 11-isopropylcryptolepine (1). The unusual incorporation of the isopropyl group at the 11-position of the indolo[3,2-b]quinoline nucleus is suggestive of a mixed biosynthetic origin for the alkaloid. PMID:10075749

  5. Non-alkaloids extract from Stemona sessilifolia enhances the activity of chemotherapeutic agents through P-glycoprotein-mediated multidrug-resistant cancer cells.

    Han, Lu; Ma, Yang-Mei; An, Li; Zhang, Qiao; Wang, Chang-Li; Zhao, Qing-Chun

    2016-01-01

    One of the major impediments to the successful treatment of cancer is the development of resistant cancer cells, which could cause multidrug resistance (MDR), and overexpression of ABCB1/P-glycoprotein (P-gp) is one of the most common causes of MDR in cancer cells. Recently, natural products or plant-derived chemicals have been investigated more and more widely as potential multidrug-resistant (MDR) reversing agents. The current study demonstrated for the first time that non-alkaloids extract from Stemona sessilifolia significantly reversed the resistance of chemotherapeutic agents, adriamycin, paclitaxel and vincristine to MCF-7/ADR cells compared with MCF-7/S cells in a dose-dependent manner. The results obtained from these studies indicated that the non-alkaloids extract from S. sessilifolia plays an important role in reversing MDR of cancer as a P-gp modulator in vitro and may be effective in the treatment of multidrug-resistant cancers. PMID:26190165

  6. Bromopyrrole Alkaloids as Lead Compounds against Protozoan Parasites

    Deniz Tasdemir

    2010-07-01

    Full Text Available In the present study,13 bromopyrrole alkaloids, including the oroidin analogs hymenidin (2, dispacamide B (3 and dispacamide D (4, stevensine (5 and spongiacidin B (6, their derivatives lacking the imidazole ring bromoaldisin (7, longamide B (8 and longamide A (9, the dimeric oroidin derivatives sceptrin (10 and dibromopalau’amine (11, and the non-oroidin bromopyrrolohomoarginin (12, manzacidin A (13, and agelongine (14, obtained from marine sponges belonging to Axinella and Agelas generahave been screened in vitro against four parasitic protozoa, i.e., two Trypanosoma species (T. brucei rhodesiense and T. cruzi, Leishmania donovani and Plasmodium falciparum (K1 strain, a chloroquine resistant strain, responsible of human diseases with high morbidity and, in the case of malaria, high mortality. Our results indicate longamide B (8 and dibromopalau’amine (11 to be promising trypanocidal and antileishmanial agents, while dispacamide B (3 and spongiacidin B (6 emerge as antimalarial lead compounds.In addition,evaluation of the activity of the test alkaloids (2–14 against three different enzymes (PfFabI, PfFabG, PfFabZ involved in the de novo fatty acid biosynthesis pathway of P. falciparum (PfFAS-II identified bromopyrrolohomoarginin (12 as a potent inhibitor of PfFabZ. The structural similarity within the series of tested molecules allowed us to draw some preliminary structure-activity relationships. Tests against the mammalian L6 cells revealed important clues on therapeutic index of the metabolites. This is the first detailed study on the antiprotozoal potential of marine bromopyrrole alkaloids.

  7. Determining important parameters related to cyanobacterial alkaloid toxin exposure

    Love, A H

    2005-09-16

    Science-based decision making required robust and high-fidelity mechanistic data about the system dynamics and impacts of system changes. Alkaloid cyanotoxins have the characteristics to warrant consideration for their potential threat. Since insufficient information is available to construct a systems model for the alkaloid cyanotoxins, saxitoxins, anatoxins, and anatoxin-a(S), an accurate assessments of these toxins as a potential threat for use for intentional contamination is not possible. Alkaloid cyanotoxin research that contributed to such a model has numerous areas of overlap for natural and intentional health effects issues that generates dual improvements to the state of the science. The use of sensitivity analyses of systems models can identify parameters that, when determined, result in the greatest impact to the overall system and may help to direct the most efficient use of research funding. This type of modeling-assisted experimentation may allow rapid progress for overall system understanding compared to observational or disciplinary research agendas. Assessment and management of risk from intentional contamination can be performed with greater confidence when mechanisms are known and the relationships between different components are validated. This level of understanding allows high-fidelity assessments that do not hamper legitimate possession of these toxins for research purposes, while preventing intentional contamination that would affect public health. It also allows for appropriate response to an intentional contamination event, even if the specific contamination had not been previous considered. Development of science-based decision making tools will only improve our ability to address the new requirements addressing potential threats to our nation.

  8. Alkaloids Induce Programmed Cell Death in Bloodstream Forms of Trypanosomes (Trypanosoma b. brucei

    Michael Wink

    2008-10-01

    Full Text Available The potential induction of a programmed cell death (PCD in Trypanosoma b. brucei by 55 alkaloids of the quinoline, quinolizidine, isoquinoline, indole, terpene, tropane, steroid, and piperidine type was studied by measuring DNA fragmentation and changes in mitochondrial membrane potential. For comparison, the induction of apoptosis by the same alkaloids in human leukemia cells (Jurkat APO-S was tested. Several alkaloids of the isoquinoline, quinoline, indole and steroidal type (berberine, chelerythrine, emetine, sanguinarine, quinine, ajmalicine, ergotamine, harmine, vinblastine, vincristine, colchicine, chaconine, demissidine and veratridine induced programmed cell death, whereas quinolizidine, tropane, terpene and piperidine alkaloids were mostly inactive. Effective PCD induction (EC50 below 10 µM was caused in T. brucei by chelerythrine, emetine, sanguinarine, and chaconine. The active alkaloids can be characterized by their general property to inhibit protein biosynthesis, to intercalate DNA, to disturb membrane fluidity or to inhibit microtubule formation.

  9. Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

    Qun Göthel; Thanchanok Sirirak; Matthias Köck

    2015-01-01

    Three new bromotyrosine-derived alkaloids 14-debromo-11-deoxyfistularin-3 (1), aplysinin A (2), and aplysinin B (3), together with 15 known compounds (4–18) were isolated from the sponge Aplysina lacunosa collected from Stirrup Cay, Bahamas. The structures of the isolated compounds were identified on the basis of MS and NMR data analysis. The 13C NMR assignment of spirocyclohexadienylisoxazoline moieties of 1 and 2 were confirmed by an 1,1-ADEQUATE experiment. Compounds 1 and 2 showed a mild ...

  10. Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa.

    Göthel, Qun; Sirirak, Thanchanok; Köck, Matthias

    2015-01-01

    Three new bromotyrosine-derived alkaloids 14-debromo-11-deoxyfistularin-3 (1), aplysinin A (2), and aplysinin B (3), together with 15 known compounds (4-18) were isolated from the sponge Aplysina lacunosa collected from Stirrup Cay, Bahamas. The structures of the isolated compounds were identified on the basis of MS and NMR data analysis. The (13)C NMR assignment of spirocyclohexadienylisoxazoline moieties of 1 and 2 were confirmed by an 1,1-ADEQUATE experiment. Compounds 1 and 2 showed a mild to moderate cytotoxic activities against KB-31 and FS4-LTM cell lines. Only aplysinin A (2) exhibited cytotoxicity against MCF-7 cells. PMID:26734082

  11. An azafluorenone alkaloid and a megastigmane from Unonopsis lindmanii (Annonaceae)

    Yoshida, Nidia C., E-mail: nidiayoshida@usp.br [Universidade de Sao Paulo (USP), SP (Brazil). Instituto de Quimica; Siqueira, Joao M. de [Universidade Federal de Sao Joao Del Rei, Divinpolis, MG (Brazil). Departamento de Farmacia; Rodrigues, Ricardo P. [Universidade de Sao Paulo (USP), Ribeirao Preto, SP (Brazil). Faculdade de Ciencias Farmaceuticas; Correia, Rodolfo P. [Universidade de Sao Paulo (USP), SP (Brazil). Instituto de Ciencias Biomedicas; Garcez, Walmir S., E-mail: walmir.garcez@ufms.br [Universidade Federal de Mato Grosso do Sul (UFMS), Campo Grande, MS (Brazil). Departamento de Quimica

    2013-04-15

    The azafluorenone alkaloid 5,8-dimethoxy-7-hydroxy-1-methyl-4-azafluoren-9-one and the megastigman (-)-(5R*, 6S*)-megastigman-3-one-10,7-olide were isolated from aerial parts of Unonopsis lindmanii (Annonaceae), along with the known compounds (3S*,5S*,8R*)-3,5-dihydroxymegastigma-6,7-dien-9-one (grasshopper ketone), N-trans-feruloyltyramine, (-)-anonaine, (-)-asimilobine, liriodenine and (-)-syringaresinol. This is the first description of the presence of megastigmanes in Annonaceae. The structures of the compounds were elucidated based on spectroscopic data. (author)

  12. Synthesis of some 11C-labelled alkaloids

    Using (11C)-methyl iodide in N-alkylation reactions in dimethylformamide (DMF), the alkaloids N-(11C-methyl)-morphine, N-(11C-methyl)-codeine, 6-N(methyl)-9, 10-dihydroergotamine, 6-N-(11C-methyl)-bromocriptine and N-(11C-methyl)-nicotine have been synthesized in radiochemical yields of 50-95%, within 5-10 min of introducing (11C)-methyl iodide into the reaction vial. (11C)-Methyl iodide was obtained within 4-7 min from (11C)-carbon dioxide prepared by the 14N(p,α)11C reaction. (Authors)

  13. Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

    Qun Göthel

    2015-11-01

    Full Text Available Three new bromotyrosine-derived alkaloids 14-debromo-11-deoxyfistularin-3 (1, aplysinin A (2, and aplysinin B (3, together with 15 known compounds (4–18 were isolated from the sponge Aplysina lacunosa collected from Stirrup Cay, Bahamas. The structures of the isolated compounds were identified on the basis of MS and NMR data analysis. The 13C NMR assignment of spirocyclohexadienylisoxazoline moieties of 1 and 2 were confirmed by an 1,1-ADEQUATE experiment. Compounds 1 and 2 showed a mild to moderate cytotoxic activities against KB-31 and FS4-LTM cell lines. Only aplysinin A (2 exhibited cytotoxicity against MCF-7 cells.

  14. Scientific Opinion on Ergot alkaloids in food and feed

    EFSA Panel on Contaminants in the Food Chain (CONTAM)

    2012-01-01

    The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs) in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread Claviceps species within the Hypocreales. A total of 20 558 analytical results for EAs in 1 716 food, 496 feed and 67 unprocessed grain samples wer...

  15. Anti-Acetylcholinesterase Alkaloids from Annona glabra Leaf.

    Lee, Shoei-Sheng; Wu, Dong-Yi; Tsai, Sheng-Fa; Chen, Chien-Kuang

    2015-06-01

    Bioassay guided fractionation and separation of the EtOH extract of Annona glabra leaf against acetylcholinesterse led to the characterization of 15 alkaloids. Among them, (-)-actinodaphnine (2) and (-)-(6aS,7R)-7-hydroxyactinodaphnine (9) are new aporphines, although (+)-2 and (±)-2 have been found in several plants. Their structures were established by spectroscopic analysis. (-)-Anolobine (5) and (-)-roemeroline (8) showed moderate inhibitory activity against eel acetylcholinesterase with IC50 values of 22.4 and 26.3 μM, respectively. PMID:26197510

  16. Bromopyrrole alkaloids from the Caribbean sponge Agelas cerebrum

    Regalado, Erik L.; Laguna, Abilio, E-mail: erikluis18@gmail.co [Center of Marine Bioproducts, Havana (Cuba). Dept. of Chemistry; Mendiola, Judith [Institute of Tropical Medicine Pedro Kouri (IPK), Havana (Cuba). Dept. of Parasitology; Thomas, Olivier P. [Universite de Nice-Sophia Antipolis (France). Lab. de Chimie des Molecules Bioactives et des Aromes; Nogueiras, Clara [University of Havana, San Lazaro y L, Havana (Cuba). Faculty of Chemistry. Center of Natural Products

    2011-07-01

    Bioguided fractionation of Agelas cerebrum crude extract resulted in isolation of four bromopyrrole and four bromopyrrole aminoimidazole alkaloids, identified as 5-bromopyrrole-2-carboxylic acid (1), 4-bromopyrrole-2-carboxylic acid (2), 3,4-bromopyrrole-2-carboxylic acid (3), 4,5-bromopyrrole-2-carboxylic acid (4), oroidin (5), bromoageliferin (6), dibromoageliferin (7) and dibromosceptrin (8) on the basis of spectroscopic data analyses (UV, IR, HRMS, 1D and 2D NMR) and comparison with literature data. This is the first report of compounds 2 and 3 in a marine sponge belonging to the Agelas genus and the first evidence of the presence of 1 from a natural source. (author)

  17. Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus.

    Zhu, Jianhua; Wang, Mingxuan; Wen, Wei; Yu, Rongmin

    2015-01-01

    Catharanthus roseus produces a wide range of terpenoid indole alkaloids (TIA). Many of them, such as vinblastine and vincristine, have significant bioactivity. They are valuable chemotherapy drugs used in combination with other drugs to treat lymphoma and leukemia. The TIA biosynthetic pathway has been investigated for many years, for scientific interest and for their potential in manufacturing applications, to fulfill the market demand. In this review, the progress and perspective of C. roseus TIA biosynthesis and its regulating enzymes are described. In addition, the culture condition, hormones, signaling molecules, precursor feeding on the accumulation of TIA, and gene expression are also evaluated and discussed. PMID:26009689

  18. Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus

    Jianhua Zhu

    2015-01-01

    Full Text Available Catharanthus roseus produces a wide range of terpenoid indole alkaloids (TIA. Many of them, such as vinblastine and vincristine, have significant bioactivity. They are valuable chemotherapy drugs used in combination with other drugs to treat lymphoma and leukemia. The TIA biosynthetic pathway has been investigated for many years, for scientific interest and for their potential in manufacturing applications, to fulfill the market demand. In this review, the progress and perspective of C. roseus TIA biosynthesis and its regulating enzymes are described. In addition, the culture condition, hormones, signaling molecules, precursor feeding on the accumulation of TIA, and gene expression are also evaluated and discussed.

  19. A Short Synthetic Route to the Calystegine Alkaloids

    Skaanderup, Philip Robert; Madsen, Robert

    2003-01-01

    An efficient strategy is described for the synthesis of enantiopure calystegine alkaloids. The key step employs a zinc-mediated fragmentation of benzyl-protected methyl 6-iodo-glycosides followed by in situ formation of the benzyl imine and Barbier-type allylation with zinc, magnesium, or indium...... metal. Stereochemistry in the pivotal allylation is controlled by the choice of the metal. The functionalized 1,8-nonadienes, thus formed, are converted into cycloheptenes by ring-closing metathesis. Regioselective hydroboration and oxidation give the corresponding cycloheptanones, which are deprotected...

  20. Ampullosine, a new isoquinoline alkaloid from Sepedonium ampullosporum (Ascomycetes).

    Quang, Dang Ngoc; Schmidt, Jürgen; Porzel, Andrea; Wessjohann, Ludger; Haid, Mark; Arnold, Norbert

    2010-06-01

    A new isoquinoline alkaloid, ampullosine (3-methyl-isoquinoline-6-carboxylic acid, 1), was isolated from Sepedonium ampullosporum and characterized by spectroscopic analysis and chemical reactions. This compound is responsible for the deep yellow color of the culture fluid of this species. Moreover, the known compounds sepedonin (2) and anhydrosepedonin (3) were detected. Twelve strains belonging to eight species of Sepedonium have been screened for these three metabolites by LC/ESI-SRM (selected reaction monitoring). Ampullosine (1) could be detected in almost all species in Sepedonium, but not in the phylogenetically more distant species S. brunneum and S. tulasneanum. Anhydrosepedonin (3) showed antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum. PMID:20614812

  1. Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus.

    Zhao, W; Wolfender, J L; Hostettmann, K; Xu, R; Qin, G

    1998-01-01

    From the root bark of Dictamnus dasycarpus (Rutaceae), four limonoid derivatives, two furoquinoline alkaloids, five limonoids, two sesquiterpenes and three steroids were isolated and their structures elucidated on the basis of various spectroscopic methods. Among the identified compounds, one was determined to be a new natural product, 6 beta-hydroxyfraxinellone, while six compounds were found to be active against the plant pathogenic fungus Cladosporium cucumerinum. The relationship between the structures of limonoid derivatives and their inhibitory activity against fungal growth was investigated. PMID:9429316

  2. New cycloartane saponin and monoterpenoid glucoindole alkaloids from Mussaenda luteola

    Mohamed, Shaymaa M.; Backheet, Enaam Y.; Bayoumi, Soad A.; Ross, Samir A.

    2016-01-01

    A new cycloartane-type saponin with unusual hydroxylation at C-17 and a unique side chain, 9 (R), 19, 22 (S), 24 (R) bicyclolanost-3β, 12α, 16β, 17α tetrol-25-one 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (1) and two new monoterpenoid glucoindole alkaloids, 10-methoxy pumiloside (2) and the previously chemically synthesized, 10-methoxy strictosidine (3) along with other five known compounds, 7α-morroniside (4), 7-epi-loganin (5), (7β)-7-O-methylmorroniside (6), 5(S)-5-carboxystrictisidine (7) and apigenin-7-O-neohesperidoside (8) were isolated from the aerial parts of Mussaenda luteola (Rubiaceae). The structural elucidation of the isolates was accomplished by extensive (1D and 2D NMR) spectroscopic data analysis and HR-ESI-MS. Compounds 4–8 were reported for the first time from the genus Mussaenda. Interestingly, this is the first report for the occurrence of the monoterpenoid glucoindole-type alkaloids in the genus which might be useful for the chemotaxonomic evaluation of the genus Mussaenda. All isolates were evaluated for their antiprotozoal activities. Compound 7 showed good antitrypanosomal activity with IC50 and IC90 values of 13.7 and 16.6 µM compared to IC50 and IC90 values of 13.06 and 28.99 µM for the positive control DFMO, difluoromethylornithine. PMID:26969788

  3. Pyrrolizidine alkaloids in food and feed on the Belgian market.

    Huybrechts, Bart; Callebaut, Alfons

    2015-01-01

    Pyrrolizidine alkaloids (PAs) are widely distributed plant toxins with species dependent hepatotoxic, carcinogenic, genotoxic and pneumotoxic risks. In a recent European Food Safety Authority (EFSA) opinion, only two data sets from one European country were received for honey, while one feed data set was included. No data are available for food or feed samples from the Belgian market. We developed an LC-MS/MS method, which allowed the detection and quantification of 16 PAs in a broad range of matrices in the sub ng g(-1) range. The method was validated in milk, honey and hay and applied to honey, tea (Camellia sinensis), scented tea, herbal tea, milk and feed samples bought on the Belgian market. The results confirmed that tea, scented tea, herbal tea and honey are important food sources of pyrrolizidine alkaloid contamination in Belgium. Furthermore, we detected PAs in 4 of 63 commercial milk samples. A high incidence rate of PAs in lucerne (alfalfa)-based horse feed and in rabbit feed was detected, while bird feed samples were less contaminated. We report for the first time the presence of monocrotaline, intermedine, lycopsamine, heliotrine and echimidine in cat food. PMID:26373269

  4. Plant-like biosynthesis of isoquinoline alkaloids in Aspergillus fumigatus.

    Baccile, Joshua A; Spraker, Joseph E; Le, Henry H; Brandenburger, Eileen; Gomez, Christian; Bok, Jin Woo; Macheleidt, Juliane; Brakhage, Axel A; Hoffmeister, Dirk; Keller, Nancy P; Schroeder, Frank C

    2016-06-01

    Natural product discovery efforts have focused primarily on microbial biosynthetic gene clusters (BGCs) containing large multimodular polyketide synthases and nonribosomal peptide synthetases; however, sequencing of fungal genomes has revealed a vast number of BGCs containing smaller NRPS-like genes of unknown biosynthetic function. Using comparative metabolomics, we show that a BGC in the human pathogen Aspergillus fumigatus named fsq, which contains an NRPS-like gene lacking a condensation domain, produces several new isoquinoline alkaloids known as the fumisoquins. These compounds derive from carbon-carbon bond formation between two amino acid-derived moieties followed by a sequence that is directly analogous to isoquinoline alkaloid biosynthesis in plants. Fumisoquin biosynthesis requires the N-methyltransferase FsqC and the FAD-dependent oxidase FsqB, which represent functional analogs of coclaurine N-methyltransferase and berberine bridge enzyme in plants. Our results show that BGCs containing incomplete NRPS modules may reveal new biosynthetic paradigms and suggest that plant-like isoquinoline biosynthesis occurs in diverse fungi. PMID:27065235

  5. Acridone alkaloids as potent inhibitors of cathepsin V.

    Severino, Richele P; Guido, Rafael V C; Marques, Emerson F; Brömme, Dieter; da Silva, M Fátima das G F; Fernandes, João B; Andricopulo, Adriano D; Vieira, Paulo C

    2011-02-15

    Cathepsin V is a lysosomal cysteine peptidase highly expressed in thymus, testis and corneal epithelium. Eleven acridone alkaloids were isolated from Swinglea glutinosa (Bl.) Merr. (Rutaceae), with eight of them being identified as potent and reversible inhibitors of cathepsin V (IC(50) values ranging from 1.2 to 3.9 μM). Detailed mechanistic characterization of the effects of these compounds on the cathepsin V-catalyzed reaction showed clear competitive inhibition with respect to substrate, with dissociation constants (K(i)) in the low micromolar range (2, K(i)=1.2 μM; 6, K(i)=1.0 μM; 7, K(i)=0.2 μM; and 11, K(i)=1.7 μM). Molecular modeling studies provided important insight into the structural basis for binding affinity and enzyme inhibition. Experimental and computational approaches, including biological evaluation, mode of action assessment and modeling studies were successfully employed in the discovery of a small series of acridone alkaloid derivatives as competitive inhibitors of catV. The most potent inhibitor (7) has a K(i) value of 200 nM. PMID:21277783

  6. New cycloartane saponin and monoterpenoid glucoindole alkaloids from Mussaenda luteola.

    Mohamed, Shaymaa M; Backheet, Enaam Y; Bayoumi, Soad A; Ross, Samir A

    2016-04-01

    A new cycloartane-type saponin with unusual hydroxylation at C-17 and a unique side chain, 9 (R), 19, 22 (S), 24 (R) bicyclolanost-3β, 12α, 16β, 17α tetrol-25-one 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside (1) and two new monoterpenoid glucoindole alkaloids, 10-methoxy pumiloside (2) and the previously chemically synthesized, 10-methoxy strictosidine (3) along with other five known compounds, 7α-morroniside (4), 7-epi-loganin (5), (7β)-7-O-methylmorroniside (6), 5(S)-5-carboxystrictisidine (7) and apigenin-7-O-neohesperidoside (8) were isolated from the aerial parts of Mussaenda luteola (Rubiaceae). The structural elucidation of the isolates was accomplished by extensive (1D and 2D NMR) spectroscopic data analysis and HR-ESI-MS. Compounds 4-8 were reported for the first time from the genus Mussaenda. Interestingly, this is the first report for the occurrence of the monoterpenoid glucoindole-type alkaloids in the genus which might be useful for the chemotaxonomic evaluation of the genus Mussaenda. All isolates were evaluated for their antiprotozoal activities. Compound 7 showed good antitrypanosomal activity with IC50 and IC90 values of 13.7 and 16.6 μM compared to IC50 and IC90 values of 13.06 and 28.99 μM for the positive control DFMO, difluoromethylornithine. PMID:26969788

  7. Catharanthus roseus (L. G. Don - plant regeneration and alkaloids content

    Mirosława Furmanowa

    2014-02-01

    Full Text Available We describe here a regeneration of plantlets of Catharanthus roseus (L. G. Don from shoot tips and axillary buds. Shoot tips were excised from 7-day-old seedlings and were incubated in solid Nitsch and Nitsch (NN medium supplemented with kinetin, benzyladenine (BA, indole-3-butyric acid (IBA and β-indolylacetic acid (IAA in various combinations. After two months in culture, regenerated rooted plantlets were cut and transferred to a new medium; the explants contained shoot tips or axillary buds. Four passages were done. We obtained about 200 rooting plantlets from one seedling. Then the plantlets were transferred to the soil and they grew under a foil tent. After five months of vegetation they were collected, dried and weighed. Chemical investigations of leaves of these plants were done. The vindoline and catharanthine were dominant alkaloids in the juvenile stage of plants (before blooming. Total amount of alkaloids, equal 2.95%, was gravimetrically determined in leaves of plants, after 4th passage, regenerated in vitro on NN medium supplemented with kinetin and IBA.

  8. Biosynthetic pathway of terpenoid indole alkaloids in Catharanthus roseus.

    Zhu, Xiaoxuan; Zeng, Xinyi; Sun, Chao; Chen, Shilin

    2014-09-01

    Catharanthus roseus is one of the most extensively investigated medicinal plants, which can produce more than 130 alkaloids, including the powerful antitumor drugs vinblastine and vincristine. Here we review the recent advances in the biosynthetic pathway of terpenoid indole alkaloids (TIAs) in C. roseus, and the identification and characterization of the corresponding enzymes involved in this pathway. Strictosidine is the central intermediate in the biosynthesis of different TIAs, which is formed by the condensation of secologanin and tryptamine. Secologanin is derived from terpenoid (isoprenoid) biosynthetic pathway, while tryptamine is derived from indole biosynthetic pathway. Then various specific end products are produced by different routes during downstream process. Although many genes and corresponding enzymes have been characterized in this pathway, our knowledge on the whole TIA biosynthetic pathway still remains largely unknown up to date. Full elucidation of TIA biosynthetic pathway is an important prerequisite to understand the regulation of the TIA biosynthesis in the medicinal plant and to produce valuable TIAs by synthetic biological technology. PMID:25159992

  9. Total Alkaloids of Sophora alopecuroides Inhibit Growth and Induce Apoptosis in Human Cervical Tumor HeLa Cells In vitro

    Li, Jian-Guang; Yang, Xiao-Yi; Huang, Wei

    2016-01-01

    Background: Uygur females of Xinjiang have the higher incidence of cervical tumor in the country. Alkaloids are the major active ingredients in Sophora alopecuroides, and its antitumor effect was recognized by the medical profession. Xinjiang is the main site of S. alopecuroides production in China so these plants are abundant in the region. Studies on the antitumor properties of total alkaloids of S. alopecuroides (TASA) can take full use of the traditional folk medicine in antitumor unique utility. Objectives: To explore the effects of TASA on proliferation and apoptosis of human cervical tumor HeLa cells in vitro. Materials and Methods: TASA was extracted, purified, and each monomer component was analyzed by high-performance liquid chromatography. The effect of TASA at different concentrations on the survival of HeLa cells was determined after 24 h using the Cell Counting Kit-8. In addition, cells were photographed using an inverted microscope to document morphological changes. The effect of TASA on apoptotic rate of HeLa cells was assessed by flow cytometry. Results: Monomers of TASA were found to be sophoridine, matrine, and sophocarpine. On treatment with 8.75 mg/ml of TASA, more than 50% of HeLa cells died, and cell death rate increased further with longer incubation. The apoptotic rates of HeLa cells in the experimental groups were 16.0% and 33.3% at concentrations of 6.25 mg/ml and 12.50 mg/ml, respectively. Conclusion: TASA can induce apoptosis in cervical tumor HeLa cells, and it has obvious inhibitory effects on cell growth. SUMMARY Total alkaloids of Sophora alopecuroides (TASA) exhibits anti-human cervical tumor propertiesMonomer component of TASA was analyzed by high-performance liquid chromatography, and its main effect component are sophoridine, matrine, and sophocarpineTASA inhibits growth and induces apoptosis in HeLa cells. Abbreviations used: TASA: Total alkaloids of S. alopecuroides, CCK-8: Cell Counting Kit-8, FBS: Fetal bovine serum, PBS

  10. Cytotoxic effects of alkaloids on cervical carcinoma cell lines: a review

    Priscilla Alencar Fernandes

    2016-07-01

    Full Text Available Cervical cancer is the fourth type of women neoplasia, with thousands of new cases annually. It is closely related to human papillomavirus (HPV infection, which has more than 13 oncogenic types, among them HPV 16 and 18 are implicated in 70% of cervical carcinoma cases. Alkaloids are nitrogenated and naturally occurring compounds, showing several uses in medical treatment, including cytotoxic and antineoplastic activities. In this work we aim to evaluate the cytotoxic and chemotherapeutic potential of alkaloids against cervical cancer. In order to accomplish this purpose, we have made a survey of potentially effective alkaloids with cytotoxic activities over HPV-16+ and HPV-18 + cells (HeLa cells. Through a literature review between the years of 1980 and 2015, we described the major alkaloid sources, distribution in nature and also discussed the mechanisms of action for their cytotoxicity. We found that alkaloids showed efficacy as cytotoxic agents, inhibiting cell growth of the HPV-transformed cells in vitro and in vivo by means of activation of intrinsic and extrinsic pathways of apoptosis, which included the clivage of caspases and PARP-1 (Poli-Adenosyl- Ribose Protease 1, increase in p53 expression, release of cytochrome C and increase of cell death receptors expression like Fas, mainly observed in HeLa (HPV- 18 + cell lines. Moreover, these secondary metabolites helped in modulating the MDR (Multi-Drug Resistance against the cell lines studied, which lead us to suggest their possible use as chemotherapeutic agents on the lesions caused by these virusesKeywords: Cervical cancer. Alkaloids. HPV. Chemotherapy. RESUMOEfeitos citotóxicos de alcaloides sobre linhagens de células do câncer cervical: uma revisãoO câncer cervical é a quarta neoplasia incidente em mulheres, com o surgimento de milhares de novos casos anualmente. Está altamente relacionado à infecção pelo papilomavírus humano (HPV, que apresenta mais de 13 tipos oncog

  11. Gas Chromatography-mass Spectrometry (GC-MS analysis of alkaloids isolated from Epipremnum aureum (Linden and Andre Bunting

    Anju Meshram

    2015-02-01

    Full Text Available Recent advances in the use of GC coupled to MS have allowed a chemically guided isolation of uncommon and bioactive alkaloids. The present study was aimed to focus on the extraction and screening of alkaloids from Epipremnum aureum (Linden and Andre Bunting. It has been observed that the plant is very rich in alkaloids and the modified method employed for the extraction of alkaloid is efficient and selective, where the interference of other secondary metabolites is negligible. The identification of each compound was made through gas chromatography-mass spectrometry (GC-MS. A total of twenty six structurally different alkaloids were identified for the first time from this plant. E. aureum is highly rich in alkaloids and twenty six different alkaloids were characterized. The present study may help in the field of natural products’ chemistry and pharmaceuticals as well as drug discovery science and technology.

  12. Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways.

