Separation and structure determination of two diastereomeric pairs of enantiomers from Dracocephalum rupestre by high-performance liquid chromatography with circular dichroism detection

被引：21

作者：

Ren, Dong-Mei ^{[1
]}

Guo, Huai-Fang ^{[1
]}

Wang, Shu-Qi ^{[1
]}

Lou, Hong-Xiang ^{[1
]}

机构：

[1] Shandong Univ, Sch Pharmaceut Sci, Jinan 250012, Peoples R China

来源：

JOURNAL OF CHROMATOGRAPHY A | 2007年 / 1161卷 / 1-2期

基金：

中国国家自然科学基金;

关键词：

dracocephalum rupestre; dracorupesins; HPLC-CD coupling analysis;

D O I：

10.1016/j.chroma.2007.06.034

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

All of the four stereoisomers of an unprecedented type of flavanones, the dracorupesins, were separated from the aerial parts of Dracocephalum rupestre simultaneously. The dracorupesins were characterized as two diastereomeric pairs of enantiomers by on-line chiral high-performance liquid chromatography-circular dichroism (HPLC-CD) analysis, which was a reliable stereoanalytical tool for natural products. The planar structures of the compounds were elucidated by means of spectroscopic methods including IR, MS, one-dimensional NMR (ID-NMR) and two-dimensional NMR (2D-NMR) techniques. (c) 2007 Elsevier B.V. All rights reserved.

引用

页码：334 / 337

页数：4

共 9 条

[1] Stereochemistry of isoplagiochin C, a macrocyclic bisbibenzyl from liverworts [J].

Bringmann, G ;

Mühlbacher, J ;

Reichert, M ;

Dreyer, M ;

Kolz, J ;

Speicher, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9283-9290

[2] The absolute configuration of(+)-isoshinanolone and in situ LC-CD analysis of its stereoisomers from crude extracts [J].

Bringmann, G ;

Messer, K ;

Saeb, W ;

Petes, EM ;

Peters, K .

PHYTOCHEMISTRY, 2001, 56 (04) :387-391

[3] Murrastifoline-F:: First total synthesis, atropo-enantiomer resolution, and stereoanalysis of an axially chiral N,C-coupled biaryl alkaloid [J].

Bringmann, G ;

Tasler, S ;

Endress, H ;

Kraus, J ;

Messer, K ;

Wohlfarth, M ;

Lobin, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2703-2711

[4] High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones [J].

Caccamese, S ;

Caruso, C ;

Parrinello, N ;

Savarino, A .

JOURNAL OF CHROMATOGRAPHY A, 2005, 1076 (1-2) :155-162

[5]

*JIANGS NEW MED CO, 1977, DICT CHIN TRAD MED S, P1347

[6] Metabolism of antioxidant in lemon fruit (Citrus limon B-URM. f.) by human intestinal bacteria [J].

Miyake, Y ;

Yamamoto, K ;

Osawa, T .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (10) :3738-3742

[7] The first 6′-O-sulfated phenylanthraquinones:: isolation from Bulbine frutescens, structural elucidation, enantiomeric purity, and partial synthesis [J].

Mutanyatta, J ;

Bezabih, M ;

Abegaz, BM ;

Dreyer, M ;

Brun, R ;

Kocher, N ;

Bringmann, G .

TETRAHEDRON, 2005, 61 (35) :8475-8484

[8]

REN DM, 2005, CHIN PHARM J, V22, P1695

[9]

Wu ZY, 1977, FLORA REIPUBLICAE PO, V65, P378

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