The Structures of some Stress Metabolites from Solanummelongena

Abstract

The structures of the acyclic sesquiterpenes 1–5 and the bicyclic sesquiterpenes 6 and 7, all isolated from eggplant fruit inoculated with fungi, were elucidated with the aid of 1H and 13C n.m.r. studies. Trienone 1 was found to be identical to 9-oxonerolidol from camphor leaf oil while 2 and 3 are isomeric alcohols derived from 1. Compounds 4 and 5 are probably artifacts. The hydroxyaldehyde 6 is identical with the potato phytoalexin lubimin, originally represented by a structure shown here to be incorrect. Enone 7 is a novel eudesmane. The stereochemistries of these compounds are discussed.