    Haarmann, Thomas; Ortel, Ingo; Tudzynski, Paul; Keller, Ullrich

    2006-04-01

    Clavines and D-lysergic acid-derived alkaloid amides and alkaloid peptides are two different families of compounds that have the indole-derived tetracyclic metergoline ring system in common. Previous work has shown that D-lysergic acid is biosynthetically derived from clavine alkaloids. Recent cloning and analysis of the ergot alkaloid biosynthesis gene cluster from the D-lysergic acid peptide (ergopeptines)-producing Claviceps purpurea, has shown that it most probably contains all genes necessary for D-lysergic acid synthesis as well as those that encode the assembly of D-lysergic acid peptides, such as ergotamine. To address the role of the oxygenase genes of alkaloid-gene clusters, the only cytochrome P450 monooxygenase gene of this cluster was inactivated by disruption. The resultant mutant accumulated agroclavine, elymoclavine, and chanoclavine in substantial amounts but not ergopeptines. Feeding the mutant with D-lysergic acid restored ergopeptine synthesis; this suggests a block in the conversion of elymoclavine to D-lysergic acid. The gene was designated cloA (for encoding a clavine oxidase, CLOA). Retransformation of the mutant with the intact cloA gene also restored ergopeptine synthesis. These data show that CLOA catalyses the conversion of clavines to D-lysergic acid, it acts as a critical enzyme in the ergot alkaloid gene cluster, and bridges the biosynthesis of the two different families of alkaloids. PMID:16538694

  13. Alkaloids: an overview of their antibacterial, antibiotic-enhancing and antivirulence activities.

    Cushnie, T P Tim; Cushnie, Benjamart; Lamb, Andrew J

    2014-11-01

    With reports of pandrug-resistant bacteria causing untreatable infections, the need for new antibacterial therapies is more pressing than ever. Alkaloids are a large and structurally diverse group of compounds that have served as scaffolds for important antibacterial drugs such as metronidazole and the quinolones. In this review, we highlight other alkaloids with development potential. Natural, semisynthetic and synthetic alkaloids of all classes are considered, looking first at those with direct antibacterial activity and those with antibiotic-enhancing activity. Potent examples include CJ-13,136, a novel actinomycete-derived quinolone alkaloid with a minimum inhibitory concentration of 0.1 ng/mL against Helicobacter pylori, and squalamine, a polyamine alkaloid from the dogfish shark that renders Gram-negative pathogens 16- to >32-fold more susceptible to ciprofloxacin. Where available, information on toxicity, structure-activity relationships, mechanisms of action and in vivo activity is presented. The effects of alkaloids on virulence gene regulatory systems such as quorum sensing and virulence factors such as sortases, adhesins and secretion systems are also described. The synthetic isoquinoline alkaloid virstatin, for example, inhibits the transcriptional regulator ToxT in Vibrio cholerae, preventing expression of cholera toxin and fimbriae and conferring in vivo protection against intestinal colonisation. The review concludes with implications and limitations of the described research and directions for future research. PMID:25130096

  14. Relationship between alkaloid contents and growth environment of Yimu Cao (Herba Leonuri)

    CHAO Zhi; YAN Gang

    2001-01-01

    To study the relationship between alkaloids contents in Chinese traditional drug Yimu Cao (the dried aerial parts ofLeonurus artemisia) and its growing environment. Methods: Samples of the drug and the soil at the growing site collected from 5 selected regions. Reference materials were checked and on-the-spot observations were carried out to investigate the growth environment. RP-HPLC was performed to determine the alkaloid contents in the drug. Results: Different regions had different environmental conditions, including climate, soil, vegetation, and so on.No matter barren or fertile the soil at the growing site was, the herb ofL. Artemisia could grow well, but the contents of alkaloid in the drug varied greatly. The drugs produced in 2 northern regions, where the soil is alkaline, had higher content of alkaloid (about 0.4%) than that produced in southern regions (0.1%-0.2%), where the soil is acid. Conclusion:The contents of organic matters, effective phosphorus, quick-acting potassium, and the pH value of the growing site soil were the factors correlating with alkaloid contents in the drug, among which the pH value of soil was an important positively correlating factor. The alkaline soils in North benefit the accumulation of alkaloids more than the acid soils in South. The other probable elements affecting the alkaloid contents in Yimu Cao were climate and genetic factors.

  15. HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus

    Paulo Mazzafera

    2008-07-01

    Full Text Available Pilocarpine, an important imidazole alkaloid, is extracted from the leaves of Pilocarpus microphyllus (Rutaceae, known in Brazil as jaborandi and used mainly for the treatment of glaucoma. Jaborandi leaves also contain other imidazole alkaloids, whose pharmacological and physiological properties are unknown, and whose biosynthetic pathways are under investigation. In the present study, a HPLC method coupled with ESI-MSn was developed for their qualitative and quantitative analysis. This method permits the chromatographic separation of the imidazole alkaloids found in extracts of jaborandi, as well as the MS/MS analysis of the individual compounds. Thus two samples: leaves of P. microphyllus and a paste that is left over after the industrial extraction of pilocarpine; were compared. The paste was found to contain significant amounts of pilocarpine and other imidazole alkaloids, but had a slightly different alkaloid profile than the leaf extract. The method is suitable for the routine analysis of samples containing these alkaloids, as well as for the separation and identification of known and novel alkaloids from this family, and may be applied to further studies of the biosynthetic pathway of pilocarpine in P. microphyllus.

  16. HPLC-ESI-MS/MS of imidazole alkaloids in Pilocarpus microphyllus.

    Sawaya, Alexandra C H F; Abreu, Ilka Nacif; Andreazza, Nathalia Luiza; Eberlin, Marcos N; Mazzafera, Paulo

    2008-01-01

    Pilocarpine, an important imidazole alkaloid, is extracted from the leaves of Pilocarpus microphyllus (Rutaceae), known in Brazil as jaborandi and used mainly for the treatment of glaucoma. Jaborandi leaves also contain other imidazole alkaloids, whose pharmacological and physiological properties are unknown, and whose biosynthetic pathways are under investigation. In the present study, a HPLC method coupled with ESI-MS(n) was developed for their qualitative and quantitative analysis. This method permits the chromatographic separation of the imidazole alkaloids found in extracts of jaborandi, as well as the MS/MS analysis of the individual compounds. Thus two samples: leaves of P. microphyllus and a paste that is left over after the industrial extraction of pilocarpine; were compared. The paste was found to contain significant amounts of pilocarpine and other imidazole alkaloids, but had a slightly different alkaloid profile than the leaf extract. The method is suitable for the routine analysis of samples containing these alkaloids, as well as for the separation and identification of known and novel alkaloids from this family, and may be applied to further studies of the biosynthetic pathway of pilocarpine in P. microphyllus. PMID:18719522

  17. Isolation, biosynthesis and biological activity of alkaloids of Tylophora asthmatica, a versatile medicinal plant

    Tylophorine and related new alkaloids have been isolated from Tylophora asthmatics, Pergularia pallida and Ficus hispida plants. Biosynthesis of this group of alkaloids has been carried out using various labelled precursors for the first time and from the systematic degradation of the isolated radiolabelled tylophorine, it has been concluded that these alkaloids arise from one molecule each of tyrosine, phenylalanine and ornithine. The interactions of Tylophora alkaloids particularly tylophorinidine with biomolecules such as lysozyme and bovine serum albumin have also been studied and binding characteristics determined. It was found that Tylophora alkaloid extract possesses antianaphylactic activity as observed in passive peritoneal anaphylaxis in rats. The drug also possessed mild antihistaminic and anticholinergic activities. Studies of the extract on the bronchial smooth muscle both in vivo and in vitro did not reveal bronchiodilator potential of the drug. In addition, the distribution and metabolism of the drug was studied in vivo using 14C radiolabelled alkaloids prepared by biosynthetic method. This study further revealed its usefulness since the drug is absorbed by vital organs and also it is not metabolised into fragments which could cause some other damage. Tylophora alkaloids have also been found to be anti-mutagenic. 10 tables, 5 figures, 24 refs. (author)

  18. Potent Antifouling Marine Dihydroquinolin-2(1H)-one-Containing Alkaloids from the Gorgonian Coral-Derived Fungus Scopulariopsis sp.

    Shao, Chang-Lun; Xu, Ru-Fang; Wang, Chang-Yun; Qian, Pei-Yuan; Wang, Kai-Ling; Wei, Mei-Yan

    2015-08-01

    Marine biofouling has a major economic impact, especially when it occurs on ship hulls or aquaculture facilities. Since the International Maritime Organization (IMO) treaty to ban the application of organotin-based paints to ships went into effect in 2008, there is an urgent demand for the development of efficient and environmentally friendly antifouling agents. Marine microorganisms have proved to be a potential source of antifouling natural compounds. In this study, six dihydroquinolin-2-one-containing alkaloids, three monoterpenoids combined with a 4-phenyl-3,4-dihydroquinolin-2(1H)-one (1-3) and three 4-phenyl-3,4-dihydroquinolin-2(1H)-one alkaloids (4-6), were isolated from the gorgonian coral-derived fungus Scopulariopsis sp. collected in the South China Sea. These dihydroquinolin-2-one-containing alkaloids were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. All of them except 6 showed strong antifouling activity. Compounds 1 and 2 were discovered to be the most promising non-toxic antilarval settlement candidates. Especially, compound 1 is the strongest antifouling compound in nature until now which showed highly potent activity with picomolar level (EC50 17.5 pM) and a very safety and high therapeutic ratio (LC50/EC50 1200). This represents an effective non-toxic, anti-larval settlement structural class of promising antifouling lead compound. PMID:25833409

  19. Two unprecedented dibromotyrosine-derived alkaloids from the Brazilian endemic marine sponge Aplysina caissara.

    Saeki, Beatriz M; Granato, Ana Claudia; Berlinck, Roberto G S; Magalhães, Alviclér; Schefer, Alexandre B; Ferreira, Antonio G; Pinheiro, Ulisses S; Hajdu, Eduardo

    2002-05-01

    Two new bromotyrosine-derived alkaloids, caissarine A (1) and caissarine B (2), along with three known biogenetically related alkaloids, aeroplysinin-1, fistularin-3, and the artifact of isolation 2-(3,5-dibromo-4-dimethoxy-1-hydroxy-2,5-cyclohexadien-1-yl)ethanamide, have been isolated from Aplysina caissara, an endemic species of marine sponge from the Southeastern Brazilian coast. The alkaloids have been identified by analysis of spectroscopic data. While caissarine A has a 2-hydroxyagmatine moiety in its structure, caissarin B is the first naturally occurring compound encompassing the unprecedented 1,7-diamino-3-hydroxyheptane moiety. PMID:12027773

  20. [HPTLC separation and fluorodensitometric determination of isoquinoline alkaloids in Chelidonine majus L].

    Niu, C Q; He, L Y

    1992-01-01

    The quantitative analysis of isoquinoline alkaloids in Chelidonine majus L. was investigated and a HPTLC method has been established. Using this method, we separated and determined eight isoquinoline alkaloids, i.e. chelidonine, protopine, berberine, coptisine, tetrahydrocoptisine, 6-methoxydihydrochelerythrine, 6-methoxydihydrosanguinarine and dihydrosanguinarine. The HPTLC method developed used one developing system on high performance silica gel plate (10 x 10 cm). After separation of these eight alkaloids, fluorescence derivatization was carried out in situ. The content was determined by fluorescence scanning. TLC fluorescence derivatization, fluorescence enhancement and fluorescence stability have been studied. Experiments showed that this method is simple, fast, highly sensitive and highly selective. PMID:1529718

  1. Weak C–H…O hydrogen bonds in alkaloids: An overview

    Rajnikant; Dinesh; Kamni

    2005-06-01

    An overview of general classification scheme, medicinal importance and crystal structure analysis with emphasis on the role of hydrogen bonding in some alkaloids is presented in this paper. The article is based on a general kind of survey while crystallographic analysis and role of hydrogen bonding are limited to only those alkaloids whose three-dimensional structure has been reported by us. The C–H…O hydrogen bonding in the solid state in alkaloids has been found to be predominant and this observation makes the role of hydrogen bonding in organic molecular assemblies very important.

  2. Anti-inflammatory Activity of Pyrrolizidine Alkaloids from the Leaves of Madhuca pasquieri (Dubard).

    Hoang, Le Son; Tran, Manh Hung; Lee, Joo Sang; To, Dao Cuong; Nguyen, Van Thu; Kim, Jeong Ah; Lee, Jeong Hyung; Woo, Mi Hee; Min, Byung Sun

    2015-01-01

    A novel pyrrolizidine alkaloids, madhumidine A (1), and two known alkaloids, lindelofidine benzoic acid ester (2) and minalobine B (3) were isolated from the leaves of Madhuca pasquieri (Dubard) H. J. LAM. The chemical structures of these alkaloids were established mainly by NMR techniques and mass spectrometry. Their anti-inflammatory activity was evaluated against lipopolysaccharide-induced nitric oxide production in macrophage RAW264.7 cell. In addition, the cytotoxic activity of all isolated compounds was tested against a panel of cancer cell lines. PMID:26027474

  3. Genotoxicity of the boldine aporphine alkaloid in prokaryotic and eukaryotic organisms.

    Moreno, P R; Vargas, V M; Andrade, H H; Henriques, A T; Henriques, J A

    1991-06-01

    The aporphine alkaloid boldine, present in Peumus boldus (boldo-do-Chile) widely used all over the world, was tested for the presence of genotoxic, mutagenic and recombinogenic activities in microorganisms. This alkaloid did not show genotoxic activity with or without metabolic activation in the SOS chromotest and Ames tester strains TA100, TA98 and TA102. It was not able to induce point and frameshift mutations in haploid Saccharomyces cerevisiae cells. However, mitotic recombinational events such as crossing-over and gene conversion were weakly induced in diploid yeast cells by this alkaloid. Also, boldine was able to induce weakly cytoplasmic 'petite' mutation in haploid yeast cells. PMID:2046695

  4. Alkaloids from Marine Invertebrates as Important Leads for Anticancer Drugs Discovery and Development

    Concetta Imperatore

    2014-12-01

    Full Text Available The present review describes research on novel natural antitumor alkaloids isolated from marine invertebrates. The structure, origin, and confirmed cytotoxic activity of more than 130 novel alkaloids belonging to several structural families (indoles, pyrroles, pyrazines, quinolines, and pyridoacridines, together with some of their synthetic analogs, are illustrated. Recent discoveries concerning the current state of the potential and/or development of some of them as new drugs, as well as the current knowledge regarding their modes of action, are also summarized. A special emphasis is given to the role of marine invertebrate alkaloids as an important source of leads for anticancer drug discovery.

  5. Hainanerectamines A–C, Alkaloids from the Hainan Sponge Hyrtios erecta

    Wen-Fei He; Duo-Qing Xue; Li-Gong Yao; Jing-Ya Li; Jia Li; Yue-Wei Guo

    2014-01-01

    Two new indole alkaloids, hainanerectamines A (1) and B (2), and one new β-carboline alkaloids, hainanerectamines C (4), along with five known related alkaloids (3, 5–8), have been isolated from the Hainan marine sponge Hyrtios erecta. The structures of new compounds 1, 2 and 4 were determined by detailed analysis of their 1D and 2D NMR spectra and by comparison of their spectroscopic data with those of related model compounds. Compounds 2–4 exhibited moderate inhibitory activity against Aur...

  6. Influence of Some Heavy Metals on Growth, Alkaloid Content and Composition in Catharanthus roseus L.

    Srivastava, N. K.; Srivastava, A. K.

    2010-01-01

    Shoot biomass production, alkaloid content and composition as influence by cadmium, manganese, nickel and lead at uniform dose of 5 mM were investigated in Catharanthus roseus plants grown in sand culture. Treatment with Mn, Ni, and Pb significantly enhanced total root alkaloid accumulation. Cd and Ni treatment resulted in two-fold where as Pb treatment resulted in three fold increase in serpentine content of roots. The non-significant affect on biomass suggests that plants can withstand metal stress at the level tested with positive affect on root alkaloid content. PMID:21969751

  7. Phenylbenzoisoquinolindione alkaloids accumulate in stamens of Xiphidium caeruleum Aubl. flowers.

    Chen, Yu; Paetz, Christian; Menezes, Riya C; Schneider, Bernd

    2016-08-01

    Xiphidium caeruleum (Haemodoraceae) flower organs such as carpels, pedicels, petals, and stamens were separately investigated for their phytochemical profile. The stamens appeared to be a rich source of previously undescribed phenylbenzoisoquinolindiones, a group of phenylphenalenone-derived alkaloids, also named aza-phenylphenalenones. Nine previously undescribed compounds with an identical aza-phenylphenalenone core structure but different amino acid-derived side chains at position 2 were isolated and their structures elucidated by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). In addition, some previously reported phenylbenzoisoquinolindiones, phenylbenzoisochromenones and flavonoids were found in stamens and other parts of the flowers. The specific occurrence of heterocyclic phenylphenalenone-type compounds in X. caeruleum suggests these are involved in physiological or ecological processes. PMID:27179683

  8. New Alkaloid De-Oxypalmitine from Coscinium fenestratum

    K. Talat

    2012-06-01

    Full Text Available Present study is aimed at to investigate phytochemically the stem bark of Coscinium fenestratum (family Menispermaceae a plant popularly and commonly known as “tree turmeric” used globally in traditional medicine to treat variety of ailments, using a standard procedure. Fractionation of its methanol extract by ethyl acetate and chloroform and subsequent column chromatography over silica gel G (60-120 mesh size led to the isolation of Berberine, Palmitine and Jatrorrhizine. The structure of palmitine was elucidated using 1H-NMR, 13C-NMR, FABMS and DEPT analysis and was confirmed. In addition, alkaloid Deoxypalmitine (1 was isolated from the methanol extract of the defatted stem of the Coscinium fenestratum. The structure of the new compound 1 was determined by means of spectral data analysis and also comparing that of reference sample of palmitine.

  9. Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

    Li, Yanran; Smolke, Christina D.

    2016-01-01

    Noscapine is a potential anticancer drug isolated from the opium poppy Papaver somniferum, and genes encoding enzymes responsible for the synthesis of noscapine have been recently discovered to be clustered on the genome of P. somniferum. Here, we reconstitute the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates, complementing and extending previous in planta and in vitro investigations. Our work provides structural validation of the secoberberine intermediates and the description of the narcotoline-4′-O-methyltransferase, suggesting this activity is catalysed by a unique heterodimer. We also reconstitute a 14-step biosynthetic pathway of noscapine from the simple alkaloid norlaudanosoline by engineering a yeast strain expressing 16 heterologous plant enzymes, achieving reconstitution of a complex plant pathway in a microbial host. Other engineered yeasts produce previously inaccessible pathway intermediates and a novel derivative, thereby advancing protoberberine and noscapine related drug discovery. PMID:27378283

  10. Synthesis of some /sup 11/C-labelled alkaloids

    Laangstroem, B.; Antoni, G.; Halldin, H.; Svaerd, H.; Bergson, G. (Univ. of Uppsala (Sweden) Inst. of Chemistry)

    1982-01-01

    Using (/sup 11/C)-methyl iodide in N-alkylation reactions in dimethylformamide (DMF), the alkaloids N-(/sup 11/C-methyl)-morphine, N-(/sup 11/C-methyl)-codeine, 6-N(methyl)-9, 10-dihydroergotamine, 6-N-(/sup 11/C-methyl)-bromocriptine and N-(/sup 11/C-methyl)-nicotine have been synthesized in radiochemical yields of 50-95%, within 5-10 min of introducing (/sup 11/C)-methyl iodide into the reaction vial. (/sup 11/C)-Methyl iodide was obtained within 4-7 min from (/sup 11/C)-carbon dioxide prepared by the /sup 14/N(p,..cap alpha..)/sup 11/C reaction.

  11. DNA binding studies of Vinca alkaloids: experimental and computational evidence.

    Pandya, Prateek; Gupta, Surendra P; Pandav, Kumud; Barthwal, Ritu; Jayaram, B; Kumar, Surat

    2012-03-01

    Fluorescence studies on the indole alkaloids vinblastine sulfate, vincristine sulfate, vincamine and catharanthine have demonstrated the DNA binding ability of these molecules. The binding mode of these molecules in the minor groove of DNA is non-specific. A new parameter of the purine-pyrimidine base sequence specificty was observed in order to define the non-specific DNA binding of ligands. Catharanthine had shown 'same' pattern of 'Pu-Py' specificity while evaluating its DNA binding profile. The proton resonances of a DNA decamer duplex were assigned. The models of the drug:DNA complexes were analyzed for DNA binding features. The effect of temperature on the DNA binding was also evaluated. PMID:22545401

  12. Alkaloids from an algicolous strain of Talaromyces sp.

    Yang, Haibin; Li, Fang; Ji, Naiyun

    2016-03-01

    Compounds isolated and identified in a culture of the alga-endophytic fungus Talaromyces sp. cf-16 included two naturally occurring alkaloids, 2-[( S)-hydroxy(phenyl)methyl]-3-methylquinazolin-4(3H)-one ( 1a) and 2-[( R)-hydroxy(phenyl)methyl]-3-methylquinazolin-4(3H)-one ( 1b), that were identified for the first time. In addition, seven known compounds ( 2- 8) were obtained from the culture. Following chiral column chromatography, compounds 1a and 1b were identified as enantiomers by spectroscopic analyses and quantum chemical calculations. Bioassay results showed that 5 was more toxic to brine shrimp than the other compounds, and that 3- 6 could inhibit Staphylococcus aureus.

  13. Cryptolepine hydrochloride: a potent antimycobacterial alkaloid derived from Cryptolepis sanguinolenta.

    Gibbons, Simon; Fallah, Fatemeh; Wright, Colin W

    2003-04-01

    The activity of cryptolepine hydrochloride, a salt of the main indoloquinoline alkaloid from the West African medicinal plant Cryptolepis sanguinolenta, was assessed against the fast growing mycobacterial species Mycobacterium fortuitum, which has recently been shown to be of use in the evaluation of antitubercular drugs. The low minimum inhibitory concentration (MIC) of this compound (16 microg/mL) prompted further evaluation against other fast growing mycobacteria namely, M. phlei, M. aurum, M. smegmatis, M. bovis BCG and M. abcessus and the MICs ranged over 2-32 microg/mL for these species. The strong activity of this agent, the need for new antibiotics with activity against Mycobacterium tuberculosis, coupled with the ethnobotanical use of C. sanguinolenta extracts to treat infections, highlight the potential of the cryptolepine template for development of antimycobacterial agents. PMID:12722159

  14. Two fast screening methods (GC-MS and TLC-ChEI assay for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures

    Ivo J.C. Vieira

    2008-09-01

    Full Text Available The pharmacotherapyfor Alzheimer's disease (AD includes the use of acetylcholinesterase inhibitors (AChEI. Recent investigations for novel AD therapeutic agents from plants suggested that Tabernaemontana genus is a promising source of novel anticholinesterasic indole alkaloids. In this work two fast screening techniques were combined in order to easily identify novel cholinesterase inhibitors (ChEI. Gas chromatography-mass spectrometry (GC-MS of the less polar alkaloidic fractions obtained from the acid-base extraction of the stalk of T. laeta revealed thirteen monoindole alkaloids, four of them confirmed by co-injection with previously isolated alkaloids. The others were tentatively identified by mass fragmentation analysis. By gas chromatography with flame ionization detection (GC-FID and using isatin as internal standard, affinisine and voachalotine were determined as major compounds. These fractions and fourteen previously isolated alkaloids, obtained from root bark of T. laeta and T. hystrix were investigated for acetyl (AChE and butyrylcholinesterase (BuChE inhibitory activities by the modified Ellman's method in thin layer chromatography(TLC-ChEI. Results showed selective inhibition of the alkaloids heyneanine and Nb-methylvoachalotine for BuChE, and 19-epi-isovoacristine for AChE, whereas olivacine, affinisine, ibogamine, affinine, conodurine and hystrixnineinhibited both enzymes. In addition to confirming that monoterpenoid indole alkaloids can be novel therapeutic agents for AD, this is the first report of the ChEI activity of olivacine, a pyridocarbazole alkaloid.Dentre os tratamentos da doença de Alzheimer (DA está o uso de inibidores da enzima acetilcolinesterase. Pesquisas recentes visando a descoberta de novos agentes terapêuticos naturais para esta doença sugerem que o gênero Tabernaemontana é uma fonte promissora de alcalóides indólicos anticolinesterásicos. Neste trabalho, duas técnicas de análise em mistura foram

  15. Three new C19-diterpenoid alkaloids from Delphinium laxicymosum var. Pilostachyum

    Ping Tang; Dong Lin Chen; Qiao Hong Chen; Xi Xian Jian; Feng Peng Wang

    2007-01-01

    Three new lycoctonine-type C19-diterpenoid alkaloids, laxicymine 1, laxicymisine 2, and laxicyminine 3 have been isolated from the whole herb of Delphinium laxicymosum var.pilostachyum W.T.Wang.Their structures were established by spectra data.

  16. Sequestration of dietary alkaloids by the spongivorous marine mollusc Tylodina perversa.

    Thoms, Carsten; Ebel, Rainer; Hentschel, Ute; Proksch, Peter

    2003-01-01

    Specimens of the spongivorous Mediterranean opisthobranch Tylodina perversa that had been collected while feeding on Aplysina acerophoba were shown to sequester the brominated isoxazoline alkaloids of their prey. Alkaloids were stored in the hepatopancreas, mantle tissues, and egg masses in an organ-specific manner. Surprisingly, the known sponge alkaloid aerothionin which is found only in A. cavernicola but not in A. aerophoba was also among the metabolites identified in wild caught specimens of T. perversa as well as in opisthobranchs with a documented feeding history on A. aerophoba. Mollusc derived aerothionin is postulated to be derived from a previous feeding encounter with A. cavernicola as T. perversa was found to freely feed on both Aplysina sponges in aquarium bioassays. The possible ecological significance of alkaloid sequestration by T. perversa is still unknown. PMID:12872940

  17. Survey of Iranian Plants For Saponins Alkaloids Flavonoids And Tannins. IV

    M.H. Salehi Surmaghi; Y. Aynehchi GH. Amin; Z. Mahmoodi

    1992-01-01

    A total of 149 plant extracts representing 49 different families has been screened for saponins, flavonoids, tannins and alkalodids. positive tests obtained were 145 (97) for saponins 74 (50%) for alkaloids 16 (51%) for fiavonoisds and 60 (40%) for tannins.

  18. Lucidimine A-D, four new alkaloids from the fruiting bodies of Ganoderma lucidum.

    Zhao, Zhen-Zhu; Chen, He-Ping; Feng, Tao; Li, Zheng-Hui; Dong, Ze-Jun; Liu, Ji-Kai

    2015-01-01

    Four new polycylic alkaloids, lucidimine A-D, were isolated from the fruiting bodies of Ganoderma lucidum. Their chemical structures were established based on 1D and 2D NMR data as well as HREIMS/HRESIMS analyses. PMID:26666338

  19. Significant differences in alkaloid content of Coptis chinensis (Huanglian, from its related American species

    Skeels Matthew

    2009-08-01

    Full Text Available Abstract Background The growing popularity of Chinese herbal medicine in the United States has prompted large-scale import of raw herbs from Asia. Many of the Asian herbs have phylogenetically related North American species. We compared three phylogenetically related species, namely Coptis chinensis (Huanglian, Hydrastis canadensis and Coptis trifolia to show whether they can be substituted by one another in terms of alkaloid content. Methods We used microwave assisted extraction to obtain alkaloids berberine, coptisine, palmatine and hydrastine. High performance liquid chromatography (HPLC was used to quantify each alkaloid. Results Hydrastis canadensis has the most berberine, whereas Coptis trifolia has the most coptisine. Hydrastine and palmatine were unique to Hydrastis canadensis and Coptis chinensis respectively. Conclusion Neither Hydrastis canadensis nor Coptis trifolia contains all the alkaloids found in Coptis chinensis used in Chinese medicine. Substitutes of this Chinese species by its American relatives are not recommended.

  20. Studies of Genetic Variation of Essential Oil and Alkaloid Content in Boldo (Peumus boldus).

    Vogel, H; Razmilic, I; Muñoz, M; Doll, U; Martin, J S

    1999-02-01

    Boldo is a tree or shrub with medicinal properties native to Chile. The leaves contain alkaloids and essential oils. Variation of total alkaloid concentration, of the alkaloid boldine, and essential oil components were studied in different populations from northern, central, and southern parts of its geographic range and in their progenies (half-sib families). Total alkaloid concentration showed genetic variation between progenies of the central population but not between populations. Boldine content found in concentrations of 0.007 to 0.009% did not differ significantly between populations. Principal components of the essential oil were determined genetically, with highest values for ascaridole in the population of the north and for P-cymene in the south. Between half-sib families genetic variation was found in the central and northern populations for these components. The high heritability coefficients found indicate considerable potential for successful selection of individuals for these characters. PMID:17260243

  1. RNA targeting by small molecules: Binding of protoberberine, benzophenanthridine and aristolochia alkaloids to various RNA structures

    Gopinatha Suresh Kumar

    2012-07-01

    Studies on RNA targeting by small molecules to specifically control certain cellular functions is an area of remarkable current interest. For this purpose, a basic understanding of the molecular aspects of the interaction of small molecules with various RNA structures is essential. Alkaloids are a group of natural products with potential therapeutic utility, and very recently, their interaction with many RNA structures have been reported. Especially noteworthy are the protoberberines and aristolochia alkaloids distributed widely in many botanical families. Many of the alkaloids of these group exhibit excellent binding affinity to many RNA structures that may be exploited to develop RNA targeted therapeutics. This review attempts to present the current status on the understanding of the interaction of these alkaloids with various RNA structures, mainly highlighting the biophysical aspects.

  2. A Journey Under the Sea: The Quest for Marine Anti-Cancer Alkaloids

    Nadine Darwiche

    2011-11-01

    Full Text Available The alarming increase in the global cancer death toll has fueled the quest for new effective anti-tumor drugs thorough biological screening of both terrestrial and marine organisms. Several plant-derived alkaloids are leading drugs in the treatment of different types of cancer and many are now being tested in various phases of clinical trials. Recently, marine-derived alkaloids, isolated from aquatic fungi, cyanobacteria, sponges, algae, and tunicates, have been found to also exhibit various anti-cancer activities including anti-angiogenic, anti-proliferative, inhibition of topoisomerase activities and tubulin polymerization, and induction of apoptosis and cytotoxicity. Two tunicate-derived alkaloids, aplidin and trabectedin, offer promising drug profiles, and are currently in phase II clinical trials against several solid and hematologic tumors. This review sheds light on the rich array of anti-cancer alkaloids in the marine ecosystem and introduces the most investigated compounds and their mechanisms of action.

  3. A journey under the sea: the quest for marine anti-cancer alkaloids.

    Tohme, Rita; Darwiche, Nadine; Gali-Muhtasib, Hala

    2011-01-01

    The alarming increase in the global cancer death toll has fueled the quest for new effective anti-tumor drugs thorough biological screening of both terrestrial and marine organisms. Several plant-derived alkaloids are leading drugs in the treatment of different types of cancer and many are now being tested in various phases of clinical trials. Recently, marine-derived alkaloids, isolated from aquatic fungi, cyanobacteria, sponges, algae, and tunicates, have been found to also exhibit various anti-cancer activities including anti-angiogenic, anti-proliferative, inhibition of topoisomerase activities and tubulin polymerization, and induction of apoptosis and cytotoxicity. Two tunicate-derived alkaloids, aplidin and trabectedin, offer promising drug profiles, and are currently in phase II clinical trials against several solid and hematologic tumors. This review sheds light on the rich array of anti-cancer alkaloids in the marine ecosystem and introduces the most investigated compounds and their mechanisms of action. PMID:22113577

  4. Alternative extraction of alkaloid anticarcinogens from Brazilian "vinca rosea" using Ion exchange chromatography

    Sérgio Freire de Carvalhaes

    2002-01-01

    Full Text Available Extracts in ethanol and ethanol-ammonia of dried leaves from Catharanthus roseus, gathered at Rio de Janeiro state, were adsorbed in a strongly acidic cation exchange resin with sulfonic acid group, using the finite bath method, resulting in an alkaloid retained fraction and an acidic and neutral unretained fraction. High Performance Liquid Chromatography showed the isolation of the alkaloid fraction to be highly selective and with good performance, with an absence of alkaloids in the unretained fraction, while the retained fraction presented 1,54-6,35 mg/g of vindoline and 0,12-0,91 mg/g of vinblastine, common for an alkaloid-rich concentrate, usually obtained by classic extraction with several steps using solvents.

