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Sample records for coumarin

  1. Coumarin embryopathy

    Energy Technology Data Exchange (ETDEWEB)

    Struwe, F.E.; Reinwein, H.; Stier, R.

    1984-02-01

    Anticoagulant therapy using Coumarin derivatives (vitamin K antagonists) during early pregnancy may result in a characteristic embryopathy appearing as a phaenocopy of chondrodysplasia punctata (Conradi-Huenermann's disease). This has been suggested in advance by observations made in newborns of mothers who had been treated previously with Warfarin or Acenocoumon. Similar observations made in a newborn after the mother's treatment with Phencoumon in early pregnancy are described in this paper. Coumarin embryopathy is proposed as a common term.

  2. Supramolecular Photodimerization of Coumarins

    Directory of Open Access Journals (Sweden)

    Koichi Tanaka

    2012-02-01

    Full Text Available Stereoselective photodimerization of coumarin and its derivatives in supra-molecular systems is reviewed. The enantioselective photodimerization of coumarin and thiocoumarin in inclusion crystals with optically active host compounds is also described.

  3. Sesquiterpene coumarins from Ferula gumosa.

    Science.gov (United States)

    Iranshahi, Mehrdad; Masullo, Milena; Asili, Ali; Hamedzadeh, Ali; Jahanbin, Bentolhoda; Festa, Michela; Capasso, Anna; Piacente, Sonia

    2010-11-29

    A new sesquiterpene coumarin, gumosin (1), two new sesquiterpene coumarin glycosides, gumosides A (2) and B (3), and 10 known compounds, namely, cauferoside (4), feselol (5), conferoside, ferilin, ferocaulidin, ligupersin A, conferol, and daucosterol, and the phenolic compounds acantrifoside E and 4-hydroxybenzoic acid 4-(6-O-sulfo)glucopyranoside, were isolated from a methanolic extract of Ferula gumosa roots. The structures of 1-3 were elucidated by spectroscopic data interpretation. The cytotoxic activity of the sesquiterpene coumarin derivatives was evaluated against a small panel of cancer cell lines.

  4. 21 CFR 189.130 - Coumarin.

    Science.gov (United States)

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Coumarin. 189.130 Section 189.130 Food and Drugs... Direct Addition or Use as Human Food § 189.130 Coumarin. (a) Coumarin is the chemical 1,2-benzopyrone... synthesized. It has been used as a flavoring compound. (b) Food containing any added coumarin as such or as...

  5. Evaluation of Halogenated Coumarins for Antimosquito Properties

    Directory of Open Access Journals (Sweden)

    Venugopala K. Narayanaswamy

    2014-01-01

    Full Text Available Mosquitoes are the major vectors of parasites and pathogens affecting humans and domestic animals. The widespread development of insecticide resistance and negative environmental effects of most synthetic compounds support an interest in finding and developing alternative products against mosquitoes. Natural coumarins and synthetic coumarin analogues are known for their several pharmacological properties, including being insecticidal. In the present study halogenated coumarins (3-mono/dibromo acetyl, 6-halogenated coumarin analogues were screened for larvicidal, adulticidal, and repellent properties against Anopheles arabiensis, a zoophilic mosquito that is one of the dominant vectors of malaria in Africa. Five compounds exerted 100% larval mortality within 24 h of exposure. All coumarins and halogenated coumarins reversibly knocked down adult mosquitoes but did not kill them after 24 h of exposure. Repellent properties could not be evidenced. Five compounds were considered potential larvicidal agents for further research and development, while adulticidal activity was considered only mild to moderate.

  6. Coumarin-fused coumarin: antioxidant story from N,N-dimethylamino and hydroxyl groups.

    Science.gov (United States)

    Xi, Gao-Lei; Liu, Zai-Qun

    2015-04-01

    Two coumarin skeletons can form chromeno[3,4-c]chromene-6,7-dione by sharing with the C ═ C in lactone. The aim of the present work was to explore the antioxidant effectiveness of the coumarin-fused coumarin via six synthetic compounds containing hydroxyl and N,N-dimethylamino as the functional groups. The abilities to quench 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+•)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical revealed that the rate constant for scavenging radicals was related to the amount of hydroxyl group in the scaffold of coumarin-fused coumarin. But coumarin-fused coumarin was able to inhibit DNA oxidations caused by (•)OH, Cu(2+)/glutathione (GSH), and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH) even in the absence of hydroxyl group. In particular, a hydroxyl and an N,N-dimethylamino group locating at different benzene rings increased the inhibitory effect of coumarin-fused coumarin on AAPH-induced oxidation of DNA about 3 times higher than a single hydroxyl group, whereas N,N-dimethylamino-substituted coumarin-fused coumarin possessed high activity toward (•)OH-induced oxidation of DNA without the hydroxyl group contained. Therefore, the hydroxyl group together with N,N-dimethylamino group may be a novel combination for the design of coumarin-fused heterocyclic antioxidants.

  7. Coumarin derivatives, but not coumarin itself, cause skin irritation via topical delivery.

    Science.gov (United States)

    Pan, Tai-Long; Wang, Pei-Wen; Aljuffali, Ibrahim A; Leu, Yann-Lii; Hung, Yi-Yun; Fang, Jia-You

    2014-04-21

    Coumarin and its derivatives are widely employed as a fragrance in cosmetics and skin care products. The skin absorption level and possible disruption to the skin by topical application of coumarins were evaluated in this study. Percutaneous absorption of osthole, daphnoretin, coumarin, byakangelicin, and 7-hydroxycoumarin was assessed in vitro and in vivo. Skin physiology measurements and immunoblotting were utilized as methodologies for validating toxicity. The relationship between structures and permeation/toxicity of coumarins was elucidated. Both equimolar concentration and saturated solubility in 30% ethanol were used as the applied dose. Osthole with the most lipophilic characteristic demonstrated the greatest skin accumulation, followed by coumarin and 7-hydroxycoumarin. Coumarin was the permeant with the highest flux across the skin. The trend of in vivo deposition was consistent with that of the in vitro profiles. Skin uptake of osthole was 8-fold higher than that of coumarin. Hair follicles played a significant role as a pathway for transport of coumarin according to the examination of follicular accumulation. Osthole and 7-hydroxycoumarin slightly, but significantly, enhanced transepidermal water loss after a consecutive 5-day administration. The immunoblotting profiling verified the role of proliferation in skin damage induced by osthole, byakangelicin, and 7-hydroxycoumarin. The proliferation-related proteins examined in this work included glucose-regulated proteins, cytokeratin, and C-myc. Daphnoretin and coumarin showed a negligible alteration on protein biomarkers. The experimental results suggested that skin irritation caused by coumarins was mainly derived from the analogs but not from coumarin itself.

  8. Novel Fluorescent Dyes Based on Coumarin System

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    Seven novel fluorescent coumarin derivatives were synthesized from 7-diethylamino-4-chloro-3-formyl coumarin. The spectra of absorption, excitation and emission were dependent not only on the structures and also on the concentration of dyes. The PPP-MO predictions can only be consistent with the spectra in dilute solutions.

  9. Growth until puberty after in utero exposure to coumarins

    NARCIS (Netherlands)

    Van Driel, D; Wesseling, J; Rosendaal, FR; Odink, RJ; Van der Veer, E; Gerver, WJ; Geven-Boere, LM; Sauer, PJJ

    2000-01-01

    Anticoagulation with coumarins is an effective therapy during pregnancy. Fetal exposure to coumarin derivatives during the first trimester, however, is associated with skeletal anomalies (warfarin or coumarin embryopathy). Information about long-term effects of prenatal coumarin exposure on the skel

  10. Coumarin: a promising scaffold for anticancer agents.

    Science.gov (United States)

    Kaur, Manjinder; Kohli, Swarandeep; Sandhu, Sonali; Bansal, Yogita; Bansal, Gulshan

    2015-01-01

    Coumarin enjoys an important place in drug discovery process due to its presence in diversity of biologically active compounds. Many compounds of plant origin are derivatives of coumarin. Taking these natural products as lead, research groups across the globe have designed and synthesized numerous coumarin analogues for treatment of varied diseases. Cancer is one of the dreadful chronic diseases, and many drugs are available for its treatment. However, due to heterogeneity of cancer, the search is still on to develop drugs for specific types of cancers. The present review is an attempt to study various coumarin derivatives of natural as well as synthetic origins, which are identified or developed for the treatment of different types of cancers. Herein, we have classified various anticancer coumarin derivatives on the basis of their origin as well as substitution around it. These are discussed under the headings of natural, semi-synthetic and synthetic coumarin derivatives. The synthetic coumarin derivatives are further classified as mono-, di- and poly-substituted and fused coumarin derivatives. Of the six positions available for substituents on coumarin nucleus, only three positions (C-3, C-4 and C-7) are exploited for the selection of functional groups appropriate for anticancer activity. The other positions (C-5, C-6 and C-8) are either unexplored or very less exploited. The present review is expected to provide the medicinal chemists a guide to choose new functional groups for substitution at different positions of coumarin nucleus for development of novel compounds for the treatment of a specific type of cancer.

  11. Synthesis and Fluorescence Properties of Coumarin Glycosides and Triazoylglycosides

    Institute of Scientific and Technical Information of China (English)

    WU Zheng; FU Xin-ling; YANG Nan; WANG Qiu-an

    2013-01-01

    Four coumarin glycosides(1-4) and four coumarin triazoylglycosides(5-8) were synthesized by phase transfer catalytic glycosylation and copper-catalyzed azide-alkyne cycloaddition(CuAAC) respectively from 4-methyl-7-hydroxyl coumarin(4-methylumbelliferone).The structures were characterized by 1H NMR,MS or IR.The fluorescent properties of the coumarin glycosides and triazoylglycosides were studied in different solvents and compared to those of 4-methyl-7-hydroxyl coumarin.

  12. Solvent-Free Synthesis of New Coumarins

    Directory of Open Access Journals (Sweden)

    Redah I. Al-Bayati

    2012-01-01

    Full Text Available A solvent-free synthesis of five series of coumarin derivatives using microwave assistant is presented herein. The synthesized compounds are fully characterized by UV-VIS, FT-IR, and NMR spectroscopy.

  13. Biologically active sesquiterpene coumarins from Ferula species.

    Science.gov (United States)

    Nazari, Zeinab Esmail; Iranshahi, Mehrdad

    2011-03-01

    Extracts from different species of the genus Ferula (Apiaceae) have had various biomedical applications for many centuries. Many biological features of this genus such as cytotoxicity, antibacterial, antiviral, P-glycoprotein (P-gp) inhibitory and antiinflammatory activity have been attributed to sesquiterpene coumarins; structures containing a common coumarin group and a sesquiterpene moiety. This both highlights the importance of sesquiterpene coumarins as biologically active natural products and necessitates further studies on these compounds. Taking into account the versatile biological properties of compounds isolated from Ferula and the unprecedented interest in the application of natural products as a new generation of therapeutics, the present review will discuss reports on biological activities of sesquiterpene coumarins of the genus Ferula, from 1990 onwards.

  14. Optical properties of coumarins containing copolymers

    Science.gov (United States)

    Skowronski, L.; Krupka, O.; Smokal, V.; Grabowski, A.; Naparty, M.; Derkowska-Zielinska, B.

    2015-09-01

    We investigate the optical properties such as absorption coefficient, refractive index, real and imaginary parts of dielectric function and energy band gap of coumarin-containing copolymers thin films by means of spectroscopic ellipsometry (SE) combined with transmittance measurements (T) and atomic force microscopy (AFM). We found that the optical properties of coumarin-containing copolymers strongly depend from length of alkyl spacer as well as the type of substitution in coumarin moiety. In our case the refractive index as well as the energy band gap of coumarin-containing copolymer decrease with increase the length of alkyl spacer. Additionally, the lengthening of the alkyl spacer brings the bathochromic shifts of the absorption spectra towards longer wavelengths.

  15. Compound list: coumarin [Open TG-GATEs

    Lifescience Database Archive (English)

    Full Text Available coumarin CMA 00027 ftp://ftp.biosciencedbc.jp/archive/open-tggates/LATEST/Human/in_vitro/coum...arin.Human.in_vitro.Liver.zip ftp://ftp.biosciencedbc.jp/archive/open-tggates/LATEST/Rat/in_vitro/coum...arin.Rat.in_vitro.Liver.zip ftp://ftp.biosciencedbc.jp/archive/open-tggates/LATEST/Rat/in_vivo/Liver/Single/coum...-tggates/LATEST/Rat/in_vivo/Liver/Repeat/coumarin.Rat.in_vivo.Liver.Repeat.zip ...

  16. Sesquiterpene coumarins from seeds of Ferula sinkiangensis.

    Science.gov (United States)

    Li, Guangzhi; Li, Xiaojin; Cao, Li; Zhang, Lijing; Shen, Liangang; Zhu, Jun; Wang, Junchi; Si, Jianyong

    2015-06-01

    A new sesquiterpene coumarin with a novel sesquiterpene carbon framework, Sinkiangenorin D, and ten known sesquiterpene coumarins were isolated from the seeds of Ferula sinkiangensis. The structures of these compounds, including the relative stereochemistry, were elucidated on the basis of spectroscopic data. All of the isolated compounds were tested against the AGS, HeLa, and K562 human cancer cell lines and showed cytotoxic activities with 50% inhibitory concentration values between 12.7 and 226.6 μM.

  17. A new coumarin glucoside, coumarins and alkaloids from Ruta corsica roots.

    Science.gov (United States)

    Bertrand, Cédric; Fabre, Nicolas; Moulis, Claude

    2004-03-01

    A new coumarin glucoside, 3'(S)-hydroxy-2',2'-dimethyl-dihydropyranocoumarin-8-beta-d-glucopyranosyl, one coumarin, five furanocoumarins, three bicoumarins, three quinoline alkaloids and one sinapoyl sucrose derivative have been isolated from the roots of Ruta corsica.

  18. Halogenated coumarin derivatives as novel seed protectants.

    Science.gov (United States)

    Brooker, N; Windorski, J; Bluml, E

    2008-01-01

    Development of new and improved antifungal compounds that are target-specific is backed by a strong Federal, public and commercial mandate. Many plant-derived chemicals have proven fungicidal properties, including the coumarins (1,2-Benzopyrone) found in a variety of plants such as clover, sweet woodruff and grasses. Preliminary research has shown the coumarins to be a highly active group of molecules with a wide range of antimicrobial activity against both fungi and bacteria. It is believed that these cyclic compounds behave as natural pesticidal defence molecules for plants and they represent a starting point for the exploration of new derivative compounds possessing a range of improved antifungal activity. Within this study, derivatives of coumarin that were modified with halogenated side groups were screened for their antifungal activity against a range of soil-borne plant pathogenic fungi. Fungi included in this in vitro screen included Macrophomina phaseolina (charcoal rot), Phytophthora spp. (damping off and seedling rot), Rhizoctonia spp. (damping off and root rot) and Pythium spp. (seedling blight), four phylogenetically diverse and economically important plant pathogens. Studies indicate that these halogenated coumarin derivatives work very effectively in vitro to inhibit fungal growth and some coumarin derivatives have higher antifungal activity and stability as compared to the original coumarin compound alone. The highly active coumarin derivatives are brominated, iodinated and chlorinated compounds and results suggest that besides being highly active, very small amounts can be used to achieve LD100 rates. In addition to the in vitro fungal inhibition assays, results of polymer seed coating compatibility and phytotoxicity testing using these compounds as seed treatments will also be reported. These results support additional research in this area of natural pesticide development.

  19. The Synthesis of a Series of Phosphoryl Coumarins

    Institute of Scientific and Technical Information of China (English)

    2005-01-01

    Different hydroxy substituted coumarins were successfully phosphorylated with diisopropylphophite (DIPPH) by the Atherton-Todd reaction in 76-89% yields. Moreover, the reaction activities of different hydroxys of the coumarins in the Atherton-Todd reaction were studied.

  20. Accumulation of coumarins in Arabidopsis thaliana.

    Science.gov (United States)

    Kai, Kosuke; Shimizu, Bun-ichi; Mizutani, Masaharu; Watanabe, Ken; Sakata, Kanzo

    2006-02-01

    The biosynthesis of coumarins in plants is not well understood, although these metabolic pathways are often found in the plant kingdom. We report here the occurrence of coumarins in Arabidopsis thaliana ecotype Columbia. Considerably high levels of scopoletin and its beta-d-glucopyranoside, scopolin, were found in the wild-type roots. The scopolin level in the roots was approximately 1200nmol/gFW, which was approximately 180-fold of that in the aerial parts. Calli accumulated scopolin at a level of 70nmol/gFW. Scopoletin and scopolin formation were induced in shoots after treatment with either 2,4-dichlorophenoxyacetic acid (at 100microM) or a bud-cell suspension of Fusarium oxysporum. In order to gain insight into the biosynthetic pathway of coumarins in A. thaliana, we analyzed coumarins in the mutants obtained from the SALK Institute collection that carried a T-DNA insertion within the gene encoding the cytochrome P450, CYP98A3, which catalyzes 3'-hydroxylation of p-coumarate units in the phenylpropanoid pathway. The content of scopoletin and scopolin in the mutant roots greatly decreased to approximately 3% of that in the wild-type roots. This observation suggests that scopoletin and scopolin biosynthesis in A. thaliana are strongly dependent on the 3'-hydroxylation of p-coumarate units catalyzed by CYP98A3. We also found that the level of skimmin, a beta-d-glucopyranoside of umbelliferone, was slightly increased in the mutant roots.

  1. Two new coumarins from Murraya paniculata.

    Science.gov (United States)

    Saied, Sumayya; Nizami, Shaikh Sirajuddin; Anis, Itrat

    2008-01-01

    Two new coumarins, murrmeranzin (1) and murralonginal (2), together with four known compounds minumicrolin (3), murrangatin (4), meranzin hydrate (5) and hainanmurpanin (6) have been isolated from the aerial parts of Murraya paniculata. The structures of these compounds were determined through spectral analysis. Minumicrolin (3) showed mild butyrylcholinesterase inhibition activity.

  2. Biogas production from coumarin-rich plants--inhibition by coumarin and recovery by adaptation of the bacterial community.

    Science.gov (United States)

    Popp, Denny; Schrader, Steffi; Kleinsteuber, Sabine; Harms, Hauke; Sträuber, Heike

    2015-09-01

    Plants like sweet clover (Melilotus spp.) are not suitable as fodder for cattle because of harmful effects of the plant secondary metabolite coumarin. As an alternative usage, the applicability of coumarin-rich plants as substrates for biogas production was investigated. When coumarin was added to continuous fermentation processes codigesting grass silage and cow manure, it caused a strong inhibition noticeable as decrease of biogas production by 19% and increase of metabolite concentrations to an organic acids/alkalinity ratio higher than 0.3(gorganic acids) gCaCO3 (-1). Microbial communities of methanogenic archaea were dominated by the genera Methanosarcina (77%) and Methanoculleus (11%). This community composition was not influenced by coumarin addition. The bacterial community analysis unraveled a divergence caused by coumarin addition correlating with the anaerobic degradation of coumarin and the recovery of the biogas process. As a consequence, biogas production resumed similar to the coumarin-free control with a biogas yield of 0.34 LN g(volatile solids) (-1) and at initial metabolite concentrations (∼ 0.2 g(organic acids) gCaCO3 (-1)). Coumarin acts as inhibitor and as substrate during anaerobic digestion. Hence, coumarin-rich plants might be suitable for biogas production, but should only be used after adaptation of the microbial community to coumarin.

  3. Coumarin amide derivatives as fluorescence chemosensors for cyanide anions

    Energy Technology Data Exchange (ETDEWEB)

    Wu, Qianqian [School of Material Science and Engineering, Shandong Provincial Key Laboratory of Preparation and Measurement of Building Materials, University of Jinan, Jinan 250022, Shandong (China); Liu, Zhiqiang [State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, Shandong (China); Cao, Duxia, E-mail: duxiacao@ujn.edu.cn [School of Material Science and Engineering, Shandong Provincial Key Laboratory of Preparation and Measurement of Building Materials, University of Jinan, Jinan 250022, Shandong (China); Guan, Ruifang, E-mail: mse_guanrf@ujn.edu.cn [School of Material Science and Engineering, Shandong Provincial Key Laboratory of Preparation and Measurement of Building Materials, University of Jinan, Jinan 250022, Shandong (China); Wang, Kangnan; Shan, Yanyan; Xu, Yongxiao; Ma, Lin [School of Material Science and Engineering, Shandong Provincial Key Laboratory of Preparation and Measurement of Building Materials, University of Jinan, Jinan 250022, Shandong (China)

    2015-07-01

    Four coumarin amide derivatives with 4-methyl coumarin or pyrene as terminal group have been synthesized. Their photophysical properties and recognition properties for cyanide anions have been examined. The results indicate that the compounds can recognize cyanide anions with obvious absorption and fluorescence spectra change, at the same time, obvious color and fluorescence change can be observed by naked eye. The in situ hydrogen nuclear magnetic resonance spectra and photophysical properties change confirm that Michael additions between the chemosensors and cyanide anions take place at the 4-position of coumarin. - Highlights: • Four coumarin amide derivatives with 4-methyl coumarin or pyrene as terminal group were synthesized. • The compounds can recognize cyanide anions with obvious absorption and fluorescence spectra change. • Michael additions between the chemosensors and cyanide anions take place at the 4-position of coumarin.

  4. Ethyl coumarin-3-carboxylate: synthesis and chemical properties

    Directory of Open Access Journals (Sweden)

    Bakr F. Abdel-Wahab

    2014-03-01

    Full Text Available Ethyl coumarin-3-carboxylate occupies an important position in the organic synthesis and is used in production of biologically active compounds. Thus, the data published over the last few years on the methods of synthesis and chemical properties of ethyl coumarin-3-carboxylate are reviewed here for the first time. The reactions were classified as coumarin ring reactions and ester group reactions, and some of these reactions have been applied successfully to the synthesis of biologically and industrially important compounds.

  5. A review of coumarin derivatives in pharmacotherapy of breast cancer.

    Science.gov (United States)

    Musa, Musiliyu A; Cooperwood, John S; Khan, M Omar F

    2008-01-01

    The coumarin (benzopyran-2-one, or chromen-2-one) ring system, present in natural products (such as the anticoagulant warfarin) that display interesting pharmacological properties, has intrigued chemists and medicinal chemists for decades to explore the natural coumarins or synthetic analogs for their applicability as drugs. Many molecules based on the coumarin ring system have been synthesized utilizing innovative synthetic techniques. The diversity oriented synthetic routes have led to interesting derivatives including the furanocoumarins, pyranocoumarins, and coumarin sulfamates (COUMATES), which have been found to be useful in photochemotherapy, antitumor and anti-HIV therapy, and as stimulants for central nervous system, antibacterials, anti-inflammatory, anti-coagulants, and dyes. Of particular interest in breast cancer chemotherapy, some coumarins and their active metabolite 7-hydroxycoumarin analogs have shown sulfatase and aromatase inhibitory activities. Coumarin based selective estrogen receptor modulators (SERMs) and coumarin-estrogen conjugates have also been described as potential antibreast cancer agents. Since breast cancer is the second leading cause of death in American women behind lung cancer, there is a strong impetus to identify potential new drug treatments for breast cancer. Therefore, the objective of this review is to focus on important coumarin analogs with antibreast cancer activities, highlight their mechanisms of action and structure-activity relationships on selected receptors in breast tissues, and the different methods that have been applied in the construction of these pharmacologically important coumarin analogs.

  6. Anti-inflammatory new coumarin from the Ammi majus L.

    Science.gov (United States)

    Selim, Yasser Abdelaal; Ouf, Nabil Hassan

    2012-01-12

    Investigation of the aerial parts of the Egyptian medicinal plant Ammi majus L. led to isolation of new coumarin, 6-hydroxy-7-methoxy-4 methyl coumarin (2) and 6-hydroxy-7-methoxy coumarin (3); this is the first time they have been isolated from this plant. The structures of the compounds (2 &3) were elucidated by spectroscopic data interpretation and showed anti-inflammatory and anti-viral activity. GRAPHICAL An efficient, one-new coumarin (2) was isolated from the aerial parts of the A. Majus L. was evaluated for their anti-viral and anti-inflammatory activities.

  7. Two new coumarin glycosides from Chimonanthus nitens.

    Science.gov (United States)

    Li, Qi-Ji; Wang, Ming-Li; Yang, Xiao-Sheng; Ma, Lin; Hao, Xiao-Jiang

    2013-01-01

    Two new coumarin glycosides, namely nitensosides A-B (1-2), together with six known compounds, scopolin (3), 5,6,7-trimethoxycoumarin (4), d-calycanthine (5), calycanthoside (6), xeroboside (7), and scopoletin (8), were isolated from Chimonanthus nitens. The structures of the new compounds were elucidated by comprehensive analysis of IR, MS, and NMR spectroscopic data. Compounds 3, 4, 7, and 8 showed moderate inhibitory activity against Micrococcus luteus.

  8. Genetically encoded fluorescent coumarin amino acids

    Science.gov (United States)

    Wang, Jiangyun; Xie, Jianming; Schultz, Peter G.

    2010-10-05

    The invention relates to orthogonal pairs of tRNAs and aminoacyl-tRNA synthetases that can incorporate the coumarin unnatural amino acid L-(7-hydroxycoumarin-4-yl) ethylglycine into proteins produced in eubacterial host cells such as E. coli. The invention provides, for example but not limited to, novel orthogonal synthetases, methods for identifying and making the novel synthetases, methods for producing proteins containing the unnatural amino acid L-(7-hydroxycoumarin-4-yl)ethylglycine and related translation systems.

  9. A new sesquiterpenoid coumarin from Ferula assafoetida.

    Science.gov (United States)

    Ghosh, Anindita; Banerji, Avijit; Mandal, Suvra; Banerji, Julie

    2009-08-01

    The gum resin of Ferula assafoetida Linn. afforded one new sesquiterpene, asimafoetida 1 and three known sesquiterpenoid coumarins. The structure has been established from extensive 2D NMR spectral studies as 7'-[7-(1R,3S)-5-Hydroxy-6,6-dimethyl-2-methylene-cyclohexyl]-9-methyl-9-pentenyl]oxy]-2H-1-benzopyran-2-one. The other three known compounds are ferulic acid, farnesiferol A and farnesiferol C.

  10. A new coumarin glycoside from Daphne giraldii

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    A new coumarin glycoside was isolated from the ethanol extract of the barks of stem of Daphne giraldii Nitsche. Its structure was defined as daphnetin 8-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside on the basis of spectral evidences.(C) 2007 Wei Dong Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  11. Genetically encoded fluorescent coumarin amino acids

    Energy Technology Data Exchange (ETDEWEB)

    Wang, Jiangyun [San Diego, CA; Xie, Jianming [San Diego, CA; Schultz, Peter G [La Jolla, CA

    2012-06-05

    The invention relates to orthogonal pairs of tRNAs and aminoacyl-tRNA synthetases that can incorporate the coumarin unnatural amino acid L-(7-hydroxycoumarin-4-yl)ethylglycine into proteins produced in eubacterial host cells such as E. coli. The invention provides, for example but not limited to, novel orthogonal synthetases, methods for identifying and making the novel synthetases, methods for producing proteins containing the unnatural amino acid L-(7-hydroxycoumarin-4-yl)ethylglycine and related translation systems.

  12. Potential antibacterial activity of coumarin and coumarin-3-acetic acid derivatives.

    Science.gov (United States)

    Chattha, Fauzia Anjum; Munawar, Munawar Ali; Nisa, Mehrun; Ashraf, Mohammad; Kousar, Samina; Arshad, Shafia

    2015-05-01

    Coumarin and coumarin-3-acetic acid derivatives were synthesized by reacting phenols with malic acid, ethyl acetoacetate and ethyl acetylsuccinate in appropriate reaction conditions. All synthesized compounds were subjected to test for their antimicrobial activities against variety of gram positive (Bacillus subtilis, Staphylococcus aureus) and gram negative bacterial stains (Shigella sonnei, Escherichia coli) by agar dilution method. Several of them exhibited appreciable good antibacterial activity against the different strains of gram positive and gram negative bacteria. These findings suggest a great potential of these compounds for screening and use as antibacterial agents for further studies with a battery of bacteria.

  13. Towards optimal dosing of coumarin derivatives: the role of pharmacogenetics

    NARCIS (Netherlands)

    van Schie, R.M.F.

    2013-01-01

    Coumarin derivatives are effective in the prevention and treatment of thromboembolic diseases. Examples of indications are atrial fibrillation and venous thromboembolism. Although coumarins are on the market for decades, it is still challenging to find the optimal dosage for each patient since couma

  14. Genetic variation in the metabolism of coumarin in mouse liver

    NARCIS (Netherlands)

    Lovell, D.P.; Iersel, van M.P.L.S.; Walters, D.G.; Price, R.J.; Lake, B.G.

    1999-01-01

    The metabolism of 50 μM [3-14C] coumarin to polar products separated by high performance liquid chromatography (HPLC) and covalently bound metabolites in liver microsomes was compared in a series of inbred strains of mice. Coumarin metabolism to total polar products was higher in female than male mi

  15. 40 CFR 721.2155 - Alkoxyamino-alkyl-coumarin (generic).

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkoxyamino-alkyl-coumarin (generic... Substances § 721.2155 Alkoxyamino-alkyl-coumarin (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as...

  16. Turning-On of Coumarin Phosphorescence in Acetylacetonato Platinum Complexes of Cyclometalated Pyridyl-Substituted Coumarins

    Directory of Open Access Journals (Sweden)

    Andrej Jackel

    2015-04-01

    Full Text Available Two pyridine-functionalized coumarins differing with respect to the site of pyridine attachment to the coumarin dye (3 in L1 or 7 in L2 and with respect to the presence (L1 or absence (L2 of a peripheral NMe2 donor were prepared and used as cyclometalating ligands towards the Pt(acac fragment. X-ray crystal structures of complexes 1 and 2 show strong intermolecular interactions by π-stacking and short Pt∙∙∙Pt or C-H∙∙∙O hydrogen bonding that result in the formation of sheetlike packing patterns. The NMe2 donor substituent has a profound influence on the absorption and emission properties of the free coumarin dyes; L1 emits strongly while L2 is only weakly emissive. On binding to Pt(acac the strong fluorescence of L1 is partially quenched while coumarin phosphorescence is observed from cyclometalated L1 and L2. The ligand-centered nature of the LUMO was confirmed by IR spectroelectrochemistry while the assignment of the phosphorescence emission as ligand-based rests on the vibrational structuring, the negligible solvatochromism, the small temperature-induced Stokes shifts on cooling to 77 K, the emission lifetimes, and strong oxygen quenching. (TD-DFT calculations confirm our experimental results and provide an assignment of the electronic transitions and the spin density distributions in the T1 state.

  17. Fungi as a source of natural coumarins production.

    Science.gov (United States)

    Costa, Tania Maria; Tavares, Lorena Benathar Ballod; de Oliveira, Débora

    2016-08-01

    Natural coumarins and derivatives are compounds that occur naturally in several organisms (plant, bacteria, and fungi) consisting of fused benzene and α-pyrone rings. These compounds show high technological potential applications in agrochemical, food, pharmaceuticals, and cosmetics industries. Therefore, the need for bulk production of coumarins and the advancement of the chemical and pharmaceutical industries led to the development of synthetic coumarin. However, biotransformation process, synthetic bioengineering, metabolic engineering, and bioinformatics have proven effective in the production of natural products. Today, these biological systems are recognized as green chemistry innovation and business strategy. This review article aims to report the potential of fungi for synthesis of coumarin. These microorganisms are described as a source of natural products capable of synthesizing many bioactive metabolites. The features, classification, properties, and industrial applications of natural coumarins as well as new molecules obtained by basidiomycetes and ascomycetes fungi are reported in order to explore a topic not yet discussed in the scientific literature.

  18. Preparation of some new coumarin dyes

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    Series of coumarins containing heterocyclic substituent in 3-position were prepared.Sulfonyl chloride, a reactive group, was drawn into the heterocycle, and further condensed withamines to give series of new compounds that contain N-alkyl sulfamide. The spectral propertiesand dyeing character of these new dyes are discussed. A bathochromic shift (10 nm), enhancedfastness in light and sublimation (1-2 grade) and larger molar extinction coefficient (increase 104L ·mol-1 ·cm-1) are apparent with these new compounds. In the meantime, larger solubility appearswith these new compounds.

  19. Simultaneous determination of 12 coumarins in bamboo leaves by HPLC.

    Science.gov (United States)

    Wang, Shuying; Tang, Feng; Yue, Yongde; Yao, Xi; Wei, Qi; Yu, Jin

    2013-01-01

    A simple, rapid, and sensitive HPLC-UV method was developed for qualitative and quantitative analysis of 12 coumarin compounds (skimin, scopolin, scopoletin, umbelliferone, 6,7-dimethoxycoumarin, coumarin, psoralen, xanthotoxin, 5,7-dimethoxycoumarin, pimpinellin, imperatorin, and osthole) in bamboo leaves. The samples were extracted with ethanol-water (70 + 30, v/v) by ultrasonication and purified by Florisil SPE. The method was validated for linearity, LOD, LOQ, accuracy, precision, and recovery. The standard curves in the corresponding ranges had good linearity. LOD was at the range of 0.19 to 0.85 mglkg and LOQ 0.64 to 2.82 mg/kg. The values of RSD for accuracy and intraday and interday precision were less than 3%, except for 6,7-dimethoxycoumarin. Recoveries from spiked samples at 30, 20, and 10 mg/kg in Dendrocalamus giganteus Munro were higher than 70%, except for scopoletin, 6,7-dimethoxycoumarin, and coumarin. The method was validated using field-collected samples taken from Beijing and Changning Counties, SiChuan, China. Six coumarins, namely, skimin, scopolin, scopoletin, umbelliferone, coumarin, and pimpinellin, were found in the extracts of 11 species of bamboo leaves. The concentrations of total coumarins were in the range of 8.67 to 99.2 mg/kg. The maximum concentration of total coumarins was found in Bambusa pervariabilis, and the minimum was in

  20. Modulation of Drug Resistance in Staphylococcus aureus with Coumarin Derivatives

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    Rodrigo Santos Aquino de Araújo

    2016-01-01

    Full Text Available Semisynthetic and commercial coumarins were investigated for their antibacterial and adjuvant properties with antibiotic agents against norfloxacin, erythromycin, and tetracycline resistant Staphylococcus aureus as based on efflux mechanisms. The coumarins and certain commercial antibiotics had their Minimum Inhibitory Concentrations determined by broth microdilution assay against resistant S. aureus strains which overexpress efflux pump proteins. For evaluation of the modulatory activity, the antibiotics MICs were determined in the presence of the coumarin derivatives at subinhibitory concentration. Although the coumarins did not display relevant antibacterial activity (MIC ≥ 128 µg/mL, they did modulate the antibiotics activities. Various coumarins, especially the alkylated derivatives in combination with antibiotics at subinhibitory concentrations, modulated antibiotic activity, reducing the MIC for tetracycline and norfloxacin by 2 to 8 times. Polar Surface Area (PSA studies were performed and the fact that the presence of apolar groups is an important factor for the modulatory activity of coumarins was corroborated. Docking on the Penicillin-Binding Protein from MRSA identified that 18 is a potential ligand presenting low Ebinding. The results indicate that coumarin derivatives modulated antibiotic resistance and may be used as potential antibiotic adjuvants, acting by bacterial efflux pump inhibition in S. aureus.

  1. The Antioxidant Activity of New Coumarin Derivatives

    Directory of Open Access Journals (Sweden)

    Abu Bakar Mohamad

    2011-09-01

    Full Text Available The antioxidant activity of two synthesized coumarins namely, N-(4,7-dioxo-2-phenyl-1,3-oxazepin-3(2H,4H,7H-yl-2-(2-oxo-2H-chromen-4-yloxyacetamide 5 and N-(4-oxo-2-phenylthiazolidin-3-yl-2-(2-oxo-2H-chromen-4-yloxyacetamide 6 were studied with the DPPH, hydrogen peroxide and nitric oxide radical methods and compared with the known antioxidant ascorbic acid. Compounds 5 and 6 were synthesized in a good yield from the addition reaction of maleic anhydride or mercaptoacetic acid to compound 4, namely N'-benzylidene-2-(2-oxo-2H-chromen-4-yloxyacetohydrazide. Compound 4 was synthesized by the condensation of compound 3, namely 2-(2-oxo-2H-chromen-4-yloxy acetohydrazide, with benzaldehyde. Compound 3, however, was synthesized from the addition of hydrazine to compound 2, namely ethyl 2-(2-oxo-2H-chromen-4-yloxyacetate, which was synthesized from the reaction of ethyl bromoacetate with 4-hydroxycoumarin 1. Structures for the synthesized coumarins 2–6 are proposed on the basis of spectroscopic evidence.

  2. Total Synthesis of Six 3,4-Unsubstituted Coumarins

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    Wenqing Gao

    2013-12-01

    Full Text Available In this article we describe a new methodology for the total synthesis of 3,4-unsubstituted coumarins from commercially available starting materials. Six examples were prepared, including five naturally occurring coumarins—7-hydroxy-6,8-dimethoxy-coumarin (isofraxidin, 7-hydroxy-6-methoxycoumarin (scopoletin, 6,7,8-trimethoxy-coumarin, 6,7-dimethoxycoumarin (scoparone, and 7,8-dihydroxycoumarin (daphnetin and one synthetic coumarin, 7-hydroxy-6-ethoxycoumarin. Moreover, five important o-hydroxybenzaldehyde intermediates were also obtained, namely 2,4-dihydroxy-3,5-dimethoxybenzaldehyde, 2,4-dihydroxy-5-methoxybenzaldehyde, 5-ethoxy-2,4-dihydroxy-benzaldehyde, 2-hydroxy-3,4,5-trimethoxybenzaldehyde, and 2-hydroxy-4,5-dimethoxy-benzaldehyde. The method developed herein involves just three or four steps and allows for the rapid synthesis of these important molecules in excellent yields. This is the first synthesis of 6,7,8-trimethoxycoumarin and 7-hydroxy-6-ethoxycoumarin.

  3. Cytotoxity of two new coumarin derivatives isolated from Launaea mucronata.

    Science.gov (United States)

    El-Sharkawy, Eman R; Mahmoud, Khaled

    2016-01-01

    The chloroform fraction of methanol (MeOH) extract of the aerial parts of Launaea mucronata was in vitro investigated for cytotoxicity against HCT116, HepG2 and MCF-7 cell lines, and resulted with IC50 = 20.0, 18.6 and 14.30 μg/mL, respectively. The chloroform fraction of the MeOH extract was subjected to further fractionation, which led to the isolation of two new coumarin compounds (6-isobutyl coumarin and 6-isobutyl-7-methyl- coumarin). The structures of the new compounds were elucidated by high field 1D and 2D NMR and ESI-MS spectroscopies. Low polar fractions revealed the isolation of other known triterpene compounds which were identified according to its spectral data and comparison with the literature. New coumarin compounds show high cytotoxicity against MCF-7, HCT116 and HepG2 cell lines.

  4. A potential low-coumarin cinnamon substitute: Cinnamomum osmophloeum leaves.

    Science.gov (United States)

    Yeh, Ting-Feng; Lin, Chun-Ya; Chang, Shang-Tzen

    2014-02-19

    The essential oils from leaves of Taiwan's indigenous cinnamon (Cinnamomum osmophloeum ct. cinnamaldehyde) have similar constituents as compared to that from commercial bark cinnamons. This indigenous cinnamon has been proven to have excellent bioactivities. To understand whether this indigenous cinnamon contains a high level of the hepatotoxic compound, coumarin, as often seen in Cassia cinnamons, current research focused on determining the coumarin content in this indigenous cinnamon and screening the low-coumarin clones. The results demonstrated that the coumarin contents in all tested indigenous cinnamon clones were much lower than that found in Cassia cinnamons. In addition, this indigenous cinnamon contains about 80% (w/w) of cinnamaldehyde and 0.4-2.7% (w/w) of eugenol in its leaf essential oils. This combination could provide this indigenous cinnamon a better shelf life compared to that of regular commercial cinnamons. These results suggested that leaves of this indigenous cinnamon could be a potential resource for a safer cinnamon substitute.

  5. Synthesis and Spectroscopic Study of Coumarin Derivatives

    Institute of Scientific and Technical Information of China (English)

    YAO Chun-feng; ZENG He-ping

    2011-01-01

    Five new coumarin amide derivatives were synthesized with coupling reagent,the structures of which were characterized by IR,1H NMR,13C NMR,MS and element analysis.Their spectral properties were studied in dichloromethane,in N,N-dimethylformamide(DMF) and in solid state.Solvent polarity has less influence on the UV-Vis maximum absorption at about 430 nm.The maximum emission wavelengths change from 464 nm to 474 nm in dichloromethane,from 476 nm to 482 nm in DMF and from 521 nm to 548 nm in solid state,respectively.The fluorescence intensities of compounds 8 and 9 were extremely strong in solvents or in solid state.Compounds 8 and 9 exhibited high fluorescenct quantumn yields in solution compared to compounds 4-7.The fluorescence lifetimes of all the compounds in solvents were measured.

  6. Two New Coumarins from Fraxinus chinensis Rexb.

    Institute of Scientific and Technical Information of China (English)

    Dong-Mei Zhang; Li-Li Wang; Jia Li; Li-Hong Hu

    2007-01-01

    The ethanol extract of the stem bark of Fraxinus chinensis Roxb. showed good inhibitory bioactivity against VEGF receptor-1 kinase (IC50:13.8 μg/mL). In order to find new and bioactive compounds, the chemical constituents of the stem bark of F. chinensis were investigated and two new coumarins, namely 6'-O-sinapinoyl esculin (compound 1) and 6'-O-vanillyl esculin (compound 2), together with eleven known compounds (compounds 3-13) were isolated.The structures of the two new compounds were identified by their physicochemical properties and spectral analysis, particularly one- and two-dimens ional nuclear magnetic resonance spectral methods. The known compound, oleuropein (compound 11), exhibited moderate activity (IC50:(8.7 ± 1.3) μmol/L) to inhibit VEGF receptor-1 kinase.

  7. Bioactive sesquiterpene coumarins from Ferula pseudalliacea.

    Science.gov (United States)

    Dastan, Dara; Salehi, Peyman; Reza Gohari, Ahmad; Ebrahimi, Samad Nejad; Aliahmadi, Atousa; Hamburger, Matthias

    2014-08-01

    One new and five known sesquiterpene coumarins were isolated from the roots of Ferula pseudalliacea. The structures were elucidated by 1D and 2D NMR, and HR-ESIMS data as 4'-hydroxy kamolonol acetate (1), kamolonol (2), szowitsiacoumarin A (3), farnesiferon B (4), farnesiferol C (5), and flabellilobin A (6). The absolute configuration of compounds 1, 2, and 4 was established by comparison of experimental and simulated electronic circular dichroism spectra using time dependence density function theory. 4'-Hydroxy kamolonol acetate and kamolonol showed antibacterial activity against Heliobacter pylori and Staphylococcus aureus at a concentration of 64 µg/mL. Kamolonol, 4'-hydroxy kamolonol acetate, and farnesiferon B displayed a cytotoxic activity in HeLa cells, with an IC50 of 3.8, 4.5, and 7.7 µM, respectively.

  8. Coumarins from the leaves of Bambusa pervariabilis McClure.

    Science.gov (United States)

    Sun, Jia; Yue, Yong-De; Tang, Feng; Guo, Xue-Feng

    2010-03-01

    A new pyrone-coumarin, 7,8-dihydroxy-3-(3-hydroxy-4-oxo-4H-pyran-2-yl)-2H-chromen-2-one (1), along with two known coumarins, scopoletin (2) and scopolin (3), was isolated from the 95% EtOH extract of the leaves of Bambusa pervariabilis McClure. Their structures were determined on the basis of spectroscopic techniques and chemical methods.

  9. [Allelopathy effects of ferulic acid and coumarin on Microcystis aeruginosa].

    Science.gov (United States)

    Guo, Ya-Li; Fu, Hai-Yan; Huang, Guo-He; Gao, Pan-Feng; Chai, Tian; Yan, Bin; Liao, Huan

    2013-04-01

    The inhibitory effects and allelopathy mechanism of ferulic acid and coumarin on Microcystis aeruginosa were investigated by measuring the D680 value, the content of chlorophyll-a, the electrical conductivity (EC) and superoxide anion radical O*- value. Ferulic acid and coumarin had allelopathic effects on the growth of M. aeruginosa and promoted the physiological metabolism at low concentrations while inhibited the metabolism at high concentrations. Obvious inhibitory effects were observed when the concentration of ferulic acid or coumarin was over 100 mg x L(-1). The average inhibitory rates reached 80.3% and 58.0% after six days when the concentration of ferulic acid or coumarin was 200 mg x L(-1). The content of chlorophyll-a was decreased while the EC value and O2*- concentration were promoted by higher concentrations of ferulic acid or coumarin, suggesting that the growth of algae was inhibited probably by the damage of cell membrane, increase in the content of O2*- and decrease in the content of chlorophyll-a. In addition, seed germination test elucidated that Ferulic acid was safer than Coumarin.

  10. Conversion of 3-Carbethoxy-4-methyl Coumarin Derivatives into Several New Annelated Coumarin Derivatives

    Institute of Scientific and Technical Information of China (English)

    BAKEER; HadeerMohammed

    2003-01-01

    The reaction of ethyl esters of 4-methyl-2-oxo-2H-l-benzo(naphtho) pyran.3-carboxylic acids (1) with aromatic aldehy-des in the presence of piperidine yielded 4-styryl-3-carboxami-dopiperidyl connmrin derivatives 4. The reaction of hydrazlne hydrate with 1 gave acetophenone hydrozone derivatives 5 and acetophenone azine derivatives 6. The reaction of 1 with prima-ry amines afforded compomlds 7—9. And the treatment of la with Grignard reagents afforded 3-aroyl-4-methyl coumarin derivatives 10.

  11. A fluorescent receptor assay for benzodiazepines using coumarin labeled desethylflumazenil as ligand

    NARCIS (Netherlands)

    Janssen, M.J; Ensing, K; de Zeeuw, R.A

    2001-01-01

    This article describes a novel nonisotopic receptor assay for benzodiazepines with fluorescence detection, As labeled ljgand (coumarin-labeled desethylflumazenil, CLDEF), a metabolite of the benzodiazepine antagonist flumazenil (desetheylflumazenil, Ro15-3890) has been coupled to a coumarin fluoroph

  12. Spectral and quantum-mechanical characterizations of 7-amino-4-trifluoromethyl coumarin

    Science.gov (United States)

    Benchea, Andreea Celia; Gaina, Marius; Dorohoi, Dana Ortansa

    2017-01-01

    Coumarins are crystalline compounds utilized in pharmaceutical, food and cosmetic industries. Our study refers to quantum-mechanical and spectral characterization of 7-amino-4-trifluoromethyl coumarin (7-NH2-4-CF3-coumarin or coumarin 151) in order to estimate its stability, reactivity and biological activity. The contribution of different types of interactions to the spectral shifts in homogeneous solutions and the limits in which the excited state dipole moment of the studied molecule can vary are established by solvatochromic study.

  13. Antimicrobial Properties of Newly Synthesized Derivatives of Coumarine

    Directory of Open Access Journals (Sweden)

    S. Govori

    2010-01-01

    Full Text Available Problem statement: Coumarins are well known for their biological activity. On the basis of that we have synthesized some new derivatives of coumarine and investigated their antimicrobial properties. Approach: 4-Heteroaryl-coumarin-3-carbaldehydes 4(a-d are synthesized by condensation of 4-chloro-coumarin-3-carbaldehydes 2 and corresponding heterorylamines 3(a-d under reflux reaction conditions. Antimicrobial properties of new coumarins 4(a-d are investigated and results are submitted for their activities against Staphylococcus aureus, Escherichia coli, Hafnia alvei, Pseudomonas aeruginosa and Enterobacter cloacae. Applying the Agar disc diffusion technique we measured diameters of the inhibition zone around discs which are previously wetted with N, N-DMF solution of compounds, 1, 3 and 5 mg L−1. Results: The inhibition zone depends from concentrations and also from sort of bacteria. The inhibition zone differ from 0 to 30mm. Two sort of bacteria, Hafnia alvei and Pseudomonas aeruginosa, are resistant to these new synthesized compounds. Conclusion: From results we may conclude that these derivates showed moderate to high activity against Staphylococcus aureus, Escherichia coli and Enterobacter cloaco. Compounds 4(a-d are more active against Staphylococcus aureus, E.coli and Enterobacter cloaco. Compounds 4(a-d are not active against Hafnia alvei and Pseudomonas aeruginosa.

  14. Current developments of coumarin compounds in medicinal chemistry.

    Science.gov (United States)

    Peng, Xin-Mei; Damu, Guri L V; Zhou, Cheng- He

    2013-01-01

    Coumarin compounds represent an important type of naturally occurring and synthetic oxygen-containing heterocycles with typical benzopyrone framework. This type of special benzopyrone structure enables its derivatives readily interact with a diversity of enzymes and receptors in organisms through weak bond interactions, thereby exhibit wide potentiality as medicinal drugs. So far, some coumarin-based drugs such as anticoagulant and antineurodegenerative agents have been extensively used in clinic. Coumarin-containing supramolecular medicinal agents as a new increasing expansion of supramolecular chemistry in pharmaceutical science have also been actively investigated in recent years. Coumarin-derived artificial ion receptors, fluorescent probes and biological stains are growing quickly and have a variety of potential applications in monitoring timely enzyme activity, complex biological events as well as accurate pharmacological and pharmacokinetic properties. This review provides a systematic summary and insight of the whole range of medicinal chemistry in the current developments of coumarin compounds as anticoagulant, antineurodegenerative, anticancer, antioxidative, antibacterial, antifungal, antiviral, antiparasitic, antiinflammatory and analgesic, antidiabetic, antidepressive and other bioactive agents as well as supramolecular medicinal drugs, diagnostic agents and pathologic probes, and biological stains. Some rational design strategies, structure-activity relationships and action mechanisms are discussed. The perspectives of the future development of coumarinbased medicinal chemistry are also presented.

  15. Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation

    Directory of Open Access Journals (Sweden)

    Kois Pavol

    2006-11-01

    Full Text Available Abstract Background Reaction of azides with triaryl phosphines under mild conditions gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e.g. aldehydes/ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation including specific labeling of nucleic acids. Results A new approach for the preparation of labeled nucleosides via intermolecular Staudinger ligation is described. Reaction of azidonucleosides with triphenylphosphine lead to iminophosphorane intermediates, which react subsequently with derivatives of coumarin or ferrocene to form coumarin or ferrocene labeled nucleosides. Fluorescent properties of coumarin labeled nucleosides are determined. Conclusion New coumarin and ferrocene labeled nucleosides were prepared via intermolecular Staudinger ligation. This reaction joins the fluorescent coumarin and biospecific nucleoside to the new molecule with promising fluorescent and electrochemical properties. The isolated yields of products depend on the structure of azidonucleoside and carboxylic acids. A detailed study of the kinetics of the Staudinger ligation with nucleoside substrates is in progress.

  16. Synthesis of new condensed coumarin derivatives

    Directory of Open Access Journals (Sweden)

    Dekić Stojadin V.

    2007-01-01

    Full Text Available Reactions of 4-chloro-2-oxo-2H-chromene-3-carbonitrile (1 with 4-methylpyridin- 2-ylamine (2 and 6-methoxy-benzothiazol-2-ylamine (3 in acetonitrile containing a catalytic amount of triethylamine gave the new coumarin derivatives 7-imino-10-methyl-7H- 5-oxa-7a,12-diaza-benzo[a]anthracen-6-one (4 and 7-imino-10-methoxy-7H-5-oxa-12- thia-7a,13-diaza-indeno[1,2-b]phenanthren-6-one (5 in 52 and 39% yields, respectively. The novel compounds were subjected to acid hydrolysis giving the corresponding oxoderivatives 10-methyl-5-oxa-7a,12-diaza-benzo[a]anthracene-6,7-dione (6 and 10- methoxy-5-oxa-12-thia-7a,13-diaza-indeno[1,2-b]phenanthrene-6,7-dione (7 in 64 and 58% yields, respectively. The structural assignments of the synthesized compounds were based on elemental analyses, IR and proton NMR spectra. .

  17. Coumarins of Matricaria chamomilla L.: aglycones and glycosides.

    Science.gov (United States)

    Petruľová-Poracká, Veronika; Repčák, Miroslav; Vilková, Mária; Imrich, Ján

    2013-11-01

    The identity and quantity of coumarin-like compounds in leaves and anthodia of Matricaria chamomilla L. were studied by LC-DAD and NMR. So far, two monosubstituted coumarins, herniarin and umbelliferone, and two herniarin precursors were identified therein. In this paper, two other coumarin glycosides and one aglycone were confirmed. Skimmin (umbelliferone-7-O-β-d-glucoside), daphnin (daphnetin-7-O-β-d-glucoside) and daphnetin (7,8-dihydroxycoumarin) were found for the first time in diploid and tetraploid leaves and anthodia of M. chamomilla L. Daphnetin is known as a strong sensitizer, so this compound and its glycosidic derivative can contribute to the allergic potential of chamomile. Commercial chamomile preparations were tested for their presence.

  18. Design and Synthesis of a Coumarin-based Acidichromic Colorant

    Directory of Open Access Journals (Sweden)

    Ding-Yah Yang

    2007-07-01

    Full Text Available This paper describes the fine-tuning of the acidichromic properties of a coumarin-containing colorant 1 by incorporation of electron-donating and electron-withdrawing substituents on the coumarin moiety. Colorant 1 can undergo two distinct and reversible color changes under both strongly acidic and basic conditions, but not in the presence of gaseous ammonia. The results indicated that the bromo-substituted compound 5b changes from red to yellow when exposed to gaseous ammonia, both in solution and on polycarbonate film, suggesting that an electron-withdrawing group at the 7-position of the coumarin moiety made the enolic hydrogen on 5b more susceptible to deprotonation by a base than in the unsubstituted compound 1.

  19. Fourier transform infrared spectroscopy for irradiation coumarin doped polystyrene polymer films by alpha ray

    Directory of Open Access Journals (Sweden)

    Mahasin F. Hadi Al-Kadhemy

    2016-07-01

    Full Text Available FTIR spectroscopy has been in use broadly to study microscopic areas in polymers for the last years. The FTIR transmission spectra of coumarin laser dye, polystyrene and coumarin doped polystyrene films with different doping ratio of coumarin solution have been studied. These spectra measured and explained for all films before and after Alpha irradiation with different irradiation times. All samples prepared by casting method. FTIR corroborate chemical bonds of coumarin dye molecules and polystyrene films by producing an IR absorption spectrum when increasing doping ratio of coumarin solution and when irradiation by Alpha source. There are some bonds disappeared after irradiation.

  20. Red emitting NLOphoric 3-styryl coumarins: Experimental and computational studies

    Science.gov (United States)

    Tathe, Abhinav B.; Sekar, Nagaiyan

    2016-01-01

    The coumarin molecules are versatile fluorophores and can be modified synthetically to give desired properties. The molecules studied have 4-cyano group as an assistance to original chromophore and imparts a red shift. These coumarins were expected to show good non-linear optical (NLO) properties. The experimental and theoretical methods were employed to determine their NLO properties. Directional components of hyperpolarizabilities were calculated and showed a variation according to the placement of electron pulling groups. Studied molecules show a very high (494-794 times of urea) total first order hyperpolarizability. The NLO properties of the molecules were found to be solvent dependant.

  1. Synthesis and Sensing Applications of Fluorescent 3-Cinnamoyl Coumarins

    Science.gov (United States)

    Yadav, Preeti; Gill, Hardeep Singh; Chand, Karam; Li, Lian; Kumar, Jayant; Sharma, Sunil K.

    2015-01-01

    We have synthesized two novel fluorescent 3-(4-diethylaminocinnamoyl) coumarins that exhibit fluorescence quenching upon exposure to a nerve agent simulant, diethylchlorophosphate (DCP), providing a basis for rapid and sensitive DCP chemosensing. Furthermore, these coumarin derivatives display two-photon fluorescence upon illumination with near-infrared laser pulses and their two-photon (TP) absorption cross-section was evaluated. The potential for TP bio-imaging of these compounds was investigated by their cellular uptake in HeLa cells by TP confocal microscopy. PMID:26703600

  2. Synthesis and Sensing Applications of Fluorescent 3-Cinnamoyl Coumarins

    Directory of Open Access Journals (Sweden)

    Preeti Yadav

    2015-12-01

    Full Text Available We have synthesized two novel fluorescent 3-(4-diethylaminocinnamoyl coumarins that exhibit fluorescence quenching upon exposure to a nerve agent simulant, diethylchlorophosphate (DCP, providing a basis for rapid and sensitive DCP chemosensing. Furthermore, these coumarin derivatives display two-photon fluorescence upon illumination with near-infrared laser pulses and their two-photon (TP absorption cross-section was evaluated. The potential for TP bio-imaging of these compounds was investigated by their cellular uptake in HeLa cells by TP confocal microscopy.

  3. Hydrogenation of coumarin to octahydrocoumarin over a Ru/C catalyst

    Institute of Scientific and Technical Information of China (English)

    Dana Bílková; Petr Jansa; Iva Paterová; Libor Červený

    2015-01-01

    The production of octahydrocoumarin, which can serve as a replacement for toxic coumarin, was investigated using 5% Ru on active carbon (Ru/C) as the catalyst for the hydrogenation of couma-rin. The hydrogenation was studied by optimizing the reaction conditions (pressure, solvent and coumarin concentration). The activity and selectivity of the Ru/C catalyst were compared for dif-ferent solvents. The mechanism of coumarin hydrogenation was deduced. The formation of side products was explained. The optimal hydrogenation reaction conditions were: 130 °C, 10 MPa, 60 wt% coumarin in methanol, and 0.5 wt% (based on coumarin) of Ru/C catalyst. At the complete conversion of coumarin, the selectivity to the desired product was 90%.

  4. Gustatory Receptors Required for Avoiding the Toxic Compound Coumarin in Drosophila melanogaster.

    Science.gov (United States)

    Poudel, Seeta; Lee, Youngseok

    2016-04-30

    Coumarin is a phenolic compound that mainly affects the liver due to its metabolization into a toxic compound. The deterrent and ovicidal activities of coumarin in insect models such as Drosophila melanogaster have been reported. Here we explore the molecular mechanisms by which these insects protect themselves and their eggs from this toxic plant metabolite. Coumarin was fatal to the flies in a dosage-dependent manner. However, coumarin feeding could be inhibited through activation of the aversive gustatory receptor neurons (GRNs), but not the olfactory receptor neurons. Furthermore, three gustatory receptors, GR33a, GR66a, and GR93a, functioned together in coumarin detection by the proboscis. However, GR33a, but not GR66a and GR93a, was required to avoid coumarin during oviposition, with a choice of the same substrates provided as in binary food choice assay. Taken together, these findings suggest that anti-feeding activity and oviposition to avoid coumarin occur via separate mechanisms.

  5. Study of excitation energy transfer from Coumarin102(donor) to Coumarin6(acceptor) doped in poly-methyl methacrylate (PMMA) thin film

    Science.gov (United States)

    Singh, Khushboo; Negi, Gauri; Joshi, G. C.

    2015-05-01

    Energy transfer from Coumarin102 to Coumarin6 has been studied. It is observed that energy transfer begins at relatively larger donor acceptor separations than the critical transfer distance for efficient dipole-dipole energy transfer by Forster mechanism. For Coumarin 102 and Coumarin 6 dye pair, the energy transfer parameters, viz overlap integral(J(λ)) and Förster distance(R0), equaling 3.4x10-13M-1cm3 and 58.7(Å), respectively have been obtained. Migration through donor-donor interaction is suggested to be the possible mechanism and Huber model has been applied to calculate the transfer rate.

  6. An efficient methodology for the synthesis of 3-styryl coumarins

    Energy Technology Data Exchange (ETDEWEB)

    Martins, Sergio M.A.; Pereira, Antonio M.D.R.L. [Centro de Quimica, Departamento de Quimica, Universidade de Evora, Evora (Portugal); Branco, Paula C.S. [REQUIMTE, Departamento de Quimica, Universidade Nova de Lisboa, Caparica (Portugal)

    2012-04-15

    Regioselective and highly efficient Heck arylation of 3-vinyl-6,7-dimethoxycoumarin has been developed to afford 3-styryl coumarins in good to very high yields. The increase in conjugation reflects on the absorbance of the synthesized compounds revealing all pronounced bathochromic shifts and hyperchromic effects. (author)

  7. Nitroketene dithioacetal chemistry: Synthesis of coumarins incorporating nitrothiophene moiety

    Indian Academy of Sciences (India)

    H Surya Prakash Rao; K Vasantham

    2011-07-01

    Alkylation of dipotassium 2-nitro-1,1-ethylenedithiolate 1 with ethyl 4-chloroacetoacetate 6 in a mixture of MeOH-H2O (2:1) furnished highly functionalized 3-nitrothiophene 5. Pechmann condensation of 5 with 2-hydroxybenzaldehydes 8a-i, 10 furnished coumarin-3-nitrothiophene conjugates 9a-i, 11.

  8. Cytotoxic Coumarins from the Bark of Mammea siamensis.

    Science.gov (United States)

    Ngo, Ngoc Trang Nhu; Nguyen, Vy Thuy; Vo, Hoa Van; Vang, Ole; Duus, Fritz; Ho, Thuy-Duong Huynh; Pham, Hung Dinh; Nguyen, Lien-Hoa Dieu

    2010-11-01

    A new geranylated coumarin, (E)-4-(1-hydroxypropyl)-5,7-dihydroxy-6-(3,7-dimethyl-2,6-octadienyl)-8-(3-methyl-1-oxobutyl)coumarin (named surangin D), was isolated from the bark of Mammea siamensis collected in Vietnam, along with four known coumarins, surangins B and C, and theraphins B and C, and seven xanthones, 1,7-dihydroxyxanthone, 7-hydroxy-1-methoxyxanthone, 1,7-dimethoxyxanthone, 1,7-dimethoxy-6-hydroxyxanthone, 1,6,7-trihydroxyxanthone, 1,3,7-trihydroxyxanthone, and 1,7-dihydroxy-3-methoxyxanthone. Their structures were determined by spectroscopic methods (mainly 1D- and 2D-NMR) and preparation of methylated derivatives. The four coumarins, surangins C and D and theraphins B and C, were tested for inhibition of cell proliferation in DLD-1 (colon cancer), MCF-7 (breast adenocarcinoma), HeLa (human cervical cancer) and NCI-H460 (human lung cancer) cell lines using the sulforhodamine B (SRB) assay. In all four cell lines, theraphin C showed the strongest activity (IC₅₀ in the range of 1.6-5.7 µM). Testing the anti-proliferative effect of the methylated derivatives showed reduced cellular effects of all derivatives, indicating that the number and position of free hydroxyl groups were very important for the anti-proliferative effect.

  9. Probing the binding of coumarins and cyclothialidines to DNA gyrase

    DEFF Research Database (Denmark)

    Kampranis, S C; Gormley, N A; Tranter, R

    1999-01-01

    DNA gyrase is the target of a number of antibacterial agents, including the coumarins and the cyclothialidines. To extend our understanding of the mechanism of action of these compounds, we have examined the previously published crystal structures of the complexes between the 24 kDa fragment of Gyr...

  10. A coumarin-based colorimetric fluorescent probe for hydrogen sulfide

    Indian Academy of Sciences (India)

    Yanqiu Yang; Yu Liu; Liang Yang; Jun Liu; Kun Li; Shunzhong Luo

    2015-03-01

    A coumarin-based fluorescent probe for selective detection of hydrogen sulfide (H2S) is presented. This `off–on’ probe exhibited high selectivity towards H2S in aqueous solution with a detection limit of 30 nM. Notably, because of its dual nucleophilicity, the probe could avoid the interference of thiols and other sulfur containing compounds.

  11. Overanticoagulation associated with combined use of lactulose and coumarin anticoagulants.

    NARCIS (Netherlands)

    Visser, L.E.; Penning-van Beest, F.J.A.; Wilson, J.H.; Vulto, A.G.; Kasbergen, A.A.H.; Smet, P.A.G.M. de; Hofman, A.W.I.M.; Stricker, B.H.C.

    2004-01-01

    Some medical textbooks on drug interactions take note of the potential interaction between laxatives and coumarin anticoagulants, but epidemiological evidence that this interaction is of practical importance is lacking. We conducted a follow-up study in a large population-based cohort to investigate

  12. Coumarin benzothiazole derivatives as chemosensors for cyanide anions.

    Science.gov (United States)

    Wang, Kangnan; Liu, Zhiqiang; Guan, Ruifang; Cao, Duxia; Chen, Hongyu; Shan, Yanyan; Wu, Qianqian; Xu, Yongxiao

    2015-06-05

    Four coumarin benzothiazole derivatives, N-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromene-3-carboxamide (1), (Z)-N-(3-methylbenzo[d]thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide (2), 7-(diethylamino)-N-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromene-3-carboxamide (3) and (Z)-7-(diethylamino)-N-(3-methylbenzo[d]thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide) (4), have been synthesized. Their crystal structures, photophysical properties in acetonitrile and recognition properties for cyanide anions have been investigated. All the compounds are generally planar, especially compound 1 exhibits perfect planarity with dihedral angle between benzothiazolyl group and coumarin group being only 3.63°. Coumarin benzothiazole compounds 1 and 3 can recognize cyanide anions by Michael addition reaction and compound 3 exhibits color change from yellow to colorless and green fluorescence was quenched completely, which can be observed by naked eye. Coumarin benzothiazolyliden compound 4 can recognize cyanide anions with fluorescence turn-on response based on the copper complex ensemble displacement mechanism.

  13. Terpenylated coumarins as SIRT1 activators isolated from Ailanthus altissima

    DEFF Research Database (Denmark)

    Dao, Trong-Tuan; Tran, Tien-Lam; Kim, Jayeon;

    2012-01-01

    Four new terpenylated coumarins (1-4) were isolated from the stem bark of Ailanthus altissima by bioactivity-guided fractionation using an in vitro SIRT1 deacetylation assay. Their structures were identified as (2'R,3'R)-7-(2',3'-dihydroxy-3',7'-dimethylocta-6'-enyloxy)-6,8-dimethoxycoumarin (1), 6......,8-dimethoxy-7-(3',7'-dimethylocta-2',6'-dienyloxy)coumarin (2), (2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctaoxy)-6,8-dimethoxycoumarin (3), and (2'R,3'R,4'S,5'S)-6,8-dimethoxy-7-(3',7'-dimethyl-4',5'-epoxy-2'-hydroxyocta-6'-enyloxy)coumarin (4). Compounds 1-4 strongly enhanced SIRT1...... activity in an in vitro SIRT1-NAD/NADH assay and an in vivo SIRT1-p53 luciferase assay. These compounds also increased the NAD-to-NADH ratio in HEK293 cells. The present results suggest that terpenylated coumarins from A. altissima have a direct stimulatory effect on SIRT1 deacetylation activity and may...

  14. Genetic and environmental factors affecting the coumarin anticoagulant level

    NARCIS (Netherlands)

    L.E. Visser (Loes)

    2004-01-01

    textabstractThis introductory chapter has illustrated that various factors, such as genetic factors, drugs, diet and intercurrent diseases may affect anticoagulation levels. Most of the clinical and pharmacological data related to coumarin anticoagulants have so far been obtained from studying warfa

  15. Coumarin incorporated triazoles: a new class of anticonvulsants.

    Science.gov (United States)

    Bhat, Mashooq A; Al-Omar, Mohammed A

    2011-01-01

    A series of coumarin incorporated 1,2,4- triazole compounds (1-14) were evaluated for their possible anticonvulsant and neurotoxic properties, log P values, pharmacophoric mapping and three dimensional structure analysis. Compound (6) with para-fluoro substitution showed significant anticonvulsant activity.

  16. Coumarins and Chromones from ’Lomatium macrocarpum’,

    Science.gov (United States)

    Roots of Lomatium macrocarpum (Hook. and Arn.)C. and R. yielded osthol(7-methoxy-8-(3-methyl-2-butenyl)-coumarin) and a chromone , 2-methyl-5-hydroxy...6(3-methyl-2-butenyl)-7-methoxychromone, identified spectroscopically and by synthesis. The serial parts of the plant also contained this chromone

  17. Current perspectives on dental patients receiving coumarin anticoagulant therapy.

    Science.gov (United States)

    Herman, W W; Konzelman, J L; Sutley, S H

    1997-03-01

    Despite approximately 40 years of experience with oral anticoagulant drugs, controversy still exists about the safety of dental treatment in a patient receiving this therapy. The authors review the topic in depth and offer detailed recommendations for the dental management of patients receiving coumarin anticoagulant therapy.

  18. Alkaloids and Coumarins from the Leaves of Amyris diatripa.

    Science.gov (United States)

    Laguna, A

    1984-02-01

    The alkaloids edulinine and (+/-) isoplatydesmine were isolated from the leaves of Amyris diatripa, being the first report of the presence of alkaloids in species of this genus. The presence of coumarins in the plant was also shown by isolation of psoralen, bergapten, marmesin, ulopterol and suberenol.

  19. Coumarin benzothiazole derivatives as chemosensors for cyanide anions

    Science.gov (United States)

    Wang, Kangnan; Liu, Zhiqiang; Guan, Ruifang; Cao, Duxia; Chen, Hongyu; Shan, Yanyan; Wu, Qianqian; Xu, Yongxiao

    2015-06-01

    Four coumarin benzothiazole derivatives, N-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromene-3-carboxamide (1), (Z)-N-(3-methylbenzo[d]thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide (2), 7-(diethylamino)-N-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromene-3-carboxamide (3) and (Z)-7-(diethylamino)-N-(3-methylbenzo[d]thiazol-2(3H)-ylidene)-2-oxo-2H-chromene-3-carboxamide) (4), have been synthesized. Their crystal structures, photophysical properties in acetonitrile and recognition properties for cyanide anions have been investigated. All the compounds are generally planar, especially compound 1 exhibits perfect planarity with dihedral angle between benzothiazolyl group and coumarin group being only 3.63°. Coumarin benzothiazole compounds 1 and 3 can recognize cyanide anions by Michael addition reaction and compound 3 exhibits color change from yellow to colorless and green fluorescence was quenched completely, which can be observed by naked eye. Coumarin benzothiazolyliden compound 4 can recognize cyanide anions with fluorescence turn-on response based on the copper complex ensemble displacement mechanism.

  20. Terpenylated coumarins as SIRT1 activators isolated from Ailanthus altissima.

    Science.gov (United States)

    Dao, Trong-Tuan; Tran, Tien-Lam; Kim, Jayeon; Nguyen, Phi-Hung; Lee, Eun-Hee; Park, Junsoo; Jang, Ik-Soon; Oh, Won-Keun

    2012-07-27

    Four new terpenylated coumarins (1-4) were isolated from the stem bark of Ailanthus altissima by bioactivity-guided fractionation using an in vitro SIRT1 deacetylation assay. Their structures were identified as (2'R,3'R)-7-(2',3'-dihydroxy-3',7'-dimethylocta-6'-enyloxy)-6,8-dimethoxycoumarin (1), 6,8-dimethoxy-7-(3',7'-dimethylocta-2',6'-dienyloxy)coumarin (2), (2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctaoxy)-6,8-dimethoxycoumarin (3), and (2'R,3'R,4'S,5'S)-6,8-dimethoxy-7-(3',7'-dimethyl-4',5'-epoxy-2'-hydroxyocta-6'-enyloxy)coumarin (4). Compounds 1-4 strongly enhanced SIRT1 activity in an in vitro SIRT1-NAD/NADH assay and an in vivo SIRT1-p53 luciferase assay. These compounds also increased the NAD-to-NADH ratio in HEK293 cells. The present results suggest that terpenylated coumarins from A. altissima have a direct stimulatory effect on SIRT1 deacetylation activity and may serve as lead molecules for the treatment of some age-related disorders.

