ISOLATION AND STRUCTURAL ELUCIDATION OF THE GEOMETRICAL-ISOMERS OF LUTEIN AND ZEAXANTHIN IN EXTRACTS FROM HUMAN PLASMA
ISOLATION AND STRUCTURAL ELUCIDATION OF THE GEOMETRICAL-ISOMERS OF LUTEIN AND ZEAXANTHIN IN EXTRACTS FROM HUMAN PLASMA
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DOI：
10.1016/0378-4347(92)80314-g
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发表时间：
1992-11-06
期刊：
影响因子：
--
通讯作者：
LUSBY, WR
中科院分区：
文献类型：
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作者：
KHACHIK, F;ENGLERT, G;LUSBY, WR
用半制备高效液相色谱法从人血浆中分离出全-E-（3R，3 'R，6' R）-叶黄素、全-E-（3R，3 'R）-玉米黄质、全-E-（3R，3'S，6' R）-3 '-表叶黄素及前两种二羟基类胡萝卜素的几何异构体。按色谱洗脱顺序，分离的组分被鉴定为全E-叶黄素、全E-玉米黄质、全E-3 '-表叶黄素、9 Z-叶黄素、9' Z-叶黄素、13 Z-叶黄素和13 'Z-叶黄素的混合物、9 Z-玉米黄质、13 Z-玉米黄质和15 Z-玉米黄质。所有化合物的结构，包括叶黄素在C（3 '）和C（6'）处的相对构型以及几何异构体中立体突变双键的位置，均通过H-1核磁共振光谱法明确确定。这三种全E化合物的绝对构型是由圆二色性推导出来的，并且也被认为对几何异构体有效。每个单独分离的化合物的紫外-可见吸收光谱和质谱也与提出的结构一致。
All-E-(3R,3'R,6'R)-lutein, all-E-(3R,3'R)-zeaxanthin, all-E-(3R,3'S,6'R)-3'-epilutein and some geometrical isomers of the former two dihydroxycarotenoids have been separated from an extract of human plasma by semipreparative high-performance liquid chromatography on a silica-based nitrile-bonded column. In the order of chromatographic elution, the isolated fractions were identified as all-E-lutein, all-E-zeaxanthin, all-E-3'-epilutein, 9Z-lutein, 9'Z-lutein, a mixture of 13Z-lutein and 13'Z-lutein, 9Z-zeaxanthin, 13Z-zeaxanthin and 15Z-zeaxanthin. The structures of all compounds, including the relative configuration at C(3') and C(6') of the luteins and the position of the stereomutated double bonds in the geometrical isomers, were unambiguously established by H-1 nuclear magnetic resonance spectroscopy. The absolute configuration of the three all-E compounds was derived by circular dichroism and is also assumed to be valid for the geometrical isomers. The ultraviolet-visible absorption and mass spectra of each of the individually isolated compounds were also in agreement with the proposed structures.