New bioactive flavonoids and stilbenes in cubé resin insecticide

J Nat Prod. 1999 Feb;62(2):205-10. doi: 10.1021/np980119+.

Abstract

Fractionation of cubé resin from Lonchocarpus utilus and L. urucu roots led to the isolation and identification of 11 minor flavonoids and stilbenes containing the gem-dimethylpyran moiety or a dihydrodiol derivative thereof. The eight new compounds were as follows: the isoflavonoid cis-4'',5''-dihydro-4'',5' '-dihydroxylonchocarpusone (2); four (2S)-6-(gamma, gamma-dimethylallyl)-6'',6''-dimethylpyran[2'',3'':7, 8]flavanones with substituents of 5-hydroxy-3',4'-dimethoxy (3), 5, 3'-dihydroxy-4'-methoxy (4), 5,4'-dihydroxy-3'-methoxy (5), and 3', 4'-dimethoxy (6); and three 6'',6''-dimethylpyran[2'',3'':3', 4']stilbenes with 4-hydroxy-5'-methoxy (9), 3,5'-dimethoxy-4-hydroxy (10) and 3,4,5-trimethoxy (11) substitution patterns. Structure-activity relationships for inhibition of NADH:ubiquinone oxidoreductase activity (bovine heart electron transport particles) and phorbol ester-induced ornithine decarboxylase activity (cultured MCF-7 cells) generally parallel those for cytotoxicity (MCF-7 and Hepa 1clc7 cells).

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Cattle
  • Cell Survival / drug effects
  • Enzyme Induction
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Humans
  • Insecticides
  • Mice
  • Molecular Structure
  • Ornithine Decarboxylase / biosynthesis
  • Plant Extracts / chemistry*
  • Spectrum Analysis
  • Stilbenes / chemistry
  • Stilbenes / isolation & purification*
  • Stilbenes / pharmacology
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Flavonoids
  • Insecticides
  • Plant Extracts
  • Stilbenes
  • Ornithine Decarboxylase