Absolute stereochemistry and anti-HIV activity of minquartynoic acid, a polyacetylene from Ochanostachys amentacea

Nat Prod Lett. 2001;15(1):21-6. doi: 10.1080/10575630108041253.

Abstract

Anti-HIV bioassay-guided fractionation of an organic extract of Ochanostachys amentacea provided an HIV-inhibitory polyacetylenic acid. The identity of this compound was established as (-)-17-hydroxy-9,11,13,15-octadecatetraynoic acid (1), also known as minquartynoic acid, by comparison of its physical and spectral data with previously reported values. Analysis of Mosher's ester derivatives of the methyl ester of 1 allowed assignment of S absolute stereochemistry to the lone chiral center. In an in vitro XTT-based anti-HIV assay, 2-5 micrograms/mL of minquartynoic acid (1) effectively inhibited human lymphoblastoid cell killing by HIV-1.

MeSH terms

  • Alkynes*
  • Anti-HIV Agents / chemistry*
  • Anti-HIV Agents / pharmacology*
  • Fatty Acids, Unsaturated / chemistry*
  • Fatty Acids, Unsaturated / pharmacology*
  • HIV-1 / drug effects
  • Humans
  • Magnoliopsida / chemistry*
  • Microbial Sensitivity Tests
  • Polyynes
  • Stereoisomerism

Substances

  • Alkynes
  • Anti-HIV Agents
  • Fatty Acids, Unsaturated
  • minquartynoic acid
  • Polyynes