  5. ISOLATION AND PURIFICATION OF ALKALOIDS FROM PLUMULA NELUMBINIS BY DOUBLE-COLUMN ADSORPTION CHROMOTOGRAPHY

    2007-01-01

    The performance of adsorption and separation for liensinine, isoliensinine and neferine was studied by double-column adsorption chromatography using macroporous adsorption and cation exchange resins. The alkaloid extract with 49.2% total contents by mass representing 10.6% liensinine, 10.6% isoliensinine and 28.0% neferine respectively was prepared by D72 cation exchange resins, in which most of the impurities were water-soluble alkaloids. Furthermore,the alkaloid extract with 82.6% total contents by mass containing 33.1%, 15.0% and 34.5% of the three adsorbates respectively was prepared by double-column adsorption chromatography using AKS-W macroporous adsorption and D72 cation exchange resins. As a result, the content of single and total alkaloids has been greatly increased by the double-column adsorption chromatography.

  6. New records of pyrrolizidine alkaloid-feeding insects. Hemiptera and Coleoptera on Senecio brasiliensis.

    Klitzke; Trigo

    2000-04-01

    New records are reported for a Hemipteran (Largus rufipennis) and a Coleopteran (Chauliognathus fallax) feeding on Senecio brasiliensis (Asteraceae) and sequestering pyrrolizidine alkaloids (PAs). Both insects are warningly colored and rejected by predators. PMID:10725590

  7. Induction of micronuclei by alkaloids extracted from Senecio brasiliensis and stored for 23 years.

    Santos-Mello, R; Deimlimg, L I; Lauer Júnior, C M; Almeida, A

    2002-04-26

    In the present study, we report the results of an investigation on pyrrolizidine alkaloids extracted from Senecio brasiliensis (Sprengel) Less., which were stored for more than 23 years under variable conditions of temperature and humidity and exposed to light. Both the crude alkaloid (integerrimine+retrorsine+impurities) and pure integerrimine conserved the ability to induce acute toxicity in mice, leading to the death of the animals in less than 24h. The alkaloids also conserved the potential to induce significant increases in micronucleus frequencies in polychromatic erythrocytes of mouse bone marrow compared to the negative control. The administration of alkaloids to lymphocyte cultures blocked with cytochalasin-B showed no significant increase in micronucleus frequency in binucleated cells, probably due to the lack of a metabolic activation mechanism. However, an antimitotic effect was observed. PMID:11943607

  8. Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography.

    Huang, Hsi-Ya; Hsieh, Shih-Huan

    2007-09-14

    In this study, an on-line concentration method which coupled cation-selective exhaustive injection (CSEI) sweeping technology with microemulsion electrokinetic chromatography (MEEKC) was used to detect and analyze several tobacco alkaloids (nornicotine, anabasine, anatabine, nicotine, myosmine and cotinine) that are commonly found in various tobacco products. First, the effects of microemulsion compositions (oil, cosurfactant and solution pH) were examined in order to optimize the alkaloid separations in conventional MEEKC. The pH value and the injection length of basic plug were found to be the predominant influences on the alkaloid stacking. This optimal CSEI sweeping MEEKC method provided approximately 180- to 540-fold increase in detection sensitivity in terms of peak height without any loss in separation efficiency when compared to normal MEEKC separation. Furthermore, this proposed CSEI sweeping MEEKC method was applied successfully for the detection of the minor alkaloids nornicotine, anabasine and anatabine in tobacco products. PMID:17644105

  9. Poor alkaloid sequestration by arrow poison frogs of the genus Phyllobates from Costa Rica.

    Mebs, Dietrich; Alvarez, Joseph Vargas; Pogoda, Werner; Toennes, Stefan W; Köhler, Gunther

    2014-03-01

    Frogs of the genus Phyllobates from Colombia are known to contain the highly toxic alkaloid batrachotoxin, but species from Central America exhibit only very low levels or are entirely free of this toxin. In the present study alcohol extracts from 101 specimens of Phyllobates lugubris and Phyllobates vittatus and 21 of three sympatric species (Dendrobates pumilio, Dendrobates auratus, Dendrobates granuliferus) from Costa Rica were analyzed by gas chromatography-mass spectrometry. Whereas the extracts of the Dendrobates species exhibited typical profiles of toxic alkaloids, those of the two Phyllobates species contained low levels of few alkaloids only, batrachotoxin was not detected. Although the feeding pattern of the Dendrobates and Phyllobates species are similar as revealed by examination of their stomach content (mainly ants and mites), the Phyllobates species are poorly sequestering alkaloids from their food source in contrast to the Dendrobates frogs. PMID:24467995

  10. Molecular geometry of alkaloids present in seeds of mexican prickly poppy

    Gobato, Ricardo; Fedrigo, Desire Francine Gobato; Gobato, Alekssander

    2015-01-01

    The work is a study of the geometry of the molecules via molecular mechanics of the main alkaloids found in the seeds of Argemone Mexicana Linn, a prickly poppy, which is considered one of the most important species of plants in traditional Mexican and Indian medicine system. The seeds have toxic properties as well as bactericide, hallucinogenic, fungicide, insecticide, in isoquinolines and sanguinarine alkaloids such as berberine. A computational study of the molecular geometry of the molecu...

  11. Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of β-ketoesters

    Wen-Bin Yi

    2012-08-01

    Full Text Available A fluorous cinchona alkaloid ester has been developed as a chiral promoter for the asymmetric fluorination of β-ketoesters. It has comparable reactivity and selectivity to the nonfluorous versions of cinchona alkaloids and can be easily recovered from the reaction mixture by simple fluorous solid-phase extraction (F-SPE and used for the next round of reaction without further purification.

  12. Currencies of Mutualisms: Sources of Alkaloid Genes in Vertically Transmitted Epichloae

    Schardl, Christopher L; Young, Carolyn A; Juan Pan; Simona Florea; Takach, Johanna E.; Panaccione, Daniel G.; Farman, Mark L.; Webb, Jennifer S.; Jolanta Jaromczyk; Charlton, Nikki D.; Padmaja Nagabhyru; Li Chen; Chong Shi; Adrian Leuchtmann

    2013-01-01

    The epichloae (Epichloë and Neotyphodium species), a monophyletic group of fungi in the family Clavicipitaceae, are systemic symbionts of cool-season grasses (Poaceae subfamily Poöideae). Most epichloae are vertically transmitted in seeds (endophytes), and most produce alkaloids that attack nervous systems of potential herbivores. These protective metabolites include ergot alkaloids and indole-diterpenes (tremorgens), which are active in vertebrate systems, and lolines and peramine, which are...

  13. Effect of Iboga Alkaloids on µ-Opioid Receptor-Coupled G Protein Activation

    Antonio, Tamara; Childers, Steven R.; Rothman, Richard B.; Dersch, Christina M.; King, Christine; Kuehne, Martin; Bornmann, William G.; Amy J Eshleman; Janowsky, Aaron; Simon, Eric R.; Reith, Maarten E. A.; Alper, Kenneth

    2013-01-01

    Objective The iboga alkaloids are a class of small molecules defined structurally on the basis of a common ibogamine skeleton, some of which modify opioid withdrawal and drug self-administration in humans and preclinical models. These compounds may represent an innovative approach to neurobiological investigation and development of addiction pharmacotherapy. In particular, the use of the prototypic iboga alkaloid ibogaine for opioid detoxification in humans raises the question of whether its ...

  14. Isolation and X-ray Crystal Structure of Tetrahydroisoquinoline Alkaloids from Calycotome Villosa Subsp. intermedias

    Mohammed Lachkar

    2004-07-01

    Full Text Available Two tetrahydroisoquinoline alkaloids were extracted from the alkaloid fraction of a methanol extract of the seeds of Calycotome Villosa Subsp. intermedia. Their structures were established as (R-1-hydroxymethyl-7-8-dimethoxy-1,2,3,4-tetrahydro- isoquinoline (1 and (S-7-hydroxymethyl-2-3-dimethoxy-7,8,9,10-tetrahydroisoquinoline chloride (2 by spectroscopic techniques and X-ray diffraction analysis.

  15. Antibacterial activity of the alkaloid extract and isolated compounds from Croton bonplandianum Baill. (Euphorbiaceae)

    Burgos, A.; J. BARUA; M.E. FLORES-GIUBI; D. BAZAN; Ferro, E.; N.L. ALVARENGA

    2015-01-01

    ABSTRACT The antibacterial activity of the alkaloid extract from the leaves of Croton bonplandianum Baill. and its main compounds, sparsiflorine and crotsparine, was tested against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa by the resazurin microtitre-plate method. Pure compounds were identified by spectroscopic techniques, mainly 1D and 2D NMR. The alkaloid extract showed activity particularly against the S. aureus and P. aeruginosa. Regarding t...

  16. Kohlenhydrat-Auxiliare in der asymmetrischen Synthese chiraler Stickstoffheterocyclen und Alkaloide

    Kranke, Birgit

    2005-01-01

    In dieser Arbeit wurden durch Verwendung eines stereodifferenzierenden Kohlenhydrat-Auxiliars chirale Stickstoffheterocyclen und enantiomerenreine Piperidin-Alkaloide synthetisiert. Alkaloide mit einer Piperidin-Grundstruktur sind in der Natur weit verbreitet und weisen vielfältige biologische Aktivitäten auf. Zusammen mit synthetischen Derivaten sind sie daher von großem Interesse für die Wirkstoffforschung. Mit dem aus D-Arabinose zugänglichen 2,3,4-Tri-O-pivaloyl-D-arabinosylamin wurden...

  17. Novel β-Carboline Alkaloid from Peganum Harmala As Antibacterial Agent

    A novel β-carboline alkaloid isolated from the aerial parts of Peganum harmala L. (Gen: Phyeophylaceae) have been characterized as l-thioformyl-8-β-D-glucopyranoside-bis-2,3-dihydro-isopyridinopyrrol. It is one of β-carboline alkaloids derivatives. The chemical structure was elucidated on the basis of elementary analysis and spectroscopic studies (UV, IR, 1H-NMR and MS). The isolated compound showed significant antibacterial activity against Streptococcus pyogenus.

  18. Alkaloids of Cynanchum vincetoxicum: Efficacy against MDA-MB-231 Mammary Carcinoma Cells

    Tanner, U.; Wiegrebe, Wolfgang

    1993-01-01

    Alkaloids 1-4 from Cynanchum vincetoxicum (asclepiadaceae) (Scheme 1) do not have affinity to the oestrogen receptor but they inhibit the growth of the hormone-independent mammary carcinoma cells MDA-MB-231 (Fig. 1) and bind to nucleosides and nucleotides (Table 1). Intercalation was not observed. Die Alkaloide 1-4 aus Cynanchum vincetoxicum (Asclepiadaceae) (Scheme 1) zeigen keine Affinität zum Oestrogen-Rezeptor, hemmen aber das Wachstum der hormonunabhängigen Mammakar...

  19. Geissoschizine methyl ether N-oxide, a new alkaloid with antiacetylcholinesterase activity from Uncaria rhynchophylla.

    Jiang, Wei-Wei; Su, Jia; Wu, Xing-De; He, Juan; Peng, Li-Yan; Cheng, Xiao; Zhao, Qin-Shi

    2015-01-01

    Geissoschizine methyl ether N-oxide, a new oxindole alkaloid, along with 14 known alkaloids, was isolated from the aerial part of Uncaria rhynchophylla. Their structures were identified by comprehensive spectral methods, including 2D NMR experiments, and confirmed by comparing with the literature data. In vitro acetylcholinesterase (AChE) inhibitory activity assay showed that the new compound exhibited anti-AChE activity with IC₅₀ value of 23.4 μM. PMID:25496282

  20. Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax.

    Pesqueira, A; Harmon, D L; Branco, A F; Klotz, J L

    2014-03-01

    The ergot alkaloid ergovaline has demonstrated a persistent and sustained contractile response in several different vascular models. It was hypothesized that different alkaloids isolated from tall fescue (Lolium arundinaceum) will contribute to this contractile response differently. The objective was to compare contractile-response patterns of single additions of the ergoline alkaloids lysergic acid, lysergol, and ergonovine and the ergopeptine alkaloids ergotamine, ergocristine, ergocryptine, ergocornine, and ergovaline (provided as tall fescue seed extract). Lateral saphenous veins were collected from 6 Holstein steers (BW = 397 ± 28 kg) immediately after slaughter, sliced into cross-sections, and suspended in myograph chambers containing oxygenated Krebs-Henseleit buffer (95% O2/5% CO2; pH = 7.4; 37°C). Treatments were added at 0 min and buffer was replaced in 15-min intervals for a 120-min incubation. In addition to maximum tension and time to reach maximum tension, percent relaxation and rate of relaxation were determined following maximum tension for each treatment. All compounds tested produced significant contractile responses (P ergotamine, ergocristine, ergocryptine, and ergocornine had slower developing contractile responses with a longer (P < 0.05) interval until maximum tension was achieved compared to the ergoline alkaloids. Maximal responses to all the ergopeptine alkaloids, however, all persisted for the 120-min duration with negligible relaxation occurring. The different classes of alkaloids differed greatly in the type of contractile response generated in the lateral saphenous vein. Persistence of contractile response is thought to be the primary contributing factor to the vasoconstriction observed in animals demonstrating signs of fescue toxicosis, where different ergot alkaloids can contribute differently. PMID:24492541

  1. Naphthylisoquinoline Alkaloids : Structural Elucidation, Metabolism and Functional Analysis of their Bioactivities

    Faber, Johan Henrik

    2007-01-01

    This thesis deals with the isolation and structural elucidation of bioactive naphthylisoquinoline alkaloids and related analogs. The mode of action of the antiplasmodial activity exhibited by the naphthylisoquinoline alkaloids was explored and compared to that of the antimalarial drug chloroquine. Furthermore, the phase 1 and 2 metabolism of dioncophyllines A and C and dioncopeltine A were investigated. In detail the following results have been obtained: • From the leaves of the recently disc...

  2. HPLC-ESI-MS/MS of Imidazole Alkaloids in Pilocarpus microphyllus

    Sawaya, Alexandra; Abreu, Ilka Nacif; Andreazza, Nathalia Luiza; Marcos N Eberlin; Mazzafera, Paulo

    2008-01-01

    Pilocarpine, an important imidazole alkaloid, is extracted from the leaves of Pilocarpus microphyllus (Rutaceae), known in Brazil as jaborandi and used mainly for the treatment of glaucoma. Jaborandi leaves also contain other imidazole alkaloids, whose pharmacological and physiological properties are unknown, and whose biosynthetic pathways are under investigation. In the present study, a HPLC method coupled with ESI-MSn was developed for their qualitative and quantitative analysis. This meth...

  3. Alkaloids isolated from the leaves of atemoya (Annona cherimola × Annona squamosa)

    Suzana V. Rabêlo; Costa, Emmanoel V.; Andersson Barison; Lívia M. Dutra; Xirley P. Nunes; José C. Tomaz; Gibson G. Oliveira; Norberto P. Lopes; Maria de Fátima C. Santos; Jackson R.G. da Silva Almeida

    2015-01-01

    AbstractAtemoya is an interspecific annonaceous hybrid between Annona cherimola Mill. and Annona squamosa L. Its phytochemical investigation led to seven alkaloids, including two aporphine (anonaine and asimilobine), three oxoaporphine (lanuginosine, liriodenine and lysicamine) and two proaporphine (pronuciferine and stepharine). These alkaloids were identified by a series of spectrometric methods, mainly MS and NMR (1D and 2D), as well as by comparison with literature data. Our findings show...

  4. Isolation and Characterization of Antineoplastic Alkaloids from Catharanthus Roseus L. Don. Cultivated in Egypt

    Shams, Khaled A; Nazif, Naglaa M; Abdel Azim, Nahla S; Abdel Shafeek, Khaled A; El-Missiry, Mostafa M.; Ismail, Shams I; Seif El Nasr, Medhat M

    2009-01-01

    Vinblastine and vincristine (the antileukemic agents) were isolated, in a pure form, from Catharanthus roseus L. Don., cultivated in Egypt, by several chromatographic techniques. Five modified methods for the preparation of total alkaloids were carried out. All the isolated mixtures were evaluated by HPLC and HPTLC analyses. The antineoplastic alkaloids; vinblastine and vincristine, were isolated by the use of vacuum liquid chromatographic column on silica gel : aluminium oxide (1:1) mixed be...

  5. Unlocking the Diversity of Alkaloids in Catharanthus roseus: Nuclear Localization Suggests Metabolic Channeling in Secondary Metabolism

    Stavrinides, Anna; Tatsis, Evangelos C.; Foureau, Emilien; Caputi, Lorenzo; Kellner, Franziska; Courdavault, Vincent; O’Connor, Sarah E.

    2015-01-01

    Summary The extraordinary chemical diversity of the plant-derived monoterpene indole alkaloids, which include vinblastine, quinine, and strychnine, originates from a single biosynthetic intermediate, strictosidine aglycone. Here we report for the first time the cloning of a biosynthetic gene and characterization of the corresponding enzyme that acts at this crucial branchpoint. This enzyme, an alcohol dehydrogenase homolog, converts strictosidine aglycone to the heteroyohimbine-type alkaloid ...

  6. A Stereoselective Hydroxylation Step of Alkaloid Biosynthesis by a Unique Cytochrome P450 in Catharanthus roseus*

    Giddings, Lesley-Ann; Liscombe, David K.; Hamilton, John P; Childs, Kevin L.; DellaPenna, Dean; Buell, C. Robin; O'Connor, Sarah E.

    2011-01-01

    Plant cytochrome P450s are involved in the production of over a hundred thousand metabolites such as alkaloids, terpenoids, and phenylpropanoids. Although cytochrome P450 genes constitute one of the largest superfamilies in plants, many of the catalytic functions of the enzymes they encode remain unknown. Here, we report the identification and functional characterization of a cytochrome P450 gene in a new subfamily of CYP71, CYP71BJ1, involved in alkaloid biosynthesis. Co-expression analysis ...

  7. Influence of Some Heavy Metals on Growth, Alkaloid Content and Composition in Catharanthus roseus L.

    Srivastava, N. K.; A.K. Srivastava

    2010-01-01

    Shoot biomass production, alkaloid content and composition as influence by cadmium, manganese, nickel and lead at uniform dose of 5 mM were investigated in Catharanthus roseus plants grown in sand culture. Treatment with Mn, Ni, and Pb significantly enhanced total root alkaloid accumulation. Cd and Ni treatment resulted in two-fold where as Pb treatment resulted in three fold increase in serpentine content of roots. The non-significant affect on biomass suggests that plants can withstand meta...

  8. Effect of Drying Methods on the Steroidal Alkaloid Content of Potato Peels, Shoots and Berries

    Hossain, Mohammad B.; Nigel P. Brunton; Rai, Dilip K.

    2016-01-01

    The present study has found that dried potato samples yielded significantly higher levels of steroidal alkaloids such as α-solanine and α-chaconine than the corresponding fresh samples, as determined by the UPLC-MS/MS technique. Among the drying techniques used, air drying had the highest effect on steroidal alkaloid contents, followed by freeze drying and vacuum oven drying. There was no significant difference between the freeze dried and vacuum oven dried samples in their α-chaconine conten...

  9. In vitro androgenetic cultures of Hyoscyamus niger L., H. albus L. and alkaloid content assay

    Maria Wesołwska

    2014-02-01

    Full Text Available In vitro cultures of Hyoscyamus niger L. and H. albus L. anthers were initiated which resulted in obtaining androgenectic plants and callus cultures. The leaves of these pants and the callus cultures were subjected to analysis (TLC, GC for the presence of alkaloids, derivatives of tropane. In the studied material, alkaloids of different qualitative and quantitative composition from that of ground-grown plants were found.

  10. Patterns of indole alkaloids synthesis in response to heat shock, 5-azacytidine and Na-butyrate treatment of cultured catharanthus roseus mesophyll protoplasts

    Alkaloids of C. roseus are in high demand for therapeutic and other reasons. Cultured Catharanthus cells can produce limited quantities of these alkaloids. The authors have found that cultured mesophyll protoplasts in the presence of 14C-Tryptamine are capable of synthesizing alkaloids. The pattern of alkaloids synthesis changes when protoplasts are subjected to a heat shock at 370C. The heat shocked protoplasts incorporated 33% more 14C-Tryptamine and produced 3 new types of alkaloids. Treatment of protoplasts with 5-azacytidine, a DNA hypomethylating agent and Na-butyrate which induces hyperacetylation of histones produced qualitative and quantitative changes in the alkaloid pattern. Four new alkaloids following the above treatments were detected by TLC and HPLC of the extracts. It is suggested that the alkaloid pattern of the cultured protoplasts can be altered by treatment with compounds known as regulators of gene expression. Work is in progress to isolate and identify these new alkaloids

  11. Patterns of indole alkaloids synthesis in response to heat shock, 5-azacytidine and Na-butyrate treatment of cultured catharanthus roseus mesophyll protoplasts

    Saleem, M.; Cutler, A.J.

    1986-04-01

    Alkaloids of C. roseus are in high demand for therapeutic and other reasons. Cultured Catharanthus cells can produce limited quantities of these alkaloids. The authors have found that cultured mesophyll protoplasts in the presence of /sup 14/C-Tryptamine are capable of synthesizing alkaloids. The pattern of alkaloids synthesis changes when protoplasts are subjected to a heat shock at 37/sup 0/C. The heat shocked protoplasts incorporated 33% more /sup 14/C-Tryptamine and produced 3 new types of alkaloids. Treatment of protoplasts with 5-azacytidine, a DNA hypomethylating agent and Na-butyrate which induces hyperacetylation of histones produced qualitative and quantitative changes in the alkaloid pattern. Four new alkaloids following the above treatments were detected by TLC and HPLC of the extracts. It is suggested that the alkaloid pattern of the cultured protoplasts can be altered by treatment with compounds known as regulators of gene expression. Work is in progress to isolate and identify these new alkaloids.

  12. Microcalorimetric investigation of effect of berberine alkaloids from Coptis chinensis Franch on intestinal diagnostic flora growth

    YAN Dan; WEI Li; XIAO XiaoHe; ZHOU DanLei; HAN YuMei

    2009-01-01

    The inhibitory effect of three berberine alkaloids (BAs) from Coptis chinensis Franch, a traditional Chinese medicinal (TCM) herb, on Bifidobacterium adolescentis growth was investigated by micro-calorimetry. The power-time curves of B. adolescentis with and without BAs were acquired, meanwhile the extent and duration of inhibitory effect on the metabolism were evaluated by the growth rate con-stant (k), half inhibitory ratio (IC50), maximum heat-output power (Pmax), peak time of maximum heat-output power (tp) and total heat production (Qt). k, Pmax and Qt decreased, and tp was prolonged with the increase of BAs concentration. The IC50 of BAs is 806 μg/mL for berberine, 341 μg/mL for cop-tisine and 236 μg/mL for palmatine. The sequence of antimicrobial activity of BAs is berberine coptisine > pal-matine. The structure-function relationship of BAs indicates that the functional group methylenedioxy or methoxyl at C2 and C3 might be the major group inducing the activities of BAs on E. coli and B. adolescentis. Meanwhile, the substituent groups at C2, C3, C9 and C10 almost have equal effect on B. shigae.

  13. Risk to human health associated with the environmental occurrence of cyanobacterial neurotoxic alkaloids anatoxins and saxitoxins.

    Testai, Emanuela; Scardala, Simona; Vichi, Susanna; Buratti, Franca M; Funari, Enzo

    2016-05-01

    Cyanobacteria are ubiquitous photosynthetic micro-organisms forming blooms and scums in surface water; among them some species can produce cyanotoxins giving rise to some concern for human health and animal life. To date, more than 65 cyanobacterial neurotoxins have been described, of which the most studied are the groups of anatoxins and saxitoxins (STXs), comprising many different variants. In freshwaters, the hepatotoxic microcystins represent the most frequently detected cyanotoxin: on this basis, it could appear that neurotoxins are less relevant, but the low frequency of detection may partially reflect an a priori choice of target analytes, the low method sensitivity and the lack of certified standards. Cyanobacterial neurotoxins target cholinergic synapses or voltage-gated ion channels, blocking skeletal and respiratory muscles, thus leading to death by respiratory failure. This review reports and analyzes the available literature data on environmental occurrence of cyanobacterial neurotoxic alkaloids, namely anatoxins and STXs, their biosynthesis, toxicology and epidemiology, derivation of guidance values and action limits. These data are used as the basis to assess the risk posed to human health, identify critical exposure scenarios and highlight the major data gaps and research needs. PMID:26923223

  14. Inhibitory effects of alkaloids from Sophora alopecuroids on feeding,development and reproduction of Clostera anastomosis

    Yang Zhende; Zhao Boguang; Zhu Lin; Fang Jie; Xia Luqing

    2006-01-01

    Alkaloids from Sophora alopecuroids were bioassayed with Clostera anastomosis for their antifeedant and growth inhibitory effects.The antifeedant rate in choice test reached 62%-86% at the dose 2.5 mg/mL,while in non-choice bioassay the rate was only 20%-29%.In choice bioassay,the anfifeedant rate increased with larval instars of C anastomosis and did not in non-choice experiment.The alkaloids also imposed a strong influence on the growth of C anastomosis larvae,i.e.,after feeding on the leaves treated with alkaloid,the larvae lost their weight,weight gain,and relative growth rate (RGR) significantly when compared with the controls.In the second day after treatment with the dose at 10 mg/mL of the alkaloid,the RGR reduced by 39.8%,and the food intake and the feces weight were respectively 57.7% and 57.4% of the controls.The approximate digestibility (AD) increased significantly,and the efficiency in converting digested food (ECD),and the efficiency in converting ingested food (ECI) decreased greatly after feeding the treated leaves.Moreover,the eggs laid per female were also inhibited by this alkaloid.The significance and prospect of the alkaloids in controlling forest insect pests were also discussed.

  15. Measurement of antiphotooxidative properties of isoquinoline alkaloids using transient thermal lens spectroscopy

    Hung, J.; Castillo, J.; Laboren, I.; Rodríguez, M.; Hassegawa, M.

    2005-11-01

    The antiphotooxidative properties of boldine and chloride berberine were studied by time-resolved thermal lensing technique. These compounds belong to isoquinoline alkaloids possessing interesting biological activity (e.g. antibacterial, antimalarial, antitumor). Antiphotooxidative properties of the alkaloids were studied by mechanism of energy transference between powerful oxidizing agents such as singlet oxygen. Singlet oxygen was produced by energy transfer from chlorophyll-sensitized photooxidation of oil by exposure of high light intensities like laser. The lifetimes of singlet oxygen in dimethylsulfoxide, methanol and water were determined to confirm the assignment of the singlet molecular oxygen O II (1Δ g) in the experiments. In order to understand the effect of the alkaloids on active oxygen species, we carried out in detail an analysis of the thermal lensing signal. It was shown that the alkaloids can act as quenchers of singlet oxygen. To demonstrate the ability of the alkaloids to act efficient singlet oxygen acceptors, we have measured the fluorescence spectra of the studied alkaloids in the presence and in the absence of singlet oxygen. The antiphotooxidative activity of boldine and chloride berberine can be explained by the ability to quench singlet oxygen.

  16. Currencies of Mutualisms: Sources of Alkaloid Genes in Vertically Transmitted Epichloae

    Christopher L. Schardl

    2013-06-01

    Full Text Available The epichloae (Epichloë and Neotyphodium species, a monophyletic group of fungi in the family Clavicipitaceae, are systemic symbionts of cool-season grasses (Poaceae subfamily Poöideae. Most epichloae are vertically transmitted in seeds (endophytes, and most produce alkaloids that attack nervous systems of potential herbivores. These protective metabolites include ergot alkaloids and indole-diterpenes (tremorgens, which are active in vertebrate systems, and lolines and peramine, which are more specific against invertebrates. Several Epichloë species have been described which are sexual and capable of horizontal transmission, and most are vertically transmissible also. Asexual epichloae are mainly or exclusively vertically transmitted, and many are interspecific hybrids with genomic contributions from two or three ancestral Epichloë species. Here we employ genome-scale analyses to investigate the origins of biosynthesis gene clusters for ergot alkaloids (EAS, indole-diterpenes (IDT, and lolines (LOL in 12 hybrid species. In each hybrid, the alkaloid-gene and housekeeping-gene relationships were congruent. Interestingly, hybrids frequently had alkaloid clusters that were rare in their sexual ancestors. Also, in those hybrids that had multiple EAS, IDT or LOL clusters, one cluster lacked some genes, usually for late pathway steps. Possible implications of these findings for the alkaloid profiles and endophyte ecology are discussed.

  17. Currencies of mutualisms: sources of alkaloid genes in vertically transmitted epichloae.

    Schardl, Christopher L; Young, Carolyn A; Pan, Juan; Florea, Simona; Takach, Johanna E; Panaccione, Daniel G; Farman, Mark L; Webb, Jennifer S; Jaromczyk, Jolanta; Charlton, Nikki D; Nagabhyru, Padmaja; Chen, Li; Shi, Chong; Leuchtmann, Adrian

    2013-06-01

    The epichloae (Epichloë and Neotyphodium species), a monophyletic group of fungi in the family Clavicipitaceae, are systemic symbionts of cool-season grasses (Poaceae subfamily Poöideae). Most epichloae are vertically transmitted in seeds (endophytes), and most produce alkaloids that attack nervous systems of potential herbivores. These protective metabolites include ergot alkaloids and indole-diterpenes (tremorgens), which are active in vertebrate systems, and lolines and peramine, which are more specific against invertebrates. Several Epichloë species have been described which are sexual and capable of horizontal transmission, and most are vertically transmissible also. Asexual epichloae are mainly or exclusively vertically transmitted, and many are interspecific hybrids with genomic contributions from two or three ancestral Epichloë species. Here we employ genome-scale analyses to investigate the origins of biosynthesis gene clusters for ergot alkaloids (EAS), indole-diterpenes (IDT), and lolines (LOL) in 12 hybrid species. In each hybrid, the alkaloid-gene and housekeeping-gene relationships were congruent. Interestingly, hybrids frequently had alkaloid clusters that were rare in their sexual ancestors. Also, in those hybrids that had multiple EAS, IDT or LOL clusters, one cluster lacked some genes, usually for late pathway steps. Possible implications of these findings for the alkaloid profiles and endophyte ecology are discussed. PMID:23744053

  18. Aptamer-Based Molecular Recognition of Lysergamine, Metergoline and Small Ergot Alkaloids

    Johan Robbens

    2012-12-01

    Full Text Available Ergot alkaloids are mycotoxins produced by fungi of the genus Claviceps, which infect cereal crops and grasses. The uptake of ergot alkaloid contaminated cereal products can be lethal to humans and animals. For food safety assessment, analytical techniques are currently used to determine the presence of ergot alkaloids in food and feed samples. However, the number of samples which can be analyzed is limited, due to the cost of the equipment and the need for skilled personnel. In order to compensate for the lack of rapid tests for the detection of ergot alkaloids, the aim of this study was to develop a specific recognition element for ergot alkaloids, which could be further applied to produce a colorimetric reaction in the presence of these toxins. As recognition elements, single-stranded DNA ligands were selected by using an iterative selection procedure named SELEX, i.e., Systematic Evolution of Ligands by EXponential enrichment. After several selection cycles, the resulting aptamers were cloned and sequenced. A surface plasmon resonance analysis enabled determination of the dissociation constants of the complexes of aptamers and lysergamine. Dissociation constants in the nanomolar range were obtained with three selected aptamers. One of the selected aptamers, having a dissociation constant of 44 nM, was linked to gold nanoparticles and it was possible to produce a colorimetric reaction in the presence of lysergamine. This system could also be applied to small ergot alkaloids in an ergot contaminated flour sample.

