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Int. J. Mol. Sci. 2013, 14(10), 19484-19493; doi:10.3390/ijms141019484
Article

Semisynthesis and Antifeedant Activity of New Derivatives of a Dihydro-β-Agarofuran from Parnassia wightiana

1,†
,
1,†
,
2
,
1
,
1
 and
1,*
1 Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Science, Northwest A&F University, Yangling 712100, Shaanxi, China 2 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 / Revised: 22 August 2013 / Accepted: 10 September 2013 / Published: 26 September 2013
(This article belongs to the Section Biochemistry, Molecular Biology and Biophysics)
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Abstract

Five new derivatives (26) 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 26 were confirmed by 1D- and 2D-NMR and HR-ESI-MS spectra. In addition, antifeedant activities of these compounds (16) 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 sesquiterpene; agarofuran; derivatives; antifeedant activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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