Trypanocidal diarylheptanoids from Aframomum letestuianum

J Nat Prod. 2003 Mar;66(3):364-7. doi: 10.1021/np020362f.

Abstract

Three new diarylheptanoids, (4Z,6E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-4,6-dien-3-one, letestuianin A (1), (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-4,6-dien-3-one, letestuianin B (2), and 1,7-bis(4-hydroxyphenyl)heptan-3,5-dione, letestuianin C (3), as well as the known (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-4,6-dien-3-one (5) were isolated from Aframomum letestuianum. The known flavonoids 3-acetoxy-5,7,4'-trihydroxyflavanone, 3-acetoxy-7-methoxy-5,4'-dihydroxyflavanone, 7-methoxy-3,5,4'-trihydroxyflavone, and 3,3',4',5,7-pentahydroxyflavan were also obtained from this plant. Their structures were determined using a combination of 1D and 2D NMR techniques. The four diarylheptanoids were tested for growth inhibitory activity in vitro versus bloodstream forms of African trypanosomes. IC(50) values in the range of 1-3 microg/mL were found for compounds 3 and 5.

Publication types

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

MeSH terms

  • Animals
  • Cameroon
  • Diarylheptanoids / chemistry
  • Diarylheptanoids / isolation & purification*
  • Diarylheptanoids / pharmacology
  • Inhibitory Concentration 50
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Seeds / chemistry
  • Stereoisomerism
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / isolation & purification*
  • Trypanocidal Agents / pharmacology
  • Trypanosoma brucei brucei / drug effects*
  • Zingiberaceae / chemistry*

Substances

  • Diarylheptanoids
  • Trypanocidal Agents
  • letestuianin A
  • letestuianin B
  • letestuianin C