Semisynthesis and antifeedant activity of new derivatives of a dihydro-β-agarofuran from Parnassia wightiana.

Jiang-Jiang Tang, Fei-Yu Zhang, Dong-Mei Wang, Jun-Mian Tian, Shuai Dong, Jin-Ming Gao

Index: Int. J. Mol. Sci. 14 , 19484-93, (2013)

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Abstract

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.