Microbial hydroxylation and glycosidation of oleanolic acid by Circinella muscae and their anti-inflammatory activities. Issue 13 (3rd July 2019)

• Record Type: Journal Article
• Authors: Yan, Sensen; Lin, Haijun; Huang, Huilian; Yang, Min; Xu, Bohui; Chen, Guangtong
• Is Part Of: Natural product research. Volume 33:Issue 13(2019)
• Page Start: 1849
• Page End: 1855
• Publication Date: 2019-07-03
• Subjects: Circinella muscae -- oleanolic acid -- biotransformation -- anti-inflammatory activity; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2018.1477150
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: Biotransformation of oleanolic acid (OA) by Circinella muscae AS 3.2695 was investigated. Nine hydroxylated and glycosylated metabolites (1–9 ) were obtained. Their structures were elucidated as 3β, 7β-dihydroxyolean-12-en-28-oic acid (1 ), 3β, 7β, 21β-trihydroxyolean-12-en-28-oic acid (2 ), 3β, 7α, 21β-trihydroxyolean-12-en- 28-oic acid (3 ), 3β, 7β, 15α-trihydroxyolean-12-en-28-oic acid (4 ), 7β, 15α-dihydroxy- 3-oxo-olean-12-en-28-oic acid (5 ), 7β-hydroxy-3-oxo-olean-12-en-28-oic acid (6 ), oleanolic acid-28-O-β-D-glucopyranosyl ester (7 ), 3β, 21β-dihydroxyolean-12-en-28- oic acid-28-O-β-D-glucopyranosyl ester (8 ), and 3β, 7β, 15α-trihydroxyolean-12-en- 28-oic acid-28-O-β-D-glucopyranosyl ester (9 ) by spectroscopic analysis. Among them, compounds4 and9 were new compounds. In addition, anti-inflammatory activities were assayed and evaluated for the isolated metabolites. Most of the metabolites exhibited significant inhibitory activities on lipopolysaccharides-induced NO production in RAW 264.7 cells. Abstract :