  1. Paniculacin, a new coumarin derivative from Murraya paniculata.

    Science.gov (United States)

    Saeed, Sumayya; Shah, Shazia; Mehmood, Rashad; Malik, Abdul

    2011-08-01

    Paniculacin (1), a new coumarin derivative, has been isolated from the ethyl acetate soluble fraction of the ethanolic extract of Murraya paniculata along with umbelliferone, scopoletin, 4-hydroxybenzoic acid, trans-cinnamic acid, and β-sitosterol. Their structures were elucidated on the basis of spectral data.

  2. A new angelol-type coumarin glucoside from Angelica pubescens

    Institute of Scientific and Technical Information of China (English)

    Xi Fei Ding; Xu Feng; Yun Fa Dong; Xing Zeng Zhao; Yu Chen; Ming Wang

    2008-01-01

    A new angelol-type coumarin glucoside,6-[(1R,2R)-1,2-dihydroxy-3-β-D-glucosyloxy-3-methylbutyl]-7-methoxycoumarin,wag isolated from the roots of Angelica pubescens.Its structure was elucidated on the basis of spectral analysis.

  3. Trypanocidal constituents in plants: 7. Mammea-type coumarins

    Directory of Open Access Journals (Sweden)

    Ricardo Reyes-Chilpa

    2008-08-01

    Full Text Available Calophyllum brasiliense and Mammea americana (Clusiaceae are two trees from the tropical rain forests of the American continent. A previous screening showed high trypanocidal activity in the extracts of these species. Several mammea-type coumarins, triterpenoids and biflavonoids were isolated from the leaves of C. brasiliense. Mammea A/AA was obtained from the fruit peels of M. americana. These compounds were tested in vitro against epimastigotes and trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas disease. The most potent compounds were mammea A/BA, A/BB, A/AA, A/BD and B/BA, with MC100 values in the range of 15 to 90 g/ml. Coumarins with a cyclized ,-dimethylallyl substituent on C-6, such as mammea B/BA, cyclo F + B/BB cyclo F, and isomammeigin, showed MC100 values > 200 g/ml. Several active coumarins were also tested against normal human lymphocytes in vitro, which showed that mammea A/AA and A/BA were not toxic. Other compounds from C. brasiliense, such as the triterpenoids, friedelin, canophyllol, the biflavonoid amentoflavone, and protocatechuic and shikimic acids, were inactive against the epimastigotes. The isopropylidenedioxy derivative of shikimic acid was inactive, and its structure was confirmed by X-ray diffraction. Our results suggest that mammea-type coumarins could be a valuable source of trypanocidal compounds.

  4. Molecular origins of optoelectronic properties in coumarin dyes: toward designer solar cell and laser applications.

    Science.gov (United States)

    Liu, Xiaogang; Cole, Jacqueline M; Waddell, Paul G; Lin, Tze-Chia; Radia, Jignesh; Zeidler, Anita

    2012-01-12

    Coumarin derivatives are used in a wide range of applications, such as dye-sensitized solar cells (DSCs) and dye lasers, and have therefore attracted considerable research interest. In order to understand the molecular origins of their optoelectronic properties, molecular structures for 29 coumarin laser dyes are statistically analyzed. To this end, data for 25 compounds were taken from the Cambridge Structural Database and compared with data for four new crystal structures of coumarin laser dyes [Coumarin 487 (C(19)H(23)NO(2)), Coumarin 498 (C(16)H(17)NO(4)S), Coumarin 510 (C(20)H(18)N(2)O(2)), and Coumarin 525 (C(22)H(18)N(2)O(3))], which are reported herein. The competing contributions of different resonance states to the bond lengths of the 4- and 7-substituted coumarin laser dyes are computed based on the harmonic oscillator stabilization energy model. Consequently, a positive correlation between the contribution of the para-quinoidal resonance state and the UV-vis peak absorption wavelength of these coumarins is revealed. Furthermore, the perturbations of optoelectronic properties, owing to chemical substituents in these coumarin laser dyes, are analyzed: it is found that their UV-vis peak absorption and lasing wavelengths experience a red shift, as the electron-donating strength of the 7-position substituent increases and/or the electron-withdrawing strength of the 3- or 4-position substituent rises; this conclusion is corroborated by quantum-chemical calculations. It is also revealed that the closer the relevant substituents align with the direction of the intramolecular charge transfer (ICT), the larger the spectral shifts and the higher the molar extinction coefficients of coumarin laser dyes. These findings are important for understanding the ICT mechanism in coumarins. Meanwhile, all structure-property correlations revealed herein will enable knowledge-based molecular design of coumarins for dye lasers and DSC applications.

  5. Coumarin Push-Pull NLOphores with Red Emission: Solvatochromic and Theoretical Approach.

    Science.gov (United States)

    Lanke, Sandip K; Sekar, Nagaiyan

    2016-05-01

    A new class of red emitting extensively conjugated donor-π-acceptor type dyes bearing coumarin units are investigated for nonlinear optical properties. The photophysical behaviour and the relation between structure and properties of the coumarin "push-pull" derivatives were investigated based on solvatochromism and experimentally observed shifts in emission maxima. The electronic coupling for the electron transfer reaction for the coumarin dyes are calculated with the generalized Mulliken-Hush method. We evaluated non-linear optical (NLO) properties of coumarin dyes using both experimental solvent dependent shift method and computational method. All the investigated coumarin dyes are showing large value for first (β) and second hyperpolarizability (γ). Density functional theory [B3LYP/6-31G(d)] and time dependent density functional theory (TDDFT) computations have been employed to have more understanding of structural, molecular, electronic and photophysical parameters of the coumarin dyes.

  6. Recent developments of C-4 substituted coumarin derivatives as anticancer agents.

    Science.gov (United States)

    Dandriyal, Jyoti; Singla, Ramit; Kumar, Manvendra; Jaitak, Vikas

    2016-08-25

    Cancer is a prominent cause of death in global. Currently, the numbers of drugs that are in clinical practice are having a high prevalence of side effect and multidrug resistance. Researchers have made an attempt to expand a suitable anticancer drug that has no MDR and side effect. Coumarin scaffold became an attractive subject due to their broad spectrum of pharmacological activities. Coumarin derivatives extensively explored for anticancer activities as it possesses minimum side effect along with multi-drug reversal activity. Coumarin derivatives can act by various mechanisms on different tumor cell lines depending on substitution pattern of the core structure of coumarin. Substitution on coumarin nucleus leads to the search for more potent compounds. In this review, we have made an effort to give a synthetic strategy for the preparation of C-4 substituted coumarin derivatives as anticancer agents based on their mechanism of action and also discuss the SAR of the most active compound.

  7. Synthesis, crystal structures and photoluminescence of anthracen- and pyrene-based coumarin derivatives.

    Science.gov (United States)

    Zhang, Hui; Tong, Hao; Zhao, Yuling; Yu, Tianzhi; Zhang, Peng; Li, Jianfeng; Fan, Duowang

    2015-11-01

    Two new anthracen- and pyrene-based coumarin derivatives, 3-(4-(anthracen-10-yl)phenyl)coumarin (4) and 3-(4-(pyrene-1-yl)phenyl)coumarin (5), were synthesized and characterized by FT-IR, (1)H NMR, element analysis and single crystal X-ray crystallography. The UV-vis absorption and photoluminescence spectra of these coumarin derivatives were investigated. The results show that compound 4 and 5 exhibit blue and blue-green emissions, respectively, under ultraviolet light excitation. Compared with the compound 4, the emission peak of compound 5 was bathochromically shifted by about 80 nm due to the more planar structure and larger π-conjugation.

  8. Reversible photochemical modifications in dicarbene-derived metallacycles with coumarin pendants.

    Science.gov (United States)

    Han, Ying-Feng; Jin, Guo-Xin; Daniliuc, Constantin G; Hahn, F Ekkehardt

    2015-04-13

    Molecular rectangles were obtained from two bis(NHC) ligands, each featuring two terminal coumarin groups and two Ag(+), Au(+), or Cu(+) ions. Upon UV irradiation (λ=365 nm), the dinuclear complexes undergo photochemical modification through a [2+2] cycloaddition reaction of two adjacent coumarin moieties to give a macrocyclic tetra(NHC) ligand. The photodimerization of the coumarin pendants proceeds stereoselectively to give the syn-head-head isomers in all cases. Subsequent irradiation at λ=254 nm initiates a photocleavage reaction with reconstitution of the initial dinuclear complexes with coumarin pendants.

  9. Coumarin Based Neutral Sensor for Biologically Important Anions

    Institute of Scientific and Technical Information of China (English)

    SHAO Jie

    2011-01-01

    A coumarin Shiff-base derivative,salicylaldehyde-N-(6-phenylazo-coumarin-3-formyl)-hydrazone(1),was obtained by simple organic synthesis from cheap and commercially available starting materials.Sensor 1 exhibits a very weak fluorescence emission,however,in the presence of acetate ions “turn-on” fluorescence is observed,which results from binding-induced conformational restriction of the fluorophore.Importantly,sensor 1 can also be used as colorimetric chemosensor for the anions with strong basicity,which is easily observed from yellow to red by naked eyes.Consequently,compound l can behave as a colorimetric and fluorescence sensor for biologically important F,CH3COO and H2PO4- in the presence of the other anions tested such as Cl-,Br- and I- in dimethyl sulfoxide(DMSO).

  10. Novel macromolecules derived from coumarin: synthesis and antioxidant activity

    Science.gov (United States)

    Al-Amiery, Ahmed A.; Al-Majedy, Yasameen K.; Kadhum, Abdul Amir H.; Mohamad, Abu Bakar

    2015-07-01

    The rational design of 4-hydroxycoumarins with tailor-made antioxidant activities is required nowadays due to the wide variety of pharmacologically significant, structurally interesting of coumarins and researcher orientation toward green chemistry and natural products. A simple and unique coumarins have been achieved by reaction of 4-hydroxycoumarin with aromatic aldehyde accompanied with the creation of a macromolecules have 2-aminothiazolidin-4-one. The molecular structures of the compounds were characterized by the Fourier transformation infrared and Nuclear magnetic resonance spectroscopies, in addition to CHN analysis. The scavenging abilities of new compounds against stable DPPH radical (DPPH•) and hydrogen peroxide were done and the results show that the compounds exhibited high antioxidant activates.

  11. Two benzoyl coumarin amide fluorescence chemosensors for cyanide anions

    Science.gov (United States)

    Wang, Zian; Wu, Qianqian; Li, Jiale; Qiu, Shuang; Cao, Duxia; Xu, Yongxiao; Liu, Zhiqiang; Yu, Xueying; Sun, Yatong

    2017-08-01

    Two new benzoyl coumarin amide derivatives with ortho hydroxyl benzoyl as terminal group have been synthesized. Their photophysical properties and recognition properties for cyanide anions in acetonitrile have also been examined. The influence of electron donating diethylamino group in coumarin ring and hydroxyl in benzoyl group on recognition properties was explored. The results indicate that the compounds can recognize cyanide anions with obvious absorption and fluorescence spectral change and high sensitivity. The import of diethylamine group increases smartly the absorption ability and fluorescence intensity of the compound, which allows the recognition for cyanide anions can be observed by naked eyes. The in situ hydrogen nuclear magnetic resonance spectra combining photophysical properties change and job's plot data confirm that Michael addition between the chemosensors and cyanide anions occurs. Molecular conjugation is interrupted, which leads to fluorescence quenching. At the same time, there is a certain extent hydrogen bond reaction between cyanide and hydroxyl group in the compounds, which is beneficial to the recognition.

  12. A new synthetic protocol for coumarin amino acid

    Directory of Open Access Journals (Sweden)

    Xinyi Xu

    2013-02-01

    Full Text Available The hydrochloride of the racemic amino acid (2-(7-hydroxycoumarin-4-ylethylglycine, which can serve as a fluorescent probe in proteins, and two halogen derivatives of it, were synthesized by using a new synthetic protocol in five steps. It is less costly and relatively easy to prepare this kind of fluorescent amino acid with the new synthetic method. Furthermore, it can be applied to synthesize other derivatives of the coumarin amino acid with some specific properties.

  13. New sesquiterpene coumarins from the roots of Ferula flabelliloba.

    Science.gov (United States)

    Iranshahi, Mehrdad; Kalategi, Farhad; Sahebkar, Amirhossein; Sardashti, Alireza; Schneider, Bernd

    2010-02-01

    Three new sesquiterpene coumarins, namely, farnesiferone B (1), flabellilobin A (2) and flabellilobin B (3), together with nine known compounds, ligupersin A, 7-epi-gamma-eudesmol, persicasulfide A, conferdione, umbelliprenin, conferone, feselol, lehmferin and farnesiferol B were isolated from the roots of Ferula flabelliloba Rech. f. & Aell. (Apiaceae). The structures of these compounds were elucidated by various 1- and 2-D NMR techniques as well as HREIMS.

  14. Elucidation of the binding mechanism of coumarin derivatives with human serum albumin.

    Directory of Open Access Journals (Sweden)

    Archit Garg

    Full Text Available Coumarin is a benzopyrone which is widely used as an anti-coagulant, anti-oxidant, anti-cancer and also to cure arthritis, herpes, asthma and inflammation. Here, we studied the binding of synthesized coumarin derivatives with human serum albumin (HSA at physiological pH 7.2 by using fluorescence spectroscopy, circular dichroism spectroscopy, molecular docking and molecular dynamics simulation studies. By addition of coumarin derivatives to HSA the maximum fluorescence intensity was reduced due to quenching of intrinsic fluorescence upon binding of coumarin derivatives to HSA. The binding constant and free energy were found to be 1.957±0.01×10(5 M(-1, -7.175 Kcal M(-1 for coumarin derivative (CD enamide; 0.837±0.01×10(5 M(-1, -6.685 Kcal M(-1 for coumarin derivative (CD enoate, and 0.606±0.01×10(5 M(-1, -6.49 Kcal M(-1 for coumarin derivative methylprop (CDM enamide. The CD spectroscopy showed that the protein secondary structure was partially unfolded upon binding of coumarin derivatives. Further, the molecular docking studies showed that coumarin derivatives were binding to HSA at sub-domain IB with the hydrophobic interactions and also with hydrogen bond interactions. Additionally, the molecular dynamics simulations studies contributed in understanding the stability of protein-drug complex system in the aqueous solution and the conformational changes in HSA upon binding of coumarin derivatives. This study will provide insights into designing of the new inspired coumarin derivatives as therapeutic agents against many life threatening diseases.

  15. Syntheses of Some 3-[1'( 1' H )-Substituent-pyrazol-5'-yl ] benzo [5,6] coumarins

    Institute of Scientific and Technical Information of China (English)

    EL-DEEN, Ibrahim Mohey; AL-WAKEEL, El-Sayed Ismail; El-MAWLA, Ahmed Gad

    2002-01-01

    3-[1' (1' H)-Substitueut-pyrazol-5'-yl] benzo [ 5, 6] coumarins and 3-(1' , 2 '-oxazol- 5 '- yl ) benzo [ 5 , 6 ] coumarin were prepared via condensation of 3-(2'-formyl-1'-chlorovinyl) benzo [ 5, 6]coumarin with hydrazine derivatives or hydroxylamine. Reaction of 3-[1' (1'H)-pyrazol-5'-yl] benzo[5, 6] coumarin with alkyl halides, olefinic compounds or acid chlorides are described.

  16. Genotype-guided coumarin dosing: Where are we now and where do we need to go next?

    NARCIS (Netherlands)

    Baranova, Ekaterina V.; Verhoef, Talitha I; Asselbergs, Folkert W.; De Boer, Anthonius; Maitland-Van Der Zee, Anke-Hilse

    2015-01-01

    Introduction: A large proportion of the coumarin dose variability is explained by environmental factors and by common genetic variants in the VKORC1 and CYP2C9 genes. Genotype-guided coumarin dosing has been proposed for a more accurate prediction of the coumarin dose in order to reduce the incidenc

  17. Genotype-guided coumarin dosing : where are we now and where do we need to go next?

    NARCIS (Netherlands)

    Baranova, Ekaterina V; Verhoef, Talitha I; Asselbergs, Folkert W; de Boer, Anthonius; Maitland-van der Zee, Anke-Hilse

    2015-01-01

    INTRODUCTION: A large proportion of the coumarin dose variability is explained by environmental factors and by common genetic variants in the VKORC1 and CYP2C9 genes. Genotype-guided coumarin dosing has been proposed for a more accurate prediction of the coumarin dose in order to reduce the incidenc

  18. Relationship between coumarin-induced hepatocellular toxicity and mitochondrial function in rats.

    Science.gov (United States)

    Tanaka, Yasuhiro; Fujii, Wataru; Hori, Hisako; Kitagawa, Yoshinori; Ozaki, Kiyokazu

    2016-04-01

    The manifestation of coumarin-induced hepatocellular toxicity may differ and depends on the frequency of administration to rats. A single coumarin dose induces hepatocellular necrosis while repeated doses induce only hepatocyte degeneration. However, the mechanism underlying these effects remains unclear. Therefore, we investigated the mechanism of coumarin-induced hepatotoxicity in rats. Coumarin was administered to male rats as a single dose or for 4 consecutive days, and samples were obtained 4 or 24 h after a single dose or 24 h after the repeated doses. A single coumarin dose significantly induced hepatocellular necrosis in rats; however, toxicity was attenuated after repeated dosing. With a single dose, hepatocellular necrosis was preceded by increased mitochondrial number and size and decreased mitochondrial function. An increased expression of granular cytochrome P450 (CYP) 2E1 protein was observed in the cytoplasm and mitochondria of coumarin-treated rats compared to the expression in the untreated controls. Nevertheless, repeated dosing showed mitochondrial function that was equivalent to that of the control while enlarged CYP2E1 protein droplets were distributed outside the mitochondria. These results suggest that mitochondrial function and CYP2E1 expression might be involved in coumarin-induced hepatocellular toxicity in rats. A reduction in mitochondrial CYP2E1 might be implicated in the acquisition of coumarin resistance after repeated doses.

  19. Coumarin: A Privileged Scaffold for the Design and Development of Antineurodegenerative Agents.

    Science.gov (United States)

    Jameel, Ehtesham; Umar, Tarana; Kumar, Jitendra; Hoda, Nasimul

    2016-01-01

    Drug development for neurodegenerative diseases (NDs) is foremost task for the medicinal chemists in the 21st century. Coumarins are exemplary of an assorted and aptitudinally useful set of drugs. Coumarins play a momentous role in several pharmacological and medicinal aspects. Its analogues are anticipated to play a significant role in the development of new therapeutic leads for NDs. Their promising applications in the field of ND medication are exemplified by clinical candidates such as nodakenin that have been potent for demoting memory impairment. Apart from ND, clinically used anticoagulant warfarin, anticoagulant dicoumarol, and antibiotic coumermycin, novobiocin and chartesium grab the interest of researchers in coumarins. It would be worthwhile to look at the different biological processes that could cause neurodegeneration, thereby establishing a link with distinct coumarin derivatives to serve the purpose of medication. This review undertakes estimation of the wide spectrum of studies focusing coumarin to the domain of drug research for ND. Herein, we search for multitarget coumarin-based inhibitors and their scope for NDs. Future challenges in coumarin-based drug development have been discussed, and emphases have been laid on the future perspectives of coumarins as possible drugs in the future for the treatment of NDs.

  20. In utero exposure to coumarins and cognition at 8 to 14 years old

    NARCIS (Netherlands)

    van Driel, Dieneke; Wesseling, Judit; Sauer, Pieter J J; van der Veer, Eveline; Touwen, Bert C L; Smrkovsky, Mila

    2001-01-01

    Objective. To assess the cognitive abilities in school-aged children who have been exposed to coumarins in utero. Background. Coumarin derivatives are an effective option for anticoagulant therapy in pregnant women. However, case reports describe anomalies of the fetal central nervous system after i

  1. The antitumor effects of mitochondria-targeted 6-(nicotinamide methyl coumarin

    Directory of Open Access Journals (Sweden)

    Wang Huanan

    2016-01-01

    Full Text Available Cancer is the second leading cause of death worldwide. Traditional antitumor drugs exhibit severe cytotoxic and side effects. Lung cancer needs new and more effective treatment approaches. Coumarin derivatives can act on various tumor cells and show anti-proliferative activity through various mechanisms, including mitochondrial signaling cascades that regulate development and apoptosis of cells. Mitochondria-targeted coumarin derivatives have not been reported yet. Taking advantage of the fact that cancer cells frequently have higher mitochondria membrane potential, we synthesized a mitochondria-targeted 6-(nicotinamide methyl coumarin by coupling 6-methyl coumarin to nicotinamide. Our results demonstrate that 6-(nicotinamide methyl coumarin preferentially kills A549 cells through inducing A549 cells apoptosis, mediated by increasing ROS level and causing mitochondrial depolarization. Strikingly, the viability of the A31 cells treated with 6-(nicotinamide methyl coumarin did not decrease, indicating that 6-(nicotinamide methyl coumarin preferentially accumulates in A549 cells and A549 cells are much more susceptible to 6-(nicotinamide methyl coumarin treatment compared with A31 cells.

  2. [Impending Coumarin-necrosis in a patient with heterozygous protein C deficiency type I].

    Science.gov (United States)

    Schulze, R; Behr, W; Wittwer, H; Harwix, S; Murmann, K; V Scheidt, W; Ehret, W; Schlimok, G

    2008-05-01

    Painful pink or magenta colored skin lesions characterized by a clear line of demarcation between the affected area and surrounding tissue appearing under therapy with coumarins may be a sign for evolving coumarin-necrosis. Immediate treatment with a protein C preparation in patients with protein C deficiency can prevent necrosis.

  3. Coumarins from Murraya paniculata var. zollingeri endemic to the Timor Islands.

    Science.gov (United States)

    Teshima, Naoko; Yamada, Hiromi; Ju-ichi, Motoharu; Uji, Tahan; Kinoshita, Takeshi; Ito, Chihiro

    2015-02-01

    Four new coumarins, murrangatin-1'-senecioate (1), 5-methoxypanial (2), mexoticin-2'-senecioate (3) and murralongic acid (4), were isolated from the leaves of Murraya paniculata var. zollingeri, together with 23 known coumarins. The structures of the new compounds were elucidated based on spectroscopic data. The taxonomic status of M. paniculata var. zollingeri is briefly discussed, along with its similarity to M. paniculata.

  4. Mito-methyl coumarin, a novel mitochondria-targeted drug with great antitumor potential was synthesized.

    Science.gov (United States)

    Wang, Huanan; Xu, Wenqing

    2017-07-15

    Due to higher transmembrane potential of tumor cells, enhanced accumulation of cationic drugs in tumor mitochondria has been attributed to a higher (more negative inside) mitochondrial transmembrane potential compared with normal cells, emerging researchers are focus on developing mitochondria-targeted antitumor drugs. Coumarins showed great potential on antitumor, but mitochondria-targeted coumarin derivatives have not been reported. In the present study, we synthesized mitochondria-targeted-methyl coumarin (mito-methyl coumarin) through coupling 6-methyl coumarin to TPP. We confirmed that mito-methyl coumarin inhibited HeLa cells proliferation selectively, induced ROS generation, reduced mitochondrial membrane potential, promoted mitochondria Ca(2+) accumulation, decreased mitochondria mass and induced HeLa cells apoptosis, but methyl coumarin did not. These results demonstrate that we succeed in synthesizing a novel mitochondria-targeted drug, mito-methyl coumarin, which is effective in inhibiting HeLa cells proliferation and inducing HeLa cells apoptosis through promoting ROS generation and mitochondria Ca(2+) accumulation. Copyright © 2017 Elsevier Inc. All rights reserved.

  5. Inhibitory Effect of Coumarin on Syntrophic Fatty Acid-Oxidizing and Methanogenic Cultures and Biogas Reactor Microbiomes.

    Science.gov (United States)

    Popp, Denny; Plugge, Caroline M; Kleinsteuber, Sabine; Harms, Hauke; Sträuber, Heike

    2017-07-01

    Coumarins are widely found in plants as natural constituents having antimicrobial activity. When considering plants that are rich in coumarins for biogas production, adverse effects on microorganisms driving the anaerobic digestion process are expected. Furthermore, coumarin derivatives, like warfarin, which are used as anticoagulating medicines, are found in wastewater, affecting its treatment. Coumarin, the structure common to all coumarins, inhibits the anaerobic digestion process. However, the details of this inhibition are still elusive. Here, we studied the impact of coumarin on acetogenesis and methanogenesis. First, coumarin was applied at four concentrations between 0.25 and 1 g · liter(-1) to pure cultures of the methanogens Methanosarcina barkeri and Methanospirillum hungatei, which resulted in up to 25% less methane production. Acetate production of syntrophic propionate- and butyrate-degrading cultures of Syntrophobacter fumaroxidans and Syntrophomonas wolfei was inhibited by 72% at a coumarin concentration of 1 g · liter(-1) Coumarin also inhibited acetogenesis and acetoclastic methanogenesis in a complex biogas reactor microbiome. When a coumarin-adapted microbiome was used, acetogenesis and methanogenesis were not inhibited. According to amplicon sequencing of bacterial 16S rRNA genes and mcrA genes, the communities of the two microbiomes were similar, although Methanoculleus was more abundant and Methanobacterium less abundant in the coumarin-adapted than in the nonadapted microbiome. Our results suggest that well-dosed feeding with coumarin-rich feedstocks to full-scale biogas reactors while keeping the coumarin concentrations below 0.5 g · liter(-1) will allow adaptation to coumarins by structural and functional community reorganization and coumarin degradation.IMPORTANCE Coumarins from natural and anthropogenic sources have an inhibitory impact on the anaerobic digestion process. Here, we studied in detail the adverse effects of the model

  6. Influence of Polarity of Solvents on the Spectral Properties of Bichromophoric Coumarins

    Directory of Open Access Journals (Sweden)

    Henrieta Stankovicova

    2010-12-01

    Full Text Available Absorption and fluorescence spectra of bichromophoric coumarins were investigated in different solvents and in polymer matrices. These bichromophoric coumarins were composed of a coumarin dimethylamino-substituted at position 7 or unsubstituted coumarin and phthalimide or a 1,8-naphthylimide linked with an iminomethyl bridge to the position 3 or 8 of the coumarin ring. Absorption spectra of 7-dimethylamino derivatives in position 3 of coumarin were quite similar, exhibiting broad bands around 430-440 nm like the parent compound 7-dimethylaminocoumarin-3-carbaldehyde. For coumarin derivatives substituted in position 8, the absorption maximum was shifted to shorter wavelength as for derivatives without position 7 dimethylamino substitution. The most intense fluorescence was observed for 7-(N,N-dimethylamino-3-[(N-phtalimidoyliminomethyl]coumarin in polar solvent, while intense fluorescence was observed for 7-(N,N-dimethylamino-3-[N-(1,3-dioxobenz[de]isoquinolinyliminomethyl]-coumarin in non polar solvent (chloroform, comparable with the fluorescence of 7-amino-4-methylcoumarin. Spectral measurements of bichromophoric coumarins in polymer matrices revealed that the maxima lies in between those for chloroform and methanol yielding more intense fluorescence then in solutions. Completely different solvent effects were observed for 7-(N,N-dimethylamino-3-[N-(1,3-dioxobenz[de]isoquinolinylimino-methyl]coumarin and 7-(N,N-dimethylamino-3-[(N-phtalimidoyliminomethyl]coumarin. With addition of polar methanol the intensity of fluorescence decreases, yielding a Stern-Volmer-like constant of 0.54 dm3 mol−1 for 7-(N,N-dimethylamino-3-[N-(1,3-dioxo-benz[de]isoquinolinyliminomethyl]coumarin and an even higher one of 1.08 dm3 mol−1 for 7-dimethylaminocoumarin-3-carbaldehyde compared to the rather low one of 0.024 dm3 mol−1 for 7-amino-4-methylcoumarin. Contrary to this, addition of methanol under identical conditions brings about an increase in fluorescence

  7. AIE Based Coumarin Chromophore - Evaluation and Correlation Between Solvatochromism and Solvent Polarity Parameters.

    Science.gov (United States)

    Lanke, Sandip K; Sekar, Nagaiyan

    2016-03-01

    A new class of red emitting extensively conjugated donor-π-acceptor type dyes bearing coumarin units have been synthesized by condensation of 7-(diethylamino)-2-oxo-2 H-chromene-3-carbaldehyde with different active methylenes. All the dyes are characterized by (1)H NMR, (13)C NMR and HRMS spectroscopy. The photophysical behaviour and the relation between structure and properties of the coumarin "push-pull" derivatives were investigated experimentally. The dyes exhibited positive solvatochromism and solvatofluorism in solution of varying polarity. These coumarin dyes show aggregation induced emission properties with red emitting fluorescence. They show absorption in the range of 501-528 and emission in the range of 547-630 nm. We evaluated photophysical properties of coumarin dyes using solvotochromism and solvent dependent shift in the emission wavelength. All the synthesized coumarin dyes COS1-COS4 are showing very good solvatochromic properties.

  8. Herbicidal Activity of Coumarin When Applied as a Pre-plant Incorporated into Soil

    Directory of Open Access Journals (Sweden)

    Amir-Hossein NAZEMI

    2015-06-01

    Full Text Available Due to having a short half-life and novel site of action, the herbicidal potential of natural compounds are lionized. Coumarin is a secondary metabolite from Lavandula sp., family Lamiacae. The impact of eight concentrations of coumarin (0, 100, 200, 400, 800, 1600, 3200 and 6400 ppm were separately used as a pre-plant incorporated into soil on six plant species under greenhouse conditions. Generally, coumarin had phytotoxic effect against all plant species. The phytotoxic effect was concentration-dependent. The high concentrations could inhibit the emergence of seedlings (probably by stopping germination of seeds. Based on ED50 parameter, the ranking of plant species for tolerance to coumarin was S. halepense > Z. mays > C. album > A. retroflexus > E. cruss-gali > P. oleracea. Based on selectivity index, coumarin at a concentration of 365.69 ppm can control P. oleracea without damaging Z. mays, whereas any concentration it cannot control other weeds without damaging Z. mays.

  9. The resolution of thermal oedema at various temperatures under coumarin treatment.

    Science.gov (United States)

    Piller, N B

    1975-02-01

    The treatment of thermal oedema with coumarin (a benzopyrone) has been found to be most effect when fast moving air of 20 degrees was blown over the burnt animals. Coumarin has two main effects: one is to cause vascular injury thus allowing extra protein and fluid into the tissues; the other is to stimulate phagocytosis, enzyme production and thus proteolysis and a subsequent removal of protein and fluid from the injured tissues. At lower temperatures the injurious nature of coumarin is prominent. At medium range temperatures the proteolytic actions of coumarin outweigh its injurious nature. Resolution thus proceeds much more rapidly. At high temperatures resolution is slowed. This is a consequence of the antioxidant effect of coumarin on adrenaline and ambient temperature on peripheral dilatation. The results obtained tie in well with those obtained by workers using water of equivalent temperature.

  10. Synthesis and characterization of tunable coumarin- linked glasses as new class of organic/inorganic phosphors

    Energy Technology Data Exchange (ETDEWEB)

    Luridiana, Alberto; Pretta, Gianluca; Secci, Francesco; Frongia, Angelo [Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, Complesso universitario di Monserrato, SS 554, bivio per Sestu, Monserrato (Canada) (Italy); Chiriu, Daniele; Carbonaro, Carlo Maria; Corpino, Riccardo [Dipartimento di Fisica, Università degli Studi di Cagliari, Complesso universitario di Monserrato, SS 554, bivio per Sestu, Monserrato (Canada) (Italy); Ricci, Pier Carlo, E-mail: carlo.ricci@dsf.unica.it [Dipartimento di Fisica, Universitá degli Studi di Cagliari, S.P. Monserrato-Sestu Km 0,700, 09042 Monserrato (Canada) (Italy)

    2014-10-21

    It is well known that stilbene with a trans conformation is highly fluorescent. From the viewpoint of molecular structure, coumarins bear a carbon-carbon double bond which is fixed as trans conformation as in trans-stilbene through a lactone structure. This can help to avoid the trans-cis transformation of the double bond under ultraviolet (UV) irradiation as observed in stilbene compounds and results in strong fluorescence and high fluorescence quantum yield and photostability in most of coumarin derivatives. Herein we report some preliminary results about the synthesis and spectroscopic characterization of tunable coumarins and the development of a new linkage protocol for the obtainment of monolayer coumarin-covalently linked glasses. The resulting organic/inorganic coumarin/silica based Self-Assembled Monolayer (SMA) film is proposed as new phosphors for the substituting of critical raw materials, like rare earths, in photonics applications.

  11. Study of Photophysical Properties on Newly Synthesized Coumarin Derivatives.

    Science.gov (United States)

    Sidarai, Ashok H; Desai, Vani R; Hunagund, Shirajahammad M; Basanagouda, Mahantesha; Kadadevarmath, Jagadish S

    2017-08-19

    Herein, we have studied the photophysical properties for three newly synthesized coumarin derivatives; 4-((2,6-dibromo-4-methylphenoxy)methyl)-2H-benzo[h]chromen-2-one (DMB), 4-((3,4-dihydro-6,7-dimethoxyisoquinolin-1-yl)methyl)-6-methyl-2H-chromen-2-one (DIM) and 4-((p-tolyloxy)methyl)-6-methoxy-2H-chromen-2-one (TMC). The absorption and emission spectra for above said molecules were recorded in different solvents at room temperature in order to calculate their ground and excited state dipole moments. The ground (μ g ) and excited state dipole (μ e ) moments of these coumarin derivatives were calculated using Lippert's, Bakshiev's and Kawski-Chamma-Viallet's equations by the solvatochromic shift method, which involves a variation of Stokes shift with the solvent dielectric constant and refractive index. Ground state dipole moments (μ g ) were also calculated from the Guggenheim method using the dielectric constant and refractive index of the solute molecule. The value of ground state dipole moment obtained from these two methods is well correlated. Further, it is notified that the excited state dipole moment is larger than the ground state dipole moment for all three solute molecules. It inferred that the excited state for above said molecules is more polar than the ground state. The present investigations may shine in the design of nonlinear optical materials. Graphical Abstract The photophysical properties for novel coumarin derivatives were studied in different solvents.Ground and excited state dipole moments were estimated by the solvatochromic shift method. The excited state dipole moment is greater than the ground state dipole moment in systems studied. The excited state is more polar than the ground state. The present investigation may be shine in the design of non linear optical materials.

  12. Synthesis and Evaluation of Some Coumarin Containing Potential Antimicrobial Agents

    Directory of Open Access Journals (Sweden)

    Sayali D. Kudale

    2012-01-01

    Full Text Available A series of the Schiff’s bases incorporating coumarin and chalcone moeities, 3-(4-(4-(substituted phenylprop-1-ene-3-one phenylimino methyl-4-chloro-2h-chromen-2-one 4(a-g were synthesized as potential antimicrobial agents. These compounds were characterized on the basis of their spectral (IR, 1H NMR data and evaluated for antimicrobial activity in vitro against gram positive and gram negative bacteria and fungi. Compound 4b was found to be most active with an MIC of 20 µg/mL against all the tested organisms.

  13. Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis?

    Science.gov (United States)

    Fonseca, André; Reis, Joana; Silva, Tiago; Matos, Maria João; Bagetta, Donatella; Ortuso, Francesco; Alcaro, Stefano; Uriarte, Eugenio; Borges, Fernanda

    2017-08-24

    Because of the lack of significant disease-modifying drugs for neurodegenerative disorders, a pressing need for new chemical entities endowed with IMAO-B still exists. Within this framework, and for the first time, a study was performed to compare coumarin- and chomone-3-phenylcarboxamide scaffolds. Compounds 10a and 10b were the most potent, selective, and reversible noncompetitive IMAO-B. The benzopyrone sp(2) oxygen atom was found to be position independent and a productive contributor for the ligand-enzyme complex stability.

  14. Novel fluorescent chemosensor for Ag+ based on coumarin fluorophore

    Institute of Scientific and Technical Information of China (English)

    Mao Xiang Wang; Xiang Ming Meng; Man Zhou Zhu; Qing Xiang Guo

    2008-01-01

    A novel chemosensor 1 (CS1) bearing one coumarin and two carbodithioate groups was synthesized and its fluorescent sensing behavior toward metal ions was investigated. Ag+ addition to a CH3COCH3/H20 (3:7, v:v) solution of CS1 gave a significantly quenched fluorescence. Other ions including Pb2+, Zn2+, Cu2+, Ca2+, Cd2+, Co2+, Mg2+, Mn2+, Hg2+, Ag+, Ni2+ induced no or much smaller spectral changes. This constitutes an ON-OFF Ag+-selective fluorescent chemosensor.

  15. Uncatalysed Production of Coumarin-3-carboxylic Acids: A Green Approach

    Directory of Open Access Journals (Sweden)

    Joel Martínez

    2016-01-01

    Full Text Available A green contribution in short reaction times with moderate yields to produce coumarin-3-carboxylic acids is offered. Five different modes to activate the reactions (microwave, near-infrared, mechanical milling, and ultrasound were compared with mantle heating in the presence or absence of ethanol, a green solvent. Near-infrared and microwave irradiations deliver the best yields in contrast to ultrasound and mechanical milling; moreover, these four processes offered shorter reaction times in comparison with the conventional mantle heating method. It is also important to highlight that the obtained molecules were produced without the requirement of a catalyst and two nonconventional energies forms are presented as new processes.

  16. Antiplatelet Aggregation Coumarins from the Leaves of Murraya omphalocarpa

    Directory of Open Access Journals (Sweden)

    Yang-Chang Wu

    2008-01-01

    Full Text Available Using a bioactivity-guided fractionation method, two coumarins: minumicrolineacetonide (1 and epimurpaniculol senecioate (2, were isolated from the leaves ofMurraya omphalocarpa Hayata (Rutaceae. Compound 1 had been previously synthesizedand was now isolated from natural sources for the first time, and compound 2, possessing anegative optical rotation value, is new. The structures and their stereochemistry were fullyelucidated on the basis of spectroscopic and X-ray crystallographic techniques. Bothcompounds 1 and 2 are active in the antiplatelet aggregation assay. Interestingly, thepossible acetonide artifact 1 displayed significant antiplatelet aggregation induced not onlyby AA and collagen but also by platelet activating factor (PAF.

  17. Expedient synthesis of coumarin-coupled triazoles via 'click chemistry' leading to the formation of coumarin-triazole-sugar hybrids.

    Science.gov (United States)

    Kumar, K Karthik; Kumar, R Mahesh; Subramanian, V; Das, T Mohan

    2010-11-02

    Coumarin-based triazoles were synthesized from 3-azidomethylcoumarin and a terminal acetylenic compound. Uncatalysed thermal conditions result in a mixture of both 1,4- and 1,5-regioisomers or the thermodynamically more stable 1,4-regioisomer, whereas the Cu(I)-catalysed reaction affords only the favourable 1,4-regioisomer. B3LYP/6-31G(d) level of theory has been used to calculate geometry and frequency features of the reactants, transition states (TSs) and products. Computational studies further reveal that 1,4-regioisomeric products are more favourable and also thermodynamically more stable compared to the 1,5-regioisomers.

  18. Photoprotective effect of coumarin and 3-hydroxycoumarin in sea urchin gametes and embryonic cells.

    Science.gov (United States)

    de Araujo Leite, Jocelmo Cássio; de Castro, Tainá Myra Xavier; Barbosa-Filho, José Maria; de Siqueira-Junior, José Pinto; Marques-Santos, Luis Fernando

    2015-05-01

    Ultraviolet radiation B (UVB) represents 5% of all solar UV radiation and chronic exposure can induce harmful biological responses, including skin cancer. Prospection of new drugs with photoprotective properties and less toxic effects is constant and natural products have been the main options in this field. Coumarins are a group of natural phenolic compounds that shows several pharmacological activities. The aim of present work was to investigate the effect of coumarin and six derivatives in sea urchin gametes and zygotes exposed to UVB. Embryonic development assay was used to monitor UVB embryotoxicity. Firstly, we demonstrated that coumarin inhibited first embryonic cell division from 5 μM (EC50 = 52.9 μM) and its derivatives showed an embryotoxic effect ten times higher. Then, gametes or zygotes were treated with coumarin compounds before or after UVB exposure (UVB doses ranged from 0.056 to 0.9 kJm(-2)). Pretreatment of gametes or zygotes with coumarin or 3-hydroxycoumarin (1 μM, both) decreased UVB embryotoxic effect. Protective effect of the compounds was observed only when cells were treated previous to UVB exposure. Coumarin derivatives 4-hydroxycoumarin, 6-hydroxycoumarin, 7-hydroxycoumarin, 6,7-dihydroxycoumarin and 6-methoxy-7-hydroxycoumarin did not exhibit photoprotective activity. Our data provides evidences that coumarin and 3-hydroxycoumarin can be a promising class of photoprotective drugs.

  19. Low doping concentration studies of doped PVA-Coumarin nanocomposite films

    Science.gov (United States)

    Tripathi, J.; Tripathi, S.; Bisen, R.; Sharma, A.; Choudhary, A.; Shripathi, T.

    2016-05-01

    The observations of combination of Poly (vinyl) alcohol and Coumarin properties in nanocmposite films are reported. The X-ray diffraction measurements reveal nanocrystalline nature of PVA film, which remains nanocrystalline after doping Coumarin but along with PVA peaks, additional peak due to dopant crystallinity is seen. The absorption edge shows a double edge feature, where distinct bandgaps for PVA host and dopant Coumarin are obtained. However at a higher doping wt % of 1 and 2, the absorption is mainly dominated by Coumarin and single absorption edge is observed giving a bandgap equal to that of bulk Coumarin (3.3 eV). The composite formation affects the bonding of host drastically and is seen through the bond modification in FTIR spectra. The results suggest that doping below 2 wt% is advantageous as combination of PVA and Coumarin properties are obtained but at 2 wt %, the properties are dominated by mainly Coumarin and the signature of PVA from optical properties is completely lost.

  20. Gustatory Receptors Required for Avoiding the Toxic Compound Coumarin in Drosophila melanogaster

    Science.gov (United States)

    Poudel, Seeta; Lee, Youngseok

    2016-01-01

    Coumarin is a phenolic compound that mainly affects the liver due to its metabolization into a toxic compound. The deterrent and ovicidal activities of coumarin in insect models such as Drosophila melanogaster have been reported. Here we explore the molecular mechanisms by which these insects protect themselves and their eggs from this toxic plant metabolite. Coumarin was fatal to the flies in a dosage-dependent manner. However, coumarin feeding could be inhibited through activation of the aversive gustatory receptor neurons (GRNs), but not the olfactory receptor neurons. Furthermore, three gustatory receptors, GR33a, GR66a, and GR93a, functioned together in coumarin detection by the proboscis. However, GR33a, but not GR66a and GR93a, was required to avoid coumarin during oviposition, with a choice of the same substrates provided as in binary food choice assay. Taken together, these findings suggest that anti-feeding activity and oviposition to avoid coumarin occur via separate mechanisms. PMID:26912085

  1. Micropatterned coumarin polyester thin films direct neurite orientation.

    Science.gov (United States)

    McCormick, Aleesha M; Maddipatla, Murthy V S N; Shi, Shuojia; Chamsaz, Elaheh A; Yokoyama, Hiroshi; Joy, Abraham; Leipzig, Nic D

    2014-11-26

    Guidance and migration of cells in the nervous system is imperative for proper development, maturation, and regeneration. In the peripheral nervous system (PNS), it is challenging for axons to bridge critical-sized injury defects to achieve repair and the central nervous system (CNS) has a very limited ability to regenerate after injury because of its innate injury response. The photoreactivity of the coumarin polyester used in this study enables efficient micropatterning using a custom digital micromirror device (DMD) and has been previously shown to be biodegradable, making these thin films ideal for cell guidance substrates with potential for future in vivo applications. With DMD, we fabricated coumarin polyester thin films into 10×20 μm and 15×50 μm micropatterns with depths ranging from 15 to 20 nm to enhance nervous system cell alignment. Adult primary neurons, oligodendrocytes, and astrocytes were isolated from rat brain tissue and seeded onto the polymer surfaces. After 24 h, cell type and neurite alignment were analyzed using phase contrast and fluorescence imaging. There was a significant difference (ppolyester thin films has proven beneficial as an axon guidance platform for future nervous system regenerative strategies.

  2. Flavonoids and coumarins from Hieracium pilosella L. (Asteraceae

    Directory of Open Access Journals (Sweden)

    Tadeusz Krzaczek

    2011-04-01

    Full Text Available Typical chromatographic methods were successfully applied to isolate nine flavonoid compounds and two coumarin glycosides from the inflorescences and the herb of Hieracium pilosella L. Repeated column chromatography, occasionally paper chromatography and recrystallization made the separation of three flavonoid aglycones and six glycosides - possible. Coumarin glycosides were isolated by preparative thin layer chromatography. Subsequent UV, NMR and MS analyses have led to identification of the following flavonoid derivatives: known for the species - apigenin, luteolin, luteolin 7-O- ß-glucopyranoside, luteolin 4’-O-ß-glucopyranoside, isoetin 7-O-ß- -glucopyranoside, isoetin 4’-O-ß-glucuronide and new for the species – kaempferol 3-methyl ether and apigenin 7-O-ß-glucopyranoside. Third isoetin glycoside contained two different sugar moieties: xylose and glucose, probably attached to the hydroxyl groups at C-4’ or C-4’ and C-2’(or 5’ of an aglycone. Umbelliferone 7-O-ß-glucopyranoside (skimmin and new for the genus Hieracium esculetin 7-O-ß-glucopyranoside (cichoriin were determined by NMR and MS methods.

  3. Aurapten, a coumarin with growth inhibition against Leishmania major promastigotes

    Directory of Open Access Journals (Sweden)

    Napolitano H.B.

    2004-01-01

    Full Text Available Several natural compounds have been identified for the treatment of leishmaniasis. Among them are some alkaloids, chalcones, lactones, tetralones, and saponins. The new compound reported here, 7-geranyloxycoumarin, called aurapten, belongs to the chemical class of the coumarins and has a molecular weight of 298.37. The compund was extracted from the Rutaceae species Esenbeckia febrifuga and was purified from a hexane extract starting from 407.7 g of dried leaves and followed by four silica gel chromatographic fractionation steps using different solvents as the mobile phase. The resulting compound (47 mg of shows significant growth inhibition with an LD50 of 30 µM against the tropical parasite Leishmania major, which causes severe clinical manifestations in humans and is endemic in the tropical and subtropical regions. In the present study, we investigated the atomic structure of aurapten in order to determine the existence of common structural motifs that might be related to other coumarins and potentially to other identified inhibitors of Leishmania growth and viability. This compound has a comparable inhibitory activity of other isolated molecules. The aurapten is a planar molecule constituted of an aromatic system with electron delocalization. A hydrophobic side chain consisting of ten carbon atoms with two double bonds and negative density has been identified and may be relevant for further compound synthesis.

  4. Toxicogenomic analysis of pharmacological active coumarins isolated from Calophyllum brasiliense.

    Science.gov (United States)

    Gomez-Verjan, J C; Estrella-Parra, E A; Gonzalez-Sanchez, I; Rivero-Segura, N A; Vazquez-Martinez, R; Magos-Guerrero, G; Mendoza-Villanueva, D; Cerbón-Cervantes, M A; Reyes-Chilpa, R

    2015-12-01

    Calophyllum brasiliense (Calophyllaceae) is a tropical rain forest tree, mainly distributed in South and Central America. It is an important source of bioactive natural products like, for instance soulatrolide, and mammea type coumarins. Soulatrolide is a tetracyclic dipyranocoumarins and a potent inhibitor of HIV-1 reverse transcriptase and Mycobacterium tuberculosis. Mammea A/BA and A/BB coumarins, pure or as a mixture, are highly active against several leukemia cell lines, Trypanosoma cruzi and Leishmania amazonensis. In the present work, a toxicogenomic analysis of Soulatrolide and Mammea A/BA + A/BB (3:1) mixture was performed in order to validate the toxicological potential of this type of compounds. Soulatrolide or mixture of mammea A/BA + A/BB (3:1) was administered orally to male mice (CD-1) at dose of 100 mg/kg/daily, for 1 week. After this time, mice were sacrificed, and RNA extracted from the liver of treated animals. Transcriptomic analysis was performed using Affymetrix Mouse Gene 1.0 ST Array. Robust microarray analysis (RMA) and two way ANOVA test revealed for mammea mixture treatment 46 genes upregulated and 72 downregulated genes; meanwhile, for soulatrolide 665 were upregulated and 1077 downregulated genes. Enrichment analysis for such genes revealed that in both type of treatments genetic expression were mainly involved in drug metabolism. Overall results indicate a safety profile. The microarray data complies with MIAME guidelines and are deposited in GEO under accession number GSE72755.

  5. Toxicogenomic analysis of pharmacological active coumarins isolated from Calophyllum brasiliense

    Directory of Open Access Journals (Sweden)

    J.C. Gomez-Verjan

    2015-12-01

    Full Text Available Calophyllum brasiliense (Calophyllaceae is a tropical rain forest tree, mainly distributed in South and Central America. It is an important source of bioactive natural products like, for instance soulatrolide, and mammea type coumarins. Soulatrolide is a tetracyclic dipyranocoumarins and a potent inhibitor of HIV-1 reverse transcriptase and Mycobacterium tuberculosis. Mammea A/BA and A/BB coumarins, pure or as a mixture, are highly active against several leukemia cell lines, Trypanosoma cruzi and Leishmania amazonensis. In the present work, a toxicogenomic analysis of Soulatrolide and Mammea A/BA + A/BB (3:1 mixture was performed in order to validate the toxicological potential of this type of compounds. Soulatrolide or mixture of mammea A/BA + A/BB (3:1 was administered orally to male mice (CD-1 at dose of 100 mg/kg/daily, for 1 week. After this time, mice were sacrificed, and RNA extracted from the liver of treated animals. Transcriptomic analysis was performed using Affymetrix Mouse Gene 1.0 ST Array. Robust microarray analysis (RMA and two way ANOVA test revealed for mammea mixture treatment 46 genes upregulated and 72 downregulated genes; meanwhile, for soulatrolide 665 were upregulated and 1077 downregulated genes. Enrichment analysis for such genes revealed that in both type of treatments genetic expression were mainly involved in drug metabolism. Overall results indicate a safety profile. The microarray data complies with MIAME guidelines and are deposited in GEO under accession number GSE72755.

  6. Cytotoxic effects of mammea type coumarins from Calophyllum brasiliense.

    Science.gov (United States)

    Reyes-Chilpa, Ricardo; Estrada-Muñiz, Elizabet; Apan, Teresa Ramírez; Amekraz, Badia; Aumelas, Andre; Jankowski, Christopher K; Vázquez-Torres, Mario

    2004-08-13

    Calophyllum brasiliense (Clusiaceae) is a big tree from the Tropical Rain Forests of the American continent. The organic extracts from the leaves yielded coumarins of the mammea type: mammea A/BA, A/BB, B/BA, B/BB, C/OA, C/OB, B/BA cyclo F, B/BB cyclo F, and isomammeigin. The triterpenoids friedelin and canophyllol, as well as the biflavonoid amentoflavone, protocatechuic and shikimic acids, were also obtained. Most of the isolated compounds were tested in vitro against K562, U251, and PC3 human tumor cell lines. The coumarins were cytotoxic against the three cell lines, the highest activity was shown by mammea A/BA (IC50 = 0.04 to 0.59 microM). The mixtures of mammea A/BA + A/BB, mammea B/BA + B/BB and mammea C/OA + C/OB were also highly active (IC50 < 4.05 microM). Friedelin was cytotoxic only against PC3, and U251 lines. Inhibition of HIV-1 reverse transcriptase was also assayed in vitro; however, none of the tested compounds (250 microM) prevented the activity of this enzyme. Most of the isolated compounds were also inactive against fourteen bacterial strains; however mammea A/BA + A/BB, and mammea C/OA + C/OB inhibited the growth of Staphylococcus aureus, S. epidermidis and Bacillus subtilis.

  7. Vasorelaxing activity of two coumarins from Murraya paniculata leaves.

    Science.gov (United States)

    Cuong, Nguyen Manh; Khanh, Pham Ngoc; Duc, Ho Viet; Huong, Tran Thu; Tai, Bui Huu; Binh, Nguyen Quoc; Durante, Miriam; Fusi, Fabio

    2014-01-01

    In the search for novel chemical scaffolds leading to potential antihypertensive agents, the methanol extract of Murraya paniculata leaves was assessed for its effects on isolated rat aorta rings. The vasorelaxing effect of the chloroform fraction of the methanol plant extract was the most potent for its vasorelaxing activity on rat aorta rings contracted by 60 mM K(+) (K60). Two coumarins were isolated from the chloroform fraction: the novel kimcuongin (1) and the known murracarpin (2). Their structures were determined from spectroscopic evidences including (1)H- and (13)C-NMR, correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY), heteronuclear multiple bond correlation (HMBC), heteronuclear single quantum correlation (HSQC), and high resolution mass spectrometry (HR-MS). Kimcuongin and, to a lesser extent, murracarpin, showed vasorelaxing activity with IC50 values of 37.7 µM and 139.3 µM, respectively. The coumarins kimcuongin and murracarpin may thus represent a novel class of vasodilators of natural source.

  8. Metabolic detoxification determines species differences in coumarin-induced hepatotoxicity.

    Science.gov (United States)

    Vassallo, Jeffrey D; Hicks, Sarah M; Daston, George P; Lehman-McKeeman, Lois D

    2004-08-01

    Hepatotoxicity of coumarin is attributed to metabolic activation to an epoxide intermediate, coumarin 3,4-epoxide (CE). However, whereas rats are most susceptible to coumarin-induced hepatotoxicity, formation of CE is greatest in mouse liver microsomes, a species showing little evidence of hepatotoxicity. Therefore, the present work was designed to test the hypothesis that detoxification of CE is a major determinant of coumarin hepatotoxicity. CE can either rearrange spontaneously to o-hydroxyphenylacetaldehyde (o-HPA) or be conjugated with gluatathione (GSH). o-HPA is hepatotoxic and is further detoxified by oxidation to o-hydroxyphenylacetic acid (o-HPAA). In vitro experiments were conducted using mouse liver microsomes to generate a constant amount of CE, and cytosols from F344 rats, B6C3F1 mice, and human liver were used to characterize CE detoxification. All metabolites were quantified by HPLC methods with UV detection. In rats and mice, GSH conjugation occurred non-enzymatically and through glutathione-S-transferases (GSTs), and the kinetics of GSH conjugation were similar in rats and mice. In rat liver cytosol, oxidation of o-HPA to o-HPAA was characterized with a high affinity K(m) of approximately 12 microM, and a V(max) of approximately 1.5 nmol/min/mg protein. In contrast, the K(m) and V(max) for o-HPA oxidation in mouse liver cytosol were approximately 1.7 microM and 5 nmol/min/mg protein, respectively, yielding a total intrinsic clearance through oxidation to o-HPAA that was 20 times higher in mouse than in rats. Human cytosols (two separate pools) detoxified CE through o-HPA oxidation with an apparent K(m) of 0.84 microM and a V(max) of 5.7 nmol/min/mg protein, for a net intrinsic clearance that was more than 50 times higher than the rat. All species also reduced o-HPA to o-hydroxyphenylethanol (o-HPE), but this was only a major reaction in rats. In the presence of a metabolic reaction replete with all necessary cofactors, GSH conjugation accounted

  9. The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems

    Directory of Open Access Journals (Sweden)

    Brian D. Wagner

    2009-01-01

    Full Text Available Coumarins, as a family of molecules, exhibit a wide range of fluorescence emission properties. In many cases, this fluorescence is extremely sensitive to the local environment of the molecule, especially the local polarity and microviscosity. In addition, coumarins show a wide range of size, shape, and hydrophobicity. These properties make them especially useful as fluorescent probes of heterogeneous environments, such as supramolecular host cavities, micelles, polymers and solids. This article will review the use of coumarins to probe such heterogeneous systems using fluorescence spectroscopy.

  10. Risk assessment of coumarin using the bench mark dose (BMD) approach: children in Norway which regularly eat oatmeal porridge with cinnamon may exceed the TDI for coumarin with several folds.

    Science.gov (United States)

    Fotland, T Ø; Paulsen, J E; Sanner, T; Alexander, J; Husøy, T

    2012-03-01

    Coumarin is a naturally occurring flavouring substance in cinnamon and many other plants. It is known that coumarin can cause liver toxicity in several species, and it is considered a non-genotoxic carcinogen in rodents. By using the bench mark dose approach we re-assessed coumarin toxicity and established a new TDI for coumarin of 0.07 mg/kg bw/day. Oral intake of coumarin is related to consumption of cinnamon-containing foods and food supplements. Cinnamon is a widely used spice in Norway, and can be used as topping on oatmeal porridge. Based on analyses of coumarin in Norwegian foods, intake calculations for children and adults were conducted, and a risk assessment of coumarin in the Norwegian population was performed. Intake estimates of coumarin show that small children eating oatmeal porridge several times a week sprinkled with cinnamon could have a coumarin intake of 1.63 mg/kg bw/day and may exceeding the TDI with several folds. Adults drinking cinnamon-based tea and consuming cinnamon supplements also can exceed TDI. The coumarin intake could exceed the TDI by 7- to 20-fold in some intake scenarios. Such large daily exceedances of TDI, even for a limited time period of 1-2 weeks, cause concern of adverse health effects. Copyright © 2011 Elsevier Ltd. All rights reserved.

  11. Quantitative DNA interstrand cross-link formation by coumarin and thymine: structure determination, sequence effect, and fluorescence detection.

    Science.gov (United States)

    Sun, Huabing; Fan, Heli; Peng, Xiaohua

    2014-12-01

    The coumarin analogues have been widely utilized in medicine, biology, biochemistry, and material sciences. Here, we report a detailed study on the reactivity of coumarins toward DNA. A series of coumarin analogues were synthesized and incorporated into oligodeoxynucleotides. A photoinduced [2 + 2] cycloaddition occurs between the coumarin moiety and the thymidine upon 350 nm irradiation forming both syn- and anti-cyclobutane adducts (17 and 18), which are photoreversible by 254/350 nm irradiation in DNA. Quantitative DNA interstrand cross-link (ICL) formation was observed with the coumarin moieties containing a flexible two-carbon or longer chain. DNA cross-linking by coumarins shows a kinetic preference when flanked by an A:T base pair as opposed to a G:C pair. An efficient photoinduced electron transfer between coumarin and dG slows down ICL formation. ICL formation quenches the fluorescence of coumarin, which, for the first time, enables fast, easy, and real-time monitoring of DNA cross-linking and photoreversibility via fluorescence spectroscopy. It can be used to detect the transversion mutation between pyrimidines and purines. Overall, this work provides new insights into the biochemical properties and possible toxicity of coumarins. A quantitative, fluorescence-detectable, and photoswitchable DNA cross-linking reaction of the coumarin moieties can potentially serve as mechanistic probes and tools for bioresearch without disrupting native biological environment.

  12. Synthesis and Characterization of Some New 4-Hydroxy-coumarin Derivatives

    Directory of Open Access Journals (Sweden)

    Yasameen K. Al-Majedy

    2014-08-01

    Full Text Available Some novel coumarins were synthesized starting from 4-hydroxycoumarin and methyl bromoacetate. The structures of the newly obtained compounds were confirmed by elemental analysis, mass, IR and NMR spectra.

  13. Light-Induced Reversible Self-Assembly of Gold Nanoparticles Surface-Immobilized with Coumarin Ligands.

    Science.gov (United States)

    He, Huibin; Feng, Miao; Chen, Qidi; Zhang, Xinqi; Zhan, Hongbing

    2016-01-18

    A novel light-induced reversible self-assembly (LIRSA) system is based on the reversible photodimerization and photocleavage of coumarin groups on the surface of gold nanoparticles (AuNPs) in THF solution. Facilitated by coumarin groups, light irradiation at 365 nm triggers the stable assembly of monodisperse AuNPs; the resulting self-assembly system can be disassembled back to the disassembled state by a relatively short exposure to benign UV light. The reversible self-assembly cycle can be repeated 4 times. A specific concentration range of coumarin ligand and the THF solvent were identified to be the two predominant factors that contribute to the LIRSA of AuNPs. This is the first successful application of reversible photodimerization based on a coumarin derivative in the field of AuNP LIRSA. This LIRSA system may provide unique opportunities for the photoregulated synthesis of many adjustable nanostructures and devices.

  14. Carrier transport and charge transfer properties in coumarin-doped bulk-heterojunction materials

    Energy Technology Data Exchange (ETDEWEB)

    Watanabe, T.; Maeda, T.; Yamashita, K. [Graduate School of Science and Technology, Kyoto Institute of Technology, Kyoto 606-8585 (Japan); Yanagi, H. [Graduate School of Materials Science, Nara Institute of Science and Technology, Nara 630-0192 (Japan)

    2012-12-15

    We have investigated photovoltaic properties of organic solar cells using polymer-fullerene bulk-heterojunction films doped with coumarin dyes. Whereas the coumarin molecules used in this study had similar absorption bands, evident difference was observed in the open-circuit voltage as well as in the short-circuit current. In particular, the doping of coumarin 307 was found to cause a distinct enhancement in the open-circuit voltage. On the other hand, the doping of coumarin 30 gave a serious degradation in the device performance. These results were strongly associated with calculated molecular energies of the doped dyes, especially with the highest occupied molecular orbital energy. (copyright 2012 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim) (orig.)

  15. Synthesis and Characterization of Coumarin-Containing Cyclic Polymer and Its Photoinduced Coupling/Dissociation.

    Science.gov (United States)

    Li, Min; Fan, Wei; Hong, Chunyan; Pan, Caiyuan

    2015-12-01

    Cyclic polystyrene (PS) with a pendant coumarin group is prepared by the combination of atom transfer radical polymerization and "click" chemistry. Fluorescence resonance energy transfer process is observed in the fluorescence measurement of coumarin-containing PS, and cyclic PS exhibits stronger emission than that of its linear precursor. When cyclic PS is irradiated under UV light at λ = 365 nm, 8-shaped PS is achieved due to the dimerization of pendant coumarin group. Subsequently, 8-shaped PS can be divided into single macrocycle under UV irradiation at λ = 254 nm via the photocleavage of coumarin dimer. The photoinduced coupling and dissociation are monitored by UV/vis spectra and gel permeation chromatography (GPC).

  16. L-Proline Catalyzed Solvent-Free Knoevenagel Condensation for the Synthesis of 3-Substituted Coumarins

    Institute of Scientific and Technical Information of China (English)

    KARADE Nandkishor. N.; GAMPAWAR Sumit V.; SHINDE Sandeep. V.; JADHAV Wamanrao. N.

    2007-01-01

    L-Proline was utilized as an efficient organo-catalyst for the environmentally benign synthesis of 3-substituted coumarins by the Knoevenagel condensation of substituted 2-hydroxybenzaldehydes with reactive methylene compounds under solvent free conditions.

  17. Rare Coumarins Induce Apoptosis, G1 Cell Block and Reduce RNA Content in HL60 Cells

    Directory of Open Access Journals (Sweden)

    Widelski Jarosław

    2017-02-01

    Full Text Available The rare coumarins stenocarpin, stenocarpin isobutyrate, oficinalin, oficinalin isobutyrate, 8-methoxypeucedanin and the known xanthotoxin, isoimperatorin, bergapten, peucedanin and 8–methoxyisoimperatorin were isolated from Peucedanum luxurians Tamamsch. (Apiaceae and identified by means of spectral data (1D and 2D NMR. Their immunomodulating activity was evaluated by flow cytometry and their influence on HL60 cells as well as on PHA-stimulated PBLs was tested. All tested coumarins induce apoptosis (maximal in the 48 h culture and decrease cell proliferation in a time- and dose-dependent manner, especially in HL60 cells. They also induce partial G1 block, but only in HL60 cells (at 100 µM concentrations. Dose-dependent reduction of RNA content was also found in G1 cells treated by the coumarins. All of the tested coumarins also possessed immunomodulatory activities. Bergapten and xanthotoxin were found to be the best candidates for further evaluation as anti-cancer drugs.

  18. Synthesis and functionalization of coumarin-containing copolymers for second order optical nonlinearities

    Science.gov (United States)

    Essaïdi, Zacaria; Krupka, Oksana; Iliopoulos, Konstantinos; Champigny, Emilie; Sahraoui, Bouchta; Sallé, Marc; Gindre, Denis

    2013-01-01

    The second-order nonlinear optical properties of photocross-linkable coumarin-based copolymers were investigated using the optical second harmonic generation (SHG) with the Maker fringes technique. High quality and transparent spin-deposited thin films of various methacrylic copolymers containing 4-methylcoumarin pendant chromophores were prepared and the coumarin units were ordered and oriented by the corona poling technique. Nonlinear optical investigations were performed using a picosecond Q-switched Nd:YAG laser working at the fundamental wavelength (λ = 1064 nm) and the second order nonlinear optical susceptibilities of the functionalized polymers were determined. The samples were irradiated using two wavelengths (λ = 254 nm and λ > 300 nm) promoting the reversible photo-induced dimerisation of coumarin moieties within the film. The latter is shown to have a significant impact on the nonlinear optical response of the corresponding material. A large SHG response of photocross-linkable coumarin-based copolymers is obtained.

  19. Assessment of Coumarin Levels in Ground Cinnamon Available in the Czech Retail Market

    Directory of Open Access Journals (Sweden)

    Jana Blahová

    2012-01-01

    Full Text Available The objective of this study was to determine the coumarin content of ground cinnamon purchased from retail markets in the Czech Republic. No sample was labelled with information on the botanical source, but, in some cases, the countries of origin were specified. For comparison, a single cinnamon sample imported directly from a plantation in Sri Lanka that came from Cinnamomum verum was analyzed. Results from 60 ground cinnamon samples comprising twelve brands confirmed a high content of coumarin, with mean levels ranging from 2 650 to 7 017 mg · kg−1. The high coumarin content confirmed that these cinnamon samples obtained from cassia cinnamon were in contrast to the sample from Sri Lanka, which was coumarin-free.

  20. Gas phase ion chemistry of coumarins: ab initio calculations used to ...

    African Journals Online (AJOL)

    Gas phase ion chemistry of coumarins: ab initio calculations used to justify ... and quadrupole mass spectrometer (qMS) coupled to a gas chromatograph is ... Ab Initio calculations, Electron ionization, Positive chemical ionization, Negative ...

  1. [Coumarins from Skimmia arborescens and its anti-inflammatory effect].

    Science.gov (United States)

    He, Lei; Yang, Shunli; Wu, Desong; Cui, Tao; Wei, Di; Ding, Zhongtao

    2012-03-01

    To investigate chemical constituents contained in Skimmia arborescens. The chemical constituents were separated by silica gel column chromatography, pharmadex LH-20, RP-C18, and 1H, 13C-NMR spectroscopic analysis were employed for the structural elucidation. Six coumarin compounds were separated from S. arborescens. Their structures were elucidated as umbelliferone (1), scopoletin (2), scopolin (3), nodakenetin (4), skimmin (5), 6, 7-dimethoxycoumarin (6), and all compounds were separated from the plant for the first time. Using the model of ear swelling caused by xylol of mice, the anti-inflammatory effect of its total extract was evaluated. The result indicated that middle and high dose groups of its total extract could obviously inhibit the ear swelling caused by xylol of mice.

  2. A new coumarin from stem bark of Mesua hexapetala.

    Science.gov (United States)

    Karunakaran, Thiruventhan; Ee, Gwendoline Cheng Lian; Teh, Soek Sin; Daud, Shaari; Mah, Siau Hui; Lim, Chan Kiang; Jong, Vivien Yi Mian; Awang, Khalijah

    2016-07-01

    A new alkylated coumarin derivative, hexapetarin (1) along with three other xanthones, trapezifolixanthone (2), cudraxanthone G (3) and 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanthone (4), and four common triterpenoids, friedelin (5), stigmasterol (6), beta-sitosterol (7) and gamma-sitosterol (8) were isolated from the stem bark of Mesua hexapetala (Clusiaceae), a plant, native to Malaysia. The structures of these compounds were elucidated and determined using spectroscopic techniques such as NMR and MS. Anti-inflammatory activity assay indicated hexapetarin (1) to possess moderate anti-inflammatory activity, while 1,3,7-trihydroxy-2,4-di (3-methyl-2-butenyl)xanthone (4) gave very good activity.

  3. Superexciplex of Coumarin Molecules using Tunable Ti-Sapphire Laser

    Science.gov (United States)

    Al-Ghamdi, Attieh Ali; Al-Dwayyan, Abdullah S.; Masilamani, Vadivel; Al-Saud, Turki Saud M.; Al-Salhi, Mohammed Saleh

    2003-10-01

    Certain highly polar dye molecules exhibit an additional optical gain band under pulsed laser excitation, while there is no such band under steady-state continuous wave (CW) lamp excitation. This new band is not due to an excimer, an exciplex or a two-photon fluorescence band but stems from the formation of a new molecular complex in which two excited molecules remain associated with a solvent molecule acting as a bridge. In this paper, the characteristics of superexciplexes of four related coumarin molecules are presented. All molecules were excited using a tunable Ti-sapphire laser pulse 10 ns in width. The distinct difference between the amplified spontaneous emission (ASE) spectra obtained with tunable laser and tunable lamp excitation demonstrated that twisted intramolecular charge transfer (TICT) conformations might also assist in the formation of these superexciplexes.

  4. Crystal structures of three 6-substituted coumarin-3-carboxamide derivatives.

    Science.gov (United States)

    Gomes, Lígia R; Low, John Nicolson; Fonseca, André; Matos, Maria João; Borges, Fernanda

    2016-07-01

    Three coumarin derivatives, viz. 6-methyl-N-(3-methyl-phen-yl)-2-oxo-2H-chromene-3-carboxamide, C18H15NO3 (1), N-(3-meth-oxy-phen-yl)-6-methyl-2-oxo-2H-chromene-3-carboxamide, C18H15NO4 (2), and 6-meth-oxy-N-(3-meth-oxy-phen-yl)-2-oxo-2H-chromene-3-carboxamide, C18H15NO5 (3), were synthesized and structurally characterized. The mol-ecules display intra-molecular N-H⋯O and weak C-H⋯O hydrogen bonds, which probably contribute to the approximate planarity of the mol-ecules. The supra-molecular structures feature C-H⋯O hydrogen bonds and π-π inter-actions, as confirmed by Hirshfeld surface analyses.

  5. Costs and effectiveness of using coumarins before, during and after coronary angioplasty.

    Science.gov (United States)

    ten Berg, Jurrien M; Kelder, Johannas C; Plokker, Thys H W; van Hout, Ben A

    2002-01-01

    In the Balloon Angioplasty and Anticoagulation Study (BAAS), coumarins added to routine aspirin therapy before coronary angioplasty reduced cardiac events at the cost of a slightly higher risk of bleeding complications. To determine the cost effectiveness of coumarin treatment, based on the occurrence of both cardiac and bleeding events. Effectiveness was measured, applying two definitions, in terms of the number of events occurring at one year. In the first definition, the occurrence of death, myocardial infarction (MI), or stroke was assessed. The second definition also included revascularisations and major bleeding episodes as an event. Costs were limited to direct medical costs. Cost effectiveness was addressed by probability ellipses representing the point estimates and uncertainties surrounding both costs and effectiveness. At 1 year, death, MI or stroke occurred 1.1% less often when treating with aspirin plus coumarins rather than aspirin therapy alone. When revascularisations and major bleeding events were also included, the difference was 5.0%. Overall, the additional costs in relation to coumarin treatment were compensated by a reduction in repeat interventions. When including all costs, the savings associated with coumarin treatment were estimated at Euros 235 per patient after 1 year. The probability that coumarins are cost saving was estimated at 0.85. The probability that coumarins combine additional effectiveness with cost savings was estimated at 0.70 when survival free of MI or stroke as an effectiveness measure was considered, and at 0.83 when survival free of MI, stroke, revascularisation or major bleeding was considered. Coumarin therapy added to routine aspirin therapy before coronary angioplasty, and continued during follow-up, may not only be considered more effective but also cost saving relative to aspirin therapy alone.

