Furan-site transformations of obacunone as potent insecticidal agents
Ping Xiang,
Qing-Hao Cao,
Qing-Miao Dong,
Xiao-Jun Yang,
Jiang-Jiang Tang,
Hongjin Bai
Affiliations
Ping Xiang
College of Plant Protection, Northwest A&F University, Yangling, 712100, PR China; Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin, Tarim University, Alar 843300, PR China
Qing-Hao Cao
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, 712100, Shaanxi, PR China
Qing-Miao Dong
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, 712100, Shaanxi, PR China
Xiao-Jun Yang
School of Chemistry & Chemical Engineering, Yanan University, Yanan 716000, Shaanxi, PR China
Jiang-Jiang Tang
Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin, Tarim University, Alar 843300, PR China; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, 712100, Shaanxi, PR China; Corresponding author.
Hongjin Bai
Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin, Tarim University, Alar 843300, PR China; Engineering Laboratory of Chemical Resources Utilization in South Xinjiang of Xinjiang Production & Construction Corps, Tarim University, Alar 843300, PR China
Furan ring is a key pharmacophore for insecticidal activity of limoninoids. To develop natural-product-based insecticidal agents, a series of furan-site transformations (2, 3 and 3a–j) of obacunone were synthesized by selective bromination and following coupling reactions without altering other functional groups. Bioassays indicated that derivatives 3e, 3f and 3j displayed more potent insecticidal activity than obacunone and toosendanin against the instar larvae of Mythimna separate Walker. Besides, their structure–activity relationships were discussed.
