Online analysis of xestodecalactones A-C, novel bioactive metabolites from the fungus Penicillium cf. montanense and their subsequent isolation from the sponge Xestospongia exigua

被引:101
作者
Edrada, RA
Heubes, M
Brauers, G
Wray, V
Berg, A
Gräfe, U
Wohlfarth, M
Mühlbacher, J
Schaumann, K
Sudarsono
Bringmann, G [1 ]
Proksch, P
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Dusseldorf, Inst Pharmazeut Biol, D-40225 Dusseldorf, Germany
[3] Gesell Biotechnol Forsch mbH, D-38124 Braunschweig, Germany
[4] Hans Knoll Inst Naturstofforsch, D-07745 Jena, Germany
[5] Stiftung Alfred Wegener Inst Polar & Meeresforsch, D-27570 Bremerhaven, Germany
[6] Gadjah Mada Univ, Fak Biol, Yogyakarta, Indonesia
来源
JOURNAL OF NATURAL PRODUCTS | 2002年 / 65卷 / 11期
关键词
D O I
10.1021/np020085c
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Fungal isolates of Penicillium cf. montanense were obtained from the marine sponge Xestospongia exigua collected from the Bali Sea, Indonesia. Culture filtrates of the fungi yielded three novel decalactone metabolites, xestodecalactones A, B, and C (1, 2a, and 2b), consisting of 10-membered macrolides with a fused 1,3-dihydroxybenzene ring. Online HPLC-NMR, ESI-MS/MS, and -CD spectra were acquired, and the structures of the new compounds were established and confirmed on the basis of offline NMR spectroscopic (H-1, C-13, COSY, ROESY, H-1-detected direct and long-range C-13-H-1 correlations) and mass spectrometric (EIMS) data. Quantum chemical calculations of the CD spectra proved to be difficult because of the conformational flexibility of the xestodecalactones. These compounds, of which 2a and 2b, due to the additional stereocenter at C-9, are diastereomeric compounds, are structurally related to a number of biologically active metabolites found in terrestrial fungal strains. Compound 2a was found to be active against the yeast Candida albicans.
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页码:1598 / 1604
页数:7
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