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255 KiB

Open AccessArticle

Preparation of Dry Extract of Mikania glomerata Sprengel (Guaco) and Determination of Its Coumarin Levels by Spectrophotometry and HPLC-UV

by Luciana Soares e Silva, Luciane Santos da Silva, Larissa Brumano, Paulo César Stringheta, Miriam Aparecida de Oliveira Pinto, Leticia Oliveira Moreira Dias, Camila De Sá Martins Muller, Elita Scio, Rodrigo Luiz Fabri, Helena C. Castro and Maria Da Penha Henriques do Amaral

Molecules 2012, 17(9), 10344-10354; https://doi.org/10.3390/molecules170910344 - 29 Aug 2012

Cited by 17 | Viewed by 10104

Abstract

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 [...] Read more.

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. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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247 KiB

Open AccessArticle

Two New Coumarins from Micromelum falcatum with Cytotoxicity and Brine Shrimp Larvae Toxicity

by Xiongming Luo, Weihong He, Hao Yin, Qingxin Li, Qiao Liu, Yongzhong Huang and Si Zhang

Molecules 2012, 17(6), 6944-6952; https://doi.org/10.3390/molecules17066944 - 6 Jun 2012

Cited by 13 | Viewed by 5846

Abstract

Two new coumarins, 7-methoxy-8-(2-hydroxmethyl-1-O-isovaleryl-4-butenyl)-coumarin (1) and 7-methoxy-8-(1-hydroxy-2-O-b-glucopyranosyl-3-methyl-4-butene-1-yl)coumarin (2), and twelve known coumarins 3–14 were isolated from the stem bark of Micromelum falcatum. The structures of compounds 1–14 were elucidated by extensive spectroscopic data analyses. The toxicity of [...] Read more.

Two new coumarins, 7-methoxy-8-(2-hydroxmethyl-1-O-isovaleryl-4-butenyl)-coumarin (1) and 7-methoxy-8-(1-hydroxy-2-O-b-glucopyranosyl-3-methyl-4-butene-1-yl)coumarin (2), and twelve known coumarins 3–14 were isolated from the stem bark of Micromelum falcatum. The structures of compounds 1–14 were elucidated by extensive spectroscopic data analyses. The toxicity of compounds 1–14 was tested using a brine shrimp assay and in vitro antiproliferative assay against mammary cancer (F10) and lung cancer (HvEvc) cell lines by the MTT method. Some compounds had moderate activities. All compounds were also tested against the microorganisms Bacillus subtilis, Bacillus thuringiensis and Escherichia coli, but no activity was observed. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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384 KiB

Open AccessArticle

Enantioseparation and Absolute Configuration Determination of Angular-Type Pyranocoumarins from Peucedani Radix Using Enzymatic Hydrolysis and Chiral HPLC-MS/MS Analysis

by Yue-Lin Song, Qing-Wen Zhang, Ya-Ping Li, Ru Yan and Yi-Tao Wang

Molecules 2012, 17(4), 4236-4251; https://doi.org/10.3390/molecules17044236 - 10 Apr 2012

Cited by 44 | Viewed by 8582

Abstract

Angular-type pyranocoumarins from Peucedani Radix (Chinese name: Qian-hu) have exhibited potential for use on treatment of cancer and pulmonary hypertension. Due to the existence of C-3′ and C-4′ chiral centers, compounds belonging to this chemical type commonly exist in enantiomers and/or diastereoisomers, which [...] Read more.

Angular-type pyranocoumarins from Peucedani Radix (Chinese name: Qian-hu) have exhibited potential for use on treatment of cancer and pulmonary hypertension. Due to the existence of C-3′ and C-4′ chiral centers, compounds belonging to this chemical type commonly exist in enantiomers and/or diastereoisomers, which may elicit distinct activities during their interactions with the human body. In the present study, a new method, which combines enzymatic hydrolysis with chiral LC-MS/MS analysis, has been developed to determine the absolute configurations of these angular-type pyranocoumarins. Pyranocoumarins isolated from Qian-hu, their enantiomers, or metabolites were individually incubated with rat liver microsomes. As the common end product from enzymatic hydrolysis of all tested pyranocoumarins, cis-khellactone was collected and its absolute configuration was determined by comparison with (+)-cis-khellactone and (−)-cis-khellactone using chiral LC-MS/MS. The absolute configurations of all tested parent pyranocoumarins were determined by combination of LC-MS/MS, NMR and polarimetric analysis. The results revealed that the metabolite cis-khellactone retained the same absolute configurations of the stereogenic carbons as the respective parent compound. This method was proven to be rapid and sensitive and also has advantages in discriminating single enantiomers and mixtures of optical isomers with different ratios. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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249 KiB