  6. Synthesis and Antimicrobial Activity of New 4-Heteroarylamino Coumarin Derivatives Containing Nitrogen and Sulfur as Heteroatoms

    Directory of Open Access Journals (Sweden)

    Biljana R. Dekić

    2010-03-01

    Full Text Available Synthesis, spectral analysis and bioactivity of new coumarin derivatives are described in this paper. Eight new coumarin derivatives were synthesized in moderate to good yields by condensation of 4-chloro-3-nitrocoumarin and the corresponding heteroarylamine. The synthesized compounds were tested for their in vitro antimicrobial activity, in a standard disk diffusion assay, against thirteen strains of bacteria and three fungal strains. They have shown a wide range of activity - from one completely inactive compound to medium active ones.

  7. Electron Donor-Acceptor Quenching and Photoinduced Electron Transfer for Coumarin Dyes.

    Science.gov (United States)

    1983-10-31

    Mechanism of cousarin photodegradation . Ithe behavior of eoiuma dyes is water ad In aqueous detergent media,. and the effsects of medism aud, additives on...D-i36 345 ELECTRON DONOR-ACCEPTOR UENCHING AND PHOTOINDUCED i/i Ai ELECTRON TRANSFER FOR COUMARIN DYES (U) BOSTON UNIY MR DEPT OF CHEMISTRY G JONES...TYPE OF REPORT & PEIOD COVERED Electron Donor-acceptor Quenching and Photo- Technical, 1/1/82-10/31/82 induced Electron Transfer for Coumarin Dyes S

  8. Functionalized 4-Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations

    Directory of Open Access Journals (Sweden)

    Olga Igglessi-Markopoulou

    2011-01-01

    Full Text Available A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-cyclization process under mild reaction conditions. The structure of 3-methoxycarbonyl-4-hydroxy coumarin has been established by X-ray diffraction analysis and its geometry was compared with optimized parameters by means of DFT calculations.

  9. Coumarin-Containing Polymers for High Density Non-Linear Optical Data Storage

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    Denis Gindre

    2016-01-01

    Full Text Available Optical data storage was performed with various thin polymer films containing coumarin-based derivatives and by using femtosecond laser pulses as well as two-photon absorption processes. Exploring the photodimerization attribute of coumarin derivatives and using appropriate irradiation wavelengths, recording/erasing processes could be carried out in the same area. Second harmonic generation microscopy was used to read the stored information.

  10. Photoinduced interaction of CdSe quantum dot with coumarins

    Energy Technology Data Exchange (ETDEWEB)

    El-Kemary, Maged, E-mail: elkemary@sci.kfs.edu.eg [Nanotechnology Center, Faculty of Science, Kafrelsheikh University, 33516 Kafrelsheikh (Egypt); Gaber, Mohamed; El-Sayed, Y.S. [Chemistry Department, Faculty of Science, University of Tanta, Tanta (Egypt); Gheat, Youssef [Nanotechnology Center, Faculty of Science, Kafrelsheikh University, 33516 Kafrelsheikh (Egypt); Chemistry Department, Faculty of Science, University of Tanta, Tanta (Egypt)

    2015-03-15

    Cadmium selenide (CdSe) quantum dots (QDs) were synthesized with a cubic shape having a diameter of ∼5.24 nm. The prepared CdSe QDs were characterized by using UV–visible, Fourier transform infrared (FTIR), powder X-ray diffraction (XRD) and transmission electron microscope (TEM) measurements. The UV–visible absorption spectra indicate that the optical band gap of CdSe QDs is ∼622 nm and the peak shift can mainly be due to the quantum size effects. The fluorescence decay kinetics for the synthesized QDs was followed by time-resolved fluorescence spectroscopy, and the spectra were analyzed in regard to a bi-exponential model to identify two lifetime values, that is, shorter-lifetime 1.37 ns (55%) and longer-lifetime 6.58 ns (45%). The interaction of coumarin 152 (C152) and coumarin 153 (C153) with QDs surface brings about further considerable changes in the absorption and fluorescence patterns. The calculated binding constant from fluorescence quenching method matches well with that determined from the absorption spectral changes. The static quenching mechanism was confirmed by large magnitude of K{sub SV} and unaltered fluorescence lifetime. - Highlights: • CdSe QDs were synthesized with a cubic shape having a diameter of ∼5.24 nm. • The UV–visible absorption spectra indicate that the optical band gap of CdSe QDs is ∼622 nm. • Picosecond fluorescence measurements of the QDs suggest bi-exponential function. • The calculated binding constant from fluorescence quenching method matches well with that determined from the absorption spectral changes. • The static quenching mechanism was confirmed by large magnitude of K{sub SV} and unaltered fluorescence lifetime.

  11. A novel method for the synthesis of coumarin laser dyes derived from 3-(1H-benzoimidazol-2-yl coumarin-2-one under microwave irradiation

    Directory of Open Access Journals (Sweden)

    Ghasem Bakhtiari

    2014-12-01

    Full Text Available We want to achieve the synthesis of 3-(1H-benzoimidazol-2-yl-7-(diethylamino coumarin-2-one (1, 3-(1H-benzoimidazol-2-yl-7-(dimethylamino coumarin-2-one (2, 3-(1H-benzoimidazol-2-yl coumarin-2-one (3 that are important dyes in industries (Soko owska et al., 2001. Methods for the synthesis of some of these compounds have been the title in some pervious patents, but enough information about separation and purification of them was not clearly indicated. We carried out several methods for the synthesis of the mentioned compound and purification with different yields. Now, we can synthesise these dyes under microwave irradiation in solid phase and solvent free methods with 80% yield, which is a high and remarkable percentage.

  12. Femtosecond study of laser coloring soluble in water: the coumarins; Etude femtoseconde de colorants laser solubles dans l`eau: les coumarines

    Energy Technology Data Exchange (ETDEWEB)

    Cassara, L.

    1996-11-29

    This thesis concerns the study of four hydro soluble coumarins A.T.C., D.M.A.T.C., D.A.T.C. et C.H.O.S., analogues of classical coumarins C120, C311, C1 and C102. These molecules are made hydro soluble because of the substitution in position 4- of the methyl group by a polyether group. The mechanisms of deactivation are studied because of fluorescence methods (resolved in time and transient absorption) which allow to study the reactional dynamics of coumarins after luminous excitement. SEveral time scales, from a few femto seconds to the nanosecond have been approachable and have allowed investigations on different processes: relaxation S{sub n} {yields} S{sub 1}, solvation dynamics, orientational diffusion of the solution and deactivation process S{sub 1} {yields} S{sub 0} of radiative and non radiative relaxation in different solvents. (N.C.)

  13. Phytotoxic Potential and Biological Activity of Three Synthetic Coumarin Derivatives as New Natural-Like Herbicides

    Directory of Open Access Journals (Sweden)

    Fabrizio Araniti

    2015-09-01

    Full Text Available Coumarin is a natural compound well known for its phytotoxic potential. In the search for new herbicidal compounds to manage weeds, three synthetic derivatives bearing the coumarin scaffold (1–3, synthesized by a carbonylative organometallic approach, were in vitro assayed on germination and root growth of two noxious weeds, Amaranthus retroflexus and Echinochloa crus-galli. Moreover, the synthetic coumarins 1–3 were also in vitro assayed on seedlings growth of the model species Arabidopsis thaliana to identify the possible physiological targets. All molecules strongly affected seed germination and root growth of both weeds. Interestingly, the effects of synthetic coumarins on weed germination were higher than template natural coumarin, pointing out ED50 values ranging from 50–115 µM. Moreover, all synthetic coumarins showed a strong phytotoxic potential on both Arabidopsis shoot and root growth, causing a strong reduction in shoot fresh weight (ED50 values ≤ 60 µM, accompanied by leaf development and a decrease in pigment content. Furthermore, they caused a strong alteration in root growth (ED50 values ≤ 170 µM and morphology with evident alterations in root tip anatomy. Taken together, our results highlight the promising potential herbicidal activity of these compounds.

  14. [Determination of five coumarins in toys by high performance liquid chromatography-tandem mass spectrometry].

    Science.gov (United States)

    Yang, Rongjing; Wei, Biwen; Gao, Huan; Yu, Wenjia

    2012-02-01

    A rapid analytical method for the determination of five coumarins (coumarin, 7-methoxycoumarin, dihydrocoumarin, 7-methyl coumarin and 7-ethoxy-4-methyl coumarin) in toys by high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) has been developed. After ultrasonic extraction in tetrahydrofuran, the samples were analyzed by HPLC-MS/MS in multi-reaction monitoring (MRM) mode. Acetonitrile and 0.1% acetic acid were used as the mobile phases with gradient elution. The linear ranges of calibration curves were 10 - 1 000 microg/L, and the limits of quantification (LOQ) (S/N > 10) were 2.0 microg/L for all the analytes, except that the LOQ for dihydrocoumarin was 5.0 microg/L. The recoveries of the five coumarins spiked in three types of samples were in the ranges of 93.2% - 105.8%, 97.3% - 103.2% and 96.8% - 102.9%, with the relative standard deviations in the ranges of 4.35% - 8.27%, 3.65% - 6.73% and 4.03% - 6.45%, respectively. The method was applied in the determination of 12 toy samples. The five analytes were found in 9 samples, and in some cases, the presence of quite high concentrations of these coumarins in the toys should be a matter of concern.

  15. Early and late effects of coumarin therapy started before percutaneous coronary intervention

    Science.gov (United States)

    ten Berg, J.M.; Kelder, J.C.; Suttorp, M.J.; Mast, E.G.; Bal, E.T.; Ernst, J.M.P.G.; Plokker, H.W.M.

    2002-01-01

    Background Coronary angioplasty frequently creates a thrombogenic surface with subsequent mural thrombosis that may lead to acute complications and possibly stimulates the development of restenosis. Whether coumarins can prevent these complications is unclear. Methods In the Balloon Angioplasty and Anticoagulation Study (BAAS), the effect of coumarins started before the procedure on early and late outcome was studied. Patients were randomised to aspirin only or to aspirin plus coumarins. Half of the patients were randomised to undergo six-month angiographic follow-up. Study medication was started one week before coronary angioplasty and the target international normalised ratio (INR) was 2.1-4.8 during angioplasty and six-month follow-up. 'Optimal' anticoagulation was defined as an INR in the target range for at least 70% of the follow-up time. In addition, cost-effectiveness of coumarin treatment was measured. Results At one year death, myocardial infarction, target-lesion revascularisation and stroke were observed in 14.3% of the 530 patients randomised to aspirin plus coumarin versus in 20.3% of the 528 patients randomised to aspirin alone (relative risk 0.71; 95% CI 0.54-0.93). The incidence of major bleedings and false aneurysms during hospitalisation was 3.2% and 1.0%, respectively, (relative risk 3.39; 95% CI 1.26-9.11). Optimal anticoagulation was an independent predictor of late thrombotic events (relative risk, 0.33; 95% CI, 0.19-0.57). Quantitative coronary analysis was performed of 301 lesions in the ASA group and of 297 lesions in the coumarin group. At six months, the minimal luminal diameter was similar in the ASA and coumarin group. However, optimal anticoagulation was an independent predictor of angiographic outcome at six months. Optimal anticoagulation led to a 0.21 mm (95% CI: 0.05-0.37) larger MLD as compared with suboptimal anticoagulation whereas aspirin use led to a 0.12 mm (95% CI -0.28-0.04) smaller MLD. When including all costs, the

  16. Effects of Different Coumarin- 3-Carboxamide Agents on Scopolamine Induced Learning and Memory Deficit in Mice

    Directory of Open Access Journals (Sweden)

    Samaneh Ghanei Nasab

    2017-06-01

    Full Text Available Introduction: It has been shown that three new synthetic coumarins-3-carboxamides including 3-fluorobenzilchloride, 4-fluorobenzilchloride and 2-hidroxy-3 metoxybenzaldehyde, have acetylcholinesterase inhibitory activity. This study was performed to estimate ameliorating effect of these new coumarin-3-carboxamides on memory impairments induced by scopolamine (1 mg/kg, induced prolongation in mice. Methods: 30 male mice were divided into five groups, 6 mice in each group. Three experiment groups received coumarins-3- carboxamides (10 mg/kg body weight 30 min before scopalamin injection and two other groups considered as normal (saline-treated groups and finally one negative control (scopalamin only group. The experiment groups were treated with coumarins of 3-fluorobenzilchloride, 4-fluorobenzilchloride and 2-hidroxy-3 metoxybenzaldehyde. The passive avoidance test was performed in an automatic conventional shuttle box set-up. The stepped down latency and number of errors was recorded. Results: With reference to saline-treated group, scopolamine-treated mice demonstrated impairment of learning and memory as a reduction of latency and an increased numbers of errors in step-down testp < 0.01. Treated mice receiving these coumarins at the dose of 10 mg/kg showed an increase in the number of avoidances on the memory tests compared to the scopolamine group (p < 0.01. Conclusion: The study has demonstrated some therapeutic effects of coumarin-3-carboxamides on learning and memory deficit induced by scopolamine. Further investigation is needed to explore whether coumarin-3-carboxamides could be beneficial for memory impairment in Alzheimer’s disease in which cholinergic deficit is one of the hallmarks. 

  17. The Relation between Hepatotoxicity and the Total Coumarin Intake from Traditional Japanese Medicines Containing Cinnamon Bark.

    Science.gov (United States)

    Iwata, Naohiro; Kainuma, Mosaburo; Kobayashi, Daisuke; Kubota, Toshio; Sugawara, Naoko; Uchida, Aiko; Ozono, Sahoko; Yamamuro, Yuki; Furusyo, Norihiro; Ueda, Koso; Tahara, Eiichi; Shimazoe, Takao

    2016-01-01

    Cinnamon bark is commonly used in traditional Japanese herbal medicines (Kampo medicines). The coumarin contained in cinnamon is known to be hepatotoxic, and a tolerable daily intake (TDI) of 0.1 mg/kg/day, has been quantified and used in Europe to insure safety. Risk assessments for hepatotoxicity by the cinnamon contained in foods have been reported. However, no such assessment of cinnamon bark has been reported and the coumarin content of Kampo medicines derived from cinnamon bark is not yet known. To assess the risk for hepatotoxicity by Kampo medicines, we evaluated the daily coumarin intake of patients who were prescribed Kampo medicines and investigated the relation between hepatotoxicity and the coumarin intake. The clinical data of 129 outpatients (18 male and 111 female, median age 58 years) who had been prescribed keishibukuryogankayokuinin (TJ-125) between April 2008 and March 2013 was retrospectively investigated. Concurrent Kampo medicines and liver function were also surveyed. In addition to TJ-125, the patients took some of the other 32 Kampo preparations and 22 decoctions that include cinnamon bark. The coumarin content of these Kampo medicines was determined by high performance liquid chromatography (HPLC). TJ-125 had the highest daily content of coumarin (5.63 mg/day), calculated from the daily cinnamon bark dosage reported in the information leaflet inserted in each package of Kampo medicine. The coumarin content in 1g cinnamon bark decoction was 3.0 mg. The daily coumarin intake of the patients was 0.113 (0.049-0.541) mg/kg/day, with 98 patients (76.0%) exceeding the TDI. Twenty-three patients had an abnormal change in liver function test value, but no significant difference was found in the incidence of abnormal change between the group consuming less than the TDI value (6/31, 19.4%) and the group consuming equal to or greater than the TDI value (17/98, 17.3%). In addition, no abnormal change related to cinnamon bark was found for individual

  18. The Relation between Hepatotoxicity and the Total Coumarin Intake from Traditional Japanese Medicines Containing Cinnamon Bark

    Science.gov (United States)

    Iwata, Naohiro; Kainuma, Mosaburo; Kobayashi, Daisuke; Kubota, Toshio; Sugawara, Naoko; Uchida, Aiko; Ozono, Sahoko; Yamamuro, Yuki; Furusyo, Norihiro; Ueda, Koso; Tahara, Eiichi; Shimazoe, Takao

    2016-01-01

    Cinnamon bark is commonly used in traditional Japanese herbal medicines (Kampo medicines). The coumarin contained in cinnamon is known to be hepatotoxic, and a tolerable daily intake (TDI) of 0.1 mg/kg/day, has been quantified and used in Europe to insure safety. Risk assessments for hepatotoxicity by the cinnamon contained in foods have been reported. However, no such assessment of cinnamon bark has been reported and the coumarin content of Kampo medicines derived from cinnamon bark is not yet known. To assess the risk for hepatotoxicity by Kampo medicines, we evaluated the daily coumarin intake of patients who were prescribed Kampo medicines and investigated the relation between hepatotoxicity and the coumarin intake. The clinical data of 129 outpatients (18 male and 111 female, median age 58 years) who had been prescribed keishibukuryogankayokuinin (TJ-125) between April 2008 and March 2013 was retrospectively investigated. Concurrent Kampo medicines and liver function were also surveyed. In addition to TJ-125, the patients took some of the other 32 Kampo preparations and 22 decoctions that include cinnamon bark. The coumarin content of these Kampo medicines was determined by high performance liquid chromatography (HPLC). TJ-125 had the highest daily content of coumarin (5.63 mg/day), calculated from the daily cinnamon bark dosage reported in the information leaflet inserted in each package of Kampo medicine. The coumarin content in 1g cinnamon bark decoction was 3.0 mg. The daily coumarin intake of the patients was 0.113 (0.049–0.541) mg/kg/day, with 98 patients (76.0%) exceeding the TDI. Twenty-three patients had an abnormal change in liver function test value, but no significant difference was found in the incidence of abnormal change between the group consuming less than the TDI value (6/31, 19.4%) and the group consuming equal to or greater than the TDI value (17/98, 17.3%). In addition, no abnormal change related to cinnamon bark was found for individual

  19. A prodrug approach to the use of coumarins as potential therapeutics for superficial mycoses.

    Directory of Open Access Journals (Sweden)

    Derry K Mercer

    Full Text Available Superficial mycoses are fungal infections of the outer layers of the skin, hair and nails that affect 20-25% of the world's population, with increasing incidence. Treatment of superficial mycoses, predominantly caused by dermatophytes, is by topical and/or oral regimens. New therapeutic options with improved efficacy and/or safety profiles are desirable. There is renewed interest in natural product-based antimicrobials as alternatives to conventional treatments, including the treatment of superficial mycoses. We investigated the potential of coumarins as dermatophyte-specific antifungal agents and describe for the first time their potential utility as topical antifungals for superficial mycoses using a prodrug approach. Here we demonstrate that an inactive coumarin glycone, esculin, is hydrolysed to the antifungal coumarin aglycone, esculetin by dermatophytes. Esculin is hydrolysed to esculetin β-glucosidases. We demonstrate that β-glucosidases are produced by dermatophytes as well as members of the dermal microbiota, and that this activity is sufficient to hydrolyse esculin to esculetin with concomitant antifungal activity. A β-glucosidase inhibitor (conduritol B epoxide, inhibited antifungal activity by preventing esculin hydrolysis. Esculin demonstrates good aqueous solubility (<6 g/l and could be readily formulated and delivered topically as an inactive prodrug in a water-based gel or cream. This work demonstrates proof-of-principle for a therapeutic application of glycosylated coumarins as inactive prodrugs that could be converted to an active antifungal in situ. It is anticipated that this approach will be applicable to other coumarin glycones.

  20. Immobilising effect of Ruta graveolens L. on human spermatozoa: coumarin compounds are involved.

    Science.gov (United States)

    Naghibi Harat, Z; Lakpour, N; Sadeghipoor, H R; Kamalinejad, M; Eshraghian, M R; Naghibi, B; Akhondi, M M; Binaafar, S; Sadeghi, M R

    2015-12-01

    This study was designed to find out Ruta graveolens L. functional components, which have immobilisation effect on human spermatozoa for contraceptive use. A five-step fractionation method was used to derive different components from rue aqueous extract by using hexane, chloroform, ethanol, acetone and ultrapure water. Gas chromatography-mass spectrophotometery (GC-MS) of all fractions and the aqueous extract were performed to determine the chemical components. The immobilisation assay and membrane integrity test were also performed with four different coumarins, which were found in GC-MS in a concentration of 10 μm. Hexane, chloroform, acetone and ethanol fractions could significantly decrease motility of sperms within the first and the second hours. Hexane fraction had also significant immediate effect. The aqueous fraction had no effect on sperm motility. Meanwhile, GC-MS revealed that aqueous extract and effective fractions had similar coumarin compounds. We performed the immobilisation assay on four different coumarins, which were found in GC-MS in a concentration of 10 μm. Reduction of sperm motility was only significant for xanthotoxin. In the sperm viability and membrane integrity tests, hexane and ethanolic fractions could impair sperm vitality significantly, in contrast to coumarins. These results indicated that a part of immobilising effect of rue could be due to its coumarins. The possible mechanism could be blocking of spermatozoa potassium channels.

  1. Properties of the Triplet State of Coumarin Substituted Compounds

    Science.gov (United States)

    Bryantseva, N. G.; Gadirov, R. M.; Nikonov, S. Yu.; Sokolova, I. V.

    2015-03-01

    The absorption spectra of the triplet excited state of coumarin sensitizers are investigated both theoretically and experimentally. The most intense triplet-triplet (TT) absorption bands are determined. The experimental spectra of the T-T absorption are compared with the theoretical T-T transitions. The phosphorescence spectra of five compounds are measured at a temperature of 77 K. The quantum phosphorescence yield is determined by the method of comparison with an etalon (8-methoxypsoralen). The phosphorescence lifetime is determined for the examined molecules at a temperature of 77 K. For 3,4-phenyl-4',5'-cyclohexylpsoralen, 4'-methyl-3,4-cycloheptylpsoralen, and 4'5'-dimethyl-3,4-cyclohexylpsoralen compounds, this time is equal to 1.1, 1.25, and 2.5 s, respectively. The main energy deactivation channel for all examined compounds is the phosphorescence. The positions of the lower excited triplet states, calculated by the quantum-chemical method of intermediate neglect of differential overlap with spectroscopic parameterization (INDO/S), are confirmed by the available experimental data.

  2. Coumarin pretreatment alleviates salinity stress in wheat seedlings.

    Science.gov (United States)

    Saleh, Ahmed Mahmoud; Madany, M M Y

    2015-03-01

    The potentiality of COU to improve plant tolerance to salinity was investigated. Wheat grains were primed with COU (50 ppm) and then grown under different levels of NaCl (50, 100, 150 mM) for two weeks. COU pretreatment improved the growth of wheat seedling under salinity, relative to COU-untreated seedlings, due to the accumulation of osmolytes such as soluble sugars and proline. Moreover, COU treatment significantly improved K(+)/Na(+) ratio in the shoots of both salt stressed and un-stressed seedlings. However, in the roots, this ratio increased only under non-salinity. In consistent with phenylalanine ammonia lyase (PAL), phenolics and flavonoids were accumulated in COU-pretreated seedlings under the higher doses of salinity, relative to COU-untreated seedlings. COU primed seedlings showed higher content of the coumarin derivative, scopoletin, and salicylic, chlorogenic, syringic, vanillic, gallic and ferulic acids, under both salinity and non-salinity conditions. Salinity stress significantly improved the activity of peroxidase (POD) in COU-pretreated seedlings. However, the effect of COU on the total antioxidant capacity (TAC) was only obtained at the highest dose of NaCl (150 mM). The present results suggest that COU pretreatment could alleviate the adverse effect of salinity on the growth of wheat seedlings through enhancing, at least partly, the osmoregulation process and antioxidant defense system.

  3. Artificial evolution of coumarin dyes for dye sensitized solar cells.

    Science.gov (United States)

    Venkatraman, Vishwesh; Abburu, Sailesh; Alsberg, Bjørn Kåre

    2015-11-07

    The design and discovery of novel molecular structures with optimal properties has been an ongoing effort for materials scientists. This field has in general been dominated by experiment driven trial-and-error approaches that are often expensive and time-consuming. Here, we investigate if a de novo computational design methodology can be applied to the design of coumarin-based dye sensitizers with improved properties for use in Grätzel solar cells. To address the issue of synthetic accessibility of the designed compounds, a fragment-based assembly is employed, wherein the combination of chemical motifs (derived from the existing databases of structures) is carried out with respect to user-adaptable set of rules. Rather than using computationally intensive density functional theory (DFT)/ab initio methods to screen candidate dyes, we employ quantitative structure-property relationship (QSPR) models (calibrated from empirical data) for rapid estimation of the property of interest, which in this case is the product of short circuit current (Jsc) and open circuit voltage (Voc). Since QSPR models have limited validity, pre-determined applicability domain criteria are used to prevent unacceptable extrapolation. DFT analysis of the top-ranked structures provides supporting evidence of their potential for dye sensitized solar cell applications.

  4. BODIPY-Coumarin Conjugate as an Endoplasmic Reticulum Membrane Fluidity Sensor and Its Application to ER Stress Models.

    Science.gov (United States)

    Lee, Hoyeon; Yang, Zhigang; Wi, Youngjin; Kim, Tae Woo; Verwilst, Peter; Lee, Yun Hak; Han, Ga-In; Kang, Chulhun; Kim, Jong Seung

    2015-12-16

    An endoplasmic reticulum (ER) membrane-selective chemosensor composed of BODIPY and coumarin moieties and a long alkyl chain (n-C18) was synthesized. The emission ratio of BODIPY to coumarin depends on the solution viscosity. The probe is localized to the ER membrane and was applied to reveal the reduced ER membrane fluidity under ER stress conditions.

  5. Cassia Cinnamon as a source of Coumarin in cinnamon-flavored food and food supplements in the United States

    Science.gov (United States)

    Cinnamon is one of the most popular flavoring agents in the United States. Some cinnamon varieties and cinnamon flavored food sold in US could be potential sources of coumarin. Coumarin is banned from food in the United States due to its potential adverse side effects. An ultra-performance liquid ch...

  6. Transport of the Coumarin Metabolite 7-Hydroxycoumarin Glucuronide Is Mediated via Multidrug Resistance-Associated Proteins 3 and 4

    NARCIS (Netherlands)

    Wittgen, Hanneke G. M.; van den Heuvel, Jeroen J. M. W.; van den Broek, Petra H. H.; Siissalo, Sanna; Groothuis, Geny M. M.; de Graaf, Inge A. M.; Koenderink, Jan B.; Russel, Frans G. M.

    2012-01-01

    Coumarin (1,2-benzopyrone) is a natural compound that has been used as a fragrance in the food and perfume industry and could have therapeutic usefulness in the treatment of lymphedema and different types of cancer. Several previous pharmacokinetic studies of coumarin have been performed in humans,

  7. Transport of the coumarin metabolite 7-hydroxycoumarin glucuronide is mediated via multidrug resistance-associated proteins 3 and 4.

    NARCIS (Netherlands)

    Wittgen, H.G.M.; Heuvel, J.J.M.W. van den; Broek, P.H.H. van den; Siissalo, S.; Groothuis, G.M.; Graaf, I.A. de; Koenderink, J.B.; Russel, F.G.M.

    2012-01-01

    Coumarin (1,2-benzopyrone) is a natural compound that has been used as a fragrance in the food and perfume industry and could have therapeutic usefulness in the treatment of lymphedema and different types of cancer. Several previous pharmacokinetic studies of coumarin have been performed in humans,

  8. Transport of the Coumarin Metabolite 7-Hydroxycoumarin Glucuronide Is Mediated via Multidrug Resistance-Associated Proteins 3 and 4

    NARCIS (Netherlands)

    Wittgen, Hanneke G. M.; van den Heuvel, Jeroen J. M. W.; van den Broek, Petra H. H.; Siissalo, Sanna; Groothuis, Geny M. M.; de Graaf, Inge A. M.; Koenderink, Jan B.; Russel, Frans G. M.

    Coumarin (1,2-benzopyrone) is a natural compound that has been used as a fragrance in the food and perfume industry and could have therapeutic usefulness in the treatment of lymphedema and different types of cancer. Several previous pharmacokinetic studies of coumarin have been performed in humans,

  9. Transport of the coumarin metabolite 7-hydroxycoumarin glucuronide is mediated via multidrug resistance-associated proteins 3 and 4.

    NARCIS (Netherlands)

    Wittgen, H.G.M.; Heuvel, J.J.M.W. van den; Broek, P.H.H. van den; Siissalo, S.; Groothuis, G.M.; Graaf, I.A. de; Koenderink, J.B.; Russel, F.G.M.

    2012-01-01

    Coumarin (1,2-benzopyrone) is a natural compound that has been used as a fragrance in the food and perfume industry and could have therapeutic usefulness in the treatment of lymphedema and different types of cancer. Several previous pharmacokinetic studies of coumarin have been performed in humans,

  10. Identification of coumarin as the sensitizer in a patient sensitive to her own perfume but negative to the fragrance mix

    DEFF Research Database (Denmark)

    Mutterer, V; Giménez Arnau, E; Lepoittevin, J P;

    1999-01-01

    obtained was afterwards tested on the patient using a ROAT and/or a patch test. Only 1 fraction gave a positive ROAT result. This fraction was analyzed and found to contain coumarin and ethyl vanillin. Coumarin, one of the most widely used fragrance compounds that is not present in the fragrance mix...

  11. Synthesis and biological evaluation of novel formyl-pyrazoles bearing coumarin moiety as potent antimicrobial and antioxidant agents.

    Science.gov (United States)

    Nagamallu, Renuka; Kariyappa, Ajay Kumar

    2013-12-01

    A series of coumarin appended formyl-pyrazoles 14-18 were synthesized by a simple and accessible approach. The reaction of 8-acetyl-4-methyl-7-hydroxy coumarin 3 and phenyl hydrazine hydrochlorides 4-8 produces the intermediate compounds 8-acetyl-4-methyl-7-hydroxy coumarin hydrazones 9-13. The reaction of compounds 9-13 and DMF in the presence of POCl3 yielded formyl-pyrazoles bearing coumarin moiety 14-18 in good yield. The synthesized new compounds 14-18 and the intermediates 8-acetyl-4-methyl-7-hydroxy coumarin hydrazones 9-13 prepared were screened in vitro for their antibacterial, antifungal antioxidant activities. The compounds 12 and 17 having chloro substitution exhibited promising antifungal and antibacterial activity against the different organisms tested. The compound 17 showed remarkable DPPH radical scavenging ability. Copyright © 2013 Elsevier Ltd. All rights reserved.

  12. Synthesis and Structure-Activity Relationships of Imidazole-Coumarin Conjugates against Hepatitis C Virus

    Directory of Open Access Journals (Sweden)

    Shwu-Chen Tsay

    2016-02-01

    Full Text Available A series of new conjugated compounds with a –SCH2– linkage were synthesized by chemical methods from imidazole and coumarin derivatives. The experimental results indicate that of the twenty newly synthesized imidazole–coumarin conjugates, three of them exhibited appealing EC50 values (5.1–8.4 μM and selective indices >20 against hepatitis C virus. Their potency and selectivity were increased substantially by modification of their structure with two factors: imidazole nucleus with a hydrogen atom at the N(1 position and coumarin nucleus with a substituent, such as Cl, F, Br, Me, and OMe. These guidelines provide valuable information for further development of conjugated compounds as anti-viral agents.

  13. Synthetic studies of coumarin derivatives from o-hydroxybenzophenones with phenylacetic acid and acetic anhydride

    Energy Technology Data Exchange (ETDEWEB)

    Kang, Soon Hee; Yang, Sung Yun [Ewha Womans Univ., Seoul (Korea, Republic of)

    1999-02-01

    The 8 coumarin derivatives have been synthesized from 8 starting materials(2-hydroxy-benzophenone, 2,2'-dihydroxybenzophenone, 2,4-dihydroxybenzophenone, 2-hydroxy-5-methylbenzophenone, 5-chloro-2-hydroxy-4-methylbenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-4'-dimethoxybenzophenone) with phenylacetic acid and Ac{sub 2}O/TEA in acetone at reflux temperature. The ratio of o-hydroxybenzophenone, phenylacetic acid, Ac{sub 2}O and TEA is 1:1:8:8 in acetone. Our results showed higher products yields of coumarin derivatives than Shama and Ray's method in previous papers. A new intermediate form was proposed to our mechanism of coumarin synthetic method.

  14. Studies on the antiplatelet and antithrombotic profile of anti-inflammatory coumarin derivatives.

    Science.gov (United States)

    Kontogiorgis, Christos; Nicolotti, Orazio; Mangiatordi, Giuseppe Felice; Tognolini, Massimiliano; Karalaki, Foteini; Giorgio, Carmine; Patsilinakos, Alexandros; Carotti, Angelo; Hadjipavlou-Litina, Dimitra; Barocelli, Elisabetta

    2015-12-01

    The interest towards coumarin-based structures stems from their polypharmacological profile. Herein, we present a series of Mannich bases and 7-azomethine-linked coumarin derivatives exhibiting antiplatelet and antithrombotic activities, in addition to the already known anti-inflammatory and antioxidant activities. Among others, compounds 15 and 16 were found to be the most potent and selective inhibitors of platelet aggregation whereas compound 3 also proved to be the most potent in the clot retraction assay. Structure-activity relationship studies were conducted to elucidate the molecular determinants responsible for the herein observed activities. The chance of inhibiting cyclooxygenase-1 was also investigated for evaluating the platelet aggregation induced by arachidonic acid. Taken together, these results suggest that the investigation of other targets connected to the antiplatelet activity, such as phosphodiesterase-3 (PDE3), could be a viable strategy to shed light on the polypharmacological profile of coumarin-based compounds. Docking simulations towards PDE3 were also carried out.

  15. Synthesis and photochemical properties of PEGylated coumarin-caged ceramides for cell studies.

    Science.gov (United States)

    Kim, Young Ah; Day, Jenna; Lirette, Carol Ann; Costain, Willard J; Johnston, Linda J; Bittman, Robert

    2016-01-01

    Caged ceramide analogues (C6-, C16-, C18-, C22- and C24-Cer) have been prepared by introducing a hydrophilic coumarin-based cage bearing a short polyethylene glycol (PEG) chain. (6-Bromo-7-mTEGylated-coumarin-4-yl)methyl (Btc) caged ceramide showed efficient photo-uncaging to release the parent ceramide upon direct exposure to 350 nm UV light; in contrast (7-mTEGylated-coumarin-4-yl)methyl (Tc) caged ceramide was photolysed more slowly. In preliminary experiments, Btc-caged ceramides were taken up by cells and their photolysis led to decreases in cell viability, but not to activation of caspase enzymes, suggesting that either reactive oxygen species or an alternate caspase-independent pathway may be responsible for the decreases in cell viability caused by photolysis of caged ceramides.

  16. Synthesis, and Fluorescence Properties of Coumarin and Benzocoumarin Derivatives Conjugated Pyrimidine Scaffolds for Biological Imaging Applications.

    Science.gov (United States)

    Al-Masoudi, Najim A; Al-Salihi, Niran J; Marich, Yossra A; Markus, Timo

    2015-11-01

    Series of coumarin and 5,6-benzomcomarin substituted pyrimidine derivatives 11-15 and 22-25 were synthesized, aiming to develop new imaging fluorescent agents. Analogously, treatment of 4-chloropyrimidine analog 16 with coumarin 3-carbohyrazide 5 under MWI condition followed by boiling with NH4OAc in HOAc furnished coumarin-1,2,4-triazolo-pyrimidine analog 18. The fluorescence property was investigated spectrophotometrically in MeOH with Rhodamine 6G as standard dye. All the compounds showed emission in the region between 331 and 495 nm. The quantum yield of all the compounds were found to be weak, except methyl benzocoumarin 3-carboxylate 22 which showed (ΦF = 0.98) in comparison to Rhodamine 6G as standard (ΦF = 0.95).

  17. Synthesis and Structure-Activity Relationships of Imidazole-Coumarin Conjugates against Hepatitis C Virus.

    Science.gov (United States)

    Tsay, Shwu-Chen; Lin, Shu-Yu; Huang, Wen-Chieh; Hsu, Ming-Hua; Hwang, Kuo Chu; Lin, Chun-Cheng; Horng, Jia-Cherng; Chen, I-Chia; Hwu, Jih Ru; Shieh, Fa-Kuen; Leyssen, Pieter; Neyts, Johan

    2016-02-18

    A series of new conjugated compounds with a -SCH₂- linkage were synthesized by chemical methods from imidazole and coumarin derivatives. The experimental results indicate that of the twenty newly synthesized imidazole-coumarin conjugates, three of them exhibited appealing EC50 values (5.1-8.4 μM) and selective indices >20 against hepatitis C virus. Their potency and selectivity were increased substantially by modification of their structure with two factors: imidazole nucleus with a hydrogen atom at the N(1) position and coumarin nucleus with a substituent, such as Cl, F, Br, Me, and OMe. These guidelines provide valuable information for further development of conjugated compounds as anti-viral agents.

  18. Antifungal Activity of Coumarin from Ageratum conyzoides L. Leaves on Candida albicans cells

    Directory of Open Access Journals (Sweden)

    Gunawan Pamudji Widodo

    2012-07-01

    Full Text Available The aim of this study was to identify the antifungal activity of coumarin isolated from Ageratum conyzoides L. leaves and to observe its influence on Candida albicans cells by scanning electron microscope (SEM and transmission electron microscope (TEM. Antifungal activity testing by disk diffusion method showed coumarin was active toward pathogenic fungus, Candida albicans with the MIC value of coumarin of 125 g mL-1. The influence of this substance on C. albicans cells was observed by scanning and transmission electron microscopies. The result showed that this compound damaged the cell by pores formation on the cell wall. The death of cells occurred due to leakage and necrotic of cytoplasmic content.

  19. Quantitative structure-toxicity relationship study of some natural and synthetic coumarins using retention parameters

    Directory of Open Access Journals (Sweden)

    Rabtti El Hadi M.A.

    2012-01-01

    Full Text Available Four lipophilicity descriptors (RM0, b, C0, PC1 for twelve coumarine derivatives were determined by reversed-phase thin-layer chromatography in order to analyze which descriptor best describes the lipophilicity of coumarines investigated. Moreover, possible chemical toxicity of coumarins, expressed as the probability of a compound to cause organ-specific health effects, was calculated using ACD/Tox Suite program. The quantitative relationships between toxicity and molecular descriptors, including experimentally determined lipophilicity descriptors obtained in current study, were investigated using partial least square regression. The best models were obtained for kidney and liver health effects. Quantitative structure-toxicity relationship models revealed the importance of electric polarization descriptors, size descriptors and lipophilicity descriptors. Obtained models were used for the selection of the structural features of the compounds that are significantly affecting their absorption, distribution, metabolism, excretion, and toxicity. [Acknowledgements. This work has been supported by the Ministry of Education and Science of Serbia, Grant 172017.

  20. Current developments of coumarin-based anti-cancer agents in medicinal chemistry.

    Science.gov (United States)

    Emami, Saeed; Dadashpour, Sakineh

    2015-09-18

    Cancer is one of the leading health hazards and the prominent cause of death in the world. A number of anticancer agents are currently in clinical practice and used for treatment of various kinds of cancers. There is no doubt that the existing arsenal of anticancer agents is insufficient due to the high incidence of side effects and multidrug resistance. In the efforts to develop suitable anticancer drugs, medicinal chemists have focused on coumarin derivatives. Coumarin is a naturally occurring compound and a versatile synthetic scaffold possessing wide spectrum of biological effects including potential anticancer activity. This review article covers the current developments of coumarin-based anticancer agents and also discusses the structure-activity relationship of the most potent compounds.

  1. Effect of anisotropic and isotropic solvent on the dipole moment of coumarin dyes.

    Science.gov (United States)

    Zakerhamidi, M S; Ghanadzadeh, A; Moghadam, M

    2011-03-01

    The ground state (μ(g)) and the excited state (μ(e)) dipole moments of two coumarin laser dyes, coumarin 440 and 460, were studied at room temperature in various solvents, viz., general solvents, alcohols and liquid crystals at 298 K. In this work, we report dipole moment of laser dyes in different anisotropic (liquid crystal) and isotropic environments for understanding the effects of environments on the molecular dipole moment and comparing them. Ground and excited state dipole moments of coumarin dyes were evaluated by means of solvatochromic shift method. It was observed that dipole moment values of excited states (μ(e)) were higher than the corresponding ground state values (μ(g)) in all media.

  2. The essential role of coumarin secretion for Fe acquisition from alkaline soil.

    Science.gov (United States)

    Clemens, Stephan; Weber, Michael

    2016-01-01

    Plant productivity is limited by the scarcity of the essential micronutrient iron particularly in alkaline soils. The root secretion of phenolics has long been recognized as a component of the acidification-reduction strategy to acquire iron (strategy I). However, very little molecular insight into this process was available until recently several research groups independently discovered the important role of coumarins for the growth of Arabidopsis thaliana under Fe-limited conditions. Genome-wide analyses of iron deficiency responses, mutant screening and metabolomics experiments all converged on the finding that the synthesis and root exudation of scopoletin, esculetin and other coumarins is essential for iron uptake from substrates with low iron availability. Here we describe the evidence supporting this conclusion and discuss important questions that now have to be addressed in order to better understand the mechanistic basis of coumarin-dependent iron uptake and its significance within the plant kingdom.

  3. Benchmark study of UV/Visible spectra of coumarin derivatives by computational approach

    Science.gov (United States)

    Irfan, Muhammad; Iqbal, Javed; Eliasson, Bertil; Ayub, Khurshid; Rana, Usman Ali; Ud-Din Khan, Salah

    2017-02-01

    A benchmark study of UV/Visible spectra of Simple coumarins and Furanocoumarins derivatives was conducted by employing the Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TD-DFT) approaches. In this study the geometries of ground and excited states, excitation energy and absorption spectra were estimated by using the DFT functional CAM-B3LYP, WB97XD, HSEH1PBE, MPW1PW91 and TD-B3LYP with 6-31 + G (d,p) basis set. CAM-B3LYP functional was found to have close agreement with the experimental values of Furranocoumarin class of coumarins while MPW1PW91 gave close results for simple coumarins. This study provided an insight about the electronic characteristics of the selected compounds and provided an effective tool for developing and designing the better UV absorber compounds.

  4. Inhibitory activity of coumarins from Artemisia capillaris against advanced glycation endproduct formation.

    Science.gov (United States)

    Jung, Hyun Ah; Park, Jin Ju; Islam, Md Nurul; Jin, Seung Eun; Min, Byung-Sun; Lee, Je-Hyun; Sohn, Hee Sook; Choi, Jae Sue

    2012-06-01

    Since glycation can lead to the onset of diabetic complications due to chronic hyperglycemia, several indigenous Artemisia species were evaluated as potential inhibitors of advanced glycation endproducts (AGE). Among them, the Artemisia capillaris plant demonstrated the highest AGE inhibitory activity. Repeated column chromatography was performed to isolate a new acylated flavonoid glycoside, acacetin-7-O-(6″-O-acetyl)-β-D-glucopyranosyl-(1→2)[α-L-rhamnopyranosyl]-(1→6)-β-D-glucopyranoside, along with 11 known flavonoids (acacetin-7-O-β-D-glucopyranosyl-(1→2)[α-L-rhamnopyranosyl]-(1→6)-β-D-glucopyranoside, linarin, quercetin, hyperoside, isorhamnetin, isorhamnetin 3-galactoside, isorhamnetin 3-glucoside, isorhamnetin 3-arabinoside, isorhamnetin 3-robinobioside, arcapillin, and cirsilineol), six coumarins (umbelliferone, esculetin, scopoletin, scopolin, isoscopolin, and scoparone), and two phenolic derivatives (4,5-di-O-caffeoylquinic acid and chlorogenic acid). In determining the structure-activity relationship (SAR), it was found that the presence and position of hydroxyl group of test coumarins (coumarin, esculin, isoscopoletin, daphnetin, 4-methylcoumarin, and six isolated coumarins) may play a crucial role in AGE inhibition. A free hydroxyl group at C-7 and a glucosyl group instead of a methoxyl group at C-6 are two important parameters for the inhibitory potential of coumarins on AGE formation. A. capillaris and five key AGE inhibitors, including 4,5-di-Ocaffeoylquinic acid, umbelliferone, esculetin, esculin, and scopoletin, were identified as potential candidates for use as therapeutic or preventive agents for diabetic complications and oxidative stress-related diseases. We understand this to be the first detailed study on the SAR of coumarins in AGE inhibition.

  5. Probe dependent anomalies in the solvation dynamics of coumarin dyes in dimethyl sulfoxide-glycerol binary solvent: confirming the local environments are different for coumarin dyes.

    Science.gov (United States)

    Koley, Somnath; Kaur, Harveen; Ghosh, Subhadip

    2014-10-28

    The solvation dynamics of coumarin dyes in dimethyl sulfoxide (DMSO)-glycerol (GLY) binary mixtures were studied across the GLY concentrations. Three coumarin dyes with widely different hydrophobicities were used for probing the entire polarity regions of this solvent mixture. Multiple anomalous concentration regions with significantly slow solvation times were detected from all three coumarin dyes. However, their precise positions were found to be probe molecule dependent. The solvation dynamics of the moderately hydrophobic dye coumarin 480 (C480) maintain a plateau region with a similar solvation time (∼550 ps) with the increase in GLY concentration until X(GLY) (the mole fraction of glycerol) reaches 0.5. This plateau region is followed by a sudden slowdown (to ∼975 ps) on the addition of more GLY to the DMSO-GLY mixture, and then this slow region persists from X(GLY)∼ 0.55 to 0.65 (peak at 0.6). On further addition of GLY (X(GLY) > 0.7), the solvation dynamics again become slower to ∼828 ps (at X(GLY)∼ 0.8) from ∼612 ps (at X(GLY)∼ 0.7). For very high GLY-content samples (X(GLY) > 0.85), the solvation times remain similar on further changes of the GLY concentrations. In contrast to C480, the most hydrophobic dye coumarin 153 (C153) shows a linear increase of solvation time in the DMSO-GLY mixture, from 102 ps (at X(GLY)∼ 0.1) to 946 ps (at X(GLY)∼ 0.9) with increase in GLY concentration, except for the concentration region, X(GLY)∼ 0.45-0.55 (peak at 0.5), where a substantial slowdown of the solvation time is observed. The highly hydrophilic probe coumarin 343 (C343) demonstrates multiple concentration regions (X(GLY)∼ 0.05-0.10, 0.25-0.35 and 0.55-0.65) where the solvation dynamics are significantly retarded. The presence of probe dependent anomalies in the DMSO-GLY mixture is a clear indication of there being different locations of probe molecules within this solvent mixture. We assume that the slowing-down of the solvation time could

  6. Solvation of coumarin6 studied by vibrational spectroscopy and density functional theory

    Science.gov (United States)

    Singh, Randhir; Sathe, Vasant; Sharma, Amit; Kaur, Sarvpreet; Saini, G. S. S.

    2016-02-01

    Effect of solvation on coumarin6 dye has been studied with density functional theory (DFT). Optimized structure of the dye has been obtained in various solvents and frequencies of various vibrational bands have been calculated in these solvents. Calculations predict shift in the frequency of certain bands in the solvents. Similar shifts have been observed experimentally in the vibrational spectra of the dye in solvents. In order to ascertain the origin of these shifts, the interactions of solvent molecules with the coumarin6 molecule have been studied using various tools of DFT like donor-acceptor interactions, Molecular Electrostatic potential (MEP) and HOMO-LUMO analysis etc.

  7. Inhibition effects of acetyl coumarines and thiazole derivatives on corrosion of zinc in acidic medium

    Indian Academy of Sciences (India)

    A V Shanbhag; T V Venkatesha; R A Prabhu; B M Praveen

    2011-06-01

    The corrosion inhibition characteristics of acetyl coumarine (AC), bromo acetyl coumarine (BAC) and thiazole derivatives (BTMQ and BTCQ) on the corrosion of zinc in 0.1 M HCl solution were investigated by weight loss, potentiodynamic polarization and impedance techniques. The inhibition efficiency increased with increase in inhibitor concentration upto 5 × 10-4 M, then gave almost same inhibition efficiency. The polarizationmeasurements indicated the mixed nature of inhibitors. The adsorption of compounds obeyed Langmuir’s adsorption isotherm. The thermodynamic functions for adsorption processes were evaluated.

  8. Cyclization of ortho-hydroxycinnamates to coumarins under mild conditions: A nucleophilic organocatalysis approach

    Directory of Open Access Journals (Sweden)

    Florian Boeck

    2012-09-01

    Full Text Available (E-Alkyl ortho-hydroxycinnamates cyclize to coumarins at elevated temperatures of 140–250 °C. We find that the use of tri-n-butylphosphane (20 mol % as a nucleophilic organocatalyst in MeOH solution allows cyclization to take place under much milder conditions (60–70 °C. Several coumarins were prepared, starting from ortho-hydroxyarylaldehydes, by Wittig reaction with Ph3P=CHCO2Me to (E-methyl ortho-hydroxycinnamates, followed by the phosphane catalyzed cyclization.

  9. Sesquiterpene coumarins from Ferula fukanensis and their pro-inflammatory cytokine gene expression inhibitory effects.

    Science.gov (United States)

    Motai, Tsunetake; Daikonya, Akihiro; Kitanaka, Susumu

    2013-01-01

    Six new sesquiterpene coumarin derivatives, fukanefuromarin H-M (1-6), were isolated from an 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated on the basis of spectroscopic evidence, particularly heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The sesquiterpene coumarin derivatives inhibited nitric oxide (NO) and inducible NO synthase (iNOS), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) gene expression in a murine macrophage-like cell line (RAW264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-γ (IFN-γ).

  10. Influence of ZnO nanoparticles on Coumarin-503 and Coumarin-540 dye mixture for energy transfer distributed feedback dye lasers

    Science.gov (United States)

    Vijayaraghavan, G. V.; Basheer Ahamed, M.

    2016-07-01

    Using organic dyes Coumarin-503 (C503) and Coumarin-540 (C540) as donor and acceptor dyes, respectively, and Nd-YAG as pumping source (355 nm), an energy transfer-distributed feedback dye laser (ETDFDL) was constructed and its characteristics studied. Theoretical studies such as critical transfer radius (Ro), critical concentration (Co), and half quenching concentration (C1/2) were carried out using the absorption and fluorescence spectra of donor and acceptor dyes. On varying the input pump energy to the nanoparticle-incorporated ETDFDL and keeping the acceptor and donor dye concentrations constant, the lasing output obtained was found to be higher than that without the use of nanoparticles. This enhancement was due to the size, shape, and coupling between nanoparticles with the dye mixture. Tunability in the range of 435-553 nm was obtained for both donor (C503) and acceptor (C540) DFDL as a function of the angle of interfering beams of the pump laser.

  11. Cassia cinnamon as a source of coumarin in cinnamon-flavored food and food supplements in the United States.

    Science.gov (United States)

    Wang, Yan-Hong; Avula, Bharathi; Nanayakkara, N P Dhammika; Zhao, Jianping; Khan, Ikhlas A

    2013-05-08

    Coumarin as an additive or as a constituent of tonka beans or tonka extracts is banned from food in the United States due to its potentially adverse side effects. However, coumarin in food from other natural ingredients is not regulated. "True Cinnamon" refers to the dried inner bark of Cinnamomum verum. Other cinnamon species, C. cassia, C. loureiroi, and C. burmannii, commonly known as cassia, are also sold in the U.S. as cinnamon. In the present study, coumarin and other marker compounds were analyzed in authenticated cinnamon bark samples as well as locally bought cinnamon samples, cinnamon-flavored foods, and cinnamon-based food supplements using a validated UPLC-UV/MS method. The experimental results indicated that C. verum bark contained only traces of coumarin, whereas barks from all three cassia species, especially C. loureiroi and C. burmannii, contained substantial amounts of coumarin. These species could be potential sources of coumarin in cinnamon-flavored food in the U.S. Coumarin was detected in all locally bought cinnamon, cinnamon-flavored foods, and cinnamon food supplements. Their chemical profiles indicated that the cinnamon samples and the cinnamon in food supplements and flavored foods were probably Indonesian cassia, C. burmannii.

  12. Allosteric Partial Inhibition of Monomeric Proteases. Sulfated Coumarins Induce Regulation, not just Inhibition, of Thrombin

    Science.gov (United States)

    Verespy III, Stephen; Mehta, Akul Y.; Afosah, Daniel; Al-Horani, Rami A.; Desai, Umesh R.

    2016-01-01

    Allosteric partial inhibition of soluble, monomeric proteases can offer major regulatory advantages, but remains a concept on paper to date; although it has been routinely documented for receptors and oligomeric proteins. Thrombin, a key protease of the coagulation cascade, displays significant conformational plasticity, which presents an attractive opportunity to discover small molecule probes that induce sub-maximal allosteric inhibition. We synthesized a focused library of some 36 sulfated coumarins to discover two agents that display sub-maximal efficacy (~50%), high potency (150-fold). Michaelis-Menten, competitive inhibition, and site-directed mutagenesis studies identified exosite 2 as the site of binding for the most potent sulfated coumarin. Stern-Volmer quenching of active site-labeled fluorophore suggested that the allosteric regulators induce intermediate structural changes in the active site as compared to those that display ~80–100% efficacy. Antithrombin inactivation of thrombin was impaired in the presence of the sulfated coumarins suggesting that allosteric partial inhibition arises from catalytic dysfunction of the active site. Overall, sulfated coumarins represent first-in-class, sub-maximal inhibitors of thrombin. The probes establish the concept of allosteric partial inhibition of soluble, monomeric proteins. This concept may lead to a new class of anticoagulants that are completely devoid of bleeding. PMID:27053426

  13. Pharmacogenetic-guided dosing of coumarin anticoagulants : Algorithms for warfarin, acenocoumarol and phenprocoumon

    NARCIS (Netherlands)

    Verhoef, Talitha I.; Redekop, William K.; Daly, Ann K.; Van Schie, Rianne M F; De Boer, Anthonius; Maitland-Van Der Zee, Anke Hilse

    2014-01-01

    Coumarin derivatives, such as warfarin, acenocoumarol and phenprocoumon are frequently prescribed oral anticoagulants to treat and prevent thromboembolism. Because there is a large inter-individual and intra-individual variability in dose-response and a small therapeutic window, treatment with couma

  14. Synthesis and Study of Novel Coumarin Derivatives Potentially Utilizable as Memory Media

    Directory of Open Access Journals (Sweden)

    Jana Donovalová

    2009-11-01

    Full Text Available Novel coumarin derivatives, 2-oxo-2H-chromenecarbaldehyde hydrazones were prepared by reaction of substituted 2-oxo-2H-chromenecarbaldehydes with N-aminoimides in ethanol in the presence of 4-toluenesulfonic acid as catalyst. The photochromic and thermochromic properties of the prepared compounds were investigated.

  15. Pathological and biochemical evaluation of coumarin and chlorophyllin against aflatoxicosis in rat.

    Science.gov (United States)

    Abdel-Latif, Mohamed S; Elmeleigy, Khaled M; Aly, Tahany A A; Khattab, Marwa S; Mohamed, Sara M

    2017-02-09

    Aflatoxin contamination of animal diet has adverse effects on animal health and productivity. This study was performed to investigate the effect of using coumarin and/or chlorophyllin in rat diet against aflatoxicosis. Fifty-four rats were assigned into 7 groups (6 rats each). G1 was a negative control. G2 received water with coumarin 0.5%. G3 received water with chlorophyllin 0.5%. G4 received water with coumarin 0.5% and chlorophyllin 0.5%. G5-8 fed aflatoxin B1 1000ppb in diet. Group 6-8 were administered similar treatments as G2-4. The experiment ended after 8 weeks. Random glucose, total lipid, total cholesterol, total triglycerides, total protein, serum ALT, AST, creatinine, and urea were measured. Histopathology of liver, kidney and pancreas and immunohistochemical staining of placental glutathione-S-transferase (GST-P) in liver were performed. The glucose serum level, cholesterol, AST, and ALT were elevated in G5 compared to G6-8. The liver and kidney lesions in G5 included vacuolation and necrosis which subsided in G6-8. The necrosis and inflammatory cells infiltration in the pancreas of G5 were absent in G6-8. GST-P positive hepatocytes were abundant in G5, few in G6 and absent in G7 and G8. In conclusion, the chlorophyllin and coumarin possessed protective and anti-carcinogenic effect against aflatoxicosis in rats.

  16. Coumarin fluorometry to quantitatively detectable OH radicals in ultrasound aqueous medium.

    Science.gov (United States)

    Hirano, Kohsuke; Kobayashi, Takaomi

    2016-05-01

    When ultrasound (US) was exposed to aqueous coumarin solution in air atmosphere, the UV-visible and fluorescence spectra of the probe were measured at different US exposure times. The US exposure was carried out at 43 kHz and 500 kHz with different out-put power. It was found that the 500 kHz US produced umbelliferone fluorescence, while the 43 kHz US had no fluorescence. In addition, the coumarin absorbance at 270 nm maximum was decreased with in cases of the US exposure time. In contrary, the fluorescent intensity of umbelliferone at 460 nm increased with increasing of US exposure time. This exhibited that the coumarin probe was converted to umbelliferone by the US exposure, when the 500 kHz US was operated. This was facted that the coumarin framework was caused with addition of OH groups which was generated by the 500 kHz US. Therefore, the umbelliferone fluorescent became a probe to estimate OH radical in US medium. Furthermore, the chemo-fluorometry showed that the emission maximum of the formed umbelliferone could probe the bulk pHs in the US aqueous medium.

  17. Interaction of coumarin with calf thymus DNA: deciphering the mode of binding by in vitro studies.

    Science.gov (United States)

    Sarwar, Tarique; Rehman, Sayeed Ur; Husain, Mohammed Amir; Ishqi, Hassan Mubarak; Tabish, Mohammad

    2015-02-01

    DNA is the major target for a wide range of therapeutic substances. Thus, there has been considerable interest in the binding studies of small molecules with DNA. Interaction between small molecules and DNA provides a structural guideline in rational drug designing and in the synthesis of new and improved drugs with enhanced selective activity and greater clinical efficacy. Plant derived polyphenolic compounds have a large number of biological and pharmacological properties. Coumarin is a polyphenolic compound which has been extensively studied for its diverse pharmacological properties. However, its mode of interaction with DNA has not been elucidated. In the present study, we have attempted to ascertain the mode of binding of coumarin with calf thymus DNA (Ct-DNA) through various biophysical techniques. Analysis of UV-visible absorbance spectra and fluorescence spectra indicates the formation of complex between coumarin and Ct-DNA. Several other experiments such as effect of ionic strength, iodide induced quenching, competitive binding assay with ethidium bromide, acridine orange and Hoechst 33258 reflected that coumarin possibly binds to the minor groove of the Ct-DNA. These observations were further supported by CD spectral analysis, viscosity measurements, DNA melting studies and in silico molecular docking.

  18. Coumarin or benzoxazinone based novel carbonic anhydrase inhibitors: synthesis, molecular docking and anticonvulsant studies.

    Science.gov (United States)

    Karataş, Mert Olgun; Uslu, Harun; Sarı, Suat; Alagöz, Mehmet Abdullah; Karakurt, Arzu; Alıcı, Bülent; Bilen, Cigdem; Yavuz, Emre; Gencer, Nahit; Arslan, Oktay

    2016-10-01

    Among many others, coumarin derivatives are known to show human carbonic anhydrase (hCA) inhibitory activity. Since hCA inhibition is one of the underlying mechanisms that account for the activities of some antiepileptic drugs (AEDs), hCA inhibitors are expected to have anti-seizure properties. There are also several studies reporting compounds with an imidazole and/or benzimidazole moiety which exert these pharmacological properties. In this study, we prepared fifteen novel coumarin-bearing imidazolium and benzimidazolium chloride, nine novel benzoxazinone-bearing imidazolium and benzimidazolium chloride derivatives and evaluated their hCA inhibitory activities and along with fourteen previously synthesized derivatives we scanned their anticonvulsant effects. As all compounds inhibited purified hCA isoforms I and II, some of them also proved protective against Maximal electroshock seizure (MES) and ScMet induced seizures in mice. Molecular docking studies with selected coumarin derivatives have revealed that these compounds bind to the active pocket of the enzyme in a similar fashion to that previously described for coumarin derivatives.

  19. Oxalic acid catalyzed solvent-free one pot synthesis of coumarins

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Oxalic acid was found to be an efficient catalyst for Pechmann condensation, which includes the reaction between phenols and β-keto esters leading to formation of coumarin derivatives. The advantages of present methods are the use of cheap and easy available catalyst, solvent-free reaction conditions, better yields and shorter reaction time.

  20. Ferulone A and ferulone B: two new coumarin esters from Ferula orientalis L. roots.

    Science.gov (United States)

    Razavi, Seyed Mehdi; Nahar, Lutfun; Talischi, Hamideh; Sarker, Satyajit Dey

    2016-10-01

    Ferula orientalis (Apiaceae) is a well-known perennial herb growing wild in Iran used in traditional medicine. To perform phytochemical studies, dried ground roots of F. orientalis were sequentially Soxhlet-extracted using n-hexane, dichloromethane and methanol. A combination of vacuum liquid chromatography and preparative thin-layer chromatographic analyses were performed to isolate coumarin esters. The structures of the isolated compounds were elucidated by spectroscopic means, and in vitro free-radical-scavenging property was determined by the DPPH assay. Two new coumarin esters, 7-O-(4,8,12,16-tetrahydroxy-4,8,12,16-tetramethyl-heptadecanoyl)-coumarinand 7-O-(4-hydroxy-4,8,12-trimethyl-trideca-7,11-dienoyl)-coumarin, named ferulone A and ferulone B, respectively, were isolated from the n-hexane extract of the roots of F. orientalis. Both compounds showed a low level of free-radical-scavenging property with the RC50 values of 0.252 and 0.556 mg/mL for compounds 1 and 2, respectively, as opposed to that of the positive control (quercetin) 0.004 mg/mL. This is the first report on the purification of coumarin esters from the genus Ferula.

  1. An Injectable PEG-BSA-Coumarin-GOx Hydrogel for Fluorescence Turn-on Glucose Detection.

    Science.gov (United States)

    Srinivasan, Gayathri; Chen, Jun; Parisi, Joseph; Brückner, Christian; Yao, Xudong; Lei, Yu

    2015-11-01

    Diabetes mellitus is a chronic metabolic disorder, requiring vigilant monitoring of blood glucose levels. In this study, an injectable fluorescent enzymatic hydrogel was designed for rapid glucose detection. The leakage-free glucose-responsive hydrogel was constructed by the covalent linkage of a multi-arm poly-(ethylene glycol) (PEG), bovine serum albumin (BSA), glucose oxidase (GOx), and 4-(aminomethyl)-6,7-dimethoxycoumarin (Coumarin-NH2). The GOx serves as glucose-recognition element and the pH-sensitive Coumarin-NH2 as a fluorescence turn-on reporter. The material properties of the fluorescent hydrogel were systematically characterized which show high elasticity with good mechanical strength. Upon the addition of glucose, the as-developed fluorescent hydrogel shows a fast response time, good sensitivity, and good reproducibility at physiological pH and ambient temperature. The glucose-sensing mechanism is based on the oxidation of the glucose by GOx that generates protons to change the local pH. Consequently, protonation of the covalently immobilized and pH-sensitive Coumarin-NH2 turns on the fluorescence of the coumarin. The fluorescence hydrogel developed holds great promise as an injectable, implantable glucose-sensing biomaterials for in vivo continuous glucose monitoring.

  2. Silica triflate as an efficient reagent for the solvent-free synthesis of coumarins

    Institute of Scientific and Technical Information of China (English)

    2007-01-01

    Silica triflate, as a new silica-based reagent, can be used for the efficient synthesis of 4-substituted coumarins via a Pechmann reaction under solvent-free reaction conditions. All reactions were performed at 80 ℃ in good to high yields.

  3. The coumarin herniarin as a sensitizer in German chamomile [Chamomilla recutita (L.) Rauschert, Compositae

    DEFF Research Database (Denmark)

    Paulsen, Evy; Otkjaer, Aksel; Andersen, Klaus E

    2010-01-01

    (7-methoxycoumarin), which is one of the possible coumarin allergens in chamomile. PATIENTS/MATERIALS/METHODS: Between 1991 and 2009, selected patients with known or suspected Compositae contact allergy were patch tested with herniarin 1% petrolatum. RESULTS: Among 36 patients tested, there was one...

  4. Differential morphological, cytological and biochemical responses of two rice cultivars to coumarin

    Science.gov (United States)

    Plants are often exposed to allelochemicals in the environment produced by neighboring plants. Coumarin is a common allelochemical produced by many higher plants. Two cultivars (susceptible BS-2000 and less susceptible BR-41) of rice (Oryza sativa L.) were selected to compare their differential root...

  5. Synthesis of a Novel Blue—light—emitting Polymer Material Bearing Coumarin Pendants

    Institute of Scientific and Technical Information of China (English)

    ZhiYunLU; TongSuoYUAN; 等

    2002-01-01

    A novel blue luminescent polymer bearing coumarin pendants was prepared. Its luminescent properties were determined indicating that it had strong blue fluorescent properies and good film formation ability. This novel polymer can be used as a blue organic electroluminescent material (OELM) in organic electroluminescent devices.

  6. On the role of a coumarin derivative for sensing applications: Nucleotide identification using a micellar system.

    Science.gov (United States)

    Bettoschi, Alexandre; Ceglie, Andrea; Lopez, Francesco; Meli, Valeria; Murgia, Sergio; Tamburro, Manuela; Caltagirone, Claudia; Cuomo, Francesca

    2016-09-01

    The recognition of nucleotides is of crucial importance because they are the basic constituents of nucleic acids. The present study is focused on the selective interaction between a novel amphiphilic fluorophore containing coumarin and imidazole, CI (1-methyl-3-(12-((2-oxo-2H-chromen-7-yl)oxy)dodecyl)-1H-imidazol-3-ium bromide), and different nucleotide-monophosphates (NMPs). It was supposed that the solubilization of the low water soluble CI in a micelle system of hexadecyltrimethylammonium chloride (CTAC) would make the coumarin moiety of CI available to the interaction with the water-soluble NMPs. Changes in CTAC critical micelle concentration suggested that CI strongly interacted with the host cationic surfactant, thus forming a positively charged interface enriched with coumarin able to interact with the anionic NMPs. Steady-state fluorescence quenching revealed that CI/CTAC system was capable of distinguish between purine- and pyrimidine-based nucleotides. A modified Stern-Volmer equation permitted the use of a quenching model that accounted for the possible interactions between the micelles and the nucleotides. The data analysis allowed calculating selective parameters that differentiated according to the type of nucleotide either at 25 or 50°C. Our results established the utility of the novel coumarin derivative fluorophore, supported by the simple and suitable micellar systems, as a tool for DNA sensing applications.

  7. Antifungal Activity of Coumarin Mammeisin Isolated from Species of the Kielmeyera Genre (Family: Clusiaceae or Guttiferae

    Directory of Open Access Journals (Sweden)

    Helcio Cassemiro Marcondes

    2015-01-01

    Full Text Available Coumarin mammeisin isolated from Kielmeyera elata was evaluated for its toxicity and antifungal activities. The toxicity of mammeisin was investigated by utilizing the Artemia salina methodology to determine its LD50 value. The minimum inhibitory concentration (MIC of fungi Candida sp. was assessed for mammeisin, presenting equivalent activity to ketoconazole but displaying better results than fluconazole.

  8. Increased Bleeding Risk With Concurrent Use of Selective Serotonin Reuptake inhibitors and Coumarins

    NARCIS (Netherlands)

    Schalekamp, Tom; Klungel, Olaf H; Souverein, Patrick C; de Boer, Anthonius

    2008-01-01

    BACKGROUND: Treatment with vitamin K antagonists (coumarins) is associated with an increased risk of bleeding. Because use of selective serotonin reuptake inhibitors (SSRIs) is also associated with an increased risk of bleeding, we assessed the odds ratio (OR) of abnormal bleeding associated with SS

  9. Statement on the safety of glucosamine for patients receiving coumarin anticoagulants

    DEFF Research Database (Denmark)

    Tetens, Inge

    2011-01-01

    The European Food Safety Authority (EFSA) asked the Panel on Dietetic Products, Nutrition and Allergies to provide a scientific statement on the safety of glucosamine for patients receiving coumarin anticoagulants. More than 40 case reports have been collected by drug-monitoring agencies that sho......The European Food Safety Authority (EFSA) asked the Panel on Dietetic Products, Nutrition and Allergies to provide a scientific statement on the safety of glucosamine for patients receiving coumarin anticoagulants. More than 40 case reports have been collected by drug-monitoring agencies...... that showed in some patients being prescribed coumarin anticoagulants, especially warfarin, that the International Normalised Ratio (INR) increased after they began taking glucosamine, which indicated an increase in the coagulation time. In most cases the increased INR values were symptomless but in some...... cases haemorrhage occurred in a variety of organs, and in one case this resulted in a persistent vegetative state. The evidence for an interaction between glucosamine and coumarin anticoagulants is strengthened by the observation that in the majority of cases the INR began to fall to normal values when...

  10. Neurological outcome in school-age children after in utero exposure to coumarins

    NARCIS (Netherlands)

    Wesseling, J; Van Driel, D; Smrkovsky, M; Van der Veer, E; Geven-Boere, LM; Sauer, PJJ; Touwen, BCL

    2001-01-01

    The effect of prenatal exposure to coumarins (acenocoumarol, phenprocoumon) on neurological outcome was assessed in a cohort of 306 children aged 7-15 years. Findings were compared with those in a non-exposed cohort of 267 children, matched for sex, age, and demographic region. We used a neurologica

  11. The effect of high pressure on the luminescent properties of coumarin 153

    CERN Document Server

    Li Hong; He Li Ming; Wu Shi Kang; Li Yi; Yang Guo Qiang

    2002-01-01

    A dual-fluorescence emitting behaviour of coumarin 153 powder has been detected at high pressure while at ambient pressure the dye exhibits only single-band emission. Because of the strong electron-withdrawal group at site 7, these two fluorescent peaks can be ascribed to local excited state emission and charge transfer state emission, respectively.

  12. Control of an Unusual Photo-Claisen Rearrangement in Coumarin Caged Tamoxifen through an Extended Spacer.

    Science.gov (United States)

    Wong, Pamela T; Roberts, Edward W; Tang, Shengzhuang; Mukherjee, Jhindan; Cannon, Jayme; Nip, Alyssa J; Corbin, Kaitlin; Krummel, Matthew F; Choi, Seok Ki

    2017-02-17

    The use of coumarin caged molecules has been well documented in numerous photocaging applications including for the spatiotemporal control of Cre-estrogen receptor (Cre-ERT2) recombinase activity. In this article, we report that 4-hydroxytamoxifen (4OHT) caged with coumarin via a conventional ether linkage led to an unexpected photo-Claisen rearrangement which significantly competed with the release of free 4OHT. The basis for this unwanted reaction appears to be related to the coumarin structure and its radical-based mechanism of uncaging, as it did not occur in ortho-nitrobenzyl (ONB) caged 4OHT that was otherwise linked in the same manner. In an effort to perform design optimization, we introduced a self-immolative linker longer than the ether linkage and identified an optimal linker which allowed rapid 4OHT release by both single-photon and two-photon absorption mechanisms. The ability of this construct to actively control Cre-ERT2 mediated gene modifications was investigated in mouse embryonic fibroblasts (MEFs) in which the expression of a green fluorescent protein (GFP) reporter dependent gene recombination was controlled by 4OHT release and measured by confocal fluorescence microscopy and flow cytometry. In summary, we report the implications of this photo-Claisen rearrangement in coumarin caged compounds and demonstrate a rational linker strategy for addressing this unwanted side reaction.

