Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin.
| Autor: | Enriz RD; Departamento de Química, Cátedra de Entomología, and Laboratorio de Alimentos, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Chacabuco y Pedernera, 5700 San Luis, Argentina. denriz@unsl.edu.ar, Baldoni HA, Zamora MA, Jáuregui EA, Sosa ME, Tonn CE, Luco JM, Gordaliza M |
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| Jazyk: | angličtina |
| Zdroj: | Journal of agricultural and food chemistry [J Agric Food Chem] 2000 Apr; Vol. 48 (4), pp. 1384-92. |
| DOI: | 10.1021/jf990006b |
| Abstrakt: | A structure-antifeedant activity relationship (SAR) study of clerodane diterpenoids was carried out. Attention was focused on the feeding-deterrent activities exhibited toward Tenebrio molitor by clerodane diterpenoids and withanolides. Azadirachtin was chosen as a reference compound. SAR studies on the clerodane compounds indicate that the stereoelectronic factors are more important than the hydrophobic aspects as determinants of antifeedant activity. A furan ring in the side chain and a carbonyl alpha,beta-unsaturated (or spiro-epoxide) group appear to be indispensable for the biological response. A conformational study indicate that the optimum interatomic distance between these moieties is a range between 9.5 and 10.5 A. In addition, a similar stereoelectronic response was found among withanolides and azadirachtin. On the basis of these results it is reasonable to imagine a closely related chemical mechanism for these compounds. |
| Databáze: | MEDLINE |
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