Open AccessArticle

Pressurized Liquid Extraction of Coumarins from Fruits of Heracleum leskowii with Application of Solvents with Different Polarity under Increasing Temperature

by Krystyna Skalicka-Woźniak and Kazimierz Głowniak

Molecules 2012, 17(4), 4133-4141; https://doi.org/10.3390/molecules17044133 - 5 Apr 2012

Cited by 32 | Viewed by 8577

Abstract

Coumarins are nowadays an important group of organic compounds from natural sources that are useful in a number of fields. Because they possess different pharmacological properties, finding the proper extraction conditions for their separation from plant matrices is a very important step. In [...] Read more.

Coumarins are nowadays an important group of organic compounds from natural sources that are useful in a number of fields. Because they possess different pharmacological properties, finding the proper extraction conditions for their separation from plant matrices is a very important step. In this report Pressurized Liquid Extraction (PLE) under different temperature conditions and with different types of extraction solvents were tested. As a matrix, fruits of Heracleum leskowii have been used. A simple reverse phase high-performance liquid chromatographic method (RP-HPLC) coupled with a photodiode array detector (DAD) has been developed for separation and quantitative analysis of the main coumarins. Umbelliferone, xanthotoxin, angelicin, isopimpinellin, bergapten, imperatorin and isoimperatorin were investigated. Bergapten and imperatorin were dominant in almost all extracts in the range of 9.92 ± 0.02–20.93 ± 0.06 and 12.19 ± 0.98–19.07 ± 0.03 mg/100 g, respectively. Dichloromethane and methanol were chosen as the most proper suitable solvents for extraction of coumarins. By increasing the temperature the amount of extracted coumarins increases in petroleum ether and dichloromethane extracts. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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267 KiB

Open AccessArticle

Soulamarin, a New Coumarin from Stem Bark of Calophyllum soulattri

by Gwendoline Cheng Lian Ee, Siau Hui Mah, Soek Sin Teh, Mawardi Rahmani, Rusea Go and Yun Hin Taufiq-Yap

Molecules 2011, 16(11), 9721-9727; https://doi.org/10.3390/molecules16119721 - 23 Nov 2011

Cited by 36 | Viewed by 6524

Abstract

The extracts of the stem bark of Calophyllum soulattri gave a new pyranocoumarin, soulamarin (1), together with five other xanthones caloxanthone B (2), caloxanthone C (3), macluraxanthone (4), trapezifolixanthone (5) and brasixanthone B [...] Read more.

The extracts of the stem bark of Calophyllum soulattri gave a new pyranocoumarin, soulamarin (1), together with five other xanthones caloxanthone B (2), caloxanthone C (3), macluraxanthone (4), trapezifolixanthone (5) and brasixanthone B (6) one common triterpene, friedelin (7), and the steroidal triterpene stigmasterol (8). The structures of these compounds were established based on spectral evidence (1D and 2D NMR). Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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492 KiB

Open AccessArticle

A Novel Cyclodione Coumarin from the Stem Bark of Mesua beccariana

by Gwendoline Cheng Lian Ee, Soek Sin Teh, Siau Hui Mah, Mawardi Rahmani, Yun Hin Taufiq-Yap and Khalijah Awang

Molecules 2011, 16(9), 7249-7255; https://doi.org/10.3390/molecules16097249 - 25 Aug 2011

Cited by 7 | Viewed by 5424

Abstract

Our ongoing investigations on the stem bark of Mesua beccariana afforded a novel cyclodione coumarin, beccamarin, together with two known xanthones, mesuarianone, mesuasinone, two anthraquinones, 4-methoxy-1,3,5-trihydroxy-anthraquinone and 2,5-dihydroxy-1,3,4-trimethoxyanthraquinone and one coumarin, mammea A/AB. The structures were elucidated by 1D and 2D NMR [...] Read more.

