Tan, R.X.
(Institut de Pharmacognosie et Phytochimie, Université)
,
Wolfender, J.-L.
(de Lausanne, B.E.P., CH-1015 Lausanne, Switzerland)
,
Zhang, L.X.
(Institut de Pharmacognosie et Phytochimie, Université)
,
Ma, W.G.
(de Lausanne, B.E.P., CH-1015 Lausanne, Switzerland)
,
Fuzzati, N.
(Institute of Biotechnology, Department of Biological Sciences and Technology, Nanjing University, Nanjing 210093, P. R. China)
,
Marston, A.
(Institut de Pharmacognosie et Phytochimie, Université)
,
Hostettmann, K.
(de Lausanne, B.E.P., CH-1015 Lausanne, Switzerland)
AbstractLC-UV-mass spectrometry and bioassay co-directed fractionation of an aqueous acetone extract of the roots of Gentiana macrophylla gave three new chromene derivatives and two novel and six known secoiridoids, along with kurarinone, kushenol I, β-sitosterol, stigmasterol, daucosterol, &...
AbstractLC-UV-mass spectrometry and bioassay co-directed fractionation of an aqueous acetone extract of the roots of Gentiana macrophylla gave three new chromene derivatives and two novel and six known secoiridoids, along with kurarinone, kushenol I, β-sitosterol, stigmasterol, daucosterol, β-sitosterol-3-O-gentiobioside, α-amyrin, oleanolic acid, isovitexin, gentiobiose and methyl 2-hydroxy-3-(1-β-D-glucopyranosyl)oxybenzoate. The structures of the new products were established from spectral and chemical evidence as 2-methoxyanofinic acid and macrophyllosides A-D. The six known secoiridoids were gentiopicroside, sweroside, 6′-O-β-d-glucosylgentiopicroside, 6′-O-β-d-glucosylsweroside, trifloroside and rindoside. The new acid (2-methoxyanofinic acid), its methyl ester, kurarinone and kushenol I were shown to be active against the plant pathogenic fungus Cladosporium cucumerinum. The methyl ester and kurarinone inhibited also the growth of the human pathogenic yeast Candida albicans. Structure-activity relationships were studied. Thus, addition of a methoxyl group to the benzene nucleus of anofinic acid (2,2-dimethyl-2H-1-benzopyran-6-carboxylic acid) increased the antifungal activity remarkably whereas glycosylation at the carboxylic moiety was found to remove the activity. Esterification of the new acid induced its activity against C. albicans, but decreased its growth inhibition properties against C. cucumerinum. Hydroxylation of kurarinone at the 3β-position removed its activity against C. albicans and decreased the inhibition of C. cucumerinum. In addition, the chemotaxonomic significance of the identified constituents is discussed.
AbstractLC-UV-mass spectrometry and bioassay co-directed fractionation of an aqueous acetone extract of the roots of Gentiana macrophylla gave three new chromene derivatives and two novel and six known secoiridoids, along with kurarinone, kushenol I, β-sitosterol, stigmasterol, daucosterol, β-sitosterol-3-O-gentiobioside, α-amyrin, oleanolic acid, isovitexin, gentiobiose and methyl 2-hydroxy-3-(1-β-D-glucopyranosyl)oxybenzoate. The structures of the new products were established from spectral and chemical evidence as 2-methoxyanofinic acid and macrophyllosides A-D. The six known secoiridoids were gentiopicroside, sweroside, 6′-O-β-d-glucosylgentiopicroside, 6′-O-β-d-glucosylsweroside, trifloroside and rindoside. The new acid (2-methoxyanofinic acid), its methyl ester, kurarinone and kushenol I were shown to be active against the plant pathogenic fungus Cladosporium cucumerinum. The methyl ester and kurarinone inhibited also the growth of the human pathogenic yeast Candida albicans. Structure-activity relationships were studied. Thus, addition of a methoxyl group to the benzene nucleus of anofinic acid (2,2-dimethyl-2H-1-benzopyran-6-carboxylic acid) increased the antifungal activity remarkably whereas glycosylation at the carboxylic moiety was found to remove the activity. Esterification of the new acid induced its activity against C. albicans, but decreased its growth inhibition properties against C. cucumerinum. Hydroxylation of kurarinone at the 3β-position removed its activity against C. albicans and decreased the inhibition of C. cucumerinum. In addition, the chemotaxonomic significance of the identified constituents is discussed.
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Yunnan Zhiwu Yanjiu Liu 16 85 1994
Shoyakugaku Zasshi Kondo 47 942 1993
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