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Sample records for chalcone

  1. Stereoselectivity of chalcone isomerase with chalcone derivatives: a computational study.

    Science.gov (United States)

    Yao, Yuan; Zhang, Hui; Li, Ze-Sheng

    2013-11-01

    Chalcone isomerase (CHI) catalyzes the intramolecular cyclization of chalcones into flavonoids. The activity of CHI is essential for the biosynthesis of flavonoids precursors of floral pigments and phenylpropanoid plant defense compounds. In the present study, we explored the detailed binding structures and binding free energies for two different active site conformations of CHI with s-cis/s-trans conformers of three chalcone compounds by performing molecular dynamics (MD) simulations and binding free energy calculations. The computational results indicate that s-cis/s-trans conformers of chalcone compounds are orientated in the similar binding position in the active site of CHI and stabilized by the different first hydrogen bond network and the same second hydrogen bond network. The first hydrogen bond network results in much lower binding affinity of s-trans conformer of chalcone compound with CHI than that of s-cis conformer. The conformational change of the active site residue T48 from indirectly interacting with the substrate via the second hydrogen bond network to directly forming the hydrogen bond with the substrates cannot affect the binding mode of both conformers of chalcone compounds, but remarkably improves the binding affinity. These results show that CHI has a strong stereoselectivity. The calculated binding free energies for three chalcone compounds with CHI are consistent with the experimental activity data. In addition, several valuable insights are suggested for future rational design and discovery of high-efficiency mutants of CHI.

  2. Heterocyclic chalcone analogues as potential anticancer agents.

    Science.gov (United States)

    Sharma, Vikas; Kumar, Vipin; Kumar, Pradeep

    2013-03-01

    Chalcones, aromatic ketones and enones acting as the precursor for flavonoids such as Quercetin, are known for their anticancer effects. Although, parent chalcones consist of two aromatic rings joined by a three-carbon α,β-unsaturated carbonyl system, various synthetic compounds possessing heterocyclic rings like pyrazole, indole etc. are well known and proved to be effective anticancer agents. In addition to their use as anticancer agents in cancer cell lines, heterocyclic analogues are reported to be effective even against resistant cell lines. In this connection, we hereby highlight the potential of various heterocyclic chalcone analogues as anticancer agents with a brief summary about therapeutic potential of chalcones, mechanism of anticancer action of various chalcone analogues, and current and future prospects related to the chalcones-derived anticancer research. Furthermore, some key points regarding chalcone analogues have been reviewed by analyzing their medicinal properties.

  3. Advances in chalcones with anticancer activities.

    Science.gov (United States)

    Karthikeyan, Chandrabose; Moorthy, Narayana S H Narayana; Ramasamy, Sakthivel; Vanam, Uma; Manivannan, Elangovan; Karunagaran, Devarajan; Trivedi, Piyush

    2015-01-01

    Chalcones are naturally occurring compounds exhibiting broad spectrum biological activities including anticancer activity through multiple mechanisms. Literature on anticancer chalcones highlights the employment of three pronged strategies, namely; structural manipulation of both aryl rings, replacement of aryl rings with heteroaryl scaffolds, molecular hybridization through conjugation with other pharmacologically interesting scaffolds for enhancement of anticancer properties. Methoxy substitutions on both the aryl rings (A and B) of the chalcones, depending upon their positions in the aryl rings appear to influence anticancer and other activities. Similarly, heterocyclic rings either as ring A or B in chalcones, also influence the anticancer activity shown by this class of compounds. Hybrid chalcones formulated by chemically linking chalcones to other prominent anticancer scaffolds such as pyrrol[2,1-c][1,4]benzodiazepines, benzothiazoles, imidazolones have demonstrated synergistic or additive pharmacological activities. The successful application of these three pronged strategies for discovering novel anticancer agents based on chalcone scaffold has resulted in many novel and chemically diverse chalcones with potential therapeutic application for many types of cancer. This review summarizes the concerted efforts expended on the design and development of anticancer chalcones recorded in recent literature and also provides an overview of the patents published in this area between 2007 and 2014 (WO2013022951, WO201201745 & US2012029489).

  4. Toxicological assessment of Ashitaba Chalcone.

    Science.gov (United States)

    Maronpot, Robert R

    2015-03-01

    The plant Angelica keiskei contains two main physiologically active flavonoid chalcones, 4-hydroxyderricin and xanthoangelol. Known as ashitaba in Japan, powder from the sap is widely consumed for its medicinal properties in Asia as a dietary supplement. Limited previously reported mammalian studies were without evidence of toxicity. GLP studies reported here, including a bacterial reverse mutation assay, a chromosome aberration assay, and an in vivo micronucleus assay are negative for genotoxicity. A GLP- compliant 90-day repeated oral gavage study of ashitaba yellow sap powder containing 8.45% chalcones in Sprague Dawley rats resulted in expected known physiological effects on coagulation parameters and plasma lipids at 300 and 1000 mg/kg/day. Ashitaba-related pathology included a dose-related male rat-specific alpha 2-urinary globulin nephropathy at 100, 300, and 1000 mg/kg/day and jejunal lymphangiectasia in both sexes at 1000 mg/kg/day. All other study parameters and histopathological changes were incidental or not of toxicological concern. Based on these studies ashitaba chalcone powder is not genotoxic with a NOAEL of 300 mg/kg in male and female rats.

  5. Solvent-Free Synthesis of Chalcones

    Science.gov (United States)

    Palleros, Daniel R.

    2004-01-01

    The synthesis of twenty different chalcones in the absence of solvent is presented. The results indicated that out of the twenty different chalcones investigated seventeen can be obtained in a matter of minutes by mixing the corresponding benzaldehyde and acetophenone in the presence of solid NaOH in a mortar with pestle.

  6. Chalcones: compounds possessing a diversity in applications

    OpenAIRE

    2012-01-01

    Chalcones are a class of α, β- unsaturated carbonyl compounds that form the central core for a variety of naturally occurring biologically active compounds. They exhibit tremendous potential to act as a pharmacological agent. Besides their various pharmacological activities, chalcones have been explored for different optical applications including second harmonic generation materials in non- linear optics, fluorescent probe for sensing different molecules.

  7. Chalcones: compounds possessing a diversity in applications

    Directory of Open Access Journals (Sweden)

    Urmila Berar

    2012-10-01

    Full Text Available Chalcones are a class of α, β- unsaturated carbonyl compounds that form the central core for a variety of naturally occurring biologically active compounds. They exhibit tremendous potential to act as a pharmacological agent. Besides their various pharmacological activities, chalcones have been explored for different optical applications including second harmonic generation materials in non- linear optics, fluorescent probe for sensing different molecules.

  8. Monoamine oxidase inhibitory activities of heterocyclic chalcones.

    Science.gov (United States)

    Minders, Corné; Petzer, Jacobus P; Petzer, Anél; Lourens, Anna C U

    2015-11-15

    Studies have shown that natural and synthetic chalcones (1,3-diphenyl-2-propen-1-ones) possess monoamine oxidase (MAO) inhibition activities. Of particular importance to the present study is a report that a series of furanochalcones acts as MAO-B selective inhibitors. Since the effect of heterocyclic substitution, other than furan (and more recently thiophene, piperidine and quinoline) on the MAO inhibitory properties of the chalcone scaffold remains unexplored, the aim of this study was to synthesise and evaluate further heterocyclic chalcone analogues as inhibitors of the human MAOs. For this purpose, heterocyclic chalcone analogues that incorporate pyrrole, 5-methylthiophene, 5-chlorothiophene and 6-methoxypyridine substitution were examined. Seven of the nine synthesised compounds exhibited IC50 values chalcones are reversible and competitive MAO inhibitors. 4h, however, may exhibit tight-binding to MAO-B, a property linked to its thiophene moiety. We conclude that high potency chalcones such as 4h represent suitable leads for the development of MAO-B inhibitors for the treatment of Parkinson's disease and possibly other neurodegenerative disorders.

  9. CHALCONE AS A VERSATILE MOIETY FOR DIVERSE PHARMACOLOGICAL ACTIVITIES

    OpenAIRE

    2012-01-01

    Chalcones are 1, 3-diphenyl-2-propene-1-one, consist of two aromatic rings linked by a three carbon α, β-unsaturated carbonyl system. The chemistry of chalcones has generated intensive scientific studies throughout the world. Especially interest has been focused on the synthesis and biodynamic activities of chalcones. These are considered to be precursors of flavonoids and isoflavonoids. The aim of this review is to summarize chalcones and their diverse pharmacological activities like antican...

  10. ANTIMICROBIAL SCREENING OF SOME NOVEL SUBSTITUTED CHALCONE DERIVATIVES

    OpenAIRE

    2012-01-01

    Chalcone is an aromatic ketone that forms the central core for the variety of important biological compounds, which are collectively known as chalcones. The derivatives of chalcones with an annular nitrogen atom in the phenyl ring were reported to have a wide range of biologically activities, such as antibacterial, anti-tuberculostatic and anti- inflammatory. The chalcones, two aromatic rings are linked by an aliphatic three carbon chain which bears a very good synthon so that variety of nove...

  11. Chalcone Scaffold in Anticancer Armamentarium: A Molecular Insight

    Directory of Open Access Journals (Sweden)

    Manik Das

    2016-01-01

    Full Text Available Cancer is an inevitable matter of concern in the medicinal chemistry era. Chalcone is the well exploited scaffold in the anticancer domain. The molecular mechanism of chalcone at cellular level was explored in past decades. This mini review provides the most recent updates on anticancer potential of chalcones.

  12. SYNTHESIS AND CHARACTERIZATION OF SOME NOVEL SUBSTITUTED CHALCONE DERIVATIVES

    Directory of Open Access Journals (Sweden)

    Ramesh Dhani

    2012-12-01

    Full Text Available Chalcone is an aromatic ketone that forms the central core for the variety of important biological compounds, which are collectively known as chalcones. The name chalcones was given by Kostanecki and Tambor. The chalcones, two aromatic rings are linked by an aliphatic three carbon chain which bears a very good synthon so that variety of novel heterocyclics with good pharmaceutical profile can be designed. Chalcones have been considered as a magic moiety possessing myriad spectrum of medicinal activities. Diversity of biological response profile has attracted considerable interest of several researchers across the globe to explore this skeleton for its assorted therapeutic significance. By using different synthetic methods new chalcone derivatives were synthesized and characterized by physicochemical analysis. Chalcone is a lead nucleus for future developments to get effective compounds.

  13. Two-photon-induced cycloreversion reaction of chalcone photodimers

    Science.gov (United States)

    Träger, J.; Härtner, S.; Heinzer, J.; Kim, H.-C.; Hampp, N.

    2008-04-01

    The photocleavage reaction of chalcone photodimers has been studied using a two-photon process. For this purpose, a novel chalcone dimer has been synthesized as a low molecular weight model substance for polymer bound chalcones and its photochemistry triggered by two-photon-absorption (2PA) has been investigated using a pulsed frequency-doubled Nd:YAG-laser. The 2PA-induced cycloreversion reaction selectively leads to the cleavage of the chalcone photodimers resulting in the formation of monomeric chalcone molecules. Hence, as an application chalcones can be used as a photosensitive linker which can be cleaved beyond an UV-absorbing barrier. The 2PA cross section of the chalcone photodimer was determined to be of 1.1 × 10 -49 cm 4 s photon -1 (11 GM).

  14. Structural Antitumoral Activity Relationships of Synthetic Chalcones

    Science.gov (United States)

    Echeverria, Cesar; Santibañez, Juan Francisco; Donoso-Tauda, Oscar; Escobar, Carlos A.; Ramirez-Tagle, Rodrigo

    2009-01-01

    Relationships between the structural characteristic of synthetic chalcones and their antitumoral activity were studied. Treatment of HepG2 cells for 24 h with synthetic 2’-hydroxychalcones resulted in apoptosis induction and dose-dependent inhibition of cell proliferation. The calculated reactivity indexes and the adiabatic electron affinities using the DFT method including solvent effects, suggest a structure-activity relationship between the Chalcones structure and the apoptosis in HepG2 cells. The absence of methoxy substituents in the B ring of synthetic 2’-hydroxychalcones, showed the mayor structure-activity pattern along the series. PMID:19333443

  15. Toxicity assessments of chalcone and some synthetic chalcone analogues in a zebrafish model.

    Science.gov (United States)

    Lee, Ya-Ting; Fong, Tsorng-Harn; Chen, Hui-Min; Chang, Chao-Yuan; Wang, Yun-Hsin; Chern, Ching-Yuh; Chen, Yau-Hung

    2014-01-07

    The aim of this study was to investigate the in vivo toxicities of some novel synthetic chalcones. Chalcone and four chalcone analogues 1a-d were evaluated using zebrafish embryos following antibody staining to visualize their morphological changes and muscle fiber alignment. Results showed that embryos treated with 3'-hydroxychalcone (compound 1b) displayed a high percentage of muscle defects (96.6%), especially myofibril misalignment. Ultrastructural analysis revealed that compound 1b-treated embryos displayed many muscle defect phenotypes, including breakage and collapse of myofibrils, reduced cell numbers, and disorganized thick (myosin) and thin (actin) filaments. Taken together, our results provide in vivo evidence of the myotoxic effects of the synthesized chalcone analogues on developing zebrafish embryos.

  16. Evaluation of the anti-inflammatory effect of chalcone and chalcone analogues in a zebrafish model.

    Science.gov (United States)

    Chen, Yau-Hung; Wang, Wei-Hua; Wang, Yun-Hsin; Lin, Zi-Yu; Wen, Chi-Chung; Chern, Ching-Yuh

    2013-02-05

    The aim of this study was to investigate novel chalcones with potent anti-inflammatory activities in vivo. Chalcone and two chalcone analogues (compound 5 and 9) were evaluated using a caudal fin-wounded transgenic zebrafish line "Tg(mpx:gfp)" to visualize the effect of neutrophil recruitment dynamically. Results showed that treatment with compound 9 not only affected wound-induced neutrophil recruitment, but also affected Mpx enzymatic activity. Moreover, protein expression levels of pro-inflammatory factors (Mpx, NFκB, and TNFα) were also regulated by compound 9. Taken together, our results provide in vivo evidence of the anti-inflammatory effects of synthesized chalcone analogues on wound-induced inflammation.

  17. Toxicity Assessments of Chalcone and Some Synthetic Chalcone Analogues in a Zebrafish Model

    Directory of Open Access Journals (Sweden)

    Ya-Ting Lee

    2014-01-01

    Full Text Available The aim of this study was to investigate the in vivo toxicities of some novel synthetic chalcones. Chalcone and four chalcone analogues 1a–d were evaluated using zebrafish embryos following antibody staining to visualize their morphological changes and muscle fiber alignment. Results showed that embryos treated with 3'-hydroxychalcone (compound 1b displayed a high percentage of muscle defects (96.6%, especially myofibril misalignment. Ultrastructural analysis revealed that compound 1b-treated embryos displayed many muscle defect phenotypes, including breakage and collapse of myofibrils, reduced cell numbers, and disorganized thick (myosin and thin (actin filaments. Taken together, our results provide in vivo evidence of the myotoxic effects of the synthesized chalcone analogues on developing zebrafish embryos.

  18. An antileishmanial chalcone from Chinese licorice roots

    DEFF Research Database (Denmark)

    Christensen, S B; Ming, C; Andersen, L

    1994-01-01

    A bioassay guided fractionation of an extract of Chinese licorice roots led to the isolation of (E)-1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-[4- hydroxy-3-(3-methyl-2-butenyl]phenyl-2-propen-1-one, which in vitro showed potent antileishmanial activity. In addition, the novel chalcone (E)-...

  19. A novel chalcone derivative from Onychium japonicum

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    A novel chalcone derivative was isolated from Onychium japonicum and its structure was elucidated by spectroscopic methods.The isolated compound showed cytotoxic activity against the human carcinoma cell lines Hela and BEL-7402 in vitro.(C) 2007 Hong Quan Duan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  20. Therapeutic potential of chalcones as cardiovascular agents.

    Science.gov (United States)

    Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar

    2016-03-01

    Cardiovascular diseases are the leading cause of death affecting 17.3 million people across the globe and are estimated to affect 23.3 million people by year 2030. In recent years, about 7.3 million people died due to coronary heart disease, 9.4 million deaths due to high blood pressure and 6.2 million due to stroke, where obesity and atherosclerotic progression remain the chief pathological factors. The search for newer and better cardiovascular agents is the foremost need to manage cardiac patient population across the world. Several natural and (semi) synthetic chalcones deserve the credit of being potential candidates to inhibit various cardiovascular, hematological and anti-obesity targets like angiotensin converting enzyme (ACE), cholesteryl ester transfer protein (CETP), diacylglycerol acyltransferase (DGAT), acyl-coenzyme A: cholesterol acyltransferase (ACAT), pancreatic lipase (PL), lipoprotein lipase (LPL), calcium (Ca(2+))/potassium (K(+)) channel, COX-1, TXA2 and TXB2. In this review, a comprehensive study of chalcones, their therapeutic targets, structure activity relationships (SARs), mechanisms of actions (MOAs) have been discussed. Chemically diverse chalcone scaffolds, their derivatives including structural manipulation of both aryl rings, replacement with heteroaryl scaffold(s) and hybridization through conjugation with other pharmacologically active scaffold have been highlighted. Chalcones which showed promising activity and have a well-defined MOAs, SARs must be considered as prototype for the design and development of potential anti-hypertensive, anti-anginal, anti-arrhythmic and cardioprotective agents. With the knowledge of these molecular targets, structural insights and SARs, this review may be helpful for (medicinal) chemists to design more potent, safe, selective and cost effective chalcone derivatives as potential cardiovascular agents.

  1. Chalcones as Promising Lead Compounds on Cancer Therapy.

    Science.gov (United States)

    León-González, Antonio J; Acero, Nuria; Muñoz-Mingarro, Dolores; Navarro, Inmaculada; Martín-Cordero, Carmen

    2015-01-01

    Chalcones constitute a group of phenolic compounds that command an increasing interest on cancer research. Natural chalcones are widespread through the plant kingdom. The most abundant and investigated chalcones are isoliquiritigenin, flavokawain and xanthohumol, which are present in the Fabaceae, Piperaceae, Cannabaceae, and Moraceae families. These chalcones have been shown to be promising lead antitumor-chemopreventive drugs by three different activities: antioxidants, cytotoxic and apoptosis inducers. In the recent years, SAR (structure-activity relationship) has contributed towards the improvement of anticancer properties of chalcones by substituting aryl rings and introducing heterocyclic moieties. This review summarizes the anticancer activities shown by natural chalcones and the SAR and describes how different chemical moiety modifications could lead them to be therapeutically useful in the treatment of cancer.

  2. CHALCONE AS A VERSATILE MOIETY FOR DIVERSE PHARMACOLOGICAL ACTIVITIES

    Directory of Open Access Journals (Sweden)

    Hatish Prashar*, Anshul Chawla, Anil Kumar Sharma and Rajeev Kharb

    2012-07-01

    Full Text Available Chalcones are 1, 3-diphenyl-2-propene-1-one, consist of two aromatic rings linked by a three carbon α, β-unsaturated carbonyl system. The chemistry of chalcones has generated intensive scientific studies throughout the world. Especially interest has been focused on the synthesis and biodynamic activities of chalcones. These are considered to be precursors of flavonoids and isoflavonoids. The aim of this review is to summarize chalcones and their diverse pharmacological activities like anticancer, antimicrobial, analgesic and antiviral activities etc.

  3. Recent trends of chalcones potentialities as antiproliferative and antiresistance agents.

    Science.gov (United States)

    Winter, Evelyn; Locatelli, Claudriana; Di Pietro, Attilio; Creczynski-Pasa, Tânia B

    2015-01-01

    Chalcones are natural compounds found in plants, fruits and vegetables. This class of compounds has shown many biological activities including antioxidant, antimicrobial, anti-inflammatory, antifungal and antihypertensive, among others. In cancer, it has been reported that chalcones interfere in several points of the signal transduction pathways related to cellular proliferation, angiogenesis, metastasis, apoptosis and the reversal of multidrug resistance. The large number of research articles and patents related to chalcones is already an indication of their importance as a lead class of compounds. This article gathers recent efforts to elucidate the molecular mechanisms of action of chalcones, associated with their anticancer and anti resistance potential.

  4. Structural Antitumoral Activity Relationships of Synthetic Chalcones

    Directory of Open Access Journals (Sweden)

    Cesar Echeverria

    2009-01-01

    Full Text Available Relationships between the structural characteristic of synthetic chalcones and their antitumoral activity were studied. Treatment of HepG2 cells for 24 h with synthetic 2’-hydroxychalcones resulted in apoptosis induction and dose-dependent inhibition of cell proliferation. The calculated reactivity indexes and the adiabatic electron affinities using the DFT method including solvent effects, suggest a structure-activity relationship between the Chalcones structure and the apoptosis in HepG2 cells. The absence of methoxy substituents in the B ring of synthetic 2’-hydroxychalcones, showed the mayor structure-activity pattern along the series.

  5. Five new prenylated chalcones from Desmodium renifolium.

    Science.gov (United States)

    Li, Yan-Ping; Yang, Yu-Chun; Li, Yin-Ke; Jiang, Zhi-Yong; Huang, Xiang-Zhong; Wang, Wei-Guang; Gao, Xue-Mei; Hu, Qiu-Fen

    2014-06-01

    Five unusual new prenylated chalcones, renifolins D-H (1-5), were isolated from whole Desmodium renifolium plants. All of their structures were determined by spectroscopic methods including 1D and 2D NMR. All of the isolates were evaluated for cytotoxicity using five tumor cell lines. Compounds 2 and 3 exhibited cytotoxicity against A549 cells, with IC50 values of 2.8 and 2.2 μM, respectively.

  6. Activation of oxidative stress response by hydroxyl substituted chalcones and cyclic chalcone analogues in mitochondria.

    Science.gov (United States)

    Guzy, J; Vasková-Kubálková, J; Rozmer, Z; Fodor, K; Mareková, M; Poskrobová, M; Perjési, P

    2010-02-05

    We investigated the effect of hydroxyl substituted chalcone (1a) and some chalcone analogues (1b-d) on isolated rat liver mitochondria to gain new insights into the cytotoxic mechanism of these compounds. We observed an inhibitory effect on phosphorylation and the partial uncoupling of compounds 1a and 1d. Increased radical generation and possible covalent interaction of the compounds with cellular thiols resulted in glutathione (GSH) depletion and modulation of the investigated mitochondrial activities. Disruption of interconnected mechanisms as electron transport chain and energetic metabolism, ROS production and insufficiency of antioxidant defensive system could lead to induction of cell death.

  7. Chalcone derivatives as potential antifungal agents: Synthesis, and antifungal activity

    Directory of Open Access Journals (Sweden)

    Deepa Gupta

    2015-01-01

    Full Text Available Much research has been carried out with the aim to discover the therapeutic values of chalcone derivatives. Chalcones possess wide range of pharmacological activity such as antibacterial, antimalarial, antiprotozoal, antitubercular, anticancer, and antifungal agents etc. The presence of reactive α,β-unsaturated keto group in chalcones is found to be responsible for their biological activity. The rapid developments of resistance to antifungal agents, led to design, and synthesize the new antifungal agents. The derivatives of chalcones were prepared using Claisen-Schmidt condensation scheme with appropriate tetralone and aldehyde derivatives. Ten derivatives were synthesized and were biologically screened for antifungal activity. The newly synthesized derivatives of chalcone showed antifungal activity against fungal species, Microsporum gypseum. The results so obtained were superior or comparable to ketoconazole. It was observed that none of the compounds tested showed positive results for fungi Candida albicans nor against fungi Aspergillus niger. Chalcone derivatives showed inhibitory effect against M. gypseum species of fungus. It was found that among the chalcone derivatives so synthesized, two of them, that is, 4-chloro derivative, and unsubstituted derivative of chalcone showed antifungal activity superior to ketoconazole. Thus, these can be the potential new molecule as antifungal agent.

  8. Chalcones Enhance TRAIL-Induced Apoptosis in Prostate Cancer Cells

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    Ewelina Szliszka

    2009-12-01

    Full Text Available Chalcones exhibit chemopreventive and antitumor effects. Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL is a naturally occurring anticancer agent that induces apoptosis in cancer cells and is not toxic to normal cells. We examined the cytotoxic and apoptotic effect of five chalcones in combination with TRAIL on prostate cancer cells. The cytotoxicity was evaluated by the MTT and LDH assays. The apoptosis was determined using flow cytometry with annexin V-FITC. Our study showed that all five tested chalcones: chalcone, licochalcone-A, isobavachalcone, xanthohumol, butein markedly augmented TRAIL-mediated apoptosis and cytotoxicity in prostate cancer cells and confirmed the significant role of chalcones in chemoprevention of prostate cancer.

  9. QTAIM electron density study of natural chalcones

    Science.gov (United States)

    González Moa, María J.; Mandado, Marcos; Cordeiro, M. Natália D. S.; Mosquera, Ricardo A.

    2007-09-01

    QTAIM atomic and bond properties, ionization potential, and O-H bond dissociation energies calculated at the B3LYP/6-311++G(2d,2p) level indicate the natural chalcones bear a significant radical scavenging activity. However, their ionization potentials indicate they decrease the electron-transfer rate between antioxidant and oxygen that yields the pro-oxidative cations less than other natural antioxidants. Rings A and B display slight and similar positive charges, whereas ring B is involved in exocycle delocalization at a larger extension.

  10. ANTIMICROBIAL SCREENING OF SOME NOVEL SUBSTITUTED CHALCONE DERIVATIVES

    Directory of Open Access Journals (Sweden)

    Ramesh Dhani

    2012-10-01

    Full Text Available Chalcone is an aromatic ketone that forms the central core for the variety of important biological compounds, which are collectively known as chalcones. The derivatives of chalcones with an annular nitrogen atom in the phenyl ring were reported to have a wide range of biologically activities, such as antibacterial, anti-tuberculostatic and anti- inflammatory. The chalcones, two aromatic rings are linked by an aliphatic three carbon chain which bears a very good synthon so that variety of novel heterocyclics with good pharmaceutical profile can be designed. Chalcones have been considered as a magic moiety possessing myriad spectrum of medicinal activities. Diversity of biological response profile has attracted considerable interest of several researchers across the globe to explore this skeleton for its assorted therapeutic significance. The synthesized chalcone derivatives were screened for antimicrobial activity by comparing with the standard drug of ciprofloxacin on two gram positive and two gram negative strains, the synthesized compounds, by using Disc-diffusion method. Chalcone is a lead nucleus for future developments to get effective compounds.

  11. The Synthesis of Photocrosslinkable Chalcone-Bearing Polyphosphazenes

    Science.gov (United States)

    1993-05-18

    Form Approvea TION PAGE oM6 No 0704ý07887 AD-A264 915 tef,j I u tepre ntcn m ~efrfve" M~10%Wf- I%.qJ( The SytessofPoocoslna lee Chalcone -Beanng...N00014-91-J- 1194 R&T Code: 4132007 Technical Report No. 13 The Synthesis of Photocrosslinkable Chalcone -Bearing Polyphosphazenes by Harry R. Allcock and...for public release and sale; its distribution is unlimited. The Synthesis of Photocrosslinkable Chalcone -Bearing Polyphosphazenes Harry R. Allcock* and

  12. New chalcone and dimeric chalcones with 1,4-p-benzoquinone residue from Combretum yunnanense.

    Science.gov (United States)

    Wu, Ming-Mei; Wang, Li-Qin; Hua, Yan; Chen, Ye-Gao; Wang, Yuan-Yuan; Li, Xing-Yao; Li, Yan; Li, Ting; Yang, Xun-Yun; Tang, Zheng-Rong

    2011-03-01

    New chalcone and dimeric chalcones with 1,4- P-benzoquinone residue, combrequinone A (1), combrequinone B (2), and combrequinone C (3), along with three known compounds (4-6), were isolated from the ethanolic extract of the stems and leaves of Combretum yunnanense, and their structures were determined by spectroscopic analysis. Compounds 1-3 were evaluated for in vitro cytotoxicity against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7, and SW480. Compounds 1, 2 and 3 were found to be most potent against HL-60 acute leukemia cells, with IC₅₀ values of 4.63, 4.07, and 1.26 µM, respectively.

  13. Synthesis and antimicrobial evaluation of some heterocyclic chalcone derivatives.

    Science.gov (United States)

    Hamada, Nagwa Mohamed Mahrous; Sharshira, Essam Mohamed

    2011-03-09

    Some new heterocyclic compounds containing isoxazole, pyrazole and oxadiazole ring systems were prepared from various chalcones. The synthesized compounds have been characterized by elemental analysis and spectral methods. These compounds were screened for their antimicrobial activities.

  14. Exploring pharmacological significance of chalcone scaffold: a review.

    Science.gov (United States)

    Sahu, N K; Balbhadra, S S; Choudhary, J; Kohli, D V

    2012-01-01

    Chalcones (1,3-diaryl-2-propen-1-ones) and their heterocyclic analogues, belong to the flavonoid family, which possess a number of interesting biological properties such as antioxidant, cytotoxic, anticancer, antimicrobial, antiprotozoal, antiulcer, antihistaminic and anti-inflammatory activities. Several pure chalcones have been approved for clinical use or tested in humans. Clinical trials have shown that these compounds reached reasonable plasma concentration and are well-tolerated. For this reason they are an object of continuously growing interest amongst the scientists. However, much of the pharmacological potential of chalcones is still not utilized. The purpose of this review is to provide an overview of the pharmacological activity of naturally occurring and synthetic chalcones. This review highlights more recent pharmacological screening of these compounds, their mechanisms of action and relevant structure-activity relationships.

  15. Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives

    Directory of Open Access Journals (Sweden)

    Essam Mohamed Sharshira

    2011-03-01

    Full Text Available Some new heterocyclic compounds containing isoxazole, pyrazole and oxadiazole ring systems were prepared from various chalcones. The synthesized compounds have been characterized by elemental analysis and spectral methods. These compounds were screened for their antimicrobial activities.

  16. Synthesis and anti-inflammatory activity of chalcone derivatives.

    Science.gov (United States)

    Herencia, F; Ferrándiz, M L; Ubeda, A; Domínguez, J N; Charris, J E; Lobo, G M; Alcaraz, M J

    1998-05-19

    Chalcones and their derivatives were synthesized and evaluated for their anti-inflammatory activity. In vitro, chalcones 2, 4, 8, 10 and 13 inhibited degranulation and 5-lipoxygenase in human neutrophils, whereas 11 behaved as scavenger of superoxide. Only four compounds (4-7) inhibited cyclo-oxygenase-2 activity. The majority of these samples showed anti-inflammatory effects in the mouse air pouch model.

  17. Synthesis and Antibacterial Activity of Chalcones and Pyrimidine-2-ones

    OpenAIRE

    2005-01-01

    Some new chalcones have been prepared by Claisen-schmidt condensation of ketone and different aromatic aldehydes. These chalcones on condensation with urea in presence of acid gave Pyrimidine-2-ones. The synthesized compounds have been characterized by elemental analysis, IR and 1H NMR spectral data. They have been screened for their antibacterial activity against Gram positive bacteria B. subtillis & S. aureus and Gram negative bacteria E. coli & S. typhi.

  18. Chalcones Enhance TRAIL-Induced Apoptosis in Prostate Cancer Cells

    OpenAIRE

    2009-01-01

    Chalcones exhibit chemopreventive and antitumor effects. Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is a naturally occurring anticancer agent that induces apoptosis in cancer cells and is not toxic to normal cells. We examined the cytotoxic and apoptotic effect of five chalcones in combination with TRAIL on prostate cancer cells. The cytotoxicity was evaluated by the MTT and LDH assays. The apoptosis was determined using flow cytometry with annexin V-FITC. Our study showe...

  19. Asymmetric cyclopropanation of chalcones using chiral phase-transfer catalysts

    OpenAIRE

    2013-01-01

    The first phase-transfer catalyzed cyclopropanation reaction of chalcones using bromomalonates as the nucleophiles in a Michael Initiated Ring Closing reaction (MIRC) was developed. Key to success was the use of a free OH-containing cinchona alkaloid ammonium salt catalyst and carefully optimized liquid/liquid reaction conditions. The reaction performed well for electron neutral and electron deficient chalcones giving the products in yields up to 98% and with enantiomeric ratios up to 91:9.

  20. Synthesis and biological evaluation of chalcone derivatives (mini review).

    Science.gov (United States)

    Bukhari, Syed Nasir Abbas; Jasamai, Malina; Jantan, Ibrahim

    2012-11-01

    Chalcones are the principal precursors for the biosynthesis of flavonoids and isoflavonoids. A three carbon α, β-unsaturated carbonyl system constitutes chalcones. Chalcones are the condensation products of aromatic aldehyde with acetophenones in attendance of catalyst. They go through an assortment of chemical reactions and are found advantageous in synthesis of pyrazoline, isoxazole and a variety of heterocyclic compounds. In synthesizing a range of therapeutic compounds, chalcones impart key role. They have showed worth mentioning therapeutic efficacy for the treatment of various diseases. Chalcone based derivatives have gained heed since they own simple structures, and diverse pharmacological actions. A lot of methods and schemes have been reported for the synthesis of these compounds. Amongst all, Aldol condensation and Claisen-Schmidt condensation still grasp high up position. Other distinguished techniques include Suzuki reaction, Witting reaction, Friedel-Crafts acylation with cinnamoyl chloride, Photo-Fries rearrangement of phenyl cinnamates etc. These inventive techniques utilize various catalysts and reagents including SOCl(2) natural phosphate, lithium nitrate, amino grafted zeolites, zinc oxide, water, Na(2)CO(3), PEG400, silicasulfuric acid, ZrCl(4) and ionic liquid etc. The development of better techniques for the synthesis of α, β- unsaturated carbonyl compounds is still in high demand. In brief, we have explained the methods and catalysts used in the synthesis of chalcones along with their biological activities in a review form to provide information for the development of new-fangled processes targeting better yield, less reaction time and least side effects with utmost pharmacological properties.

  1. Radiation and quantum chemical studies of chalcone derivatives.

    Science.gov (United States)

    Gaikwad, P; Priyadarsini, K I; Naumov, S; Rao, B S M

    2010-08-05

    The reactions of oxidizing radicals ((*)OH, Br(2)(*-), and SO(4)(*-)) with -OH-, -CH(3)-, or -NH(2)-substituted indole chalcones and hydroxy benzenoid chalcones were studied by radiation and quantum chemical methods. The (*)OH radical was found to react by addition at diffusion-controlled rates (k = 1.1-1.7 x 10(10) dm(3) mol(-1) s(-1)), but Br(2)(*-) radical reacted by 2 orders of magnitude lower. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory have shown that the (C2-OH)(*), (C11-OH)(*), and (C10-OH)(*) adducts of the indole chalcones and the (C7-OH)(*) and (C8-OH)(*) adducts of the hydroxy benzenoid chalcones are more stable with DeltaH = -39 to -28 kcal mol(-1) and DeltaG = -32 to -19 kcal mol(-1). This suggests that (*)OH addition to the alpha,beta-unsaturated bond is a major reaction channel in both types of chalcones and is barrierless. The stability and lack of dehydration of the (*)OH adducts arise from two factors: strong frontier orbital interaction due to the low energy gap between interacting orbitals and the negligible Coulombic repulsion due to small absolute values of Mulliken charges. The transient absorption spectrum measured in the (*)OH radical reaction with all the indole chalcone derivatives exhibited a maximum at 390 nm, which is in excellent agreement with the computed value (394 nm). The formation of three phenolic products under steady-state radiolysis is in line with the three stable (*)OH adducts predicted by theory. Independent of the substituent, identical spectra (lambda(max) = 330-360 and approximately 580 nm) were obtained on one-electron oxidation of the three indole chalcones. MO calculations predict the deprotonation from the -NH group is more efficient than from the substituent due to the larger electron density on the N1 atom forming the chalcone indolyl radical. Its reduction potential was determined to be 0.56 V from the ABTS(*-)/ABTS(2-) couple. In benzenoid chalcones, the (*)OH adduct spectrum is

  2. Leishmanicidal activity of synthetic chalcones in Leishmania (Viannia) braziliensis.

    Science.gov (United States)

    de Mello, Tatiane F P; Bitencourt, Heriberto R; Pedroso, Raissa B; Aristides, Sandra M A; Lonardoni, Maria V C; Silveira, Thais G V

    2014-01-01

    The treatment of American cutaneous leishmaniasis (ACL) is based on a small group of compounds that were developed decades ago, all of which are highly toxic and have a high rate of treatment failure. The chalcones show leishmanicidal activity, yet few studies have evaluated this activity against Leishmania (Viannia) braziliensis, one of the most important species of Leishmania across Latin America. Four new synthetic chalcones (1-4) were evaluated for inhibitory activity in vitro against promastigotes and intracellular parasites 24h post infection of L. (V.) braziliensis, cytotoxicity for macrophages J774.A1 and red blood cells, and the ability to stimulate nitric oxide production. The results for the inhibitory concentration for 50% of the promastigotes (IC50) (1.38±1.09-6.36±2.04μM), cytotoxic concentration for 50% of the macrophages (CC50) (13.49±3.13-199.43±4.11μM), and selectivity index (SI) (3.76 to 33.94) indicate that all chalcones (1-4) showed an effect on promastigotes of L. (V.) braziliensis; chalcone 2 had the highest SI. The haemolytic assay with chalcones 1 (301.93μM), 2 (534.18μM), 3 (419.46μM) and 4 (381.11μM) showed 0.00%, 2.33%, 0.57% and 1.74% haemolysis, respectively. All chalcones significantly reduced the infection index of macrophages by parasites; for chalcones (1-3) this effect may be dependent on nitric-oxide production by macrophages. The chalcones tested exhibited inhibitory activity for promastigotes and intracellular parasites of L. (V.) braziliensis, with low toxicity for macrophages and red blood cells. The anti-Leishmania activity of chalcones (1-3) may depend on the stimulation of nitric-oxide production in the initial stage of infection. These results show an initially encouraging potential for the use of chalcones (1-4) to treat ACL.

  3. Naringenin Chalcone Suppresses Allergic Asthma by Inhibiting the Type-2 Function of CD4 T Cells

    Directory of Open Access Journals (Sweden)

    Chiaki Iwamura

    2010-01-01

    Conclusions: : The results of this study suggest that naringenin chalcone suppresses asthmatic symptoms by inhibiting Th2 cytokine production from CD4 T cells. Thus, naringenin chalcone may be a useful supplement for the suppression of allergic symptoms in humans.

  4. Modifications of the alpha,beta-double bond in chalcones only marginally affect the antiprotozoal activities

    DEFF Research Database (Denmark)

    Nielsen, S F; Kharazmi, A; Christensen, S B

    1998-01-01

    Methods for selective alkylation of chalcones in the alpha- or beta-position and for selective reduction of the alpha,beta-double bond have been developed. The antiparasitic potencies of the alpha,beta-double bond modified chalcones only differ marginally from the potencies of the parent chalcones...

  5. Synthesis and Biological Evaluation of Retinoid-Chalcones as Inhibitors of Colon Cancer Cell Growth

    Science.gov (United States)

    Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids were designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer ce...

  6. Synthesis of Chalcones with Anticancer Activities

    Directory of Open Access Journals (Sweden)

    Syam Mohan

    2012-05-01

    Full Text Available Several chalcones were synthesized and their in vitro cytotoxicity against various human cell lines, including human breast adenocarcinoma cell line MCF-7, human lung adenocarcinoma cell line A549, human prostate cancer cell line PC3, human adenocarcinoma cell line HT-29 (colorectal cancer and human normal liver cell line WRL-68 was evaluated. Most of the compounds being active cytotoxic agents, four of them with minimal IC50 values were chosen and studied in detail with MCF-7 cells. The compounds 1, 5, 23, and 25 were capable in eliciting apoptosis in MCF-7 cells as shown by multiparameter cytotoxicity assay and caspase-3/7, -8, and -9 activities (p < 0.05. The ROS level showed 1.3-fold increase (p < 0.05 at the low concentrations used and thus it was concluded that the compounds increased the ROS level eventually leading to apoptosis in MCF-7 cells through intrinsic as well as extrinsic pathways.

  7. Synthesis of Novel Chalcones as Acetylcholinesterase Inhibitors

    Directory of Open Access Journals (Sweden)

    Thanh-Dao Tran

    2016-07-01

    Full Text Available A new series of benzylaminochalcone derivatives with different substituents on ring B were synthesized and evaluated as inhibitors of acetylcholinesterase. The study is aimed at identification of novel benzylaminochalcones capable of blocking acetylcholinesterase activity for further development of an approach to Alzheimer’s disease treatment. These compounds were produced in moderate to good yields via Claisen-Schmidt condensation and subjected to an in vitro acetylcholinesterase inhibition assay, using Ellman’s method. The in silico docking procedure was also employed to identify molecular interactions between the chalcone compounds and the enzyme. Compounds with ring B bearing pyridin-4-yl, 4-nitrophenyl, 4-chlorophenyl and 3,4-dimethoxyphenyl moieties were discovered to exhibit significant inhibitory activities against acetylcholinesterase, with IC50 values ranging from 23 to 39 µM. The molecular modeling studies are consistent with the hypothesis that benzylaminochalcones could exert their effects as dual-binding-site acetylcholinesterase inhibitors, which might simultaneously enhance cholinergic neurotransmission and inhibit β-amyloid aggregation through binding to both catalytic and peripheral sites of the enzyme. These derivatives could be further developed to provide novel leads for the discovery of new anti-Alzheimer drugs in the future.

  8. The antileishmanial activity of novel oxygenated chalcones and their mechanism of action

    DEFF Research Database (Denmark)

    Zhai, L; Chen, M; Blom, J

    1999-01-01

    and the mechanism of action of a group of new oxygenated chalcones. The tested oxygenated chalcones inhibited the in-vitro growth of Leishmania major promastigotes and Leishmania donovani amastigotes. Treatment of hamsters infected with L. donovani with intraperitoneal administration of two oxygenated chalcones...... the ultrastructure of the mitochondria of L. major promastigote. The data clearly indicate that this group of oxygenated chalcones has a strong antileishmanial activity and might be developed into a new antileishmanial drug. The antileishmanial activity of oxygenated chalcones might be the result of interference...

  9. Nitric oxide-scavenging properties of some chalcone derivatives.

    Science.gov (United States)

    Herencia, Felipe; López-García, M Pilar; Ubeda, Amalia; Ferrándiz, M Luisa

    2002-03-01

    The implication of NO in many inflammatory diseases has been well documented. We have previously reported that some chalcone derivatives can control the iNOS pathway in inflammatory processes. In the present study, we have assessed the NO-scavenging capacity of three chalcone derivatives (CH8, CH11, and CH12) in a competitive assay with HbO(2), a well-known physiologically relevant NO scavenger. Our data identify these chalcones as new NO scavengers. The estimated second-order rate constants (k(s)) for the reaction of the three derivatives with NO is in the same range as the value obtained for HbO(2), with CH11 exerting the greatest effect. These results suggest an additional action of these compounds on NO regulation.

  10. Bis-chalcones and flavones: synthesis and antimicrobial activity.

    Science.gov (United States)

    Husain, Asif; Rashid, Mohd; Mishra, Ravinesh; Kumar, Deepak

    2013-01-01

    A series of bis-chalcones (3a-g) and their flavones derivatives (4a-g) were synthesized and evaluated for their antimicrobial activity. Bis-chalcones were prepared by condensing 1,1'-(4,6-dihydroxy-1,3-phenylene)diethanone (2) with appropriate aryl aldehydes following Claisen-Schmidt reaction conditions. Oxidative cyclization of bis-chalcones (3a-g) in DMSO in the presence of iodine furnished flavones (4a-g). The synthesized compounds were evaluated for their antibacterial and antifungal actions against some selected microbes. The results of antimicrobial evaluation showed that some of the synthesized compounds were good in their antibacterial and antifungal actions.

  11. Second harmonic generation and crystal growth of new chalcone derivatives

    Science.gov (United States)

    Patil, P. S.; Dharmaprakash, S. M.; Ramakrishna, K.; Fun, Hoong-Kun; Sai Santosh Kumar, R.; Narayana Rao, D.

    2007-05-01

    We report on the synthesis, crystal structure and optical characterization of chalcone derivatives developed for second-order nonlinear optics. The investigation of a series of five chalcone derivatives with the second harmonic generation powder test according to Kurtz and Perry revealed that these chalcones show efficient second-order nonlinear activity. Among them, high-quality single crystals of 3-Br-4'-methoxychalcone (3BMC) were grown by solvent evaporation solution growth technique. Grown crystals were characterized by X-ray powder diffraction (XRD), laser damage threshold, UV-vis-NIR and refractive index measurement studies. Infrared spectroscopy, thermogravimetric analysis and differential thermal analysis measurements were performed to study the molecular vibration and thermal behavior of 3BMC crystal. Thermal analysis does not show any structural phase transition.

  12. Synthesis and anti-inflammatory activity of three nitro chalcones.

    Science.gov (United States)

    Gómez-Rivera, Abraham; Aguilar-Mariscal, Hidemí; Romero-Ceronio, Nancy; Roa-de la Fuente, Luis F; Lobato-García, Carlos E

    2013-10-15

    The aim of this study was to synthesize three nitro substituted chalcones and to evaluate their anti-inflammatory activity in the model of carrageenan induced edema in rats. The nitro chalcone were prepared by aldol condensation using of mechanical agitation and environmentally friendly solvents with 72-73% yields in approximately 2h. The three structures were evaluated on biological activity at dose of 200mg/kg and they showed anti-inflammatory protective effect by both oral and intraperitoneal administration, this effect was time dependent.

  13. Anti-breast cancer activity of heteroaryl chalcone derivatives.

    Science.gov (United States)

    Solomon, V Raja; Lee, Hoyun

    2012-04-01

    In an attempt to develop effective anticancer therapeutics, a new series of heteroaryl chalcone compounds were designed, synthesized, and examined for their antiproliferative effects on two breast cancer cell lines and one matching non-cancer breast cell line. The structure-activity relationship (SAR) analysis suggested that the compounds derived from thiophene chalcones (6-17) exhibited generally better antiproliferative activity than those derived from bioisoteric replacement of furan chalcones (18-29) on MDA-MB231 breast cancer cells. In contrast, the compounds derived from furan chalcones showed generally better antiproliferative activity on MDA-MB468 breast cancer cells. Among 24 compounds examined, compounds 21 and 23 showed significantly improved antiproliferative activity against MDA-MB231 and MDA-MB468 cancer cells. However, compound 23 ((E)-1-(4-chlorophenyl)-3-(5-(4-methoxyphenyl)furan-2-yl)prop-2-en-1-one) is considered to be most desirable among this series, since its antiproliferative activity was 3 to 7-fold higher on cancer than non-cancer cells. Compound 23 showed not only more effective activity than the widely prescribed cisplatin on cancer cells, but it also showed differential antiproliferative activity against cancer cells, a property that is not shown with cisplatin. If this property shown in cell culture stands in vivo test, compound 23 can be an effective and safe anticancer drug.

  14. Inhibition of sortase A by chalcone prevents Listeria monocytogenes infection.

    Science.gov (United States)

    Li, Hongen; Chen, Yutao; Zhang, Bing; Niu, Xiaodi; Song, Meng; Luo, Zhaoqing; Lu, Gejin; Liu, Bowen; Zhao, Xiaoran; Wang, Jianfeng; Deng, Xuming

    2016-04-15

    The critical role of sortase A in gram-positive bacterial pathogenicity makes this protein a good potential target for antimicrobial therapy. In this study, we report for the first time the crystal structure of Listeria monocytogenes sortase A and identify the active sites that mediate its transpeptidase activity. We also used a sortase A (SrtA) enzyme activity inhibition assay, simulation, and isothermal titration calorimetry analysis to discover that chalcone, an agent with little anti-L. monocytogenes activity, could significantly inhibit sortase A activity with an IC50 of 28.41 ± 5.34 μM by occupying the active site of SrtA. The addition of chalcone to a co-culture of L. monocytogenes and Caco-2 cells significantly inhibited bacterial entry into the cells and L. monocytogenes-mediated cytotoxicity. Additionally, chalcone treatment decreased the mortality of infected mice, the bacterial burden in target organs, and the pathological damage to L. monocytogenes-infected mice. In conclusion, these findings suggest that chalcone is a promising candidate for the development of treatment against L. monocytogenes infection.

  15. ANDROECHIN, A NEW CHALCONE GLUCOSIDE FROM ANDROGRAPHIS ECHIOIDES

    Institute of Scientific and Technical Information of China (English)

    B.JAYAPRAKASAM; D.GUNASEKAR; K.V.RAO; A.BLOND; B.BODO

    2001-01-01

    A new chalcone glucoside, androechin, and a known flavone glucoside, echioidinin 5-O-gluco side, were isolated from the whole plant of Andrographis echioides. Androechin was character ized as 2,2',6'-trihydroxy-4'-methoxychalcone 2'-O-,β-D-glucopyranoside by spectral and chemical studies.

  16. Synthesis and Characterization of a-Bromo Chalcone Derivatives

    Institute of Scientific and Technical Information of China (English)

    BUDAK Yakup; CEYLAN Mustafa

    2009-01-01

    a-Bromo chalcones containing 2-thiene ring were prepared in good yields by the condensation of 1-(thien-3-yl)ethanone with aromatic aldehydes,followed by bromination with bromine and selective dehydrobromination with triethyl amine at room temperature.

  17. A new chalcone from the aerial roots of Ficus microcarpa

    Institute of Scientific and Technical Information of China (English)

    Hui Xu; Xiang Min Wang; Xing Wei; Jing Yuan Li; Ke Liu

    2009-01-01

    A new flavonoid with chalcone skeleton was isolated from the dried aerial roots of Ficus microcarpa.The structure of the compound was elucidated on the basis of spectral methods including ID and 2D NMR.The new compound showed weak inhibitory effect on nitric oxide production and cytotoxicity against K562 and PC3 ceils.

  18. New flavan and unusual chalcone glycosides from Drypetes parvifolia

    Institute of Scientific and Technical Information of China (English)

    Viviane Nadege Nenkep; Jovita Chi Shirri; Hanh Trinh Van-Dufat; Falindor Sipepnou; Philippe Verite; Elisabeth Seguin; Francis Tillequin; Jean Wandji

    2008-01-01

    Two new compounds 7-hydroxy-5-O-(β-D-glucopyranoside) flavan (1) and (Z)-4',6'-dihydroxy-2'-O-(β-D-glucopyranoside) chalcone (2), along with eight known compounds, were isolated from the stem bark of Drypetes parvifolia (Euphorbiaceae). Their structures were established on the basis of spectroscopic analysis and chemical evidence.

  19. Ab initio calculations of the absorption spectrum of chalcone

    Science.gov (United States)

    Oumi, Manabu; Maurice, David; Head-Gordon, Martin

    1999-03-01

    The excitation energies and excited states of trans-chalcone ( trans-( s-cis)-1,3-diphenylpropenone), and several related molecules ( trans-( s-cis)-3-phenylpropenal, s-cis-1-phenylpropenone, propenal, trans-( s-cis)-1-(4-hydroxyphenyl)-3-phenylpropenone, trans-( s-cis)3-(4-hydroxyphenyl)-1-phenylpropenone) have been calculated using single reference ab initio molecular orbital methods, and characterized by attachment-detachment density analysis. The results suggest assignments for the lowest three electronic transitions observed experimentally for trans-( s-cis)-chalcone in solution. The extent of localization of the electronic transitions is established by calculations on the excited states of trans-( s-cis)-3-phenylpropenal, s-cis-1-phenylpropenone and propenal, as well as analysis of the chalcone calculations. Contrary to some previous work, none of these excitations are strongly delocalized over the entire molecule. Calculated substituent shifts for the hydroxy chalcones are in qualitative agreement with experimental data, and support the localized interpretation of the main π→ π* transition.

  20. Antimalarial activity of newly synthesized chalcone derivatives in vitro.

    Science.gov (United States)

    Yadav, Neesha; Dixit, Sandeep K; Bhattacharya, Amit; Mishra, Lokesh C; Sharma, Manish; Awasthi, Satish K; Bhasin, Virendra K

    2012-08-01

    Twenty-seven novel chalcone derivatives were synthesized using Claisen-Schmidt condensation and their antimalarial activity against asexual blood stages of Plasmodium falciparum was determined. Antiplasmodial IC(50) (half-maximal inhibitory concentration) activity of a compound against malaria parasites in vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was 1-(4-benzimidazol-1-yl-phenyl)-3-(2, 4-dimethoxy-phenyl)-propen-1-one with IC(50) of 1.1 μg/mL, while that of the natural phytochemical, licochalcone A is 1.43 μg/mL. The presence of methoxy groups at position 2 and 4 in chalcone derivatives appeared to be favorable for antimalarial activity as compared to other methoxy-substituted chalcones. Furthermore, 3, 4, 5-trimethoxy groups on chalcone derivative probably cause steric hindrance in binding to the active site of cysteine protease enzyme, explaining the relative lower inhibitory activity.

  1. Genetic control of chalcone isomerase activity in flowers of Dianthus caryophyllus.

    Science.gov (United States)

    Forkmann, G; Dangelmayr, B

    1980-06-01

    In flowers of Dianthus caryophyllus (carnation), the gene I is concerned with a discrete step in flavonoid biosynthesis, Genotypes with recessive (ii) alleles produce yellow flowers, which contain the chalcone isosalipurposide (naringenin-chalcone-2'-glucoside) as the major petal pigment, but in genotypes with wild-type alleles flavonols and anthocyanins can be formed and the flowers are white or red. Enzymatic measurements on petal extracts of four strains with different flower coloration revealed a clear correlation between accumulation of chalcone in recessive genotypes and deficiency of chalcone isomerase (E.C. 5.5.1.6) activity. From the chemogenetic and enzymological evidence it can be concluded that naringenin-chalcone is the first product of the synthesis of the flavonoid skeleton and that only the conversion of naringenin-chalcone to naringenin furnishes the substrate for the further reactions to flavonol and anthocyanin.

  2. A chalcone with potent inhibiting activity against biofilm formation by nontypeable Haemophilus influenzae.

    Science.gov (United States)

    Kunthalert, Duangkamol; Baothong, Sudarat; Khetkam, Pichit; Chokchaisiri, Suwadee; Suksamrarn, Apichart

    2014-10-01

    Nontypeable Haemophilus influenzae (NTHi), an important human respiratory pathogen, frequently causes biofilm infections. Currently, resistance of bacteria within the biofilm to conventional antimicrobials poses a major obstacle to effective medical treatment on a global scale. Novel agents that are effective against NTHi biofilm are therefore urgently required. In this study, a series of natural and synthetic chalcones with various chemical substituents were evaluated in vitro for their antibiofilm activities against strong biofilm-forming strains of NTHi. Of the test chalcones, 3-hydroxychalcone (chalcone 8) exhibited the most potent inhibitory activity, its mean minimum biofilm inhibitory concentration (MBIC50 ) being 16 μg/mL (71.35 μM), or approximately sixfold more active than the reference drug, azithromycin (MBIC50 419.68 μM). The inhibitory activity of chalcone 8, which is a chemically modified chalcone, appeared to be superior to those of the natural chalcones tested. Significantly, chalcone 8 inhibited biofilm formation by all studied NTHi strains, indicating that the antibiofilm activities of this compound occur across multiple strong-biofilm forming NTHi isolates of different clinical origins. According to antimicrobial and growth curve assays, chalcone 8 at concentrations that decreased biofilm formation did not affect growth of NTHi, suggesting the biofilm inhibitory effect of chalcone 8 is non-antimicrobial. In terms of structure-activity relationship, the possible substituent on the chalcone backbone required for antibiofilm activity is discussed. These findings indicate that 3-hydroxychalcone (chalcone 8) has powerful antibiofilm activity and suggest the potential application of chalcone 8 as a new therapeutic agent for control of NTHi biofilm-associated infections.

  3. Synthesis and Biological Evaluation of Some New Chalcones Containing 2,5-Dimethylfuran Moiety

    OpenAIRE

    2011-01-01

    A series of new chalcones (3a-g) were prepared by Claisen-Schmidt condensation of 3-acetyl-2,5-dimethylfuran with various substituted aromatic aldehydes in presence of aqueous solution of potassium hydroxide and ethanol at room temperature. The synthesized chalcones were characterized by means of their IR, 1H NMR spectral data and elemental analyses. When these chalcones were evaluated for antimicrobial and anti-inflammatory activities, some of them were found to possess significant activity,...

  4. In vitro and in vivo anti-Leishmania activity of polysubstituted synthetic chalcones

    OpenAIRE

    2010-01-01

    The in vitro screening of 43 polysubstituted chalcones against Leishmania amazonensis axenic amastigotes, led to the evaluation of 9 of them in a macrophage-infected model with the two other most infectious Leishmania species prevalent in Peru (L. braziliensis and L. peruviana). The five most active and selective chalcones were studied in vivo, resulting on the identification of two chalcones with high reduction parasite burden percentages.

  5. A review of anti-infective and anti-inflammatory chalcones.

    Science.gov (United States)

    Nowakowska, Zdzisława

    2007-02-01

    Chalcones, considered as the precursors of flavonoids and isoflavonoids, are abundant in edible plants, and have also been shown to display a diverse array of pharmacological activities. The purpose of this review is to provide an overview of the pharmacological activity of synthetic and naturally occurring chalcones. This review is complementary to earlier reviews and covers more recent reports of antimicrobial activity of chalcones (antibacterial and antifungal), as well as antileishmanial, antimalarial, antiviral and anti-inflammatory activities of these compounds.

  6. Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience

    Science.gov (United States)

    Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr.

    2002-09-01

    A guided inquiry experiment involving the synthesis and characterization of substituted benzalacetophenones (chalcones) is described. The chalcones are produced in the aldol condensation of substituted benzaldehydes with substituted acetophenones. Each student is assigned a different target chalcone and conducts online and printed literature searches on the target. After completing the synthesis and purification of their product, the students compare their data with those found in the literature.

  7. Synthesis, spectral correlation and insect antifeedant activities of some 2-benzimidazole chalcones

    OpenAIRE

    2016-01-01

    Some substituted styryl 2-benzimidazole ketones have been synthesised by fly-ash:H2SO4 catalysed aldol condensation of 2-benzimidazole methyl ketone and various substituted benzaldehydes in microwave oven. The yields of these chalcones are more than 70%. The purities of synthesised benzimidazole chalcones were checked by their physical constants and spectral data earlier published in the literature. The spectral frequencies of these chalcones have been correlated with Hammett substituent cons...

  8. A novel bioactive chalcone of Morus australis inhibits tyrosinase activity and melanin biosynthesis in B16 melanoma cells.

    Science.gov (United States)

    Takahashi, Makoto; Takara, Kensaku; Toyozato, Tomonao; Wada, Koji

    2012-01-01

    The methanol extract of Morus australis (shimaguwa) acts as a whitening agent due to the inhibition of tyrosinase activity. In order to explore the mechanism(s) of the whitening action, constituents of the 95% methanol extract from the dried stems of shimaguwa were isolated and their skin-whitening capacity was examined. Bioassay-guided fractionation of the methanol soluble extract of shimaguwa led to the isolation of 2, 4, 2', 4'-hydroxycalcone (chalcone 1) and three analogues of chalcone 1 with 3'-substituted resorcinol moieties (chalcones 2-4). Chalcone derivative 4 proved to be a novel compound and was fully characterized. Chalcones 1-4 were evaluated for inhibition activity on mushroom tyrosinase using L-tyrosine as the substrate. The parent chalcone 1 was a highly effective inhibitor of tyrosinase activity (IC₅₀ = 0.21 μM) compared to arbutin (IC₅₀ = 164 μM). Compared to chalcone 1, chalcones 2 and 3, which possess 3'-substituted isoprenyl or bulky 2-benzoylbiphenyl, showed significantly decreased tyrosinase activity, while chalcone 4, possessing 3'-substituted 2-hydroxy-1-pentene group, showed slightly increased activity.The effects of chalcones 1-4 on melanin synthesis, without affecting cell growth, were assayed in melanin-producing B16 murine melanoma cells. Chalcone 3 significantly reduced cell viability before reaching the IC₅₀ value for melanin synthesis. In contrast, the inhibitory effects of chalcones 1, 2 and 4 were more than 100-fold greater than that of arbutin, with little or no cytotoxicity. More significantly, chalcone 2, which exhibited less tyrosinase inhibitory activity compared to the parent chalcone 1, showed the highest inhibition of melanin synthesis in B16 cells among the chalcones tested. Accordingly, chalcones 1 and 2, and the novel chalcone 4 might be the active components responsible for the whitening ability of shimaguwa. Moreover, whitening ability was not exclusively due to tyrosinase inhibition.

  9. Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes.

    Science.gov (United States)

    El Sayed Aly, Mohamed Ramadan; Abd El Razek Fodah, Hamadah Hamadah; Saleh, Sherif Yousef

    2014-04-09

    Four sets of rationally designed chalcones were prepared for evaluation of their antiobesity, antioxidant and cytotoxicity activities. These sets include nine oleoyl chalcones as mimics of oleoyl estrone, three monohydroxy chalcones (chalcone ligands), Schiff base-derived chalcones and four copper as well as zinc complexes. Oleoyl chalcones 4d, 4e and particularly 6a as an isosteric isomer of oleoyl estrone, were as active as Orlistat on weight loss and related metabolic parameters using male SD rats in vivo. Chalcone ligands 10a-c and Schiff base-derived chalcones 11 and 14a,b were weakly antioxidants, while, the copper and zinc complexes 15a-d were good antioxidants with zinc chelates 15b,d being more active than their copper analogues 15a,cin vitro. Compounds 10c and 14a showed good cytotoxicity activities as Doxorubicin against PC3 cancer cell line in vitro, while, the copper complex 15c showed promising activity with IC₅₀ value of 5.95 μM. The estimated IC₅₀ value for Doxorubicin was 8.7 μM. Chalcones 14a,b are bifunctional probes for potential investigations in cancer diagnosis and radiotherapy by complexation with Gd(3+) or metal radioisotopes followed by posttranslation of Shiga toxin B-subunits that target globotriosyl ceramide expressing cancer cells.

  10. Cellular and molecular mechanisms activating the cell death processes by chalcones: Critical structural effects.

    Science.gov (United States)

    Champelovier, Pierre; Chauchet, Xavier; Hazane-Puch, Florence; Vergnaud, Sabrina; Garrel, Catherine; Laporte, François; Boutonnat, Jean; Boumendjel, Ahcène

    2013-12-01

    Chalcones are naturally occurring compounds with diverse pharmacological activities. Chalcones derive from the common structure: 1,3-diphenylpropenone. The present study aims to better understand the mechanistic pathways triggering chalcones anticancer effects and providing evidences that minor structural difference could lead to important difference in mechanistic effect. We selected two recently investigated chalcones (A and B) and investigated them on glioblastoma cell lines. It was found that chalcone A induced an apoptotic process (type I PCD), via the activation of caspase-3, -8 and -9. Chalcone A also increased CDK1/cyclin B ratios and decreased the mitochondrial transmembrane potential (ΔΨm). Chalcone B induced an autophagic cell death process (type II PCD), ROS-related but independent of both caspases and protein synthesis. Both chalcones increased Bax/Bcl2 ratios and decreased Ki67 and CD71 antigen expressions. The present investigation reveals that despite the close structure of chalcones A and B, significant differences in mechanism of effect were found.

  11. Synthesis of novel chalcone derivatives and their stabilization effect of spiropyran in PMMA films

    Institute of Scientific and Technical Information of China (English)

    Zheng Kai Si; Qing Zhang; Min Zhao Xue; Yuan Yuan Zhu; Liang Ming; Qiao Rong Sheng; Yan Gang Liu

    2011-01-01

    Three novel bis-chalcone derivatives with different alkyldioxy spacers were synthesized and dispersed into polymethyl methacrylate (PMMA) chloroform solution with 6-nitro-1'-ethyl-3',3'-dimethylspiro-2H-1-benzopyran-2,2'-indoline (ESP) to prepare photochromic PMMA films in a facile way. After irradiation with 365 nm UV light, the photocrosslinking reaction between chalcone units was proved to retard the decolorization of merocyanine form of the photochromic spiropyran effectively, as results of the steric hindrance produced by photocycloaddition of chalcone groups. It has been found that the bis-chalcone molecule with the shortest spacer has the most effective stabilizing effect on retardation of decoloration of spiropyran.

  12. SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME CHALCONE DERIVATIVES AND THEIR COPPERCOMPLEXES

    Directory of Open Access Journals (Sweden)

    P. M. Rachmale

    2012-03-01

    Full Text Available In the present investigation, 4-chloro acetophenone on condensation with 2-nitro benzaldehydes in methanolic NaOH solution yielded the corresponding chalcone. These chalcone were further reacted with Isonicotyl hydrazide and semicarbazide in ethanol which led to the formation of chalcone Isonicotyl hydrazone and chalcone semicarbazone derivatives respectively. The newly synthesized derivatives and there copper complexes were characterized on the basis of their chemical properties and spectroscopic data such as IR, NMR and UV. All newly synthesized compounds were evaluated for their antibacterial activities against E. coli and S. aureus also for antifungal activities against P. notatum.

  13. Molecular evolution and sequence divergence of plant chalcone synthase and chalcone synthase-Like genes.

    Science.gov (United States)

    Han, Yingying; Zhao, Wenwen; Wang, Zhicui; Zhu, Jingying; Liu, Qisong

    2014-06-01

    Plant chalcone synthase (CHS) and CHS-Like (CHSL) proteins are polyketide synthases. In this study, we evaluated the molecular evolution of this gene family using representative types of CHSL genes, including stilbene synthase (STS), 2-pyrone synthase (2-PS), bibenzyl synthase (BBS), acridone synthase (ACS), biphenyl synthase (BIS), benzalacetone synthase, coumaroyl triacetic acid synthase (CTAS), and benzophenone synthase (BPS), along with their CHS homologs from the same species of both angiosperms and gymnosperms. A cDNA-based phylogeny indicated that CHSLs had diverse evolutionary patterns. STS, ACS, and 2-PS clustered with CHSs from the same species (late diverged pattern), while CTAS, BBS, BPS, and BIS were distant from their CHS homologs (early diverged pattern). The amino-acid phylogeny suggested that CHS and CHSL proteins formed clades according to enzyme function. The CHSs and CHSLs from Polygonaceae and Arachis had unique evolutionary histories. Synonymous mutation rates were lower in late diverged CHSLs than in early diverged ones, indicating that gene duplications occurred more recently in late diverged CHSLs than in early diverged ones. Relative rate tests proved that late diverged CHSLs had unequal rates to CHSs from the same species when using fatty acid synthase, which evolved from the common ancestor with the CHS superfamily, as the outgroup, while the early diverged lineages had equal rates. This indicated that late diverged CHSLs experienced more frequent mutation than early diverged CHSLs after gene duplication, allowing obtaining new functions in relatively short period of time.

  14. Synthesis and Cytotoxicity of Chalcones and 5-Deoxyflavonoids

    Directory of Open Access Journals (Sweden)

    Jing Zhang

    2013-01-01

    Full Text Available Chalcones 1~8 and 5-deoxyflavonoids 9~22 were synthesized in good yields by aldol condensation, Algar-Flynn-Oyamada reaction, glycosidation, and deacetylation reaction, respectively, starting from 2-acetyl phenols substituted by methoxy or methoxymethoxy group and appropriately benzaldehydes substituted by methoxy, methoxymethoxy group, or chlorine. Among them, 13 and 17~22 are new compounds. The cytotoxicity bioassays of these chalcones and 5-deoxyflavonoids were screened using the sulforhodamine B (SRB protein staining method, and the results showed that compounds 2, 4, 5, 6, 10, 15, and 19 exhibited moderate cytotoxicity against the cancer cell line of MDA-MB-231, U251, BGC-823, and B16 in comparison with control drugs (HCPT, Vincristine, and Taxol.

  15. Synthesis and Antimicrobial Activity of SomeNovel Benzimidazolyl Chalcones

    Directory of Open Access Journals (Sweden)

    B. A. Baviskar

    2009-01-01

    Full Text Available Some novel benzimidazolyl chalcones were synthesized by condensation of N-(4-(1H-benzo[d]imidazol-2-ylphenylacetamide with aromatic aldehydes in presence of aqueous potassium hydroxide solution at room temperature. All the synthesized compounds were characterized on the basis of their IR, 1H NMR spectroscopic data and elemental analysis. All the compounds have been screened for antimicrobial activity by the cup-plate method.

  16. Synthesis and Antimicrobial Activity of SomeNovel Benzimidazolyl Chalcones

    OpenAIRE

    2009-01-01

    Some novel benzimidazolyl chalcones were synthesized by condensation of N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)acetamide with aromatic aldehydes in presence of aqueous potassium hydroxide solution at room temperature. All the synthesized compounds were characterized on the basis of their IR, 1H NMR spectroscopic data and elemental analysis. All the compounds have been screened for antimicrobial activity by the cup-plate method.

  17. Synthesis and Antimicrobial Activity of Some Chalcone Derivatives

    Directory of Open Access Journals (Sweden)

    Y. Rajendra Prasad

    2008-01-01

    Full Text Available In an effort to develop antimicrobial agents, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with appropriate aromatic aldehydes in the presence of aqueous solution of potassium hydroxide and ethanol at room temperature. The synthesized compounds were characterized by means of their IR, 1H-NMR spectral data and elemental analysis. All the compounds were tested for their antibacterial and antifungal activities by the cup plate method.

  18. Molecular Targeted Approaches to Cancer Therapy and Prevention Using Chalcones

    OpenAIRE

    Jandial, Danielle D.; Blair, Christopher A.; Zhang, Saiyang; Krill, Lauren S; Zhang, Yan-Bing; Zi, Xiaolin

    2014-01-01

    There is an emerging paradigm shift in oncology that seeks to emphasize molecularly targeted approaches for cancer prevention and therapy. Chalcones (1,3-diphenyl-2-propen-1-ones), naturally-occurring compounds with widespread distribution in spices, tea, beer, fruits and vegetables, consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α, β-unsaturated carbonyl system. Due to their structural diversity, relative ease of chemical manipulation and reacti...

  19. Chalcone and curcumin derivatives: a way ahead for malarial treatment.

    Science.gov (United States)

    Kumar, Dileep; Kumar, Manish; Kumar, Ashok; Singh, Sushil Kumar

    2013-12-01

    Malaria has been a major cause of morbidity and mortality in developing countries, particularly in Sub-Saharan Africa and South Asia. The global malaria situation is increasingly being challenging owing to lack of credible malaria vaccine and the emergence of drug resistance to most of the available antimalarials. They demand search for novel generation of drugs. Versatility and flexibility for structural modification of natural and synthetic analogues of curcumin and chalcone have been explored extensively for designing new antimalarial agent. Recent advances to our knowledge of parasite biology as well as the availability of the genome sequence, have opened up new vista in the firmament of antimalarial drug designing for identifying novel molecular targets. Curcumin and chalcones has been reported to exert anti-malarial effect by binding directly to numerous signaling molecules, such as histone acetyltransferase, histone deacetylase, sarco (endo) plasmic reticulum Ca(2+)-ATPase, cysteine proteases etc. This review highlights insights the more recent antimalarial activities of these compounds, their mechanisms of action, molecular targets and relevant structureactivity relationship studies. Natural lead compounds like chalcone and curcumin have shown good and optimal binding to many enzymes present in parasite and can be explored as molecular targets for in silico studies to develop new, affordable and effective antimalarial drugs. With no credible malaria vaccine in sight, there is an imperative need to develop new drugs with different mechanisms of action to help preclude issues of cross-resistance.

  20. Polyanthumin, a novel cyclobutane chalcone trimmer from Memecylon polyanthum.

    Science.gov (United States)

    Chen, Guan; Cui, Cheng-Bin; Qi, Ai-Di; Li, Chang-Wei; Tao, Zun-Wei; Ren, Rong

    2015-01-01

    A novel unusual trimmer chalcone, polyanthumin (1), together with five known compounds myricetin 3-O-(3″-O-galloyl)-α-l-rhamnopyranoside (2), sulfuretin (3), fustin (4), gallic acid (5), and ethyl gallate (6), was isolated from the dry stems of Memecylon polyanthum H.L. Li. Among them, compound 1 is a new chalcone trimmer with a novel cyclobutane skeleton in nature. Compounds 3 and 4 are flavonoids carrying a single 7-OH in A ring, which provided the first example of these class flavonoids from the family Melastomataceae. In addition, the antitumor activities for 2-4 were reported for the first time in this study. The antitumor effects of the isolated compounds 1-6 in vitro were assayed by the SRB method using human cancer K562 cells, with the inhibition rates ranging from 39.4% to 54.5% at 100 μg/ml. The IC50 values of compounds 1 and 3 for the inhibition of K562 cell proliferation were determined to be 45.4 and 30.5 μg/ml, respectively. To the best of our knowledge, compound 1 was the second sample as chalcone trimer. In addition, the antitumor activities for 2-4 were reported for the first time in this study.

  1. Anti-cancer chalcones: Structural and molecular target perspectives.

    Science.gov (United States)

    Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar; Asati, Vivek

    2015-06-15

    Chalcone or (E)-1,3-diphenyl-2-propene-1-one scaffold remained a fascination among researchers in the 21st century due to its simple chemistry, ease of synthesis and a wide variety of promising biological activities. Several natural and (semi) synthetic chalcones have shown anti-cancer activity due to their inhibitory potential against various targets namely ABCG2/P-gp/BCRP, 5α-reductase, aromatase, 17-β-hydroxysteroid dehydrogenase, HDAC/Situin-1, proteasome, VEGF, VEGFR-2 kinase, MMP-2/9, JAK/STAT signaling pathways, CDC25B, tubulin, cathepsin-K, topoisomerase-II, Wnt, NF-κB, B-Raf and mTOR etc. In this review, a comprehensive study on molecular targets/pathways involved in carcinogenesis, mechanism of actions (MOAs), structure activity relationships (SARs) and patents granted have been highlighted. With the knowledge of molecular targets, structural insights and SARs, this review may be helpful for (medicinal) chemists to design more potent, safe, selective and cost effective anti-cancer chalcones.

  2. Synthetic and Antimicrobial Studies of Some new Chalcones of 3-Bromo-4-(p-tolyl sulphonamido acetophenone

    Directory of Open Access Journals (Sweden)

    Miss Rashmi Jain

    2004-01-01

    Full Text Available Eleven new chalcones have been sysnthesised by condensing 3-bromo-4-(p-tolyl sulphonamido acetophenone with different aromatic aldehydes using the method or Rohrman et al. The antimicrobial activity of these chalcones has been tested by adopting “paper disc diffusion plate method”, against various pathogenic fungi and bacteria. It has been found that the chalcones have considerable antifungal activity but less antibacterial activity. The results show that these chalcones may find use as antifungal agents.

  3. Synthetic and Antimicrobial Studies of Some new Chalcones of 3-Bromo-4-(p-tolyl sulphonamido) acetophenone

    OpenAIRE

    2004-01-01

    Eleven new chalcones have been sysnthesised by condensing 3-bromo-4-(p-tolyl sulphonamido) acetophenone with different aromatic aldehydes using the method or Rohrman et al. The antimicrobial activity of these chalcones has been tested by adopting “paper disc diffusion plate method”, against various pathogenic fungi and bacteria. It has been found that the chalcones have considerable antifungal activity but less antibacterial activity. The results show that these chalcones may find use as a...

  4. Fly-ash:H2SO4 catalyzed solvent free efficient synthesis of some aryl chalcones under microwave irradiation

    Science.gov (United States)

    Thirunarayanan, G.; Mayavel, P.; Thirumurthy, K.

    2012-06-01

    Some 2E aryl chalcones have been synthesized using greener catalyst Fly-ash:H2SO4 assisted solvent free environmentally benign Crossed-Aldol reaction. The yields of chalcones are more than 90%. The synthesized chalcones are characterized by their physical constants and spectral data.

