叶片精油中的修饰葎草烷类化合物

Modified Clerodanes from the Essential Oil of Leaves.

机构信息

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.

Institut de Chimie des Substances Naturelles, CNRS, 91110 Gif-sur-Yvette, France.

出版信息

Molecules. 2020 Feb 14;25(4):850. doi: 10.3390/molecules25040850.

DOI:10.3390/molecules25040850

PMID:32075135

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7070720/

Abstract

(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.

摘要

（L.）来自印度洋留尼汪岛的 Jacq 被研究了其叶精油成分。该植物通过水蒸馏提取，并用气相色谱-质谱联用技术分析其精油。这项研究表明，含氧的诺二萜和二萜是主要的化学类之一（>50%），主要由三个含有双环[5.4.0]十一烷环系的改性环丙基克列班多烷组成：一个新的呋喃型诺二萜，dodovisate C，和两个呋喃型二萜，已知的甲基 dodovisate A 和新的甲基异-dodovisate A。这三种化合物通过液相色谱分离，并根据光谱研究确定了它们的结构。通过实验和理论（B3LYP/6-311+G(d,p)）电子圆二色性研究联合阐明了 dodovisate C 的绝对构型。使用（B3LYP/6-311+G(d,p)）方法，通过理论化学位移与实验值的线性回归，确定了甲基 dodovisate A 和甲基异-dodovisate A 的相对构型。