title: Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens.
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.
authors.affiliation: Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Koeduka
authors.forename: K
authors.initials: K
authors.lastname: Sugimoto
authors.forename: B
authors.initials: B
authors.lastname: Watanabe
authors.forename: N
authors.initials: N
authors.lastname: Someya
authors.forename: D
authors.initials: D
authors.lastname: Kawanishi
authors.forename: T
authors.initials: T
authors.lastname: Gotoh
authors.forename: R
authors.initials: R
authors.lastname: Ozawa
authors.forename: J
authors.initials: J
authors.lastname: Takabayashi
authors.forename: K
authors.initials: K
authors.lastname: Matsui
authors.forename: J
authors.initials: J
authors.lastname: Hiratake
mesh_terms: D000818:Animals; D060467:Disease Resistance; D005054:Eugenol / Q000031:analogs & derivatives / Q000378:metabolism*; D005658:Fungi; D029523:Illicium / Q000378:metabolism* / Q000382:microbiology / Q000502:physiology; D008925:Mites; D015394:Molecular Structure; D009822:Oils, Volatile / Q000737:chemistry; D010935:Plant Diseases / Q000382:microbiology; D018515:Plant Leaves / Q000378:metabolism*; D054876:Prenylation; D013329:Structure-Activity Relationship
chemical_list: D009822:Oils, Volatile; D005054:Eugenol; C036643:isoeugenol
keywords: Antifungal activity; O-prenylation; oviposition; phenolic hydroxy groups; volatiles