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
来源：
PHYTOCHEMISTRY | 2012年 / 80卷
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
相关论文
共 50 条
  • [1] ent-Labdane Diterpenoids from the Aerial Parts of Eupatorium obtusissmum
    Castillo, Quirico A.
    Triana, Jorge
    Eiroa, Jose L.
    Calcul, Laurent
    Rivera, Edwin
    Wojtas, Lukasz
    Padron, Jose M.
    Boberieth, Lise
    Keramane, Mehdi
    Abel-Santos, Ernesto
    Baez, Luis A.
    Germosen, Evelyn A.
    JOURNAL OF NATURAL PRODUCTS, 2016, 79 (04): : 907 - 913
  • [2] Determination of the absolute configuration of (-)-mirtazapine by vibrational circular dichroism
    Freedman, TB
    Dukor, RK
    van Hoof, PJCM
    Kellenbach, ER
    Nafie, LA
    HELVETICA CHIMICA ACTA, 2002, 85 (04) : 1160 - 1165
  • [3] Absolute configuration of labdanes and ent-clerodanes from Chrormolaena pulchella by vibrational circular dichroism
    Gomez-Hurtado, Mario A.
    Martin Torres-Valencia, J.
    Manriquez-Torres, Jesus
    del Rio, Rosa E.
    Motilva, Virginia
    Garcia-Maurino, Sofia
    Avila, Javier
    Talero, Elena
    Cerda-Garcia-Rojas, Carlos M.
    Joseph-Nathan, Pedro
    PHYTOCHEMISTRY, 2011, 72 (4-5) : 409 - 414
  • [4] Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism
    Freedman, TB
    Cao, XL
    Oliveira, RV
    Cass, QB
    Nafie, LA
    CHIRALITY, 2003, 15 (02) : 196 - 200
  • [5] The determination of enantiomeric purity and absolute configuration by vibrational circular dichroism spectroscopy
    Nafie, LA
    Long, FJ
    Freedman, TB
    Buijs, H
    Rilling, A
    Roy, JR
    Dukor, RK
    FOURIER TRANSFORM SPECTROSCOPY, 1998, (430): : 432 - 434
  • [6] Determination of the absolute configuration of a novel tetrasubstituted isoindolinone by vibrational circular dichroism
    Massa, Antonio
    Rizzo, Paola
    Scorzelli, Francesco
    Monaco, Guglielmo
    Zanasi, Riccardo
    JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2017, 144 : 52 - 58
  • [7] Absolute configuration of eremophilanoids by vibrational circular dichroism
    Burgueno-Tapia, Eleuterio
    Joseph-Nathan, Pedro
    PHYTOCHEMISTRY, 2008, 69 (11) : 2251 - 2256
  • [8] Absolute configuration of (-)-myrtenal by vibrational circular dichroism
    Burgueno-Tapia, Eleuterio
    Gerardo Zepeda, L.
    Joseph-Nathan, Pedro
    PHYTOCHEMISTRY, 2010, 71 (10) : 1158 - 1161
  • [9] Determination of the absolute configuration and solution conformation of a novel disubstituted pyrrolidine acid A by vibrational circular dichroism
    Freedman, Teresa B.
    Cao, Xiaolin
    Phillips, Linda M.
    Cheng, Peter T. W.
    Dalterio, Richard
    Shu, Yue-Zhong
    Zhang, Hao
    Zhao, Ning
    Shukla, Rajesh B.
    Tymiak, Adrienne
    Gozo, Stephen K.
    Nafie, Laurence A.
    Gougoutas, Jack Z.
    CHIRALITY, 2006, 18 (09) : 746 - 753
  • [10] Exploring machine learning methods for absolute configuration determination with vibrational circular dichroism
    Vermeyen, Tom
    Brence, Jure
    Van Echelpoel, Robin
    Aerts, Roy
    Acke, Guillaume
    Bultinck, Patrick
    Herrebout, Wouter
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2021, 23 (35) : 19781 - 19789
12345