  5. Discovery and structure activity relationships of 2-pyrazolines derived from chalcones from a pest management perspective

    Science.gov (United States)

    Synthesis of chalcones and 2-pyrazoline derivatives has been an active field of research due to the established pharmacological effects of these compounds. In this study, a series of chalcone (1a-i), 2-pyrazoline-1-carbothioamides (2a-i) and 2-pyrazoline-1-carboxamide derivatives (3a-g) were synthes...

  6. SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY OF SOME NOVEL ARYL AND HETROARYL CHALCONE ANALOGUES

    Directory of Open Access Journals (Sweden)

    Tribhuvan Singh

    2012-07-01

    Full Text Available A new series of Heterocyclic chalcones showed diversified biological activities. In view of potential biological activities of Heterocyclic chalcones derivative were prepared by claisen-Schmidt condensation technique. The compound were screened for anti-inflammatory and antibacterial activity.

  7. SYNTHESIS AND GREEN BROMINATION OF SOME CHALCONES AND THEIR ANTIMICROBIAL SCREENING

    OpenAIRE

    2013-01-01

    Chalcones are the versatile molecules having the structural flexibility which permits structural transformations into flavonoids, flavanones, pyrazoles, oxazoles, pyrimidines etc. Changes in their structure have offered the development of new medicinal agents having improved pharmacological potency. Their derivatives have attracts increasing attention due to numerous pharmacological potential. In the present communication we report the synthesis of chalcones from various acetophenone derivat...

  8. Antileishmanial chalcones: statistical design, synthesis, and three-dimensional quantitative structure-activity relationship analysis

    DEFF Research Database (Denmark)

    Nielsen, S F; Christensen, S B; Cruciani, G

    1998-01-01

    A large number of substituted chalcones have been synthesized and tested for antileishmanial and lymphocyte-suppressing activities. A subset of the chalcones was designed by using statistical methods. 3D-QSAR analyses using 67 (antileishmanial activity) and 63 (lymphocyte-suppressing activity...

  9. Solvent-dependent regioselective oxidation of trans-chalcones using aqueous hydrogen peroxide

    Energy Technology Data Exchange (ETDEWEB)

    Peng, Wang; Jiabin, Yang; Lushen, Li, E-mail: jimin@seu.edu.cn [Southeast University, Nanjing (China). School of Biological Science and Medical Engineering; Jin, Cai; Chunlong, Sun; Min, Ji [Southeast University, Nanjing (China). School of Chemistry and Chemical Engineering

    2013-03-15

    A novel method for regioselective oxidation of trans-chalcones with hydrogen peroxide in acetonitrile to afford cinnamic acids is reported. Only trans-b-arylacrylic acids were observed. A wide range of functionalized products can be effectively produced from various chalcones in good to excellent yields. (author)

  10. Identification and quantification of metabolites of orally administered naringenin chalcone in rats.

    Science.gov (United States)

    Yoshimura, Mineka; Sano, Atsushi; Kamei, Jun-Ichi; Obata, Akio

    2009-07-22

    Naringenin chalcone is the main active component of tomato skin extract, which has an antiallergic activity. In this study, naringenin chalcone was orally administered to rats, and the chemical structures and levels of the major metabolites in the plasma and urine of rats were determined. HPLC analysis indicated the presence of three major metabolites in the urine. LC-MS and NMR analyses tentatively identified these as naringenin chalcone-2'-O-beta-D-glucuronide, naringenin-7-O-beta-D-glucuronide, and naringenin-4'-O-beta-D-glucuronide. Naringenin chalcone-2'-O-beta-D-glucuronide was the only metabolite detected in the plasma, and its peak plasma level was observed 1 h after naringenin chalcone administration. Naringenin chalcone-2'-O-beta-D-glucuronide also inhibited histamine release from rat peritoneal mast cells stimulated with compound 48/80. This activity might contribute to the antiallergic activity of naringenin chalcone in vivo. To the best of the authors' knowledge, this study is the first to report determination of naringenin chalcone metabolites in rat plasma and urine.

  11. Solvent-dependent regioselective oxidation of trans-chalcones using aqueous hydrogen peroxide

    OpenAIRE

    2013-01-01

    A novel method for regioselective oxidation of trans-chalcones with hydrogen peroxide in acetonitrile to afford cinnamic acids is reported. Only trans-b-arylacrylic acids were observed. A wide range of functionalized products can be effectively produced from various chalcones in good to excellent yields.

  12. Synthesis and evaluation of chalcone analogues based pyrimidines as angiotensin converting enzyme inhibitors.

    Science.gov (United States)

    Bukhari, S N A; Butt, A M; Amjad, M W B; Ahmad, W; Shah, V H; Trivedi, A R

    2013-11-01

    Hypertension is a widespread and frequently progressive ailment that imparts a foremost threat for cardiovascular and renal disorders. Mammoth efforts are needed for the synthesis of innovative antihypertensive agents to combat this lethal disease. Chalcones have shown antihypertensive activity through inhibition of Angiotensin Converting Enzyme (ACE). Hence, a series of chalcone analogues is synthesized and used as precursor for the synthesis of novel series of pyrimidines. Precursor chalcones were prepared by reacting aldehydes and ketones in presence of sodium hydroxide followed by synthesis of corresponding pyrimidines by reaction with urea in presence of potassium hydroxide. Both groups were then evaluated for their effects on ACE. The results depicted that pyrimidines were more active than chalcones with methoxy (C5 and P5) substitution showing best results to inhibit ACE. Given that chalcone analogues and pyrimidines show a potential as the angiotensin converting enzyme inhibitors.

  13. Six new chalcones from Angelica keiskei inducing adiponectin production in 3T3-L1 adipocytes.

    Science.gov (United States)

    Ohnogi, Hiromu; Kudo, Yoko; Tahara, Kenichi; Sugiyama, Katsumi; Enoki, Tatsuji; Hayami, Shoko; Sagawa, Hiroaki; Tanimura, Yuko; Aoi, Wataru; Naito, Yuji; Kato, Ikunoshin; Yoshikawa, Toshikazu

    2012-01-01

    Angelica keiskei (Ashitaba in Japanese), a traditional herb in Japan, contains abundant prenylated chalcones. It has been reported that the chalcones from A. keiskei showed such bioactivities as anti-bacterial, anti-cancer and anti-diabetic effects. Xanthoangelol, 4-hydroxyderricin and six new chalcones were isolated in this study from an ethanol extract of A. keiskei by octadecyl silyl (ODS) and silica gel chromatography, and identified by 1D- and 2D-nuclear magnetic resonance (NMR) and high-resolution mass spectrometric analyses. The chalcones from A. keiskei markedly increased the expression of the adiponectin gene and the production of adiponectin in 3T3-L1 adipocytes. These results suggest that the chalcones from A. keiskei might be useful for preventing the metabolic syndrome.

  14. Green synthesis of chalcones derivatives as intermediate of flavones and their antibacterial activities

    Energy Technology Data Exchange (ETDEWEB)

    VH, Elfi Susanti, E-mail: elsantivh@yahoo.com; Redjeki, Tri, E-mail: tri-redjeki@yahoo.com [Universitas Sebelas Maret, Ir Sutami 36A Surakarta Indonesia, 57126 (Indonesia); Matsjeh, Sabirin, E-mail: sabirin-mara@yahoo.com; Wahyuningsih, Tutik Dwi, E-mail: mustofajogya@yahoo.co.id [Department of Chemistry FMJPA Universitas Gadjah Mada, Jl Sekip Utara, Yogyakarta Indonesia 55281 (Indonesia); Mustofa, E-mail: tutikdw@hotmail.com [Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta Jl. Sekip Utara Yogyakarta Indonesia, 55281 (Indonesia)

    2016-02-08

    Four chalcones derivatives have been synthesized from 3,4-dimethoxybenzaldehyde and acetophenone derivatives (2-hydroxy acetophenone, 2,4-dihydroxy acetophenone, 2,5-dihydroxy acetophenone and 2,6-dihydroxy acetophenone). The synthesis of these chalcones were conducted by Claisen-Schmidt condensation using grinding techniques at room temperature in the absence of solvents. The chalcones were prepared by grinding together equivalent amount of the approriate hydroxyacetophenone and 3,4-dimethoxybenzaldehyde in the presence of solid sodium hydroxide. Grinding techniques for synthesis of the chalcones derivatives is simple, efficient and environmentally benign compared to conventional methods. Then, the four chalcones derivatives undergo cyclization reactions to produce four flavones after reacted with iodine. The synthesized compounds were characterized by spectrometry (IR, {sup 1}H-NMR, {sup 13}C-NMR and MS)

  15. Effective solubilization of chalcones in micellar phase: Conductivity and voltammetric study

    Science.gov (United States)

    Ahmed, Safeer; Khan, Gul Tiaz; Shah, Syed Sakhawat

    2013-12-01

    The solubilization of four chalcones, between aqueous and micellar phases of ionic surfactants (SDS and CTAB), was investigated by conductivity and cyclic voltammetry (CV) techniques. From conductivity data, a decrease in the critical micellar concentration (CMC) of the surfactants, in presence of the chalcones was ascribed to the decreased charge density over the surfactants. The results were seconded by thermodynamic parameters including degree of ionization (α), counter ion binding (β), and standard Gibbs free energy of micellization (Δ G {m/○}). The added surfactant decreased the peak current of the oxidized chalcone and shifted the peak potential either positively (in presence of SDS) or negatively (in presence of CTAB). The effect is rationalized as chalcone-surfactant interaction and quantitated as binding constant ( K b) assorting values from 8.78 to 552.97 M-1. The preferred solubilization of the chalcones in the micellar phase has been inferred.

  16. Green synthesis of chalcones derivatives as intermediate of flavones and their antibacterial activities

    Science.gov (United States)

    VH, Elfi Susanti; Matsjeh, Sabirin; Wahyuningsih, Tutik Dwi; Mustofa, Redjeki, Tri

    2016-02-01

    Four chalcones derivatives have been synthesized from 3,4-dimethoxybenzaldehyde and acetophenone derivatives (2-hydroxy acetophenone, 2,4-dihydroxy acetophenone, 2,5-dihydroxy acetophenone and 2,6-dihydroxy acetophenone). The synthesis of these chalcones were conducted by Claisen-Schmidt condensation using grinding techniques at room temperature in the absence of solvents. The chalcones were prepared by grinding together equivalent amount of the approriate hydroxyacetophenone and 3,4-dimethoxybenzaldehyde in the presence of solid sodium hydroxide. Grinding techniques for synthesis of the chalcones derivatives is simple, efficient and environmentally benign compared to conventional methods. Then, the four chalcones derivatives undergo cyclization reactions to produce four flavones after reacted with iodine. The synthesized compounds were characterized by spectrometry (IR, 1H-NMR, 13C-NMR and MS).

  17. Second- and third-order nonlinear optical properties of unsubstituted and mono-substituted chalcones

    Science.gov (United States)

    Abegão, Luis M. G.; Fonseca, Ruben D.; Santos, Francisco A.; Souza, Gabriela B.; Barreiros, André Luis B. S.; Barreiros, Marizeth L.; Alencar, M. A. R. C.; Mendonça, Cleber R.; Silva, Daniel L.; De Boni, Leonardo; Rodrigues, J. J.

    2016-03-01

    This work describes the second and third orders of nonlinear optics properties of unsubstituted chalcone (C15H12O) and mono-substituted chalcone (C16H14O2) in solution, using hyper-Rayleigh scattering and Z-Scan techniques to determine the first molecular hyperpolarizability (β) and the two-photon absorption (2PA) cross section respectively. β Values of 25.4 × 10-30 esu and 31.6 × 10-30 esu, for unsubstituted and mono-substituted chalcone, respectively, dissolved in methanol have been obtained. The highest values of 2PA cross-sections obtained were 9 GM and 14 GM for unsubstituted and mono-substituted chalcone, respectively. The experimental 2PA cross sections obtained for each chalcone are in good agreement with theoretical results.

  18. Activity of synthetic chalcones in hamsters experimentally infected with Leishmania (Viannia) braziliensis.

    Science.gov (United States)

    de Mello, Tatiane F P; Cardoso, Bruna M; Lopes, Sara N; Bitencourt, Heriberto R; Voltarelli, Evandra M; Hernandes, Luzmarina; Aristides, Sandra M A; Lonardoni, Maria V C; Silveira, Thais G V

    2015-10-01

    The purpose of this study is to evaluate the toxicity of synthetic chalcones 1 and 2 in uninfected hamsters and anti-Leishmania activity of synthetic chalcones 1 and 2 in hamsters infected with Leishmania (Viannia) braziliensis. For the toxicity test, uninfected animals were treated with chalcones 1 and 2, and clinical and biochemical parameters and histological aspects of the liver and kidneys were assessed. Chalcones 1 and 2 were then intraperitoneally or topically administered (10 mg/kg body weight) three times per week in animals infected with promastigotes of L. (V.) braziliensis. We monitored the thickness of the infected footpads, determined parasitic load, performed histological analysis, and detected apoptosis in situ. The results were analyzed using Student's t test and Mann-Whitney test at a significance level of 5%. Neither of the chalcones showed toxicity. Chalcone 2 administered intraperitoneally significantly reduced the thickness of the infected footpad compared with the beginning of treatment. The parasite load of the lymph node and spleen was reduced in the groups treated with chalcones 1 (topical) and 2 (intraperitoneal). Chalcone 2 (topical) reduced parasite burden only in the lymph node. The histological analysis revealed reconstitution of the tissue and reductions of inflammation and apoptosis in the infected footpad in these groups. The synthetic chalcones 1 (topical) and 2 (intraperitoneal and topical) at a dose of 10 mg/kg showed anti-Leishmania activity in vivo, no renal or hepatic toxicity, and a reduction of apoptosis of the cells in the lesions. These chalcones may have substantial potential for the treatment of cutaneous leishmaniasis.

  19. A new member of the chalcone synthase (CHS family in sugarcane

    Directory of Open Access Journals (Sweden)

    Contessotto Miriam G.G.

    2001-01-01

    Full Text Available Sequences from the sugarcane expressed sequence tag (SUCEST database were analyzed based on their identities to genes encoding chalcone-synthase-like enzymes. The sorghum (Sorghum bicolor chalcone-synthase (CHS, EC 2.3.1.74 protein sequence (gi|12229613 was used to search the SUCEST database for clusters of sequencing reads that were most similar to chalcone synthase. We found 121 reads with homology to sorghum chalcone synthase, which we were then able to sort into 14 clusters which themselves were divided into two groups (group 1 and group 2 based on the similarity of their deduced amino acid sequences. Clusters in group 1 were more similar to the sorghum enzyme than those in group 2, having the consensus sequence of the active site of chalcone and stilbene synthase. Analysis of gene expression (based on the number of reads from a specific library present in each group indicated that most of the group 1 reads were from sugarcane flower and root libraries. Group 2 clusters were more similar to the amino acid sequence of an uncharacterized pathogen-induced protein (PI1, gi|9855801 from the S. bicolor expressed sequence tag (EST database. The group 2 clusters sequences and PI1 proteins are 90% identical, having two amino acid changes at the chalcone and stilbene synthase consensi but conserving the cysteine residue at the active site. The PI1 EST has not been previously associated with chalcone synthase and has a different consensus sequence from the previously described chalcone synthase of sorghum. Most of the group 2 reads were from libraries prepared from sugarcane roots and plants infected with Herbaspirillum rubrisubalbicans and Gluconacetobacter diazotroficans. Our results indicate that we have identified a sugarcane chalcone synthase similar to the pathogen-induced PI1 protein found in the sorghum cDNA libraries, and it appears that both proteins represent new members of the chalcone and stilbene synthase super-family.

  20. Chalcone inhibitors of the NorA efflux pump in Staphylococcus aureus whole cells and enriched everted membrane vesicles.

    Science.gov (United States)

    Holler, Jes Gitz; Slotved, Hans-Christian; Mølgaard, Per; Olsen, Carl Erik; Christensen, Søren Brøgger

    2012-07-15

    A library of 117 chalcones was screened for efflux pump inhibitory (EPI) activity against NorA mediated ethidium bromide efflux. Five of the chalcones (5-7, 9, and 10) were active and two chalcones (9 and 10) were equipotent to reserpine with IC(50)-values of 9.0 and 7.7 μM, respectively. Twenty chalcones were subsequently proved to be inhibitors of the NorA efflux pump in everted membrane vesicles. Compounds 5, 7, and 9 synergistically increased the effect of ciprofloxacin on Staphylococcus aureus. Our results suggest that chalcones might be developed into drugs for overcoming multidrug resistance based on efflux transporters of microorganisms.

  1. Quantitative analysis of flavanones and chalcones from willow bark.

    Science.gov (United States)

    Freischmidt, A; Untergehrer, M; Ziegler, J; Knuth, S; Okpanyi, S; Müller, J; Kelber, O; Weiser, D; Jürgenliemk, G

    2015-09-01

    Willow bark extracts are used for the treatment of fever, pain and inflammation. Recent clinical and pharmacological research revealed that not only the salicylic alcohol derivatives, but also the polyphenols significantly contribute to these effects. Quantitative analysis of the European Pharmacopoeia still focuses on the determination of the salicylic alcohol derivatives. The objective of the present study was the development of an effective quantification method for the determination of as many flavanone and chalcone glycosides as possible in Salix purpurea and other Salix species as well as commercial preparations thereof. As Salix species contain a diverse spectrum of the glycosidated flavanones naringenin, eriodictyol, and the chalcone chalconaringenin, a subsequent acidic and enzymatic hydrolysis was developed to yield naringenin and eriodictyol as aglycones, which were quantified by HPLC. The 5-O-glucosides were cleaved with 11.5% TFA before subsequent hydrolysis of the 7-O-glucosides with an almond β-glucosidase at pH 6-7. The method was validated with regard to LOD, LOQ, intraday and interday precision, accuracy, stability, recovery, time of hydrolysis, robustness and applicability to extracts. All 5-O- and 7-O-glucosides of naringenin, eriodictyol and chalconaringenin were completely hydrolysed and converted to naringenin and eriodictyol. The LOD of the HPLC method was 0.77 μM of naringenin and 0.45 μM of eriodictyol. The LOQ was 2.34 μM of naringenin and 1.35 μM for eriodictyol. The method is robust with regard to sample weight, but susceptible concerning enzyme deterioration. The developed method is applicable to the determination of flavanone and chalcone glycosides in willow bark and corresponding preparations.

  2. The Preparation of Some Novel Indazole Derivatives by Using Chalcones

    Institute of Scientific and Technical Information of China (English)

    Javad Safaei-Ghomi; Zohreh Alishahi

    2005-01-01

    @@ 1Introduction Indazole and its derivatives have little biological significance and have not been found in natural products due to the difficulty for living organisms to construct an N - N bond. Indazole derivatives exhibit variety of pharmacological properties such as anti-inflammatory, antidepressant, antitumor, antiarthritic and analgesic activities[1]. Different synthetic pathways generate these compounds. For instance, ring closure of pyrazole moiety, addition of hydrazine derivatives to carbonyl compounds[2] and cycloaddition reaction[3]. Herein, we report the synthesis of some new indazole derivatives by using chalcones as starting materials.

  3. Cytotoxic and apoptotic effects of chalcone derivatives of 2-acetyl thiophene on human colon adenocarcinoma cells.

    Science.gov (United States)

    de Vasconcelos, Alana; Campos, Vinicius Farias; Nedel, Fernanda; Seixas, Fabiana Kömmling; Dellagostin, Odir A; Smith, Kevin R; de Pereira, Cláudio Martin Pereira; Stefanello, Francieli Moro; Collares, Tiago; Barschak, Alethéa Gatto

    2013-06-01

    Recent studies report that chalcones exhibit cytotoxicity to human cancer cell lines. Typically, the form of cell death induced by these compounds is apoptosis. In the context of the discovery of new anticancer agents and in light of the antitumour potential of several chalcone derivatives, in the present study, we synthesized and tested the cytotoxicity of six chalcone derivatives on human colon adenocarcinoma cells. Six derivatives of 3-phenyl-1-(thiophen-2-yl) prop-2-en-1-one were prepared and characterized on the basis of their (1) H and (13) C NMR spectra. HT-29 cells were treated with synthesized chalcones on two concentrations by three different incubation times. Cells were evaluated by cell morphology, Tetrazolium dye (MTT) colorimetric assay, live/dead, flow cytometry (annexin V) and gene expression analyses to determine the cytotoxic way. Chalcones 3-(4-bromophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C06) and 3-(2-nitrophenyl)-1-(thiophen-2-yl)prop-2-en-1-one (C09) demonstrated higher cytotoxicity than other chalcones as shown by cell morphology, live/dead and MTT assays. In addition, C06 induced apoptosis on flow cytometry annexin V assay. These data were confirmed by a decreased expression of anti-apoptotic genes and increased pro-apoptotic genes. Our findings indicate in summary that the cytotoxic activity of chalcone C06 on colorectal carcinoma cells occurs by apoptosis.

  4. New administration model of trans-chalcone biodegradable polymers for the treatment of experimental leishmaniasis.

    Science.gov (United States)

    Piñero, Jose; Temporal, Rosane M; Silva-Gonçalves, Antonio J; Jiménez, I A; Bazzocchi, Isabel L; Oliva, Alexis; Perera, Antonio; Leon, Leonor L; Valladares, Basilio

    2006-04-01

    The present study was designed to investigate a new administration model and the antileishmanial activity of a semi-synthetic chalcone, benzylideneacetophenone (trans-chalcone). The antileishmanial activity of this product was first tested in vitro against promastigotes of L. braziliensis, L. tropica, L. infantum and L. amazonensis. An in vivo experiment was carried out using subcutaneous administration of trans-chalcone and implants of synthetic biodegradable polymers, polylactic acid (PLA) and polylactic/glycolic acid (PLGA). This compound showed potent inhibitory effects on the growth of all Leishmania strains examinated. Subcutaneous administration of trans-chalcone at a single dose of 4 mg/kg of body weight reduced lesion development in mice infected with L. amazonensis. A similar inhibition of the lesion growth in mice treated with trans-chalcone and pentamidine was observed. PLA and PGLA implants of trans-chalcone at 4 mg/kg were administered to mice infected with L. amazonensis. PLGA implants induced a highest reduction in the lesion size (31.25%) than PLA implants (10.75%). Treatment in vitro with trans-chalcone at IC50, completely inhibited the pathogenicity of this parasite in vivo. The development of this model provides a new practical technique for delivering drugs and can be useful for experimental leishmaniasis treatment.

  5. Evaluation of potential antidepressant-like activity of chalcone-1203 in various murine experimental depressant models.

    Science.gov (United States)

    Guan, Li-Ping; Tang, Li-Ming; Pan, Cheng-Yan; Zhao, Shui-Lian; Wang, Si-Hong

    2014-02-01

    Two classic animal behavior despair tests-the forced swimming test (FST) and the tail suspension test (TST) were used to evaluate antidepressant-like activity of a new chalcone compound, chalcone-1203 in mice. It was observed that chalcone-1203 at dose of 1, 5, and 10 mg/kg significantly reduced the immobility time in the FST and TST in mice 30 min after treatment. In addition, chalcone-1203 was found to exhibit significant oral activity in the FST in mice. It also produced a reduction in the ambulation in the open-field test in mice not previously habituated to the arena, but no effect in the locomotor activity in mice previously habituated to the open-field. The main monoamine neurotransmitters and their metabolites in mouse brain regions were also simultaneously determined by HPLC-ECD. It was found that chalcone-1203 significantly increased the concentrations of the main neurotransmitters 5-HT and NE in the hippocampus, hypothalamus and cortex. Chalcone-1203 also significantly reduced the ratio of 5-HIAA/5-HT in the hippocampus and cortex, shown down 5-HT metabolism compared with mice treated with stress vehicle. In conclusion, chalcone-1203 produced significant antidepressant-like activity, and the mechanism of action may be due to increased 5-HT and NE in the mouse hippocampus and cortex.

  6. INTERACTION OF CHALCONES WITH CT-DNA BY SPECTROPHOTOMETRIC ANALYSIS AND THEORETICALSIMULATIONS

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    Ximena Zarate

    Full Text Available Chalcones are open chain molecules precursors of flavonoids and isoflavonoids, found spread in edible plants. Because they are easily accessible trough Claisen Shmidt condensation, a great variety of derivatives are available. They have also shown potential in pharmacological and biological applications. It is known that chalcone derivatives display a role in the treatment of complex diseases such as cancer, among others, where the DNA is considered as the target for the action of these kinds of compounds. This action is commonly explained as the inhibition of the DNA replications and transcriptions through interactions. However, not conclusive associations between these DNA-Drug interactions and toxicity have been found. This research focuses on the capacity of a chalcone`s family to interact with DNA. Therefore, the binding constants for each compounds with Calf Thymus DNA [CT-DNA] were determined by spectrophotometric titration at room temperature. In addition, the effect of increasing the chalcone`s concentration over the relative viscosity of CT-DNA at room temperature was assessed. On the other hand, with the aim to find the optimal DNA-chalcone configurations, as well as consistently predict their binding, a computational work was undertaken. To accomplish these goals within a reasonable time framework, an empirical scoring function (AScore and a docking engine (ShapeDock were performed using the ArgusLab package. The results of viscosity and docking measurement provided structural insights which suggest that chalcones bind with DNA via interaction as well as intercalation. The presence of interactions is also evidenced by the spectrophotometric study which showed luminescence quenching of the chalcones upon interaction with CT-DNA.

  7. Synthesis of Urea based Chalcone Derivatives and Evaluate its Biological Activity

    Directory of Open Access Journals (Sweden)

    Arpita Desai

    2016-05-01

    Full Text Available Chalcones have been the center of attraction for researchers from several decades due to nits innumerous therapeutic application, Efforts have been done in my research to synthesized chalcones and their derivatives that further reacts with various substituted aldehyde to give corresponding substituted chalcone derivatives. Now these derivatives on condensation with Guanidine nitrate gives the vast range of phenyl pyrimidine amine Derivatives. Structure elucidation of synthesized compound had been made on the basis of element analysis, 1H NMR Spectra studies. The microbial activity of the synthesized compounds has been studied against the species bacillus subtillis, staphylococcus aureus, Escherichia coli, and salmonella typhi.

  8. Synthesis and Biological Evaluation of Some New Chalcones Containing 2,5-Dimethylfuran Moiety

    Directory of Open Access Journals (Sweden)

    S. Sridhar

    2011-01-01

    Full Text Available A series of new chalcones (3a-g were prepared by Claisen-Schmidt condensation of 3-acetyl-2,5-dimethylfuran with various substituted aromatic aldehydes in presence of aqueous solution of potassium hydroxide and ethanol at room temperature. The synthesized chalcones were characterized by means of their IR, 1H NMR spectral data and elemental analyses. When these chalcones were evaluated for antimicrobial and anti-inflammatory activities, some of them were found to possess significant activity, when compared to standard drugs.

  9. Ferrocenyl chalcone difluoridoborates inhibit HIV-1 integrase and display low activity towards cancer and endothelial cells.

    Science.gov (United States)

    Monserrat, Jean-Philippe; Al-Safi, Rasha I; Tiwari, Keshri Nath; Quentin, Lionel; Chabot, Guy G; Vessières, Anne; Jaouen, Gérard; Neamati, Nouri; Hillard, Elizabeth A

    2011-10-15

    We report here the discovery of a potent series of HIV-1 integrase (IN) inhibitors based on the ferrocenyl chalcone difluoridoborate structure. Ten new compounds have been synthesized and were generally found to have similar inhibitory activities against the IN 3' processing and strand transfer (ST) processes. IC(50) values were found to be in the low micromolar range, and significantly lower than those found for the non-coordinated ferrocenyl chalcones and other ferrocene molecules. The ferrocenyl chalcone difluoridoborates furthermore exhibited low cytotoxicity against cancer cells and low morphological activity against epithelial cells.

  10. Design, synthesis and anticancer activity of nitric oxide donating/chalcone hybrids.

    Science.gov (United States)

    Mourad, Mai A E; Abdel-Aziz, Mohamed; Abuo-Rahma, Gamal El-Din A A; Farag, Hassan H

    2012-08-01

    A group of nitric oxide (NO) donating chalcone derivatives was prepared by binding amino chalcones with different NO-donating moieties including; nitrate esters, oximes and furoxans. Screening of the anticancer activity of the target compounds revealed that the selected NO-donating compounds exhibited from mild to strong cytotoxic activity. The NO/chalcone hybrids 3a and 3b exhibited remarkable activity against different types of cancer cell lines especially against the colon and melanoma cancer cell lines. The nitrate ester 3a exhibited moderate selectivity toward colon cancer subpanel with selectivity ratio of 5.87 at TGI level.

  11. SYNTHESIS AND GREEN BROMINATION OF SOME CHALCONES AND THEIR ANTIMICROBIAL SCREENING

    Directory of Open Access Journals (Sweden)

    Mayur R. Adokar

    2013-04-01

    Full Text Available Chalcones are the versatile molecules having the structural flexibility which permits structural transformations into flavonoids, flavanones, pyrazoles, oxazoles, pyrimidines etc. Changes in their structure have offered the development of new medicinal agents having improved pharmacological potency. Their derivatives have attracts increasing attention due to numerous pharmacological potential. In the present communication we report the synthesis of chalcones from various acetophenone derivatives with different aromatic aldehydes and green chemistry approach to their bromination with the help of Tetrabutylammonium Tribromide (TBATB. All the synthesized chalcone dibromides were screened for their antimicrobial activity against Aspergillus flavus, Rhizopus sp., Fusarium solani and Aspergillus niger.

  12. Synthesis, cytotoxicity, and anti-Trypanosoma cruzi activity of new chalcones.

    Science.gov (United States)

    Aponte, José C; Verástegui, Manuela; Málaga, Edith; Zimic, Mirko; Quiliano, Miguel; Vaisberg, Abraham J; Gilman, Robert H; Hammond, Gerald B

    2008-10-09

    Synthesis of a cytotoxic dihydrochalcone, first isolated from a traditional Amazonian medicinal plant Iryanthera juruensis Warb (Myristicaceae), followed by a comprehensive SAR analysis of saturated and unsaturated chalcone synthetic intermediates, led to the identification of analogues with selective and significant in vitro anti- Trypanosoma cruzi activity. Further SAR studies were undertaken with the synthesis of 21 new chalcones containing two allyloxy moieties that resulted in the discovery of 2',4'-diallyloxy-6'-methoxy chalcones with improved selectivity against this parasite at concentrations below 25 microM, four of which exhibited a selectivity index greater than 12.

  13. Antidyslipidemic and antioxidant effects of novel Lupeol-derived chalcones.

    Science.gov (United States)

    Srivastava, Shishir; Sonkar, Ravi; Mishra, Sunil Kumar; Tiwari, Avinash; Balaramnavar, Vishal M; Balramnavar, Vishal; Mir, Snober; Bhatia, Gitika; Saxena, Anil K; Lakshmi, Vijai

    2013-10-01

    A series of Lupeol-based chalcones have been synthesized aiming to enhance the therapeutic efficacy of parent compound, the novel compounds were evaluated for their antidyslipidemic activity in triton-WR 1339 induced hyperlipidemic rats. Among the ten synthesized chalcones, the most active K4, K8, and K9 reversed the plasma levels of TC by (24, 25, 27 %), phospholipid by (25, 26, 25 %) and triacylglycerol by (27, 24, 24 %) respectively. In addition, the compounds showed significant in vitro antioxidant activity. The lipid lowering activity of these compounds were mediated through lipoprotein lipase activation (12-21 %) and enhanced post-heparin lipolytic activity (15-16 %). The compounds also displayed noteworthy inhibitory effect on 3-hydroxy-3-methyl-glutaryl reductase activity (in vitro). The in vitro effect of the most active compounds on MDI-induced adipogenesis using 3T3-L1 preadipocytes at 10 and 20 μM concentrations showed significant inhibition (20-32 %) of adipogenesis.

  14. Novel Halogenated Pyrazine-Based Chalcones as Potential Antimicrobial Drugs

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    Marta Kucerova-Chlupacova

    2016-10-01

    Full Text Available Chalcones, i.e., compounds with the chemical pattern of 1,3-diphenylprop-2-en-1-ones, exert a wide range of bio-activities, e.g., antioxidant, anti-inflammatory, anticancer, anti-infective etc. Our research group has been focused on pyrazine analogues of chalcones; several series have been synthesized and tested in vitro on antifungal and antimycobacterial activity. The highest potency was exhibited by derivatives with electron withdrawing groups (EWG in positions 2 and 4 of the ring B. As halogens also have electron withdrawing properties, novel halogenated derivatives were prepared by Claisen-Schmidt condensation. All compounds were submitted for evaluation of their antifungal and antibacterial activity, including their antimycobacterial effect. In the antifungal assay against eight strains of selected fungi, growth inhibition of Candida glabrata and Trichophyton interdigitale (formerly T. mentagrophytes was shown by non-alkylated derivatives with 2-bromo or 2-chloro substitution. In the panel of selected bacteria, 2-chloro derivatives showed the highest inhibitory effect on Staphylococcus sp. In addition, all products were also screened for their antimycobacterial activity against Mycobacterium tuberculosis H37RV My 331/88, M. kansasii My 235/80, M. avium 152/80 and M. smegmatis CCM 4622. Some of the examined compounds, inhibited growth of M. kansasii and M. smegmatis with minimum inhibitory concentrations (MICs comparable with those of isoniazid.

  15. Synthesis and anticonvulsant activity of certain chalcone based pyrazoline compounds

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    Sudhakara Rao Gerapati

    2015-09-01

    Full Text Available Convulsions are involuntary, violent, spasmodic and prolonged contractions of skeletal muscles. That means a patient may have epilepsy without convulsions and vice versa. Epilepsy is a common neurological abnormality affecting about 1% of the world population. The primary objectives of these synthesized compounds are to suppress seizures and provide neuroprotection by minimizing the effects from seizure attacks. Here some of the chalcones and chalcone based various pyrazolines were evaluated for anticonvulsant activity. Their structures have been elucidated on the basis of elemental analyses and spectroscopic studies (IR, 1H-NMR & Mass spectroscopy. A preliminary evaluation of the prepared compounds has indicated that some of them exhibit moderate to significant anticonvulsant activity compared to a diazepam standard1-3.  All compounds were tested for their anticonvulsant activity using maximal electroshock induced convulsions (MES in mice at a dose level of 4 mg/kg.b.w. The compounds  Ph1, Ph2 , Py2 ,Py3 and Py4 have shown  to  good anticonvulsant activity when doses are administered as 25mg/ kg.b.w  , reduced the phases of seizures severity and  found to be active and also  increased survival rate. Remaining compounds are less efficacious.

  16. Development of fluorescent FeIII sensor based on chalcone

    Energy Technology Data Exchange (ETDEWEB)

    Wei Yanli, E-mail: weiyanli@sxu.edu.cn [Research Center of Environmental Science and Engineering, Shanxi University, Taiyuan 030006 (China); Qin Guojie [Institute of Horticulture, Shanxi Academy of Agriculture Science, Taiyuan 030031 (China); Wang Wenyan; Bian Wei; Shuang Shaomin [Research Center of Environmental Science and Engineering, Shanxi University, Taiyuan 030006 (China); Dong Chuan, E-mail: dc@sxu.edu.cn [Research Center of Environmental Science and Engineering, Shanxi University, Taiyuan 030006 (China)

    2011-08-15

    In this paper, 4-dimethylamino 2,5-dihydroxy chalcone (DMADHC), which exhibits excited state intramolecular charge transfer (ICT) characteristics, was synthesized and characterized. A sensitive optochemical sensor for Fe{sup 3+} ion was developed using DMADHC as fluorescence receptor. The fluorescence of DMADHC was gradually quenched with the addition of Fe{sup 3+} ion, which attributed to the formation of 1:1 complex between DMADHC and Fe{sup 3+} ion. The sensor exhibited excellent selectivity for Fe{sup 3+} ion over a large number of cation ions such as alkali, alkaline earth and transitional metal ions with a linear range of 3.984x10{sup -7}-1.135x10{sup -5} and a limit of detection of 8.223x10{sup -8} mol/L. On this basis, the sensor was preliminary applied to the determination of the content of iron ions in multi-vitamin tablet with satisfied results and the recoveries were in the 95-100% interval, and precision (n=5) was better than 5%. - Highlights: > A fluorescence receptor, 4-dimethylamino 2,5-dihydroxy chalcone was synthesis by one-step reaction. > Its intramolecular charge transfer fluorescence characteristics could be blocked by Fe{sup 3+} ion. > Based on this, an optochemical sensor for Fe{sup 3+} ion was developed. > Importantly, our proposed method is particularly useful for determination of Fe{sup 3+} ion in real sample.

  17. Effects of chalcone derivatives on players of the immune system.

    Science.gov (United States)

    Lee, Jian Sian; Bukhari, Syed Nasir Abbas; Fauzi, Norsyahida Mohd

    2015-01-01

    The immune system is the defense mechanism in living organisms that protects against the invasion of foreign materials, microorganisms, and pathogens. It involves multiple organs and tissues in human body, such as lymph nodes, spleen, and mucosa-associated lymphoid tissues. However, the execution of immune activities depends on a number of specific cell types, such as B cells, T cells, macrophages, and granulocytes, which provide various immune responses against pathogens. In addition to normal physiological functions, abnormal proliferation, migration, and differentiation of these cells (in response to various chemical stimuli produced by invading pathogens) have been associated with several pathological disorders. The unwanted conditions related to these cells have made them prominent targets in the development of new therapeutic interventions against various pathological implications, such as atherosclerosis and autoimmune diseases. Chalcone derivatives exhibit a broad spectrum of pharmacological activities, such as immunomodulation, as well as anti-inflammatory, anticancer, antiviral, and antimicrobial properties. Many studies have been conducted to determine their inhibitory or stimulatory activities in immune cells, and the findings are of significance to provide a new direction for subsequent research. This review highlights the effects of chalcone derivatives in different types of immune cells.

  18. Ultrasound accelerated Claisen Schmidt condensation: A green route to chalcones

    Science.gov (United States)

    Calvino, V.; Picallo, M.; López-Peinado, A. J.; Martín-Aranda, R. M.; Durán-Valle, C. J.

    2006-06-01

    Chalcones have been synthesized under sonochemical irradiation by Claisen-Schmidt condensation between benzaldehyde and acetophenone. Two basic activated carbons (Na and Cs-Norit) have been used as catalysts. The effect of the ultrasound activation has been studied. A substantial enhancing effect in the yield was observed when the carbon catalyst was activated under ultrasonic waves. This "green" method (combination of alkaline-doped carbon catalyst and ultrasound waves) has been applied to the synthesis of several chalcones with antibacterial properties achieving, in all cases, excellent activities and selectivities. A comparative study under non-sonic activation has showed that the yields are lower in silent conditions, indicating that the sonication exerts a positive effect on the activity of the catalyst. Cs-doped carbon is presented as the optimum catalyst, giving excellent activity for this type of condensation. Cs-Norit carbon catalyst can compete with the traditional NaOH/EtOH when the reaction is carried out under ultrasounds. The role of solvent in this reaction was studied with ethanol. High conversion was obtained in absence of solvent. The carbons were characterized by thermal analysis, nitrogen adsorption and X-ray photoelectron spectroscopy.

  19. Novel chalcone-based fluorescent human histamine H3 receptor ligands as pharmacological tools

    Directory of Open Access Journals (Sweden)

    Holger eStark

    2012-03-01

    Full Text Available Novel fluorescent chalcone-based ligands at human histamine H3 receptors (hH3R have been designed, synthesized and characterized. Compounds described are non-imidazole analogues of ciproxifan with a tetralone motif. Tetralones as chemical precursors and related fluorescent chalcones exhibit affinities at hH3R in the same concentration range like that of the reference antagonist ciproxifan (hH3R pKi value of 7.2. Fluorescence characterization of our novel ligands shows emission maxima about 570 nm for yellow fluorescent chalcones and ≥600 nm for the red fluorescent derivatives. Interferences to cellular autofluorescence could be excluded. All synthesized chalcone compounds could be taken to visualize hH3R proteins in stably transfected HEK-293 cells using confocal laser scanning fluorescence microscopy. These novel fluorescent ligands possess high potential to be used as pharmacological tools for hH3R visualization in different tissues.

  20. Catalytic Hydrogenation Reaction of Naringin-Chalcone. Study of the Electrochemical Reaction

    Directory of Open Access Journals (Sweden)

    B. A. López de Mishima

    2000-03-01

    Full Text Available The electrocatalytic hydrogenation reaction of naringin derivated chalcone is studied. The reaction is carried out with different catalysts in order to compare with the classic catalytic hydrogenation.

  1. Pro-Angiogenic Effects of Chalcone Derivatives in Zebrafish Embryos in Vivo.

    Science.gov (United States)

    Chen, Yau-Hung; Chang, Chao-Yuan; Chang, Chiung-Fang; Chen, Po-Chih; Lee, Ya-Ting; Chern, Ching-Yuh; Tsai, Jen-Ning

    2015-07-09

    The aim of this study was to investigate novel chalcones with potent angiogenic activities in vivo. Chalcone-based derivatives were evaluated using a transgenic zebrafish line with fluorescent vessels to real-time monitor the effect on angiogenesis. Results showed that the chalcone analogues did not possess anti-angiogenic effect on zebrafish vasculatures; instead, some of them displayed potent pro-angiogenic effects on the formation of the sub-intestinal vein. Similar pro-angiogenic effects can also be seen on wild type zebrafish embryos. Moreover, the expression of vegfa, the major regulator for angiogenesis, was also upregulated in their treatment. Taken together, we have synthesized and identified a series of novel chalcone-based derivatives as potent in vivo pro-angiogenic compounds. These novel compounds hold potential for therapeutic angiogenesis.

  2. Xanthohumol, a prenylated chalcone from Humulus lupulus L., inhibits cholesteryl ester transfer protein.

    Science.gov (United States)

    Hirata, Hiroshi; Takazumi, Koji; Segawa, Shuichi; Okada, Yukio; Kobayashi, Naoyuki; Shigyo, Tatsuro; Chiba, Hitoshi

    2012-10-01

    High density lipoprotein (HDL)-cholesterol levels are correlated with a low risk of atherosclerosis. The inhibition of cholesteryl ester transfer protein (CETP), which catalyses cholesterol transfer between lipoproteins, leads to an increase in HDL-cholesterol and is expected to be the next anti-atherogenic target. This study revealed that xanthohumol, a prenylated chalcone, showed the highest inhibition against CETP from screening of natural products in various plants. We investigated the inhibitory activity of some chalcones and flavanones. Naringenin chalcone showed weak CETP inhibition compared with xanthohumol. In addition, isoxanthohumol and naringenin drastically decreased the inhibitory activity. These results suggest that the prenyl group and chalcone structure of xanthohumol were responsible for the CETP inhibitory activity.

  3. Chalcones from Chinese liquorice inhibit proliferation of T cells and production of cytokines

    DEFF Research Database (Denmark)

    Barfod, Lea; Kemp, Kåre; Hansen, Majbritt;

    2002-01-01

    of cytokines revealed that the chalcones inhibited the production rather than the release of the cytokines. Taken together, these results indicate that LicA and some analogues may have immunomodulatory effects, and may thus be candidates not only as anti-microbial agents, but also for the treatment of other......Licochalcone A (LicA), an oxygenated chalcone, has been shown to inhibit the growth of both parasites and bacteria. In this study, we investigated the effect of LicA and four synthetic analogues on the activity of human peripheral blood mononuclear cell proliferation and cytokine production. Four...... out of five chalcones tested inhibited the proliferation of lymphocytes measured by thymidine incorporation and by flow cytometry. The production of pro- and anti-inflammatory cytokines from monocytes and T cells was also inhibited by four of five chalcones. Furthermore, intracellular detection...

  4. Synthesis, crystal growth and studies on non-linear optical property of new chalcones

    Science.gov (United States)

    Sarojini, B. K.; Narayana, B.; Ashalatha, B. V.; Indira, J.; Lobo, K. G.

    2006-09-01

    The synthesis, crystal growth and non-linear optical (NLO) property of new chalcone derivatives are reported. 4-Propyloxy and 4-butoxy benzaldehydes were made to under go Claisen-Schmidt condensation with 4-methoxy, 4-nitro and 4-phenoxy acetophenones to form corresponding chalcones. The newly synthesized compounds were characterized by analytical and spectral data. The Second harmonic generation (SHG) efficiency of these compounds was measured by powder technique using Nd:YAG laser. Among tested compounds three chalcones showed NLO property. The chalcone 1-(4-methoxyphenyl)-3-(4-propyloxy phenyl)-2-propen-1-one exhibited SHG conversion efficiency 2.7 times that of urea. The bulk crystal of 1-(4-methoxyphenyl)-3-(4-butoxyphenyl)-2-propen-1-one (crystal size 65×28×15 mm 3) was grown by slow-evaporation technique from acetone. Microhardness of the crystal was tested by Vicker's microhardness method.

  5. Bidentate coordinating behaviour of chalcone based ligands towards oxocations: VO(IV) and Mo(V)

    Science.gov (United States)

    Thaker, B. T.; Barvalia, R. S.

    2013-08-01

    We synthesized and studied the coordinating behaviour of chalcone based ligands derived from DHA and n-alkoxy benzaldehyde and their complexes of VO(IV) and MoO(V). The chalcone ligands are characterized by elemental analyses, UV-visible, IR, 1H NMR, and mass spectra. The resulting oxocation complexes are also characterized by elemental analyses, IR, 1H NMR, electronic, electron spin resonance spectra, magnetic susceptibility measurement and molar conductance studies. The IR and 1H NMR spectral data suggest that the chalcone ligands behave as a monobasic bidentate with O:O donor sequence towards metal ion. The molar conductivity data show them to be non-electrolytes. From the electronic, magnetic and ESR spectral data suggest that all the chalcone ligand complexes of VO(IV) and MoO(V) have distorted octahedral geometry.

  6. Chemical reactivity and biological activity of chalcones and other α,β-unsaturated carbonyl compounds.

    Science.gov (United States)

    Maydt, Daniela; De Spirt, Silke; Muschelknautz, Christian; Stahl, Wilhelm; Müller, Thomas J J

    2013-08-01

    Abstract 1. Chalcones are structural analogues of benzalacetophenone (BAP). Several derivatives have been identified in plants and anticarcinogenic and anti-inflammatory properties were attributed to the compounds, probably related to their direct antioxidant activity or stimulatory effects on the expression of endogenous defence enzymes like hemeoxygenase-1 (HO-1). HO-1 expression is triggered by the Nrf2-Keap1 signalling pathway, initiated by the addition of chalcones to thiol groups of Keap1 via Michael-type reaction. 2. The present study used a model system estimating the reactivity of different synthetic chalcones and other α,β-unsaturated carbonyl compounds with thiols and compared the chemical reactivity with the biological activity, measured by HO-1 expression in human dermal fibroblasts. 3. Chemical reactivity with the thiol group of N-acetylcysteine was determined with 5,5'-dithiobis-(2-nitrobenzoic acid) and followed chemical principles of structure-reactivity relationship. Most reactive were sulforaphane, dimethylfumarate, chalcone 3 ((2E)-1-phenyl-3-pyrimidin-2-ylprop-2-en-1-one) and chalcone 7 (1,3-diphenylprop-2-yn-1-one). This result demonstrates that α,β-unsaturated carbonyl derivatives react with thiols differently. All compounds were also biologically active; however, expression of HO-1 was not only related to the chemical reactivity but also to the lipophilicity of the molecules which likely affected transmembrane uptake. Most efficient inducers of HO-1 expression were BAP, 4-hydroxynonenal and chalcone 1 (4-[(1E)-3-oxo-3-phenylprop-1-en-1-yl]benzonitrile), chalcone 5 ((2E)-1-phenyl-3-[4-(trifluoromethyl)-phenyl]prop-2-en-1-one) and chalcone 7.

  7. Different effects of two cyclic chalcone analogues on redox status of Jurkat T cells.

    Science.gov (United States)

    Rozmer, Zsuzsanna; Berki, Tímea; Maász, Gábor; Perjési, Pál

    2014-12-01

    Chalcones are intermediary compounds of the biosynthetic pathway of the naturally flavonoids. Previous studies have demonstrated that chalcones and their conformationally rigid cyclic analogues have tumour cell cytotoxic and chemopreventive effects. It has been shown that equitoxic doses of the two cyclic chalcone analogues (E)-2-(4'-methoxybenzylidene)-(2) and (E)-2-(4'-methylbenzylidene)-1-benzosuberone (3) have different effect on cell cycle progress of the investigated Jurkat cells. It was also found that the compounds affect the cellular thiol status of the treated cells and show intrinsic (non-enzyme-catalyzed) reactivity towards GSH under cell-free conditions. In order to gain new insights into the cytotoxic mechanism of the compounds, effects on the redox status and glutathione level of Jurkat cells were investigated. Detection of intracellular ROS level in Jurkat cells exposed to 2 and 3 was performed using the dichlorofluorescein-assay. Compound 2 did not influence ROS activity either on 1 or 4h exposure; in contrast, chalcone 3 showed to reduce ROS level at both timepoints. The two compounds had different effects on cellular glutathione status as well. Compound 2 significantly increased the oxidized glutathione (GSSG) level showing an interference with the cellular antioxidant defence. On the contrary, chalcone 3 enhanced the reduced glutathione level, indicating enhanced cellular antioxidant activity. To investigate the chalcone-GSH conjugation reactions under cellular conditions, a combination of a RP-HPLC method with electrospray ionization mass spectrometry (ESI-MS) was performed. Chalcone-GSH adducts could not be observed either in the cell supernatant or the cell sediment after deproteinization. The investigations provide further details of dual - cytotoxic and chemopreventive - effects of the cyclic chalcone analogues.

  8. Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds.

    Science.gov (United States)

    Guantai, Eric M; Ncokazi, Kanyile; Egan, Timothy J; Gut, Jiri; Rosenthal, Philip J; Smith, Peter J; Chibale, Kelly

    2010-12-01

    A targeted series of chalcone and dienone hybrid compounds containing aminoquinoline and nucleoside templates was synthesized and evaluated for in vitro antimalarial activity. The Cu(I)-catalyzed cycloaddition of azides and terminal alkynes was applied as the hybridization strategy. Several chalcone-chloroquinoline hybrid compounds were found to be notably active, with compound 8b the most active, exhibiting submicromolar IC(50) values against the D10, Dd2 and W2 strains of Plasmodium falciparum.

  9. Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation

    OpenAIRE

    2013-01-01

    Chalcone derivatives have attracted increasing attention due to their numerous pharmacological activities. Changes in their structures have displayed high degree of diversity that has proven to result in a broad spectrum of biological activities. The present study highlights the synthesis of some halogen substituted chalcones 3(a–i) containing the 5-chlorothiophene moiety, their X-ray crystal structures and the evaluation of possible biological activities such as antibacterial, antifungal and...

  10. Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

    Energy Technology Data Exchange (ETDEWEB)

    Silva, Wender A.; Andrade, Carlos Kleber Z.; Napolitano, Hamilton B., E-mail: wender@unb.br, E-mail: ckleber@unb.br [Universidade de Brasilia (LaQMOS/UnB), DF (Brazil). Inst. de Quimica; Vencato, Ivo; Castro, Miriam R.C. de; Camargo, Ademir J. [Universidade Estadual de Goias (UEG), Anapolis, GO (Brazil). Ciencias Exatas e Tecnologicas; Lariucci, Carlito [Universidade Estadual de Goias (UEG), Goiania, GO (Brazil). Inst. de Fisica

    2013-01-15

    The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structure activity relationship. (author)

  11. Natural chalcones as dual inhibitors of HDACs and NF-κB

    OpenAIRE

    2012-01-01

    Histone deacetylase enzymes (HDACs) are emerging as a promising biological target for cancer and inflammation. Using a fluorescence assay, we tested the in vitro HDAC inhibitory activity of twenty-one natural chalcones, a widespread group of natural products with well-known anti-inflammatory and antitumor effects. Since HDACs regulate the expression of the transcription factor NF-κB, we also evaluated the inhibitory potential of the compounds on NF-κB activation. Only four chalcones, isoliqui...

  12. Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells.

    Science.gov (United States)

    Ramirez-Tagle, Rodrigo; Escobar, Carlos A; Romero, Valentina; Montorfano, Ignacio; Armisén, Ricardo; Borgna, Vincenzo; Jeldes, Emanuel; Pizarro, Luis; Simon, Felipe; Echeverria, Cesar

    2016-02-22

    Hepatocellular carcinoma (HCC) is one of the most commonly diagnosed cancers worldwide. Chemoprevention of HCC can be achieved through the use of natural or synthetic compounds that reverse, suppress or prevent the development of cancer progression. In this study, we investigated the antiproliferative effects and the mechanism of action of two compounds, 2,3,4'-trimethoxy-2'-hydroxy-chalcone (CH1) and 3'-bromo-3,4-dimethoxy-chalcone (CH2), over human hepatoma cells (HepG2 and Huh-7) and cultured mouse hepatocytes (HepM). Cytotoxic effects were observed over the HepG2 and Huh-7, and no effects were observed over the HepM. For HepG2 cells, treated separately with each chalcone, typical apoptotic laddering and nuclear condensation were observed. Additionally, the caspases and Bcl-2 family proteins activation by using Western blotting and immunocytochemistry were studied. Caspase-8 was not activated, but caspase-3 and -9 were both activated by chalcones in HepG2 cells. Chalcones also induced reactive oxygen species (ROS) accumulation after 4, 8 and 24 h of treatment in HepG2 cells. These results suggest that apoptosis in HepG2 was induced through: (i) a caspase-dependent intrinsic pathway; and (ii) by alterations in the cellular levels of Bcl-2 family proteins, and also, that the chalcone moiety could be a potent candidate as novel anticancer agents acting on human hepatomas.

  13. Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells

    Directory of Open Access Journals (Sweden)

    Rodrigo Ramirez-Tagle

    2016-02-01

    Full Text Available Hepatocellular carcinoma (HCC is one of the most commonly diagnosed cancers worldwide. Chemoprevention of HCC can be achieved through the use of natural or synthetic compounds that reverse, suppress or prevent the development of cancer progression. In this study, we investigated the antiproliferative effects and the mechanism of action of two compounds, 2,3,4′-trimethoxy-2′-hydroxy-chalcone (CH1 and 3′-bromo-3,4-dimethoxy-chalcone (CH2, over human hepatoma cells (HepG2 and Huh-7 and cultured mouse hepatocytes (HepM. Cytotoxic effects were observed over the HepG2 and Huh-7, and no effects were observed over the HepM. For HepG2 cells, treated separately with each chalcone, typical apoptotic laddering and nuclear condensation were observed. Additionally, the caspases and Bcl-2 family proteins activation by using Western blotting and immunocytochemistry were studied. Caspase-8 was not activated, but caspase-3 and -9 were both activated by chalcones in HepG2 cells. Chalcones also induced reactive oxygen species (ROS accumulation after 4, 8 and 24 h of treatment in HepG2 cells. These results suggest that apoptosis in HepG2 was induced through: (i a caspase-dependent intrinsic pathway; and (ii by alterations in the cellular levels of Bcl-2 family proteins, and also, that the chalcone moiety could be a potent candidate as novel anticancer agents acting on human hepatomas.

  14. Chalcones and Dihydrochalcones Augment TRAIL-Mediated Apoptosis in Prostate Cancer Cells

    Directory of Open Access Journals (Sweden)

    Wojciech Krol

    2010-08-01

    Full Text Available Chalcones and dihydrochalcones exhibit chemopreventive and antitumor activity. TRAIL (tumor necrosis factor-related apoptosis-inducing ligand is a natural endogenous anticancer agent. We examined the cytotoxic and apoptotic effect of chalcones and dihydrochalcones on TRAIL-mediated apoptosis in LNCaP prostate cancer cells. The cytotoxicity was evaluated by the MTT and LDH assays. The apoptosis was detected using annexin V-FITC by flow cytometry and fluorescence microscopy. The ΔΨm was evaluated using DePsipher staining by fluorescence microscopy. Our study showed that two tested chalcones (chalcone and 2’,6’dihydroxy-4’-methoxychalcone and three dihydrochalcones (2’,6’-dihydroxy-4’4-dimethoxydihydrochalcone, 2’,6’-dihydroxy-4’-methoxydihydro- chalcone,  and 2’,4’,6’-trihydroxydihydrochalcone, called phloretin markedly augmented TRAIL-induced apoptosis and cytotoxicity in LNCaP cells and confirmed the significant role of chalcones in chemoprevention of prostate cancer.

  15. 1H and 13C NMR spectral assignments of chalcones bearing pyrazoline-carbothioamide groups.

    Science.gov (United States)

    Yoon, Hyuk; Ahn, Seunghyun; Park, Mijoo; Kim, Dong-Wook; Kim, Sang Ho; Koh, Dongsoo; Lim, Yoongho

    2013-08-01

    Chalcones are known to act on various physiological targets. As a result, structural modifications of chalcones have been studied extensively. Benzochalcones, in which the A-ring of chalcone is substituted with a naphthalene unit, inhibits breast cancer resistance protein. Chalcones in which the α,β-unsaturated carbonyl group is switched with a pyrazoline moiety are potent cytotoxic agents against various cancer cell lines, and chalcones with a pyrazoline-1-carbothioamide group instead of an α,β-unsaturated carbonyl group exhibit antimicrobial activities. The present report describes hybrid molecules designed from benzochalcone and pyrazoline-carbothioamide. Methoxylation of plant-derived polyphenols alters their hydrophobicity, resulting in changes in biological function and intracellular compartmentation. In the current study, 22 novel methoxylated 3-(naphthalen-2-yl)-N,5-diphenyl-pyrazoline-1-carbothioamide derivatives were prepared. This report provides complete assignments of their (1)H and (13)C NMR data, which can be used to subsequently identify chalcones bearing pyrazoline-carbothioamide groups.

  16. Cloning, functional expression, and characterization of a chalcone 3-hydroxylase from Cosmos sulphureus.

    Science.gov (United States)

    Schlangen, Karin; Miosic, Silvija; Thill, Jana; Halbwirth, Heidi

    2010-07-01

    A chalcone 3-hydroxylase (CH3H) cDNA clone was isolated and characterized from Cosmos sulphureus petals accumulating butein (2',3,4,4'-tetrahydroxychalcone) derivatives as yellow flower pigments. The recombinant protein catalyses the introduction of an additional hydroxyl group in the B-ring of chalcones, a reaction with high similarity to the hydroxylation of flavonoids catalysed by the well-studied flavonoid 3'-hydroxylase (F3'H). CH3H shows high specificity for chalcones, but a low F3'H activity was also detected. By contrast, the common F3'H from C. sulphureus does not accept chalcones as substrates and is therefore unlikely to be involved in the creation of the B-ring hydroxylation pattern of the yellow flower pigments. CH3H was primarily expressed in young buds, the main tissue for chalcone pigment formation. Expression levels in open flowers and 3-d-old seedlings were lower and almost no CH3H expression was observed in leaves. F3'H, in contrast, showed the highest expression also in buds, but comparable expression rates in all other tissues tested. Recombinant hybrid proteins constructed from CH3H and F3'H fragments demonstrated that amino acid residues at a substrate recognition site and an insertion of four amino acid residues in a putative loop region have an impact on chalcone acceptance. This is the first identification of a CH3H cDNA from any plant species.

  17. Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells

    Science.gov (United States)

    Ramirez-Tagle, Rodrigo; Escobar, Carlos A.; Romero, Valentina; Montorfano, Ignacio; Armisén, Ricardo; Borgna, Vincenzo; Jeldes, Emanuel; Pizarro, Luis; Simon, Felipe; Echeverria, Cesar

    2016-01-01

    Hepatocellular carcinoma (HCC) is one of the most commonly diagnosed cancers worldwide. Chemoprevention of HCC can be achieved through the use of natural or synthetic compounds that reverse, suppress or prevent the development of cancer progression. In this study, we investigated the antiproliferative effects and the mechanism of action of two compounds, 2,3,4′-trimethoxy-2′-hydroxy-chalcone (CH1) and 3′-bromo-3,4-dimethoxy-chalcone (CH2), over human hepatoma cells (HepG2 and Huh-7) and cultured mouse hepatocytes (HepM). Cytotoxic effects were observed over the HepG2 and Huh-7, and no effects were observed over the HepM. For HepG2 cells, treated separately with each chalcone, typical apoptotic laddering and nuclear condensation were observed. Additionally, the caspases and Bcl-2 family proteins activation by using Western blotting and immunocytochemistry were studied. Caspase-8 was not activated, but caspase-3 and -9 were both activated by chalcones in HepG2 cells. Chalcones also induced reactive oxygen species (ROS) accumulation after 4, 8 and 24 h of treatment in HepG2 cells. These results suggest that apoptosis in HepG2 was induced through: (i) a caspase-dependent intrinsic pathway; and (ii) by alterations in the cellular levels of Bcl-2 family proteins, and also, that the chalcone moiety could be a potent candidate as novel anticancer agents acting on human hepatomas. PMID:26907262

  18. Solvent-free Michael addition reaction of fluorene with chalcon

    Institute of Scientific and Technical Information of China (English)

    Fu Feng

    2011-01-01

    A series of novel Michael addition products of fluorene to chalcone were obtained in the presence of sodium hydroxide under solvent-free condition. The advantages of this procedure were mild reaction conditions, simple protocol, and high yields. The structures of the products were characterized by IR, 1H NMR, MS and X-ray diffraction. The crystal of the new compound 3 h is y= 64.2440(10)°, V = 2.4137(3) nm3, Z= 4, Dc=1.220 g/cm3, μ = 0.286 mm-1, F(000) = 920, R = 0.0656 and wR = 0.1554 for 5664 observed reflection with I > 2σ(I).

  19. NMR studies of chalcones isolated from Neoraputia magnifica; Estudos por RMN de chalconas isoladas de Neoraputia magnifica

    Energy Technology Data Exchange (ETDEWEB)

    Tomazela, Daniela M.; Rodrigues Filho, Edson; Silva, M. Fatima das G. F. da; Fernandes, Joao B.; Vieira, Paulo C. [Sao Carlos Univ., SP (Brazil). Dept. de Quimica

    1997-12-31

    From Neoraputia magnifica (Rutaceae) we isolated two chalcones belonging to the 1,3-diarylprop-2-en-1-one group. The two chalcones presented two or three methoxyl groups at ring B; a dimethychromene between C-5`and O-6`and also an additional methoxyl at ring A. It has been noted that H-{beta} and C-{beta} of a chalcone are more deshielded than H-{alpha}. However, HMOC and HMBC experiments of the chalcones described here showed the opposite situation where H-{alpha} is more deshielded than H-{beta}. (author) 5 refs., 4 figs., 7 tabs.

  20. Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities.

    Science.gov (United States)

    Kil, Yun-Seo; Choi, Seul-Ki; Lee, Yun-Sil; Jafari, Mahtab; Seo, Eun-Kyoung

    2015-10-23

    Five new chalcones, 4,2',4'-trihydroxy-3'-[(2E,5E)-7-methoxy-3,7-dimethyl-2,5-octadienyl]chalcone (1), (±)-4,2',4'-trihydroxy-3'-[(2E)-6-hydroxy-7-methoxy-3,7-dimethyl-2-octenyl]chalcone (2), 4,2',4'-trihydroxy-3'-[(2E)-3-methyl-5-(1,3-dioxolan-2-yl)-2-pentenyl]chalcone (3), 2',3'-furano-4-hydroxy-4'-methoxychalcone (4), and (±)-4-hydroxy-2',3'-(2,3-dihydro-2-methoxyfurano)-4'-methoxychalcone (5), were isolated from the aerial parts of Angelica keiskei Koidzumi together with eight known chalcones, 6-13, which were identified as (±)-4,2',4'-trihydroxy-3'-[(6E)-2-hydroxy-7-methyl-3-methylene-6-octenyl]chalcone (6), xanthoangelol (7), xanthoangelol F (8), xanthoangelol G (9), 4-hydroxyderricin (10), xanthoangelol D (11), xanthoangelol E (12), and xanthoangelol H (13), respectively. Chalcones 1-13 were evaluated for their promoter activity on heat shock protein 25 (hsp25, murine form of human hsp27). Compounds 1 and 6 activated the hsp25 promoter by 21.9- and 29.2-fold of untreated control at 10 μM, respectively. Further protein expression patterns of heat shock factor 1 (HSF1), HSP70, and HSP27 by 1 and 6 were examined. Compound 6 increased the expression of HSF1, HSP70, and HSP27 by 4.3-, 1.5-, and 4.6-fold of untreated control, respectively, without any significant cellular cytotoxicities, whereas 1 did not induce any expression of these proteins. As a result, 6 seems to be a prospective HSP inducer.

  1. In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

    KAUST Repository

    Zenger, Katharina

    2015-07-19

    Xanthohumol (XN), the major prenylated chalcone from hops (Humulus lupulus L.), has received much attention within the last years, due to its multiple pharmacological activities including anti-proliferative, anti-inflammatory, antioxidant, pro-apoptotic, anti-bacterial and anti-adhesive effects. However, there exists a huge number of metabolites and structurally-related chalcones, which can be expected, or are already known, to exhibit various effects on cells. We have therefore analyzed the effects of XN and 18 other chalcones in a panel, consisting of multiple cell-based assays. Readouts of these assays addressed distinct aspects of cell-toxicity, like proliferation, mitochondrial health, cell cycle and other cellular features. Besides known active structural elements of chalcones, like the Michael system, we have identified several moieties that seem to have an impact on specific effects and toxicity in human liver cells in vitro. Based on these observations, we present a structure-toxicity model, which will be crucial to understand the molecular mechanisms of wanted effects and unwanted side-effects of chalcones.

  2. Study of the antibacterial and antifungal activities of synthetic benzyl bromides, ketones, and corresponding chalcone derivatives

    Science.gov (United States)

    Shakhatreh, Muhamad Ali K; Al-Smadi, Mousa L; Khabour, Omar F; Shuaibu, Fatima A; Hussein, Emad I; Alzoubi, Karem H

    2016-01-01

    Several applications of chalcones and their derivatives encouraged researchers to increase their synthesis as an alternative for the treatment of pathogenic bacterial and fungal infections. In the present study, chalcone derivatives were synthesized through cross aldol condensation reaction between 4-(N,N-dimethylamino)benzaldehyde and multiarm aromatic ketones. The multiarm aromatic ketones were synthesized through nucleophilic substitution reaction between 4-hydroxy acetophenone and benzyl bromides. The benzyl bromides, multiarm aromatic ketones, and corresponding chalcone derivatives were evaluated for their activities against eleven clinical pathogenic Gram-positive, Gram-negative bacteria, and three pathogenic fungi by the disk diffusion method. The minimum inhibitory concentration was determined by the microbroth dilution technique. The results of the present study demonstrated that benzyl bromide derivatives have strong antibacterial and antifungal properties as compared to synthetic chalcone derivatives and ketones. Benzyl bromides (1a and 1c) showed high ester activity against Gram-positive bacteria and fungi but moderate activity against Gram-negative bacteria. Therefore, these compounds may be considered as good antibacterial and antifungal drug discovery. However, substituted ketones (2a–b) as well as chalcone derivatives (3a–c) showed no activity against all the tested strains except for ketone (2c), which showed moderate activity against Candida albicans. PMID:27877017

  3. Photogeneration of reactive oxygen species and photoinduced plasmid DNA cleavage by novel synthetic chalcones.

    Science.gov (United States)

    Yesuthangam, Y; Pandian, S; Venkatesan, K; Gandhidasan, R; Murugesan, R

    2011-03-02

    This paper describes the synthesis and photodynamic properties of six different chalcone derivatives. Using N,N-dimethyl-4-nitrosoaniline (RNO) bleaching assay, the singlet oxygen generating efficiencies of these chalcones are determined relative to rose bengal (RB). Superoxide dismutase (SOD) inhibitable cytochrome c reduction assay and electron magnetic resonance (EMR) spin trapping techniques are used to determine the superoxide anion radical (O₂·⁻) yield upon photoirradiation. Photoinduced DNA scission studies show that O₂·⁻ is involved in the DNA strand break. In addition, antimicrobial activity of these chalcones is also investigated. Structure activity relationship accounts for the difference in the photogeneration of reactive oxygen species (ROS) by these sensitizers. Presence of electron releasing -OCH₃ groups enhances the photogeneration of ROS. Cyclic voltammetry studies indicate a correlation between enzymatic O₂·⁻ generation efficiency and redox potential of chalcones. Both O₂·⁻ (Type I) and ¹O₂ (Type II) paths are involved in the photosensitization of chalcones. The LUMO energies obtained by molecular modeling correlate with the one-electron reduction potentials.

  4. Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers.

    Science.gov (United States)

    Hofmann, Emily; Webster, Jonathan; Do, Thuy; Kline, Reid; Snider, Lindsey; Hauser, Quintin; Higginbottom, Grace; Campbell, Austin; Ma, Lili; Paula, Stefan

    2016-02-15

    In this study, we evaluated the abilities of a series of chalcones to inhibit the activity of the enzyme xanthine oxidase (XO) and to scavenge radicals. 20 mono- and polyhydroxylated chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and then tested for inhibitory potency against XO, a known generator of reactive oxygen species (ROS). In parallel, the ability of the synthesized chalcones to scavenge a stable radical was determined. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. Moreover, the most effective radical scavengers had two neighboring hydroxyl groups on at least one of the two phenyl rings. Since it has been proposed previously that XO inhibition and radical scavenging could be useful properties for reduction of ROS-levels in tissue, we determined the chalcones' effects to rescue neurons subjected to ROS-induced stress created by the addition of β-amyloid peptide. Best protection was provided by chalcones that combined good inhibitory potency with high radical scavenging ability in a single molecule, an observation that points to a potential therapeutic value of this compound class.

  5. In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells.

    Science.gov (United States)

    Zenger, Katharina; Dutta, Subhajit; Wolff, Horst; Genton, Marc G; Kraus, Birgit

    2015-10-02

    Xanthohumol (XN), the major prenylated chalcone from hops (Humulus lupulus L.), has received much attention within the last years, due to its multiple pharmacological activities including anti-proliferative, anti-inflammatory, antioxidant, pro-apoptotic, anti-bacterial and anti-adhesive effects. However, there exists a huge number of metabolites and structurally-related chalcones, which can be expected, or are already known, to exhibit various effects on cells. We have therefore analyzed the effects of XN and 18 other chalcones in a panel, consisting of multiple cell-based assays. Readouts of these assays addressed distinct aspects of cell-toxicity, like proliferation, mitochondrial health, cell cycle and other cellular features. Besides known active structural elements of chalcones, like the Michael system, we have identified several moieties that seem to have an impact on specific effects and toxicity in human liver cells in vitro. Based on these observations, we present a structure-toxicity model, which will be crucial to understand the molecular mechanisms of wanted effects and unwanted side-effects of chalcones.

  6. SYNTHESIS AND BIOLOGICAL ACTIVITY OF IMIDAZOLE DERIVED CHALCONES AND IT’S PYRIMIDINES

    Directory of Open Access Journals (Sweden)

    Pavan Kumar Padarthi

    2013-06-01

    Full Text Available Microbial contribution increasing rapidly due to invasion by the pathogenic organisms like bacteria, fungi and virus in the present disease burden of human health. To treat these diseases many potent and broad spectrum antibiotics were discovered e.g., ampicillin, amoxicillin, carbenicillin, ofloxacin and tetracycline etc., Even though antibiotics are life saving drugs in therapeutics but they are potentially harmful. These harmful effects include allergic and anaphylactic reaction, development of resistance, destruction of normal non-pathogenic bacterial flora and selective toxicity like aplastic anemia, kidney damage. As the microbial resistance make anti-microbial therapy very complex, there is a definite need of novel anti-microbials or drugs for combination therapy with standard antibiotics. Our aim was to synthesize and explore the anti-microbial activity of chalcones and its derived pyrimidines against various pathological micro organisms. Novel imidazole derived chalcones were synthesized and characterization was carried out by analyzing melting point, IR, 1H NMR data. The synthesized chalcones and pyrimidines are tested for their antimicrobial activity against various bacteria as well as fungi. Further synthesis of novel heterocyclic chalcones, structural elucidation, spectral analysis, biological activity of synthesized chalcones and its derived pyrimidines gives a hope for enhanced biological action using QSAR Studies.

  7. Antifungal dimeric chalcone derivative kamalachalcone E from Mallotus philippinensis.

    Science.gov (United States)

    Kulkarni, Roshan R; Tupe, Santosh G; Gample, Suwarna P; Chandgude, Macchindra G; Sarkar, Dhiman; Deshpande, Mukund V; Joshi, Swati P

    2014-01-01

    From the red coloured extract (Kamala) prepared through acetone extraction of the fresh whole uncrushed fruits of Mallotus philippinensis, one new dimeric chalcone (1) along with three known compounds 1-(5,7-dihydroxy-2,2,6-trimethyl-2H-1-benzopyran-8-yl)-3-phenyl-2-propen-1-one (2), rottlerin (3) and 4'-hydroxyrottlerin (4) were isolated. The structure of compound 1 was elucidated by 1D and 2D NMR analyses that included HSQC, HMBC, COSY and ROESY experiments along with the literature comparison. Compounds 1-4 were evaluated for antifungal activity against different human pathogenic yeasts and filamentous fungi. The antiproliferative activity of the compounds was evaluated against Thp-1 cell lines. Compounds 1 and 2 both exhibited IC50 of 8, 4 and 16 μg/mL against Cryptococcus neoformans PRL518, C. neoformans ATCC32045 and Aspergillus fumigatus, respectively. Compound 4, at 100 μg/mL, showed 54% growth inhibition of Thp-1 cell lines.

  8. Synthesis and Phase Transition Behaviours of New Chalcone Derivatives

    Directory of Open Access Journals (Sweden)

    S. T. Ha

    2013-01-01

    Full Text Available A series of new chalcone derivatives with a general formula of C11H27COOC6H4COCH=CHC6H4X where X=F, Cl, Br, and NO2 were well synthesized and crystallized from organic solution. The physical properties as well as the chemical formulations of these compounds were determined by spectroscopic techniques (FTIR, and 1H and 13C NMR. Differential scanning calorimetry (DSC and polarizing optical microscopy (POM techniques were employed to study their transition temperatures and mesophase characteristics. DSC thermograms of compounds with fluoro and nitro substituents displayed direct isotropization and recrystallization during heating and cooling processes. Chloro and bromo analogues exhibited Cr1-to-Cr2 transition within the crystal phase region. It was also found that enone linkage showed fewer tendencies to exhibit mesomorphic property compared to imine linkage. However, when enone linkage is combined with other central linkages and additional phenyl rings, it turns conducive to mesomorphism.

  9. Synthesis of novel chalcone derivatives by conventional and microwave irradiation methods and their pharmacological activities

    Directory of Open Access Journals (Sweden)

    Mohammed Rayees Ahmad

    2016-09-01

    Full Text Available Chalcones are abundant in edible plants and are considered to be the precursors of flavonoids and isoflavonoids. Chalcones belong to an important class of flavonoids, which may be prepared by Claisen–Schmidt condensation. They possess a wide range of biological activities and industrial applications. The cytotoxicity against tumour cell lines may be the result of disruption of the cell cycle, inhibition of angiogenesis, interference with p53-MDM2 interaction, mitochondrial uncoupling or induction of apoptosis. Chalcones are synthesized by conventional and microwave assisted synthesis methods. By microwave assisted synthesis, a considerable increase in the reaction rate has been observed and that too, with better yields. The compounds have been screened for cytotoxic activity and antioxidant activity.

  10. Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones.