  13. Valorisation des plantes médicinales à coumarines des marchés de ...

    African Journals Online (AJOL)

    SARAH

    30 janv. 2015 ... Résultats : Au total, 38 espèces végétales à coumarines dont 25 herbacées et 13 ligneuses ont ... These species are mostly cultivated and leaves, fruits and seeds are generally used for ... substances naturelles, organiques et.

  14. Non-cytotoxic antibacterial silver-coumarin complex doped sol-gel coatings.

    Science.gov (United States)

    Jaiswal, Swarna; Bhattacharya, Kunal; Sullivan, Maeve; Walsh, Maureen; Creaven, Bernadette S; Laffir, Fathima; Duffy, Brendan; McHale, Patrick

    2013-02-01

    Microbial colonisation on clinical and industrial surfaces is currently of global concern and silane based sol-gel coatings are being proposed as potential solutions. Sol-gels are chemically inert, stable and homogeneous and can be designed to act as a reservoir for releasing antimicrobial agents over extended time periods. In the present study, silver nitrate (AgN) and a series of silver coumarin complexes based on coumarin-3-carboxylatosilver (AgC) and it is 6, 7 and 8 hydroxylated analogues (Ag6, Ag7, Ag8) were incorporated into sol-gel coatings. The comparative antibacterial activity of the coatings was determined against meticillin resistant Staphylococcus aureus (MRSA) and multidrug resistance Enterobacter cloacae WT6. The percentage growth inhibitions were found in the range of 9.2 (±2.7)-66.0 (±1.2)% at low silver loadings of 0.3% (w/w) with E. cloacae being the more susceptible. Results showed that among the Ag coumarin complexes, the Ag8 doped coating had the highest antibiofilm property. XPS confirmed the presence of silver in the nanoparticulate state (Ag(0)) at the coating surface where it remained after 4 days of exposure to bacterial culture. Comparative cytotoxicity studies revealed that the Ag-complex coatings were less toxic than the AgN coating. Thus, it can be concluded that a sol-gel matrix with Ag-coumarin complexes may provide non-toxic surfaces with antibacterial properties.

  15. Increased Bleeding Risk With Concurrent Use of Selective Serotonin Reuptake inhibitors and Coumarins

    NARCIS (Netherlands)

    Schalekamp, Tom; Klungel, Olaf H; Souverein, Patrick C; de Boer, Anthonius

    2008-01-01

    BACKGROUND: Treatment with vitamin K antagonists (coumarins) is associated with an increased risk of bleeding. Because use of selective serotonin reuptake inhibitors (SSRIs) is also associated with an increased risk of bleeding, we assessed the odds ratio (OR) of abnormal bleeding associated with

  16. One-pot four component synthesis of novel 3-furyl coumarin derivatives

    Indian Academy of Sciences (India)

    Venkata Prasad Jalli; Suvratha Krishnamurthy; Tetsuji Moriguchi; Akihiko Tsuge

    2016-02-01

    Efficient and facile synthesis of 3-furyl coumarin derivatives have been achieved by reaction of 4-chloro-3-formylcoumarin, secondary amines, dialkyl acetylenedicarboxylates and diversely substituted isocyanides using four component, one-pot reaction. All the products were isolated as yellow color fluorescent solids by column chromatography in quantitative yield and characterized with 1H NMR, 13C NMR, IR and FAB mass.

  17. Sesquiterpene coumarins from the roots of Ferula sinkiangensis and Ferula teterrima.

    Science.gov (United States)

    Yang, Jun-Rong; An, Zheng; Li, Zhi-Hong; Jing, Song; Qina, Hai-Lin

    2006-11-01

    Three new natural sesquiterpene coumarins, isofeterin (1), lehmannolol (3), sinkianone (4), and one known compound, lehmannolone (2), were isolated from the roots of Ferula teterrima and Ferula sinkiangensis. Their chemical structures were established on the basis of spectroscopic analysis, including X-ray crystallography and CD spectrum measurements for determining the absolute configuration of compound 2.

  18. Synthesis of a Novel Blue- light- emitting Polymer Material Bearing Coumarin Pendants

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    A novel blue luminescent polymer bearing coumarin pendants was prepared. Its luminescent properties were determined indicating that it had strong blue fluorescent properties and good film formation ability. This novel polymer can be used as a blue organic electroluminescent material (OELM) in organic electroluminescent devices.

  19. Two New O-terpenoidal Coumarins, Excavacoumarin A and B from Clausena excavata

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    Two new O-terpenoidal coumarins named excavacoumarin A (2), B (3), and a known one 1 were isolated from the leaves of Clausena excavata Burm. f. (Rutaceae) collected in Xishuangbanna, Yunnan. Structure elucidation and unambiguous NMR assignments for the title compounds were carried out on the basis of 1D and 2D NMR experiments.

  20. LATE NEUROLOGICAL, COGNITIVE AND BEHAVIORAL SEQUELAE OF PRENATAL EXPOSURE TO COUMARINS - A PILOT-STUDY

    NARCIS (Netherlands)

    OLTHOF, E; DEVRIES, TW; TOUWEN, BCL; SMRKOVSKY, M; GEVENBOERE, LM; HEIJMANS, HSA; VANDERVEER, E

    1994-01-01

    Neurological, cognitive and behavioural development were assessed in a group of 21, 8- to 10-year old children whose mothers took coumarins during pregnancy. Findings were compared with those in a group of 17 control children. The study was performed to test whether it is feasible to carry out a rel

  1. Amburosides C-H and 6-O-protocatechuoyl coumarin from Amburana cearensis

    Energy Technology Data Exchange (ETDEWEB)

    Canuto, Kirley M.; Lima, Mary Anne S.; Silveira, Edilberto R., E-mail: edil@ufc.b [Universidade Federal do Ceara (UFC), Fortaleza, CE (Brazil). Dept. de Quimica Organica e Inorganica

    2010-07-01

    Six new amburosides (1-6) and a novel 6-coumaryl protocatechuate (7) were isolated from the seeds and trunk bark of Amburana cearensis, together with coumarin, 6-hydroxycoumarin, isokaempferide, formononetin, vanillic acid, amburoside A and (E)-o-coumaric acid. The chemical structures of the new compounds were elucidated by means of NMR (COSY, HSQC, HMBC and NOESY) and HRMS spectral analyses. (author)

  2. Synthesis and Photooxygenation of Furo[3,2-c]coumarin Derivatives as Antibacterial and DNA Intercalating Agent

    Institute of Scientific and Technical Information of China (English)

    Al-Sehemi, Abdullah G.; EI-Gogary, Sameh R.

    2012-01-01

    Syntheses of 2,3-dimethyl-4H-furo[3,2-c]coumarin and 3-phenyl-4H-furo[3,2-c]coumarin as angular furocou- marins were carried out through Williamson reaction of 4-hydroxycoumarin with a-haloketones followed by cycli- zation. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3-dimethyl-4H-furo[3,2-c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8-methoxypsoralen (8-MOP).

  3. [Microcirculatory consequences of a venous striction in the rat. Effect of a coumarine-rutine association].

    Science.gov (United States)

    Laemmel, E; Stücker, O; Pons, C; Duverger, J P; Dedieu, F; Leutenegger, E

    1998-06-01

    The aim of this study was to investigate the consequences of a venous striction on capillary red blood cell distribution and venular blood return and the effect of a coumarin derivative-rutoside combination. The study was conducted, in vivo, in the rat cremaster muscle using intravital microscopy. The striction lasted thirty minutes and was obtained by clamping the epigastric vein. This mechanical constraint was sufficient to induce microcirculatory modifications without disrupting microvessels. Before the striction (t-5 min), the velocities and diameters of the veins and arteries were comparable in all groups. After the striction (t5 min), in the control group, venous blood flow decreased by 60%, from 0.48 +/- 0.09 mm3/s (t-5 min) to 0.20 +/- 0.06 mm3/s (t5 min). The results showed that after thirty minutes reperfusion, venular blood flow in the control animals was only 34% of initial blood flow. The mean red blood cell velocity dropped by 56%, the percentage of low perfused capillaries increased from 7.5% to 50%. Treatment of animals with a coumarin derivative-rutoside combination, particularly at 4 mg/kg coumarin derivative-100 mg/kg rutoside, has significantly improved the microcirculation. After thirty minutes reperfusion venular blood flow was 60% and the percentage of low perfused capillaries was only 10%. The effect seemed to be more pronounced for rutoside than coumarin derivatives. The interest of this study was to set up an experimental model of a venous striction not too severe to induce micro-hemorrages but enough to modify microcirculation. This model was used to quantify the beneficial effects of a coumarin derivative-rutoside combination.

  4. Design, synthesis and vasorelaxant evaluation of novel coumarin-pyrimidine hybrids.

    Science.gov (United States)

    Amin, Kamilia M; Awadalla, Fadi M; Eissa, Amal A M; Abou-Seri, Sahar M; Hassan, Ghaneya S

    2011-10-15

    The main objective of the present work depends on the hybridization of coumarin moiety as a vasorelaxant scaffold and pyrimidine ring with known potential cardiovascular activity in order to prepare some new potent antihypertensive candidates. Hence, two groups of pyrimidinyl coumarin derivatives were synthesized and evaluated for their vasorelaxing activity. These compounds were prepared via two routes; either preparation of the guanidinocoumarin 4 followed by a cocktail of cyclization reactions to yield a different array of 6-(substituted pyrimidin-2-yl)aminocoumarins 5-17, or through cyclization of the precursor chalcones 22a-g with guanidine hydrochloride to generate the corresponding final compounds, 8-(6-aryl-2-aminopyrimidin-4-yl)-7-methoxycoumarins 23a-g. The effect of these compounds and the coumarin intermediates 3, 4, 21 and 22a-g on nor-epinephrine induced contracture in thoracic rat aortic rings was investigated using prazocin as reference drug. Several derivatives showed promising activities either equal or even better than that of prazocin (IC(50) 0.487 mM). The most prospective compounds; the pyrimidinylamino coumarin derivatives 8, 17 (IC(50) 0.411, IC(50) 0.421 mM) and the chalcones 22b, 22e (IC(50) 0.371, 0.374 mM) that displayed the highest activity can be a base for lead optimization and simple but efficient design of new compounds. 2D-QSAR analysis was applied to find a correlation between the experimental vasorelaxant activities of the newly synthesized coumarin derivatives and their different physicochemical parameters. The result of this study showed that the increase in aqueous solubility while retaining good hydrophobic character of the overall molecule is the key for maintaining high relaxation activity.

  5. Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents.

    Science.gov (United States)

    Keri, Rangappa S; Sasidhar, B S; Nagaraja, Bhari Mallanna; Santos, M Amélia

    2015-07-15

    Tuberculosis (TB) is still a challenging worldwide health problem and mycobacterium tuberculosis (MTB) remains one of the most deadly human pathogens. TB is the second leading infectious cause of mortality today behind only HIV/AIDS. The impetus for developing new structural classes of antituberculosis drugs comes from the emergence of multi-drug resistant (MDR) strains. The development of MDR strains to commonly used drugs is due to, longer durations of therapy as results of resistance, and the resurgence of the disease in immune compromised patients. Therefore, there is an urgent need to explore new antitubercular (anti-TB) agents. Ironically, the low number of potentially new chemical entities which can act as anti-TB candidates is of great importance at present situation. Considering the severity of the problem, WHO has prepared a strategic plan in Berlin declaration 2007 to stop TB, globally. Among the oxygen heterocycles, coumarin derivatives are important motifs, which can be widely found in many natural products, and many of them displaying diverse biological activities. This spectacular spectrum of applications has intrigued organic and medicinal chemists for decades to explore the natural coumarins or their synthetic analogs for their applicability as anti-TB drugs. To pave the way for the future research, there is a need to collect the latest information in this promising area. In the present review, we collated published reports on coumarin derivatives to shed light on the insights on different types of methods reported for their preparations, characterizations and anti-TB applications, so that its full therapeutic potential class of compounds can be utilized for the treatment of tuberculosis. Therefore, the objective of this review is to focus on important coumarin analogs with anti-TB activities, and structure-activity relationships (SAR) for designing the better anti-TB agents. It is hoped that, this review will be helpful for new thoughts in the

  6. Identification of natural coumarin compounds that rescue defective DeltaF508-CFTR chloride channel gating.

    Science.gov (United States)

    Xu, Li-Na; Na, Wan-Li; Liu, Xin; Hou, Shu-Guang; Lin, Sen; Yang, Hong; Ma, Tong-Hui

    2008-08-01

    1. Deletion of phenylalanine at position 508 (DeltaF508) of the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel is the most common mutation causing cystic fibrosis (CF). Effective pharmacological therapy of CF caused by the DeltaF508-CFTR mutation requires the rescue of both intracellular processing and channel gating defects. 2. We identified a class of natural coumarin compounds that can correct the defective DeltaF508-CFTR chloride channel gating by screening a collection of 386 single natural compounds from Chinese medicinal herbs. Screening was performed with an iodide influx assay in Fischer rat thyroid epithelial cells coexpressing DeltaF508-CFTR and an iodide-sensitive fluorescent indicator (YFP-H148Q/I152L). 3. Dose-dependent potentiation of defective DeltaF508-CFTR chloride channel gating by five coumarin compounds was demonstrated by the fluorescent iodide influx assay and confirmed by an Ussing chamber short-circuit current assay. Activation was fully abolished by the specific CFTR inhibitor CFTR(inh)-172. Two potent compounds, namely imperatorin and osthole, have activation K(d) values of approximately 10 micromol/L, as determined by the short-circuit current assay. The active coumarin compounds do not elevate intracellular cAMP levels. Activation of DeltaF508-CFTR by the coumarin compounds requires cAMP agonist, suggesting direct interaction with the mutant CFTR molecule. Kinetics analysis indicated rapid activation of DeltaF508-CFTR by the coumarin compounds, with half-maximal activation of CFTR activators may represent a new class of natural lead compounds for the development of pharmacological therapies for CF caused by the DeltaF508 mutation.

  7. Differential inhibition of cytochromes P450 3A4 and 3A5 by the newly synthesized coumarin derivatives 7-coumarin propargyl ether and 7-(4-trifluoromethyl)coumarin propargyl ether.

    Science.gov (United States)

    Sridar, Chitra; Kent, Ute M; Noon, Kate; McCall, Alecia; Alworth, Bill; Foroozesh, Maryam; Hollenberg, Paul F

    2008-11-01

    The abilities of 7-coumarin propargyl ether (CPE) and 7-(4-trifluoromethyl)coumarin propargyl ether (TFCPE) to act as mechanism-based inactivators of P450 3A4 and 3A5 in the reconstituted system have been investigated using 7-benzyloxy-4-(trifluoromethyl)coumarin (BFC) and testosterone as probes. CPE inhibited the BFC O-debenzylation activity of P450 3A4 in a time-, concentration-, and NADPH-dependent manner characteristic of a mechanism-based inactivator with a half-maximal inactivation (K(I)) of 112 microM, a maximal rate of inactivation (k(inact)) of 0.05 min(-1), and a t(1/2) of 13.9 min. Similarly, TFCPE inhibited the BFC O-debenzylation activity of P450 3A4 in a time-, concentration-, and NADPH-dependent manner with a K(I) of 14 microM, a k(inact) of 0.04 min(-1), and a t(1/2) of 16.5 min. Parallel losses of P450 3A4 enzymatic activity and heme were observed with both compounds as measured by high-performance liquid chromatography and reduced CO spectra. Interestingly, neither compound inhibited the BFC O-debenzylation activity of P450 3A5. Reactive intermediates of CPE and TFCPE formed by P450 3A4 were trapped with glutathione, and the resulting adducts were identified using tandem mass spectral analysis. Metabolism studies using TFCPE resulted in the identification of a single metabolite that is formed by P450 3A4 but not by P450 3A5 and that may play a role in the mechanism-based inactivation.

  8. Easy Access to Coumarin Derivatives Using Alumina Sulfuric Acid as an Efficient and Reusable Catalyst under Solvent-Free Conditions

    Directory of Open Access Journals (Sweden)

    Ali Amoozadeh

    2013-01-01

    Full Text Available A new and efficient condition for the use of alumina sulfuric acid (ASA as a heterogeneous catalyst in the Pechmann condensation reaction in solvent-free condition for the formation of coumarins has been reported.

  9. Microwave assisted synthesis and biological activity of 3-aryl-furo[3,2-c]coumarins

    Directory of Open Access Journals (Sweden)

    Ankit R. Kaneria

    2017-02-01

    Full Text Available The synthesis of various 3-aryl-furo[3,2-c]coumarins 4a–l has been carried out by employing two different methodologies under microwave irradiation condition. In the first method different 3-aryl-furo[3,2-c]coumarins 4a–l have been synthesized by reacting various 4-hydroxy coumarins 1a–d with appropriate 2-aryl-1-nitro ethenes 2a–c under Nef reaction condition, while in the second method the same target compounds have been synthesized by reacting various 4-hydroxy coumarins 1a–d with appropriate aroylmethyl bromides 3a–c under Feist–Benary reaction condition. All the synthesized compounds were characterized by elemental analysis and IR, 1H NMR, 13C NMR, DEPT-90 spectral analysis. All the synthesized compounds 4a–l were screened for their antimicrobial activity.

  10. Broadband Light-Harvesting Molecular Triads with High FRET Efficiency Based on the Coumarin-Rhodamine-BODIPY Platform.

    Science.gov (United States)

    He, Longwei; Zhu, Sasa; Liu, Yong; Xie, Yinan; Xu, Qiuyan; Wei, Haipeng; Lin, Weiying

    2015-08-17

    Broadband capturing and FRET-based light-harvesting molecular triads, CRBs, based on the coumarin-rhodamine-BODIPY platform were rationally designed and synthesized. The absorption band of CRBs starts from blue-green to yellow-orange regions (330-610 nm), covering the strong radiation scope of sunlight. The peripheral coumarin and BODIPY chromophore energy could transfer to the central acceptor rhodamine by a one-step direct way. The energy of the coumarin moiety could also transfer to the BODIPY unit, subsequently transferring to the rhodamine core by two-step sequential ways. Both the efficiencies of the coumarin moiety and the BODIPY unit to the rhodamine core in CRBs, determined by two different ways, are very high.

  11. Solvation and rotational relaxation of coumarin 153 in a new hydrophobic ionic liquid: An excitation wavelength dependence study

    Energy Technology Data Exchange (ETDEWEB)

    Kumar Das, Sudhir [School of Chemical Sciences, National Institute of Science Education and Research, Bhubaneswar 751005 (India); Sarkar, Moloy, E-mail: moloysarkar@gmail.com [School of Chemical Sciences, National Institute of Science Education and Research, Bhubaneswar 751005 (India)

    2012-02-15

    The solvent relaxation and rotational dynamics of coumarin 153 have been investigated in a new room temperature ionic liquid, 1-(2-methoxyethyl)-1-methylpyrrolidiniumtris (pentafluorethyl)trifluorophosphate [[MOEMPL][FAP

  12. Synthesis of spiro[indolo-1,5-benzodiazepines] from 3-acetyl coumarins for use as possible antianxiety agents

    Indian Academy of Sciences (India)

    Raviraj A Kusanur; Manjunath Ghate; Manohar V Kulkarni

    2004-08-01

    3-Acetyl coumarins (1) when allowed react with isatin (2) gave corresponding 3-(3'-hydroxy-2'-oxo indolo) acetyl coumarins (3), which on dehydration afforded the corresponding ,-unsaturated ketones (4). Cyclocondensation of (4) with substituted -phenylene diamines resulted in novel 3-coumarinyl spiro[indolo-1,5-benzodiazepines] (5). Structures of all the compounds have been established on the basis of their IR, NMR and mass spectral data and have been screened for their antimicrobial activity and antianxiety activity in mice.

  13. Preparation and Antimicrobial Activity of s-Triazine Hydrazones of 7-Hydroxy Coumarin and Their Metal Complexes

    Directory of Open Access Journals (Sweden)

    G. R. Jani

    2009-01-01

    Full Text Available Metal complexes of 7-hydroxy coumarin hydrazone of s-triazine derivatives derived from 7-hydroxy-8-aceto-N-(4',6’-dichloro-1',3',5'-s-triazine coumarin hydrazone and transition metals have been synthesized and screened for their antibacterial, antifungal and antiseptic activity. The geometry of the complexes has been proposed. The ligand system co-ordinates with the metal ion in a bidentate manner through the nitrogen atom of hydrazone group.

  14. ZnO nanoparticle as catalyst for efficient green one-pot synthesis of coumarins through Knoevenagel condensation

    Indian Academy of Sciences (India)

    B Vinay Kumar; Halehatty S Bhojya Naik; D Girija; B Vijaya Kumar

    2011-09-01

    Green chemistry protocols with the reusability of the nano particle as catalyst in the synthesis of coumarins is described. The zinc oxide (ZnO) nanoparticles functions as highly effective catalyst for the reactions of various -hydroxy benzaldehydes with 1,3-dicarbonyl compounds under microwave and thermal conditions to afford the corresponding coumarins in moderate to good yields. The catalyst is inexpensive, stable, can be easily recycled and reused for several cycles with consistent activity.

  15. Fragmentation pathways of synthetic and naturally occurring coumarin derivatives by ion trap and quadrupole time-of-flight mass spectrometry.

    Science.gov (United States)

    Liang, Xianrui; Han, Xiaomei

    2015-09-15

    Synthetic and natural coumarin derivatives possess a wide range of biological activities. Fragmentation pathway studies are important in identifying both naturally occurring coumarins and synthetic coumarins with novel structures and properties. The fragmentation pathways of eleven coumarin derivatives are investigated by electrospray ionization (ESI) ion-trap mass spectrometry (ESI-ITMS(n) ) and ESI quadrupole time-of-flight mass spectrometry (QTOFMS) in positive mode. Compounds 1-9 in this study were newly synthesized in our laboratory. Compounds 10 and 11 were isolated from the root of Zanthoxylum armatum. The major fragmentation pathways for 11 coumarin derivatives are greatly affected by the heterocyclic ring structures and the side-chain substituents. Typical losses of small neutral molecules, such as CH3 CH2 OH, CH2 =CH2 , CO, and H2 O, are observed for compounds 1-5. Compounds 6-9 share similar fragmentation pathways through losses of CO, aromatic rings, and the coumarin skeleton. The main product ions at m/z 205, 219, and 220 observed for compounds 10 and 11 are produced by the loss of C5 H12 O2 , C4 H10 O2 , and the C4 H9 O2 radical, respectively. The fragmentation pathways of 11 coumarin derivatives are elucidated based on ITMS(n) and QTOFMS spectral data. Differences in the structures of the heterocyclic rings and side-chain substituents strongly affect the fragmentation pathways of the coumarins. The present results will facilitate further research into the fragmentation pathways and structural characterization of these classes of compounds with diverse structures. Copyright © 2015 John Wiley & Sons, Ltd. Copyright © 2015 John Wiley & Sons, Ltd.

  16. Inhibition of P-Glycoprotein Mediated Efflux of Paclitaxel by Coumarin Derivatives in Cancer Stem Cells: An In Silico Approach.

    Science.gov (United States)

    Tripathi, Anushree; Misra, Krishna

    2016-01-01

    P-glycoprotein (P-gp) is well known to cause multidrug resistance (MDR) in cancer cells. This MDR leads to cancer recurrence which is a major obstacle in cancer treatment. High P-gp expression has been observed in the population of cancer stem cells (CSCs) having self-renewal potential. Early detection and inhibition of these CSCs is directly beneficial to cancer treatment. In this study coumarin derivatives are used to inhibit efflux process and thereby enhance bioavailability of various drugs like paclitaxel (PTX). This drug is most commonly used for the treatment of cancers of breast, ovary, head and neck. Coumarin derivatives can be used to reduce the growth of breast cancer stem cells through P-gp mediated efflux inhibition and paclitaxel bioavailability enhancement. With the use of computational approaches including molecular docking simulation and pharmacophore study, few coumarin derivatives have been found to be more potential inhibitors of P-gp mediated efflux. Based on high affinity inhibitors, new coumarin derivatives have been designed and docked at active site cavity of P-gps. Some newly designed coumarin derivatives were found to be more potent due to their higher binding affinity towards target protein. The finding that newly designed coumarins can be exploited for inhibition of P-gp mediated efflux in order to enhance paclitaxel bioavailability and can inhibit breast cancer stem cell growth is significant for designing potent anticancer drugs.

  17. Comparison of seven structurally related coumarins on the inhibition of Quorum sensing of Pseudomonas aeruginosa and Chromobacterium violaceum.

    Science.gov (United States)

    D'Almeida, R E; Molina, R D I; Viola, C M; Luciardi, M C; Nieto Peñalver, C; Bardón, A; Arena, M E

    2017-08-01

    Quorum sensing (QS) is a cell-to-cell signaling communication system that controls the virulence behavior of a broad spectrum of bacterial pathogens, participating also in the development of biofilms, responsible of the antibiotic ineffectiveness in many infections. Therefore, QS system is an attractive target for antimicrobial therapy. In this study, we compare the effect of seven structurally related coumarins against bacterial growth, biofilm formation and elastase activity of Pseudomonas aeruginosa. In addition, the anti-pathogenic capacity of the seven coumarins was evaluated on the wild type and the biosensor strain of Chromobacterium violaceum. The comparative study of coumarins showed that molecules with hydroxyl groups on the aromatic ring displayed higher activity on the inhibition of biofilm formation of P. aeruginosa over coumarins with substituents in positions 3 and 4 or without the double 3,4-bond. These 3 or 4-hydroxylated positions caused a decrease in the anti-biofilm activity obtained for coumarin. However, the hydroxyl group in position 3 of the pyrone ring was important for the inhibition of C. violaceum QS and elastolytic activity of P. aeruginosa. The effects observed were active independently of any effect on growth. According to our results, coumarin and its hydroxylated derivatives represent an interesting group of compounds to use as anti-virulence agents against the human pathogen P. aeruginosa. Copyright © 2017 Elsevier Inc. All rights reserved.

  18. Binding of coumarins to human serum albumin. Study by equilibrium dialysis; Union de cumarinas a seroalbumina humana. Estudio por dialisis en el equilibrio

    Energy Technology Data Exchange (ETDEWEB)

    Zaton Lopez, A.M.L.; Ferrer Lopez, J.M. [Departamento de Bioquimica y Biologia Molecular, Universidad del Pais Vasco, Facultad de Farmacia, Vitoria (Spain)

    1995-12-31

    In order to find the typical structure of ligands that could displace the binding of warfarin on human serum albumin, the binding parameters of several coumarin derivatives have been compared. Warfarin, hydroxy coumarin, coumarin, acetyl coumarin and chromanol, bind to two different sites on seroalbumin. In the primary binding site, the affinity for the 4-hydroxyl compounds (4-chromanol, warfarin and 4-hidroxycoumarin) are larger than for coumarin and 3-acetyl coumarin. this high-affinity binding site, warfarin binding site, is the region in which the specific binding of warfarin and 4-hydroxybenzopyrans occurs. the 4-chromanol is the smallest ligand which binds to seroalbumin with high-affinity, and its structure is typical in ligands which specifically bind to the warfarin binding site. (Author) 23 refs.

  19. Synthesis and molecular structure of 2-bromo-N-(4-(7-(diethylamino)-coumarin-3-yl)phenyl)propanamide: New coumarin-based fluorescent ATRP initiator

    Science.gov (United States)

    Kulai, Ihor; Mallet-Ladeira, Sonia

    2016-01-01

    The 2-bromo-N-(4-(7-(diethylamino)-coumarin-3-yl)phenyl)propanamide was synthesized and analyzed by NMR and FT-IR spectroscopies, high resolution mass-spectrometry and single crystal X-ray diffraction. The crystal structure belongs to the monoclinic system, P21/c space group with a = 14.9120(7) Å, b = 11.3177(5) Å, c = 12.0106(5) Å, α = 90°, β = 94.758(2)°, γ = 90° and V = 2020.04(16) Å3. Furthermore, it was shown to be an efficient fluorescent ATRP initiator in polymerizations of acrylates.

  20. Co-mutagenicity of coumarin (1,2-benzopyrone) with aflatoxin B1 and human liver S9 in mammalian cells.

    Science.gov (United States)

    Goeger, D E; Hsie, A W; Anderson, K E

    1999-06-01

    Coumarin (1,2-benzopyrone), a natural dietary constituent and drug currently under evaluation for treatment of certain cancers and lymphedema, reduces polycyclic aromatic hydrocarbon-induced neoplasms in rodents. Because most rodents metabolize coumarin through 3,4-epoxidation, whereas 7-hydroxylation predominates in humans, their suitability as a model for coumarin effects in humans has been questioned. We examined coumarin chemoprotection against the promutagen and dietary contaminant aflatoxin B1 with human liver S9 bioactivation in the Chinese hamster ovary cell/hypoxanthine-guanine phosphoribosyltransferase mutation assay. Coumarin in the absence of aflatoxin B1 was not mutagenic or cytotoxic up to 500 microM. When included with either 1 or 10 microM aflatoxin B1, coumarin produced a dose-dependent increase in mutant frequency and cytotoxicity. At concentrations greater than 50 microM, coumarin stimulated human liver S9 bioactivation of aflatoxin B1 to the mutagenic 8,9-epoxide. This increase was 12- and fivefold at 500 microM coumarin with 1 and 10 microM aflatoxin B1, respectively, compared with incubations with aflatoxin B1 alone. These findings differ from previous results with liver S9 from other species, and indicate that coumarin co-mutagenicity with aflatoxin B1 and human liver S9 is through increased aflatoxin B1 bioactivation.

  1. Synergistic inhibition of kale seed germination by coumarin and (2-chloroethyl)-trimethylammonium chloride, and its reversal by kinetin and gibberellic acid.

    Science.gov (United States)

    Knypl, J S

    1966-09-01

    1. The retarding effect of (2-chloroethyl)trimethylammonium chloride (CCC) on germination of kale seeds is reduced and overcome by either kinetin or gibberellic acid (GA). 2. Coumarin inhibition of germination is reduced by kinetin but not by GA. 3. Germination of seeds treated with coumarin in combination with CCC is blocked; both kinetin and GA reduce the synergistic, inhibitory effect of coumarin and CCC. It is suggested that coumarin and CCC block alternative metabolic pathways which lead to germination in kale seed; these pathways are directly controlled by kinetin.

  2. Synthesis and evaluation of 4-substituted coumarins as novel acetylcholinesterase inhibitors.

    Science.gov (United States)

    Razavi, Seyyede Faeze; Khoobi, Mehdi; Nadri, Hamid; Sakhteman, Amirhossein; Moradi, Alireza; Emami, Saeed; Foroumadi, Alireza; Shafiee, Abbas

    2013-06-01

    A series of 4-hydroxycoumarin derivatives were designed and synthesized as new acetylcholinesterase (AChE) inhibitors which could be considered for Alzheimer's disease therapeutics. Among the 19 coumarin-derived compounds tested toward Electrophorus electricus acetylcholinesterase (eelAChE) and horse serum butyrylcholinesterase (eqBChE), N-(1-benzylpiperidin-4-yl)acetamide derivative 4m displayed highest AChE inhibitory activity (IC50 = 1.2 μM) and good selectivity (37 times). The docking study of the most potent compound 4m, indicated that Phe330 is responsible for ligand recognition and trafficking by forming π-cation interaction with benzylpiperidine moiety. Furthermore, the formation of an additional π-π interaction between coumarin moiety and Trp279 of peripheral anionic site could stabilize the ligand in the active site resulting in more potent inhibition of the enzyme. Copyright © 2013 Elsevier Masson SAS. All rights reserved.

  3. Synthesis of novel coumarin appended bis(formylpyrazole) derivatives: Studies on their antimicrobial and antioxidant activities.

    Science.gov (United States)

    Nagamallu, Renuka; Srinivasan, Bharath; Ningappa, Mylarappa B; Kariyappa, Ajay Kumar

    2016-01-15

    A series of novel coumarin pyrazole hybrids of biological interest were synthesized from the hydrazones, carbazones and thiocarbazones via Vilsmeier Haack formylation reaction. These intermediates and formyl pyrazoles were evaluated for antimicrobial and antioxidant activities. Among the series, compounds 6g and 6h showed excellent antimicrobial activity against different bacterial and fungal strains and compounds 7g, 7h were found to be potent antioxidant agents in both DPPH and hydroxyl radical scavenging assays. Further, detailed quantitative structure-activity relationship (QSAR) analysis indicated the molecular parameters that contribute to increased potency of inhibition. The above findings would further encourage our understanding in employing coumarin pyrazole hybrids as potential antibiotic agents for treating infections caused by pathogenic microbes and fungi. Further, it also paves the way for exploration of these compounds as potential therapeutic agents to treat conditions arising because of excessive oxidative damage.

  4. In vitro inhibition effect of some coumarin compounds on purified human serum paraoxonase 1 (PON1).

    Science.gov (United States)

    Gokce, Basak; Gencer, Nahit; Arslan, Oktay; Karatas, Mert Olgun; Alici, Bulent

    2016-08-01

    Human serum paraoxonase 1 (PON1; EC 3.1.8.1) is a high-density lipoprotein associated, calcium-dependent enzyme that hydrolyses aromatic esters, organophosphates and lactones and can protect the low-density lipoprotein against oxidation. In this study, in vitro effect of some hydroxy and dihydroxy ionic coumarin derivatives (1-20) on purified PON1 activity was investigated. Among these compounds, derivatives 11-20 are water soluble. In investigated compounds, compounds 6 and 13 were found the most active (IC50 = 35 and 34 µM) for PON1, respectively. The present study has demonstrated that PON1 activity is very highly sensitive to studied coumarin derivatives.

  5. Modulation of the antibiotic activity against multidrug resistant strains of coumarins isolated from Rutaceae species.

    Science.gov (United States)

    Madeiro, Sara A L; Borges, Nathalie H P B; Souto, Augusto L; de Figueiredo, Pedro T R; Siqueira-Junior, José P; Tavares, Josean F

    2017-03-01

    The first occurrences and dissemination of resistant microorganisms led to the inefficacy of many antibiotics, available in the market nowadays, therefore, the search for new substances with antimicrobial activity from natural sources has gained a great importance. The purpose of this work is to evaluate the antibacterial activity and modulation of drug resistance in Staphylococcus aureus by coumarins such as bergapten, xantotoxin, isopimpinellin and imperatorin obtained from two Rutaceae species (Metrodorea mollis and Pilocarpus spicatus). The antimicrobial activity was assessed based on the minimum inhibitory concentration (MIC), using the microdilution method. The MIC was >256 g/mL for all coumarins tested. Regarding the modulation of drug resistance assay, the isopimpinellin reducted the MIC of erytromicin by 4 times, whereas imperatorin exhibited the best result, reducing the MIC of tetracycline (2 times), erytomicin (4 times) and norfloxacin (4 times). By reducing the MIC of ethidium bromide, the imperatorin is consider in fact, as a putative efflux pump inhibitor of bacteria.

  6. DYE-SENSITIZED PHOTOPOLYMERIZATION OF METHYL METHACRYLATE INITIATED BY COUMARIN DYE/IODONIUM SALT SYSTEM

    Institute of Scientific and Technical Information of China (English)

    Fang Gao; Yong-yuan Yang

    1999-01-01

    The photosensitive initiating system composed of 7-diethylamino-3-(2'-benzimidazolyl)coumarin dye (DEDC) and diphenyliodonium hexafluorophosphate (DIHP) which act as the sensitizer and the initiator respectively, can be used to initiate the polymerization of methyl methacrylate (MMA). The results showed that when exposed to visible light, coumarin dye/iodonium salt undergoes quick electron transfer from DEDC to DIHP and free radicals are produced. The visible light photoinduced reaction between DEDC and DIHP is mainly through the excited singlet state of DEDC and thus it is a little sensitive to O2. The influence of concentration of DEDC, DIHP and MMA on the rate of photopolymerization of MMA was also investigated.

  7. In-vitro antibacterial, antifungal and cytotoxic activities of some coumarins and their metal complexes.

    Science.gov (United States)

    Rehman, Saeed U; Chohan, Zahid H; Gulnaz, Farzana; Supuran, Claudiu T

    2005-08-01

    A series of new antibacterial and antifungal coumarin-derived compounds and their transition metal complexes [cobalt (II), copper (II), nickel (II) and zinc (II)] have been synthesized, characterized and screened for their in vitro antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Salmonella typhi, Shigella dysenteriae, Bacillus cereus, Corynebacterium diphtheriae, Staphylococcus aureus and Streptococcus pyogenes bacterial strains and for in vitro antifungal activity against Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium solani, Candida glaberata. The results of these studies show the metal complexes to be more antibacterial and antifungal as compared to the uncomplexed coumarins. The brine shrimp bioassay was also carried out to study their in vitro cytotoxic properties.

  8. Coumarin and alkaloids of Rauia resinosa (Rutaceae); Cumarinas e alcaloides de Rauia resinosa (Rutaceae)

    Energy Technology Data Exchange (ETDEWEB)

    Albarici, Tatiane Regina; Vieira, Paulo Cezar; Fernandes, Joao Batista; Silva, Maria Fatima das Gracas Fernandes da, E-mail: paulo@dq.ufscar.b [Universidade Federal de Sao Carlos (UFSCAR), SP (Brazil). Dept. de Quimica; Pirani, Jose Rubens [Universidade de Sao Paulo (USP), SP (Brazil). Inst. de Biociencias. Dept. de Botanica

    2010-07-01

    The genus Rauia, that is poorly chemically studied, belongs to the Rutaceae family. This family has been known to contain a large variety of secondary metabolites. Our phytochemical investigation of the stem and leaves of Rauia resinosa has led to the identification of the structurally related coumarins: murralongin (1), murrangatin (2), munomicrolin (3), murrangatin diacetate (4), umbelliferone (5), rauianin (6) and one novel coumarin: 3-ethylrauianin (7); the alkaloids: N-methyl-4-methoxy-2-quinolone (8), mirtopsine (9), dictamine (10), g-fagarine (11), skimmianine (12), Z-dimethylrhoifolinate (13), zantodioline (14), zantobungeanine (15), veprissine (16), one novel alkaloid 7-hydroxy-8-methoxy-N-methylflindersine (17) and 8-hydroxy-N-methylflindersine (18) that is described as a natural product for the first time, and a mixture of steroids: as sitosterol and stigmasterol. (author)

  9. Cumarinas e alcaloides de Rauia resinosa (rutaceae Coumarins and alkaloids from Rauia resinosa (rutaceae

    Directory of Open Access Journals (Sweden)

    Tatiane Regina Albarici

    2010-01-01

    Full Text Available The genus Rauia, that is poorly chemically studied, belongs to the Rutaceae family. This family has been known to contain a large variety of secondary metabolites. Our phytochemical investigation of the stem and leaves of Rauia resinosa has led to the identification of the structurally related coumarins: murralongin (1, murrangatin (2, munomicrolin (3, murrangatin diacetate (4, umbelliferone (5, rauianin (6 and one novel coumarin: 3-ethylrauianin (7; the alkaloids: N-methyl-4-methoxy-2-quinolone (8, mirtopsine (9, dictamine (10, γ-fagarine (11, skimmianine (12, Z-dimethylrhoifolinate (13, zantodioline (14, zantobungeanine (15, veprissine (16, one novel alkaloid 7-hydroxy-8-methoxy-N-methylflindersine (17 and 8-hydroxy-N-methylflindersine (18 that is described as a natural product for the first time, and a mixture of steroids: as sitosterol and stigmasterol.

  10. Photo-controlled release of fipronil from a coumarin triggered precursor.

    Science.gov (United States)

    Gao, Zhenhong; Yuan, Pengtao; Wang, Donghui; Xu, Zhiping; Li, Zhong; Shao, Xusheng

    2017-06-01

    Developing efficient controlled release system of insecticide can facilitate the better use of insecticide. We described here a first example of photo-controlled release of an insecticide by linking fipronil with photoresponsive coumarin covalently. The generated coumarin-fipronil (CF) precursor could undergo cleavage to release free fipronil in the presence of blue light (420nm) or sunlight. Photophysical studies of CF showed that it exhibited strong fluorescence properties. The CF had no obvious activity against mosquito larvae under dark, but it can be activated by light inside the mosquito larvae. The released Fip from CF by blue light irradiation in vitro retained its activity to armyworm (Mythimna separate) with LC50 value of 24.64μmolL(-1). This photocaged molecule provided an alternative delivery method for fipronil. Copyright © 2017. Published by Elsevier Ltd.

  11. Coumarin-bearing triarylamine sensitizers with high molar extinction coefficient for dye-sensitized solar cells

    Science.gov (United States)

    Zhong, Changjian; Gao, Jianrong; Cui, Yanhong; Li, Ting; Han, Liang

    2015-01-01

    Coumarin unit is introduced into triarylamine and three organic sensitizers are designed and synthesized with triarylamine bearing coumarin moiety as the electron donor, conjugated system containing thiophene unit as the π-bridge, and cyanoacetic acid moiety as the electron acceptor. The light-harvesting capabilities and photovoltaic performance of these dyes are investigated systematically with the comparison of different π-bridges. High molar extinction coefficients are observed in these triarylamine dyes and the photocurrent and photovoltage are increased with the introduction of another thiophene or benzene. Optimal photovoltaic performance (η = 6.24%, Voc = 690 mV, Jsc = 14.33 mA cm-2, and ff = 0.63) is observed in the DSSC based on dye with thiophene-phenyl unit as the π-conjugated bridge under 100 mW cm-2 simulated AM 1.5 G solar irradiation.

  12. Extraction optimization of coumarins from radix angelicae pubescentis by HPLC-DAD coupled with uniform design

    Institute of Scientific and Technical Information of China (English)

    GUO Fang-qiu; HUANG Lan-fang; ZHOU Huo-fei; JIANG Qiu-ju

    2006-01-01

    Uniform design was used to optimize extraction condition of direct refluence extraction of coumarins from the Chinese traditional medicine of radix angelicae pubescentis(Duhuo); the sum peak area of coumarins separated with high performance liquid chromatography(HPLC) at detection wavelength of 320 nm was considered as detection index, two factors of solvent concentration and extraction time were mainly studied at extraction temperature of 85 ℃ and a volume ratio of solvent to sample of 10: 1. Optimal subclass, quadric polynomial step by step aggression and neural network method were applied to process the experimental results. The results show that the first and second methods give the same factors combination (concentration of ethanol: 95 %, extraction time: 3.6 h) and the second method is much better than the first one. The extraction model is consequently developed.

  13. Anisotropic media effect on the dipole moment of some coumarin dyes.

    Science.gov (United States)

    Zakerhamidi, M S; Ghanadzadeh, A; Moghadam, M; Tajalli, H

    2010-11-01

    The ground state (μ(g)) and the excited state (μ(e)) dipole moments of two coumarin laser dyes, C500 and C503, were studied at room temperature in various solvents, viz., aprotic solvents, alcohols and liquid crystals at 298 K. We report dipole moment of laser dyes in different anisotropic (liquid crystals) and isotropic environments. The dipole moments values in different media help to investigate environment effects on the molecular dipole moment and provide a straightforward method for comparing their properties. Ground and excited state dipole moments of coumarin dyes were evaluated by means of solvatochromic shift method. It was observed that dipole moment values of excited states (μ(e)) were higher than corresponding ground state values (μ(g)), indicating a substantial redistribution of the π-electron densities in a more polar excited state for the dyes investigated.

  14. Disesquiterpene and sesquiterpene coumarins from Ferula pseudalliacea, and determination of their absolute configurations.

    Science.gov (United States)

    Dastan, Dara; Salehi, Peyman; Reza Gohari, Ahmad; Zimmermann, Stefanie; Kaiser, Marcel; Hamburger, Matthias; Reza Khavasi, Hamid; Ebrahimi, Samad Nejad

    2012-06-01

    The first disesquiterpene coumarin, sanandajin, five sesquiterpene coumarins, kamolonol acetate, fekrynol acetate, ethyl galbanate, methyl galbanate, farnesiferol B, and a sesquiterpene, aristolone, were isolated from a n-hexane extract of Ferula pseudalliacea roots. The structures were elucidated by 1D and 2D NMR, HR-ESIMS data, and kamolonol acetate was confirmed by single-crystal X-ray analysis. The absolute configuration of compounds was established by comparison of experimental and simulated ECD spectra using time dependence density function theory (TDDFT). In vitro antiplasmodial activity against Plasmodium falciparum K1 strain was determined. sanandajin, kamolonol acetate and methyl galbanate showed moderate antiplasmodial activity, with IC(50) values of 2.6, 16.1 and 7.1 μM, respectively.

  15. Coumarins and flavonoid from Murraya paniculata (L.) Jack: Antibacterial and anti-inflammation activity.

    Science.gov (United States)

    Rodanant, Pirasut; Khetkam, Pichit; Suksamrarn, Apichart; Kuvatanasuchati, Jintakorn

    2015-11-01

    The ethyl acetate extract of leaves of Murraya paniculata (L.) Jack was described in the previous in vitro study on the inhibition effect on the growth of periodontopathic bacteria and the reduction of cytokines from LPS-stimulated macrophages. In this study, four coumarins including murrangatin (1), murrangatin acetate (2), murranganonesenecionate (3), micropubescin (4) and one flavonoid, 3', 4', 5', 7-tetramethoxyflavone (5) were isolated from the leaves of ethyl acetate extract of M. paniculata. MTT assay was used to test cytotoxicity on human gingival fibroblast and monocytes. The isolated compounds were evaluated for their antibacterial effect against Porphyromonas gingivalis (ATCC33277) and anti-inflammation on lipopolysaccharide-stimulated inflammation using monocyte cells. All isolated compounds exhibited antibacterial activity against P. gingivalis (ATCC 33277). Murranganonesenecionate (3) was highly potent anti-inflammation properties. The coumarin constituents from M. paniculata leaves might be potential lead molecules for the development of antimicrobial drugs for treating periodontal disease.

  16. Novel sesquiterpene and coumarin constituents from the whole herbs of Crossostephium chinense.

    Science.gov (United States)

    Wu, Qi; Zou, Lei; Yang, Xiu-Wei; Fu, De-Xian

    2009-01-01

    Novel sesquiterpene, named crossostephin (1), and coumarin, named biscopoletin (2), together with four known compounds, artesin, tanacetin, scopoletin, and scopolin, were isolated from the 70% ethanolic extract of the whole herbs of Crossostephium chinense (L.) Makino. Their structures were determined by spectroscopic methods, including IR, UV, EIMS, HRFTICRMS, 1D and 2D NMR spectral analyses. Both scopoletin and scopolin were isolated from the title plant for the first time.

  17. Synthesis and bioactivity of novel coumarin derivatives containing (E)-methyl 2-(methoxyimino)-2-phenylacetates

    Institute of Scientific and Technical Information of China (English)

    Ai Ying Guan; Chang Ling Liu; Zhi Nian Li; Ming Xing Zhang

    2011-01-01

    Ten coumarin derivatives containing (E)-methyl 2-(methoxyimino)-2-phenylacetate were synthesized and bioassayed. The compounds were identified by IR, 1H NMR and elemental analyses. The test results indicated that compound 5j (R1 is methyl and R2 is n-C6H13) was the optimal structure in this paper with good fungicidal activity against CDM (85%) at 6.25 mg/L concentration.

  18. Synthesis and properties of novel calix[4]arene derivatives bearing fluorogenic coumarin units

    Institute of Scientific and Technical Information of China (English)

    He Wen Wang; Ya Qing Feng; Jin Qiang Xue; Chan Xiao

    2008-01-01

    Four novel calix[4]arene derivatives 5-8 bearing four fluorogenic coumarin units attached via imino group acting also as binding sites at the upper rim have been prepared and characterized by IR, 1H NMR and MS. Compounds 5-8 adopt a cone conformation. Their complexation properties to different heavy and transition metal ions have been studied by UV-vis spectroscopy. Compounds 5, 6, 8 show selective recognition to Fe3+ and Cr3+.

  19. Two new coumarin glucosides biosynthesized by transgenic hairy roots of Polygonum multiflorum

    Institute of Scientific and Technical Information of China (English)

    Rong Min Yu; Liang Bin Zhou; Chun Yan Yan; Guo Yan Duan; Yu Zhao

    2008-01-01

    The glycosylation of hydroxylcoumarin was investigated by using suspension cultures of hairy roots of Polygonum multiflorum,Two new coumarin glucosides (3 and 4) were biosysthesized by regioselectively glycosylation of corresponding substrates (1 and 2)in the system. The structures of two products were identified as 7-hydroxy-4-methylcoumarin 5-O-β-D-glucopyranoside and 7-hydroxy-3,4-dimethylcoumarin 5-O-β-D-glucopyranoside on the ground of chemical and spectroscopic methods, respectively.

  20. Extraction and Quantitative HPLC Analysis of Coumarin in Hydroalcoholic Extracts of Mikania glomerata Spreng: ("guaco" Leaves

    Directory of Open Access Journals (Sweden)

    Celeghini Renata M. S.

    2001-01-01

    Full Text Available Methods for preparation of hydroalcoholic extracts of "guaco" (Mikania glomerata Spreng. leaves were compared: maceration, maceration under sonication, infusion and supercritical fluid extraction. Evaluation of these methods showed that maceration under sonication had the best results, when considering the ratio extraction yield/extraction time. A high performance liquid chromatography (HPLC procedure for the determination of coumarin in these hydroalcoholic extracts of "guaco" leaves is described. The HPLC method is shown to be sensitive and reproducible.

  1. Heavy atom quenched coumarin probes for sensitive and selective detection of biothiols in living cells.

    Science.gov (United States)

    Ji, Wengang; Ji, Yuzhuo; Jin, Qingqing; Tong, Qingxiao; Tang, Xinjing

    2015-07-07

    A series of turn-on fluorescent probes with halogen acetyl amide at the 3-position of coumarin derivatives were synthesized. Fluorescence of these probes was efficiently quenched by heavy halogen atoms (Br and I, not Cl), which could be successfully used for selective detection of biothiols with the sensitivity of Cys > GSH > Hcy and much higher than thiol containing proteins. These represent the smallest fluorescence quenchers in designing fluorescent probes for detecting both endogenous and exogenous biothiols in living cells.

  2. Synthesis, cholinesterase inhibition and molecular modelling studies of coumarin linked thiourea derivatives.

    Science.gov (United States)

    Saeed, Aamer; Zaib, Sumera; Ashraf, Saba; Iftikhar, Javeria; Muddassar, Muhammad; Zhang, Kam Y J; Iqbal, Jamshed

    2015-12-01

    Alzheimer's disease is among the most widespread neurodegenerative disorder. Cholinesterases (ChEs) play an indispensable role in the control of cholinergic transmission and thus the acetylcholine level in the brain is enhanced by inhibition of ChEs. Coumarin linked thiourea derivatives were designed, synthesized and evaluated biologically in order to determine their inhibitory activity against acetylcholinesterases (AChE) and butyrylcholinesterases (BChE). The synthesized derivatives of coumarin linked thiourea compounds showed potential inhibitory activity against AChE and BChE. Among all the synthesized compounds, 1-(2-Oxo-2H-chromene-3-carbonyl)-3-(3-chlorophenyl)thiourea (2e) was the most potent inhibitor against AChE with an IC50 value of 0.04±0.01μM, while 1-(2-Oxo-2H-chromene-3-carbonyl)-3-(2-methoxyphenyl)thiourea (2b) showed the most potent inhibitory activity with an IC50 value of 0.06±0.02μM against BChE. Molecular docking simulations were performed using the homology models of both cholinesterases in order to explore the probable binding modes of inhibitors. Results showed that the novel synthesized coumarin linked thiourea derivatives are potential candidates to develop for potent and efficacious acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors.

  3. Novel coumarin-benzimidazole derivatives as antioxidants and safer anti-inflammatory agents.

    Science.gov (United States)

    Arora, Radha Krishan; Kaur, Navneet; Bansal, Yogita; Bansal, Gulshan

    2014-10-01

    Inspired from occurrence of anti-inflammatory activity of 3-substituted coumarins and antiulcer activity of various 2-substituted benzimidazoles, novel compounds have been designed by coupling coumarin derivatives at 3-position directly or through amide linkage with benzimidazole nucleus at 2-position. The resultant compounds are expected to exhibit both anti-inflammatory and antioxidant activities along with less gastric toxicity profile. Two series of coumarin-benzimidazole derivatives (4a-e and 5a-e) were synthesized and evaluated for anti-inflammatory activity and antioxidant activity. Compounds 4c, 4d and 5a displayed good anti-inflammatory (45.45%, 46.75% and 42.85% inhibition, respectively, versus 54.54% inhibition by indomethacin) and antioxidant (IC50 of 19.7, 13.9 and 1.2 µmol/L, respectively, versus 23.4 µmol/L for butylatedhydroxytoluene) activities. Evaluation of ulcer index and in vivo biochemical estimations for oxidative stress revealed that compounds 4d and 5a remain safe on gastric mucosa and did not induce oxidative stress in tissues. Calculation of various molecular properties suggests the compounds to be sufficiently bioavailable.

  4. Antiproliferative evaluation of terpenoids and terpenoid coumarins from Ferulago macrocarpa (Fenzl Boiss. fruits

    Directory of Open Access Journals (Sweden)

    Seyed-Ebrahim Sajjadi

    2015-01-01

    Full Text Available Background: Ferulago macrocarpa is a plant used as flavoring agent and protectant in the food industry and as a folk medicinal plant in Iran with no available information on its chemical identity. Ferulago spp. showed to contain biologically terpenoids and coumarins. Objective: The objective was to isolate and characterize terpenoids and coumarins from the acetone extract of F. macrocarpa fruits and to evaluate their antiproliferative effects on several cell lines. Materials and Methods: A series of normal and reverse phase gravity and high-performance liquid chromatography analyses were used to purify constituents. Compounds 1-5 and 7 were evaluated for their cytotoxic effects on MCF-7, HT-29 and H-1299 cell lines. Results: Six compounds including bornyl acetate (1, 1,10-di-epi-cubenol (2, stigmasterol (3 and three coumarins grandivittin (4, prantschimgin (5 and 4"-hydroxygrandivittin (7 along with mixtures of feruloyl derivatives (6a-6c have been purified. Their structures were established by spectroscopic methods including nuclear magnetic resonance and MS analyses. Compound 2 showed moderate cytotoxicity effect with IC 50 values of 5.0 and 6.7 mM on MCF-7 and HT-29, respectively. Conclusion: 1,10-di-epi-Cubenol could be considered as a potential proliferation inhibitor of MCF-7 and HT-29 cell lines.

  5. Melanogenesis stimulation in murine b16 melanoma cells by umberiferae plant extracts and their coumarin constituents.

    Science.gov (United States)

    Matsuda, Hideaki; Hirata, Noriko; Kawaguchi, Yoshiko; Yamazaki, Miho; Naruto, Shunsuke; Shibano, Makio; Taniguchi, Masahiko; Baba, Kimiye; Kubo, Michinori

    2005-07-01

    Melanogenesis stimulation activities of seven ethanolic extracts obtained from Umbelliferae plants used as Chinese crude drugs, namely the roots of Angelica dahurica BENTH. et HOOK., A. biserrata SHEN et YUAN, Notopterygium incisum TING, Heracleum lanatum MICHX., and H. candicans WALL., and the fruits of Cinidium monnieri (L.) CUSSON and C. formosanum YABE, were examined by using cultured murine B16 melanoma cells. Among them, the extract (5, 25 microg/ml) of H. lanatum showed a potent stimulatory effect on melanogenesis with significant enhancement of cell proliferation in a dose-dependent manner. The melanogenesis stimulatory effects of sixteen coumarins (1-16) isolated from the seven Umbelliferae crude drugs were also examined. Among them, linear-furocoumarins [psoralen (1), xanthotoxin (2), bergapten (3), and isopimpinellin (4)] and angular-furocoumarin [sphondin (13)] exhibited potent melanogenesis stimulation activity. From the view point of structure-activity relationships, it may be assumed that a linear-furocoumarin ring having a hydrogen and/or methoxyl group at 5 and 8 positions such as 1, 2, 3 and 4 was preferable for the melanogenesis stimulation activity. The introduction of a prenyl group into the furocoumarin ring was disadvantageous. Coumarin derivatives having a simple coumarin ring were inactive.

  6. Analysis of fluorescence quenching of coumarin derivatives by 4-hydroxy-TEMPO in aqueous solution.

    Science.gov (United States)

    Żamojć, Krzysztof; Wiczk, Wiesław; Zaborowski, Bartłomiej; Jacewicz, Dagmara; Chmurzyński, Lech

    2014-05-01

    The fluorescence quenching of different coumarin derivatives (7-hydroxy-4-methylcoumarin, 5,7-dimethoxycoumarin, 7-amino-4-methyl-3-coumarinylacetic acid, 7-ethoxy-4-methylcoumarin, 7-methoxycoumarin, 7-hydroxycoumarin, 7-hydroxy-4-methyl-3-coumarinylacetic acid and 7-amino-4-methylcoumarin) by 4-hydroxy-TEMPO in aqueous solutions at the room temperature was studied with the use of UV-Vis absorption spectroscopy as well as a steady-state and time-resolved fluorescence spectroscopy. In order to understand the mechanism of quenching the absorption and fluorescence emission spectra of all coumarins along with fluorescence decays were recorded under the action of 4-hydroxy-TEMPO. The Stern-Volmer plots (both from time-averaged and time-resolved measurements) displayed no positive (upward) deviation from a linearity. The fluorescence quenching mechanism was found to be entirely dynamic, what was additionally confirmed by the registration of Stern-Volmer plots at different temperatures. The Stern-Volmer quenching constants and bimolecular quenching rate constants were obtained for all coumarins studied at the room temperature. The findings demonstrate the possibility of developing an analytical method for the quantitative determination of the free radicals' scavenger, 4-hydroxy-TEMPO.

  7. Theoretical investigation of the substituent effects on the electronic and optical properties of 6-substituted coumarin derivatives

    Science.gov (United States)

    Bai, Yihui; Zhang, Fang; Ying, Jin; Wu, Yingzi

    2015-06-01

    The electronic structures, absorption and emission spectra of selected 6-substituted coumarins were investigated and compared with unsubstituted coumarin by using density functional theory (DFT) and time-dependent DFT (TD-DFT) methods with Gaussian 09 software package. Results revealed that the presented absorption and emission spectra were affected by the substituent groups apparently. The maximum absorption wavelength of a coumarin molecule can be shifted to a longer one by introducing a large conjugated substituent, an electron donating group or a group which can form a rigid structure with the parent moiety at 6-position. The lowest energy emission of a 6-substituted coumarin can be greatly red-shifted by modifying the substituent to one which can be strongly conjugated with the phenyl ring. A group which has a strongly electron-withdrawing effect may cause a large excitation intensity and a short wavelength in emission. Most selected molecules are predicted to give the lowest-energy emissions in the purple or blue light region, which are supposed to be selected and modified as purple or blue luminescent materials. 6-nitrocoumarin is predicted as an invisible fluorescent material. 6,7-benzocoumarin, which forms a rigid conjugated ring with the parent moiety, is expected to be modified as a green luminescent material. Many of these 6-substituted coumarins are expected to be potential candidates as large Stokes shift dyes for multicolor labeling and fluorescence-activated cell sorting (FACS), especially those molecules, which bear sbnd CONH2, sbnd CN, and sbnd CH3 respectively.

  8. Thiosemicarbazone modification of 3-acetyl coumarin inhibits Aβ peptide aggregation and protect against Aβ-induced cytotoxicity.

    Science.gov (United States)

    Ranade, Dnyanesh S; Bapat, Archika M; Ramteke, Shefali N; Joshi, Bimba N; Roussel, Pascal; Tomas, Alain; Deschamps, Patrick; Kulkarni, Prasad P

    2016-10-01

    Aggregation of amyloid β peptide (Aβ) is an important event in the progression of Alzheimer's disease. Therefore, among the available therapeutic approaches to fight with disease, inhibition of Aβ aggregation is widely studied and one of the promising approach for the development of treatments for Alzheimer's disease. Thiosemicarbazone compounds are known for their variety of biological activities. However, the potential of thiosemicarbazone compounds towards inhibition of Aβ peptide aggregation and the subsequent toxicity is little explored. Herein, we report synthesis and x-ray crystal structure of novel compound 3-acetyl coumarin thiosemicarbazone and its efficacy toward inhibition of Aβ(1-42) peptide aggregation. Our results indicate that 3-acetyl coumarin thiosemicarbazone inhibits Aβ(1-42) peptide aggregation up to 80% compared to the parent 3-acetyl coumarin which inhibits 52%. Further, 3-acetyl coumarin thiosemicarbazone provides neuroprotection against Aβ-induced cytotoxicity in SH-SY5Y cell line. These findings indicate that thiosemicarbazone modification renders 3-acetyl coumarin neuroprotective properties.

  9. Deciphering the role of coumarin as a novel quorum sensing inhibitor suppressing virulence phenotypes in bacterial pathogens.

    Science.gov (United States)

    Gutiérrez-Barranquero, José A; Reen, F Jerry; McCarthy, Ronan R; O'Gara, Fergal

    2015-04-01

    The rapid unchecked rise in antibiotic resistance over the last few decades has led to an increased focus on the need for alternative therapeutic strategies for the treatment and clinical management of microbial infections. In particular, small molecules that can suppress microbial virulence systems independent of any impact on growth are receiving increased attention. Quorum sensing (QS) is a cell-to-cell signalling communication system that controls the virulence behaviour of a broad spectrum of bacterial pathogens. QS systems have been proposed as an effective target, particularly as they control biofilm formation in pathogens, a key driver of antibiotic ineffectiveness. In this study, we identified coumarin, a natural plant phenolic compound, as a novel QS inhibitor, with potent anti-virulence activity in a broad spectrum of pathogens. Using a range of biosensor systems, coumarin was active against short, medium and long chain N-acyl-homoserine lactones, independent of any effect on growth. To determine if this suppression was linked to anti-virulence activity, key virulence systems were studied in the nosocomial pathogen Pseudomonas aeruginosa. Consistent with suppression of QS, coumarin inhibited biofilm, the production of phenazines and swarming motility in this organism potentially linked to reduced expression of the rhlI and pqsA quorum sensing genes. Furthermore, coumarin significantly inhibited biofilm formation and protease activity in other bacterial pathogens and inhibited bioluminescence in Aliivibrio fischeri. In light of these findings, coumarin would appear to have potential as a novel quorum sensing inhibitor with a broad spectrum of action.

  10. A toxicogenomics-based parallelogram approach to evaluate the relevance of coumarin-induced responses in primary human hepatocytes in vitro for humans in vivo

    NARCIS (Netherlands)

    Kienhuis, A.S.; Poll, M.C.G. van de; Jong, C.H.C. de; Gottschalk, R.; Herwijnen, M. van; Boorsma, A.; Kleinjans, J.C.S.; Stierum, R.H.; Delft, J.H.M. van

    2009-01-01

    A compound for which marked species differences have been reported in laboratory animals and humans is coumarin. In rats, metabolites of coumarin are highly toxic, whereas in humans, the compound is mainly metabolized to non-toxic metabolites. In the present study, a toxicogenomics-based parallelogr

  11. Tendências evolutivas de famílias produtoras de cumarinas em angiospermae Evolutionary tendency of coumarin-bearing families in angiospermae

    Directory of Open Access Journals (Sweden)

    Claudia Valeria Campos Ribeiro

    2002-07-01

    Full Text Available Coumarins are special metabolites well distributed in the Angiospermae, either in Monocotyledoneae or Dicotyledoneae. Simple coumarins, the most widespread type, is found in all coumarin-producing families, such as: Apiaceae, Rutaceae, Asteraceae, Fabaceae, Oleaceae, Moraceae e Thymelaeaceae. The other types, linear- and angular furanocoumarins, linear- and angular pyranocoumarins, lignocoumarins, bis- and triscoumarins, are of more restricted circumscription. Among the families with occurrence numbers (NO > 100, the more advanced ones are specialized in the production of only one or two coumarin types, while the primitive families are very well diversified in types. Calculations of percentual numbers of occurrence (%NO show relevant meaning of coumarin-types in the taxonomic positioning of the producing taxa.

  12. Extraction and quantitation of coumarin from cinnamon and its effect on enzymatic browning in fresh apple juice: a bioinformatics approach to illuminate its antibrowning activity.

    Science.gov (United States)

    Thada, Rajarajeshwari; Chockalingam, Shivashri; Dhandapani, Ramesh Kumar; Panchamoorthy, Rajasekar

    2013-06-05

    Enzymatic browning by polyphenoloxidase (PPO) affects food quality and taste in fruits and vegetables. Thus, the study was designed to reduce browning in apple juice by coumarin. The ethanolic extract of cinnamon was prepared and its coumarin content was quantitated by HPLC, using authentic coumarin (AC) as standard. The effect of cinnamon extract (CE) and AC on enzymatic browning, its time dependent effects, and the specific activity of PPO and peroxidase (POD) were studied in apple juice. The docking of coumarin with PPO and POD was also performed to elucidate its antibrowning mechanism. The CE (73%) and AC (82%) showed better reduction in browning, maintained its antibrowning effect at all time points, and significantly (p < 0.05) reduced the specific activity of PPO and POD when compared with controls. Coumarin showed strong interaction with binding pockets of PPO and POD, suggesting its potential use as inhibitor to enzyme mediated browning in apple juice.

  13. Predictive Modeling of Antioxidant Coumarin Derivatives Using Multiple Approaches: Descriptor-Based QSAR, 3D-Pharmacophore Mapping, and HQSAR

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    Indrani MITRA

    2016-09-01

    Full Text Available The inability of the systemic antioxidants to alleviate the exacerbation of free radical formation from metabolic outputs and environmental pollutants claims an urgent demand for the identification and design of new chemical entities with potent antioxidant activity. In the present work, different QSAR approaches have been utilized for identifying the essential structural attributes imparting a potential antioxidant activity profile of the coumarin derivatives. The descriptor-based QSAR model provides a quantitative outline regarding the structural prerequisites of the molecules, while 3D pharmacophore and HQSAR models emphasize the favourable spatial arrangement of the various chemical features and the crucial molecular fragments, respectively. All the models infer that the fused benzene ring and the oxygen atom of the pyran ring constituting the parent coumarin nucleus capture the prime pharmacophoric features, imparting superior antioxidant activity to the molecules. The developed models may serve as indispensable query tools for screening untested molecules belonging to the class of coumarin derivatives.

  14. Synthesis, NMR characterization, X-ray structural analysis and theoretical calculations of amide and ester derivatives of the coumarin scaffold

    Science.gov (United States)

    Matos, Maria J.; Uriarte, Eugenio; Santana, Lourdes; Vilar, Santiago

    2013-06-01

    Compounds 1 (4-methyl-N-(coumarin-3-yl)benzamide) and 2 ((coumarin-3-yl)-4-methylbenzoate) were synthesized by linking the coumarin system (3-aminocoumarin or 3-hydroxycoumarin, respectively) to a p-toluoylchloride. 1H and 13C NMR and X-ray diffractometry determined the molecular structures of both derivatives. The X-ray results were compared to those obtained by conformational analysis followed by semiempirical methodologies (AM1 and PM3). The theoretical calculations yielded results reproducing the whole three-dimensional (3D) structure of both molecules in a good agreement with X-ray structural analysis. The global structures of the two compounds are very similar in the two studied environments, meaning that the structural determination in the gas phase can be extrapolated. A comparative study between compounds 1 and 2, based on the structural results, was carried out.

  15. Evaluation of the interaction of coumarins with biomembrane models studied by differential scanning calorimetry and Langmuir-Blodgett techniques.

    Science.gov (United States)

    Sarpietro, Maria Grazia; Giuffrida, Maria Chiara; Ottimo, Sara; Micieli, Dorotea; Castelli, Francesco

    2011-04-25

    Three coumarins, scopoletin (1), esculetin (2), and esculin (3), were investigated by differential scanning calorimetry and Langmuir-Blodgett techniques to gain information about the interaction of these compounds with cellular membranes. Phospholipids assembled as multilamellar vesicles or monolayers (at the air-water interface) were used as biomembrane models. Differential scanning calorimetry was employed to study the interaction of these coumarins with multilamellar vesicles and to evaluate their absorption by multilamellar vesicles. These experiments indicated that 1-3 interact in this manner to different extents. The Langmuir-Blodgett technique was used to study the effect of these coumarins on the organization of phospholipids assembled as a monolayer. The data obtained were in agreement with those obtained in the calorimetric experiments.

  16. The influence of naphthaleneacetic acid (NAA) and coumarin on flavonoid production by fungus Phellinus sp.: modeling of production kinetic profiles.

    Science.gov (United States)

    Ma, Xiao-Kui; Li, Le; Peterson, Eric Charles; Ruan, Tingting; Duan, Xiaoyi

    2015-11-01

    For the purpose of improving the fungal production of flavonoids, the influence of naphthaleneacetic acid (NAA) and coumarin on flavonoid production by fungus Phellinus sp. P0988 was investigated by developing the corresponding kinetics of flavonoid production in a 7-L bioreactor. Phellinus sp. was confirmed to form flavonoids in pellets and broth when cultivated in basic medium, and the optimum concentration of NAA and coumarin in medium for flavonoid production were determined to be 0.03 and 0.02 g/L, respectively. The developed unstructured mathematical models were in good agreement with the experimental results with respect to flavonoid production kinetic profiles with NAA and coumarin supplementation at optimum levels and revealed significant accuracy in terms of statistical consistency and robustness. Analysis of these kinetic processes indicated that NAA and coumarin supplementations imposed a stronger positive influence on flavonoid production and substrate consumption compared to their effects on cell growth. The separate addition of NAA and coumarin resulted in enhancements in final product accumulation and productivity, achieving final flavonoid concentrations of 3.60 and 2.75 g/L, respectively, and glucose consumption showed a significant decrease compared to the non-supplemented control as well. Also, the separate presence of NAA and coumarin respectively decreased maintenance coefficients (M s) from 2.48 in the control to 1.39 and 0.22, representing decreases of 43.9 and 91.1 %, respectively. The current study is the first known application of mathematical kinetic models to explore the influence of medium components adding on flavonoid production by fungi.

  17. Effect of coumarins started before coronary angioplasty on acute complications and long-term follow-up: a randomized trial.

    Science.gov (United States)

    ten Berg, J M; Kelder, J C; Suttorp, M J; Mast, E G; Bal, E; Ernst, S M; Verheugt, F W; Plokker, H W

    2000-07-25

    Coronary angioplasty frequently creates a thrombogenic surface, with subsequent mural thrombosis that may lead to acute complications and possibly stimulates the development of restenosis. Whether coumarins can prevent these complications is unclear. The objective of this open, randomized trial was to assess the clinical effect of coumarins started before coronary angioplasty and continued for 6 months. Before coronary angioplasty, 530 patients were randomly assigned to aspirin plus coumarins and 528 patients to aspirin alone. At the start of the angioplasty, the mean international normalized ratio was 2.7+/-1.1; during follow-up, it was 3.0+/-1.1. At 30 days, the composite end point of death, myocardial infarction, target-lesion revascularization, and stroke was observed in 18 patients (3.4%) treated with aspirin plus coumarin compared with 34 patients (6.4%) treated with aspirin alone (relative risk, 0.53; 95% CI, 0.30 to 0.92). At 1 year, these figures were 14.3% and 20.3%, respectively (relative risk, 0.71; 95% CI, 0.54 to 0.93). The incidence of major bleeding and false aneurysm during hospitalization was 3.2% and 1.0%, respectively (relative risk, 3.39; 95% CI, 1.26 to 9.11). The benefit of coumarins was observed in both stented and nonstented patients. Coumarins in addition to aspirin started before PTCA and continued for 6 months was more effective than aspirin alone in the prevention of acute and late complications after coronary angioplasty. This benefit was accompanied by a small but significant increase in bleeding complications.

