Bioactivity of naturalO-prenylated phenylpropenes fromIllicium anisatumleaves and their derivatives against spider mites and fungal pathogens
| Autor: | Koichi Sugimoto, D. Kawanishi, Takao Koeduka, N. Someya, Jun Hiratake, Rika Ozawa, Kenji Matsui, Junji Takabayashi, Tetsuo Gotoh, Bunta Watanabe |
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| Rok vydání: | 2013 |
| Předmět: |
Illicium anisatum
Plant Science Illicium Structure-Activity Relationship chemistry.chemical_compound Prenylation Eugenol Oils Volatile Mite Animals Organic chemistry Ecology Evolution Behavior and Systematics Disease Resistance Plant Diseases Mites Molecular Structure biology Fungi General Medicine Fungal pathogen biology.organism_classification Plant Leaves Isoeugenol chemistry Biochemistry Guaiacol Toxicant |
| Zdroj: | Plant Biology. 16:451-456 |
| ISSN: | 1435-8603 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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