New prenylated anthraquinones and xanthones from Vismia guineensis

J Nat Prod. 2000 Jan;63(1):16-21. doi: 10.1021/np990226j.

Abstract

From the roots of Vismia guineensis 23 structurally related compounds were isolated and identified. Ten of them are new constituents, namely 3-O-(2-hydroxy-3-methylbut-3-enyl)-emodin (1); 3-O-(2-methoxy-3-methylbut-3-enyl)-emodin (2); 1, 8-dihydroxy-3-(2-methoxy-3-methylbut-3-enyloxy)-6-methylx anthone (3); 1,8-dihydroxy-3-geranyloxy-6-methylxanthone (4); 1, 8-dihydroxy-3-isoprenyloxy-6-methylxanthone (5); 1,8-dihydroxy-3-(3, 7-dimethyl-7-methoxyoct-2-enyloxy)-6-methylxanthone (6); 3-O-(E-3-hydroxymethylbut-2-enyl)-emodin (7); 3-O-(3-hydroxymethyl-4-hydroxybut-2-enyl)-emodin (8); 1, 8-dihydroxy-3-(E-3-hydroxymethylbut-2-enyloxy)-6-methylxa nthone (9); and 1, 8-dihydroxy-3-(3-hydroxymethyl-4-hydroxybut-2-enyloxy)-6- methylxantho ne (10). Their structures were established by means of EIMS and a combination of homonuclear and heteronuclear 2D NMR techniques. Furthermore, an in vitro preliminary screening of antimitotic activity of all the isolated compounds was also evaluated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology
  • Cell Cycle / drug effects
  • Ericales / chemistry*
  • Humans
  • Male
  • Molecular Structure
  • Mutagens / pharmacology
  • Spectrum Analysis
  • Xanthenes / chemistry
  • Xanthenes / isolation & purification*
  • Xanthenes / pharmacology
  • Xanthones*

Substances

  • Anthraquinones
  • Mutagens
  • Xanthenes
  • Xanthones
  • xanthone