Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity

J Nat Prod. 2008 Jan;71(1):153-5. doi: 10.1021/np0704396. Epub 2007 Dec 19.

Abstract

Two new cucurbitacins, endecaphyllacins A (1) and B (2), together with six known analogues (3-8), were isolated from the tubers of Hemsleya endecaphylla. The structures of 1 and 2 were elucidated by NMR and MS spectroscopic analysis. The relative stereochemistry of 1 was determined by single-crystal X-ray diffraction. Compound 4 (cucurbitacin B) showed potent anti-HIV-1 in C8166 cells (EC=0.09 microg/mL) with a selectivity index of 16.7.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / isolation & purification*
  • Anti-HIV Agents / pharmacology*
  • Crystallography, X-Ray
  • Cucurbitaceae / chemistry*
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • HIV-1 / drug effects*
  • Molecular Structure
  • Plant Tubers / chemistry
  • Plants, Medicinal / chemistry*
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*

Substances

  • Anti-HIV Agents
  • Drugs, Chinese Herbal
  • Triterpenes
  • endecaphyllacin A
  • endecaphyllacin B