  19. A Stereoselective Hydroxylation Step of Alkaloid Biosynthesis by a Unique Cytochrome P450 in Catharanthus roseus*

    Giddings, Lesley-Ann; Liscombe, David K.; Hamilton, John P.; Childs, Kevin L.; DellaPenna, Dean; Buell, C. Robin; O'Connor, Sarah E.

    2011-01-01

    Plant cytochrome P450s are involved in the production of over a hundred thousand metabolites such as alkaloids, terpenoids, and phenylpropanoids. Although cytochrome P450 genes constitute one of the largest superfamilies in plants, many of the catalytic functions of the enzymes they encode remain unknown. Here, we report the identification and functional characterization of a cytochrome P450 gene in a new subfamily of CYP71, CYP71BJ1, involved in alkaloid biosynthesis. Co-expression analysis of putative cytochrome P450 genes in the Catharanthus roseus transcriptome identified candidate genes with expression profiles similar to known terpene indole alkaloid biosynthetic genes. Screening of these candidate genes by functional expression in Saccharomyces cerevisiae yielded a unique P450-dependent enzyme that stereoselectively hydroxylates the alkaloids tabersonine and lochnericine at the 19-position of the aspidosperma-type alkaloid scaffold. Tabersonine, which can be converted to either vindoline or 19-O-acetylhörhammericine, represents a branch point in alkaloid biosynthesis. The discovery of CYP71BJ1, which forms part of the pathway leading to 19-O-acetylhörhammericine, will help illuminate how this branch point is controlled in C. roseus. PMID:21454651

  20. Binary stress induces an increase in indole alkaloid biosynthesis in Catharanthus roseus.

    Zhu, Wei; Yang, Bingxian; Komatsu, Setsuko; Lu, Xiaoping; Li, Ximin; Tian, Jingkui

    2015-01-01

    Catharanthus roseus is an important medicinal plant, which produces a variety of indole alkaloids of significant pharmaceutical relevance. In the present study, we aimed to investigate the potential stress-induced increase of indole alkaloid biosynthesis in C. roseus using proteomic technique. The contents of the detectable alkaloids ajmalicine, vindoline, catharanthine, and strictosidine in C. roseus were significantly increased under binary stress. Proteomic analysis revealed that the abundance of proteins related to tricarboxylic acid cycle and cell wall was largely increased; while, that of proteins related to tetrapyrrole synthesis and photosynthesis was decreased. Of note, 10-hydroxygeraniol oxidoreductase, which is involved in the biosynthesis of indole alkaloid was two-fold more abundant in treated group compared to the control. In addition, mRNA expression levels of genes involved in the indole alkaloid biosynthetic pathway indicated an up-regulation in their transcription in C. roseus under UV-B irradiation. These results suggest that binary stress might negatively affect the process of photosynthesis in C. roseus. In addition, the induction of alkaloid biosynthesis appears to be responsive to binary stress. PMID:26284098

  1. Binary Stress Induces an Increase in Indole Alkaloid Biosynthesis in Catharanthus roseus

    Wei eZhu

    2015-07-01

    Full Text Available Catharanthus roseus is an important medicinal plant, which produces a variety of indole alkaloids of significant pharmaceutical relevance. In the present study, we aimed to investigate the potential stress-induced increase of indole alkaloid biosynthesis in C. roseus using proteomic technique. The contents of the detectable alkaloids ajmalicine, vindoline, catharanthine, and strictosidine in C. roseus were significantly increased under binary stress. Proteomic analysis revealed that the abundance of proteins related to tricarboxylic acid cycle and cell wall was largely increased; while, that of proteins related to tetrapyrrole synthesis and photosynthesis was decreased. Of note, 10-hydroxygeraniol oxidoreductase, which is involved in the biosynthesis of indole alkaloid was two-fold more abundant in treated group compared to that in control. In addition, mRNA expression levels of genes involved in the indole alkaloid biosynthetic pathway indicated an up-regulation in their transcription in C. roseus under UV-B irradiation. These results suggest that binary stress might negatively affect the process of photosynthesis in C. roseus. In addition, the induction of alkaloid biosynthesis appears to be responsive to binary stress.

  2. The Total Synthesis of Galbulimima Alkaloid (+/-) G. B. 13 and the Development of an Anomalous Heck Reaction

    Larson, Kimberly Katherine

    2009-01-01

    This dissertation describes our strategy for the total synthesis of Galbulimima alkaloid ()-G. B. 13. First, an overview of the isolation and structural classification of the twenty-eight alkaloids in the Galbulimima family is presented. Proposals for the biosyntheses of these natural products as well as the determination of their absolute stereochemical relationships are discussed. Additionally, the biological and medicinal properties of himbacine, another Galbulimima alkaloid, are present...

  3. Mass spectra of alkaloids from cissampelos pareira L Mass spectra of alkaloids from cissampelos pareira L.

    Aguirre Gálviz Luis Enrique

    1988-06-01

    -bidi-font-family:"Times New Roman"; mso-bidi-theme-font:minor-bidi; mso-fareast-language:EN-US;} .MsoPapDefault {mso-style-type:export-only; margin-bottom:10.0pt; line-height:115%;} @page WordSection1 {size:612.0pt 792.0pt; margin:70.85pt 3.0cm 70.85pt 3.0cm; mso-header-margin:36.0pt; mso-footer-margin:36.0pt; mso-paper-source:0;} div.WordSection1 {page:WordSection1;} -->

    The mass spectra of the tertiary bis-benzyl-isoquinoline alkaloids, warifteine and methyl-warifteine, extracted from the ethnobotanically important species, Cissampelos pareira L.. are discussed. Infonnation about the reltive positions of two hydroxyl and two methoxyl groups in warifteine and the presence of a p-xylyl moiety in both compounds in provided.

    Se presenta una discusión de los espectros de masas de warifteina y metilwarifteina, dos alcaloides

  4. Evidence of maternal provisioning of alkaloid-based chemical defenses in the strawberry poison frog Oophaga pumilio.

    Stynoski, Jennifer L; Torres-Mendoza, Yaritbel; Sasa-Marin, Mahmood; Saporito, Ralph A

    2014-03-01

    Many organisms use chemical defenses to reduce predation risk. Aposematic dendrobatid frogs sequester alkaloid-based chemical defenses from a diet of arthropods, but research on these defenses has been limited to adults. Herein, we investigate chemical defense across development in a dendrobatid frog, Oophaga pumilio. This species displays complex parental care: at hatching, mothers transport tadpoles to phytotelmata, and then return to supply them with an obligate diet of nutritive eggs for about six weeks. We collected eggs, tadpoles, juveniles, and adults of O. pumilio, and detected alkaloids in all life stages. The quantity and number of alkaloids increased with frog and tadpole size. We did not detect alkaloids in the earliest stage of tadpoles, but alkaloids were detected as trace quantities in nutritive eggs and as small quantities in ovarian eggs. Tadpoles hand-reared with eggs of an alkaloid-free heterospecific frog did not contain alkaloids. Alkaloids that are sequestered from terrestrial arthropods were detected in both adults and phytotelm-dwelling tadpoles that feed solely on nutritive eggs, suggesting that this frog may be the first animal known to actively provision post-hatch offspring with chemical defenses. Finally, we provide experimental evidence that maternally derived alkaloids deter predation of tadpoles by a predatory arthropod. PMID:24804437

  5. Changes in plant defense chemistry (pyrrolizidine alkaloids) revealed through high-resolution spectroscopy

    Carvalho, Sabrina; Macel, Mirka; Schlerf, Martin; Moghaddam, Fatemeh Eghbali; Mulder, Patrick P. J.; Skidmore, Andrew K.; van der Putten, Wim H.

    2013-06-01

    Plant toxic biochemicals play an important role in defense against natural enemies and often are toxic to humans and livestock. Hyperspectral reflectance is an established method for primary chemical detection and could be further used to determine plant toxicity in the field. In order to make a first step for pyrrolizidine alkaloids detection (toxic defense compound against mammals and many insects) we studied how such spectral data can estimate plant defense chemistry under controlled conditions. In a greenhouse, we grew three related plant species that defend against generalist herbivores through pyrrolizidine alkaloids: Jacobaea vulgaris, Jacobaea erucifolia and Senecio inaequidens, and analyzed the relation between spectral measurements and chemical concentrations using multivariate statistics. Nutrient addition enhanced tertiary-amine pyrrolizidine alkaloids contents of J. vulgaris and J. erucifolia and decreased N-oxide contents in S. inaequidens and J. vulgaris. Pyrrolizidine alkaloids could be predicted with a moderate accuracy. Pyrrolizidine alkaloid forms tertiary-amines and epoxides were predicted with 63% and 56% of the variation explained, respectively. The most relevant spectral regions selected for prediction were associated with electron transitions and Csbnd H, Osbnd H, and Nsbnd H bonds in the 1530 and 2100 nm regions. Given the relatively low concentration in pyrrolizidine alkaloids concentration (in the order of mg g-1) and resultant predictions, it is promising that pyrrolizidine alkaloids interact with incident light. Further studies should be considered to determine if such a non-destructive method may predict changes in PA concentration in relation to plant natural enemies. Spectroscopy may be used to study plant defenses in intact plant tissues, and may provide managers of toxic plants, food industry and multitrophic-interaction researchers with faster and larger monitoring possibilities.

  6. Relationships among Ergot Alkaloids, Cytochrome P450 Activity, and Beef Steer Growth

    Rosenkrans, Charles; Ezell, Nicholas

    2015-03-01

    Determining a grazing animal’s susceptibility to ergot alkaloids has been a research topic for decades. Our objective was to determine if the Promega™ P450-Glo assay could be used to indirectly detect ergot alkaloids or their metabolites in urine of steers. The first experiment validated the effects of ergot alkaloids [0, 20, and 40 μM of ergotamine (ET), dihydroergotamine (DHET), and ergonovine (EN)] on human CYP3A4 using the P450-Glo assay (Promega™ V9800). With this assay, luminescence is directly proportional to CYP450 activity. Relative inhibition of in vitro cytochrome P450 activity was affected (P experiment 2, urine was collected from Angus-sired crossbred steers (n = 39; 216 ± 2.6 d of age; 203 ± 1.7 kg) after grazing tall fescue pastures for 105 d. Non-diluted urine was added to the Promega™ P450-Glo assay, and observed inhibition (3.7 % ± 2.7 of control). Urine content of total ergot alkaloids (331.1 ng/mg of creatinine ± 325.7) was determined using enzyme linked immunosorbent assay. Urine inhibition of CYP450 activity and total alkaloids were correlated (r = -0.31; P animals that are susceptible to ergot alkaloids. Although, additional research is needed, we demonstrate that the Promega™ P450-Glo assay is sensitive to ergot alkaloids and urine from steers grazing tall fescue. With some refinement the P450-Glo assay has potential as a tool for screening cattle for their exposure to fescue toxins.

  7. Effect of Drying Methods on the Steroidal Alkaloid Content of Potato Peels, Shoots and Berries

    Mohammad B. Hossain

    2016-03-01

    Full Text Available The present study has found that dried potato samples yielded significantly higher levels of steroidal alkaloids such as α-solanine and α-chaconine than the corresponding fresh samples, as determined by the UPLC-MS/MS technique. Among the drying techniques used, air drying had the highest effect on steroidal alkaloid contents, followed by freeze drying and vacuum oven drying. There was no significant difference between the freeze dried and vacuum oven dried samples in their α-chaconine contents. However, freeze dried potato shoots and berries had significantly higher α-solanine contents (825 µg/g dry weight (DW in shoots and 2453 µg/g DW in berries than the vacuum oven dried ones (325 µg/g dry weight (DW in shoots and 2080 µg/g DW in berries. The kinetics of steroidal alkaloid contents of potato shoots during air drying were monitored over a period of 21 days. Both α-solanine and α-chaconine content increased to their maximum values, 875 µg/g DW and 3385 µg/g DW, respectively, after 7 days of drying. The steroidal alkaloid contents of the shoots decreased significantly at day 9, and then remained unchanged until day 21. In line with the potato shoots, air dried potato tuber peels also had higher steroidal alkaloid content than the freeze dried and vacuum oven dried samples. However, a significant decrease of steroidal alkaloid content was observed in air dried potato berries, possibly due to degradation during slicing of the whole berries prior to air drying. Remarkable variation in steroidal alkaloid contents among different tissue types of potato plants was observed with the potato flowers having the highest content.

  8. Effect of Drying Methods on the Steroidal Alkaloid Content of Potato Peels, Shoots and Berries.

    Hossain, Mohammad B; Brunton, Nigel P; Rai, Dilip K

    2016-01-01

    The present study has found that dried potato samples yielded significantly higher levels of steroidal alkaloids such as α-solanine and α-chaconine than the corresponding fresh samples, as determined by the UPLC-MS/MS technique. Among the drying techniques used, air drying had the highest effect on steroidal alkaloid contents, followed by freeze drying and vacuum oven drying. There was no significant difference between the freeze dried and vacuum oven dried samples in their α-chaconine contents. However, freeze dried potato shoots and berries had significantly higher α-solanine contents (825 µg/g dry weight (DW) in shoots and 2453 µg/g DW in berries) than the vacuum oven dried ones (325 µg/g dry weight (DW) in shoots and 2080 µg/g DW in berries). The kinetics of steroidal alkaloid contents of potato shoots during air drying were monitored over a period of 21 days. Both α-solanine and α-chaconine content increased to their maximum values, 875 µg/g DW and 3385 µg/g DW, respectively, after 7 days of drying. The steroidal alkaloid contents of the shoots decreased significantly at day 9, and then remained unchanged until day 21. In line with the potato shoots, air dried potato tuber peels also had higher steroidal alkaloid content than the freeze dried and vacuum oven dried samples. However, a significant decrease of steroidal alkaloid content was observed in air dried potato berries, possibly due to degradation during slicing of the whole berries prior to air drying. Remarkable variation in steroidal alkaloid contents among different tissue types of potato plants was observed with the potato flowers having the highest content. PMID:27023503

  9. Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway

    Plasswilm Ludwig

    2006-01-01

    from chemical synthesis. Instead, the Chelidonium majus L. alkaloids chelidonine, sanguinarine, chelerythrine, protopine and allocryptopine were identified as major components of Ukrain. Apart from sanguinarine and chelerythrine, chelidonine turned out to be a potent inducer of apoptosis triggering cell death at concentrations of 0.001 mM, while protopine and allocryptopine were less effective. Similar to Ukrain, apoptosis signalling of chelidonine involved Bcl-2 controlled mitochondrial alterations and caspase-activation. Conclusion The potent proapoptotic effects of Ukrain are not due to the suggested "Ukrain-molecule" but to the cytotoxic efficacy of Chelidonium majus L. alkaloids including chelidonine.

  10. Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity.

    Gadhiya, Satishkumar; Madapa, Sudharshan; Kurtzman, Thomas; Alberts, Ian L; Ramsey, Steven; Pillarsetty, Nagavara-Kishore; Kalidindi, Teja; Harding, Wayne W

    2016-05-01

    Two series of analogues of the tetrahydroprotoberberine (THPB) alkaloid (±)-stepholidine that (a) contain various alkoxy substituents at the C10 position and, (b) were de-rigidified with respect to (±)-stepholidine, were synthesized and evaluated for affinity at dopamine and σ receptors in order to evaluate effects on D3 and σ2 receptor affinity and selectivity. Small n-alkoxy groups are best tolerated by D3 and σ2 receptors. Among all compounds tested, C10 methoxy and ethoxy analogues (10 and 11 respectively) displayed the highest affinity for σ2 receptors as well as σ2 versus σ1 selectivity and also showed the highest D3 receptor affinity. De-rigidification of stepholidine resulted in decreased affinity at all receptors evaluated; thus the tetracyclic THPB framework is advantageous for affinity at dopamine and σ receptors. Docking of the C10 analogues at the D3 receptor, suggest that an ionic interaction between the protonated nitrogen atom and Asp110, a H-bond interaction between the C2 phenol and Ser192, a H-bond interaction between the C10 phenol and Cys181 as well as hydrophobic interactions of the aryl rings to Phe106 and Phe345, are critical for high affinity of the compounds. PMID:27032890

  11. Microwave Spectroscopy of Alkaloids: the Conformational Shapes of Nicotine

    Grabow, Jens-Uwe; Mata, S.; López, J. C.; Peńa, I.; Cabezas, C.; Blanco, S.; Alonso, J. L.

    2010-06-01

    Nicotinoid alkaloids consist of two ring systems connected via a C-C σ-bond: Joining pyridine either with a (substituted) pyrrolidine or piperidine ring system, pyrrolidinic or piperidinic nicotinoids are formed. Nicotine itself, consisting of pyridine and N-methylpyrrolidine, is the prototype pyrrolidinic nicotinoid. Its coupled heteoaromatic and heteroaliphatic ring systems exhibit three sites that allow for conformational flexibility: (I) puckering of the pyrrolidine ring (Eq./Ax. positions of the pyridine), (II) inversion of the N-methyl group (Eq./Ax. positions of the hydrogen), and (III) relative orientation of the two rings (Syn-Anti). Two conformations of nicotine have been observed using the In-phase/quadrature-phase-Modulation Passage-Acquired-Coherence Technique (IMPACT) Fourier Transform Microwave (FTMW) spectrometer in Valladolid. The preferred conformations are characterized by an equatorial (Eq.) pyridine moiety and equatorial (Eq.) N-CH_3 stereochemistry. The planes of two rings are almost perpendicular with respect to each other while exhibiting two low energy conformations, Syn and Anti, that differ by a 180° rotation about the C-C σ-bond. The Eq.-Eq. conformational preference is likely due to a weak hydrogen bond interaction between the nitrogen lone pair at the N-methylpyrroline and the closest hydrogen in pyridine. Supporting quantum-chemical calculations are also provided. Lavrich, R. J.; Suenram, R. D.; Plusquellic, D. F.; Davis, S. 58th International Symposium on Molecular Spectroscopy, Columbus, OH 2003, RH13.

  12. Antitumor effects of the benzophenanthridine alkaloid sanguinarine: Evidence and perspectives.

    Gaziano, Roberta; Moroni, Gabriella; Buè, Cristina; Miele, Martino Tony; Sinibaldi-Vallebona, Paola; Pica, Francesca

    2016-01-15

    Historically, natural products have represented a significant source of anticancer agents, with plant-derived drugs becoming increasingly explored. In particular, sanguinarine is a benzophenanthridine alkaloid obtained from the root of Sanguinaria canadensis, and from other poppy Fumaria species, with recognized anti-microbial, anti-oxidant and anti-inflammatory properties. Recently, increasing evidence that sanguinarine exibits anticancer potential through its capability of inducing apoptosis and/or antiproliferative effects on tumor cells, has been proved. Moreover, its antitumor seems to be due not only to its pro-apoptotic and inhibitory effects on tumor growth, but also to its antiangiogenic and anti-invasive properties. Although the precise mechanisms underlying the antitumor activity of this compound remain not fully understood, in this review we will focus on the most recent findings about the cellular and molecular pathways affected by sanguinarine, together with the rationale of its potential application in clinic. The complex of data currently available suggest the potential application of sanguinarine as an adjuvant in the therapy of cancer, but further pre-clinical studies are needed before such an antitumor strategy can be effectively translated in the clinical practice. PMID:26798435

  13. Hobartine: a tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui).

    Paz Robles, Cristian; Badilla Vidal, Natalia; Suarez, Sebastián; Baggio, Ricardo

    2014-11-01

    The natural compound hobartine {systematic name: (1R)-3-[(1S,5S)-(4,4,8-trimethylbicyclo[3.3.1]non-7-en-2-yl)methyl]-2,3-dihydro-1H-indole}, C20H26N2, (I), is an indole alkaloid isolated from Aristotelia chilensis as part of a study of secondary metabolites from Chilean flora. The colourless compound has a tetracyclic structure closely related to the strongly coloured polymorphic structures discussed in Paz et al. [Acta Cryst. (2013), C69, 1509-1512] and Watson et al. [Acta Cryst. (1989), C45, 1322-1324]. The main differences reside in the absence of a keto group in (I) compared with the previous structures, as well as an endo double bond in (I) contrasting with the exo double bond found in the previous structures. The supramolecular structure of (I) in strongly related to the twofold screw axis, around which isolated chains build up, internally linked by an N-H···N hydrogen bond which is the only significant intermolecular interaction present in the structure. PMID:25370110

  14. Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua.

    Hillwig, Matthew L; Zhu, Qin; Liu, Xinyu

    2014-02-21

    Ambiguines belong to a family of hapalindole-type indole alkaloid natural products, with many of the members possessing up to eight consecutive carbon stereocenters in a fused pentacyclic 6-6-6-5-7 ring scaffold. Here, we report the identification of a 42 kbp ambiguine (amb) biosynthetic gene cluster that harbors 32 protein-coding genes in its native producer Fischerella ambigua UTEX1903. Association of the amb cluster with ambiguine biosynthesis was confirmed by both bioinformatic analysis and in vitro characterizations of enzymes responsible for 3-((Z)-2'-isocyanoethenyl) indole and geranyl pyrophosphate biosynthesis and a C-2 indole dimethylallyltransferase that regiospecifically tailors hapalindole G to ambiguine A. The presence of five nonheme iron-dependent oxygenase coding genes (including four Rieske-type oxygenases) within the amb cluster suggests late-stage C-H activations are likely responsible for the structural diversities of ambiguines by regio- and stereospecific chlorination, hydroxylation, epoxidation, and sp(2)-sp(3) C-C bond formation. PMID:24180436

  15. Anti-Allergic Properties of Curine, a Bisbenzylisoquinoline Alkaloid

    Jaime Ribeiro-Filho

    2015-03-01

    Full Text Available Curine is a bisbenzylisoquinoline alkaloid isolated from Chondrodendron platyphyllum (Menispermaceae. Recent findings have shed light on the actions of curine in different models of allergy and inflammation. Here we review the properties and mechanisms of action of curine focusing on its anti-allergic effects. Curine pre-treatment significantly inhibited the scratching behavior, paw edema and systemic anaphylaxis induced by either ovalbumin (OVA in sensitized animals or compound 48/80, through mechanisms of mast cell stabilization and inhibition of mast cell activation to generate lipid mediators. In addition, oral administration of curine significantly inhibited eosinophil recruitment and activation, as well as, OVA-induced airway hyper-responsiveness in a mouse model of asthma, through inhibition of the production of IL-13 and eotaxin, and of Ca2+ influx. In conclusion, curine exhibit anti-allergic effects in models of lung, skin and systemic allergy in the absence of significant toxicity, and as such has the potential for anti-allergic drug development.

  16. In vitro biological activities of alkaloids from Cryptolepis sanguinolenta.

    Cimanga, K; De Bruyne, T; Lasure, A; Van Poel, B; Pieters, L; Claeys, M; Berghe, D V; Kambu, K; Tona, L; Vlietinck, A J

    1996-02-01

    In our biological screening of higher plants, an aqueous and an 80% EtOH extract from the root bark of Cryptolepis sanguinolenta showed potent antibacterial, anticomplementary, and moderate antiviral activities, but no antifungal effect could be detected. Bioassay-guided fractionation of the 80% EtOH extract led to the isolation of three alkaloids: quindoline (1), hydroxycryptolepine (2), cryptolepine.HCl (3), and the corresponding base cryptolepine (4). All compounds strongly inhibited the growth of Gram-positive bacteria (MIC 500 micrograms/ml) against selected Gram-negative bacteria. They also possessed a bactericidal effect depending on the bacterial strain. Compounds 1, 2 and 3 displayed a dose-dependent inhibitory effect on the classical pathway of the complement system while compounds 2 and 3 activated the alternative pathway, except for compound 1. Compound 3 was found to possess an antiherpetic activity. Compounds 1 and 4 showed no antiviral effect, but were quite cytotoxic in the antiviral test system down to a concentration of 1 microgram/ml. PMID:8720383

  17. Bis and tris indole alkaloids from marine organisms: new leads for drug discovery.

    Gupta, Leena; Talwar, Archna; Chauhan, Prem M S

    2007-01-01

    The marine organisms are a rich source of varied natural products with unique functionality. Marine natural products chemistry has undergone an explosive growth during the past three decades. A variety of natural products of new molecular structures with diverse biological activities have been reported from marine flora and fauna, thus ensuring motivation in the search of newer natural products. The bis and trisindole alkaloids are a class of marine natural products that show unique promise in the development of new drug leads. 3-hydroxy staurosporine 51, an indolo carbazole having powerful antiproliferative activity. Hamacanthin A 1 and B 2, pyrazinone alkaloids have significant antimicrobial activity. Coscinamides 60-62 and Chondriamides 63-65 an indolic enamides which have anti-HIV and cytotoxic activity respectively. Gelluisine A 66 and B 67, trisindole alkaloids have strong anti-serotonin activity and strong affinity with somatostatin and neuropeptide Y receptors in receptor-binding assays. This report reviews the literature on these alkaloids of marine origin and highlights the isolation, structure, latest synthesis and specific biological activities including cytotoxicity, antiviral, antiparasitic, serotonin antagonism and other pharmacological activities of sixty-nine bis and trisindole alkaloids. PMID:17627517

  18. Wild Argentinian Amaryllidaceae, a New Renewable Source of the Acetylcholinesterase Inhibitor Galanthamine and Other Alkaloids

    Gabriela E. Feresin

    2012-11-01

    Full Text Available The Amaryllidaceae family is well known for its pharmacologically active alkaloids. An important approach to treat Alzheimer’s disease involves the inhibition of the enzyme acetylcholinesterase (AChE. Galanthamine, an Amaryllidaceae alkaloid, is an effective, selective, reversible, and competitive AchE inhibitor. This work was aimed at studying the alkaloid composition of four wild Argentinian Amarillydaceae species for the first time, as well as analyzing their inhibitory activity on acetylcholinesterase. Alkaloid content was characterized by means of GC-MS analysis. Chloroform basic extracts from Habranthus jamesonii, Phycella herbertiana, Rhodophiala mendocina and Zephyranthes filifolia collected in the Argentinian Andean region all contained galanthamine, and showed a strong AChE inhibitory activity (IC50 between 1.2 and 2 µg/mL. To our knowledge, no previous reports on alkaloid profiles and AChEIs activity of wild Argentinian Amarillydaceae species have been publisihed. The demand for renewable sources of industrial products like galanthamine and the need to protect plant biodiversity creates an opportunity for Argentinian farmers to produce such crops.

  19. Luminescence and binding properties of two isoquinoline alkaloids chelerythrine and sanguinarine with ctDNA

    Li, Junfen; Li, Baohong; Wu, Yanbo; Shuang, Shaomin; Dong, Chuan; Choi, Martin M. F.

    2012-09-01

    The binding mode and mechanism of the interactions between two planar cationic alkaloids chelerythrine (Che) and sanguinarine (San) with calf thymus DNA (ctDNA) were systematically investigated at pH 5.40 using UV-vis absorption spectroscopy, fluorescence spectroscopy and cyclic voltammetry. Che and San show strong fluorescence at 570 and 589 nm, respectively. Che displays fluorescence enhancement with ctDNA whereas the fluorescence of San is quenched on interaction with ctDNA. In addition, UV-vis spectra of both alkaloids show apparent hypochromicity and are bathochromic shifted, indicating that they could intercalate into ctDNA bases. The fluorescence polarization of Che and San increases in the presence of ctDNA, again implying the intercalation of two alkaloids with ctDNA. This conclusion was also supported by the results obtained from anion quenching and cyclic voltammetry. The binding constants of both alkaloids with ctDNA were calculated in the order of 105 L/mol. San binds with ctDNA 3-fold stronger than Che. The stoichiometric bindings are five nucleotides per Che or San. Electrostatic binding also exists between the alkaloids and DNA helix. Finally, theoretical calculations show that only certain parts of Che and San molecules intercalate into the DNA helix.

  20. Optimization of Extraction and Enrichment of Steroidal Alkaloids from Bulbs of Cultivated Fritillaria cirrhosa

    Dongdong Wang

    2014-01-01

    Full Text Available The bulbs of cultivated Fritillaria cirrhosa (BCFC are used in China both for food and folk medicine due to its powerful biological activities. The aim of this study is to optimize the extraction and enrichment conditions of alkaloids from BCFC. Firstly, the orthogonal experimental design was used to optimize and evaluate four variables (ethanol concentration, solid-liquid ratio, extraction time, and temperature. Thereafter, resin adsorption was as a means to enrich alkaloids. Among 16 tested resins, H-103 resin presented higher adsorption capacity and desorption ratio. The equilibrium experimental data of the adsorption of total alkaloids, imperialine, and peimisine were well-fitted to the pseudo-first-order kinetics model, Langmuir and Freundlich isotherms models. Finally, in order to optimize the parameters for purifying alkaloids, dynamic adsorption and desorption tests were carried out. After one run treatment with H-103 resin, the contents of total alkaloids, imperialine, and peimisine in the product were 21.40-, 18.31-, and 22.88-fold increased with recovery yields of 94.43%, 90.57%, and 96.16%, respectively.

