Oleanane triterpenoids from Rubia philippinensis and their inhibitory effect on 20-HETE synthesis

Nat Prod Res. 2021 Apr;35(8):1267-1273. doi: 10.1080/14786419.2019.1645656. Epub 2019 Jul 25.

Abstract

A new oleanane triterpenoid (2) was isolated from the roots of Rubia philippinensis. The structure of 2 was determined by analysis of HRMS and NMR data and identified as a rubiprasin analogue, 16β-hydroxyrubiprasin B. Four related known compounds were also encountered which include rubiprasin B (1), maslinic acid (3), 4-epi-hederagenin (4) and oleanolic acid (5). The compounds 3-5 displayed moderate inhibitory activity against the synthesis of the eicosanoid 20-HETE.

Keywords: 16β-hydroxyrubiprasin B; 20-HETE; Oleanane triterpenoids; Rubia philippinensis.

MeSH terms

  • Humans
  • Hydroxyeicosatetraenoic Acids / biosynthesis*
  • Magnetic Resonance Spectroscopy
  • Microsomes / drug effects
  • Microsomes / metabolism
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry
  • Plant Roots / chemistry
  • Rubia / chemistry*
  • Structure-Activity Relationship
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology*

Substances

  • Hydroxyeicosatetraenoic Acids
  • Triterpenes
  • oleanane
  • Oleanolic Acid
  • 20-hydroxy-5,8,11,14-eicosatetraenoic acid
  • maslinic acid