First Discovery of Insecticidal Activity of 9,9′-Epoxylignane and Dihydroguaiaretic Acid against Houseflies and the Structure–Activity Relationship

• Published in: Journal of agricultural and food chemistry 2013-05, Vol.61 (18), p.4318-4325
• Main Authors: Wukirsari, Tuti, Nishiwaki, Hisashi, Hasebe, Ayaka, Shuto, Yoshihiro, Yamauchi, Satoshi
• Format: Article
• Language: English
• Subjects: Animals; Biological and medical sciences; Epoxy Compounds - pharmacology; Food industries; Fundamental and applied biological sciences. Psychology; Guaiacol - analogs & derivatives; Guaiacol - pharmacology; Houseflies; insecticidal properties; Insecticides - pharmacology; Lignans - pharmacology; Musca domestica; plant extracts; Plant Extracts - pharmacology; Stereoisomerism; Structure-Activity Relationship; structure-activity relationships
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf400300n

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.