Isolation, biological evaluation and 3D-QSAR studies of insecticidal/narcotic sesquiterpene polyol esters.
For the first time, a set of (43) natural sesquiterpene polyol esters isolated from the root bark of Celastrus angulatus Maxim and Euonymus japonicus Thunb were subjected to 3D-QSAR comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) studies, with the aim of proposing novel sesquiterpene-based compounds with optimal narcotic or insecticidal activities. The established 3D-QSAR models exhibit reasonable statistical quality and prediction capabilities, with internal cross-validated Q (2) values of ∼ 0.5 and external predicted R (2) values of >0.9, respectively. The relative contributions of the steric/electrostatic fields of the 3D-QSAR models show that the electronic effect governs the narcotic activities of the molecules, but the hybrid effect of the electrostatic and hydrophobic interactions is more influential in the insecticidal activities of the compounds. These findings may have valuable implications for the development of novel natural insecticides.
Institute of Pesticide Science, Northwest Agricultural & Forestry University, Shaanxi 712100, China.
Shao-peng
SP
Wei
Zhi-qin
ZQ
Ji
Hui-xiao
HX
Zhang
Ji-wen
JW
Zhang
Yong-hua
YH
Wang
Wen-jun
WJ
Wu
D000818:Animals; D004952:Esters; D007306:Insecticides / Q000737:chemistry* / Q000302:isolation & purification; D007814:Larva; D007928:Lethal Dose 50; D008958:Models, Molecular; D009036:Moths; D011108:Polymers / Q000737:chemistry / Q000302:isolation & purification; D021281:Quantitative Structure-Activity Relationship; D015203:Reproducibility of Results; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification
D004952:Esters; D007306:Insecticides; D011108:Polymers; D012717:Sesquiterpenes; C024617:polyol