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Bioactivity of natural O ‐prenylated phenylpropenes from I llicium anisatum leaves and their derivatives against spider mites and fungal pathogens
Author(s) -
Koeduka T.,
Sugimoto K.,
Watanabe B.,
Someya N.,
Kawanishi D.,
Gotoh T.,
Ozawa R.,
Takabayashi J.,
Matsui K.,
Hiratake J.
Publication year - 2014
Publication title -
plant biology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.871
H-Index - 87
eISSN - 1438-8677
pISSN - 1435-8603
DOI - 10.1111/plb.12054
Subject(s) - eugenol , isoeugenol , biology , spider mite , antifungal , stereochemistry , terpene , botany , mite , chemistry , biochemistry , organic chemistry , microbiology and biotechnology
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 I llicium 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.