Modified Clerodanes from the Essential Oil of Dodonea viscosa Leaves

Dodonea viscosa (L.) Jacq from Reunion Island (Indian Ocean) was investigated for its leaf essential oil composition. The plant was extracted by hydrodistillation and its essential oil analysed by gas chromatography coupled to mass spectrometry. This study revealed that oxygenated nor-diterpenes and diterpenes were one of the major chemical classes (> 50%) mainly consisting of three modified cyclopropylclerodanes containing a bicyclo[5.4.0]undecane ring system: one new furanoid norditerpene, dodovisate C, and two furanoid diterpenes, the known methyl dodovisate A and the new methyl iso-dodovisate A. These three compounds were isolated by liquid chromatography and their structures established on the basis of spectroscopic studies. The absolute configuration of dodovisate C was elucidated through a joint experimental and theoretical (B3LYP/6-311+G(d,p)) electronic circular dichroism study. The relative configurations of methyl dodovisate A and methyl iso-dodovisate A were determined using linear regressions of theoretical chemical shifts versus experimental values with the (B3LYP/6-311+G(d,p)) method.