  18. Comparison of coumarin-induced toxicity between sandwich-cultured primary rat hepatocytes and rats in vivo: a toxicogenomics approach.

    Science.gov (United States)

    Kienhuis, Anne S; Wortelboer, Heleen M; Hoflack, Jean-Christophe; Moonen, Edwin J; Kleinjans, Jos C S; van Ommen, Ben; van Delft, Joost H M; Stierum, Rob H

    2006-12-01

    Sandwich-cultured primary rat hepatocytes are often used as an in vitro model in toxicology and pharmacology. However, loss of liver-specific functions, in particular, the decline of cytochrome P450 (P450) enzyme activity, limits the value of this model for prediction of in vivo toxicity. In this study, we investigated whether a hepatic in vitro system with improved metabolic competence enhances the predictability for coumarin-induced in vivo toxicity by using a toxicogenomics approach. Therefore, primary rat hepatocytes were cultured in sandwich configuration in medium containing a mixture of low concentrations of P450 inducers, phenobarbital, dexamethasone, and beta-naphthoflavone. The toxicogenomics approach used enabled comparison of similar mechanistic end-points at the molecular level between in vitro and in vivo conditions, namely, compound-induced changes in multiple genes and signaling pathways. Toxicant-induced cytotoxic effects and gene expression profiles observed in hepatocytes cultured in modified medium and hepatocytes cultured in standard medium (without inducers) were compared with results from a rat in vivo study. Coumarin was used as a model compound because its toxicity depends on bioactivation by P450 enzymes. Metabolism of coumarin toward active metabolites, coumarin-induced cytotoxicity, and gene expression modulation were more pronounced in hepatocytes cultured in modified medium compared with hepatocytes cultured in standard medium. In addition, more genes and biological pathways were similarly affected by coumarin in hepatocytes cultured in modified medium and in vivo. In conclusion, these experiments showed that for coumarin-induced toxicity, sandwich-cultured hepatocytes maintained in modified medium better represent the situation in vivo compared with hepatocytes cultured in standard medium.

  19. Anticholinesterase activity evaluation of alkaloids and coumarin from stems of Conchocarpus fontanesianus

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    Rodrigo S. Cabral

    2012-04-01

    Full Text Available Conchocarpus fontanesianus (A. St.-Hill. Kallunki & Pirani, Rutaceae, popularly known as pitaguará, is a native and endemic tree from São Paulo and Rio de Janeiro States, Brazil. Based in the information that anticholinesterasic derivatives could act as new prototypes to treatment of Alzheimer disease, this work describes the fractionation guided by evaluation of the anticholinesterase activity of the ethanolic stems extract from C. fontanesianus. This procedure afforded the alkaloids dictamnine (1, γ-fagarine (2, skimianine (3, and 2-phenyl-1-methyl-4-quinolone (4, as well as the coumarin marmesin (5.

  20. TD-DFT study of the pKa∗ for coumarins

    Science.gov (United States)

    Houari, Ymène; Jacquemin, Denis; Laurent, Adèle D.

    2013-09-01

    The excited state acid dissociation constants (pKa∗) of a panel of five coumarins have been studied using several PCM-TD-DFT protocols including both vibrational and state-specific (SS) effects. The pKa∗ have been calculated using the excited state thermodynamical cycle and the Förster cycle. For this set of compounds the addition of explicit water molecules does not improve the computed acidity constants computed with the thermodynamical cycle. However, the addition of explicit water molecules to the PCM model apparently improves the quality of the optical spectra and hence the Förster estimates. State specific effects do not bring significant improvements in this case.

  1. Synthesis of modified pyridine and bipyridine substituted coumarins as potent antimicrobial agents

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    Lad Hemali B.

    2015-01-01

    Full Text Available In search for new antimicrobial agents a series of new modified pyridine and bipyridine substituted coumarins 5a-y was designed and synthesized by adopting molecular hybridization strategy. All the synthesized compounds were evaluated for their in vitro antimicrobial activity using broth dilution method against selected bacterial (Gram-positive and Gram-negative and fungal strains. Compounds 5a, 5f, 5g, 5n, 5r, 5t, 5w, 5x and 5y demonstrated promising antibacterial activity while other derivatives showed comparable activity to standard drugs used as reference.

  2. Novel coumarin-based fluorescent probe for selective detection of Cu(II)

    Science.gov (United States)

    Bekhradnia, Ahmadreza; Domehri, Elham; Khosravi, Masome

    2016-01-01

    We report an efficient and convenient method for preparing nitro-3-carboxamide coumarin derivatives, proposed as novel fluorescent chemosensor, through microwave irradiation. This compound can be used as fluorescent probe for Cu2+ with selectivity over other metal ions in aqueous solution. The fluorescence of 6-nitro-N-[2-(dimethylamino)ethyl]-2-oxo-2H-chromene-3-carboxamide(3) is the highest in the presence of Cu2+, with stronger excitation at λ = 320 nm than for the other cations tested.

  3. Solid State Dye Lasers Based on Coumarin 440 and Pyrromethene 567 Codoped Polymethyl Methacrylate

    Institute of Scientific and Technical Information of China (English)

    FAN Rong-Wei; LI Xiao-Hui; XIA Yuan-Qin; JIANG Yu-Gang; HE Wei-Ming; CHEN De-Ying

    2008-01-01

    Laser dye coumarin 440(C440) is codoped with pyrromethene 567 (PM567) into polymethyl methacrylate (PMMA ).The effects of C440 concentration on the performance of the solid state dye medium,including spectra property,slope efficiency and photostability,are studied.When C440 is codoped with PM567 at the same concentration 1 × 10-4 mol/L,the highest efficiency and photostability can be obtained.Compared with the medium based on pure PM567 doped PMMA,about 50% increase in slope efficiency and at least five-fold enhancement in the photostabifity are observed.

  4. Colorimetric and fluorescence detection of G-quadruplex nucleic acids with a coumarin-benzothiazole probe.

    Science.gov (United States)

    Yan, Jin-wu; Tian, Yi-guang; Tan, Jia-heng; Huang, Zhi-shu

    2015-11-01

    A colorimetric and red-emitting fluorescent dual probe for G-quadruplexes was devised with a conjugated coumarin-benzothiazole scaffold. Its significant and distinct changes in both color and fluorescence enable the label-free and visual detection of G-quadruplex structures. In addition, this probe gives a distinct strong emission response to the nucleoli in fixed cells imaging, which might be attributed to the interaction between the probe and rDNA G-quadruplex based on the chromatin immunoprecipitation assay. All these results suggest its promising application prospects in the G-quadruplex research field.

  5. Coumarin Antifungal Lead Compounds from Millettia thonningii and Their Predicted Mechanism of Action

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    Daniel M. Ayine-Tora

    2016-10-01

    Full Text Available Fungal pathogens continue to pose challenges to humans and plants despite efforts to control them. Two coumarins, robustic acid and thonningine-C isolated from Millettia thonningii, show promising activity against the fungus Candida albicans with minimum fungicidal concentration of 1.0 and 0.5 mg/mL, respectively. Molecular modelling against the putative bio-molecular target, lanosterol 14α-demethylase (CYP51, revealed a plausible binding mode for the active compounds, in which the hydroxyl group binds with a methionine backbone carboxylic group blocking access to the iron catalytic site. This binding disrupts the synthesis of several important sterols for the survival of fungi.

  6. Synthesis of new conjugated coumarin-benzimidazole hybrids and their anticancer activity.

    Science.gov (United States)

    Paul, Kamaldeep; Bindal, Shweta; Luxami, Vijay

    2013-06-15

    A series of novel coumarin-benzimidazole hybrids, 3-(1H-benzo[d]imidazol-2-yl)-7-(substituted amino)-2H-chromen-2-one derivatives of biological interest were synthesized. Six out of the newly synthesized compounds were screened for in vitro antitumor activity against preliminary 60 tumor cell lines panel assay. A significant inhibition for cancer cells was observed with compound 8 (more than 50% inhibition) compared with other compounds and active known drug 5-fluorouracil (in some cell lines) as positive control. Compound 8 displayed appreciable anticancer activities against leukemia, colon cancer and breast cancer cell lines.

  7. Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata

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    Xiang-Mei Li

    2016-09-01

    Full Text Available Abstract Four hitherto unknown prenylated coumarins, namely 6″-O-β-d-apiofuranosylapterin (1, 4′-O-isobutyroylpeguangxienin (2, 6-(3-methyl-2-oxobutyroyl-7-methoxycoumarin (3, and 6-hydroxycoumurrayin (4, were isolated from the ethanol extract of Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata, respectively. Their chemical structures were established on the basis of extensive spectroscopic analysis. Compound 2 exhibited in vitro cytotoxic activity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480 with IC50 values ranging from 15.9 to 23.2 μM. Graphical Abstract

  8. Synthesis of (iso)quinoline, (iso)coumarin and (iso)chromene derivatives from acetylene compounds

    Science.gov (United States)

    Ryabukhin, D. S.; Vasilyev, A. V.

    2016-06-01

    Published data on the methods of synthesis of quinoline, isoquinoline, coumarin, isocoumarin, chromene and isochromene derivatives from acetylene compounds are summarized. The reactions catalyzed by metal complexes (Pd, Pt, Ru, Rh, Au, Ag, Ni, Cu, etc.) and transformations induced by various electrophilic reagents (Brynsted and Lewis acids) are considered. Moieties of the mentioned heterocyclic systems are present in many biologically active natural products and pharmaceutical agents. Besides, derivatives of these heterocycles are used in the manufacture of catalysts, dyes, perfumery and cosmetic products, corrosion inhibitors and so on. The bibliography includes 211 references.

  9. Synthesis and biological activity of some heterocyclic compounds containing quinoxaline and coumarin moieties

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    M. E. ABD EL-FATTAH

    2000-02-01

    Full Text Available 2,3-Dichloroquinoxaline (2 condensed with 7,8-dihydroxy-4-methylcoumarin to give the 1,4-dioxane derivative 4. 2.3-Dichloroquinoxaline (2 reacted with 4-hydroxycoumarin, 7-hydroxy-4-methylcoumarin and acyl hydrazide 13 to give either the 2,3-(dicoumarin-4-yloxyquinoxaline (6 or the 2,3-di-(4-methylcoumarin-7-yloxyquinoxaline (7 or the 2-chloro-3-(coumarin-4-yloxyquinoxaline (8 or the 2-chloro-3-(4-methylcoumarin-7-yloxy quinoxaline (9 or the ditriazoloquinoxaline 14 or the oxa-diazinoquinoxaline 16, depending on the relative ratios of the reactants and the reaction conditions.

  10. Rational Design, Synthesis and Evaluation of Coumarin Derivatives as Protein-protein Interaction Inhibitors.

    Science.gov (United States)

    De Luca, Laura; Agharbaoui, Fatima E; Gitto, Rosaria; Buemi, Maria Rosa; Christ, Frauke; Debyser, Zeger; Ferro, Stefania

    2016-09-01

    Herein we describe the design and synthesis of a new series of coumarin derivatives searching for novel HIV-1 integrase (IN) allosteric inhibitors. All new obtained compounds were tested in order to evaluate their ability to inhibit the interaction between the HIV-1 IN enzyme and the nuclear protein lens epithelium growth factor LEDGF/p75. A combined approach of docking and molecular dynamic simulations has been applied to clarify the activity of the new compounds. Specifically, the binding free energies by using the method of molecular mechanics-generalized Born surface area (MM-GBSA) was calculated, whereas hydrogen bond occupancies were monitored throughout simulations methods.

  11. Asimafoetidnol: a new sesquiterpenoid coumarin from the gum resin of Ferula assa-foetida.

    Science.gov (United States)

    Bandyopadhyay, Debasish; Banerjeeb, Manas; Laskar, Subrata; Basak, Bidyut

    2011-02-01

    Chemical investigation of the gum resin of Ferula assa-foetida L. resulted in the isolation of a new sesquiterpenoid coumarin, 7-(((E)-5-((1S,3S,6S)-3,6-dihydroxy-2,2,6-trimethylcyclohexyl)-3-methylpent-2-en-1-yl)oxy)-2H-chromen-2-one (asimafoetidnol), together with several other known compounds. The structure of asimafoetidnol was established on the basis of spectroscopic analyses. Geometry optimization of the compound has been carried out using a DFT/B3LYP/3-21G* method.

  12. Interest of antioxidant agents in parasitic diseases. The case study of coumarins.

    Science.gov (United States)

    Figueroa-Guiñez, Roberto; Matos, Maria João; Vazquez-Rodriguez, Saleta; Santana, Lourdes; Uriarte, Eugenio; Borges, Fernanda; Olea-Azar, Claudio; Maya, Juan Diego

    2015-01-01

    Tropical parasitic diseases, especially those produced by protozoan parasites, are a major public health problem in many countries, and their impact in the health burden is significant. Oxidative processes proved to be related to these diseases, being the antioxidant agents promising therapeutic solutions for them. Therefore, this review provides an overview of published manuscripts regarding both activities. In particular, the interest of the coumarin derivatives as antioxidant agents with application in parasitic diseases is discussed in this manuscript. The recent findings in this field are highlighted.

  13. Prenylated Coumarins from Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata.

    Science.gov (United States)

    Li, Xiang-Mei; Jiang, Xian-Jun; Yang, Ku; Wang, Li-Xia; Wen, Shi-Zhen; Wang, Fei

    2016-10-01

    Four hitherto unknown prenylated coumarins, namely 6″-O-β-D-apiofuranosylapterin (1), 4'-O-isobutyroylpeguangxienin (2), 6-(3-methyl-2-oxobutyroyl)-7-methoxycoumarin (3), and 6-hydroxycoumurrayin (4), were isolated from the ethanol extract of Heracleum stenopterum, Peucedanum praeruptorum, Clausena lansium, and Murraya paniculata, respectively. Their chemical structures were established on the basis of extensive spectroscopic analysis. Compound 2 exhibited in vitro cytotoxic activity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480) with IC50 values ranging from 15.9 to 23.2 μM.

  14. Synthesis and biological activity of some heterocyclic compounds containing quinoxaline and coumarin moieties

    OpenAIRE

    M. E. ABD EL-FATTAH; I. M. EL-DEEN

    2000-01-01

    2,3-Dichloroquinoxaline (2) condensed with 7,8-dihydroxy-4-methylcoumarin to give the 1,4-dioxane derivative 4. 2.3-Dichloroquinoxaline (2) reacted with 4-hydroxycoumarin, 7-hydroxy-4-methylcoumarin and acyl hydrazide 13 to give either the 2,3-(dicoumarin-4-yloxy)quinoxaline (6) or the 2,3-di-(4-methylcoumarin-7-yloxy)quinoxaline (7) or the 2-chloro-3-(coumarin-4-yloxy)quinoxaline (8) or the 2-chloro-3-(4-methylcoumarin-7-yloxy) quinoxaline (9) or the ditriazoloquinoxaline 14 or the oxa-diazi...

  15. Design, synthesis and biological evaluation of novel coumarin thiazole derivatives as α-glucosidase inhibitors.

    Science.gov (United States)

    Wang, Guangcheng; He, Dianxiong; Li, Xin; Li, Juan; Peng, Zhiyun

    2016-04-01

    A new series of coumarin thiazole derivatives 7a-7t were synthesized, characterized by (1)H NMR, (13)C NMR and element analysis, evaluated for their α-glucosidase inhibitory activity. The majority of the screened compounds displayed potent inhibitory activities with IC50 values in the range of 6.24±0.07-81.69±0.39μM, when compared to the standard acarbose (IC50=43.26±0.19μM). Structure-activity relationship (SAR) studies suggest that the pattern of substitution in the phenyl ring is closely related to the biological activity of this class of compounds. Among all the tested molecules, compound 7e (IC50=6.24±0.07μM) was found to be the most active compound in the library of coumarin thiazole derivatives. Enzyme kinetic studies showed that compound 7e is a non-competitive inhibitor with a Ki of 6.86μM. Furthermore, the binding interactions of compound 7e with the active site of α-glucosidase were confirmed through molecular docking. This study has identified a new class of potent α-glucosidase inhibitors for further investigation.

  16. Zirconia-based catalyst for the one-pot synthesis of coumarin through Pechmann reaction

    Science.gov (United States)

    Khan, Shahid Ali; Khan, Sher Bahadar; Asiri, Abdullah M.; Ahmad, Ikram

    2016-07-01

    Coumarins play an important role in drug development with diverse biological applications. Herein, we present the synthesis of coumarin through Pechmann reaction by using zirconia-based heterogeneous catalysts (ZrO2-TiO2, ZrO2-ZnO, and ZrO2/cellulose) in a solvent-free condition at room temperature. ZrO2-TiO2, ZrO2-ZnO, and ZrO2/cellulose were identified through spectroscopic techniques such as FESEM, X-ray, EDS, XPS, and FT-IR. ZrO2-TiO2 showed the best catalytic performance while ZrO2/cellulose was inactive. The kinetic parameters were observed in a solvent-free condition as well as in toluene and ethanol. The temperature effect was extensively studied which revealed that increasing the temperature will increase the rate of reaction. The rate of reaction in a solvent-free condition, ethanol, and toluene were 1.7 × 10-3, 1.7 × 10-2, and 5.6 × 10-3 g mol-1 min-1, respectively.

  17. Fluorescence quenching of coumarin 153 by hydroxyl-functionalized room temperature ionic liquids

    Science.gov (United States)

    Li, Shuang; Yu, Anchi; Lu, Rong

    2016-08-01

    Steady-state absorption and fluorescence as well as time-resolved fluorescence of coumarin 151 (C151) and coumarin 153 (C153) were measured in hydroxyl-functionalized ionic liquids ([HOEmim][BF4] and [HOEmim][N(CN)2]) and in nonhydroxyl-functionalized ionic liquids ([Emim][BF4] and [Emim][N(CN)2]). Both the steady-state fluorescence and time-resolved fluorescence observations reveal that hydroxyl-functionalized ionic liquid quenches the fluorescence of C153 while the nonhydroxyl-functionalized ionic liquid does not. We also measured the time-resolved fluorescence anisotropy of C151 and C153 in both [HOEmim][BF4] and [Emim][BF4]. It is found that the ratio of the rotational relaxation lifetime of C153 in [HOEmim][BF4] with respect to that in [Emim][BF4] is about 15% larger than that of C151 in [HOEmim][BF4] with respect to that in [Emim][BF4], indicating extra interaction between C153 and [HOEmim][BF4] exists except the effect of the viscosity of ionic liquid.

  18. Formation and control of excimer of a coumarin derivative in Langmuir–Blodgett films

    Energy Technology Data Exchange (ETDEWEB)

    Chakraborty, Santanu; Bhattacharjee, D.; Hussain, Syed Arshad, E-mail: sa_h153@hotmail.com

    2014-01-15

    In this communication we report the formation and control of excimer of a coumerin derivative 7-Hydroxy-N-Octadecyl Coumarin-3-Carboxamide (7HNO3C) assembled onto Langmuir–Blodgett (LB) films. Surface pressure–area per molecule isotherm revealed that 7HNO3C formed stable Langmuir monolayer at the air–water interface. Spectroscoipic characterizations confirmed the formation of excimer of 7HNO3C in the LB film prepared at 20 mN/m surface pressure. The excimer band remains present even when 7HNO3C molecules are diluted with a long chain fatty acid stearic acid in LB films. The excimer formation of 7HNO3C can be controlled by incorporating clay particle laponite in the LB film. The excimer band is totally absent in the hybrid 7HNO3C–laponite LB films. In-situ fluorescence imaging microscopy and atomic force microscopy confirmed the incorporation of clay laponite onto LB films. -- Highlights: • Formation of Langmuir monolayer and Langmuir–Blodgett (LB) film of a coumarin derivative. • Presence of excimeric species in the LB film lifted at 20 mN/m surface pressure is confirmed from the spectroscopic studies. • Control of excimer formation by incorporating clay particle laponite on to the LB film. • In-situ fluorescence imaging microscopy and atomic force microscopy confirmed the incorporation of clay laponite onto LB films.

  19. Rigid Coumarins: a Complete DFT, TD-DFT and Non Linear Optical Property Study.

    Science.gov (United States)

    Lanke, Sandip K; Sekar, Nagaiyan

    2015-09-01

    The electronic structures and photophysical properties of rigid coumarin dyes have been studied by using quantum chemical methods. The ground-state geometries of these dyes were optimized using the Density Functional Theory (DFT) methods. The lowest singlet excited state was optimized using Time -Dependent Density Functional Theory [TD-B3LYP/6-31G(d)]. On the basis of ground- and excited-state geometries, the absorption and emission spectra have been calculated using the DFT and TD-DFT method. All the calculations were carried out in gas phase and in acetonitrile medium. The results show that the absorption maxima and fluorescence emission maxima calculated using the Time-Dependent Density Functional Theory is in good agreement with the available experimental results. To understand the Non- Linear Optical properties of coumarin dyes we computed dipole moment (μ), electronic polarizability (α), mean first hyperpolarizability (βo) and second hyperpolarizability (γ) using B3LYP density functional theory method in conjunction with 6-31G(d) basis set.

  20. A new ester coumarin from Ferula Persica wild, indigenous to Iran.

    Science.gov (United States)

    Razavi, Seyed Mehdi; Janani, Mehrnoush

    2015-01-01

    Ferula persica wild (Apiaceae) is a perennial herb indigenous to Iran. It has been used in folk medicine for treatment of diabetes, lowering of blood pressure and for antispasmodic, carminative, laxative and expectorant effects in central Iran. Dried ground roots of F. persica (150 g) were extracted sequentially with n-hexane, dichloromethane and methanol (MeOH), 500 ml each, using a Soxhlet apparatus. The n-hexane extract of the roots (3 g) was subjected to vacuum liquid chromatography on silica gel, eluting with solvent mixtures of increasing polarity: 100% n-hexane-ethyl acetate (EtOAc), to yield a number of fractions, Fraction 4 (80% EtOAc in n-hexane) was further analysed by preparative TLC (mobile phase was 12% acetone in chloroform) to yield a coumarin ester (10.1 mg, Rf = 0.31, blue florescent). The structure of the isolated compound was elucidated by spectroscopic means. The compound is 7-O-(4,8,12 -trihydroxy-4,8,12-trimethyl-tridecanoyl)-coumarin, named, ferulone C as a new natural product.

  1. Rapid Identification of Coumarins from Micromelum falcatum by UPLC-HRMS/MS and Targeted Isolation of Three New Derivatives

    Directory of Open Access Journals (Sweden)

    Eirini Kouloura

    2014-09-01

    Full Text Available Micromelum falcatum, a medicinal plant of the Rutaceae family, has been used in the Traditional Chinese Medicine (TCM mainly against colds and rheumatoid arthritis. Despite its traditional use the association of its constituents with possible anti-inflammatory activity has not been explored. During this study, a rapid UPLC-ESI(+-HRMS method was developed for the profiling of M. falcatum leave extracts and the targeted isolation of coumarin constituents. Based on chromatographic, spectroscopic and spectrometric features several 7-oxygenated coumarin derivatives were detected. After targeted isolation, eight coumarins, among them three new natural products, namely microfalcrin, microcoumaririn and micromelosidester, were purified using semi-preparative HPLC and unambiguously identified by 1 and 2D NMR. Furthermore, important spectrometric characteristics were revealed based on the HRMS and HRMS/MS spectra of the isolated 7-oxygenated coumarins facilitating their identification in complex mixtures. Finally, the anti-inflammatory properties of the extracts and representative compounds were evaluated by measuring the inhibition of the pro-inflammatory mediator NF-κB induction and nitric oxide (NO production.

  2. Optopharmacological control of TRPC channels by coumarin-caged lipids is associated with a phototoxic membrane effect.

    Science.gov (United States)

    Tiapko, Oleksandra; Bacsa, Bernadett; de la Cruz, Gema Guedes; Glasnov, Toma; Groschner, Klaus

    2016-08-01

    Photouncaging of second messengers has been successfully employed to gain mechanistic insight of cellular signaling pathways. One of the most enigmatic processes of ion channel regulation is lipid recognition and lipid-gating of TRPC channels, which represents pivotal mechanisms of cellular Ca(2+) homeostasis. Recently, optopharmacological tools including caged lipid mediators became available, enabling an unprecedented level of temporal and spatial control of the activating lipid species within a cellular environment. Here we tested a commonly used caged ligand approach for suitability to investigate TRPC signaling at the level of membrane conductance and cellular Ca(2+) handling. We report a specific photouncaging artifact that is triggered by the cage structure coumarin at UV illumination. Electrophysiological characterization identified a light-dependent membrane effect of coumarin. UV light (340 nm) as used for photouncaging, initiated a membrane conductance specifically in the presence of coumarin as low as 30 μmol L(-1) concentrations. This conductance masked the TRPC3 conductance evoked by photouncaging, while TRPC-mediated cellular Ca(2+) responses were largely preserved. The observed light-induced membrane effects of the released caging moiety may well interfere with certain cellular functions, and prompt caution in using coumarin-caged second messengers in cellular studies.

  3. Synthesis and carbonic anhydrase inhibitory properties of amino acid - coumarin/quinolinone conjugates incorporating glycine, alanine and phenylalanine moieties.

    Science.gov (United States)

    Küçükbay, F Zehra; Küçükbay, Hasan; Tanc, Muhammet; Supuran, Claudiu T

    2016-12-01

    N-Protected amino acids (Gly, Ala and Phe) were reacted with amino substituted coumarin and quinolinone derivatives, leading to the corresponding N-protected amino acid-coumarin/quinolinone conjugates. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against various human (h) isoforms, such as hCA I, hCA II, hCA IV and hCA XII. The quinolinone conjugates were inactive as enzyme inhibitors, whereas the coumarins were ineffective hCA I/II inhibitors (KIs > 50 μM) but were submicromolar hCA IV and XII inhibitors, with inhibition constants ranging between 92 nM and 1.19 μM for hCA IV, and between 0.11 and 0.79 μM for hCA XII. These coumarin derivatives, as many others reported earlier, thus show an interesting selective inhibitory profile for the membrane-bound over the cytosolic CA isoforms.

  4. Shape-persistent macrocycles functionalised with coumarin dyes: acid-controlled energy- and electron-transfer processes.

    Science.gov (United States)

    Giansante, Carlo; Ceroni, Paola; Venturi, Margherita; Balzani, Vincenzo; Sakamoto, Junji; Schlüter, A Dieter

    2008-01-01

    We have investigated the spectroscopic properties (absorption spectra, emission spectra, emission lifetimes) of three triads in CH(2)Cl(2): C2-M-C2, C343-M-C343, and C2-M-C343, in which M is a shape-persistent macrocyclic hexagonal backbone composed of two 2,2'-bipyridine (bpy) units embedded in opposing sides, and C2 and C343 are coumarin 2 and coumarin 343, respectively. All the components are strongly fluorescent species (Phi=0.90, 0.79, and 0.93 for M, C2, and C343, respectively, as established by investigating suitable model compounds). In each triad excitation of M leads to almost quantitative energy transfer to the lowest coumarin-localised excited state. Upon addition of acid, the two bpy units of the M component undergo independent protonation leading to monoprotonated (e.g., C2-MH(+)-C2) and diprotonated (e.g., C2-M2 H(+)-C2) species. Further addition of acid leads to protonation of the coumarin component so that each triad is involved in four protonation equilibria. Protonation causes strong (and reversible, upon addition of base) changes in the absorption and fluorescence properties of the triads because of inversion of the excited-state order and/or the occurrence of electron-transfer quenching processes.

  5. Melamine-formaldehyde resin supported H+: A mild and inexpensive reagent for synthesis of coumarins under mild conditions

    Institute of Scientific and Technical Information of China (English)

    Ramin Rezaei; Leila Dorosty; Maryam Rajabzadeh; Reza Khalifeh

    2011-01-01

    Melamine-formaldehyde resin supported H+ is used as an efficient catalyst in the Pechmann condensation reaction of phenols with β-ketoesters, in solvent-free media leading to the formation of coumarin derivatives using conventional heating and microwave irradiation in excellent yields with good purity.

  6. Supercritical CO2 Extraction of Lavandula angustifolia Mill. Flowers: Optimisation of Oxygenated Monoterpenes, Coumarin and Herniarin Content.

    Science.gov (United States)

    Jerković, Igor; Molnar, Maja; Vidović, Senka; Vladić, Jelena; Jokić, Stela

    2017-07-14

    Lavandula angustifolia is good source of oxygenated monoterpenes containing coumarins as well, which are all soluble in supercritical CO2 (SC-CO2 ). The study objective is to investigate SC-CO2 extraction parameters on: the total yield; GC-MS profile of the extracts; relative content of oxygenated monoterpenes; the amount of coumarin and herniarin; and to determine optimal SC-CO2 extraction conditions by response surface methodology (RSM). SC-CO2 extraction was performed under different pressure, temperature and CO2 flow rate determined by Box-Behnken design (BBD). The sample mass and the extraction time were kept constant. The chemical profiles and relative content of oxygenated monoterpenes (as coumarin equivalents, CE) were determined by GC-MS. Coumarin and herniarin concentrations were dosed by HPLC. SC-CO2 extracts contained linalool (57.4-217.9 mg CE/100 g), camphor (10.6-154.4 mg CE/100 g), borneol (6.2-99.9 mg CE/100 g), 1,8-cineole (5.0-70.4 mg CE/100 g), linalyl acetate (86.1-267.9 mg CE/100 g), coumarin (0.95-18.16 mg/100 g), and herniarin (0.95-13.63 mg/100 g). The interaction between the pressure and CO2 flow rate as well as between the temperature and CO2 flow rate showed statistically significant influence on the extraction yield. Applying BBD, the optimum extraction conditions for higher monoterpenes and lower coumarin content were at 10 MPa, 41°C and CO2 flow rate 2.3 kg/h, and at 30 MPa, 50°C and CO2 flow rate 3 kg/h for higher monoterpenes and coumarin content. SC-CO2 extraction is a viable technique for obtaining lavender extracts with desirable flavour components. The second-order model based on BBD predicts the results for SC-CO2 extraction quite satisfactorily. Copyright © 2017 John Wiley & Sons, Ltd. Copyright © 2017 John Wiley & Sons, Ltd.

  7. In silico genotoxicity of coumarins: application of the Phenol-Explorer food database to functional food science.

    Science.gov (United States)

    Guardado Yordi, E; Matos, M J; Pérez Martínez, A; Tornes, A C; Santana, L; Molina, E; Uriarte, E

    2017-08-01

    Coumarins are a group of phytochemicals that may be beneficial or harmful to health depending on their type and dosage and the matrix that contains them. Some of these compounds have been proven to display pro-oxidant and clastogenic activities. Therefore, in the current work, we have studied the coumarins that are present in food sources extracted from the Phenol-Explorer database in order to predict their clastogenic activity and identify the structure-activity relationships and genotoxic structural alerts using alternative methods in the field of computational toxicology. It was necessary to compile information on the type and amount of coumarins in different food sources through the analysis of databases of food composition available online. A virtual screening using a clastogenic model and different software, such as MODESLAB, ChemDraw and STATISTIC, was performed. As a result, a table of food composition was prepared and qualitative information from this data was extracted. The virtual screening showed that the esterified substituents inactivate molecules, while the methoxyl and hydroxyl substituents contribute to their activity and constitute, together with the basic structures of the studied subclasses, clastogenic structural alerts. Chemical subclasses of simple coumarins and furocoumarins were classified as active (xanthotoxin, isopimpinellin, esculin, scopoletin, scopolin and bergapten). In silico genotoxicity was mainly predicted for coumarins found in beer, sherry, dried parsley, fresh parsley and raw celery stalks. The results obtained can be interesting for the future design of functional foods and dietary supplements. These studies constitute a reference for the genotoxic chemoinformatic analysis of bioactive compounds present in databases of food composition.

  8. Application of chitin and chitosan as elicitors of coumarins and fluoroquinolone alkaloids in Ruta graveolens L. (common rue).

    Science.gov (United States)

    Orlita, Aleksandra; Sidwa-Gorycka, Matylda; Paszkiewicz, Monika; Malinski, Edmund; Kumirska, Jolanta; Siedlecka, Ewa M; Łojkowska, Ewa; Stepnowski, Piotr

    2008-10-01

    Common rue (Ruta graveolens L.) accumulates various types of secondary metabolites, such as coumarins furanocoumarins, acridone and quinolone alkaloids and flavonoids. Elicitation is a tool extensively used for enhancing secondary-metabolite yields. Chitin and chitosan are examples of elicitors inducing phytoalexin accumulation in plant tissue. The present paper describes the application of chitin and chitosan as potential elicitors of secondary-metabolite accumulation in R. graveolens shoots cultivated in vitro. The simple coumarins, linear furanocoumarins, dihydrofuranocoumarins and fluoroquinolone alkaloids biosynthesized in the presence of chitin and chitosan were isolated, separated and identified. There was a significant increase in the growth rate of R. graveolens shoots in the presence of either chitin or chitosan. Moreover, the results of the elicitation of coumarins and alkaloids accumulated by R. graveolens shoots in the presence of chitin and chitosan show that both compounds induced a significant increase in the concentrations of nearly all the metabolites. Adding 0.01% chitin caused the increase in the quantity (microg/g dry weight) of coumarins (pinnarin up to 116.7, rutacultin up to 287.0, bergapten up to 904.3, isopimpinelin up to 490.0, psoralen up to 522.2, xanhotoxin up to 1531.5 and rutamarin up to 133.7). The higher concentration of chitosan (0.1%) induced production of simple coumarins (pinnarin up to 116.7 and rutacultin up to 287.0), furanocoumarins (bergapten up to 904.3, isopimpinelin up to 490.0, psoralen up to 522.2, xanhotoxin up to 1531.5) and dihydrofuranocoumarins (chalepin up to 18 and rutamarin up to 133.7). Such a dramatic increase in the production of nearly all metabolites suggests that these compounds may be participating in the natural resistance mechanisms of R. graveolens. The application of chitin- and chitosan-containing media may be considered a promising prospect in the biotechnological production of xanthotoxin

  9. In vitro inhibition effect of some dihydroxy coumarin compounds on purified human serum paraoxonase 1 (PON1).

    Science.gov (United States)

    Erzengin, Mahmut; Basaran, Ismet; Cakir, Umit; Aybey, Aynur; Sinan, Selma

    2012-11-01

    Human serum paraoxonase 1 (PON1; EC 3.1.8.1) is a high-density lipoprotein associated, calcium-dependent enzyme that hydrolyses aromatic esters, organophosphates and lactones and can protect the low-density lipoprotein against oxidation. In this study, in vitro inhibition effect of some dihydroxy coumarin compounds namely 6,7-dihydroxy-3-(2-methylphenyl)-2H-chromen-2-one (A), 6,7-dihydroxy-3-(3-methylphenyl)-2H-chromen-2-one (B) and 6,7-dihydroxy-3-(4-methylphenyl)-2H-chromen-2-one (C) on purified PON1 were investigated by using paraoxon as a substrate. PON1 was purified using two-step procedures, namely ammonium sulphate precipitation and Sepharose-4B-L-tyrosine-1-naphthylamine hydrophobic interaction chromatography. The purified enzyme had a specific activity of 11.76 U/mg. The dihydroxy coumarin derivatives of A and B compounds inhibited PON1 enzyme activity in a noncompetitive inhibition manner with K(i) of 0.0080±0.256 and 0.0003±0.018 mM values, respectively. C compound exerted an uncompetitive inhibition of PON1 enzyme activity with K(i) of 0.0010±0.173 mM. Moreover, dihydroxy coumarin derivatives of A, B and C compounds were effective inhibitors on purified human serum PON1 activity with IC(50) of 0.012, 0.022 and 0.003 mM values, respectively. IC(50) value of unsubstituted 6,7 dihydroxy coumarin was found as 0.178 mM. The present study has demonstrated that PON1 activity is very highly sensitive to studied coumarin derivatives.

  10. Synergistic of a coumarin derivative with potassium iodide on the corrosion inhibition of aluminum alloy in 1.0 M H2SO4

    Science.gov (United States)

    Mohamad, Abu Bakar; Kadhum, Abdul Amir H.; Al-Amiery, Ahmed A.; Ying, Lim Chai; Musa, Ahmed Y.

    2014-05-01

    Synergistic effects of the addition of KI on the corrosion inhibitive performance of a coumarin derivative on an aluminum alloy in 1.0 M H2SO4 at different temperatures were studied using various electrochemical measurements. Density functional theory was used to calculate the quantum chemical parameters of the coumarin derivative. The experimental results showed that the coumarin derivative is considered as a mixedtype inhibitor. The corrosion potential values were almost unchanged upon the addition of PBBC to the acidic solution. The inhibition efficiency increases with increasing inhibitor concentration and increases further in the presence of 6.02 mM KI but decreases significantly at higher temperature. The adsorption of PBBC obeyed the Langmuir isotherm, and being chemically adsorbed at lower temperatures, while physical adsorption is favoured at higher temperature. The theoretical results indicated that the coumarin derivative was adsorbed onto the surface of Al2024 through the sulfur, oxygen and nitrogen atoms.

  11. Cascade Wittig reaction-double Claisen and Cope rearrangements: one-pot synthesis of diprenylated coumarins gravelliferone, balsamiferone, and 6,8-diprenylumbelliferone

    Digital Repository Service at National Institute of Oceanography (India)

    Patre, R.E.; Shet, J.B.; Parameswaran, P.S.; Tilve, S.G.

    A cascade Wittig reaction-double Claisen and Cope rearrangements has been employed for a one-pot synthesis of diprenylated coumarins gravelliferone, balsamiferone, and 6,8-diprenylumbelliferone from a common precursor 2,4-diprenyloxybenzaldehyde...

  12. A Method for LC-MS/MS Profiling of Coumarins in Zanthoxylum zanthoxyloides (Lam.) B. Zepernich and Timler Extracts and Essential Oils

    National Research Council Canada - National Science Library

    Tine, Yoro; Renucci, Franck; Costa, Jean; Wélé, Alassane; Paolini, Julien

    2017-01-01

    .... In this work, a targeted liquid chromatography (LC) coupled with tandem mass spectrometry (MS2) was developed for the screening of 39 reference standards of coumarins and furocoumarins in essential oils and plant extracts...

  13. Bismuth triflate:A highly efficient catalyst for the synthesis of bio-active coumarin compoundsvia one-pot multi-component reaction

    Institute of Scientific and Technical Information of China (English)

    2015-01-01

    A series of coumarin-chalcone hybrid compounds and coumarins linked to pyrazoline was synthe-sized in good yield and short time using a simple and efficient method. This method involved the one-pot reaction of salicylaldehyde, an α-ketoester and an aromatic aldehyde (in the case of the coumarin-chalcone derivatives) in addition to hydrazine hydrate (in the case of the pyrazolyl cou-marins) in the presence of a catalytic amount of bismuth triflate [Bi(OTf)3, 5 mol%]. The synthesized compounds showed scavenging activity towards the free radical 2,2-diphenyl-1-picrylhydrazyl. All compounds were characterized using IR,1H NMR and13C NMR spectroscopy.

  14. Attenuating effect of bioactive coumarins from Convolvulus pluricaulis on scopolamine-induced amnesia in mice.

    Science.gov (United States)

    Malik, Jai; Karan, Maninder; Vasisht, Karan

    2016-01-01

    Convolvulus pluricaulis Chois. (Convolvulaceae) has been used in Ayurveda as Medhya Rasyana (nervine tonic) to treat various mental disorders. This study was designed to isolate the bioactive compound(s) of this plant and to evaluate their effect against scopolamine-induced amnesia. Column chromatography of the chloroform and ethyl-acetate fractions led to the isolation of three coumarins identified as scopoletin, ayapanin and scopolin. All the three compounds at 2.5, 5, 10 and 15 mg/kg, p.o. were evaluated for memory-enhancing activity against scopolamine-induced amnesia using elevated plus maze and step down paradigms. Effect on acetylcholinesterase activity in mice brain was also evaluated. Scopoletin and scopolin, in both the paradigms, significantly and dose dependently attenuated the scopolamine-induced amnesic effect. Furthermore, these compounds at 10 and 15 mg/kg exhibited activity comparable to that of standard drug, donepezil. The compounds also exhibited significant acetylcholinesterase inhibitory activity.

  15. Flavonoids, cinnamic acids and coumarins from the different tissues and medicinal preparations of Taraxacum officinale.

    Science.gov (United States)

    Williams, C A; Goldstone, F; Greenham, J

    1996-05-01

    Three flavonoid glycosides: luteolin 7-glucoside and two luteolin 7-diglucosides were isolated from dandelion flowers and leaves together with free luteolin and chrysoeriol in the flower tissue. The hydroxycinnamic acids, chicoric acid, monocaffeyltartaric acid and chlorogenic acid were found throughout the plant and the coumarins, cichoriin and aesculin were identified in the leaf extracts. This represents the first report of free chrysoeriol (luteolin 3'-methyl ether) in Taraxacum officinale agg. An earlier provisional identification of chicoric acid, chlorogenic acid, cichoriin and aesculin in a phenolic survey of the tribe Cichorieae is confirmed. Chicoric acid and the related monocaffeyltartaric acid were found to be the major phenolic constituents in flowers, roots, leaves and involucral bracts and also in the medicinal preparations tested.

  16. A coumarin-indole based colorimetric and 'turn on' fluorescent probe for cyanide

    Science.gov (United States)

    Xu, Yu; Dai, Xi; Zhao, Bao-Xiang

    2015-03-01

    A novel coumarin-indole based chemodosimeter with a simple structure was designed and prepared via a condensation reaction in high yield. The probe exhibited very high selectivity towards cyanide on both fluorescence and UV-vis spectra, which allowed it to quantitatively detect and imaging cyanide ions in organic-aqueous solution by either fluorescence enhancement or colorimetric changes. Confirmed by 1H NMR and HRMS spectra, the detection mechanism was proved to be related with the Michael addition reaction induced by cyanide ions, which blocked the intramolecular charge transfer (ICT) of the probe. Moreover, the probe was able to be utilized efficiently in a wide pH range (7.5-10) with negligible interference from other anions and a low detection limit of 0.51 μM. Application in 5 kinds of natural water source and accurate detection of cyanide in tap water solvent system also indicated the high practical significance of the probe.

  17. Isolationand structure elucidation of coumarin and cinamate derivatives from Lycium ruthenicum

    Directory of Open Access Journals (Sweden)

    Hassan Valizadeh

    2014-10-01

    Full Text Available Lyciumspecies is a popular medicinal plant in the traditional Chinese medicine and Lycium ru-thenicum is a native medicinal plant of Iran. Lycium genus has several biologically important properties too. Investigation of chemical composition of ethyl acetate extract of this plant is the goal of this study. Two coumarins (Scopoletin and Sculetin and Methyl-2-hydroxy-4-undecanoxy-trans-cinamate were isolated and characterized as the major constituents using 1H NMR, 13C NMR and FT-IR spectroscopic data, MS spectrometry, elemental analysis and by comparison with the literature values. Phytochemical investigation of Lyciumruthenicum demonstrated the presence of important biologically active compounds. This is the first phyto-chemical study of this species in Iran.

  18. Antimycobacterial activity of novel hydrazide-hydrazone derivatives with 2H-chromene and coumarin scaffold.

    Science.gov (United States)

    Angelova, Violina T; Valcheva, Violeta; Vassilev, Nikolay G; Buyukliev, Rosen; Momekov, Georgi; Dimitrov, Ivan; Saso, Luciano; Djukic, Mirjana; Shivachev, Boris

    2017-01-15

    This study reports the synthesis of new 2H-chromene or coumarin based acylhydrazones, which were evaluated for their in vitro antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and compared to the first-line antituberculosis drugs, isoniazid (INH) and ethambutol (EMB). The most active compounds 7m (MIC 0.13μM), 7o (MIC 0.15μM) and 7k (MIC 0.17μM) demonstrated antimycobacterial activity at submicromolar concentration level and remarkably minimal associated cytotoxicity in the human embryonic kidney cell line HEK-293T. Structure-activity relationship for this class of compounds has been established. Copyright © 2016 Elsevier Ltd. All rights reserved.

  19. Surface-enhanced Raman scattering of coumarin 343 on silver colloidal nanoparticles

    Science.gov (United States)

    Hussain, Shafqat; Pang, Yoonsoo

    2016-09-01

    Surface-enhanced Raman scattering (SERS) of coumarin 343 (C343) adsorbed on silver colloidal nanoparticles reduced by sodium citrate was investigated and the surface adsorption geometry of C343 on Ag was sought by optimizing C343-Ag complexes for neutral and deprotonated C343 molecules in the DFT simulations. The SERS of C343 showed a number of spectral changes upon solution pH change. We found that deprotonated C343 adsorbs on the Ag nanoparticles through the carboxylate group keeping a perpendicular geometry to the surface. When protonated, the adsorption geometry of C343 is changed into more or less flat to the surface as the cyclic ester group becomes a preferred surface adsorption site.

  20. Fluorescent coumarin-based probe for cysteine and homocysteine with live cell application

    Science.gov (United States)

    Wei, Ling-Fang; Thirumalaivasan, Natesan; Liao, Yu-Cheng; Wu, Shu-Pao

    2017-08-01

    Cysteine (Cys) and homocysteine (Hcy) are two of important biological thiols and function as important roles in several biological processes. The development of Cys and Hcy probes will help to explore the functions of biothiols in biological systems. In this work, a new coumarin-based probe AC, containing an acryloyl moiety, was developed for Cys and Hcy detection in cells. Cys and Hcy undergo a nucleophilic addition and subsequent cyclization reaction to remove to the acryloyl group and yield a fluorescent product, 7-hydroxylcomuarin. The probe AC showed good selectivity for cysteine and homocysteine over glutathione and other amino acids and had low detection limits of 65 nM for Cys and 79 nM for Hcy, respectively. Additionally, confocal imaging experiments demonstrated that the probe AC can be applied to visualize Cys and Hcy in living cells.

  1. Sesquiterpene coumarin and sesquiterpene chromone derivatives from Ferula ferulaeoides (Steud.) Korov.

    Science.gov (United States)

    Meng, He; Li, Guoyu; Huang, Jian; Zhang, Ke; Wang, Hangyu; Wang, Jinhui

    2013-04-01

    Five novel compounds - three sesquiterpene coumarin derivatives, ferulin A (1), B (2), and C (3), and two sesquiterpene chromone derivatives, ferulin D (4) and E (5), together with eleven known compounds (6-16) have been isolated from the roots of Ferula ferulaeoides (Steud.) Korov. Their structures were established by comprehensive spectroscopic analysis. The biosynthetic pathways leading to these compounds were proposed. The cytotoxicity of all these isolates against HepG2, MCF-7, and C6 cancer cell lines was evaluated and compound 7 displayed the highest potency against HepG2, MCF-7, and C6 with IC50 values 39.9 μM, 37.7 μM, and 16.0 μM, respectively. Copyright © 2013 Elsevier B.V. All rights reserved.

  2. Antidotes to coumarins, isoniazid, methotrexate and thyroxine, toxins that work via metabolic processes.

    Science.gov (United States)

    Bateman, D Nicholas; Page, Colin B

    2016-03-01

    Some toxins cause their effects by affecting physiological processes that are fundamental to cell function or cause systemic effects as a result of cellular interaction. This review focuses on four examples, coumarin anticoagulants, isoniazid, methotrexate and thyroxine from the context of management of overdose as seen in acute general hospitals. The current basic clinical pharmacology of the toxin, the clinical features in overdose and evidence base for specific antidotes are discussed. The treatment for this group is based on an understanding of the toxic mechanism, but studies to determine the optimum dose of antidote are still required in all these toxins except thyroxine, where treatment dose is based on symptoms resulting from the overdose.

  3. Ab-Initio Calculation of Molecular Aggregation Effects: a Coumarin-343 Case Study

    CERN Document Server

    Lee, Donghyun; Sarovar, Mohan; Whaley, K Birgitta

    2013-01-01

    We present time-dependent density functional theory (TDDFT) calculations for single and dimerized Coumarin-343 molecules in order to investigate the quantum mechanical effects of chromophore aggregation in extended systems designed to function as a new generation of sensors and light-harvesting devices. Using the single-chromophore results, we describe the construction of effective Hamiltonians to predict the excitonic properties of aggregate systems. We compare the electronic coupling properties predicted by such effective Hamiltonians to those obtained from TDDFT calculations of dimers, and to the coupling predicted by the transition density cube (TDC) method. We determine the accuracy of the dipole-dipole approximation and TDC with respect to the separation distance and orientation of the dimers. In particular, we investigate the effects of including Coulomb coupling terms ignored in the typical tight-binding effective Hamiltonian. We also examine effects of orbital relaxation which cannot be captured by e...

  4. Tetracyclic triterpenoids and terpenylated coumarins from the bark of Ailanthus altissima ("Tree of Heaven").

    Science.gov (United States)

    Hong, Zhi-Lai; Xiong, Juan; Wu, Shi-Biao; Zhu, Jing-Jing; Hong, Jun-Lin; Zhao, Yun; Xia, Gang; Hu, Jin-Feng

    2013-02-01

    Tetracyclic triterpenoids (named as altissimanins A-E, 1-5) and a terpenylated coumarin (denominated as altissimacoumarin G, 6), along with fifteen known compounds (7-21) were isolated from the bark of Ailanthus altissima. Structures of compounds 1-6 were established by spectroscopic methods and chemical transformations. Altissimanin A (1) is a tirucallane-type triterpenoid bearing an uncommon oxetane ring in the side-chain, while altissimanins D (4) and E (5) are two unprecedented dimers each consisting of one tirucallane-type and one dammarane-type triterpenoid moiety. All the isolates were evaluated for their cytotoxic effects against a small panel of human cancer cell lines. Copyright © 2012 Elsevier Ltd. All rights reserved.

  5. Antibacterial activity of crude extracts from Mexican medicinal plants and purified coumarins and xanthones.

    Science.gov (United States)

    Yasunaka, Kakuko; Abe, Fumiko; Nagayama, Ariaki; Okabe, Hikaru; Lozada-Pérez, Lucio; López-Villafranco, Edith; Muñiz, Elizabeth Estrada; Aguilar, Abigail; Reyes-Chilpa, Ricardo

    2005-02-28

    Thirty-two extracts from 22 Mexican medicinal plants of 15 different families were assayed to determine their antibacterial activity against Escherichia coli and Staphylococcus aureus. Seventeen plants showed antibacterial activity, while five plants showed no activity against both bacteria. All of the extracts showed higher activity against Staphylococcus aureus (methicillin-sensitive and methicillin-resistant) than against Escherichia coli, except one. Among the plants examined, Bursera simaruba (L.) Sarg. (Burseraceae), Haematoxylum brasiletto H. Karst. (Fabaceae), Calophyllum brasiliense Cambess. (Clusiaceae), and Mammea americana L. (Clusiaceae) were highly active against Staphylococcus aureus. Coumarins (mammea A/BA and mammea A/AA) and xanthones, namely jacareubin and 1,3,5,6-tetrahydroxy-2-(3,3-dimethylallyl) xanthone, were isolated as the principle compounds from the last two plants.

  6. Electrochemiluminescence Study of Europium (III Complex with Coumarin3-Carboxylic Acid

    Directory of Open Access Journals (Sweden)

    Stefan Lis

    2008-01-01

    Full Text Available The europium (III complex of coumarin-3-carboxylic acid (C3CA has been prepared and characterized on the basis of elemental analysis, IR, and emission (photoluminescence and electrochemiluminescence spectroscopy. The synthesised complex having a formula Eu(C3CA2(NO3(H2O2 was photophysically characterized in solution and in the solid state. Electrochemiluminescence, ECL, of the system containing the Eu(III/C3CA complex was studied using an oxide-covered aluminium electrode. The goal of these studies was to show the possibility of the use of electrochemical excitation of the Eu(III ion in aqueous solution for emission generation. The generated ECL emission was very weak, and therefore its measurements and spectral analysis were carried out with the use of cut-off filters method. The studies proved a predominate role of the ligand-to-metal energy transfer (LMET in the generated ECL.

  7. A ratiometric fluorescent probe for gasotransmitter hydrogen sulfide based on a coumarin-benzopyrylium platform.

    Science.gov (United States)

    Duan, Yu-Wei; Yang, Xiao-Feng; Zhong, Yaogang; Guo, Yuan; Li, Zheng; Li, Hua

    2015-02-15

    A ratiometric fluorescent probe for H2S was developed based on a coumarin- benzopyrylium platform. The ratiometric sensing is realized by a selective conversion of acyl azide to the corresponding amide, which subsequently undergoes an intramolecular spirocyclization to alter the large π-conjugated system of CB fluorophore. Compared with the traditional azide-based H2S probes, the proposed probe utilizes the acyl azide as the recognition moiety and exhibits a rapid response (∼1min) towards H2S, which is superior to most of the azide-based H2S probes. Preliminary fluorescence imaging experiments show that probe 1 has potential to track H2S in living cells.

  8. A New Strategy for the Synthesis of 3-Acyl-coumarin Using Mesoporous Molecular Sieve MCM-41 as a Novel and Efficient Catalyst

    Institute of Scientific and Technical Information of China (English)

    HERAVI,Majid M; POORMOHAMMAD,Nargess; BEHESHTIGA,Yahia Sh; BAGHERNEJAD,Bita; MALAKOOTI,Reihaneh

    2009-01-01

    3-Acyl-coumarins were obtained in high yields from ortho-hydroxybenzaldehydes and ethyl acetoacetate or ethyl benzoylacetate in acetonitrile in the presence of a catalytic amount of mesoporous molecular sieve MCM-41. 3-Acyl-coumarins were obtained in high yields from ortho-hydroxybenzaldehydes and ethyl acetoacetate or ethyl benzoylacetate in acetonitrile in the presence of a catalytic amount of mesoporous molecular sieve MCM-41.

  9. Poligalen, a new coumarin from Polygala boliviensis, reduces the release of TNF and IL-6 independent of NF-kB downregulation.

    Science.gov (United States)

    Silva, Danielle F; Alves, Clayton Q; Brandão, Hugo N; David, Jorge M; David, Juceni P; Silva, Rangel L; Franchin, Marcelo; Cunha, Thiago M; Martins, Felipe T; Oliveira, Cecilia M A

    2016-09-01

    An unusually substituted coumarin, named poligalen, was isolated from a chloroform extract of the aerial parts of Polygala boliviensis. This coumarin was identified by one- and two-dimensional NMR techniques, and the structure of the compound was confirmed by X-ray diffraction. Poligalen exhibits immunomodulatory effects, reducing the levels of IL-6 and TNF after LPS stimulation in peritoneal macrophages. However, poligalen potentiates NF-kB activation.

  10. Phebaclavin I, a novel 3-prenylated coumarin, and trichoclin acetate, a new natural furocoumarin, from the aerial parts of Phebalium aff. tuberculosum (Rutaceae).

    Science.gov (United States)

    Roux, Delphine; Muyard, Frédéric; Girard, Corinne; Colombain, Michel; Tillequin, François; Waterman, Peter G; Bévalot, Françoise

    2006-03-01

    Phebaclavin I, a novel 3-prenylated coumarin, was isolated from the aerial parts of Phebalium aff. tuberculosum (Rutaceae) together with five known related compounds, Phebaclavin A, B, D, G, H. The structure of phebaclavin I was established by spectroscopic methods. Several other known coumarins were obtained, including trichoclin acetate, a furocoumarin isolated for the first time from a natural source, but previously described from acetylation of trichoclin.

  11. Self assembly of C-methyl resorcin[4]arene with coumarin and thiocoumarin: A nanotubular array with a near perfect lock and key fit

    Indian Academy of Sciences (India)

    Lepakshaiah Mahalakshmi; Partha P Das; Tayur N Guru Row

    2008-01-01

    The host-guest complex of -methyl resorcin[4]arene with coumarin and thiocoumarin has been characterized by single crystal X-ray diffraction technique. Structural analysis shows that the host forms an infinitie nanotubular array in which the guest coumarin shows a `head to tail’ arrangement of dimers held together by $\\ldots$ interaction in the host framework. Similar structural motif is observed when thiocoumarin used as a guest.

  12. A coumarin-specific prenyltransferase catalyzes the crucial biosynthetic reaction for furanocoumarin formation in parsley.

    Science.gov (United States)

    Karamat, Fazeelat; Olry, Alexandre; Munakata, Ryosuke; Koeduka, Takao; Sugiyama, Akifumi; Paris, Cedric; Hehn, Alain; Bourgaud, Frédéric; Yazaki, Kazufumi

    2014-02-01

    Furanocoumarins constitute a sub-family of coumarin compounds with important defense properties against pathogens and insects, as well as allelopathic functions in plants. Furanocoumarins are divided into two sub-groups according to the alignment of the furan ring with the lactone structure: linear psoralen and angular angelicin derivatives. Determination of furanocoumarin type is based on the prenylation position of the common precursor of all furanocoumarins, umbelliferone, at C6 or C8, which gives rise to the psoralen or angelicin derivatives, respectively. Here, we identified a membrane-bound prenyltransferase PcPT from parsley (Petroselinum crispum), and characterized the properties of the gene product. PcPT expression in various parsley tissues is increased by UV irradiation, with a concomitant increase in furanocoumarin production. This enzyme has strict substrate specificity towards umbelliferone and dimethylallyl diphosphate, and a strong preference for the C6 position of the prenylated product (demethylsuberosin), leading to linear furanocoumarins. The C8-prenylated derivative (osthenol) is also formed, but to a much lesser extent. The PcPT protein is targeted to the plastids in planta. Introduction of this PcPT into the coumarin-producing plant Ruta graveolens showed increased consumption of endogenous umbelliferone. Expression of PcPT and a 4-coumaroyl CoA 2'-hydroxylase gene in Nicotiana benthamiana, which does not produce furanocoumarins, resulted in formation of demethylsuberosin, indicating that furanocoumarin production may be reconstructed by a metabolic engineering approach. The results demonstrate that a single prenyltransferase, such as PcPT, opens the pathway to linear furanocoumarins in parsley, but may also catalyze the synthesis of osthenol, the first intermediate committed to the angular furanocoumarin pathway, in other plants.

  13. Quenching of coumarin emission by CdSe and CdSe/ZnS quantum dots: Implications for fluorescence reporting

    Energy Technology Data Exchange (ETDEWEB)

    Baride, Aravind [Department of Chemistry, University of South Dakota, Vermillion, SD 57069 (United States); Engebretson, Daniel [Biomedical Engineering, University of South Dakota, Vermillion, SD 57069 (United States); Berry, Mary T. [Department of Chemistry, University of South Dakota, Vermillion, SD 57069 (United States); Stanley May, P., E-mail: smay@usd.edu [Department of Chemistry, University of South Dakota, Vermillion, SD 57069 (United States)

    2013-09-15

    The photoinduced release of highly fluorescent 7-diethylamino coumarin (7DEAC) from CdSe quantum dots (QD) modified with a thiocinnamate ligand (11-mercapto undecyl-E-3-(4-(N,N-diethylamino)-2-hydroxy phenyl) propenoate, [4DEATC]) has been previously described. Coumarin fluorescence was used to ‘report’ the photochemical reaction. The current study quantifies the quenching effect of the QDs on the coumarin emission in this system. A systematic study is presented on the quenching of 7DEAC by CdSe and CdSe/ZnS quantum dots capped with 2-[2-(2-methoxyethoxy)ethoxy] ethanethiol (PEG-thiol). A new method for the functionalization of CdSe and CdSe/ZnS QDs with PEG-thiol was developed, which does not require isolation of the as-synthesized QDs. Stern–Volmer analysis was applied to quantify the effect of the PEG-CdSe and PEG-CdSe/ZnS on 7DEAC emission. The Stern–Volmer constant, K{sub SV}, was shown to be inversely proportional to temperature for quenching by PEG-CdSe, and the fluorescence lifetime of 7DEAC was shown to be independent of PEG-CdSe concentration. Room-temperature K{sub SV} values were similar for the PEG-CdSe and PEG-CdSe/ZnS quenchers. The large magnitude of K{sub SV}, the temperature dependence of K{sub SV}, the lifetime data, and the similarity of K{sub SV} values for the core and core–shell QD quenchers are all consistent with a static quenching mechanism. Assuming a static quenching mechanism, the temperature dependence of the coumarin-QD binding constant, K{sub b}, was used to estimate the ΔH and ΔS for the binding process. -- Highlights: • Quenching of a coumarin derivative by CdSe and CdSe/ZnS quantum dots is demonstrated • Stern–Volmer analysis is performed as a function of temperature • Fluorescence lifetime analysis was used to support Stern–Volmer analysis • Data overwhelmingly support quenching via a Static Mechanism • Quenching of coumarin by quantum dots is significant and must be considered in any release and report

  14. 香豆素类化合物在肿瘤治疗上的应用%Application of Anticancer Drugs with Coumarin Structures

    Institute of Scientific and Technical Information of China (English)

    黄月芬

    2015-01-01

    Coumarins are a group of compounds with anα-benzopyrone structure.In recent years,the researchers have explored the influence of coumarins on enzymes and cell pathways related to the metabolism of tumor cells,and isolated or synthesized many structurally specific coumarin derivatives with excellent anti-tumor activity,which proves adequately the importance of coumarin skeleton in the research and development of anticancer drugs.In this paper, we reviewed the application of many natural and synthetic coumarins which are classified by classical coumarin struc-tures on exploring new anticancer drugs.%香豆素( Coumarins)的基本结构是苯骈α-吡喃酮的一类化合物。近年来研究者报道了在肿瘤细胞信号转导通路和代谢的影响上香豆素具有的作用,从而发现了香豆素类化合物具有的抗肿瘤活性,并充分证明了目前香豆素类化合物在抗癌药物研发中的重要性。本文以香豆素的基本结构进行分类,对香豆素类化合物的抗肿瘤作用的研究进展进行综述。

  15. Bioactivation of coumarin in rat olfactory mucosal microsomes: Detection of protein covalent binding and identification of reactive intermediates through analysis of glutathione adducts.

    Science.gov (United States)

    Zhuo, Xiaoliang; Zhao, Weiping; Zheng, Joanna; Humphreys, W Griffith; Shu, Yue-Zhong; Zhu, Mingshe

    2009-10-07

    The presence of high levels, as well as tissue-specific forms, of cytochrome P450 enzymes in mammalian olfactory mucosa (OM) has important implications in the bioactivation and toxicity of xenobiotics entering the tissue. Previous studies have shown that coumarin, a known olfactory toxicant in rats, is bioactivated by OM microsomal P450s to a number of products, presumably via coumarin-3,4-epoxide and other epoxide intermediates. The aim of the current study was to obtain direct evidence for the formation of such reactive intermediates in rat OM through the detection of protein covalent binding and glutathione (GSH) adduct formation. Protein covalent binding experiments with [(14)C]coumarin (10microM) displayed a 7-9-fold higher NADPH-dependent radioactivity binding in rat OM microsomes (2.5nmol/mg/30min) compared to those in rat and human liver microsomes; the binding value in rat OM microsomes was substantially but not completely reduced by the addition of GSH (5mM). LC/MS analyses detected a number of GSH adducts in GSH-supplemented coumarin metabolism reaction in rat OM microsomes; 3-glutathionyl coumarin was found to be the major one, indicating 3,4-epoxidation as the main bioactivation pathway. Additional GSH adducts were identified, presumably forming via the same pathway or epoxidation on the benzene moiety. Our findings provide direct evidence for the formation of multiple coumarin reactive intermediates in rat OM, leading to protein covalent binding and GSH conjugation.

  16. Interaction of ionic liquid with water with variation of water content in 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6])/TX-100/water ternary microemulsions monitored by solvent and rotational relaxation of coumarin 153 and coumarin 490.

    Science.gov (United States)

    Seth, Debabrata; Chakraborty, Anjan; Setua, Palash; Sarkar, Nilmoni

    2007-06-14

    The interaction of water with room temperature ionic liquid (RTIL) [bmim][PF6] has been studied in [bmim][PF6]/TX-100/water ternary microemulsions by solvent and rotational relaxation of coumarin 153 (C-153) and coumarin 490 (C-490). The rotational relaxation and average solvation time of C-153 and C-490 gradually decrease with increase in water content of the microemulsions. The gradual increase in the size of the microemulsion with increase in w0 (w0=[water]/[surfactant]) is evident from dynamic light scattering measurements. Consequently the mobility of the water molecules also increases. In comparison to pure water the retardation of solvation time in the RTIL containing ternary microemulsions is very less. The authors have also reported the solvation time of C-490 in neat [bmim][PF6]. The solvation time of C-490 in neat [bmim][PF6] is bimodal with time constants of 400 ps and 1.10 ns.

  17. Coumarins from the Herb Cnidium monnieri and Chemically Modified Derivatives as Antifoulants against Balanus albicostatus and Bugula neritina Larvae

    Directory of Open Access Journals (Sweden)

    Zhan-Chang Wang

    2013-01-01

    Full Text Available In the search for new environmental friendly antifouling (AF agents, four coumarins were isolated from the herbal plant Cnidium monnieri, known as osthole (1, imperatorin (2, isopimpinellin (3 and auraptenol (4. Furthermore, five coumarin derivatives, namely 8-epoxypentylcoumarin (5, meranzin hydrate (6, 2'-deoxymetranzin hydrate (7, 8-methylbutenalcoumarin (8, and micromarin-F (9 were synthesized from osthole. Compounds 1, 2, 4, 7 showed high inhibitory activities against larval settlement of Balanus albicostatus with EC50 values of 4.64, 3.39, 3.38, 4.67 μg mL−1. Compound 8 could significantly inhibit larval settlement of Bugula neritina with an EC50 value of 3.87 μg mL−1. The impact of functional groups on anti-larval settlement activities suggested that the groups on C-5' and C-2'/C-3' of isoamylene chian could affect the AF activities.

  18. Tetrapeptide-coumarin conjugate 3D networks based on hydrogen-bonded charge transfer complexes: gel formation and dye release.

    Science.gov (United States)

    Guo, Zongxia; Gong, Ruiying; Jiang, Yi; Wan, Xiaobo

    2015-08-14

    Oligopeptide-based derivatives are important synthons for bio-based functional materials. In this article, a Gly-(L-Val)-Gly-(L-Val)-coumarin (GVGV-Cou) conjugate was synthesized, which forms 3D networks in ethanol. The gel nanostructures were characterized by UV-vis spectroscopy, FT-IR spectroscopy, X-ray diffraction (XRD), SEM and TEM. It is suggested that the formation of charge transfer (CT) complexes between the coumarin moieties is the main driving force for the gel formation. The capability of the gel to encapsulate and release dyes was explored. Both Congo Red (CR) and Methylene Blue (MB) can be trapped in the CT gel matrix and released over time. The present gel might be used as a functional soft material for guest encapsulation and release.

  19. Effect of coumarin and xanthotoxin on mitochondrial structure, oxygen uptake, and succinate dehydrogenase activity in onion root cells.

    Science.gov (United States)

    Kupidlowska, E; Dobrzynska, K; Parys, E; Zobel, A M

    1994-10-01

    At concentrations in which they occur on the plant surface and retard mitosis, coumarin and xanthotoxin lowered uptake of oxygen (by 60 and 30%, respectively) by meristematic cells ofAllium cepa root tips. They caused changes in the structure of the mitochondrial matrix to become dense, and protrusions of mitochondrial membranes were visible parallelling their hypertrophy, indicating alteration in the structure and physiology of these organelles. Coumarin and, to a lesser extent, xanthotoxin increased succinate dehydrogenase production in mitochondria and also in the cytoplasm, indicating changes in membrane permeability. Changes in oxygen uptake and mitochondrial structure, in addition to the retardation of mitosis, may be the reason these compounds act as allelochemicals after they have been removed from the plant surface and reach the root meristem.

  20. Coumarin based fluorescent ‘turn-on’ chemosensor for Zn{sup 2+}: An experimental and theoretical study

    Energy Technology Data Exchange (ETDEWEB)

    Sarkar, Deblina; Pramanik, Ajoy Kumar; Mondal, Tapan Kumar, E-mail: tkmondal@chemistry.jdvu.ac.in

    2014-02-15

    A highly sensitive and selective coumarin based chemosensor (HL) for the efficient detection of Zn{sup 2+} cation has been developed in a very facile and economically cheap route with an excellent yield. The distinct color change on addition of Zn{sup 2+} to the sensor is visible under naked eye. Moreover the rapid enhancement of fluorescence emission intensity on addition of Zn{sup 2+} also provides a wonderful detection technique for Zn{sup 2+}. The chemosensor is also efficient in detection of Zn{sup 2+} even in the presence of other metals and shows high selectivity towards Zn{sup 2+}. Experimental results have been verified with DFT and TDDFT calculations. -- Highlights: • Coumarin based fluorescent ‘turn-on’ chemosensor for Zn{sup 2+}. • Selective and efficient detection of Zn{sup 2+}. • Study of electronic structure of chemosensor (HL) and its zinc-complex. • Theoretical calculations.

  1. A TPA-caged precursor of (imino)coumarin for "turn-on" fluorogenic detection of Cu(.).

    Science.gov (United States)

    Hu, Zhangjun; Hu, Jiwen; Wang, Hui; Zhang, Qiong; Zhao, Meng; Brommesson, Caroline; Tian, Yupeng; Gao, Hongwen; Zhang, Xuanjun; Uvdal, Kajsa

    2016-08-24

    We strategize to utilize the precursors of (imino)coumarin fluorophores to deliver novel reactive Cu(+) probes, where tris[(2-pyridyl)-methyl] amine (TPA) works as a reactive receptor towards Cu(+). To verify this strategy, CP1, a representative probe and relevant sensing behaviors towards Cu(+) are presented here. CP1 features good solubility and fast response for monitoring labile copper in aqueous solution and live cells. The sensing mechanism of CP1 is determined by HPLC titration and mass spectrometric analysis. The probe CP1 exhibits a 60-fold fluorescence enhancement and a detection limitation of 10.8 nM upon the detection of Cu(+). CP1 is further applied for imaging labile copper in live cells. This work provides a starting point for future development of Cu(+) probes, based on in situ formation of (imino)coumarin scaffolds, as well as their further investigations of copper signaling and biological events.

  2. Synthesis and Study of Second-order Nonlinear Optical Properties of 3-Substituted-6- (substituted-phenylazo) coumarins

    Institute of Scientific and Technical Information of China (English)

    SONG Hua-Can; WEN Huan; LIANG Dong; SUN Yi-Feng

    2003-01-01

    @@ It has attracted a lot of attentions to synthesize and investigate the behaviors of organic second-order nonlinear optical (NLO) materials. [1,2] We have ever reported that acridine derivatives ,[3] 4-substituted-benzylideneoxazol-5(4H)-one[4] and 4,4′-di-styryl-biphenyl derivatives[5] possess good second-order NLO properties. Coumarin derivatives are good organic optical materials and azobenzene derivatives possess a higher second-order nonlinear polarization values, however, there are few reports about the study on the synthetic method, optical behavior, especially,second-order NLO properties of 3-substitued-6-(substituted-phenylazo) coumarin derivatives. Therefore, a series of the following compounds were prepared in order to investigate their NLO behavior.

