丹参酮的真菌生物转化导致[4+2]环加成与蛇床素醇反应：酶催化和增强抗菌活性的证据。

Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity.

机构信息

Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China.

University of Chinese Academy of Sciences, Beijing, 100049, China.

出版信息

Appl Microbiol Biotechnol. 2016 Oct;100(19):8349-57. doi: 10.1007/s00253-016-7488-6. Epub 2016 May 20.

DOI:10.1007/s00253-016-7488-6

PMID:27198724

Abstract

The biotransformation of tanshinone IIA to a new antibacterial agent tanshisorbicin (1) by the fungus Hypocrea sp. (AS 3.17108) is described. The structure of tanshisorbicin is a hybrid of tanshinone IIA (2) and sorbicillinol (3). The latter is a metabolite produced by Hypocrea sp. The structure of tanshisorbicin was determined using mass spectrometry, NMR spectroscopy, and ECD calculations. The anti-MRSA activity of 1 was found to be significantly higher than that of the parent substrate Tan IIA. Preliminary experiments indicate that tanshisorbicin is formed via a [4+2] cycloaddition reaction that is likely catalyzed by microbial enzyme.

摘要

该文描述了真菌Hypocrea sp.（AS 3.17108）将丹参酮 IIA 生物转化为新型抗菌剂丹参辛（1）。丹参辛的结构是丹参酮 IIA（2）和山梨醇（3）的杂合体。后者是 Hypocrea sp. 产生的代谢物。通过质谱、NMR 光谱和 ECD 计算确定了丹参辛的结构。发现 1 的抗耐甲氧西林金黄色葡萄球菌（MRSA）活性明显高于母体底物 Tan IIA。初步实验表明，丹参辛是通过[4+2]环加成反应形成的，该反应可能由微生物酶催化。