Modified Clerodanes from the Essential Oil of <i>Dodonea viscosa</i> Leaves
Arnaud Marvilliers,
Bertrand Illien,
Emmanuelle Gros,
Jonathan Sorres,
Yoel Kashman,
Hermann Thomas,
Jacqueline Smadja,
Anne Gauvin-Bialecki
Affiliations
Arnaud Marvilliers
Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de la Réunion, 15 Avenue René Cassin, CS 92003, 97744 St Denis, Messag CEDEX 9, La Réunion, France
Bertrand Illien
Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de la Réunion, 15 Avenue René Cassin, CS 92003, 97744 St Denis, Messag CEDEX 9, La Réunion, France
Emmanuelle Gros
Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de la Réunion, 15 Avenue René Cassin, CS 92003, 97744 St Denis, Messag CEDEX 9, La Réunion, France
Jonathan Sorres
Institut de Chimie des Substances Naturelles, CNRS, 91110 Gif-sur-Yvette, France
Yoel Kashman
School of Chemistry, Tel Aviv University, Tel Aviv 69978, Israel
Hermann Thomas
Parc national de La Réunion, Secteur Nord, 165 allée des spinelles Bellepierre, 97400 St-Denis, France
Jacqueline Smadja
Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de la Réunion, 15 Avenue René Cassin, CS 92003, 97744 St Denis, Messag CEDEX 9, La Réunion, France
Anne Gauvin-Bialecki
Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de la Réunion, 15 Avenue René Cassin, CS 92003, 97744 St Denis, Messag CEDEX 9, La Réunion, France
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.
