title: Biotransformation of 11-keto-β-boswellic acid by Cunninghamella blakesleana.
abstract: 11-Keto-β-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 7β-hydroxy-11-keto-β-boswellic acid; 7β, 15α-dihydroxy-11-keto-β-boswellic acid ; 7β, 16β-dihydroxy-11-keto-β-boswellic acid; 7β, 16α-dihydroxy-11-keto-β-boswellic acid; 7β, 22β-dihydroxy-11-keto-β-boswellic acid; 7β, 21β-dihydroxy-11-keto-β-boswellic acid; 7β, 20β-dihydroxy-11-keto-β-boswellic acid; 7β, 30-dihydroxy-11-keto-β-boswellic acid; 3α, 7β-dihydroxy-11-oxours-12-ene-24, 30-dioic acid and 3α, 7β-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.
authors: The First Affiliated Hospital of Liaoning Medical University, Jinzhou 121001, China. Electronic address: wangyuejz2013@163.com.
authors: Yue
authors: Y
authors: Wang
authors: Yan
authors: Y
authors: Sun
authors: Chao
authors: C
authors: Wang
authors: Xiaokui
authors: X
authors: Huo
authors: Pinduan
authors: P
authors: Liu
authors: Changyuan
authors: C
authors: Wang
authors: Baojing
authors: B
authors: Zhang
authors: Libin
authors: L
authors: Zhan
authors: Houli
authors: H
authors: Zhang
authors: Sa
authors: S
authors: Deng
authors: Yanyan
authors: Y
authors: Zhao
authors: Xiaochi
authors: X
authors: Ma
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001711:Biotransformation / Q000187:drug effects; D029743:Boswellia / Q000378:metabolism; D020093:Cunninghamella / Q000378:metabolism*; D007155:Immunologic Factors / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D010084:Oxidation-Reduction; D012116:Resins, Plant / Q000737:chemistry; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology
chemical_list: C447943:11-keto-boswellic acid; D000893:Anti-Inflammatory Agents; D007155:Immunologic Factors; D008070:Lipopolysaccharides; D012116:Resins, Plant; D014315:Triterpenes; D009569:Nitric Oxide
keywords: 11-Keto-β-boswellic acid; Biotransformation; Boswellia serrata; Burseraceae; Cunninghamella blakesleana AS 3.970; NO inhibition