論文

査読有り
2014年3月

Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens

PLANT BIOLOGY
  • T. Koeduka
  • ,
  • K. Sugimoto
  • ,
  • B. Watanabe
  • ,
  • N. Someya
  • ,
  • D. Kawanishi
  • ,
  • T. Gotoh
  • ,
  • R. Ozawa
  • ,
  • J. Takabayashi
  • ,
  • K. Matsui
  • ,
  • J. Hiratake

16
2
開始ページ
451
終了ページ
456
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1111/plb.12054
出版者・発行元
WILEY-BLACKWELL

A variety of volatile phenylpropenes, C-6-C-3 compounds are widely distributed in the plant kingdom, whereas prenylated phenylpropenes are limited to a few plant species. In this study, we analysed the volatile profiles from Illicium anisatum leaves and identified two O-prenylated phenylpropenes, 4-allyl-2-methoxy-1-[(3-methylbut-2-en-1-yl)oxy]benzene [O-dimethylallyleugenol (9)] and 5-allyl-1,3-dimethoxy-2-(3-methylbut-2-en-1-yl)oxy]benzene [O-dimethylallyl-6-methoxyeugenol (11)] as major constituents. The structure-activity relationship of a series of eugenol derivatives showed that specific phenylpropenes, including eugenol (1), isoeugenol (2) and 6-methoxyeugenol (6), with a phenolic hydroxy group had antifungal activity for a fungal pathogen, whereas guaiacol, a simple phenolic compound, and allylbenzene had no such activity. The eugenol derivatives that exhibited antifungal activity, in turn, had no significant toxicant property for mite oviposition. Interestingly, O-dimethylallyleugenol (9) in which the phenolic oxygen was masked with a dimethylallyl group exhibited a specific, potent oviposition deterrent activity for mites. The sharp contrast in structural requirements of phenylpropenes suggested distinct mechanisms underlying the two biological activities and the importance of a phenolic hydroxy group and its dimethylallylation for the structure-based design of new functional properties of phenylpropenes.

リンク情報
DOI
https://doi.org/10.1111/plb.12054
PubMed
https://www.ncbi.nlm.nih.gov/pubmed/23889818
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000331874700017&DestApp=WOS_CPL
ID情報
  • DOI : 10.1111/plb.12054
  • ISSN : 1435-8603
  • eISSN : 1438-8677
  • PubMed ID : 23889818
  • Web of Science ID : WOS:000331874700017

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