Our ongoing investigations on the stem bark of Mesua beccariana afforded a novel cyclodione coumarin, beccamarin, together with two known xanthones, mesuarianone, mesuasinone, two anthraquinones, 4-methoxy-1,3,5-trihydroxy-anthraquinone and 2,5-dihydroxy-1,3,4-trimethoxyanthraquinone and one coumarin, mammea A/AB. The structures were elucidated by 1D and 2D NMR and MS techniques. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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199 KiB

Open AccessArticle

Electrochemical Reduction of Coumarins at a Film-Modified Electrode and Determination of Their Levels in Essential Oils and Traditional Chinese Herbal Medicines

by Lai-Hao Wang and Hsiu-Hua Liu

Molecules 2009, 14(9), 3538-3550; https://doi.org/10.3390/molecules14093538 - 11 Sep 2009

Cited by 24 | Viewed by 9263

Abstract

The electrochemical reduction of coumarins on glassy carbon and electrodeposited metal electrodes was investigated in a Britton-Robinson buffer (pH 1.87-11.98). The effects of various factors, such as the deposition material, time, and concentration of mercury, on the precision of the analysis were explored. [...] Read more.

The electrochemical reduction of coumarins on glassy carbon and electrodeposited metal electrodes was investigated in a Britton-Robinson buffer (pH 1.87-11.98). The effects of various factors, such as the deposition material, time, and concentration of mercury, on the precision of the analysis were explored. The possible reaction mechanism of the reduction process with regards to scan rates, peak potentials, and currents is discussed. Electroreduction was used to quantitatively determine the levels of coumarins in some essential oils and traditional Chinese herbal medicines. A comparison with high performance liquid chromatography analysis results shows good agreement. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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212 KiB

Open AccessArticle

Coumarins from Angelica Lucida L. - Antibacterial Activities

by Jaroslaw Widelski, Milena Popova, Konstantia Graikou, Kazimierz Glowniak and Ioanna Chinou

Molecules 2009, 14(8), 2729-2734; https://doi.org/10.3390/molecules14082729 - 27 Jul 2009

Cited by 63 | Viewed by 14841

Abstract

The first phytochemical investigation of the fruits of Angelica lucida has led to the isolation and characterization of five known coumarins (imperatorin, isoimperatorin, heraclenol, oxypeucedanin hydrate and heraclenin). All isolated compounds were identified by means of spectral and literature data. The extracts and [...] Read more.

The first phytochemical investigation of the fruits of Angelica lucida has led to the isolation and characterization of five known coumarins (imperatorin, isoimperatorin, heraclenol, oxypeucedanin hydrate and heraclenin). All isolated compounds were identified by means of spectral and literature data. The extracts and the isolated constituents from A. lucida have been also evaluated for their antimicrobial activity against six Gram positive and negative bacteria, two oral pathogens and three human pathogenic fungi, exhibiting an interesting antimicrobial profile. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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243 KiB

Open AccessArticle

Tyrosinase Inhibitor Activity of Coumarin-Resveratrol Hybrids

by Antonella Fais, Marcella Corda, Benedetta Era, M. Benedetta Fadda, Maria Joao Matos, Elias Quezada q, Lourdes Santana, Carmen Picciau, Gianni Podda and Giovanna Delogu

Molecules 2009, 14(7), 2514-2520; https://doi.org/10.3390/molecules14072514 - 13 Jul 2009

Cited by 66 | Viewed by 16676

Abstract

In the present work we report on the contribution of the coumarin moiety to tyrosinase inhibition. Coumarin-resveratrol hybrids 1-8 have been resynthesized to investigate the structure-activity relationships and the IC₅₀ values of these compounds were measured. The results showed that these compounds [...] Read more.

