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

Faculty of Pharmacy

Assiut University

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

Research Authors
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.
Research Department
Department of Pharmacognosy
Research Journal
Applied Microbiology and Biotechnology
Research Publisher
Springer
Research Rank
1
Research Vol
Volume 100, Issue 19
Research Website
http://link.springer.com/article/10.1007/s00253-016-7488-6
Research Year
2016
Research Member
Wael Mostafa Abdel-Mageed Mostafa
Research Abstract

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.