Semisynthesis and antifeedant activity of new derivatives of a dihydro-β-agarofuran from Parnassia wightiana.
Five new derivatives (2-6) were semi-synthesized using compound 1, a dihydro-β-agarofuran sesquiterpene with C-2 ketone obtained from Parnassia wightiana, as the starting material by acylation, oxidation, reduction, esterification, and amination, respectively. Structures of 2-6 were confirmed by 1D- and 2D-NMR and HR-ESI-MS spectra. In addition, antifeedant activities of these compounds (1-6) were tested against the 3rd-instar larvae of Mythimna separata. Antifeedant effects of compounds 2 and 4 were greater than the parent compound 1 whereas other compounds exhibited low to no feeding deterrent effects against third instar M. separata larvae in lab bioassays. Therefore, our results suggest that acylated and reduced derivatives at C-8 and C-2, respectively, of 1 may improve the antifeeding effect. This preliminary information will be useful in designing new insect control agents against M. separata and other important pests.
Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China. jinminggao@nwsuaf.edu.cn.
Jiang-Jiang
JJ
Tang
Fei-Yu
FY
Zhang
Dong-Mei
DM
Wang
Jun-Mian
JM
Tian
Shuai
S
Dong
Jin-Ming
JM
Gao
D000818:Animals; D007300:Insect Control / Q000379:methods; D007814:Larva / Q000187:drug effects*; D009036:Moths / Q000187:drug effects*; D010936:Plant Extracts / Q000737:chemistry* / Q000494:pharmacology*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology*
D010936:Plant Extracts; D012717:Sesquiterpenes; C079978:dihydroagarofuran