Structure-retention correlation of isomeric bile acids in inclusion high-performance liquid chromatography with methyl β-cyclodextrin
Structure-retention correlation of isomeric bile acids in inclusion high-performance liquid chromatography with methyl β-cyclodextrin
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DOI：
10.1007/s11745-998-0185-y
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发表时间：
1998-01-01
期刊：
影响因子：
1.9
通讯作者：
Nambara, T
中科院分区：
文献类型：
--
作者：
Momose, T;Yamaguchi, Y;Nambara, T
通过向流动相中加入甲基β-环糊精(Me-β-CD)，研究了不同C(24)胆汁酸异构体的结构-保留相关性。所研究的化合物包括一系列与胆酸有关的单取代胆汁酸，它们在C-3、C-6、C-7或C-12位置上的含氧官能团(羟基或氧基)的位置和构型以及类固醇核中A/B环融合的立体化学(反式5α-H和顺式5β-H)不同。Me-β-CD包合高效液相色谱也用于生物活性重要的4-β-和6-羟基胆汁酸，5-β-甾体核内3~4个羟基取代胆汁酸。这些咬合酸样品被转换成预先标记的24-吡喃酰基酯的荧光衍生物，并在Capcell Pak C(18)柱上进行层析，在存在或不存在5 mM Me-β-CD的情况下，用甲醇-水混合物洗脱。Me-β-CD对各化合物保留率的影响与容量因子的下降率和主客体相互作用的相对强度有定量关系。在保留数据的基础上，讨论了胆汁酸与Me-β-CD之间的特异性和非特异性氢键相互作用。
The structure-retention correlation of various C(24) bile acid isomers was studied by the addition of methyl beta-cyclodextrin (Me-beta-CD) to mobile phases in reversed-phase highperformance liquid chromatography (HPLC). The compounds examined include a series of monosubstituted bile acids related to cholanoic acids differing from one another in the position and configuration of an oxygen-containing function (hydroxyl or oxo group) at the position C-3, C-6, C-7, or C-12 and the stereochemistry of the A/B-ring fusion (trans 5 alpha-H and cis 5 beta-H) in the steroid nucleus. The inclusion HPLC with Me-beta-CD was also applied to biologically important 4 beta- and 6-hydroxylated bile acids substituted by three to four hydroxyl groups in the 5 beta-steroid nucleus. These bite acid samples were converted into their fluorescence prelabeled 24-pyrenacyl ester derivatives and chromatographed on a Capcell Pak C(18) column eluted with methanol-water mixtures in the presence or absence of 5 mM Me-beta-CD. The effects of Me-beta-CD on the retentions of each compound were correlated quantitatively to the decreasing rate of capacity factors and the relative strength of host-guest interactions. On the basis of the retention data, specific and nonspecific hydrogen-bonding interactions between the bile acids and the Me-beta-CD were discussed.