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黄曲霉 Aspergillus flavipes QCS12 中四种具有全新碳骨架的 merocytochalasans:aspergilasines A-D。

Aspergilasines A-D: Four Merocytochalasans with New Carbon Skeletons from Aspergillus flavipes QCS12.

机构信息

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology , Wuhan 430030, China.

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650204, China.

出版信息

Org Lett. 2017 Aug 18;19(16):4399-4402. doi: 10.1021/acs.orglett.7b02146. Epub 2017 Aug 7.

DOI:10.1021/acs.orglett.7b02146
PMID:28783364
Abstract

Aspergilasines A-D (1-4), four merocytochalasans with new skeletons, were isolated from the liquid culture broth of Aspergillus flavipes QCS12. Aspergilasine A (1) possesses a uniquely caged pentacyclo[7.2.0.1.0.0]dodecane skeleton with an unexpected cyclobutane ring that formed by the fusion of two epicoccine moieties via two [3 + 2] cycloadditions. Aspergilasines B-D (2-4) are key biosynthetic intermediates of epicochalasine B that fit well with our previous biosynthetic proposal.

摘要

黄曲霉毒素 A-D(1-4),四种具有新骨架的单环倍半萜生物碱,从黄曲霉 QCS12 的液体培养物中分离得到。黄曲霉毒素 A(1)具有独特的笼状五环[7.2.0.1.0.0]十二烷骨架,其中一个意想不到的环丁烷环是通过两个 epicoccine 部分通过两个 [3 + 2] 环加成融合形成的。黄曲霉毒素 B-D(2-4)是 epicochalasine B 的关键生物合成中间体,与我们之前的生物合成假设相符。

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