Biocatalysis of ursolic acid by the fungus Gliocladium roseum CGMCC 3.3657 and resulting anti-HCV activity

Shaobin Fu; Qingfeng Meng; Junshan Yang; Jiajia Tu; Di-An Sun

doi:10.1039/c8ra01217b

Biocatalysis of ursolic acid by the fungus Gliocladium roseum CGMCC 3.3657 and resulting anti-HCV activity

RSC Adv. 2018 May 3;8(29):16400-16405. doi: 10.1039/c8ra01217b. eCollection 2018 Apr 27.

Authors

Shaobin Fu^{1

2}, Qingfeng Meng³, Junshan Yang¹, Jiajia Tu², Di-An Sun¹

Affiliations

¹ Institute of Medical Plant Development, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100193 China diansun@sina.com fushb@126.com +86-0851-28609493 +86-10-57833298 +86-0851-28642513.
² Pharmacy School of Zunyi Medical University Zunyi 563000 China.
³ Department of Public Health, Zunyi Medical University Zunyi 563000 China.

Abstract

Biocatalysis of ursolic acid (UA 1) by Gliocladium roseum CGMCC 3.3657 was investigated. Baeyer-Villiger oxidation was found to occur during the reaction. Four metabolites were isolated from the cultures and their structures were identified as 21-oxo,A-homo-3a-oxa-urs-12-en-3-one-28-oic acid (2), 21-oxo-3,4-seco-ursan-4(23),12-dien-3,28-dioic acid (3), 21β-hydroxyl-A-homo-3a-oxa-urs-12-en-3-one-28-oic acid (4) and 21β-hydroxyl-3,4-seco-ursan-4(23),12-dien-3,28-dioic acid (5), based on their NMR and MS spectral data. All of the four metabolites were new and their anti-HCV activity was tested. Their biotransformation pathway was also proposed.