title: First discovery of insecticidal activity of 9,9'-epoxylignane and dihydroguaiaretic acid against houseflies and the structure-activity relationship.
abstract: The insecticidal activity of (-)-(8R,8'R)-3,3'-dimethoxy-9,9'-epoxylignane-4,4'-diol (1) against houseflies was clarified for the first time. The activities of other stereoisomers were weaker than that of the (8R,8'R)-stereoisomer. In the course of research into structure-activity relationships involving 30 newly synthesized (8R,8'R)-derivatives, 5-fold higher activity (ED50 = 0.91 nmol/fly) was observed for (-)-(8R,8'R)-3,3',4-trimethoxy-9,9'-epoxylignan-4'-ol (21) than for the naturally occurring compound (1). The activity of 1 was weaker than that of (-)-(8R,8'R)-dihydroguaiaretic acid ((-)-DGA) (4); however, compound 21 showed almost the same level of activity as 4.
authors.affiliation: Faculty of Agriculture, Ehime University, Matsuyama, Ehime, Japan.
authors.forename: Tuti
authors.initials: T
authors.lastname: Wukirsari
authors.forename: Hisashi
authors.initials: H
authors.lastname: Nishiwaki
authors.forename: Ayaka
authors.initials: A
authors.lastname: Hasebe
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Shuto
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
mesh_terms: D000818:Animals; D004852:Epoxy Compounds / Q000494:pharmacology*; D006139:Guaiacol / Q000031:analogs & derivatives* / Q000494:pharmacology; D006793:Houseflies; D007306:Insecticides / Q000494:pharmacology*; D017705:Lignans / Q000494:pharmacology*; D010936:Plant Extracts / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C585727:3,3',4-trimethoxy-9,9'-epoxylignan-4'-ol; D004852:Epoxy Compounds; D007306:Insecticides; D017705:Lignans; D010936:Plant Extracts; C015816:dihydroguaiaretic acid; D006139:Guaiacol