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

Phytochemistry. 2013 Dec;96:330-6. doi: 10.1016/j.phytochem.2013.07.018. Epub 2013 Aug 17.

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.

Keywords: 11-Keto-β-boswellic acid; Biotransformation; Boswellia serrata; Burseraceae; Cunninghamella blakesleana AS 3.970; NO inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Biotransformation / drug effects
  • Boswellia / metabolism
  • Cunninghamella / metabolism*
  • Immunologic Factors / pharmacology
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Oxidation-Reduction
  • Resins, Plant / chemistry
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / metabolism
  • Triterpenes / pharmacology

Substances

  • 11-keto-boswellic acid
  • Anti-Inflammatory Agents
  • Immunologic Factors
  • Lipopolysaccharides
  • Resins, Plant
  • Triterpenes
  • Nitric Oxide