  3. Rational Design of Coumarin Derivatives as CK2 Inhibitors by Improving the Interaction with the Hinge Region.

    Science.gov (United States)

    Zhang, Na; Chen, Wen-Juan; Zhou, Yue; Zhao, Hongtao; Zhong, Ru-Gang

    2016-01-01

    Design of novel coumarin derivatives as CK2 inhibitors were attempted by targeting the interaction with the hinge region. A set of substituents capable of forming a hydrogen bond or halogen bond with the hinge region were screened in silico, and trifluoromethyl emerges as a promising motif by forming favorable electrostatic interaction and a presumable halogen bond with the hinge region. As proof of concept, three trifluoromethyl derivatives of coumarin were synthesized and tested in vitro. The results indicated that replacement of methyl by trifluoromethyl leads to a modest 5-fold improvement in potency, with the most active compound being 0.4 µM. The newly designed compounds were further screened on one lung cancer cell line A549, showing low micromolar anti-proliferative activity.

  4. Coumarin-based fluorescence hybrid silica material used for selective detection and absorption of Hg2+ in aqueous media

    Science.gov (United States)

    Meng, Qingtao; Jia, Hongmin; Wang, Cuiping; Zhao, Hongbin; Lu, Gonghao; Hu, Zhizhi; Zhang, Zhiqiang; Duan, Chunying

    2014-11-01

    An inorganic-organic hybrid fluorescence material (C-SBA-15) was prepared by covalent immobilization of a coumarin derivative within the channels of SBA-15. The characterization results of XRD, TEM micrographs, FT-IR and UV-vis demonstrate that coumarin is successfully grafted onto the inner surface of SBA-15 and its organized structure is preserved. C-SBA-15 can detect Hg2+ with high selectivity to Pb2+, Zn2+, Cu2+, Mn2+, Cd2+, Co2+, Ag+, Fe3+, Ni2+, K+, Na+, Ca2+, Mg2+ and Li+ in water. Furthermore, the fluorogenical response is reversible by treating with EDTA and do not vary over a broad pH range (5.0-10.5). C-SBA-15 features more outstanding absorbing capacity for Hg2+ among other HTM ions in water.

  5. Early and late effects of coumarin therapy started before percutaneous coronary intervention: Clinical, angiographic and cost-effective outcome of the Balloon Angioplasty and Anticoagulation Study (BAAS).

    Science.gov (United States)

    Ten Berg, J M; Kelder, J C; Suttorp, M J; Mast, E G; Bal, E T; Ernst, J M P G; Plokker, H W M

    2002-05-01

    Coronary angioplasty frequently creates a thrombogenic surface with subsequent mural thrombosis that may lead to acute complications and possibly stimulates the development of restenosis. Whether coumarins can prevent these complications is unclear. In the Balloon Angioplasty and Anticoagulation Study (BAAS), the effect of coumarins started before the procedure on early and late outcome was studied. Patients were randomised to aspirin only or to aspirin plus coumarins. Half of the patients were randomised to undergo six-month angiographic follow-up. Study medication was started one week before coronary angioplasty and the target international normalised ratio (INR) was 2.1-4.8 during angioplasty and six-month follow-up. 'Optimal' anticoagulation was defined as an INR in the target range for at least 70% of the follow-up time. In addition, cost-effectiveness of coumarin treatment was measured. At one year death, myocardial infarction, target-lesion revascularisation and stroke were observed in 14.3% of the 530 patients randomised to aspirin plus coumarin versus in 20.3% of the 528 patients randomised to aspirin alone (relative risk 0.71; 95% CI 0.54-0.93). The incidence of major bleedings and false aneurysms during hospitalisation was 3.2% and 1.0%, respectively, (relative risk 3.39; 95% CI 1.26-9.11). Optimal anticoagulation was an independent predictor of late thrombotic events (relative risk, 0.33; 95% CI, 0.19-0.57). Quantitative coronary analysis was performed of 301 lesions in the ASA group and of 297 lesions in the coumarin group. At six months, the minimal luminal diameter was similar in the ASA and coumarin group. However, optimal anticoagulation was an independent predictor of angiographic outcome at six months. Optimal anticoagulation led to a 0.21 mm (95% CI: 0.05-0.37) larger MLD as compared with suboptimal anticoagulation whereas aspirin use led to a 0.12 mm (95% CI -0.28-0.04) smaller MLD. When including all costs, the savings associated with coumarin

  6. Growth, essential oil content, and content of coumarin in young plants of guaco (Mikania glomerata Sprengel cultivated under colored nets

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    Girlene Santos Souza

    2011-09-01

    Full Text Available Mikania glomerata Sprengel is a medicinal plant widely used in folk medicine, mainly to treat respiratory disorders, which acts by dilating the bronchi, being coumarin one of the substances associated with this effect. Therefore, understanding the physiological behavior of this species and its responses to the environmental conditions is necessary to improve the cultivation methods. In this context, the aim of this work was to evaluate the effect of light spectrum control on growth, the essential oil content, and the content of coumarin in Mikania glomerata Sprengel. Plants were grown for four months under nets with 50% shading in gray, red, blue, and exposed to full sunlight (0%. The essential oil was extracted from fresh leaves through hydrodistillation in a modified Clevenger apparatus. The identification and quantification of coumarin were performed through high performance liquid chromatography (HPLC. The results showed the blue fabric allowed an increase in total dry matter accumulation and leaf area, as plants under red shading presented higher dry matter allocation to the roots. The smallest quantity of dry leaves was observed in plants grown under full sun exposure. Changes were not observed, however, in leaf weight ratio and in root/shoot proportion. The essential oil content of plants grown under blue net was 0.14%, which corresponded to an increase of 142% over the level found in plants grown under full sun exposure, as the coumarin content was not influenced by the net color. These results show that light can be modulated during cultivation, in order to obtain desirable morphological characteristics and maximize the production of active principles in this species.

  7. Microwave promoted one-pot synthesis of 3-(2'-amino-3'-cyano-4'-arylpyrid-6'-yl) coumarins

    Institute of Scientific and Technical Information of China (English)

    Jian Feng Zhou; Gui Xia Gong; Feng Xia Zhu; San Jun Zhi

    2009-01-01

    A facile procedure for the synthesis of 3-(2'-amino-3'-cyano-4'-arylpyrid-6'-yl) coumarins are being reported starting from 3-acetylcoumarin, aromatic aldehydes and malononitrile. The reactions were carded out on microwave irradiation in good yield with short time and easy work-up. The structures of all the compounds have been confirmed on the basis of their analytical, IR,1H NMR,and mass spectral data.

  8. 4-Trifluoromethyl-substituted coumarins with large Stokes shifts: synthesis, bioconjugates, and their use in super-resolution fluorescence microscopy.

    Science.gov (United States)

    Schill, Heiko; Nizamov, Shamil; Bottanelli, Francesca; Bierwagen, Jakob; Belov, Vladimir N; Hell, Stefan W

    2013-12-02

    Bright and photostable fluorescent dyes with large Stokes shifts are widely used as sensors, molecular probes, and light-emitting markers in chemistry, life sciences, and optical microscopy. In this study, new 7-dialkylamino-4-trifluoromethylcoumarins have been designed for use in bioconjugation reactions and optical microscopy. Their synthesis was based on the Stille reaction of 3-chloro-4-trifluoromethylcoumarins and available (hetero)aryl- or (hetero)arylethenyltin derivatives. Alternatively, the acylation of 2-trifluoroacetyl-5-dialkylaminophenols with available (hetero)aryl- or (hetero)arylethenylacetic acids followed by intramolecular condensation afforded coumarins with 3-(hetero)aryl or 3-[2-(hetero)aryl]ethenyl groups. Hydrophilic properties were provided by the introduction of a sulfonic acid residue or by phosphorylation of a primary hydroxy group attached at C-4 of the 2,2,4-trimethyl-1,2-dihydroquinoline fragment fused to the coumarin fluorophore. For use in immunolabeling procedures, the dyes were decorated with an (activated) carboxy group. The positions of the absorption and emission maxima vary in the ranges 413-480 and 527-668 nm, respectively. The phosphorylated dye, 9,CH=CH-2-py,H, with the 1-(3-carboxypropyl)-4-hydroxymethyl-2,2-dimethyl-1,2-dihydroquinoline fragment fused to the coumarin fluorophore bearing the 3-[2-(2-pyridyl)ethenyl] residue (absorption and emission maxima at 472 and 623 nm, respectively) was used in super-resolution light microscopy with stimulated emission depletion and provided an optical resolution better than 70 nm with a low background signal. As a result of their large Stokes shifts, good fluorescence quantum yields, and adequate photostabilities, phosphorylated coumarins enable two-color imaging (using several excitation sources and a single depletion laser) to be combined with subdiffractional optical resolution.

  9. 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...

  10. Identification of sesquiterpene coumarins of oleo-gum resin of Ferula assa-foetida L. from the Yasuj region.

    Science.gov (United States)

    Asghari, J; Atabaki, V; Baher, E; Mazaheritehrani, M

    2016-01-01

    Chemical investigation of the oleo-gum resin of Ferula assa-foetida L. from Yasuj region led to the identification of five sesquiterpene coumarins namely, conferone (1), badrakemin (2), feslol (3), isosamarcandin (4) and samarcandin (5). The compounds were characterised by detailed 1D ((1)H and (13)C) and 2D NMR (HMBC, HSQC and NOESY) experiments. Among these compounds, conferone (1) and isosamarcandin (4) are being newly reported in F. assa-foetida L.

  11. 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...

  12. 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.

  13. Investigation of role of silver nanoparticles on spectroscopic properties of biologically active coumarin dyes 4PTMBC and 1IPMBC.

    Science.gov (United States)

    Raghavendra, U P; Basanagouda, Mahantesha; Thipperudrappa, J

    2015-01-01

    The role of silver nanoparticles on spectroscopic properties of biologically active coumarin dyes 4-p-tolyloxymethyl-benzo[h]coumarin (4PTMBC) and 1-(4-iodophenoxymethyl)-benzo[f]coumarin (1IPMBC) has been investigated using absorption and fluorescence spectroscopy. Silver nanoparticles are synthesized by chemical reduction method and the estimated size by Mie theory is 12 nm. The absorption spectral changes of dyes in the presence of silver nanoparticles suggest their possible interaction with silver nanoparticles. The apparent association constants of the interaction are estimated using Benesi-Hildebrand model. Fluorescence quenching has been observed in both the dyes with the addition of silver nanoparticles. The Stern-Volmer plots of fluorescence quenching are found to be nonlinear showing positive deviation. The magnitudes of quenching rate parameter and fluorescence lifetime measurements indicate the presence of both collisional and static quenching mechanisms. The binding constants and the number of binding sites for the static type of quenching have been estimated from the fluorescence data. The role of diffusion, energy transfer and electron transfer processes in fluorescence quenching mechanism has been discussed.

  14. Synthesis, biological activity evaluation and molecular docking studies of novel coumarin substituted thiazolyl-3-aryl-pyrazole-4-carbaldehydes.

    Science.gov (United States)

    Vaarla, Krishnaiah; Kesharwani, Rajesh Kumar; Santosh, Karnewar; Vedula, Rajeswar Rao; Kotamraju, Srigiridhar; Toopurani, Murali Krishna

    2015-12-15

    A novel series of coumarin substituted thiazolyl-3-aryl-pyrazole-4-carbaldehydes (4a-o) were synthesized via an efficient, one-pot multicomponent approach involving 3-(2-bromoacetyl)coumarins (1a-g), thiosemicarbazide (2) and substituted acetophenones (3a-c) utilizing Vilsmeier-Haack reaction condition with good yields. The title compounds structure was elucidated by spectroscopic data (IR, NMR and Mass) and elemental analysis. All the synthesized compounds were screened for their in vitro cytotoxic activity against MCF-7, DU-145 and HeLa cell lines and studied detailed about molecular interaction of probable target protein human microsomal cytochrome CYP450 2A6 using docking simulation. These coumarin derivatives were exhibiting moderate to appreciable cytotoxic activities. The compounds 4m and 4n exhibited significant cytotoxic activity with IC50 values having 5.75 and 6.25μM against HeLa cell line. Similarly compound 4n also exhibiting good anti cancer property and antibacterial activity against DU-145 cell line and Gram negative bacterial strains.

  15. Genetic alterations for increased coumarin production lead to metabolic changes in the medicinally important Pelargonium sidoides DC (Geraniaceae).

    Science.gov (United States)

    Colling, J; Groenewald, J-H; Makunga, N P

    2010-11-01

    The medicinal plant Pelargonium sidoides is fast becoming threatened due to the overharvest of its tubers from the wild to produce a phytopharmaceutical for treating respiratory infections. The action of the coumarins is implicated in the efficacy of the commercial herbal extract with the highly oxygenated coumarins exhibiting the best anti-bacterial and anti-viral activity. Through this work we aimed at exploring the metabolic effects of Agrobacterium rhizogenes transformation. After confirmation of transgenesis using PCR amplification of the rol A (320 bp), rol B (400 bp) and rol C (600 bp) genes, metabolite profiles indicated a high level of variability between the different transgenic clones but these had more compounds compared to non-transgenic control cultures. This was represented by a two- to four-fold increase in detected metabolites in transgenic clones. We quantified several commercially important coumarins, flavonoids and phenolic acids. One of the clones had six out of nine of these metabolites. Overall, the concentration of these metabolites of interest were significantly changed in transgenic root cultures, for instance shikimic acid was recorded at the highest level in clone A4T-A. Production of key metabolites at significantly higher concentrations due to transgenesis and positive anti-bacterial activity exhibited by transgenic roots lends support to the idea of developing these clones as an alternative source that will allow for sustainable access to economically valuable secondary compounds of P. sidoides.

  16. Different susceptibilities of Leishmania spp. promastigotes to the Annona muricata acetogenins annonacinone and corossolone, and the Platymiscium floribundum coumarin scoparone.

    Science.gov (United States)

    Vila-Nova, Nadja Soares; de Morais, Selene Maia; Falcão, Maria José Cajazeiras; Alcantara, Terezinha Thaize Negreiros; Ferreira, Pablito Augusto Travassos; Cavalcanti, Eveline Solon Barreira; Vieira, Icaro Gusmão Pinto; Campello, Cláudio Cabral; Wilson, Mary

    2013-03-01

    Leishmaniasis is a zoonotic disease that can manifest itself in visceral and cutaneous form. The aim of this study was to search for new leishmanicidal compounds. Preliminarily, Artemia salina assay was applied to compounds from two plants found in Northeastern Brazil, Platymiscium floribundum and Annona muricata. Then these compounds were tested against three Leishmania species (Leishmania donovani, Leishmania mexicana and Leishmania major). A screening assay using luciferase-expressing promastigote form were used to measure the viability of promastigote One coumarin, scoparone, isolated from P. floribundum and two acetogenins, annonacinone and corossolone isolated from A. muricata showed leishmanicidal activity in all species tested. Nevertheless, Leishmania species indicated different susceptibilities in relation to the tested compounds: L. mexicana was more sensitive to scoparone followed by L. major and L. donovani. The three species presented similar inhibition to corossolone and annonacinone. Acetogenin annonacinone (EC(50)=6.72-8.00 μg/mL) indicated high leishmanicidal activity; corossolone (EC(50)=16.14-18.73 μg/mL) and scoparone (EC(50)=9.11-27.51 μg/mL) moderate activity. A. saline larvae were less sensitive to the coumarin scoparone and acetogenin corossolone was the most toxic. In conclusion, the leishmanicidal activity demonstrated by the coumarin and acetogenins indicate these compounds for further studies aiming the development of new leishmanicidal agents.

  17. Anti-Alzheimer's disease potential of coumarins from Angelica decursiva and Artemisia capillaris and structure-activity analysis.

    Science.gov (United States)

    Ali, Md Yousof; Jannat, Susoma; Jung, Hyun Ah; Choi, Ran Joo; Roy, Anupom; Choi, Jae Sue

    2016-02-01

    To use structure-activity analysis to study the anti-Alzheimer's disease (anti-AD) activity of natural coumarins isolated from Angelica decursiva and Artemisia capillaris, along with one purchased coumarin (daphnetin). Umbelliferone, umbelliferone 6-carboxylic acid, scopoletin, isoscopoletin, 7-methoxy coumarin, scoparone, scopolin, and esculetin have been previously isolated; however 2'-isopropyl psoralene was isolated from Angelica decursiva for the first time to evaluate their inhibitory effects against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and β-site amyloid precursor protein cleaving enzyme 1 (BACE1) enzyme activity. We scrutinized the potentials of coumarins as cholinesterase and BACE1 inhibitors via enzyme kinetics and molecular docking simulation. Among the test compounds, umbelliferone 6-carboxylic acid, esculetin and daphnetin exhibited potent inhibitory activity against AChE, BChE and BACE1. Both esculetin and daphnetin have a catechol group and exhibit significant anti-AD activity against AChE and BChE. In contrast, presence of a sugar moiety and methoxylation markedly reduced the anti-AD activity of the coumarins investigated in this study. With respect to BACE1 inhibition, umbelliferone 6-carboxylic acid, esculetin and daphnetin contained carboxyl or catechol groups, which significantly contributed to their anti-AD activities. To further investigate these results, we generated a 3D structure of BACE1 using Autodock 4.2 and simulated binding of umbelliferone 6-carboxylic acid, esculetin and daphnetin. Docking simulations showed that different residues of BACE1 interacted with hydroxyl and carboxylic groups, and the binding energies of umbelliferone 6-carboxylic acid, esculetin and daphnetin were negative (-4.58, -6.25 and -6.37 kcal/mol respectively). Taken together, our results suggest that umbelliferone 6-carboxylic acid, esculetin and daphnetin have anti-AD effects by inhibiting AChE, BChE and BACE1, which might be useful

  18. Coumarin Compounds of Biebersteinia Multifida Roots Show Potential Anxiolytic Effects In Mice

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    Hamid Reza Monsef-Esfahani

    2013-06-01

    Full Text Available Background:Traditional preparations of the root of Biebersteinia multifida DC (Geraniaceae, a native medicinal plant of Irano-Turanian floristic region, have been used for the treatment of phobias as anxiolytic herbal preparation.Methods:We utilized the phobic behavior of mice in an elevated plus-maze as a model to evaluate the anxiolytic effect of the plant extract and bio-guided fractionation was applied to isolate the active compounds. Total root extract, alkaline and ether fraction were administered to mice at different doses 30 and 90 min prior to the maze test. Saline and diazepam were administered as negative and positive controls, respectively. The time spent in open and closed arms, an index of anxiety behavior and entry time, was measured as an index of animal activity.Results:The total root extract exhibited anxiolytic effect which was comparable to diazepam but with longer duration. This sustained effect of the crude extract was sustained for 90 min and was even more after injection of 45 mg/kg while the effect of diazepam had been reduced by 90 min. The anxiolytic effect factor was only present in the alkaline fraction and displayed its effect at lower doses than diazepam while pure vasicinone as the previously known alkaloid did not shown anxiolytic effect. The effect of the alkaline fraction was in a dose dependent manner starting at 0.2 mg/kg with a maximum at 1.0 mg/kg. Bio-guided fractionation using a variety of chromatographic methods led to isolation and purification of three coumarin derivatives from the bioactive fraction, including umbelliferone, scopoletin, and ferulic acid.Conclusion:For the first time, bio-guided fractionation of the root extract of B. multifida indicates significant sustained anxiolytic effects which led to isolation of three coumarin derivatives with well-known potent MAO inhibitory and anti-anxiety effects. These data contribute to evidence-based traditional use of B. multifida root for anxiety

  19. Accumulation and Secretion of Coumarinolignans and other Coumarins in Arabidopsis thaliana Roots in Response to Iron Deficiency at High pH

    Directory of Open Access Journals (Sweden)

    Patricia Sisó-Terraza

    2016-11-01

    Full Text Available Root secretion of coumarin-phenolic type compounds has been recently shown to be related to Arabidopsis thaliana tolerance to Fe deficiency at high pH. These studies revealed the identity of a few simple coumarins occurring in roots and exudates of Fe-deficient A. thaliana plants, and left open the possible existence of other unknown phenolics. We used HPLC-UV-VIS-ESI-MS(TOF, HPLC/ESI-MSn(ion trap and HPLC-ESI-MS-MS(Q-TOF to characterize (identify and quantify phenolic-type compounds accumulated in roots or secreted into the nutrient solution of A. thaliana plants in response to Fe deficiency. Plants grown with or without Fe and using nutrient solutions buffered at pH 5.5 or 7.5 enabled to identify an array of phenolics. These include several coumarinolignans not previously reported in A. thaliana (cleomiscosins A, B, C and D and the 5’-hydroxycleomiscosins A and/or B, as well as some coumarin precursors (ferulic acid and coniferyl and sinapyl aldehydes, and previously reported cathecol (fraxetin and non-cathecol coumarins (scopoletin, isofraxidin and fraxinol, some of them in hexoside forms not previously characterized. The production and secretion of phenolics were more intense when the plant accessibility to Fe was diminished and the plant Fe status deteriorated, as it occurs when plants are grown in the absence of Fe at pH 7.5. Aglycones and hexosides of the four coumarins were abundant in roots, whereas only the aglycone forms could be quantified in the nutrient solution. A comprehensive quantification of coumarins, first carried out in this study, revealed that the catechol coumarin fraxetin was predominant in exudates (but not in roots of Fe-deficient A. thaliana plants grown at pH 7.5. Also, fraxetin was able to mobilize efficiently Fe from a Fe(III-oxide at pH 5.5 and pH 7.5. On the other hand, non-catechol coumarins were much less efficient in mobilizing Fe and were present in much lower concentrations, making unlikely that they

  20. Radioiodination of 2,3-dimethyl-4H-furo[3,2-c]coumarin and biological evaluation in solid tumor bearing mice.

    Science.gov (United States)

    Abd Elhalim, S M; Ibrahim, I T

    2014-10-22

    Compound 2,3-dimethyl-4H-furo[3,2-c]coumarin is a coumarin derivative that could be labeled with (125)I. The process of labeling was started using 1mg of the compound, 50µg CAT oxidizing agent, 30min as reaction time at pH with a yield about 95%. The (125)I-coumarin derivative was stable for about 48h. Radiochemical purity of the labeled compound was performed by electrophoresis and HPLC. The labeled compound was separated with purity about 95%. Tumor transplantation to produce a solid tumor in the right leg of albino mice was made by intramuscular injection of 2×10(6) EAC (Ehrlish acittes carcinoma cells). Biodistribution study of (125)I-coumarin derivative revealed that the uptake in tumor bearing leg was over 5% at 1h and 4h post-injection. This uptake encourages the use of (123)I-coumarin derivative in imaging of tumor sites.

  1. A new colorimetric and fluorescent bis(coumarin)methylene probe for fluoride ion detection based on the proton transfer signaling mode

    Energy Technology Data Exchange (ETDEWEB)

    Mahapatra, Ajit Kumar, E-mail: akmahapatra@rediffmail.com; Maiti, Kalipada; Sahoo, Prithidipa; Nandi, Prasanta Kumar

    2013-11-15

    A new turn-on fluorescent and colorimetric sensor, oxidized bis(coumarin)methane (1) for fluoride in acetonitrile was designed and synthesized. The binding ability evaluated by UV–vis and fluorescence titration experiments reveals that 1 can selectively interact with fluoride. Upon addition of fluoride to receptor 1 in acetonitrile solution, the appearance of a new absorption band around 349 nm showed a color change from colorless to yellow, which can provide a way of ‘naked eye’ detection of fluorides. The spectral change of 1 is due to the anion induced deprotonation and hence an increase in charge density and rigidity of the receptor molecule. Furthermore, the binding mode with fluoride was investigated by {sup 1}H NMR titration experiments. Again, the deprotonation of oxidized bis(coumarin)methane 1 is responsible for the color change. -- Graphical abstract: A new colorimetric and fluorescent bis(coumarin)methylene probe for fluoride ion detection based on the proton transfer signaling mode. Highlights: • The first report of conjugated biscoumarin-based colorimetric chemosensor. • Oxidized bis(coumarin)methane acts as colorimetric reporter. • The oxidized coumarin moiety might modulate the internal charge transfer (ICT). • Fluorescence turn-on sensing of fluoride.

  2. "Reduced" Coumarin Dyes with an O-Phosphorylated 2,2-Dimethyl-4-(hydroxymethyl)-1,2,3,4-tetrahydroquinoline Fragment: Synthesis, Spectra, and STED Microscopy.

    Science.gov (United States)

    Nizamov, Shamil; Sednev, Maksim V; Bossi, Mariano L; Hebisch, Elke; Frauendorf, Holm; Lehnart, Stephan E; Belov, Vladimir N; Hell, Stefan W

    2016-08-01

    Large Stokes-shift coumarin dyes with an O-phosphorylated 4-(hydroxymethyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline fragment emitting in the blue, green, and red regions of the visible spectrum were synthesized. For this purpose, N-substituted and O-protected 1,2-dihydro-7-hydroxy-2,2,4-trimethylquinoline was oxidized with SeO2 to the corresponding α,β-unsaturated aldehyde and then reduced with NaBH4 in a "one-pot" fashion to yield N-substituted and 7-O-protected 4-(hydroxymethyl)-7-hydroxy-2,2-dimethyl-1,2,3,4-tetrahydroquinoline as a common precursor to all the coumarin dyes reported here. The photophysical properties of the new dyes ("reduced coumarins") and 1,2-dihydroquinoline analogues (formal precursors) with a trisubstituted C=C bond were compared. The "reduced coumarins" were found to be more photoresistant and brighter than their 1,2-dihydroquinoline counterparts. Free carboxylate analogues, as well as their antibody conjugates (obtained from N-hydroxysuccinimidyl esters) were also prepared. All studied conjugates with secondary antibodies afforded high specificity and were suitable for fluorescence microscopy. The red-emitting coumarin dye bearing a betaine fragment at the C-3-position showed excellent performance in stimulation emission depletion (STED) microscopy.

  3. Benzopyrone coumarin leads to an inhibition of ochratoxin biosynthesis in representatives of Aspergillus and Penicillium spp. via a type of feedback response mechanism.

    Science.gov (United States)

    Mayer, L S L; Stoll, D A; Geisen, R; Schmidt-Heydt, M

    2014-04-01

    Growth and mycotoxin biosynthesis of the ochratoxin-producing fungal strains Aspergillus carbonarius, Aspergillus steynii, Penicillium verrucosum, and Penicillium nordium were analyzed on standard laboratory growth medium supplemented with different amounts of coumarin, an organic compound of the benzopyrone class. Neither the growth nor the phenotypic morphology of the filamentous fungi analyzed was affected by using coumarin concentrations equivalent to 2.5 to 25 μg/ml of medium. In contrast, the ochratoxin biosynthesis was strongly inhibited in both strains of the Aspergillus species and nearly completely inhibited in both Penicillium strains at coumarin concentrations above 8.75 μg/ml. Analyzing the transcriptional activity of the otapksPN polyketide synthase gene in P. nordicum using real-time PCR revealed a strong concentration-dependent decrease in gene expression. Taken together, the data show that ochratoxin biosynthesis in representative strains of the genera Aspergillus and Penicillium could be effectively inhibited by coumarin in a concentration-dependent manner. It could be suggested that the molecular background behind this inhibition is some kind of feedback response mechanism, based on the structural similarity of coumarin to the benzopyrone moiety of the ochratoxin molecule.

  4. Combined spectroscopic and DFT studies on 6-bromo-4-chloro-3-formyl coumarin.

    Science.gov (United States)

    Raj, R K; Gunasekaran, S; Gnanasambandan, T; Seshadri, S

    2015-03-15

    The FTIR and FT-Raman spectra of 6-bromo-4-chloro-3-formyl coumarin (6B4C3FC) have been recorded in the region 4000-400 and 4000-100 cm(-1), respectively. The optimized geometry, frequency and intensity of the vibrational bands were obtained by the density functional theory (DFT) using 6-31G(d,p) basis set. The harmonic vibrational frequencies were scaled and compared with experimental values. The observed and the calculated frequencies were found to be in good agreement. The UV-Visible spectrum was also recorded and compared with the theoretical values. The calculated HOMO and LUMO energies show that charge transfer occurs within molecule. The first order hyperpolarizability (β0) of 6B4C3FC is 21 times greater than that of urea. Stability of the molecule arising from hyperconjugative interactions, charge delocalization have been analyzed using natural bond orbital (NBO) analysis. Information about the charge density distribution of the molecule and its chemical reactivity has been obtained by mapping molecular electrostatic potential surface. In addition, the non-linear optical properties were discussed from the dipole moment values and the excitation wavelength in the UV-Visible region. Copyright © 2014 Elsevier B.V. All rights reserved.

  5. Anti-Inflammatory Screening and Molecular Modeling of Some Novel Coumarin Derivatives

    Directory of Open Access Journals (Sweden)

    Radwan El-Haggar

    2015-03-01

    Full Text Available Coumarin and their derivatives have drawn much attention in the pharmacological and pharmaceutical fields due to their broad range and diverse biological activities. In the present work, starting from the 6-amino-7-hydroxy-4-methyl-2H-chromen-2-one, a series of 6-(substituted benzylamino-7-hydroxy-4-methyl-2H-chromen-2-ones 1–11 was synthesized and assessed for their anti-inflammatory activity using the carrageenan-induced hind paw edema method. Compounds 2, 3, 4 and 9 showed significant (p < 0.001 reduction of rat paw edema volume after 1 h from the administration of the carrageenan compared to the reference drug, indomethacin. On the other hand, compounds 4 and 8 showed the highest anti-inflammatory activity, surpassing indomethacin after 3 h with 44.05% and 38.10% inhibition, respectively. Additionally, a molecular docking study was performed against the COX enzyme using the MOE 10.2010 software.

  6. Coumarins as Potential Antioxidant Agents Complemented with Suggested Mechanisms and Approved by Molecular Modeling Studies

    Directory of Open Access Journals (Sweden)

    Yasameen K. Al-Majedy

    2016-01-01

    Full Text Available Syntheses of coumarins, which are a structurally interesting antioxidant activity, was done in this article. The modification of 7-hydroxycoumarin by different reaction steps was done to yield target compounds. Molecular structures were characterized by different spectroscopical techniques (Fourier transformation infrared and nuclear magnetic resonance. Antioxidant activities were performed by using various in vitro spectrophometric assays against 1,1-diphenyl-2-picrylhydrazyl (DPPH radical and hydrogen peroxide (H2O2. All compounds exhibited high efficiency as antioxidants compared to ascorbic acid. The highest efficiency scavenging activity was found for compound 3 (91.0 ± 5.0, followed by compounds 2 and 4 (88.0 ± 2.00; and 87.0 ± 3.00. Ascorbic acid C was used as a standard drug with a percentage inhibition of 91.00 ± 1.5. The mechanism of the synthesized compounds as antioxidants was also studied. Hartree–Fock–based quantum chemical studies have been carried out with the basis set to 3-21G, in order to obtain information about the three-dimensional (3D geometries, electronic structure, molecular modeling, and electronic levels, namely HOMO (highest occupied molecular orbital and LUMO (lowest unoccupied molecular orbital, to understand the antioxidant activity for the synthesized compounds.

  7. Design, Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry

    Directory of Open Access Journals (Sweden)

    Ye Tian

    2016-06-01

    Full Text Available In order to develop novel chemotherapeutic agents with potent anticancer activities, we designed four series of novel compounds employing hybridization strategy. Twenty novel dihydroartemisinin-coumarin hybrids, 10a–e, 11a–e, 12a–e, 13a–e, were synthesized via click chemistry in this study and their structures were characterized by HRMS and NMR. The cytotoxic activities were measured by MTT assay against three cancer cell lines (HCT-116, MDA-MB-231, and HT-29 under normoxic or anoxic conditions, respectively. The target compounds exhibited moderate activity with IC50 values in the 0.05–125.40 μM range, and these compounds exhibited better activity against HT-29 cell line under anoxic condition. The cytotoxic activities of most compounds under anoxic condition displayed one- to 10-fold greater activity than under normoxic condition. Compounds 10a–e showed better selectivity against the HT-29 cell line than the other two cell lines. These results indicated that our design of CA IX inhibitors does correspond with its action mode to some degree and deserves further investigation.

  8. Synthesis, Structure-Activity Relationships (SAR and in Silico Studies of Coumarin Derivatives with Antifungal Activity

    Directory of Open Access Journals (Sweden)

    José M. Barbosa-Filho

    2013-01-01

    Full Text Available The increased incidence of opportunistic fungal infections, associated with greater resistance to the antifungal drugs currently in use has highlighted the need for new solutions. In this study twenty four coumarin derivatives were screened in vitro for antifungal activity against strains of Aspergillus. Some of the compounds exhibited significant antifungal activity with MICs values ranging between 16 and 32 µg/mL. The structure-activity relationships (SAR study demonstrated that O-substitutions are essential for antifungal activity. It also showed that the presence of a short aliphatic chain and/or electron withdrawing groups (NO2 and/or acetate favor activity. These findings were confirmed using density functional theory (DFT, when calculating the LUMO density. In Principal Component Analysis (PCA, two significant principal components (PCs explained more than 60% of the total variance. The best Partial Least Squares Regression (PLS model showed an r2 of 0.86 and q2cv of 0.64 corroborating the SAR observations as well as demonstrating a greater probe N1 interaction for active compounds. Descriptors generated by TIP correlogram demonstrated the importance of the molecular shape for antifungal activity.

  9. Synthesis and Characterization of New Thiazolidinones Containing Coumarin Moieties and Their Antibacterial and Antioxidant Activities

    Directory of Open Access Journals (Sweden)

    Alary Fabienne

    2012-08-01

    Full Text Available New coumarin derivatives, namely (2-(4-methyl-2-oxo-2H-chromen-7-yloxy-N-(4-oxo-2-phenylthiazolidin-3-ylacetamide, N-(2-(3-methoxyphenyl-4-oxothiazolidin-3-yl-2-(4-methyl-2-oxo-2H-chromen-7-yloxyacetamide, 2-(4-methyl-2-oxo-2H-chromen-7-yloxy-N-(4-oxo-2-(2,3,4trimethoxyphenylthiazolidin-3-ylacetamide and N-(2-(4-bromophenyl-4-oxothiazolidin-3-yl-2-(4-methyl-2-oxo-2H-chromen-7-yloxyacetamide were synthesized starting from 4-methyl-7-hydroxycoumarin. The structures of the obtained compounds were confirmed by analytical IR and NMR spectra to elucidate the different positions of protons and carbons and as well as theoretical studies (DFT/B3LYP. The new compounds were screened for antibacterial activity. Most of them are more active against E. coli S. aureus and B. subtilis than standard references.

  10. A New Coumarin-Based Colorimetric and Fluorometric Sensor for Cu{sup 2+}

    Energy Technology Data Exchange (ETDEWEB)

    An, Kyounglyong; Jun, Kun [Korea Research Institute of Chemical Technology, Daejeon (Korea, Republic of); Park, Koon Ha [Chungnam National Univ., Daejeon (Korea, Republic of)

    2014-07-15

    We have developed a new colorimetric and fluorescent 'turn-off' sensor for Cu{sup 2+} based on coumarin Shiff base of hydroxycinnamaldehyde. It displays a 50 nm red-shift of maximum absorption band with color change from colorless to greenish-yellow upon addition of Cu{sup 2+} in 10 mM tris-HCl buffer solution (acetonitrile/water = 9:1, pH = 7.01). And also remarkable fluorescence quenching was observed upon the addition of Cu{sup 2+}. The 1:2 stoichiometry of sensor complex (sensor A + Cu{sup 2+}) was confirmed by Job's plot based on absorption titration. Chemosensors, small chemical compounds that sense the presence of analytes or energy, typically consist of two components: a receptor moiety that interacts with the target analytes and a read-out system that signals binding. And one of the most utilized research tool for the study of chemosensors employs a colorimetric and fluorometric spectroscopic techniques. So far successful reports on metal ion sensors have been documented including our recent result. Many different kinds of optical or fluorescent sensors have several advantages (such as high sensitivity and selectivity, non-destructive analysis, low cost and real-time monitoring), which allow naked-eye detection of color and fluorescent emission change upon metal ion binding without the use of any expensive spectroscopic equipment.

  11. Screening of Natural Organic Volatiles from Prunus mahaleb L. Honey: Coumarin and Vomifoliol as Nonspecific Biomarkers

    Directory of Open Access Journals (Sweden)

    Mladenka Malenica Staver

    2011-03-01

    Full Text Available Headspace solid-phase microextraction (HS-SPME; PDMS/DVB fibre and ultrasonic solvent extraction (USE; solvent A: pentane and diethyl ether (1:2 v/v, solvent B: dichloromethane followed by gas chromatography and mass spectrometry (GC, GC-MS were used for the analysis of Prunus mahaleb L. honey samples. Screening was focused toward chemical composition of natural organic volatiles to determine if it is useful as a method of determining honey-sourcing. A total of 34 compounds were identified in the headspace and 49 in the extracts that included terpenes, norisoprenoids and benzene derivatives, followed by minor percentages of aliphatic compounds and furan derivatives. High vomifoliol percentages (10.7%–24.2% in both extracts (dominant in solvent B and coumarin (0.3%–2.4% from the extracts (more abundant in solvent A and headspace (0.9%–1.8% were considered characteristic for P. mahaleb honey and highlighted as potential nonspecific biomarkers of the honey’s botanical origin. In addition, comparison with P. mahaleb flowers, leaves, bark and wood volatiles from our previous research revealed common compounds among norisoprenoids and benzene derivatives.

  12. Antihypertensive effect of auraptene, a monoterpene coumarin from the genus Citrus, upon chronic administration

    Directory of Open Access Journals (Sweden)

    Bibi Marjan Razavi

    2015-02-01

    Full Text Available Objective(s: Auraptene, a monoterpene coumarin from Citrus species, exhibits cardioprotective effects.In this study, the effects of auraptene administration were investigated on blood pressure of normotensive and desoxycorticosterone acetate (DOCA salt induced hypertensive rats. Materials and Methods: Five weeks administration of auraptene (2, 4, 8 and 16 mg/kg/day and nifedipine (0.25, 0.5, 1, 2 and 4 mg/kg/day in different groups of normotensive and hypertensive rats (at the end of 3 weeks treatment by DOCA salt was carried out and their effects on mean systolic blood pressure (MSBP and mean heart rate (MHR were evaluated using tail cuff method. Results: Our results indicated that chronic administration of auraptene (2, 4, 8 and 16 mg/kg/day significantly reduced the MSBP in DOCA salt treated rats in a dose and time dependent manner. The percent of decreases in MSBP levels by the highest dose of auraptene (16 mg/kg at the end of 4 th to 8 th weeks, were 7.00%, 10.78%, 16.07%, 21.28% and 27.54% respectively(P

  13. Synthesis and Self-assembling of Coumarin-based Low-molecular Weight Organogelators

    Institute of Scientific and Technical Information of China (English)

    CHEN Guo-jun; XUE Peng-chong; LU Ran; SONG Dong-po; BAO Chun-yan; XU Ting-hua; ZHAO Ying-ying

    2009-01-01

    Four coumarin derivatives(4a-4d) with different alkoxy chains were synthesized.It was found that compound 4d showed a better gelation ability than the other compounds,for example,it could self-assemble into organogeis in various organic fluids via ultrasound treatment or heating-cooling process,whereas compound 4c could only gel in a few mixed solvents and compounds 4a,4b could not form organogel.The results from fluorescent and F%IR spectra indicate that π-π interaction had an effect on the formation of the organogels of compound 4d besides H-bonding and van der Waals interaction,which were the driving forces for the self-assembling of compound 4c in gel state.The gel of compound 4d in toluene could emit strong fluorescence under UV irradiation and the [2+2]cyclo-addition was suggested by 1H NMR and fluorescence spectroscopy.This light-sensitive organogel might find application in optical materials.

  14. A bioassay using Artemia salina for detecting phototoxicity of plant coumarins.

    Science.gov (United States)

    Ojala, T; Vuorela, P; Kiviranta, J; Vuorela, H; Hiltunen, R

    1999-12-01

    Artemia salina (brine shrimp) has been successfully used for toxicity testing, and a screening test for phototoxicity has been developed based on this method. The ability of the method to test the phototoxic potential of seven known compounds was investigated. Athamantin (an angular furanocoumarin) and umbelliferone (a simple coumarin) showed no phototoxicity, while linear furanocoumarins exhibited phototoxic activity in the following order: psoralen > bergapten > peucedanin > xanthotoxin. The applicability of this method was also tested in screening the phototoxicity of plant material. Six plants from Apiaceae [Aegopodium podagraria L., Anethum graveolens L., Angelica archangelica L., Levisticum officinalis Koch, Petroselinum crispum (P. Mill) A. W. Hill., and Peucedanum palustre (L.) Moench] and one from Rutaceae (Ruta graveolens L.) were selected, all of them known to contain furanocoumarins. Extracts from leaves collected at different times during the growth period were used in the screening. Our results were in accordance with the furanocoumarin content of these plants and with the results of other phototoxicity tests. The Artemia salina method proved to be rapid, simple and inexpensive, and is therefore ideal in the initial biological screening of large numbers of samples for simultaneous detection of both toxicity and phototoxicity.

  15. RP TLC-based lipophilicity assessment of some natural and synthetic coumarins

    Energy Technology Data Exchange (ETDEWEB)

    Rabtti, El Hadi M.A.; Natic, Maja M.; Milojkovic-Opsenica, Dusanka M.; Trifkovic, Jelena D.; Vuckovic, Ivan M.; Tesic, Zivoslav Lj., E-mail: ztesic@chem.bg.ac.rs [Faculty of Chemistry, University of Belgrade, Belgrade (Serbia); Vajs, Vlatka E. [Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade (Serbia)

    2012-03-15

    The lipophilic character of twelve coumarins was investigated by reversed-phase thin-layer chromatography (RP TLC) on RP-18 silica. The three different binary solvent systems composed of water and organic modifier (methanol, tetrahydrofuran or acetonitrile) were used in order to determine retention parameter (R{sub M}{sup 0}) and octanol-water partition coefficient (log P{sub OW})as a measure of the lipophilicity of the tested compounds. Lipophilicity parameter (log P{sub OW}) was experimentally determined using eight standard solutes with known log P{sub OW} values which were analyzed under the same chromatographic conditions as the target substances. Lipophilicity parameters together with 2D molecular descriptors were subjected to the multivariate statistical analysis (principal component analysis (PCA) and partial least square (PLS) regression) in order to reveal the most influential factors governing the retention, i.e., lipophilicity of the investigated compounds. The quantitative structure-retention relationship models reveal the importance of descriptors which describe the size and the shape of the molecule as well as their polar properties. (author)

  16. Crystal Structure, Photoluminescent, and Theoretical Studies of 3-Acetyl-8-methoxy-coumarin

    Institute of Scientific and Technical Information of China (English)

    LI Jing; LI Xiang-Gao; WANG Shi-Rong

    2012-01-01

    The structure of 3-acetyl-8-methoxy-coumarin (AMC) was verified by single-crystal X-ray crystallography. It crystallizes in monoclinic, space group C2/c with a=15.073(3), b=13.068(3), c=11.549(2), β=119.92(3)o, V=1971.7(7)3 , Z=8, F(000)=912, D c=1.470 Mg/m3 , Mr=218.20, μ=0.111 mm-1 , the final R=0.0340 and wR=0.0968 for 1446 observed reflections with I 〉 2σ(I). The UV-vis absorption and fluorescence of AMC were discussed. The compound exhibits strong blue emission under ultraviolet light excitation. The molecular structure of AMC was optimized using density functional theory (DFT) at the B3LYP/6-31G(d) level, showing that the optimized geometer parameters are in good agreement with the experiment data. In addition, the HOMO and LUMO levels of AMC were deduced.

  17. Some new indole-coumarin hybrids; Synthesis, anticancer and Bcl-2 docking studies.

    Science.gov (United States)

    Kamath, Pooja R; Sunil, Dhanya; Ajees, A Abdul; Pai, K S R; Das, Shubhankar

    2015-12-01

    Hybrid molecules have attracted attention for their improved biological activity, selectivity and lesser side effects profile, distinct from their individual components. In the quest for novel anticancer drug entities, three series of indole-coumarin hybrids - 3-(1-benzyl-1H-indol-2-yl)-2H-chromen-2-ones, 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehydes and 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carboxylic acids were synthesized. All the synthesized compounds were characterized by spectral techniques like IR, (1)H NMR, (13)C NMR, mass spectrometry and elemental analysis. In silico docking studies of synthesized molecules with apoptosis related gene Bcl-2 that is recognized to play an important role in tumerogenesis were carried out. Dose-dependent cytotoxic effect of the compounds in human breast adenocarcinoma (MCF-7) and normal cell lines were assessed using MTT assay and compared with that of the standard marketed drug, Vincristine. Compound 4c had a highly lipophilic bromine substituent capable of forming halogen bond and was identified as a potent molecule both in docking as well as cytotoxicity studies. Flow cytometric cell cycle analysis of 4c exhibited apoptotic mode of cell death due to cell cycle arrest in G2/M phase. Structure activity relationship of these hybrid molecules was also studied to determine the effect of steric and electronic properties of the substituents on cell viability.

  18. A TDDFT/EFP1 study on hydrogen bonding dynamics of coumarin 151 in water

    Science.gov (United States)

    Ramegowda, Mariyappa

    2015-02-01

    Change in energy of hydrogen bonds (HBs) upon excitation, plays an important role on the spectra of chemical and biological molecules. Effective fragment potential (EFP) method of explicit water molecules embedded in polarizable continuum medium (PCM) is used for the solvation of 7-Amino-4-(trifluoromethyl)coumarin (C151). Time dependent density functional theory (TDDFT) calculations combined with EFP/PCM had been carried out to study the electronic structure and the exited state properties of C151 with five water molecules (C151-(H2O)5 complex). S0 state and S1 state geometries were optimized using DFT/TDDFT with PBE0 functional combined with cc-pVDZ basis set, the transition energies are computed with same basis set and functional. Change in HB energy is calculated using the procedure proposed by T. Nagata et al. to calculate solute-solvent interaction energy in Nagata et al. (2011). Upon photoexcitation of C151-(H2O)5 complex, A type (N⋯Hsbnd O) HB is weakened with decrease of energy by 4.37 kJ/mol, whereas B and C type (Cdbnd O⋯Hsbnd O and Nsbnd H⋯O) HBs are strengthened with increase of 5.62 and 10.21 kJ/mol energy, respectively. This study again confirmed that the intermolecular hydrogen bonds between C151 chromophore and aqueous solvents are strengthened, not cleaved upon electronic excitation.

  19. Combined spectroscopic and DFT studies on 6-bromo-4-chloro-3-formyl coumarin

    Science.gov (United States)

    Raj, R. K.; Gunasekaran, S.; Gnanasambandan, T.; Seshadri, S.

    2015-03-01

    The FTIR and FT-Raman spectra of 6-bromo-4-chloro-3-formyl coumarin (6B4C3FC) have been recorded in the region 4000-400 and 4000-100 cm-1, respectively. The optimized geometry, frequency and intensity of the vibrational bands were obtained by the density functional theory (DFT) using 6-31G(d,p) basis set. The harmonic vibrational frequencies were scaled and compared with experimental values. The observed and the calculated frequencies were found to be in good agreement. The UV-Visible spectrum was also recorded and compared with the theoretical values. The calculated HOMO and LUMO energies show that charge transfer occurs within molecule. The first order hyperpolarizability (β0) of 6B4C3FC is 21 times greater than that of urea. Stability of the molecule arising from hyperconjugative interactions, charge delocalization have been analyzed using natural bond orbital (NBO) analysis. Information about the charge density distribution of the molecule and its chemical reactivity has been obtained by mapping molecular electrostatic potential surface. In addition, the non-linear optical properties were discussed from the dipole moment values and the excitation wavelength in the UV-Visible region.

  20. The fluorescence quenching mechanism of coumarin 120 with CdS nanoparticles in aqueous suspension

    Energy Technology Data Exchange (ETDEWEB)

    Acar, Murat; Bozkurt, Ebru; Meral, Kadem; Arık, Mustafa; Onganer, Yavuz, E-mail: yonganer@atauni.edu.tr

    2015-01-15

    The interaction of coumarin 120 (C120) with CdS nanoparticles (CdS NPs) in aqueous suspension was examined by using UV–vis absorption, steady-state, time-resolved fluorescence, and electron paramagnetic resonance (EPR) spectroscopy techniques. The fluorescence intensity of C120 was quenched with increasing the amount of CdS NPs in the aqueous suspension. The spectroscopic data revealed that the C120 molecules adsorbed on CdS NPs via electrostatic interactions. The apparent association constant (K{sub app}) and the degree of association (α) for C120/CdS NPs were determined as 130.3 M{sup −1} and 0.51 for 4 nm CdS NPs and 624.3 M{sup −1} and 0.71 for 8 nm CdS NPs, respectively. The photoinduced EPR studies exhibited that no electron transfers between CdS and C120 taking place. The results revealed that the fluorescence quenching of C120 with different CdS NPs is due to the formation of a non-fluorescent complex. - Highlights: • Interaction of C120 with CdS NPs in aqueous solution was spectroscopically examined. • Nonfluorescent C120–CdS NPs complexes in aqueous solution were formed. • In the system, CdS NPs in aqueous solution acted as a fluorescence quencher.

  1. A coumarin-indole based colorimetric and "turn on" fluorescent probe for cyanide.

    Science.gov (United States)

    Xu, Yu; Dai, Xi; Zhao, Bao-Xiang

    2015-03-05

    A novel coumarin-indole based chemodosimeter with a simple structure was designed and prepared via a condensation reaction in high yield. The probe exhibited very high selectivity towards cyanide on both fluorescence and UV-vis spectra, which allowed it to quantitatively detect and imaging cyanide ions in organic-aqueous solution by either fluorescence enhancement or colorimetric changes. Confirmed by (1)H NMR and HRMS spectra, the detection mechanism was proved to be related with the Michael addition reaction induced by cyanide ions, which blocked the intramolecular charge transfer (ICT) of the probe. Moreover, the probe was able to be utilized efficiently in a wide pH range (7.5-10) with negligible interference from other anions and a low detection limit of 0.51μM. Application in 5 kinds of natural water source and accurate detection of cyanide in tap water solvent system also indicated the high practical significance of the probe. Copyright © 2014 Elsevier B.V. All rights reserved.

  2. Synthesis and experimental-computational characterization of nonlinear optical properties of triazacyclopentafluorene-coumarin derivatives

    Science.gov (United States)

    García, Santiago; Vázquez, Juan L.; Rentería, Marvin; Aguilar-Garduño, Isis G.; Delgado, Francisco; Trejo-Durán, Mónica; García-Revilla, Marco A.; Alvarado-Méndez, Edgar; Vázquez, Miguel A.

    2016-12-01

    A series of novel 3-(2,2a,3-triazacyclopenta[jk]fluoren-1-yl)-2H-chromen-2-one derivatives 5a-c have been synthesized by [8 + 2] cycloaddition reaction between the corresponding 3-(imidazo[1,2-a]pyrimidines)-2-yl)-2H-chromen-2-one 4a-c with 2-(trimethylsilyl)phenyl triflates as benzyne precursor in 65-80% yields. The strategic incorporation of triazacyclopentafluorene group at the 3-position of the coumarin molecules resulted in dyes with excellent nonlinear optical properties. The nonlinear optical properties of third order (compounds 5a-c) were studied using Z-scan technique. The high nonlinear response is of 10-7 cm2/W order. The nonlinearity of the compounds is an indication of a promising material for applications at low power, such as optical switching, waveguides, nonlinear contrast phase, among others. Theoretical results of HOMO-LUMO gaps and oscillator strengths are used to rationalize the high efficiency of the novel compound in the nonlinear optical behavior. In particular, 5b displays the best nonlinear optical properties and at the same time the smaller HOMO-LUMO gap and the highest oscillator strength.

  3. Inhibition of Mild Steel Corrosion in Hydrochloric Acid Solution by New Coumarin

    Directory of Open Access Journals (Sweden)

    Abdul Amir H. Kadhum

    2014-06-01

    Full Text Available A new coumarin derivative, N,N′-((2E,2′E-2,2′-(1,4-phenylenebis (methanylylidenebis(hydrazinecarbonothioylbis(2-oxo-2H-chromene-3-carboxamide PMBH, was synthesized and its chemical structure was elucidated and confirmed using spectroscopic techniques (Infrared spectroscopy IR, Proton nuclear  magnetic resonance, 1H-NMR and carbon-13 nuclear magnetic resonance 13C-NMR. The corrosion inhibition effect of PMBH on mild steel in 1.0 M HCl was investigated using corrosion potential (ECORR, potentiodynamic polarization, electrochemical impedance spectroscopy (EIS, and electrochemical frequency modulation (EFM measurements. The obtained results indicated that PMBH has promising inhibitive effects on the corrosion of mild steel in 1.0 M HCl across all of the conditions examined. Scanning electron microscopy (SEM was used to investigate the morphology of the mild steel before and after immersion in 1.0 M HCl solution containing 0.5 mM of PMBH. Surface analysis revealed improvement of corrosion resistance in presence of PMBH.

  4. Molecular structure, vibrational spectroscopic studies and natural bond orbital analysis of 7-amino-4-trifluoromethyl coumarin

    Indian Academy of Sciences (India)

    M K Subramanian; P M Anbarasan; S Manimegalai

    2010-05-01

    Quantum mechanical calculations of energies, geometries and vibrational wave numbers of 7-amino-4-trifluoromethyl coumarin (7A4TFMC) were carried out using Hartree–Fock (HF) and density functional theory (DFT) using hybrid functional BLYP and B3LYP with 6-31G(d,p) as basis set. The optimized geometrical parameters obtained by HF and DFT calculations are in good agreement with the experimental X-ray data. The best method to reproduce the experimental wave numbers is B3LYP method with the 6-31G(d,p) basis set. The difference between the observed and scaled wave number values of most of the fundamentals is very small. A detailed interpretation of the infrared spectra of 7A4TFMC was also reported. The entropy of the title compound was also performed at HF using the hybrid functional BLYP and B3LYP with 6-31 G(d,p) as basis set levels of theory. Natural bond orbital (NBO) analysis of the title molecule is also carried out. The theoretical spectrogram for FTIR spectra of the title molecule has been constructed.

  5. New Coumarins and Anti-Inflammatory Constituents from the Fruits of Cnidium monnieri

    Directory of Open Access Journals (Sweden)

    Tzong-Huei Lee

    2014-05-01

    Full Text Available The fruit of Cnidium monnieri is commercially used as healthcare products for the improvement of impotence and skin diseases. Three new coumarins, 3'-O-methylmurraol (1, rel-(1'S,2'S-1'-O-methylphlojodicarpin (2, and (1'S,2'S-1'-O-methylvaginol (3, have been isolated from the fruits of C. monnieri, together with 14 known compounds (4–17. The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 4–12, and 14–17 exhibited inhibition (IC50 ≤ 7.31 µg/mL of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB. Compounds 7, 9–11, 15, and 17 inhibited fMLP/CB-induced elastase release with IC50 values ≤7.83 µg/mL. This investigation reveals that bioactive isolates (especially 6, 7, 14, and 17 could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases.

  6. Inhibition viral RNP and anti-inflammatory activity of coumarins against influenza virus.

    Science.gov (United States)

    Wang, YuTao; Yan, Wen; Chen, QiaoLian; Huang, WanYi; Yang, Zifeng; Li, Xiong; Wang, XinHua

    2017-03-01

    Influenza viruses pose a severe threat to human health and a significant increase in antiviral drug-resistant among influenza viruses worldwide has been observed. Therefore, there is an urgent need to develop the new antiviral drugs, specifically from the natural products. In this study, the anti-viral and anti-inflammatory activities of coumarins against influenza A virus in vitro were investigated. One of the derivatives eleutheroside B1 showed a wide spectrum of anti- human influenza virus effect with the IC50 value of 64-125μg/ml in vitro, but it showed no effects against avian influenza virus. The time of addition was done and the results indicated that it had a potent antiviral effect when added at 0-6h, and also the virus yield was reduced by 60%. The influenza virus ribonucleoprotein was inhibited at 200μg/ml, and also the NP mRNA expression was inhibited at 50 and 200μg/ml. The expression level of cytokines and chemokines influenced by eleutheroside B1 was further demonstrated, the IL-6, CXCL-8, CCL-2 expression were all inhibited by the eleuthe roside B1 at concentration 200μg/ml. The findings of study suggest that eleutheroside B1 can be as potential agent to develop for the prevention and treatment of influenza A virus.

  7. Synthesis and Purification of 7-Prenyloxycoumarins and Herniarin as Bioactive Natural Coumarins

    Directory of Open Access Journals (Sweden)

    Mahdi Askari, Amirhossein Sahebkar, Mehrdad Iransahi

    2009-06-01

    Full Text Available Objective(s7-prenyloxycoumarins including 7-isopentenyloxycoumarin, auraptene and umbelliprenin, and herniarinhave been widely recognized as bioactive coumarins. This paper presents the ways to synthesis thesecompounds.Materials and Methods7-prenyloxycoumarins were synthesized by reaction between 7-hydroxycoumarin (1 M and relevant prenylbromides (1.5 M in acetone at room temperature. The reaction was carried out in the presence of DBU(1, 8-diazabicyclo [5.4.0] undec-7-ene (2 M. After 24 hr, the mixture was concentrated under reducedpressure. The compounds were purified by column chromatography.ResultsThree bioactive 7-prenyloxycoumarins, namely, umbelliprenin, auraptene and 7-isopentenyloxycoumarin,together with herniarin were synthesized from 7-hydroxycoumarin under alkaline conditions (DBU and thenpurified by column chromatography. The structures of the products were characterized by NMRspectroscopic method including 1H- and 13C-NMR experiments.ConclusionThe method of synthesis for 7-prenyloxycoumarins and herniarin which is presented here has not beenreported yet. Moreover, for the first time, umbelliprenin was chemically prepared in this work.Keywords: Auraptene, Herniarin, 7- Isopentenyloxycoumarin, 7-Prenyloxycoumarins, Synthesis,Umbelliprenin

  8. Coumarin Dyes for Dye-Sensitized Solar Cells - A Long-Range-Corrected Density Functional Study

    CERN Document Server

    Wong, Bryan M; 10.1063/1.3025924

    2010-01-01

    The excited-state properties in a series of coumarin solar cell dyes are investigated with a long-range-corrected (LC) functional which asymptotically incorporates Hartree-Fock exchange. Using time-dependent density functional theory (TDDFT), we calculate excitation energies, oscillator strengths, and excited-state dipole moments in each of the dyes as a function of the range-separation paramenter, mu. To investigate the acceptable range of mu and assess the quality of the LC-TDDFT formalism, an extensive comparison is made between LC-BLYP excitation energies and approximate coupled cluster singles and doubles (CC2) calculations. When using a properly-optimized value of mu, we find that the LC technique provides a consistent picture of charge-transfer excitations as a function of molecular size. In contrast, we find that the widely-used B3LYP hybrid functional severely overestimates excited-state dipole moments and underestimates vertical excitations energies, especially for larger dye molecules. The results ...

  9. Molecular modification of coumarin dyes for more efficient dye sensitized solar cells

    Energy Technology Data Exchange (ETDEWEB)

    Sanchez-de-Armas, Rocio; San-Miguel, Miguel A.; Oviedo, Jaime; Sanz, Javier Fdez. [Department of Physical Chemistry, University of Seville, Seville (Spain)

    2012-05-21

    In this work, new coumarin based dyes for dye sensitized solar cells (DSSC) have been designed by introducing several substituent groups in different positions of the NKX-2311 structure. Two types of substitutions have been considered: the introduction of three electron-donating groups (-OH, -NH{sub 2}, and -OCH{sub 3}) and two different substituents with steric effect: -CH{sub 2}-CH{sub 2}-CH{sub 2}- and -CH{sub 2}-HC=CH-. The electronic absorption spectra (position and width of the first band and absorption threshold) and the position of the LUMO level related to the conduction band have been used as theoretical criteria to evaluate the efficiency of the new dyes. The introduction of a -NH{sub 2} group produces a redshift of the absorption maximum position and the absorption threshold, which could improve the cell efficiency. In contrast, the introduction of -CH{sub 2}-CH{sub 2}-CH{sub 2}- does not modify significantly the electronic structure of NKX-2311, but it might prevent aggregation. Finally, -CH{sub 2}-HC=CH- produces important changes both in the electronic spectrum and in the electronic structure of the dye, and it would be expected as an improvement of cell efficiency for these dyes.

  10. Solution-phase Synthesis of a Combinatorial Library of 3-[4-(Coumarin-3-yl-1,3-thiazol-2-ylcarbamoyl]propanoic acid Amides

    Directory of Open Access Journals (Sweden)

    V. Chernykh

    2005-02-01

    Full Text Available The parallel solution-phase synthesis of a new combinatorial library of 3-[4-(R1-coumarin-3-yl-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides 9 has been developed. The synthesis involves two steps: 1 the synthesis of core building blocks – 3- [4-(coumarin-3-yl-1,3-thiazol-2-ylcarbamoyl]propanoic acids, 6 – by the reaction of 3-(ω-bromacetylcoumarins 1 with 3-amino(thioxomethylcarbamoylpropanoic acid (5; 2 the synthesis of the corresponding 3-[4-(coumarin-3-yl-1,3-thiazol-2-yl- carbamoyl]propanoic acids amides 9 using 1,1’-carbonyldimidazole as a coupling reagent. The advantages of the method compared to existing ones are discussed.

  11. Simultaneous Determination of Troxerutin and Coumarin in Troxerutin Coumarin Tablets by HPLC%HPLC法同时测定曲克芦丁香豆素片中曲克芦丁和香豆素的含量

    Institute of Scientific and Technical Information of China (English)

    施洁明; 林玲

    2013-01-01

    目的:建立同时测定曲克芦丁香豆素片中曲克芦丁和香豆素含量的方法.方法:采用高效液相色谱法.色谱柱为Venusil C18,以0.1 mol/L磷酸二氢钠溶液(用磷酸调节pH值至4.4)为流动相A,乙腈为流动相B,梯度洗脱,流速为0.5 ml/min,检测波长为276 nm.结果:曲克芦丁和香豆素检测质量浓度线性范围分别为1.00~200.98、1.05~42.19 μg/ml(r均为0.999 9),平均回收率分别为99.8%、99.5%,RSD分别为0.6%、0.8%(n=9).结论:该方法简便、准确,可用于曲克芦丁香豆素片的质量控制.%OBJECTIVE:To establish a method for simultaneous determination of troxerutin and coumarin in Troxerutin coumarin tablets.METHODS:HPLC method was adopted.The determination was performed on Venusil C18 column with mobile phase consisted of 0.1 mol/L NaH2PO4 solution (pH adjusted to 4.4 with phosphoric acid) as mobile phase A and acetonitrile as mobile phase B (gradient elution) at the flow rate of 0.5 ml/min.The detection wavelength was 276 nm.RESULTS:The linear ranges were 1.00-200.98 μg/ml for troxerutin (r=0.999 9) and 1.05-42.19 μg/ml for coumarin (r=0.999 9).The average recoveries were 99.8% (RSD=0.6%,n=9) and 99.5% (RSD=0.8%,n=9).CONCLUSIONS:The method is simple and accurate,and suitable for quality control of Troxerutin coumarin tablets.

  12. Coumarins as new matrices for matrix-assisted laser-desorption/ionization Fourier transform ion cyclotron resonance mass spectrometric analysis of hydrophobic compounds

    Energy Technology Data Exchange (ETDEWEB)

    Wang, Hang, E-mail: hangwang@sjtu.edu.cn [Instrumental Analysis Center, Shanghai Jiao Tong University, Dongchuan Road 800, Shanghai 200240 (China); Dai, Bona [Instrumental Analysis Center, Shanghai Jiao Tong University, Dongchuan Road 800, Shanghai 200240 (China); Liu, Bin [Key Laboratory of Kidney Disease Pathogenesis and Intervention of Hubei Province, College of Medicine, Hubei Polytechnic University, Huangshi, Hubei 435003 (China); Lu, Han [Department of Anesthesiology, Ruijin Hospital, Shanghai Jiao Tong University School of Medicine (SJTU-SM), 197, Rui Jin Er Road, Shanghai 200025 (China)

    2015-07-02

    Highlights: • Coumarins were used as new MALDI matrices. • Coumarins were used for MALDI-FT ICR MS detection of hydrophobic compounds. • DCA had improvement in detection sensitivity, stability, selectivity and reproducibility. • DCA was applied to sterols detection in yeast cells. - Abstract: Hydrophobic compounds with hydroxyl, aldehyde or ketone groups are generally difficult to detect using matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS), because these compounds have low proton affinity and are poorly ionized by MALDI. Herein, coumarins have been used as new matrices for MALDI-MS analysis of a variety of hydrophobic compounds with low ionization efficiency, including steroids, coenzyme Q10, a cyclic lipopeptide and cholesterol oleate. Five coumarins, including coumarin, umbelliferone, esculetin, 7-hydroxycoumarin-3-carboxylic acid (HCA) and 6,7-dihydroxycoumarin-3-carboxylic acid (DCA), were compared with the conventional matrices of 2,5-dihydroxybenzoic acid (DHB) and α-cyano-4-hydroxycinnamic acid (CHCA). Coumarins with hydroxyl or carboxylic acid groups enabled detection. Taking DCA as an example, this matrix proved to be superior to DHB or CHCA in detection sensitivity, stability, spot-to-spot and sample-to-sample reproducibility, and accuracy. DCA increased the stability of the target compounds and decreased the loss of water. The [M + Na]{sup +} peaks were observed for all target compounds by adding NaCl as an additive, and the [M − H{sub 2}O + H]{sup +} and [M + H]{sup +} peaks decreased. DCA was selected for the identification of sterols in yeast cells, and thirteen sterols were detected by Fourier transform ion cyclotron resonance (FT ICR) mass spectrometry. This work demonstrates the potential of DCA as a new matrix for detection of hydrophobic molecules by MALDI-MS and provides an alternative tool for screening sterols in antifungal research.

  13. 包载荧光探针香豆素-6的PLGA纳米粒的制备%Preparation of Fluorescent Probe Coumarin-6 Loaded PLGA Nanoparticles

    Institute of Scientific and Technical Information of China (English)

    李晓芳; 马艳结; 张晓; 陈钢

    2011-01-01

    OBJECTIVE To prepare fluorescent probe coumarin-6 loaded nanoparticles using the biodegradable material poly(lactic-co-glycolic acid)(PLGA) as carrier. METHODS Coumarin-6 loaded PLGA nanoparticles were prepared by emulsification solvent evaporation method. The formulation was optimized by orthogonal design using utilization ratio and entrapment efficiency as the indexes. RESULTS The mean entrapment efficiency of coumarin-6 loaded PLGA nanoparticles was 51.6% and the utilization ratio was 81.9%. The average size was 135 nm and the in vitro cumulative release of coumarin-6 from nanoparticles was less than 2% in 72 h. CONCLUSION The preparation process of coumarin-6 loaded PLGA nanoparticles is simple and feasible, and coumarin-6 can be used as fluorescence marker for in vivo tracing and targeting study of nanoparticles.%目的 以生物可降解材料聚乳酸-羟基乙酸共聚物(PLGA)为材料,制备包载荧光探针香豆素-6纳米粒,并进行处方优化.方法 采用乳化-溶剂挥发法制备香豆素-6-PLGA纳米粒,以利用率和包封率为考察指标,正交试验对处方进行优化.结果 制得香豆素-6纳米粒的包封率为51.6%,利用率为81.9%,平均粒径135nm,香豆素-6体外72 h泄漏率低于2%.结论 香豆素-6 PLGA纳米粒制备工艺简便可行,香豆素-6可作为荧光探针,用于纳米粒的动物体内示踪及靶向性研究.

  14. 3D QSAR studies on binding affinities of coumarin natural products for glycosomal GAPDH of Trypanosoma cruzi

    Science.gov (United States)

    Menezes, Irwin R. A.; Lopes, Julio C. D.; Montanari, Carlos A.; Oliva, Glaucius; Pavão, Fernando; Castilho, Marcelo S.; Vieira, Paulo C.; Pupo, M.^onica T.

    2003-05-01

    Drug design strategies based on Comparative Molecular Field Analysis (CoMFA) have been used to predict the activity of new compounds. The major advantage of this approach is that it permits the analysis of a large number of quantitative descriptors and uses chemometric methods such as partial least squares (PLS) to correlate changes in bioactivity with changes in chemical structure. Because it is often difficult to rationalize all variables affecting the binding affinity of compounds using CoMFA solely, the program GRID was used to describe ligands in terms of their molecular interaction fields, MIFs. The program VolSurf that is able to compress the relevant information present in 3D maps into a few descriptors can treat these GRID fields. The binding affinities of a new set of compounds consisting of 13 coumarins, for one of which the three-dimensional ligand-enzyme bound structure is known, were studied. A final model based on the mentioned programs was independently validated by synthesizing and testing new coumarin derivatives. By relying on our knowledge of the real physical data (i.e., combining crystallographic and binding affinity results), it is also shown that ligand-based design agrees with structure-based design. The compound with the highest binding affinity was the coumarin chalepin, isolated from Rutaceae species, with an IC50 value of 55.5 μM towards the enzyme glyceraldehyde-3-phosphate dehydrogenase (gGAPDH) from glycosomes of the parasite Trypanosoma cruzi, the causative agent of Chagas' disease. The proposed models from GRID MIFs have revealed the importance of lipophilic interactions in modulating the inhibition, but without excluding the dependence on stereo-electronic properties as found from CoMFA fields.

  15. Anti-inflammatory coumarins with short- and long-chain hydrophobic groups from roots of Angelica dahurica cv. Hangbaizhi.

    Science.gov (United States)

    Wei, Wei; Wu, Xiu-Wen; Deng, Gai-Gai; Yang, Xiu-Wei

    2016-03-01

    The (1)H NMR-guided fractionation of a cyclohexane soluble portion of the 75% ethanolic extract of the roots of Angelica dahurica cv. Hangbaizhi led to the isolation of two coumarins, namely, 5-(3"-hydroxy-3"-methylbutyl)-8-hydroxyfuranocoumarin, and isobyakangelicin hydrate-3"-ethyl ether, and ten coumarins with short- or long-chain hydrophobic groups, namely, andafocoumarins A-J. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of the C-2" secondary alcohols in ten of these compounds were deduced via the circular dichroism data of the in situ formed [Rh2(OCOCF3)4] complex, and oxidation reactions were utilized to determine location of the double bonds in the lipid chain of andafocoumarins H and I, respectively. The long-chain hydrophobic group of andafocoumarin J was determined by the method of chemical degradation and GC-MS analysis. It was the first time that coumarins with short- or long-chain hydrophobic groups in this plant had been comprehensively investigated. All isolates were assayed for their inhibitory effect against nitric oxide (NO) production in a lipopolysaccharide (LPS)-activated RAW264.7 macrophage cell line, among which andafocoumarins A and B exhibited a potent inhibition on LPS-activated NO production with IC50 values of 19.7 and 13.9 μM, respectively, indicating their stronger inhibitory activity than l-N(6)-(1-iminoethyl)-lysine (IC50=23.7 μM), a selective inhibitor of inducible nitric oxide synthase.