    Science.gov (United States)

    Konduru, Naveen Kumar; Dey, Sunita; Sajid, Mohammad; Owais, Mohammad; Ahmed, Naseem

    2013-01-01

    Two series of chalcone based sulfone and bisulfone derivatives were synthesized using chalcone, thiophenol and sodium metal at room temperature, followed by oxidation of chalcone sulfides with m-CPBA at 0 °C in a novel method. Both sulfones and bisulfones were evaluated for their antimicrobial activities against Aspergillus niger and Candida albicans (yeast), Bacillus subtilis and Staphylococcus aureus (Gram (+) bacteria) and Pseudomonas aeruginosa and Salmonella typhimurium (Gram (-) bacteria) strains. Among them, compounds 2c, 3c, 6c, 7c, 8c and 9c have shown high antifungal activity against C. albicans compare to reference drugs viz. Amphotericin-B and Nystatin. Compound 1c has shown slightly better antibacterial activity against B. subtilis and compounds 5c, 6c and 7c have shown excellent antibacterial activity against S. typhimurium in compare to reference drugs Ampicillin and Kanamycin.

  11. Study on third-order nonlinear optical properties of 4-methylsulfanyl chalcone derivatives using picosecond pulses

    Energy Technology Data Exchange (ETDEWEB)

    D' silva, E.D., E-mail: deepak.dsilva@gmail.com [Department of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574199 (India); Podagatlapalli, G. Krishna [Advanced Centre of Research in High Energy Materials (ACRHEM), University of Hyderabad, Hyderabad 500046 (India); Venugopal Rao, S., E-mail: soma_venu@yahoo.com [Advanced Centre of Research in High Energy Materials (ACRHEM), University of Hyderabad, Hyderabad 500046 (India); Dharmaprakash, S.M. [Department of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574199 (India)

    2012-11-15

    Graphical abstract: Photograph and schematic representation of Z-scan experimental setup used to investigate third order nonlinear properties of the chalcone materials. Highlights: ► Br and NO{sub 2} substituted chalcone derivatives were exposed to picosecond laser pulses. ► Third-order nonlinear optical (NLO) properties were investigated. ► Compounds show promising third-order and optical limiting properties. ► These materials found suitable for electrical and optical applications. -- Abstract: In this paper we present results from the experimental study of third-order nonlinear optical (NLO) properties of three molecules of Br and NO{sub 2} substituted chalcone derivatives namely (2E)-1-(4-bromophenyl)-3-[4(methylsulfanyl)phenyl]prop-2-en-1-one (4Br4MSP), (2E)-1-(3-bromophenyl)-3-[4-(methylsulfanyl) phenyl]prop-2-en-1-one (3Br4MSP) and (2E)-3[4(methylsulfanyl) phenyl]-1-(4-nitrophenyl)prop-2-en-1-one (4N4MSP). The NLO properties have been investigated by Z-scan technique using 2 ps laser pulses at 800 nm. The nonlinear refractive indices, nonlinear absorption coefficient, and the magnitude of third-order susceptibility have been determined. The values obtained are of the order of 10{sup −7} cm{sup 2}/GW, 10{sup −3} cm/GW and 10{sup −14} esu respectively. The molecular second hyperpolarizability for the chalcone derivatives is of the order of 10{sup −32} esu. The coupling factor, excited state cross section, ground state cross section etc. were determined. The optical limiting (OL) property was studied. The results suggest that the nonlinear properties investigated for present chalcones are comparable with some of the reported chalcone derivatives and can be desirable for NLO applications.

  12. Spectral, stoichiometric ratio, physicochemical, polarity and photostability studies of newly synthesized chalcone dye in organized media

    Energy Technology Data Exchange (ETDEWEB)

    Marwani, Hadi M., E-mail: hmarwani@kau.edu.sa [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Asiri, Abdullah M. [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Khan, Salman A. [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia)

    2013-04-15

    The main focus of this study was to investigate spectroscopic properties, stoichiometric ratios, physicochemical parameters, polarity and photostability behaviors of newly synthesized chalcone dye in organized media. The chalcone dye, 1-(2,5-Dimethyl-thiophen-3-yl)-3-(9-etnyl-9H-carbazol-3-yl)-propenone (DTEP), was prepared by the reaction of carbazole aldehyde with 3-acetyl-2,5-dimethythiophene. Data obtained from FT-IR, {sup 1}H-–NMR, {sup 13}C-NMR and elemental analysis were consistent with chemical structure of newly prepared DTEP. Increases in fluorescence intensities of DTEP with cetyltrimethyl ammonium bromide (CTAB) were observed. In comparison of fluorescence intensities for DTEP with CTAB, reductions in fluorescence intensities for DTEP with sodium dodecyl sulfate (SDS) were noticed under the same experimental and instrumental conditions. Additionally, Benesi–Hildebrand method was applied to determine stoichiometric ratios and association constants of DTEP with CTAB and SDS. Stern–Volmer plot was used in order to further confirm the stoichiometric ratio and association constant of DTEP with SDS. Physicochemical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment and fluorescence quantum yield of DTEP were also determined. Fluorescence polarity study displayed that DTEP was sensitive to the polarity of the microenvironment provided by different solvents. Finally, fluorescence steady-state measurements revealed that DTEP has high photostability against photobleaching. -- Highlights: ► Mechanistic understanding of molecular structure of newly synthesized chalcone dye. ► Exploring spectral behaviors and physicochemical parameters of chalcone dye. ► Determination of stoichiometric ratios and association constants of chalcone dye. ► Determination of fluorescence quantum yield in different solvents. ► High photostability against photobleaching of chalcone dye was observed.

  13. Synthesis and Antimicrobial Screening of New Pyrazolines Derived From Chalcones of Vanillin Analog

    Directory of Open Access Journals (Sweden)

    Krushnkumar Karangiya

    2016-03-01

    Full Text Available In present study the new series of 3-(Aryl-5-[4-(2, 4-Dichlorophenylmethoxy-3-methoxyphenyl]-4, 5-dihydro pyrazoline (2a-k and 3-(Aryl-5-[4-(2, 4-Dichlorophenylmethoxy-3-methoxyphenyl]-4, 5-dihydroacetyl pyrazoline (3a-k derivatives were synthesized from various substituted 3-Methoxy-4-(2, 4-Dichlorophenyl methoxy chalcones (1a-k. The new chalcones were synthesized using various acetophenones with newly synthesized aldehyde of vanillin analog by Claisen-Schmidt condensation. Characterization of pyrazoline derivatives have been established on the basis of IR, NMR, Mass and elemental analyses. The derivatives were screened for their in vitro antimicrobial Screening.

  14. Design and synthesis of novel chalcones as potent selective monoamine oxidase-B inhibitors.

    Science.gov (United States)

    Hammuda, Arwa; Shalaby, Raed; Rovida, Stefano; Edmondson, Dale E; Binda, Claudia; Khalil, Ashraf

    2016-05-23

    A novel series of substituted chalcones were designed and synthesized to be evaluated as selective human MAO-B inhibitors. A combination of either methylsulfonyl or trifluoromethyl substituents on the aromatic ketone moiety with a benzodioxol ring on the other end of the chalcone scaffold was investigated. The compounds were tested for their inhibitory activities on both human MAO-A and B. All compounds appeared to be selective MAO-B inhibitors with Ki values in the micromolar to submicromolar range. Molecular modeling studies have been performed to get insight into the binding mode of the synthesized compounds to human MAO-B active site.

  15. Synthesis of apoptotic chalcone analogues in HepG2 human hepatocellular carcinoma cells.

    Science.gov (United States)

    Park, Cheon-Soo; Ahn, Yongchel; Lee, Dahae; Moon, Sung Won; Kim, Ki Hyun; Yamabe, Noriko; Hwang, Gwi Seo; Jang, Hyuk Jai; Lee, Heesu; Kang, Ki Sung; Lee, Jae Wook

    2015-12-15

    Eight chalcone analogues were prepared and evaluated for their cytotoxic effects in human hepatoma HepG2 cells. Compound 5 had a potent cytotoxic effect. The percentage of apoptotic cells was significantly higher in compound 5-treated cells than in control cells. Exposure to compound 5 for 24h induced cleavage of caspase-8 and -3, and poly (ADP-ribose) polymerase (PARP). Our findings suggest that compound 5 is the active chalcone analogue that contributes to cell death in HepG2 cells via the extrinsic apoptotic pathway.

  16. Simple synthesis of novel diphenylsulfapyrimidine acetates from chalcones and their antimicrobial activity.

    Science.gov (United States)

    Wasfy, A A F; Aly, A A

    2003-01-01

    Given the significant low yield (19-43%) in reported results on the cyclocondensation of sulfaguanidine acetate with chalcones, a careful reinvestigation was carried out. A new series of chalcones, bearing electron-attracting groups in the aromatic moiety, have been used as precursors in the synthesis of diphenylsulfapyrimidine acetates with good yield. All synthesized compounds were active against G(+)- and G(-)-bacteria, and fungi. Combination of substituents (Cl, OMe, NO2, etc.) enhanced antimicrobial activity. Derivative with two NO2 groups exhibits an activity comparable with sulfadiazine.

  17. Piperidine-mediated synthesis of thiazolyl chalcones and their derivatives as potent antimicrobial agents.

    Science.gov (United States)

    Venkatesan, P; Maruthavanan, T

    2012-01-01

    A series of new thiazolyl chalcones, 1-[2-amino-4-methyl-1,3-thiazol-5-yl]-3-aryl-prop-2-en-1-one were prepared by piperidine mediated Claisen-Schmidt condensation of thiazolyl ketone with aromatic aldehyde. These chalcones on cyclisation gave 2-amino-6-(2-amino-4-methyl-1,3-thiazol-5-yl)-4-aryl-4H-pyridine-3-carbonitrile and 2-amino-6-(2-amino-4-methyl-1,3-thiazol-5-yl)-4-aryl-4H-pyran-3-carbonitrile. The result showed that the compounds exhibited marked potency as antimicrobial agents.

  18. Synthesis and Antimicrobial Screening of New Pyrazolines Derived From Chalcones of Vanillin Analog

    OpenAIRE

    2016-01-01

    In present study the new series of 3-(Aryl)-5-[4-(2, 4-Dichlorophenylmethoxy)-3-methoxyphenyl]-4, 5-dihydro pyrazoline (2a-k) and 3-(Aryl)-5-[4-(2, 4-Dichlorophenylmethoxy)-3-methoxyphenyl]-4, 5-dihydroacetyl pyrazoline (3a-k) derivatives were synthesized from various substituted 3-Methoxy-4-(2, 4-Dichlorophenyl methoxy) chalcones (1a-k). The new chalcones were synthesized using various acetophenones with newly synthesized aldehyde of vanillin analog by Claisen-Schmidt condensation. Character...

  19. Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus.

    Science.gov (United States)

    Vogel, Susanne; Heilmann, Jörg

    2008-07-01

    The minor hop ( Humulus lupulus) chalcones 3'-geranylchalconaringenin (3), 5'-prenylxanthohumol (4), flavokawin (5), xanthohumol H (8), xanthohumol C (9), and 1'',2''-dihydroxanthohumol C (10) were synthesized. The non-natural chalcones 3'-geranyl-6'-O-methylchalconaringenin (2), 3'-methylflavokawin (6), and 2'-O-methyl-3'-prenylchalconaringenin (7) were also synthesized. Cytotoxicity was investigated in HeLa cells, and these compounds all had IC 50 values comparable to xanthohumol (8.2-19.2 microM). The ORAC-fluorescein assay revealed potent antioxidative activity for 7 and 8 with 5.2 and 4.8 Trolox equivalents, respectively.

  20. Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum trin

    Energy Technology Data Exchange (ETDEWEB)

    Correa, Marivaldo J.C.; Nunes, Fatima M.; Bitencourt, Heriberto R.; Borges, Fabio C.; Guilhon, Giselle M.S.P.; Arruda, Mara S.P.; Marinho, Andrey M. R.; Santos, Alberdan S.; Alves, Claudio N.; Santos, Lourivaldo S., E-mail: lss@ufpa.b [Universidade Federal do Para (IQ/FEQ/UFPA), Belem, PA (Brazil). Inst. de Tecnologia. Faculdade de Engenharia Quimica; Brasil, Davi S.B. [Universidade Federal do Para (PPGQ/IQ/UFPA), Belem, PA (Brazil). Inst. de Quimica. Programa de Pos-Graduacao em Quimica

    2011-07-01

    The fungus Aspergillus flavus isolated as endophytic of the plant Paspalum maritimum Trin. was evaluated for its potential application in biotransformation reactions. The compounds chalcone (1), 3,4,5-trimethoxychalcone (2) and 2,3,4,4'-tetramethoxy chalcone (3) were biotransformed, respectively, in dihydrochalcone (4), 3,4,5-trimethoxydihydrochalcone (5) and 2,3,4,4'-tetramethoxydihydrochalcone (6). The structures were elucidated by spectroscopic methods including 1D and 2D NMR techniques, and MS analysis. The dihydrochalcones 5 and 6 are new compounds. (author)

  1. Employing NMR Spectroscopy To Evaluate Transmission of Electronic Effects in 4-Substituted Chalcones

    Science.gov (United States)

    Wachter-Jurcsak, Nanette; Zamani, Hossein

    1999-05-01

    Described is an organic synthesis experiment that demonstrates the electronic transmission by substituents. The effect of substitution at the para-position of the styryl ring of 1,3-diphenyl-2-propenones (chalcones) by typical electron-donating or -accepting groups can be observed by proton and carbon-13 NMR spectroscopy. A linear correlation is observed when the differences in chemical shift measurements for H are plotted against the corresponding Hammett substituent constant values. Good correlation between carbon-13 chemical shifts of the alpha carbon are also observed. The syntheses of the 4-substituted chalcones is presented as well as a brief discussion of the theory.

  2. Cytotoxic activity of substituted chalcones in terms of molecular electronic properties.

    Science.gov (United States)

    Kupcewicz, Bogumiła; Jarzęcki, Andrzej A; Małecka, Magdalena; Krajewska, Urszula; Rozalski, Marek

    2014-09-01

    Global chemical reactivity descriptors and lipophilicity (logP) were evaluated via density functional theory in order to clarify the structure-cytotoxic activity relationships of substituted chalcones. Stepwise multiple regression was employed to establish correlation between descriptors and cytotoxic activity against three cancer cell lines (HL-60, NALM-6 and WM-115) for 11 compounds. Regression analysis revealed that electrophilicity index and chemical potential significantly contributed in explaining of chalcones cytotoxic potential. Moreover, the established structure-activity relationships based on electronic structure properties allow indicating the substructures responsible for their cytotoxic activity. The study has also been supported by crystallographic data of 2-chloro-2'-hydroxychalcone.

  3. Synthesis and evaluation of novel prenylated chalcone derivatives as anti-leishmanial and anti-trypanosomal compounds.

    Science.gov (United States)

    Passalacqua, Thais Gaban; Dutra, Luiz Antonio; de Almeida, Letícia; Velásquez, Angela Maria Arenas; Torres, Fabio Aurelio Esteves; Yamasaki, Paulo Renato; dos Santos, Mariana Bastos; Regasini, Luis Octavio; Michels, Paul A M; Bolzani, Vanderlan da Silva; Graminha, Marcia A S

    2015-08-15

    Chalcones form a class of compounds that belong to the flavonoid family and are widely distributed in plants. Their simple structure and the ease of preparation make chalcones attractive scaffolds for the synthesis of a large number of derivatives enabling the evaluation of the effects of different functional groups on biological activities. In this Letter, we report the successful synthesis of a series of novel prenylated chalcones via Claisen-Schmidt condensation and the evaluation of their effect on the viability of the Trypanosomatidae parasites Leishmania amazonensis, Leishmania infantum and Trypanosoma cruzi.

  4. Synthesis and in vitro antiplasmodial evaluation of 7-chloroquinoline-chalcone and 7-chloroquinoline-ferrocenylchalcone conjugates.

    Science.gov (United States)

    Raj, Raghu; Saini, Anu; Gut, Jiri; Rosenthal, Philip J; Kumar, Vipan

    2015-05-05

    The manuscript describes the synthesis of novel amide tethered 7-chloroquinoline-chalcone and 7-chloroquinoline-ferrocenylchalcone bifunctional hybrids and their evaluation as antimalarial agents against W2 resistant strain of Plasmodium falciparum. The antiplasmodial activity of 7-chloroquinoline-ferrocenylchalcones was found to be less than their corresponding simple chalcone conjugates. The presence of a methoxy substituent at para position of ring B on chalcones and longer alkyl chain length markedly improved the antiplasmodial profiles of the synthesized scaffolds with the most potent of the test compound exhibiting an IC50 value of 17.8 nM.

  5. Metabolite profiling of Arabidopsis thaliana (L.) plants transformed with an antisense chalcone synthase gene

    DEFF Research Database (Denmark)

    Le Gall, G.; Metzdorff, Stine Broeng; Pedersen, Jan W.;

    2005-01-01

    A metabolite profiling study has been carried out on Arabidopsis thaliana (L.) Heynh. ecotype Wassilewskija and a series of transgenic lines of the ecotype transformed with a CHS (chalcone synthase) antisense construct. Compound identifications by LC/MS and H-1 NMR are discussed. The glucosinolate...

  6. A Solid Phase Synthesis of Chalcones by Claisen-Schmidt Condensations

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    In order to accelerate the development of relatively inexpensive antimalarials that are effective against chloroquine-resistant strains of Plasmodium falclparum, a methodology for the solid phase synthesis of chalcone (l, 3-diphenyl-2-propen-l-one) analogues in reasonably high yields has been developed.

  7. Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols

    NARCIS (Netherlands)

    Muir, S.R.; Collins, G.J.; Robinson, S.; Hughes, S.G.; Bovy, A.G.; Vos, de C.H.R.; Tunen, van A.J.; Verhoeven, M.E.

    2001-01-01

    Tomatoes are an excellent source of the carotenoid lycopene, a compound that is thought to be protective against prostate cancer. They also contain small amounts of flavonoids in their peel (|[sim]|5–10 mg/kg fresh weight), mainly naringenin chalcone and the flavonol rutin, a quercetin glycoside. Fl

  8. Enantioselective Conjugate Addition of Diethylzinc to Chalcones Catalysed by Chiral Ni(II) Aminoalcohol Complexes

    NARCIS (Netherlands)

    Vries, André H.M. de; Jansen, Johan F.G.A.; Feringa, Bernard

    1994-01-01

    Conjugate addition of diethylzinc to chalcones is catalysed by complexes prepared in situ from Ni(acac)2 and cis-exo-N,N-dialkyl-3-aminoisoborneols or (+)-cis-endo-N,N-dimethyl-3-aminoborneol ((+)-DAB) (13b). The products are obtained with enantioselectivities up to 84 %. When scalemic (-)-cis-exo-N

  9. Synthesis and Antimicrobial Activity of Some New Chalcones of 2-Acetyl Pyridine

    Directory of Open Access Journals (Sweden)

    Y. Rajendra Prasad

    2008-01-01

    Full Text Available Six new chalcones were synthesised by condensing 2-acetyl pyridine with aldehyde derivatives in dilute ethanolic potassium hydroxide solution at room temperature according to Claisen-Schmidt condensation. All these compounds were characterised by means of their IR, 1H NMR spectroscopic data and microanalyses. The antimicrobial activity of these compounds was evaluated by the cup plate method.

  10. ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONES CATALYZED BY CHIRAL NI(II) AMINOALCOHOL COMPLEXES

    NARCIS (Netherlands)

    DEVRIES, AHM; JANSEN, JFGA; FERINGA, BL

    1994-01-01

    Conjugate addition of diethylzinc to chalcones is catalysed by complexes prepared in situ from Ni(acac)(2) and cis-exo-N,N-dialkyl-3-aminoisoborneols or (+)-cis-endo-N,N-dimethyl-3-aminoborneol ((+)- DAB) (13b). The products are obtained with enantioselectivities up to 84 %. When scalemic (-)-cis-ex

  11. Chalcones isolated from Angelica keiskei inhibit cysteine proteases of SARS-CoV.

    Science.gov (United States)

    Park, Ji-Young; Ko, Jin-A; Kim, Dae Wook; Kim, Young Min; Kwon, Hyung-Jun; Jeong, Hyung Jae; Kim, Cha Young; Park, Ki Hun; Lee, Woo Song; Ryu, Young Bae

    2016-01-01

    Two viral proteases of severe acute respiratory syndrome coronavirus (SARS-CoV), a chymotrypsin-like protease (3CL(pro)) and a papain-like protease (PL(pro)) are attractive targets for the development of anti-SARS drugs. In this study, nine alkylated chalcones (1-9) and four coumarins (10-13) were isolated from Angelica keiskei, and the inhibitory activities of these constituents against SARS-CoV proteases (3CL(pro) and PL(pro)) were determined (cell-free/based). Of the isolated alkylated chalcones, chalcone 6, containing the perhydroxyl group, exhibited the most potent 3CL(pro) and PL(pro) inhibitory activity with IC50 values of 11.4 and 1.2 µM. Our detailed protein-inhibitor mechanistic analysis of these species indicated that the chalcones exhibited competitive inhibition characteristics to the SARS-CoV 3CL(pro), whereas noncompetitive inhibition was observed with the SARS-CoV PL(pro).

  12. Chemistry of isoflavone heteroanalogs. 11. Benzodioxane analogs of chalcone, flavone, and isoflavone

    Energy Technology Data Exchange (ETDEWEB)

    Khilya, V.P.; Aitmambetov, A.; Turov, A.V.; Kornilov, A.M.; Litkei, D.; Patonai, T.

    1986-08-01

    Benzodioxane analogs of chalcones and their epoxides have been prepared. Different types of analogs of natural flavonolignan - silibin - have been synthesized from these compounds. The PMR spectra of the new compounds and the results of the preliminary biological testings are reported and discussed.

  13. Synthesis and Hydrogenation of Disubstituted Chalcones: A Guided-Inquiry Organic Chemistry Project

    Science.gov (United States)

    Mohrig, Jerry R.; Hammond, Christina Noring; Schatz, Paul F.; Davidson, Tammy A.

    2009-01-01

    Guided-inquiry experiments offer the same opportunities to participate in the process of science as classical organic qualitative analysis used to do. This three-week guided-inquiry project involves an aldol-dehydration synthesis of a chalcone chosen from a set of nine, followed by a catalytic transfer hydrogenation reaction using ammonium formate…

  14. Synthesis and Antimicrobial Activity of Some New Chalcones of 2-Acetyl Pyridine

    OpenAIRE

    2008-01-01

    Six new chalcones were synthesised by condensing 2-acetyl pyridine with aldehyde derivatives in dilute ethanolic potassium hydroxide solution at room temperature according to Claisen-Schmidt condensation. All these compounds were characterised by means of their IR, 1H NMR spectroscopic data and microanalyses. The antimicrobial activity of these compounds was evaluated by the cup plate method.

  15. Studies on third-order nonlinear optical properties of chalcone derivatives in polymer host

    Science.gov (United States)

    Shettigar, Seetharam; Umesh, G.; Chandrasekharan, K.; Sarojini, B. K.; Narayana, B.

    2008-04-01

    In this paper we present the experimental study of the third-order nonlinear optical properties of two chalcone derivatives, viz., 1-(4-methoxyphenyl)-3-(4-butyloxyphenyl)-prop-2-en-1-one and 1-(4-methoxyphenyl)-3-(4-propyloxyphenyl)-prop-2-en-1-one in PMMA host, with the prospective of reaching a compromise between good processability and high nonlinear optical properties. The nonlinear optical properties have been investigated by Z-scan technique using 7 ns laser pulses at 532 nm. The nonlinear refractive index, nonlinear absorption coefficient, magnitude of third-order susceptibility and the coupling factor have been determined. The values obtained are of the order of 10 -14 cm 2/W, 1 cm/GW, 10 -13 esu and 0.2, respectively. The molecular second hyperpolarizability for the chalcone derivatives in polymer is of the order of 10 -31 esu. Different guest/host concentrations have also been studied. The results suggest that the nonlinear properties of the chalcones have been improved when they are used as dopants in polymer matrix. The nonlinear parameters obtained are comparable with the reported values of II-VI compound semiconductors. Hence, these chalcons are a promising class of nonlinear optical dopant materials for optical device applications.

  16. Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin.

    Science.gov (United States)

    Dias, Tatiana A; Duarte, Cecília L; Lima, Cristovao F; Proença, M Fernanda; Pereira-Wilson, Cristina

    2013-07-01

    A series of chalcone and flavonol derivatives were synthesized in good yield by an eco-friendly approach. A pharmacological evaluation was performed with the human colorectal carcinoma cell line HCT116 and revealed that the anticancer activity of flavonols was higher when compared with that of the respective chalcone precursors. The antiproliferative activity of halogenated derivatives increases as the substituent in the 3- or 4-positon of the B-ring goes from F to Cl and to Br. In addition, halogens in position 3 enhance anticancer activity in chalcones whereas for flavonol derivatives the best performance was registered for the 4-substituted derivatives. Flow cytometry analysis showed that compounds 3p and 4o induced cell cycle arrest and apoptosis as demonstrated by increased S, G2/M and sub-G1 phases. These data were corroborated by western blot and fluorescence microscopy analysis. In summary, halogenated chalcones and flavonols were successfully prepared and presented high anticancer activity as shown by their cell growth and cell cycle inhibitory potential against HCT116 cells, superior to that of quercetin, used as a positive control.

  17. 3-(Substituted Aryl-1-benzofuranyl-2-propenones: Antimicrobial Properties of Some Chalcones-Type Compounds and their 2-Pyrazoline Derivatives

    Directory of Open Access Journals (Sweden)

    Demet Coskun

    2011-01-01

    Full Text Available 2-Acetylbenzofuran on condensation with furan-2-carboxaldehyde and pyrrole-2-carboxaldehyde in methanolic KOH solution yielded the corresponding benzofuran chalcones. These two compounds and nine benzofuran chalcones were synthesized before, were further reacted with hydrazine hydrate in ethanol which led to the formation of 2-pyrazoline derivatives. All the synthesized compounds were characterized by elemental analysis, melting point determination, infrared spectroscopy and nuclear magnetic resonance spectroscopy. Nine chalcone-type compounds and eleven 2-pyrazolines were evaluated for their biological activities against the six bacteria and the three yeast and it was seen that thirteen compounds showed activity. Four of them are chalcone-type compounds showed more or less activity.

  18. Synthesis of heterocyclic chalcone derivatives and their radical scavenging ability toward 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals

    Energy Technology Data Exchange (ETDEWEB)

    Hwang, Kijun; Kim, Hoseok; Kim, Beomtae [Research Center of Bioactive Materials, Hwaseong (Korea, Republic of); Han, Incheol [Chonbuk National Univ., Jeonju (Korea, Republic of)

    2012-04-15

    A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones were higher than those of furan ring containing chalcones, and the presence of methyl substituent of heterocyclic ring distinctly affected the activities compared with non-substituted heterocycles in an opposite manner, with the 4'-methyl group of thiophene ring increasing activity and the 3'-methyl group of the furan ring decreasing activity. The distinct isosteric effect of heterocycles (i.e., thiophene or furan ring) on radical scavenging activities of heterocyclic chalcones was distinctly demonstrated in our work.

  19. Synthesis and Antimicrobial Activity of Some Novel Chalcones of 2-Hydroxy -1-Acetonapthone and 3-Acetyl Coumarin

    OpenAIRE

    2006-01-01

    Five novel chalcones were synthesised by condensing 2-hydroxy-1-acetonaphthone with aldehyde derivatives in dilute ethanolic potassium hydroxide solution at room temperature according to Claisen-Schmidt condensation and another five novel chalcones were prepared by refluxing 3-acetyl coumarin with aldehydes in the presence of piperidine in ethanol. All these compounds were characterised by means of their IR, 1H NMR spectroscopic data and microanalyses. The antimicrobial activity of these comp...

  20. Synthesis and Antimicrobial Activity of Some Novel Chalcones of 2-Hydroxy -1-Acetonapthone and 3-Acetyl Coumarin

    Directory of Open Access Journals (Sweden)

    Y. Rajendra Prasad

    2006-01-01

    Full Text Available Five novel chalcones were synthesised by condensing 2-hydroxy-1-acetonaphthone with aldehyde derivatives in dilute ethanolic potassium hydroxide solution at room temperature according to Claisen-Schmidt condensation and another five novel chalcones were prepared by refluxing 3-acetyl coumarin with aldehydes in the presence of piperidine in ethanol. All these compounds were characterised by means of their IR, 1H NMR spectroscopic data and microanalyses. The antimicrobial activity of these compounds were evaluated by the cup plate method.

  1. Antibacterial activity of three newly-synthesized chalcones & synergism with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus

    OpenAIRE

    2014-01-01

    Background & objectives: Multidrug-resistance of methicillin-resistant Staphylococcus aureus (MRSA) is a serious therapeutical problem. Chalcones belong to a group of naturally occurring flavonoids, usually found in various plant species, and have potent antibacterial, antiviral and antifungal activities. The goal of this study was to evaluate the antibacterial effect of three newly-synthesized chalcones against clinical isolates of MRSA, and their synergism with β-lactam and non- β-lactam an...

  2. Antibacterial activity of three newly-synthesized chalcones & synergism with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus

    Directory of Open Access Journals (Sweden)

    Dragana D Bozic

    2014-01-01

    Interpretation & conclusions: o0 ur study demonstrated that three newly-synthesized chalcones exhibited significant anti-MRSA effect and synergism with non-β-lactam antibiotics. The most effective compound was 1,3-Bis-(2-hydroxy-phenyl-propenone. Our results provide useful information for future research of possible application of chalcones in combination with conventional anti-MRSA therapy as promising new antimicrobial agents.

  3. Studies on chalcone derivatives: complex formation, thermal behavior, stability constant and antioxidant activity.

    Science.gov (United States)

    El-Sayed, Yusif S; Gaber, M

    2015-02-25

    The chalcone 3-[4'-dimethylaminophenyl]-1-(2-pyridyl) prop-2-en-1-one (DMAPP) and 3-(4'-diethylaminophenyl)-1-(2-pyridinyl) prop-2-en-1-one abbreviated as DEAPP have been synthesized and characterized with IR, (1)H NMR, (13)C NMR spectroscopic techniques as described previously (El-Daly et al., 2008; Gaber et al., 2009; El-Sayed, 2013). By using UV visible spectroscopy method the mole fraction ratio for copper with DMAPP and DEAPP complexes were determined and it was found to be 1:1. The stability constants of this complex have been determined by Job's method. The stability constant (Kf) of copper with DMAPP and DEAPP complexes in universal buffer pH=3.2 was determined to be 9.9×10(4) and 5.2×10(4) respectively. The effect of Cu(II) ion on the emission spectrum of the free chalcone is also assigned. Adherence to Beer's law and Ringbom optimum concentration ranges are determined. The thermal decomposition of the metal complexes is studied by TGA technique. The kinetic parameters like activation energy, pre-exponential factor and entropy of activation are estimated. The structure of complexes was energetically optimized through molecular mechanics applying MM(+) force field coupled with molecular dynamics simulation. The bond lengths and bond angles have been calculated to confirm the geometry of the ligands and their Cu(II) complexes. The mode of interaction of the chalcone to copper nanoparticles was studied. The apparent association constants of the colloidal copper nanoparticles:chalcone complexes in solution were evaluated using the spectral method and compared with the formation constant of the Cu(II) chalcone complexes. Antioxidant activity of these chalcones was evaluated by using 1,1'-diphenyl-2-picrylhydrazyl (DPPH) radicals scavenging method, which showed that the antioxidant activity of DMAPP has higher value than the DEAPP. Semi-empirical study results showed that DMAPP have higher dipole moment than DEAPP.

  4. Studies on chalcone derivatives: Complex formation, thermal behavior, stability constant and antioxidant activity

    Science.gov (United States)

    El-Sayed, Yusif S.; Gaber, M.

    2015-02-01

    The chalcone 3-[4‧-dimethylaminophenyl]-1-(2-pyridyl) prop-2-en-1-one (DMAPP) and 3-(4‧-diethylaminophenyl)-1-(2-pyridinyl) prop-2-en-1-one abbreviated as DEAPP have been synthesized and characterized with IR, 1H NMR, 13C NMR spectroscopic techniques as described previously (El-Daly et al., 2008; Gaber et al., 2009; El-Sayed, 2013). By using UV visible spectroscopy method the mole fraction ratio for copper with DMAPP and DEAPP complexes were determined and it was found to be 1:1. The stability constants of this complex have been determined by Job's method. The stability constant (Kf) of copper with DMAPP and DEAPP complexes in universal buffer pH = 3.2 was determined to be 9.9 × 104 and 5.2 × 104 respectively. The effect of Cu(II) ion on the emission spectrum of the free chalcone is also assigned. Adherence to Beer's law and Ringbom optimum concentration ranges are determined. The thermal decomposition of the metal complexes is studied by TGA technique. The kinetic parameters like activation energy, pre-exponential factor and entropy of activation are estimated. The structure of complexes was energetically optimized through molecular mechanics applying MM+ force field coupled with molecular dynamics simulation. The bond lengths and bond angles have been calculated to confirm the geometry of the ligands and their Cu(II) complexes. The mode of interaction of the chalcone to copper nanoparticles was studied. The apparent association constants of the colloidal copper nanoparticles:chalcone complexes in solution were evaluated using the spectral method and compared with the formation constant of the Cu(II) chalcone complexes. Antioxidant activity of these chalcones was evaluated by using 1,1‧-diphenyl-2-picrylhydrazyl (DPPHrad) radicals scavenging method, which showed that the antioxidant activity of DMAPP has higher value than the DEAPP. Semi-empirical study results showed that DMAPP have higher dipole moment than DEAPP [1].

  5. Biotechnological methods for chalcone reduction using whole cells of Lactobacillus, Rhodococcus and Rhodotorula strains as a way to produce new derivatives.

    Science.gov (United States)

    Stompor, Monika; Kałużny, Mateusz; Żarowska, Barbara

    2016-10-01

    Microbial strains of the genera Dietzia, Micrococcus, Pseudomonas, Rhodococcus, Gordonia, Streptomyces, Pseudomonas, Bacillus, Penicillium, Rhodotorula and Lactobacillus were screened for the ability to convert chalcones. Synthesis of chalcones was performed by the Claisen-Schmidt reaction. There were three groups of chalcones obtained as the products, which included the derivatives containing 4-substituted chalcone, 2'-hydroxychalcone and 4'-methoxychalcone. The B ring of the chalcones was substituted in the para position with different groups, such as halide, hydroxyl, nitro, methyl, ethyl and ethoxy one. The structure-activity relationship of the tested chalcones in biotransformation processes was studied. It has been proven that Gram-positive bacterial strains Rhodococcus and Lactobacillus catalyzed reduction of C=C bond in the chalcones to give respective dihydrochalcones. The strain Rhodotorula rubra AM 82 transformed chalcones into dihydrochalcones and respective secondary alcohols. These results suggest that the probiotic strain of Lactobacillus can be used for biotransformations of chalcones, which has not been described before. The structure of new metabolites 14a and 15b were established as 4-ethoxy-4'-methoxydihydrochalcone and 3-(4-bromophenyl)-1-(4'-O-methylphenyl)-2-propan-1-ol, respectively, which was confirmed by (1)H NMR and (13)C NMR analysis.

  6. Flemingin-Type Prenylated Chalcones from the Sarawak Rainforest Plant Desmodium congestum.

    Science.gov (United States)

    Rees, Karlee A; Bermudez, Cindy; Edwards, David J; Elliott, Alysha G; Ripen, Jovita E; Seta, Cynthia; Huang, Johnny X; Cooper, Matthew A; Fraser, James A; Yeo, Tiong Chia; Butler, Mark S

    2015-08-28

    In an ongoing program to identify new anti-infective leads, an extract derived from whole plant material of Desmodium congestum collected in the Sarawak rainforest was found to have anti-MRSA activity. Bioassay-guided isolation led to the isolation of two new prenylated chalcones, 5'-O-methyl-3-hydroxyflemingin A (1) and 5'-O-methylflemingin C (2), which were closely related to the flemingins previously isolated from various Flemingia species. Chalcones 1 and 2, which were determined to be 4:6 enantiomeric mixtures by chiral HPLC, exhibited moderate activity against a panel of Gram-positive bacteria and were also cytotoxic to the HEK293 human embryonic kidney cell line.

  7. Cytotoxic C-benzylated chalcone and other constituents of Ellipeiopsis cherrevensis.

    Science.gov (United States)

    Wirasathien, Lalita; Pengsuparp, Thitima; Moriyasu, Masataka; Kawanishi, Kazuko; Suttisri, Rutt

    2006-06-01

    A new natural C-benzylated chalcone, 2',4'-dihydroxy-3'-(2-hydroxybenzyl)-6'-methoxychalcone (2), along with two other flavonoids, tiliroside and kaempferol 3-O-rutinoside, and an oxoaporphine alkaloid, lanuginosine were isolated from the aerial parts of Ellipeiopsis cherrevensis (Annonaceae). Two known polyoxygenated cyclohexene derivatives, ferrudiol and zeylenol, and a new analog, ellipeiopsol D, were also isolated. The chalcone 2 exhibited cytotoxic activity against human small-cell lung-cancer (NCI-H187), epidermoid carcinoma (KB) and breast cancer (BC) cell lines with IC50 values of 1.40, 5.31 and 13.92 microg/mL, respectively. This compound also showed antimalarial activity against Plasmodium falciparum with an IC50 value of 7.1 microg/mL as well as antimicrobacterial activity against Mycobacterium tuberculosis with a MIC of 25 mg/mL.

  8. Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2013-10-01

    Full Text Available Chalcone derivatives have attracted increasing attention due to their numerous pharmacological activities. Changes in their structures have displayed high degree of diversity that has proven to result in a broad spectrum of biological activities. The present study highlights the synthesis of some halogen substituted chalcones 3(a–i containing the 5-chlorothiophene moiety, their X-ray crystal structures and the evaluation of possible biological activities such as antibacterial, antifungal and reducing power abilities. The results indicate the tested compounds show a varied range of inhibition values against all the tested microbial strains. Compound 3c with a p-fluoro substituent on the phenyl ring exhibits elevated antimicrobial activity, whereas the compounds 3e and 3f displayed the least antimicrobial activities. The compounds 3d, 3e, 3f and 3i showed good ferric and cupric reducing abilities, and the compounds 3b and 3c showed the weakest reducing power in the series.

  9. Synthetic chalcone derivatives as inhibitors of cathepsins K and B, and their cytotoxic evaluation.

    Science.gov (United States)

    Ramalho, Suelem Demuner; Bernades, Aline; Demetrius, Giulio; Noda-Perez, Caridad; Vieira, Paulo Cezar; Dos Santos, Caio Yu; da Silva, James Almada; de Moraes, Manoel Odorico; Mousinho, Kristiana Cerqueira

    2013-11-01

    A series of chalcone derivatives, 1-15, were prepared by Claisen-Schmidt condensation and evaluated for their cytotoxicities on tumor cell lines and also against proteolytic enzymes such as cathepsins B and K. Of the compounds synthesized, (E)-3-(3,4-dimethoxyphenyl)-1-phenylprop-2-en-1-one (12), (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (13), (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (14), and (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one (15) showed significant cytotoxicities. The most effective compound was 15, which showed high cytotoxic activity with an IC50 value lower than 1 μg/ml, and no selectivity on the tumor cells evaluated. Substituents at C(4) of ring B were found to be essential for cytotoxicity. In addition, it was also demonstrated that some of these chalcones are moderate inhibitors of cathepsin K and have no activity against cathepsin B.

  10. Heteroaryl chalcones: design, synthesis, X-ray crystal structures and biological evaluation.

    Science.gov (United States)

    Kumar, C S Chidan; Loh, Wan-Sin; Ooi, Chin Wei; Quah, Ching Kheng; Fun, Hoong-Kun

    2013-10-15

    Chalcone derivatives have attracted increasing attention due to their numerous pharmacological activities. Changes in their structures have displayed high degree of diversity that has proven to result in a broad spectrum of biological activities. The present study highlights the synthesis of some halogen substituted chalcones 3(a-i) containing the 5-chlorothiophene moiety, their X-ray crystal structures and the evaluation of possible biological activities such as antibacterial, antifungal and reducing power abilities. The results indicate the tested compounds show a varied range of inhibition values against all the tested microbial strains. Compound 3c with a p-fluoro substituent on the phenyl ring exhibits elevated antimicrobial activity, whereas the compounds 3e and 3f displayed the least antimicrobial activities. The compounds 3d, 3e, 3f and 3i showed good ferric and cupric reducing abilities, and the compounds 3b and 3c showed the weakest reducing power in the series.

  11. Synthesis and antimicrobial studies of hydroxylated chalcone derivatives with variable chain length.

    Science.gov (United States)

    Ngaini, Zainab; Fadzillah, Siti M Haris; Hussain, Hasnain

    2012-01-01

    A series of (E)-1-(4-alkyloxyphenyl)-3-(hydroxyphenyl)-prop-2-en-1-one have been successfully synthesised via Claisen-Schmidt condensation. The synthesised chalcone derivatives consisted of hydroxyl groups at either ortho, meta or para position and differed in the length of the alkyl groups, C (n) H(2) (n) (+1,) where n = 6, 10, 12 and 14. The structures of all compounds were defined by elemental analysis, IR, (1)H- and (13)C-NMR. The antimicrobial studies were carried out against wild-type Escherichia coli American Type Culture Collection 8739 to evaluate the effect of the hydroxyl and the alkyl groups of the synthesised chalcones. All the synthesised compounds have shown significant antimicrobial activities. The optimum inhibition was dependent on the position of the hydroxyl group as well as the length of the alkyl chains.

  12. Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents.

    Science.gov (United States)

    Solankee, Anjani; Kapadia, Kishor; Ana Cirić; Soković, Marina; Doytchinova, Irini; Geronikaki, Athina

    2010-02-01

    Base catalysed condensation of ketone 5 with different aldehydes give chalcones, 2.4-bis-(phenylamino)-6-[4'-{3''-(4'''-substituted phenyl/2'''-furanyl/2'''-thienyl)-2''-propenon-1''-yl}phenylamino]-s-thriazines 6a-e. These chalcones on cyclization with hydrazine hydrate in the presence of glacial acetic acid, guanidine nitrate in the presence of alkali and malononitrile in the presence of ammonium acetate give the corresponding acetylpyrazolines 7a-e, aminopyrimidines 8a-e and cyanopyridines 9a-e respectively. The products 6a-e, 7a-e, 8a-e and 9a-e were fully characterized by spectroscopic and elemental analysis and also tested for antibacterial activity.

  13. Thermal solvent-free synthesis of chromonyl chalcones, pyrazolines and their in vitro antibacterial, antifungal activities.

    Science.gov (United States)

    Siddiqui, Zeba N; Praveen, Shagufta; Musthafa, T N Mohammed; Ahmad, Anis; Khan, Asad U

    2012-02-01

    A facile and ecofriendly synthesis of new chromonyl chalcones 3a-b from 3-formylchromone 1 and active methyl compounds 2a-b is reported under thermal solvent-free heating condition in good yields. The chromonyl chalcones 3a-b were used as intermediates under green condition for the synthesis of new bioactive pyrazoline derivatives 4a-f. The compounds were tested for antimicrobial activity by disk diffusion assay with slight modifications against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. The investigation of antimicrobial screening revealed that compounds 3a-b and 4a-f showed antibacterial and antifungal activities.

  14. A quantitative analysis of weak intermolecular interactions & quantum chemical calculations (DFT) of novel chalcone derivatives

    Science.gov (United States)

    Chavda, Bhavin R.; Gandhi, Sahaj A.; Dubey, Rahul P.; Patel, Urmila H.; Barot, Vijay M.

    2016-05-01

    The novel chalcone derivatives have widespread applications in material science and medicinal industries. The density functional theory (DFT) is used to optimized the molecular structure of the three chalcone derivatives (M-I, II, III). The observed discrepancies between the theoretical and experimental (X-ray data) results attributed to different environments of the molecules, the experimental values are of the molecule in solid state there by subjected to the intermolecular forces, like non-bonded hydrogen bond interactions, where as isolated state in gas phase for theoretical studies. The lattice energy of all the molecules have been calculated using PIXELC module in Coulomb -London -Pauli (CLP) package and is partitioned into corresponding coulombic, polarization, dispersion and repulsion contributions. Lattice energy data confirm and strengthen the finding of the X-ray results that the weak but significant intermolecular interactions like C-H…O, Π- Π and C-H… Π plays an important role in the stabilization of crystal packing.

  15. Development of fluorescent lead II sensor based on an anthracene derived chalcone.

    Science.gov (United States)

    Prabhu, J; Velmurugan, K; Nandhakumar, R

    2015-06-05

    A simple anthracene based chalcone as a fluorescent chemosensor 1, capable of detecting Pb(2+) in aqueous media, has been synthesized by the reaction between pyridine 2-carboxaldehyde and 9-acetyl anthracene. The Pb(2+) recognition processes follows a photo induced electron transfer (PET) mechanism and are scarcely influenced by other coexisting metal ions. In addition, determination of lead in a variety of samples was also determined.

  16. Synthesis of β-ionone derived chalcones as potent antimicrobial agents.

    Science.gov (United States)

    Sharma, Vishal; Singh, Gurpreet; Kaur, Harpreet; Saxena, Ajit K; Ishar, Mohan Paul S

    2012-10-15

    A series of chalcones (3a-v) have been synthesized by condensation of β-ionone (1) with a variety of aldehydes (2a-v). The synthesized compounds have been screened for their in vitro antimicrobial activity against five bacterial and five fungal strains, using disc diffusion assay. The evaluated compounds display a wide range of activities, from completely inactive to the highly active compounds. Some of the compounds are also active against methicillin resistant staphylococcus aureus (MRSA).

  17. Thiazole-based chalcones as potent antimicrobial agents. Synthesis and biological evaluation.

    Science.gov (United States)

    Liaras, K; Geronikaki, A; Glamočlija, J; Cirić, A; Soković, M

    2011-05-15

    As part of ongoing studies in developing new antimicrobials, we report the synthesis of a new class of structurally novel derivatives, that incorporate two known bioactive structures a thiazole and chalcone, to yield a class of compounds with interesting antimicrobial properties. Evaluation of antibacterial activity showed that almost all the compounds exhibited greater activity than reference drugs and thus could be promising novel drug candidates.

  18. An efficient synthesis of pyrazole chalcones under solvent free conditions at room temperature

    Institute of Scientific and Technical Information of China (English)

    Parvin Kumar; Sunil Kumar; Khalid Husain; Ashwani Kumar

    2011-01-01

    An easy,safe,solvent free and effective method for the synthesis of pyrazole-substituted chalcones has been achieved by grinding pyrazole aldehydes and acetophenones in the presence of activated barium hydroxide(C-200) in high yield within short span of time.All reactions were carried out just by grinding the two reactants in the presence of activated barium hydroxide(C-200).Results are also compared with sodium hydroxide and potassium hydroxide.

  19. In silico analysis reveals the anti-malarial potential of quinolinyl chalcone derivatives.

    Science.gov (United States)

    Thillainayagam, Mahalakshmi; Pandian, Lavanya; Murugan, Kumar Kalavathy; Vijayaparthasarathi, Vijayakumar; Sundaramoorthy, Sarveswari; Anbarasu, Anand; Ramaiah, Sudha

    2015-01-01

    In this study, the correlation between chemical structures and various parameters such as steric effects and electrostatic interactions to the inhibitory activities of quinolinyl chalcone derivatives is derived to identify the key structural elements required in the rational design of potent and novel anti-malarial compounds. The molecular docking simulations and Comparative Molecular Field Analysis (CoMFA) are carried out on 38 chalcones derivatives using Plasmodium falciparum lactate dehydrogenase (PfLDH) as potential target. Surflex-dock is used to determine the probable binding conformations of all the compounds at the active site of pfLDH and to identify the hydrogen bonding interactions which could be used to alter the inhibitory activities. The CoMFA model has provided statistically significant results with the cross-validated correlation coefficient (q(2)) of .850 and the non-cross-validated correlation coefficient (r(2)) of .912. Standard error of estimation (SEE) is .280 and the optimum number of component is five. The predictive ability of the resultant model is evaluated using a test set comprising of 13 molecules and the predicted r(2) value is .885. The results provide valuable insight for optimization of quinolinyl chalcone derivatives for better anti-malarial therapy.

  20. Synthesis and anti-parasitic activity of a novel quinolinone-chalcone series.

    Science.gov (United States)

    Roussaki, Marina; Hall, Belinda; Lima, Sofia Costa; da Silva, Anabela Cordeiro; Wilkinson, Shane; Detsi, Anastasia

    2013-12-01

    A series of novel quinolinone-chalcone hybrids and analogues were designed, synthesized and their biological activity against the mammalian stages of Trypanosoma brucei and Leishmania infantum evaluated. Promising molecular scaffolds with significant microbicidal activity and low cytotoxicity were identified. Quinolinone-chalcone 10 exhibited anti-parasitic properties against both organisms, being the most potent anti-L. infantum agent of the entire series (IC50 value of 1.3±0.1 μM). Compounds 4 and 11 showed potency toward the intracellular, amastigote stage of L. infantum (IC50 values of 2.1±0.6 and 3.1±1.05 μM, respectively). Promising trypanocidal compounds include 5 and 10 (IC50 values of 2.6±0.1 and 3.3±0.1 μM, respectively) as well as 6 and 9 (both having IC50 values of chalcone scaffold were performed on selected compounds in order to investigate the influence of these structural features on antiparasitic activity.

  1. Dual emission of chalcone-analogue dyes emitting in the red region

    Energy Technology Data Exchange (ETDEWEB)

    Fayed, Tarek A.; Awad, Mohamed K

    2004-08-23

    The photophysical properties of new synthesized chalcones namely; 1-(4{sup '}-R-phenyl)-5-(4{sup '}-dimethylaminophenyl)-2,4- pentadien-1-one, [R=H (1), Cl (2) and OCH{sub 3} (3)] were studied in different solvents by using steady-state absorption and emission spectroscopy. The fluorescence spectra of these chalcones exhibit dual emission in medium and polar solvents. The dual emission was attributed to population of a polar locally excited (LE) state and a highly dipolar intramolecular charge transfer (ICT) state. The changes in dipole moments upon excitation were calculated from the solvatochromic plots. The total fluorescence quantum yields (phi{sub f}) were also determined, and their values are strongly dependent on the nature of substitutent and the solvent polarity. Semiempirical molecular orbital calculations using the atom superposition and electron delocalization molecular orbital (ASED-MO) method were also performed to investigate the molecular and electronic structures of these chalcones in both the ground and excited state. The change of the dipole moment upon excitation was explained on the basis of changes in the charge redistribution over the whole skeleton of the molecules, which agree well with the experimental results. Also, the nature and energy of the electronic transitions were elucidated and discussed in relation to the experimental data.

  2. Potent and Selective Monoamine Oxidase-B Inhibitory Activity: Fluoro- vs. Trifluoromethyl-4-hydroxylated Chalcone Derivatives.

    Science.gov (United States)

    Mathew, Bijo; Mathew, Githa Elizabeth; Uçar, Gülberk; Baysal, Ipek; Suresh, Jerad; Mathew, Sincy; Haridas, Abitha; Jayaprakash, Venkatesan

    2016-08-01

    For various neurodegenerative disorders like Alzheimer's and Parkinson's diseases, selective and reversible MAO-B inhibitors have a great therapeutic value. In our previous study, we have shown that a series of methoxylated chalcones with F functional group exhibited high binding affinity toward human monoamine oxidase-B (hMAO-B). In continuation of our earlier study and to extend the understanding of the structure-activity relationships, a series of five new chalcones were studied for their inhibition of hMAO. The results demonstrated that these compounds are reversible and selective hMAO-B inhibitors with a competitive mode of inhibition. The most active compound, (2E)-1-(4-hydroxyphenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one, exhibited a Ki value of 0.33 ± 0.01 μm toward hMAO-B with a selectivity index of 26.36. A molecular docking study revealed that the presence of a H-bond network in hydroxylated chalcone with the N(5) atom of FAD is crucial for MAO-B selectivity and potency.

  3. Isobavachalcone, a chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma.

    Science.gov (United States)

    Nishimura, Reiko; Tabata, Keiichi; Arakawa, Motoki; Ito, Yoshihisa; Kimura, Yumiko; Akihisa, Toshihiro; Nagai, Hisashi; Sakuma, Atsuko; Kohno, Hideki; Suzuki, Takashi

    2007-10-01

    Six chalcones from Angelica keiskei KOIDZUMI (Ashitaba in Japanese) and two chalcones from Humulus lupulus L. (hop) were examined for their cytotoxicity in two human neuroblastoma cell lines (IMR-32 and NB-39) and normal cells (primary culture of rat cerebellar granule cells) by [3-(4,5)-dimethyl-2-thiazolyl]-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay. All chalcones exhibited cytotoxicity against neuroblastoma cells, and two of them (isobavachalcone and xanthoangelol H) had no effect on normal cells even at high concentration (10(-4) M) exposure. Typical morphologic features of apoptosis, including cell shrinkage, chromatin condensation, nuclear fragmentation and formation of apoptotic bodies, were observed in isobavachalcone-treated cells by Hoechst 33342 staining. Western blot analysis showed that isobavachalcone significantly reduced pro-caspase-3 and pro-caspase-9, and subsequently increased the level of cleaved caspase-3 and cleaved caspase-9 in both neuroblastoma cell lines. Moreover, Bax was markedly induced by isobavachalcone application. These results suggest that isobavachalcone induces apoptotic cell death in neuroblastoma via the mitochondrial pathway and has no cytotoxicity against normal cells. Therefore, isobavachalcone may be applicable as an efficacious and safe drug for the treatment of neuroblastoma.

  4. Synthesis, characterization, and computational study of a new dimethoxy-chalcone.

    Science.gov (United States)

    Ternavisk, Ricardo R; Camargo, Ademir J; Machado, Francisco B C; Rocco, José A F F; Aquino, Gilberto L B; Silva, Valter H C; Napolitano, Hamilton B

    2014-12-01

    Chalcones are an important class of medicinal compounds and are known for taking part in various biological activities as in anti-inflammatory, anti-leishmania, antimitotic, and antiviral. Chemically, chalcones consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. The wide action spectrum has attracted our attention to synthesize, crystallize, and characterize the dimethoxy-chalcone C18H18O3. Aiming to understand the process of crystal lattice stabilization, a combination of technique has been used including X-ray diffraction, infrared spectroscopy and computational molecular modeling. The theoretical calculations were carried out by the density functional method (DFT) with the M06-2X functional, with the 6-311+G(d,p) basis set. The vibrational wavenumbers were calculated and the scaled values were compared with experimental FT-IR spectrum. The intermolecular interactions were quantified and intercontacts in the crystal structure were analyzed using Hirshfeld surfaces. Bond distances and angles described by the X-ray diffraction and theoretical calculation are very similar. The C-H….O contacts contributing to assemble the supramolecular architecture are also responsible for the molecular structure assembly.

  5. Ferrocenyl-cymantrenyl hetero-bimetallic chalcones: Synthesis, structure and biological properties

    Science.gov (United States)

    Mishra, Sasmita; Tirkey, Vijaylakshmi; Ghosh, Avishek; Dash, Hirak R.; Das, Surajit; Shukla, Madhulata; Saha, Satyen; Mobin, Sheikh M.; Chatterjee, Saurav

    2015-04-01

    Two new ferrocenyl-cymantrenyl bimetallic chalcones, [(CO)3Mn(η5-C5H4)C(O)CHdbnd CH(η5-C5H4)Fe(η5-C5H5)] (1) and [{(CO)3Mn(η5-C5H4)C(O)CHdbnd CH(η5-C5H4)}2Fe] (2) have been synthesized. Their reactivity study with triphenylphosphine and bis-(diphenylphosphino)ferrocene led to the isolation of phosphine substituted bimetallic chalcones (3-6). Single crystal X-ray structural characterization for 1 and its phosphine analogue (3) reveals their different conformational identity with anti-conformation for 1, while syn-conformation for 3. Investigation of antimalarial and antibacterial activities was carried out for compounds 1 and 2 against two strains of Plasmodium falciparum (3D7, K1) and four bacterial strains. TD-DFT calculation was performed for compound 1 and electrochemical properties were studied for bimetallic chalcone compounds by cyclic voltammetric technique.

  6. Dual emission of chalcone-analogue dyes emitting in the red region

    Science.gov (United States)

    Fayed, Tarek A.; Awad, Mohamed K.

    2004-08-01

    The photophysical properties of new synthesized chalcones namely; 1-(4 '-R-phenyl)-5-(4 '-dimethylaminophenyl)-2,4- pentadien-1-one, [R=H ( 1), Cl ( 2) and OCH 3 ( 3)] were studied in different solvents by using steady-state absorption and emission spectroscopy. The fluorescence spectra of these chalcones exhibit dual emission in medium and polar solvents. The dual emission was attributed to population of a polar locally excited (LE) state and a highly dipolar intramolecular charge transfer (ICT) state. The changes in dipole moments upon excitation were calculated from the solvatochromic plots. The total fluorescence quantum yields ( φf) were also determined, and their values are strongly dependent on the nature of substitutent and the solvent polarity. Semiempirical molecular orbital calculations using the atom superposition and electron delocalization molecular orbital (ASED-MO) method were also performed to investigate the molecular and electronic structures of these chalcones in both the ground and excited state. The change of the dipole moment upon excitation was explained on the basis of changes in the charge redistribution over the whole skeleton of the molecules, which agree well with the experimental results. Also, the nature and energy of the electronic transitions were elucidated and discussed in relation to the experimental data.

  7. Viscosity and medium effects on the fluorescence and photochemical behaviour of some aryl chalcones

    Science.gov (United States)

    Ebeid, El-Zeiny M.; Abdel-Kader, Mahmood H.; Issa, Raafat M.; El-Daly, Samy A.

    1988-05-01

    The emission, excitation and absorption spectra toghether with the fluorescence and photochemical quantum yields of some chalcone derivatives have been studied in organic solvents and micellar and microemulsion media. Both 4-[2-(2-pyridyl)ethenyl] ( I) and 4-[2-(4-pyridyl)ethenyl ( II) chalcones show large positive solvatochromic effects. The fluorescence quantum yields increase substantially as the medium viscosity increases with a subsequent decrease in the photochemical quatum yield. Compounds I and II undergo excited-state molecular aggregation in concentrated solutions giving excimer-like emission that coincides with emission from crystalline samples. The enthalpies of photoassociation have been estimated. The chalcone derivative I acts as an efficient quencher of the fluorescence of the laser dye 1,4-bis (β-pyridyl-2-vinyl)benzene via a long-range mechanism. The excited-state lifetimes of both I and II are short and at 20°C their τ values are less than 800 ps.

  8. Molecular cloning and transgenic characterization of the genes encoding chalcone synthase and chalcone isomerase from the Tibetan herbal plant Mirabilis himalaica.

    Science.gov (United States)

    Lan, Xiaozhong; Quan, Hong; Xia, Xinli; Yin, Weilun; Zheng, Weilie

    2016-05-01

    Mirabilis himalaica is an endangered medicinal plant species in the Tibetan Plateau. The two genes respectively encoding chalcone synthase (MhCHS) and chalcone isomerase (MhCHI) were isolated and characterized from M. himalaica. The sequence analysis revealed that the two genes were similar with their corresponding homologous genes in other plants. The tissue profiles showed that both MhCHS and MhCHI had higher expression levels in roots than in stems and leaves. Transgenic hairy root cultures respectively with overexpressing MhCHS and MhCHI were established. The genomic PCR detection confirmed the authority of transgenic hairy root lines, in which either MhCHS or MhCHI expression levels were much higher than that in non-transgenic hairy root line. Finally, the HPLC detection results demonstrated that the rotenoid contents in MhCHS/MhCHI-transformed hairy root lines were enhanced. This study provided two candidate genes that could be used to genetic engineering rotenoid biosynthesis in M. himalaica and an alternative method to produce rotenoid using transgenic hairy root cultures.

  9. Experimental and quantum chemical studies of a novel synthetic prenylated chalcone

    Directory of Open Access Journals (Sweden)

    Espinoza-Hicks José C

    2013-01-01

    Full Text Available Abstract Background Chalcones are ubiquitous natural compounds with a wide variety of reported biological activities, including antitumoral, antiviral and antimicrobial effects. Furthermore, chalcones are being studied for its potential use in organic electroluminescent devices; therefore the description of their spectroscopic properties is important to elucidate the structure of these molecules. One of the main techniques available for structure elucidation is the use of Nuclear Magnetic Resonance Spectroscopy (NMR. Accordingly, the prediction of the NMR spectra in this kind of molecules is necessary to gather information about the influence of substituents on their spectra. Results A novel substituted chalcone has been synthetized. In order to identify the functional groups present in the new synthesized compound and confirm its chemical structure, experimental and theoretical 1H-NMR and 13C-NMR spectra were analyzed. The theoretical molecular structure and NMR spectra were calculated at both the Hartree-Fock and Density Functional (meta: TPSS; hybrid: B3LYP and PBE1PBE; hybrid meta GGA: M05-2X and M06-2X levels of theory in combination with a 6-311++G(d,p basis set. The structural parameters showed that the best method for geometry optimization was DFT:M06-2X/6-311++G(d,p, whereas the calculated bond angles and bond distances match experimental values of similar chalcone derivatives. The NMR calculations were carried out using the Gauge-Independent Atomic Orbital (GIAO formalism in a DFT:M06-2X/6-311++G(d,p optimized geometry. Conclusion Considering all HF and DFT methods with GIAO calculations, TPSS and PBE1PBE were the most accurate methods used for calculation of 1H-NMR and 13C-NMR chemical shifts, which was almost similar to the B3LYP functional, followed in order by HF, M05-2X and M06-2X methods. All calculations were done using the Gaussian 09 software package. Theoretical calculations can be used to predict and confirm the structure of

  10. Targeting death receptor TRAIL-R2 by chalcones for TRAIL-induced apoptosis in cancer cells.

    Science.gov (United States)

    Szliszka, Ewelina; Jaworska, Dagmara; Ksek, Małgorzata; Czuba, Zenon P; Król, Wojciech

    2012-11-20

    Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) induces apoptosis in cancer cells without toxicity to normal cells. TRAIL binds to death receptors, TRAIL-R1 (DR4) and TRAIL-R2 (DR5) expressed on cancer cell surface and activates apoptotic pathways. Endogenous TRAIL plays an important role in immune surveillance and defense against cancer cells. However, as more tumor cells are reported to be resistant to TRAIL mediated death, it is important to search for and develop new strategies to overcome this resistance. Chalcones can sensitize cancer cells to TRAIL-induced apoptosis. We examined the cytotoxic and apoptotic effects of TRAIL in combination with four chalcones: chalcone, isobavachalcone, licochalcone A and xanthohumol on HeLa cancer cells. The cytotoxicity was measured by MTT and LDH assays. The apoptosis was detected using annexin V-FITC staining by flow cytometry and fluorescence microscopy. Death receptor expression was analyzed using flow cytometry. The decreased expression of death receptors in cancer cells may be the cause of TRAIL-resistance. Chalcones enhance TRAIL-induced apoptosis in HeLa cells through increased expression of TRAIL-R2. Our study has indicated that chalcones augment the antitumor activity of TRAIL and confirm their cancer chemopreventive properties.

  11. Synthesis and anti-cancer activity evaluation of novel prenylated and geranylated chalcone natural products and their analogs.

    Science.gov (United States)

    Wang, Hao-Meng; Zhang, Li; Liu, Jiang; Yang, Zhao-Liang; Zhao, Hong-Ye; Yang, Yao; Shen, Di; Lu, Kui; Fan, Zhen-Chuan; Yao, Qing-Wei; Zhang, Yong-Min; Teng, Yu-Ou; Peng, Yu

    2015-03-06

    Four natural chalcones bearing prenyl or geranyl groups, i.e., bavachalcone (1a), xanthoangelol (1b), isobavachalcone (1c), and isoxanthoangelol (1d) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. The first total synthesis of isoxanthoangelol (1d) was achieved in 36% overall yield. A series of diprenylated and digeranylated chalcone analogs were also synthesized by alkylation, regio-selective iodination, aldol condensation, Suzuki coupling and [1,3]-sigmatropic rearrangement. The structures of the 11 new derivatives were confirmed by (1)H NMR, (13)C NMR and HRMS. The anticancer activity of these new chalcone derivatives against human tumor cell line K562 were evaluated by MTT assay in vitro. SAR studies suggested that the 5'-prenylation/geranylation of the chalcones significantly enhance their cytotoxic activity. Among them, Bavachalcone (1a) displayed the most potent cytotoxic activity against K562 with IC50 value of 2.7 μM. The morphology changes and annexin-V/PI staining studies suggested that those chalcone derivatives inhibited the proliferation of K562 cells by inducing apoptosis.

  12. Synthesis and Regioselective Reaction of Some Unsymmetrical Heterocyclic Chalcone Derivatives and Spiro Heterocyclic Compounds as Antibacterial Agents.

    Science.gov (United States)

    El-Hashash, Maher A; Rizk, Sameh A; Atta-Allah, Saad R

    2015-12-10

    A number of novel heterocyclic chalcone derivatives can be synthesized by thermal and microwave tools. Treatment of 4-(4-Acetylamino- and/or 4-bromo-phenyl)-4-oxobut-2-enoic acids with hydrogen peroxide in alkaline medium were afforded oxirane derivatives 2. Reaction of the epoxide 2 with 2-amino-5-aryl-1,3,4-thiadiazole derivatives yielded chalcone of imidazo[2,1-b]thiadiazole derivative 4 via two thermal routes. In one pot reaction of 4-bromoacetophenone, diethyloxalate, and 2-amino-5-aryl-1,3,4-thiadiazole derivatives in MW irradiation (W 250 and T 150 °C) under eco-friendly conditions afforded an unsuitable yield of the desired chalcone 4d. The chalcone derivatives 4 were used as a key starting material to synthesize some new spiroheterocyclic compounds via Michael and aza-Michael adducts. The chalcone 4f was similar to the aryl-oxo-vinylamide derivatives for the inhibition of tyrosine kinase and cancer cell growth. The electron-withdrawing substituents, such as halogens, and 2-amino-1,3,4-thiadiazole moeity decreasing the electron density, thereby decreasing the energy of HOMO, and the presence of imidazothiadiazole moiety should improve the antibacterial activity. Thus, the newly synthesized compounds were evaluated for their anti-bacterial activity against (ATCC 25923), (ATCC 10987), (ATCC 274,) and (SM514). The structure of the newly synthesized compounds was confirmed by elemental analysis and spectroscopic data.

  13. Targeting Death Receptor TRAIL-R2 by Chalcones for TRAIL-Induced Apoptosis in Cancer Cells

    Directory of Open Access Journals (Sweden)

    Małgorzata Ksek

    2012-11-01

    Full Text Available Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL induces apoptosis in cancer cells without toxicity to normal cells. TRAIL binds to death receptors, TRAIL-R1 (DR4 and TRAIL-R2 (DR5 expressed on cancer cell surface and activates apoptotic pathways. Endogenous TRAIL plays an important role in immune surveillance and defense against cancer cells. However, as more tumor cells are reported to be resistant to TRAIL mediated death, it is important to search for and develop new strategies to overcome this resistance. Chalcones can sensitize cancer cells to TRAIL-induced apoptosis. We examined the cytotoxic and apoptotic effects of TRAIL in combination with four chalcones: chalcone, isobavachalcone, licochalcone A and xanthohumol on HeLa cancer cells. The cytotoxicity was measured by MTT and LDH assays. The apoptosis was detected using annexin V-FITC staining by flow cytometry and fluorescence microscopy. Death receptor expression was analyzed using flow cytometry. The decreased expression of death receptors in cancer cells may be the cause of TRAIL-resistance. Chalcones enhance TRAIL-induced apoptosis in HeLa cells through increased expression of TRAIL-R2. Our study has indicated that chalcones augment the antitumor activity of TRAIL and confirm their cancer chemopreventive properties.

  14. Hydroxyapatite catalyzed aldol condensation: Synthesis, spectral linearity, antimicrobial and insect antifeedant activities of some 2,5-dimethyl-3-furyl chalcones

    Science.gov (United States)

    Subramanian, M.; Vanangamudi, G.; Thirunarayanan, G.

    2013-06-01

    A series of 2,5-dimethyl-3-furyl chalcones [2E-1-(2,5-dimethyl-3-furyl)-3-(substituted phenyl)-2-propen-1-ones] have been synthesized by Hydrotalcite catalyzed aldol condensation between 3-acetyl-2,5-dimethylfuron and substituted benzaldehydes. Yields of chalcones are more than 80%. These chalcones were characterized by their physical constants and spectral data. The group frequencies of infrared ν(cm-1) of CO s-cis and s-trans, CH in-plane and out of plane, CHdbnd CH out of plane, lbond2 Cdbnd Crbond2 out of plane modes, NMR chemical shifts δ(ppm) of Hα, Hβ, CO, Cα and Cβ of these chalcones were correlated with Hammett substituent constants, F and R parameters using single and multi-regression analyses. From the results of statistical analyses, the effects of substituents on the group frequencies are explained. Antibacterial, antifungal and insect antifeedant activities of these chalcones have been studied.

  15. Hydroxyapatite catalyzed aldol condensation: synthesis, spectral linearity, antimicrobial and insect antifeedant activities of some 2,5-dimethyl-3-furyl chalcones.

    Science.gov (United States)

    Subramanian, M; Vanangamudi, G; Thirunarayanan, G

    2013-06-01

    A series of 2,5-dimethyl-3-furyl chalcones [2E-1-(2,5-dimethyl-3-furyl)-3-(substituted phenyl)-2-propen-1-ones] have been synthesized by Hydrotalcite catalyzed aldol condensation between 3-acetyl-2,5-dimethylfuron and substituted benzaldehydes. Yields of chalcones are more than 80%. These chalcones were characterized by their physical constants and spectral data. The group frequencies of infrared ν(cm(-1)) of CO s-cis and s-trans, CH in-plane and out of plane, CH=CH out of plane, C=C out of plane modes, NMR chemical shifts δ(ppm) of Hα, Hβ, CO, Cα and Cβ of these chalcones were correlated with Hammett substituent constants, F and R parameters using single and multi-regression analyses. From the results of statistical analyses, the effects of substituents on the group frequencies are explained. Antibacterial, antifungal and insect antifeedant activities of these chalcones have been studied.

  16. Chalcones as positive allosteric modulators of α7 nicotinic acetylcholine receptors: a new target for a privileged structure.

    Science.gov (United States)

    Balsera, Beatriz; Mulet, José; Fernández-Carvajal, Asia; de la Torre-Martínez, Roberto; Ferrer-Montiel, Antonio; Hernández-Jiménez, José G; Estévez-Herrera, Judith; Borges, Ricardo; Freitas, Andiara E; López, Manuela G; García-López, M Teresa; González-Muñiz, Rosario; Pérez de Vega, María Jesús; Valor, Luis M; Svobodová, Lucie; Sala, Salvador; Sala, Francisco; Criado, Manuel

    2014-10-30

    The α7 acetylcholine nicotine receptor is a ligand-gated ion channel that is involved in cognition disorders, schizophrenia, pain and inflammation among other diseases. Therefore, the development of new agents that target this receptor has great significance. Positive allosteric modulators might be advantageous, since they facilitate receptor responses without directly interacting with the agonist binding site. Here we report the search for and further design of new positive allosteric modulators having the relatively simple chalcone structure. From the natural product isoliquiritigenin as starting point, chalcones substituted with hydroxyl groups at defined locations were identified as optimal and specific promoters of α7 nicotinic function. The most potent compound (2,4,2',5'-tetrahydroxychalcone, 111) was further characterized showing its potential as neuroprotective, analgesic and cognitive enhancer, opening the way for future developments around the chalcone structure.

  17. Genotoxic, Cytotoxic, Antigenotoxic, and Anticytotoxic Effects of Sulfonamide Chalcone Using the Ames Test and the Mouse Bone Marrow Micronucleus Test.

    Directory of Open Access Journals (Sweden)

    Carolina Ribeiro E Silva

    Full Text Available Chalcones present several biological activities and sulfonamide chalcone derivatives have shown important biological applications, including antitumor activity. In this study, genotoxic, cytotoxic, antigenotoxic, and anticytotoxic activities of the sulfonamide chalcone N-{4-[3-(4-nitrophenylprop-2-enoyl]phenyl} benzenesulfonamide (CPN were assessed using the Salmonella typhimurium reverse mutation test (Ames test and the mouse bone marrow micronucleus test. The results showed that CPN caused a small increase in the number of histidine revertant colonies in S. typhimurium strains TA98 and TA100, but not statistically significant (p > 0.05. The antimutagenicity test showed that CPN significantly decreased the number of His+ revertants in strain TA98 at all doses tested (p 0.05. Additionally, CPN co-administered with MMC significantly increased PCE/NCE ratio at all doses tested, demonstrating its anticytotoxic effect. In summary, CPN presented genotoxic, cytotoxic, antigenotoxic, and anticytotoxic properties.

  18. Novel anti-inflammatory chalcone derivatives inhibit the induction of nitric oxide synthase and cyclooxygenase-2 in mouse peritoneal macrophages.

    Science.gov (United States)

    Herencia, F; Ferrándiz, M L; Ubeda, A; Guillén, I; Dominguez, J N; Charris, J E; Lobo, G M; Alcaraz, M J

    1999-06-18

    In a previous work, we tested a series of chalcone derivatives as possible anti-inflammatory compounds. We now investigate the effects of three of those compounds, CHI, CH8 and CH12, on nitric oxide and prostanoid generation in mouse peritoneal macrophages stimulated with lipopolysaccharide and in the mouse air pouch injected with zymosan, where they showed a dose-dependent inhibition with inhibitory concentration 50% values in the microM range. This effect was not the consequence of a direct inhibitory action on enzyme activities. Our results demonstrated that chalcone derivatives inhibited de novo inducible nitric oxide synthase and cyclooxygenase-2 synthesis, being a novel therapeutic approach for inflammatory diseases.

  19. Synthesis and in vitro biological evaluation of new pyrazole chalcones and heterocyclic diamides as potential anticancer agents

    Directory of Open Access Journals (Sweden)

    Sankappa Rai U.

    2015-05-01

    Full Text Available Synthesis and characterization of new heterocyclic pyrazole chalcones (4a–e and diamide (6a–e derivatives are described. Pyrazole chalcones were synthesized by the reaction of pyrazole aldehydes and suitable aromatic ketones. Diamides were synthesized by the reaction of phthalic acid and amines. Newly synthesized compounds were characterized by spectral studies and their biological activity was assessed in vitro using MCF-7 (human breast adenocarcinoma and HeLa (human cervical tumor cells cell lines. Few of the synthesized molecules inhibited the growth of the human breast cancer cell lines and human cervical tumor cell lines at low micromolar to nanomolar concentrations.

  20. Continuous-Flow Synthesis of Deuterium-Labeled Antidiabetic Chalcones: Studies towards the Selective Deuteration of the Alkynone Core

    Directory of Open Access Journals (Sweden)

    Sándor B. Ötvös

    2016-03-01

    Full Text Available Flow chemistry-based syntheses of deuterium-labeled analogs of important antidiabetic chalcones were achieved via highly controlled partial C≡C bond deuteration of the corresponding 1,3-diphenylalkynones. The benefits of a scalable continuous process in combination with on-demand electrolytic D2 gas generation were exploited to suppress undesired over-reactions and to maximize reaction rates simultaneously. The novel deuterium-containing chalcone derivatives may have interesting biological effects and improved metabolic properties as compared with the parent compounds.

  1. Solvent-induced chemical shifts of methoxyl nuclear resonance signals in chalcones by benzene and trifluoroacetic acid

    Science.gov (United States)

    Khurana, Shashi K.; Krishnamoorthy, V.; Parmar, Virinder S.

