New water soluble glycosides of 11-keto-β-boswellic acid: A paradigm

Nat Prod Res. 2018 Jan;32(2):154-161. doi: 10.1080/14786419.2017.1342084. Epub 2017 Jun 18.

Abstract

Though several glycosides of various triterpenes are known, but surprisingly no boswellic acid glycosides are reported so far. With a view to make water soluble boswellic acids, prepared glycosides of 11-keto boswellic acid for the first time. Naturally occurring boswellic acids which are anti-inflammatory agents are lipophylic in nature and thus, become a limiting factor in terms of their bioavailability. Among boswellic acids, 11-keto-β-boswellic acid is found to exhibit superior biological activity and hence successfully prepared its glucosyl and maltosyl derivatives viz., 11-keto-β-boswellic acid-24-O-β-D-glucopyranoside (9) and 11-keto-β-boswellic acid-24-O-α-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside (15) which are water soluble. Both these compounds are soluble in water to the extent of 10% (w/w) which is very significant.

Keywords: Boswellia seratta; bioavailability; boswellic acids; glycosylation.

MeSH terms

  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacokinetics*
  • Biological Availability
  • Boswellia / chemistry
  • Glycosides / chemical synthesis
  • Glycosides / chemistry
  • Glycosides / pharmacokinetics*
  • Solubility
  • Triterpenes / chemical synthesis*
  • Triterpenes / chemistry
  • Water / chemistry

Substances

  • 11-keto-boswellic acid
  • Anti-Inflammatory Agents
  • Glycosides
  • Triterpenes
  • Water
  • boswellic acid