Structures of antifungal diarylheptenones, gingerenones A, B, C and isogingerenone B, isolated from the rhizomes of Zingiber officinale

Katsuya Endo, Emi Kanno, Yoshiteru Oshima

Research output: Contribution to journalArticlepeer-review

77 Citations (Scopus)

Abstract

Four new diarylheptenones, 1,7-bis(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one (gingerenone A), 7-(3,5-dimethoxy-4-hydroxyphenyl)-1-(4-hydroxy-3-methoxyphenyl) hept-4-en-3-one(gingerenone B), 1-(3,5-dimethoxy-4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hept-4-en-3-one (isogingerenone B) and 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hept-4-en-3-one (gingerenone C) have been isolated from the rhizomes of Zingiber officinale, and their structures established by spectral methods and some chemical transformations. The results indicate the similarity in the metabolic fates of the curcuminoid constituents to those of the arylalkanoids (dehydrogingerdione → gingerol → shogaol) of zingiberaceous plants. Gingerenone A exhibited a moderate anticoccidium activity in vitro and a strong antifungal effect to Pyricularia oryzae.

Original languageEnglish
Pages (from-to)797-799
Number of pages3
JournalPhytochemistry
Volume29
Issue number3
DOIs
Publication statusPublished - 1990 Jan 1

Keywords

  • Zingiber officinale
  • Zingiberaceae
  • anticoccidium activity
  • antifungal activity.
  • diarylheptenone
  • gingerenone A
  • gingerenone B
  • gingerenone C
  • isogingerenone B

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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