  1. Managing murine food allergy with Cissampelos sympodialis Eichl (Menispermaceae) and its alkaloids.

    Costa, Hermann Ferreira; Leite, Fagner Carvalho; Alves, Adriano Francisco; Barbosa-Filho, José Maria; dos Santos, Claudio Roberto Bezerra; Piuvezam, Marcia Regina

    2013-10-01

    Food allergy is a severe human disease with imminent risk of life. Cissampelos sympodialis (Menispermaceae) is a native Brazilian plant used in Brazilian folk medicine for the treatment of respiratory allergies. In this study the experimental model of food allergy induced by ovalbumin (OVA) was used to determine whether the alcoholic extract of the plant (AFL) and its alkaloids match a therapeutic approach for this disease. Animal weight, diarrhea, OVA-specific IgE levels, inflammatory cell and cytokine profiles, mucus production and proportion of T cells on the mesenteric lymph node (MLN) were evaluated. Warifteine (W) or methyl-warifteine (MW) alkaloids slightly improve diarrhea score independently of AFL and all treatments decreased the OVA-specific IgE levels. Stimulated mesenteric lymph node (MLN) cells in the presence of the alkaloids diminished the IL-12p70 levels independently of IFN-γ or IL-13 secretion. The alkaloids increased the number of Treg cells on MLN and reduced the number of eosinophils and mast cells as well as mucus production in the gut. Therefore, the alkaloids modulate the immune response in food allergy by increasing regulatory T cells in MLN independently of Th1 or Th2 profiles. PMID:23810408

  2. Studies on quantitative determination of total alkaloids and berberine in five origins of crude medicine "Sankezhen".

    Li, Luyang; Long, Weifang; Wan, Xiangluan; Ding, Qi; Zhang, Fei; Wan, Dingrong

    2015-02-01

    The roots of Berberis plants are widely used as a traditional Chinese medicine called "Sankezhen", having the activities of antibacterial and anti-inflammatory, and the ingredients are alkaloids. This work aims to study and compare the total alkaloids and individual alkaloid (berberine) contents in roots and stems from five origins of Berberis plants (Berberis soulieana Schneid., B. henryana Schneid., B. triacanthophora Fedde, B. gagnepainii Schneid. and B. bergmanniae Schneid.) and provides some references for resource and quality evaluation of the medicine. Acid dye colorimetry and high-performance liquid chromatography were used in the determination. The results showed that the contents for the total alkaloids in root and stem samples were in the range of 1.60-4.72% and 0.76-2.70%, while those of the berberine were 0.70-2.92% and 0.23-1.07%. With higher contents of the total alkaloids and berberine, the roots of B. soulieana, B. gagnepainii and B. bergmanniae were good sources of "Sankezhen". Meanwhile, the contents were also high in stems of the three plants, indicating that the stems were likely to be alternative sources of "Sankezhen" after further research. As the results of precision, stability and recovery tests shown, the methods were simple, rapid and reliable, and provided valuable basis for quality evaluation and new resource investigation of "Sankezhen". PMID:25013028

  3. Qualitative and quantitative analyses of alkaloids in Uncaria species by UPLC-ESI-Q-TOF/MS.

    Wang, Hai-Bo; Qi, Wen; Zhang, Lin; Yuan, Dan

    2014-01-01

    An ultra performance liquid chromatography (UPLC) coupled with quadrupole time-of-flight mass spectrometry (Q-TOF/MS) method has been optimized and established for the rapid analysis of the alkaloids in 22 samples originating from five Uncaria (U.) species. The accurate mass measurement of all the protonated molecules and subsequent fragment ions offers higher quality structural information for the interpretation of fragmentation pathways of the various groups of alkaloids. A total of 19 oxindole alkaloids, 16 indole alkaloids and 1 flavone were identified by co-chromatography of the sample extract with authentic standards, comparison of the retention time, characteristic molecular ions and fragment ions, or were tentatively identified by MS/MS determination. Moreover, the method was validated for the simultaneous quantification of the 24 components within 10.5 min. The potential chemical markers were identified for classification of the U. species samples by principal component analysis (PCA) and orthogonal partial least squared discriminant analysis (OPLS-DA). The results demonstrate the similarity and differences in alkaloids among the five U. species, which is helpful for the standardization and quality control of the medical materials of the U. Ramulus Cum Unics (URCU). Furthermore, with multivariate statistical analysis, the determined markers are more definite and useful for chemotaxonomy of the U. genus. PMID:25366313

  4. Alkaloid Accumulation in Catharanthus roseus Increases with Addition of Seawater Salts to the Nutrient Solution

    WANG Jing-Yan; LIU Zhao-Pu

    2010-01-01

    A sand culture experiment was conducted to determine the effects of different seawater (5% and 10%) treatments on plant growth,inorganic ions,indole alkaloid concentrations and yields of Catharanthus roseus,in an effort to increase the alkaloid yield by artificial cultivation.The total fresh and dry weights and tissue K+ concentrations decreased,but Na+ concentrations increased in the plant roots,stems and leaves of C.roseus under seawater stress as compared to the control.The concentrations and yields of vindoline,catharanthine,vinblastine and vincristine increased under seawater stress.The concentrations and yields of these alkaloids were higher in 5% seawater-treated plants than those in the 10% seawater-treated plants.Considering the industrial production,5% seawater treatments could reduce the cost of producing alkaloid.In the control plants,the highest alkaloid concentrations reached a peak at 100 days after planting,suggesting that plant harvest must be optimized in terms of growth duration.

  5. Tobacco alkaloids reduction by casings added/enzymatic hydrolysis treatments assessed through PLSR analysis.

    Lin, Shunshun; Zhang, Xiaoming; Song, Shiqing; Hayat, Khizar; Eric, Karangwa; Majeed, Hamid

    2016-03-01

    Based on encouraged development of potential reduced-exposure products (PREPs) by the US Institute of Medicine, casings (glucose and peptides) added treatments (CAT) and enzymatic (protease and xylanase) hydrolysis treatments (EHT) were developed to study their effect on alkaloids reduction in tobacco and cigarette mainstream smoke (MS) and further investigate the correlation between sensory attributes and alkaloids. Results showed that the developed treatments reduced nicotine by 14.5% and 24.4% in tobacco and cigarette MS, respectively, indicating that both CAT and EHT are potentially effective for developing lower-risk cigarettes. Sensory and electronic nose analysis confirmed the significant influence of treatments on sensory and cigarette MS components. PLSR analysis demonstrated that tobacco alkaloids were positively correlated to the off-taste, irritation and impact attributes, and negatively correlated to the aroma and softness attributes. Additionally, nicotine and anabasine from tobacco leaves positively contributed to the impact attribute, while they negatively contributed to the aroma attribute (P<0.05). Meanwhile, most alkaloids in cigarette MS positively contributed to the impact and irritation attributes (P<0.05). Hence, this study paved a way to better understand the correlation between tobacco alkaloids and sensory attributes. PMID:26739812

  6. Pyrrolizidine Alkaloid-Protein Adducts: Potential Non-invasive Biomarkers of Pyrrolizidine Alkaloid-Induced Liver Toxicity and Exposure.

    Xia, Qingsu; Zhao, Yuewei; Lin, Ge; Beland, Frederick A; Cai, Lining; Fu, Peter P

    2016-08-15

    Pyrrolizidine alkaloids (PAs) are phytochemicals present in hundreds of plant species from different families widely distributed in many geographical regions around the world. PA-containing plants are probably the most common type of poisonous plants affecting livestock, wildlife, and humans. There have been many large-scale human poisonings caused by the consumption of food contaminated with toxic PAs. PAs require metabolic activation to generate pyrrolic metabolites to exert their toxicity. In this study, we developed a novel method to quantify pyrrole-protein adducts present in the blood. This method involves the use of AgNO3 in acidic ethanol to cleave the thiol linkage of pyrrole-protein (DHP-protein) adducts, and the resulting 7,9-di-C2H5O-DHP is quantified by HPLC-ES-MS/MS multiple reaction monitoring analysis in the presence of a known quantity of isotopically labeled 7,9-di-C2D5O-DHP internal standard. Using this method, we determined that diester-type PAs administered to rats produced higher levels of DHP-protein adducts than other types of PAs. The results suggest that DHP-protein adducts can potentially serve as minimally invasive biomarkers of PA exposure. PMID:27388689

  7. Antibacterial Properties of Alkaloid Extracts from Callistemon citrinus and Vernonia adoensis against Staphylococcus aureus and Pseudomonas aeruginosa.

    Mabhiza, Donald; Chitemerere, Tariro; Mukanganyama, Stanley

    2016-01-01

    The development of new antibiotics from new chemical entities is becoming more and more expensive, time-consuming, and compounded by emerging strains that are drug resistant. Alkaloids are plant secondary metabolites which have been shown to have potent pharmacological activities. The effect of alkaloids from Callistemon citrinus and Vernonia adoensis leaves on bacterial growth and efflux pump activity was evaluated on Staphylococcus aureus and Pseudomonas aeruginosa. At a concentration of 1.67 mg/mL, the alkaloids inhibited bacterial growth with comparable effects to ampicillin, a standard antibiotic. The alkaloids from C. citrinus were the most potent against S. aureus with an MIC of 0.0025 mg/mL and MBC of 0.835 mg/mL. It was shown that effects on P. aeruginosa by both plant alkaloids were bacteriostatic. P. aeruginosa was most susceptible to drug efflux pump inhibition by C. citrinus alkaloids which caused an accumulation of Rhodamine 6G of 121% compared to the control. Thus, C. citrinus alkaloids showed antibacterial activity as well as inhibiting ATP-dependent transport of compounds across the cell membrane. These alkaloids may serve as potential courses of compounds that can act as lead compounds for the development of plant-based antibacterials and/or their adjunct compounds. PMID:26904285

  8. Antibacterial Properties of Alkaloid Extracts from Callistemon citrinus and Vernonia adoensis against Staphylococcus aureus and Pseudomonas aeruginosa

    Donald Mabhiza

    2016-01-01

    Full Text Available The development of new antibiotics from new chemical entities is becoming more and more expensive, time-consuming, and compounded by emerging strains that are drug resistant. Alkaloids are plant secondary metabolites which have been shown to have potent pharmacological activities. The effect of alkaloids from Callistemon citrinus and Vernonia adoensis leaves on bacterial growth and efflux pump activity was evaluated on Staphylococcus aureus and Pseudomonas aeruginosa. At a concentration of 1.67 mg/mL, the alkaloids inhibited bacterial growth with comparable effects to ampicillin, a standard antibiotic. The alkaloids from C. citrinus were the most potent against S. aureus with an MIC of 0.0025 mg/mL and MBC of 0.835 mg/mL. It was shown that effects on P. aeruginosa by both plant alkaloids were bacteriostatic. P. aeruginosa was most susceptible to drug efflux pump inhibition by C. citrinus alkaloids which caused an accumulation of Rhodamine 6G of 121% compared to the control. Thus, C. citrinus alkaloids showed antibacterial activity as well as inhibiting ATP-dependent transport of compounds across the cell membrane. These alkaloids may serve as potential courses of compounds that can act as lead compounds for the development of plant-based antibacterials and/or their adjunct compounds.

  9. An analysis of Sorghum halepense’s behavior in presence of tropane alkaloids from Datura stramonium extracts

    Butnariu Monica

    2012-07-01

    Full Text Available Abstract Background This study aimed to quantify the allelopathic potential of Datura stramonium (Jimson weed. Sorghum halepense (Johnsongrass tolerance was assessed by germinating, seed and growing seedlings, dosing of photo-synthesis pigments, followed by treatment with D. stramonium extract tropane alkaloids. Results Preliminary chemical analysis of the extracts showed the presence of alkaloids. The presence of alkaloids was confirmed through HPLC–UV system analysis. Various concentrations of analytic purity alkaloids had similar effects on germination and development of S. halepense’s root systems with those of extracts from of D. stramonium. Germination was not affected by any of the tested extracts, but growth was inhibited by the presence of tropane alkaloids. Extracts had effects at higher alkaloid concentrations. Seedlings of S. halepense developed toxicity symptoms in the presence of alkaloid extracts, but the occurrence of several chlorotic and necrotic areas was noticed in the flower extract biotest. Conclusions Results show that the tested species is sensitive to alkaloids in their growth environment. This research justifies the fact that aqueous extracts from D. stramonium are adequate to the situations in which S. halepense becomes damaging.

  10. Colonial Agro-Industrialism : Science, Industry and the State in the Dutch Golden Alkaloid Age, 1850-1950

    Roersch van der Hoogte, A.

    2015-01-01

    This thesis is about what I call the Dutch Golden Alkaloid Age between roughly the 1850s and 1950s. I follow the historical trajectory of the production and distribution of the anti-febrifuge cinchona bark tree (Cinchona officinalis Lin.) and its most powerful and therapeutically applied alkaloid in

  11. Effects of the ergot alkaloids dihydroergotamine, ergonovine, and ergotamine on growth of Escherichia coli O157:H7 in vitro

    A series of experiments were conducted to evaluate the effects of ergot alkaloids (dihydroergotamine, ergonovine, and ergotamine) on E. coli O157:H7 in both pure and mixed ruminal fluid culture. Alkaloids were added to solutions of E. coli O157:H7 strains 933 (pure and ruminal cultures) and 6058 (r...

  12. Calcium antagonist properties of the bisbenzylisoquinoline alkaloid cycleanine.

    Martínez, J A; Bello, A; Rubio, L L; Rodríguez, C; Galán, L; Caudales, E; Alvarez, J L

    1998-01-01

    The alkaloid cycleanine ([12aR-(12aR,24aR)]-2,3,12a,13,14,15,24,24a-octa hydro-5,6,17,18- tetramethoxy-1,13-dimethyl-8, 11:20,23-dietheno-1H,12H [1,10]dioxacyclooctadecino[2,3,4-ij:11,12,13-i'j']diisoquinolin e) was extracted from the bulbs of Stephania glabra (Roxb) Miers and its effects on cardiac and smooth muscle preparations were studied and compared to those of nifedipine (1,4-dihydro-2, 6-dimethyl-4-(2-nitrophenyl)-3,5-pyridine dicarboxylic acid dimethylesther). Cycleanine inhibited the KCl-induced contraction of rabbit aortic rings with higher potency than nifedipine. IC50s for cycleanine and nifedipine were 0.8 and 7.10(-9) M respectively. Cycleanine had minor effects on the norepinephrine-induced contraction of rabbit aortic rings. Cycleanine and nifedipine also depressed the contraction of rat ventricular preparations but with lower potency (IC50 = 3 and 0.03.10(-6) M respectively). Action potential duration of rat right ventricular strips was decreased by both compounds. L-type Ca-current (ICaL) of single rat ventricular cardiomyocytes was inhibited by cycleanine in a voltage- and frequency-dependent manner. With a higher potency nifedipine inhibited ICaL in a tonic and almost frequency-independent manner. The results suggest that cycleanine can act as a potent vascular selective Ca-antagonist. PMID:9565772

  13. Assessment of Mechanisms Involved in Antinociception Produced by the Alkaloid Caulerpine

    Luiz Henrique Agra Cavalcante-Silva

    2014-09-01

    Full Text Available In previous works we showed that oral administration of caulerpine, a bisindole alkaloid isolated from algae of the genus Caulerpa, produced antinociception when assessed in chemical and thermal models of nociception. In this study, we evaluated the possible mechanism of action of this alkaloid in mice, using the writhing test. The antinociceptive effect of caulerpine was not affected by intraperitoneal (i.p. pretreatment of mice with naloxone, flumazenil, l-arginine or atropine, thus discounting the involvement of the opioid, GABAergic, l-arginine-nitric oxide and (muscarinic cholinergic pathways, respectively. In contrast, i.p. pretreatment with yohimbine, an α2-adrenoceptor antagonist, or tropisetron, a 5-HT3 antagonist, significantly blocked caulerpine-induced antinociception. These results suggest that caulerpine exerts its antinociceptive effect in the writhing test via pathways involving α2-adrenoceptors and 5-HT3 receptors. In summary, this alkaloid could be of interest in the development of new dual-action analgesic drugs.

  14. Exposure to Ergot Alkaloids During Gestation Reduces Fetal Growth in Sheep

    Duckett, Susan; Pratt, Scott; Andrae, John

    2014-08-01

    Tall fescue [Lolium arundinaceum (Schreb.) Darbysh; Schedonorus phoenix (Scop.) Holub] is the primary cool season perennial grass in the eastern U.S. Most tall fescue contains an endophyte (Neotyphodium coenophialum), which produces ergot alkaloids that cause vasoconstriction and could restrict blood flow to the fetus in pregnant animals. The objective of this study was to examine fetal growth during maternal exposure to ergot alkaloids during gestation. Pregnant ewes (n = 16) were randomly assigned to one of two dietary treatments: 1) endophyte-infected (Neotyphodium coenophialum) tall fescue seed (E+; 0.8 ug of ergovaline /g diet DM) and 2) endophyte-free tall fescue seed (E-; 0.0 ug of ergovaline/g diet DM). Birth weight of lambs was reduced by 37% for E+ compared to E-. Organ and muscle weights were also lighter for E+ than E-. Exposure to ergot alkaloids in utero reduces fetal growth and muscle development.

  15. Large scale extraction of pyrrolizidine alkaloids from tansy ragwort (Senecio jacobaea).

    Craig, A M; Sheggeby, G; Wicks, C e

    1984-04-01

    A new technique of large-scale pyrrolizidine alkaloid (PA) extraction was developed in response to toxicity studies on food animals. Results of toxicity experiments on cattle vary from those on rodents (2); therefore, dose/response studies need to be germaine to the appropriate species. This new technique for extraction utilizes protonation of the ring nitrogen and partition of solvent to preferentially extract the alkaloid. The primary equipment used in the system we developed includes a large stainless-steel extraction/separation tank, holding tanks, and a 100-liter vacuum distillation system. From 23 kg of plant material of Senecio jacobaea , our system was able to produce 8-10 g of alkaloid per run, compared to the 3 g which we achieved using other extraction methods (2,4). Additional advantages of our system include a lower labor cost and the ability to recycle the organic solvent. PMID:6730295

  16. Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids

    Kettmann Viktor

    2007-07-01

    Full Text Available Abstract Roots and stem-bark of Mahonia aquifolium (Oregon grape (Berberidaceae are effectively used in the treatment of skin inflammatory conditions. In the present study, the effect of Mahonia aquifolium crude extract and its two representative alkaloid fractions containing protoberberine and bisbenzylisoquinoline (BBIQ alkaloids on activity of 12-lipoxygenase (12-LOX, was studied. The reactivity with 1,1-diphenyl-2-picryl-hydrazyl (DPPH, a free stable radical, was evaluated to elucidate the rate of possible lipid-derived radical scavenging in the mechanism of the enzyme inhibition. The results indicate that although the direct radical scavenging mechanism cannot be ruled out in the lipoxygenase inhibition by Mahonia aquifolium and its constituents, other mechanisms based on specific interaction between enzyme and alkaloids could play the critical role in the lipoxygenase inhibition rather than non-specific reactivity with free radicals.

  17. A QSAR Toxicity Study of a Series of Alkaloids with the Lycoctonine Skeleton

    Bakhtiyor F. Rasulev

    2004-12-01

    Full Text Available A QSAR toxicity analysis has been performed for a series of 19 alkaloids with the lycoctonine skeleton. GA-MLRA (Genetic Algorithm combined with Multiple Linear Regression Analysis technique was applied for the generation of two types of QSARs: first, models containing exclusively 3D-descriptors and second, models consisting of physicochemical descriptors. As expected, 3D-descriptor QSARs have better statistical fits. Physicochemical-descriptor containing models, that are in a good agreement with the mode of toxic action exerted by the alkaloids studied, have also been identified and discussed. In particular, TPSA (Topological Polar Surface Area and nC=O (number of –C(O– fragments parameters give the best statistically significant mono- and bidescriptor models (when combined with lipophilicity, MlogP confirming the importance of H-bonding capability of the alkaloids for binding at the receptor site.

  18. Main Alkaloids of Peganum harmala L. and Their Different Effects on Dicot and Monocot Crops

    Chi Zhang

    2013-02-01

    Full Text Available Alkaloids with allelopathic activity are not as well-known as other allelochemicals. Our study revealed that total alkaloids from seeds of the medicinal plant Peganum harmala L. possessed significant growth inhibitory effect on four treated plants, with dicot plants (lettuce and amaranth being more sensitive than the tested monocot plants (wheat and ryegrass. Further investigation led to the isolation of harmaline and harmine as the main active ingredients in the total alkaloids of P. harmala seeds. Harmaline exerted potent inhibitory effects on seedling growth of treated plants, especially dicots, inhibiting root elongation of lettuce and amaranth by 31% and 47% at a very low concentration (5 µg/mL, whereas harmine exhibited much weaker non-selective inhibitory effect on the plants. Considering the high yield and poor utilization of P. harmala in China, we anticipate that this plant could be exploited as an alternative weed management tool in the future.

  19. Cases of ergotism in livestock and associated ergot alkaloid concentrations in feed

    A. Morrie Craig

    2015-02-01

    Full Text Available Ergot-induced disease was known long before Biblical times and has been the root cause for countless human epidemics spanning from the early fourteenth century to the late sixteenth century. In contrast, many of these same ergot alkaloids have been utilized for their medicinal properties to mitigate migraine headaches and have had indications as anticarcinogens. Although ergot alkaloids have been used for centuries, basic pharmacokinetic data has not been documented for clinical disease. Consequently, a threshold dose and accurate dose-response data have yet to be established. Throughout the past several years, new detection techniques have emerged to detect these alkaloids at the parts per billion which have allowed for new efforts to be made with respect to determining threshold levels and making accurate clinical diagnoses. This perspectives article provides a critical initial step for establishing a uniform interpretation of ergot toxicosis from limited existing data.

  20. The inhibition activity of selected beta-carboline alkaloids on enzymes of acetylcholinesterase and butyrylcholinesterase.

    Krsková, Zuzana; Martin, Jan; Dusek, Jaroslav

    2011-06-01

    This thesis deals with testing of inhibition activity beta-carboline alkaloids on activity of enzymes acetylcholinesterase (ACHE) and butyrylcholinesterase (BUCHE) using test "Fast Blue B salt" at TLC desk and Ellman's test using spectrophotometer. It was also investigated how dimethylsulfoxide used as a solvent in combination with water affects activity of enzymes and alkaloids. Results show harmine in form of base and salt in water and in mixture of DMSO and water has the hightest inhibition activity on ACHE using eserine as reference substance. Harmalol in form of salt in water and harmine in form of base and salt in mixture of DMSO and water has the hightest activity on BUCHE. It was find out that DMSO considerably affects activity of enzymes and alkaloids. PMID:21838142

  1. Subcellular Localization of Enzymes Involved in Indole Alkaloid Biosynthesis in Catharanthus roseus1

    De Luca, Vincenzo; Cutler, Adrian J.

    1987-01-01

    The subcellular localization of enzymes involved in indole alkaloid biosynthesis in leaves of Catharanthus roseus has been investigated. Tryptophan decarboxylase and strictosidine synthase which together produce strictosidine, the first indole alkaloid of this pathway, are both cytoplasmic enzymes. S-Adenosyl-l-methionine: 16-methoxy-2,3-dihydro-3-hydroxytabersonine-N-methyltransferase which catalyses the third to last step in vindoline biosynthesis could be localized in the chloroplasts of Catharanthus leaves and is specifically associated with thylakoids. Acetyl-coenzyme-A-deacetylvindoline-O-acetyltransferase which catalyses the last step in vindoline biosynthesis could also be localized in the cytoplasm. The participation of the chloroplast in this pathway suggests that indole alkaloid intermediates enter and exit this compartment during the biosynthesis of vindoline. PMID:16665811

  2. Two new vinblastine-type N-oxide alkaloids from Catharanthus roseus.

    Zhang, Wei-Ku; Xu, Jie-Kun; Tian, Hai-Yan; Wang, Lei; Zhang, Xiao-Qi; Xiao, Xu-Zhi; Li, Ping; Ye, Wen-Cai

    2013-10-01

    Two new vinblastine-type N-oxide alkaloids, 17-desacetoxyvinblastine N'b-oxide (1) and 20'-deoxyvinblastine N'b-oxide (2), were isolated from the leaves of Catharanthus roseus. The structures of 1 and 2 were established by the analysis of their nuclear magnetic resonance and HR-ESI-MS spectroscopic data. All alkaloids were evaluated for their cytotoxic activities against the human hepatocellular carcinoma (HepG2) cell line, human colorectal carcinoma (Lovo) cell line and human breast carcinoma (MCF-7) cell line by the MTT method in vitro, respectively. The results showed that cytotoxic activities of alkaloids 1 and 2 exhibited moderate inhibitory activity on the proliferation of three cancer cells. PMID:23621523

  3. Isolation of Cells Specialized in Anticancer Alkaloid Metabolism by Fluorescence-Activated Cell Sorting.

    Carqueijeiro, Inês; Guimarães, Ana Luísa; Bettencourt, Sara; Martínez-Cortés, Teresa; Guedes, Joana G; Gardner, Rui; Lopes, Telma; Andrade, Cláudia; Bispo, Cláudia; Martins, Nuno Pimpão; Andrade, Paula; Valentão, Patrícia; Valente, Inês M; Rodrigues, José A; Duarte, Patrícia; Sottomayor, Mariana

    2016-08-01

    Plant specialized metabolism often presents a complex cell-specific compartmentation essential to accomplish the biosynthesis of valuable plant natural products. Hence, the disclosure and potential manipulation of such pathways may depend on the capacity to isolate and characterize specific cell types. Catharanthus roseus is the source of several medicinal terpenoid indole alkaloids, including the low-level anticancer vinblastine and vincristine, for which the late biosynthetic steps occur in specialized mesophyll cells called idioblasts. Here, the optical, fluorescence, and alkaloid-accumulating properties of C. roseus leaf idioblasts are characterized, and a methodology for the isolation of idioblast protoplasts by fluorescence-activated cell sorting is established, taking advantage of the distinctive autofluorescence of these cells. This achievement represents a crucial step for the development of differential omic strategies leading to the identification of candidate genes putatively involved in the biosynthesis, pathway regulation, and transmembrane transport leading to the anticancer alkaloids from C. roseus. PMID:27356972

  4. Development of transcriptomic resources for interrogating the biosynthesis of monoterpene indole alkaloids in medicinal plant species.

    Elsa Góngora-Castillo

    Full Text Available The natural diversity of plant metabolism has long been a source for human medicines. One group of plant-derived compounds, the monoterpene indole alkaloids (MIAs, includes well-documented therapeutic agents used in the treatment of cancer (vinblastine, vincristine, camptothecin, hypertension (reserpine, ajmalicine, malaria (quinine, and as analgesics (7-hydroxymitragynine. Our understanding of the biochemical pathways that synthesize these commercially relevant compounds is incomplete due in part to a lack of molecular, genetic, and genomic resources for the identification of the genes involved in these specialized metabolic pathways. To address these limitations, we generated large-scale transcriptome sequence and expression profiles for three species of Asterids that produce medicinally important MIAs: Camptotheca acuminata, Catharanthus roseus, and Rauvolfia serpentina. Using next generation sequencing technology, we sampled the transcriptomes of these species across a diverse set of developmental tissues, and in the case of C. roseus, in cultured cells and roots following elicitor treatment. Through an iterative assembly process, we generated robust transcriptome assemblies for all three species with a substantial number of the assembled transcripts being full or near-full length. The majority of transcripts had a related sequence in either UniRef100, the Arabidopsis thaliana predicted proteome, or the Pfam protein domain database; however, we also identified transcripts that lacked similarity with entries in either database and thereby lack a known function. Representation of known genes within the MIA biosynthetic pathway was robust. As a diverse set of tissues and treatments were surveyed, expression abundances of transcripts in the three species could be estimated to reveal transcripts associated with development and response to elicitor treatment. Together, these transcriptomes and expression abundance matrices provide a rich resource

  5. High-performance liquid chromatographic, capillary electrophoretic and capillary electrophoretic-electrospray ionisation mass spectrometric analysis of selected alkaloid groups.

    Stöckigt, Joachim; Sheludk, Yuri; Unger, Matthias; Gerasimenko, Irina; Warzecha, Heribert; Stöckigt, Detlef

    2002-08-16

    Systems for efficient separation of selected alkaloid groups by high performance liquid chromatography (HPLC), capillary electrophoresis (CE) and capillary electrophoresis coupled with electrospray ionisation mass spectrometry (CE-ESI-MS) are described. The optimized HPLC system was applied for the separation of 23 standard indole alkaloids as well as for qualitative and quantitative analyses of crude alkaloid extracts of Rauvolfia serpentina X Rhazya stricta hybrid cell cultures. The developed conditions for CE analysis proved to be efficient for separation of mixtures of standard indole and beta-carboline alkaloids. The described buffer system is also applicable in the combination of CE with electrospray ionisation mass spectrometry. This analytical technique allowed the separation and identification of components of standard indole alkaloid mixture as well as crude extracts of R. serpentina roots, R. serpentina cell suspension cultures and cortex of Aspidosperma quebracho-blanco. The influence of buffer composition and analyte structures on separation is discussed. PMID:12219932

  6. Variation in the expression of ergot alkaloids between individual tillers of perennial ryegrass

    Wade Jeffray Mace

    2014-11-01

    Full Text Available Epichloë fungal endophytes of cool season grasses are well known to produce a range of alkaloids of benefit to the host. Some of these compounds are advantageous to agriculture due to qualities that promote pasture persistence (e.g. the loline class of alkaloids confer insect protection while others are detrimental to the wellbeing of grazing livestock. The ergot alkaloids (e.g. ergovaline, produced in ryegrass and tall fescue associations, causes poor animal health in farming regions in many countries around the world and further study is required to improve our knowledge on this class of compounds. Here we present the application of a quantitative LC-MS/MS (liquid chromatography coupled to mass spectrometry method measuring eight ergot alkaloids (chanoclavine, agroclavine, elymoclavine, lysergol, lysergic acid, ergine, lysergyl alanine, ergovaline produced by endophyte infected grasses, to monitor levels in individual tillers from multiple plants of a single cultivar of perennial ryegrass (Lolium perenne cv. ‘Grasslands Samson’ infected with a common toxic endophyte strain (Epichloë festucae var. lolii. Monitoring the expression in individual tillers allows an estimation of the variability within a plant (between tillers as well as between plants.The study showed that there is significant variation in the concentration of the ergot alkaloids between tillers of a single plant, at or exceeding the level of variation observed between individual plants of a population. This result emphasizes the fundamental importance of robust experimental design and sampling procedures when alkaloid expression assessment is required and these need to be rigorously tailored to the hypothesis being tested.

  7. Variation in the expression of ergot alkaloids between individual tillers of perennial ryegrass

    Mace, Wade; Lunn, Kristy; Lloyd-West, Catherine

    2014-11-01

    Epichloë fungal endophytes of cool season grasses are well known to produce a range of alkaloids of benefit to the host. Some of these compounds are advantageous to agriculture due to qualities that promote pasture persistence (e.g. the loline class of alkaloids confer insect protection) while others are detrimental to the wellbeing of grazing livestock. The ergot alkaloids (e.g. ergovaline), produced in ryegrass and tall fescue associations, causes poor animal health in farming regions in many countries around the world and further study is required to improve our knowledge on this class of compounds. Here we present the application of a quantitative LC-MS/MS (liquid chromatography coupled to mass spectrometry) method measuring eight ergot alkaloids (chanoclavine, agroclavine, elymoclavine, lysergol, lysergic acid, ergine, lysergyl alanine, ergovaline) produced by endophyte infected grasses, to monitor levels in individual tillers from multiple plants of a single cultivar of perennial ryegrass (Lolium perenne cv. ‘Grasslands Samson’) infected with a common toxic endophyte strain (Epichloë festucae var. lolii). Monitoring the expression in individual tillers allows an estimation of the variability within a plant (between tillers) as well as between plants. The study showed that there is significant variation in the concentration of the ergot alkaloids between tillers of a single plant, at or exceeding the level of variation observed between individual plants of a population. This result emphasizes the fundamental importance of robust experimental design and sampling procedures when alkaloid expression assessment is required and these need to be rigorously tailored to the hypothesis being tested.

  8. Characterization of Alkaloid Uptake by Catharanthus roseus (L.) G. Don Protoplasts 1

    McCaskill, David G.; Martin, DeAndra L.; Scott, A. Ian

    1988-01-01

    The accumulation of alkaloids by protoplasts of Catharanthus roseus (L.) G. Don var. Little Bright Eye was studied to determine the specificity of uptake and the role of ion trapping in the storage of alkaloids. Accumulation of the indole alkaloids vindoline, ajmalicine, tabersonine, and vinblastine was found to be biphasic, with an initial burst of uptake followed by a slow, prolonged phase of accumulation. The concentration and pH dependence of the initial burst of uptake for vindoline suggested that uptake occurred by simple diffusion. Uptake of nicotine was monophasic, with a half life of 5.2 minutes. The accumulation ratio (Ci/Ce) for nicotine at steady state and for the initial burst of uptake for vindoline and ajmalicine suggested that accumulation was driven by the pH gradient between the vacuole and the external assay medium. The second, sustained phase of uptake of vindoline was sensitive to inhibition by either 20 millimolar NaN3 or 0.5 millimolar Cu2+. In azide-treated protoplasts, the uptake for vindoline conformed to the kinetics of simple diffusion, with a half life of 4 minutes. The second phase of uptake for ajmalicine, although sensitive to inhibition by Cu2+, was insensitive to inhibition by NaN3. The biphasic uptake of the indole alkaloids was not due to any significant metabolism. It is concluded that accumulation and storage of the indole alkaloids is due only partly to ion trapping of the alkaloids by the low pH of the vacuole lumen. In the case of vindoline, there appears to be a specific energy-requiring uptake that is not seen with nicotine (which is not endogenous to Catharanthus). Accumulation of ajmalicine appears to involve both ion trapping and an azide-insensitive component, which may be due to complexation with organic counterions and phenolics. PMID:16666154

  9. Potent Antifouling Marine Dihydroquinolin-2(1H)-one-Containing Alkaloids from the Gorgonian Coral-Derived Fungus Scopulariopsis sp.