    The 1H NMR spectra of eight different methoxylated chalcones have separately been recorded, (1) in deuterated chloroform; (2) in a mixture (1:1) of deuterated chloroform and benzene; and (3) in a mixture of deuterated chloroform, benzene and trifluoroacetic acid (2:2:1) and the benzene induced and TFA induced shift values have been assigned to different methoxyl groups. These shift values can serve as a guide in determining the structures of natural or new chalcones. The steric, electronic and conformational factors are discussed to explain the shift values.

  2. In vitro and in vivo anti-glioma activity of a chalcone-quinoxaline hybrid.

    Science.gov (United States)

    Loch-Neckel, Gecioni; Bicca, Maíra Assunção; Leal, Paulo César; Mascarello, Alessandra; Siqueira, Jarbas Mota; Calixto, João B

    2015-01-27

    Chalcones are important compounds that exhibit multiple biological activities, including anti-inflammatory, antimitotic and antibacterial properties. In the present study, we have analyzed the potential anti-cancer activity of a chalcone named N9 (a hybrid chalcone-quinoxaline compound) using in vitro and in vivo experimental glioma models. Here, we report N9-induced inhibition of cell proliferation and also N9-induced cell death in a concentration-dependent manner in U87-MG glioma cells. These effects of N9 appear to be associated with its ability to inhibit the expression of cell cycle-associated proteins, and also the augmentation in the expression of the p21 (p21/Cip1) protein, a cyclin-dependent kinase inhibitor. Additionally, N9 also potentiates the production of the pro-apoptotic markers Bax and p53 via inhibition of MDM2. Moreover, our results show that N9 also significantly enhanced apoptosis of U87-MG cells with disruption of mitochondrial membrane potential, generation of ROS and caspase-9 activation. In vivo experiments carried out in a murine xenograft model of U87-MG revealed that N9 produced a significant reduction of tumors volume when compared to vehicle treated mice. Collectively, data demonstrate that N9 possess in vitro and in vivo anti-cancer activity, an effect that seems to involve the induction of p53 and p21 proteins, as well as, the activation of mitochondrial apoptosis pathway associated with the inhibition of protein MDM2. Overall, this study suggests N9 is affecting a variety of intracellular pathways related to tumor apoptosis. Perhaps N9 or derivate molecules could represent new potential drugs for cancer therapeutics.

  3. Lineage-Specific Expansion of the Chalcone Synthase Gene Family in Rosids.

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    Kattina Zavala

    Full Text Available Rosids are a monophyletic group that includes approximately 70,000 species in 140 families, and they are found in a variety of habitats and life forms. Many important crops such as fruit trees and legumes are rosids. The evolutionary success of this group may have been influenced by their ability to produce flavonoids, secondary metabolites that are synthetized through a branch of the phenylpropanoid pathway where chalcone synthase is a key enzyme. In this work, we studied the evolution of the chalcone synthase gene family in 12 species belonging to the rosid clade. Our results show that the last common ancestor of the rosid clade possessed six chalcone synthase gene lineages that were differentially retained during the evolutionary history of the group. In fact, of the six gene lineages that were present in the last common ancestor, 7 species retained 2 of them, whereas the other 5 only retained one gene lineage. We also show that one of the gene lineages was disproportionately expanded in species that belonged to the order Fabales (soybean, barrel medic and Lotus japonicas. Based on the available literature, we suggest that this gene lineage possesses stress-related biological functions (e.g., response to UV light, pathogen defense. We propose that the observed expansion of this clade was a result of a selective pressure to increase the amount of enzymes involved in the production of phenylpropanoid pathway-derived secondary metabolites, which is consistent with the hypothesis that suggested that lineage-specific expansions fuel plant adaptation.

  4. Crystal structure of the chalcone (E-3-(furan-2-yl-1-phenylprop-2-en-1-one

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    Oscar F. Vázquez-Vuelvas

    2015-02-01

    Full Text Available The title chalcone derivative, C13H10O2, adopts an E conformation about the C=C double bond. The molecule is composed of a furanyl and a phenyl ring, bridged by an α,β-unsaturated carbonyl system, which are inclined to one another by 24.07 (7°. In the crystal, molecules are connected by weak C—H...O hydrogen bonds involving the carbonyl O atom acting as a trifurcated acceptor and C—H...π interactions, forming ribbons extending along the c-axis direction.

  5. Chalcones as novel influenza A (H1N1) neuraminidase inhibitors from Glycyrrhiza inflata

    DEFF Research Database (Denmark)

    Dao, Trong Tuan; Nguyen, Phi Hung; Lee, Hong Sik;

    2011-01-01

    The emergence of highly pathogenic influenza A virus strains, such as the new H1N1 swine influenza (novel influenza), represents a serious threat to global human health. During our course of an anti-influenza screening program on natural products, one new licochalcone G (1) and seven known (2......-8) chalcones were isolated as active principles from the acetone extract of Glycyrrhiza inflata. Compounds 3 and 6 without prenyl group showed strong inhibitory effects on various neuraminidases from influenza viral strains, H1N1, H9N2, novel H1N1 (WT), and oseltamivir-resistant novel H1N1 (H274Y) expressed...

  6. Chalcone-derived Diels-Alder adducts as NF-κB inhibitors from Morus alba.

    Science.gov (United States)

    Phung, Thi Xuan Binh; Tran, Thi Hong Hanh; Dan, Thi Thuy Hang; Chau, Van Minh; Hoang, Thanh Huong; Nguyen, Tien Dat

    2012-01-01

    A bioassay-guided phytochemical fractionation of the methanol extract of the Morus alba root barks led to the isolation of two chalcone-derived Diels-Alder adducts (1 and 2). Their structures were elucidated as kuwanon J 2,4,10″-trimethyl ether (1) and kuwanon R (2) by means of spectroscopic methods. Both compounds strongly inhibited nuclear transcription factor.κB activity with the IC₅₀ values of 4.65 and 7.38 μM, respectively.

  7. Features of the reaction of heterocyclic analogs of chalcone with lanthanide shift reagents

    Energy Technology Data Exchange (ETDEWEB)

    Turov, A.V.; Khilya, V.P. [Taras Shevchenko Kiev Univ. (Russian Federation)

    1994-10-01

    The PMR spectra of heterocyclic analogs of 2-hydroxychalcone containing thiazole, benzofuran, triazole, imidazole, benzodioxane, or pyridine rings in the presence of lanthanide shift reagents are studied. It is found that the most effective reagent for modifying the spectra of these compounds is Yb(fod)3. The broadening of the spectra of 2-hydroxy chalcones in the presence of lanthanide shift reagents is explained by the dynamic effects of complex formation. An example is given of the determination of the conformation of molecules of 2-hydroxychalcone by the simultaneous use of lanthanide shift reagents and the homonuclear Overhauser effect. 9 refs., 1 fig., 1 tab.

  8. Synthesis and antimicrobial evaluation of new chalcones containing piperazine or 2,5-dichlorothiophene moiety.

    Science.gov (United States)

    Tomar, V; Bhattacharjee, G; Kamaluddin; Kumar, Ashok

    2007-10-01

    Two new series of chalcones have been synthesized by reacting 1-(4-piperazin-1-yl-phenyl)ethanone and 1-(2,5-dichloro-3-thienyl)-1-ethanone with different substituted benzaldehydes in turn by Claisen-Schmidt condensation. The compounds have been characterized by IR, (1)H NMR spectral and microanalysis data. All the synthesized compounds have been evaluated for antimicrobial activity. Some of these derivatives are potentially active against Gram-positive bacteria, Staphylococcus aureus and Escherichia coli while the most potent compound (1) in this study showed MIC(50) value of 2.22 microg/mL against Candida albicans.

  9. IR and NMR spectral studies of 4-bromo-1-naphthyl chalcones-assessment of substituent effects

    Science.gov (United States)

    Thirunarayanan, G.; Gopalakrishnan, M.; Vanangamudi, G.

    2007-07-01

    Infrared νCO (cm -1) of s-cis and s-trans frequencies and nuclear magnetic resonance chemical shifts δ1H (ppm) of H-α and H-β, δ13C (ppm) of C-α and C-β data were assigned from their respective spectra of a series of various substituted styryl 4-bromo-1-naphthyl chalcones. These values are correlated with various Hammett substituent constants. From the results of statistical analysis, the effect of substituents can be explained.

  10. Inhibition of mitogen activated protein kinases increases the sensitivity of A549 lung cancer cells to the cytotoxicity induced by a kava chalcone analog.

    Science.gov (United States)

    Warmka, Janel K; Solberg, Eric L; Zeliadt, Nicholette A; Srinivasan, Balasubramanian; Charlson, Aaron T; Xing, Chengguo; Wattenberg, Elizabeth V

    2012-08-03

    We are interested in investigating the biological activity of chalcones, a major class of compounds found in the beverage kava, in order to develop potent and selective chemopreventive candidates. Consumption of kava in the South Pacific Islands is inversely correlated with cancer incidence, even among smokers. Accordingly, chalcones have anti-cancer activities in animal and cell culture models. To investigate signaling pathways that affect chalcone action we studied a potent analog, (E)-3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (chalcone-24). Chalcone-24 was selected from a series of chalcone analogs that were synthesized based on the structures derived from flavokawain compounds found in kava, and screened in A549 lung cancer cells for induction of cytotoxicity and inhibition of NF-κB, a transcription factor associated with cell survival. Incubation of A549 cells with chalcone-24 resulted in a dose-dependent inhibition of cell viability, inhibition of NF-κB, activation of caspases, and activation of extracellular signal regulated kinase 1/2 (ERK1/2) and c-Jun N-terminal kinase (JNK); ERK1/2 and JNK are mitogen activated protein kinases that play central roles in regulating cell fate. Pharmacological inhibitors of ERK1/2 or JNK increased the sensitivity of A549 cells to chalcone-24-induced cytotoxicity, without affecting NF-κB or caspase activity. These results will help refine the synthesis of chalcone analogs to maximize the combination of actions required to prevent and treat cancer.

  11. Kinetics and mechanism of OsOsub(4) catalyzed oxidation of chalcones by Cesub(4) in aqueous acetic sulfuric acid media

    Energy Technology Data Exchange (ETDEWEB)

    Srinivasulu, P.V.; Adinarayana, M.; Sethuram, B.; Rao, T.N. (Osmania Univ., Hyderabad (India). Dept. of Chemistry)

    1985-01-01

    Kinetics of OsOsub(4) catalyzed oxidation of chalcones by Cesup(4+) was studied in aqueous acetic-sulfuric acid medium in the temperature range 313 to 338 K. The order in oxidant is zero while the order with respect to substrate and catalyst are each fractional. The rate of the reaction decreased with increase in percentage of acetic acid while (Hsup(+)) had practically no effect on the rate. The rates of various substituted chalcones are given. A mechanism in which formation of a cyclic ester between chalcone and OsOsub(4) in a fast step followed by its decomposition in a rate-determining step is envisaged.

  12. Optical anisotropy of polyimide and polymethacrylate containing photocrosslinkable chalcone group in the side chain under irradiation of a linearly polarized UV light

    CERN Document Server

    Choi, D H

    2002-01-01

    Photocrosslinkable soluble polyimide and polymethacrylate compound were synthesized for studying the optically induced anisotropy of the thin films. Chalcone group was introduced into the side chain unit of two polymers. We observed a photodimerization behavior between the double bonds in the chalcone group and an optical anisotropy of these materials by irradiation of a linearly polarized UV light (LPL). Optical anisotropy of the thin film was also investigated by using polarized UV absorption spectroscopy.The dynamic property of optical anisotropy in photoreactive polyimide was compared to that in polymethacrylate containing chalcone group in the side chain.

  13. Synthesis and in vitro biological evaluation of dihydroartemisinyl-chalcone esters.

    Science.gov (United States)

    Smit, Frans J; van Biljon, Riëtte A; Birkholtz, Lyn-Marie; N'Da, David D

    2015-01-27

    A series of dihydroartemisinyl-chalcone esters were synthesized through esterification of chalcones with dihydroartemisinin (DHA). The hybrids were screened against chloroquine (CQ) sensitive (3D7) and CQ resistant (W2) strains of intraerythrocytic Plasmodium falciparum parasites, and were all found to be active, with IC50 values ranging between 1.5 and 11 nM against both strains, with SI values over 5800. The esters featuring oxygenated aryl rings (7, 10 and 11), were found to be equipotent to DHA, but were 2-3 times more active than artesunate against the 3D7 and W2 strains of the malaria parasites. They were also screened in vitro against a panel of three cancer cell lines consisting of TK-10, UACC-62 and MCF-7. Compound 7, bearing a furan ring, displayed the most potent overall antitumor activity against all three cancer cell lines. TGA revealed that the targeted hybrids were all thermally more stable than DHA, which may be beneficial to the high temperature storage conditions that prevail in malaria endemic countries. During this study, ester 7 was identified as the best candidate for further investigation as a potential drug in search for new, safe and effective antimalarial drugs.

  14. Iodobenzene diacetate-mediated isomerization of pyrazolyl chalcones and their cytotoxicity and anti-microbial activity

    Indian Academy of Sciences (India)

    Mahavir Parshad; Vikas Verma; Devinder Kumar; Balasubramanian Narasimhan; Smit Kour; Shashank Singh; Payare Lal Sangwan

    2015-03-01

    Synthesis of cis (E)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenyl/aryl/heteroarylprop-2-en-1-ones from 1-phenyl-3-methyl-4-acetylpyrazol-5-one was achieved in good yield. s-cis (E)-1-(5-Hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-arylprop-2-en-1-ones were isomerized to s-trans (E)-4-(3-(phenyl/aryl/heteroaryl)acryloyl)-5-methyl-2-phenyl-1H-pyrazol-3(2H)-ones using iodobenzene diacetate in dichloromethane at room temperature in excellent yield. The structure and geometry of these , -unsaturated ketones (pyrazolyl ketones) were established with the help of NMR, 2D NMR and HRMS techniques. The cytotoxicity of pyrazolyl chalcones showed that s-cis (E) 1-(5-Hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(4-methylphenyl)-prop-2-en-1-one is active at very low concentrations (IC50 13.3 M) against colon cancer cell line (HCT-116). The in vitro anti-microbial studies of pyrazolyl chalcones were also tested against grampositive (B. subtilis, S. aureus) and gram-negative bacteria (E. coli) and for anti-fungal activity against C. albicans and A. niger.

  15. Influence of S-Oxidation on Cytotoxic Activity of Oxathiole-Fused Chalcones.

    Science.gov (United States)

    Konieczny, Marek T; Buɬakowska, Anita; Pirska, Danuta; Konieczny, Wojciech; Skladanowski, Andrzej; Sabisz, Michal; Wojciechowski, Marek; Lemke, Krzysztof

    2016-10-01

    Synthesis, in vitro cytotoxic activity, and interaction with tubulin of oxidized, isomeric 1-(5-alkoxybenzo[d][1,3]oxathiol-6-yl)-3-phenylprop-2-en-1-ones and 1-(6-alkoxybenzo[d][1,3]oxathiol-5-yl)-3-phenylprop-2-en-1-ones are described. Most of the compounds demonstrated cytotoxic activity at submicromolar concentrations. It was found that oxidation of sulfur atom of the oxathiole-fused chalcones strongly influenced activity of the parent compounds, and that depending on relative position of the sulfur atom in the molecule, the activity was either increased or diminished. For isomers with sulfur atom para to the chalcone carbonyl group, oxidation led to increase in activity, while for isomers with sulfur atom meta to the carbonyl the activity dropped down. It was demonstrated that the compounds interact with tubulin at the colchicine binding site, and the interaction was evaluated using molecular modeling. It was concluded that the observed profound influence of oxidation of the sulfur atom on cytotoxic activity cannot be solely related to interaction of the compounds with tubulin.

  16. Ultrasound accelerated Claisen-Schmidt condensation: A green route to chalcones

    Energy Technology Data Exchange (ETDEWEB)

    Calvino, V. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Picallo, M. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Lopez-Peinado, A.J. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Martin-Aranda, R.M. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain)]. E-mail: rmartin@ccia.uned.es; Duran-Valle, C.J. [Dpto. de Quimica Inorganica, Facultad de Ciencias, Universidad de Extremadura, Avenida de Elvas s/n., 06071 Badajoz (Spain)

    2006-06-30

    Chalcones have been synthesized under sonochemical irradiation by Claisen-Schmidt condensation between benzaldehyde and acetophenone. Two basic activated carbons (Na and Cs-Norit) have been used as catalysts. The effect of the ultrasound activation has been studied. A substantial enhancing effect in the yield was observed when the carbon catalyst was activated under ultrasonic waves. This 'green' method (combination of alkaline-doped carbon catalyst and ultrasound waves) has been applied to the synthesis of several chalcones with antibacterial properties achieving, in all cases, excellent activities and selectivities. A comparative study under non-sonic activation has showed that the yields are lower in silent conditions, indicating that the sonication exerts a positive effect on the activity of the catalyst. Cs-doped carbon is presented as the optimum catalyst, giving excellent activity for this type of condensation. Cs-Norit carbon catalyst can compete with the traditional NaOH/EtOH when the reaction is carried out under ultrasounds. The role of solvent in this reaction was studied with ethanol. High conversion was obtained in absence of solvent. The carbons were characterized by thermal analysis, nitrogen adsorption and X-ray photoelectron spectroscopy.

  17. Antimicrobial effects of Piper hispidum extract, fractions and chalcones against Candida albicans and Staphylococcus aureus.

    Science.gov (United States)

    Costa, G M; Endo, E H; Cortez, D A G; Nakamura, T U; Nakamura, C V; Dias Filho, B P

    2016-09-01

    Three chalcones, 2'-hydroxy-4,4',6'-trimethoxychalcone, 2'-hydroxy-4,4',6'-tetramethoxychalcone, and 3,2'-dihydroxy-4,4',6'-trimethoxychalcone, were isolated from the leaves of Piper hispidum in a bioguided fractionation of crude extract. The antimicrobial activity of crude extract of P. hispidum leaves was determined against bacteria Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, Staphylococcus aureus and yeasts Candida albicans, C. parapsilosis and C. tropicalis. Fractions and chalcones were tested against C. albicans and S. aureus. The checkerboard assay was performed to assess synergic interactions between extract and antifungal drugs, and the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) reduction assay was used to evaluate anti-biofilm effects of extract. The extract was active against yeasts, S. aureus and B. subtilis with MIC values between 15.6 and 62.5μg/mL. Synergistic effects of extract associated with fluconazole and nystatin were observed against C. albicans, with fractional inhibitory concentration indices of 0.37 and 0.24, respectively. The extract was also effective against C. albicans and S. aureus biofilm cells at concentrations of 62.5 and 200μg/mL, respectively. Thus, P. hispidum may be a possible source of bioactive substances with antimicrobial properties.

  18. Chalcone scaffolds as anti-infective agents: structural and molecular target perspectives.

    Science.gov (United States)

    Mahapatra, Debarshi Kar; Bharti, Sanjay Kumar; Asati, Vivek

    2015-08-28

    In recent years, widespread outbreak of numerous infectious diseases across the globe has created havoc among the population. Particularly, the inhabitants of tropical and sub-tropical regions are mainly affected by these pathogens. Several natural and (semi) synthetic chalcones deserve the credit of being potential anti-infective candidates that inhibit various parasitic, malarial, bacterial, viral, and fungal targets like cruzain-1/2, trypanopain-Tb, trans-sialidase, glyceraldehyde-3-phosphate dehydrogenase (GAPDH), fumarate reductase, falcipain-1/2, β-hematin, topoisomerase-II, plasmepsin-II, lactate dehydrogenase, protein kinases (Pfmrk and PfPK5), and sorbitol-induced hemolysis, DEN-1 NS3, H1N1, HIV (Integrase/Protease), protein tyrosine phosphatase A/B (Ptp-A/B), FtsZ, FAS-II, lactate/isocitrate dehydrogenase, NorA efflux pump, DNA gyrase, fatty acid synthase, chitin synthase, and β-(1,3)-glucan synthase. In this review, a comprehensive study (from Jan. 1982 to May 2015) of the structural features of anti-infective chalcones, their mechanism of actions (MOAs) and structure activity relationships (SARs) have been highlighted. With the knowledge of molecular targets, structural insights and SARs, this review may be helpful for (medicinal) chemists to design more potent, safe, selective and cost effective anti-infective agents.

  19. Biotransformation of Flavokawains A, B, and C, Chalcones from Kava (Piper methysticum), by Human Liver Microsomes.

    Science.gov (United States)

    Zenger, Katharina; Agnolet, Sara; Schneider, Bernd; Kraus, Birgit

    2015-07-22

    The in vitro metabolism of flavokawains A, B, and C (FKA, FKB, FKC), methoxylated chalcones from Piper methysticum, was examined using human liver microsomes. Phase I metabolism and phase II metabolism (glucuronidation) as well as combined phase I+II metabolism were studied. For identification and structure elucidation of microsomal metabolites, LC-HRESIMS and NMR techniques were applied. Major phase I metabolites were generated by demethylation in position C-4 or C-4' and hydroxylation predominantly in position C-4, yielding FKC as phase I metabolite of FKA and FKB, helichrysetin as metabolite of FKA and FKC, and cardamonin as metabolite of FKC. To an even greater extent, flavokawains were metabolized in the presence of uridine diphosphate (UDP) glucuronic acid by microsomal UDP-glucuronosyl transferases. For all flavokawains, monoglucuronides (FKA-2'-O-glucuronide, FKB-2'-O-glucuronide, FKC-2'-O-glucuronide, FKC-4-O-glucuronide) were found as major phase II metabolites. The dominance of generated glucuronides suggests a role of conjugated chalcones as potential active compounds in vivo.

  20. Hydrogenation of chalcones using hydrogen permeating through a Pd and palladized Pd electrodes

    Energy Technology Data Exchange (ETDEWEB)

    Gutierrez, M., E-mail: mcgutier@unse.edu.a [INQUINOA - CONICET, Instituto de Ciencias Quimicas, Facultad de Agronomia Agroindustrias, Universidad Nacional de Santiago del Estero, Avda, Belgrano (S) 1912, 4200, Santiago del Estero (Argentina); Nazareno, M.A. [INQUINOA - CONICET, Instituto de Ciencias Quimicas, Facultad de Agronomia Agroindustrias, Universidad Nacional de Santiago del Estero, Avda, Belgrano (S) 1912, 4200, Santiago del Estero (Argentina); Sosa, V. [Departamento de Quimica Organica, Facultad de Ciencias Quimicas, Universidad Nacional de Cordoba, Agencia postal 4, Casilla 61, 5000, Cordoba (Argentina); Lopez de Mishima, B.A., E-mail: bmishima@unse.edu.a [INQUINOA - CONICET, Instituto de Ciencias Quimicas, Facultad de Agronomia Agroindustrias, Universidad Nacional de Santiago del Estero, Avda, Belgrano (S) 1912, 4200, Santiago del Estero (Argentina); Mishima, H.T. [INQUINOA - CONICET, Instituto de Ciencias Quimicas, Facultad de Agronomia Agroindustrias, Universidad Nacional de Santiago del Estero, Avda, Belgrano (S) 1912, 4200, Santiago del Estero (Argentina)

    2010-08-01

    The hydrogenation of benzalacetone and benzalacetophenone was carried out using atomic hydrogen permeating through a palladium membrane. A two-compartment cell separated by a Pd sheet or a palladized Pd (Pd/Pd black) sheet electrode was employed. The reduction products were identified by (GC) gas chromatography, UV-vis absorption spectroscopy and NMR spectroscopy. The carbon-carbon double bond was hydrogenated and the benzylacetone and benzylacetophenone were obtained as products using palladium catalyst. The current efficiency for hydrogenation reaction increases when the current density for water electrolysis decreases and depends on the initial chalcone concentration. It is over 90% at the concentration of 10 mmol L{sup -1}. The hydrogen absorption and diffusion into and through a palladium membrane electrode has been studied by using an electrochemical impedance spectroscopy method. The impedance results would indicate that the hydrogen permeated through the membrane is consumed by the chalcone during the hydrogenation process keeping as the permeable boundary condition in the outer side of the Pd membrane the hydrogen activity almost zero. The hydrogen entering the metal through an adsorbed state and the rate of hydrogen absorption is diffusion-controlled.

  1. Chalcone derivatives from the fern Cyclosorus parasiticus and their anti-proliferative activity.

    Science.gov (United States)

    Wei, Han; Zhang, Xuenong; Wu, Guanghua; Yang, Xian; Pan, Songwei; Wang, Yanyan; Ruan, Jinlan

    2013-10-01

    Three new chalcone derivatives, named parasiticins A-C (1-3), were isolated from the leaves of Cyclosorus parasiticus, together with four known chalcones, 5,7-dihydroxy-4-phenyl-8-(3-phenyl-trans-acryloyl)-3,4-dihydro-1-benzopyran-2-one (4), 2'-hydroxy-4',6'-dimethoxychalcone (5), 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (6), 2',4'-dihydroxy-6'-methoxy-3'-methylchalcone (7). The chemical structures of the new isolated compounds were elucidated unambiguously by spectroscopic data analysis. The cytotoxic activities of compounds 1-7 were evaluated against six human cancer cell lines in vitro. Compounds 3 and 6 exhibited substantial cytotoxicity against all six cell lines, especially toward HepG2 with the IC₅₀ values of 1.60 and 2.82 μM, respectively. Furthermore, we demonstrated that compounds 3 and 6 could induce apoptosis in the HepG2 cell line, which may contribute significantly to their cytotoxicity.

  2. Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents.

    Science.gov (United States)

    Siddiqui, Zeba N; Musthafa, T N Mohammed; Ahmad, Anis; Khan, Asad U

    2011-05-15

    A novel approach was adopted for the synthesis of series of new pyrazolyl chalcones (3a-c) by the reaction of 5-chloro-3-methyl-1-phenylpyrazole-4-carboxaldehyde (1) with different 5-acetylbarbituric acid derivatives (2a-c) under thermal solvent-free condition. The chalcones were then converted to the corresponding pyrazolines (4a-c) under the same condition in excellent yields. All the synthesized compounds were characterized using elemental analysis and spectral data (IR, (1)H NMR, and mass spectrometry). The synthesized compounds were tested for their antimicrobial activity by disk diffusion assay with slight modifications against Gram-positive, Gram-negative strains of bacteria as well as fungal strains. The investigation of antimicrobial screening revealed that compounds (3a-4c) showed good antibacterial and antifungal activities, respectively. Among the screened compounds, 3b showed more potent inhibitory activity (MIC=12.5 μg/ml) nearly to that of standard antibiotics ciprofloxacin, griseofulvin and fluconazole.

  3. Chalcone-based Selective Inhibitors of a C4 Plant Key Enzyme as Novel Potential Herbicides

    Science.gov (United States)

    Nguyen, G. T. T.; Erlenkamp, G.; Jäck, O.; Küberl, A.; Bott, M.; Fiorani, F.; Gohlke, H.; Groth, G.

    2016-06-01

    Weeds are a challenge for global food production due to their rapidly evolving resistance against herbicides. We have identified chalcones as selective inhibitors of phosphoenolpyruvate carboxylase (PEPC), a key enzyme for carbon fixation and biomass increase in the C4 photosynthetic pathway of many of the world’s most damaging weeds. In contrast, many of the most important crop plants use C3 photosynthesis. Here, we show that 2‧,3‧,4‧,3,4-Pentahydroxychalcone (IC50 = 600 nM) and 2‧,3‧,4‧-Trihydroxychalcone (IC50 = 4.2 μM) are potent inhibitors of C4 PEPC but do not affect C3 PEPC at a same concentration range (selectivity factor: 15–45). Binding and modeling studies indicate that the active compounds bind at the same site as malate/aspartate, the natural feedback inhibitors of the C4 pathway. At the whole plant level, both substances showed pronounced growth-inhibitory effects on the C4 weed Amaranthus retroflexus, while there were no measurable effects on oilseed rape, a C3 plant. Growth of selected soil bacteria was not affected by these substances. Our chalcone compounds are the most potent and selective C4 PEPC inhibitors known to date. They offer a novel approach to combat C4 weeds based on a hitherto unexplored mode of allosteric inhibition of a C4 plant key enzyme.

  4. New antimicrobial combinations: substituted chalcones- oxacillin against methicillin resistant Staphylococcus aureus

    Directory of Open Access Journals (Sweden)

    Juan Manuel Talia

    2011-06-01

    Full Text Available Staphylococcus aureus, the most virulent Staphylococcus species, is also the prevalent pathogen isolated from hospitalized patients and the second most common from patients in outpatient settings. In general, bacteria have the genetic ability to transmit and acquire resistance to drugs, which are utilized as therapeutic agents. Related studies of antimicrobial activity indicate that crude extracts containing flavonoids, triterpenes and steroids have showed significative activity against several Staphylococcus aureus strains. Combination effects between flavonoids and antibiotics also have been reported. The aim of the present work was to investigate in vitro synergism between several chalcones substituted in combination with oxacillin, an antibiotic used conventionally against S. aureus ATCC 43 300 that is resistant to meticillin, using the kinetic turbidimetric method developed earlier. The results were satisfactory for all assayed combinations and in accordance with the mechanism of bacteriostatic inhibition previously proposed, except for 2´,4´-dihydroxy-3´-methoxychalcone - oxacillin. The best combination was 2´,3´-dihydroxychalcone - oxacillin (MIC: 11.2 μg/mL. Further investigations are needed to characterize the interaction mechanism with antibiotics. Thus, chalcones - oxacillin combination could lead to the development of new antibiotics against methicillin resistant S. aureus infection.

  5. Synthesis, Antiviral Bioactivity of Novel 4-Thioquinazoline Derivatives Containing Chalcone Moiety

    Directory of Open Access Journals (Sweden)

    Zhihua Wan

    2015-06-01

    Full Text Available A series of novel 4-thioquinazoline derivatives containing chalcone moiety were designed, synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited moderate to good anti-TMV activity. In particular, compounds M2 and M6 possessed appreciable protection activities against TMV in vivo, with 50% effective concentration (EC50 values of 138.1 and 154.8 μg/mL, respectively, which were superior to that of Ribavirin (436.0 μg/mL. The results indicated that chalcone derivatives containing 4-thioquinazoline moiety could effectively control TMV. Meanwhile, the structure-activity relationship (SAR of the target compounds, studied using the three-dimensional quantitative structure-activity relationship (3D-QSAR method of comparative molecular field analysis (CoMFA based on the protection activities against TMV, demonstrated that the CoMFA model exhibited good predictive ability with the cross-validated q2 and non-cross-validated r2 values of 0.674 and 0.993, respectively. Meanwhile, the microscale thermophoresis (MST experimental showed that the compound M6 may interaction with the tobacco mosaic virus coat protein (TMV CP.

  6. RMN 13C de chalcones protonées: Factorisation des interactions intramoléculaires

    Science.gov (United States)

    Membrey, François; Doucet, Jean-Pierre

    13C study of protonated para, para' disubstituted chalcones XC 6H 4CHCHC(OH) +C 6H 4Y, shows for the chemical shift of the carbenium center important deviations from a strict additivity of Substituent Induced Shifts observed in the corresponding monosubstituted ions. By collecting the experimental data into sub-populations where only one substituent (X or Y) varies—the other remaining fixed—a network of linear homogeneous correlations (δ/δ) is obtained. Their largely variable slopes indicate that the susceptibility of the carbenium site to the perturbations induced by one of the substituent groups depends on the nature of the other substituent group. The definition of 'Intrinsic Substituent Parameters' (derived from the SCS observed, in these ions, on the aromatic para positions) allows to separate the action of a substituent group on the electronic interaction mechanism and the global perturbation detected on the observation site. For a quantitative evaluation of these interactions, a Factorization Model is proposed, where deviations to additivity of the SCS are expressed as a product of the intrinsic parameters of X and Y groups. This model is successfully applied to 13C spectra of protonated chalcones and benzophenones. The parallelism between these intrinsic group effects and the SCS observed in monosubstituted benzenes points out the prime importance in these cationic systems, of π polarisation effects modulating the electron transfer toward the carbenium center within a concerted π-inductive mesomeric action.

  7. Nonlinear optical studies on 1,3-disubstituent chalcones doped polymer films

    Science.gov (United States)

    Poornesh, P.; Shettigar, Seetharam; Umesh, G.; Manjunatha, K. B.; Prakash Kamath, K.; Sarojini, B. K.; Narayana, B.

    2009-04-01

    We report the measurements of the third-order nonlinear optical properties of recently synthesized and characterized two different 1,3-disubstituent chalcones doped PMMA films, with the prospective of reaching a good compromise between processability and high nonlinear optical properties. The measurements were done using nanosecond Z-scan at 532 nm. The Z-scan spectra reveal a large negative nonlinear refraction coefficient n2 of the order 10 -11 esu and the molecular two photon absorption cross section is 10 -46 cm 4 s/photon. The doped films exhibit good optical power limiting property under nanosecond regime and the two photon absorption (TPA) is the dominating process leading to the nonlinear behavior. The improvement in the nonlinear properties has been observed when methylenedioxy group is replaced by dimethoxy group due to increase in conjugation length. The observed nonlinear parameters of chalcone derivatives doped PMMA film is comparable with stilbazolieum derivatives, a well-known class of optical materials for photonics and biophotonics applications, which suggests that, these moieties have potential for the application of all-optical limiting and switching devices.

  8. Chalcone synthesis and hydroxylation of flavonoids in 3'-position with enzyme preparations from flowers of Dianthus caryophyllus L. (carnation).

    Science.gov (United States)

    Spribille, R; Forkmann, G

    1982-07-01

    Chalcone synthase activity was demonstrated in enzyme preparations from flowers of defined genotypes of Dianthus caryophyllus L. (carnation). In the absence of chalcone isomerase activity, which could be completely excluded by genetic methods, the first product formed from malonyl-CoA and 4-coumaroyl-CoA proved to be naringenin chalcone, followed by formation of naringenin as a result of chemical cyclization. In the presence of chalcone isomerase activity, however, naringenin was the only product of the synthase reaction. In vitro, both 4-coumaryl-CoA and caffeoyl-CoA were found to be used as substrates for the condensation reaction with respective pH optima of 8.0 and 7.0. The results of chemogenetic and enzymatic studies, however, showed that in vivo only 4-coumaroyl-CoA serves as substrate for the formation of the flavonoid skeleton. In confirmation of these results, an NADPH-dependent microsomal 3'-hydroxylase activity could be demonstrated, catalyzing hydroxylation of naringenin and dihydrokaempferol in 3'-position. Furthermore, a strict correlation was found between 3'-hydroxylase activity and the gene r which is known to control the formation of 3', 4'-hydroxylated flavonoid compounds.

  9. Design, synthesis, molecular docking and biological evaluation of new dithiocarbamates substituted benzimidazole and chalcones as possible chemotherapeutic agents.

    Science.gov (United States)

    Bacharaju, Keerthana; Jambula, Swathi Reddy; Sivan, Sreekanth; Jyostnatangeda, Saritha; Manga, Vijjulatha

    2012-05-01

    A series of novel dithiocarbamates with benzimidazole and chalcone scaffold have been designed synthesised and evaluated for their antimitotic activity. Compounds 4c and 9d display the most promising antimitotic activity with IC(50) of 1.66 μM and 1.52 μM respectively.

  10. Synthesis and Biological Activity of Some 3,5-Diaryl-1-Benzothiazolopyrazoline Derivatives: Reaction of Chalcones with 2-Hyrazinobenzothiazoles

    Directory of Open Access Journals (Sweden)

    Vandana Sharma

    2009-01-01

    Full Text Available A series of 3,5-diaryl-1-benzothiazolopyrazoline derivatives were synthesized by the reaction of appropriately substituted chalcones and 2-hydrazinobenzothiazole in ethanol. The synthesized heterocycles have been characterized on the basis of their chemical properties and spectroscopic data. These compounds were tested for biological activity against a variety of test organisms.

  11. Synthesis and Biological Activity of Some 3, 5-Diarylisoxazoline Derivatives: Reaction of Substituted Chalcones with Hydroxylamine Hydrochloride

    Directory of Open Access Journals (Sweden)

    Vandana Sharma

    2010-01-01

    Full Text Available A series of 3-aryl-5-styrylisoxazoline/ 3,5-diarylisoxazoline derivatives were synthesized by the reaction of appropriately substituted chalcones and hydroxylamine hydrochloride in presence of alkali in ethanol. The synthesized heterocycles have been characterized on the basis of their chemical properties and spectroscopic data. These compounds were tested for biological activity against a variety of test organisms

  12. Iodine-catalyzed addition of 2-mercaptoethanol to chalcone derivatives: Synthesis of the novel β-mercapto carbonyl compounds

    Directory of Open Access Journals (Sweden)

    Gürkan Yerli

    2012-01-01

    Full Text Available In this study, a series of novel β-mercapto carbonyl derivatives (3-(2-hydroxyethylthio-1,3-diarylpropan-1-one (5a-i were prepared by addition of 2-mercaptoethanol (4 to chalcones (3a-i in the presence of catalytic amount of iodine (10 mol % in CH 2Cl 2.

  13. Conjugate Addition of Indoles to α,β-Unsaturated Ketones (Chalcones) Catalyzed by KHSO4 under Ultrasonic Conditions

    Institute of Scientific and Technical Information of China (English)

    ZENG Xiao-Fei; JI Shun-Jun; SHEN Shu-Su

    2007-01-01

    Conjugate addition of indoles to a variety of α,β-unsaturated ketones (chalcones) mediated by a catalytic amount of KHSO4 at room temperature under ultrasonic conditions to afford the corresponding Michael adducts in good to excellent yields was reported.

  14. Fungal plasma membrane H+-ATPase inhibitory activity of o-hydroxybenzylated flavanones and chalcones from Uvaria chamae P. Beauv

    DEFF Research Database (Denmark)

    Kongstad, Kenneth Thermann; Wubshet, Sileshi Gizachew; Kjellerup, Lasse;

    2015-01-01

    to identification of a series of uncommon o-hydroxybenzylated flavanones and chalcones, i.e., chamanetin (8), isochamanetin (9), isouvaretin (10), uvaretin (11), dichamanetin (12), and diuvaretin (15). Preparative-scale isolation of the active metabolites allowed determination of IC50 values for inhibition...

  15. HIGHLY DIASTEREOSELECTIVE MICHAEL ADDITION OF FLAVANONE TO ITS CHALCONE PRECURSOR UNDER SOLVENT-FREE CONDITIONS USING MICROWAVES

    Science.gov (United States)

    Substituted 2'-hydroxychalcones were found to give an equilibrium mixture of the starting chalcone and the corresponding flavanone in 4:6 - 1:3 ratio in the presence of various supports and MW irradiation. MW irradiation of 2'-hydroxychalcones in the presence of DBU gave two hit...

  16. HIGHLY DISATEREOSELECTIVE MICHAEL ADDITION OF FLAVANONE TO ITS CHALCONE PRECURSOR UNDER SOLVENT-FREE CONDITIONS USING MICROWAVES [POSTER

    Science.gov (United States)

    Substituted 2'-hydroxychalcones were found to give an equilibrium mixture of the starting chalcone and the corresponding flavanone inf 4.6-1:3 ratio in the presence of DBU gave two hitherto unknown diasteromeric dimers in a highly diastereoselective Michael addition of the carban...

  17. Ferrocenyl Chalcone with 2-Anthracenyl Group (2-Anth-C(O)CH=CHFc): Electrochemical and Fluorescent Properties

    Energy Technology Data Exchange (ETDEWEB)

    Lee, Su Kyung; Lim, Chae Mi; Lee, Ji Yeon; Noh, Dong Youn [Seoul Women' s University, Seoul (Korea, Republic of)

    2011-01-15

    In this study, a ferrocenyl chalcone with a 2-anthracenyl group, an analogue of was prepared. Unlike is fluorescent and its fluorescence was investigated in relation to its solvent's polarity. Its electrochemical properties were also studied and the local geometry of is suggested from {sup 1}H NMR results. Ferrocenyl chalcones, in which ferrocenyl and aromatic groups are linked by an enone bridge, are versatile compounds exhibiting antiplasmodial and antitumor activities, fluorescent and electrochemical properties, and molecular chemosensor activity. Ferrocenyl chalcones bearing the fluorophores such as 2-naphthalene, 9-anthracene, 1-pyrene, and N-ethyl carbazole, are regarded as good candidates for new fluorescent material. However, ferrocenyl chalcones containing 9-anthracene and 2-naphthalene derivatives have been reported as being not fluorescent, while those containing 1-pyrene and N-ethyl carbazole derivatives are fluorescent. It means that the ferrocenyl group, known as an effective quencher of exited states, is therefore not the only reason why they are non-fluorescent. Some derivatization of fluoro-phores can also disable fluorescence, as demonstrated by 2-acetylanthracene being fluorescent while 9-acetylanthracene is not.

  18. Synthesis of a novel series of chalcones and pyrazolines, possessing indole with 4-(2,2,2-trifluroethoxy pyridine moiety

    Directory of Open Access Journals (Sweden)

    Mazahar Farooqui

    2012-02-01

    Full Text Available A new method for the construction of novel fluorine-containing indole ring system has been reported. These indoles were converted into a new series of fluorine-containing indolyl chalcones (1a-g and pyrazolines (2a-g. All the newly synthesized compounds were characterized with the help of IR, MS and NMR spectroscopic data.

  19. Newly-synthesized chalcones-inhibition of adherence and biofilm formation of methicillin-resistant Staphylococcus aureus.

    Science.gov (United States)

    Bozic, Dragana D; Milenkovic, Marina; Ivkovic, Branka; Cirkovic, Ivana

    2014-01-01

    Biofilm formation and adherence of bacteria to host tissue are one of the most important virulence factors of methicillin-resistant strains of Staphylococcus aureus (MRSA). The number of resistant strains is seriously increasing during the past years and bacteria have become resistant, not only to methicillin, but also to other commonly used antistaphylococcal antibiotics. There is a great need for discovering a novel antimicrobial agent for the treatment of staphylococcal infections. One of the most promising groups of compounds appears to be chalcones. In present study we evaluated the in vitro effect of three newly synthesized chalcones: 1,3- Bis-(2-hydroxy-phenyl)-propenone, 3-(3-Hydroxy-phenyl)-1-(2-hydroxy-phenyl)-propenone and 3-(4-Hydroxy-phenyl)-1-(2-hydroxy-phenyl)-propenone on glycocalyx production, biofilm formation and adherence to human fibronectin of clinical isolates and laboratory control strain of MRSA (ATCC 43300). Subinhibitory concentrations of the tested compounds reduced the production of glycocalyx, biofilm formation and adherence to human fibronectin of all MRSA strains. Inhibition of biofilm formation was dose dependent and the most effective was 1,3- Bis-(2-hydroxy-phenyl)-propenone. In our study we demonstrated that three newly-synthesized chalcones exhibited significant effect on adherence and biofilm formation of MRSA strains. Chalcones may be considered as promising new antimicrobial agents that can be used for prevention of staphylococcal infections or as adjunct to antibiotics in conventional therapy.

  20. Newly-synthesized chalcones-inhibition of adherence and biofilm formation of methicillin-resistant Staphylococcus aureus

    Directory of Open Access Journals (Sweden)

    Dragana D. Bozic

    2014-01-01

    Full Text Available Biofilm formation and adherence of bacteria to host tissue are one of the most important virulence factors of methicillin-resistant strains of Staphylococcus aureus (MRSA. The number of resistant strains is seriously increasing during the past years and bacteria have become resistant, not only to methicillin, but also to other commonly used antistaphylococcal antibiotics. There is a great need for discovering a novel antimicrobial agent for the treatment of staphylococcal infections. One of the most promising groups of compounds appears to be chalcones. In present study we evaluated the in vitro effect of three newly synthesized chalcones: 1,3-Bis-(2-hydroxy-phenyl-propenone, 3-(3Hydroxy-phenyl-1-(2-hydroxy-phenyl-propenone and 3-(4-Hydroxy-phenyl-1-(2-hydroxyphenyl-propenone on glycocalyx production, biofilm formation and adherence to human fibronectin of clinical isolates and laboratory control strain of MRSA (ATCC 43300. Subinhibitory concentrations of the tested compounds reduced the production of glycocalyx, biofilm formation and adherence to human fibronectin of all MRSA strains. Inhibition of biofilm formation was dose dependent and the most effective was 1,3-Bis-(2-hydroxy-phenyl-propenone. In our study we demonstrated that three newly-synthesized chalcones exhibited significant effect on adherence and biofilm formation of MRSA strains. Chalcones may be considered as promising new antimicrobial agents that can be used for prevention of staphylococcal infections or as adjunct to antibiotics in conventional therapy.

  1. Effects of a herbal gel containing carvacrol and chalcones on alveolar bone resorption in rats on experimental periodontitis.

    Science.gov (United States)

    Botelho, Marco Antonio; Rao, Vietla Satyanarayana; Montenegro, Danusa; Bandeira, Mary Anne Menezes; Fonseca, Said Gonçalves Cruz; Nogueira, Nadia Accioly Pinto; Ribeiro, Ronaldo Albuquerque; Brito, Gerly Anne Castro

    2008-04-01

    Carvacrol and dimeric chalcones are the respective bioactive components of Lippia sidoides and Myracrodruon urundeuva, popular medicinal plants of Northeastern Brazil with proven antimicrobial and antiinflammatory properties. Periodontal disease is associated with inflammation and microbiological proliferation, thus the study aimed to investigate the effect of a topical gel based on carvacrol and chalcones in the experimental periodontal disease (EPD) in rats. Animals were treated with carvacrol and/or chalcones gel, immediately after EPD induction, three times a day for 11 days. Appropriate controls were included in the study. Animals were weighed daily. They were killed on day 11, the mandibles dissected and alveolar bone loss was measured. The periodontium were examined at histopathology and the neutrophil influx into the gingiva was assayed using myeloperoxidase activity. The bacterial flora were assessed through culture of the gingival tissue. Alveolar bone loss was significantly (p gel, compared with the vehicle and non-treated groups. The treatment with the combined gel reduced tissue lesion at histopathology, decreased myeloperoxidase activity in gingival tissue and inhibited the growth of oral microorganisms as well as the weight loss. Carvacrol and chalcones combination gel has a beneficial effect upon EPD in this model.

  2. 17O NMR studies on 4- and 4'-substituted chalcones and p-substituted β-nitrostyrenes

    Science.gov (United States)

    Boykin, D. W.; Baumstark, A. L.; Balakrishnan, P.; Perjéssy, A.; Hrnc˜iar, P.

    The 17O NMR chemical shift data for 17O-enriched 4- and 4'-chalcones in toluene at 90°C and for p-substituted β-nitrostyrenes (natural abundance) in acetonitrile at 70°C are reported. The SCS (substituent chemical shift) range for the 4-chalcones p-CH 3O to p-NO 2 is 16.3 ppm; the range for the 4'-chalcones p-CH 3O to p-NO 2 is 32.4 ppm. The SCS range for the p-substituted-β-nitrostyrenes p-CH 3O to p-NO 2 is 13.2 ppm. The data for the three series gave good correlations with σ + constants, while the Dual Substitutent Parameter treatment only slightly improved the correlations using σ R+ constants. Plots of the 17O chemical shifts for both 4- and 4'-chalcones with 17O data for acetophenones and correlation of 17O chemical shift data for the β-nitrostyrenes with that of nitrobenzenes gave good correlations. Plots of the 17O data for all the three series with their respective functional group stretching frequencies gave fair correlations.

  3. Differential Effects of Structural Modifications on the Competition of Chalcones for the PIB Amyloid Imaging Ligand-Binding Site in Alzheimer's Disease Brain and Synthetic Aβ Fibrils.

    Science.gov (United States)

    Fosso, Marina Y; McCarty, Katie; Head, Elizabeth; Garneau-Tsodikova, Sylvie; LeVine, Harry

    2016-02-17

    Alzheimer's disease (AD) is a complex brain disorder that still remains ill defined. In order to understand the significance of binding of different clinical in vivo imaging ligands to the polymorphic pathological features of AD brain, the molecular characteristics of the ligand interacting with its specific binding site need to be defined. Herein, we observed that tritiated Pittsburgh Compound B ((3)H-PIB) can be displaced from synthetic Aβ(1-40) and Aβ(1-42) fibrils and from the PIB binding complex purified from human AD brain (ADPBC) by molecules containing a chalcone structural scaffold. We evaluated how substitution on the chalcone scaffold alters its ability to displace (3)H-PIB from the synthetic fibrils and ADPBC. By comparing unsubstituted core chalcone scaffolds along with the effects of bromine and methyl substitution at various positions, we found that attaching a hydroxyl group on the ring adjacent to the carbonyl group (ring I) of the parent member of the chalcone family generally improved the binding affinity of chalcones toward ADPBC and synthetic fibrils F40 and F42. Furthermore, any substitution on ring I at the ortho-position of the carbonyl group greatly decreases the binding affinity of the chalcones, potentially as a result of steric hindrance. Together with the finding that neither our chalcones nor PIB interact with the Congo Red/X-34 binding site, these molecules provide new tools to selectively probe the PIB binding site that is found in human AD brain, but not in brains of AD pathology animal models. Our chalcone derivatives also provide important information on the effects of fibril polymorphism on ligand binding.

  4. A facile synthesis of 1,2,3-triazolyl indole hybrids via SbCl3-catalysed Michael addition of indoles to 1,2,3-triazolyl chalcones

    Indian Academy of Sciences (India)

    Poovan Shanmugavelan; Murugan Sathishkumar; Sangaraiah Nagarajan; Alagusundaram Ponnuswamy

    2012-07-01

    An efficient, facile and environmentally benign synthesis of a library of 1,2,3-triazolyl chalcone hybrids (3a-u) has been accomplished by grinding the reactants at room temperature in excellent yields in very short reaction time. Subsequently, SbCl3 catalysed Michael addition of indoles to the chalcones afford 1,2,3-triazolyl indole hybrids (5a-l) in excellent yields.

  5. Design, synthesis and antiproliferative activity studies of novel dithiocarbamate-chalcone derivates.

    Science.gov (United States)

    Fu, Dong-Jun; Zhang, Sai-Yang; Liu, Ying-Chao; Zhang, Li; Liu, Jun-Ju; Song, Jian; Zhao, Ruo-Han; Li, Feng; Sun, Hui-Hui; Liu, Hong-Min; Zhang, Yan-Bing

    2016-08-15

    A series of novel dithiocarbamate-chalcone derivates were designed, synthesized and evaluated for antiproliferative activity against three selected cancer cell lines (EC-109, SK-N-SH and MGC-803). Majority of the synthesized compounds exhibited moderate to potent activity against all the cancer cell lines assayed. Particularly, compounds II2 and II5 exhibited the excellent growth inhibition against SK-N-SH with IC50 values of 2.03μM and 2.46μM, respectively. Further mechanism studies revealed that compound II2 could obviously inhibit the proliferation of SK-N-SH cells by inducing apoptosis and arresting the cell cycle at G0/G1 phase.

  6. Structural effects and thermal decomposition kinetics of chalcones under non-isothermal conditions

    Directory of Open Access Journals (Sweden)

    G. Manikandan

    2016-09-01

    Full Text Available Two chalcones namely, 1,5-bis(4-hydroxy-3-methoxyphenylpentan-1,4-dien-3-one (BHMPD and 2,5-bis(4-hydroxy-3-methoxybenzylidenecyclopentanone (BHMBC have been synthesised and characterized by microanalysis, FT-IR, mass spectra and NMR (1H and 13C techniques. The thermal decomposition of these compounds was studied by TGA and DTA under dynamic nitrogen atmosphere at different heating rates of 10, 15 and 20 K min−1. The kinetic parameters were calculated using model-fitting (Coats–Redfern, CR and model-free methods (Friedman, Kissinger–Akahira–Sunose, KAS and Flynn–Wall–Ozawa, FWO. The decomposition process of BHMPD and BHMBC followed a single step mechanism as evidenced from the data. Existence of compensation effect was noticed for the decomposition of these compounds. Invariant kinetic parameters are consistent with the average values obtained by Friedman and KAS isoconversional method in both compounds.

  7. An anther-specific chalcone synthase-like gene D5 related to rice pollen development

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    It was shown in a previous analysis that D5 gene from rice (Oryza sativa L.) was an anther-specific gene encoding a chalcone synthase-related protein. In this study, D5 gene was found specifically expressed in tapetum cells as well as in the peripheral cells of the vascular bundle of rice anthers by RNA in situ hybridization. In order to study its function, D5 was transformed into rice in both sense and antisense directions driven by a rice Actin 1 promoter. It has been observed that the pollen grains from the antisense D5 transgenic rice plants are abnormal, indicating that D5 plays a critical role in rice pollen development.

  8. Microwave-assisted synthesis and tyrosinase inhibitory activity of chalcone derivatives.

    Science.gov (United States)

    Liu, Jinbing; Chen, Changhong; Wu, Fengyan; Zhao, Liangzhong

    2013-07-01

    A series of chalcones and their derivatives were synthesized, and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activity, and four compounds exhibited more potent tyrosinase inhibitory activity than the reference standard inhibitor kojic acid (5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one). Specifically, 1-(-1-(4-methoxyphen- yl)-3-phenylallylidene)thiosemicarbazide (18) exhibited the most potent tyrosinase inhibitory activity with IC₅₀ value of 0.274 μM. The inhibition mechanism analysis of 1-(-1-(2,4-dihydroxyphenyl)-3-phenylallylidene) thiosemicarbazide (16) and 1-(-1-(4-methoxyphenyl)-3-phenylallylidene) thiosemicarbazide (18) demonstrated that the inhibitory effects of the two compounds on the tyrosinase were irreversible. Preliminary structure activity relationships' analysis suggested that further development of such compounds might be of interest.

  9. Synthesis of novel carbazole chalcones as radical scavenger, antimicrobial and cancer chemopreventive agents.

    Science.gov (United States)

    Bandgar, Babasaheb P; Adsul, Laxman K; Lonikar, Shrikant V; Chavan, Hemant V; Shringare, Sadanand N; Patil, Sachin A; Jalde, Shivkumar S; Koti, Basawaraj A; Dhole, Nagesh A; Gacche, Rajesh N; Shirfule, Amol

    2013-06-01

    A series of novel carbazole chalcones has been synthesised and evaluated for radical scavenging activity, cytotoxicity and antimicrobial activities. Compounds 12m, 12o and 12c exhibited good 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, compounds 12e, 12m and 12d were excellent hydroxyl radical scavengers and compounds 12a, 12e, 12g, 12n and 12m have shown inhibition of oxidative DNA damage induced by 2,2'-azobis (2-amidinopropane hydrochloride). Compounds 12j, 12i, 12n, 12c, 12m and 12e were most active against the selected cancer cell lines. Compounds 12a, 12e and 12m showed good antibacterial activity and compounds 12h and 12m have shown good antifungal activity. All the compounds were subjected for absorption, distribution, metabolism and excretion (ADME) predictions by computational method and found that these molecules could be considered as potential candidates for oral drug development.

  10. Synthesis antimicrobial and antioxidant studies of new oximes of steroidal chalcones.

    Science.gov (United States)

    Lone, Imtiyaz H; Khan, Khaliquz Z; Fozdar, Bharat I; Hussain, Fida

    2013-09-01

    A convenient synthesis of oximes of steroidal chalcones (4a-4j) was performed and structural assignment of the products was confirmed on the basis of IR, (1)HNMR, (13)C NMR, MS and analytical data. The synthesized compounds were screened for in vitro antioxidant activity by using DPPH method and in vitro antimicrobial activity against different bacterial and fungal strains by agar diffusion method. The activity of the tested compounds against each microbe varied due to structural differences between them. Presence and position of different substituents on the benzene ring of the chalconyl pendent had a marked effect on the activity of the compounds. From the results it can be inferred that the compounds 4a-j showed significant antioxidant activity and antimicrobial activity against all microbial strains used for testing.

  11. Structural Correlation of Some Heterocyclic Chalcone Analogues and Evaluation of Their Antioxidant Potential

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2013-09-01

    Full Text Available A series of six novel heterocyclic chalcone analogues 4(a–f has been synthesized by condensing 2-acetyl-5-chlorothiophene with benzaldehyde derivatives in methanol at room temperature using a catalytic amount of sodium hydroxide. The newly synthesized compounds are characterized by IR, mass spectra, elemental analysis and melting point. Subsequently; the structures of these compounds were determined using single crystal X-ray diffraction. All the synthesized compounds were screened for their antioxidant potential by employing various in vitro models such as DPPH free radical scavenging assay, ABTS radical scavenging assay, ferric reducing antioxidant power and cupric ion reducing antioxidant capacity. Results reflect the structural impact on the antioxidant ability of the compounds. The IC50 values illustrate the mild to good antioxidant activities of the reported compounds. Among them, 4f with a p-methoxy substituent was found to be more potent as antioxidant agent.

  12. Co-suppression in transgenic Petunia hybrida expressing chalcone synthase A (chsA)

    Institute of Scientific and Technical Information of China (English)

    李艳; 惠有为; 张仲凯; 黄兴奇; 李毅

    2001-01-01

    Chalcone synthase A is a key enzyme in the anthocyanin biosynthesis pathway. Expression of chsA gene in transgenic Petunia hybrida resulted in flower color alterations and co-suppression of transgenes and endogenous genes. We fused the β-glucuronidase (uidA) gene to the C-terminal of chsA gene, and transferred the fusion gene into Petunia hybrida via Agrobacterium tumefaciens. GUS histochemical staining analysis showed that co-suppression occurred specifically during the development of flowers and co-suppression required the mutual interaction of endogenous genes and transgenes. RNA in situ hybridization analysis suggested that co-suppression occurred in the entire plant, and RNA degradation occurred in the cytoplasm.

  13. Efficient ultrasound-assisted synthesis, spectroscopic, crystallographic and biological investigations of pyrazole-appended quinolinyl chalcones

    Science.gov (United States)

    Prasath, R.; Bhavana, P.; Sarveswari, S.; Ng, Seik Weng; Tiekink, Edward R. T.

    2015-02-01

    Two series of new quinolinyl chalcones containing a pyrazole group, 3a-f and 4a-r, have been synthesized by Claisen-Schmidt condensation of the derivatives of 2-methyl-3-acetylquinoline with either substituted 1,3-diphenyl-1H-pyrazole-4-carbaldehyde or 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde in 76-93% yield under ultrasonic method. The compounds were characterized using IR, 1H NMR and ESI-MS spectroscopic methods and, for representative compounds, by X-ray crystallography. An E-configuration about the Cdbnd C ethylene bond has been established via 1H NMR spectroscopy and X-ray crystallography. These compounds show promising anti-microbial properties, with 4a and 3e being the most potent against bacterial and fungal strains, respectively and the methoxy substituted compounds showed moderate anti-oxidant activity.

  14. Synthesis, characterization and calculated non-linear optical properties of two new chalcones

    Science.gov (United States)

    Singh, Ashok Kumar; Saxena, Gunjan; Prasad, Rajendra; Kumar, Abhinav

    2012-06-01

    Two new chalcones viz 3-(4-(benzyloxy)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1) and 3-(4-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (2) have been prepared and characterized by micro analyses, 1H NMR, IR, UV-Vis spectroscopy and single crystal X-ray. The first static hyperpolarizability (β) for both the compounds has been investigated by density functional theory (DFT). Also, the solvent-induced effects on the non-linear optical properties (NLO) were studied by using self-consistent reaction field (SCRF) method. As the solvent polarity increases, the β value increases monotonically. The electronic absorption bands of both 1 and 2 have been assigned by time dependent density functional theory (TD-DFT). Both the compounds displayed better non-linear optical (NLO) responses than the standard p-nitroaniline (pNA).

  15. Substituent Dependence of Third-Order Optical Nonlinearity in Chalcone Derivatives

    Science.gov (United States)

    Kiran, Anthony John; Satheesh Rai, Nooji; Chandrasekharan, Keloth; Kalluraya, Balakrishna; Rotermund, Fabian

    2008-08-01

    The third-order nonlinear optical properties of derivatives of dibenzylideneacetone were investigated using the single beam z-scan technique at 532 nm. A strong dependence of third-order optical nonlinearity on electron donor and acceptor type of substituents was observed. An enhancement in χ(3)-value of one order of magnitude was achieved upon the substitution of strong electron donors compared to that of the molecule substituted with an electron acceptor. The magnitude of nonlinear refractive index of these chalcones is as high as of 10-11 esu. Their nonlinear optical coefficients are larger than those of widely used thiophene oligomers and trans-1-[p-(p-dimethylaminobenzyl-azo)-benzyl]-2-(N-methyl-4-pyridinium)-ethene iodide (DABA-PEI) organic compounds.

  16. Chalcone-imidazolone conjugates induce apoptosis through DNA damage pathway by affecting telomeres

    Directory of Open Access Journals (Sweden)

    Kamal Ahmed

    2011-04-01

    Full Text Available Abstract Background Breast cancer is one of the most prevalent cancers in the world and more than one million women are diagnosed leading to 410,000 deaths every year. In our previous studies new chalcone-imidazolone conjugates were prepared and evaluated for their anticancer activity in a panel of 53 human tumor cell lines and the lead compounds identified were 6 and 8. This prompted us to investigate the mechanism of apoptotic event. Results Involvement of pro-apoptotic protein (Bax, active caspase-9 and cleavage of retinoblastoma protein was studied. Interestingly, the compounds caused upregulation of p21, check point proteins (Chk1, Chk2 and as well as their phosphorylated forms which are known to regulate the DNA damage pathway. Increased p53BP1 foci by immunolocalisation studies and TRF1 suggested the possible involvement of telomere and associated proteins in the apoptotic event. The telomeric protein such as TRF2 which is an important target for anticancer therapy against human breast cancer was extensively studied along with proteins involved in proper functioning of telomeres. Conclusions The apoptotic proteins such as Bax, active caspase-9 and cleaved RB are up-regulated in the compound treated cells revealing the apoptotic nature of the compounds. Down regulation of TRF2 and upregulation of the TRF1 as well as telomerase assay indicated the decrease in telomeric length revealing telomeric dysfunction and thereby controlling the rapid rate of cell proliferation. In summary, chalcone-imidazolone conjugates displayed significant DNA damage activity particularly at telomeres and caused both apoptosis and senescence-like growth arrest which suggested that these compounds have potential activity against breast carcinoma.

  17. Molecular cloning and expression profiling of a chalcone synthase gene from Lamiophlomis rotata

    Indian Academy of Sciences (India)

    Qiao Feng; Geng Gui-Gong; Zeng Yang; Xie Hui-Chun; Jin Lan; Shang Jun; Chen Zhi

    2015-06-01

    Lamiophlomis rotata is a renowned Chinese medicinal plant. Chalcone synthase (CHS) is important in flavonoid and isoflavonoid biosynthesis, catalysing the formation of naringenin chalcone in plants. A full-length cDNA encoding the CHS gene was cloned from L. rotata based on the highly conserved CHS gene sequences of Labiatae plants. A blast search showed its homology (named LrCHS) with other CHS genes of Labiate plants. The full-length genomic DNA of LrCHS was 2026 bp with one intron of 651 bp, two exons of 178 bp and 998 bp, flanked by a 73 bp $5'$-UTR and a 126 bp $3'$-UTR. The cDNA sequence of the LrCHS gene had an 1176 bp open reading frame encoding a 391 amino acid protein of 42,798 Da. The CHS protein predicted from L. rotata showed 79–86% identity with CHS of other plant species. We conducted a phylogenetic analysis of nine families containing 48 plants and L. rotata based on the full amino acid sequences of CHS proteins. Consequently, LrCHS was located in the Labiatae branch. Additionally, we examined LrCHS gene expression patterns in different tissues by quantitative real-time PCR with specific primers. The expression analysis showed preferential expression of LrCHS in flowers and leaves during the flowering stage. Total flavonoid content and CHS gene expression exhibited similar patterns during L. rotata organ development. In agreement with its function as an elicitor-responsive gene, LrCHS expression was coordinated by methyl jasmonate and UV light, and induced between 6 and 18 h. These results provide a molecular basis for additional functional studies of LrCHS in L. rotata.

  18. Chalcones and N-acylhydrazones: direct analogues? Exploratory data analysis applied to potential novel antileishmanial agents

    Directory of Open Access Journals (Sweden)

    Daniela Gonçalves Rando

    2010-06-01

    Full Text Available Leishmaniasis is an important health and social problem for which there is limited effective therapy. Chalcones and N-acylhydrazones have been studied as promising antileishmanial agents in enzymatic inhibition and in vitro assays. Since these chemical classes of compounds also resemble each other structurally, it would be useful to investigate whether they share direct analogy. Exploratory data analysis was applied to a library of chalcones and nitrated N-acylhydrazones assayed against Leishmania donovani to investigate their similarity. Under the conditions applied in the present study, the two classes did not present functional or structural analogy.As leishmanioses são importantes problemas sociais e de saúde pública para os quais a terapia farmacológica atual é, ainda, limitada. Chalconas e N-acilidrazonas têm sido estudadas como promissores agentes leishmanicidas tanto em ensaios in vitro quanto em ensaios de inibição de cisteíno-proteases importantes para o parasito. Uma vez que estas classes de compostos apresentam similaridade bidimensional, seria interessante estudar se estes compostos guardariam relação de analogia direta entre si. Análise exploratória de dados foi aplicada, então, à biblioteca de chalconas e N-acilidrazonas nitradas ensaiadas contra Leishmania donovani para investigar suas relações de similaridade. Os resultados mostraram que, ao menos sob as condições consideradas neste estudo, as duas classes de compostos não apresentam analogia estrutural e funcional simultaneamente, embora elas apresentem alguma similaridade estrutural.

  19. Synthesis and evaluation of chalcone derivatives as inhibitors of neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species.

    Science.gov (United States)

    Bukhari, Syed N A; Tajuddin, Yasmin; Benedict, Vannessa J; Lam, Kok W; Jantan, Ibrahim; Jalil, Juriyati; Jasamai, Malina

    2014-02-01

    Inhibitory effects on neutrophils' chemotaxis, phagocytosis and production of reactive oxygen species (ROS) are among the important targets in developing anti-inflammatory agents and immunosuppressants. Eight series of chalcone derivatives including five newly synthesized series were assessed for their inhibitory effects on chemotaxis, phagocytosis and ROS production in human polymorphonuclear neutrophils (PMNs). Inhibition of PMNs' chemotaxis and phagocytosis abilities were investigated using the Boyden chamber technique and the Phagotest kit, respectively, while ROS production was evaluated using luminol- and lucigenin-based chemiluminescence assay. The new derivatives (4d and 8d), which contain 4-methylaminoethanol functional group were active in all the assays performed. It was also observed that some of the compounds were active in inhibiting chemotaxis while others suppressed phagocytosis and ROS production. The information obtained gave new insight into chalcone derivatives with the potential to be developed as immunomodulators.

  20. Theoretical and Experimental Study of Inclusion Complexes of β-Cyclodextrins with Chalcone and 2',4'-Dihydroxychalcone.

    Science.gov (United States)

    Sancho, Matias I; Andujar, Sebastian; Porasso, Rodolfo D; Enriz, Ricardo D

    2016-03-31

    The inclusion complexes formed by chalcone and 2',4'-dihydroxychalcone with β-cyclodextrin have been studied combining experimental (phase solubility diagrams, Fourier transform infrared spectroscopy) and molecular modeling (molecular dynamics, quantum mechanics/molecular mechanics calculations) techniques. The formation constants of the complexes were determined at different temperatures, and the thermodynamic parameters of the process were obtained. The inclusion of chalcone in β-cyclodextrin is an exothermic process, while the inclusion of 2',4'-dihydroxychalcone is endothermic. Free energy profiles, derived from umbrella sampling using molecular dynamics simulations, were constructed to analyze the binding affinity and the complexation reaction at a molecular level. Hybrid QM/MM calculations were also employed to obtain a better description of the energetic and structural aspects of the complexes. The intermolecular interactions that stabilize both inclusion complexes were characterized by means of quantum atoms in molecules theory and reduce density gradient method. The calculated interactions were experimentally observed using FTIR.

  1. An initio computation of electron affinities of substituted benzalacetophenones (chalcones): a new approach to substituent effects in organic electrochemistry

    Energy Technology Data Exchange (ETDEWEB)

    Hicks, L.D.; Fry, A.J.; Kurzweil, V.C. [Wesleyan University, Middletown, CT (United States). Chemistry Dept.

    2004-12-15

    The electron affinities (EAs) of a training set of 29 monosubstituted benzalacetophenones (chalcones) were computed at the ab initio density functional B3LYP/6-31G level of theory. The EAs and experimental reduction potentials of the training set are highly linearly correlated (correlation coefficient of 0.969 and standard deviation of 10.8 mV). An additional 72 di-, tri-, and tetrasubstituted chalcones were then synthesized. Their reduction potentials were predicted from computed EAs using the linear correlation derived from the training set. Agreement between the experimental and computed reduction potentials is remarkably good, with a standard deviation of less than 22 mV for this very large set of substances whose potentials extend over a range of almost 700 mV. (author)

  2. Ab initio computation of electron affinities of substituted benzalacetophenones (chalcones): a new approach to substituent effects in organic electrochemistry

    Energy Technology Data Exchange (ETDEWEB)

    Hicks, L.D.; Fry, A.J.; Kurzweil, V.C. [Wesleyan Univ., Middletown, CT (United States). Hall-Atwater Lab.

    2004-12-15

    The electron affinities (EAs) of a training set of 29 monosubstituted benzalacetophenones (chalcones) were computed at the ab initio density functional B3LYP/6-31G* level of theory. The EAs and experimental reduction potentials of the training set are highly linearly correlated (correlation coefficient of 0.969 and standard deviation of 10.8 mV). An additional 72 di-, tri-, and tetrasubstituted chalcones were then synthesized. Their reduction potentials were predicted from computed EAs using the linear correlation derived from the training set. Agreement between the experimental and computed reduction potentials is remarkably good, with a standard deviation of less than 22 mV for this very large set of substances whose potentials extend over a range of almost 700 mV. (Author)

  3. Synthesis and biological evaluation of a novel series of chalcones incorporated pyrazole moiety as anticancer and antimicrobial agents.

    Science.gov (United States)

    Mohamed, Magda F; Mohamed, Mervat S; Shouman, Samia A; Fathi, Mohamed M; Abdelhamid, Ismail Abdelshafy

    2012-11-01

    A newly synthesized series of chalcone derivatives containing pyrazole rings were synthesized and evaluated for their cytotoxic activities in vitro against several human cancer cell lines. Most of the prepared compounds showed potential cytotoxicity against human breast cancer cell lines MCF-7, HEPG-2, and HCT-116. Also the compounds were evaluated as antimicrobial agents. The three compounds 3, 4, and 5 were proved to be better anticancer agents than the positive standard doxorubicin with IC50 values (4.7, 4.4, and 3.9 μg/ml) against the same human cancer cell lines, whereas compounds 5 and 6 showed the most active antimicrobial compounds in comparison to the other chalcones.

  4. Antibacterial activity of two chalcones, xanthoangelol and 4-hydroxyderricin, isolated from the root of Angelica keiskei KOIDZUMI.

    Science.gov (United States)

    Inamori, Y; Baba, K; Tsujibo, H; Taniguchi, M; Nakata, K; Kozawa, M

    1991-06-01

    Two chalcones, xanthoangelol (I) and 4-hydroxyderricin (II), isolated from the root of Angelica keiskei KOIDZUMI (Umbelliferae) showed antibacterial activity against gram-positive pathogenic bacteria. The activity of I on Micrococcus luteus IFO-12708 (minimum inhibitory concentration (MIC), 0.76 microgram/ml) was the same potency as that of gentamicin, which is used as a standard. Although the activity of both chalcones on plant-pathogenic bacteria was lower than that of streptomycin sulfate, used as a positive control, they also exhibited growth-inhibitory effects. The antibacterial activity of I isolated from Angelica keiskei KOIDZUMI is being reported here for the first time. The growth-inhibitory effect of II on plant-pathogenic bacteria is also reported for the first time in this paper.

  5. Effects of structural modifications on the metal binding, anti-amyloid activity, and cholinesterase inhibitory activity of chalcones.

    Science.gov (United States)

    Fosso, Marina Y; LeVine, Harry; Green, Keith D; Tsodikov, Oleg V; Garneau-Tsodikova, Sylvie

    2015-09-28

    As the number of individuals affected with Alzheimer's disease (AD) increases and the availability of drugs for AD treatment remains limited, the need to develop effective therapeutics for AD becomes more and more pressing. Strategies currently pursued include inhibiting acetylcholinesterase (AChE) and targeting amyloid-β (Aβ) peptides and metal-Aβ complexes. This work presents the design, synthesis, and biochemical evaluation of a series of chalcones, and assesses the relationship between their structures and their ability to bind metal ions and/or Aβ species, and inhibit AChE/BChE activity. Several chalcones were found to exhibit potent disaggregation of pre-formed N-biotinyl Aβ1-42 (bioAβ42) aggregates in vitro in the absence and presence of Cu(2+)/Zn(2+), while others were effective at inhibiting the action of AChE.

  6. Benzophenone Synthase and Chalcone Synthase Accumulate in the Mesophyll of Hypericum perforatum Leaves at Different Developmental Stages

    OpenAIRE

    Belkheir, Asma K.; Gaid, Mariam; Liu, Benye; Hänsch, Robert; Beerhues, Ludger

    2016-01-01

    The active medicinal constituents in Hypericum perforatum, used to treat depression and skin irritation, include flavonoids and xanthones. The carbon skeletons of these compounds are formed by chalcone synthase (CHS) and benzophenone synthase (BPS), respectively. Polyclonal antisera were raised against the polyketide synthases from Hypericum androsaemum and their IgG fractions were isolated. Immunoblotting and immunotitration were used to test the IgGs for crossreactivity and monospecificity ...

  7. Targeting breast cancer using retinoic acid trifloromethyl chalcone: A promising therapeutic strategy in the treatment of breast cancer

    OpenAIRE

    Hao Ding; Ben-Zhong Wang; Hua-Qing Zhu; Liu-Yi Dong; Yu-Fang Gu; Yu Zhao

    2015-01-01

    The study was devised to investigate the effect of retinoic acid trifloromethyl chalcone (RAFC) on mammary carcinogenesis in female rats. The data revealed a significant decrease in number of rats with mammary tumor, number of tumors per rat and tumor volume by 54, 72 and 75% respectively in RAFC group compared to control group. The ibuprofen treated rats also showed a significant decrease in number of rats with tumor, number of tumors per rat and tumor volumes by 43%, 55%, and 59%, respectiv...

  8. Synthesis, Leishmanicidal and Cytotoxic Activity of Triclosan-Chalcone, Triclosan-Chromone and Triclosan-Coumarin Hybrids

    OpenAIRE

    Elver Otero; Sebastián Vergara; Robledo, Sara M.; Wilson Cardona; Miguel Carda; Vélez,Ivan D; Carlos Rojas; Felipe Otálvaro

    2014-01-01

    Twelve hybrids derived from triclosan were obtained via Williamson etherification of O-triclosan alkyl bromide plus chalcone and O-coumarin or O-chromone alkyl bromide plus triclosan, respectively. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes. Cytotoxic activity was also evaluated against mammalian U-937 cells. Compounds 7–9 and 17, were active against Leishmani...

  9. New eco-friendly animal bone meal catalysts for preparation of chalcones and aza-Michael adducts

    Directory of Open Access Journals (Sweden)

    Riadi Yassine

    2012-06-01

    Full Text Available Abstract Two efficient reactions were successfully carried out using Animal Bone Meal (ABM and potassium fluoride or sodium nitrate doped ABMs as new heterogeneous catalysts under very mild conditions. After preparation and characterization of the catalysts, we first report their use in a simple and convenient synthesis of various chalcones by Claisen–Schmidt condensation and then in an aza-Michael addition involving several synthesized chalcones with aromatic amines. All the reactions were carried out at room temperature in methanol; the chalcone synthesis was also achieved in water environment under microwave irradiation. Doping ABM enhances the rate and yield at each reaction. Catalytic activities are discussed and the ability to re-use the ABM is demonstrated. Results For Claisen–Schmidt the use of ABM alone, yields never exceeded 17%. In each entry, KF/ABM and NaNO3/ABM (79-97% gave higher yields than using ABM alone under thermic condition. Also the reaction proceeded under microwave irradiation in good yields (72-94% for KF/ABM and 81-97% for NaNO3/ABM and high purity. For aza-Michael addition the use of ABM doped with KF or NaNO3 increased the catalytic activity remarkably. The very high yields could be noted (84-95% for KF/ABM and 81-94% for NaNO3/ABM. Conclusion The present method is an efficient and selective procedure for the synthesis of chalcones an aza-Michael adducts. The ABM and doped ABMs are a new, inexpensive and attractive solid supports which can contribute to the development of catalytic processes and reduced environmental problems.

