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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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