  16. Antihypertensive effect of auraptene, a monoterpene coumarin from the genus Citrus, upon chronic administration

    Science.gov (United States)

    Razavi, Bibi Marjan; Arasteh, Ebrahim; Imenshahidi, Mohsen; Iranshahi, Mehrdad

    2015-01-01

    Objective(s): Auraptene, a monoterpene coumarin from Citrus species, exhibits cardioprotective effects. In this study, the effects of auraptene administration were investigated on blood pressure of normotensive and desoxycorticosterone acetate (DOCA) salt induced hypertensive rats. Materials and Methods: Five weeks administration of auraptene (2, 4, 8 and 16 mg/kg/day) and nifedipine (0.25, 0.5, 1, 2 and 4 mg/kg/day) in different groups of normotensive and hypertensive rats (at the end of 3 weeks treatment by DOCA salt) was carried out and their effects on mean systolic blood pressure (MSBP) and mean heart rate (MHR) were evaluated using tail cuff method. Results: Our results indicated that chronic administration of auraptene (2, 4, 8 and 16 mg/kg/day) significantly reduced the MSBP in DOCA salt treated rats in a dose and time dependent manner. The percent of decreases in MSBP levels by the highest dose of auraptene (16 mg/kg) at the end of 4 th to 8 th weeks, were 7.00%, 10.78%, 16.07%, 21.28% and 27.54% respectively (P<0.001). Moreover the antihypertensive effect of auraptene was less than nifedipine (ED50 value of nifedipine = 0.7 mg/kg at 8th week and ED50 value of auraptene = 5.64 mg/kg at 8 week). Conclusion: Auraptene considerably reduced MSBP in hypertensive rats, but not in normotensive (normal saline treated) rats. The results of MHR measurement showed that the increase in MHR was not significant in comparison with DOCA treated rats. PMID:25810889

  17. Aflatoxin B1 Degradation by Stenotrophomonas Maltophilia and Other Microbes Selected Using Coumarin Medium

    Directory of Open Access Journals (Sweden)

    Tiangui Niu

    2008-08-01

    Full Text Available Aflatoxin B1 (AFB1 is one of the most harmful mycotoxins in animal production and food industry. A safe, effective and environmentally sound detoxification method is needed for controlling this toxin. In this study, 65 samples were screened from various sources with vast microbial populations using a newly developed medium containing coumarin as the sole carbon source. Twenty five single-colony bacterial isolates showing AFB1 reduction activity in a liquid culture medium were selected from the screen. Isolate 35-3, obtained from tapir feces and identified to be Stenotrophomonas maltophilia, reduced AFB1 by 82.5% after incubation in the liquid medium at 37 °C for 72 h. The culture supernatant of isolate 35-3 was able to degrade AFB1 effectively, whereas the viable cells and cell extracts were far less effective. Factors influencing AFB1 degradation by the culture supernatant were investigated. Activity was reduced to 60.8% and 63.5% at 20 °C and 30 °C, respectively, from 78.7% at 37 °C. The highest degradation rate was 84.8% at pH 8 and the lowest was only 14.3% at pH 4.0. Ions Mg2+ and Cu2+ were activators for AFB1 degradation, howeverï��Œion Zn2+ was a strong inhibitor. Treatments with proteinase K, proteinase K plus SDS and heating significantly reduced or eradicated the degradation activity of the culture supernatant. The results indicated that the degradation of AFB1 by S. maltophilia 35-3 was enzymatic and could have a great potential in industrial applications.

  18. Growth inhibition and apoptosis induced by osthole, a natural coumarin, in hepatocellular carcinoma.

    Directory of Open Access Journals (Sweden)

    Lurong Zhang

    Full Text Available BACKGROUND: Hepatocellular carcinoma (HCC is one of the most commonly diagnosed tumors worldwide and is known to be resistant to conventional chemotherapy. New therapeutic strategies are urgently needed for treating HCC. Osthole, a natural coumarin derivative, has been shown to have anti-tumor activity. However, the effects of osthole on HCC have not yet been reported. METHODS AND FINDINGS: HCC cell lines were treated with osthole at various concentrations for 24, 48 and 72 hours. The proliferations of the HCC cells were measured by MTT assays. Cell cycle distribution and apoptosis were determined by flow cytometry. HCC tumor models were established in mice by subcutaneously injection of SMMC-7721 or Hepa1-6 cells and the effect of osthole on tumor growths in vivo and the drug toxicity were studied. NF-κB activity after osthole treatment was determined by electrophoretic mobility shift assays and the expression of caspase-3 was measured by western blotting. The expression levels of other apoptosis-related genes were also determined by real-time PCR (PCR array assays. Osthole displayed a dose- and time-dependent inhibition of the HCC cell proliferations in vitro. It also induced apoptosis and caused cell accumulation in G2 phase. Osthole could significantly suppress HCC tumor growth in vivo with no toxicity at the dose we used. NF-κB activity was significantly suppressed by osthole at the dose- and time-dependent manner. The cleaved caspase-3 was also increased by osthole treatment. The expression levels of some apoptosis-related genes that belong to TNF ligand family, TNF receptor family, Bcl-2 family, caspase family, TRAF family, death domain family, CIDE domain and death effector domain family and CARD family were all increased with osthole treatment. CONCLUSION: Osthole could significantly inhibit HCC growth in vitro and in vivo through cell cycle arrest and inducing apoptosis by suppressing NF-κB activity and promoting the expressions of

  19. Growth Inhibition and Apoptosis Induced by Osthole, A Natural Coumarin, in Hepatocellular Carcinoma

    Science.gov (United States)

    Zhang, Lurong; Jiang, Guorong; Yao, Fei; He, Yan; Liang, Guoqiang; Zhang, Yinsheng; Hu, Bo; Wu, Yan; Li, Yunsen; Liu, Haiyan

    2012-01-01

    Background Hepatocellular carcinoma (HCC) is one of the most commonly diagnosed tumors worldwide and is known to be resistant to conventional chemotherapy. New therapeutic strategies are urgently needed for treating HCC. Osthole, a natural coumarin derivative, has been shown to have anti-tumor activity. However, the effects of osthole on HCC have not yet been reported. Methods and Findings HCC cell lines were treated with osthole at various concentrations for 24, 48 and 72 hours. The proliferations of the HCC cells were measured by MTT assays. Cell cycle distribution and apoptosis were determined by flow cytometry. HCC tumor models were established in mice by subcutaneously injection of SMMC-7721 or Hepa1-6 cells and the effect of osthole on tumor growths in vivo and the drug toxicity were studied. NF-κB activity after osthole treatment was determined by electrophoretic mobility shift assays and the expression of caspase-3 was measured by western blotting. The expression levels of other apoptosis-related genes were also determined by real-time PCR (PCR array) assays. Osthole displayed a dose- and time-dependent inhibition of the HCC cell proliferations in vitro. It also induced apoptosis and caused cell accumulation in G2 phase. Osthole could significantly suppress HCC tumor growth in vivo with no toxicity at the dose we used. NF-κB activity was significantly suppressed by osthole at the dose- and time-dependent manner. The cleaved caspase-3 was also increased by osthole treatment. The expression levels of some apoptosis-related genes that belong to TNF ligand family, TNF receptor family, Bcl-2 family, caspase family, TRAF family, death domain family, CIDE domain and death effector domain family and CARD family were all increased with osthole treatment. Conclusion Osthole could significantly inhibit HCC growth in vitro and in vivo through cell cycle arrest and inducing apoptosis by suppressing NF-κB activity and promoting the expressions of apoptosis

  20. Solvation dynamics of coumarin 153 in alcohols confined in silica nanochannels.

    Science.gov (United States)

    Kamijo, Toshio; Yamaguchi, Akira; Suzuki, Shintaro; Teramae, Norio; Itoh, Tetsuji; Ikeda, Takuji

    2008-11-20

    Solvation dynamics in alcohols confined in silica nanochannels was examined by time-resolved fluorescence spectroscopy using coumarin 153 (C153) as a fluorescent probe. Surfactant-templated mesoporous silica was fabricated inside the pores of an anodic alumina membrane. The surfactant was removed by calcination to give mesoporous silica (Cal-NAM) containing one-dimensional (1D) silica nanochannels (diameter, 3.1 nm) whose inner surface was covered with silanol groups. By treating Cal-NAM with trimethylchlorosilane, trimethylsilyl (TMS) groups were formed on the inner surface of the silica nanochannels (TMS-NAM). Fluorescence dynamic Stokes shifts of C153 were measured in alcohols (ethanol, butanol, hexanol, and decanol) confined in the silica nanochannels of Cal- and TMS-NAMs, and the time-dependent fluorescence decay profiles could be best fitted by a biexponential function. The estimated solvent relaxation times were much larger than those observed in bulk alcohols for both Cal- and TMS-NAMs when ethanol or butanol was used as a solvent, indicating that the mobility of these alcohol molecules was restricted within the silica nanochannels. However, hexanol or decanol in Cal- and TMS-NAMs did not cause a remarkable increase in the solvent relaxation time in contrast to ethanol or butanol. Therefore, it was concluded that a relatively rigid assembly of alcohols (an alcohol chain) was formed within the silica nanochannels by hydrogen bonding interaction and van der Waals force between the surface functional groups of the silica nanochannels and alcohol molecules and by the successive interaction between alcohol molecules when alcohol with a short alkyl chain (ethanol or butanol) was used as a solvent.

  1. Bioassay-Guided Isolation of Sesquiterpene Coumarins from Ferula narthex Bioss: A New Anticancer Agent

    Science.gov (United States)

    Alam, Mahboob; Khan, Ajmal; Wadood, Abdul; Khan, Ayesha; Bashir, Shumaila; Aman, Akhtar; Jan, Abdul Khaliq; Rauf, Abdur; Ahmad, Bashir; Khan, Abdur Rahman; Farooq, Umar

    2016-01-01

    The main objective of cancer management with chemotherapy (anticancer drugs) is to kill the neoplastic (cancerous) cell instead of a normal healthy cell. The bioassay-guided isolation of two new sesquiterpene coumarins (compounds 1 and 2) have been carried out from Ferula narthex collected from Chitral, locally known as “Raw.” Anticancer activity of crude and all fractions have been carried out to prevent carcinogenesis by using MTT assay. The n-hexane fraction showed good activity with an IC50 value of 5.434 ± 0.249 μg/mL, followed by crude MeFn extract 7.317 ± 0.535 μg/mL, and CHCl3 fraction 9.613 ± 0.548 μg/mL. Compounds 1 and 2 were isolated from chloroform fraction. Among tested pure compounds, compound 1 showed good anticancer activity with IC50 value of 14.074 ± 0.414 μg/mL. PASS (Prediction of Activity Spectra) analysis of the compound 1 was carried out, in order to predicts their binding probability with anti-cancer target. As a results the compound 1 showed binding probability with human histone acetyltransferase with Pa (probability to be active) value of 0.303. The compound 1 was docked against human histone acetyltransferase (anti-cancer drug target) by using molecular docking simulations. Molecular docking results showed that compound 1 accommodate well in the anti-cancer drug target. Moreover the activity support cancer chemo preventive activity of different compounds isolated from the genus Ferula, in accordance with the previously reported anticancer activities of the genus. PMID:26909039

  2. A novel coumarin-quinone derivative SV37 inhibits CDC25 phosphatases, impairs proliferation, and induces cell death.

    Science.gov (United States)

    Bana, Emilie; Sibille, Estelle; Valente, Sergio; Cerella, Claudia; Chaimbault, Patrick; Kirsch, Gilbert; Dicato, Mario; Diederich, Marc; Bagrel, Denyse

    2015-03-01

    Cell division cycle (CDC) 25 proteins are key phosphatases regulating cell cycle transition and proliferation by regulating CDK/cyclin complexes. Overexpression of these enzymes is frequently observed in cancer and is related to aggressiveness, high-grade tumors and poor prognosis. Thus, targeting CDC25 by compounds, able to inhibit their activity, appears a good therapeutic approach. Here, we describe the synthesis of a new inhibitor (SV37) whose structure is based on both coumarin and quinone moieties. An analytical in vitro approach shows that this compound efficiently inhibits all three purified human CDC25 isoforms (IC50 1-9 µM) in a mixed-type mode. Moreover, SV37 inhibits growth of breast cancer cell lines. In MDA-MB-231 cells, reactive oxygen species generation is followed by pCDK accumulation, a mark of CDC25 dysfunction. Eventually, SV37 treatment leads to activation of apoptosis and DNA cleavage, underlining the potential of this new type of coumarin-quinone structure.

  3. Red Emitting Coumarin-Azo Dyes : Synthesis, Characterization, Linear and Non-linear Optical Properties-Experimental and Computational Approach.

    Science.gov (United States)

    Tathe, Abhinav B; Sekar, Nagaiyan

    2016-07-01

    The coumarin molecules with 7-(N,N-diethylamino) substitution and aryl azo (Ar-N=N-) at 3-position were synthesized, by reacting diazonium salt of substituted amines and 7-(N, N-diethylamino)-4-hydroxy coumarin under basic conditions. They were found to be fluorescent despite the presence of azo group. The azo group rotation was blocked by complexing with -BF2, so as to get a red shift in absorption. The azo molecules show charge transfer, whereas BF2-complexes do not. The dipole moment ratios between the ground and excited states calculated suggest highly polar excited state and an intra-molecular charge transfer at the excited state in the case of azo dyes. The NLO properties were calculated by solvatochromic method and computationally. Second order hyperpolarizability was found to be 46 to 1083 times more than urea. DFT and TDTDF calculations were performed to understand the electronic properties of the molecules at the ground as well as excited states.

  4. Novel oxime-bearing coumarin derivatives act as potent Nrf2/ARE activators in vitro and in mouse model.

    Science.gov (United States)

    Chang, Ken-Ming; Chen, Huang-Hui; Wang, Tai-Chi; Chen, I-Li; Chen, Yu-Tsen; Yang, Shyh-Chyun; Chen, Yeh-Long; Chang, Hsin-Huei; Huang, Chih-Hsiang; Chang, Jang-Yang; Shih, Chuan; Kuo, Ching-Chuan; Tzeng, Cherng-Chyi

    2015-12-01

    We have designed and synthesized certain novel oxime- and amide-bearing coumarin derivatives as nuclear factor erythroid 2 p45-related factor 2 (Nrf2) activators. The potency of these compounds was measured by antioxidant responsive element (ARE)-driven luciferase activity, level of Nrf2-related cytoprotective genes and proteins, and antioxidant activity. Among them, (Z)-3-(2-(hydroxyimino)-2-phenylethoxy)-2H-chromen-2-one (17a) was the most active, and more potent than the positive t-BHQ in the induction of ARE-driven luciferase activity. Exposure of HSC-3 cells to various concentrations of 17a strongly increased Nrf2 nuclear translocation and the expression level of Nrf2-mediated cytoprotective proteins in a concentration-dependent manner. HSC-3 cells pretreated with 17a significantly reduced t-BOOH-induced oxidative stress. In the animal experiment, Nrf2-mediated cytoprotective proteins, such as aldo-keto reductase 1 subunit C-1 (AKR1C1), glutathione reductase (GR), and heme oxygenase (HO-1), were obviously elevated in the liver of 17a-treated mice than that of control. These results suggested that novel oxime-bearing coumarin 17a is able to activate Nrf2/ARE pathway in vivo and are therefore seen as a promising candidate for further investigation.

  5. Coumarin-Based Turn-On Fluorescence Probe for Specific Detection of Glutathione over Cysteine and Homocysteine.

    Science.gov (United States)

    He, Longwei; Xu, Qiuyan; Liu, Yong; Wei, Haipeng; Tang, Yonghe; Lin, Weiying

    2015-06-17

    We have prepared a turn-on fluorescent probe for biothiols based on bromoketo coumarin (KC-Br). The emission intensity of the coumarin chromophore is modulated by both the heavy atom effect and internal charge transfer (ICT) process. The probe KC-Br is intrinsically nonfluorescent; however, after being reacted with thiols, the bromide moiety is substituted by the -SH group, which elicits a significant fluorescence increase. We surmised the free -NH2 group would further react with carbonyl in the Cys/Hcy-substituted intermediate product yielding to Schiff base compound KC-Cys/KC-Hcy, but not in compound KC-GSH. The ICT effect has a stronger influence in compound KC-GSH than that in compound KC-Cys/KC-Hcy, resulting in compound KC-GSH having a stronger fluorescence. Thus, the probe has a good selectivity for GSH over other various biologically relevant species and even two other similar biothiols (Cys/Hcy) and could image glutathione (GSH) in living cells. We expect the design concept presented in this work would be widely used for the design of fluorescent probes for distinguishing among biothiols.

  6. Multi-Fluorinated Azido Coumarins for Rapid and Selective Detection of Biological H2 S in Living Cells.

    Science.gov (United States)

    Zhu, Zhentao; Li, Yanyan; Wei, Chao; Wen, Xin; Xi, Zhen; Yi, Long

    2016-01-01

    Hydrogen sulfide (H2 S) is an endogenously produced gaseous signaling molecule with multiple biological functions. In order to visualize the endogenous in situ production of H2 S in living cells in real time, here we developed multi-fluorinated azido coumarins as fluorescent probes for the rapid and selective detection of biological H2 S. Kinetic studies indicated that an increase in fluorine substitution leads to an increased rate of H2 S-mediated reduction reaction, which is also supported by our theoretical calculations. To our delight, tetra-fluorinated coumarin 1 could react with H2 S fast (t1/2 ≈1 min) and selectively, which could be further used for continuous enzymatic assays and for visualization of intracellular H2 S. Bioimaging results obtained with 1 revealed that d-Cys could induce a higher level of endogenous H2 S production than l-Cys in a time-dependent manner in living cell.

  7. Determination of vanillin, ethyl vanillin, and coumarin in infant formula by liquid chromatography-quadrupole linear ion trap mass spectrometry.

    Science.gov (United States)

    Shen, Yan; Han, Chao; Liu, Bin; Lin, Zhengfeng; Zhou, Xiujin; Wang, Chengjun; Zhu, Zhenou

    2014-02-01

    A simple, precise, accurate, and validated liquid chromatography-quadrupole linear ion trap mass spectrometry method was developed for the determination of vanillin, ethyl vanillin, and coumarin in infant formula samples. Following ultrasonic extraction with methanol/water (1:1, vol/vol), and clean-up on an HLB solid-phase extraction cartridge (Waters Corp., Milford, MA), samples were separated on a Waters XSelect HSS T3 column (150 × 2.1-mm i.d., 5-μm film thickness; Waters Corp.), with 0.1% formic acid solution-acetonitrile as mobile phase at a flow rate of 0.25 mL/min. Quantification of the target was performed by the internal standard approach, using isotopically labeled compounds for each chemical group, to correct matrix effects. Data acquisition was carried out in multiple reaction monitoring transitions mode, monitoring 2 multiple reaction monitoring transitions to ensure an accurate identification of target compounds in the samples. Additional identification and confirmation of target compounds were performed using the enhanced product ion modus of the linear ion trap. The novel liquid chromatography-quadrupole linear ion trap mass spectrometry platform offers the best sensitivity and specificity for characterization and quantitative determination of vanillin, ethyl vanillin, and coumarin in infant formula and fulfills the quality criteria for routine laboratory application.

  8. Improving the antidepressant action and the bioavailability of sertraline by co-crystallization with coumarin 3-carboxylate. Structural determination.

    Science.gov (United States)

    Escudero, Graciela E; Laino, Carlos H; Echeverría, Gustavo A; Piro, Oscar E; Martini, Nancy; Rodríguez, Ailén N; Martínez Medina, Juan J; López Tévez, Libertad L; Ferrer, Evelina G; Williams, Patricia A M

    2016-04-05

    To improve the antidepressant action of sertraline a new salt with coumarin-3-carboxylate anion (SerH-CCA) has been synthesized by two different methods and characterized by FTIR spectroscopy and structural determinations by X-ray diffraction methods. The new salt is stabilized by strong intermolecular H-bonds involving the protonated amine group of SerH and the deprotonated carboxylate group of CCA. These findings can be correlated with the interpretation of the infrared spectrum. The salt, sertraline (SerHCl) and the sodium salt of coumarin-3-carboxylate (NaCCA) were orally administered male Wistar rats (10 mg/kg, based on sertraline). Rats were evaluated in separate groups by means of the forced swimming (FST). SerH-CCA produced antidepressant effects in a magnitude that exceeded SerHCl individual effects. None of these treatments affected activity levels by the open field OFT tests. We have also determined that the ion pair also improve the binding to bovine serum albumin (BSA) of the drug but retain its antimicrobial activity. It is reasonable to conclude that the replacement of chloride anion by a large organic anion in sertraline strengthens the pharmacological action of the native drug, binding to BSA with higher activity and retaining the antimicrobial activity of the antidepressant compound.

  9. Inhibition of gastric H+,K+-ATPase activity by flavonoids, coumarins and xanthones isolated from Mexican medicinal plants.

    Science.gov (United States)

    Reyes-Chilpa, Ricardo; Baggio, Cristiane Hatsuko; Alavez-Solano, Dagoberto; Estrada-Muñiz, Elizabeth; Kauffman, Frederick C; Sanchez, Rosa I; Mesia-Vela, Sonia

    2006-04-21

    Medicinal plants are commonly used in Latin American folk medicine for the treatment of gastric problems. In order to understand the properties of some of their chemical constituents, four natural xanthones, an acetylated derivative, two coumarins (mammea A/BA and mammea C/OA) isolated from Calophyllum brasiliense Cambess and two flavonoids (minimiflorin and mundulin) isolated from Lonchocarpus oaxacensis Pittier, and the chalcone lonchocarpin isolated from Lonchocarpus guatemalensis Benth were tested for their activities on gastric H+,K+-ATPase isolated from dog stomach. All the compounds tested inhibited H+,K+-ATPase activity with varied potency. The xanthones inhibited the H+,K+-ATPase with IC50 values ranging from 47 microM to 1.6 mM. Coumarins inhibited H+,K+-ATPase with IC50 values of 110 and 638 microM. IC50 values for the flavonoids ranged from 9.6 to 510 microM among which minimiflorin was the most potent. The results suggest that H+,K+-ATPase is sensitive to inhibition by several types of structurally different natural compounds. The potency of the effects on gastric H+,K+-ATPase depends on the presence, position and number of hydroxyls groups in the molecule. Collectively, these results suggest a potential for important pharmacological and toxicological interactions by these types of natural products at the level of H+,K+-ATPase which may explain, at least in part, the gastroprotective properties, indicated by traditional medicine, of the plants from which these compounds were isolated.

  10. 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.

  11. Coumarins from the aerial parts of Prangos uloptera (Apiaceae Cumarinas das partes aéreas de Prangos uloptera (Apiaceae

    Directory of Open Access Journals (Sweden)

    Seyed Mehdi Razavi

    2008-03-01

    Full Text Available Phytochemical studies on the aerial parts of Prangos uloptera, an endemic Iranian species of the genus Prangos, yielded five coumarins, xanthotoxin (1, prangenin (2, scopoletin (3, deltoin (4 and prangolarin (5. The structures of these coumarins were elucidated by spectroscopic means, and the antioxidant potential of 1-5 was evaluated by the DPPH assay. The chemotaxonomic significance of 1-5 is also discussed.Os estudos fitoquímicos das partes aéreas de Prangos uloptera, uma espécie do gênero Prangos endêmica do Irã, forneceram cinco cumarinas, xantotoxina (1, prangenina (2, escopoletina (3, deltoína (4 e prangolarina (5. As estruturas destas cumarinas foram elucidas através de métodos espectroscópicos e o potencial antioxidante de 1-5 foi avaliado pelo ensaio de DPPH. O significado quimiotaxonômico de 1-5 também é discutido.

  12. Isoquinoline-catalyzed reaction between 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one and dialkyl acetylene dicarboxylates: synthesis of coumarin and pyranopyrane derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Anary-Abbasinejad, Mohammad; Anaraki-Ardakani, Hossein; Mosslemin, Mohammad Hossein [Islamic Azad University, Yazd (Iran, Islamic Republic of). Dept. of Chemistry; Khavasi, Hamid Reza [Shahid Beheshti University, Tehran (Iran, Islamic Republic of). Dept. of Chemistry

    2010-07-01

    In this work we report the reaction between dialkyl acetylenedicarboxylates and enolic systems such as 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclohexanedione, 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one in the presence of isoquinoline, which leads to new coumarin and pyranopyran derivatives. (author)

  13. Coumarin-containing-star-shaped 4-arm-polyethylene glycol: targeted fluorescent organic nanoparticles for dual treatment of photodynamic therapy and chemotherapy.

    Science.gov (United States)

    Gangopadhyay, Moumita; Singh, Tanya; Behara, Krishna Kalyani; Karwa, S; Ghosh, S K; Singh, N D Pradeep

    2015-07-01

    Single component fluorescent organic polymeric nanoparticles (NPs) have been synthesized based on a star shaped 4-arm PEG containing coumarin chromophore for the concomitant employment of photodynamic therapy (PDT) and chemotherapy synergistically to wipe out tumour cells with a high efficiency. Polymeric NPs are emerging as the most promising nanoparticulates in the area of drug delivery systems due to their ability to overcome the disadvantages like premature and imprecise control over the drug release, lack of loading capacity etc. Among polymeric NPs, star shaped branched polymers have attracted great attention mainly due to their multiple functionalization properties. Hence, herein we have made use of a multi-arm PEG, functionalized with a targeting unit biotin and a coumarin fluorophore for site-specific and image guided synergic treatment of cancer cells. The anticancer drug chlorambucil is released by the coumarin chromophore in a photocontrolled manner. In addition to that, coumarin also generated singlet oxygen upon irradiation with UV/vis light (≥365 nm) with a moderate quantum yield of ∼0.37. In vitro application of thus prepared organic polymeric nanoparticles (PEG-Bio-Cou-Cbl) in the HeLa cell line shows a reduction of cell viability by up to ∼5% in the case of a combined treatment of PDT and chemotherapy whereas analogous organic polymeric NPs without the chemotherapeutic drug (PEG-Bio-Cou) result in ∼49% cell viability by means of PDT process only.

  14. Prediction of the metabolic clearance of benzophenone-2, and its interaction with isoeugenol and coumarin using cryopreserved human hepatocytes in primary culture.

    Science.gov (United States)

    de Sousa, Georges; Teng, Sophie; Salle-Siri, Romain; Pery, Alexandre; Rahmani, Roger

    2016-04-01

    Benzophenone-2 (BP2) is widely used as a UV screen in both industrial products and cosmetic formulations, where it is frequently found associated with fragrance compounds, such as isoeugenol and coumarin. BP2 is now recognized as an endocrine disruptor, but to date, no information has been reported on its fate in humans. The intrinsic clearance (Clint) and metabolic interactions of BP2 were explored using cryopreserved human hepatocytes in primary cultures. In vitro kinetic experiments were performed to estimate the Michaelis-Menten parameters. The substrate depletion method demonstrated that isoeugenol was cleared more rapidly than BP2 or coumarin (Clint = 259, 94.7 and 0.40 μl/min/10(6) cells respectively). This vitro model was also used to study the metabolic interactions between BP2 and isoeugenol and coumarin. Coumarin exerted no effects on either isoeugenol or BP2 metabolism, because of its independent metabolic pathway (CYP2A6). Isoeugenol appeared to be a potent competitive substrate inhibitor of BP2 metabolism, equivalent to the specific UGT1A1 substrate: estradiol. Despite the fact that inhibition of UGT by xenobiotics is not usually considered to be a major concern, the involvement of UGT1A1 in BP2 metabolism may have pharmacokinetic and pharmacological consequences, due to the its polymorphisms in humans and its pure estrogenic effect.

  15. TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes: A novel method for the solid-phase synthesis of dihydrocoumarins and coumarins

    Institute of Scientific and Technical Information of China (English)

    E Tang; Wen Li; Zhang Yong Gao; Xi Gu

    2012-01-01

    TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl seleaide as the selenium source.This catalytic process provides an efficient method for the regioselective synthesis of dihydrocoumarins possessing a seleno-functionality,followed by traceless cleavage of selenium linker to provide dihydrocoumarins and coumarins in good yields and purities.

  16. Structure-cytotoxicity relationships of a series of natural and semi-synthetic simple coumarins as assessed in two human tumour cell lines

    NARCIS (Netherlands)

    Kolodziej, H; Kayser, O; Woerdenbag, HJ; vanUden, W; Pras, N

    1997-01-01

    The cytotoxicity of 22 natural and semi-synthetic simple coumarins was evaluated in GLC(4), a human small cell lung carcinoma cell line, and in COLO 320, a human colorectal cancer cell line, using the microculture tetrazolium (MTT) assay. With IC50 values > 100 mu M, following a continuous (96h) inc

  17. Screening of promising chemotherapeutic candidates from plants against human adult T-cell leukemia/lymphoma (V): coumarins and alkaloids from Boenninghausenia japonica and Ruta graveolens.

    Science.gov (United States)

    Nakano, Daisuke; Ishitsuka, Kenji; Matsuda, Narumi; Kouguchi, Ai; Tsuchihashi, Ryota; Okawa, Masafumi; Okabe, Hikaru; Tamura, Kazuo; Kinjo, Junei

    2017-01-01

    During the course of our studies towards the identification of promising chemotherapeutic candidates from plants against two human T-cell lymphotropic virus type I-infected T-cell lines (MT-1 and MT-2), we screened 17 extracts from 9 rutaceous plants against MT-1 and MT-2 cells. The extracts from the aerial parts and roots of Boenninghausenia japonica, as well as the leaves and roots of Ruta graveolens showed potent antiproliferative effects. After activity-guided fractionation, we isolated 44 compounds from two rutaceous plants, including three new compounds (1-3), which were classified into 26 coumarin analogs (13 coumarins, 8 furanocoumarins, 4 dihydrofuranocoumarins and one dihydropyranocoumarin), 15 alkaloid analogs (7 quinolone alkaloids, 4 acridone alkaloids, 3 furanoquinoline alkaloids and one tetrahydroacridone alkaloid) and 3 flavonoid glycosides. Structure-activity relationship studies were also evaluated. The coumarin compounds (2, 3 and 7-9) bearing a 3-dimethylallyl moiety showed potent activity. Similarly, of all the furanocoumarins evaluated in the current study, compound 17 bearing a 3-dimethylallyl group also showed potent activity. A dihydrofuranocoumarin (27) bearing a 3-dimethylallyl moiety showed the most potent activity. Following 27, compound 28 showed potent activity. These results therefore suggested that the presence of a 3-dimethylallyl moiety was important to the antiproliferative activity of these coumarin analogs.

  18. Monte Carlo Method Based QSAR Modeling of Coumarin Derivates as Potent HIV‐1 Integrase Inhibitors and Molecular Docking Studies of Selected 4‐phenyl Hydroxycoumarins

    Directory of Open Access Journals (Sweden)

    Veselinović Jovana

    2014-06-01

    Full Text Available In search for new and promising coumarin compounds as HIV-1 integrase inhibitors, chemoinformatic methods like quantitative structure-activity relationships (QSAR modeling and molecular docking have an important role since they can predict desired activity and propose molecule binding to enzyme.

  19. Solvent organization around the perfluoro group of coumarin 153 governs its photophysical properties: An experimental and simulation study of coumarin dyes in ethanol as well as fluorinated ethanol solvents

    Science.gov (United States)

    Mondal, Saptarsi; Halder, Ritaban; Biswas, Biswajit; Jana, Biman; Singh, Prashant Chandra

    2016-05-01

    The self-aggregation property of the perfluoro group containing molecules makes it important in the research fields of biology and polymer and organic synthesis. In the quest of understanding the role of the perfluoro group on the photophysical properties of perfluoro-containing molecules in biologically important fluoroethanol solvents, we have applied photophysical as well as molecular dynamics simulation techniques to explore the properties of perfluoro groups containing molecule coumarin-153 (C153) in ethanol (ETH), monofluoroethanol (MFE), difluoroethanol (DFE), and trifluoroethanol (TFE) and compared them with the molecules without perfluoro moiety, namely coumarin-6H (C6H) and coumarin-480 (C480). In contrast to C6H and C480, the excited state lifetime of C153 in fluorinated ETHs is not monotonic. The excited state lifetime of C153 decreases in MFE and DFE as compared to ETH, whereas in TFE, it increases as compared to MFE and DFE. Molecular dynamics simulation reveals that the carbon terminal away from the OH group of fluorinated ETHs has a preferential orientation near the perfluoro (CF3) group of C153. In MFE and DFE, the CF3 group of C153 prefers to have a CF2—F⋯H —(CHF) type of electrostatic interaction over CF2—F⋯F —(CH2) kind of dispersion interaction which increases the rate of nonradiative decay, probably due to the electrostatic nature of the CF2—F⋯H —(CHF) hydrogen bond. On the other hand, in TFE, C—F⋯ F—C type of dispersion interaction, also known as fluorous interaction, takes place between the CF3 groups of C153 and TFE which decreases the rate of nonradiative rate as compared to MFE and DFE, leading to the increased lifetime of C153 in TFE. Photophysical and MD simulation studies clearly depict that the structural organization of solvents and their interaction with the fluorocarbon group are crucial factors for the photophysical behavior of the fluorocarbon containing molecules.

  20. Investigation of binding mechanism of novel 8-substituted coumarin derivatives with human serum albumin and α-1-glycoprotein.

    Science.gov (United States)

    Yeggoni, Daniel Pushpa Raju; Manidhar, Darla Mark; Suresh Reddy, Cirandur; Subramanyam, Rajagopal

    2016-09-01

    Coumarin molecules have biological activities possessing lipid-controlling activity, anti-hepatitis C activity, anti-diabetic, anti-Parkinson activity, and anti-cancer activity. Here, we have presented an inclusive study on the interaction of 8-substituted-7-hydroxy coumarin derivatives (Umb-1/Umb-2) with α-1-glycoprotein (AGP) and human serum albumin (HSA) which are the major carrier proteins in the human blood plasma. Binding constants obtained from fluorescence emission data were found to be KUmb-1=3.1 ± .01 × 10(4) M(-1), KUmb-2 = 7 ± .01 × 10(4) M(-1), which corresponds to -6.1 and -6.5 kcal/mol of free energy for Umb-1 and Umb-2, respectively, suggesting that these derivatives bind strongly to HSA. Also these molecules bind to AGP with binding constants of KUmb-1-AGP=3.1 ± .01 × 10(3) M(-1) and KUmb-2-AGP = 4.6 ± .01 × 10(3) M(-1). Further, the distance, r between the donor (HSA) and acceptor (Umb-1/Umb-2) was calculated based on the Forster's theory of non-radiation energy transfer and the values were observed to be 1.14 and 1.29 nm in Umb-1-HSA and Umb-2-HSA system, respectively. The protein secondary structure of HSA was partially unfolded upon binding of Umb-1 and Umb-2. Furthermore, site displacement experiments with lidocaine, phenylbutazone (IIA), and ibuprofen (IIIA) proves that Umb derivatives significantly bind to subdomain IIIA of HSA which is further supported by docking studies. Furthermore, Umb-1 binds to LYS402 with one hydrogen bond distance of 2.8 Å and Umb-2 binds to GLU354 with one hydrogen bond at a distance of 2.0 Å. Moreover, these molecules are stabilized by hydrophobic interactions and hydrogen bond between the hydroxyl groups of carbon-3 of coumarin derivatives.

  1. Method development and validation for the simultaneous determination of four coumarins in Saussurea superba by capillary zone electrophoresis.

    Science.gov (United States)

    Chen, Juan; Chen, Li; Zhang, Hong-Li; Shi, Yan-Ping

    2010-01-01

    A capillary zone electrophoretic method has been developed for the determination of four coumarins--skimmin, scopolin, scopoletin, and umbelliferone-in Saussurea superba with UV detection at 254 nm. The capillary temperature was kept constant at 25 degrees C. Effects of buffer pH, electrolyte concentration, organic modifier, and applied voltage on migration behavior were studied systematically. The optimum conditions for separation were achieved by using 30 mM borate buffer at pH 9.02 containing 15% (v/v) methanol as the electrolyte and 25 kV as the applied voltage. For all analytes a good linear regression relationship (r > 0.999) was obtained between peak area and concentration over a relatively wide range. The method was validated for repeatability, precision, and accuracy. The validated method was successfully applied to the simultaneous determination of the four analytes in S. superba.

  2. New Coumarin Derivatives and Other Constituents from the Stem Bark of Zanthoxylum avicennae: Effects on Neutrophil Pro-Inflammatory Responses

    Directory of Open Access Journals (Sweden)

    Jih-Jung Chen

    2015-04-01

    Full Text Available Three new coumarin derivatives, 8-formylalloxanthoxyletin (1, avicennone (2, and (Z-avicennone (3, have been isolated from the stem bark of Zanthoxylum avicennae (Z. avicennae, together with 15 known compounds (4–18. The structures of these new compounds were determined through spectroscopic and MS analyses. Compounds 1, 4, 9, 12, and 15 exhibited inhibition (half maximal inhibitory concentration (IC50 values ≤7.65 µg/mL of superoxide anion generation by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB. Compounds 1, 2, 4, 8 and 9 inhibited fMLP/CB-induced elastase release with IC50 values ≤8.17 µg/mL. This investigation reveals bioactive isolates (especially 1, 2, 4, 8, 9, 12 and 15 could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases.

  3. Synthesis, characterization and antimicrobial activities of novel silver(I) complexes with coumarin substituted N-heterocyclic carbene ligands.

    Science.gov (United States)

    Karataş, Mert Olgun; Olgundeniz, Begüm; Günal, Selami; Özdemir, İlknur; Alıcı, Bülent; Çetinkaya, Engin

    2016-02-15

    Eight new coumarin substituted silver(I) N-heterocyclic carbene (NHC) complexes were synthesized by the interaction of the corresponding imidazolium or benzimidazolium chlorides and Ag2O in dichloromethane at room temperature. Structures of these complexes were established on the basis of elemental analysis, (1)H NMR, (13)C NMR, IR and mass spectroscopic techniques. The antimicrobial activities of carbene precursors and silver NHC complexes were tested against standard strains: Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and the fungi Candida albicans and Candida tropicalis. Results showed that all the compounds inhibited the growth of the all bacteria and fungi strains and some complexes performed good activities against different microorganisms. Among all the compounds, the most lipophilic complex bis[1-(4-methylene-6,8-dimethyl-2H-chromen-2-one)-3-(naphthalene-2-ylmethyl)benzimidazol-2-ylidene]silver(I) dichloro argentate (5e) was found out as the most active one.

  4. Study on DNA binding behavior and light switch effect of new coumarin-derived Ru(II) complexes

    Science.gov (United States)

    Liu, Xue-Wen; Shen, You-Ming; Li, Zhi-Xin; Zhong, Xiao; Chen, Yuan-Dao; Zhang, Song-Bai

    2015-10-01

    A new ligand mhcip (mhcip = 2-(4-methyl-7-hydroxyl-8-coumarinyl)imidazo[4,5-f]-[1,10]phenanthroline) and its ruthenium complexes, [Ru(L)2mhcip]2+ (L = bpy (2,2‧-bipyridine), phen (1,10-phenanthroline)), have been synthesized and characterized. The introduction of coumarin ring may play an important role in the strong fluorescence of the complexes. Intercalative binding mode between both complexes and CT-DNA was determined by UV-visible spectroscopy, fluorescence spectroscopy and viscosity measurements. The two complexes show efficient DNA photocleavage under irradiation at 365 nm. The cycling of light switch off and on has been achieved for both complexes through the introduction of Cu2+ and EDTA in the absence or presence of DNA.

  5. A quick response fluorescent probe based on coumarin and quinone for glutathione and its application in living cells

    Energy Technology Data Exchange (ETDEWEB)

    Dai, Xi [Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100 (China); Du, Zhi-Fang [Taishan College, Shandong University, Jinan 250100 (China); Wang, Li-Hong; Miao, Jun-Ying [Institute of Developmental Biology, School of Life Science, Shandong University, Jinan 250100 (China); Zhao, Bao-Xiang, E-mail: bxzhao@sdu.edu.cn [Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100 (China)

    2016-05-30

    We have designed and synthesized a simple but effective fluorescent probe for sensing glutathione (GSH) by PET process based on coumarin and quinone, which worked as fluorophore and reaction site, respectively. The probe could discriminate GSH from cysteine and homocysteine within 1 min in PBS-buffered solution. The sensing mechanism was confirmed by density functional theory (DFT), viscosity test, fluorescence spectrum analysis and HRMS, respectively. The probe has a low limit of detection (0.1 μM) and finally been used in cell imaging successfully. - Highlights: • This probe can discriminate glutathione from sulfhydryl compound by PET process. • This probe can be used to determine glutathione in aqueous solution within 1 min. • This probe has been successfully applied in living cell image.

  6. Altering intra- to inter-molecular hydrogen bonding by dimethylsulfoxide: A TDDFT study of charge transfer for coumarin 343

    Science.gov (United States)

    Liu, Xiaochun; Yin, Hang; Li, Hui; Shi, Ying

    2017-04-01

    DFT and TDDFT methods were carried out to investigate the influences of intramolecular and intermolecular hydrogen bonding on excited state charge transfer for coumarin 343 (C343). Intramolecular hydrogen bonding is formed between carboxylic acid group and carbonyl group in C343 monomer. However, in dimethylsulfoxide (DMSO) solution, DMSO 'opens up' the intramolecular hydrogen bonding and forms solute-solvent intermolecular hydrogen bonded C343-DMSO complex. Analysis of frontier molecular orbitals reveals that intramolecular charge transfer (ICT) occurs in the first excited state both for C343 monomer and complex. The results of optimized geometric structures indicate that the intramolecular hydrogen bonding interaction is strengthened while the intermolecular hydrogen bonding is weakened in excited state, which is confirmed again by monitoring the shifts of characteristic peaks of infrared spectra. We demonstrated that DMSO solvent can not only break the intramolecular hydrogen bonding to form intermolecular hydrogen bonding with C343 but also alter the mechanism of excited state hydrogen bonding strengthening.

  7. Optical properties and chemical behavior of Laser-dye Coumarin-500 and the influence of atmospheric corona discharges.

    Science.gov (United States)

    Keskin, S Sinan; Aslan, Necdet; Bayrakçeken, Fuat

    2009-03-01

    Structure elucidation of Coumarin-500 Laser-dye in cyclohexane at room temperature has been studied by UV-Vis, Raman, and FTIR spectroscopic techniques. Optical properties and chemical behavior under the influence of atmospheric positive electric pulsed corona discharges were also examined. The effects of UV-Vis irradiation changed some optical parameters, such as decrease in optical density on the absorption spectrum and formation of photoproducts, due to the chromaticity removal. No significant optical changes were observed in the light absorption upon UV-irradiation but large changes in absorption spectrum were observed after positive electric corona discharge treatments, FTIR and Raman spectra in non-polar solvent are recorded and interpreted.

  8. Synthesis and Study on the Complexation of Dithidiaza 21-Cown-7- Bearing Appended Coumarin or 1-Aminonaphthene as Sidearms

    Institute of Scientific and Technical Information of China (English)

    SONG Hua-Can; MOU De-Hai; CHEN Yi-Wen; XU Zun-Le

    2003-01-01

    @@ The high toxicity of many transition and post-transition metal ions, especially Hg2+ and Pb2 + , is well recognized and a lot of attention has been paid to control contamination of water supplies by toxic metal ions and to monitor the level of these metal ions in the environment. For the application purpose in controlling and monitoring the concentrations of specific metal ions in a complex matrix continuously and remotely by using ion-selective sensory devices, chemical sensors based on the synthetic fluoroionophores and chromoionophores capable of signaling complexation of metal ions have been reported, [1~ 5], and a series of dithidiaza 21-rown-7 bearing appended coumarin or 1-aminonaphthene as sidearms was synthesized. [6

  9. A novel off–on fluorescence chemosensor for Ca{sup 2+} based on Rhodamine–Coumarin Schiff base derivative

    Energy Technology Data Exchange (ETDEWEB)

    An, Jun-mei [College of Chemistry and Chemical Engineering and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China); Yang, Zheng-yin, E-mail: yangzy@lzu.edu.cn [College of Chemistry and Chemical Engineering and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China); Yan, Mi-hui; Li, Tian-rong [College of Chemistry and Chemical Engineering and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China)

    2013-07-15

    A novel sensor, 7-Hydroxy-4-methylcoumarin-8-carbaldehyde-(rhodamine) hydrazone (l) has been synthesized and investigated as a fluorescence chemosensor for Ca{sup 2+} in acetonitrile. The compound is found preferential binding to Ca{sup 2+} in presence of large excess of other competitive ions with associated changes in its optical and fluorescence spectral behavior. Upon the addition of Ca{sup 2+}, an overall emission change of 64-fold was observed. Photoinduced electron transfer (PET) process, coupled with the intramolecular charge transfer (ICT) process, are proposed to explain the observed spectral response. -- Highlights: ► A novel fluorescent sensor based on rhodamine and coumarin has been synthesized to detect Ca{sup 2+}. ► Sensesor shows high sensitivity and selectivity to Ca{sup 2+} with detection limit of 30 ppb.► The sensor can distinguish Ca{sup 2+} and Mg{sup 2+} effectively.

  10. Development of a coumarin-furan conjugate as Zn2 + ratiometric fluorescent probe in ethanol-water system

    Science.gov (United States)

    Li, Chao-rui; Li, Si-liang; Yang, Zheng-yin

    2017-03-01

    In this study, a novel coumarin-derived compound bearing the furan moiety called 7-diethylamino-3-formylcoumarin (2‧-furan formyl) hydrazone (1) has been designed, synthesized and evaluated as a Zn2 + ratiometric fluorescent probe in ethanol-water system. This probe 1 showed good selectivity and high sensitivity towards Zn2 + over other metal ions investigated, and a decrease in fluorescence emission intensity at 511 nm accompanied by an enhancement in fluorescence emission intensity at 520 nm of this probe 1 was observed in the presence of Zn2 + in ethanol-water (V : V = 9 : 1) solution, which provided ratiometric fluorescence detection of Zn2 +. Additionally, the ratiometric fluorescence response of 1 to Zn2 + was nearly completed within 0.5 min, which suggested that this probe 1 could be utilized for sensing and monitoring Zn2 + in environmental and biological systems for real-time detection.

  11. Study on the interaction between gliadins and a coumarin as molecular model system of the gliadins-anthocyanidins complexes.

    Science.gov (United States)

    Tozzi, Silvia; Zanna, Nicola; Taddei, Paola

    2013-12-15

    To clarify the conformational changes of gliadins (Glia) upon complexation with anthocyanidins (in particular cyanidin, Cya), the interaction of Glia with a coumarin derivative (3-ethoxycarbonylcoumarin, 3-EcC), having a benzocondensed structure similar to that of Cya, has been investigated by NMR, IR, and Raman spectroscopy under acidic and neutral conditions. Raman spectra showed that both molecules produce a similar effect on the Glia structure, i.e. an increase in the α-helix conformation and a decrease in β-sheet and β-turns content. In the presence of both molecules, this effect is more marked; the spectroscopic results showed that both Cya and 3-EcC interact with Glia and 3-EcC favors the complex formation with Glia. The results obtained in this study provide new insights into anthocyanidins-Glia interactions and may have relevance to human health, in the field of the attempts to modify gluten proteins to decrease allergen immunoreactivity.

  12. Solvation dynamics of coumarin 153 embedded in AOT + phenol organogels studied by time-resolved fluorescence spectroscopy

    Science.gov (United States)

    Nishiyama, Katsura; Takata, Kei; Watanabe, Keiichi; Shigematsu, Hirotake

    2012-03-01

    We investigate solvation dynamics of organogel utilizing ps-ns fluorescence spectroscopy. The organogel studied in this Letter comprises bis(2-ethylhexyl) sulfosuccinate (AOT) and p-chlorophenol in the m-xylene solvent, that produce an organogel architecture with self-assembly. Within the organogel, an emitting probe, coumarin 153 (C153), is embedded. We then obtain dynamic response functions of solvation derived from the time-resolved fluorescence spectra of C153. We propose that total energy of the C153-organogel system relaxes with a relaxation time of 3.9 ns, whereas the entire rearrangement of the organogel structure around C153 is achieved with that of 6.1 ns, respectively.

  13. Effect of light on contents of coumarin compounds in shoots of Ruta graveolens L. cultivated in vitro

    Directory of Open Access Journals (Sweden)

    Halina Ekiert

    2014-01-01

    Full Text Available Shoots of Ruta graveolens L. (Rutaceae were cultivated in stationary liquid culture under different light conditions: constant artificial light (900 lx, darkness, constant artificial light (900 ix following irradiation with UV-C light. The contents of five furanocoumarins: psoralen, bergapten, xanthotoxin, isopimpinellin and imperatorin, as well as biogenetic precursor of these metabolites, umbelliferone, were determined by HPLC method in shoots cultivated in vitro and in overground parts of plants growing in open air. It was shown that light conditions, tested in these experiments, significantly influenced contents of the metabolites in shoots cultivated in in vitro culture. Total content of the coumarin compounds in shoots cultivated under constant artificial light (900 lx was equal or higher than in plants growing under natural conditions. Therefore, it is suggested that stationary liquid shoot culture of R. graveolens. can be an alternative source for obtaining biologically active furanocoumarins.

  14. Modeling Solvent Broadening on the Vibronic Spectra of a Series of Coumarin Dyes. From Implicit to Explicit Solvent Models.

    Science.gov (United States)

    Cerezo, Javier; Avila Ferrer, Francisco J; Prampolini, Giacomo; Santoro, Fabrizio

    2015-12-08

    We present a protocol to estimate the solvent-induced broadening of electronic spectra based on a model that explicitly takes into account the environment embedding the solute. Starting from a classical approximation of the solvent contribution to the spectrum, the broadening arises from the spread of the excitation energies due to the fluctuation of the solvent coordinates, and it is represented as a Gaussian line shape that convolutes the vibronic spectrum of the solute. The latter is computed in harmonic approximation at room temperature with a time-dependent approach. The proposed protocol for the computation of spectral broadening exploits molecular dynamics (MD) simulations performed on the solute-solvent system, keeping the solute degrees of freedom frozen, followed by the computation of the excitation properties with a quantum mechanics/molecular mechanics (QM/MM) approach. The factors that might influence each step of the protocol are analyzed in detail, including the selection of the empirical force field (FF) adopted in the MD simulations and the QM/MM partition of the system to compute the excitation energies. The procedure is applied to a family of coumarin dyes, and the results are compared with experiments and with the predictions of a very recent work (Cerezo et al., Phys. Chem. Chem. Phys. 2015, 17, 11401-11411), where an implicit model was adopted for the solvent. The final spectra of the considered coumarins were obtained without including ad hoc phenomenological parameters and indicate that the broadenings computed with explicit and implicit models both follow the experimental trend, increasing as the polarity change from the initial to the final state increases. More in detail, the implicit model provides larger estimations of the broadening that are closer to the experimental evidence, while explicit models appear to better capture relative differences arising from different solvents or different solutes. Possible inaccuracies of the adopted

  15. Unraveling the Alkaline Phosphatase Inhibition, Anticancer, and Antileishmanial Potential of Coumarin-Triazolothiadiazine Hybrids: Design, Synthesis, and Molecular Docking Analysis.

    Science.gov (United States)

    Ibrar, Aliya; Zaib, Sumera; Jabeen, Farukh; Iqbal, Jamshed; Saeed, Aamer

    2016-07-01

    A series of new coumarin-triazolothiadiazine hybrid compounds (5a-j) was designed and synthesized by using the molecular hybridization concept. The cyclocondensation reaction involves the coumarinyl 4-amino-1,2,4-triazole and a range of bromo-acetophenones, delivering the desired products in good yields. The structures of the synthesized compounds were established on the basis of spectro-analytical data. The prepared compounds were evaluated against alkaline phosphatase (ALP) where compound 5j incorporating bis-coumarinyl motifs at the 3- and 6-positions of the heteroaromatic core turned out to be a potent inhibitor with an IC50 value of 1.15 ± 1.0 µM. The synthesized compounds were also tested against Leishmania major and 5h was the lead member with an IC50 value of 0.89 ± 0.08 μM. Anticancer activity was also determined using kidney fibroblast (BHK-21) and lung carcinoma (H-157) cancer cell lines. Compound 5i showed highest cytotoxic potential against H-157 cells with an IC50 value of 1.01 ± 0.12 μM, which is an improved inhibition compared to the standards (vincristine and cisplatin) used in this assay. Molecular docking studies were carried out on the synthesized library of coumarin-triazolothiadiazine hybrids against ALP. Almost all of the compounds showed strong interactions with the key residues of the active site of the receptor. In case of compounds 5a-c, 5h, and 5j, docking results positively complemented the experimental screening. These results provided substantial evidence for the further development of these compounds as potent inhibitors of ALP.

  16. Separation of 20 coumarin derivatives using the capillary electrophoresis method optimized by a series of Doehlert experimental designs.

    Science.gov (United States)

    Woźniakiewicz, Michał; Gładysz, Marta; Nowak, Paweł M; Kędzior, Justyna; Kościelniak, Paweł

    2017-05-15

    The aim of this study was to develop the first CE-based method enabling separation of 20 structurally similar coumarin derivatives. To facilitate method optimization a series of three consequent Doehlert experimental designs with the response surface methodology was employed, using number of peaks and the adjusted time of analysis as the selected responses. Initially, three variables were examined: buffer pH, ionic strength and temperature (No. 1 Doehlert design). The optimal conditions provided only partial separation, on that account, several buffer additives were examined at the next step: organic cosolvents and cyclodextrin (No. 2 Doehlert design). The optimal cyclodextrin type was also selected experimentally. The most promising results were obtained for the buffers fortified with methanol, acetonitrile and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin. Since these additives may potentially affect acid-base equilibrium and ionization state of analytes, the third Doehlert design (No. 3) was used to reconcile concentration of these additives with optimal pH. Ultimately, the total separation of all 20 compounds was achieved using the borate buffer at basic pH 9.5 in the presence of 10mM cyclodextrin, 9% (v/v) acetonitrile and 36% (v/v) methanol. Identity of all compounds was confirmed using the in-lab build UV-VIS spectra library. The developed method succeeded in identification of coumarin derivatives in three real samples. It demonstrates a huge resolving power of CE assisted by addition of cyclodextrins and organic cosolvents. Our unique optimization approach, based on the three Doehlert designs, seems to be prospective for future applications of this technique.

  17. Cytochrome P450 isoenzymes in rat and human liver microsomes associate with the metabolism of total coumarins in Fructus Cnidii.

    Science.gov (United States)

    Hu, Xiao; Huang, Wei; Yang, Yuan

    2015-12-01

    Fructus Cnidii (Cnidium) is isolated from the dry and ripe fruit of Cnidium monnier (L.) Cuss (umbelifera), an annual herb. It is demonstrated that the active constituents of Fructus Cnidii are coumarins, known as Total Coumarins of Cnidium Monnier (TCCM). Osthole (Ost) and imperatorin (Imp) are the most active constituents of TCCM which are usually regarded as the quality indicators of medicinal Fructus Cnidii. The aim is to study the metabolism of Fructus Cnidii effective monomer osthole and imperatorin in vitro by liver microsomes. CYP3A4 inhibitor ketoconazole, CYP2D6 inhibitor qunidine, CYP2C8 inhibitor trimethoprim, CYP2C9 inhibitor sulfaphenazole, and CYP1A2 inhibitor α-naphthoflavone were used to investigate the metabolism from incubation time, substrate concentration and liver microsomal concentration, respectively. The concentration of liver microsomes was 0.2 mg/ml. Ost (0.8/3.2/12.8 uM) was incubated at 37 °C for 20 min while Imp (1.6/6.4/19.2 uM) was incubated for 30 min. Qunidine, trimethoprim and α-naphthoflavone could significantly inhibit the disappearance of Imp; meanwhile ketoconazole, sulfaphenazole and qunidine could inhibit the disappearance of Ost. CYP1A, CYP2C are involved in the metabolism of Imp and CYP3A mediates the metabolism of Ost in rat liver microsomes. In human liver microsomes, CYP1A2, CYP2C8, CYP2D6 are involved in the metabolism of Imp; CYP3A4 is involved in the metabolism of Ost at all the tested concentrations of Ost, while CYP2C9, CYP2D6 mediate the metabolism at high concentration of Ost.

  18. Antitumor effect of a copper (II) complex of a coumarin derivative and phenanthroline on lung adenocarcinoma cells and the mechanism of action.

    Science.gov (United States)

    Zhu, Taofeng; Chen, Ruhua; Yu, Hao; Feng, Yan; Chen, Jianqiang; Lu, Qin; Xie, Jing; Ding, Weiliang; Ma, Tieliang

    2014-11-01

    In order to investigate the effect of a copper (II) complexes of a coumarin derivative and phenanthroline (hereinafter referred to as the coumarin-copper drug) on lung adenocarcinoma cells in vivo and in vitro, along with the mechanism of action, LA795 lung adenocarcinoma cells were treated with different concentrations of coumarin-copper drug. An MTT assay was performed to determine the cell proliferation ratio, cell apoptosis was detected by Annexin V/propidium iodide staining with flow cytometric analysis and western blot analysis was employed to evaluate the expression levels of apoptosis-associated proteins. In addition, an LA795 cell xenograft tumor model was established in nude mice, with mice receiving intraperitoneal injection once a week for three weeks of either 2 or 4 mg/kg in three divided doses coumarin‑copper drug, or phosphate‑buffered saline. The tumor growth curves were drawn and the tumor growth inhibition rates were calculated. The apoptotic index of subcutaneously transplanted tumor cells was determined by terminal deoxynucleotidyl‑transferase‑mediated dUTP nick end‑labeling assay. The coumarin-copper drug effectively inhibited the proliferation of LA795 cells in a dose‑ and time‑dependent manner, with the half maximal inhibitory concentration equaling 2.0 µmol/l. The coumarin-copper drug also significantly induced LA795 cell apoptosis in a time-dependent manner (P<0.05), which was accompanied by upregulation p35 and B-cell lymphoma-2 (Bcl-2)-associated X protein (Bax), and downregulation of Bcl-2. Furthermore, the coumarin‑copper drug significantly inhibited the growth of LA795 tumors in a dose dependent manner (P<0.05), in accordance with the apoptotic index. In conclusion, the coumarin-copper drug may inhibit the proliferation of LA795 cells through the induction of cell apoptosis, which may be associated with the upregulation of p53 and Bax, with concurrent downregulation of Bcl-2.

  19. A randomized trial assessing the effect of coumarins started before coronary angioplasty on restenosis: results of the 6-month angiographic substudy of the Balloon Angioplasty and Anticoagulation Study (BAAS).

    Science.gov (United States)

    ten Berg, Jurriën M; Kelder, Johannes C; Suttorp, Maarten Jan; Verheugt, Freek W A; Plokker, H W Thijs

    2003-01-01

    Thrombus formation during coronary angioplasty may play a role in the restenosis process. The effect of pretreatment with coumarins on 6-month angiographic outcome was studied. In addition, the effect of "optimal" anticoagulation, defined as an international normalized ratio >70% of the follow-up time in the target range, was studied. A total of 261 patients were assigned to aspirin alone (ASA group) and 270 patients to aspirin plus coumarins started 1 week before the procedure (coumarin group). The mean international normalized ratio was 2.7 +/- 1.2 at the start of the procedure and 3.1 +/- 0.5 during follow up. Quantitative coronary analysis was performed on 301 lesions in the ASA group and of 297 lesions in the coumarin group. At 6 months, the minimal luminal diameter was similar in the ASA and coumarin groups. Optimal anticoagulation, however, was an independent predictor of a larger minimal luminal diameter at follow up (P =.01). Overall, coumarins do not improve angiographic outcome 6 months after coronary angioplasty.

  20. Modeling of thermodynamic and physico-chemical properties of coumarins bioactivity against Candida albicans using a Levenberg-Marquardt neural network.

    Science.gov (United States)

    Mousavi, Seyyedeh Soghra; Bokharaie, Hanieh; Rahimi, Shadi; Soror, Sima Azadi; Hamidi, Mehrdad

    2010-01-01

    In recent years, due to vital need for novel fungicidal agents, investigation on natural antifungal resources has been increased. The special features exhibited by neural network classifiers make them suitable for handling complex problems like analyzing different properties of candidate compounds in computer-aided drug design. In this study, by using a Levenberg-Marquardt (LM) neural network (the fastest of the training algorithms), the relation between some important thermodynamic and physico-chemical properties of coumarin compounds and their biological activities (tested against Candida albicans) has been evaluated. A set of already reported antifungal bioactive coumarin and some well-known physical descriptors have been selected and using LM training algorithm the best architecture of neural model has been designed for forecasting the new bioactive compounds.

  1. Density Functional Theory (DFT Study of Coumarin-based Dyes Adsorbed on TiO2 Nanoclusters—Applications to Dye-Sensitized Solar Cells

    Directory of Open Access Journals (Sweden)

    Mihai A. Gîrţu

    2013-06-01

    Full Text Available Coumarin-based dyes have been successfully used in dye-sensitized solar cells, leading to photovoltaic conversion efficiencies of up to about 8%. Given the need to better understand the behavior of the dye adsorbed on the TiO2 nanoparticle, we report results of density functional theory (DFT and time-dependent DFT (TD-DFT studies of several coumarin-based dyes, as well as complex systems consisting of the dye bound to a TiO2 cluster. We provide the electronic structure and simulated UV-Vis spectra of the dyes alone and adsorbed to the cluster and discuss the matching with the solar spectrum. We display the energy level diagrams and the electron density of the key molecular orbitals and analyze the electron transfer from the dye to the oxide. Finally, we compare our theoretical results with the experimental data available and discuss the key issues that influence the device performance.

  2. Synthesis of polymeric fluorescent brightener based on coumarin and its performances on paper as light stabilizer, fluorescent brightener and surface sizing agent

    Science.gov (United States)

    Zhang, Guanghua; Zheng, Hua; Guo, Mingyuan; Du, Lun; Liu, Guojun; Wang, Peng

    2016-03-01

    In this work, a novel polymeric fluorescent brightener based on coumarin (PFBC) was synthesized, using three-step synthetic route, from 7-amino-4-methylcoumarin, coumarin monomer (FBC), Acrylamide (AM) and methacrylatoethyl trimethyl ammonium chloride (DMC). The structure of PFBC was characterized by FT-IR, 1HNMR and GPC. PFBC was applied to paper fiber as light stabilizer, fluorescent brightener and surface sizing agent and its performances were evaluated by measuring the UV-vis, fluorescence, thermal stability, the cationic degree, surface strength and smoothness of paper, the brightness degree of paper and the PC value of paper. Results showed that PFBC had better solubility in water than that of FBC, by measuring the optical properties. Through the surface sizing experiment and UV aging experiment, PFBC not only enhanced the surface strength and smoothness of paper as a surface sizing agent, but also had better effect on anti-UV aging than that of FBC as light stabilizer and fluorescent brightener.

  3. 3-Substituted-7-(diethylamino)coumarins as molecular scaffolds for the bottom-up self-assembly of solids with extensive π-stacking

    Science.gov (United States)

    Arcos-Ramos, Rafael; Maldonado-Domínguez, Mauricio; Ordóñez-Hernández, Javier; Romero-Ávila, Margarita; Farfán, Norberto; Carreón-Castro, María del Pilar

    2017-02-01

    In this study, a set of molecular crystals derived from 3-substituted-7-(diethylamino)-2H-chromen-2-ones 1-8 were studied to sample the aggregation of coumarins into ordered solids. Crystals of parent compound 1a and its brominated derivative 2 were obtained and solved in the P-1 and C2/c space groups, respectively. All the crystalline coumarins studied display extensive π-stacking in the solid-state. Theoretical valence-conduction band gaps for derivatives 3b and 5 are close to crystalline rubrene, highlighting the importance of cooperativity and periodicity of π-stacking, in organic semiconductors; given their synthetic accessibility, electronic tunability and self-assembly via stacking, dipolar and H-bonding interactions, these systems arise as candidates for the bottom-up construction of organic crystals with extensive π-stacking and high polarizability.

  4. Synthesis and Use of Coumarin and Certain Derivative%香豆素及其衍生物的合成与用途

    Institute of Scientific and Technical Information of China (English)

    尚尔才

    2011-01-01

    Synthesis methods and the application of coumarin and certain derivative, especially their use in pesticide, medicine and laser dye were reviewed in this paper.%综述了香豆素和某些衍生物的合成方法及用途,主要介绍了其在农药、医药、香料及激光染料方面的应用。

  5. Novel microtubule-targeted agent 6-chloro-4-(methoxyphenyl) coumarin induces G2-M arrest andapoptosis in HeLa cells

    Institute of Scientific and Technical Information of China (English)

    Yi-ming MA; Yu-bo ZHOU; Chuan-ming XIE; Dong-mei CHEN; Jia LI

    2012-01-01

    To identify a novel coumarin analogue with the highest anticancer activity and to further investigate its anticancer mechanisms.Methods:The viability of cancer cells was investigated using the MTT assay.The cell cycle progression was evaluated using both flow cytometric and Western blotting analysis.Microtubule depolymerization was observed with immunocytochemistry in vivo and a tubu-lin depolymerization assay in vitro.Apoptosis was demonstrated using Annexin V/Propidium Iodide (PI) double-staining and sub-G1analysis.Results:Among 36 analogues of coumarin,6-chloro-4-(methoxyphenyl) coumarin showed the best anticancer activity (IC50 value about 200 nmol/L) in HCT116 cells.The compound had a broad spectrum of anticancer activity against 9 cancer cell lines derived from colon cancer,breast cancer,liver cancer,cervical cancer,leukemia,epidermoid cancer with IC5o value of 75 nmol/L-1.57 μmol/L but with low cytotocitity against WI-38 human lung fibroblasts (IC50 value of 12.128 μmol/L).The compound (0.04-10 μmol/L) induced G2-M phase arrest in HeLa cells in a dose-dependent manner,which was reversible after the compound was removed.The compound (10-300 μmol/L) induced the depolymerization of purified porcine tubulin in vitro.Finally,the compound (0.04-2.5 μmol/L) induced apoptosis of HeLa cells in dose- and time-dependent manners.Conclusion:6-Chloro-4-(methoxyphenyl) coumarin is a novel microtubule-targeting agent that induces G2-M arrest and apoptosis in HeLa cells.

  6. 香豆素类化合物的药理作用研究进展%The Study Progress on Pharmacological Action of Coumarins

    Institute of Scientific and Technical Information of China (English)

    张国铎; 李航

    2011-01-01

    香豆素(coumarins)是一类广泛存在于自然界中的天然化合物,具有广泛的药理作用,如抗肿瘤、抗人类免疫缺陷病毒(HIV)、抗氧化、抗茵、抗凝血、光敏等.同时已有研究证实,其药理作用与化学结构密切相关,因此可进一步研究开发更多的香豆素类化合物,从中寻找有效的先导化舍物和活性基团,通过结构修饰和筛选,开发出高效低毒的临床药物.该文就近年来香豆素类化合物在肿瘤、艾滋病等治疗领域的研究作一综述.%Coumarins are a group of important natural compounds,and have been found to have multi-biological activities such as anti tumor, anti - HIV, antioxidant, anti - microbial, anticoagulation, photoresponse, etc.At the same time, some researches had confirmed that its pharmacological effect is closely related to its chemical structure.Therefore, more coumarin compounds could be developed by further researches, from which we could find effective leading compounds and active groups.High efficiency and low toxin clinical drugs can be developed by structure modification and selection.Progress on pharmacological action of coumarins were overviewed in this paper.

  7. Structure-Function Analysis of Mammalian CYP2B Enzymes Using 7-Substituted Coumarin Derivatives as Probes: Utility of Crystal Structures and Molecular Modeling in Understanding Xenobiotic Metabolism.

    Science.gov (United States)

    Shah, Manish B; Liu, Jingbao; Huo, Lu; Zhang, Qinghai; Dearing, M Denise; Wilderman, P Ross; Szklarz, Grazyna D; Stout, C David; Halpert, James R

    2016-04-01

    Crystal structures of CYP2B35 and CYP2B37 from the desert woodrat were solved in complex with 4-(4-chlorophenyl)imidazole (4-CPI). The closed conformation of CYP2B35 contained two molecules of 4-CPI within the active site, whereas the CYP2B37 structure demonstrated an open conformation with three 4-CPI molecules, one within the active site and the other two in the substrate access channel. To probe structure-function relationships of CYP2B35, CYP2B37, and the related CYP2B36, we tested the O-dealkylation of three series of related substrates-namely, 7-alkoxycoumarins, 7-alkoxy-4-(trifluoromethyl)coumarins, and 7-alkoxy-4-methylcoumarins-with a C1-C7 side chain. CYP2B35 showed the highest catalytic efficiency (kcat/KM) with 7-heptoxycoumarin as a substrate, followed by 7-hexoxycoumarin. In contrast, CYP2B37 showed the highest catalytic efficiency with 7-ethoxy-4-(trifluoromethyl)coumarin (7-EFC), followed by 7-methoxy-4-(trifluoromethyl)coumarin (7-MFC). CYP2B35 had no dealkylation activity with 7-MFC or 7-EFC. Furthermore, the new CYP2B-4-CPI-bound structures were used as templates for docking the 7-substituted coumarin derivatives, which revealed orientations consistent with the functional studies. In addition, the observation of multiple -Cl and -NH-π interactions of 4-CPI with the aromatic side chains in the CYP2B35 and CYP2B37 structures provides insight into the influence of such functional groups on CYP2B ligand binding affinity and specificity. To conclude, structural, computational, and functional analysis revealed striking differences between the active sites of CYP2B35 and CYP2B37 that will aid in the elucidation of new structure-activity relationships.

  8. Achievement of over 1.4 V photovoltage in a dye-sensitized solar cell by the application of a silyl-anchor coumarin dye

    OpenAIRE

    Kenji Kakiage; Hiroyuki Osada; Yohei Aoyama; Toru Yano; Keiji Oya; Shinji Iwamoto; Jun-ichi Fujisawa; Minoru Hanaya

    2016-01-01

    A dye-sensitized solar cell (DSSC) fabricated by using a novel silyl-anchor coumarin dye with alkyl-chain substitutes, a Br3 −/Br− redox electrolyte solution containing water, and a Mg2+-doped anatase-TiO2 electrode with twofold surface modification by MgO and Al2O3 exhibited an open-circuit photovoltage over 1.4 V, demonstrating the possibility of DSSCs as practical photovoltaic devices.

  9. Achievement of over 1.4 V photovoltage in a dye-sensitized solar cell by the application of a silyl-anchor coumarin dye

    Science.gov (United States)

    Kakiage, Kenji; Osada, Hiroyuki; Aoyama, Yohei; Yano, Toru; Oya, Keiji; Iwamoto, Shinji; Fujisawa, Jun-Ichi; Hanaya, Minoru

    2016-10-01

    A dye-sensitized solar cell (DSSC) fabricated by using a novel silyl-anchor coumarin dye with alkyl-chain substitutes, a Br3‑/Br‑ redox electrolyte solution containing water, and a Mg2+-doped anatase-TiO2 electrode with twofold surface modification by MgO and Al2O3 exhibited an open-circuit photovoltage over 1.4 V, demonstrating the possibility of DSSCs as practical photovoltaic devices.

  10. Selective Activation of Nociceptor TRPV1 Channel and Reversal of Inflammatory Pain in Mice by a Novel Coumarin Derivative Muralatin L from Murraya alata*

    OpenAIRE

    Wei, Ning-Ning; Lv, Hai-Ning; Wu, Yang; Yang, Shi-Long; Sun, Xiao-Ying; Lai, Ren; Yong JIANG; Wang, KeWei

    2015-01-01

    Coumarin and its derivatives are fragrant natural compounds isolated from the genus Murraya that are flowering plants widely distributed in East Asia, Australia, and the Pacific Islands. Murraya plants have been widely used as medicinal herbs for relief of pain, such as headache, rheumatic pain, toothache, and snake bites. However, little is known about their analgesic components and the molecular mechanism underlying pain relief. Here, we report the bioassay-guided fractionation and identifi...