  10. Inhibition of fumarate reductase in Leishmania major and L. donovani by chalcones

    DEFF Research Database (Denmark)

    Chen, M; Zhai, L; Christensen, S B

    2001-01-01

    of mitochondrial dehydrogenases of Leishmania parasites. The present study was designed to further investigate the mechanism of action of chalcones, focusing on the parasite respiratory chain. The data show that licochalcone A inhibited the activity of fumarate reductase (FRD) in the permeabilized Leishmania major....... Since FRD exists in the Leishmania parasite and does not exist in mammalian cells, it could be an excellent target for antiprotozoal drugs....

  11. The Effect of Trans-Chalcone on Amylase Activity, Blood Glucose and Lipid Levels in Diabetic and Non Diabetic Rats

    Directory of Open Access Journals (Sweden)

    M Najafian

    2011-04-01

    Full Text Available Introduction & Objective: Alpha amylase is the most important decomposing enzyme in starch. Digestion and absorption of starch in the intestine can be prevented and also the blood sugar levels can be controlled by restrain and control of alpha amylase. The aim of this study was to evaluate the effect of trans-chalcone on amylase activity, blood glucose and lipid levels in diabetic and non diabetic rats. Materials & Methods: This experimental study was conducted in 1388 at Tehran University of Medical Sciences. Sixty rats were randomly divided to ten equal groups: non diabetic control, diabetic control, four non diabetic experiments and four diabetic experiments. Control groups received grape seed oil and experimental groups received 2, 8,16 and 32 mg/kg of body weight in a period of 24 days with a gastric cannula. Blood sugar, every two days, serum insulin levels in days 0,12, and 24 and at the end of the experiment, lipoproteins and alpha amylase activity were measured.The data were analyzed by one way analysis of variance, ANOVA, followed by Turkey,s test with SPSS soft ware . Results: On average Chalcone reduced 25.5% of blood sugar in normal and diabetic rats. IT also decreased the serum insulin level. On average, chalcone decreased 34.9% of alpha amylase activity in normal and diabetic rats. Following disturbances in lipids metabolism caused by diabetes, this drug improved lipoproteins metabolism and reduced water, food and urine volume. Conclusion: This study shows that trans-Chalcone reduces blood sugar and body weight via inhibition of alpha amylas. Moreover, improvement of lipoprotein metabolism may happen via the inhibitory effect of this drug on hydroxyl methyl glutaryl -COA reductase and phosphodiesterase.

  12. In vitro and in vivo Effects of Free and Chalcones-Loaded Nanoemulsions: Insights and Challenges in Targeted Cancer Chemotherapies

    OpenAIRE

    2014-01-01

    Several obstacles are encountered in conventional chemotherapy, such as drug toxicity and poor stability. Nanotechnology is envisioned as a strategy to overcome these effects and to improve anticancer therapy. Nanoemulsions comprise submicron emulsions composed of biocompatible lipids, and present a large surface area revealing interesting physical properties. Chalcones are flavonoid precursors, and have been studied as cytotoxic drugs for leukemia cells that induce cell death by different ap...

  13. Heterocyclic chalcone activators of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) with improved in vivo efficacy.

    Science.gov (United States)

    Lounsbury, Nicole; Mateo, George; Jones, Brielle; Papaiahgari, Srinivas; Thimmulappa, Rajash K; Teijaro, Christiana; Gordon, John; Korzekwa, Kenneth; Ye, Min; Allaway, Graham; Abou-Gharbia, Magid; Biswal, Shyam; Childers, Wayne

    2015-09-01

    Nrf2 activators represent a good drug target for designing agents to treat diseases associated with oxidative stress. Building upon previous work, we designed and prepared a series of heterocyclic chalcone-based Nrf2 activators with reduced lipophilicity and, in some cases, greater in vitro potency compared to the respective carbocyclic scaffold. These changes resulted in enhanced oral bioavailability and a superior pharmacodynamic effect in vivo.

  14. Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity.

    Science.gov (United States)

    Machala, M; Kubínová, R; Horavová, P; Suchý, V

    2001-03-01

    A series of homoisoflavonoids and chalcones, isolated from the endemic tropical plant Dracaena cinnabari Balf. (Agavaceae), were tested for their potential to inhibit cytochrome P4501A (CYP1A) enzymes and Fe-enhanced in vitro peroxidation of microsomal lipids in C57B1/6 mouse liver. The effects of the polyphenolic compounds were compared with those of prototypal flavonoid modulators of CYP1A and the well-known antioxidant, butylated hydroxytoluene. 2-Hydroxychalcone and partly 4,6-dihydroxychalcone were found to be strong inhibitors of CYP1A-dependent 7-ethoxyresorufin O-deethylase (EROD) activity in vitro comparable to the effects of quercetin and chrysin. The first screening of flavonoids and chalcones of Dracaena cinnabari for antioxidant activity was done in an in vitro microsomal peroxidation assay. While chalcones were shown to be poor antioxidants, 7,8-methylenedioxy-3(4-hydroxybenzyl) chromane, as one of the tested homoisoflavonoids, exhibited a strong antioxidant activity comparable to that of the strongest flavonol antioxidant, quercetin.

  15. Synthesis of Chalcone with Phosphotungstic Acid Catalyst%磷钨酸催化合成查尔酮

    Institute of Scientific and Technical Information of China (English)

    谭昌会; 郑荣选; 罗淑云; 林俏焰

    2012-01-01

    文章研究了以间硝基苯甲醛和苯乙酮为原料,磷钨酸为催化剂,缩合反应合成查尔酮。考察了催化剂用量、反应温度、反应时间及溶剂醋酸用量等因素对反应的影响。结果表明合成查尔酮的较佳条件是:反应温度是118℃,反应的时间5 h,磷钨酸为4 g,乙酸用量为20 mL的条件下,查尔酮的收率达到63.7%。%The paper studied chalcone was synthesized by condensation reaction of nitrobenzaldehyde and acetophenone using phosphotungstic acid as catalyst.The results showed that the better synthesis of chalcone conditions: reaction temperature 118 ℃,reaction time 5 h,phosphotungstic acid 4 g,20 mL acetic acid under the conditions of dosage,the yield of chalcone reached 63.7 %.

  16. Inhibition of PAI-1 release from human endothelial cells by Angelica keiskei Koidzumi (Ashitaba chalcones is structure-dependent

    Directory of Open Access Journals (Sweden)

    Naoki Ohkura

    2015-12-01

    Full Text Available Angelica keiskei Koidzumi (Ashitaba is a traditional herbal medicine and it is also regarded in Japan as a health food that might have antithrombotic properties. Ashitaba exudate suppresses lipopolysaccharide (LPS-induced plasma plasminogen activator inhibitor 1 (PAI-1, a risk factor for thrombotic diseases in mice. Xanthoangelol (XA and 4-hydroxyderricin (4-HD comprise > 95% of total chalcones from Ashitaba exudates that also contain trace amounts of other chalcone subtypes. The present study aimed to determine the effects of Ashitaba chalcones including xanthoangelols B (XB, D (XD, E (XE, F (XF and XA as well as 4-HD on PAI-1 levels in the medium of stimulated human EA.hy926 endothelial cells. Xanthoangelol (10 and #61549;M inhibited PAI-1 production at a rate of 77.1%, whereas the inhibition rates of XB, XD, XE and 4-HD were not significant. Xanthoangelol F was highly cytotoxic and thus its ability to inhibit PAI-1 production could not be evaluated. The side hydrocarbon chain of XA played an important role in the excretion of inhibitory activity. Small modifications of the hydrocarbon chain or small functional groups on the A ring measurably influenced the inhibitory activity of xanthoangelols. These findings warrant future research towards an understanding of the mechanism of antithrombotic action of Ashitaba as herbal medicine or antithrombotic health food. [J Intercult Ethnopharmacol 2015; 4(4.000: 355-357

  17. Genotoxic, Cytotoxic, Antigenotoxic, and Anticytotoxic Effects of Sulfonamide Chalcone Using the Ames Test and the Mouse Bone Marrow Micronucleus Test.

    Science.gov (United States)

    Silva, Carolina Ribeiro E; Borges, Flávio Fernandes Veloso; Bernardes, Aline; Perez, Caridad Noda; Silva, Daniela de Melo E; Chen-Chen, Lee

    2015-01-01

    Chalcones present several biological activities and sulfonamide chalcone derivatives have shown important biological applications, including antitumor activity. In this study, genotoxic, cytotoxic, antigenotoxic, and anticytotoxic activities of the sulfonamide chalcone N-{4-[3-(4-nitrophenyl)prop-2-enoyl]phenyl} benzenesulfonamide (CPN) were assessed using the Salmonella typhimurium reverse mutation test (Ames test) and the mouse bone marrow micronucleus test. The results showed that CPN caused a small increase in the number of histidine revertant colonies in S. typhimurium strains TA98 and TA100, but not statistically significant (p > 0.05). The antimutagenicity test showed that CPN significantly decreased the number of His+ revertants in strain TA98 at all doses tested (p micronucleus test indicated that CPN significantly increased the frequency of micronucleated polychromatic erythrocytes (MNPCE) at 24 h and 48 h, revealing a genotoxic effect of this compound. Also, a significant decrease in polychromatic/normochromatic erythrocyte ratio (PCE/NCE) was observed at the higher doses of CPN at 24 h and 48 h (p tested at 24 h (p 0.05). Additionally, CPN co-administered with MMC significantly increased PCE/NCE ratio at all doses tested, demonstrating its anticytotoxic effect. In summary, CPN presented genotoxic, cytotoxic, antigenotoxic, and anticytotoxic properties.

  18. Studies of manufacturing controlled-release graphene acid and catalyzing synthesis of chalcone with Claisen-Schmidt condensation reaction

    Science.gov (United States)

    Li, Jihui; Feng, Jia; Li, Mei; Wang, Qiaolian; Su, Yumin; Jia, Zhixin

    2013-07-01

    In the paper, graphene acid (GA) was manufactured, using flake graphite as raw material, and the acidity and the structure of GA were characterized as well as. Then, chalcone was synthesized in the presence of GA, using acetophenone and benzaldehyde as the reactant. The results showed that the acidity of GA was for pH = 1.12 in aqueous solution, and it was structured by the graphene sheets with the spaces between the graphene sheet and the graphene sheet and sulfuric acid (H2SO4) and acetic acid (CH3CO2H) inside the spaces. At the same time, the results also exhibited that the chalcone yield was able to reach 60.36% when GA dosage was 5 g, and the chalcone yields could attain apart 60.36, 52.05 and 31.16% when 5 g of GA was used thrice. This shows that GA is not only a high-performance catalyst, but also a controlled-release catalyst.

  19. Chalcones suppress fatty acid-induced lipid accumulation through a LKB1/AMPK signaling pathway in HepG2 cells.

    Science.gov (United States)

    Zhang, Tianshun; Yamamoto, Norio; Ashida, Hitoshi

    2014-06-01

    Excessive lipid accumulation in the liver has been proposed to cause hyperlipidemia, diabetes and fatty liver disease. 4-Hydroxyderricin (4HD), xanthoangelol (XAG), cardamonin (CAR) and flavokawain B (FKB) are chalcones that have exhibited various biological effects against obesity, inflammation, and diabetes; however, little is known about the inhibitory effects of these chalcones on fatty liver disease. In the present study, we investigated the ability of 4HD, XAG, CAR, and FKB to reduce lipid accumulation in hepatocytes. When HepG2 cells were treated with a mixture of fatty acids (FAs; palmitic acid : oleic acid = 1 : 2 ratio), significant lipid accumulation was observed. Under the same experimental conditions, addition of chalcones at 5 μM significantly suppressed the FA-induced lipid accumulation. We found that the expression of sterol regulatory element-binding protein-1 (SREBP-1), a key molecule involved in lipogenesis, was decreased in these chalcone-treated cells. We also found that these chalcones increased the expression of peroxisome proliferator-activated receptor α (PPARα), which is involved in FA oxidation. Moreover, these chalcones increased phosphorylation of AMP-activated protein kinase (AMPK) and liver kinase B1 (LKB1), upstream regulators of SREBP-1 and PPARα. We confirmed that an AMPK inhibitor, compound C, reversed chalcone-induced changes in SREBP-1 and PPARα expression in the HepG2 cells. Collectively, we found that 4HD, XAG, CAR, and XAG attenuated lipid accumulation through activation of the LKB1/AMPK signaling pathway in HepG2 cells.

  20. Antitumor effects of the flavone chalcone: inhibition of invasion and migration through the FAK/JNK signaling pathway in human gastric adenocarcinoma AGS cells.

    Science.gov (United States)

    Lin, Su-Hsuan; Shih, Yuan-Wei

    2014-06-01

    Chalcones (benzylideneacetophenone) are cancer-preventive food components found in a human diet rich in fruits and vegetables. In this study, we first report the chemopreventive effect of chalcone in human gastric adenocarcinoma cell lines: AGS. The results showed that chalcone could inhibit the abilities of the adhesion, invasion, and migration by cell-matrix adhesion assay, Boyden chamber invasion/migration assay, and wound-healing assay. Molecular data showed that the effect of chalcone in AGS cells might be mediated via sustained inactivation of the phosphorylation of focal adhesion kinase (FAK) and c-Jun N-terminal kinase 1 and 2 (JNK1/2) signal involved in the downregulation of the expressions of matrix metalloproteinase-2 (MMP-2) and matrix metalloproteinase-9 (MMP-9). Next, chalcone-treated AGS cells showed tremendous decrease in the phosphorylation and degradation of inhibitor of kappaBα (IκBα), the nuclear level of NF-κB, and the binding ability of NF-κB to NF-κB response element. Furthermore, treating FAK small interfering RNA (FAK siRNA) and specific inhibitor for JNK (SP600125) to AGS cells could reduce the phosphorylation of JNK1/2 and the activity of MMP-2 and MMP-9. Our results revealed that chalcone significantly inhibited the metastatic ability of AGS cells by reducing MMP-2 and MMP-9 expressions concomitantly with a marked reduction on cell invasion and migration through suppressing and JNK signaling pathways. We suggest that chalcone may offer the application in clinical medicine.

  1. Identification of Chalcones as Fasciola hepatica Cathepsin L Inhibitors Using a Comprehensive Experimental and Computational Approach

    Science.gov (United States)

    Ferraro, Florencia; Merlino, Alicia; dell´Oca, Nicolás; Gil, Jorge; Tort, José F.; Gonzalez, Mercedes; Cerecetto, Hugo; Cabrera, Mauricio

    2016-01-01

    Background Increased reports of human infections have led fasciolosis, a widespread disease of cattle and sheep caused by the liver flukes Fasciola hepatica and Fasciola gigantica, to be considered an emerging zoonotic disease. Chemotherapy is the main control measure available, and triclabendazole is the preferred drug since is effective against both juvenile and mature parasites. However, resistance to triclabendazole has been reported in several countries urging the search of new chemical entities and target molecules to control fluke infections. Methodology/Principle Findings We searched a library of forty flavonoid derivatives for inhibitors of key stage specific Fasciola hepatica cysteine proteases (FhCL3 and FhCL1). Chalcones substituted with phenyl and naphtyl groups emerged as good cathepsin L inhibitors, interacting more frequently with two putative binding sites within the active site cleft of the enzymes. One of the compounds, C34, tightly bounds to juvenile specific FhCL3 with an IC50 of 5.6 μM. We demonstrated that C34 is a slow-reversible inhibitor that interacts with the Cys-His catalytic dyad and key S2 and S3 pocket residues, determinants of the substrate specificity of this family of cysteine proteases. Interestingly, C34 induces a reduction in NEJ ability to migrate through the gut wall and a loss of motility phenotype that leads to NEJ death within a week in vitro, while it is not cytotoxic to bovine cells. Conclusions/Significance Up to date there are no reports of in vitro screening for non-peptidic inhibitors of Fasciola hepatica cathepsins, while in general these are considered as the best strategy for in vivo inhibition. We have identified chalcones as novel inhibitors of the two main Cathepsins secreted by juvenile and adult liver flukes. Interestingly, one compound (C34) is highly active towards the juvenile enzyme reducing larval ability to penetrate the gut wall and decreasing NEJ´s viability in vitro. These findings open new avenues

  2. Identification of Chalcones as Fasciola hepatica Cathepsin L Inhibitors Using a Comprehensive Experimental and Computational Approach.

    Directory of Open Access Journals (Sweden)

    Florencia Ferraro

    2016-07-01

    Full Text Available Increased reports of human infections have led fasciolosis, a widespread disease of cattle and sheep caused by the liver flukes Fasciola hepatica and Fasciola gigantica, to be considered an emerging zoonotic disease. Chemotherapy is the main control measure available, and triclabendazole is the preferred drug since is effective against both juvenile and mature parasites. However, resistance to triclabendazole has been reported in several countries urging the search of new chemical entities and target molecules to control fluke infections.We searched a library of forty flavonoid derivatives for inhibitors of key stage specific Fasciola hepatica cysteine proteases (FhCL3 and FhCL1. Chalcones substituted with phenyl and naphtyl groups emerged as good cathepsin L inhibitors, interacting more frequently with two putative binding sites within the active site cleft of the enzymes. One of the compounds, C34, tightly bounds to juvenile specific FhCL3 with an IC50 of 5.6 μM. We demonstrated that C34 is a slow-reversible inhibitor that interacts with the Cys-His catalytic dyad and key S2 and S3 pocket residues, determinants of the substrate specificity of this family of cysteine proteases. Interestingly, C34 induces a reduction in NEJ ability to migrate through the gut wall and a loss of motility phenotype that leads to NEJ death within a week in vitro, while it is not cytotoxic to bovine cells.Up to date there are no reports of in vitro screening for non-peptidic inhibitors of Fasciola hepatica cathepsins, while in general these are considered as the best strategy for in vivo inhibition. We have identified chalcones as novel inhibitors of the two main Cathepsins secreted by juvenile and adult liver flukes. Interestingly, one compound (C34 is highly active towards the juvenile enzyme reducing larval ability to penetrate the gut wall and decreasing NEJ´s viability in vitro. These findings open new avenues for the development of novel agents to control

  3. Fotoquímica de chalconas fluoradas no estado sólido Photochemistry of fluorinated chalcones in the solid state

    Directory of Open Access Journals (Sweden)

    Dari Cesarin-Sobrinho

    2002-02-01

    Full Text Available Chalcone and its fluorinated derivatives were synthesized and photolyzed in the solid state. UV irradiation of chalcone and its monosubstituted fluorine derivatives (3- and 4-fluorchalcone resulted in a mixture of anti-head-head (gamma-truxinic, sin-head-tail (alpha-truxilic and anti-head-tail (epsilon-truxilic dimers. On the other hand, upon irradiation of 3,4- and 3,5-difluorchalcone a stereoselective formation of the alpha-truxilic photodimer was observed, whereas for 2-substituted chalcones (2,3difluorchalcone, 2,5-difluorchalcone, 2,6-difluorchalcone and 2,3,4-trifluorchalcone the beta-truxilic dimer was stereoselectively obtained. 2',3',4',5',6'-pentafluorchalcone was the less reactive of all chalcones studied and at least one of the possible photodimers, i.e the anti-head-head isomer, was identified. Irradiation of polyfluorinated chalcones such as 2,3,5,6-tetrafluor-, 2,3,4,5,6-pentafluor-, and 2,2',3,3',4,4',5,5',6,6'-decafluorchalcone led only to polymerization and/or decomposition products.

  4. Cloning and expression analysis of chalcone synthase gene from Coleus forskohlii.

    Science.gov (United States)

    Awasthi, Praveen; Mahajan, Vidushi; Jamwal, Vijay Lakshmi; Kapoor, Nitika; Rasool, Shafaq; Bedi, Yashbir S; Gandhi, Sumit G

    2016-09-01

    Flavonoids are an important class of secondary metabolites that play various roles in plants such as mediating defense, floral pigmentation and plant-microbe interaction. Flavonoids are also known to possess antioxidant and antimicrobial activities. Coleus forskohlii (Willd.) Briq. (Lamiaceae) is an important medicinal herb with a diverse metabolic profile, including production of a flavonoid, genkwanin. However, components of the flavonoid pathway have not yet been studied in this plant. Chalcone synthase (CHS) catalyses the first committed step of flavonoid biosynthetic pathway. Full-length cDNA, showing homology with plant CHS gene was isolated from leaves of C. forskohlii and named CfCHS (GenBank accession no. KF643243). Theoretical translation of CfCHS nucleotide sequence shows that it encodes a protein of 391 amino acids with a molecular weight of 42.75 kDa and pI 6.57. Expression analysis of CfCHS in different tissues and elicitor treatments showed that methyl jasmonate (MeJA) strongly induced its expression. Total flavonoids content and antioxidant activity of C. forskohlii also got enhanced in response to MeJA, which correlated with increased CfCHS expression. Induction of CfCHS by MeJA suggest its involvement in production of flavonoids, providing protection from microbes during herbivory or mechanical wounding. Further, our in silico predictions and experimental data suggested that CfCHS may be posttranscriptionally regulated by miR34.

  5. Synthesis, growth, structure and characterization of chalcone crystal: A novel organic NLO material

    Science.gov (United States)

    Agilandeshwari, R.; Meenatchi, V.; Meenakshisundaram, S. P.

    2016-08-01

    Single crystals of a chalcone, (E)-3-(4-bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (BHP), were grown by the slow evaporation solution growth technique. The structure is elucidated by single-crystal X-ray diffraction analysis and the crystal belongs to the monoclinic system with noncentrosymmetric space group P21. Optical studies reveal that the absorption is minimum in the visible region and the cut-off wavelength is at ∼468 nm. The band-gap energy was estimated by the application of the Kubelka-Munk algorithm. The powder X-ray diffraction pattern reveals the good crystallinity of the as-grown specimen. The vibrational patterns in FT-IR are used to identify the functional groups and thermal studies indicate the stability of the material. The second harmonic generation efficiency (SHG), as estimated by Kurtz and Perry powder technique, reveals the superior nonlinear optical character of this material. Hirshfeld surface analysis is done to quantify the intermolecular interactions, responsible for developing a nonlinear atmosphere. As-grown crystals were further characterized by SEM, NMR, mass spectrometry and elemental analysis.

  6. Novel metronidazole-chalcone conjugates with potential to counter drug resistance in Trichomonas vaginalis.

    Science.gov (United States)

    Anthwal, Amit; Rajesh, U Chinna; Rawat, M S M; Kushwaha, Bhavana; Maikhuri, Jagdamba P; Sharma, Vishnu L; Gupta, Gopal; Rawat, Diwan S

    2014-05-22

    Trichomoniasis is the most prevalent, curable sexually transmitted disease (STD), which increases risk of viral STDs and HIV. However, drug resistance has been developed by some strains of Trichomonas vaginalis against Metronidazole (MTZ), the FDA approved drug against trichomoniasis. In the present study twenty two chalcone hybrids of metronidazole have been synthesized in a quest to get new molecules with higher potential against metronidazole-resistant T. vaginalis. All new hybrid molecules were found active against T. vaginalis with varying levels of activity against MTZ-susceptible and resistant strains. Eight compounds (4a, 4c, 4d, 4e, 4f, 4h, 4q and 4s) were found as active as the standard drug with an MIC of 1.56 μg/ml against MTZ-susceptible strain. However, compounds 4e, 4h and 4m were 4-times more active than MTZ against drug-resistant T. vaginalis, amongst which 4e and 4h were most promising against both susceptible and resistant strains.

  7. Molecular and Biochemical Analysis of Chalcone Synthase from Freesia hybrid in flavonoid biosynthetic pathway.

    Directory of Open Access Journals (Sweden)

    Wei Sun

    Full Text Available Chalcone synthase (CHS catalyzes the first committed step in the flavonoid biosynthetic pathway. In this study, the cDNA (FhCHS1 encoding CHS from Freesia hybrida was successfully isolated and analyzed. Multiple sequence alignments showed that both the conserved CHS active site residues and CHS signature sequence were found in the deduced amino acid sequence of FhCHS1. Meanwhile, crystallographic analysis revealed that protein structure of FhCHS1 is highly similar to that of alfalfa CHS2, and the biochemical analysis results indicated that it has an enzymatic role in naringenin biosynthesis. Moreover, quantitative real-time PCR was performed to detect the transcript levels of FhCHS1 in flowers and different tissues, and patterns of FhCHS1 expression in flowers showed significant correlation to the accumulation patterns of anthocyanin during flower development. To further characterize the functionality of FhCHS1, its ectopic expression in Arabidopsis thaliana tt4 mutants and Petunia hybrida was performed. The results showed that overexpression of FhCHS1 in tt4 mutants fully restored the pigmentation phenotype of the seed coats, cotyledons and hypocotyls, while transgenic petunia expressing FhCHS1 showed flower color alteration from white to pink. In summary, these results suggest that FhCHS1 plays an essential role in the biosynthesis of flavonoid in Freesia hybrida and may be used to modify the components of flavonoids in other plants.

  8. Emerging role of Garcinol, the antioxidant chalcone from Garcinia indica Choisy and its synthetic analogs.

    Science.gov (United States)

    Padhye, Subhash; Ahmad, Aamir; Oswal, Nikhil; Sarkar, Fazlul H

    2009-09-02

    Garcinol, harvested from Garcinia indica, has traditionally been used in tropical regions and appreciated for centuries; however its biological properties are only beginning to be elucidated. There is ample data to suggest potent antioxidant properties of this compound which have been used to explain most of its observed biological activities. However, emerging evidence suggests that garcinol could be useful as an anti-cancer agent, and it is increasingly being realized that garcinol is a pleiotropic agent capable of modulating key regulatory cell signaling pathways. Here we have summarized the progress of our current research knowledge on garcinol and its observed biological activities. We have also provided an explanation of observed properties based on its chemical structure and provided an insight into the structure and properties of chalcones, the precursors of garcinol. The available data is promising but more detailed investigations into the various properties of this compound, particularly its anti-cancer activity are urgently needed, and it is our hope that this review will stimulate further research for elucidating and appreciating the value of this nature's wonder agent.

  9. Emerging role of Garcinol, the antioxidant chalcone from Garcinia indica Choisy and its synthetic analogs

    Directory of Open Access Journals (Sweden)

    Oswal Nikhil

    2009-09-01

    Full Text Available Abstract Garcinol, harvested from Garcinia indica, has traditionally been used in tropical regions and appreciated for centuries; however its biological properties are only beginning to be elucidated. There is ample data to suggest potent antioxidant properties of this compound which have been used to explain most of its observed biological activities. However, emerging evidence suggests that garcinol could be useful as an anti-cancer agent, and it is increasingly being realized that garcinol is a pleiotropic agent capable of modulating key regulatory cell signaling pathways. Here we have summarized the progress of our current research knowledge on garcinol and its observed biological activities. We have also provided an explanation of observed properties based on its chemical structure and provided an insight into the structure and properties of chalcones, the precursors of garcinol. The available data is promising but more detailed investigations into the various properties of this compound, particularly its anti-cancer activity are urgently needed, and it is our hope that this review will stimulate further research for elucidating and appreciating the value of this nature's wonder agent.

  10. Spectral, biological screening of metal chelates of chalcone based Schiff bases of N-(3-aminopropyl) imidazole.

    Science.gov (United States)

    Kalanithi, M; Rajarajan, M; Tharmaraj, P; Sheela, C D

    2012-02-15

    Tridentate chelate complexes of Co(II), Ni(II), Cu(II) and Zn(II) have been synthesized from the chalcone based ligands 2-[1-(3-(1H-imidazol-1-yl)propylimino)-3-(phenylallyl)]phenol(HL(1)), 2-[1-(3-(1H-imidazol-1-yl)propylimino)-3-p-tolylallyl]phenol(HL(2)), 2-[1-(3-(1H-imidazol-1-yl)propylimino)-3-4-nitrophenylallyl]phenol(HL(3)). Microanalytical data, UV-vis spectrophotometric method, magnetic susceptibility measurements, IR, 1H NMR, Mass, and EPR techniques were used to characterize the structure of chelates. The electronic absorption spectra and magnetic susceptibility measurements suggest a distorted square planar geometry for the copper(II) ion. The other metal complexes show distorted tetrahedral geometry. The coordination of the ligands with metal(II) ions was further confirmed by solution fluorescence spectrum. The antimicrobial activity of the ligands and metal(II) complexes against the species Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Candida albigans and Aspergillus niger has been carried out and compared. The electrochemical behavior of copper(II) complex is studied by cyclic voltammetry.

  11. Ruthenium(II) carbonyl complexes containing chalconates and triphenylphosphine/arsine

    Indian Academy of Sciences (India)

    P Viswanathamurthi; M Muthukumar

    2011-09-01

    A series of new hexa-coordinated ruthenium(II) carbonyl complexes of the type [RuCl(CO)(EPh3)(B)(L1−4)] (4-15) (E = P or As; B = PPh3, AsPh3 or Py; L = 2'-hydroxychalcone) were synthesized from the reaction of [RuHCl(CO)(EPh3)2(B)] (1-3) (E = P or As; B = PPh3, AsPh3 or Py) with equimolar chalcone in benzene under reflux. The new complexes have been characterized by analytical and spectroscopic (IR, electronic, 1H, 31P{1H}, and 13C NMR) methods. On the basis of data obtained, an octahedral structure has been assigned for all the complexes. The complexes exhibit catalytic activity for the oxidation of primary and secondary alcohols into their corresponding aldehydes and ketones in the presence of -methylmorpholine--oxide (NMO) as co-oxidant and were also found to be efficient transfer hydrogenation catalysts. The antifungal properties of the ligands and their complexes have also been examined and compared with standard Bavistin.

  12. Transient silencing of CHALCONE SYNTHASE during fruit ripening modifies tomato epidermal cells and cuticle properties.

    Science.gov (United States)

    España, Laura; Heredia-Guerrero, José A; Reina-Pinto, José J; Fernández-Muñoz, Rafael; Heredia, Antonio; Domínguez, Eva

    2014-11-01

    Tomato (Solanum lycopersicum) fruit ripening is accompanied by an increase in CHALCONE SYNTHASE (CHS) activity and flavonoid biosynthesis. Flavonoids accumulate in the cuticle, giving its characteristic orange color that contributes to the eventual red color of the ripe fruit. Using virus-induced gene silencing in fruits, we have down-regulated the expression of SlCHS during ripening and compared the cuticles derived from silenced and nonsilenced regions. Silenced regions showed a pink color due to the lack of flavonoids incorporated to the cuticle. This change in color was accompanied by several other changes in the cuticle and epidermis. The epidermal cells displayed a decreased tangential cell width; a decrease in the amount of cuticle and its main components, cutin and polysaccharides, was also observed. Flavonoids dramatically altered the cuticle biomechanical properties by stiffening the elastic and viscoelastic phase and by reducing the ability of the cuticle to deform. There seemed to be a negative relation between SlCHS expression and wax accumulation during ripening that could be related to the decreased cuticle permeability to water observed in the regions silencing SlCHS. A reduction in the overall number of ester linkages present in the cutin matrix was also dependent on the presence of flavonoids.

  13. Cloning and expression analysis of chalcone synthase gene from Coleus forskohlii

    Indian Academy of Sciences (India)

    PRAVEEN AWASTHI; VIDUSHI MAHAJAN; VIJAY LAKSHMI JAMWAL; NITIKA KAPOOR; SHAFAQ RASOOL; YASHBIR S. BEDI; SUMIT G. GANDHI

    2016-09-01

    Flavonoids are an important class of secondary metabolites that play various roles in plants such as mediating defense, floral pigmentation and plant–microbe interaction. Flavonoids are also known to possess antioxidant and antimicrobial activities. Coleus forskohlii (Willd.) Briq. (Lamiaceae) is an important medicinal herb with a diverse metabolic profile, including production of a flavonoid, genkwanin. However, components of the flavonoid pathway have not yet been studied in this plant. Chalcone synthase (CHS) catalyses the first committed step of flavonoid biosynthetic pathway. Full-length cDNA, showing homology with plantCHS gene was isolated from leaves of C. forskohlii and named CfCHS (GenBank accession no. KF643243). Theoretical translation of CfCHS nucleotide sequence shows that it encodes a protein of 391 amino acids with a molecular weight of 42.75 kDa and pI 6.57. Expression analysis of CfCHS in different tissues and elicitor treatments showed that methyl jasmonate (MeJA) strongly induced its expression. Total flavonoids content and antioxidant activity of C.forskohlii also got enhanced in response to MeJA, which correlated with increased CfCHS expression. Induction ofCfCHS by MeJA suggest its involvement in production of flavonoids, providing protection from microbes during herbivory or mechanical wounding. Further, ourin silico predictions and experimental data suggested that CfCHS may be posttranscriptionally regulated by miR34.

  14. Structural, electrochemical and theoretical study of a new chalcone derivative containing 3-thiophene rings

    Science.gov (United States)

    Baggio, Ricardo; Brovelli, Francisco; Moreno, Yanko; Pinto, Marcela; Soto-Delgado, Jorge

    2016-11-01

    The title chalcone, 1,3-di(thiophene-3-yl)prop-2-en-1-one (C11H8OS2) is an essentially planar molecular with its terminal thiophene rings subtending an angle of 8.9°. The crystal structure consists in the π··π stacking of molecules defining columns along [010], further linked along c by non conventional Csbnd H⋯O bonds, thus determining broad planar arrays parallel to (100). In addition, there are weak S⋯S contacts connecting these weakly interacting 2D substructures. The experimental results obtained from single crystal X-ray diffraction data and the theoretical geometry calculated by molecular mechanics are in good agreement. Electrochemical records reveal an anodic profile with an unsymmetrical irreversible peak at 1.77 V and a shoulder at 1.62 V vs SCE, a behavior interpretable as due to the oxidation of reactive sites present in the molecule. On the other hand, the electrochemical reduction shows a narrow peak at -1.58 V vs SCE, a fact attributable to the carbonyl group. Finally, the values for the energy involved in the departure/arrival of electrons from border orbitals, as calculated using DFT, is compared with experimental data from cyclic voltammetry.

  15. Antiinvasive effect of xanthohumol, a prenylated chalcone present in hops (Humulus lupulus L.) and beer.

    Science.gov (United States)

    Vanhoecke, Barbara; Derycke, Lara; Van Marck, Veerle; Depypere, Herman; De Keukeleire, Denis; Bracke, Marc

    2005-12-20

    The female inflorescences of the hop plant (Humulus lupulus L.) are essential during brewing to add taste and flavor to beer and to stabilize beer foam. Xanthohumol, the main prenylated chalcone in hops, was investigated for its antiinvasive activity on human breast cancer cell lines (MCF-7 and T47-D) in vitro. Xanthohumol was able to inhibit the invasion of MCF-7/6 cells at 5 microM in the chick heart invasion assay and of T47-D cells in the collagen invasion assay. Xanthohumol inhibited growth of MCF-7/6 and T47-D cells, but not of chick heart cells. Moreover, it induced apoptosis of these tumor cells as demonstrated by the cleavage of nuclear PARP after 48 hr treatment. To probe the mechanism of the antiinvasive effect of xanthohumol, involvement of the E-cadherin/catenin invasion-suppressor complex was investigated. An aggregation assay demonstrated stimulation of aggregation of MCF-7/6 cells in the presence of 5 microM xanthohumol and this could be completely inhibited by an antibody against E-cadherin. Xanthohumol upregulates the function of the E-cadherin/catenin complex and inhibits invasion in vitro, indicating a possible role as an antiinvasive agent in vivo as well.

  16. Co-suppression in transgenic Petunia hybrida expressing chalcone synthase A (chsA)

    Institute of Scientific and Technical Information of China (English)

    LI; Yan; (

    2001-01-01

    [1]Napoli, C., Lemieux, C., Jorgensen, R., Introduction of a chimeric chalone synthase gene into petunia results in reversible cosuppession of homologous genes in trans, The Plant Cell, 1990, 2: 279-289.[2]Van der Krol, A.R., Mur, L.A., Beld, M. M. et al., Flavonnoid genes in petunia: addition of a limited number of gene copies may lead to a suppression of gene expression, The Plant Cell, 1990, 2: 291-299.[3]Manika, P.B., Bhadra, U., Birchler, J., Cosuppression in Drosophila: gene silencing of Alcohol dehydrogenase by White-Adh transgene is Polycomb dependent, Cell, 1997, 90: 479-498.[4]de Carvalho Niebel, F., Frendo, P., Van Montagu, M. et al., Post-transcriptional cosuppression of ?-1,3-glucanase transgene expression in homozygous plants, EMBO J., 1992, 11: 2595-2602.[5]Van Blokland, R., Van der Geest, N., Mol, J. N. M. et al., Transgene-mediated suppression of chalcone synthase expression in Petunia hybrida results from an increase in RNA turnover, The Plant Cell, 1994, 6: 861-877.[6]Stam, M., Mol, J. N. M., Kooter, J. M., The silence of genes in transgenic plants, Annals of Bot., 1997, 79: 3-12.[7]Vaucheret, H., Beclin, C., Elmayan, T. et al., Transgene-induced gene silencing in plants, Plant J., 1998, 16(6): 651-659.[8]Shao, L., Li, Y., Yang, M. Z. et al., Transformation of Petunia hybrida with chalcone synthase A (chsA) resulting flower colour alteration and male sterility, Acta Botanica Sinica (in Chinese), 1996, 38(7): 517-524.[9]Koes, R. E., Spelt, C. E., Mol, J. N. M., The chalcone synthase multigene family of Petunia hybrida (V30): differential, light-regulated expression during flower development and UV light induction, Plant Mol. Biol., 1989, 12: 213-225.[10]Drews, G. N., Beals, T. P., Bul, A. Q. et al., Regional and cell-specific expression patterns during petal development, The Plant Cell, 1992, 4: 1383-1404.[11]Martin, C., Gerats, T., Control of pigment biosynthesis genes during petal development, The

  17. Genome-Wide Identification, Characterization and Expression Analysis of the Chalcone Synthase Family in Maize.

    Science.gov (United States)

    Han, Yahui; Ding, Ting; Su, Bo; Jiang, Haiyang

    2016-01-27

    Members of the chalcone synthase (CHS) family participate in the synthesis of a series of secondary metabolites in plants, fungi and bacteria. The metabolites play important roles in protecting land plants against various environmental stresses during the evolutionary process. Our research was conducted on comprehensive investigation of CHS genes in maize (Zea mays L.), including their phylogenetic relationships, gene structures, chromosomal locations and expression analysis. Fourteen CHS genes (ZmCHS01-14) were identified in the genome of maize, representing one of the largest numbers of CHS family members identified in one organism to date. The gene family was classified into four major classes (classes I-IV) based on their phylogenetic relationships. Most of them contained two exons and one intron. The 14 genes were unevenly located on six chromosomes. Two segmental duplication events were identified, which might contribute to the expansion of the maize CHS gene family to some extent. In addition, quantitative real-time PCR and microarray data analyses suggested that ZmCHS genes exhibited various expression patterns, indicating functional diversification of the ZmCHS genes. Our results will contribute to future studies of the complexity of the CHS gene family in maize and provide valuable information for the systematic analysis of the functions of the CHS gene family.

  18. Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship

    Science.gov (United States)

    Akhtar, Muhammad Nadeem; Sakeh, Nurshafika M.; Zareen, Seema; Gul, Sana; Lo, Kong Mun; Ul-Haq, Zaheer; Shah, Syed Adnan Ali; Ahmad, Syahida

    2015-04-01

    Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC50 14.20-14.38 μM values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1-3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discover of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry.

  19. Synthesis, fluorescence, TGA and crystal structure of thiazolyl-pyrazolines derived from chalcones

    Science.gov (United States)

    Suwunwong, T.; Chantrapromma, S.; Fun, H.-K.

    2015-04-01

    Thiazolyl-pyrazolines 3a-3d were synthesized in a three step procedure using chalcones as starting materials and characterized by FT-IR, UV-Vis, and 1H NMR techniques. The crystal structure of compound 3a was also determined by X-ray diffraction analysis. Compound 3a crystallized out in the orthorhombic P212121 space group with the unit cell dimensions: a = 5.2106(2) Å, b = 12.4341(5) Å, c = 33.3254(13) Å, α = β = γ = 90°, V = 2159.12(15) Å3, Z = 4, D cald = 1.372 M gm-3 and F(000) = 928. Fluorescence of 3a-3d were studied in solid state and acetonitrile solution. It was found that, these compounds exhibit the green fluorescence light (506-508 nm) in both solid and solution states. The pH stability on fluorescence property and the thermal gravimetric analysis of compound 3a were specifically carried out. It was revealed that 3a shows high thermal stability up to around 250°C and presenting high stability in various pH ranges in the acetonitrilewater matrix.

  20. Spectral, biological screening of metal chelates of chalcone based Schiff bases of N-(3-aminopropyl) imidazole

    Science.gov (United States)

    Kalanithi, M.; Rajarajan, M.; Tharmaraj, P.; Sheela, C. D.

    2012-02-01

    Tridentate chelate complexes of Co(II), Ni(II), Cu(II) and Zn(II) have been synthesized from the chalcone based ligands 2-[1-(3-(1H-imidazol-1-yl)propylimino)-3-(phenylallyl)]phenol( HL1), 2-[1-(3-(1H-imidazol-1-yl)propylimino)-3-p-tolylallyl]phenol( HL2), 2-[1-(3-(1H-imidazol-1-yl)propylimino)-3-4-nitrophenylallyl]phenol( HL3). Microanalytical data, UV-vis spectrophotometric method, magnetic susceptibility measurements, IR, 1H NMR, Mass, and EPR techniques were used to characterize the structure of chelates. The electronic absorption spectra and magnetic susceptibility measurements suggest a distorted square planar geometry for the copper(II) ion. The other metal complexes show distorted tetrahedral geometry. The coordination of the ligands with metal(II) ions was further confirmed by solution fluorescence spectrum. The antimicrobial activity of the ligands and metal(II) complexes against the species Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Candida albigans and Aspergillus niger has been carried out and compared. The electrochemical behavior of copper(II) complex is studied by cyclic voltammetry.

  1. Photo-alignment of low-molecular mass nematic liquid crystals on photochemically bifunctional chalcone-epoxy film by irradiation of a linearly polarized UV light

    CERN Document Server

    Choi, D H

    2002-01-01

    Photocrosslinkable chalcone-epoxy compound comprising 1,3-bis-(4-hydroxy-phenyl)-propenone was synthesized for fabricating the photo-alignment layer of liquid crystals. Chalcone group was introduced into the main chain unit of the epoxy oligomer. We observed a photodimerization behavior and an optical anisotropy of this material by irradiation of a linearly polarized UV(LP-UV) light. With a trace amount of cationic photo initiator (TRS-HFA), polymerization of epoxy groups was also conducted at the similar wavelength range used for photodimerization . Linearly polarized UV irradiation on the chalcone-epoxy films with cationic photoinitiator induced optical anisotropy of the film and the resultant film can be used for alignment layers for low molecular weight nematic liquid crystals.

  2. Study Progress on Synthesis 3′,5′-Hydrocarbon Chalcones%3′,5′-烃基查尔酮的合成进展

    Institute of Scientific and Technical Information of China (English)

    陈泓霖; 黄初升; 刘红星; 杨进华; 郑少龙

    2015-01-01

    Isopentenyl and geranyl structure units generally exist in flavonoids ,chalcone and other natural products .Chalcone in isopentenyl and geranyl structure has anti‐cancer ,antioxidant activity which is popularly favored .There are domestic and foreign reports about many synthesis methods of prenylated and geranyl chalcone .In this paper ,two research directions from acetophenone or chalcone as raw material base are summarized ,making a summary on methods for synthesis of 3′,5′position as in isopentenyl or geranyl chalcones in recent years ,and providing more new methods for developing synthesis of 3′,5′position with reference to isopentenyl or geranyl chalcone.%异戊烯基和香叶基结构单元普遍存在于黄酮类、查尔酮类等天然产物。异戊烯基和香叶基结构的查尔酮具有抗癌、抗氧化活性等生理活性而备受青睐。国内外报道了许多异戊烯基和香叶基结构的查尔酮合成方法。本文从苯乙酮或查尔酮为原料基础的两个研究方向进行总结,综述了近年来关于3′,5′位为异戊烯基或香叶基的查尔酮的合成方法,为更多3′,5′位为异戊烯基或香叶基的查尔酮的合成新方法被研发提供参考。

  3. Synthesis and structure elucidation of a series of pyranochromene chalcones and flavanones using 1D and 2D NMR spectroscopy and X-ray crystallography.

    Science.gov (United States)

    Pawar, Sunayna S; Koorbanally, Neil A

    2014-06-01

    A series of novel pyranochromene chalcones and corresponding flavanones were synthesized. This is the first report on the confirmation of the absolute configuration of chromene-based flavanones using X-ray crystallography. These compounds were characterized by 2D NMR spectroscopy, and their assignments are reported herein. The 3D structure of the chalcone 3b and flavanone 4g was determined by X-ray crystallography, and the structure of the flavanone was confirmed to be in the S configuration at C-2.

  4. Excision of transposable elements from the chalcone isomerase and dihydroflavonol 4-reductase genes may contribute to the variegation of the yellow-flowered carnation (Dianthus caryophyllus).

    Science.gov (United States)

    Itoh, Yoshio; Higeta, Daisuke; Suzuki, Akane; Yoshida, Hiroyuki; Ozeki, Yoshihiro

    2002-05-01

    In the "Rhapsody" cultivar of the carnation, which bears white flowers variegated with red flecks and sectors, a transposable element, dTdic1, belonging to the Ac/Ds superfamily, was found within the dihydroflavonol 4-reductase (DFR) gene. The red flecks and sectors of "Rhapsody" may be attributable to a reversion to DFR activity after the excision of dTdic1. The yellow color of the carnation petals is attributed to the synthesis and accumulation of chalcone 2'-glucoside. In several of the carnation cultivars that bear yellow flowers variegated with white flecks and sectors, both the chalcone isomerase (CHI) and DFR genes are disrupted by dTdic1.

  5. Nanoemulsions containing a synthetic chalcone as an alternative for treating cutaneous leshmaniasis: optimization using a full factorial design.

    Science.gov (United States)

    de Mattos, Cristiane Bastos; Argenta, Débora Fretes; Melchiades, Gabriela de Lima; Cordeiro, Marlon Norberto Sechini; Tonini, Maiko Luis; Moraes, Milene Hoehr; Weber, Tanara Beatriz; Roman, Silvane Souza; Nunes, Ricardo José; Teixeira, Helder Ferreira; Steindel, Mário; Koester, Letícia Scherer

    2015-01-01

    Nanoemulsions are drug delivery systems that may increase the penetration of lipophilic compounds through the skin, enhancing their topical effect. Chalcones are compounds of low water solubility that have been described as promising molecules for the treatment of cutaneous leishmaniasis (CL). In this context, the aim of this work was to optimize the development of a nanoemulsion containing a synthetic chalcone for CL treatment using a 2(2) full factorial design. The formulations were prepared by spontaneous emulsification and the experimental design studied the influence of two independent variables (type of surfactant - soybean lecithin or sorbitan monooleate and type of co-surfactants - polysorbate 20 or polysorbate 80) on the physicochemical characteristics of the nanoemulsions, as well as on the skin permeation/retention of the synthetic chalcone in porcine skin. In order to evaluate the stability of the systems, the antileishmanial assay was performed against Leishmania amazonensis 24 hours and 60 days after the preparation of the nanoemulsions. The formulation composed of soybean lecithin and polysorbate 20 presented suitable physicochemical characteristics (droplet size 171.9 nm; polydispersity index 0.14; zeta potential -39.43 mV; pH 5.16; and viscosity 2.00 cP), drug content (91.09%) and the highest retention in dermis (3.03 µg·g(-1)) - the main response of interest - confirmed by confocal microscopy. This formulation also presented better stability of leishmanicidal activity in vitro against L. amazonensis amastigote forms (half maximal inhibitory concentration value 0.32±0.05 µM), which confirmed the potential of the nanoemulsion soybean lecithin and polysorbate 20 for CL treatment.

  6. Synthetic cyclohexenyl chalcone natural products possess cytotoxic activities against prostate cancer cells and inhibit cysteine cathepsins in vitro.

    Science.gov (United States)

    Deb Majumdar, Ishita; Devanabanda, Arvind; Fox, Benjamin; Schwartzman, Jacob; Cong, Huan; Porco, John A; Weber, Horst C

    2011-12-16

    A number of cyclohexenyl chalcone Diels-Alder natural products possess promising biological properties including strong cytotoxicity in various human cancer cells. Herein, we show that natural products in this class including panduratin A and nicolaioidesin C inhibit cysteine cathepsins as indicated by protease profiling assays and cell-free cathepsin L enzyme assays. Owing to the critical roles of cathepsins in the biology of human tumor progression, invasion, and metastasis, these findings should pave the way for development of novel antitumor agents for use in clinical settings.

  7. Enantioselective Conjugate Addition of Diethylzinc to Chalcone Catalyzed by Ni(acac)2 and Chiralβ-Amino Alcohols

    Institute of Scientific and Technical Information of China (English)

    EnantioselectiveConjugateAdditionofDiethylzinctoChalconeCatalyzedbyNi(acac)2andChiral/I-AminoAlcohols; 王恒山; 达朝山; 辛卓群; 粟武; 肖亦男; 刘大学; 王锐

    2003-01-01

    Enantioselectivge conjugate addition of diethyzinc to chalcone was carried out in the presenee of Ni (acac)2 complexed with five pyrrolidfumyimethanois derived from L-proline. (S)-N-Benzyl-2-(l-hydroxy.l-methylethyl) pyrrolidlne was found to be the best ngnd in asymmetric conjugate addition among the five ligands. The products were obtained with up to 70% ee.The configuration of the product was determined jointly by the substituents on the carbon of the hydroxy group and the nitrogen atom.

  8. Synthesis of 2-pyrazolines from pyridine based chalcone by conventional and microwave techniques: Their comparison and antimicrobial studies

    Directory of Open Access Journals (Sweden)

    Navin B. Patel

    2016-09-01

    Full Text Available 2-Pyrazolines from pyridine based chalcones by conventional and microwave techniques have been synthesized and their antimicrobial activity as well as a comparison study between conventional and microwave techniques has been done. Antimicrobial activity was carried out according to the broth micro dilution method and it was observed that compound 2d was found to be most active against gram negative bacteria and fungus Candida albicans. Microwave technique has been found superior over the conventional method in view of reaction time and energy requirement. Compounds have been characterized by 1H NMR, 13C NMR, IR and Mass spectral analyses.

  9. Nanoemulsions containing a synthetic chalcone as an alternative for treating cutaneous leshmaniasis: optimization using a full factorial design

    Directory of Open Access Journals (Sweden)

    Mattos CB

    2015-09-01

    Full Text Available Cristiane Bastos de Mattos,1 Débora Fretes Argenta,1 Gabriela de Lima Melchiades,1 Marlon Norberto Sechini Cordeiro,2 Maiko Luis Tonini,3 Milene Hoehr Moraes,3 Tanara Beatriz Weber,4 Silvane Souza Roman,4 Ricardo José Nunes,2 Helder Ferreira Teixeira,1 Mário Steindel,3 Letícia Scherer Koester1 1Faculdade de Farmácia, Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Rio Grande do Sul, Porto Alegre, Rio Grande do Sul, Brazil; 2Departamento de Química, 3Departamento de Microbiologia, Imunologia e Parasitologia, Universidade Federal de Santa Catarina, Florianópolis, Santa Catarina, Brazil; 4Departamento de Ciências Biológicas, Universidade Regional Integrada do Alto Uruguai e das Missões, Erechim, Rio Grande do Sul, Brazil Abstract: Nanoemulsions are drug delivery systems that may increase the penetration of lipophilic compounds through the skin, enhancing their topical effect. Chalcones are compounds of low water solubility that have been described as promising molecules for the treatment of cutaneous leishmaniasis (CL. In this context, the aim of this work was to optimize the development of a nanoemulsion containing a synthetic chalcone for CL treatment using a 22 full factorial design. The formulations were prepared by spontaneous emulsification and the experimental design studied the influence of two independent variables (type of surfactant – soybean lecithin or sorbitan monooleate and type of co-surfactants – polysorbate 20 or polysorbate 80 on the physicochemical characteristics of the nanoemulsions, as well as on the skin permeation/retention of the synthetic chalcone in porcine skin. In order to evaluate the stability of the systems, the antileishmanial assay was performed against Leishmania amazonensis 24 hours and 60 days after the preparation of the nanoemulsions. The formulation composed of soybean lecithin and polysorbate 20 presented suitable physicochemical characteristics (droplet size

  10. A Malus crabapple chalcone synthase gene, McCHS, regulates red petal color and flavonoid biosynthesis.

    Directory of Open Access Journals (Sweden)

    Deqiang Tai

    Full Text Available Chalcone synthase is a key and often rate-limiting enzyme in the biosynthesis of anthocyanin pigments that accumulate in plant organs such as flowers and fruits, but the relationship between CHS expression and the petal coloration level in different cultivars is still unclear. In this study, three typical crabapple cultivars were chosen based on different petal colors and coloration patterns. The two extreme color cultivars, 'Royalty' and 'Flame', have dark red and white petals respectively, while the intermediate cultivar 'Radiant' has pink petals. We detected the flavoniods accumulation and the expression levels of McCHS during petals expansion process in different cultivars. The results showed McCHS have their special expression patterns in each tested cultivars, and is responsible for the red coloration and color variation in crabapple petals, especially for color fade process in 'Radiant'. Furthermore, tobacco plants constitutively expressing McCHS displayed a higher anthocyanins accumulation and a deeper red petal color compared with control untransformed lines. Moreover, the expression levels of several anthocyanin biosynthetic genes were higher in the transgenic McCHS overexpressing tobacco lines than in the control plants. A close relationship was observed between the expression of McCHS and the transcription factors McMYB4 and McMYB5 during petals development in different crabapple cultivars, suggesting that the expression of McCHS was regulated by these transcription factors. We conclude that the endogenous McCHS gene is a critical factor in the regulation of anthocyanin biosynthesis during petal coloration in Malus crabapple.

  11. Potent inhibition of human neutrophil activations by bractelactone, a novel chalcone from Fissistigma bracteolatum

    Energy Technology Data Exchange (ETDEWEB)

    Wu, Yang-Chang [Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan (China); Graduate Institute of Integrated Medicine, College of Chinese Medicine, China Medical University, Taichung 404, Taiwan (China); Sureshbabu, Munisamy; Fang, Yao-Ching; Wu, Yi-Hsiu [Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan (China); Lan, Yu-Hsuan [School of Pharmacy, China Medical University, Taichung 404, Taiwan (China); Chang, Fang-Rong [Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan (China); Chang, Ya-Wen [Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan (China); Hwang, Tsong-Long, E-mail: htl@mail.cgu.edu.tw [Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, Taiwan (China); Chinese Herbal Medicine Research Team, Healthy Aging Research Center, Chang Gung University, Kweishan, Taoyuan 333, Taiwan (China)

    2013-02-01

    Fissistigma bracteolatum is widely used in traditional medicine to treat inflammatory diseases. However, its active components and mechanisms of action remain unclear. In this study, (3Z)-6,7-dihydroxy-4-methoxy-3-(phenylmethylidene)-5-(3-phenylpropanoyl) -1-benzofuran-2(3H) (bractelactone), a novel chalcone from F. bracteolatum, showed potent inhibitory effects against superoxide anion (O{sub 2}{sup ·−}) production, elastase release, and CD11b expression in formyl-L-methionyl-L-leucyl-L-phenylalanine (FMLP)-induced human neutrophils. However, bractelactone showed only weak inhibition of phorbol myristate acetate-caused O{sub 2}{sup ·−} production. The peak cytosolic calcium concentration ([Ca{sup 2+}]{sub i}) was unaltered by bractelactone in FMLP-induced neutrophils, but the decay time of [Ca{sup 2+}]{sub i} was significantly shortened. In a calcium-free solution, changes in [Ca{sup 2+}]{sub i} caused by the addition of extracellular Ca{sup 2+} were inhibited by bractelactone in FMLP-activated cells. In addition, bractelactone did not alter the phosphorylation of p38 MAPK, ERK, JNK, or AKT or the concentration of cAMP. These results suggest that bractelactone selectively inhibits store-operated calcium entry (SOCE). In agreement with this concept, bractelactone suppressed sustained [Ca{sup 2+}]{sub i} changes in thapsigargin-activated neutrophils. Furthermore, bractelactone did not alter FMLP-induced formation of inositol 1,4,5-triphosphate. Taken together, our results demonstrate that the anti-inflammatory effects of bractelactone, an active ingredient of F. bracteolatum, in human neutrophils are through the selective inhibition of SOCE. Highlights: ► Bractelactone isolated from Fissistigma bracteolatum. ► Bractelactone inhibited FMLP-induced human neutrophil activations. ► Bractelactone had no effect on IP3 formation. ► Bractelactone did not alter MAPKs, AKT, and cAMP pathways. ► Bractelactone inhibited store-operated calcium entry.

  12. Synthesis of phenstatin/isocombretastatin-chalcone conjugates as potent tubulin polymerization inhibitors and mitochondrial apoptotic inducers.

    Science.gov (United States)

    Kamal, Ahmed; Kumar, G Bharath; Vishnuvardhan, M V P S; Shaik, Anver Basha; Reddy, Vangala Santhosh; Mahesh, Rasala; Sayeeda, Ibrahim Bin; Kapure, Jeevak Sopanrao

    2015-04-07

    A series of phenstatin/isocombretastatin–chalcones were synthesized and screened for their cytotoxic activity against various human cancer cell lines. Some representative compounds exhibited significant antiproliferative activity against a panel of sixty human cancer cell lines of the NCI, with GI50 values in the range of 0.11 to 19.0 μM. Three compounds (3b, 3c and 3e) showed a broad spectrum of antiproliferative efficacy on most of the cell lines in the sub-micromolar range. In addition, all the synthesized compounds (3a–l and 4a–l) displayed moderate to excellent cytotoxicity against breast cancer cells such as MCF-7 and MDA-MB-231 with IC50 values in the range of 0.5 to 19.9 μM. Moreover, the tubulin polymerization assay and immunofluorescence analysis results suggest that some of these compounds like 3c and 3e exhibited significant inhibitory effect on the tubulin assembly with an IC50 value of 0.8 μM and 0.6 μM respectively. A competitive binding assay suggested that these compounds bind at the colchicine-binding site of tubulin. A cell cycle assay revealed that these compounds arrest at the G2/M phase and lead to apoptotic cell death. Furthermore, this was confirmed by Hoechst 33258 staining, activation of caspase 9, DNA fragmentation, Annexin V-FITC and mitochondrial membrane depolarization. Molecular docking studies indicated that compounds like 3e occupy the colchicine binding site of tubulin.

  13. Synthesis of some pyrazolines and pyrimidines derived from polymethoxy chalcones as anticancer and antimicrobial agents.

    Science.gov (United States)

    Rostom, Sherif A F; Badr, Mona H; Abd El Razik, Heba A; Ashour, Hayam M A; Abdel Wahab, Abeer E

    2011-09-01

    The synthesis of a series of certain polymethoxy chalcones and some derived pyrazole, pyrimidine, and thiazolopyrimidine ring structures is reported. Eleven compounds 4, 6, 9, 11, 14-17, 22, 24, and 25 were selected by the National Cancer Institute (NCI) to be screened for their in-vitro anticancer activity, whereas all the synthesized compounds were evaluated for their in-vitro antimicrobial activity. Compounds 4, 6, and 11 were found to possess a significant broad spectrum antitumor potential against most of the tested subpanel tumor cell lines. The pyrazolines 4 and 6 displayed remarkable growth inhibitory activities (GI(50) MG-MID values of 2.10 and 1.38 µM, respectively), together with moderate cytostatic effects (TGI MG-MID values of 47.9 and 42.7 µM, respectively). Meanwhile, the pyrimidin-2-one 11 showed a noticeable overall tumor growth inhibitory activity, together with high cytostatic and cytotoxic efficacies (GI(50) , TGI and LC(50) MG-MID values of 3.39, 17.4, and 61.7 µM, respectively). On the other hand, compounds 3, 4, 13, 15, 19, 20, and 23 were found to be the most active antimicrobial members in this investigation with a broad spectrum of activity. Compound 23 was four times superior to ampicillin against Pseudomonas aeruginosa. The best antifungal activity was demonstrated by compounds 4, 5, and 11 which possessed almost half the activity of clotrimazole against Candida albicans. Collectively, the obtained biological results suggest that compound 4 could be considered as a possible dual antimicrobial-anticancer agent.

  14. The chalcone compound isosalipurposide (ISPP) exerts a cytoprotective effect against oxidative injury via Nrf2 activation

    Energy Technology Data Exchange (ETDEWEB)

    Han, Jae Yun [College of Pharmacy, Chosun University, Gwangju 501-759 (Korea, Republic of); Cho, Seung Sik [College of Pharmacy, Mokpo National University, Muan, Jeonnam 535-729 (Korea, Republic of); Yang, Ji Hye; Kim, Kyu Min; Jang, Chang Ho [College of Pharmacy, Chosun University, Gwangju 501-759 (Korea, Republic of); Park, Da Eon [College of Pharmacy, Mokpo National University, Muan, Jeonnam 535-729 (Korea, Republic of); Bang, Joon Seok [Graduate School of Clinical Pharmacy, Sookmyung Women' s University, Seoul (Korea, Republic of); Jung, Young Suk [College of Pharmacy, Pusan National University, Busan (Korea, Republic of); Ki, Sung Hwan, E-mail: shki@chosun.ac.kr [College of Pharmacy, Chosun University, Gwangju 501-759 (Korea, Republic of)

    2015-08-15

    The chalcone compound isosalipurposide (ISPP) has been successfully isolated from the native Korean plant species Corylopsis coreana Uyeki (Korean winter hazel). However, the therapeutic efficacy of ISPP remains poorly understood. This study investigated whether ISPP has the capacity to activate NF-E2-related factor (Nrf2)-antioxidant response element (ARE) signaling and induce its target gene expression, and to determined the protective role of ISPP against oxidative injury of hepatocytes. In HepG2 cells, nuclear translocation of Nrf2 is augmented by ISPP treatment. Consistently, ISPP increased ARE reporter gene activity and the protein levels of glutamate cysteine ligase (GCL) and hemeoxygenase (HO-1), resulting in increased intracellular glutathione levels. Cells pretreated with ISPP were rescued from tert-butylhydroperoxide-induced reactive oxygen species (ROS) production and glutathione depletion and consequently, apoptotic cell death. Moreover, ISPP ameliorated the mitochondrial dysfunction and apoptosis induced by rotenone which is an inhibitor of complex 1 of the mitochondrial respiratory chain. The specific role of Nrf2 activation by ISPP was demonstrated using an ARE-deletion mutant plasmid and Nrf2-knockout cells. Finally, we observed that extracellular signal-regulated kinase (ERK) and AMP-activated protein kinase (AMPK), but not protein kinase C (PKC)-δ or other mitogen-activated protein kinases (MAPKs), are involved in the activation of Nrf2 by ISPP. Taken together, our results demonstrate that ISPP has a cytoprotective effect against oxidative damage mediated through Nrf2 activation and induction of its target gene expression in hepatocytes. - Highlights: • We investigated the effect of ISPP on Nrf2 activation. • ISPP increased Nrf2 activity and its target gene expression. • ISPP inhibited the mitochondrial dysfunction and ROS production. • Nrf2 activation by ISPP is dependent on ERK1/2 and AMPK phosphorylation. • ISPP may be a promising

  15. Synthesis and photophysical properties of novel chloroquinoline based chalcone derivates containing 1,2,3-triazole moiety

    Energy Technology Data Exchange (ETDEWEB)

    Singh, Harjinder; Sindhu, Jayant; Khurana, Jitender M., E-mail: jmkhurana@chemistry.du.ac.in

    2015-02-15

    A series of novel chloroquinoline based chalcones containing 1,2,3-triazole moiety were synthesized. All new compounds were characterized by {sup 1}H NMR, {sup 13}C NMR, mass spectra and single crystal X-ray diffraction study. The absorbance, fluorescence spectra and quantum yield of all compounds were investigated in methanol. Photophysical properties of 1-(1-(7-chloroquinolin-4-yl)-5-methyl-1H-1,2,3-triazol-4-yl) -3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (3a) were investigated in detail. The effect of various solvents over emission spectra of 3a was studied using Kamlet–Taft and Catalan polarity scales. The quantum yield of 3a in various solvents was also recorded. The ground state and excited state dipole moments of compound 3a were determined using solvatochromic methods. The ground state dipole moment was estimated to be 1.081 D, while excited state dipole moment was found in the range of 11.969–3.801 D. Thermal stability of compound 3a and its precursor was also investigated using thermogravimetric analysis. - Highlights: • Novel quinoline based chalcones-1,2,3-triazole derivatives were synthesized. • The photophysical properties of all compounds were investigated in methanol. • The excited state and ground state dipole moment is estimated from various methods. • Kamlet–Taft and Catalan solvatochromism was investigated.

  16. Synthesis, biological evaluation and 3D-QSAR studies of new chalcone derivatives as inhibitors of human P-glycoprotein.

    Science.gov (United States)

    Parveen, Zahida; Brunhofer, Gerda; Jabeen, Ishrat; Erker, Thomas; Chiba, Peter; Ecker, Gerhard F

    2014-04-01

    P-glycoprotein (P-gp) is an ATP-dependent multidrug resistance efflux transporter that plays an important role in anticancer drug resistance and in pharmacokinetics of medicines. Despite a large number of structurally and functionally diverse compounds, also flavonoids and chalcones have been reported as inhibitors of P-gp. The latter share some similarity with the well studied class of propafenones, but do not contain a basic nitrogen atom. Furthermore, due to their rigidity, they are suitable candidates for 3D-QSAR studies. In this study, a set of 22 new chalcone derivatives were synthesized and evaluated in a daunomycin efflux inhibition assay using the CCRF.CEM.VCR1000 cell line. The compound 10 showed the highest activity (IC50=42nM), which is one order of magnitude higher than the activity for an equilipohillic propafenone analogue. 2D- and 3D-QSAR studies indicate the importance of H-bond acceptors, methoxy groups, hydrophobic groups as well as the number of rotatable bonds as pharmacophoric features influencing P-gp inhibitory activity.

  17. Differential modification of flavonoid and isoflavonoid biosynthesis with an antisense chalcone synthase construct in transgenic Lotus corniculatus.

    Science.gov (United States)

    Colliver, S P; Morris, P; Robbins, M P

    1997-11-01

    Three clonal genotypes of Lotus corniculatus L. (bird's foot trefoil) were transformed with an antisense chalcone synthase (CHS) gene construct made using a stress induced CHS17 cDNA from Phaseolus vulgaris under the control of the constitutive CaMV 35S promoter and Nos terminator via Agrobacterium rhizogenes. After initial screening, ten antisense and five control co-transformation events from each recipient clonal genotype were analysed. After elicitation with glutathione, the level of tannin accumulation was found to be increased in a number of antisense root cultures derived from the low (S33) and moderate (S50) tannin recipient genotypes. Six antisense and four control transformed lines from genotype S50 were selected for more detailed study. The antisense CHS construct was found to be integrated into the genome, with a copy number ranging from 1 to 5 and antisense orientation was confirmed by PCR. In transformed root cultures, increased CHS transcript levels were noted in a number of antisense lines. Biochemical analyses of glutathione-elicited-root cultures indicated a significant increase in tannin accumulation in antisense CHS lines and mean vestitol levels were reduced. These results show that the introduction of a heterologous antisense chalcone synthase construct into L. corniculatus resulted in an unpredicted molecular and biochemical phenotype. Such findings are discussed in relation to manipulation of this complex multigene family.

  18. Binding of the hop (Humulus lupulus L.) chalcone xanthohumol to cytosolic proteins in Caco-2 intestinal epithelial cells.

    Science.gov (United States)

    Pang, Yan; Nikolic, Dejan; Zhu, Dongwei; Chadwick, Lucas R; Pauli, Guido F; Farnsworth, Norman R; van Breemen, Richard B

    2007-07-01

    Used in the brewing of beer, hops (Humulus lupulus L.) contain the prenylated chalcone xanthohumol, which is under investigation as a cancer chemoprevention agent and as a precursor for the estrogenic flavanones isoxanthohumol and 8-prenylnaringenin. The uptake, transport and accumulation of xanthohumol were studied using the human intestinal epithelial cell line Caco-2 to help understand the poor bioavailability of this chalcone. Studies were carried out using Caco-2 cell monolayers 18-21 days after seeding. The apparent K(m) and V(max) values of xanthohumol accumulation in Caco-2 cells were determined, and the protein binding of xanthohumol in sub-cellular fractions of Caco-2 cells was investigated. Approximately 70% of xanthohumol added to the apical side of Caco-2 cells accumulated inside the cells, while 93% of the intracellular xanthohumol was localized in the cytosol. Xanthohumol accumulation was temperature dependent and saturable with an apparent K(m )value of 26.5 +/- 4.66 muM and an apparent V(max) of 0.215 +/- 0.018 nmol/mg protein/min. Facilitated transport was not responsible for the uptake of xanthohumol, instead, accumulation inside the Caco-2 cells was apparently the result of specific binding to cytosolic proteins. These data suggest that specific binding of xanthohumol to cytosolic proteins in intestinal epithelial cells contributes to the poor oral bioavailability observed previously in vivo.

  19. Synthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents.

    Science.gov (United States)

    Pingaew, Ratchanok; Saekee, Amporn; Mandi, Prasit; Nantasenamat, Chanin; Prachayasittikul, Supaluk; Ruchirawat, Somsak; Prachayasittikul, Virapong

    2014-10-06

    A new series of chalcone-coumarin derivatives (9-19) linked by the 1,2,3-triazole ring were synthesized through the azide/alkyne dipolar cycloaddition. Hybrid molecules were evaluated for their cytotoxic activity against four cancer cell lines (e.g., HuCCA-1, HepG2, A549 and MOLT-3) and antimalarial activity toward Plasmodium falciparum. Most of the synthesized hybrids, except for analogs 10 and 16, displayed cytotoxicity against MOLT-3 cell line without affecting normal cells. Analogs (10, 11, 16 and 18) exhibited higher inhibitory efficacy than the control drug, etoposide, in HepG2 cells. Significantly, the high cytotoxic potency of the hybrid 11 was shown to be non-toxic to normal cells. Interestingly, the chalcone-coumarin 18 was the most potent antimalarial compound affording IC50 value of 1.60 μM. Molecular docking suggested that the cytotoxicity of reported hybrids could be possibly due to their dual inhibition of α- and β-tubulins at GTP and colchicine binding sites, respectively. Furthermore, falcipain-2 was identified to be a plausible target site of the hybrids given their antimalarial potency.

  20. Application of chalcones in heterocycles synthesis: Synthesis of 2-(isoxazolo, pyrazolo and pyrimido) substituted analogues of 1,4-benzodiazepin-5-carboxamides linked through an oxyphenyl bridge

    Indian Academy of Sciences (India)

    N Kaur; D Kishore

    2013-05-01

    Versatility of chalcone derivative of 2-(4'-acetyl)-phenoxyl-5-carboxamido-1,4-benzodiazepin-5-(4'-methylpiperazinyl)-carboxamide (6) was explored to provide an easy one-pot access to its 2-(isoxazolo, pyrazolo and pyrimido) substituted analogues 9, 10, 11, 12, 13, 14, 15, and 16.

  1. Green Synthesis, Spectrofluorometric Characterization and Antibacterial Activity of Heterocyclic Compound from Chalcone on the Basis of in Vitro and Quantum Chemistry Calculation.

    Science.gov (United States)

    Khan, Salman A

    2017-02-08

    2-amino-4-(4-bromophenyl)-8-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (ABDC) was synthesized by the reaction of (2E)-2-(4 bromobenzylidene) - 6 -methoxy-3,4-dihydronaphthalen-1(2H)-one (Chalcone) with malononitrile and ammonium acetate under microwave irradiation. Chalcone was synthesised by the reaction 4-bromobenzaldehyd, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one under the same condition. Structure of ABDC was conformed by (1)H and (13)C NMR, FT-IR, EI-MS spectral studies and elemental analysis. The electronic absorption and fluorescence spectra of ABDC have been studied in solvents of different polarities, and the data were used to study the solvatochromic properties such as excitation coefficient, stokes shift, oscillator strength, transition dipole moment and fluorescence quantum yield. The absorption maximum and fluorescence emission maximum was observed red shift when increase solvent polarity n-Hexane to DMSO. ABDC undergoes solubilization in different micelles and may be used as a probe and quencher to determine the critical micelle concentration (CMC) of CTAB and SDS. The anti-bacterial activity of chalcone and its cyclized product ABDC was tested in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria was determined with the reference of standard drug Tetracycline. Results showed that the ABDC is better anti-bacterial agent as compared to chalcone. The anti-bacterial activity was further supported by the quantum chemistry calculation.

  2. Direct Asymmetric Michael Additions of Ketones to Nitroolefins and Chalcones Catalyzed by a Chiral C2-Symmetric Pyrrolidine-based Tetraamine

    Institute of Scientific and Technical Information of China (English)

    马世俊; 吴璐璐; 刘明; 王永梅

    2012-01-01

    C2-Symmetric pyrrolidine-based tetraamine, available from commercially starting materials, showed good cata- lytic activity for asymmetric Michael additions of ketones to nitroalkenes especially to chalcones. The reactions proceeded to give the corresponding products in good yields and in a highly selective manner.

  3. "N"-Heterocyclic Carbene-Catalyzed Reaction of Chalcone and Cinnamaldehyde to Give 1,3,4-Triphenylcyclopentene Using Organocatalysis to Form a Homoenolate Equivalent

    Science.gov (United States)

    Snider, Barry B.

    2015-01-01

    In this experiment, students carry out a modern organocatalytic reaction using IMes·HCl and NaOH to catalyze the formation of 1,3,4-triphenylcyclopentene from cinnamaldehyde and chalcone in water. Deprotonation of IMes·HCl with NaOH forms the "N"-heterocyclic carbene IMes that reacts with cinnamaldehyde to form a homoenolate equivalent…

  4. One-pot synthesis of new series 3,4,5-trisubstituted-dihydroisoxazoline derivatives via 1,3-dipolar cycloaddition of nitrile oxides with chalcones

    Indian Academy of Sciences (India)

    Raad Kasim Yhya; K M Lokanatha Rai; Ebraheem Abdu Musad

    2013-07-01

    We have synthesized a series of novel isoxazolines via 1,3-dipolar cycloaddition reaction. Aromatic aldoximes undergo oxidative-dehydrogenation with chloramine-T to give nitrile oxides, which were reacted with chalcones to afford of 3,4,5-trisubstituted 4,5-dihydroisoxazolines in a good yield.

  5. Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect.

