Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity
Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity
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丹参酮的真菌生物转化导致[4 2]与山梨西林醇的环加成：酶催化和抗菌活性增加的证据
DOI：
10.1007/s00253-016-7488-6
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发表时间：
2016-10-01
影响因子：
5
通讯作者：
Liu, Xueting
中科院分区：
文献类型：
--
作者：
He, Wenni;Liu, Miaomiao;Liu, Xueting
本文报道了一株肉座菌（Hypocreasp.）（AS 3.17108）对丹参酮Ⅱ A的生物转化作用。丹参素的结构是丹参酮IIA（2）和山梨醇（3）的杂合物。后者是由肉座菌属产生的代谢产物。使用质谱法、NMR光谱法和ECD计算确定了丹参素的结构。发现1的抗MRSA活性显著高于母体底物Tan IIA。初步实验表明，丹参素可能是通过微生物酶催化的[4+2]环加成反应形成的。
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.