New compounds from an extract of Vernonia colorata leaves with anti-inflammatory activity

J Nat Prod. 2004 Mar;67(3):389-94. doi: 10.1021/np030337p.

Abstract

Bioassay-directed fractionation of an anti-inflammatory CHCl(3)-MeOH (9:1) extract of leaves of Vernonia colorata, using a carrageenan-induced rat paw model, led to the isolation of six new compounds (1-6). These were assigned as two new androst-8-en glycosides, 3-O-[beta-d-galactopyranosyl-(1-2)-[beta-d-glucopyranosyl-(1-->6)]-beta-d-glucopyranoside]-5alpha,14alpha-androst-8-ene (1) and 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside]-5alpha,14alpha-androst-8-ene (2), two new stigmastane-type glycosides, 3beta,21,24-trihydroxy-21,23;22,28;26,28-triepoxy-5alpha-stigmasta-8(9),14(15)-dien-3-O-beta-d-galactopyranosyl-(1-->2)-beta-d-glucopyranoside (3) and 3beta,21,24-trihydroxy-21,23;22,28;26,28-triepoxy-5alpha-stigmasta-8(9),14(15)-dien-3-O-beta-d-galactopyranosyl-(1-->2)-beta-d-(6-acetyl)glucopyranoside (4), and two new stigmastane-type steroids, 3beta,25,29-trihydroxy-5alpha-stigmasta-8(9),14(15),24Z(28)-triene (5) and 3beta,23,25-trihydroxy-24,28-epoxy-5alpha-stigmasta-8(9),14(15)-diene (6). The structures of 1-6 were elucidated by spectral and chemical studies. Compounds 1-6 were tested for the anti-inflammatory activity, but all were inactive or weakly inactive as anti-inflammatory agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androstenes / chemistry
  • Androstenes / isolation & purification*
  • Androstenes / pharmacology
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Mali
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Stigmasterol / analogs & derivatives*
  • Stigmasterol / chemistry
  • Stigmasterol / isolation & purification*
  • Stigmasterol / pharmacology
  • Vernonia / chemistry*

Substances

  • Androstenes
  • Anti-Inflammatory Agents
  • Glycosides
  • Stigmasterol