Bioactivity of natural O‐prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens |
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Authors: | T Koeduka K Sugimoto B Watanabe N Someya D Kawanishi T Gotoh R Ozawa J Takabayashi K Matsui J Hiratake |
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Institution: | 1. Institute for Chemical Research, Kyoto University, , Uji, Kyoto, 611‐0011 Japan;2. Center for Ecological Research, Kyoto University, , Ohtsu, Shiga, 520‐2113 Japan;3. Hokkaido Agricultural Research Center, National Agriculture and Food Research Organization, , Memuro, Kasai, Hokkaido, 082‐0081 Japan;4. Laboratory of Applied Entomology and Zoology, Faculty of Agriculture, Ibaraki University, , Ami, Ibaraki, 300‐0393 Japan;5. Department of Biological Chemistry, Faculty of Agriculture, Department of Applied Molecular Medicine, Graduate School of Medicine, Yamaguchi University, , Yamaguchi, 753‐8515 Japan |
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Abstract: | A variety of volatile phenylpropenes, C6‐C3 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. |
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Keywords: | Antifungal activity O‐prenylation oviposition phenolic hydroxy groups volatiles |
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