    Shao, Chang Lun

    2015-04-02

    Marine biofouling has a major economic impact, especially when it occurs on ship hulls or aquaculture facilities. Since the International Maritime Organization (IMO) treaty to ban the application of organotin-based paints to ships went into effect in 2008, there is an urgent demand for the development of efficient and environmentally friendly antifouling agents. Marine microorganisms have proved to be a potential source of antifouling natural compounds. In this study, six dihydroquinolin-2-one-containing alkaloids, three monoterpenoids combined with a 4-phenyl-3,4-dihydroquinolin-2(1H)-one (1–3) and three 4-phenyl-3,4-dihydroquinolin-2(1H)-one alkaloids (4–6), were isolated from the gorgonian coral-derived fungus Scopulariopsis sp. collected in the South China Sea. These dihydroquinolin-2-one-containing alkaloids were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. All of them except 6 showed strong antifouling activity. Compounds 1 and 2 were discovered to be the most promising non-toxic antilarval settlement candidates. Especially, compound 1 is the strongest antifouling compound in nature until now which showed highly potent activity with picomolar level (EC50 17.5 pM) and a very safety and high therapeutic ratio (LC50/EC50 1200). This represents an effective non-toxic, anti-larval settlement structural class of promising antifouling lead compound. © 2015 Springer Science+Business Media New York

  10. Distribution of toxic alkaloids in tissues from three herbal medicine Aconitum species using laser micro-dissection, UHPLC-QTOF MS and LC-MS/MS techniques.

    Jaiswal, Yogini; Liang, Zhitao; Ho, Alan; Wong, LaiLai; Yong, Peng; Chen, Hubiao; Zhao, Zhongzhen

    2014-11-01

    Aconite poisoning continues to be a major type of poisoning caused by herbal drugs in many countries. Nevertheless, despite its toxic characteristics, aconite is used because of its valuable therapeutic benefits. The aim of the present study was to determine the distribution of toxic alkaloids in tissues of aconite roots through chemical profiling. Three species were studied, all being used in traditional Chinese Medicine (TCM) and traditional Indian medicine (Ayurveda), namely: Aconitum carmichaelii, Aconitum kusnezoffii and Aconitum heterophyllum. Laser micro-dissection was used for isolation of target microscopic tissues, such as the metaderm, cortex, xylem, pith, and phloem, with ultra-high performance liquid chromatography equipped with quadrupole time-of-flight mass spectrometry (UHPLC-QTOF MS) employed for detection of metabolites. Using a multi-targeted approach through auto and targeted LC-MS/MS, 48 known compounds were identified and the presence of aconitine, mesaconitine and hypaconitine that are the biomarkers of this plant was confirmed in the tissues. These results suggest that the three selected toxic alkaloids were exclusively found in A. carmichaelii and A. kusnezoffii. The most toxic components were found in large A. carmichaelii roots with more lateral root projections, and specifically in the metaderm, cork and vascular bundle tissues. The results from metabolite profiling were correlated with morphological features to predict the tissue specific distribution of toxic components and toxicity differences among the selected species. By careful exclusion of tissues having toxic diester diterpenoid alkaloids, the beneficial effects of aconite can still be retained and the frequency of toxicity occurrences can be greatly reduced. Knowledge of tissue-specific metabolite distribution can guide users and herbal drug manufacturers in prudent selection of relatively safer and therapeutically more effective parts of the root. The information provided from

  11. Unified Synthesis of 10-Oxygenated Lycopodium Alkaloids: Impact of C10-Stereochemistry on Reactivity.

    Saha, Mrinmoy; Li, Xin; Collett, Nathan D; Carter, Rich G

    2016-07-15

    The pronounced impact of the C10 stereochemistry on the successful construction of a polycyclic Lycopodium alkaloid scaffold has been explored. A wide range of reaction conditions and functionality were investigated to control a keto sulfone Michael addition to construct the C7-C12 linkage. An unexpected, overriding impact of the C10 stereochemistry in stereoselectivity and reaction rate in the Michael addition was observed. Furthermore, divergent reactivity of a conformationally accelerated, intramolecular Mannich cyclization based on the C10 stereochemistry was discovered. The successful execution of this synthetic route resulted in the total synthesis of all three known 10-oxygenated Lycopodium alkaloids: 10-hydroxylycopodine, paniculine, and deacetylpaniculine. PMID:27353498

  12. Biosynthesis of a defensive insect alkaloid: epilachnene from oleic acid and serine.

    Attygalle, A.B.; Blankespoor, C L; Eisner, T; Meinwald, J.

    1994-01-01

    The biosynthesis of the azamacrolide epilachnene by the coccinellid beetle Epilachna varivestis has been studied with 2H-labeled oleic acid, 2H-labeled L-serine, and 13C,15N-labeled L-serine. The incorporation of these precursors into epilachnene defines the origin of the alkaloid's entire carbon/nitrogen skeleton. GC/MS and GC/IR studies of alkaloid produced by Epilachna fed with deuteriated oleic acid show that oleic acid loses four carbon atoms from its carboxyl end during the biosynthesis...

  13. Antitrypanosomal alkaloids from Polyalthia suaveolens (Annonaceae): their effects on three selected glycolytic enzymes of Trypanosoma brucei.

    Ngantchou, Igor; Nyasse, Barthélemy; Denier, Colette; Blonski, Casimir; Hannaert, Véronique; Schneider, Bernd

    2010-06-15

    In continuation of our study on medicinal plants of Cameroon, stem barks of Polyalthia suaveolens were phytochemically studied. This investigation yielded a new indolosesquiterpene alkaloid, named polysin (1) and four hitherto known alkaloids (2-5). Polysin (1) appeared as a competitive reversible inhibitor (K(i)=10 microM) of phosphofructo kinase (PFK) of Trypanosoma brucei with respect to fructose-6-phosphate (K(i)/K(M)=0.05) and could be used in the design of new trypanocidal drugs. The other isolated compounds (2-5) also exhibited interesting inhibitory effects on selected glycolytic enzymes (PFK, glyceraldehyde-3-phosphate dehydrogenase and aldolase). PMID:20529682

  14. Activities and Effects of Ergot Alkaloids on Livestock Physiology and Production

    James L. Klotz

    2015-07-01

    Full Text Available Consumption of feedstuffs contaminated with ergot alkaloids has a broad impact on many different physiological mechanisms that alters the homeostasis of livestock. This change in homeostasis causes an increased sensitivity in livestock to perturbations in the ambient environment, resulting in an increased sensitivity to such stressors. This ultimately results in large financial losses in the form of production losses to livestock producers around the world. This review will focus on the underlying physiological mechanisms that are affected by ergot alkaloids that lead to decreases in livestock production.

  15. Activities and Effects of Ergot Alkaloids on Livestock Physiology and Production.

    Klotz, James L

    2015-08-01

    Consumption of feedstuffs contaminated with ergot alkaloids has a broad impact on many different physiological mechanisms that alters the homeostasis of livestock. This change in homeostasis causes an increased sensitivity in livestock to perturbations in the ambient environment, resulting in an increased sensitivity to such stressors. This ultimately results in large financial losses in the form of production losses to livestock producers around the world. This review will focus on the underlying physiological mechanisms that are affected by ergot alkaloids that lead to decreases in livestock production. PMID:26226000

  16. Gene Clusters for Insecticidal Loline Alkaloids in the Grass-Endophytic Fungus Neotyphodium uncinatum

    Spiering, Martin J.; Moon, Christina D; Wilkinson, Heather H.; Schardl, Christopher L

    2005-01-01

    Loline alkaloids are produced by mutualistic fungi symbiotic with grasses, and they protect the host plants from insects. Here we identify in the fungal symbiont, Neotyphodium uncinatum, two homologous gene clusters (LOL-1 and LOL-2) associated with loline-alkaloid production. Nine genes were identified in a 25-kb region of LOL-1 and designated (in order) lolF-1, lolC-1, lolD-1, lolO-1, lolA-1, lolU-1, lolP-1, lolT-1, and lolE-1. LOL-2 contained the homologs lolC-2 through lolE-2 in the same ...

  17. (--8-Oxohobartine a New İndole Alkaloid from Aristotelia chilensis (Mol. Stuntz

    Cristian Paz

    2015-08-01

    Full Text Available The fruit of Aristotelia chilensis is considered a “super fruit” due to its high concentration of polyphenols displaying exceptional antioxidant capacities ORAC. From maqui berries have been reported several anthocyanins and glycosylated flavonoids, those benefits increase the attention to restudy the plant. From the leaves of A. chilensis several indole alkaloids have been reported, we in addition to aristoteline, aristone, aristoquinoline and 3-fromylindole report the spectroscopic elucidation of 8-oxo-9-dehydromakomakine (1, hobartine (2 and a new alkaloid named 8-oxohobartine (3. Compound 1 to 3 did not show bactericidal activity against E. coli and S. aureus till 200 μg.

  18. Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis.

    Hohmann, Judit; Forgo, Peter; Molnár, Joseph; Wolfard, Krisztina; Molnár, Annamária; Thalhammer, Theresia; Máthé, Imre; Sharples, Derek

    2002-05-01

    Seven alkaloids were isolated from Sprekelia formosissima, and five from Hymenocallis x festalis. Tazettine, lycorine, haemanthidine and haemanthamine were evaluated for antiproliferative and multidrug resistance (mdr) reversing activity on mouse lymphoma cells. Lycorine, haemanthidine and haemanthamine displayed pronounced cell growth inhibitory activities against both drug-sensitive and drug-resistant cell lines, but did not significantly inhibit mdr-1 p-glycoprotein. Thus, the tested alkaloids are apparently not substrates for the mdr efflux pump. Assays for interactions with DNA and RNA revealed that the antiproliferative effects of lycorine and haemanthamine result from their complex formation with RNA. PMID:12058326

  19. Comparative Research on Alkaloid!fl Quantity among Clone Plants of Pinellia Ternate

    Jianhong Zeng; Zhengsong Peng

    2009-01-01

    Determine the quantity of Alkaloid among 15 clone plants of Pinellia ternate (Thunb.) Breit so as to offer theoretical basis on boosting the enrichment of effective elements in Pinellia ternate in plants!fl bodies.According to the principle of acid-dye colorimetry, adopt the method of chloroform extraction to determine under 417nm wavelength and make analysis of variance. Obtain favorable linear relationship (r=0.9989) and recovery (100.1%). RSD is 2.3%. The quantity of Alkaloid among the 15 ...

  20. Two New Koumine-Type Indole Alkaloids from Gelsemium elegans Benth.

    Huanhuan Gao

    2013-01-01

    Full Text Available Two new indole alkaloids, 21-oxokoumine (1 and furanokoumine (2, were isolated from the roots of Gelsemium elegans Benth together with three known compounds. The structures of the two novel compounds were elucidated by spectroscopic methods, including NMR, HR-ESI-MS, UV, IR, CD and molecular modeling. Compound 1 is the first instance of a koumine-type alkaloid with a carbonyl at the C-21 position, while compound 2 possesses a tetrahydrofuran ring located on C-20 and C-21.

  1. Design and synthesis of de novo cytotoxic alkaloids by mimicking the bioactive conformation of paclitaxel

    Sun, Liang; Veith, Jean M.; Pera, Paula; Bernacki, Ralph J.; Ojima, Iwao

    2010-01-01

    Novel paclitaxel-mimicking alkaloids were designed and synthesized based on a bioactive conformation of paclitaxel, i.e., REDOR-Taxol. The alkaloid 2 bearing a 5-7-6 tricyclic scaffold mimics REDOR-Taxol best among the compounds designed and was found to be the most potent compound against several drug-sensitive and drug-resistant human cancer cell lines. MD simulation study on the paclitaxel mimics 1 and 2 as well as REDOR-Taxol bound to the 1JFF tubulin structure was quite informative to ev...

  2. Relationships among Ergot Alkaloids, Cytochrome P450 Activity, and Beef Steer Growth

    Charles F. Rosenkrans

    2015-03-01

    Full Text Available Determining a grazing animal’s susceptibility to ergot alkaloids has been a research topic for decades. Our objective was to determine if the Promega™ P450-Glo assay could be used to indirectly detect ergot alkaloids or their metabolites in urine of steers. The first experiment validated the effects of ergot alkaloids [0, 20, and 40 μM of ergotamine (ET, dihydroergotamine (DHET, and ergonovine (EN] on human CYP3A4 using the P450-Glo assay (Promega™ V9800. With this assay, luminescence is directly proportional to CYP450 activity. Relative inhibition of in vitro cytochrome P450 activity was affected (P < 0.001 by an interaction between alkaloids and concentration. That interaction resulted in no concentration effect of EN, but within ET and DHET 20 and 40 µM concentrations inhibited CYP450 activity when compared with controls. In experiment 2, urine was collected from Angus-sired crossbred steers (n = 39; 216 ± 2.6 d of age; 203 ± 1.7 kg after grazing tall fescue pastures for 105 d. Non-diluted urine was added to the Promega™ P450-Glo assay, and observed inhibition (3.7 % ± 2.7 of control. Urine content of total ergot alkaloids (331.1 ng/mg of creatinine ± 325.7 was determined using enzyme linked immunosorbent assay. Urine inhibition of CYP450 activity and total alkaloids were correlated (r = -0.31; P < 0.05. Steers were genotyped at CYP450 single nucleotide polymorphism, C994G. Steer genotype affected (P < 0.03 inhibition of CYP450 activity by urine; heterozygous steers had the least amount of CYP450 inhibition suggesting that genotyping cattle may be a method of identifying animals that are susceptible to ergot alkaloids. Although, additional research is needed, we demonstrate that the Promega™ P450-Glo assay is sensitive to ergot alkaloids and urine from steers grazing tall fescue. With some refinement the P450-Glo assay has potential as a tool for screening cattle for their exposure to fescue toxins.

  3. Unlocking the diversity of alkaloids in Catharanthus roseus: nuclear localization suggests metabolic channeling in secondary metabolism.

    Stavrinides, Anna; Tatsis, Evangelos C; Foureau, Emilien; Caputi, Lorenzo; Kellner, Franziska; Courdavault, Vincent; O'Connor, Sarah E

    2015-03-19

    The extraordinary chemical diversity of the plant-derived monoterpene indole alkaloids, which include vinblastine, quinine, and strychnine, originates from a single biosynthetic intermediate, strictosidine aglycone. Here we report for the first time the cloning of a biosynthetic gene and characterization of the corresponding enzyme that acts at this crucial branchpoint. This enzyme, an alcohol dehydrogenase homolog, converts strictosidine aglycone to the heteroyohimbine-type alkaloid tetrahydroalstonine. We also demonstrate how this enzyme, which uses a highly reactive substrate, may interact with the upstream enzyme of the pathway. PMID:25772467

  4. Caavuranamide, a novel steroidal alkaloid from the ripe fruits of Solanum caavurana Vell. (Solanaceae)

    Vaz, Nelissa Pacheco; Santos, Erica L.; Marques, Francisco A.; Maia, Beatriz H.L.N. Sales, E-mail: noronha@ufpr.br [Departamento de Quimica, Universidade Federal do Parana, Centro Politecnico, Curitiba, PR (Brazil); Costa, Emmanoel V. [Departamento de Quimica, Universidade Federal de Sergipe, Sao Cristovao, SE (Brazil); Mikich, Sandra Bos [Laboratorio de Ecologia, Embrapa Florestas, Colombo, PR (Brazil); Braga, Raquel M. [Instituto de Quimica, Universidade Estadual de Campinas, SP (Brazil); Delarmelina, Camila; Duarte, Marta C.T. [Divisao de Microbiologia, Centro Pluridisciplinar de Pesquisas Quimicas Biologicas e Agricolas (CPQBA), Universidade Estadual de Campinas, SP (Brazil); Duarte, Marta C.T.; Ruiz, Ana Lucia T.G.; Souza, Vanessa H.S.; Carvalho, Joao E. de [Divisa de Farmacologia e Toxicologia, Centro Pluridisciplinar de Pesquisas Quimicas Biologicas e Agricolas (CPQBA), Universidade Estadual de Campinas, SP (Brazil)

    2012-07-01

    Phytochemical investigation of the ripe fruits of Solanum caavurana Vell. (Solanaceae) afforded a novel steroidal alkaloid with spirosolane-type skeleton, named as caavuranamide, together with the alkaloids 4-tomatiden-3-one and 5{alpha}-tomatidan-3-one. Their structures were elucidated on the basis of spectroscopic methods. The antiproliferative and antimicrobial activities for the ethanolic extract, sub-fractions obtained from partition and acid-base treatment were also evaluated. Caavuranamide showed antibacterial activity similar to the chloramphenicol positive control against Rhodococcus equi. (author)

  5. Total Synthesis of the Strychnos Alkaloid (+)-Minfiensine: Tandem Enantioselective Intramolecular Heck–Iminium Ion Cyclization

    Dounay, Amy B.; Humphreys, Philip G.; Overman, Larry E.; Wrobleski, Aaron D.

    2008-01-01

    A 1,2,3,4-tetrahydro-9a,4a-(iminoethano)-9H-carbazole (4) is a central structural feature of the Strychnos alkaloid minfiensine (1) and akuammiline alkaloids such as vincorine (5) and echitamine (6). A cascade catalytic asymmetric Heck-iminium cyclization was developed that rapidly provides 3,4-dihydro-9a,4a-(iminoethano)-9H-carbazoles in high enantiomeric purity. Two sequences were developed for advancing 3,4-dihydro-9a,4a-(iminoethano)-9H-carbazole 27 to (+)-minfiensine. In our first-genera...

  6. Scientific Opinion on Ergot alkaloids in food and feed

    EFSA Panel on Contaminants in the Food Chain

    2012-07-01

    Full Text Available

    The European Food Safety Authority (EFSA was asked by the European Commission to deliver a scientific opinion on ergot alkaloids (EAs in food and feed. EAs are produced by several members within the fungal orders of Hypocreales and Eurotiales. In Europe, Claviceps purpurea is the most widespread Claviceps species within the Hypocreales. A total of 20 558 analytical results for EAs in 1 716 food, 496 feed and 67 unprocessed grain samples were considered in this opinion. Based on the EAs identified in sclerotia of C. purpurea, and recent literature data, the EFSA Panel on Contaminants in the Food Chain (CONTAM Panel based its risk assessment on the main C. purpurea EAs, namely ergometrine, ergotamine, ergosine, ergocristine, ergocryptine (which is a mixture of α- and β- isomers, ergocornine, and the corresponding –inine epimers. The CONTAM Panel performed estimates of both chronic and acute exposure for various age groups across European countries. A BMDL10 of 0.33 mg/kg b.w. per day was calculated for the incidence of tail muscular atrophy in a 13-week rat feeding study of ergotamine. This effect was considered representative of the vasoconstrictive effects of EAs and provided a suitable reference point for establishment of a group acute reference dose of 1 μg/kg body weight (b.w. and a group tolerable daily intake of 0.6 μg/kg b.w. per day. The Panel concluded that whilst the available data do not indicate a concern for any population subgroup, the dietary exposure estimates relate to a limited number of food groups and a possible unknown contribution from other foods cannot be discounted. Estimates of exposure for livestock based on example diets and levels of EAs in cereal grains reported suggest that under normal conditions the risk of toxicosis is low.

  7. Characterization of the variation in the imidazole alkaloid profile of Pilocarpus microphyllus in different seasons and parts of the plant by electrospray ionization mass spectrometry fingerprinting and identification of novel alkaloids by tandem mass spectrometry.

    Abreu, Iika N; Mazzafera, Paulo; Eberlin, Marcos N; Zullo, Marco António T; Sawaya, Alexandra C H F

    2007-01-01

    Pilocarpus microphyllus (Rutaceae), popularly known as jaborandi, is the only commercial source of an imidazole alkaloid named pilocarpine. In the present study, the variation in the profile of imidazole alkaloids in different seasons and in different parts of the P. microphyllus plant during the summer was analyzed by electrospray ionization mass spectrometry in the positive ion mode [ESI(+)-MS]. The fingerprints of these extracts repeatedly presented similar ions which were mass-selected and studied by tandem mass spectrometry (ESI-MS/MS and ESI-MS/MS/MS) and high-resolution mass spectrometry, resulting in the characterization of eight imidazole alkaloids. The data from the ESI(+)-MS fingerprints were analyzed by principal component analysis (PCA), showing that pilocarpine was present mainly in the summer, whereas in the autumn mainly pilosine and winter anhydropilosine were found. Three alkaloids, reported for the first time in extracts of P. microphyllus, were found. Analysis of the distribution of alkaloids in different parts of the plant during the summer showed that, although pilocarpine was present throughout the plant, 13-nor-8(11)-dihydropilocarpine was found mainly in the stem, pilosine and anhydropilosine were present mainly in the intermediary leaves, and the three new alkaloids were mainly found in the leaflets and petioles. Based on the dissociation patterns of these alkaloids, we observed that there were three structurally related groups of alkaloids differing in their distribution in the plant tissues and responding differently to seasonal variations. These results also indicate that these three groups of alkaloids could belong to intermediate, parallel or competitive pathways for pilocarpine formation biosynthesis. PMID:17330216

  8. Efficient synthesis of the C/D rings of atisine-type C20-diterpenoid alkaloids

    De Lin Chen; Feng Peng Wang

    2012-01-01

    A bicyclo[2.2.2]octane C/D ring system,with a lactonic ring at C-8 and C-9,of the atisine-type C20-diterpenoid alkaloids,was successfully synthesized,using an oxidative dearomatization/intramolecular Diels-Alder reaction.

  9. Berbanine: a new isoquinoline-isoquinolone alkaloid from Berberis vulgaris (Berberidaceae)

    Hošťálková, A.; Novák, Z.; Pour, M.; Jirošová, Anna; Opletal, L.; Kuneš, J.; Cahlíková, L.

    2013-01-01

    Roč. 8, č. 4 (2013), s. 441-442. ISSN 1934-578X Institutional support: RVO:61388963 Keywords : Berberis vulgaris * Berberidaceae * alkaloid * isoquinoline-isoquinolone dimer * berbanine Subject RIV: CC - Organic Chemistry Impact factor: 0.924, year: 2013

  10. Two new β-carboline-type alkaloids from Stellaria dichotoma var.lanceolata

    Jian Guang Luo; Li Hua Cao; Ling Yi Kong

    2012-01-01

    Two new β-carboline-type alkaloids,dichotomine K (1) and dichotomine L (2),were isolated from the roots of Chinese medicinal plant Stellaria dichotoma L.var.lanceolata Bge.Structures of 1 and 2 were determined on the basis of chemical and spectroscopic means.

  11. Sequestration and possible role of dietary alkaloids in the sponge-feeding mollusk Tylodina perversa.

    Thoms, C; Ebel, R; Proksch, P

    2006-01-01

    Opisthobranchs of the genus Tylodina are found at exceedingly distant geographical regions in the marine environment but are always associated with sponges of the order Verongida (e.g., Aplysina species) which serve as prey for these gastropods. We investigated the chemical ecology of the Mediterranean species T. perversa that commonly feeds on A. aerophoba. The gastropod sequesters a set of sponge-derived brominated isoxazoline alkaloids which are accumulated in the mantle and egg masses and are furthermore exuded as part of the mucus when the animal is molested. Based on the documented feeding deterrent properties of the sponge alkaloids against fish, it is speculated that the sequestered sponge alkaloids serve also as a defense for T. perversa. Interestingly, specimens of T. perversa that were either collected while feeding on A. aerophoba or had been kept on these sponges under controlled conditions for several weeks almost always contained the brominated alkaloid aerothionin, which is not detected in A. aerophoba but occurs in the sibling species A. cavernicola instead. The latter sponge is also accepted as a food source by the gastropod, at least under experimental conditions. The possible origin of aerothionin in T. perversa is discussed. PMID:17153347

  12. Study on adsorptive separation of berberine alkaloids in Coptis Japonica makino by molecular dynamics simulation

    Wang, D.; Sakoda, A.; Suzuki, M. [University of Tokyo, Tokyo (Japan). Institure of Industrial Science

    1997-12-01

    A calculation approach to discuss the solvent effect on liquid phase adsorption has been developed by using the molecular dynamics simulation method and solvophobic theory. The distinctive feature of the approach is that the calculations of the potential energy changes related to the solvent effect can be achieved on the basis of the molecular structure only, without using any experimental physicochemical property of the solute. This approach is applied to adsorption of five berberine alkaloids contained in Coptis japonica Makino onto the graphite surface from six solvents. Detailed analysis of the potential energy changes due to the solvent effect derived by molecular dynamics calculations yields an outline of the relative adsorption capacities of the alkaloids. Furthermore, the prediction of the preferential adsorption of alkaloids onto a graphite surface from the liquid phase and the eluent strength of solvents for desorption of the alkaloids from graphite surface were obtained. The calculated results are in good agreement with experimental data. 25 refs., 11 figs., 4 tabs.

  13. Root damage and aboveground herbivory change concentration and composition of pyrrolizidine alkaloids of Senecio jacobaea

    Hol, W.H.G.; Macel, M.; Van Veen, J.A.; van der Meijden, E.

    2004-01-01

    Thus far not many studies focussed on how herbivory in one plant part affects plant defence in the other. The effects of root damage and a leaf-feeding herbivore (Mamestra brassicae) on pyrrolizidine alkaloid (PA) levels of Senecio jacobaea were investigated in a controlled environment. Three cloned

  14. Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)

    Kagiyama, Ippei; Kato, Hikaru; Nehira, Tatsuo;

    2016-01-01

    Seven new prenylated indole alkaloids, taichunamides A–G, were isolated from the fungus Aspergillus taichungensis (IBT 19404). Taichunamides A and B contained an azetidine and 4‐pyridone units, respectively, and are likely biosynthesized from notoamide S via (+)‐6‐epi‐stephacidin A. Taichunamides...

  15. Extraction Optimization of Tinospora cordifolia and Assessment of the Anticancer Activity of Its Alkaloid Palmatine

    Huma Ali

    2013-01-01

    Full Text Available Objective. To optimize the conditions for the extraction of alkaloid palmatine from Tinospora cordifolia by using response surface methodology (RSM and study its anticancerous property against 7,12-dimethylbenz(aanthracene (DMBA induced skin carcinogenesis in Swiss albino mice. Methods. The effect of three independent variables, namely, extraction temperature, time, and cycles was investigated by using central composite design. A single topical application of DMBA (100 μg/100 μL of acetone, followed 2 weeks later by repeated application of croton oil (1% in acetone three times a week for 16 weeks, exhibited 100 percent tumor incidence (Group 2. Results. The highest yield of alkaloid from Tinospora cordifolia could be achieved at 16 hours of extraction time under 40°C with 4 extraction cycles. Alkaloid administration significantly decreases tumor size, number, and the activity of serum enzyme when compared with the control (Group 2. In addition, depleted levels of reduced glutathione (GSH, superoxide dismutase (SOD, and catalase and increased DNA damage were restored in palmatine treated groups. Conclusion. The data of the present study clearly indicate the anticancer potential of palmatine alkaloid in DMBA induced skin cancer model in mice.

  16. Persistence of echimidine, a hepatotoxic pyrrolizidine alkaloid, from honey into mead

    Honey produced by bees foraging on Echium plantagineum is known to contain dehydropyrrolizidine alkaloids characteristic of the plant. Following a prolific growth of E. plantagineum in the wake of Australian bushfires, two samples of mead, a fermented drink made from honey, and the honey used to pre...

  17. Effects of solar UV radiation on alkaloid production in Erythroxylum novogranatense var. novogranatense

    Cocaine-producing species of Erythroxylum have been cultivated in South America for centuries, yet little is know of environmental effects on alkaloid production in these species. Given the high incidence of UV radiation in the equatorial and high altitude environments in which cocaine-producing sp...

  18. Plant alkaloids that cause developmental defects through the disruption of cholinergic neurotransmission.

    Green, Benedict T; Lee, Stephen T; Welch, Kevin D; Panter, Kip E

    2013-12-01

    The exposure of a developing embryo or fetus to alkaloids from plants, plant products, or plant extracts has the potential to cause developmental defects in humans and animals. These defects may have multiple causes, but those induced by piperidine and quinolizidine alkaloids arise from the inhibition of fetal movement and are generally referred to as multiple congenital contracture-type deformities. These skeletal deformities include arthrogyrposis, kyposis, lordosis, scoliosis, and torticollis, associated secondary defects, and cleft palate. Structure-function studies have shown that plant alkaloids with a piperidine ring and a minimum of a three-carbon side-chain α to the piperidine nitrogen are teratogenic. Further studies determined that an unsaturation in the piperidine ring, as occurs in gamma coniceine, or anabaseine, enhances the toxic and teratogenic activity, whereas the N-methyl derivatives are less potent. Enantiomers of the piperidine teratogens, coniine, ammodendrine, and anabasine, also exhibit differences in biological activity, as shown in cell culture studies, suggesting variability in the activity due to the optical rotation at the chiral center of these stereoisomers. In this article, we review the molecular mechanism at the nicotinic pharmacophore and biological activities, as it is currently understood, of a group of piperidine and quinolizidine alkaloid teratogens that impart a series of flexure-type skeletal defects and cleft palate in animals. PMID:24339035

  19. Seasonal Variation of Bioactive Alkaloid Contents in Macleaya microcarpa (Maxim. Fedde

    Jana Gregorová

    2011-04-01

    Full Text Available Macleaya microcarpa (Maxim. Fedde belongs to the genus Macleaya, family Papaveraceae. Together with the better known and more frequently studied species M. cordata (Willd. R. Br. it is a main source of quaternary benzo[c]phenanthridine alkaloids. Using HPLC we determined the content of eight isoquinoline alkaloids in the aerial and underground parts of 1-, 2-, 12- and 13-year old plants and followed their changes during the vegetative period. The dominant alkaloid of all samples collected in the end of this period was allocryptopine (3.8–13.6 mg/g for aerial parts, 24.2–48.9 mg/g for underground parts. Chelerythrine, sanguinarine and protopine were also present in both parts of the plant. Additionally, measurable concentrations of chelilutine (CL, chelirubine (CR, macarpine (MA and sanguirubine (SR were detected in underground parts. The most important finding was that contents of CR, CL, SR and MA in the 12- and 13-year old plant roots were significantly higher (approximately 3-fold for CR, 6-fold for CL, 5-fold for SR, and at least 14-fold for MA than in 1- or 2-year old plants. The proportion of individual alkaloids in aerial and underground parts thus changed significantly during the vegetative period.

  20. Currencies of mutualisms: Sources of alkaloid genes in vertically transmitted epichloae

    The epichloae (Epichloë and Neotyphodium species), a monophyletic group of fungi in the family Clavicipitaceae, are systemic symbionts of cool-season grasses (Poaceae subfamily Poöideae). Most epichloae are vertically transmitted in seeds (endophytes), and most produce alkaloids that attack nervous ...

  1. Heliotropium europaeum Poisoning in Cattle and Analysis of its Pyrrolizidine Alkaloid Profile

    Shimshoni, J.A.; Mulder, P.P.J.; Bouznach, A.; Edery, N.; Pasval, I.; Barel, S.; Khaliq, M.A.E.; Perl, S.

