Chemical Studies on Mexican Plants Used in Traditional Medicine, VI. Additional New 4-Phenylcoumarins from Exostema caribaeum

Mata, Rachel; Calzada, Fernando; García, María del Rosario

doi:10.1021/np50059a006

Cited by 34 publications

(20 citation statements)

References 6 publications

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“…Previous reports indicated that 5,7-dimethoxy-4-pmethoxylphenylcoumarin was produced by numerous species of plants, including Hintonia latiflora (Mata et al, 1990), Exostema caribaeum (Mata et al, 1988) and Coutarea hexandra (Delle Monache et al, 1983), but nothing is known about its activity. Our study is the first in which 5,7-dimethoxy-4-p-methoxylphenylcoumarin from culture filtrates of an endophytic Streptomyces species was isolated from the root tissue of Z. officinale.…”

Section: Discussionmentioning

confidence: 99%

Secondary metabolites from endophytic Streptomyces aureofaciens CMUAc130 and their antifungal activity

et al. 2005

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Streptomyces aureofaciens CMUAc130 was isolated from the root tissue of Zingiber officinale Rosc. (Zingiberaceae). It was an antagonist of Colletotrichum musae and Fusarium oxysporum, the causative agents of anthracnose of banana and wilt of wheat, respectively. Evidence for the in vitro antibiosis of S. aureofaciens CMUAc130 was demonstrated by the zone of fungal-growth inhibition. Microscopic observations showed thickness and bulbous structures at the edges of the inhibited fungal hyphae. The culture filtrate and crude extract from this strain were all inhibitory to tested phytopathogenic fungi. The major active ingredients from the culture filtrate of S. aureofaciens CMUAc130 were purified by silica gel-column chromatography and identified to be (i) 5,7-dimethoxy-4-p-methoxylphenylcoumarin and (ii) 5,7-dimethoxy-4-phenylcoumarin by NMR and mass-spectral data, respectively. Bioassay studies showed that compounds (i) and (ii) had antifungal activities against tested fungi, and their MICs were found to be 120 and 150 mg ml "1 , respectively. This is the first report of compounds (i) and (ii) from micro-organisms as active ingredients for the control of phytopathogenic fungi.

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Section: Discussionmentioning

confidence: 99%

Secondary metabolites from endophytic Streptomyces aureofaciens CMUAc130 and their antifungal activity

et al. 2005

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“…Hypoglycemic and antimalarial 4-Phenylcoumarins Sanchez-Viesca (1969), Mata et al (1987Mata et al ( , 1988, Noster and Kraus (1990), Pinto et al (1997) and Slijepcevic et al (1997). Gnaphalium sp.…”

Section: Introductionmentioning

confidence: 99%

Acute toxicity and mutagenic activity of Mexican plants used in traditional medicine

Déciga-Campos

Rivero‐Cruz

Arriaga-Alba

et al. 2007

Journal of Ethnopharmacology

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182

106

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“…Even with 2D NMR it was not possible to assign exactly the quaternary carbons C-4, C-4a, and C-8a, and the position of the phenyl ring. These positions had to be assigned by comparing the shifts with literature data (10), (11), (12). Compounds with a phenyl substituent at C-4 show 13 C-shifts of 112 ± 114 ppm for C-3 and 155 ± 156 ppm for C-4 (10), (11), (12), while a substituent at C-3 shows 13 C-shifts of 122 ppm for C-3 and 139 ppm for C-4 (13).…”

Section: Resultsmentioning

confidence: 99%

Bioactive Coumarin Derivatives from the Fern Cyclosorus interruptus

Quadri-Spinelli

Heilmann²,

Rali³

et al. 2000

Planta med

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Three new coumarin derivatives, compounds 1-3, three new furanocoumarins, compounds 4-6, and a novel dioxocane derivative, compound 7, were isolated from the fern Cyclosorus interruptus (Willd.) H. Itô. Based on spectrometric and spectroscopic analysis (FAB or El mass spectrometry as well as 1D and 2D NMR experiments) their structures were characterised as 5,7-dihydroxy-6-methyl-4-phenyl-8-(3-phenylpropionyl)-1-benzopyran-2-one (1), 5,7-dihydroxy-6-methyl-4-phenyl-8-(3-phenyl-trans-acryloyl)-1- benzopyran-2-one (2), 5,7-dihydroxy-8-(2-hydroxy-3-phenylpropionyl)-6-methyl-4-phenyl-1- benzopyran-2-one (3), 8-benzyl-5,8-dihydroxy-6-methyl-4-phenylfuro[2,3-h]-1-benzopyran-2,9- dione (4), 8-benzyl-5,8 beta,9 beta-trihydroxy-6-methyl-4-phenyl-8,9-dihydro- furo[2,3-h]-1-benzopyran-2-one (5), 8-benzyl-5,8 beta,9 alpha-trihydroxy-6-methyl-4-phenyl-8,9-dihydro- furo[2,3-h]-1-benzopyran-2-one (6) and 5,11-dihydroxy-6-methyl-4-phenyl-11-(1-phenylmethyl)-7,10-dioxocane [5,6-h]-1-benzopyran-2,12-dione (7). For these compounds we propose the trivial names interruptins A-F. Compounds 1, 5/6 and 7 showed antibacterial activity while compounds 1 and 2 were cytotoxic to a KB cell line.

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Chemical Studies on Mexican Plants Used in Traditional Medicine, VI. Additional New 4-Phenylcoumarins from Exostema caribaeum

Cited by 34 publications

References 6 publications

Secondary metabolites from endophytic Streptomyces aureofaciens CMUAc130 and their antifungal activity

Secondary metabolites from endophytic Streptomyces aureofaciens CMUAc130 and their antifungal activity

Acute toxicity and mutagenic activity of Mexican plants used in traditional medicine

Bioactive Coumarin Derivatives from the Fern Cyclosorus interruptus

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