The title diterpenoid, C20H20O5, is a plant metabolite from Salvia wagneriana Polak. The molecule is characterized by a pentacyclic structure derived from a rearranged clerodane skeleton and shows, in addition to A and B rings, two olide systems forming C and D rings. Moreover, a beta-substituted furan ring is present on the C ring. The crystal packing is mainly governed by normal van der Waals interactions. In the crystal structure, one non-classical hydrogen bond is also present, involving the carbonyl O atom of the gamma-lactone ring and one activated C atom of a screw-related furan system. The structure exhibits a remarkable isomorphism with that of the previously characterized salviarin. The antifeedant activity of dehydrosalviarin against the insect Spodoptera littoralis, a destructive pest for tropical and subtropical agriculture, is also reported.
1, 10 - Dehydrosalviarin
BISIO, ANGELA;ROMUSSI, GIOVANNI;
2006-01-01
Abstract
The title diterpenoid, C20H20O5, is a plant metabolite from Salvia wagneriana Polak. The molecule is characterized by a pentacyclic structure derived from a rearranged clerodane skeleton and shows, in addition to A and B rings, two olide systems forming C and D rings. Moreover, a beta-substituted furan ring is present on the C ring. The crystal packing is mainly governed by normal van der Waals interactions. In the crystal structure, one non-classical hydrogen bond is also present, involving the carbonyl O atom of the gamma-lactone ring and one activated C atom of a screw-related furan system. The structure exhibits a remarkable isomorphism with that of the previously characterized salviarin. The antifeedant activity of dehydrosalviarin against the insect Spodoptera littoralis, a destructive pest for tropical and subtropical agriculture, is also reported.
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