In the present work we report on the contribution of the coumarin moiety to tyrosinase inhibition. Coumarin-resveratrol hybrids 1-8 have been resynthesized to investigate the structure-activity relationships and the IC₅₀ values of these compounds were measured. The results showed that these compounds exhibited tyrosinase inhibitory activity. Compound 3-(3’,4’,5’-trihydroxyphenyl)-6,8-dihydroxycoumarin (8)is the most potentcompound (0.27 mM), more so than umbelliferone (0.42 mM), used as reference compound. The kinetic studies revealed that compound 8 caused non-competitive tyrosinase inhibition. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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248 KiB

Open AccessArticle

Pseudo-cyclic Face-to-face Rigid Structure Caused by the Intramolecular Ion Pair Effect

by Sheng-Ling Zhang, Zhi-Shu Huang and Lian-Quan Gu

Molecules 2009, 14(4), 1546-1560; https://doi.org/10.3390/molecules14041546 - 14 Apr 2009

Cited by 1 | Viewed by 10125

Abstract

Six 3-methylpyridine zwitterions and six quinoline zwitterions were synthesized through the reaction of 4-hydroxycoumarins, p-benzoquinone and the corresponding N-aromatics. The novel pseudo-cyclic face-to-face rigid structure of the zwitterion was elucidated by ¹H-NMR at different temperatures, and assumed to be caused [...] Read more.

Six 3-methylpyridine zwitterions and six quinoline zwitterions were synthesized through the reaction of 4-hydroxycoumarins, p-benzoquinone and the corresponding N-aromatics. The novel pseudo-cyclic face-to-face rigid structure of the zwitterion was elucidated by ¹H-NMR at different temperatures, and assumed to be caused by both the intramolecular ion pair attraction and the steric interaction. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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253 KiB

Open AccessArticle

Synthesis and Molecular Descriptor Characterization of Novel 4-Hydroxy-chromene-2-one Derivatives as Antimicrobial Agents

by Milan Mladenović, Nenad Vuković, Neda Nićiforović, Slobodan Sukdolak and Slavica Solujić

Molecules 2009, 14(4), 1495-1512; https://doi.org/10.3390/molecules14041495 - 14 Apr 2009

Cited by 47 | Viewed by 12312

Abstract

Several novel 4-hydroxy-chromene-2-one derivatives 2b-16b were easily prepared through condensation reactions with microwave heating and characterized by elemental analysis, IR, ¹H-NMR and mass spectrometry. Geometry optimization of these compounds was executed by PM3, PM5 and Minimize Energy methods to describe them via [...] Read more.

Several novel 4-hydroxy-chromene-2-one derivatives 2b-16b were easily prepared through condensation reactions with microwave heating and characterized by elemental analysis, IR, ¹H-NMR and mass spectrometry. Geometry optimization of these compounds was executed by PM3, PM5 and Minimize Energy methods to describe them via molecular descriptors. The antimicrobial activity of the synthesized compounds was evaluated against different microbial strains using two different methods: the diffusion method and the micro-dilution method. All data indicated that the products possess antimicrobial activity which depends on the nature of substituent attached to the benzopyran moiety. In general, after 24 h the MIC values of most tested coumarins was 0.13 mg/mL, but compounds 1 and 6b displayed the strongest antimicrobial activity on the tested cultures of bacteria after 48 h. Compound 13b has the strongest growth inhibitory potential on fungus C. albicans, tested by diffusion method,with an inhibition zone of 30-37 mm at a concentration of 150 µg/mL. The conclusion of this experiment is that the synthesized compounds have varied and different influence on different classes of bacteria and the fungus C. albicans. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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293 KiB

Open AccessArticle

Evaluation of Photoluminescence Properties of Some Poly(ethylene glycol) – Supported Coumarin Derivatives

by Graziella Tocco, Carlo Maria Carbonaro, Gabriele Meli and Gianni Podda

Molecules 2009, 14(3), 1044-1055; https://doi.org/10.3390/molecules14031044 - 5 Mar 2009

Cited by 9 | Viewed by 13054

Abstract

The immobilization of some coumarin derivatives on modified poly(ethylene glycol)s is reported and the influence of the polymeric support on the photoluminescence activity of the compounds is discussed. Upon ultraviolet excitation, the derivatives showed coumarin - related emission properties whose peak position and [...] Read more.