    Science.gov (United States)

    Vogel, Susanne; Barbic, Matej; Jürgenliemk, Guido; Heilmann, Jörg

    2010-06-01

    Besides 2',4'-dihydroxy-4,6'-dimethoxy-3'-prenylchalcone (1) and 4-acetoxy-2',4'-dihydroxy-6'-methoxy-3'-prenylchalkon (2), both phase II metabolites of xanthohumol in rats, also a principally new chalcone 3'-coumaroyl-2',4,4'-trihydroxy-6'-methoxychalcone (3), structurally derived from helichrysetin (4) by introducing a second coumaroyl substructure at C-3' was synthesized. Furthermore new chalcones were synthesized by combination of the B-Ring fragments of helichrysetin, xanthohumol, xanthohumol C and xanthohumol H with ferulic or caffeic acid moieties in Ring A. Compound 3 showed the highest cytotoxic activity against HeLa cells with an IC50 value of 7.3+/-0.4 microM. Anti-oxidative effects were determined in the ORAC assay and revealed very strong activity for 3 and 3-methoxyhelichrysetin (6) exhibiting 7.7+/-0.3 and 6.0+/-1.3 Trolox equivalents, respectively. The anti-inflammatory activity of all compounds was measured in an in vitro ICAM-1 assay with human microvascular endothelial cells (HMEC-1) and compared with the activity of other structurally related chalcones. The results showed increasing anti-inflammatory activity for the new synthetic chalcones exhibiting a caffeoyl substructure with 3-hydroxyhelichrysetin (5) and 3-hydroxyxanthohumol H (14) being the most active. At 10 microM the TNFalpha induced expression of ICAM-1 was significantly reduced to 65.8 and 69.6% of control, respectively.

  6. 新型查尔酮衍生物的合成及酪氨酸酶活性%Synthesis and Activity on Tyrosinase of Novel Chalcone Derivatives

    Institute of Scientific and Technical Information of China (English)

    牛超; 李根; 买迪娜; 阿吉艾克拜尔·艾萨

    2014-01-01

    合成了8个新型含苯并噻唑环的查尔酮衍生物及8个酰胺查尔酮,并对化合物的结构进行了表征.生物活性测试结果表明,化合物4d,4h,5d,7b 和7d 表现出一定的酪氨酸酶激动活性,其中化合物7d 对酪氨酸酶的活性最好,其 EC50=9.6μmol/ L,优于阳性对照药8-MOP(EC50=14.8μmol/ L).%Ver-nohia anthelmintica L was endemic plant in Xinjiang, which was often used in the treatment of Vitiligo. It was believed that the chalcone compounds of Ver-nohia anthelmintica L played an important role in this treatment. Since it may activate tyrosinase and improve the melanin production, many chalcone com-pounds and derivatives were described as potential inhibitor on tyrosinase which may act as skin lightening and whitening agents. However, chalcones which showed activator effect were seldom reported. In order to search for chalcones with high activities on tyrosinase, eight novel chalcone derivatives containing benzothiazole and eight amide-derived chalcones were synthesized in this work. All the compounds were identified by 1 H NMR, 13 C NMR, IR, HRMS and evaluated their activator effect on tyrosinase by measuring the oxidation rate of L-dopa. Compared with the reference drug 8-methoxypsoralen, compounds 4d, 4h, 5d, 7b and 7d showed some activator effect on tyrosinase. Amomg them, compound 7d demonstrated more potent activity with EC50 =9. 6 μmol/ L than 8-methoxypsoralen, which EC50 value was 14. 8 μmol/ L. Further structural modification of this novel chalcones containing benzothiazole will be required for improving the solubility of them.

  7. On Michael Addition Reactions of Chalcones%查尔酮类化合物的 Michael加成反应

    Institute of Scientific and Technical Information of China (English)

    张鹏会; 李艳春; 蒲雯

    2016-01-01

    A series of chalcones are synthesized from aromatic aldehyde and acetophenone ,with H2 O as the solvent and sodium hydroxide as the catalyst .A series of Michael addition products are obtained from these chalcones and ethyl acetoacetate , catalyzed by sodium hydroxide and anhydrous sodium carbonate under the assistance of ultrasonic irradiation .And the inflences of the addition reaction condition on the yield are studied .The premium condition are determined by followings:the molar ratio of chalcone and ethyl acetoacetate is 1/1.5,sodium hydroxide/anhydrous sodium carbonate is 1/1.5 under PEG -400/H2O in 40oC,the desired product is obtained,and the yield can be up to 91.2%.The method of this syn-thesis has advantages such as simple to operate ,short reaction time and high yield .%以芳香醛与苯乙酮为原料, NaOH 为催化剂,在水相中合成了一系列查尔酮化合物。在超声辅助下,研究了混合碱( NaOH-Na2 CO3)催化查尔酮与三乙(乙酰乙酸乙酯)的 Michael加成反应,合成了一系列Michael加成产物,并对影响反应的因素进行了探究,得出最佳反应条件为:40oC 下,在 PEG -400/H2O 介质中,n查尔酮/n三乙=1/1.5,nNaOH/nNa2CO3=1/1.5,得到目标产物的产率最好,高达91.2%。此方法操作简单,反应时间短,产率高。

  8. New chalcone and pterocarpoid derivatives from the roots of Flemingia philippinensis with antiproliferative activity and apoptosis-inducing property.

    Science.gov (United States)

    Kang, Wen-Jia; Li, Da-Hong; Han, Tong; Sun, Lin; Fu, Yan-Bin; Sai, Chun-Mei; Li, Zhan-Lin; Hua, Hui-Ming

    2016-07-01

    Investigation of the roots of Flemingia philippinensis resulted in the isolation of two new chalcones, flemiphilippinones B (1) and C (2), and one new pterocarpoid, demethylwedelolactone-11-methyl ether (3), together with 12 known compounds (4-15). The antiproliferative activity against PC-3 cells was evaluated and most compounds showed cytotoxicity, among which, compound 2 exhibited GI50 value of 14.12μM. The antiproliferative activity of 2 against Bel-7402 and CaEs-17 cells was also measured, with GI50 values of 1.91 and 2.58μM, respectively. Intensive mechanism study showed that 2 caused cell-cycle arrest at S/G2 phase and induced apoptosis in Bel-7402 cells through mitochondria-related pathway.

  9. Design, synthesis and anticancer activity of matrine-1H-1,2,3-triazole-chalcone conjugates.

    Science.gov (United States)

    Zhao, Lihui; Mao, Lina; Hong, Ge; Yang, Xiaojiao; Liu, Tianjun

    2015-06-15

    A series of novel matrine-1H-1,2,3-triazole-chalcone conjugates was synthesized and their anticancer activity against A549, Bel-7402, Hela, and MCF-7 cancer cells was evaluated. Most of the conjugates displayed higher potency than their components. Compounds 6h and 6i exhibited more potent anticancer activity than 5-fluorouracil against the four tested human cancer cell lines and lower cytotoxicity to NIH3T3 normal cells. Flow cytometry tests demonstrated that compound 6h could induce apoptosis of A549 cells in a concentration-dependent manner. Moreover, 6h could efficiently suppress human tumor growth in mouse xenograft model without causing obvious toxicities.

  10. Benzophenone Synthase and Chalcone Synthase Accumulate in the Mesophyll of Hypericum perforatum Leaves at Different Developmental Stages

    Science.gov (United States)

    Belkheir, Asma K.; Gaid, Mariam; Liu, Benye; Hänsch, Robert; Beerhues, Ludger

    2016-01-01

    The active medicinal constituents in Hypericum perforatum, used to treat depression and skin irritation, include flavonoids and xanthones. The carbon skeletons of these compounds are formed by chalcone synthase (CHS) and benzophenone synthase (BPS), respectively. Polyclonal antisera were raised against the polyketide synthases from Hypericum androsaemum and their IgG fractions were isolated. Immunoblotting and immunotitration were used to test the IgGs for crossreactivity and monospecificity in H. perforatum leaf protein extract. Immunofluorescence localization revealed that both CHS and BPS are located in the mesophyll. The maximum fluorescence levels were observed in approx. 0.5 and 1 cm long leaves, respectively. The fluorescence intensity observed for CHS significantly exceeded that for BPS. Using histochemical staining, flavonoids were detected in the mesophyll, indicating that the sites of biosynthesis and accumulation coincide. Our results help understand the biosynthesis and underlying regulation of active H. perforatum constituents. PMID:27446151

  11. Benzophenone Synthase and Chalcone Synthase Accumulate in the Mesophyll of Hypericum perforatum Leaves at Different Developmental Stages.

    Science.gov (United States)

    Belkheir, Asma K; Gaid, Mariam; Liu, Benye; Hänsch, Robert; Beerhues, Ludger

    2016-01-01

    The active medicinal constituents in Hypericum perforatum, used to treat depression and skin irritation, include flavonoids and xanthones. The carbon skeletons of these compounds are formed by chalcone synthase (CHS) and benzophenone synthase (BPS), respectively. Polyclonal antisera were raised against the polyketide synthases from Hypericum androsaemum and their IgG fractions were isolated. Immunoblotting and immunotitration were used to test the IgGs for crossreactivity and monospecificity in H. perforatum leaf protein extract. Immunofluorescence localization revealed that both CHS and BPS are located in the mesophyll. The maximum fluorescence levels were observed in approx. 0.5 and 1 cm long leaves, respectively. The fluorescence intensity observed for CHS significantly exceeded that for BPS. Using histochemical staining, flavonoids were detected in the mesophyll, indicating that the sites of biosynthesis and accumulation coincide. Our results help understand the biosynthesis and underlying regulation of active H. perforatum constituents.

  12. Targeting breast cancer using retinoic acid trifloromethyl chalcone: A promising therapeutic strategy in the treatment of breast cancer

    Directory of Open Access Journals (Sweden)

    Hao Ding

    2015-03-01

    Full Text Available The study was devised to investigate the effect of retinoic acid trifloromethyl chalcone (RAFC on mammary carcinogenesis in female rats. The data revealed a significant decrease in number of rats with mammary tumor, number of tumors per rat and tumor volume by 54, 72 and 75% respectively in RAFC group compared to control group. The ibuprofen treated rats also showed a significant decrease in number of rats with tumor, number of tumors per rat and tumor volumes by 43%, 55%, and 59%, respectively. Treatment of rats with RAFC also increased the latency period of tumor induction significantly. Median detection period (50% of tumors was 92, 83 and 56 days respectively in the rats from RAFC, ibuprofen and control groups respectively after DMBA induction. These results demonstrate that RAFC possesses strong chemopreventive activity against mammary carcinogenesis.

  13. Synthesis and biological evaluation of benzo[d][1,3]dioxol-5-yl chalcones as antiproliferating agents.

    Science.gov (United States)

    Kamal, Ahmed; Balakrishna, Moku; Loka Reddy, Velatooru; Riyaz, Syed; Bagul, Chandrakant; Satyanarayana, Bethu Murali; Venkateswar Rao, Janapala

    2015-11-01

    A series of chalcone derivatives were designed, synthesized, and evaluated for their cytotoxic potential. These molecules have showed promising cytotoxic activity with IC50 values ranging from 5.24 to 63.12 μm. Among them, conjugates 16k, 16m and 16t showed significant antiproliferative activity with IC50 values ranging from 5.24 to 10.39 μm in MDA-MB-231 cell line. These compounds were further investigated for their effect on cell membrane blebbing, chromatin condensation, DNA fragmentation, Hoechst staining, annexin V, and cell cycle arrest (G2/M). The Western blot experiments revealed up regulation of pro-apoptotic Bax and downregulation of antiapoptotic Bcl-2. The studies also indicated reduction of mitochondrial membrane potential and increase in the levels of caspase-3 and caspase-7.

  14. Synthesis and characterization of new homologous series of unsymmetrical liquid crystalline compounds based on chalcones and 3, 5-disubstituted isoxazoles

    Indian Academy of Sciences (India)

    SOWMYA P T; K M LOKANATHA RAI

    2017-01-01

    Two homologous series of unsymmetrical alkylated chalcones and 3,5-diaryl isoxazoles, consisting of 20 members, with various n-alkyl bromides (n=2−7, 10, 12, 14, 16) have been synthesized and studied for their liquid crystalline property. Simple strategy was employed to achieve the target materials. Flexibilityin the synthesized molecules is provided by attaching straight alkoxy chains, where one terminal group is fixed and other terminal group is varied. The synthesized compounds were characterized on the basis of Mass, IR and NMR spectroscopy. The stability and the range of the mesophases increased with the length of the chain on the isoxazoles. The melting point, transition temperatures and enantiotropic liquid crystal morphologies were determined by polarizing optical microscopy (POM) in conjunction with a hot stage and by differential scanning calorimetry (DSC).

  15. Design, synthesis and biological evaluation of novel (E)-α-benzylsulfonyl chalcone derivatives as potential BRAF inhibitors.

    Science.gov (United States)

    Li, Qing-Shan; Li, Cui-Yun; Lu, Xiang; Zhang, Hui; Zhu, Hai-Liang

    2012-04-01

    Activating mutations in the BRAF serine/threonine kinase are found in more than 70% of human melanomas, >90% of which are BRAF(V600E). It provides new therapeutic opportunities in malignant melanoma. In silico and in vitro screening of our compound collection has identified Hit 2 as BRAF(V600E) inhibitor. Based on its structure, a series of novel (E)-α-benzylsulfonyl chalcone derivatives (13-40) were designed and synthesized. Compound 38 exhibited the most potent inhibitory activity with an IC(50) value of 0.17 μM for BRAF(V600E) and GI(50) value of 0.52 μM for mutant BRAF-dependent cells. The results of cell based pERK activity and cellular selectivity suggested that those compounds could selectively inhibit proliferation of mutant BRAF-dependent melanoma cell line through inhibition of oncogenic BRAF.

  16. SYNTHESIS AND IN VITRO ANTIMICROBIAL EVALUATION OF PIPERAZINE SUBSTITUTED QUINAZOLINE-BASED THIOUREA/THIAZOLIDINONE/CHALCONE HYBRIDS.

    Science.gov (United States)

    Shah, D R; Lakum, H P; Chikhalia, K H

    2015-01-01

    In frames of the search for new biological entities to fight against recent drug-resistant microbial strains, we report a library of quinazoline-based thiourea/4-thiazolidinone/chalcone hybrids. The newly synthesized compounds were studied for efficacy against several bacteria (Staphylococcus aureus, Bacillus cereus, Pseudomonas aeruginosa, and Klebsiella pneumoniae) and fungi (Candida albicans and Aspergillus clavatus) using the broth dilution technique. From the biological evaluation, (E)-3-(3,4-dimethoxyphenyl)-1-(4-((4-(4-ethylpiperazin-1-yl)quinazolin-2-yl)amino)phenyl)prop-2-en-1-one was found to be the most active analogue (microbial inhibition concentration 3.12 μg/mL) to inhibit the bacterial growth. The rest of the compounds showed equipotent efficacy (3.12-12.5 μg/mL) as compared to the standard. Final compounds were characterized by FT-IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis.

  17. Inhibition of gastric H+, K(+)-ATPase by chalcone derivatives, xanthoangelol and 4-hydroxyderricin, from Angelica keiskei Koidzumi.

    Science.gov (United States)

    Murakami, S; Kijima, H; Isobe, Y; Muramatsu, M; Aihara, H; Otomo, S; Baba, K; Kozawa, M

    1990-10-01

    Two chalcone derivatives, xanthoangelol (1) and 4-hydroxyderricin (II) isolated from Angelica keiskei Koidzumi, inhibited pig gastric H+, K(+)-ATPase with IC50 values of 1.8 and 3.3 microM, respectively. The inhibition by I or II was competitive with respect to ATP and was non-competitive with respect to K+ I and II also inhibited K+, stimulated p-nitrophenyl phosphatase, with IC50 values of 1.3 and 3.5 microM, respectively. Proton transport in-vitro was inhibited by I or II, in a dose-dependent manner, 1 at 100 mg kg-1, i.p. significantly inhibited acid secretion and the formation of stress-induced gastric lesions. These results suggest that the antisecretory effect of 1 is due to the inhibition of gastric H+, K(+)-ATPase.

  18. Xanthohumol, a prenylated chalcone derived from hops, inhibits proliferation, migration and interleukin-8 expression of hepatocellular carcinoma cells.

    Science.gov (United States)

    Dorn, Christoph; Weiss, Thomas S; Heilmann, Jörg; Hellerbrand, Claus

    2010-02-01

    Xanthohumol, the major prenylated chalcone found in hops, is well known to exert anti-cancer effects, but information regarding the impact on hepatocellular carcinoma (HCC) cells and potential adverse effects on non-tumorous hepatocytes is limited. Here, we show that xanthohumol at a concentration of 25 microM induced apoptosis in two HCC cell lines (HepG2 and Huh7). Furthermore, xanthohumol repressed proliferation and migration, as well as TNF induced NF-kappaB activity and interleukin-8 expression in both cell lines at even lower concentrations. In contrast, xanthohumol concentrations up to 100 microM did not affect viability of primary human hepatocytes in vitro. In summary, our data showed that xanthohumol can ameliorate different pro-tumorigenic mechanisms known to promote HCC progression, indicating its potential as promising therapeutic agent that selectively affects cancer cells.

  19. The inhibitory effects of xanthohumol, a prenylated chalcone derived from hops, on cell growth and tumorigenesis in human pancreatic cancer.

    Science.gov (United States)

    Jiang, Weiliang; Zhao, Senlin; Xu, Ling; Lu, Yingying; Lu, Zhanjun; Chen, Congying; Ni, Jianbo; Wan, Rong; Yang, Lijuan

    2015-07-01

    Pancreatic cancer (PC) is one of the most lethal human malignancies worldwide. Here, we demonstrated that xanthohumol (XN), the most abundant prenylated chalcone isolated from hops, inhibited the growth of cultured PC cells and their subcutaneous xenograft tumors. XN treatment was found to induce cell cycle arrest and apoptosis of PC cells (PANC-1, BxPC-3) by inhibiting phosphorylation of signal transducer and activator of transcription 3 (STAT3) and expression of its downstream targeted genes cyclinD1, survivin, and Bcl-xL at the messenger RNA level, which involved in regulation of apoptosis and the cell cycle. Overall, our results suggested that XN presents a promising candidate therapeutic agent against human PC and the STAT3 signaling pathway is its key molecular target.

  20. Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi

    Energy Technology Data Exchange (ETDEWEB)

    Borchhardt, Deise M.; Oliva, Glaucius; Andricopulo, Adriano D. [Universidade de Sao Paulo, Sao Carlos (USP), SP (Brazil). Centro de Biotecnologia Molecular Estrutural. Lab. de Quimica Medicinal e Computacional; Mascarello, Alessandra; Chiaradia, Louise Domeneghini; Nunes, Ricardo J.; Yunes, Rosendo A. [Universidade Federal de Santa Catarina (UFSC), Florianopolis, SC (Brazil). Centro de Ciencias Fisicas e Matematicas. Lab. Estrutura e Atividade

    2010-07-01

    Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC{sub 50} values in the range of 20-60 {mu}M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series. (author)

  1. One type of chalcone synthase gene expressed during embryogenesis regulates the flavonoid accumulation in citrus cell cultures.

    Science.gov (United States)

    Moriguchi, T; Kita, M; Tomono, Y; EndoInagaki, T; Omura, M

    1999-06-01

    To elucidate the relationship between the expression of chalcone synthase (CHS) genes and the production of flavonoid in citrus cell cultures, two cDNA clones encoding CHS were isolated (CitCHS1 and CitCHS2) from the citrus. The accumulation of CitCHS2 mRNA was notably induced by embryogenesis but CitCHS1 mRNA was not. There was no detectable accumulation of flavonoid in the undifferentiated calli, but flavonoid accumulated after the morphological changes to embryoids. These results indicate that two CHS genes differentially expressed during citrus somatic embryogenesis and CitCHS2 may regulate the accumulation of flavonoid in citrus cell cultures.

  2. In vivo phase II-enzymes inducers, as potential chemopreventive agents, based on the chalcone and furoxan skeletons.

    Science.gov (United States)

    Cabrera, Mauricio; Mastandrea, Ignacio; Otero, Gabriel; Cerecetto, Hugo; González, Mercedes

    2016-04-15

    Cancer chemoprevention involves prevention/delay/reverse of the carcinogenic process through administration of cancer chemopreventive agents (CCA). Compounds which are able to induce detoxification-enzymes, especially monofunctional phase II enzymes, have become in excellent approaches for new CCA. Herein, we report the synthesis of new furoxanyl chalcone-like hybrid compounds as CCA. In vitro studies showed that phenylfuroxanyl derivatives 6 and 9 displayed the best activities being 9 the greatest monofunctional-inducer. Additionally, compounds were non-mutagenic against TA98 Salmonella typhimurium strain (Ames test) and could be used in the prevention of the progression of pre-malignant lesions for their cytotoxic activity against tumoral cells. In vivo proof of concept showed increment on phase II-enzymes activities in liver, colon and mammary gland having derivative 9 the best induction profiles. We probed Nrf2 nuclear translocation is operative for both compounds allowing to exert protective effects via expression of downstream phase-II enzymes.

  3. Synergistic combination of fluoro chalcone and doxorubicin on HeLa cervical cancer cells by inducing apoptosis

    Science.gov (United States)

    Arianingrum, Retno; Arty, Indyah Sulistyo; Atun, Sri

    2017-03-01

    Doxorubicin (Dox), a primary chemotherapeutic agent used for cancer treatment is known to have various side effect included multidrug resistance (MDR) phenomenon. Combination chemotherapy is one of some approaches to reduce Dox side effect. Chalcones have been reported to reduce the proliferation of many cancer cells. The research were conducted to investigate the cytotoxic activity and apoptosis induction of a chalcone derivate which is containing fluoro substituent [1 - (4" - fluorophenyl) -3 - (4' - hydroxy - 3' - methoxyphenyl) - 2 - propene - 1 -on] (FHM) and its combination with Dox on HeLa cells line. The observation of the cytotoxic activity was conducted using MTT [3 - (4, 5 - dimethyl thiazol - 2 - y1) - 2.5 - diphenyltetrazolium bromide] assay. Apoptosis induction was determined by flow cytometric. The changes of cell morphology were observed using phase contrast microscopy. The combination index (CI) was used to determine the effect of the combination. The study showed that FHM inhibited the HeLa cell growth with IC50 of 34 μM, while the IC50 of Dox was 1 μM. The combination had a higher inhibitory effect on cell growth compare to the single treatment of FHM and Dox. All of the combination doses under IC50 of FHM and Dox gave synergistic (CI: - 0.7) up to strong synergistic effect (CI: 0.l - 0.3). The synergistic effects of the combination were due to their ability to induce apoptosis in the HeLa cells. According to the result, FHM was potential to be developed as a co-chemotherapeutic agent with Dox for cervical cancer.

  4. Cytotoxic effects of new geranyl chalcone derivatives isolated from the leaves of Artocarpus communis in SW 872 human liposarcoma cells.

    Science.gov (United States)

    Fang, Song-Chwan; Hsu, Chin-Lin; Yu, Yu-Shen; Yen, Gow-Chin

    2008-10-08

    Breadfruit (Artocarpus communis Moraceae) is cultivated in tropical and subtropical regions as a traditional starch crop and also has potential medicinal properties. The aim of this work was to study the in vitro anticancer activity of compounds isolated from the leaves of Artocarpus communis. Three new geranyl chalcone derivatives including isolespeol (1), 5'-geranyl-2',4',4-trihydroxychalcone (2), and 3,4,2',4'-tetrahydroxy-3'-geranyldihydrochalcone (3), together with two known compounds lespeol (4) and xanthoangelol (5), were isolated from the leaves of Artocarpus communis. The structures of 1- 5 were elucidated by spectroscopy and through comparison with data reported in the literature. The effects of geranyl chalcone derivatives (1- 5) on the viability of human cancer cells (including SW 872, HT-29, COLO 205, Hep3B, PLC5, Huh7, and HepG2 cells) were investigated. The results indicate that isolespeol (1) showed the highest inhibitory activity with an IC 50 value of 3.8 muM in SW 872 human liposarcoma cells. Treatment of SW 872 human liposarcoma cells with isolespeol (1) caused the loss of mitochondrial membrane potential (DeltaPsim). Western blotting revealed that isolespeol (1) stimulated increased protein expression of Fas, FasL, and p53. The expression ratios of pro- and antiapoptotic Bcl-2 family members were also changed by isolespeol (1) treatment to subsequently induce the activation of caspase-9 and caspase-3, which was followed by cleavage of poly (ADP-ribose) polymerase (PARP). These results demonstrate that isolespeol (1) induces apoptosis in SW 872 cells through Fas- and mitochondria-mediated pathways.

  5. Endogenous, tissue-specific short interfering RNAs silence the chalcone synthase gene family in glycine max seed coats.

    Science.gov (United States)

    Tuteja, Jigyasa H; Zabala, Gracia; Varala, Kranthi; Hudson, Matthew; Vodkin, Lila O

    2009-10-01

    Two dominant alleles of the I locus in Glycine max silence nine chalcone synthase (CHS) genes to inhibit function of the flavonoid pathway in the seed coat. We describe here the intricacies of this naturally occurring silencing mechanism based on results from small RNA gel blots and high-throughput sequencing of small RNA populations. The two dominant alleles of the I locus encompass a 27-kb region containing two perfectly repeated and inverted clusters of three chalcone synthase genes (CHS1, CHS3, and CHS4). This structure silences the expression of all CHS genes, including CHS7 and CHS8, located on other chromosomes. The CHS short interfering RNAs (siRNAs) sequenced support a mechanism by which RNAs transcribed from the CHS inverted repeat form aberrant double-stranded RNAs that become substrates for dicer-like ribonuclease. The resulting primary siRNAs become guides that target the mRNAs of the nonlinked, highly expressed CHS7 and CHS8 genes, followed by subsequent amplification of CHS7 and CHS8 secondary siRNAs by RNA-dependent RNA polymerase. Most remarkably, this silencing mechanism occurs only in one tissue, the seed coat, as shown by the lack of CHS siRNAs in cotyledons and vegetative tissues. Thus, production of the trigger double-stranded RNA that initiates the process occurs in a specific tissue and represents an example of naturally occurring inhibition of a metabolic pathway by siRNAs in one tissue while allowing expression of the pathway and synthesis of valuable secondary metabolites in all other organs/tissues of the plant.

  6. Design, synthesis, physicochemical studies, solvation, and DNA damage of quinoline-appended chalcone derivative: comprehensive spectroscopic approach toward drug discovery.

    Science.gov (United States)

    Kumar, Himank; Chattopadhyay, Anjan; Prasath, R; Devaraji, Vinod; Joshi, Ritika; Bhavana, P; Saini, Praveen; Ghosh, Sujit Kumar

    2014-07-01

    The present study epitomizes the design, synthesis, photophysics, solvation, and interaction with calf-thymus DNA of a potential antitumor, anticancer quinoline-appended chalcone derivative, (E)-3-(anthracen-10-yl)-1-(6,8-dibromo-2-methylquinolin-3-yl)prop-2-en-1-one (ADMQ) using steady state absorption and fluorescence spectroscopy, molecular modeling, molecular docking, Fourier-transform infrared spectroscopy (FTIR), molecular dynamics (MD) simulation, and gel electrophoresis studies. ADMQ shows an unusual photophysical behavior in a variety of solvents of different polarity. The dual emission has been observed along with the formation of twisted intramolecular charge transfer (TICT) excited state. The radiationless deactivation of the TICT state is found to be promoted strongly by hydrogen bonding. Quantum mechanical (DFT, TDDFT, and ZINDO-CI) calculations show that the ADMQ is sort of molecular rotor which undergoes intramolecular twist followed by a complete charge transfer in the optimized excited state. FTIR studies reveals that ADMQ undergoes important structural change from its native structure to a β-hydroxy keto form in water at physiological pH. The concentration-dependent DNA cleavage has been identified in agarose gel DNA electrophoresis experiment and has been further supported by MD simulation. ADMQ forms hydrogen bond with the deoxyribose sugar attached with the nucleobase adenine DA-17 (chain A) and result in significant structural changes which potentially cleave DNA double helix. The compound does not exhibit any deleterious effect or toxicity to the E. coli strain in cytotoxicity studies. The consolidated spectroscopic research described herein can provide enormous information to open up new avenues for designing and synthesizing chalcone derivatives with low systematic toxicity for medicinal chemistry research.

  7. Design, Synthesis and Structure-Activity Relationships of Novel Chalcone-1,2,3-triazole-azole Derivates as Antiproliferative Agents

    Directory of Open Access Journals (Sweden)

    Sai-Yang Zhang

    2016-05-01

    Full Text Available A series of novel chalcone-1,2,3-triazole-azole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three selected cancer cell lines (SK-N-SH, EC-109 and MGC-803. Most of the synthesized compounds exhibited moderate to good activity against all the cancer cell lines selected. Particularly, compound I-21 showed the most excellent antiproliferative activity with an IC50 value of 1.52 μM against SK-N-SH cancer cells. Further mechanism studies revealed that compound I-21 induced morphological changes of SK-N-SH cancer cells possibly by inducing apoptosis. Novel chalcone-1,2,3-triazole-azole derivatives in this work might be a series of promising lead compounds to develop anticancer agents for treating neuroblastoma.

  8. The chalcone 2'-hydroxy-4',5'-dimethoxychalcone activates death receptor 5 pathway and leads to apoptosis in human nonsmall cell lung cancer cells.

    Science.gov (United States)

    Yang, Lina; Su, Ling; Cao, Congmei; Xu, Linyan; Zhong, Diansheng; Xu, Lijia; Liu, Xiangguo

    2013-06-01

    Natural chalcones have been proved to inhibit cancer cells with therapeutic potential, but the underlying molecular mechanism is still largely unexplored. Here, we identified a novel chalcone, 2'-hydroxy-4',5'-dimethoxychalcone (HDMC) and demonstrated that HDMC induced apoptosis in various nonsmall cell lung cancer cells. Further study showed that HDMC elevated cellular reactive oxygen species (ROS) levels, thus inducing expressions of ATF4 and C/EBP homologous protein (CHOP). Then, death receptor 5 (DR5) was upregulated through ATF4-CHOP axis and eventually resulted in apoptosis. We also found that downregulation of c-FLIPL contributed to HDMC-induced apoptosis. In conclusion, HDMC induces apoptosis in human nonsmall cell lung cancer cells via activation of DR5 signaling pathway, and ROS-mediated ATF4-CHOP axis is involved in the process. Our results further supported the potential for HDMC to be developed as a new antitumor agent for cancer therapy or chemoprevention.

  9. Structure-based drug design of a novel family of chalcones as PPARα agonists: virtual screening, synthesis, and biological activities in vitro

    Institute of Scientific and Technical Information of China (English)

    Xiang-hua LI; Han-jun ZOU; An-hui WU; Yang-liang YE; Jian-hua SHEN

    2007-01-01

    Aim: To design and synthesize a novel class of peroxisome proliferator-activated receptors (PPAR)α agonists, which is obtained by the combination of the classi- cal fibrate "head group", a linker with appropriate length and a chalcone. Methods: Thirty seven compounds were designed and identified employing the virtual screening approach. Six compounds were then selected for synthesis and bioas- say according to the virtual screening results, structural similarity, and synthetic complexity. Results: Six new compounds (4b and 4d-h) were synthesized and bioassayed. All were found to be potent PPARα agonists, compound 4 h being the most prominent with a 50% effective concentration value of 0.06 μmol/L. Conclusion: This study provides a promising novel family of chalcones with a potential hypolipidemic effect.

  10. Anti-HIV cytotoxicity enzyme inhibition and molecular docking studies of quinoline based chalcones as potential non-nucleoside reverse transcriptase inhibitors (NNRT).

    Science.gov (United States)

    Hameed, Asima; Abdullah, Muhammad Imran; Ahmed, Ejaz; Sharif, Ahsan; Irfan, Ahmad; Masood, Sara

    2016-04-01

    A series of fourteen (A1 - A14) qunioline based chalcones were screened for reverse transcriptase inhibitors (RT) and found potentially active against RT. Bioassay, theoretical and dockings studies with RT (the enzyme required for reverse transcription of viral RNA) results showed that the type and positions of the substituents seemed to be critical for their inhibition against RT. The bromo and chloro substituted chalcone displayed high degree of inhibition against RT. The A4 andA6 showed high interaction with RT, contributing high free binding energy (ΔG -9.30 and -9.13kcal) and RT inhibition value (IC50 0.10μg/ml and 0.11μg/ml).

  11. Design, Synthesis and Structure-Activity Relationships of Novel Chalcone-1,2,3-triazole-azole Derivates as Antiproliferative Agents.

    Science.gov (United States)

    Zhang, Sai-Yang; Fu, Dong-Jun; Yue, Xiao-Xin; Liu, Ying-Chao; Song, Jian; Sun, Hui-Hui; Liu, Hong-Min; Zhang, Yan-Bing

    2016-05-19

    A series of novel chalcone-1,2,3-triazole-azole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three selected cancer cell lines (SK-N-SH, EC-109 and MGC-803). Most of the synthesized compounds exhibited moderate to good activity against all the cancer cell lines selected. Particularly, compound I-21 showed the most excellent antiproliferative activity with an IC50 value of 1.52 μM against SK-N-SH cancer cells. Further mechanism studies revealed that compound I-21 induced morphological changes of SK-N-SH cancer cells possibly by inducing apoptosis. Novel chalcone-1,2,3-triazole-azole derivatives in this work might be a series of promising lead compounds to develop anticancer agents for treating neuroblastoma.

  12. Structure elucidation and DFT-study on substrate-selective formation of chalcones containing ferrocene and phenothiazine units. Study on ferrocenes, Part 17

    Science.gov (United States)

    Lovász, Tamás; Túrós, György; Găină, Luiza; Csámpai, Antal; Frigyes, Dávid; Fábián, Balázs; Silberg, Ioan A.; Sohár, Pál

    2005-09-01

    By means of base-catalysed condensation of 1-acyl-/1,1'-diacylferrocenes (acyl dbnd6 formyl or acetyl) with 3-formyl- and 3,7-diacetylphenothiazines a series of novel mono- and bis-chalcones were prepared. The enhanced reactivity of the enolate anions of the mono-chalcone intermediates relative to that of the enolates of the corresponding diacetyl-substituted precursor was interpreted by the electron-releasing effect of the ferrocenyl- or phenothiazinyl group present in the β position of the enone subunit. The structures of the novel products were evidenced by IR, 1H and 13C NMR spectroscopy including 2D-COSY, 2D-HSQC and 2D-HMBC measurements.

  13. The impact of position and number of methoxy group(s) to tune the nonlinear optical properties of chalcone derivatives: a dual substitution strategy.

    Science.gov (United States)

    Muhammad, Shabbir; Al-Sehemi, Abdullah G; Irfan, Ahmad; Chaudhry, Aijaz R; Gharni, Hamid; AlFaify, S; Shkir, Mohd; Asiri, Abdullah M

    2016-04-01

    Using the state-of-art computational techniques, we limelight a structure-property relationship for the position and number of methoxy group(s) to tune the optical and nonlinear optical (NLO) properties (first hyperpolarizability) of chalcone derivatives. Based on our previously synthesized chalcones [system 1 ((E)-1-(2,5-dimethylthiophen-3-yl)-3-(2-methoxyphenyl)prop-2-en-1-one and system 4 (E)-1-(2,5-dimethylthiophen-3-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one)], we systematically design several novel derivatives with tuned optical and NLO properties. For instance, the rotation of methoxy group substitutions at three different possible ortho, meta, and para positions on phenyl ring show significant changes in NLO properties of these chalcones derivatives. The system 3 has shown β tot amplitude of 1776 a.u. with terminal 4-methoxyphenyl group (para-methoxy substitution), which is ~2.2 and 2.4 times larger than that of ortho- and meta-methoxyphenyl systems 1 and 2, respectively. Additionally, systems 3a and 4a, which are cyano derivatives of the systems 3 and 4 show significantly large β tot amplitudes of 3280 and 4388 a.u., respectively, which are about 3 and 4 times larger than that of para-nitro aniline (PNA) molecule (a typical donor-acceptor molecule) at the same LC-wPBE/6-311G** level of theory. The origin of larger β tot amplitudes has been traced in lower transition energies and higher oscillator strengths for crucial transitions of designed derives. Thus, our investigation reveals that the chalcones derivatives with para-methoxyphenyl groups possess reasonably large amplitudes of their first hyperpolarizability and good optical transparency (3.0-4.7 eV), which can make them attractive candidates for nonlinear optical applications.

  14. Research advance of the anti-cancer activity of chalcone compounds%查尔酮类化合物的抗癌活性研究进展

    Institute of Scientific and Technical Information of China (English)

    王永波; 木合布力·阿布力孜

    2015-01-01

    Objective To screen the lead compounds of anti‐cancer with the characteristics of novel structure ,strong biological activ‐ity ,safe and effective from the traditional natural medicines .Methods Varieties of heterocyclic structure and its anticancer mecha‐nism of chalcone were analyzed and discussed .Results In the structure of chalcone ,the biological activity of chalcone compounds can be improved by the introduction of different groups ,changing the structure of relative configuration and so on .Conclusion Heterocyclic chalcones have strong anti‐cancer biological activity .According to its structure‐activitity relationship ,lead com‐pounds of anti‐cancer ,which have novel structure ,strong biological activity ,safe and effective ,could be selected from the tradi‐tional natural medicines .%目的:从传统天然药物中筛选出结构新颖、生物活性较强、安全有效的抗癌先导化合物。方法通过比较多种含杂环结构查尔酮类化合物及其抗癌机制来进行分析论证。结果在查尔酮结构中,引入不同的基团、改变结构相对构型等使所得化合物的抗癌活性有所提高。结论杂环查尔酮类化合物显示出较强的抗癌生物活性,根据其构型关系,从传统天然药物筛选出结构新颖、生物活性较强、安全有效的抗癌先导化合物。

  15. Structural features of substituted triazole-linked chalcone derivatives as antimalarial activities against D10 strains ofPlasmodium falciparum:A QSAR approach

    Institute of Scientific and Technical Information of China (English)

    Mukesh C. Sharma

    2015-01-01

    A quantitative structure–activity relationship (QSAR) was performed to analyze antimalarial activities against the D10 strains ofPlasmodium falciparum of triazole-linked chalcone and dienone hybrid derivatives using partial least squares regression coupled with stepwise forward–backward variable selection method. QSAR analyses were performed on the available IC50 D10 strains ofPlasmodium falciparum data based on theoretical molecular descriptors. The QSAR model developed gave good predictive correlation coefficient (r2) of 0.8994, significant cross validated correlation coefficient (q2) of 0.7689,r2 for external test set(p2)redr of 0.8256, coefficient of correlation of predicted data set)(p2sered,r of 0.3276. The model shows that antimalarial activity is greatly affected by donor and electron-withdrawing substituents. The study implicates that chalcone and dienone rings should have strong donor and electron-withdrawing substituents as they increase the activity of chalcone. Results show that the predictive ability of the model is satisfactory, and it can be used for designing similar group of antimalarial compounds. The findings derived from this analysis along with other molecular modeling studies will be helpful in designing of the new potent antimalarial activity of clinical utility.

  16. Synergistic effect of iodide ions on the corrosion inhibition of steel in 0.5 M H 2SO 4 by new chalcone derivatives

    Science.gov (United States)

    Bouklah, M.; Hammouti, B.; Aouniti, A.; Benkaddour, M.; Bouyanzer, A.

    2006-07-01

    The effect of addition of 4',4-dihydroxychalcone (P 1), 4-aminochalcone (P 2) and 4-bromo, 4'-methoxychalcone (P 3) on the corrosion of steel in 0.5 M sulphuric acid has been studied by weight loss measurements, potentiodynamic and EIS measurements. We investigate the synergistic effect of iodide ions on the corrosion inhibition of steel in the presence of chalcone derivatives. The corrosion rates of the steel decrease with the increase of the chalcones concentration, while the inhibition efficiencies increase. The addition of iodide ions enhances the inhibition efficiency considerably. The presence of iodide ions increases the degree of surface coverage. The synergism parameters SΘ and SI, calculated from surface coverage and the values of inhibition efficiency, in the case of chalcone derivatives are found to be larger than unity. The enhanced inhibition efficiency in the presence of iodide ions is only due to synergism and there is a definite contribution from the inhibitors molecules. E (%) obtained from the various methods is in good agreement. Polarisation measurements show also that the compounds act as cathodic inhibitors.

  17. Binary classification of chalcone derivatives with LDA or KNN based on their antileishmanial activity and molecular descriptors selected using the Successive Projections Algorithm feature-selection technique.

    Science.gov (United States)

    Goodarzi, Mohammad; Saeys, Wouter; de Araujo, Mario Cesar Ugulino; Galvão, Roberto Kawakami Harrop; Vander Heyden, Yvan

    2014-01-23

    Chalcones are naturally occurring aromatic ketones, which consist of an α-, β-unsaturated carbonyl system joining two aryl rings. These compounds are reported to exhibit several pharmacological activities, including antiparasitic, antibacterial, antifungal, anticancer, immunomodulatory, nitric oxide inhibition and anti-inflammatory effects. In the present work, a Quantitative Structure-Activity Relationship (QSAR) study is carried out to classify chalcone derivatives with respect to their antileishmanial activity (active/inactive) on the basis of molecular descriptors. For this purpose, two techniques to select descriptors are employed, the Successive Projections Algorithm (SPA) and the Genetic Algorithm (GA). The selected descriptors are initially employed to build Linear Discriminant Analysis (LDA) models. An additional investigation is then carried out to determine whether the results can be improved by using a non-parametric classification technique (One Nearest Neighbour, 1NN). In a case study involving 100 chalcone derivatives, the 1NN models were found to provide better rates of correct classification than LDA, both in the training and test sets. The best result was achieved by a SPA-1NN model with six molecular descriptors, which provided correct classification rates of 97% and 84% for the training and test sets, respectively.

  18. Newly synthesized 'hidabeni' chalcone derivatives potently suppress LPS-induced NO production via inhibition of STAT1, but not NF-κB, JNK, and p38, pathways in microglia.

    Science.gov (United States)

    Hara, Hirokazu; Ikeda, Ryoko; Ninomiya, Masayuki; Kamiya, Tetsuro; Koketsu, Mamoru; Adachi, Tetsuo

    2014-01-01

    Chalcones are open-chain flavonoids that are biosynthesized in various plants. Some of them possess anti-inflammatory activity. We previously found that chalcone glycosides from Brassica rapa L. 'hidabeni' suppress lipopolysaccharide (LPS)-induced nitric oxide (NO) production in rat microglia highly aggressively proliferating immortalized (HAPI) cells. In this study, to explore chalcone derivatives with potent NO inhibitory activity, we synthesized ten compounds based on 'hidabeni' chalcone and examined their effects on LPS-triggered inducible NO synthase (iNOS) expression and NO production. Compounds C4 and C10 potently inhibited NO production (IC50: 4.19, 2.88 µM, respectively). C4 and C10 suppressed LPS-induced iNOS expression via the inhibition of the signal transduction and activator of transcription 1 (STAT1), but not nuclear factor-kappa B (NF-κB), c-Jun N terminal kinase (JNK), and p38, pathways. C10, but not C4, inhibited activation of the MEK/extracellular signal-regulated kinase (ERK) pathway. C4 and C10 also suppressed LPS-induced expression of interferon regulatory factor 1 (IRF-1), which is an important transcription factor involved in iNOS expression. Our findings indicate that these chalcone derivatives are candidate compounds for preventing microglia-mediated neuroinflammation.

  19. Structure-activity relationship studies of chalcone leading to 3-hydroxy-4,3',4',5'-tetramethoxychalcone and its analogues as potent nuclear factor kappaB inhibitors and their anticancer activities.

    Science.gov (United States)

    Srinivasan, Balasubramanian; Johnson, Thomas E; Lad, Rahul; Xing, Chengguo

    2009-11-26

    Chalcone is a privileged structure, demonstrating promising anti-inflammatory and anticancer activities. One potential mechanism is to suppress nuclear factor kappa B (NF-kappaB) activation. The structures of chalcone-based NF-kappaB inhibitors vary significantly that there is minimum information about their structure-activity relationships (SAR). This study aims to establish SAR of chalcone-based compounds to NF-kappaB inhibition, to explore the feasibility of developing simple chalcone-based potent NF-kappaB inhibitors, and to evaluate their anticancer activities. Three series of chalcones were synthesized in one to three steps with the key step being aldol condensation. These candidates demonstrated a wide range of NF-kappaB inhibitory activities, some of low micromolar potency, establishing that structural complexity is not required for NF-kappaB inhibition. Lead compounds also demonstrate potent cytotoxicity against lung cancer cells. Their cytotoxicities correlate moderately well with their NF-kappaB inhibitory activities, suggesting that suppressing NF-kappaB activation is likely responsible for at least some of the cytotoxicities. One lead compound effectively inhibits lung tumor growth with no signs of adverse side effects.

  20. Activity of chalcones derived from 2,4,5-trimethoxybenzaldehyde against Meloidogyne exigua and in silico interaction of one chalcone with a putative caffeic acid 3-O-methyltransferase from Meloidogyne incognita.

    Science.gov (United States)

    Nunes, Alexandro Silva; Campos, Vicente Paulo; Mascarello, Alessandra; Stumpf, Taisa Regina; Chiaradia-Delatorre, Louise Domenghini; Machado, Alan Rodrigues Teixeira; Santos Júnior, Helvécio Martins; Yunes, Rosendo Augusto; Nunes, Ricardo José; Oliveira, Denilson Ferreira

    2013-12-01

    Meloidogyne exigua is a parasitic nematode of plants that causes great losses to coffee farmers. In an effort to develop parasitic controls, 154 chalcones were synthesized and screened for activity against this nematode. The best results were obtained with (2E)-1-(4'-nitrophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (6) with a 50% lethal concentration (LC50) of 171 μg/ml against M. exigua second-stage juveniles, in comparison to the commercially-available nematicide carbofuran which had an LC50 of 260 μg/ml under the same conditions. When coffee plants were used, 6 reduced the nematode population to ~50% of that observed in control plants. To investigate the mechanism of action of 6, an in silico study was carried out, which indicated that 6 may act against M. exigua through inhibition of a putative caffeic acid 3-O-methyltransferase homodimer, the amino acid sequence of which was determined by examining the genome of Meloidogyne incognita.

  1. Silencing CHALCONE SYNTHASE in Maize Impedes the Incorporation of Tricin into Lignin and Increases Lignin Content1[OPEN

    Science.gov (United States)

    2017-01-01

    Lignin is a phenolic heteropolymer that is deposited in secondary-thickened cell walls, where it provides mechanical strength. A recent structural characterization of cell walls from monocot species showed that the flavone tricin is part of the native lignin polymer, where it is hypothesized to initiate lignin chains. In this study, we investigated the consequences of altered tricin levels on lignin structure and cell wall recalcitrance by phenolic profiling, nuclear magnetic resonance, and saccharification assays of the naturally silenced maize (Zea mays) C2-Idf (inhibitor diffuse) mutant, defective in the CHALCONE SYNTHASE Colorless2 (C2) gene. We show that the C2-Idf mutant produces highly reduced levels of apigenin- and tricin-related flavonoids, resulting in a strongly reduced incorporation of tricin into the lignin polymer. Moreover, the lignin was enriched in β-β and β-5 units, lending support to the contention that tricin acts to initiate lignin chains and that, in the absence of tricin, more monolignol dimerization reactions occur. In addition, the C2-Idf mutation resulted in strikingly higher Klason lignin levels in the leaves. As a consequence, the leaves of C2-Idf mutants had significantly reduced saccharification efficiencies compared with those of control plants. These findings are instructive for lignin engineering strategies to improve biomass processing and biochemical production. PMID:27940492

  2. Synthesis, docking and ADMET studies of novel chalcone triazoles for anti-cancer and anti-diabetic activity.

    Science.gov (United States)

    Chinthala, Yakaiah; Thakur, Sneha; Tirunagari, Shalini; Chinde, Srinivas; Domatti, Anand Kumar; Arigari, Niranjana Kumar; K V N S, Srinivas; Alam, Sarfaraz; Jonnala, Kotesh Kumar; Khan, Feroz; Tiwari, Ashok; Grover, Paramjit

    2015-03-26

    A series of novel chalcone-triazole derivatives were synthesized and screened for in vitro anticancer activity on the human cancer cell lines IMR32 (neuroblastoma), HepG2 (hepatoma) and MCF-7 (breast adenocarcinoma), DU-145 (prostate carcinoma), and A549 (lung adenocarcinoma). Among the tested compounds, 4r showed the most promising anticancer activity in all the cell lines whereas, compounds 4c (IC50 65.86 μM), 4e (IC50 66.28 μM), 4o (IC50 35.81 μM), 4q (IC50 50.82 μM) and 4s (IC50 48.63 μM) showed better activity than the standard doxorubicin (IC50 69.33 μM) in A549 cell line alone. Rat intestinal α-glucosidase inhibitory activity of the synthesized derivatives showed 4m (IC50 67.77 μM), 4p (IC50 74.94 in μM) and 4s (IC50 102.10 μM) as most active compared to others. The in silico docking of synthesized derivatives 4a-4t with DNA topoisomerase IIα revealed the LibDock score in the range of 71.2623-118.29 whereas, compounds 4h, 4m, 4p and 4s with docking target α-glucosidase were in the range of 100.372-107.784.

  3. Prenylated Chalcone 2 Acts as an Antimitotic Agent and Enhances the Chemosensitivity of Tumor Cells to Paclitaxel.

    Science.gov (United States)

    Fonseca, Joana; Marques, Sandra; Silva, Patrícia M A; Brandão, Pedro; Cidade, Honorina; Pinto, Madalena M; Bousbaa, Hassan

    2016-07-29

    We previously reported that prenylated chalcone 2 (PC2), the O-prenyl derivative (2) of 2'-hydroxy-3,4,4',5,6'-pentamethoxychalcone (1), induced cytotoxicity of tumor cells via disruption of p53-MDM2 interaction. However, the cellular changes through which PC2 exerts its cytotoxic activity and its antitumor potential, remain to be addressed. In the present work, we aimed to (i) characterize the effect of PC2 on mitotic progression and the underlying mechanism; and to (ii) explore this information to evaluate its ability to sensitize tumor cells to paclitaxel in a combination regimen. PC2 was able to arrest breast adenocarcinoma MCF-7 and non-small cell lung cancer NCI-H460 cells in mitosis. All mitosis-arrested cells showed collapsed mitotic spindles with randomly distributed chromosomes, and activated spindle assembly checkpoint. Live-cell imaging revealed that the compound induced a prolonged delay (up to 14 h) in mitosis, culminating in massive cell death by blebbing. Importantly, PC2 in combination with paclitaxel enhanced the effect on cell growth inhibition as determined by cell viability and proliferation assays. Our findings demonstrate that the cytotoxicity induced by PC2 is mediated through antimitotic activity as a result of mitotic spindle damage. The enhancement effects of PC2 on chemosensitivity of cancer cells to paclitaxel encourage further validation of the clinical potential of this combination.

  4. Synthesis, leishmanicidal and cytotoxic activity of triclosan-chalcone, triclosan-chromone and triclosan-coumarin hybrids.

    Science.gov (United States)

    Otero, Elver; Vergara, Sebastián; Robledo, Sara M; Cardona, Wilson; Carda, Miguel; Vélez, Ivan D; Rojas, Carlos; Otálvaro, Felipe

    2014-08-28

    Twelve hybrids derived from triclosan were obtained via Williamson etherification of O-triclosan alkyl bromide plus chalcone and O-coumarin or O-chromone alkyl bromide plus triclosan, respectively. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes. Cytotoxic activity was also evaluated against mammalian U-937 cells. Compounds 7-9 and 17, were active against Leishmania parasites (EC50=9.4; 10.2; 13.5 and 27.5 µg/mL, respectively) and showed no toxicity toward mammalian cells (>200 µg/mL). They are potential candidates for antileishmanial drug development. Compounds 25-27, were active and cytotoxic. Further studies using other cell types are needed in order to discriminate whether the toxicity shown by these compounds is against tumor or non-tumor cells. The results indicate that compounds containing small alkyl chains show better selectivity indices. Moreover, Michael acceptor moieties may modify both the leishmanicidal activity and cytotoxicity. Further studies are required to evaluate if the in vitro activity against Leishmania panamensis demonstrated here is also observed in vivo.

  5. Synthesis, Leishmanicidal and Cytotoxic Activity of Triclosan-Chalcone, Triclosan-Chromone and Triclosan-Coumarin Hybrids

    Directory of Open Access Journals (Sweden)

    Elver Otero

    2014-08-01

    Full Text Available Twelve hybrids derived from triclosan were obtained via Williamson etherification of O-triclosan alkyl bromide plus chalcone and O-coumarin or O-chromone alkyl bromide plus triclosan, respectively. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V panamensis amastigotes. Cytotoxic activity was also evaluated against mammalian U-937 cells. Compounds 7–9 and 17, were active against Leishmania parasites (EC50 = 9.4; 10.2; 13.5 and 27.5 µg/mL, respectively and showed no toxicity toward mammalian cells (>200 µg/mL. They are potential candidates for antileishmanial drug development. Compounds 25–27, were active and cytotoxic. Further studies using other cell types are needed in order to discriminate whether the toxicity shown by these compounds is against tumor or non-tumor cells. The results indicate that compounds containing small alkyl chains show better selectivity indices. Moreover, Michael acceptor moieties may modify both the leishmanicidal activity and cytotoxicity. Further studies are required to evaluate if the in vitro activity against Leishmania panamensis demonstrated here is also observed in vivo.

  6. The chalcone derivative Chana 1 protects against amyloid β peptide-induced oxidative stress and cognitive impairment.

    Science.gov (United States)

    Kwak, Jieun; Kim, Mi-Jeong; Choi, Kyung-Chul; Choi, Hyo-Kyung; Jun, Woojin; Park, Hyun-Jin; Lee, Yoo-Hyun; Yoon, Ho-Geun

    2012-07-01

    Alzheimer's disease (AD) is the most common neurodegenerative disease to cause dementia in the elderly. Amyloid β (Aβ)-peptide induced oxidative stress causes the initiation and progression of AD. Recently, new chalcone derivatives termed the Chana series were synthesized. Among them, Chana 1 showed high free radical scavenging activity (72.5%), as measured by a DPPH (1,1-diphenyl-2-picrylhydrazyl) assay. In this study, we investigated the effect of Chana 1 against Aβ-induced cytotoxicity and cognitive deficits. Additionally, we sought to estimate the lethal dose, 50% (LD50) of Chana 1 in mice using an acute oral toxicity test. We found that Chana 1 significantly protected against Aβ-induced neuronal cell death in PC12 cells. Oral administration of Chana 1 at a dose of 50 mg/kg body weight/day significantly improved Aβ-induced learning and memory impairment in mice, as measured in Y-maze and passive avoidance tests. In acute toxicity tests, the LD50 in mice was determined to be 520.44 mg/kg body weight. The data are valuable for future studies and suggest that Chana 1 has therapeutic potential for the management of neurodegenerative disease.

  7. Synthesis and evaluation of ethyleneoxylated and allyloxylated chalcone derivatives for imaging of amyloid β plaques by SPECT.

    Science.gov (United States)

    Fuchigami, Takeshi; Yamashita, Yuki; Haratake, Mamoru; Ono, Masahiro; Yoshida, Sakura; Nakayama, Morio

    2014-05-01

    We report radioiodinated chalcone derivatives as new SPECT imaging probes for amyloid β (Aβ) plaques. The monoethyleneoxy derivative 2 and allyloxy derivative 8 showed a high affinity for Aβ(1-42) aggregates with Ki values of 24 and 4.5 nM, respectively. Fluorescent imaging demonstrated that 2 and 8 clearly stained thioflavin-S positive Aβ plaques in the brain sections of Tg2576 transgenic mice. In vitro autoradiography revealed that [(125)I]2 displayed no clear accumulation toward Aβ plaques in the brain sections of Tg2576 mice, whereas the accumulation pattern of [(125)I]8 matched with the presence of Aβ plaques both in the brain sections of Tg2576 mice and an AD patient. In biodistribution studies using normal mice, [(125)I]2 showed preferable in vivo pharmacokinetics (4.82%ID/g at 2 min and 0.45%ID/g at 60 min), while [(125)I]8 showed only a modest brain uptake (1.62%ID/g at 2 min) with slow clearance (0.56%ID/g at 60 min). [(125)I]8 showed prospective binding properties for Aβ plaques, although further structural modifications are needed to improve the blood brain barrier permeability and washout from brain.

  8. Tetramethoxychalcone, a chalcone derivative, suppresses proliferation, blocks cell cycle progression, and induces apoptosis of human ovarian cancer cells.

    Science.gov (United States)

    Qi, Zihao; Liu, Mingming; Liu, Yang; Zhang, Meiqin; Yang, Gong

    2014-01-01

    In the present study, we investigated the in vitro antitumor functions of a synthetic chalcone derivative 4,3',4',5'- tetramethoxychalcone (TMOC) in ovarian cancer cells. We found that TMOC inhibited the proliferation and colony formation of cisplatin sensitive cell line A2780 and resistant cell line A2780/CDDP, as well as ovarian cancer cell line SKOV3 in a time- and dose-dependent manner. Treatment of A2780 cells with TMOC resulted in G0/G1 cell cycle arrest through the down-regulation of cyclin D1 and CDK4, and the up-regulation of p16, p21 and p27 proteins. We demonstrated that TMOC might induce cell apoptosis through suppressing Bcl-2 and Bcl-xL, but enhancing the expression of Bax and the cleavage of PARP-1. Treatment of TMOC also reduced the invasion and migration of A2780 cells. Finally, we found that TMOC inhibited the constitutive activation of STAT3 signaling pathway and induced the expression of the tumor suppressor PTEN regardless of the p53 status in cell lines. These data suggest that TMOC may be developed as a potential chemotherapeutic agent to effectively treat certain cancers including ovarian cancer.

  9. Benzofuran-chalcone hybrids as potential multifunctional agents against Alzheimer's disease: synthesis and in vivo studies with transgenic Caenorhabditis elegans.

    Science.gov (United States)

    Sashidhara, Koneni V; Modukuri, Ram K; Jadiya, Pooja; Dodda, Ranga Prasad; Kumar, Manoj; Sridhar, Balasubramaniam; Kumar, Vikash; Haque, Rizwanul; Siddiqi, Mohammad Imran; Nazir, Aamir

    2014-12-01

    In the search for effective multifunctional agents for the treatment of Alzheimer's disease (AD), a series of novel hybrids incorporating benzofuran and chalcone fragments were designed and synthesized. These hybrids were screened by using a transgenic Caenorhabditis elegans model that expresses the human β-amyloid (Aβ) peptide. Among the hybrids investigated, (E)-3-(7-methyl-2-(4-methylbenzoyl)benzofuran-5-yl)-1-phenylprop-2-en-1-one (4 f), (E)-3-(2-benzoyl-7-methylbenzofuran-5-yl)-1-phenylprop-2-en-1-one (4 i), and (E)-3-(2-benzoyl-7-methylbenzofuran-5-yl)-1-(thiophen-2-yl)prop-2-en-1-one (4 m) significantly decreased Aβ aggregation and increased acetylcholine (ACh) levels along with the overall availability of ACh at the synaptic junction. These compounds were also found to decrease acetylcholinesterase (AChE) levels, reduce oxidative stress in the worms, lower lipid content, and to provide protection against chemically induced cholinergic neurodegeneration. Overall, the multifunctional effects of these hybrids qualify them as potential drug leads for further development in AD therapy.

  10. Prenylated Chalcone 2 Acts as an Antimitotic Agent and Enhances the Chemosensitivity of Tumor Cells to Paclitaxel

    Directory of Open Access Journals (Sweden)

    Joana Fonseca

    2016-07-01

    Full Text Available We previously reported that prenylated chalcone 2 (PC2, the O-prenyl derivative (2 of 2′-hydroxy-3,4,4′,5,6′-pentamethoxychalcone (1, induced cytotoxicity of tumor cells via disruption of p53-MDM2 interaction. However, the cellular changes through which PC2 exerts its cytotoxic activity and its antitumor potential, remain to be addressed. In the present work, we aimed to (i characterize the effect of PC2 on mitotic progression and the underlying mechanism; and to (ii explore this information to evaluate its ability to sensitize tumor cells to paclitaxel in a combination regimen. PC2 was able to arrest breast adenocarcinoma MCF-7 and non-small cell lung cancer NCI-H460 cells in mitosis. All mitosis-arrested cells showed collapsed mitotic spindles with randomly distributed chromosomes, and activated spindle assembly checkpoint. Live-cell imaging revealed that the compound induced a prolonged delay (up to 14 h in mitosis, culminating in massive cell death by blebbing. Importantly, PC2 in combination with paclitaxel enhanced the effect on cell growth inhibition as determined by cell viability and proliferation assays. Our findings demonstrate that the cytotoxicity induced by PC2 is mediated through antimitotic activity as a result of mitotic spindle damage. The enhancement effects of PC2 on chemosensitivity of cancer cells to paclitaxel encourage further validation of the clinical potential of this combination.

  11. Hesperidin methyl chalcone inhibits oxidative stress and inflammation in a mouse model of ultraviolet B irradiation-induced skin damage.

    Science.gov (United States)

    Martinez, Renata M; Pinho-Ribeiro, Felipe A; Steffen, Vinicius S; Caviglione, Carla V; Vignoli, Josiane A; Baracat, Marcela M; Georgetti, Sandra R; Verri, Waldiceu A; Casagrande, Rubia

    2015-07-01

    Hesperidin methyl chalcone (HMC) is a safe flavonoid used to treat chronic venous diseases, but its effects and mechanisms on UVB irradiation-induced inflammation and oxidative stress have never been described in vivo. Thus, the purpose of this study was to evaluate the effects of systemic administration of HMC in skin oxidative stress and inflammation induced by UVB irradiation. To induce skin damage, hairless mice were exposed to an acute UVB irradiation dose of 4.14 J/cm(2), and the dorsal skin samples were collected to evaluate oxidative stress and inflammatory response. The intraperitoneal treatment with HMC at the dose of 300 mg/kg inhibited UVB irradiation-induced skin edema, neutrophil recruitment, and matrix metalloproteinase-9 activity. HMC also protected the skin from UVB irradiation-induced oxidative stress by maintaining ferric reducing antioxidant power (FRAP), 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) radical (ABTS) scavenging ability and antioxidant levels (reduced glutathione and catalase). Corroborating, HMC inhibited UVB irradiation-induced superoxide anion generation and gp91phox (NADPH oxidase subunit) mRNA expression. Furthermore, the antioxidant effect of HMC resulted in lower production of inflammatory mediators, including lipid hydroperoxides and a wide range of cytokines. Taken together, these results unveil a novel applicability of HMC in the treatment of UVB irradiation-induced skin inflammation and oxidative stress.

  12. 查耳酮类化合物的合成及其生物活性研究进展%Advances in Synthetic Methods and Biological Activity of Chalcones

    Institute of Scientific and Technical Information of China (English)

    夏雅平; 崔冬梅

    2011-01-01

    近年来,随着查耳酮类化合物的生物活性的发现,对它的研究越来越多。本文以不同的底物出发概述了查耳酮类化合物的合成方法,并对其的生物活性做了一下总结。%Chalcones have important biological effects,so they get more attentions. In this paper, we summarize some synthetic methods of the chalcones derivatives from different starting substrates, and give a introduction about it's bioactivity.

  13. 查耳酮的合成及体外抗真菌活性%Synthesis of a New Series of Chalcone Derivatives and Their Antifungal Activities

    Institute of Scientific and Technical Information of China (English)

    李正香; 李安良

    2004-01-01

    目的合成查耳酮类化合物并测定其抗真菌活性. 方法利用Claisen-Schmidt反应合成查耳酮,并针对四种真菌(白色念珠菌、新生隐球菌、烟曲霉菌、红色毛癣菌)做了体外抗真菌活性筛选. 结果显示所合成化合物大多具有体外抗真菌活性,尤其化合物8, 其针对浅表菌的抗真菌活性与氟康唑相当.本文还对部分查耳酮的合成做了一些探索.结论所合成的查耳酮均有不同程度的抗真菌活性,其化学结构差异与抗菌活性相关.%Aim To study the antifungal effect of chalcone derivatives. Methods Sixteen chalcone derivatives were synthesized and confirmed by 1H NMR and IR spectra, and tested for antifungal activity against four common pathogenic fungi. Their structure-activity relationship is discussed. Results Among 16 title compounds, there were 5 new compounds, which have not been reported before. The preliminary antifungal test showed that all title compounds exhibited antifungal activities to a certain extent. The activity of compound 8 against Trichophyton rubrum had a potency equal to that of fluconazole, with a MIC of 4 μg·mL-1. Conclusion Sixteen chalcones were prepared and their antifungal activities against four common pathogenic fungi in vitro were examined. Some of them exhibited antifungal activities to a certain extent.

  14. Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity

    Directory of Open Access Journals (Sweden)

    Rakesh N. Mistry

    2005-01-01

    Full Text Available 1, 2 - Dichloro benzene on chlorosulphonation by chlorosulphonic acid gives 1, 2 - [dichloro] - benzene sulphonyl chloride which on condensation with p –amino acetophenone gives 1-[acetyl] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative. This derivative undergo condensation with 2,4- dichloro benzaldehyde gives 1- [3” - (sub. phenyl - 2” - propene - 1” - one] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative which on reaction with 99% hydrazine hydrate and glacial acetic acid gives 1-[acetyl]-3- [1’ , 2’ - (dichloro - dibenz sulphonamide] -5 - [2” , 4” - dichloro phenyl] - 2 - pyrazoline derivative. This derivative reacts with various substituted aldehydes to give corresponding substituted chalcone derivatives [1(a-j]. Now, these chalcone derivatives [1(a-j] on condensation with urea gives corresponding substituted pyrimidine - 2 - one derivatives [2(a-j] and on condensation with thio-urea gives corresponding substituted pyrimidine- 2 -thione derivatives [3(a-j]. Further, these chalcone derivatives [1(a-j] on reaction with 99% hydrazine hydrate gives 1 - [1’ - (H - 5’ - (sub. phenyl - 2’ - pyrazoline]- 3 - [1” , 2” - (dichloro - dibenz sulphonamide] - 5 - [2’’’ , 4’’’ - dichloro phenyl]-2- pyrazoline derivatives [4(a-j] as an intermediate compounds, which on condensation with p-acetanilide sulphonyl chloride gives corresponding substituted p - acetanilide sulphonyl derivatives [5(a-j] and on condensation with benzoyl chloride gives corresponding substituted benzoyl derivatives [6(a-j]. Structure elucidation of synthesised compounds has been made on the basis of elemental analysis, I.R. spectral studies and 1H N.M.R. spectral studies. The antimicrobial activity of the synthesised compounds has been studied against the cultures “Staphylococcus aureus”, “Escherichia coli” and “Candela albicans”.

  15. Molecular docking based screening of novel designed chalcone series of compounds for their anti-cancer activity targeting EGFR kinase domain

    Science.gov (United States)

    Rao, Chennu Maruthi Malya Prasada; Yejella, Rajendra Prasad; Rehman, Rehman Shaik Abdul; Basha, Syed Hussain

    2015-01-01

    Epidermal growth factor receptors (EGFR) are critical for the growth of many tumors and expressed at high levels in about one third of epithelial cancers. Hence, blockade of the binding sites for EGFR has been hypothesized as an effective anti-cancer therapy. Chalcone derivative compounds have been shown to be highly effective anti-cancer agents, however there are still so many novel derivatives possible, one of which might get us the best targeted EGFR inhibitor. In this effort directed towards the discovery of novel, potent anti-tumor agents for the treatment of cancer, in the present study a library of novel chalcone series of compounds has been designed and evaluated for their anti-cancer activity targeting EGFR kinase domain using various computational approaches. Among the twenty five novel designed chalcone series of compounds, all of them have found to be successfully docking inside the active binding domain of EGFR receptor target with a binding energy in a range of -6.10 to -9.25 Kcal/mol with predicted IC50 value range of 33.50 micor molar to 164.66 nano molar respectively. On the other hand, calculated 2DQSAR molecular descriptor properties of the compounds showed promising ADME parameters and found to be well in compliance with Lipinski׳s rule of five. Among all the twenty five compounds tested, compound 21 ((2E)-3-(anthracen-9-yl)-1-phenylprop-2-2n-1- one) was found to be the best lead like molecule with a binding energy of -9.25 kcal/mol with predicted IC50 value of 164.66 nano molar. Conclusively, novel designed compound 21 of the present study have shown promising anti-cancer potential worth considering for further evaluations. PMID:26339147

  16. 4'-Acetoamido-4-hydroxychalcone, a chalcone derivative, inhibits glioma growth and invasion through regulation of the tropomyosin 1 gene

    Energy Technology Data Exchange (ETDEWEB)

    Ku, Bo Mi [Department of Anatomy and Neurobiology, Institute of Health Sciences, School of Medicine, Gyeongsang National University, Jinju 660-751 (Korea, Republic of); Ryu, Hyung Won [Division of Applied Life Science (BK21 Program), EB-NCRC, Institute of Agriculture Life Science, Graduate School of Gyeongsang National University, Jinju 660-701 (Korea, Republic of); Lee, Yeon Kyung; Ryu, Jinhyun; Jeong, Joo Yeon; Choi, Jungil [Department of Anatomy and Neurobiology, Institute of Health Sciences, School of Medicine, Gyeongsang National University, Jinju 660-751 (Korea, Republic of); Cho, Hee Jun [Department of Microbiology, Research Institute of Life Science, College of Natureal Sciences, Gyeongsang National University, Jinju 660-701 (Korea, Republic of); Park, Ki Hun, E-mail: khpark@gnu.ac.kr [Division of Applied Life Science (BK21 Program), EB-NCRC, Institute of Agriculture Life Science, Graduate School of Gyeongsang National University, Jinju 660-701 (Korea, Republic of); Kang, Sang Soo, E-mail: kangss@gnu.ac.kr [Department of Anatomy and Neurobiology, Institute of Health Sciences, School of Medicine, Gyeongsang National University, Jinju 660-751 (Korea, Republic of)

    2010-11-19

    Research highlights: {yields} 4'-Acetoamido-4-hydroxychalcone (AHC) has anti-cancer property for glioma. {yields} 4'-Acetoamido-4-hydroxychalcone (AHC) increased tropomyosin expreesion through activattion of PKA signaling. {yields} 4'-Acetoamido-4-hydroxychalcone (AHC) inhibits glioma cell migration and invasion. {yields} In vivo administration of 4'-acetoamido-4-hydroxychalcone (AHC) reduced tumor growth. -- Abstract: Chalcones are precursors of flavonoids and have been shown to have anti-cancer activity. Here, we identify the synthetic chalcone derivative 4'-acetoamido-4-hydroxychalcone (AHC) as a potential therapeutic agent for the treatment of glioma. Treatment with AHC reduced glioma cell invasion, migration, and colony formation in a concentration-dependent manner. In addition, AHC inhibited vascular endothelial growth factor-induced migration, invasion, and tube formation in HUVECs. To determine the mechanism underlying the inhibitory effect of AHC on glioma cell invasion and migration, we investigated the effect of AHC on the gene expression change and found that AHC affects actin dynamics in U87MG glioma cells. In actin cytoskeleton regulating system, AHC increased tropomyosin expression and stress fiber formation, probably through activation of PKA. Suppression of tropomyosin expression by siRNA or treatment with the PKA inhibitor H89 reduced the inhibitory effects of AHC on glioma cell invasion and migration. In vivo experiments also showed that AHC inhibited tumor growth in a xenograft mouse tumor model. Together, these data suggest that the synthetic chalcone derivative AHC has potent anti-cancer activity through inhibition of glioma proliferation, invasion, and angiogenesis and is therefore a potential chemotherapeutic candidate for the treatment of glioma.

  17. Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism

    Directory of Open Access Journals (Sweden)

    Patrice Vanelle

    2007-04-01

    Full Text Available An electron-transfer chain reaction between 2-nitropropane anion and α-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-ylethanone or 2-bromo-1-(4-nitrophenylethanone were reacted with several cyclic nitronate anions to form α,β-unsaturated ketones via a SRN1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues.

  18. Organobase catalyzed 1,4-conjugate addition of 4-hydroxycoumarin on chalcones: Synthesis, NMR and single-crystal X-ray diffraction studies of novel warfarin analogues

    Science.gov (United States)

    Talhi, Oualid; Fernandes, José A.; Pinto, Diana C. G. A.; Almeida Paz, Filipe A.; Silva, Artur M. S.

    2015-08-01

    The synthesis of a new series of warfarin analogues by convenient organobase catalyzed 1,4-conjugate addition of 4-hydroxycoumarin to chalcone derivatives is described. 1H NMR spectroscopy evidenced the presence of a predominant acyclic open-form together with the cyclic hemiketal tautomers of the resulting Michael adducts. The acyclic open-form has been unequivocally proved by single-crystal X-ray diffraction analysis. The use of the B ring ortho-hydroxychalcone synthons in this reaction has led to a diastereoselective synthesis of warfarin bicyclo[3.3.1]nonane ketal derivatives.

  19. In vitro anti-inflammatory, cytotoxic and antioxidant activities of boesenbergin A, a chalcone isolated from Boesenbergia rotunda (L.) (fingerroot)

    Energy Technology Data Exchange (ETDEWEB)

    Isa, N.M. [UPM-MAKNA Cancer Research Laboratory, Institute of Bioscience, University Putra Malaysia, Serdang, Selangor (Malaysia); Abdelwahab, S.I. [Department of Pharmacy, Faculty of Medicine, University of Malaya, Kuala Lumpur, (Malaysia); Mohan, S. [Centre of Natural Products and Drug Discovery, Department of Pharmacology, Faculty of Medicine, University of Malaya, Kuala Lumpur, (Malaysia); Abdul, A.B. [UPM-MAKNA Cancer Research Laboratory, Institute of Bioscience, University Putra Malaysia, Serdang, Selangor (Malaysia); Sukari, M.A. [Department of Chemistry, Faculty of Science, University Putra Malaysia, Serdang, Selangor (Malaysia); Taha, M.M.E.; Syam, S. [UPM-MAKNA Cancer Research Laboratory, Institute of Bioscience, University Putra Malaysia, Serdang, Selangor (Malaysia); Narrima, P.; Cheah, S.Ch. [Centre of Natural Products and Drug Discovery, Department of Pharmacology, Faculty of Medicine, University of Malaya, Kuala Lumpur, (Malaysia); Ahmad, S. [Faculty of Biotechnology, University Putra Malaysia, Serdang, Selangor (Malaysia); Mustafa, M.R. [Centre of Natural Products and Drug Discovery, Department of Pharmacology, Faculty of Medicine, University of Malaya, Kuala Lumpur, (Malaysia)

    2012-02-27

    The current in vitro study was designed to investigate the anti-inflammatory, cytotoxic and antioxidant activities of boesenbergin A (BA), a chalcone derivative of known structure isolated from Boesenbergia rotunda. Human hepatocellular carcinoma (HepG2), colon adenocarcinoma (HT-29), non-small cell lung cancer (A549), prostate adenocarcinoma (PC3), and normal hepatic cells (WRL-68) were used to evaluate the cytotoxicity of BA using the MTT assay. The antioxidant activity of BA was assessed by the ORAC assay and compared to quercetin as a standard reference antioxidant. ORAC results are reported as the equivalent concentration of Trolox that produces the same level of antioxidant activity as the sample tested at 20 µg/mL. The toxic effect of BA on different cell types, reported as IC{sub 50}, yielded 20.22 ± 3.15, 10.69 ± 2.64, 20.31 ± 1.34, 94.10 ± 1.19, and 9.324 ± 0.24 µg/mL for A549, PC3, HepG2, HT-29, and WRL-68, respectively. BA displayed considerable antioxidant activity, when the results of ORAC assay were reported as Trolox equivalents. BA (20 µg/mL) and quercetin (5 µg/mL) were equivalent to a Trolox concentration of 11.91 ± 0.23 and 160.32 ± 2.75 µM, respectively. Moreover, the anti-inflammatory activity of BA was significant at 12.5 to 50 µg/mL and without any significant cytotoxicity for the murine macrophage cell line RAW 264.7 at 50 µg/mL. The significant biological activities observed in this study indicated that BA may be one of the agents responsible for the reported biological activities of B. rotunda crude extract.

