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Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana
Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China
College of Forestry, Northwest A&F University, Yangling 712100, Shaanxi, China
These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 1 July 2013; in revised form: 22 August 2013 / Accepted: 10 September 2013 / Published: 26 September 2013
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.
Keywords: sesquiterpene; agarofuran; derivatives; antifeedant activity
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MDPI and ACS Style
Tang, J.-J.; Zhang, F.-Y.; Wang, D.-M.; Tian, J.-M.; Dong, S.; Gao, J.-M. Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana. Int. J. Mol. Sci. 2013, 14, 19484-19493.
Tang J-J, Zhang F-Y, Wang D-M, Tian J-M, Dong S, Gao J-M. Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana. International Journal of Molecular Sciences. 2013; 14(10):19484-19493.
Tang, Jiang-Jiang; Zhang, Fei-Yu; Wang, Dong-Mei; Tian, Jun-Mian; Dong, Shuai; Gao, Jin-Ming. 2013. "Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana." Int. J. Mol. Sci. 14, no. 10: 19484-19493.