Structure–Activity Relationship of Clerodane Diterpenoids Acting as Antifeedant Agents

ENRIZ, R.D.; BALDONI, H.A.; JAUREGUI, E.A.; SOSA, M.E.; TONN, C.E.; GIORDANO, O.S.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

AMER CHEMICAL SOC

Año: 1994 vol. 42 p. 2958 - 2963

0021-8561

Considering the feeding-deterrent activities exhibited toward Tenebrio molitor (L.) (Coleoptera: Tenebrionidae) of several diterpenes with the clerodane skeleton isolated in our laboratory, a structure-activity relationship study was undertaken. A series of different clerodane diterpenoids was analyzed by performing an exhaustive study of their electronic and conformational behaviors. The results indicate that the antifeedant activity of these clerodane diterpenoids is mediated, at least, through two binding sites. Apparently one important factor contributing to the biological activity is a high conformational flexibility for the torsion angle of the β-furyl group. © 1994, American Chemical Society. All rights reserved.