Open AccessIdentification of C 19 O 2 and C 21 O 2 Steroids in the Mono‐ and Disulphate Fractions of Human Faeces
Author(s) -
Laatikainen T.,
Vihko R.
Publication year - 1970
Publication title -
european journal of biochemistry
Language(s) - English
Resource type - Journals
eISSN - 1432-1033
pISSN - 0014-2956
DOI - 10.1111/j.1432-1033.1970.tb00957.x
Subject(s) - diol , pregnane , chemistry , chromatography , sephadex , fraction (chemistry) , pregnenolone , hydrolysis , gas chromatography , steroid , stereochemistry , organic chemistry , biochemistry , enzyme , hormone
Steroid monosulphate and disulphate fractions were obtained from human faeces by chromatography on Sephadex LH‐20 and solvolysed. The steroids liberated were fractionated on silicic acid. Fractions containing C 19 O 2 and C 21 O 2 steroids were studied by thin‐layer chromatography, gas‐liquid chromatography and gas chromatography‐mass spectrometry. Dehydroepiandrosterone, 5α‐androstane‐3α,17α‐diol, 5α‐androstane‐3α,17β‐diol, 5α‐androstane‐3β,17α‐diol, 5α‐androstane‐3β,17β‐diol, 5β‐androstane‐3α,17β‐diol, 5‐androstene‐3α,17β‐diol, 5‐androstene‐3β,17α‐diol, 5‐androstene‐3β,17β‐diol, 5α‐pregnane‐3α,20α‐diol, 5α‐pregnane‐3β,20α‐diol, 5β‐pregnane‐3α,20α‐diol, 5β‐pregnane‐3β,20α‐diol,pregnenolone, 5‐pregnene‐3α,20α‐diol and 5‐pregnene‐3β,20α‐diol were found in the monosulphate fraction and 5‐androstene‐3β,17α‐diol as well as 5‐androstene‐3β,17β‐diol in the disulphate fraction of human faeces. Several steroids identified earlier in the disulphate fraction of human bile were found in the monosulphate fraction of human faeces, indicating partial hydrolysis of diconjugates in the intestine. The androstanediols and pregnanediols found in the faeces were primarily of a 3β‐hydroxy‐5α‐ or 3β‐hydroxy‐5β‐structure, whereas those in the bile were of a 3α‐hydroxy‐5α‐ or 3α‐hydroxy‐5β‐structure. This suggests conversion of a 3α‐hydroxyl to a 3β‐hydroxyl in the intestine in vivo .