  20. Synthesis of a novel chalcone derivative%新型查尔酮类衍生物的合成

    Institute of Scientific and Technical Information of China (English)

    侯玲; 李依南; 刘若灿; 张波; 杨迪; 蔡志强

    2014-01-01

    A new chalcone derivative was PrePared from acetoPhenone in the catalysis of thionyl chloride, and then in the BPO induced by bromination,hydrolyzed to generate the target Product. The structure identification was Performed by IR,ESI-MS,1 H NMR. The affecting factors of the condensation reaction were discussed so as to select the best reaction conditions. The results show that the better reaction condi-tions of the aldol condensation are as follows:n(acetoPhenone):n(SOCl2)= 1. 2:1,the reaction tem-Perature is room temPerature,the reaction time is 30 min,and the aldol reaction yield can reach 72%.%以苯乙酮为原料进行自身羟醛缩合反应,生成1,3-二苯基-2-丁烯-1-酮,然后在BPO引发下,用NBS进行溴代,经水解后生成新型查尔酮衍生物( Z)-1,3-二苯基-4-羟基-2-丁烯-1-酮,并采用IR、ESI-MS、1 H NMR对其结构进行了表征。考察羟醛缩合反应催化剂、温度、物料配比等因素对合成的影响。结果表明,缩合反应的较佳条件是:n(苯乙酮):n(氯化亚砜)=1.2:1,反应温度为室温,反应时间为30 min,缩合产物收率达72%。

  1. Analysis of the relationship between Chalcone Isomerase gene expression level and rutin production in Ficus deltoidea var. deltoidea and F. deltoidea var. angustifolia

    Science.gov (United States)

    Najid, Najihah Mohd; Zain, Che Radziah Che Mohd; Zainal, Zamri

    2016-11-01

    Ficus deltoidea (moraceae) is a herbal plant with medicinal values. Previous studies reported that the F. deltoidea contains a high level of bioactive compounds such as flavonoids. A cDNA encodes for chalcone isomerase was identified from F. deltoidea, designated as FdCHI, which involved in the isomerization of naringenin chalcone to naringenin. Naringenin is a key branch point for the synthesis of rutin, which is believed involved in defense mechanism in the plant. Therefore, we hypothesized that there might be a direct relationship between FdCHI expression level and rutin production in leaves of F. deltoidea var. deltoidea (FDD) and F. deltoidea var. angustifolia (FDA). Our result showed that expression level of FdCHI in leaves FDD was greater than FDA. Analysis of High Performance Liquid Chromatography (HPLC) revealed that rutin was only detected in FDA leaves. Based on the results between FdCHI expression and rutin production, this study concluded that there is no relationship between FdCHI expression and rutin production in leaves of FDA and FDD.

  2. 对甲苯磺酸催化查尔酮的合成%Synthtsis of Chalcone Catalyzed by P-toluenesulfonic Acid

    Institute of Scientific and Technical Information of China (English)

    谭昌会; 郑荣选; 罗淑云; 林俏焰

    2012-01-01

    研究了查耳酮的制备方法和缩合反应的影响因素选择最佳的反应条件,实验的结果表明,合成查尔酮的缩合反应的较佳条件是:n(苯乙酮)加(间硝基苯甲醛)=1∶1,反应温度是70℃,反应的时间3h,对甲笨磺酸为3 g,乙酸用量为20 mL,在此条件下查尔酮的收率达71.6%.%Synthesis methods of chalcone were studied, affecting factors of the condensation reaction were discussed so as to select the best reaction conditions. The experimental results show that the better reaction conditions of the synthesis are as follows: n (m-nitrobenzaldehyde) / n (preparation) = 1 : 1, the reaction temperature is 70 ℃, the reaction time is 3 h, p-toluene sulfonic acid dosage and acetic acid dosage are 3 g and 20 mL , respectively. Under above conditions, the chalcone yield can reach 71.6%.

  3. Anti-tumour activity of a novel coumarin-chalcone hybrid is mediated through intrinsic apoptotic pathway by inducing PUMA and altering Bax/Bcl-2 ratio.

    Science.gov (United States)

    Singh, Neetu; Sarkar, Jayanta; Sashidhara, Koneni V; Ali, Shakir; Sinha, Sudhir

    2014-06-01

    Coumarins and chalcones are secondary plant metabolites which have shown an array of pharmacological properties including anti-tumour activity. We have previously reported on the synthesis and anti-proliferative activity of a series of novel coumarin-chalcone hybrids. Now we report on the in vivo efficacy as well as mechanism of action of the most potent molecule of the series, S009-131. Oral administration of this molecule resulted in regression of tumours induced by HeLa cell xenografts in nod SCID mice. The molecule inhibited proliferation of cervical cancer cells (HeLa and C33A) by inducing apoptosis and arresting cell cycle at G2/M phase. Apoptosis was induced through induction of caspase-dependent intrinsic pathway and alterations in the cellular levels of Bcl-2 family proteins. The mitochondrial transmembrane potential got highly depleted in S009-131 treated cells due to an increase in Bax/Bcl-2 ratio and intracellular ROS. The molecule induced release of cytochrome c into the cytosol and activation of initiator caspase-9 and executioner caspases-3/7. Tumour suppressor protein p53 and its transcriptional target PUMA were up regulated, suggesting their role in mediating the cell death. These results suggest that S009-131 is a potent candidate for the chemotherapy of cervical carcinoma.

  4. CoMFA, CoMSIA, HQSAR and molecular docking analysis of ionone-based chalcone derivatives as antiprostate cancer activity

    Directory of Open Access Journals (Sweden)

    R Sharma

    2016-01-01

    Full Text Available Androgen receptor has been proved to be effective site for treatment of prostate cancer. Molecular modeling methods performed on forty-three ionone based chalcones derivatives as anti-prostate cancer activity. The designed comparative molecular field analysis, comparative similarity indices analysis and hologram quantitative structure activity relationship models produced statistically significant results with the cross-validated correlation coefficients (q2 of 0.527, 0.550 and 0.670, non-cross-validated correlation coefficients (r2 0.636, 0.671 and 0.746 and predicted r2 (Pred r2 of 0.621, 0.563 and 0.732, respectively. Furthermore, bioactive conformation was explored and explained by docking of the potent compound 25 into the binding site of androgen receptor. Present study deals with comparative molecular field analysis, comparative similarity indices analysis and hologram quantitative structure activity relationship and molecular docking studies of the ionone-based chalcones and their derivatives, obtained from literature. The model obtained could be effectively used as a channeling tool for further structure modification and designing of some novel potent anti-prostate cancer compounds.

  5. The Plant-Derived Chalcone 2,2',5'-Trihydroxychalcone Provides Neuroprotection against Toll-Like Receptor 4 Triggered Inflammation in Microglia.

    Science.gov (United States)

    Jiwrajka, Manasi; Phillips, Alexandra; Butler, Matt; Rossi, Miriam; Pocock, Jennifer M

    2016-01-01

    Chalcones are plant metabolites with potential for therapeutic exploitation as antioxidant, anti-inflammatory, and antiproliferative agents. Here we explored the neuroprotective effects of 2,2',5'-trihydroxychalcone (225THC), a potent antioxidant with radical-scavenging properties. 225THC was found to be a potent inhibitor of apoptosis in stimulated primary rat neuronal cultures. This was likely mediated by an anti-inflammatory effect on microglial cells since 225THC inhibited LPS-stimulated TNF-α and IL-6 secretion from primary rat microglia and modulated the cytokine/chemokine profile of BV2 microglial cells. Additionally, 225THC inhibited LPS-evoked inducible nitric oxide synthase expression but did not influence endogenous superoxide generation. Microglial flow cytometric analyses indicated the 225THC treatment induced a shift from an M1-like phenotype to a more downregulated microglial profile. Taken together these data suggest that the chalcone 2,2',5'-trihydroxychalcone can modulate neuroinflammatory activation in brain-derived microglia and holds promise as a therapeutic in neuroinflammatory conditions.

  6. The Plant-Derived Chalcone 2,2′,5′-Trihydroxychalcone Provides Neuroprotection against Toll-Like Receptor 4 Triggered Inflammation in Microglia

    Directory of Open Access Journals (Sweden)

    Manasi Jiwrajka

    2016-01-01

    Full Text Available Chalcones are plant metabolites with potential for therapeutic exploitation as antioxidant, anti-inflammatory, and antiproliferative agents. Here we explored the neuroprotective effects of 2,2′,5′-trihydroxychalcone (225THC, a potent antioxidant with radical-scavenging properties. 225THC was found to be a potent inhibitor of apoptosis in stimulated primary rat neuronal cultures. This was likely mediated by an anti-inflammatory effect on microglial cells since 225THC inhibited LPS-stimulated TNF-α and IL-6 secretion from primary rat microglia and modulated the cytokine/chemokine profile of BV2 microglial cells. Additionally, 225THC inhibited LPS-evoked inducible nitric oxide synthase expression but did not influence endogenous superoxide generation. Microglial flow cytometric analyses indicated the 225THC treatment induced a shift from an M1-like phenotype to a more downregulated microglial profile. Taken together these data suggest that the chalcone 2,2′,5′-trihydroxychalcone can modulate neuroinflammatory activation in brain-derived microglia and holds promise as a therapeutic in neuroinflammatory conditions.

  7. Synthesis of Novel Chalcone-piperazine Derivatives%新型查尔酮哌嗪衍生物的合成

    Institute of Scientific and Technical Information of China (English)

    王秀丽; 王子杰; 毛泽伟

    2016-01-01

    4-Dimethylamino-4′-(1-piperazinyl)chalcone(2) was preapared by aldol condensation and substitution , using 4-dimethylaminobenzaldehyde and 4′-fluoroacetophenone as materials .Six novel chalcone-piperazine derivatives , in yields of 71% ~88%, were synthesized by reaction of 2 with haloalkanes.The structures were characterized by 1 H NMR, 13 C NMR and HR-MS.%以4-二甲氨基苯甲醛和2-溴-4′-氟苯乙酮为原料,经缩合和取代反应制得4-二甲氨基-4′-(1-哌嗪基)查尔酮(2);2与卤代烃反应合成了6个新型的查尔酮哌嗪衍生物,收率71%~88%,其结构经1 H NMR,13 C NMR和HR-MS表征。

  8. The novel oxygenated chalcone, 2,4-dimethoxy-4'-butoxychalcone, exhibits potent activity against human malaria parasite Plasmodium falciparum in vitro and rodent parasites Plasmodium berghei and Plasmodium yoelii in vivo

    DEFF Research Database (Denmark)

    Chen, M; Brøgger Christensen, S; Zhai, L;

    1997-01-01

    Previous studies have shown that licochalcone A, an oxygenated chalcone, exhibits antileishmanial and antimalarial activities. The present study was designed to examine the antimalarial activity of an analog of licochalcone A, 2,4-dimethoxy-4'-butoxychalcone (2,4mbc). 2,4mbc inhibited the in vitro...

  9. Cloning and Sequence Analyzing of Chalcone Synthase Gene in Loropetalum chinense var.Rubrum%红花檵木CHS基因的克隆与序列分析

    Institute of Scientific and Technical Information of China (English)

    许威; 于晓英; 陈己任; 符红艳; 胡博文; 陈彦斌; 李达

    2013-01-01

    查尔酮合酶(chalcone synthase,CHS)是进入类黄酮和花色素苷次生代谢的第1个关键酶.根据植物查尔酮合成酶保守区序列设计引物,以红花檵木Loropetalurn chinense var.Rubrum)大叶红的嫩叶为材料,用RT-PCR方法,分离得到了一个查尔酮合成酶基因的eDNA(GenBank登录号为JQ609678),将该基因命名为Lc vrCHS1.该序列长927 bp,编码232个氨基酸残基.其核苷酸序列与GenBank已登录的同样来源的核桃、山茶属植物CHS序列同源性达83%,与其他科植物(绣球花、葡萄、桃、马铃薯、甘草、领春木属)CHS序列同源性也达到80%以上;其编码的氨基酸序列与山茶属、葡萄、鳄梨、洋梨、沙梨、映山红CHS基因编码的氨基酸序列同样具有高度同源性,同源性高达98%.%Chalcone synthase (chalcone synthase, CHS) is the key enzyme that catalyzes the first step in flavonoids biosynthesis and anthocyanins secondary metabolites. A full-length cDNA encoding CHS was cloned from the young leaves of Loropetalurn chinense var. rubrum by RT-PCR using specific primers based on the highly conserved sequences of plant CHS that had already known. Blast search revealed that it was a new gene, and was named as LcvrCHSl (GenBank accession: JQ609678). The sequence was 927 bp, encoding 232 amino acid residues. It had 83% sequence homology with walnut and camellia that had been logged in GenBank; with other genus plants (hydrangea, grapes, peaches, potatoes, licorice, Euptelea genus), CHS sequence homology was also more than 80%; with other plants (camellia, grapes, avocados, bartlett pear, sand pear, azalea), CHS sequence also had high homology, up to 98% homology.

  10. New structure–activity relationships of chalcone inhibitors of breast cancer resistance protein: polyspecificity toward inhibition and critical substitutions against cytotoxicity

    Directory of Open Access Journals (Sweden)

    Rangel LP

    2013-09-01

    Full Text Available Luciana Pereira Rangel,1,2,* Evelyn Winter,1,3,* Charlotte Gauthier,1 Raphaël Terreux,4 Louise D Chiaradia-Delatorre,5 Alessandra Mascarello,5 Ricardo J Nunes,5 Rosendo A Yunes,5 Tania B Creczynski-Pasa,3 Sira Macalou,1 Doriane Lorendeau,1 Hélène Baubichon-Cortay,1 Antonio Ferreira-Pereira,2 Attilio Di Pietro11Equipe Labellisée Ligue 2013, BMSSI UMR 5086 CNRS/Université Lyon 1, Institut de Biologie et Chimie des Protéines, Lyon, France; 2Department of General Microbiology, Institute of Microbiology, Federal University of Rio de Janeiro, Rio de Janeiro, Brazil; 3Department of Pharmaceutical Sciences, PPGFAR, Federal University of Santa Catarina, Florianopolis, Santa Catarina, Brazil; 4Equipe BISI, BMSSI UMR 5086 CNRS/Université Lyon 1, Institut de Biologie et Chimie des Protéines, Lyon, France; 5Department of Chemistry, Federal University of Santa Catarina, Florianopolis, Santa Catarina, Brazil*These authors contributed equally to this workAbstract: Adenosine triphosphate-binding cassette subfamily G member 2 (ABCG2 plays a major role in cancer cell multidrug resistance, which contributes to low efficacy of chemotherapy. Chalcones were recently found to be potent and specific inhibitors, but unfortunately display a significant cytotoxicity. A cellular screening against ABCG2-mediated mitoxantrone efflux was performed here by flow cytometry on 54 chalcone derivatives from three different series with a wide panel of substituents. The identified leads, with submicromolar IC50 (half maximal inhibitory concentration values, showed that the previously identified 2'-OH-4',6'-dimethoxyphenyl, as A-ring, could be efficiently replaced by a 2'-naphthyl group, or a 3',4'-methylenedioxyphenyl with lower affinity. Such a structural variability indicates polyspecificity of the multidrug transporter for inhibitors. At least two methoxyl groups were necessary on B-ring for optimal inhibition, but substitution at positions 3, 4, and 5 induced cytotoxicity

  11. Antioxidant activities of [60]fullerene derivatives from chalcone, flavone and flavanone: A ONIOM approach via H-atom and electron transfer mechanism

    Science.gov (United States)

    Thong, Nguyen Minh; Dao, Duy Quang; Ngo, Thi Chinh; Huyen, Trinh Le; Nam, Pham Cam

    2016-05-01

    Antioxidant properties of C60 flavonoid conjugates were computationally examined via their O-H bond dissociation enthalpies (BDEs) and ionization energies (IEs) using two-layer ONIOM and PM6 methods, respectively. Eight ONIOM((RO)B3LYP/6-311++G(2df,2p):PM6) models were evaluated by computing BDE(O-H)s of a series of polyphenol. Synthetic mechanism of C60 flavonoid conjugates was also explored via the potential energy surfaces of reaction between C60 and malonate flavonoid derivatives (chalcone, flavone and flavanone) at the B3LYP/6-31G(d)//PM6. Antioxidant activities of C60 flavonoid conjugates were discussed via hydrogen atom transfer, single electron transfer mechanisms and the effect of C60 on the BDE(O-H)s and IEs of these compounds.

  12. Designing, synthesis of selective and high-affinity chalcone-benzothiazole hybrids as Brugia malayi thymidylate kinase inhibitors: In vitro validation and docking studies.

    Science.gov (United States)

    Sashidhara, Koneni V; Avula, Srinivasa Rao; Doharey, Pawan Kumar; Singh, L Ravithej; Balaramnavar, Vishal M; Gupta, Jyoti; Misra-Bhattacharya, Shailja; Rathaur, Sushma; Saxena, Anil K; Saxena, Jitendra Kumar

    2015-10-20

    In our continuing search for safe and efficacious antifilarials, a series of novel chalcone-benzothiazole hybrids have been synthesized and evaluated for their Brugia malayi thymidylate kinase (BmTMK) enzyme inhibition activity. Their selectivity towards BmTMK was studied and compared to the human TMK (HsTMK) by an in silico method. Out of seventeen derivatives, compounds 34 and 42 showed higher interactions with the BmTMK active site. MolDock docking model revealed the interactions of these two derivatives and the results corroborated well with their in vitro antifilarial activities. Our studies suggest that these hybrids are selective towards the BmTMK enzyme and may serve as potential therapeutic agents against filariasis.

  13. Antiproliferative activity and induction of apoptosis in PC-3 cells by the chalcone cardamonin from Campomanesia adamantium (Myrtaceae) in a bioactivity-guided study.

    Science.gov (United States)

    Pascoal, Aislan Cristina Rheder Fagundes; Ehrenfried, Carlos Augusto; Lopez, Begoña Gimenez-Cassina; de Araujo, Thiago Matos; Pascoal, Vinicius D'ávila Bitencourt; Gilioli, Rovilson; Anhê, Gabriel Forato; Ruiz, Ana Lúcia Tasca Goes; Carvalho, João Ernesto de; Stefanello, Maria Elida Alves; Salvador, Marcos José

    2014-02-07

    The Myrtaceae family is a common source of medicines used in the treatment of numerous diseases in South America. In Brazil, fruits of the Campomanesia species are widely used to make liqueurs, juices and sweets, whereas leaves are traditionally employed as a medicine for dysentery, stomach problems, diarrhea, cystitis and urethritis. Ethanol extracts of Campomanesia adamantium (Myrtaceae) leaves and fruits were evaluated against prostate cancer cells (PC-3). The compound (2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one, cardamonin) was isolated from ethanol extracts of C. adamantium leaves in a bioactivity-guided study and quantified by UPLC-MS/MS. In vitro studies showed that the isolated chalcone cardamonin inhibited prostate cancer cell proliferation and decreased the expression of NFkB1. Moreover, analysis by flow cytometry showed that this compound induced DNA fragmentation, suggesting an effect on apoptosis induction in the PC-3 cell line.

  14. Review on the molecular biology of plant chalcone synthase%植物查尔酮合成酶分子生物学研究进展

    Institute of Scientific and Technical Information of China (English)

    王燕; 许锋; 程水源

    2007-01-01

    查尔酮合成酶(chalcone synthase,CHS,EC 2.3.1.74),是植物类黄酮物质合成途径中的第一个酶,也是植物次生代谢途径中的关键酶之一,对植物具有非常重要的生理意义.为此,综述了查尔酮合成酶基因结构、基因进化、表达调控机理以及诱导因子,概述了查尔酮合成酶基因工程在植物生理方面的研究,并进一步对查尔酮合成酶的分子生物学研究做了展望.

  15. A Study on Synthesis Process of 2-Hydroxyl Chalcon%2-羟基查耳酮合成工艺的研究

    Institute of Scientific and Technical Information of China (English)

    刘健

    2015-01-01

    Chalcone is a key intermediate for pharmaceutical synthesis of flavonoids widely used as medicine. The classical method of synthesis of 2- hydroxy chalcone uses trimethoxy benzene as raw material, and uses acetyl chloride reaction to produce trimethoxy acetophenone, and then it reacts with two methoxy phenyl ac-etaldehyde to produce chalcones. Experimental results show that using the aluminum chloride as catalyst in carbon disulfide solution, when trimethoxy benzene and acetyl chloride ratio is1:1.05, stirring at a constant temperature of 40 DEG C, 2, 4, 6-trimethoxy phenyl ethyl ketone yield can reach the highest percentage, 92%. 2, 4, 6-trimethoxy phenyl ethyl ketone react with 2,4-two methoxy benzaldehydeto produce 2- hydroxy chalcone, with reactant ratio of ethanol solution of 1:1. When 2, 4, 6-trimethoxy acetophenone and amount of 50% KOH ratio is 1:4, the reaction yield is 96%, the total yield of the reaction 88%,which is the optimal re-action condition for industrial production.%查尔酮是合成广泛应用的医药黄酮类化合物的关键中间体,2-羟基查耳酮的经典合成方法是以三甲氧基苯为原料,与乙酰氯反应生成三甲氧基苯乙酮,再与二甲氧基苯乙醛发生反应生成查耳酮。实验结果表明,以三氯化铝为催化剂,在二硫化碳溶液中,三甲氧基苯和乙酰氯配比为1:1.05时,在恒温40℃搅拌,得到的2,4,6-三甲氧基苯乙酮产率最高,为92%。2,4,6-三甲氧基苯乙酮再与2,4-二甲氧基苯甲醛反应得到2-羟基查耳酮,大量的乙醇溶液中反应物配比1:1,2,4,6-三甲氧基苯乙酮与50%的KOH加入量配比为1:4,反应收率为96%,最后总反应收率为88%,为工业生产最佳反应条件。

  16. Synthesis and biological evaluation of beta-chloro vinyl chalcones as inhibitors of TNF-alpha and IL-6 with antimicrobial activity.

    Science.gov (United States)

    Bandgar, Babasaheb P; Patil, Sachin A; Korbad, Balaji L; Nile, Shivraj H; Khobragade, Chandrahase N

    2010-06-01

    A series of beta-chloro vinyl chalcones have been synthesized by Claisen-Schmidt condensation. beta-chloro vinyl aldehyde has been synthesized by the Vilsmayer-Hack formylation reaction. The structures of the newly synthesized compounds were confirmed by 1H NMR, IR and Mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-alpha and IL-6) and antimicrobial (antibacterial and antifungal) activity. Compounds 5a, 5d, 5e, 5g and 5i exhibited promising activity against IL-6 with 58-83% inhibition at 10 microM concentration. None of the compound was found to be cytotoxic in CCK-8 cells at 10 microM concentration. Whereas compounds 5b, 5d, 5e and 5i showed very good antibacterial activity and compounds 5a, 5b, 5e and 5i showed good antifungal activity.

  17. Synthesis and biological evaluation of α-triazolyl chalcones as a new type of potential antimicrobial agents and their interaction with calf thymus DNA and human serum albumin.

    Science.gov (United States)

    Yin, Ben-Tao; Yan, Cong-Yan; Peng, Xin-Mei; Zhang, Shao-Lin; Rasheed, Syed; Geng, Rong-Xia; Zhou, Cheng-He

    2014-01-01

    A series of α-triazolyl chalcones were efficiently synthesized. Most of the prepared compounds showed effective antibacterial and antifungal activities. Noticeably, α-triazolyl derivative 9a exhibited low MIC value of 4 μg/mL against MRSA and Micrococcus luteus, which was comparable or even superior to reference drugs. The further research revealed that compound 9a could effectively intercalate into Calf Thymus DNA to form 9a-DNA complex which might block DNA replication to exert their powerful antimicrobial activities. Competitive interactions between 9a and metal ions to Human Serum Albumin (HSA) suggested the participation of Fe(3+), K(+) and Mg(2+) ions in 9a-HSA system could increase the concentration of free 9a, shorten its storage time and half-life in the blood, thus improving its antimicrobial efficacy.

  18. Synthesis and antimicrobial evaluation of L-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone.

    Science.gov (United States)

    Jin, Xin; Zheng, Chang-Ji; Song, Ming-Xia; Wu, Yan; Sun, Liang-Peng; Li, Yin-Jing; Yu, Li-Jun; Piao, Hu-Ri

    2012-10-01

    Four novel series of compounds, including the l-phenylalanine-derived C5-substituted rhodanine (6a-q, 7a-j) and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone (9a-e, 11a-e) have been designed, synthesized, characterized, and evaluated for their antibacterial activity. Some of these compounds showed significant antibacterial activity against Gram-positive bacterias, especially against the strains of multidrug-resistant clinical isolates, among which compounds 6c-e, 6g, 6i, 6j and 6q exhibiting high levels of antimicrobial activity against Staphylococcus aureus RN4220 with minimum inhibitory concentration (MIC) values of 2 μg/mL. Compound 6q showed the most potent activity of all of the compounds against all of the test multidrug-resistant clinical isolates tested. Unfortunately, however, none of the compounds were active against Gram-negative bacteria at 64 μg/mL.

  19. A novel chalcone derivative attenuates the diabetes-induced renal injury via inhibition of high glucose-mediated inflammatory response and macrophage infiltration

    Energy Technology Data Exchange (ETDEWEB)

    Fang, Qilu [Chemical Biology Research Center, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang (China); Zhao, Leping [Department of Pharmacy, the Affiliated Yueqing Hospital, Wenzhou Medical University, Wenzhou, Zhejiang (China); Wang, Yi; Zhang, Yali [Chemical Biology Research Center, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang (China); Li, Zhaoyu [Department of International High School, Shanghai Jiaotong University Nanyang Affiliated (Kunshan) School, Minhang District, Shanghai (China); Pan, Yong; Kanchana, Karvannan; Wang, Jingying; Tong, Chao [Chemical Biology Research Center, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang (China); Li, Dan, E-mail: yqyyld@163.com [Department of Nephrology, the Affiliated Yueqing Hospital, Wenzhou Medical University, Wenzhou, Zhejiang (China); Liang, Guang, E-mail: wzmcliangguang@163.com [Chemical Biology Research Center, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang (China)

    2015-01-15

    Inflammation plays a central role in the development and progression of diabetic nephropathy (DN). Researches on novel anti-inflammatory agents may offer new opportunities for the treatment of DN. We previously found a chalcone derivative L6H21 could inhibit LPS-induced cytokine release from macrophages. The aim of this study was to investigate whether L6H21 could ameliorate the high glucose-mediated inflammation in NRK-52E cells and attenuate the inflammation-mediated renal injury. According to the results, L6H21 showed a great inhibitory effect on the expression of pro-inflammatory cytokines, cell adhesion molecules, chemokines, and macrophage adhesion via down-regulation of NF-κB/MAPKs activity in high glucose-stimulated renal NRK-52E cells. Further, in vivo oral administration with L6H21 at a dosage of 20 mg/kg/2 days showed a decreased expression of pro-inflammatory cytokines, cell adhesion molecules, which subsequently contributed to the inhibition on renal macrophage infiltration, the reduction of serum creatinine and BUN levels, and the improvement on the fibrosis and pathological changes in the renal tissues of diabetic mice. These findings provided that chalcone derived L6H21 may be a promising anti-inflammatory agent and have the potential in the therapy of diabetic nephropathy, and importantly, MAPK/NF-κB signaling system may be a novel therapeutic target for human DN in the future. - Highlights: • Inflammation plays a central role in the development of diabetic nephropathy. • Compound L6H21 reduced the high glucose-mediated inflammation in NRK-52E cells. • Compound L6H21 attenuated the inflammation-mediated renal injury. • L6H21 exhibited anti-inflammatory effects via inactivation of NF-κB/MAPKs. • MAPKs/NF-κB may be a novel therapeutic target in diabetic nephropathy treatment.

  20. Research on the Extraction Technology of Chalcone from the Angelica Keiskei by Ultrasonic Wave%超声波辅助提取明日叶查尔酮的工艺优化

    Institute of Scientific and Technical Information of China (English)

    宁鸿珍; 陈欣华; 王曼曼; 王茜; 刘楠; 马东; 王丹丹; 高胜海

    2014-01-01

    To investigate the optimum extraction of chalcone from the Angelica keiskei by ultrasonic wave, and to determine the content of chalcone. According to single factor experiment, the influence of five parameters on the extraction rate of chalcone were investigated, including the ultrasonic power, ethanol concentration, the ratio of material and solvent, the extracting time,the extracting temperature. Then orthogonal experiment was employed to determine the optimum extraction of chalcone from the Angelica keiskei by ultrasonic wave. The influencing order of each factor on the yield of chalcone was solid to liquid ratio>extraction temperature>concentration of ethanol>extraction time>ultrasonic power,and the optimal conditions of chalcone extraction from the Angelica keiskei were:ultrasonic power of 300 W, ethanol concentration of 70%,extraction temperature of 50℃, solid to liquid ratio of 1∶50, extraction time of 20 min. The Angelica keiskei was extracted twice under those conditions,the chalcone extraction yield was 7.53 mg/g. The cholcone content is high. This extraction technology is simple, efficient,energy-saving, feasible, which can provide reference for industrial extraction of chalcone from the Angelica keiskei.%探讨超声波辅助萃取技术在明日叶查尔酮提取应用中的最佳工艺,并测定明日叶中查尔酮的含量。采用单因素实验研究超声功率、乙醇浓度、料液比、提取时间、提取温度对明日叶查尔酮提取率的影响,在此基础上,利用正交试验确定超声波辅助提取明日叶中查尔酮的最佳工艺条件。在所探讨的因素中,对明日叶中查尔酮提取的影响程度为:料液比>乙醇浓度>提取温度>提取时间>超声功率。最佳工艺参数:超声波功率300 W,乙醇浓度为70%,提取温度为50℃,料液比为1∶50,萃取时间为20 min,提取二次后吸光值为1.191,查尔酮得率为7.53 mg/g。明日叶中查尔酮含量较高,优化

  1. Research progress of the anti-cancer,anti-inflammatory activities of chalcone as bioactive plant constituents%查尔酮的结构修饰及抗癌、抗炎活性研究进展

    Institute of Scientific and Technical Information of China (English)

    李湘洲; 郭远良; 旷春桃; 贺义昌

    2011-01-01

    Chalcone, which are abundant in plants as a class of flavonoids, are confirmed to possess a diverse array of pharmacological activities and considered as a promising template for drug design. The studying progress on anticancer, anti-inflammatory activities of chalcone, and the structure-activity relationship(SAR)was summarized. The findings indicate that chalcone has widely pharmacology activity, safety, simple structure, preparation convenient,and is a kind of good primer for drug development.%查尔酮类化合物是广泛存在于自然界中一种黄酮类化合物,具有抗癌、抗炎症、抗菌、抗寄生虫、抗病毒等生物活性,是一类很具有前途的药物模板.重点阐述了近年来杳尔酮类化合物的抗癌、抗炎症活性以及构效关系研究进展.结果表明查尔酮类化合物药理活性广泛、安全、结构简单且制备方便,是一个良好的药物开发先导物.

  2. A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors.

    Science.gov (United States)

    Salian, Vinutha V; Narayana, Badiadka; Yathirajan, Hemmige S; Akkurt, Mehmet; Çelik, Ömer; Ersanlı, Cem Cüneyt; Glidewell, Christopher

    2015-07-01

    Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)-1-(2,4-Dichlorophenyl)-3- [4-(prop-1-en-2-yl)phenyl]prop-2-en-1-one, C18H14Cl2O, (I), prepared from 4-(prop-1-en-2-yl)benzaldehyde and 2,4-dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)-3-(4-chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one reacts with acetone to produce (5RS)-3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]cyclohex-2-en-1-one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3-oxobutanoate to give methyl (1RS,6SR)-4-(4-chlorophenyl)-6-[4-(propan-2-yl)phenyl]-2-oxocyclohex-3-ene-1-carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, of ethyl (1RS,6SR)-6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4''-bromo-4-fluoro-5'-hydroxy-1,1':3',1''-terphenyl-4'-carboxylate, C21H16BrFO3, (IV), which crystallizes with Z' = 2 in the space group P-1. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C-H...O and C-H...π(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion-related pairs of C-H...O hydrogen bonds and the other from inversion-related pairs of C-H...π(arene) hydrogen bonds. Comparisons are made with related compounds.

  3. Involvement of Salicylic Acid on Antioxidant and Anticancer Properties, Anthocyanin Production and Chalcone Synthase Activity in Ginger (Zingiber officinale Roscoe Varieties

    Directory of Open Access Journals (Sweden)

    Ehsan Karimi

    2012-11-01

    Full Text Available The effect of foliar application of salicylic acid (SA at different concentrations (10−3 M and 10−5 M was investigated on the production of secondary metabolites (flavonoids, chalcone synthase (CHS activity, antioxidant activity and anticancer activity (against breast cancer cell lines MCF-7 and MDA-MB-231 in two varieties of Malaysian ginger, namely Halia Bentong and Halia Bara. The results of high performance liquid chromatography (HPLC analysis showed that application of SA induced the synthesis of anthocyanin and fisetin in both varieties. Anthocyanin and fisetin were not detected in the control plants. Accordingly, the concentrations of some flavonoids (rutin and apigenin decreased significantly in plants treated with different concentrations of SA. The present study showed that SA enhanced the chalcone synthase (CHS enzyme activity (involving flavonoid synthesis and recorded the highest activity value of 5.77 nkat /mg protein in Halia Bara with the 10−5 M SA treatment. As the SA concentration was decreased from 10−3 M to 10−5 M, the free radical scavenging power (FRAP increased about 23% in Halia Bentong and 10.6% in Halia Bara. At a concentration of 350 μg mL−1, the DPPH antioxidant activity recorded the highest value of 58.30%–72.90% with the 10−5 M SA treatment followed by the 10−3 M SA (52.14%–63.66% treatment. The lowest value was recorded in the untreated control plants (42.5%–46.7%. These results indicate that SA can act not only as an inducer but also as an inhibitor of secondary metabolites. Meanwhile, the highest anticancer activity against MCF-7 and MDA-MB-231 cell lines was observed for H. Bara extracts treated with 10−5 M SA with values of 61.53 and 59.88%, respectively. The results suggest that the high anticancer activity in these varieties may be related to the high concentration of potent anticancer components including fisetin and anthocyanin. The results thus indicate that the synthesis of

  4. Synthesis of newer 1,2,3-triazole linked chalcone and flavone hybrid compounds and evaluation of their antimicrobial and cytotoxic activities.

    Science.gov (United States)

    Kant, Rama; Kumar, Dharmendra; Agarwal, Drishti; Gupta, Rinkoo Devi; Tilak, Ragini; Awasthi, Satish Kumar; Agarwal, Alka

    2016-05-04

    The present study was carried out in an attempt to synthesize a new class of antimicrobial and antiplasmodial agents by copper catalyzed click chemistry to afford 25 compounds 10-14(a-e) of 1,4-disubstituted-1,2,3-triazole derivatives of chalcones and flavones. The structures of the newly synthesized compounds were established by elemental analysis, IR, (1)H NMR, (13)C NMR and Mass spectral data. The newly synthesized compounds were evaluated for their antibacterial activity against Gram positive bacteria (Staphylococcus aureus, Enterococcus faecalis), Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Shigella boydii, Klebsiella pneumoniae) and antifungal activity against (Candida albicans, Candida tropicalis, Candida parapsilosis, Cryptococcus neoformans, Dermatophyte) as well as molds (Aspergillus niger, Aspergillus fumigatus). The antiplasmodial and cytotoxic activities of these compounds were also evaluated against human malaria parasite Plasmodium falciparum strain 3D7 and human hepato-cellular carcinoma cells (Huh-7), respectively. Compounds 10a, 10c, 10d, 12c and 14e showed promising antibacterial activity while compounds 10e, 11d, 11e, 12c, 13a, 13b, 13e, 14a and 14d showed good antifungal activity as compared to the corresponding standard drugs. Compound 10b was found to be the most active against Plasmodium falciparum while the remaining compounds showed moderate to weak antiplasmodial activity. However, cytotoxic activities of all compounds were found ineffective against Huh-7 cells.

  5. Electrochemical and Fluorescent Properties of Ferrocenyl Chalcones Containing 1-Naphthalenyl Group: X-ray Crystal Structure of Fc-C(O)CH=CH-(1-Naph)

    Energy Technology Data Exchange (ETDEWEB)

    Suh, Woo Young; Jeon, Hyo Kyung; Lee, Ji Yeon; Lim, Chae Mi; Lee, Su Kyung; Noh, Dong Youn [Seoul Women' s University, Seoul (Korea, Republic of)

    2012-02-15

    Ferrocenyl chalcones (Fc-C(O)CH=CH-Ar: Fc-Ar) with mono- and di-1-naphthalenyl moieties (Fc-1Naph and Fc-d1Naph) were prepared and spectroscopically characterized. The enone bridge was in the s-cis conformation and the π-electrons on the C=C bond were further delocalized on the bridge. The naphthalenyl moiety deviates greatly from the enone-Cp plane by 26.9(1) .deg. . Cyclic voltammetry measurements for Fc-1Naph exhibit one reversible cycle for the redox of the ferrocenyl moiety at a lower potential, and one irreversible oxidation peak at the higher potential region. For Fc-d1Naph, the cyclic voltammogram is more featureless. Fluorescence properties for both compounds are active in polar solvents with λem = 500 nm (EtOH) and λem = 512 nm (MeOH) for Fc-1Naph and λem = 496 nm (EtOH) and λem = 508 nm (MeOH) for Fc-d1Naph. The intensity of Fc-d1Naph is more than twice than that of Fc-1Naph. The fluorescence properties for both compounds are inactive in the less polar solvents such as CH{sub 3}CN, CH{sub 2}Cl{sub 2} and CHCl{sub 3}.

  6. Synthesis and biological screening of a combinatorial library of beta-chlorovinyl chalcones as anticancer, anti-inflammatory and antimicrobial agents.

    Science.gov (United States)

    Bandgar, Babasaheb P; Gawande, Shrikant S

    2010-03-01

    A combinatorial library of beta-chlorovinyl chalcones (4) were synthesized by Claisen-Schmidt condensation reaction. Catalytic reaction of substituted 3-chloro-3-phenyl-propenal (2) and 1-(2,4-dimethoxy-phenyl)-ethanone or 1-(4-methoxy-phenyl)-ethanone (3) in alkaline conditions furnished the target compound 5-chloro-1-(2,4-dimethoxy-phenyl)-5-phenyl-penta-2,4-dien-1-one (4). The synthesized compounds were screened for their biological activity viz. anticancer, anti-inflammatory and antimicrobial activities. Synthesized compounds 4g and 4h revealed promising anti-inflammatory activity (66-67% TNF-alpha and 95-97% IL-6 inhibitory activity at 10 microM). Cytotoxicity of the compounds checked using CCK-8 cell lines and found to be nontoxic to slightly toxic. Furthermore, the anticancer activity (30-40%) was shown by compounds 4d, 4e, 4h and 4b at 10 microM concentrations against ACHN followed by Calu 1, Panc1, HCT116 and H460 cell lines. Some of the compounds 4d, 4e, 4a, 4i and 4b revealed promising antimicrobial activity at MIC 50-100 microg/mL against selected pathogenic bacteria and fungi.

  7. Synthesis, characterization and biological activities of some Ru(II) complexes with substituted chalcones and their applications as chemotherapeutics against breast cancer

    Science.gov (United States)

    Singh, Ashok K.; Saxena, Gunjan; Dixit, Shivani; Hamidullah; Singh, Sachin K.; Singh, Sudheer K.; Arshad, M.; Konwar, Rituraj

    2016-05-01

    Four new Ru(II) DMSO complexes with substituted chalcone ligands viz. (E)-1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (HL1), (E)-1-(2-hydroxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (HL2), (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (HL3) and (E)-1-(2-hydroxyphenyl)-3-(4-Chlorophenyl)prop-2-en-1-one (HL4) have been synthesized, and characterized by micro-analyses, IR, 1H NMR, UV-Vis and ESI-MS and screened for anti-cancer activity against breast cancer cell lines (MCF-7 and MDA MB-231). Compounds HL4 and [Ru(HL1) (O-DMSO)3(S-DMSO)]Cl (M1R) showed significant anti-breast cancer activity as evident from cytotoxicity, morphological and nuclear changes, DNA fragmentation and cell cycle arrest in breast cancer cells. UV-Vis and CD-spectra analysis showed HL4 and M1R interfered with DNA absorption spectra possibly due to DNA binding whereas these compounds were devoid of DNA topoisomerase inhibiting activity. Thus, these Ru(II) compounds have been established as new leads for future optimization by improving anti-cancer potency and safety.

  8. Xanthohumol, a main prenylated chalcone from hops, reduces liver damage and modulates oxidative reaction and apoptosis in hepatitis C virus infected Tupaia belangeri.

    Science.gov (United States)

    Yang, Mingbo; Li, Na; Li, Fang; Zhu, Qianqian; Liu, Xi; Han, Qunying; Wang, Yawen; Chen, Yanping; Zeng, Xiaoyan; Lv, Yi; Zhang, Pingping; Yang, Cuiling; Liu, Zhengwen

    2013-08-01

    Hepatitis C virus (HCV) infection in Tupaia belangeri (Tupaia) represents an important model of HCV infection. Xanthohumol (XN), a major prenylated chalcone from hops, has various biological activities including hepatopreventive and anti-viral activities. In this study, Tupaias infected with HCV RNA positive serum were used to evaluate the effects of XN on liver damage, oxidative reaction, apoptosis and viral protein expression in liver tissues. The Tupaias inoculated with HCV positive serum had elevated serum aminotransferase levels and inflammation, especially hepatic steatosis, and HCV core protein expression in liver tissue. In the animals inoculated with HCV positive serum, XN significantly decreased aminotransferase levels, histological activity index, hepatic steatosis score and transforming growth factor β1 expression in liver tissue compared with the animals without XN intervention. XN reduced HCV core protein expression in liver tissue compared with those without XN intervention but the difference was not significant. XN significantly decreased malondialdehyde, potentiated superoxide dismutase and glutathione peroxidase, reduced Bax expression, promoted Bcl-xL and inhibited caspase 3 activity in liver tissues compared with the animals without XN intervention. These results indicate that XN may effectively improve hepatic inflammation, steatosis and fibrosis induced by HCV in Tupaias primarily through inhibition of oxidative reaction and regulation of apoptosis and possible suppression of hepatic stellate cell activation. The anti-HCV potential of XN needs further investigation.

  9. Synthesis, spectral behaviour and photophysics of donor-acceptor kind of chalcones: Excited state intramolecular charge transfer and fluorescence quenching studies

    Science.gov (United States)

    Pannipara, Mehboobali; Asiri, Abdullah M.; Alamry, Khalid A.; Arshad, Muhammad N.; El-Daly, Samy A.

    2015-02-01

    The spectral and photophysical properties of two chalcones containing electron donating and accepting groups with intramolecular charge transfer characteristics were synthesized and characterized by 1H NMR, 13C NMR and X-ray crystallography. Both compounds show very strong solvent polarity dependent changes in their photophysical characteristics, namely, remarkable red shift in the emission spectra with increasing solvent polarity, large change in Stokes shift, significant reduction in the fluorescence quantum yield; indicating that the fluorescence states of these compounds are of intramolecular charge transfer (ICT) character. The solvent effect on the photophysical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment, fluorescence spectra, and fluorescence quantum yield of both compounds have been investigated comprehensively. For both dyes, Lippert-Mataga and Reichardt's correlations were used to estimate the difference between the excited and ground state dipole moments (Δμ). The interactions of dyes with colloidal silver nanoparticles (Ag NPs) were also studied in ethanol using steady state fluorescence quenching measurements. The fluorescence quenching data reveal that dynamic quenching and energy transfer play a major role in the fluorescence quenching of dyes by Ag NPs.

  10. 自旋标记查耳酮类化合物的合成及抗肿瘤活性%Synthesis and biological evaluation of spin-labelled derivatives of chalcones

    Institute of Scientific and Technical Information of China (English)

    金岩; 刘杰; 陈世武

    2013-01-01

    目的 发现高效自旋标记查耳酮类抗肿瘤药物.方法 通过乙酰苯与芳醛在碱性条件下缩合生成查耳酮,进一步与稳定氮氧自由基酸发生酰化反应合成了一系列自旋标记的查耳酮化合物,用MTT法对合成的化合物进行体外抗肿瘤活性研究(P3SS、A549、HT-29、MDA-MB-231、8GC-7901、BEL-7402).结果 化合物3a和3c在10 μg/mL时对所有测试瘤株的抑制率均大于60%.结论 自旋标记的查耳酮酰胺类化合物具有较高的体外抗肿瘤活性.%Objective To find new spin labelled chalcones as anti-tumor drugs with potent activities and low toxicities. Methods A series spin labelled chalcones were synthesized by condensation reaction of aromatic aldehyde and acetpophenone, following acetylation. The cytotoxic activities against six tumor cell lines (P388, A-549, HT-29, MDA-MB-231, SGC-7901, BEL-7402) in vitro of synthetic compounds were also evaluated by MTT method. Results Compounds 3a and 3c showed more than 60% proliferation inhibitions against all six tested tumor cell lines in vitro. Conclusion The amides of spin-labelled chalcones present better anti-tumor activities in vitro.

  11. NaOH催化无溶剂下肉桂醛类查尔酮的不饱和酮的合成%Synthesis of cinnamaldehyde's chalcone under solvent-free catalyzed by NaOH

    Institute of Scientific and Technical Information of China (English)

    丁润梅; 田大年

    2011-01-01

    Cinnamaldehyde's Chalcones have been efficiently prepared by condensation of arone and cinnamaldehyde by using NaOH as catalyst under room temperature condition. Compared with traditional methods,this method is more convenient due to the milder condition,%使用NaOH为催化剂在无溶剂条件下,在室温条件下,制备了8种肉桂醛类查尔酮化合物。结果表明该方法操作简单,条件温和,反应速度快,产率高,对环境友好,后处理简便。

  12. Synthesis of ferrocenyl chalcone compounds and their anti-breast cancer activities%二茂铁基查耳酮类化合物的合成及其抗乳腺癌活性研究

    Institute of Scientific and Technical Information of China (English)

    陈善龙; 谭娟

    2015-01-01

    Objective To design and synthesize ferrocenyl chalcone compounds, and to study their anti-breast cancer activities. Methods A series of ferrocenyl chalcones were synthesized by Claisen-Schmidt condensation reaction, and the anti-breast cancer activity was assessed by MTT method. Results Nine ferrocenyl chalcone compounds were synthesized and characterized by 1H-NMR and 13C-NMR. The preliminary biological results showed that target compounds 1 — 9 displayed significant inhibitory activities on both MCF-7 and MDA-MB-231 cell lines. Specifically, compound 6 showed the best inhibitory activity against MDA-MB-231. Conclusion This study provides reference for development of chalcone compounds with inhibitory activity in hormone-independent breast cancer.%目的:设计并合成了二茂铁基查耳酮类化合物,并对其抗乳腺癌活性进行研究。方法通过 Claisen-Schmidt 缩合反应合成含有二茂铁基的查耳酮类化合物,并通过MTT法对目标化合物的抗乳腺癌活性进行研究。结果合成了9个含有二茂铁基查耳酮类化合物,其结构均通过1H-NMR、13C-NMR进行了表征。生物活性结果表明,目标化合物1~9对MCF-7和MDA-MB-23均具有较强的抑制活性,其中化合物6对MDA-MB-231的抑制活性最强。结论本研究为开发具有抗荷尔蒙非依赖型乳腺癌活性的查耳酮类化合物提供了参考。

  13. A chalcone-related small molecule that induces methuosis, a novel form of non-apoptotic cell death, in glioblastoma cells

    Directory of Open Access Journals (Sweden)

    Bhanot Haymanti

    2011-06-01

    Full Text Available Abstract Background Methuosis is a unique form of non-apoptotic cell death triggered by alterations in the trafficking of clathrin-independent endosomes, ultimately leading to extreme vacuolization and rupture of the cell. Results Here we describe a novel chalcone-like molecule, 3-(2-methyl-1H- indol-3-yl-1-(4-pyridinyl-2-propen-1-one (MIPP that induces cell death with the hallmarks of methuosis. MIPP causes rapid accumulation of vacuoles derived from macropinosomes, based on time-lapse microscopy and labeling with extracellular fluid phase tracers. Vacuolization can be blocked by the cholesterol-interacting compound, filipin, consistent with the origin of the vacuoles from non-clathrin endocytic compartments. Although the vacuoles rapidly acquire some characteristics of late endosomes (Rab7, LAMP1, they remain distinct from lysosomal and autophagosomal compartments, suggestive of a block at the late endosome/lysosome boundary. MIPP appears to target steps in the endosomal trafficking pathway involving Rab5 and Rab7, as evidenced by changes in the activation states of these GTPases. These effects are specific, as other GTPases (Rac1, Arf6 are unaffected by the compound. Cells treated with MIPP lose viability within 2-3 days, but their nuclei show no evidence of apoptotic changes. Inhibition of caspase activity does not protect the cells, consistent with a non-apoptotic death mechanism. U251 glioblastoma cells selected for temozolomide resistance showed sensitivity to MIPP-induced methuosis that was comparable to the parental cell line. Conclusions MIPP might serve as a prototype for new drugs that could be used to induce non-apoptotic death in cancers that have become refractory to agents that work through DNA damage and apoptotic mechanisms.

  14. Structure, expression profile and phylogenetic inference of chalcone isomerase-like genes from the narrow-leafed lupin (Lupinus angustifolius L. genome

    Directory of Open Access Journals (Sweden)

    Łucja ePrzysiecka

    2015-04-01

    Full Text Available Lupins, like other legumes, have a unique biosynthesis scheme of 5-deoxy-type flavonoids and isoflavonoids. A key enzyme in this pathway is chalcone isomerase (CHI, a member of CHI-fold protein family, encompassing subfamilies of CHI1, CHI2, CHI-like (CHIL, and fatty acid-binding (FAP proteins. Here, two Lupinus angustifolius (narrow-leafed lupin CHILs, LangCHIL1 and LangCHIL2, were identified and characterized using DNA fingerprinting, cytogenetic and linkage mapping, sequencing and expression profiling. Clones carrying CHIL sequences were assembled into two contigs. Full gene sequences were obtained from these contigs, and mapped in two L. angustifolius linkage groups by gene-specific markers. Bacterial artificial chromosome fluorescence in situ hybridization approach confirmed the localization of two LangCHIL genes in distinct chromosomes. The expression profiles of both LangCHIL isoforms were very similar. The highest level of transcription was in the roots of the third week of plant growth; thereafter, expression declined. The expression of both LangCHIL genes in leaves and stems was similar and low. Comparative mapping to reference legume genome sequences revealed strong syntenic links; however, LangCHIL2 contig had a much more conserved structure than LangCHIL1. LangCHIL2 is assumed to be an ancestor gene, whereas LangCHIL1 probably appeared as a result of duplication. As both copies are transcriptionally active, questions arise concerning their hypothetical functional divergence. Screening of the narrow-leafed lupin genome and transcriptome with CHI-fold protein sequences, followed by Bayesian inference of phylogeny and cross-genera synteny survey, identified representatives of all but one (CHI1 main subfamilies. They are as follows: two copies of CHI2, FAPa2 and CHIL, and single copies of FAPb and FAPa1. Duplicated genes are remnants of whole genome duplication which is assumed to have occurred after the divergence of Lupinus, Arachis

  15. Growth inhibitory effect of paratocarpin E, a prenylated chalcone isolated from Euphorbia humifusa Wild., by induction of autophagy and apoptosis in human breast cancer cells.

    Science.gov (United States)

    Gao, Suyu; Sun, Dejuan; Wang, Guan; Zhang, Jin; Jiang, Yingnan; Li, Guoyu; Zhang, Ke; Wang, Lei; Huang, Jian; Chen, Lixia

    2016-12-01

    Five flavones, including four flavonoids and one prenylated chalcone (paratocarpin E), were isolated from E. humifusa. and their chemical structures were established by spectroscopic analyses. We assessed the efficacy of these compounds against the growth of human breast cancer, leukemic, kidney cancer cell lines. Among them, paratocarpin E showed significant cytotoxicity against these cancer cell lines with an IC50 of 19.6μM on the growth of MCF-7 cells. Paratocarpin E treatment of MCF-7 cells resulted in typical apoptotic features via increasing expression of activated caspase-8 and -9 and PARP cleavage. Moreover, paratocarpin E altered the expression of Bax and Bcl-2, leading to the release of cytochrome c from the mitochondria into the cytosol, suggesting that the mitochondria-mediated apoptosis was initiated. In addition, paratocarpin E increased the MDC-positive autophagic vacuoles, the ratio of LC3-II/LC3-I protein levels of Beclin-1, but decreased p62 expression, indicating the potent pro-autophagic effects of paratocarpin E in MCF-7 cells. Mechanistically, cell death induced by paratocarpin E is able to induce apoptosis of MCF-7 cells by activating p38 and JNK signaling pathway while inhibiting Erk pathway. Furthermore, paratocarpin E promotes the activation and nuclear translocation of NF-κB, which plays an important role in balancing paratocarpin E-mediated apoptosis and autophagy. The molecular docking study also revealed that paratocarpin E bound to Fas and NF-κB complex. These findings provide initial evidences that paratocarpin E can be used as a potential anti-cancer drug in future for breast cancer therapy.

  16. Simultaneous post-transcriptional gene silencing of two different chalcone synthase genes resulting in pure white flowers in the octoploid dahlia.

    Science.gov (United States)

    Ohno, Sho; Hosokawa, Munetaka; Kojima, Misa; Kitamura, Yoshikuni; Hoshino, Atsushi; Tatsuzawa, Fumi; Doi, Motoaki; Yazawa, Susumu

    2011-11-01

    Garden dahlias (Dahlia variabilis) are autoallooctoploids with redundant genes producing wide color variations in flowers. There are no pure white dahlia cultivars, despite its long breeding history. However, the white areas of bicolor flower petals appear to be pure white. The objective of this experiment was to elucidate the mechanism by which the pure white color is expressed in the petals of some bicolor cultivars. A pigment analysis showed that no flavonoid derivatives were detected in the white areas of petals in a star-type cultivar 'Yuino' and the two seedling cultivars 'OriW1' and 'OriW2' borne from a red-white bicolor cultivar, 'Orihime', indicating that their white areas are pure white. Semi-quantitative RT-PCR showed that in the pure white areas, transcripts of two chalcone synthases (CHS), DvCHS1 and DvCHS2 which share 69% nucleotide similarity with each other, were barely detected. Premature mRNA of DvCHS1 and DvCHS2 were detected, indicating that these two CHS genes are silenced post-transcriptionally. RNA gel blot analysis revealed that small interfering RNAs (siRNAs) derived from CHSs were produced in these pure white areas. By high-throughput sequence analysis of small RNAs in the pure white areas with no mismatch acceptance, small RNAs were mapped to two alleles of DvCHS1 and two alleles of DvCHS2 expressed in 'Yuino' petals. Therefore, we concluded that simultaneous siRNA-mediated post-transcriptional gene silencing of redundant CHS genes results in the appearance of pure white color in dahlias.

  17. Cloning and Prokaryotic Expression Vector Construction of Cassia tora Chalcone Synthase%决明查尔酮合成酶全长cDNA的克隆及其原核表达载体的构建

    Institute of Scientific and Technical Information of China (English)

    方袁梦梦; 崔润泽; 陈访访; 周嘉裕; 廖海

    2011-01-01

    从决明子叶中提取查尔酮合成酶(Chalcone synthase)总RNA,经过RT-PCR获得查尔酮合成酶cDNA,纯化后与pMD18-T载体连接,转化大肠杆菌Top10,获得了查尔酮合成酶全长基因序列.序列测定表明,查尔酮合成酶全长核苷酸长度为1 173 bp,编码390个氨基酸.与GenBank中已发表序列EU430077进行比较,核苷酸同源性为100%.将该基因片段克隆到原核表达栽体pET-28a(+)中,构建重组质粒pET-28a(+)/Chalcone synthase,所获重组质粒经过双酶切、PCR和序列测定,证实含有目的片段,且连接、构建正确,为查尔酮合成酶的进一步表达奠定了基础.

  18. Inhibition of mitogen-activated protein kinases/nuclear factor κB-dependent inflammation by a novel chalcone protects the kidney from high fat diet-induced injuries in mice.

    Science.gov (United States)

    Fang, Qilu; Deng, Liancheng; Wang, Lintao; Zhang, Yali; Weng, Qiaoyou; Yin, Haimin; Pan, Yong; Tong, Chao; Wang, Jingying; Liang, Guang

    2015-11-01

    The prevalence of obesity has increased dramatically worldwide leading to increases in obesity-related complications, such as obesity-related glomerulopathy (ORG). Obesity is a state of chronic, low-grade inflammation, and increased inflammation in the adipose and kidney tissues has been shown to promote the progression of renal damage in obesity. Current therapeutic options for ORG are fairly limited and, as a result, we are seeing increased rates of progression to end-stage renal disease. Chalcones are a class of naturally occurring compounds with various pharmacological properties. 1-(3,4-Dihydroxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one (L2H17) is a chalcone that we have previously synthesized and found capable of inhibiting the lipopolysaccharide-induced inflammatory response in macrophages. In this study, we investigated L2H17's effect on obesity-induced renal injury using palmitic acid-induced mouse peritoneal macrophages and high fat diet-fed mice. Our results indicate that L2H17 protects against renal injury through the inhibition of the mitogen-activated protein kinase/nuclear factor κB pathways significantly by decreasing the expression of proinflammatory cytokines and cell adhesion molecules and improving kidney histology and pathology. These findings lead us to believe that L2H17, as an anti-inflammatory agent, can be a potential therapeutic option in treating ORG.

  19. Changes in phytochemical synthesis, chalcone synthase activity and pharmaceutical qualities of sabah snake grass (Clinacanthus nutans L.) in relation to plant age.

    Science.gov (United States)

    Ghasemzadeh, Ali; Nasiri, Alireza; Jaafar, Hawa Z E; Baghdadi, Ali; Ahmad, Izham

    2014-10-30

    In the current study, changes in secondary metabolite synthesis and the pharmaceutical quality of sabah snake grass leaves and buds were considered in relation to plant age (1 month, 6 months, and 1 year old). The activity of the enzyme chalcone synthase (CHS, EC 2.3.1.74) was measured, as it is a key enzyme for flavonoid production. Significant differences in total flavonoid (TF) production were observed between the three plant growth periods and the different plant parts. The highest contents of TF (6.32 mg/g dry weight [DW]) and total phenolic (TP) (18.21 mg/g DW) were recorded in 6-month-old buds. Among the flavonoids isolated in this study the most important ones based on concentration were from high to low as follows: catechin > quercetin > kaempferol > luteolin. Production of phenolic acids increased from 1 to 6 months, but after 6 months up to 1 year of age, they decreased significantly. The highest contents of caffeic acid (0.307 mg/g DW) and gallic acid (5.96 mg/g DW) were recorded in 1-year and 6-month-old buds, respectively. The lowest and highest activity of CHS was recorded in 1-month and 6-month-old buds with values of 3.6 and 9.5 nkat/mg protein, respectively. These results indicate that the increment in flavonoids and phenolic acids in 6-month-old buds can be attributed to an increase in CHS activity. The highest 1,1-diphenyl-2-picrylhydrazyl (DPPH) activity was observed in the extract of 1-year-old buds followed by 6-month-old buds, with 50% of free radical scavenging (IC50) values of 64.6 and 73.5 µg/mL, respectively. Interestingly, a ferric reducing antioxidant power (FRAP) assay showed a higher activity in 6-month-old buds (488 μM of Fe(II)/g) than in 1-year-old buds (453 μM of Fe(II)/g), in contrast to the DPPH result. Significant correlations (p < 0.05) were observed between CHS enzyme activity and FRAP activity, TF, catechin, and kaempferol content. Extracts of 6-month-old bud exhibited a significant in vitro anticancer activity against

  20. Changes in Phytochemical Synthesis, Chalcone Synthase Activity and Pharmaceutical Qualities of Sabah Snake Grass (Clinacanthus nutans L. in Relation to Plant Age

    Directory of Open Access Journals (Sweden)

    Ali Ghasemzadeh

    2014-10-01

    Full Text Available In the current study, changes in secondary metabolite synthesis and the pharmaceutical quality of sabah snake grass leaves and buds were considered in relation to plant age (1 month, 6 months, and 1 year old. The activity of the enzyme chalcone synthase (CHS, EC 2.3.1.74 was measured, as it is a key enzyme for flavonoid production. Significant differences in total flavonoid (TF production were observed between the three plant growth periods and the different plant parts. The highest contents of TF (6.32 mg/g dry weight [DW] and total phenolic (TP (18.21 mg/g DW were recorded in 6-month-old buds. Among the flavonoids isolated in this study the most important ones based on concentration were from high to low as follows: catechin > quercetin > kaempferol > luteolin. Production of phenolic acids increased from 1 to 6 months, but after 6 months up to 1 year of age, they decreased significantly. The highest contents of caffeic acid (0.307 mg/g DW and gallic acid (5.96 mg/g DW were recorded in 1-year and 6-month-old buds, respectively. The lowest and highest activity of CHS was recorded in 1-month and 6-month-old buds with values of 3.6 and 9.5 nkat/mg protein, respectively. These results indicate that the increment in flavonoids and phenolic acids in 6-month-old buds can be attributed to an increase in CHS activity. The highest 1,1-diphenyl-2-picrylhydrazyl (DPPH activity was observed in the extract of 1-year-old buds followed by 6-month-old buds, with 50% of free radical scavenging (IC50 values of 64.6 and 73.5 µg/mL, respectively. Interestingly, a ferric reducing antioxidant power (FRAP assay showed a higher activity in 6-month-old buds (488 μM of Fe(II/g than in 1-year-old buds (453 μM of Fe(II/g, in contrast to the DPPH result. Significant correlations (p < 0.05 were observed between CHS enzyme activity and FRAP activity, TF, catechin, and kaempferol content. Extracts of 6-month-old bud exhibited a significant in vitro anticancer activity

  1. Study on the Microwave-assistant Extraction of Chalcones from Angelica keiskei Leaves%微波辅助提取明月草叶查尔酮工艺研究

    Institute of Scientific and Technical Information of China (English)

    尹慧丹; 田大永; 方波

    2011-01-01

    对微波辅助提取明月草叶查尔酮的工艺进行了研究。在微波功率320 W条件下研究了乙醇浓度、液料比、提取时间和提取次数对明月草叶查尔酮提取量的影响,最优条件为乙醇体积浓度70%,液料比40︰1(mL/g),提取时间2 min,提取3次。最优条件下,提取物中查尔酮含量为1.039%。对明月草叶查尔酮粗提液进行清除羟基自由基(-OH)研究,结果表明其对羟基自由基具有较好的清除作用,10 mg/mL明月草叶查尔酮粗提液对羟基自由基清除率达到87.04%。%The microwave-assistant extraction of chalcones from the leaves of Angelica keiskei(LAK) was studied.The microwave power was controlled at 320 W,the effects of ethanol concentration,the ratio of extractant volume to LAK weight,microwave treating time and extraction times on the extraction yield of chalcones were studied.The results showed that the optimum extraction conditions were as follows: the concentration of ethanol was 70%(v/v),the ratio of extractant volume to LAK weight was 40︰1(mL/g),the extraction time was 2 min and the extract 3 times.Under these conditions the yield of chalcones was 1.039%.The extract isolated from LAK had good scavenging activities on hydroxyl radical(-OH).The scavenging percentage of hydroxyl radical reached 87.03% when the concentration of the LAK extract was 10 mg/mL.

  2. 三种查尔酮类化合物与人血清白蛋白相互作用及其构效关系研究%Study on the Interaction and Structure-activity Relationship between Three Chalcones and Human Serum Albumin

    Institute of Scientific and Technical Information of China (English)

    张爱平; 郝娟; 黄茜; 高晓亚; 文雯

    2013-01-01

    The interaction and structure-activity relationship of human serum albumin with chalcone, 4'-methoxychalcone and 4'-chlorochalcone were investigated by ultraviolet spectroscopy, fluorescence spectroscopy and synchronous fluorescence spectroscopy under the simulative human physiological conditions. The binding constants, the number of binding sites and the thermodynamic parameters were calculated and the effects of the three compounds on the conformation of HSA were studied. The results showed that the intrinsic fluorescence of HSA was significantly quenched by chalcone, 4 -methoxychalcone and 4- respectively. The mechanism of fluorescence quenching was mainly static quenching with non-radiation energy transfer. The 1:1 compound was formed between each chalcone and HSA. The binding parameters of chalcone,4'-methoxychalcone and 4'-chlorochalcone with HSA were as follows: the binding constants K were 2. 50×104,6. 97×103 and 2.77×103L?moL-1 ,the binding distances r were 3. 78,3. 93 and 4. 25 nm,respectively. The driving forces were mainly hydrogen bond and Vander Waals according to the thermodynamic parameters. The synchronous fluorescence spectra indicated that the binding sites of chalcone,4'-methoxychalcone and 4'-chlorochalcone with HSA were closer to tryptophan residues. The interaction of the three compounds with HSA could result in the decrease of tryptophan residues hydrophobicity and the change of HSA conformation. The results demonstrated that the different substituent in chalcones played an important role in the interaction between chalcones and HSA,and the order of the interaction strength between chalcones and HSA were chalcone >4'-methoxychalcone >4 -chlorochalcone.%在模拟人体生理条件下,采用紫外光谱法、荧光光谱法和同步荧光光谱法研究查尔酮、4′-甲氧基查尔酮和4′-氯查尔酮与人血清白蛋白(HSA)的相互作用及其构效关系.实验表明:三种查尔酮类化合物对HSA的荧光猝灭机制主

  3. Michael Addition of Carbon and Nitrogen Nucleophiles with Chalcone Catalyzed by Semicarbazide%氨基脲催化下碳亲核试剂和氮亲核试剂对查尔酮的Michael加成反应

    Institute of Scientific and Technical Information of China (English)

    程贺龙; 高玉华; 聂士鹏; 陆鸿飞

    2014-01-01

    An efficient Michael addition of chalcone and malonate, malononitrile, aniline catalyzed by phenylalanine-urea in water has been disclosed at 60 ℃ with trifluoromethanesulfonate, affording the corresponding adducts in good yields, while the catalyst was easy to handle up and the solvent was environmentally friendly.%以查尔酮、丙二酸酯、丙二腈、苯胺为原料,水为溶剂,苯丙氨酸脲化合物为催化剂,三氟甲磺酸为助剂60℃下反应,高产率得到Michael加成产物。该方法具有催化剂合成简单、环境友好等优点。

  4. The Synthesis and Evaluation of Novel Hydroxyl Substituted Chalcone Analogs with in Vitro Anti-Free Radicals Pharmacological Activity and in Vivo Anti-Oxidation Activity in a Free Radical-Injury Alzheimer’s Model

    Directory of Open Access Journals (Sweden)

    Ying Pan

    2013-01-01

    Full Text Available Alzheimer’s disease (AD pathogenesis involves an imbalance between free radical formation and destruction. In order to obtain a novel preclinical anti-AD drug candidate, we synthesized a series of novel hydroxyl chalcone analogs which possessed anti-free radical activity, and screened their effects on scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH and OH free radicals in vitro. Compound C7, 4,2'-dihydroxy-3,5-dimethoxychalcone was found to have potent activity in these anti-free radical activity tests. Further research revealed that C7 could elevate glutathione peroxidase (GSH-PX and super oxide dismutase (SOD levels and lower malonaldehyde (MDA level in vivo in the Alzheimer’s model. The indication of C7’s effect on AD needs further study.

  5. Purification of glucose-6-phosphate dehydrogenase and glutathione reductase enzymes from the gill tissue of Lake Van fish and analyzing the effects of some chalcone derivatives on enzyme activities.

    Science.gov (United States)

    Kuzu, Muslum; Aslan, Abdulselam; Ahmed, Ishtiaq; Comakli, Veysel; Demirdag, Ramazan; Uzun, Naim

    2016-04-01

    Glucose-6-phosphate dehydrogenase (G6PD) and glutathione reductase (GR) are metabolically quite important enzymes. Within this study, these two enzymes were purified for the first time from the gills of Lake Van fish. In the purifying process, ammonium sulfate precipitation and 2',5'-ADP Sepharose 4B affinity column chromatography techniques for glucose-6-phosphate dehydrogenase, temperature degradation and 2',5'-ADP Sepharose 4B affinity column chromatography for glutathione reductase enzyme were used. The control of the enzyme purity and determination of molecular weight were done with sodium dodecyl sulfate polyacrylamide gel electrophoresis. K(M) and V(max) values were determined with Lineweaver-Burk plot. Besides, the effects of some chalcone derivatives on the purified enzymes were analyzed. For the ones showing inhibition effect, % activity-[I] figures were drawn and IC50 values were determined. K(i) value was calculated by using Cheng-Prusoff equation.

  6. E-2-Benzylidenebenzocycloalkanones. IV. Studies on transmission of substituent effects on 13C NMR chemical shifts of E-2-(X-benzylidene)-1-tetralones, and -benzosuberones. Comparison with the 13C NMR data of chalcones and E-2-(X-benzylidene)-1-indanones

    Science.gov (United States)

    Perjési, Pál; Linnanto, Juha; Kolehmainen, Erkki; Ősz, Erzsébet; Virtanen, Elina

    2005-04-01

    Single substituent parameter (SSP) and dual substituent parameter (DSP) analyses were applied to study the transmission of substituent effects on selected 13C NMR chemical shifts of the cyclic chalcone analogues, E-2-(4'-X-benzylidene)-1-tetralones ( 2) and E-2-(4'-X-benzylidene)-1-benzosuberones ( 3). In order to study how the geometry of the cyclic chalcone analogues affects the transmission of substituent effects similar investigations with the respective chalcones ( 4) were also performed. The results obtained earlier with the five-membered analogue E-2-(4'-X-benzylidene)-1-indanones ( 1) were also involved in the comparisons. Geometry optimization of the unsubstituted 1a, 2a, 3a and 4a as well as the substituted 2 and 3 was performed by ab initio quantum chemical calculations. Both SSP and DSP analyses reflected that resonance effects contribute more to the chemical shift of C-α (C2), while inductive effects primarily affect that of C-β (C10) of the enone moiety of all the four series. This latter effect, however, is far not as pronounced as that of the former one. It was found that DSP analysis data ( ρF and ρR values) of transmission of substituent effects on the δC2 data can serve as a measure of choice to study the conformation (planarity) of the investigated enones in the four series.

  7. COCHINCHINENIN—A NEW CHALCONE DIMER FROM THE CHINESE DRAGON BLOOD%剑叶血竭素国产血竭中一个新的二聚查耳酮

    Institute of Scientific and Technical Information of China (English)

    周志宏; 王锦亮; 杨崇仁

    2001-01-01

    目的研究国产商品血竭的活性成分。方法用甲醇提取,Sephadex L-20, MCI gel和硅胶柱色谱进行分离纯化,用现代波谱学方法进行结构鉴定。结果从国产雨林牌血竭的甲醇浸提物中得到9个查耳酮化合物,分别鉴定为:1-[5-(2,4,4′-三羟基二氢查耳酮基)]-1-对羟基苯基-3-(2-甲氧基-4-羟基苯基)-丙烷(1), 2′-methoxysocotrin-5′-ol (2), socotrin-4′-ol (3), 2-甲氧基-4,4′-二羟基二氢查耳酮(4), 2,4,4′-三羟基二氢查耳酮(5), 2,4,4′-三羟基-6-甲氧基二氢查耳酮(6), 2′,4′,4-三羟基查耳酮(7), 2-甲氧基-4,4′-二羟基查耳酮(8), 2′-甲氧基-4′,4-二羟基查耳酮(9)。结论 1为一新的查耳酮二聚体,命名为剑叶血竭素(cochinchinenin),2-9为首次从该血竭中分离得到。%AIM To study the active constituents of Dracaena cochinchinensis (Lour.) S.C.Chen. in the commercial dragon blood. METHODS Various column chromatographies with Sephadex L-20 gel, MCI gel and silica gel were employed for the isolation and purification. The structures of compounds were elucidated by spectral analysis. RESULTS Nine chalcones were isolated from the commercial dragon's blood which was made of D.cochinchinensis (Lour.) S.C.Chen.. By means of spectral data, they were identified as 1-[5-(2,4,4′-trihydroxydihydrochalconyl)]-1-(p-hydroxyphenyl)-3-(2-methoxy-4-hydroxy-phenyl)-propane (1), 2′-methoxysocotrin-5′-ol (2), socotrin-4′-ol (3), 2-methoxy-4,4′-dihydroxydihydrochalcone (4), 2,4,4′-trihydroxy-dihydrochalcone (5), 2,4,4′-trihydroxy-6-methoxydihydrochalcone (6), 2′,4′,4-trihydroxy-chalcone (7), 2-methoxy-4,4′-dihydroxychalcone (8) and 2′-methoxy-4′,4-dihydroxychalcone (9). CONCLUSION Compound 1 is a new chalcone dimer and named as cochinchinenin. Compounds 2-9 were isolated from D.cochinchinensis (Lour.) S.C.Chen. for the first time.

