Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia

J Nat Prod. 2000 Feb;63(2):238-42. doi: 10.1021/np9902441.

Abstract

From a methanolic extract of the wood of Xanthoceras sorbifolia, two new compounds, 29-hydroxy-3-oxotirucalla-7,24-dien-21-oic acid (3, xanthocerasic acid) and epigallocatechin-(4beta-->8, 2beta-->O-7)-epicatechin (6), were isolated, together with 11 known compounds. Of the isolated compounds, 3-oxotirucalla-7, 24-dien-21-oic acid (2), oleanolic acid (4), and 6 were found to be inhibitory substances against human immunodeficiency virus (HIV-1) protease, with their 50% inhibitory concentrations (IC(50)) being 20, 10, and 70 microg/mL, respectively. Condensed tannins of high molecular weights with epicatechin and epiafzelechin as the main extender units were found to be the most active principles of this plant (IC(50) values ca. 6.0 microg/mL).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthocyanins / isolation & purification*
  • Anthocyanins / pharmacology
  • Catechin* / analogs & derivatives*
  • Crystallography, X-Ray
  • HIV Protease Inhibitors / isolation & purification*
  • HIV Protease Inhibitors / pharmacology
  • HIV Protease*
  • Humans
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Plants, Medicinal / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology
  • Wood

Substances

  • Anthocyanins
  • HIV Protease Inhibitors
  • Triterpenes
  • epigallocatechin-(4-8,2-O-7)epicatechin
  • xanthocerasic acid
  • Catechin
  • HIV Protease