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木贼镰刀菌对抑菌剂 2β-甲氧基环烷-9α-醇的代谢产物。

Metabolites of the fungistatic agent 2β-methoxyclovan-9α-ol by Macrophomina phaseolina.

机构信息

HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan.

出版信息

J Agric Food Chem. 2011 Apr 13;59(7):3234-8. doi: 10.1021/jf104314f. Epub 2011 Mar 10.

DOI:10.1021/jf104314f
PMID:21391597
Abstract

Biotransformation of 2β-methoxyclovan-9α-ol (1), a fungistatic agent against Botrytis cinerea, was investigated with Macrophomina phaseolina. Demethoxylation, regioselective oxidation at C-9 and C-13, and inversion of the configuration at C-9 of compound 1 afforded six oxidative metabolites, 2β-methoxyclovan-9-one (2), clovan-2β,9β-diol (3), clovan-2β,9α-diol (4), clovan-2β,13-diol-9-one (5), 2β-methoxyclovan-9α,13-diol (6), and clovan-2β,9β,13-triol (7). Compounds 5-7 are described here for the first time, and their structures were deduced by different spectroscopic techniques. The antifungal activity of new metabolites 5-7 was also evaluated against B. cinerea.

摘要

用木贼镰刀菌(Macrophomina phaseolina)研究了具有抗灰葡萄孢(Botrytis cinerea)活性的 2β-甲氧基环伐醇(1)的生物转化。化合物 1 的脱甲氧基、C-9 和 C-13 的区域选择性氧化以及 C-9 构型的反转生成了六个氧化代谢物,2β-甲氧基环伐酮(2)、克洛万-2β,9β-二醇(3)、克洛万-2β,9α-二醇(4)、克洛万-2β,13-二醇-9-酮(5)、2β-甲氧基环伐醇-9α,13-二醇(6)和克洛万-2β,9β,13-三醇(7)。化合物 5-7 为首次在此报道,其结构通过不同的光谱技术推导得出。还评估了新代谢物 5-7 对灰葡萄孢的抗真菌活性。

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