    2015-01-01

    Pyrrolizidine alkaloids (PAs) are carcinogenic and genotoxic phytochemicals found exclusively in angiosperms. The ingestion of PA-containing plants often results in acute and chronic toxicities in man and livestock, targeting mainly the liver. During February 2014, a herd of 15-18-month-old mixed-br

  2. Analysis of several irdoid and indole precursors of terpenoid indole alkaloids with a single HPLC run

    Dagnino, Denise; Schripsema, Jan; Verpoorte, Robert

    1996-01-01

    An isocratic HPLC system is described which allows the separation of the iridoid and indole precursors of terpenoid indole alkaloids, which are present in a single crude extract. The system consists of a column of LiChrospher 60 RP select B 5 my, 250x4 mm (Merck) with an eluent of 1 % formic acid...

  3. Doppler ultrasonography for evaluating vascular responses to ergopeptine alkaloids in livestock

    Ergot alkaloids are produced by non-spore producing fungal endophytes that infect certain species of grasses, most notably tall fescue [Lolium arundinaceum (Schreb.) Darbysh.] and perennial ryegrass (Lolium perenne L.), and the spore producing Claviceps spp. that infect seed heads of certain grasses...

  4. Crinane Alkaloids of the Amaryllidaceae with Cytotoxic Effects in Human Cervical Adenocarcinoma (HeLa) Cells

    Nair, J. J.; Rárová, L.; Strnad, Miroslav; Bastida, J.; Cheesman, L.; van Staden, J.

    2014-01-01

    Roč. 9, č. 4 (2014), s. 461-466. ISSN 1934-578X R&D Projects: GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : Alkaloid * Amaryllidaceae * Apoptosis Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 0.906, year: 2014

  5. A new antitumor isoquinoline alkaloid from the marine nudibranch Jorunna funebris

    Fontana, A.; Cavaliere, P.; Wahidullah, S.; Naik, C.G.; Cimino, G.

    A new dimeric isoquinoline alkaloid, jorumycin (3), has been isolated from the skin and the mucus of the Pacific nudibranch Jorunna funebris. The structure has been fully elucidated on the grounds of ESMS data and of an extensive 2D NMR analysis...

  6. A novel norsesquiterpene alkaloid from the mushroom-forming fungus Flammulina velutipes

    Zhen-Yu Xu; Zhi-Ang Wu; Kai-Shun Bi

    2013-01-01

    A new norsesquiterpe alkaloid (1) was isolated from the solid culture of mushroom-forming fungus Flammulina velutipes fermented on rice.The structure of 1 was elucidated by spectroscopic methods.The absolute configuration of C-1 in 1 was determined using the circular dichroism data of their [Rh2(OCOCF3)4] complex.

  7. Signaling Pathways Used by Ergot Alkaloids to Inhibit Bovine Sperm Motility

    Ergot alkaloids exert their toxic or pharmaceutical effects through membrane receptor-mediated activities. This study investigated the signaling pathways involved in the in vitro inhibitory effects of both ergotamine (ET) and dihydroergotamine (DEHT) on bovine sperm motility using specific inhibitor...

  8. Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

    Louis P. Sandjo

    2015-09-01

    Full Text Available This review focuses on pyridoacridine-related metabolites as one biologically interesting group of alkaloids identified from marine sources. They are produced by marine sponges, ascidians and tunicates, and they are structurally comprised of four to eight fused rings including heterocycles. Acridine, acridone, dihydroacridine, and quinolone cores are features regularly found in these alkaloid skeletons. The lack of hydrogen atoms next to quaternary carbon atoms for two or three rings makes the chemical shift assignment a difficult task. In this regard, one of the aims of this review is the compilation of previously reported, pyridoacridine 13C NMR data. Observations have been made on the delocalization of electrons and the presence of some functional groups that lead to changes in the chemical shift of some carbon resonances. The lack of mass spectra information for these alkaloids due to the compactness of their structures is further discussed. Moreover, the biosynthetic pathways of some of these metabolites have been shown since they could inspire biomimetic synthesis. The synthesis routes used to prepare members of these marine alkaloids (as well as their analogues, which are synthesized for biological purposes are also discussed. Pyridoacridines were found to have a large spectrum of bioactivity and this review highlights and compares the pharmacophores that are responsible for the observed bioactivity.

  9. Two New Alkaloids from a Marine-derived Fungus Neosartorya fischeri

    Bin Wu

    2015-04-01

    Full Text Available Investigation of EtOAc extract from the fermentation broth of the fungus Neosartorya fischeri led to the isolation of two novel alkaloids and one known compound with antitumor activity against HL-60 cell lines. Their structures were elucidated mainly by NMR and HR-TOF-MS, as well as on comparison with the reported data.

  10. Seasonal variation in pyrrolizidine alkaloid concentration and plant development in Senecio madagascariensis poir. (Asteraceae) in Brazil

    This chapter presents the results of studies conducted in the municipality of Eldorado do Sul, State of Rio Grande do Sul, Brazil, in July and October 2007 and January and May 2008 to measure the pyrrolizidine alkaloid (PA) concentrations of S. madagascariensis plant material (including leaves, flow...

  11. Molecular docking and pharmacogenomics of alkaloids and their monomeric precursors; vindoline and catharanthine

    Sertel, Serkan; Fu, Yujie; Zu, Yuangang; Rebacz, Blanka; Konkimalla, Badireenath; Plinkert, Peter K.; Krämer, Alwin; Gertsch, Jürg; Efferth, Thomas

    2011-01-01

    Abstract Vinblastine and vincristine are dimeric indole alkaloids derived from Catharanthus roseus (formerly: Vinca rosea). Their monomeric precursor molecules are vindoline and catharanthine. While vinblastine and vincristine are well-known mitotic spindle poisons, not much is known about vindoline and catharanthine. Vindoline and catharanthine showed weak cytotoxicity, while vinblastine, vincristine, and the semisynthetic vindesine and vinorelbine revealed high cytotoxicity towar...

  12. Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora.

    Koyama, Koichiro; Hirasawa, Yusuke; Hosoya, Takahiro; Hoe, Teh Chin; Chan, Kit-Lam; Morita, Hiroshi

    2010-06-15

    Eight new indole alkaloids, alpneumines A-H (1-8) were isolated from the Malaysian Alstonia pneumatophora (Apocynaceae) and their structures were determined by MS and 2D NMR spectroscopic methods. Alpneumines E and G (5 and 7), vincamine, and apovincamine showed anti-melanogenesis in B16 mouse melanoma cells. PMID:20576577

  13. Radiation Processed Carrageenan Improves Plant Growth, Physiological Activities, and Alkaloids Production in Catharanthus roseus L.

    M. Naeem

    2015-01-01

    Full Text Available Catharanthus roseus (L. G. Don (Apocynaceae is a medicinal plant that produces indole alkaloids used in cancer chemotherapy. Commercially important antineoplastic alkaloids, namely, vinblastine and vincristine, are mainly present in the leaves of C. roseus. Gamma-rays irradiated carrageenan (ICR has been proven as plant growth promoting substance for a number of medicinal and agricultural plants. Considering the importance of ICR as a promoter of plant growth and alkaloids production in C. roseus, a pot experiment was carried out to explore the effect of ICR on the plant growth, physiological activities, and production of anticancer alkaloids in C. roseus at 120 and 150 days after planting (DAP. Foliar application of ICR (at 0, 20, 40, 60, 80, and 100 mg L−1 significantly improved the performance of C. roseus. 80 mg L−1 of ICR enhanced the leaf yield by 29.2 and 35.4% and the herbage yield by 32.5 and 37.4% at 120 and 150 DAP, respectively, over the control. The spray of ICR at 80 mg L−1 increased the yield of vinblastine by 64.3 and 65.0% and of vincristine by 75.5 and 77.0% at 120 and 150 DAP, respectively, as compared to the control.

  14. A virus-induced gene silencing approach to understanding alkaloid metabolism in Catharanthus roseus

    Liscombe, David K.; O’Connor, Sarah E.

    2011-01-01

    The anticancer agents vinblastine and vincristine are bisindole alkaloids derived from coupling vindoline and catharanthine, monoterpenoid indole alkaloids produced exclusively by Madagascar periwinkle (Catharanthus roseus) plants. Industrial production of vinblastine and vincristine currently relies on isolation from C. roseus leaves, a process that affords these compounds in 0.0003–0.01% yields. Metabolic engineering efforts to improve alkaloid content or provide alternative sources of the bisindole alkaloids ultimately rely on the isolation and characterization of the genes involved. Several vindoline biosynthetic genes have been isolated, and the cellular and subcellular organization of the corresponding enzymes has been well studied. However, due to the leaf-specific localization of vindoline biosynthesis, and the lack of production of this precursor in cell suspension and hairy root cultures of C. roseus, further elucidation of this pathway demands the development of reverse genetics approaches to assay gene function in planta. The bipartite pTRV vector system is a Tobacco Rattle Virus-based virus-induced gene silencing (VIGS) platform that has provided efficient and effective means to assay gene function in diverse plant systems. We have developed a VIGS method to investigate gene function in C. roseus plants using the pTRV vector system. The utility of this approach in understanding gene function in C. roseus leaves is demonstrated by silencing known vindoline biosynthetic genes previously characterized in vitro. PMID:21802100

  15. A vacuolar class III peroxidase and the metabolism of anticancer indole alkaloids in Catharanthus roseus

    Duarte, Patrícia; Figueiredo, Raquel; Ros Barceló, Alfonso

    2008-01-01

    Plants possess a unique metabolic diversity commonly designated as secondary metabolism, of which the anticancer alkaloids from Catharanthus roseus are among the most studied. Recently, in a classical function-to-protein-to-gene approach, we have characterized the main class III peroxidase (Prx) expressed in C. roseus leaves, CrPrx1, implicated in a key biosynthetic step of the anticancer alkaloids. We have shown the vacuolar sorting determination of CrPrx1 using GFP fusions and we have obtained further evidence supporting the role of this enzyme in alkaloid biosynthesis, indicating the potential of CrPrx1 as a molecular tool for the manipulation of alkaloid metabolism. Here, we discuss how plant cells may regulate Prx reactions. In fact, Prxs form a large multigenic family whose members accept a broad range of substrates and, in their two subcellular localizations, the cell wall and the vacuole, Prxs co-locate with a large variety of secondary metabolites which can be accepted as substrates. How then, are Prx reactions regulated? Localization data obtained in our lab suggest that arabinogalactan proteins (AGPs) and Prxs may be associated in membrane microdomains, evocative of lipid rafts. Whether plasma membrane and/or tonoplast microcompartmentation involve AGPs and Prxs and whether this enables metabolic channeling determining Prx substrate selection are challenging questions ahead. PMID:19704535

  16. Cyclopamine and related steroidal alkaloid teratogens: their occurrence, structural relationship, and biologic effects.

    Keeler, R F

    1978-10-01

    A spontaneous congenital deformity is produced in lambs whose dams consume Veratrum californicum on the 14th day of gestation. The deformity is generally expressed as cyclopia, cebocephaly, anophthalmia, or microphthalmia. This teratogenic effect is produced by certain steroidal alkaloid teratogens from the plant - most notably the compound cyclopamine. Cyclopamine is a C-nor-D-homo steroid with fused furanopiperidine rings E and F at right angles to the plane of the steroid because of spiro attachment at C-17 of the steroid. Among veratrum alkaloids, only those with an intact furan ring E were teratogenic in sheep, whereas those in which the peperidine ring is not rigidly positioned at right angles to the steroid were not. Many ruminants and laboratory animals are susceptible to the teratogen. It has wide species and tissue specificity and appears to have a direct effect on the embryo, not as a consequence of metabolic alteration of its structure nor as an indirect effect through a maternal influence. Other plant sources, notably potatoes, tomatoes, and eggplant contain related spirosolane steroidal alkaloids. Among naturally occurring spirosolanes, solasodine is teratogenic in hamsters, but neither tomatidine not diosgenin, the non-nitrogen containing analog of solasodine, is teratogenic. Results of these and other studies suggest that a basic nitrogen positioned alpha with respect to the steroidal plane and at appropriate distance beyond the D ring confers the teratogenicity on the molecule. Potato sprouts with high alkaloid content are teratogenic in hamsters, but tubers and peels are not. PMID:723484

  17. Methanol extracts of Hamelia patens containing oxindole alkaloids relax KCl-induced contraction in rat myometrium.

    Reyes-Chilpa, Ricardo; Rivera, Jesús; Oropeza, Martha; Mendoza, Pilar; Amekraz, Badia; Jankowski, Christopher; Campos, Maria

    2004-10-01

    Hamelia patens JAQC. (Rubiaceae) is a medicinal bush widely distributed in tropical areas of the American continent. It is used in Mexican Traditional Medicine for the treatment of menstrual disorders, therefore suggesting that its chemical constituents may have some effect on myometrium contractility. Physiological effects might differ due to quantitative variations in the content of alkaloids arising from its wide geographical distribution. To test this hypothesis, the content of oxindole alkaloids in methanol extracts of five different samples collected in Mexico was quantified by GC-MS. Each extract was assayed on contractility of estrogen-primed rat myometrium. Variations in the content of alkaloids were observed among the different samples. All samples relaxed in a concentration-dependent manner the high KCl-induced contraction in rat myometrium. Those which lack rumberine and/or maruquine displayed a higher relaxant effect than samples containing them, suggesting that these alkaloids might counteract the effects of isopteropodine. However, in contrast with verapamil, Hamelia patens metanol extracts are poor relaxants. PMID:15467206

  18. A Palladium-Catalyzed Vinylcyclopropane (3 + 2) Cycloaddition Approach to the Melodinus Alkaloids

    Goldberg, Alexander F. G.

    2011-08-19

    A palladium-catalyzed (3+2) cycloaddition of a vinylcyclopropane and a β-nitrostyrene is employed to rapidly assemble the cyclopentane core of the Melodinus alkaloids. The ABCD ring system of the natural product family is prepared in six steps from commercially available materials.

  19. Seasonal pharmacological properties and alkaloid content in Cyrtanthus contractus NE Br

    Ncube, B.; Nair, J. J.; Rárová, Lucie; Strnad, Miroslav; Finnie, J.F.; van Staden, J.

    2015-01-01

    Roč. 97, MAR 2015 (2015), s. 69-76. ISSN 0254-6299 R&D Projects: GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : Acetylcholinesterase * Alkaloids * Cyrtanthus Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 0.978, year: 2014

  20. Towards a Molecular Understanding of the Biosynthesis of Amaryllidaceae Alkaloids in Support of Their Expanding Medical Use

    Adam M. Takos

    2013-05-01

    Full Text Available The alkaloids characteristically produced by the subfamily Amaryllidoideae of the Amaryllidaceae, bulbous plant species that include well know genera such as Narcissus (daffodils and Galanthus (snowdrops, are a source of new pharmaceutical compounds. Presently, only the Amaryllidaceae alkaloid galanthamine, an acetylcholinesterase inhibitor used to treat symptoms of Alzheimer’s disease, is produced commercially as a drug from cultivated plants. However, several Amaryllidaceae alkaloids have shown great promise as anti-cancer drugs, but their further clinical development is restricted by their limited commercial availability. Amaryllidaceae species have a long history of cultivation and breeding as ornamental bulbs, and phytochemical research has focussed on the diversity in alkaloid content and composition. In contrast to the available pharmacological and phytochemical data, ecological, physiological and molecular aspects of the Amaryllidaceae and their alkaloids are much less explored and the identity of the alkaloid biosynthetic genes is presently unknown. An improved molecular understanding of Amaryllidaceae alkaloid biosynthesis would greatly benefit the rational design of breeding programs to produce cultivars optimised for the production of pharmaceutical compounds and enable biotechnology based approaches.

  1. Alkaloids from beach spider lily (Hymenocallis littoralis) induce apoptosis of HepG-2 cells by the fas-signaling pathway.

    Ji, Yu-Bin; Chen, Ning; Zhu, Hong-Wei; Ling, Na; Li, Wen-Lan; Song, Dong-Xue; Gao, Shi-Yong; Zhang, Wang-Cheng; Ma, Nan-Nan

    2014-01-01

    Alkaloids are the most extensively featured compounds of natural anti-tumor herbs, which have attracted much attention in pharmaceutical research. In our previous studies, a mixture of major three alkaloid components (5, 6-dihydrobicolorine, 7-deoxy-trans-dihydronarciclasine, littoraline) from Hymenocallis littoralis were extracted, analyzed and designated as AHL. In this paper, AHL extracts were added to human liver hepatocellular cells HepG-2, human gastric cancer cell SGC-7901, human breast adenocarcinoma cell MCF-7 and human umbilical vein endothelial cell EVC-304, to screen one or more AHL-sensitive tumor cell. Among these cells, HepG-2 was the most sensitive to AHL treatment, a very low dose (0.8μg/ml) significantly inhibiting proliferation . The non- tumor cell EVC-304, however, was not apparently affected. Effect of AHL on HepG-2 cells was then explored. We found that the AHL could cause HepG-2 cycle arrest at G2/M checkpoint, induce apoptosis, and interrupt polymerization of microtubules. In addition, expression of two cell cycle-regulated proteins, CyclinB1 and CDK1, was up-regulated upon AHL treatment. Up-regulation of the Fas, Fas ligand, Caspase-8 and Caspase-3 was observed as well, which might imply roles for the Fas/FsaL signaling pathway in the AHL-induced apoptosis of HepG-2 cells. PMID:25422219

  2. Virus-induced gene silencing identifies Catharanthus roseus 7-deoxyloganic acid-7-hydroxylase, a step in iridoid and monoterpene indole alkaloid biosynthesis.

    Salim, Vonny; Yu, Fang; Altarejos, Joaquín; De Luca, Vincenzo

    2013-12-01

    Iridoids are a major group of biologically active molecules that are present in thousands of plant species, and one versatile iridoid, secologanin, is a precursor for the assembly of thousands of monoterpenoid indole alkaloids (MIAs) as well as a number of quinoline alkaloids. This study uses bioinformatics to screen large databases of annotated transcripts from various MIA-producing plant species to select candidate genes that may be involved in iridoid biosynthesis. Virus-induced gene silencing of the selected genes combined with metabolite analyses of silenced plants was then used to identify the 7-deoxyloganic acid 7-hydroxylase (CrDL7H) that is involved in the 3rd to last step in secologanin biosynthesis. Silencing of CrDL7H reduced secologanin levels by at least 70%, and increased the levels of 7-deoxyloganic acid to over 4 mg g(-1) fresh leaf weight compared to control plants in which this iridoid is not detected. Functional expression of this CrDL7H in yeast confirmed its biochemical activity, and substrate specificity studies showed its preference for 7-deoxyloganic acid over other closely related substrates. Together, these results suggest that hydroxylation precedes carboxy-O-methylation in the secologanin pathway in Catharanthus roseus. PMID:24103035

  3. Developmental patterning and segregation of alkaloids in areca nut (seed of Areca catechu) revealed by magnetic resonance and mass spectrometry imaging.

    Srimany, Amitava; George, Christy; Naik, Hemanta R; Pinto, Danica Glenda; Chandrakumar, N; Pradeep, T

    2016-05-01

    Areca nut (seed of Areca catechu) is consumed by people from different parts of Asia, including India. The four major alkaloids present in areca nut are arecoline, arecaidine, guvacoline and guvacine. Upon cutting, the nut reveals two kinds of regions; white and brown. In our present study, we have monitored the formation of these two regions within the nut during maturation, using the non-invasive techniques of magnetic resonance imaging (MRI) and volume localized magnetic resonance spectroscopy (MRS). Electrospray ionization mass spectrometry (ESI MS) and desorption electrospray ionization mass spectrometry (DESI MS) imaging have been used to study the associated change in the alkaloid contents of these two regions during the growth of the nut. Our study reveals that white and brown regions start forming within the nut when the liquid within starts solidifying. At the final stage of maturity, arecoline, arecaidine and guvacoline get segregated in the brown region whereas guvacine gets to the white region of the nut. The transport of molecules with maturity and corresponding pattern formation are expected to be associated with a multitude of physiochemical changes. PMID:26896852

  4. Target analysis and retrospective screening of veterinary drugs, ergot alkaloids, plant toxins and other undesirable substances in feed using liquid chromatography-high resolution mass spectrometry.

    León, Nuria; Pastor, Agustín; Yusà, Vicent

    2016-03-01

    A comprehensive strategy combining a quantitative method for 77 banned veterinary drugs, mycotoxins, ergot alkaloids and plant toxins, and a post-target screening for 425 substances including pesticides and environmental contaminants in feed were developed using a QuEChERS-based extraction and an ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry (UHPLC-HRMS). The quantitative method was validated after previous statistical optimisation of the main parameters governing ionisation, and presented recoveries ranging, in general, from 80 to 120%, with a precision in terms of Relative Standard Deviation (RSD) lower than 20%. The full-scan accurate mass data were acquired with a resolving power of 50000 FWHM and a mass accuracy lower than 5ppm. The method LOQ was lower than 12.5µgkg(-1) for the majority of the veterinary drugs and plant toxins and 20µgkg(-1) for ergot alkaloids. For post-target screening a customised theoretical database including the exact mass, the polarity of acquisition and the expected adducts was built and used for post-run retrospective screening. The analytical strategy was applied to 32 feed samples collected from farms of the Valencia Region (Spain). Florfenicol, zearalenone and atropine were identified and quantified at concentrations around 10µgkg(-1). In the post-target screening of the real samples, Sulfadiazine, Thrimetoprin and Pirimiphosmethyl were tentatively identified. PMID:26717812

  5. Staphylococcal enterotoxin A gene-carrying Staphylococcus aureus isolated from foods and its control by crude alkaloid from papaya leaves.

    Handayani, Lita; Faridah, Didah Nur; Kusumaningrum, Harsi D

    2014-11-01

    Staphylococcus aureus is a known pathogen causing intoxication by producing enterotoxins in food. Staphylococcal enterotoxin A is one of the enterotoxins commonly implicated in staphylococcal food poisoning. The ability of crude alkaloid extract from papaya leaves to inhibit the growth of S. aureus and staphylococcal enterotoxin A synthesis was investigated. Staphylococcal enterotoxin A gene-carrying S. aureus was isolated from raw milk and ready-to-eat foods. Crude alkaloid was extracted from ground, dried papaya leaves using ultrasonic-assisted extraction, and a MIC of the alkaloid was determined by the broth macrodilution method. Furthermore, S. aureus isolate was exposed to the crude alkaloid extract at one- and twofold MIC, and the expression of sea was subsequently analyzed using a quantitative reverse transcription real-time PCR. Ten isolates of S. aureus were obtained, and nine of those isolates were sea carriers. The yield of crude alkaloid extract was 0.48 to 1.82% per dry weight of papaya leaves. A MIC of crude alkaloid to S. aureus was 0.25 mg/ml. After exposure to the alkaloid at 0.25 and 0.5 mg/ml for 2 h, a significant increase in cycle threshold values of sea was observed. The sea was expressed 29 and 41 times less when S. aureus was exposed to crude alkaloid at one- and twofold MIC, respectively. This study revealed that crude alkaloid of papaya leaves could control staphylococcal enterotoxin A gene-carrying S. aureus by suppressing the expression of sea, in addition to the ability to inhibit the growth of S. aureus. The expression of sea was successfully quantified. PMID:25364936

  6. Mutagenesis as a Functional Genomics Platform for Pharmaceutical Alkaloid Biosynthetic Gene Discovery in Opium Poppy

    Opium poppy (Papaver somniferum) accumulates the analgesic benzyl-isoquinoline alkaloids morphine, codeine and thebaine, and remains one of the world's most important medicinal plants. The development of varieties that accumulate valuable compounds, such as thebaine and codeine, but not morphine precludes the illicit synthesis of heroin (O,O-diacetylmorphine) and has led to the establishment of alternative cash crops. Novel cDNAs encoding a growing number of biosynthetic enzymes have been isolated, and various -omics resources including EST databases and DNA microarray chips have been established. However, the full potential of functional genomics as a tool for gene discovery in opium poppy remains limited by the relative inefficiency of genetic transformation protocols, which also restricts the application of metabolic engineering for both experimental and commercial purposes. We are establishing an effective functional genomics initiative based on induced mutagenesis and recently developed reverse genetics methodology, such as TILLING (Targeting Induced Local Lesions IN Genomes), with the aim of identifying biosynthetic genes that can be used to engineer opium poppy for the production of copious levels of high-value pharmaceutical alkaloids. Mutagenesis involves the treatment of seeds with ethyl methane sulfonate (EMS) or by fast-neutron bombardment (FNB). In preliminary experiments with EMS-treated seeds, the screening of 1,250 independent M2 plants led to the isolation of four mutants that displayed two distinctly altered alkaloid profiles. Two lines accumulated the central pathway intermediate reticuline and relatively low levels of morphine, codeine and thebaine compared to wild-type plants. Two other lines showed the unusual accumulation in the latex of the antimicrobial alkaloid sanguinarine, which is the product of a branch pathway distinct from that leading to morphine. The present status of -omics resources and functional genomics platforms available to

  7. Mutagenesis as a functional genomics platform for pharmaceutical alkaloid biosynthetic gene discovery in opium poppy

    Opium poppy (Papaver somniferum) accumulates the analgesic alkaloids morphine, codeine and thebaine, and remains one of the world's most important medicinal plants. The development of varieties that accumulate valuable compounds, such as thebaine and codeine, but not morphine precludes the illicit synthesis of heroin (O,O-diacetylmorphine) and has created opportunities to establish alternative cash crops. Novel cDNAs encoding more than a dozen biosynthetic enzymes have been isolated, and substantial EST databases and DNA microarray chips have been established. The full potential of functional genomics as a tool for gene discovery in opium poppy remains limited by the relative inefficiency of genetic transformation protocols, which also restricts the application of metabolic engineering for both experimental and commercial purposes. We are establishing an effective functional genomics initiative based on induced mutagenesis and TILLING (Targeting Induced Local Lesions IN Genomes) and with the aim of identifying biosynthetic genes that can be used to engineer opium poppy to produce copious levels of high-value pharmaceutical alkaloids. Mutagenesis involves the treatment of seeds by fast-neutron bombardment (FNB) or with ethyl methane sulfonate (EMS). Mutagenized opium poppy plants are cultivated in a secure underground growth facility in partnership with a Canadian biotechnology company. In preliminary experiments with EMS-treated seeds, the screening of 1,250 independent M2 plants led to the isolation of four mutants that displayed two distinctly altered alkaloid profiles. Two lines accumulated the central pathway intermediate (S)- reticuline and only low levels of morphine, codeine and thebaine. Two other lines showed the unusual accumulation of the antimicrobial alkaloid sanguinarine, which is the product of a branch pathway distinct from that leading to morphine, in the latex. The present status of -omics resources and functional genomics platforms available to

  8. Rapid in situ detection of alkaloids in plant tissue under ambient conditions using desorption electrospray ionization.

    Talaty, Nari; Takáts, Zoltán; Cooks, R Graham

    2005-12-01

    Desorption electrospray ionization (DESI) mass spectrometry is applied to the in situ detection of alkaloids in the tissue of poison hemlock (Conium maculatum), jimsonweed (Datura stramonium) and deadly nightshade (Atropa belladonna). The experiment is carried out by electrospraying micro-droplets of solvent onto native or freshly-cut plant tissue surfaces. No sample preparation is required and the mass spectra are recorded under ambient conditions, in times of a few seconds. The impact of the sprayed droplets on the surface produces gaseous ions from organic compounds originally present in the plant tissue. The effects of operating parameters, including the electrospray high voltage, heated capillary temperature, the solvent infusion rate and the carrier gas pressure on analytical performance are evaluated and optimized. Different types of plant material are analyzed including seeds, stems, leaves, roots and flowers. All the previously reported alkaloids have been detected in C. maculatum, while fifteen out of nineteen known alkaloids for D. stramonium and the principal alkaloids of A. belladonna were also identified. All identifications were confirmed by tandem mass spectrometry. Results obtained show similar mass spectra, number of alkaloids, and signal intensities to those obtained when extraction and separation processes are performed prior to mass spectrometric analysis. Evidence is provided that DESI ionization occurs by both a gas-phase ionization process and by a droplet pick-up mechanism. Quantitative precision of DESI is compared with conventional electrospray ionization mass spectrometry (after sample workup) and the RSD values for the same set of 25 dicotyledonous C. maculatum seeds (one half of each seed analyzed by ESI and the other by DESI) are 9.8% and 5.2%, respectively. PMID:16284661

  9. Evaluation of antibiotic potential of alkaloids of Tribulus terrestris L. against some pathogenic microorganisms

    Alka Jindal

    2013-01-01

    Full Text Available Context: Antibiotic resistance has become a global concern. There has been an increasing incidence of multiple resistances in human pathogenic microorganisms in recent years, largely due to indiscriminate use of commercial antimicrobial drugs commonly employed in the treatment of infectious diseases. Tribulus terrestris (Family: Zygophyllaceae is a well-known medicinal plant and has been used world-wide for the treatment of infectious diseases. Alkaloids are group of naturally occurring chemical compounds, which are known to have antimicrobial properties. Aim: The present study is designed to evaluate the antimicrobial potential of alkaloids of T. terrestris L. Materials and Methods: Alkaloids extracted from different parts (root, stem, leaf and fruits of T. terrestris were screened by Disc diffusion assay against three bacterial strains: gram positive (Staphylococcus aureus, gram negative (Escherichia coli and Proteus mirabilis and two fungal strains: Aspergillus flavus and Aspergillus niger. Minimum inhibitory concentration of the extracts was evaluated by micro broth dilution method while minimum bactericidal/fungicidal concentration was determined by sub culturing the relevant samples. Total activity of the extracts against each sensitive test pathogens was also calculated. Statistical Analysis: Mean value and standard error mean were calculated for the results of disc diffusion assay and data were analysed by one-way analysis of variance and P values were considered significant at P < 0.05. Results: The alkaloid extracts of T. terrestris showed significant antibacterial potential as all test extracts were found active against both the gram positive and negative bacteria, but were inactive against the tested fungi. Conclusion: The present study indicates the broad spectrum antibacterial potential of the alkaloids of T. terrestris, hence may be exploited for future antibacterial drugs.

  10. Enzymatic and Chemo-Enzymatic Approaches Towards Natural and Non-Natural Alkaloids: Indoles, Isoquinolines, and Others

    Stöckigt, Joachim; Chen, Zhong; Ruppert, Martin

    The multi-step enzyme catalysed biosyntheses of monoterpenoid indole and isoquinoline alkaloids are described. Special emphasis is placed on those pathways leading to alkaloids of pharmacological and medicinal significance which have been fully elucidated at the enzyme level. The successful identification and cloning of cDNAs of single enzymes and their application provides great opportunities to develop novel strategies for both in vitro and in vivo alkaloid production in whole plants or tissue cultures, as well as in microbial systems such as Escherichia coli and yeast.

  11. Permeability of ergot alkaloids across the blood-brain barrier in vitro and influence on the barrier integrity

    Mulac, Dennis; Hüwel, Sabine; Galla, Hans-Joachim; Humpf, Hans-Ulrich

    2011-01-01

    Scope Ergot alkaloids are secondary metabolites of Claviceps spp. and they have been in the focus of research for many years. Experiments focusing on ergotamine as a former migraine drug referring to the ability to reach the brain revealed controversial results. The question to which extent ergot alkaloids are able to cross the blood-brain barrier is still not answered. Methods and results In order to answer this question we have studied the ability of ergot alkaloids to penetrate the blood-b...

  12. An integrated strategy for the systematic characterization and discovery of new indole alkaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbitrap-MS.