  8. Cloning and Expression Analysis of Chilling-induced Chalcone Synthase Gene from Jatropha curcas%小桐子低温诱导查耳酮合酶基因的克隆及其表达分析

    Institute of Scientific and Technical Information of China (English)

    王海波; 邹竹荣; 龚明

    2015-01-01

    In order to understand the function of chalcone synthase in cold resistance of Jatropha curcas, a chilling-induced chalcone synthase gene, named as JcCHS, was cloned from J. curcas based on data of transcriptome and digital gene expression proifling (DGE), and the expression patterns were analyzed by semi-quantitative RT-PCR. The results showed that the full length of JcCHS cDNA was 1386 bp, with entire open reading frame (ORF) of 1170 bp encoding 389 amino acids. The theoretical molecular weight of JcCHS was 42.2 kDa with pI of 6.53. JcCHS protein shared 93.6%identity with CHS from Ricinus communis (Euphorbiaceae), and belong to the type-III polyketide synthase family containing conserved domains of chalcone synthase/styrene synthase. The expression of JcCHS was detected in all tissues with the highest expression in root. In addition, the over-expression of JcCHS in yeast enhanced its resistance to low temperature. So, it was suggested that JcCHS gene would involve in the cold-resistance formation in J. curcas.%为了解查耳酮合酶在小桐子(Jatropha curcas)抗冷性形成中的作用,基于小桐子低温锻炼转录组和数字基因表达谱数据,克隆了低温新诱导表达的小桐子查耳酮合酶基因(JcCHS),并分析了该基因的表达特性和功能。结果表明,JcCHS基因的cDNA全长为1386 bp,包含完整开放阅读框(ORF)1170 bp,编码389个氨基酸,JcCHS的理论分子量为42.2 kDa、等电点为6.53,与蓖麻CHS蛋白序列的相似性高达93.6%,具有III型聚酮合酶家族保守的查耳酮合酶/对苯乙烯合酶结构域。半定量RT-PCR分析表明,JcCHS在小桐子各组织中都有表达,其中根的表达量较高。JcCHS基因的表达能在一定程度上提高重组酵母菌的低温抵抗能力,这说明JcCHS基因可能参与了小桐子的抗低温响应。

  9. 查尔酮类似化合物的合成及其抑菌活性研究%Study on Synthesis and Antifungal Activity of Chalcone Analogues

    Institute of Scientific and Technical Information of China (English)

    田珈源; 罗青春; 梁华忠; 谌晓洪

    2011-01-01

    [目的]合成查尔酮类似化合物,并研究其抑菌活性,以寻找高效、安全的抑菌活性化合物.[方法]以苯甲酰氯类化合物和胺类化合物为原料,通过酰氯的胺解反应设计并合成了16种查尔酮类似化合物,对其分子结构经红外光谱(IR)和氢核磁共振波谱(1H NMR)进行确认.[结果]该类化合物具有一定的抑菌活性,当浓度为100 mg/L时,化合物A2(2-氯-N-苯基苯甲酰胺)对水稻纹枯病(Rhizoctonia solani)和油菜菌核病菌(Sclerotiua sclerotiorum的抑制率分别达90.27%和92.56%.[结论]产物A2为查尔酮的类似化合物,且属于天然产物,在自然界中能够自然降解,不会引起环境污染;而且其化学结构简单,人工合成也比较容易,可以以此为先导化合物对其结构进行优化和改造;研究其结构和活性之间的关系,开发出高效、低毒、对非靶标生物安全的新型抑菌剂.%[Objective] To synthesize chalcone analogues and study their antifungal activity so as to find high-efficient and safe compounds with antifungal activity. [Method] With benzoyl chloride compounds and amines as the materials, 16 chalcone analogues were designed and synthe sized through the aminolysis reaction of acyl chloride, and their molecular structures were determined by IR and ' H NMR. [ Result ] The chal cone analogues had certain antifungal activity. The antifungal rate of 100 mg/L compound A2 (2-chloro-N-phenyl benzamide) against Rhizoctonia solani and Sclerotiua sclerotiorum reached 90. 27% and 92.56% , respectively. [Conclusion] Product A2 was an analogue of the natural product chalcone that could naturally degrade without causing environmental pollution. What's more, its chemical structure was simple and easy to pre pare. Using A2 as a lead compound, new high-efficient and low-toxic antifungal agents which were safe to the non-target organisms could be de veloped through optimizing its chemical structure and studying the relationship

  10. Studies on antioxidant and antimicrobial activities of a novel chalcone compound TPY%新型查尔酮类化合物TPY的抗氧化及抗菌活性研究

    Institute of Scientific and Technical Information of China (English)

    裘观荣; 丁晓丽; 黄巧珍; 关丽萍

    2013-01-01

    OBJECTIVE To study the antioxidant and antimicrobial activities of chalcone compound TPY.METHODS The antioxidant are evaluated in vitro by the capability of TPY for scavenging the DPPH free radical and reducing power.The antimicrobial activities are tested by using Escherichia coli,Staphylococcus aureus,Bacillus subtilis,Proteus and Salmonella.RESULTS The results showed that compound TPY has significant antioxidant activities,and dose dependent.In addition,compound TPY has more effective activity against the various bacillus.CONCLUSION The compound TPY is perfect additives as antioxidants and inhibiting microorganisms.%目的 研究查尔酮类化合物TPY的抗氧化、抗菌活性.方法 测定TPY对DPPH·清除能力和总还原能力,测定TPY对大肠杆菌、金黄色葡萄球菌、枯草芽孢杆菌、沙门氏菌和变形杆菌等菌种的体外抑菌作用.结果 TPY的抗氧化能力呈现出明显的剂量依赖关系,具有良好的抗氧化活性.TPY对5种病菌具有不同程度的抑制作用.结论 TPY可作为一种理想的抗氧化和抑菌添加剂.

  11. Development of a stability-indicating LC method for determination of a synthetic chalcone derivative in a nanoemulsion dosage form and identification of the main photodegradation product by LC-MS.

    Science.gov (United States)

    Mattos, Cristiane B; Deponti, Vânia B; Barreto, Fabiano; Simões, Cláudia M O; Andrighetti-Frohner, Carla R; Nunes, Ricardo J; Steindel, Mário; Teixeira, Helder F; Koester, Letícia S

    2012-11-01

    This study aimed to develop and validate a stability indicating LC for the determination of 5-(2-benzoylethenyl)-N-benzyl-2 methoxybenzenesulfonamide (SCD - a synthetic chalcone derivative), and evaluate the degradation profile of the compound under different stress conditions recommended by International Conference on Harmonization (ICH). Chromatographic separation was performed on a silica C18 column, methanol-water mobile phase 70:30 (v:v), pH 5.0 adjusted with the addition of trifluoroacetic acid (TFA) at a flow rate of 1.0 mL min(-1); detection by UV absorption at 330 nm. The method was validated for linearity, precision, accuracy, robustness and specificity. The SCD was subjected to forced degradation and peak photodegradation product was well separated from the pure substance, with retention times significantly different, indicating the specificity of the method. Second-order degradation kinetics of SCD was observed under photodegradation and base-induced degradation. In order to identify the product formed under photodegradation, liquid chromatography-tandem mass spectrometry (LC-MS/MS) was performed. These results indicate that the method can be successfully used in order to assay SCD in a nanoemulsion dosage form, and that this formulation has a protective effect over SCD degradation.

  12. Absence of genotoxic effects of the chalcone (E)-1-(2-hydroxyphenyl)-3-(4-methylphenyl)-prop-2-en-1-one) and its potential chemoprevention against DNA damage using in vitro and in vivo assays

    Science.gov (United States)

    2017-01-01

    The chalcone (E)-1-(2-hydroxyphenyl)-3-(4-methylphenyl)-prop-2-en-1-one), or 2HMC, displays antileishmanial, antimalarial, and antioxidant activities. The aim of this study was to investigate the cytotoxic, genotoxic, mutagenic, and protective effects of 2HMC using the Ames mutagenicity test, the mouse bone marrow micronucleus test, and the comet assay in mice. In the assessment using the Ames test, 2HMC did not increase the number of His+ revertants in Salmonella typhimurium strains, demonstrating lack of mutagenicity. 2HMC showed no significant increase in micronucleated polychromatic erythrocyte frequency (MNPCE) in the micronucleus test, or in DNA strand breaks using the comet assay, evidencing absence of genotoxicity. Regarding cytotoxicity, 2HMC exhibited moderate cytotoxicity in mouse bone marrow cells by micronucleus test. 2HMC showed antimutagenic action in co-administration with the positive controls, sodium azide (SA) and 4-nitroquinoline-1-oxide (4NQO), in the Ames test. Co-administered and mainly pre-administered with cyclophosphamide (CPA), 2HMC caused a decrease in the frequency of MNPCE using the micronucleus test and in DNA strand breaks using the comet assay. Thus, 2HMC exhibited antimutagenic and antigenotoxic effects, displaying a DNA-protective effect against CPA, SA, and 4NQO carcinogens. In conclusion, 2HMC presented antimutagenic, antigenotoxic and moderate cytotoxic effects; therefore it is a promising molecule for cancer prevention. PMID:28207781

  13. Effect of Angelica keiskei Koidz Chalcone on PCNA and BCL-2 Protein Expression of Mice Hepatocarcinoma Cells%明日叶查尔酮对小鼠肝癌细胞PCNA和BCL-2蛋白表达影响

    Institute of Scientific and Technical Information of China (English)

    孙赫; 钟进义; 孟扬; 李帅; 杨青

    2011-01-01

    目的:研究明日叶(Angelica keiskei Koidz)查尔酮对小鼠肝癌细胞PCNA和BCL-2蛋白表达的影响.方法:将50只皮下接种肝癌H22细胞株的小鼠随机分为5组,每组10只.高、中、低剂量组分别每日经口灌胃给予40、20、5mg/kg的查尔酮,肿瘤对照组给予等量生理盐水,连续10d,环磷酰胺组隔天腹腔注射环磷酰胺20mg/kg.取肝癌组织用四甲基偶氮噻唑蓝(MTT)法测各组小鼠肝癌细胞增殖活性,免疫组化法检测各组肝癌细胞增殖细胞核抗原(PCNA)和凋亡相关蛋白BCL-2表达水平.结果:高剂量查尔酮组和肿瘤对照组的肝癌细胞增殖活性分别为(0.716±0.018)和(1.135±0.032),差别有显著性(P<0.05).高剂量组PCNA和BCL-2蛋白表达率分别为28.33%和16.77%.肿瘤对照组分别为72.77%和65.17%,差异均有显著性(P<0.05).结论:查尔酮可降低小鼠肝癌细胞PCNA和BCL-2表达水平,对肝癌细胞增殖有一定抑制作用.%Objective: To investigate the effect of angelica keiskei koidz chalcone on the expression of PCNA and BCL-2 in mice hepatocarcinoma cells. Methods: Fifty mice were inoculated with hepatocarcinoma H22 cells and divided into five groups, with 10 mice per group. High, medium and low chalcone groups were given 40, 20, Smg/kg/d of chalcone by mouth, respectively. The tumor control group was given saline by mouth and the cylophosphamide group was given 20mg/kg cyclophosphamide by intraperitoneal injection every other day. Ten days later all mice were sacrificed. The proliferation activity of hepatocarcinoma cells was determined by methy tetrazolium (MTT) assay, and the levels of the proliferating cell nuclear antigen (PCNA) and BCL-2 protein expression were detected by immunohisto chemistry method. Results: The cell proliferation activity of high dose chalcone group and tumor control group were (0.716±0.018) and(1.135± 0.032). The difference was significant (P<0.05). The expression of PCNA and BCL-2 protein in high dose

  14. 查尔酮及其螺杂环衍生物的合成、晶体结构、抗氧化活性研究%Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues

    Institute of Scientific and Technical Information of China (English)

    吴建章; 李物兰; 陈玲姿; 楚生辉; 赵承光; 卫涛; 杨树林; 李校堃

    2012-01-01

    To synthesize new structure type chalcone analogues, and obtain chalcone analogues with good antioxidant activity. Two types of chalcone analogs, chalcones A and spiro-heterocyclic B were designed and synthesized, and the structures of 21 compounds were characterized by 1H NMR, ESI-MS and ESI-HRMS. Single-crystal of spiro-heterocyclic B was cultured, and its single-crystal structure was determined by X-ray diffraction study. The crystal structure of Bl was monoclinic system, space group C2/c, with cell dimensions of a=21.350(3) A, 6=8.6256(10) A, e=26.161(3) A. Spiro-heterocyclic B is the new structure type, and obtained by one-pot synthesis which is 1,3-dipolar cycloaddition reaction and no catalyst. The synthesis of spiro-heterocyclic B is not only high regioselectivity and stereoselectivity, but also environmentally friendly. The antioxidant activities in vitro were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Many compounds, which can have strong activity of scavenging DPPH free radicals, were screened. In the 2 types' of chalcones analogs, the compounds with 3,4-(OH)2 in "a" ring have excellent antioxidant activities. The chalcone analogs with o-dihydroxy in benzene ring maybe have good antioxidant activities.%为了合成新结构类型查尔酮衍生物,发现具有抗氧化活性的查尔酮类化合物,设计合成了查尔酮A和螺杂环B两种类型,共21个查尔酮类似物,结构经ESI-MS,ESI-HRMS和1H NMR确认.培养出螺杂环B1的单晶,通过X衍射确证了其为单斜晶系.其中螺杂环B为新结构类型化合物,通过1,3-偶极环加成反应,用不需加催化剂的“一锅煮”方法合成,该反应具有很好的立体选择性和区域选择性、且环境友好.用DPPH法测试了所有化合物的抗氧化活性,筛选出了多个对1,1-二苯基-2-三硝基苯肼(DPPH)自由基具有良好清除率的化合物,a环3,4-OH取代的两类化合物都具有良好的抗氧化活性,苯环邻位二羟基取代的查尔

  15. 苦荞查尔酮合成酶基因序列特征及分子进化分析%Characterize of Sequences and Molecular Evolution Analysis of Chalcone Synthase in Fagopyrum Tartaricum

    Institute of Scientific and Technical Information of China (English)

    孙朝霞; 侯思宇; 郭彬; 令狐斌; 黄可盛; 许冬梅; 韩渊怀

    2014-01-01

    Compared to other grain crops, Fagopyrum tataricum contain high levels of flavonoids, especially rutin. It has important significance for the research of key enzymes in the rutin biosynthesis pathway. This study focuses on the rutin biosynthesis pathway first key gene-chalcone synthase. Two genes FtCHS1 (1 430 bp, Genbank number:KJ130961) and FtCHS2 (1 454 bp, Gnebank number: KJ139980) were assembing and sequenced according to flo-wer transcriptom in F. tataricum. Protein 3D structure domain analysis showed that FtCHS contains three active site, 11 product binding sites, five acetyl coenzyme A binding sites. The amino acid sequences were aligned and compared to orthologous sequences from other plants, such as F. esculentum, F. dibotrys and P. cuspidatum. The phylogenetic tree showed that 22 polygonaceae plants was divided into two categories: (Ⅰ and Ⅱ), FtCHS1 and FtCHS2 belong to different categories. Gene expression of different tissues for FtCHS were analysed by semi-quantitive and real-time PCR. It showed that it had a higher expression level in immature embryo and flower for FtCHS1 and FtCHS2, and the expression level were decreased in roots and stems. Our work provides a strategy to improve rutin content, which could also be used to study molecular mechanism of rutin biosynthesis pathway.%相比其他杂粮作物,苦荞(Fagopyrum tataricum)植株中含有高含量的黄酮类物质--‘芦丁’,因此对其生物合成途径中关键酶的研究具有十分重要意义。查尔酮合成酶(chalcone synthase)是黄酮类物质生物合成的第一个关键酶,本研究基于转录组数据库同源搜索方法,核酸序列拼接获得两个查尔酮合成酶基因,分别命名为 FtCHS1(Genbank 登录号: KJ130961)和 FtCHS2(Genbank 登录号: KJ139980)。生物信息学分析结果表明,这两个基因编码的蛋白序列有3个保守结构域,其结构域上包含3个活性位点,11个产物结合位点,5个乙酰辅酶 A 结合

  16. Atividade alelopática de chalcona sintética, de seus precursores e de cetonas e aldeídos relacionados Allelopathic activity of synthetic chalcone, its precursors and of related cetones and aldehydes

    Directory of Open Access Journals (Sweden)

    H.R. Bitencourt

    2007-12-01

    objective of this work was to evaluate the allelopathic activity of synthetic chalcone, 2,4'-dimethoxychalcone, its precursors, 4-methoxyacetophenone (A and ortho-anisaldehyde (B, and some of their chemical alterations. The bioassays were developed under 25 ºC and photoperiod of 12 hours. The allelopathic effects of the compounds were tested on seed germination of Mimosa pudica and Senna obtusifolia weeds, under a concentration of 100, 200 and 300 mg L-1 of the compounds. The results indicated that precursor A (4-methoxyacetophenone plays an important role in allelopathic activity of the chalcones. These results show that synthesis is a possible pathway, helping to overcome problems such as characterization and isolation of natural products with herbicidal activity against weed species.

  17. Time courses for phytochrome-induced enzyme levels in phenylpropanoid metabolism (phenylalanine ammonia-lyase, naringenin-chalcone synthase) compared with time courses for phytochrome-mediated end-product accumulation (anthocyanin, quercetin).

    Science.gov (United States)

    Brödenfeldt, R; Mohr, H

    1988-12-01

    Time course for changes in the levels of enzymes characteristic of general phenylpropanoid metabolism (phenylalanine ammonia-lyase, PAL; EC 4.3.1.5) and of the flavonoid-glycoside branch pathway (naringenin-chalcone synthase, CHS; EC 2.3.1.74) were measured in the cotyledons of mustard (Sinapis alba L.) seedlings and compared with the rates of accumulation of related end products (anthocyanin and quercetin). Induction of enzyme levels and of end-product accumulation was carried out with red and far-red (FR) light, operating via phytochrome. The data are compatible with the concept that the phytochrome-mediated appearance of enzymes such as PAL and CHS is indeed a prerequisite for the appearance of anthocyanins and flavonols. However, there is no close correlation between enzyme levels and the rates of synthesis of end products which could justify the identification of specific rate-limiting enzymes. Rather, the data indicate that there is a second phytochrome-dependent step, beyond enzyme induction, where the actual rate of flavonoid accumulation is determined. Anthocyanin and quercetin accumulation respond differently to light. However, the relative action of continuous FR, red light pulses and 'stored phytochrome signal' is the same in both cases. This indicates that the mode of operation of phytochrome is the same in both cases. The two syntheses differ only in the degree of responsiveness towards phytochrome. The time course for changes in CHS levels in continuous FR, i.e. under conditions of phytochrome photosteady state, is similar to the time course for PAL levels whereas the time courses in darkness, following transfer from FR to darkness, are totally different. In the case of CHS, a transient rise is observed whereas, with PAL, an instantaneous drop in enzyme level occurs after transfer from FR to darkness. It is concluded that the 'stored phytochrome signal' operates in darkness in the case of CHS but not in the case of PAL.

  18. 查耳酮-2-羟基苯甲酰腙的超声波合成与热稳定性%Ultrasonic synthesis and thermal stability of chalcone-2-hydroxy benzoyl hydrazone

    Institute of Scientific and Technical Information of China (English)

    王燕燕; 郑长征; 王亮

    2015-01-01

    A compound of chalcone‐2‐hydroxybenzoyl hydrazone was ultrasonic synthesized through the condensation of chalcone and 2‐hydroxybenzoyl hydrazine ,and the effects of the reaction time ,the amount of solvent ,the temperature and the material ratio on the yield were discussed .Results show that under the condition of ultrasonic , the reaction time of 4. 5h , 10mL of the volume of solvent ,temperature of 75℃ and material ratio of 1∶1.2 is more ap‐propriate .The compound was characterized by elemental analysis ,infrared spectroscopy and 1 H NMR .The thermogravimetric analysis shows that the compound is stable below 190.98℃ .%以查耳酮和2‐羟基苯甲酰肼为原料,采用超声波合成查耳酮‐2‐羟基苯甲酰腙,研究反应时间、溶剂量、温度和摩尔比对收率的影响.结果表明,在超声波条件下,反应时间4.5h ,溶剂量10mL ,温度75℃和摩尔比1∶1.2较为适宜.通过元素分析、红外光谱和核磁共振氢谱对其结构进行了表征.热重分析表明标题化合物处于190.98℃以下时较为稳定.

  19. Millepachine, a novel chalcone, induces G2/M arrest by inhibiting CDK1 activity and causing apoptosis via ROS-mitochondrial apoptotic pathway in human hepatocarcinoma cells in vitro and in vivo.

    Science.gov (United States)

    Wu, Wenshuang; Ye, Haoyu; Wan, Li; Han, Xiaolei; Wang, Guangcheng; Hu, Jia; Tang, Minhai; Duan, Xingmei; Fan, Yi; He, Shichao; Huang, Li; Pei, Heying; Wang, Xuewei; Li, Xiuxia; Xie, Caifeng; Zhang, Ronghong; Yuan, Zhu; Mao, Yongqiu; Wei, Yuquan; Chen, Lijuan

    2013-07-01

    In this study, we reported millepachine (MIL), a novel chalcone compound for the first time isolated from Millettia pachycarpa Benth (Leguminosae), induced cell cycle arrest and apoptosis in human hepatocarcinoma cells in vitro and in vivo. In in vitro screening experiments, MIL showed strong antiproliferation activity in several human cancer cell lines, especially in HepG2 cells with an IC50 of 1.51 µM. Therefore, we chose HepG2 and SK-HEP-1 cells to study MIL's antitumor mechanism. Flow cytometry showed that MIL induced a G2/M arrest and apoptosis in a dose-dependent manner. Western blot demonstrated that MIL-induced G2/M arrest was correlated with the inhibition of cyclin-dependent kinase 1 activity, including a remarkable decrease in cell division cycle (cdc) 2 synthesis, the accumulation of phosphorylated-Thr14 and decrease of phosphorylation at Thr161 of cdc2. This effect was associated with the downregulation of cdc25C and upmodulation of checkpoint kinase 2 in response to DNA damage. MIL also activated caspase 9 and caspase 3, and significantly increased the ratio of Bax/Bcl-2 and stimulated the release of cytochrome c into cytosol, suggesting MIL induced apoptosis via mitochondrial apoptotic pathway. Associated with those effects, MIL also induced the generation of reactive oxygen species. In HepG2 tumor-bearing mice models, MIL remarkably and dose dependently inhibited tumor growth. Treatment of mice with MIL (20mg/kg intravenous [i.v.]) caused more than 65% tumor inhibition without cardiac damage compared with 47.57% tumor reduction by 5mg/kg i.v. doxorubicin with significant cardiac damage. These effects suggested that MIL and its easily modified structural derivative might be a potential lead compound for antitumor drug.

  20. Structure and nonlinear optical properties of (E)-1-(4-aminophenyl)-3-(3-chlorophenyl) prop-2-en-1-one: A promising new D-π-A-π-D type chalcone derivative crystal for nonlinear optical devices

    Science.gov (United States)

    Ekbote, Anusha; Patil, P. S.; Maidur, Shivaraj R.; Chia, Tze Shyang; Quah, Ching Kheng

    2017-02-01

    In this paper, we present the structure and nonlinear optical (NLO) studies of a D-π-A-π-D type chalcone derivative, (E)-1-(4-aminophenyl)-3-(3-chlorophenyl) prop-2-en-1-one (abbreviated as 3CAMC). The compound was synthesized by Claisen-Schmidt condensation and single crystals were grown by slow evaporation solution growth technique. The structure was confirmed by FT-IR, 1H NMR and single-crystal X-ray diffraction techniques. The 3CAMC crystal is crystallized in the monoclinic crystal system with non-centrosymmetric space group P21 with the unit cell parameters a = 8.0013 (19) Å, b = 4.6630 (11) Å, c = 16.883 (4) Å, β = 95.568 (3)° and Z = 2. The optical absorption spectrum was recorded using UV-Vis-NIR spectrophotometer and the band gap was calculated. The title crystal has a direct band gap of 2.96 eV. TGA/DTA thermal analysis revealed that the crystal has a good thermal stability. The second harmonic generation (SHG) efficiency was investigated using the modified Kurtz-Perry powder test at 1064 nm wavelength with nanosecond (ns) laser pulses. The SHG efficiency is found to be 7 times higher than the well-studied urea. The third-order nonlinear optical properties of 3CAMC at different concentrations were investigated in DMF using Z-scan technique with continuous wave (CW) DPSS laser at 532 nm wavelength. The molecule shows a strong two-photon absorption (2PA) and significant negative nonlinear refraction characteristic (self-defocusing) in the CW regime. Further, we observed the optical limiting behavior in the compound, and evaluated the one-photon and two-photon figures of merit. The encouraging results of NLO studies suggest that the 3CAMC crystal is a promising material for photonics devices, optical switches, and optical power limiting applications.

  1. Cloning and Expression Analysis of Chalcone Isomerase Gene from Narcissus tazetta var.chinensis%中国水仙查尔酮异构酶基因的克隆与表达分析

    Institute of Scientific and Technical Information of China (English)

    蔡雪玲; 陈晓静; 叶一江; 何玮毅; 申艳红

    2011-01-01

    Chalcone isomerase(CHI)is one of the key enzymes in the biosynthesis pathway of flavonoids and plays an important role in the process of flower color development. Three genes, named NtCHIW, NtCHIJ and NtCHIY respectively, were cloned from Narcissus tazetta var. Chinensis petal by RT-PCR and RACE. The open reading frame encompassed 735 bp encoding a polypeptide of 244 amino acids. Sequencing analysis showed that the amino acid sequence of Baihua Narcissus was 93.03%, 93.44%, 64.75%, 55.42%, 50.58%, 59.43%, and 58.20% homologous with CHI genes from Jinzhanyintai Narcissus, Huanghua Narcissus, Allium cepa, Elaeis oleifera, Vitis labrusca, Oryza saliva Japonica, Arabidopsis thaliana, respectively. The result of real time RT-PCR showed that the transcription expression of CHI gene changed accordingly during flower blooming, indicating the possible role of CHI genes in the change of flower color.%查尔酮异构酶(CHI)是影响类黄酮合成的一个重要限速酶,在植物花色发育过程中起着重要作用.通过RT-PCR和RACE技术从中国水仙的花瓣中克隆得到3条CHI基因,分别命名为NtCHIW、NtCHIJ和NtCHIY.3个基因均含有一个735 bp的开放阅读框(ORF),编码244个氨基酸.氨基酸序列分析表明:白花水仙与金盏银台、黄花水仙、洋葱、粳稻、拟南芥、油棕榈、葡萄相应基因的氨基酸序列同源性分别为93.03%、93.44%、64.75%、55.42%、50.58%、59.43%、58.20%.荧光定量PCR分析表明:随着花开放的过程,中国水仙的CHI基因转录水平发生变化,说明CHI基因可能参与花色变化的过程.

  2. Synthesis and Anti-fungal Activity of Chalcones with Pyridyls%吡啶基查尔酮类化合物合成及其抑菌活性

    Institute of Scientific and Technical Information of China (English)

    詹帅军; 金洪; 陶科; 侯太平

    2016-01-01

    为了发现高效、低毒的农用先导化合物,本文采用活性亚结构拼接原理,设计并合成了一类含吡啶基查尔酮类化合物。初步抑菌活性测试结果表明,在测试浓度为100μg/mL时,大多数化合物对供试的水稻纹枯病菌(Rhizoctorzia solani)、苹果轮纹病(Physolospora piricola)、小麦赤霉病菌(Fusarium graminearum)、玉米小斑病菌(Bipolaris maydis)四种植物病原菌均具有一定的抑菌活性,其中化合物I9,I15和I16对水稻纹枯病菌的抑制率在90%以上。病原菌毒力测试表明,化合物I16的EC50值为35.43μg/mL,高于对照药多菌灵(40.56μg/mL)的值,此外,化合物I16还表现出了较宽的抑菌谱,其对四种植物病原菌的抑菌率均大于80%。%In order to find new anti-fungal leading compounds with high performance and low toxicity, this paper designed and synthesized a series of chalcone analogs with pyridyls according to a principle of splice. Bioassays showed that most of target compounds had a certain anti-fungal activities against Rhizoctorzia solani, Physalospora piricola, Fusarium graminearum and Bipolaris maydis at a dosage of 100μg/mL. Inhibition rates of compounds I9, I15 and I16 were more than 90%. The EC50 value of compound I16 was 35.43 μg/mL, which was higher than the control group Carbendazim(40.56μg/mL). Furthermore, compound I16 showed a broad-spectrum fungicidal activity, its fungicidal rate against four kinds of fungi were greater than 80%.

  3. Cloning of the Soybean Chalcone Reductase Gene GmCHR and Construction of Its Plant Expression Vector%大豆查尔酮还原酶基因GmCHR的克隆与植物表达载体构建

    Institute of Scientific and Technical Information of China (English)

    刘江; 陈沛; 邢光南; 赵团结; 李艳; 盖钧镒

    2013-01-01

    黄酮类化合物在植物中参与过滤紫外线、固氮和花色形成等过程,异黄酮对人体有抗氧化、预防乳腺癌等保健作用.查尔酮还原酶(chalcone reductase,CHR)是植物中参与黄酮类化合物代谢的重要酶.克隆大豆查尔酮还原酶基因并构建植物表达载体,有助于进一步研究其功能和异黄酮的代谢过程.采用RT-PCR方法,从栽培大豆(Gly-cine mx)南农1138-2中,克隆得到了第14号染色体上的一个编码大豆查尔酮还原酶(chalcone reductase,CHR)的基因,命名为GmCHR.该基因含有948 bp长的编码区序列(Coding DNA Sequence,CDS),编码315个氨基酸.预测其蛋白质分子量为35.5 kDa,等电点为6.32.与其他豆科植物中的查尔酮还原酶相比,GmCHR蛋白序列与葛藤(Puerariae montana)CHR的相似性最高,达94%.组织表达分析表明,在自然生长条件下GmCHR在叶中的表达量最大;其次是种子;在花和茎中相同;在根中的表达量最小.利用Gateway方法获得植物过表达载体pMDC83-GmCHR,经检测表明过表达载体已成功转化农杆菌EHA105,为今后进一步了解GmCHR在大豆异黄酮代谢过程中的功能提供材料基础.%Flavonoids are involved in UV filtration,symbiotic nitrogen fixation and floral pigmentation in plants. Isoflavones have potential effects on human health,such as antioxirlant activity,preventing breast cancer and other cancers. Chalcone reductase ( CHR) is an important enzyme involved in flavonoid biosynthesis. Cloning of soybean chalcone reductase and construction of its plant expression vector would help study its function and the phenylpropanoid pathway. A gene encoding CHR on chromosome 14 was cloned from the cultivated soybean( Giycine max)cultivar Nannong 1138-2 using RT-PCR,and was designated as GmCHR. This gene contains a coding DNA sequence(CDS)of 948 bp,and the corresponding protein consists of 315 a-mino acids. The protein is estimated to have a molecular weight of 35.5 kDa and

  4. 非洲菊查尔酮合酶基因的克隆、序列分析及在大肠杆菌中的表达%Chalcone Synthase Gene Cloning in Gerbera hybrida and Expression in E.coli

    Institute of Scientific and Technical Information of China (English)

    谢修志; 陈兆平; 王小菁

    2004-01-01

    利用RT-PCR方法,从非洲菊(Gerbera hybrida)花瓣的cDNA中克隆到了查尔酮合酶(Chalcone Synthase,CHS)基因CHS,进行了序列分析.结果表明,克隆到的CHS基因全长为1197 bps,编码一个由398个氨基酸残基组成的多肽,与Helariutta等发表的非洲菊查尔酮合酶CHS1基因的cDNA序列的CHS基因同源性高达99%.进一步将该基因克隆到表达载体pET32a上,经IPTG诱导表达,得到高效表达的融合蛋白.

  5. SYNTHESIS OF CHALCONES, 1, 3-THIAZINES AND 1, 3-PYRIMIDINES DERIVATIVES AND THEIR BIOLOGICAL EVALUATION FOR ANTIINFLAMMATORY, ANALGESIC AND ULCEROGENIC ACTIVITY SYNTHESIS von Chalkonen, 1, 3-Thiazine AND 1, 3-PYRIMIDINE DERIVATE UND IHRE BIOLOGISCHE EVALUATION FOR entzündungshemmende, schmerzstillende und ulcerogene ACTIVITY

    Directory of Open Access Journals (Sweden)

    Vijay V. Dabholkar and Sagar D. Parab

    2011-08-01

    Full Text Available Series of chalcones 2 and 2-amino-4-(2'-amino-5'-substitued phenylmercapto-6-phenyl pyrimidine 3, 2-substituted guanidino-4-(2'-amino-5'-substitued phenylmercapto-6-phenyl-1, 3- thiazine 4, Schiff base of 2-amino-4-(2'-amino-5'-substitued phenylmercapto-6-phenyl pyrimidine 5, 2-[2"-(substituted phenyl-4"-oxo-5"H-thiazol-3"-yl-4-{2'-[2"'- (substitutedphenyl-4"'-oxo-5"'H-thiazol-3"'-yl]-5'-substitued phenyl}mercapto-6-phenyl pyrimidine 6 were synthesized and studied by IR, NMR and Mass spectroscopy. The new products showed anti-inflammatory, analgesic, and ulcerogenic activities comparable to that of indomethacin and acetylsalicylic acid, respectively.

  6. 超声辅助或无溶剂Claisen-Schmidt反应合成含胡椒环的吲哚查尔酮%A facile synthesis of 1,3-benzodioxole-bearing indole-based chalcone via ultrasound-assisted or solvent-free Claisen-Schmidt condensation reaction

    Institute of Scientific and Technical Information of China (English)

    李阳

    2014-01-01

    A structurally novel 1,3-benzodioxole-bearing indole-based chalcone,namely(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-chloro-1-(4-chlorobenzyl)-1H-indol-3-yl) prop-2-en-1-one(3) was synthesized,involving the ultrasound-assisted or solvent-free Claisen-Schmidt condensation reaction of 3-acetyl-2-chloro-1-(4-chlorobenzyl) indole and piperonaldehyde. The ultrasound-assisted Claisen-Schmidt condensation reaction was carried out using 1,4-dioxane as solvent and KOH as catalyst at room temperature to give the product 3 in 78%yield. Alternatively,the reaction could also be conducted under solvent-free condition by physical grinding in a mortar and pestle to obtain 3 in comparable yield of 75%. The two procedures offered easy access to 1,3-benzodioxole-bearing indole-based chalcone in short reaction time and good yield under mild conditions.%3-乙酰基-2-氯-1-(4-氯苄基)吲哚与胡椒醛通过超声辅助或无溶剂的Claisen-Schmidt缩合反应首次合成含胡椒环的吲哚查尔酮,即(E)-3-(5-胡椒基)-1-(2-氯-1-(4-氯苄基)-1H-3-吲哚查尔酮(3)。超声辅助的合成方法使用5%KOH作为催化剂,1,4-二氧六环作为溶剂,以78%的收率得到产品3。另外,这一 Claisen-Schmidt反应也可以在无溶剂研磨条件下进行,同样也以类似的收率获得产品3(75%)。这两种方法具有操作简便、反应条件温和、收率高等优点。

  7. 新型查耳酮衍生物的合成及其初步抗蛋白酪氨酸激酶(PTKs)活性研究%Synthesis of new chalcone derivatives and the in vitro PTKs inhibitory activity

    Institute of Scientific and Technical Information of China (English)

    樊睿; 班树荣; 方莲花; 李青山

    2011-01-01

    目的 设计合成一系列全新的查耳酮类衍生物,并初步测试其蛋白酪氨酸激酶(PTKs)抑制活性.方法 以间二甲苯为原料,经硝化、还原、水解、甲氧甲基保护等反应得到中间体取代苯乙酮,该中间体再与取代苯甲醛发生羟醛缩合反应后脱保护基得到目标化合物.采用酶联免疫吸附法(ELISA),以金雀异黄素为阳性对照,对目标化合物进行体外PTKs抑制活性检测.结果 与结论合成了10个查耳酮衍生物,其中9个是未见报道的新化合物,10个化合物的结构经核磁共振氢谱和质谱确证.化合物6a及新化合物6b、6c和6d对PTKs具有良好的抑制活性.%As one kind of flavone family compounds, chalcone is a kind of high-value compounds bearing common skeleton of diphenyl acrylketone with a variety of pharmacological activities.In our previous work,flavanone derivatives were found have good inhibitory activity against protein tyrosine kinases (PTKs).Now the structural modification of flavanone derivatives was made mainly on the B ring as a new way to prepare chalcone derivatives.Ten target compounds, among them nine are new derivatives, were synthesized by aldol condensation of benzaldehyde derivatives with substituted acetophenone which were obtained by successive nitration, reduction and hydrolysis of m-xylene, followed by methoxymethyl-group protection and then deprotection.Their structures were confirmed by 1H-NMR and ESI-MS.And their protein tyrosine kinases (PTKs)inhibitory activity was investigated by ELISA with genistein as a positive control compound.The results showed that compounds 6a,6b ,6c and 6d exhibited moderate inhibitory activities against protein tyrosine kinases, with inhibition rates varied from 28.44% to 53.12%, while genistein was 50.54%.The results showed that compounds with an ortho electron-withdrawing substituent on the B ring have good activity.

  8. Chemoselective biohydrogenation of chalcone (2{Epsilon})-3-(1,3-benzodioxole-5-yl)-1-phenyl-2-propen-1-one mediated by baker yeasts immobilized in polymeric supports; Bioidrogenacao quimioseletiva da chalcona (2{Epsilon})-3-(1,3-benzodioxol-5-il)-1-fenil-2-propen-1-ona mediada por fermentos de pao imobilizado em suportes polimericos

    Energy Technology Data Exchange (ETDEWEB)

    Mundstock, Flavia L.S.; Silva, Vanessa D.; Nascimento, Maria da G., E-mail: mundstock@qmc.ufsc.b [Universidade Federal de Santa Catarina (DQ/UFSC), Florianopolis, SC (Brazil). Dept. de Quimica

    2009-07-01

    In this study, the yeast Saccharomyces cerevisiae, baker's yeast (BY) was immobilized in poly(ethylene oxide) (PEO), poly(vinyl alcohol) (PVA), sodium caseinate (SC), gelatin (G) films and in agar (A) and gelatin (G) gels, and used as a biocatalyst in the biohydrogenation reaction of (2{Epsilon})-3-(1,3-benzodioxyl-5-yl)-1-phenyl-2-propen-1-one (1). The transformation of (1) into the corresponding dehydro chalcone (2) through biohydrogenation reactions was carried out in n-hexane at 25 or 35 deg C, for 4-48 h reaction. The product conversion, under different experimental conditions, was evaluated by hydrogen nuclear magnetic resonance, {sup 1}H NMR.The highest conversion degrees were achieved using BY immobilized in agar gel, (29-47%), depending also on the temperature. Using BY immobilized in PEO, PVA, SC and G films, the conversion into (2) was lower (0-21%). The results show the feasibility of the use of BY immobilized in polymeric materials to reduce a,b-unsaturated carbonyl compounds. (author)

  9. Effect of Angelica keiskei chalcone on the expression of apoptosis-regulating proteins of mice hepatocarcinoma cells%明日叶查尔酮对小鼠肝癌细胞凋亡相关蛋白表达的影响

    Institute of Scientific and Technical Information of China (English)

    Yang Meng; Jinyi Zhong; He Sun

    2011-01-01

    Objective: The aim of our study was to investigate the effect of Angelica keiskei chalcone (AC) on the expression of Caspase-3 and Bax in mice hepatocarcinoma cells. Methods: Fifty mice inoculated hepatocarcinoma 22 cells were divided into five groups, 10 mice per group. Mice were given 5, 20, 40 mg/kg AC daily by mouth in low, middle and high dose groups respectively. Saline were given to the tumor control group by mouth. Twenty mg/kg cytoxan (CTX) by injection every other day were given to the positive control group. Ten days later, all mice were sacrificed. The levels of the Caspase-3 and Bax protein expression were measured by immunohistochemistry method and the proliferation activity of hepatocarcinoma cells was determined by MTT assay. Results: The expression level of Caspase-3 and Bax protein in tumor control group were 5.00%and 4.68%, respectively, and those of the high-dose group were 38.52% and 35.76%. The differences between two groups were significant (P < 0.05). The cell proliferation activity of tumor control group and high-dose group were 1.135 ± 0.032 and 0.716 ± 0.018. The difference was significant (P < 0.05). Conclusion:AC can increase the expression of Caspase-3 and Bax protein, and inhibit the proliferative activity of mice hepatocarcinoma cells.

  10. 含噻唑烷二酮-3-乙酸结构查尔酮衍生物的合成及抗菌活性的研究%Synthesis and Anti-bacterial Activity of Novel Chalcone Derivatives Containing 2,4-Thiazolidinedione-3-acetic Acid Moiety

    Institute of Scientific and Technical Information of China (English)

    孟凡领; 郑昌吉; 李因晶; 孙良鹏; 刘学坤; 张天一; 朴虎日

    2012-01-01

    A series of novel chalcone derivatives bearing the 2,4-thiazolidinedione-3-acetic acid moieties (8a~8p) were synthesized, and evaluated for their anti-bacterial activity. The results demonstrated that some compounds presented good antimicrobial activities against four multidrug-resistant clinical isolates, among which compounds 8g, 8i, 81 and 8m with minimum inhibitory concentration (MIC) value of 4 ug/mL showed as active as the standard drug, norfloxacin, against methi-cillin-resistant S. Aureus. None of the compounds exhibited obvious activity against the Gram-negative bacteria E. Coli 1356 at 64 μg/mL.%合成了一系列含噻唑烷二酮-3-乙酸结构的新型查尔酮衍生物,并对化合物进行了抗菌活性测定.结果显示,一些化合物对4种多重耐药菌显示出较强的抗菌活性,其中化合物8g,8i,8l和8m在抗耐甲氧西林金黄色葡萄球菌的最小抑制浓度(MIC)达到4 μg/mL,与对照药诺氟沙星(norfloxacin)相当.另外,在64 μg/mL浓度下,所有化合物对大肠杆菌1356均无明显抑制活性.

  11. Synthesis, XRD crystal structure, spectroscopic characterization (FT-IR, 1H and 13C NMR), DFT studies, chemical reactivity and bond dissociation energy studies using molecular dynamics simulations and evaluation of antimicrobial and antioxidant activities of a novel chalcone derivative, (E)-1-(4-bromophenyl)-3-(4-iodophenyl)prop-2-en-1-one

    Science.gov (United States)

    Zainuri, D. Alwani; Arshad, Suhana; Khalib, N. Che; Razak, I. Abdul; Pillai, Renjith Raveendran; Sulaiman, S. Fariza; Hashim, N. Shafiqah; Ooi, K. Leong; Armaković, Stevan; Armaković, Sanja J.; Panicker, C. Yohannan; Van Alsenoy, C.

    2017-01-01

    In the present study, the title compound named as (E)-1-(4-bromophenyl)-3-(4-iodophenyl)prop-2-en-1-one was synthesized and structurally characterized by single-crystal X-ray diffraction. The compound crystallizes in the monoclinic system with P21/c space group with the unit cell parameters of a = 16.147 (2) Å, b = 14.270 (2) Å, c = 5.9058 (9) Å, β = 92.577 (3)° and Z = 4. The molecular geometry obtained from X-Ray structure determination was optimized by Density Functional Theory (DFT) using B3LYP/6-31G+(d, p)/Lanl2dz(f) method in the ground state. The IR spectrum was recorded and interpreted in details with the aid of Density Functional Theory (DFT) calculations and Potential Energy Distribution (PED) analysis. In order to investigate local reactivity properties of the title molecule, we have conducted DFT calculations of average local ionization energy surface and Fukui functions which were mapped to the electron density surface. In order to predict the open air stability and possible degradation properties, within DFT approach, we have also calculated bond dissociation energies. 1H and 13C NMR spectra were recorded and chemical shifts were calculated theoretically and compared with the experimental values. In addition, in vitro antimicrobial results show that the title compound has great potential of antibacterial activity against Staphylococcus aureus, Staphylococcus epidermidis and Micrococcus luteus bacteria and antifungal activity against Candida albicans in comparison to some reported chalcone derivatives. Antioxidant studies revealed the highest metal chelating activity of this compound.

  12. A versatile route to benzodiazocine and spiropyran derivatives through chalcones

    Indian Academy of Sciences (India)

    Johnson George; Saurabh Singh; Rahul Joshi; Ramchand T Pardasani

    2013-05-01

    Syntheses of 3-(phenyl)-benzo[b]thiophene [2, 3-d][1,2] benzodiazocine derivatives have been accomplished by the reaction of 3-phenacylidine-2-benzo[b]thiophene-2-ones with o-phenylene diamine. The photolytic reaction with trans-stilbene resulted in the exclusive formation of spiro{2',5',6'-triphenyl-2H-pyran-4',3}-benzo[b]thiophene-2-one derivatives. Theoretical calculations have been performed to study the mechanism and stereoselectivity of products. Good yield and broad scope of usable substrates of industrial relevance are other prominent features of the present methodologies.

  13. Metabolic changes in Arabidopsis thaliana plants overexpressing chalcone synthase

    NARCIS (Netherlands)

    Dao, Thi Thanh Hien

    2010-01-01

    The study has shown that it is possible to introduce the heterologous CHS gene in Arabidopsis thaliana and common multicopies of transgenes containing plants were obtained. Analysis of the change in metabolome of CHS transgenic plants, high expression transgenic lines can be identified by markers su

  14. Structure-biological activity relationship of synthetic trihydroxilated chalcones

    Directory of Open Access Journals (Sweden)

    Devia Cristina M.

    1998-01-01

    Full Text Available The bacteriostatic activity of 2?,4?,2-trihydroxychalcone; 2?,4?,3-trihydroxychalcone and 2?,4?,4-trihydroxychalcone, prepared by condensation of 2,4-dihydroxyacetophenone and benzaldehyde substituted, against Staphylococcus aureus ATCC 25923 was assayed by agar plate method. The three compounds presented important inhibition halos. In order to elucidate structure-activity relationships, the minimal inhibitory concentrations against S. aureus were determined by the broth dilution method and the results obtained were compared to that of 2',4'-dihydroxychalcone. The sequence observed was: MIC 2?,4?,3-(OH3 > MIC 2?,4?-(OH2 > MIC 2?,4?,4-(OH3 > > MIC 2?,4?,2-(OH3. These results showed that the introduction of an electron donating group (-OH in the aromatic B-ring causes an increase in bioactivity, and that the intensity of action depends on the position of the OH substitute.

  15. 含查尔酮结构N-取代饶丹宁衍生物的合成及抗菌活性研究%Synthesis and biological evaluation of N-substituted rhodanine derivatives bearing chalcone moiety as potent antimicrobial agents

    Institute of Scientific and Technical Information of China (English)

    邢肖兰; 刘婷婷; 宋明霞; 李亚茹; 张雨; 李燕; 李花淑; 郑昌吉; 朴虎日

    2013-01-01

    目的 设计合成两个系列含L-异亮氨酸或L-色氨酸结构的饶丹宁与查尔酮拼合衍生物(4a~4n和5a ~5n),并对其进行体外抗菌活性评价.方法 以取代苯乙酮为原料,经缩合反应和Knoevenagel反应得到目标化合物.采用连续稀释法,以诺氟沙星和苯唑西林为阳性对照药,选取7种金黄色葡萄球菌(S.aureus RN 4220、S.aureus KCTC 503、S.aureus KCTC 209、MRSA CCARM 3167、MRSA CCARM 3506、QRSA CCARM3505、QRSA CCARM 3519)和大肠杆菌(E.coli 1356)为测试菌株对目标化合物进行体外抗菌活性评价.结果与结论 合成了28个未见文献报道的新化合物:(2R)-3-甲基-2-((Z)-4-氧代-5-(4-((E)-3-取代苯基-3-氧代丙-1-烯基)苯亚甲基)-2-硫代噻唑烷-2,4-二酮-3-基)戊酸(4a~4n)和(R)-3-(1H-吲哚-3-基)-2-((Z)-4-氧代-5-(4-((E)-3-取代苯基-3-氧代丙-1-烯基)苯亚甲基)-2-硫代噻唑烷-2,4-二酮-3-基)丙酸(5a~5n).两个系列化合物的结构经1H-NMR和IR谱确证.体外活性测试结果显示,所合成的大部分化合物具有较好的抗菌活性,其中,化合物4n、5g和5j的抗菌活性最好,它们对4种耐药菌的MIC值均为2μg· mL-1.%Two new series of chalcone-based rhodanine derivatives bearing L-isoleucine or L-tryptophane moiety were designed. The target compounds were synthesized from different substituted acetophenones via condensation and Knoevenagel reaction and their in vitro antibacterial activities against seven Staphylococcus aureus strains(5. aureus RN 4220,S. aureus KCTC 503,5. aureus KCTC 209,MRSA CCARM 3167, MR-SA CCARM 3506,QRSA CCARM 3505 and QRSA CCARM 3519) and Escherichia coli 1356 were tested using oxacillin and norfloxacin as positive controls. Twenty-eight new compounds, including (2/R)-2-( (Z)-5-(4-( ( E) -3-( substituted-phenyl) -3-oxoprop-1-en-1-yl) benzylidene) -4-oxo-2-thioxothiazolidin-3-yl) -3-methylpentanoic acid(4a-4n) and (R)-2-( (Z)-5-(4-( (E)-3-(substituted-phenyl)-3-oxoprop-1-en-1-yl) benzylidene

  16. 新型离子负载羟基(对甲苯磺酰氧基)碘苯对α,β-查尔酮及其衍生物的加成产物用于1,4,5-三芳基吡唑的合成%Synthesis of 1,4,5-Triarylpyrazoles from the Addition Products ofα,β-Chalcones with New Ion-Supported [Hydrox-yl(tosyloxy)iodo]benzenes

    Institute of Scientific and Technical Information of China (English)

    郑纯智; 徐小丹; 王雅珍; 赵德建; 张继振

    2015-01-01

    Three newN-(4-iodophenyl)pyridinium salts7~9 were synthesized from pyridine and1-chloro-2,4-dinitrobenzene by three steps. In these steps,N-(2,4-dinitrophenyl)pyridinium chloride5was prepared through the nucleophilic substitution reaction at first. ThenN-(4-iodophenyl)pyridinium chloride was obtained from 4-iodoaniline and5 through the Zincke’s reac-tion. At last the salts7~9weregot in aqueous solution by anion exchange. And then three new pyridinium salts supported [4-hydroxy(tosyloxy)iodo]benzene conjugated reagents [N-(4-hydroxyl(tosyloxy)iodophenyl)pyridinium p-toluenesulfonate 10,N-(4-hydroxyl(tosyloxy)iodophenyl)pyridinium tetrafluoroborate11 andN-(4-hydroxyl(tosyloxy)iodophenyl)pyridinium hexafluorostibnate12]were prepared fromthe salts7~9 and p-toluenesulfonic acid withm-chlorobenzo-peroxoic as oxidizer. These reagents were solid at room temperature and had not the moisture absorption property. The adducts ofα,β-chalcones, 1,3-diaryl-2,3-di(tosyloxy)-1-acetone14(two of them were new compounds), were prepared using the reagents10, 11 and N-[4-hydroxyl(tosyloxy)iodobenzyl]pyridinium tetrafluoroborate4 respectively. The yields of compounds14from reagents10, 11 were also found to be higher than that from reagent4. Finally, 1-phenyl-4,5-diarylpyrazoles (two of them were new com-pounds) were prepared from14 and phenylhydrazine by cyclization reaction. After the addition reaction, the reagents were transformed into the corresponding ion-supported iodobenzenes, which could be easily recovered and regenerated with no lost of the addition reaction activity.%以吡啶和2,4-二硝基氯苯为起始原料,经过三步反应,合成了三种N-(4-碘苯基)吡啶盐新化合物7~9,然后在间氯过氧苯甲酸氧化下,7~9分别与对甲苯磺酸反应制备了三种新的吡啶盐负载羟基(对甲苯磺酰氧基)碘苯共轭试剂: N-[4-羟基(对甲苯磺酰氧基)碘苯基]吡啶对甲苯磺酸盐10、四氟硼酸盐11和六氟锑酸盐12.三种新试剂

  17. 蓝粒小麦花青素合成途径中的查尔酮合酶基因和类黄酮3′5′-羟化酶基因3′末端的克隆和表达分析%Cloning and Expression of Two Chalcone Synthase and a Flavonoid 3′5′- Hydroxylase 3′-end cDNAs from Developing Seeds of Blue-grained Wheat Involved in Anthocyanin Biosynthetic Pathway

    Institute of Scientific and Technical Information of China (English)

    杨国华; 李滨; 高建伟; 刘建中; 赵学强; 郑琪; 童依平; 李振声

    2004-01-01

    DNA ends (RACE) strategies, two chalcone synthase (CHS) cDNAs were cloned from developing seeds of blue-grained wheat, both of the deduced peptides contain 394 amino acids, and share 98.9% of amino acid sequence identity and the nucleotide sequences have the identity of 96.0%, and one flavonoid 3′5′-hydroxylase (F3 ′5 ′H) 3′-end cDNA was isolated. Four CHS genomic DNAs were cloned from Thinopyrum ponticum (Podp.) Z. W. Liu et R. R.-C. Wang (ThpCHS.tg), blue-grained wheat (TaCHS.bg), white-grained offspring of light blue-grained wheat (TaCHS. wg) and Chinese Spring (2n=42)( TaCHS. csg), respectively.Although these four genomic DNAs were isolated from different materials, they are very high homologous and each has one intron. The difference of the four CHS genomic DNAs mainly exists in intron. Through DNA alignment we found that one CHS cDNA ( TaCHS. t1) came from one of the parents, Th. ponticum, the other one ( TaCHS. w1) had the identity of 100% with white grain parent. This indicated that CHS genes from two parents expressed at the same developing stage in blue-grained wheat. Southern blotting analysis showed that they have at least four copies in wheat, the copy numbers in different color grains are not significantly different, but they are different from that of Th. ponticum. CHS in blue-grained wheat belongs to a CHS multifamily. Reverse Northern analysis indicated that the CHS expressed strongly in the developing blue-grained seeds at early stage (15 d after flowering, DAF), but F3 ′5 ′Hand dihydroflavonol 4-reductase (DFR) transcripts accumulated less than that of CHS at early stage. However, at the later developing stage (21 DAF), F3 ′5′Hand DFR transcripts accumulated more than that of CHS, the transcripts of CHS could hardly be detected. The expression order of the three genes is the same as the order of the biosynthetic steps in anthocyanin biosynthesis. At the same time, CHS genes cloned from seeds have not been detected in leaves of blue

  18. Inhibitory Evaluation of Sulfonamide Chalcones on β-Secretase and Acylcholinesterase

    OpenAIRE

    Dae Wook Kim; Heung Joo Yuk; Hye Jin Kim; Jin Hyo Kim; Hyung Won Ryu; Marcus J. Curtis-Long; Jung Keun Cho; Jae Eun Kang; Ki Hun Park

    2012-01-01

    The action of β-secretase (BACE1) is strongly correlated with the onset of Alzheimer’s disease (AD). Aminochalcone derivatives were examined for their ability to inhibit BACE1. Parent aminochalcones showed two digit micromolar IC50s against BACE1. Potency was enhanced 10-fold or more by introducing benzenesulfonyl derivatives to the amino group: 1 (IC50 = 48.2 μM) versus 4a (IC50 = 1.44 μM) and 2 (IC50 = 17.7 μM) versus 5a (IC50 = 0.21 μM...

  19. Mosquito activity of a series of chalcones and 2-pyrazoline derivatives against Aedes aegypti

    Science.gov (United States)

    Aedes aegypti (L.) (Diptera: Culicidae) transmit pathogens to humans, leading to diseases such as yellow fever and dengue fever. Repellents and insecticides are two common interventions to reduce mosquito biting and thereby disease risk. However, overreliance on a chemical or class of chemicals c...

  20. Eco-friendly Synthesis of Ceria Foam via Carboxymethylcellulose Gelation: Application for the Epoxidation of Chalcone

    Science.gov (United States)

    A simple and innovative process is described for the eco-friendly preparation of ceria foams via the carboxymethylcellulose gelation by Ce4+ cations; heat treatment of the ensuing xerogels produces ceria foams. The influence of the concentration of cerium and of the calcination t...

  1. SYNTHESIS AND CHARACTERIZATION OF A DERIVATIVE CYCLOHEXANONE CHALCONE-TYPE, AS AN INTEGRAL LABORATORY EXPERIENCE

    Directory of Open Access Journals (Sweden)

    Perla E. Hernández-González

    2015-03-01

    Full Text Available At present, chemistry teachers are searching new models that allow integrative laboratory experiences, converging interdisciplinary knowledge of the Chemistry field. With this framework of ideas, this work describes the synthesis and characterization of the (2E,6E-2,6-bis(4-methoxybenzylidenecyclohexanone compound as axis of knowledge in order to encourage the students to develop their cognitive skills, such as critical thinking and problem solving, and also interpretation and analysis of results. The compound was synthesized by a Claisen-Schmidt condensation reaction, involving an aromatic aldehyde and cyclohexanone. The compound was characterized spectroscopically by NMR, IR and UV-Vis. Melting point and solubility tests were also performed. The chemical structure was confirmed by single crystal X-Ray diffraction. In conclusion, this laboratory experience allows students to get involved with the techniques and procedures commonly used in the organic chemistry laboratory to the synthesis and characterization of organic compounds.

  2. Synthesis, growth and characterization of π conjugated organic nonlinear optical chalcone derivative

    Energy Technology Data Exchange (ETDEWEB)

    Prabhu, A.N., E-mail: ashwatha.prabhu@manipal.edu [Department of Physics, Manipal Institute of Technology, Manipal University, Manipal 576 104 (India); Upadhyaya, V. [Department of Physics, Manipal Institute of Technology, Manipal University, Manipal 576 104 (India); Jayarama, A., E-mail: jayaram@mite.ac.in [Department of Physics, Mangalore Institute of Technology and Engineering (MITE), Moodabidri 574225 (India); Subrahmanya Bhat, K. [Department of Chemistry, Manipal Institute of Technology, Manipal University, Manipal 576 104 (India)

    2013-02-15

    A new potentially useful nonlinear optical organic material, 1-(5-chlorothiophen-2-yl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one, has been synthesized and grown as a high-quality single crystal by the slow evaporation technique. The grown crystals were characterized by FT-IR, NMR, thermal analysis, and UV–visible spectroscopy. The material is thermally stabile up to 111 °C. The mechanical property of the grown crystals was studied using Vickers microhardness tester and the load dependence hardness was observed. The third order nonlinear optical properties of the material such as real and imaginary part of χ{sup (3)}, nonlinear absorption coefficient and nonlinear refractive index were determined using nanosecond laser pulses at 532 nm wavelength by employing Z-scan technique. The nonlinear refractive index is found to be of the order of 10{sup −11} cm{sup 2} W{sup −1}. The magnitude of third order susceptibility is of the order of 10{sup −13} esu. The observed increase in the third order nonlinearity in these molecules clearly indicates the electronic origin. The compounds exhibit good optical limiting at 532 nm. The best optical limiting behavior of this molecule is due to the substituted strong electron donor. - Highlights: ► A novel thiophene substituted NLO crystal has been grown using methanol as solvent. ► The crystals were characterized by using FTIR, TGA/DTA and UV–visible spectroscopy. ► The n{sub 2} and χ{sup (3)} values is of the order of 10{sup −11} cm{sup 2} W{sup −1} and 10{sup −13} esu respectively. ► The crystals show better optical limiting behavior.

  3. Crystal growth and second harmonic generation efficiency of a chalcone derivative

    Energy Technology Data Exchange (ETDEWEB)

    Meenatchi, V.; Muthu, K.; Rajasekar, M.; Meenakshisundaram, SP., E-mail: aumats2009@gmail.com

    2013-06-15

    Single crystals of (2E,6E)-2-(4-fluorobenzylidine)-6-(4-methoxybenzylidine)cyclohexanone (FBMBC) have been grown by a slow evaporation solution growth technique from ethanol at room temperature. The single crystal X-ray diffraction study reveals that the FBMBC belongs to triclinic system and the cell parameters are a=9.790(6) Å, b=12.08(7) Å, c=14.09(9) Å and V=1577 Å{sup 3}. The structure and the crystallinity of the material were further confirmed by powder X-ray diffraction analysis. The various functional groups present in the molecule are confirmed by Fourier transform infrared spectral analysis. The scanning electron microscopy study reveals the surface morphology of the as-grown crystal. Thermogravimetric/differential thermal analysis studies reveal the purity of the material and the crystals are transparent in the visible region having a low optical cut-off at ∼475 nm. The second harmonic generation efficiency of FBMBC is estimated by the Kurtz and Perry technique. Theoretical calculations were performed using the Hartree–Fock method with 6-31 G(d,p) as the basis set to derive the optimized geometry and the first-order molecular hyperpolarizability (β) values.

  4. Growth and structure of a new photonic crystal: Chlorine substituted chalcone

    Energy Technology Data Exchange (ETDEWEB)

    Sarveshwara, H. P., E-mail: sarvesh.heggadde@gmail.com; Menezes, Anthoni Praveen [Department of Physics, Mangalore Institute Of Technology And Engineering (MITE), Moodabidri-574225 (India); Raghavendra, S.; Dharmaprakash, S. M. [Department of Studies in Physics, Mangalore University, Mangalore -575199 (India); A, Jayarama [Department of Physics, Sadguru Swami Nithyananda Institute of Technology (SSNIT), Kanhangad 671315 (India)

    2015-06-24

    A new organic photonic material 3-(2, 4-dichlorophenyl)-1-(2,5-dimethylthiophen-3-yl)propan-1-one(DMTP) has been synthesized and crystallised in acetone solution. The functional groups present in the new material were identified by FTIR spectroscopy. The material is optically transparent in the wavelength range of 400–1100 nm. The crystal structure of DMTP was determined by single crystal X-ray diffraction. The title compound crystallizes in monoclinic system with a centrosymmetric space group P2{sub 1}/c. The Z-scan study revealed that the optical limiting property exhibited by the DMTP molecule is based on the reverse saturable absorption phenomena.

  5. SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME NOVEL PYRAZOLINE DERIVATIVES DERIVED FROM N-SUBSTITUTED QUINOLINYL CHALCONES

    Directory of Open Access Journals (Sweden)

    Jennifer Fernandes

    2013-10-01

    Full Text Available A series of novel substituted 1-amino-3-(5-phenyl-4, 5-dihydro-1H-pyrazol-3-yl quinolin-2(1H-one (AJP1-AJP8 have been synthesized upon reaction with 1-amino-3-cinnamoyl-quinolin-2(1H-one by using hydrazine hydrate as cyclising medium in alcohol medium. 1-amino-3-cinnamoyl-quinolin-2(1H-one were synthesized by condensing 3-acetyl-1-amino-quinolin-2-one with different substituted benzaldehyde in presence of ethanolic KOH. The structures of the final synthesized compounds were confirmed by IR, 1H NMR and mass spectra. The synthesized compounds were screened for their antibacterial and antifungal activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Candida albicans, Aspergillus niger respectively by cup plate method. Compounds AJP1, AJP3, AJP4, AJP5, AJP6 and AJP7 showed good antibacterial activity compared to the standard drug amoxicillin. Compounds AJP1, AJP3, AJP5 and AJP7 showed moderate antifungal activity compared to the standard drug fluconazole. The synthesized compounds were screened for their anti-inflammatory activity by Carrageenan induced paw edema method. Compounds AJP1 and AJP7 showed significant anti-inflammatory activity compared to the standard drug diclofenac sodium.

  6. Synthesis and topoisomerase II inhibitory and cytotoxic activity of oxiranylmethoxy- and thiiranylmethoxy-chalcone derivatives.

    Science.gov (United States)

    Na, Younghwa; Nam, Jung-Min

    2011-01-01

    In order to find potential anticancer drug candidate targeting topoisomerases enzyme, we have designed and synthesized oxiranylmethoxy- and thiiranylmethoxy-retrochalcone derivatives and evaluated their pharmacological activity including topoisomerases inhibitory and cytotoxic activity. Of the compounds prepared compound 25 showed comparable or better cytotoxic activity against cancer cell lines tested. Compound 25 inhibited MCF7 (IC(50): 0.49 ± 0.21 μM) and HCT15 (IC(50): 0.23 ± 0.02 μM) carcinoma cell growth more efficiently than references. In the topoisomerases inhibition test, all the compounds were inactive to topoisomerase I but moderate inhibitors to topoisomerase II enzyme. Especially, compound 25 inhibited topoisomerase II activity with comparable extent to etoposide at 100 μM concentrations. Correlation between cytotoxicity and topoisomerase II inhibitory activity implies that compound 25 can be a possible lead compound for anticancer drug impeding the topoisomerase II function.

  7. Selective Reduction of Aryl Substituted Chalcones with Zn/Ammonium/Ethanol/Water

    Institute of Scientific and Technical Information of China (English)

    WANG Yu-Lu; ZHOU Yong-Bo

    2003-01-01

    @@ The selective reduction of carbon-carbon double bonds of α, β-unsaturated carbonyl compounds has attracted great interest in organic synthesis. Of many reductive systems described in the literature, transitional metal such as Pd, Rh, Pt, Ni, Cu, Ir and their complexes are usually utilized as catalysts, hydrides of Sn, Se, Te, B and sodium dithionite have been developed to catalyze selective reduction of α, β-unsaturated carbonyl compounds.

  8. Phytochemical and Antimicrobial Screening of Flavanones and Chalcones from Galenia africana and Dicerothamnus rhinocerotis.

    Science.gov (United States)

    Ticha, Lawrence A; Klaasen, Jeremy A; Green, Ivan R; Naidoo, Sivapregasen; Baker, Bienyameen; Pietersen, Ray-Dean

    2015-07-01

    This study focused on an 80% ethanol:water extract of Galenia africana and Dicerothamnus rhinocerotis in which a phytochemical study revealed the presence of flavonoids as the major secondary plant metabolites. Eleven pure flavonoids viz., (E)-2',4'-dihydroxychalcone 1, (S)-7-hydroxyflavanone 2, (E)-2',4'-dihydroxy-2,3-dihydrochalcone 3, (S)-5,7-dihydroxyflavanone 4, (S)-2',5,7,-trihydroxyflavanone 5, (S)-5,7-dihydroxy-2'-methoxyflavanone 6, 5,7-dihydroxy-4H-chromen-4-one 7, (S)-5-hydroxy-7-methoxyflavanone 8 and (E)-2-hydroxy-3',6'-dimethoxychalcone 9 were isolated from G. africana, while [sakuranetin] (S)-4',5-dihydroxy-7-methoxyflavanone 10 and [eriodictyol-3',7-dimethyl ether] (S)-4',5-dihydroxy-3',7-dimethoxyflavanone 11 were isolated from D. rhinocerotis. Compounds 6 and 9 are new while this is the first reported isolation of 1, 2, 3, 4, 5, 7, 8, 10 and 11 from these plants. All isolated compounds were tested for their antimycobacterial activity against the reference strain Mtb H37Rv. The most active compound, 9, demonstrated a MIC99 of 5 μM against Mtb H37Rv American Type Culture (ATCC) and (ATCC27294), which were also sensitive to Isoniazid (INH) and Rifampicin. The antibacterial activity of 9 might be ascribed to the presence of features such as the α,β-unsaturated ketone and the substitution patterns on the A and B rings.

  9. SYNTHESIS AND BIOLOGICAL ACTIVITY OF IMIDAZOLE DERIVED CHALCONES AND IT’S PYRIMIDINES

    OpenAIRE

    2013-01-01

    Microbial contribution increasing rapidly due to invasion by the pathogenic organisms like bacteria, fungi and virus in the present disease burden of human health. To treat these diseases many potent and broad spectrum antibiotics were discovered e.g., ampicillin, amoxicillin, carbenicillin, ofloxacin and tetracycline etc., Even though antibiotics are life saving drugs in therapeutics but they are potentially harmful. These harmful effects include allergic and anaphylactic reaction, developme...

  10. Rapid microwave assisted synthesis and antimicrobial bioevaluation of novel steroidal chalcones.

    Science.gov (United States)

    Kakati, Dwipen; Sarma, Rupak K; Saikia, Ratul; Barua, Nabin C; Sarma, Jadab C

    2013-03-01

    A novel class of chalconoyl pregnenolones has been prepared via Claisen-Schmidt condensation under microwave activation and solvent free reaction conditions. The compounds were screened for antimicrobial activity against two bacterial strains Bacillus subtilis and Escherichia coli and two fungal strains Aspergillus niger and Candida albicans. Some of the compounds exhibited significant inhibitory activity against the microbial strains. Presence of the α,β-unsaturated carbonyl moiety in the synthesized compounds was found to be essential for the activity as manipulation of the same through epoxidation of the double bond diminished the activity.

  11. Synthesis, characterization, electrochemical studies and antitumor activity of some new chalcone analogues containing ferrocenyl pyrazole moiety.

    Science.gov (United States)

    Ratković, Zoran; Juranić, Zorica D; Stanojković, Tatjana; Manojlović, Dragan; Vukićević, Rastko D; Radulović, Niko; Joksović, Milan D

    2010-02-01

    A series of new alpha,beta-unsaturated conjugated ketones containing ferrocenyl pyrazole unit were synthesized and fully characterized by IR and NMR spectroscopy. Electrochemical characterization of subject compounds was performed by means of cyclic voltametry. The in vitro cytotoxic activity of all the synthesized compounds was studied against cervix adenocarcinoma HeLa, melanoma Fem-x and myelogenous leukemia K562 cell lines by the MTT method. Derivative 1l containing 3-pyridyl moiety exhibited a better cytotoxic activity in the cell growth inhibition of K562 cell lines in comparison with cisplatin as a reference compound.

  12. Synthesis, spectroscopic and computational characterization of the tautomerism of pyrazoline derivatives from chalcones.

    Science.gov (United States)

    Miguel, Fábio Balbino; Dantas, Juliana Arantes; Amorim, Stefany; Andrade, Gustavo F S; Costa, Luiz Antônio Sodré; Couri, Mara Rubia Costa

    2016-01-05

    In the present study a series of novel pyrazolines derivatives has been synthesized, and their structures assigned on the basis of FT-Raman, (1)H and (13)C NMR spectral data and computational DFT calculations. A joint computational study using B3LYP/6-311G(2d,2p) density functional theory and FT-Raman investigation on the tautomerism of 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carbothioamide and 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carboxamide are presented. The structures were characterized as a minimum in the potential energy surface using DFT. The calculated Raman and NMR spectra were of such remarkable agreement to the experimental results that the equilibrium between tautomeric forms has been discussed in detail. Our study suggests the existence of tautomers, the carboxamide/carbothioamide group may tautomerize, in the solid state or in solution. Thermodynamic data calculated suggests that the R(CS)NH2 and R(CO)NH2 species are more stable than the R(CNH)SH and R(CNH)OH species. Additionally, results found for the (1)H NMR shifting, pointed out to which structure is present.

  13. Xanthohumol, a prenylated chalcone from beer hops, acts as an α-glucosidase inhibitor in vitro.

    Science.gov (United States)

    Liu, Ming; Yin, Hua; Liu, Ge; Dong, Jianjun; Qian, Zhonghua; Miao, Jinlai

    2014-06-18

    Xanthohumol (XN) is a unique prenylated flavonoid in hops (Humulus lupulus L.) and beer. XN alleviates hyperglycemia and has potential usage in the treatment of type 2 diabetes. In the present study, a series of in vitro experiments were performed to investigate whether XN was an effective inhibitor of α-glucosidase. The results showed that XN inhibited α-glucosidase in a reversible and noncompetitive manner, with an IC50 value of 8.8 μM and that XN inhibited the release of glucose from the maltose in the apical side of the Caco-2 cell monolayer. Fluorescence and circular dichroism spectra results indicated that XN directly bound to α-glucosidase and induced minor conformational changes of the enzyme. These results demonstrated that XN is a promising α-glucosidase inhibitor, which therefore could be used as functional food to alleviate postprandial hyperglycemia and as a potential candidate for the development of an antidiabetic agent.

  14. Growth and structure of a new photonic crystal: Chlorine substituted chalcone

    Science.gov (United States)

    Sarveshwara, H. P.; Raghavendra, S.; A, Jayarama; Menezes, Anthoni Praveen; Dharmaprakash, S. M.

    2015-06-01

    A new organic photonic material 3-(2, 4-dichlorophenyl)-1-(2,5-dimethylthiophen-3-yl)propan-1-one(DMTP) has been synthesized and crystallised in acetone solution. The functional groups present in the new material were identified by FTIR spectroscopy. The material is optically transparent in the wavelength range of 400-1100 nm. The crystal structure of DMTP was determined by single crystal X-ray diffraction. The title compound crystallizes in monoclinic system with a centrosymmetric space group P21/c. The Z-scan study revealed that the optical limiting property exhibited by the DMTP molecule is based on the reverse saturable absorption phenomena.

  15. Synthesis, spectroscopic and computational characterization of the tautomerism of pyrazoline derivatives from chalcones

    Science.gov (United States)

    Miguel, Fábio Balbino; Dantas, Juliana Arantes; Amorim, Stefany; Andrade, Gustavo F. S.; Costa, Luiz Antônio Sodré; Couri, Mara Rubia Costa

    2016-01-01

    In the present study a series of novel pyrazolines derivatives has been synthesized, and their structures assigned on the basis of FT-Raman, 1H and 13C NMR spectral data and computational DFT calculations. A joint computational study using B3LYP/6-311G(2d,2p) density functional theory and FT-Raman investigation on the tautomerism of 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carbothioamide and 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carboxamide are presented. The structures were characterized as a minimum in the potential energy surface using DFT. The calculated Raman and NMR spectra were of such remarkable agreement to the experimental results that the equilibrium between tautomeric forms has been discussed in detail. Our study suggests the existence of tautomers, the carboxamide/carbothioamide group may tautomerize, in the solid state or in solution. Thermodynamic data calculated suggests that the R(Cdbnd S)NH2 and R(Cdbnd O)NH2 species are more stable than the R(Cdbnd NH)SH and R(Cdbnd NH)OH species. Additionally, results found for the 1H NMR shifting, pointed out to which structure is present.

  16. RNA interference silencing of chalcone synthase, the first step in the flavonoid biosynthesis pathway, leads to parthenocarpic tomato fruits

    NARCIS (Netherlands)

    Schijlen, E.G.W.M.; Vos, de C.H.; Martens, S.; Jonker, H.H.; Rosin, F.M.A.; Molthoff, J.W.; Tikunov, Y.M.; Angenent, G.C.; Tunen, van A.J.; Bovy, A.G.

    2007-01-01

    Parthenocarpy, the formation of seedless fruits in the absence of functional fertilization, is a desirable trait for several important crop plants, including tomato (Solanum lycopersicum). Seedless fruits can be of great value for consumers, the processing industry, and breeding companies. In this a

  17. Duplication and divergent evolution of the CHS and CHS-like genes in the chalcone synthase (CHS) superfamily

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    The enzymes of the CHS-superfamily are responsible for biosynthesis of a wide range of natural products in plants. They are important for flower pigmentation, protection against UV light and defense against phytopathogens. Many plants were found to contain multiple copies of CHS genes. This review summarizes the recent progress in the studies of the CHS-superfamily, focusing on the duplication and divergent evolution of the CHS and CHS-like genes. Comparative analyses of gene structure, expression patterns and catalytic properties revealed extensive differentiation in both regulation and function among duplicate CHS genes. It is also proposed that the CHS-like enzymes in the CHS-superfamily evolved from CHS at different times in various organisms. The CHS-superfamily thus offers a valuable model to study the rates and patterns of sequence divergence between duplicate genes.

  18. Highly Catalytic Enantioselective Addition of Diethyl Zinc to Aldehydes and Chalcone in the Presence of Chiral Ligands

    Institute of Scientific and Technical Information of China (English)

    WANG; Rui

    2001-01-01

    Catalytic asymmetric carbon-carbon bond formation is one of the most important reactions and have attracted much attention to develop more efficient enantioselective C-C formation methods in organic synthesis. In this field, asymmetric addition of diethylzinc to aldehydes[1] and conjugate addition to enones[2] have drawn special interests and have been greatly developed. Regardless of it, much spaces in these areas still exist, so it needs more extensive and intensive researches for the purpose of as follows: (1) attaching ligands to a polymer for the easy separation of the catalysts so as to be able to allow very efficient recovery and reuse of the catalysts, and the possibility of carrying out the desired transfomation in continuous mode in a flow reactor, etc., (2) searching for novel chiral catalysts with such features as more suitable for more extensive substrates varieties, and more convenient and economical as well as possessing applicable prospect, and so on. Here we report some works in these areas done in our laboratory.  ……

  19. Anti-proliferative effect of chalcone derivatives through inactivation of NF-κB in human cancer cells.

    Science.gov (United States)

    Venkateswararao, Eeda; Sharma, Vinay K; Yun, Jieun; Kim, Youngsoo; Jung, Sang-Hun

    2014-07-01

    To investigate the anti-proliferative effect of NF-κB inhibitor, a series of analogs of (E)-1-(2-hydroxy-6-(isopentyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5a) were prepared and evaluated for their NF-κB inhibition and anti-proliferative activity against various human cancer cell lines. Compounds (E)-1-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (5e) and (E)-4-(3-(2-(3,3-dimethylbutoxy)-6-hydroxyphenyl)-3-oxoprop-1-enyl)benzenesulfonamide (5p) showed good NF-κB inhibition as well as potent anti-proliferative activity. SAR studies showed that all the compounds with potent or moderate NF-κB inhibition displayed good anti-proliferative activity. All the analogs (5b-r) maintained a good correlation between their NF-κB inhibition and anti-proliferative activity though the extent is not directly proportional to each other.

  20. Solvent‐free synthesis, spectral correlations and antimicrobial activities of some 3,4‐ dimethoxy chalcones

    Directory of Open Access Journals (Sweden)

    V. Mala

    2012-03-01

    Full Text Available Background: The aim of this study was to synthesise some substituted styryl 3,4-dimethoxy phenyl ketones using solvent-free SiO2-H2SO4 catalyzed aldol condensation between 3,4- dimethoxy acetophenone and substituted benzaldehydes under microwave irradiation. Then to characterize them by their analytical, physical and spectroscopic data, and also to study their the spectral correlation and antimicrobial activities.