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Structure‐retention correlation of isomeric bile acids in inclusion high‐performance liquid chromatography with methyl β‐cyclodextrin
Author(s) -
Momose Toshiaki,
Yamaguchi Yoshiya,
Iida Takashi,
Goto Junichi,
Nambara Toshio
Publication year - 1998
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-998-0185-y
Subject(s) - chemistry , high performance liquid chromatography , steroid , bile acid , chromatography , elution , amino acid , methanol , stereochemistry , organic chemistry , biochemistry , hormone
The structure‐retention correlation of various C 24 bile acid isomers was studied by the addition of methyl β‐cyclodextrin (Me‐β‐CD) to mobile phases in reversed‐phase high‐performance 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 5α‐H and cis 5β‐H) in the steroid nucleus. The inclusion HPLC with Me‐β‐CD was also applied to biologically important 4β‐ and 6‐hydroxylated bile acids substituted by three to four hydroxyl groups in the 5β‐steroid nucleus. These bile 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‐β‐CD. The effects of Me‐β‐CD on the retentions of each compound were correlated quantitatively to the decreasing rate of capacity factors and the relative strength of host‐guest inter‐actions. On the basis of the retention data, specific and nonspecific hydrogen‐bonding interactions between the bile acids and the Me‐β‐CD were discussed.