The immobilization of some coumarin derivatives on modified poly(ethylene glycol)s is reported and the influence of the polymeric support on the photoluminescence activity of the compounds is discussed. Upon ultraviolet excitation, the derivatives showed coumarin - related emission properties whose peak position and efficiency depended on the loading of the polymer and on the mesomeric effects of the substituents. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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202 KiB

Open AccessArticle

Antimicrobial and Antioxidant Activities of Coumarins from the Roots of Ferulago campestris (Apiaceae)

by Adriana Basile, Sergio Sorbo, Vivienne Spadaro, Maurizio Bruno, Antonella Maggio, Nicoletta Faraone and Sergio Rosselli

Molecules 2009, 14(3), 939-952; https://doi.org/10.3390/molecules14030939 - 27 Feb 2009

Cited by 224 | Viewed by 18770

Abstract

We report the isolation of several coumarins and the stereochemical assessment of some pyranocoumarins, as well as the antibacterial and antioxidant activities of the three most abundant ones (grandivittin, agasyllin and aegelinol benzoate) isolated from the roots of Ferulago campestris collected in Sicily [...] Read more.

We report the isolation of several coumarins and the stereochemical assessment of some pyranocoumarins, as well as the antibacterial and antioxidant activities of the three most abundant ones (grandivittin, agasyllin and aegelinol benzoate) isolated from the roots of Ferulago campestris collected in Sicily and of the hydrolysis product (aegelinol). Aegelinol and agasyllin showed antibacterial activity against nine ATCC and the same clinically isolated Gram-positive and Gram-negative bacterial strains. At a concentration between 16 and 125 mg/mL both coumarins showed a significant antibacterial effect against both Gram-negative and Gram-positive bacteria. In particular the ATCC strains Staphylococcus aureus, Salmonella thypii, Enterobacter cloacae and Enterobacter earogenes (MIC = 16 and 32 mg/mL for aegelinol and agasyllin, respectively) were the most inhibited. Antibacterial activity was also found against Helicobacter pylori: a dose-dependent inhibition was shown between 5 and 25 mg/mL. The antioxidant activity of the coumarins was evaluated by their effects on human whole blood leukocytes (WB) and on isolated polymorphonucleate (PMN) chemiluminescence (CL), PMA-stimulated and resting. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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119 KiB

Open AccessArticle

A New O-Terpenoidal Coumarin from Clausena anisum-olens Merr.

by Yun-Song Wang, Hong-Yi Xu, Da-Xiang Wang and Jing-Hua Yang

Molecules 2009, 14(2), 771-776; https://doi.org/10.3390/molecules14020771 - 13 Feb 2009

Cited by 9 | Viewed by 13076

Abstract

A new O-terpenoidal coumarin 1, named hekumarone, was isolated from the leaves and twigs of Clausena anisum-olens Merr.(Rutaceae) collected in Hekou County in Yunnan Province, P. R. China. Structure elucidation and unambiguous NMR assignments for the title compound was carried out on [...] Read more.

A new O-terpenoidal coumarin 1, named hekumarone, was isolated from the leaves and twigs of Clausena anisum-olens Merr.(Rutaceae) collected in Hekou County in Yunnan Province, P. R. China. Structure elucidation and unambiguous NMR assignments for the title compound was carried out on the basis of 1D and 2D NMR experiments. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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Review

Jump to: Research

563 KiB

Open AccessReview

Supramolecular Photodimerization of Coumarins

by Koichi Tanaka

Molecules 2012, 17(2), 1408-1418; https://doi.org/10.3390/molecules17021408 - 3 Feb 2012

Cited by 31 | Viewed by 7509

Abstract

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. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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224 KiB

Open AccessReview

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

by Brian D. Wagner

Molecules 2009, 14(1), 210-237; https://doi.org/10.3390/molecules14010210 - 6 Jan 2009

Cited by 355 | Viewed by 27425

Abstract

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 [...] Read more.

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. Full article

(This article belongs to the Special Issue Coumarins and Xanthones)

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