Synthesis and insect antifeedant activity of stilbene derivatives against Brontispa longissima Larvae
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Med Chem Res (2013) 22:2196–2206 DOI 10.1007/s00044-012-0212-x
ORIGINAL RESEARCH
Synthesis and insect antifeedant activity of stilbene derivatives against Brontispa longissima Larvae Ying-Qian Liu • Xiao-Jing Li • Chun-Yan Zhao • Yan Lu • Wen-Qun Li • Zhen-Ling Liu • Gang Feng Liu Yang
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Received: 9 April 2011 / Accepted: 20 August 2012 / Published online: 6 September 2012 Ó Springer Science+Business Media, LLC 2012
Abstract Continuing our search for natural productbased compounds for the control of B. longissima Larvae, 25 stilbene analogs were synthesized and evaluated for insect antifeedant activity against third-instar larvae of B. longissima for the first time. Among all the tested compounds, especially compounds 3a, 3c, and 6 showed pronounced antifeedant activities with AFC50 values of 0.218, 0.327, and 0.226 mg/mL, respectively. The different antifeedant activity ranges of these compounds indicated that variation of chemical structures in the stilbene skeleton markedly affected the activity profiles of this compound class, and some important SAR information has been revealed from it. In addition, to understand the structural requirements for antifeedant activities of the 25 synthesized stilbene analogs, a comparative molecular field analysis (CoMFA) model, which yielded the leave-one-out (LOO) cross-validated correlation coefficient (q2) of 0.533 and a non-cross-validated correlation coefficient (r2) of Y.-Q. Liu (&) X.-J. Li C.-Y. Zhao Y. Lu W.-Q. Li School of Pharmacy, Lanzhou University, Lanzhou 730000, People’s Republic of China e-mail: [email protected] G. Feng Environment and Plant Protection Institute, Chinese Academy of Tropical Agricultural Science, Danzhou 571737, People’s Republic of China L. Yang Environmental and Municipal Engineering School, Lanzhou Jiaotong University, Lanzhou 730000, People’s Republic of China Z.-L. Liu State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People’s Republic of China
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0.929, was constructed. Together, these preliminary results may be useful in guiding further modification of stilbenes in the development of potential new antifeedants. Keywords Stilbenes insect antifeedants Brontispa longissima CoMFA 3D-QSAR study
Introduction Brontispa longissima (Gestro) (B. longissima), which is mainly distributed in Southeast Asia and the Pacific Ocean islands, is a destructive pest to palm plants (Zhou et al., 2004; Su et al., 2009). Control of the B. longissima larvae is frequently dependent on continued applications of conventional pesticides such as organochlorine, organophosphorus, carbamate, formamidines, and pyrethroid insecticides. Although effective, their repeated use has produced risks in the development of insect resistance and residues to humans and to the environment (Luo et al., 2005; Xie et al., 2007). These problems have highlighted the need for the development of new, more ecologically acceptable methods for B. longissima larvae control. Accordingly, botanical antifeedants, plant-based compounds ma
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