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盾叶鬼臼和淡紫拟青霉对芳基四氢萘酮和芳基四氢萘类木脂素的微生物转化。

Microbial transformations of aryltetralone and aryltetralin lignans by Cunninghamella echinulata and Beauveria bassiana.

机构信息

SW Center for Natural Products Research and Commercialization, Office of Arid Lands Studies, School of Natural Resources and the Environment, College of Agriculture and Life Sciences, University of Arizona, 250 E. Valencia Road, Tucson, Arizona 85706-6800, United States.

出版信息

J Nat Prod. 2010 Nov 29;73(11):1933-7. doi: 10.1021/np100607s. Epub 2010 Oct 20.

Abstract

Microbiological transformation of the aryltetralone lignan (-)-8'-epi-aristoligone (1) with Cunninghamella echinulata ATCC 10028B afforded two known natural lignans, (-)-holostyligone (3) and (-)-arisantetralone (4). Incubation of the aryltetralin lignan (-)-isogalbulin (2), obtained by chemical transformation of 1, with C. echinulata ATCC 10028B afforded the known lignan aryltetralol (5) and seven new metabolites, (-)-8-hydroxyisogalbulin (6), (-)-7-methoxyisogalbulin (7), (-)-4'-O-demethyl-8-hydroxyisogalbulin (8), (-)-7-methoxy-8-hydroxyisogalbulin (9), (-)-4'-O-demethyl-7-methoxyisogalbulin (10), (-)-4',5-O-didemethylcyclogalgravin (11), and (-)-4'-O-demethylcyclogalgravin (12). When 2 was subjected to biotransformation with Beauveria bassiana ATCC 7159, (-)-8-hydroxyisogalbulin (6) was the only isolable product. The structures of all new compounds were established by detailed analysis of their spectroscopic data.

摘要

用卷枝毛霉(Cunninghamella echinulata)ATCC 10028B 对芳基四氢萘木脂素(-)-8'-表aristoligone(1)进行微生物转化,得到两种已知的天然木脂素,(-)-holostyligone(3)和(-)-arisantetralone(4)。用 C. echinulata ATCC 10028B 对芳基四氢萘木脂素(-)-异橄榄脂素(2)进行化学转化得到的芳基四氢萘木脂素,得到已知的木脂素 aryltetralol(5)和七种新代谢物,(-)-8-羟基异橄榄脂素(6),(-)-7-甲氧基异橄榄脂素(7),(-)-4'-O-去甲基-8-羟基异橄榄脂素(8),(-)-7-甲氧基-8-羟基异橄榄脂素(9),(-)-4'-O-去甲基-7-甲氧基异橄榄脂素(10),(-)-4',5-O-二去甲基环橄榄木脂素(11)和(-)-4'-O-去甲基环橄榄木脂素(12)。当 2 用淡紫拟青霉(Beauveria bassiana)ATCC 7159 进行生物转化时,(-)-8-羟基异橄榄脂素(6)是唯一可分离的产物。所有新化合物的结构均通过其光谱数据的详细分析确定。

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