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

Wenni He; Miaomiao Liu; Xiaolin Li; Xiaoping Zhang; Wael M Abdel-Mageed; Li Li; Wenzhao Wang; Jingyu Zhang; Jianying Han; Huanqin Dai; Ronald J Quinn; Hung-Wen Liu; Houwei Luo; Lixin Zhang; Xueting Liu

doi:10.1007/s00253-016-7488-6

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

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Peer reviewed

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

Wenni He, Miaomiao Liu, Xiaolin Li, Xiaoping Zhang, Wael M Abdel-Mageed, Li Li, Wenzhao Wang, Jingyu Zhang, Jianying Han, Huanqin Dai, …

Applied microbiology and biotechnology, Vol.100(19), pp.8349-8357

01/10/2016

DOI: https://doi.org/10.1007/s00253-016-7488-6

PMID: 27198724

Abstract

Anti-Infective Agents - chemistry

Anti-Infective Agents - metabolism

Biotransformation

Cycloaddition Reaction

Cyclohexanones - chemistry

Cyclohexanones - metabolism

Diterpenes, Abietane - metabolism

Mass Spectrometry

Methicillin-Resistant Staphylococcus aureus - drug effects

Microbial Sensitivity Tests

Models, Molecular

Molecular Structure

Trichoderma - metabolism

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.

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Title: Fungal biotransformation of tanshinone results in [4+2] cycloaddition with sorbicillinol: evidence for enzyme catalysis and increased antibacterial activity
Creators - without role: Wenni He - Institute of Microbiology
Miaomiao Liu - University of Chinese Academy of Sciences
Xiaolin Li - Sichuan Academy of Agricultural Sciences
Xiaoping Zhang - Sichuan Agricultural University
Wael M Abdel-Mageed - King Saud University
Li Li - Chinese Academy of Medical Sciences & Peking Union Medical College
Wenzhao Wang - Institute of Microbiology
Jingyu Zhang - Institute of Microbiology
Jianying Han - University of Chinese Academy of Sciences, Beijing, 100049, China
Huanqin Dai - Institute of Microbiology
Ronald J Quinn - Griffith University
Hung-Wen Liu - The University of Texas at Austin
Houwei Luo - Department of Natural Products, China Pharmaceutical University, Nanjing, 210009, China
Lixin Zhang - Institute of Microbiology
Xueting Liu - Institute of Microbiology
Publication Details: Applied microbiology and biotechnology, Vol.100(19), pp.8349-8357
Identifiers: 9946751608331
Academic Unit: King Saud University
Language: English
Resource Type: Journal article