Determination of absolute configuration of salvic acid, an ent-labdane from Eupatorium salvia, by vibrational circular dichroism

被引:15
|
作者
Munoz, Marcelo A. [2 ]
Urzua, Alejandro [3 ]
Echeverria, Javier [3 ]
Bucio, Maria A. [1 ]
Hernandez-Barragan, Angelina [1 ]
Joseph-Nathan, Pedro [1 ]
机构
[1] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico
[2] Univ Austral Chile, Fac Ciencias, Inst Ciencias Quim, Valdivia, Chile
[3] Univ Santiago Chile, Fac Quim & Biol, Santiago, Chile
关键词
Eupatorium salvia; Asteraceae; VCD; Salvic acid; ent-Labdane; Absolute configuration; X-ray crystal structure; DITERPENES; CONSTITUENTS;
D O I
10.1016/j.phytochem.2012.04.014
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The relative stereochemistry at C13 and the absolute configuration of salvic acid, a constituent of the leaves of Eupatorium salvia, were established as the 13-(R)-ent-labdane 1. The results follow from vibrational circular dichroism measurements of the derived 0-methyl ether methyl ester 3 which were compared to OFT B3LYP/DGDZVP calculated spectra. The relative stereochemistry of salvic acid at C13 was independently verified by single crystal X-ray diffraction measurements of 1, and of its derived diol 4. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:109 / 114
页数:6
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