Biotransformation of 11-keto-尾-boswellic acid by Cunninghamella blakesleana

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• 作者：Yue Wang ; Yan Sun ; Chao Wang ; Xiaokui Huo ; Pinduan Liu ; Changyuan Wang ; Baojing Zhang ; Libin Zhan ; Houli Zhang ; Sa Deng ; Yanyan Zhao ; Xiaochi Ma
• 关键词：Cunninghamella blakesleana AS 3.970 ; Boswellia serrata ; Biotransformation ; 11-Keto-尾-boswellic acid ; Burseraceae ; NO inhibition
• 刊名：Phytochemistry
• 出版年：December, 2013
• 年：2013
• 卷：96
• 期：Complete
• 页码：330-336
• 全文大小：427 K

文摘

11-Keto-尾-boswellic acid (KBA), as one of the active constituents in the gum resin of Boswellia serrata, possesses significant biological activities including anti-inflammatory activity. However, its extensive metabolism and low polarity has limited the systemic availability of KBA. The present research was aimed to obtain and explore the various possible derivatives of KBA through biotransformation by Cunninghamella blakesleana AS 3.970. A total of ten transformed compounds were isolated and purified, and their chemical structures were characterized as 7尾-hydroxy-11-keto-尾-boswellic acid; 7尾, 15伪-dihydroxy-11-keto-尾-boswellic acid ; 7尾, 16尾-dihydroxy-11-keto-尾-boswellic acid; 7尾, 16伪-dihydroxy-11-keto-尾-boswellic acid; 7尾, 22尾-dihydroxy-11-keto-尾-boswellic acid; 7尾, 21尾-dihydroxy-11-keto-尾-boswellic acid; 7尾, 20尾-dihydroxy-11-keto-尾-boswellic acid; 7尾, 30-dihydroxy-11-keto-尾-boswellic acid; 3伪, 7尾-dihydroxy-11-oxours-12-ene-24, 30-dioic acid and 3伪, 7尾-dihydroxy-30-(2-hydroxypropanoyloxy)-11-oxours-12-en-24-oic acid by various spectroscopic methods. The biotransformation processes include hydroxylation, oxidation and esterification. Primary structure-activity relationships (SAR) of inhibitory effects on NO production in RAW 264.7 macrophage cells are discussed.