    Pan, Huiqin; Yang, Wenzhi; Zhang, Yibei; Yang, Min; Feng, Ruihong; Wu, Wanying; Guo, Dean

    2015-08-01

    The exploration of new chemical entities from herbal medicines may provide candidates for the in silico screening of drug leads. However, this significant work is hindered by the presence of multiple classes of plant metabolites and many re-discovered structures. This study presents an integrated strategy that uses ultrahigh-performance liquid chromatography/linear ion-trap quadrupole/Orbitrap mass spectrometry (UHPLC/LTQ-Orbitrap-MS) coupled with in-house library data for the systematic characterization and discovery of new potentially bioactive molecules. Exploration of the indole alkaloids from Uncaria rhynchophylla (UR) is presented as a model study. Initially, the primary characterization of alkaloids was achieved using mass defect filtering and neutral loss filtering. Subsequently, phytochemical isolation obtained 14 alkaloid compounds as reference standards, including a new one identified as 16,17-dihydro-O-demethylhirsuteine by NMR analyses. The direct-infusion fragmentation behaviors of these isolated alkaloids were studied to provide diagnostic structural information facilitating the rapid differentiation and characterization of four different alkaloid subtypes. Ultimately, after combining the experimental results with a survey of an in-house library containing 129 alkaloids isolated from the Uncaria genus, a total of 92 alkaloids (60 free alkaloids and 32 alkaloid O-glycosides) were identified or tentatively characterized, 56 of which are potential new alkaloids for the Uncaria genus. Hydroxylation on ring A, broad variations in the C-15 side chain, new N-oxides, and numerous O-glycosides, represent the novel features of the newly discovered indole alkaloid structures. These results greatly expand our knowledge of UR chemistry and are useful for the computational screening of potentially bioactive molecules from indole alkaloids. Graphical Abstract A four-step integrated strategy for the systematic characterization and efficient discovery of new indole

  13. Major Sport Venues

    Department of Homeland Security — The Major Public Venues dataset is composed of facilities that host events for the National Association for Stock Car Auto Racing, Indy Racing League, Major League...

  14. Analysis of Indole Alkaloids from Rhazya stricta Hairy Roots by Ultra-Performance Liquid Chromatography-Mass Spectrometry

    Amir Akhgari

    2015-12-01

    Full Text Available Rhazya stricta Decne. (Apocynaceae contains a large number of terpenoid indole alkaloids (TIAs. This study focused on the composition of alkaloids obtained from transformed hairy root cultures of R. stricta employing ultra-performance liquid chromatography-mass spectrometry (UPLC-MS. In the UPLC-MS analyses, a total of 20 TIAs were identified from crude extracts. Eburenine and vincanine were the main alkaloids followed by polar glucoalkaloids, strictosidine lactam and strictosidine. Secodine-type alkaloids, tetrahydrosecodinol, tetrahydro- and dihydrosecodine were detected too. The occurrence of tetrahydrosecodinol was confirmed for the first time for R. stricta. Furthermore, two isomers of yohimbine, serpentine and vallesiachotamine were identified. The study shows that a characteristic pattern of biosynthetically related TIAs can be monitored in Rhazya hairy root crude extract by this chromatographic method.

  15. Screening of penicillium species and optimisation of culture conditions for the production of ergot alkaloids using surface culture fermentation process

    Abstract. The present study deals with the screening of fungal species and suitable fermentation medium for the production of ergot alkaloids. Various species of genus Penicillium were grown on different fermentation media by employing surface culture fermentation technique to achieve the most suitable medium and the best Penicillium sp. The results showed that medium M5 gave maximum yield with Penicillium commune. Different culture conditions such as effect of different carbon and nitrogen sources, their concentration levels, different pH values and sizes of inoculum on the production of ergot alkaloids were also studied to improve the yield. Maximum production of ergot alkaloids (4.32 mg/L) was achieved with 15 mL spore suspension at pH 5 in fermentation medium containing 35% (w/v) sucrose. All these results indicate that culture conditions are very much crucial to improve the yield of ergot alkaloids produced by Penicillium commune through surface culture process. (author)

  16. Ancistrotanzanine C and related 5,1 '- and 7,3 '-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis

    Bringmann, G.; Dreyer, M.; Faber, J.H.; Dalsgaard, Petur; Steerk, D.; Jaroszewski, J.W.; Ndangalasi, H.; Mbago, F.; Brun, R.; Christensen, S.B.

    2004-01-01

    from this newly discovered plant species. The structural elucidation was achieved by chemical, spectroscopic, and chiroptical methods. The biological activities of the alkaloids against the pathogens causing malaria tropica, leishmaniasis, Chagas' disease, and African sleeping sickness were evaluated....

  17. Development and validation of a LC-MS method for quantitation of ergot alkaloids in lateral saphenous vein tissue

    A liquid chromatography-mass spectrometry (LC/MS) method for simultaneous quantitation of seven ergot alkaloids (lysergic acid, ergonovine, ergovaline, ergocornine, ergotamine, ergocryptine and ergocrystine) in vascular tissue was developed and validated. Reverse-phase chromatography, coupled to an...

  18. Molluscicidal activity of Hammada scoparia (Pomel Iljin leaf extracts and the principal alkaloids isolated from them against Galba truncatula

    R Mezghani-Jarraya

    2009-11-01

    Full Text Available The molluscicidal activity of Hammada scoparia leaf extracts and the principal alkaloids isolated from them (carnegine and N-methylisosalsoline were tested against the mollusc gastropod, Galba truncatula, the intermediate host of Fasciola hepatica in Tunisia. The results indicated that the molluscicidal activity was correlated with the presence of alkaloids. A significant molluscicidal value, according to the World Health Organization, was found with the methanol extract (LC50 = 28.93 ppm. Further fractionation of the methanolic extract led to the isolation of two principal alkaloids: carnegine and N-methylisosalsoline. These alkaloids are isoquinolines that have not previously been characterised for their molluscicidal activity. The N-methylisosalsoline possesses the highest molluscicidal activity (LC50 = 0.47 μM against G. truncatula.

  19. Multiple shoot cultures of Atropa belladonna: Effect of physico-chemical factors on growth and alkaloid formation

    Multiple shoot cultures were established from shoot tip and axillary meristem of the plant Atropa belladonna. The cultures were initially raised on agar medium and subsequently maintained on liquid medium of Murashige and Skoog (1962) supplemented with BA. These cultures were subjected to different doses of -y-irradiation. Recovery from the radiation effects was observed in tissues subjected to 29 Gy during four successive passages. Plant growth regulators influenced the growth and morphogenetic events of the tissues. The precursors of tropane alkaloids marginally increased the alkaloid synthesis during the stationary phase of growth. Shoot cultures, established from different field grown plants varying in alkaloid content, were morphologically similar and did not exhibit the parental characteristics with respect to alkaloid formation

  20. Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures

    Schriemer David C; Khan Morgan F; Desgagné-Penix Isabel; Cram Dustin; Nowak Jacek; Facchini Peter J

    2010-01-01

    Abstract Background Papaver somniferum (opium poppy) is the source for several pharmaceutical benzylisoquinoline alkaloids including morphine, the codeine and sanguinarine. In response to treatment with a fungal elicitor, the biosynthesis and accumulation of sanguinarine is induced along with other plant defense responses in opium poppy cell cultures. The transcriptional induction of alkaloid metabolism in cultured cells provides an opportunity to identify components of this process via the i...

  1. Antibacterial Properties of Alkaloid Extracts from Callistemon citrinus and Vernonia adoensis against Staphylococcus aureus and Pseudomonas aeruginosa

    Donald Mabhiza; Tariro Chitemerere; Stanley Mukanganyama

    2016-01-01

    The development of new antibiotics from new chemical entities is becoming more and more expensive, time-consuming, and compounded by emerging strains that are drug resistant. Alkaloids are plant secondary metabolites which have been shown to have potent pharmacological activities. The effect of alkaloids from Callistemon citrinus and Vernonia adoensis leaves on bacterial growth and efflux pump activity was evaluated on Staphylococcus aureus and Pseudomonas aeruginosa. At a concentration of 1....

  2. Effects of Mitragynine and a Crude Alkaloid Extract Derived from Mitragyna speciosa Korth. on Permethrin Elimination in Rats

    Kachamas Srichana; Benjamas Janchawee; Sathaporn Prutipanlai; Pritsana Raungrut; Niwat Keawpradub

    2015-01-01

    Detoxification and elimination of permethrin (PM) are mediated by hydrolysis via carboxylesterase (CES). Mitragyna speciosa (kratom) contains mitragynine (MG) and other bioactive alkaloids. Since PM and MG have the same catalytic site and M. speciosa is usually abused by adding other ingredients such as pyrethroid insecticides, the effects of MG and an alkaloid extract (AE) on the elimination of PM were investigated in rats. Rats were subjected to single and multiple pretreatment with MG and ...

  3. Distribution coefficients of purine alkaloids in water-ammonium sulfate-alkyl acetate-dialkyl phthalate systems

    Korenman, Ya. I.; Krivosheeva, O. A.; Mokshina, N. Ya.

    2012-12-01

    The distribution of purine alkaloids (caffeine, theobromine, theophylline) was studied in the systems: alkyl acetates-dialkyl phtalate-salting-out agent (ammonium sulfate). The quantitative characteristics of the extraction-distribution coefficients ( D) and the degree of extraction ( R, %) are calculated. The relationships between the distribution coefficients of alkaloids and the length of the hydrocarbon radical in the molecule of alkyl acetate (dialkyl phtalate) are determined. The possibility of predicting the distribution coefficients is demonstrated.

  4. Detection by UPLC/ESI-TOF-MS of alkaloids in three Lycopodiaceae species from French Polynesia and their anticholinesterase activity.

    Ho, Raimana; Marsousi, Niloufar; Eugster, Philippe; Bianchini, Jean-Pierre; Raharivelomanana, Phila

    2009-10-01

    Three Lycopodiaceae species from French Polynesia, Lycopodium venustulum C. Gaudichaud, Lycopodiella cernua (C. Linnaeus) R. E. Pichi Sermolli and Lycopodium henryanum E. D. Brown were investigated for their alkaloidal composition by UHPLC/ESI-TOF-MS. Ten alkaloids were identified, with lycopodine and lycodoline being the main constituents in the three species. The acetylcholinesterase-inhibitory activities of the three species are probably due to the occurrence of huperzine A, huperzine B, huperzine E, huperzinine and lycopodine. PMID:19911569

  5. Colonial Agro-Industrialism : Science, Industry and the State in the Dutch Golden Alkaloid Age, 1850-1950

    Roersch van der Hoogte, A.

    2015-01-01

    This thesis is about what I call the Dutch Golden Alkaloid Age between roughly the 1850s and 1950s. I follow the historical trajectory of the production and distribution of the anti-febrifuge cinchona bark tree (Cinchona officinalis Lin.) and its most powerful and therapeutically applied alkaloid in the Dutch empire—quinine, an antimalarial medicine. During this period, scientists, planters, traders, industrialists and state officials in the Netherlands and the former Dutch colony of the Neth...

  6. Screening for total ergot alkaloids in rye flour by planar solid phase extraction-fluorescence detection and mass spectrometry.

    Oellig, Claudia; Melde, Tina

    2016-04-01

    The analysis of ergot alkaloids is generally performed by high-performance liquid chromatography (HPLC) coupled to fluorescence detection (FLD) or mass selective detection. As for monitoring only the sum of ergot alkaloids is relevant, a fast and easy screening method for the determination of the total alkaloid content was developed using planar solid phase extraction (pSPE). Applying pSPE, recently introduced for pesticide residue analysis in fruits and vegetables (Oellig and Schwack, 2011) and tea (Oellig and Schwack, 2012), all ergot alkaloids are concentrated in a target zone followed by detection as the sum. The herein presented method includes an ammonium acetate buffered extraction step, followed by a fast liquid-liquid partitioning pre-cleaning before pSPE is performed on high-performance thin-layer chromatography (HPTLC) amino plates with a single methanol development to separate the ergot alkaloids from the remaining matrix and to collect them in a single zone. For quantitation, the native fluorescence was used after dipping the plate in n-hexane/paraffin solution for fluorescence enhancement. Limits of detection and quantitation of 0.07 and 0.24mg/kg rye, respectively, expressed as ergocristine, were well below the currently applied quality criterion limit for rye. Near-100% recoveries were obtained at relevant spiking levels for different rye flour samples. Hence, the fast pSPE-FLD is an efficient and reliable method to screen for the total ergot alkaloid content in rye and a rapid alternative to the HPLC determination of individual alkaloids and to summing them up. HPTLC-MS additionally enables the identification of the ergot alkaloid composition by a single mass spectrum, when utilized as a fingerprint, offering an easy differentiation of Secale cornutum from different origins. PMID:26947163

  7. Neocryptolepine: A Promising Indoloisoquinoline Alkaloid with Interesting Biological Activity. Evaluation of the Drug and its Most Relevant Analogs.

    Larghi, Enrique L; Bracca, Andrea B J; Arroyo Aguilar, Abel A; Heredia, Daniel A; Pergomet, Jorgelina L; Simonetti, Sebastian O; Kaufman, Teodoro S

    2015-01-01

    Plants are one of the most important resources for the discovery of new drugs. The potential of natural compounds as new drug leads is clearly illustrated by the discovery and development of many modern medicines. This is an encouraging factor that drives natural products research in the vegetable kingdom. Neocryptolepine is a tetracyclic nitrogen heterocycle isolated from the African climber Cryptolepis sanguinolenta, which is widely used in traditional African medicine in many countries of Central and West Africa. The natural product is one of the representative examples of the small family of indolo[2,3-b]quinoline alkaloids, being endowed of multiple biological activities, including DNA-binding and inhibition of the enzyme topoisomerase II. It is also cytotoxic, antibacterial, antifungal and molluscicidal, also displaying antiprotozoal activity, particularly as antitrypanosomal, antileishmanial, antischistosomal and antiplasmodial. Some of these activities have been related to the product's ability to bind to DNA and to inhibit topoisomerase II; however, the exact mechanisms behind all of the observed bioactivities have not been comprehensively clarified. Major research activities regarding neocryptolepine have been focused into two seemingly opposite fields, related to its cytotoxic and antimalarial properties. Optimization of the natural product as a cytotoxic agent implied improvements in its bioavailability and activity, while the need of non-cytotoxic compounds guided the design and optimization of antimalarial agents. Therefore, the aim of the present article is to systematically review the current knowledge about the diversity of the biological activities related to neocryptolepine, its analogs and derivatives. PMID:25915612

  8. Preparative separation of alkaloids from Picrasma quassioides (D. Don) Benn. by conventional and pH-zone-refining countercurrent chromatography.

    Zhang, Qinghai; Shu, Xikai; Jing, Feng; Wang, Xiao; Lin, Changhu; Luo, Aiqin

    2014-01-01

    Two high-speed countercurrent chromatography (HSCCC) modes were compared by separation of major alkaloids from crude extract of Picrasma quassioides. The conventional HSCCC separation was performed with a two-phase solvent system composed of petroleum ether-ethyl acetate-methanol-water (5:5:4.5:5.5, v/v/v/v) with 200 mg loading. pH-Zone-refining CCC was performed with two-phase solvent system composed of petroleum ether-ethyl acetate-n-butanol-water (3:2:7:9, v/v/v/v) where triethylamine (10 mM) was added to the upper organic stationary phase and hydrochloric acid (5 mM) was added to the lower aqueous phase with 2 g loading. From 2 g of crude extract, 87 mg of 5-methoxycanthin-6-one (a), 38 mg of 1-methoxy-β-carboline (b), 134 mg of 1-ethyl-4,8-dimethoxy-β-carboline (c), 74 mg of 1-ethoxycarbonyl-β-carboline (d), 56 mg of 1-vinyl-4,8-dimethoxy-β-carboline (e) and 26 mg of 1-vinyl-4-dimethoxy-β-carboline (f) were obtained with purities of over 97.0%. The results indicated that pH-zone-refining CCC is an excellent separations tool at the multigram level. PMID:24968331

  9. Preparative Separation of Alkaloids from Picrasma quassioides (D. Don Benn. by Conventional and pH-Zone-Refining Countercurrent Chromatography

    Qinghai Zhang

    2014-06-01

    Full Text Available Two high-speed countercurrent chromatography (HSCCC modes were compared by separation of major alkaloids from crude extract of Picrasma quassioides. The conventional HSCCC separation was performed with a two-phase solvent system composed of petroleum ether–ethyl acetate–methanol–water (5:5:4.5:5.5, v/v/v/v with 200 mg loading. pH-Zone-refining CCC was performed with two-phase solvent system composed of petroleum ether–ethyl acetate–n-butanol–water (3:2:7:9, v/v/v/v where triethylamine (10 mM was added to the upper organic stationary phase and hydrochloric acid (5 mM was added to the lower aqueous phase with 2 g loading. From 2 g of crude extract, 87 mg of 5-methoxycanthin-6-one (a, 38 mg of 1-methoxy-β-carboline (b, 134 mg of 1-ethyl-4,8-dimethoxy-β-carboline (c, 74 mg of 1-ethoxycarbonyl-β-carboline (d, 56 mg of 1-vinyl-4,8-dimethoxy-β-carboline (e and 26 mg of 1-vinyl-4-dimethoxy-β-carboline (f were obtained with purities of over 97.0%. The results indicated that pH-zone-refining CCC is an excellent separations tool at the multigram level.

  10. Plant-Derived Antimalarial Agents: New Leads and Efficient Phytomedicines. Part II. Non-Alkaloidal Natural Products

    Alaíde Braga de Oliveira

    2009-08-01

    Full Text Available Malaria is still the most destructive and dangerous parasitic infection in many tropical and subtropical countries. The burden of this disease is getting worse, mainly due to the increasing resistance of Plasmodium falciparum against the widely available antimalarial drugs. There is an urgent need for new, more affordable and accessible antimalarial agents possessing original modes of action. Natural products have played a dominant role in the discovery of leads for the development of drugs to treat human diseases, and this fact anticipates that new antimalarial leads may certainly emerge from tropical plant sources. This present review covers most of the recently-published non-alkaloidal natural compounds from plants with antiplasmodial and antimalarial properties, belonging to the classes of terpenes, limonoids, flavonoids, chromones, xanthones, anthraquinones, miscellaneous and related compounds, besides the majority of papers describing antiplasmodial crude extracts published in the last five years not reviewed before. In addition, some perspectives and remarks on the development of new drugs and phytomedicines for malaria are succinctly discussed.

  11. Evaluation of antioxidant and antibacterial activities of aqueous, methanolic and alkaloid extracts from Mitragyna speciosa (Rubiaceae family) leaves.

    Parthasarathy, Suhanya; Bin Azizi, Juzaili; Ramanathan, Surash; Ismail, Sabariah; Sasidharan, Sreenivasan; Said, Mohd I Mohd; Mansor, Sharif Mahsufi

    2009-01-01

    Studies on the antioxidant and antimicrobial activities of Mitragyna speciosa leaf extracts are lacking. In this study the antioxidant properties of water, methanolic and alkaloid M. speciosa leaf extracts were evaluated using the DPPH (2,2-diphenyl-1- picrylhydrazyl) radical scavenging method. The amount of total phenolics and flavanoid contents were also estimated. The DPPH IC(50) values of the aqueous, alkaloid and methanolic extracts were 213.4, 104.81 and 37.08 microg/mL, respectively. The total phenolic content of the aqueous, alkaloid and methanolic extracts were 66.0 mg, 88.4, 105.6 mg GAE/g, respectively, while the total flavanoid were 28.2, 20.0 and 91.1 mg CAE/g respectively. The antioxidant activities were correlated with the total phenolic content. This result suggests that the relatively high antioxidant activity of the methanolic extract compared to aqueous and alkaloid extract could be possibly be due to its high phenolic content. The aqueous, alkaloid and methanolic extracts were screened for antimicrobial activity. The extracts showed antimicrobial activity against Salmonella typhi and Bacillus subtilis. The minimum inhibitory concentrations (MICs) of extracts determined by the broth dilution method ranged from 3.12 to 6.25 mg/mL. The alkaloid extract was found to be most effective against all of the tested organisms. PMID:19924042

  12. Evaluation of Antioxidant and Antibacterial Activities of Aqueous, Methanolic and Alkaloid Extracts from Mitragyna Speciosa (Rubiaceae Family Leaves

    Mohd I. Mohd. Said

    2009-10-01

    Full Text Available Studies on the antioxidant and antimicrobial activities of Mitragyna speciosa leaf extracts are lacking. In this study the antioxidant properties of water, methanolic and alkaloid M. speciosa leaf extracts were evaluated using the DPPH (2,2-diphenyl-1- picrylhydrazyl radical scavenging method. The amount of total phenolics and flavanoid contents were also estimated. The DPPH IC50 values of the aqueous, alkaloid and methanolic extracts were 213.4, 104.81 and 37.08 μg/mL, respectively. The total phenolic content of the aqueous, alkaloid and methanolic extracts were 66.0 mg, 88.4, 105.6 mg GAE/g, respectively, while the total flavanoid were 28.2, 20.0 and 91.1 mg CAE/g respectively. The antioxidant activities were correlated with the total phenolic content. This result suggests that the relatively high antioxidant activity of the methanolic extract compared to aqueous and alkaloid extract could be possibly be due to its high phenolic content. The aqueous, alkaloid and methanolic extracts were screened for antimicrobial activity. The extracts showed antimicrobial activity against Salmonella typhi and Bacillus subtilis. The minimum inhibitory concentrations (MICs of extracts determined by the broth dilution method ranged from 3.12 to 6.25 mg/mL. The alkaloid extract was found to be most effective against all of the tested organisms.

  13. Metabolic activation of pyrrolizidine alkaloids leading to phototoxicity and photogenotoxicity in human HaCaT keratinocytes.

    Wang, Chia-Chi; Xia, Qingsu; Li, Meng; Wang, Shuguang; Zhao, Yuewei; Tolleson, William H; Yin, Jun-Jie; Fu, Peter P

    2014-01-01

    Pyrrolizidine alkaloids, produced by a large number of poisonous plants with wide global distribution, are associated with genotoxicity, tumorigenicity, and hepatotoxicity in animals and humans. Mammalian metabolism converts pyrrolizidine alkaloids to reactive pyrrolic metabolites (dehydropyrrolizidine alkaloids) that form covalent protein and DNA adducts. Although a mechanistic understanding is currently unclear, pyrrolizidine alkaloids can cause secondary (hepatogenous) photosensitization and induce skin cancer. In this study, the phototoxicity of monocrotaline, riddelliine, dehydromonocrotaline, dehydroriddelliine, and dehydroretronecine (DHR) in human HaCaT keratinocytes under ultraviolet A (UVA) irradiation was determined. UVA irradiation of HaCaT cells treated with dehydromonocrotaline, dehydroriddelline, and DHR resulted in increased release of lactate dehydrogenase and enhanced photocytotoxicity proportional to the UVA doses. UVA-induced photochemical DNA damage also increased proportionally with dehydromonocrotaline and dehydroriddelline. UVA treatment potentiated the formation of 8-hydroxy-2'-deoxyguanosine DNA adducts induced by dehydromonocrotaline in HaCaT skin keratinocytes. Using electron spin resistance trapping, we found that UVA irradiation of dehydromonocrotaline and dehydroriddelliine generates reactive oxygen species (ROS), including hydroxyl radical, singlet oxygen, and superoxide, and electron transfer reactions, indicating that cytotoxicity and genotoxicity of these compounds could be mediated by ROS. Our results suggest that dehydropyrrolizidine alkaloids formed or delivered to the skin cause pyrrolizidine alkaloid-induced secondary photosensitization and possible skin cancer. PMID:25436474

  14. Quantitative Determination of Alkaloids in Lotus Flower (Flower Buds of Nelumbo nucifera and Their Melanogenesis Inhibitory Activity

    Toshio Morikawa

    2016-07-01

    Full Text Available A quantitative analytical method for five aporphine alkaloids, nuciferine (1, nornuciferine (2, N-methylasimilobine (3, asimilobine (4, and pronuciferine (5, and five benzylisoquinoline alkaloids, armepavine (6, norarmepavine (7, N-methylcoclaurine (8, coclaurine (9, and norjuziphine (10, identified as the constituents responsible for the melanogenesis inhibitory activity of the extracts of lotus flowers (the flower buds of Nelumbo nucifera, has been developed using liquid chromatography-mass spectrometry. The optimum conditions for separation and detection of these 10 alkaloids were achieved on a πNAP column, a reversed-phase column with naphthylethyl group-bonded silica packing material, with CH3CN–0.2% aqueous acetic acid as the mobile phase and using mass spectrometry equipped with a positive-mode electrospray ionization source. According to the protocol established, distributions of these 10 alkaloids in the petal, receptacle, and stamen parts, which were separated from the whole flower, were examined. As expected, excellent correlations were observed between the total alkaloid content and melanogenesis inhibitory activity. Among the active alkaloids, nornuciferine (2 was found to give a carbamate salt (2′′ via formation of an unstable carbamic acid (2′ by absorption of carbon dioxide from the air.

  15. Effects of tryptophan derivatives and β-carboline alkaloids on radiation- and peroxide-induced transformations of ethanol

    The subject of this study was investigation of interactions of tryptophan and its derivatives, including structurally related β-carboline alkaloids with oxygen- and carbon-centered radicals being formed during radiation- and peroxide-induced transformations of ethanol. It was shown that the above named compounds suppressed recombination and disproportionation reactions of α-hydroxyethyl radicals. The inhibitory effects of tryptophan, 5-hydroxytryptophan and serotonin were mainly realized by means of reduction and addition reactions, while those of β-carboline alkaloids – harmine, harmane and harmaline – were due to oxidation reactions. Melatonin displayed low reactivity towards α-hydroxyethyl radicals. Tryptophan derivatives and β-carboline alkaloids were found to inhibit radiation-induced oxidation of ethanol while being virtually not used up. The low transformation yields of tryptophan, 5-hydroxytryptophan and serotonin, as well as β-carboline alkaloids, indicate their capability of regeneration, which could occur on interaction of tryptophan with O·−2 and HO·2, or on oxidation of α-hydroxyethyl radicals by β-carboline alkaloids. - Highlights: • Tryptophan, 5-hydroxytryptophane and serotonin can reduce or add α-HER. • β-Carboline alkaloids – harmane, harmine, harmaline – can oxidize α-HER. • Tryptophan and its derivatives can reduce oxygen-centered radicals

  16. In Vitro Activity of Plant Extracts and Alkaloids against Clinical Isolates of Extended-Spectrum b-Lactamase (ESBL-Producing Strains

    Qing Zhang

    2011-06-01

    Full Text Available The antibacterial activity of 80% ethanol extracts of 10 medicinal plants collected in Yunnan (Southwest China, was tested against clinical isolates of extended-spectrum b-lactamase (ESBL-producing strains. Their MIC values ranged between 1.56–12.50 mg/mL. The most active plant extract was Chelidonium majus L. (MIC = 1.56 mg/mL. Two potent isoquinoline alkaloids, 8-hydroxydihydrosanguinarine and 8-hydroxydihydrochelerythrine, were identified as the major active principles through bioassay-guided fractionation and identification of the active ethyl acetate fraction from C. majus, with minimum MIC/MBC values of 15.63/62.50 mg/mL.

  17. Cumarinas e alcaloides de Rauia resinosa (rutaceae Coumarins and alkaloids from Rauia resinosa (rutaceae

    Tatiane Regina Albarici

    2010-01-01

    Full Text Available The genus Rauia, that is poorly chemically studied, belongs to the Rutaceae family. This family has been known to contain a large variety of secondary metabolites. Our phytochemical investigation of the stem and leaves of Rauia resinosa has led to the identification of the structurally related coumarins: murralongin (1, murrangatin (2, munomicrolin (3, murrangatin diacetate (4, umbelliferone (5, rauianin (6 and one novel coumarin: 3-ethylrauianin (7; the alkaloids: N-methyl-4-methoxy-2-quinolone (8, mirtopsine (9, dictamine (10, γ-fagarine (11, skimmianine (12, Z-dimethylrhoifolinate (13, zantodioline (14, zantobungeanine (15, veprissine (16, one novel alkaloid 7-hydroxy-8-methoxy-N-methylflindersine (17 and 8-hydroxy-N-methylflindersine (18 that is described as a natural product for the first time, and a mixture of steroids: as sitosterol and stigmasterol.

  18. Coumarin and alkaloids of Rauia resinosa (Rutaceae); Cumarinas e alcaloides de Rauia resinosa (Rutaceae)

    Albarici, Tatiane Regina; Vieira, Paulo Cezar; Fernandes, Joao Batista; Silva, Maria Fatima das Gracas Fernandes da, E-mail: paulo@dq.ufscar.b [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica; Pirani, Jose Rubens [Universidade de Sao Paulo (USP), SP (Brazil). Inst. de Biociencias. Dept. de Botanica

    2010-07-01

    The genus Rauia, that is poorly chemically studied, belongs to the Rutaceae family. This family has been known to contain a large variety of secondary metabolites. Our phytochemical investigation of the stem and leaves of Rauia resinosa has led to the identification of the structurally related coumarins: murralongin (1), murrangatin (2), munomicrolin (3), murrangatin diacetate (4), umbelliferone (5), rauianin (6) and one novel coumarin: 3-ethylrauianin (7); the alkaloids: N-methyl-4-methoxy-2-quinolone (8), mirtopsine (9), dictamine (10), g-fagarine (11), skimmianine (12), Z-dimethylrhoifolinate (13), zantodioline (14), zantobungeanine (15), veprissine (16), one novel alkaloid 7-hydroxy-8-methoxy-N-methylflindersine (17) and 8-hydroxy-N-methylflindersine (18) that is described as a natural product for the first time, and a mixture of steroids: as sitosterol and stigmasterol. (author)

  19. Cytotoxic and antimicrobial aporphine alkaloids from Fissistigma poilanei (Annonaceae) collected in Vietnam.

    Thuy, Tran Thi Thanh; Quan, Tran Duc; Anh, Nguyen Thi Hoang; Sung, Tran Van

    2012-01-01

    Two new aporphine alkaloids: 8-hydroxy-9-methoxy-1,2-methylenedioxyaporphine (1) and 8-hydroxy-3,9-dimethoxy-1,2-methylenedioxyaporphine (2) were isolated from the ethyl acetate extract of Fissistigma poilanei along with five known compounds: oxocrebanine (3), kuafumine (4), (2R,3R)-3',4',5,7-tetrahydroxydihydroflavonol-3-O-α-L-rhamnopyranoside (5), (+)-catechin 3-O-α-L-rhamnopyranoside (6) and quercetine 3,7-dimethoxy-3'-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranoside (7). These two new aporphine alkaloids exhibited a moderate cytotoxic activity against four human cancer cell lines (KB, Hep-G2, MCF-7, LU) as well as antimicrobial activity against Lactobacillus fermentum, Enterococcus faecium, Staphylococcus aureus and Bacillus subtillis. PMID:22077457

  20. Synthesis of Carbazole Alkaloids by Ring-Closing Metathesis and Ring Rearrangement-Aromatization.

    Dhara, Kalyan; Mandal, Tirtha; Das, Joydeb; Dash, Jyotirmayee

    2015-12-21

    Aprocess for the assembly of carbazole alkaloids has been developed on the basis of ring-closing metathesis (RCM) and ringrearrangement-aromatization (RRA) as the key steps. This method is based on allyl Grignard addition to isatin derivatives to provide smooth access to 2,2-diallyl 3-oxindole derivatives through a 1,2-allyl shift. The diallyl derivatives were used as RCM precursors to afford a novel class of spirocyclopentene-3-oxindole derivatives, which underwent a novel RRA reaction to afford carbazole derivatives. The synthetic sequence to carbazoles was shortened by combining the RCM and RRA steps in an orthogonal tandem catalytic process. The utility of this methodology was further demonstrated by the straightforward synthesis of carbazole alkaloids, including amukonal derivative, girinimbilol, heptaphylline, and bis(2-hydroxy-3-methylcarbazole). PMID:26768698