  11. Fluorophores as Chemosensors for Sr(sup 2+) and Cs(sup +) Based on Calix[4]arenes and Coumarin Reporter Groups

    Energy Technology Data Exchange (ETDEWEB)

    Gorestzki, Gudrun; Brown, Gilbert M.; Bonnesen, Peter V.

    2003-09-10

    Fluorescent sensors are being developed for Cs + and Sr2+ which combine a molecular recognition element with an optical transduction element. Such sensors will be needed for real-time application in the characterization of nuclear waste and waste process streams. The fluorescent method is very important due to its high sensitivity and direct visual perception even in highly dilute solutions and its potential for remote application utilizing fiber optics. Crown ether bridged calix[4]arenes have been widely used as a three-dimensional platform for selective metal ion recognition. Coumarins show interesting photochemical and photophysical properties and are widely used in laser dye applications. These fluorescence probes increase their dipolar moment when excited. We will report the synthesis of calix[4]arene-crown-6 derivatives possessing 1,3-alternate conformation and incorporating a coumarin based fluorescence reporter group. Selectivity for Sr2+ over Cs + is obtained by using azacrowns and the sensitivity will be determined by varying the donor atom set as well as the substitution pattern of the coumarin.

  12. Modeling of thermodynamic and physico-chemical properties of coumarins bioactivity against Candida albicans using a Levenberg–Marquardt neural network

    Directory of Open Access Journals (Sweden)

    Seyyedeh Soghra Mousavi

    2010-08-01

    Full Text Available Seyyedeh Soghra Mousavi1, Hanieh Bokharaie2, Shadi Rahimi3, Sima Azadi Soror4, Mehrdad Hamidi51Department of Biotechnology, School of Pharmacy, Zanjan University of Medical Science, Zanjan, Iran; 2Genetic Group, Biology Department, Faculty of Basic Sciences, Science and Research Branch, Islamic Azad University, Tehran, Iran; 3Department of Biology, Faculty of Science, Tarbiat Moallem University, Tehran, Iran: 4Plant Protection Department, Faculty of Agriculture, Bu-Ali Sina University, Hamedan, Iran; 5Department of Pharmaceutics, School of Pharmacy, Zanjan University of Medical Science, Zanjan, IranAbstract: In recent years, due to vital need for novel fungicidal agents, investigation on natural antifungal resources has been increased. The special features exhibited by neural ­network classifiers make them suitable for handling complex problems like analyzing ­different properties of candidate compounds in computer-aided drug design. In this study, by using a Levenberg–­Marquardt (LM neural network (the fastest of the training algorithms, the ­relation between some important thermodynamic and physico-chemical properties of coumarin compounds and their biological activities (tested against Candida albicans has been evaluated. A set of already reported antifungal bioactive coumarin and some well-known physical descriptors have been selected and using LM training algorithm the best architecture of neural model has been designed for forecasting the new bioactive compounds.Keywords: Levenberg–Marquardt algorithm, coumarin, neural network

  13. Metal-enhanced fluorescence of mixed coumarin dyes by silver and gold nanoparticles: Towards plasmonic thin-film luminescent solar concentrator

    Energy Technology Data Exchange (ETDEWEB)

    El-Bashir, S.M., E-mail: elbashireg@yahoo.com [Department of Physics and Astronomy, Science College, King Saud University, Riyadh, KSA (Saudi Arabia); Department of Physics Faculty of Science, Benha University (Egypt); Barakat, F.M.; AlSalhi, M.S. [Department of Physics and Astronomy, Science College, King Saud University, Riyadh, KSA (Saudi Arabia)

    2013-11-15

    Poly(methyl methacrylate) (PMMA) nanocomposite films doped with mixed coumarin dyestuffs and noble metal nanoparticles (60 nm silver and 100 nm gold) were prepared by spin coating technique. The effect of silver and gold nanoparticles on the film properties was studied by Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), transmission electron microscopy (TEM), scanning electron microscopy (SEM), UV–vis absorption and fluorescence spectroscopy measurements. DSC measurements indicated the increase of the glass transition temperature of the films by increasing nanogold concentration, recommending their promising thermal stability towards hot climates. It was found that the fluorescence signals of the mixed coumarin dyes were amplified by 5.4 and 7.15 folds as a result of metal enhanced fluorescence (MEF). The research outcomes offered a potential application of these films in solar energy conversion by plasmonic thin film luminescent solar concentrator (PTLSC). -- Graphical abstract: Plasmonic thin film luminescent solar concentrators. Highlights: • Metal enhanced fluorescence was achieved for mixed coumarin dyes doped in PMMA nanocomposite films. • The amplification of the fluorescence signals is dependent on the concentration of silver and gold nanoparticles. • These films is considered as potential candidates for plasmonic thin film luminescent solar concentrators (PTLSCs)

  14. Syntheses of coumarin-tacrine hybrids as dual-site acetylcholinesterase inhibitors and their activity against butylcholinesterase, Aβ aggregation, and β-secretase.

    Science.gov (United States)

    Sun, Qi; Peng, Da-Yong; Yang, Sheng-Gang; Zhu, Xiao-Lei; Yang, Wen-Chao; Yang, Guang-Fu

    2014-09-01

    Exploring small-molecule acetylcholinesterase (AChE) inhibitors to slow the breakdown of acetylcholine (Ach) represents the mainstream direction for Alzheimer's disease (AD) therapy. As the first acetylcholinesterase inhibitor approved for the clinical treatment of AD, tacrine has been widely used as a pharmacophore to design hybrid compounds in order to combine its potent AChE inhibition with other multi-target profiles. In present study, a series of novel tacrine-coumarin hybrids were designed, synthesized and evaluated as potent dual-site AChE inhibitors. Moreover, compound 1g was identified as the most potent candidate with about 2-fold higher potency (Ki=16.7nM) against human AChE and about 2-fold lower potency (Ki=16.1nM) against BChE than tacrine (Ki=35.7nM for AChE, Ki=8.7nM for BChE), respectively. In addition, some of the tacrine-coumarin hybrids showed simultaneous inhibitory effects against both Aβ aggregation and β-secretase. We therefore conclude that tacrine-coumarin hybrid is an interesting multifunctional lead for the AD drug discovery.

  15. 超声波提取独活中总香豆素的工艺研究%Ultrasonic assisted extraction of total coumarin from radix angelicae pubescentis

    Institute of Scientific and Technical Information of China (English)

    郑秀玉; 李滔; 陈赟

    2013-01-01

    研究超声波提取独活中总香豆素的工艺影响因素.采用紫外可见分光光度法作为分析手段,以总香豆素的提取得率为评价标准.通过单因素分析,得到最佳提取条件为:溶剂倍量10倍,乙醇体积分数60%,超声波功率240 W,提取时间20 min,提取温度30℃,粒度40~100目.%The extraction conditions of total coumarin by the ultrasonic from the radix angelicae pubescentis are studied. The content of total coumarin is determined by UV spectrophotometry. The yield of total coumarin is as the detective marker. Through univariate analysis, the optimal conditions are as follows: the material-liquid ratio 1:10, ethanol solution 60%, ultrasonic power 240W, extraction time 20 min, extraction temperature 30 ℃ and material granularity 40-100 mesh.

  16. Preparation of Dry Extract of Mikania glomerata Sprengel (Guaco and Determination of Its Coumarin Levels by Spectrophotometry and HPLC-UV

    Directory of Open Access Journals (Sweden)

    Maria da Penha Henriques do Amaral

    2012-08-01

    Full Text Available Guaco (Mikania glomerata Sprengel syrup is one of the most popular herbal medicines used to treat the symptoms of asthmatic bronchitis, cough and hoarseness. The coumarin 2H-1-benzopyran-2-one, is one of the major constituents of Guaco and contributes to its pharmacological effects. The pharmaceutical capsule form of dry extract of Guaco is recommended by the Brazilian Program of Medicinal Plants and Herbal Medicines and used in primary health care. In order to identify a new protocol to obtain the raw material for Guaco capsule production we evaluated two methods, including a freeze-drying process (lyophilization and the spray-dryer technique, as well as the use of two adjuvants, Maltodextrins and Aerosil®, in different concentrations. The coumarin levels of the dried extracts were analyzed by UV-spectrophotometry and HPLC-UV/DAD. The adjuvant Aerosil® 8% showed better dry powder physical appearance. Lyophilization was observed to be the best process to obtain the dry extract of Guaco based on the measured coumarin levels.

  17. Sodium desoxycholate-assisted capillary electrochromatography with methacrylate ester-based monolithic column on fast separation and determination of coumarin analogs in Angelica dahurica extract.

    Science.gov (United States)

    Chen, Zhao; Wang, Jiajing; Chen, Danxia; Fan, Guorong; Wu, Yutian

    2012-09-01

    A rapid and sensitive CEC method with methacrylate ester-based monolithic column has been developed for separation and determination of five coumarins (byakangelicin, oxypeucedanin hydrate, xanthotoxol, 5-hydroxy-8-methoxypsoralen and bergapten) in Angelica dahurica extract. Surfactant sodium desoxycholate (SDC) was introduced into the mobile phase as the pseudostationary to dynamically increase the selectivity of analytes instead of increasing the hydrophobicity of stationary phase. In addition, other factors, pH of phosphate buffer, ACN content and applied voltage, for instance, have also an obvious effect on the resolution but little on the retention time. Satisfactory separation of these five coumarins was achieved within 6 min under a 30:70 v/v ACN-buffer containing 20 mM sodium dihydrogen phosphate (NaH(2) PO(4) ) and 0.25 mM SDC at pH 2.51. The RSDs of intraday and interday for relative peak areas were less than 3.0% and 4.7%, respectively; and the recoveries were between 87.5% and 95.0%. The LODs were lower than 0.15 μg/mL and the LOQs were lower than 0.30 μg/mL, respectively, while calibration curves showed a good linearity (r(2) > 0.9979). Finally, five target coumarins from the crude extracts of A. dahurica were separated, purified, and concentrated by D-101 macroporous resin, and were successfully separated and quantitatively determined within 6 min.

  18. Computational and experimental evaluation of selective substitution of thiolated coumarin derivatives on gold nanoparticles: Surface enhancing Raman scattering and electrochemical studies

    Science.gov (United States)

    Mlambo, Mbuso; Harris, Richard A.; Mashazi, Philani; Sabela, Myalowenkosi; Kanchi, Suvardhan; Madikizela, Lawrence M.; Shumbula, Prince N.; Moloto, Nosipho; Hlatshwayo, Thulani T.; Mdluli, Phumlani S.

    2017-02-01

    Gold nanoparticles (AuNPs) of various sizes were prepared and treated with a mixture of HS-(CH2)11-NHCO-coumarin (act as Raman reporter) and HS-PEG-(CH2)11COOH (as co-stabilizer and also to attach biomarkers on activated sbnd COOH) to produce mixed monolayer protected clusters of gold (AuMMPCs). In this paper, we demonstrate the significance of the HS-(CH2)11-NHCO-coumarin concentration (percentage ratio) on the enhancement factor (EF), and the geometry of the adsorbed ligands on AuNPs of different sizes. The calculated EFs from Raman spectra reveal a significant decrease with an increase in AuNPs sizes. Molecular dynamics calculations were carried out to obtain the adsorption energies for different ratios of HS-PEG-(CH2)11COOH to HS-(CH2)11-NHCO-coumarin. It was found that molecules that adsorb strongly on the surface of the metal, underwent changes in their polarizability and consequently enhanced Raman intensities were observed, and this was in agreement with experimental data.

  19. Extraction time and temperature affect the extraction efficiencies of coumarin and phenylpropanoids from Cinnamomum cassia bark using a microwave-assisted extraction method.

    Science.gov (United States)

    Kim, Jung-Hoon

    2017-09-15

    Microwave-assisted extraction (MAE), an efficient extraction tool, was employed to extract a coumarin and five phenylpropanoids (cinnamic acid, cinnamyl alcohol, cinnamaldehyde, 2-hydroxycinnamadehyde, and 2-methoxycinnamaldehyde) from Cinnamomum cassia bark using water as the extraction solvent. Six marker compounds were quantified by high-performance liquid chromatography-diode array detector using a validated analytical method. To investigate the influences of temperature and time on the extraction yields of the six marker compounds, the water extracts of C. cassia bark were prepared using a MAE method at six different extraction temperatures (70, 75, 80, 85, 90, and 95°C) and times (2, 4, 6, 8, 10, and 12min). Their influences were assessed by multiple regression analysis. The results obtained demonstrated that higher extraction temperature and longer extraction time positively affected coumarin and cinnamyl alcohol contents, but negatively affected extract contents of cinnamic acid, cinnamaldehyde and 2-hydroxycinnamaldehyde (all p-extraction of 2-methoxycinnamaldehyde was affected by both positively and negatively by increasing temperature and time. These changes during MAE were assumed by the chemical natures of the marker compounds with various functional groups. In conclusion, temperature and times significantly affected the extraction efficiencies of a coumarin and five phenylpropanoids from C. cassia bark when a water-based MAE method was used. This study provides a novel approach to the preparation of the water extract of C. cassia bark using MAE. Copyright © 2017 Elsevier B.V. All rights reserved.

  20. Preparation and characterization of mesoporous ZnO-ZrO2 doped by Cr, Nd and Dy as a catalyst for conversion of coumarin using ultrasensitive fluorometric method

    Science.gov (United States)

    Ibrahim, M. M.

    2017-04-01

    Doping of mesoporous ZnO-ZrO2 nanoparticles with transition metal and lanthanides (Cr, Nd, Dy) were used as a catalyst to develop an ultrasensitive fluorometric method for the conversion of non fluorescent coumarin to highly fluorescent 7-hydroxycoumarin using H2O2 or light. It was found that doped- ZnO-ZrO2 mixed oxide can catalyze the decomposition of H2O2 to produce •OH radicals, which in turn convert coumarin to 7-hydroxycoumarin. At contrast, the doping has deleterious effect on conversion of coumarin by light due to high band gap and high concentrations of doping increase the recombination rate of electron and holes. Doped mixed oxides prepared by impregnation method and characterized by studying their structural, surface and optical properties. Chromium doped ZnO-ZrO2 had the highest rate of formation of hydroxyl radical due to decomposition of H2O2 and therefore 7-hydroxycoumarin due to surface area, small crystal size and high redox potential.

  1. Pharmacokinetics Research Advances of Coumarin Compounds in Vivo%香豆素类化合物的体内代谢研究进展

    Institute of Scientific and Technical Information of China (English)

    雷震; 马卫东; 於凯芹; 杨光义; 张晨宁; 魏晋宝; 张永红

    2016-01-01

    Coumarins, the components of Chinese herbal medicine, have multiple obvious biological activities. Document and literature about coumarins reported in recent tears were analtzed, concluded and summarized in the paper. Especiallt, pharmaceutics research advances of coumarin compounds in vivo were speciallt analtzed. It will lat the foundation of clinical rational use of drugs and design of appropri-ate dosage forms.%香豆素类化合物是中草药中一类重要成分,具有明显的药理活性。该文就近几年国内外关于香豆素类的文献资料进行分析、归纳和总结,对其药代动力学研究进展进行了相关分析,对香豆素类化合物的药代动力学的研究,将有利于临床用药指导和适宜剂型设计,为合理用药奠定基础。

  2. Novel D-π-A-π-A coumarin dyes for highly efficient dye-sensitized solar cells: Effect of π-bridge on optical, electrochemical, and photovoltaic performance

    Science.gov (United States)

    Feng, Haijing; Li, Ranran; Song, Yicong; Li, Xiaoyan; Liu, Bo

    2017-03-01

    The direct connection of coumarin and auxiliary acceptor in D-A-π-A construction will cause large dihedral angle between these two planes, thus affecting the intramolecular charge transfer process. Herein, with an additional π-bridge between coumarin and auxiliary acceptor, two novel coumarin sensitizers, CS-1 and CS-2, based on D-π-A-π-A construction have been designed and synthesized. With this modification, the planarity of donor-to-auxiliary acceptor part is effectively improved, thus resulting in smoother ICT process and less energy loss. Along with the planarization of molecule, the energy levels of the dyes are also effectively optimized. Moreover, the introduction of additional π-bridge will not affect the photostability of the dye. Accordingly, a record high PCE of 8.03% is obtained by CS-2 sensitized DSSCs, with a JSC of 16.38 mA cm-2, a VOC of 694 mV, and a ff of 0.707, while only around 3.5% decline in PCE is found after 1000 h aging test. Our results demonstrate that good planarity is obviously preferred to optimize the energy level and photovoltaic performance of sensitizer, providing a powerful strategy for the development of highly efficient organic sensitizers in the future.

  3. 6种新型香豆素类衍生物的拉曼光谱研究%Raman spectra studies on six new coumarin derivatives

    Institute of Scientific and Technical Information of China (English)

    刘婵; 周吉; 刘丽娜; 任华华; 叶勇

    2013-01-01

    The coumarins have been widely used as the organic heterocyclic compounds .It has very high medicine value duce to its biological activities in preventing HIV , preventing cancer , lowering blood pressure and preventing arrhythmia .In this study ,six new derivatives of coumarin were synthesized by using the tertiary amine as catalyst ,and then these coumarin derivatives were characterized by Raman spectra .Besides ,the characteristic spectra of the compound were assigned and we discussed the effects of structure in different components on the Raman spectra .%  香豆素是一类应用很广泛的有机杂环化合物,具有抗 HIV、抗癌、降压、抗心律失常等多种生物活性,具有很高的药用价值。本实验利用叔胺催化,合成了6种新型香豆素衍生物,采用激光显微拉曼光谱对其结构进行研究,归属各化合物拉曼谱峰,并探讨分子结构差异对拉曼光谱的影响。

  4. Coumarin-thiazole and -oxadiazole derivatives: Synthesis, bioactivity and docking studies for aldose/aldehyde reductase inhibitors.

    Science.gov (United States)

    Ibrar, Aliya; Tehseen, Yildiz; Khan, Imtiaz; Hameed, Abdul; Saeed, Aamer; Furtmann, Norbert; Bajorath, Jürgen; Iqbal, Jamshed

    2016-10-01

    In continuation of our previous efforts directed towards the development of potent and selective inhibitors of aldose reductase (ALR2), and to control the diabetes mellitus (DM), a chronic metabolic disease, we synthesized novel coumarin-thiazole 6(a-o) and coumarin-oxadiazole 11(a-h) hybrids and screened for their inhibitory activity against aldose reductase (ALR2), for the selectivity against aldehyde reductase (ALR1). Compounds were also screened against ALR1. Among the newly designed compounds, 6c, 11d, and 11g were selective inhibitors of ALR2. Whereas, (E)-3-(2-(2-(2-bromobenzylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one 6c yielded the lowest IC50 value of 0.16±0.06μM for ALR2. Moreover, compounds (E)-3-(2-(2-benzylidenehydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6a; IC50=2.94±1.23μM for ARL1 and 0.12±0.05μM for ARL2) and (E)-3-(2-(2-(1-(4-bromophenyl)ethylidene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6e; IC50=1.71±0.01μM for ARL1 and 0.11±0.001μM for ARL2) were confirmed as dual inhibitors. Furthermore, compounds 6i, 6k, 6m, and 11b were found to be selective inhibitors for ALR1, among which (E)-3-(2-(2-((2-amino-4-chlorophenyl)(phenyl)methylene)hydrazinyl)thiazol-4-yl)-2H-chromen-2-one (6m) was most potent (IC50=0.459±0.001μM). Docking studies performed using X-ray structures of ALR1 and ALR2 with the given synthesized inhibitors showed that coumarinyl thiazole series lacks the carboxylate function that could interact with the anionic binding site being a common ALR1/ALR2 inhibitors trait. Molecular docking study with dual inhibitor 6e also suggested plausible binding modes for the ALR1 and ALR2 enzymes. Hence, the results of this study revealed that coumarinyl thiazole and oxadiazole derivatives could act as potential ALR1/ALR2 inhibitors.

  5. New fluorescent probes of the hydroxyl radical: characterisation and modelization of the reactivity of coumarin derivatives with HO; Developpement de sondes fluorescentes du radical hydroxyle: caracterisation et modelisation de la reactivite de molecules derivees de la coumarine avec HO

    Energy Technology Data Exchange (ETDEWEB)

    Louit, G.

    2005-10-15

    The hydroxyl radical is involved in a wide range of different fields, from oxidative stress to atmospheric chemistry. In addition to the study of oxidative damage in biological media, the hydroxyl radical detection allows to perform a dosimetry when it is produced by ionising radiation. The aims of this work have been double: - to improve the detection of the hydroxyl radical by the design of new probes - to improve knowledge on the reactive pathways in which the hydroxyl radical is involved. We have studied the coumarin molecule, as well as 6 derivatives that we have synthesised, as fluorescent probes of the hydroxyl radical. Firstly, fluorescence spectroscopy and HPLC chromatography have allowed the evaluation of the sensibility and selectivity of detection of the probes. Consequently to this study, two applications have been developed, concerning the determination of rate constants by competition kinetics and bidimensional dosimetry. Secondly, we have studied the reactivity of the hydroxyl radical through the regioselectivity of its addition on the aromatic cycle. This problem was addressed by the combined use of experimental methods such as time resolved kinetics and HPLC along with interpretation from classical and ab initio modelization. (author)

  6. 白芷香豆素的抑菌及稳定性研究%Research on AntibacteriaI Effect and StabiIity of Coumarin of Angelicae dahuricae

    Institute of Scientific and Technical Information of China (English)

    杨柳; 刘长姣; 李玉邯; 陈宇飞; 王磊; 张一

    2016-01-01

    The antibacterial effect and stability of coumarin of Angelicae dahuricae are studied in the paper.Through the detection on bacteriostasis rate of coumarin on bacteria and fungi,the effect of minimum inhibitory concentration (MIC),illumination,oxidant,temperature,pH on bacteriostasis rate of coumarin,it is obtained that the antibacterial effect of coumarin of Angelicae dahuricae on bacteria is better.When the concentration of coumarin is 200 mg/mL,the bacteriostasis rate reaches above 90%.MIC of Staphylococcusaureus is 12.5 mg/mL.The antibacterial ability of coumarin on yeast is the worst.The antibacterial effect of illumination,temperature,pH below 7 .0 on coumarin is greater,and the effect of coumarin on oxidant is relatively stable. This study has provided a theoretical reference for the application of coumarin of Angelicae dahuricae .%研究白芷香豆素的抑菌效果和稳定性。通过测定香豆素对细菌和真菌的抑菌率、最低抑菌浓度(MIC)、光照、氧化剂、温度、pH 对香豆素抑菌率的影响实验。得出香豆素对细菌抑制效果较好,浓度为200 mg/mL的香豆素,抑菌率达90%以上,金黄色葡萄球菌的 MIC 为12.5 mg/mL,对酵母菌的抑菌能力最差;光照、温度及pH 为酸性时,对香豆素的抑菌效果影响较大,而香豆素对氧化剂相对稳定。该研究为白芷香豆素的应用提供理论参考。

  7. 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.

  8. Binding of Coumarin 334 with β-Cyclodextrin and with C-Hexylpyrogallol[4]arene: Opposite Fluorescence Behavior

    Directory of Open Access Journals (Sweden)

    Chandrasekaran Sowrirajan

    2013-01-01

    Full Text Available We report here the structure of the host-guest complexes of Coumarin 334 (C334 with β-cyclodextrin (β-CD and with C-hexylpyrogallol[4]arene (C-HPA and the effect of acidity on the neutral-cation equilibrium of C334 in water and in the presence of the host molecules. The structures of the host-guest complexes are proposed on the basis of the change of fluorescence on the addition of β-CD or C-HPA to C334 and by 2D ROESY spectroscopy. Opposite fluorescence behaviors, that is, quenching of fluorescence in β-CD and enhancement of fluorescence in C-HPA are observed. Time-resolved fluorescence analysis is done for the complexation, and biexponential decay pattern is observed. The possible strong inclusion complexation with C-HPA is explained. The ground and the excited state pKa values for the protonation equilibrium of C334 in water and the difficulty of protonation in the presence of the host molecules are discussed.

  9. Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents.

    Science.gov (United States)

    Ji, Qinggang; Ge, Zhiqiang; Ge, Zhixing; Chen, Kaizhi; Wu, Hualong; Liu, Xiaofei; Huang, Yanrong; Yuan, Lvjiang; Yang, Xiaolan; Liao, Fei

    2016-01-27

    A series of novel phosphoramidate derivatives of coumarin have been designed and synthesized as chitin synthase (CHS) inhibitors. All the synthesized compounds have been screened for their chitin synthase inhibition activity and antimicrobial activity in vitro. The bioactive assay manifested that most of the target compounds exhibited good efficacy against CHS and a variety of clinically important fungal pathogens. In particular, compound 7t with IC50 of 0.08 mM against CHS displayed stronger efficiency than the reference Polyoxin B with IC50 of 0.16 mM. In addition, the apparent Ki values of compound 7t was 0.096 mM while the Km of Chitin synthase prepared from Candida tropicalis was 3.86 mM for UDP-N-acetylglucosamine, and the result of the Ki showed that the compounds was a non-competitive inhibitor of the CHS. As far as the antifungal activity is concerned, compounds 7o, 7r and 7t were highly active against Aspergillus flavus with MIC values in the range of 1 μg/mL to 2 μg/Ml while the results of antibacterial screening showed that these compounds have negligible actions to the tested bacteria. These results indicated that the design of these compounds as antifungal agents was rational.

  10. Coumarin-based 'turn-off' fluorescent chemosensor with high selectivity for Cu2+ in aqueous solution

    Science.gov (United States)

    Xu, Wen-Jun; Qi, De-Qiang; You, Jin-Zong; Hu, Fei-Fei; Bian, Jia-Ying; Yang, Chun-Xia; Huang, Juan

    2015-07-01

    Coumarin-based "turn-off" fluorescent chemosensor, 3-acetoacetyl-7-diethylaminocoumarin (1), has been synthesized and structurally characterized by IR, 1H NMR and X-ray crystal structure analysis. The fluorescence behaviors in the presence of various metal ions were investigated in aqueous media. 1 Exhibits highly selective and sensitive absorbance and fluorescence sensing ability for Cu2+ over other metal ions. Addition of Cu2+ to the aqueous solution of 1 gave rise to obvious absorbance change and fluorescence quenching. Other competing ions, such as Mg2+, Ba2+, Mn2+, Fe3+, Co2+, Ni2+, Zn2+, Pb2+, Cd2+, Hg2+, induced negligible absorbance and fluorescence changes under the same conditions. The job's plot showed that the stoichiometry between 1 and Cu2+ was estimated to be 1:1. The fluorescence intensity varied almost linearly vs. the concentration of Cu2+ (1.0-7.0 μM), and the detection limit of Cu2+ was estimated to be 1.81 nM, indicating that 1 can be used as "turn-off" fluorescent chemosensor to selectively detect Cu2+ in aqueous solution.

  11. In vitro characterization of 6-Coumarin loaded solid lipid nanoparticles and their uptake by immunocompetent fish cells.

    Science.gov (United States)

    Trapani, Adriana; Mandracchia, Delia; Di Franco, Cinzia; Cordero, Héctor; Morcillo, Patricia; Comparelli, Roberto; Cuesta, Alberto; Esteban, Maria Angeles

    2015-03-01

    The primary aim of the present work was to evaluate the in vitro uptake of 6-Coumarin (6COUM) loaded solid lipid nanoparticles (SLN) by two gilthead seabream (Sparus aurata L.) cell types: an established cell line (SAF-1 cells) and the primary cultures of head-kidney (HK)-the main haemopoietic organ in fish, equivalent to mammalian bone marrow-leucocytes. For this purpose, after the physicochemical characterization of SLN, the uptake by those immunocompetent fish cells was evaluated using flow cytometry and confocal microscopy. Concomitantly, the uptake of 6-COUM loaded SLN was compared with that achieved with 6-COUM loaded pectin microparticles (MPs), which were selected as a competitor of the delivery carriers. After SLN and MP physicochemical characterization, the results demonstrated that SAF-1 cells were able to internalize high percentages of 6-COUM SLNs when incubated for 4, 8 and 24h, with the highest SLN concentration tested (10 μg/ml). The ability of HK leucocytes to internalize SLN was also found to vary depending on both incubation time and SLN concentration. The highest values of HK leucocytes internalizing SLN particles (around 16%) were detected at the maximum SLN concentration (20 μg/ml) at incubation times of 4 or 8h. Conversely, HK leucocytes were unable to internalize MPs at any tested concentration and incubation time. A possible mechanism explaining the uptake into cells is proposed. The present work constitutes the first approximation to consider SLN as nanocarriers for delivering biologically active substances to fish.

  12. Coumarin sulfonamides derivatives as potent and selective COX-2 inhibitors with efficacy in suppressing cancer proliferation and metastasis.

    Science.gov (United States)

    Lu, Xiao-Yuan; Wang, Zhong-Chang; Ren, Shen-Zhen; Shen, Fa-Qian; Man, Ruo-Jun; Zhu, Hai-Liang

    2016-08-01

    Cyclooxygenase-2 is frequently overexpression in malignant tumors and the product PGE2 promotes cancer cell progression and metastasis. We designed novel series of coumarin sulfonamides derivatives to improve biological activities of COX-2 inhibition and anticancer. Among them, compound 7t showed most powerful selective inhibitory and antiproliferative activity (IC50=0.09μM for COX-2, IC50=48.20μM for COX-1, IC50=0.36μM against HeLa cells), comparable to the control positive compound Celecoxib (0.31μM, 43.37μM, 7.79μM). Cancer cell apoptosis assay were performed and results indicated that compound 7t effectively fuels HeLa cells apoptosis in a dose and time-dependent manner. Moreover, 7t could significantly suppress cancer cell adhesion, migration and invasion which were essential process of cancer metastasis. Docking simulations results was further indicated that compound 7t could bind well to the COX-2 active site and guided a reasonable design of selective COX-2 inhibitor with anticancer activities in future.

  13. Synthesis, Structural Elucidation, and Antibacterial Evaluation of Some New Molecules Derived from Coumarin, 1,3,4-Oxadiazole, and Acetamide

    Directory of Open Access Journals (Sweden)

    Shahid Rasool

    2016-01-01

    Full Text Available Because of the reported biological activities of coumarin, 1,3,4-oxadiazole, and acetamides, some new compounds incorporating these moieties were synthesized and evaluated for their biological potential against Gram-positive and Gram-negative bacteria. In the present work, 4-chlororesorcinol (1 and ethyl acetoacetate (2 were mixed in a strong acidic medium to synthesize 6-chloro-7-hydroxy-4-methyl-2-oxo-2H-chromene (3 which was subjected to the intermolecular cyclization after consecutive three steps to synthesize 5-[(6-chloro-4-methyl-2-oxo-2H-chromen-7-yloxy]methyl-1,3,4-oxadiazol-2-thiol (6. A series of acetamoyl electrophiles, 8a–o, were synthesized from aralkyl/alkyl/aryl amines, 7a–o, in an aqueous basic medium. The final compounds, 9a–o, were synthesized by the reaction of compounds 6 and 8a–o in DMF/NaH. The synthesized compounds were structurally elucidated by spectral data analysis of IR, 1H-NMR, and EIMS. The most of the synthesized compounds remained moderate to excellent antibacterial agents. The molecules, 9e, 9j, and 9k, were the most efficient ones against all the five bacterial strains taken into account.

  14. New Limonoids from Hortia oreadica and Unexpected Coumarin from H. superba Using Chromatography over Cleaning Sephadex with Sodium Hypochlorite

    Directory of Open Access Journals (Sweden)

    Vanessa G.P. Severino

    2014-08-01

    Full Text Available Previous investigations of H. oreadica reported the presence of a wide spectrum of complex limonoids and dihydrocinnamic acids. Our interest in the Rutaceae motivated a reinvestigation of H. oreadica, H. brasiliana and H. superba searching for other secondary metabolites present in substantial amounts for taxonomic analysis. In a continuation of the investigation of the H. oreadica, three new limonoids have now been isolated 9α-hydroxyhortiolide A, 11β-hydroxyhortiolide C and 1(S*-acetoxy-7(R*-hydroxy-7-deoxoinchangin. All the isolated compounds from the Hortia species reinforce its position in the Rutaceae. With regard to limonoids the genus produces highly specialized compounds, whose structural variations do not occur in any other member of the Rutaceae, thus, it is evident from limonoid data that Hortia takes an isolated position within the family. In addition, H. superba afforded the unexpected coumarin 5-chloro-8-methoxy-psoralen, which may not be a genuine natural product. Solid-state cross-polarisation/magic-angle-spinning 13C nuclear magnetic resonance, X-Ray fluorescence and Field-emission gun scanning electron microscopy experiments show that the Sephadex LH-20 was modified after treatment with NaOCl, suggesting that when xanthotoxin (8-methoxy-psoralen was extracted from cleaning of the gel column, chlorination of the aromatic system occurred.

  15. 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.

  16. DFT modeling and spectroscopic study of metal ligand bonding in La(III) complex of coumarin-3-carboxylic acid

    Science.gov (United States)

    Mihaylov, Tz.; Trendafilova, N.; Kostova, I.; Georgieva, I.; Bauer, G.

    2006-09-01

    The binding mode of coumarin-3-carboxylic acid (HCCA) to La(III) is elucidated at experimental and theoretical level. The complexation ability of the deprotonated ligand (CCA -) to La(III) is studied using elemental analysis, DTA and TGA data as well as FTIR, 1H NMR and 13C NMR spectra. The experimental data suggest the complex formula La(CCA) 2(NO 3)(H 2O) 2. B3LYP, BHLYP, B3P86, B3PW91, PW91P86 and MPW1PW91 functionals are tested for geometry and frequency calculations of the neutral ligand and all of them show bond length deviations bellow 1%. B3LYP/6-31G(d) level combined with large quasi-relativistic effective core potential for lanthanum is selected to describe the molecular, electronic and vibrational structures as well as the conformational behavior of HCCA, CCA - and La-CCA complex. The metal-ligand binding mode is predicted through molecular modeling and energy estimation of different La-CCA structures. The calculated atomic charges and the bonding orbital polarizations point to strong ionic metal-ligand bonding in La-CCA complex and insignificant donor acceptor interaction. Detailed vibrational analysis of HCCA, CCA - and La(CCA) 2(NO 3)(H 2O) 2 systems based on both calculated and experimental frequencies confirms the suggested metal-ligand binding mode.

  17. Subclinical hyperthyroidism seems not to have a significant impact on systemic anticoagulation in patients with coumarin therapy.

    Science.gov (United States)

    Bucerius, Jan; Naubereit, Anna; Joe, Alexius Y; Ezziddin, Samer; Biermann, Kim; Risse, Jörn; Palmedo, Holger; Oldenburg, Johannes; Biersack, Hans-Jürgen

    2008-11-01

    There is little data regarding the impact of subclinical hyperthyroidism on coagulation metabolism in patients undergoing systemic anticoagulation therapy with coumarin derivates. In this retrospective analysis we studied 233 patients with benign thyroid disorders receiving therapeutic iodine-131, as well as concomitant systemic anticoagulation therapy (subclinical hyperthyroidism: n = 178; overt hyperthyroidism: n = 15; euthyroidism: n = 40). Multivariate regression analyses were performed in the total study population as well as in the subgroup of patients with subclinical hyperthyroidism to identify the possible impact of several variables on anticoagulation therapy, large enough to push the International Normalized Ratio (INR) level out of the therapeutic range (INR 3.0). Therapy with antibiotics or nitrates was significantly associated with INR-values >3.0 in the total population, while ACE inhibitors were associated with lower incidence of INR-values subclinical hyperthyroidism, therapy with antibiotics was predictive of INR-values >3.0, whereas therapy with thyroid suppressive drugs or TSH-values subclinical hyperthyroidism and euthyroidism intraindividual comparison with regard to the possible impact on anticoagulation therapy was performed which failed to show any significant differences in INR-values between the two thyroid metabolic conditions. In conclusion, subclinical hyperthyroidism seems to have no significant impact on coagulation metabolism in patients receiving anticoagulation therapy.

  18. Multimodal use of new coumarin-based fluorescent chemosensors: towards highly selective optical sensors for Hg(2+) probing.

    Science.gov (United States)

    Bazzicalupi, Carla; Caltagirone, Claudia; Cao, Zenfeng; Chen, Qibin; Di Natale, Corrado; Garau, Alessandra; Lippolis, Vito; Lvova, Larisa; Liu, Honglai; Lundström, Ingemar; Mostallino, M Cristina; Nieddu, Mattia; Paolesse, Roberto; Prodi, Luca; Sgarzi, Massimo; Zaccheroni, Nelsi

    2013-10-18

    Despite several types of fluorescent sensing molecules have been proposed and examined to signal Hg(2+) ion binding, the development of fluorescence-based devices for in-field Hg(2+) detection and screening in environmental and industrial samples is still a challenging task. Herein, we report the synthesis and characterization of three new coumarin-based fluorescent chemosensors featuring mixed thia/aza macrocyclic framework as receptors units, that is, ligands L1-L3. These probes revealed an OFF-ON selective response to the presence of Hg(2+) ions in MeCN/H2 O 4:1 (v/v), which allowed imaging of this metal ion in Cos-7 cells in vitro. Once included in silica core-polyethylene glycol (PEG) shell nanoparticles or supported on polyvinyl chloride (PVC)-based polymeric membranes, ligands L1-L3 can also selectively sense Hg(2+) ions in pure water. In particular we have developed an optical sensing array tacking advantage of the fluorescent properties of ligand L3 and based on the computer screen photo assisted technique (CSPT). In the device ligand L3 is dispersed into PVC membranes and it quantitatively responds to Hg(2+) ions in natural water samples.

  19. A coumarin based Schiff base probe for selective fluorescence detection of Al3 + and its application in live cell imaging

    Science.gov (United States)

    Sen, Bhaskar; Sheet, Sanjoy Kumar; Thounaojam, Romita; Jamatia, Ramen; Pal, Amarta Kumar; Aguan, Kripamoy; Khatua, Snehadrinarayan

    2017-02-01

    A new coumarin based Schiff base compound, CSB-1 has been synthesized to detect metal ion based on the chelation enhanced fluorescence (CHEF). The cation binding properties of CSB-1 was thoroughly examined in UV-vis and fluorescence spectroscopy. In fluorescence spectroscopy the compound showed high selectivity toward Al3 + ion and the Al3 + can be quantified in mixed aqueous buffer solution (MeOH: 0.01 M HEPES Buffer; 9:1; v/v) at pH 7.4 as well as in BSA media. The fluorescence intensity of CSB-1 was enhanced by 24 fold after addition of only five equivalents of Al3 +. The fluorescence titration of CSB-1 with Al3 + in mixed aqueous buffer afforded a binding constant, Ka = (1.06 ± 0.2) × 104 M- 1. The colour change from light yellow to colourless and the appearance of blue fluorescence, which can be observed by the naked eye, provides a real-time method for Al3 + sensing. Further the live cell imaging study indicated that the detection of intracellular Al3 + ions are also readily possible in living cell.

  20. Development of an in Silico Model of DPPH• Free Radical Scavenging Capacity: Prediction of Antioxidant Activity of Coumarin Type Compounds

    Directory of Open Access Journals (Sweden)

    Elizabeth Goya Jorge

    2016-06-01

    Full Text Available A quantitative structure-activity relationship (QSAR study of the 2,2-diphenyl-l-picrylhydrazyl (DPPH• radical scavenging ability of 1373 chemical compounds, using DRAGON molecular descriptors (MD and the neural network technique, a technique based on the multilayer multilayer perceptron (MLP, was developed. The built model demonstrated a satisfactory performance for the training ( R 2 = 0.713 and test set ( Q ext 2 = 0.654 , respectively. To gain greater insight on the relevance of the MD contained in the MLP model, sensitivity and principal component analyses were performed. Moreover, structural and mechanistic interpretation was carried out to comprehend the relationship of the variables in the model with the modeled property. The constructed MLP model was employed to predict the radical scavenging ability for a group of coumarin-type compounds. Finally, in order to validate the model’s predictions, an in vitro assay for one of the compounds (4-hydroxycoumarin was performed, showing a satisfactory proximity between the experimental and predicted pIC50 values.

  1. Solvent Effects on Spectral Property and Dipole Moment of the Lowest Excited State of Coumarin 343 Dye

    Institute of Scientific and Technical Information of China (English)

    Li-lin Jiang; Wei-long Liu; Yun-fei Song; Xing He; Yang Wang; Hong-lin Wu; Yan-qiang Yang

    2012-01-01

    Steady-state absorption and fluorescence spectra,and time-resolved fluorescence spectra of coumarin 343 (C343) were measured in different solvents.The effect of the solvent on the spectral properties and dipole moment of the lowest excited state of C343 were investigated.It was found that the absorption and fluorescence spectra red-shifted slightly and strongly with increasing solvent polarity,respectively,because the charge distribution of the excited state leaded to the increasing difference between the absorption and fluorescence spectra with increasing solvent polarity.The dipole moment of the lowest excited state of C343 was determined from solvatochromic measurements and the quantum chemical calculation,and the results obtained from these two methods were fully consistent.Investigations of the time-resolved fluorescence of C343 in different solvents indicated that the fluorescence lifetimes increased nearly linearly with increasing solvent polarity from 3.09 ns in toluene to 4.45 ns in water.This can be ascribed to the intermolecular hydrogen bonding interactions between C343 and hydrogen donating solvents.

  2. Induction of two prenyltransferases for the accumulation of coumarin phytoalexins in elicitor-treated Ammi majus cell suspension cultures.

    Science.gov (United States)

    Hamerski, D; Schmitt, D; Matern, U

    1990-01-01

    Two dimethylallyl diphosphate:umbelliferone dimethylallyltransferase (prenyltransferase) activities, catalysing the 6-prenylation and the 7-O-prenylation, respectively, of umbelliferone in the course of phytoalexin synthesis, increased in Ammi majus cell suspension cultures in response to elicitor treatment. Both enzyme activities were dependent on Mg2+ or Mn2+ with significant preference for Mg2+ in the 6-prenylation reaction. Whereas dark-grown cells did not contain these activities, both prenyltransferase activities were induced rapidly by the addition of elicitor reaching a first maximum after 10-14 hr and a second maximum beyond 30 hr. Other coumarin specific, elicitor-induced enzyme activities of A. majus cells, in contrast, showed only one maximum of activity within the 50 hr experimental period, while the pattern of induction of phenylalanine ammonia-lyase activity resembled that of the prenyltransferases with maxima at ca 8 hr and 20-30 hr. Preliminary data suggest that the apparent biphasic induction of these enzyme activities is due to post-translational enzyme modifications.

  3. Statistical methods for estimating the probability of spontaneous abortion in observational studies--analyzing pregnancies exposed to coumarin derivatives.

    Science.gov (United States)

    Meister, Reinhard; Schaefer, Christof

    2008-09-01

    Spontaneous abortion rates are of general interest when investigating pregnancy outcome. In most studies observations are left truncated as pregnant women enter with a delay of several weeks after conception. Apart from spontaneous abortion pregnancy may end in induced abortion or live birth. These outcomes are considered as competing events (risks). Although statistical methods for handling this setting are available since more than 10 years, studies on pregnancy outcome after drug exposure usually report crude rates of spontaneous abortions, ignoring left truncation and competing risks. The authors propose simple methods which remove bias inherent to crude rates. The probability of spontaneous abortion is estimated using an event-history based approach for the subdistribution of competing risks that handles left truncation appropriately. Variance estimation enables the construction of approximate confidence intervals and of a simple test-statistic for comparing rates between different cohorts. The proposed methods are applied to a comparative prospective study on the association of spontaneous abortion and exposure to coumarin derivatives. The naive analysis using crude rates gives substantially different results than those based on the proposed methods, with up to a twofold change. Correctly incorporating left truncation into the analysis may increase the variance of the estimators, relative to an ideal sample where all pregnancies are followed from the time of conception. The consequences of such truncation for study design are discussed. Combining corrections for left truncation and competing risks offers a powerful method for analyzing miscarriage risk.

  4. Microwave assisted synthesis, spectroscopic, electrochemical and DNA cleavage studies of lanthanide(III) complexes with coumarin based imines.

    Science.gov (United States)

    Kapoor, Puja; Fahmi, Nighat; Singh, R V

    2011-12-01

    The present work stems from our interest in the synthesis, characterization and biological evaluation of lanthanide(III) complexes of a class of coumarin based imines which have been prepared by the interaction of hydrated lanthanide(III) chloride with the sodium salts of 3-acetylcoumarin thiosemicarbazone (ACTSZH) and 3-acetylcoumarin semicarbazone (ACSZH) in 1:3 molar ratio using thermal as well as microwave method. Characterization of the ligands as well as the metal complexes have been carried out by elemental analysis, melting point determinations, molecular weight determinations, magnetic moment, molar conductance, IR, (1)H NMR, (13)C NMR, electronic, EPR, X-ray powder diffraction and mass spectral studies. Spectral studies confirm ligands to be monofunctional bidentate and octahedral environment around metal ions. The redox behavior of one of the synthesized metal complex was investigated by cyclic voltammetry. Further, free ligands and their metal complexes have been screened for their antimicrobial as well as DNA cleavage activity. The results of these findings have been presented and discussed.

  5. The Synthesis of a Coumarin Carbohydrazide Dinuclear Copper Complex Based Fluorescence Probe and Its Detection of Thiols.

    Science.gov (United States)

    He, Guangjie; Li, Jing; Yang, Lu; Hou, Chunhua; Ni, Tianjun; Yang, Zhijun; Qian, Xinlai; Li, Changzheng

    2016-01-01

    Small-molecule thiols, such as cysteine (CYS) and glutathione (GSH), are essential for maintaining the cellular redox environment and play important roles in regulating various cellular physiological functions. A fluorescence probe (compound 1-Cu2+) for thiols based on coumarin carbohydrazide dinuclear copper complex was developed. Compound 1 was synthesized from the reaction of 7-(diethylamino)-2-oxo-2H-chromene-3-carbohydrazide with 4-tert-butyl-2,6- diformylphenol. Accordingly, the copper complex (compound 1-Cu2+) was prepared by mixing compound 1 with 2 equivalents copper ions. Compound 1 had strong fluorescence while compound 1-Cu2+ hardly possessed fluorescence owing to the quenching nature of paramagnetism Cu2+ to the fluorescence molecule excited state. However, the fluorescence intensity of compound 1-Cu2+ was increased dramatically after the addition of thiol-containing amino acids, but not the other non-sulfhydryl amino acids. UV-vis absorption and fluorescence spectra indicated that compound 1-Cu2+ had good selectivity and sensitivity for thiols such as glutathione in CH3CN:H2O (3:2, v/v) PBS solution. The fluorescence imaging experiments implied that compound 1-Cu2+ has potential application in thiol-containing amino acids detection in living cells.

  6. Impact of Substituents on Excited-State and Photosensitizing Properties in Cationic Iridium(III) Complexes with Ligands of Coumarin 6.

    Science.gov (United States)

    Takizawa, Shin-Ya; Ikuta, Naoya; Zeng, Fanyang; Komaru, Shohei; Sebata, Shinogu; Murata, Shigeru

    2016-09-01

    A series of bis-cyclometalated cationic iridium (Ir) complexes were synthesized employing two coumarin 6 ligands and a 2,2'-bipyridine (bpy) with various substituents as new sensitizers, realizing both features of strong visible-light absorption and long-lived excited state. Complexes 2-4, with electron-donating methyl and methoxy groups, absorbed visible light strongly (ε: 126 000-132 000 M(-1) cm(-1)) and exhibited room-temperature phosphorescence with remarkably long lifetimes (21-23 μs) in dichloromethane. In contrast, the excited state of prototype complex 1 without any substituents was short-lived, particularly in highly polar acetonitrile. Phosphorescence of complex 5 with the strong electron-withdrawing CF3 groups was too weak to be detected at room temperature even in less polar dichloromethane. The triplet energies of their coumarin ligand-centered ((3)LC) phosphorescent states were almost invariable, demonstrating that selective tuning of the excited-state lifetime is possible through this "simple chemical modification of the bpy ligand" (we name it the "SCMB" method). The spectroscopic and computational investigations in this study suggest that a potential source of the nonradiative deactivation is a triplet ligand-to-ligand charge-transfer state ((3)LLCT state, coumarin 6 → bpy) and lead us to conclude that the energy level of this dark (3)LLCT state, as well as its thermal population, is largely dependent on the substituents and solvent polarity. In addition, the significant difference in excited-state lifetime was reflected in the photosensitizing ability of complexes 1-5 in visible-light-driven hydrogen generation using sodium ascorbate and a cobalt(III) diglyoxime complex as an electron donor and a water-reduction catalyst, respectively. This study suggests that the SCMB method should be generally effective in controlling the excited state of other bis-cyclometalated cationic Ir(III) complexes.

  7. Derivatives containing both coumarin and benzimidazole potently induce caspase-dependent apoptosis of cancer cells through inhibition of PI3K-AKT-mTOR signaling.

    Science.gov (United States)

    Liu, Haitao; Wang, Yubin; Sharma, Ashok; Mao, Rui; Jiang, Na; Dun, Boying; She, Jin-Xiong

    2015-07-01

    Coumarins are a large family of compounds derived from a wide range of plants, fungi, and bacteria, and coumarin derivatives can have extremely variable structures and consequently diverse biological properties including antitumor activity. Compounds that bear a benzimidazole moiety are known to possess antitumor activity and a variety of other biological activities. High-throughput screening of a compound library identified a coumarin-containing and a benzimidazole-containing compound [#32, 7-(diethylamino)-3-(1-methyl-1H-benzimidazol-2-yl)-2H-chromen-2-one] that has potent anticancer activity. Evaluation of 17 additional analogs further identified three compounds with anticancer activity in 14 different human cancer cell lines. Fluorescence-activated cell sorting and western blotting analyses suggested that these compounds can induce caspase-dependent apoptosis. Real-time reverse transcriptase PCR analyses of 26 cancer-related genes revealed that seven genes (NPPB, ATF3, DDIT4, CDH10, TSPAN14, TXNIP, and AXL) were significantly upregulated and nine genes (PAGE4, LRP8, SNCAIP, IGFBP5, SLCO2A1, CLDN2, ESRRG, D2HGDH, and PDGFRA) were significantly downregulated. The most upregulated gene is natriuretic peptide precursor B (NPPB) or brain natriuretic peptide, which is increased by 7-, 27-, and 197-fold at 12, 24, and 48 h, respectively. The second most upregulated gene is ATF3, which is increased by 23-fold at the 48 h timepoint. PAGE4 and IGFBP5 are the two most downregulated genes, with a 17-fold reduction in both genes. The expression of several genes (DDIT4, PDGFRA, LRP8, IGFBP5) and western blotting data on key signaling proteins indicate that compound #32 significantly inhibits the PI3K-AKT-mTOR pathway, an intracellular signaling pathway critical in cell proliferation and apoptosis.

  8. 香豆素类成分在球花石斛Dendrobium thyrsiflorum 叶和根中的分布与动态变化%Distribution and dynamic change of coumarins in leaf and root of Dendrobium thyrsiflorum

    Institute of Scientific and Technical Information of China (English)

    郑艳; 徐珞珊; 王峥涛; 张超英

    2009-01-01

    目的:探讨球花石斛Dendrobium thyrsiflorum不同生长发育时期叶和根中香豆素类(coumarins)成分的分布与动态变化,为充分利用药用石斛资源提供实验依据.方法:采集球花石斛营养生长期和生殖生长期的叶、根,利用激光共聚焦显微技术观察、分析其所含香豆素类成分.结果:球花石斛的叶除叶脉近上、下表皮处的维管束纤维群外,其他部位均有香豆素类成分的存在;球花石斛根的各部位均有香豆素类成分存在,尤其在皮层以内细胞的壁和壁内周.球花石斛叶、根的香豆素类成分的相对含量在生殖生长中的盛花期均高于营养生长期;在生殖生长进入始果期二者均几无香豆素类成分分布.结论:为充分利用药用植物,可从球花石斛的叶、根中提取香豆素类成分.%Objective: To study the distribution and dynamic change of coumarins in the leaf and root of Dendrobium thyrsiflo-rum at different developmental stages, and provide an experimental evidence for utilizing the medicinal plant. Method: The leaf and root materials were collected at vegetative and reproductive stage. By applying laser scanning confocal microscopy, relative quantity of coumarins of each sample was observed and analyzed. Result: Coumarins located in D. thyrsiflorum leaf except fibers in vascular bun-dles which were close to the upper or lower epidermis. Coumarins were found in D. thyrsiflorum root structure at different developmen-tal stages and walls of cells within cortex were especial appropriate places for the components distribution. Relative quantity of couma-rins was changed obviously when plant was growing. The components reached the highest level during profuse flowering period whereas there were less coumarins at vegetative period and little during initial fruit period. Conclusion: In order to utilize D. thyrsiflorum rea-sonably and thoroughly, coumarins should be extracted from the plant leaf and root.

  9. Quantum dynamical simulation of photoinduced electron transfer processes in dye-semiconductor systems: theory and application to coumarin 343 at TiO2

    Science.gov (United States)

    Li, Jingrui; Kondov, Ivan; Wang, Haobin; Thoss, Michael

    2015-04-01

    A recently developed methodology to simulate photoinduced electron transfer processes at dye-semiconductor interfaces is outlined. The methodology employs a first-principles-based model Hamiltonian and accurate quantum dynamics simulations using the multilayer multiconfiguration time-dependent Hartree approach. This method is applied to study electron injection in the dye-semiconductor system coumarin 343-TiO2. Specifically, the influence of electronic-vibrational coupling is analyzed. Extending previous work, we consider the influence of Dushinsky rotation of the normal modes as well as anharmonicities of the potential energy surfaces on the electron transfer dynamics.

  10. A Coumarin-Based Luminescent Chemosensor for Recognition of Cu(2+) and its In-Situ Complex for CN(-) Sensing via Cu(2+) Displacement Approach.

    Science.gov (United States)

    Mukherjee, Soma; Talukder, Shrabani

    2016-11-22

    A new coumarin based chemosensor has been developed for selective fluorescent recognition of Cu(2+) in MeOH/H2O (4:1, v/v at pH = 7.2 aqueous solution) medium with 1:1 binding stoichiometry. The in-situ prepared Cu(2+) complex displays high selectivity towards CN(-) via Cu(2+) displacement approach with detection limit in the micro molar range. Moreover, in presence of Cu(2+), the receptor exhibits reversible emission change with EDTA and thus offers an interesting property of molecular 'IMPLICATION' logic gate with Cu(2+) and EDTA as chemical inputs.

  11. A fluorescent coumarin-thiophene hybrid as a ratiometric chemosensor for anions: Synthesis, photophysics, anion sensing and orbital interactions

    Science.gov (United States)

    Yanar, Ufuk; Babür, Banu; Pekyılmaz, Damla; Yahaya, Issah; Aydıner, Burcu; Dede, Yavuz; Seferoğlu, Zeynel

    2016-03-01

    A colorimetric and fluorimetric fluorescent chemosensor (CT-2), having a coumarin ring as a signaling unit and an acetamido thiophene ring as an H-donor receptor, has been synthesized from amino derivative (CT-1) of CT-2 for the purpose of recognition of anions in DMSO. The absorption and emission maxima were both determined for the fluorescent dye in different solvents. Both hypsochromic shift at the absorption maximum, and quenching of fluorescence after interactions between the anions and the receptoric part, were observed. This phenomenon was explained using orbital interactions based on quantum chemical calculations. The selectivity and sensitivity of CT-2 for F-, Cl-, Br-, I-, AcO-, CN-, H2PO4-, HSO4- and ClO4- anions were determined with spectrophotometric, fluorimetric and 1H NMR titration techniques and it was found that CT-2 be utilized for the detection of CN-, F- and AcO- in the presence of other ions as competitors. Color and fluorescence changes visible to the naked eye and under UV (365 nm) were observed upon addition of CN-, F- and AcO- to the solution of chemosensor (CT-2) in DMSO. The sensor showed no colorimetric and fluorimetric response for the anions such as Cl-, Br-, I-, H2PO4-, HSO4-, and ClO4-. However, 1H NMR titration shows that the chemosensor was more sensitive to CN-, than F- and AcO- at the stochiometric ratio of 1:2.5 respectively. Additionally, the compounds CT-1 and CT-2 showed good thermal stability for practical applications.

  12. Evidence for the TICT mediated nonradiative deexcitation process for the excited coumarin-1 dye in high polarity protic solvents

    Energy Technology Data Exchange (ETDEWEB)

    Barik, Atanu [Radiation Chemistry and Chemical Dynamics Division, Bhabha Atomic Research Center, Trombay, Mumbai 400 085 (India); Kumbhakar, Manoj [Radiation Chemistry and Chemical Dynamics Division, Bhabha Atomic Research Center, Trombay, Mumbai 400 085 (India); Nath, Sukhendu [Radiation Chemistry and Chemical Dynamics Division, Bhabha Atomic Research Center, Trombay, Mumbai 400 085 (India); Pal, Haridas [Radiation Chemistry and Chemical Dynamics Division, Bhabha Atomic Research Center, Trombay, Mumbai 400 085 (India)], E-mail: hpal@apsara.barc.ernet.in

    2005-08-29

    Photophysical properties of coumarin-1 (C1) dye in different protic solvents have been investigated using steady-state and time-resolved fluorescence measurements. Correlation of the Stokes' shifts ({delta}{nu}-bar ) with the solvent polarity ({delta}f) suggests the intramolecular charge transfer (ICT) character for the dye fluorescent state. Fluorescence quantum yields ({phi}{sub f}) and lifetimes ({tau}{sub f}) of the dye show an abrupt reduction in high polarity solvents having {delta}f >{approx}0.28. In these solvents {tau}{sub f} is seen to be strongly temperature dependent, though it is temperature independent in solvents with {delta}f <{approx}0.28. It is inferred that in high polarity protic solvents there is a participation of an additional nonradiative decay process via the involvement of twisted intramolecular charge transfer (TICT) state. Unlike present results, no involvement of TICT state was observed even in strongly polar aprotic solvent like acetonitrile. It is indicated that the intermolecular hydrogen bonding of the dye with protic solvents in addition with the solvent polarity helps in the stabilization of the TICT state for C1 dye. Unlike most TICT molecules, the activation barrier ({delta}E{sub a}) for the TICT mediated nonradiative process for C1 dye is seen to increase with solvent polarity. This is rationalized on the basis of the assumption that the TICT to ground state conversion is the activation-controlled rate-determining step for the present system than the usual ICT to TICT conversion as encountered for most other TICT molecules.

  13. DFT modeling and spectroscopic study of metal-ligand bonding in La(III) complex of coumarin-3-carboxylic acid

    Energy Technology Data Exchange (ETDEWEB)

    Mihaylov, Tz. [Institute of General and Inorganic Chemistry, Bulgarian Academy of Sciences, 1113 Sofia (Bulgaria); Trendafilova, N. [Institute of General and Inorganic Chemistry, Bulgarian Academy of Sciences, 1113 Sofia (Bulgaria)], E-mail: ntrend@svr.igic.bas.bg; Kostova, I. [Department of Chemistry, Faculty of Pharmacy, Medical University, Sofia 1000 (Bulgaria); Georgieva, I. [Institute of General and Inorganic Chemistry, Bulgarian Academy of Sciences, 1113 Sofia (Bulgaria); Bauer, G. [Institute of Chemical Technologies and Analytics, Technical University of Vienna, Vienna A-1060 (Austria)

    2006-09-11

    The binding mode of coumarin-3-carboxylic acid (HCCA) to La(III) is elucidated at experimental and theoretical level. The complexation ability of the deprotonated ligand (CCA{sup -}) to La(III) is studied using elemental analysis, DTA and TGA data as well as FTIR, {sup 1}H NMR and {sup 13}C NMR spectra. The experimental data suggest the complex formula La(CCA){sub 2}(NO{sub 3})(H{sub 2}O){sub 2}. B3LYP, BHLYP, B3P86, B3PW91, PW91P86 and MPW1PW91 functionals are tested for geometry and frequency calculations of the neutral ligand and all of them show bond length deviations bellow 1%. B3LYP/6-31G(d) level combined with large quasi-relativistic effective core potential for lanthanum is selected to describe the molecular, electronic and vibrational structures as well as the conformational behavior of HCCA, CCA{sup -} and La-CCA complex. The metal-ligand binding mode is predicted through molecular modeling and energy estimation of different La-CCA structures. The calculated atomic charges and the bonding orbital polarizations point to strong ionic metal-ligand bonding in La-CCA complex and insignificant donor acceptor interaction. Detailed vibrational analysis of HCCA, CCA{sup -} and La(CCA){sub 2}(NO{sub 3})(H{sub 2}O){sub 2} systems based on both calculated and experimental frequencies confirms the suggested metal-ligand binding mode.

  14. Solvent effect on the absorption spectra of coumarin 120 in water: A combined quantum mechanical and molecular mechanical study.

    Science.gov (United States)

    Sakata, Tetsuya; Kawashima, Yukio; Nakano, Haruyuki

    2011-01-07

    The solvent effect on the absorption spectra of coumarin 120 (C120) in water was studied utilizing the combined quantum mechanical∕molecular mechanical (QM∕MM) method. In molecular dynamics (MD) simulation, a new sampling scheme was introduced to provide enough samples for both solute and solvent molecules to obtain the average physical properties of the molecules in solution. We sampled the structure of the solute and solvent molecules separately. First, we executed a QM∕MM MD simulation, where we sampled the solute molecule in solution. Next, we chose random solute structures from this simulation and performed classical MD simulation for each chosen solute structure with its geometry fixed. This new scheme allowed us to sample the solute molecule quantum mechanically and sample many solvent structures classically. Excitation energy calculations using the selected samples were carried out by the generalized multiconfigurational perturbation theory. We succeeded in constructing the absorption spectra and realizing the red shift of the absorption spectra found in polar solvents. To understand the motion of C120 in water, we carried out principal component analysis and found that the motion of the methyl group made the largest contribution and the motion of the amino group the second largest. The solvent effect on the absorption spectrum was studied by decomposing it in two components: the effect from the distortion of the solute molecule and the field effect from the solvent molecules. The solvent effect from the solvent molecules shows large contribution to the solvent shift of the peak of the absorption spectrum, while the solvent effect from the solute molecule shows no contribution. The solvent effect from the solute molecule mainly contributes to the broadening of the absorption spectrum. In the solvent effect, the variation in C-C bond length has the largest contribution on the absorption spectrum from the solute molecule. For the solvent effect on the

  15. Evaluation of Antifungal Activity and Mode of Action of New Coumarin Derivative, 7-Hydroxy-6-nitro-2H-1-benzopyran-2-one, against Aspergillus spp.

    Directory of Open Access Journals (Sweden)

    Felipe Queiroga Sarmento Guerra

    2015-01-01

    Full Text Available Aspergillus spp. produce a wide variety of diseases. For the treatment of such infections, the azoles and Amphotericin B are used in various formulations. The treatment of fungal diseases is often ineffective, because of increases in azole resistance and their several associated adverse effects. To overcome these problems, natural products and their derivatives are interesting alternatives. The aim of this study was to examine the effects of coumarin derivative, 7-hydroxy-6-nitro-2H-1-benzopyran-2-one (Cou-NO2, both alone and with antifungal drugs. Its mode of action against Aspergillus spp. Cou-NO2 was tested to evaluate its effects on mycelia growth and germination of fungal conidia of Aspergillus spp. We also investigated possible Cou-NO2 action on cell walls (0.8 M sorbitol and on Cou-NO2 to ergosterol binding in the cell membrane. The study shows that Cou-NO2 is capable of inhibiting both the mycelia growth and germination of conidia for the species tested, and that its action affects the structure of the fungal cell wall. At subinhibitory concentration, Cou-NO2 enhanced the in vitro effects of azoles. Moreover, in combination with azoles (voriconazole and itraconazole Cou-NO2 displays an additive effect. Thus, our study supports the use of coumarin derivative 7-hydroxy-6-nitro-2H-1-benzopyran-2-one as an antifungal agent against Aspergillus species.

  16. Triazole tethered C5-curcuminoid-coumarin based molecular hybrids as novel antitubulin agents: Design, synthesis, biological investigation and docking studies.

    Science.gov (United States)

    Singh, Harbinder; Kumar, Mandeep; Nepali, Kunal; Gupta, Manish K; Saxena, Ajit K; Sharma, Sahil; Bedi, Preet Mohinder S

    2016-06-30

    Keeping in view the confines allied with presently accessible antitumor agents and success of C5-curcuminoid based bifunctional hybrids as novel antitubulin agnets, molecular hybrids of C5-curcuminoid and coumarin tethered by triazole ring have been synthesized and investigated for in-vitro cytotoxicity against THP-1, COLO-205, HCT-116 and PC-3 human tumor cell lines. The results revealed that the compounds A-2 to A-9, B-2, B-3, B-7 showed significant cytotoxic potential against THP-1, COLO-205 and HCT-116 cell lines, while the PC-3 cell line among these was found to be almost resistant. Structure activity relationship revealed that the nature of Ring X and the length of carbon-bridge (n) connecting triazole ring with coumarin moiety considerably influence the activity. Methoxy substituted phenyl ring as Ring X and two carbon-bridges were found to be the ideal structural features. The most potent compounds (A-2, A-3 and A-7) were further tested for tubulin polymerization inhibition. Compound A-2 was found to significantly inhibit the tubulin polymerization (IC50 = 0.82 μM in THP-1 tumor cells). The significant cytotoxicity and tubulin polymerization inhibition by A-2 was further rationalized by docking studies where it was docked at the curcumin binding site of tubulin.

  17. Fluorescence sensing of phosdrin pesticide by the luminescent Eu(III)- and Tb(III)-bis(coumarin-3-carboxylic acid) probes

    Science.gov (United States)

    Hussein, Belal H. M.; Khairy, Gasser M.; Kamel, Rasha M.

    2016-04-01

    Luminescence quenching of the Eu(III)- and Tb(III)-bis (coumarin-3-carboxylic acid) (Ln(III)-(CCA)2) probes has been studied in the presence of organophosphorus or organochlorine pesticides; Phosdrin (P1), Malathion (P2), Profenofos (P3), Formothion (P4), Heptachlor (P5), and Endosulfan (P6). The luminescence intensity of lanthanide complex probes Ln(III)-(CCA)2 decreases as the concentration of the Phosdrin pesticide increases, while the other investigated pesticides have no significant influence on the lanthanide fluorescent intensities. It is observed that the quenching of Eu(III) and Tb(III)-coumarin-3-carboxylic acid by Phosdrin proceeds via static quenching processes according to Stern-Volmer plot. The binding constants (K) and the thermodynamic parameters of the interaction of Ln(III)-(CCA)2 with Phosdrin have been determined. A direct method for the determination of the Phosdrin in ethanol has been developed based on the luminescence changes of the Ln(III)-(CCA)2-phosdrin ternary complexes. The detection limits of P1 were 6.28 and 1.07 μM in case of Eu(III) and Tb(III)-complex, respectively. The influence of various interfering species on the detection of P1 has been investigated to assess the analytical applicability of the method. The new method was applied to determine the Phosdrin pesticide in different types of water samples.

  18. A Bifunctional Thioether Linked Coumarin Appended Calix[4]arene Acquires Selectivity Toward Cu(2+) Sensing on Going from Solution to SAM on Gold.

    Science.gov (United States)

    Samanta, Kushal; Rao, Chebrolu Pulla

    2016-02-10

    A bifunctional calix[4]arene molecule bearing coumarin moiety on the lower rim and thioether moiety on the upper rim (L1), has been synthesized and well characterized by (1)H, (13)C NMR and mass spectrometry. Suitably functionalized coumarin moieties are well suited for selective recognition of various cations and anions. Among the 10 different metal ions studied, only Cu(2+) and Fe(3+) exhibit appreciable changes in the absorption spectra owing to the availability of functional moieties present at both the lower as well as the upper rim of free L1 in acetonitrile solution. To bring better selectivity, we blocked one of these functional moieties by coating on to a surface so that only the other one is exposed to the environment for sensing. Such a study carried out in the present case using the self-assembled monolayer (SAM) of L1 on Au(111) resulted in selective sensing of Cu(2+) over several other metal ions as studied by surface plasmon resonance (SPR). The SAM of L1 on Au(111) was confirmed by different techniques, such as grazing incidence FT-IR, contact angle measurement, cyclic voltammetry and scanning tunneling microscopy. Thus, L1 is proven to be a suitable sensor for Cu(2+) when attached to gold surface.

  19. Thiol-chromene click chemistry: a coumarin-based derivative and its use as regenerable thiol probe and in bioimaging applications.

    Science.gov (United States)

    Yang, Yutao; Huo, Fangjun; Yin, Caixia; Zheng, Anmin; Chao, Jianbin; Li, Yingqi; Nie, Zongxiu; Martínez-Máñez, Ramón; Liu, Diansheng

    2013-09-15

    The synthesis and characterization of a coumarin-chromene (8, 9-dihydro-2H-cyclopenta[b]pyrano[2,3-f]chromene-2,10(7aH)-dione) (1) derivative and its use for thiol chemosensing in water was reported. Experimental details showed 1 acts as a probe for the detection of thiols including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), whereas amino acids which do not contain thiols induced no changes in UV-vis spectra and fluorescence emission properties of 1. A possible detection mechanism is a nucleophilic attack of thiols to the α,β-unsaturated ketone in 1 that resulted in a fluorescent coumarin derivative. Further studies showed that 1-thiol derivatives can be applied to the design of regenerative chemodosimeters for Cu(2+), Hg(2+) and Cd(2+) in water based on M(n+)-promoted desulfurization and recovery of 1. Furthermore, the optical properties of the probe and its Cys-addition product were theoretically studied. The ability of probe 1 to detect thiols in living cells (HepG2 cells) via an enhancement of the fluorescence was proved. Moreover, the applicability of 1 for the direct determination of biorelevant thiols in a complex matrix such as human plasma was also demonstrated. Copyright © 2013 Elsevier B.V. All rights reserved.

  20. Evaluation of Antifungal Activity and Mode of Action of New Coumarin Derivative, 7-Hydroxy-6-nitro-2H-1-benzopyran-2-one, against Aspergillus spp.

    Science.gov (United States)

    Guerra, Felipe Queiroga Sarmento; de Araújo, Rodrigo Santos Aquino; de Sousa, Janiere Pereira; Pereira, Fillipe de Oliveira; Mendonça-Junior, Francisco J B; Barbosa-Filho, José M; de Oliveira Lima, Edeltrudes

    2015-01-01

    Aspergillus spp. produce a wide variety of diseases. For the treatment of such infections, the azoles and Amphotericin B are used in various formulations. The treatment of fungal diseases is often ineffective, because of increases in azole resistance and their several associated adverse effects. To overcome these problems, natural products and their derivatives are interesting alternatives. The aim of this study was to examine the effects of coumarin derivative, 7-hydroxy-6-nitro-2H-1-benzopyran-2-one (Cou-NO2), both alone and with antifungal drugs. Its mode of action against Aspergillus spp. Cou-NO2 was tested to evaluate its effects on mycelia growth and germination of fungal conidia of Aspergillus spp. We also investigated possible Cou-NO2 action on cell walls (0.8 M sorbitol) and on Cou-NO2 to ergosterol binding in the cell membrane. The study shows that Cou-NO2 is capable of inhibiting both the mycelia growth and germination of conidia for the species tested, and that its action affects the structure of the fungal cell wall. At subinhibitory concentration, Cou-NO2 enhanced the in vitro effects of azoles. Moreover, in combination with azoles (voriconazole and itraconazole) Cou-NO2 displays an additive effect. Thus, our study supports the use of coumarin derivative 7-hydroxy-6-nitro-2H-1-benzopyran-2-one as an antifungal agent against Aspergillus species.