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乙醇代谢对体内甾体3 - 硫酸盐中C - 17处氧化还原和分子间氢转移的影响。

Effects of ethanol metabolism on oxidoreduction and intermolecular hydrogen transfer at C-17 in steroid 3-sulphates in vivo.

作者信息

Cronholm T, Rudqvist U

出版信息

Biochim Biophys Acta. 1982 Apr 15;711(1):159-65. doi: 10.1016/0005-2760(82)90022-4.

DOI:10.1016/0005-2760(82)90022-4
PMID:7066369
Abstract

Steroid sulphates were infused intravenously in female rats, and metabolites were isolated from bile. Infused 3 beta-hydroxy-5 alpha-androstan-17-one 3-sulphate was excreted together with 5 alpha-androstane-3 beta,17 beta-diol disulphate, which formed a large part after ethanol administration. Results from infusions of the 3-sulphates of 5 alpha-[17 alpha-2H]androstane-2 beta,17 beta-diol and 3 beta-hydroxy-5 alpha-[2,2,4,4-2H4]androstan-17-one indicated that ethanol decreased the extent of transfer of the 17 alpha-deuterium and increased the reduction of 17-oxosteroid without affecting the oxidation of 17 beta-hydroxysteroid. Ethanol metabolism decreased the deuterium transfer from [17 alpha-2H]estradiol 3-sulphate to C-17 of 3 beta-hydroxy-5 alpha-androstan-17-one 3-sulphate. The results indicate that NADH from ethanol metabolism increased the concentration of oxidoreductase-NADH complex without affecting the corresponding complex with NAD+. The effects of ethanol on steroid reduction were dependent on the initial redox state of the enzyme-coenzyme complex. This redox state was modified by substrates for the enzyme, indicating slow dissociation of the complex. Thus, ethanol metabolism may interfere with the interactions between steroid oxidoreductions.

摘要

将甾体硫酸盐静脉注射到雌性大鼠体内,然后从胆汁中分离代谢物。静脉注射的3β-羟基-5α-雄甾烷-17-酮3-硫酸盐与5α-雄甾烷-3β,17β-二醇二硫酸盐一起排泄,在给予乙醇后,后者占了很大一部分。对5α-[17α-2H]雄甾烷-2β,17β-二醇和3β-羟基-5α-[2,2,4,4-2H4]雄甾烷-17-酮的3-硫酸盐进行静脉注射的结果表明,乙醇降低了17α-氘的转移程度,并增加了17-氧代甾体的还原,而不影响17β-羟基甾体的氧化。乙醇代谢降低了[17α-2H]雌二醇3-硫酸盐向3β-羟基-5α-雄甾烷-17-酮3-硫酸盐C-17位的氘转移。结果表明,乙醇代谢产生的NADH增加了氧化还原酶-NADH复合物的浓度,而不影响与NAD+形成的相应复合物。乙醇对甾体还原的影响取决于酶-辅酶复合物的初始氧化还原状态。这种氧化还原状态被该酶的底物所改变,表明复合物的解离缓慢。因此,乙醇代谢可能会干扰甾体氧化还原之间的相互作用。

相似文献

1
Effects of ethanol metabolism on oxidoreduction and intermolecular hydrogen transfer at C-17 in steroid 3-sulphates in vivo.乙醇代谢对体内甾体3 - 硫酸盐中C - 17处氧化还原和分子间氢转移的影响。
Biochim Biophys Acta. 1982 Apr 15;711(1):159-65. doi: 10.1016/0005-2760(82)90022-4.
2
Hydrogen exchange during oxidoreduction and epimerization at C-3 of C19 steroid sulphates in the rat.大鼠体内C19甾体硫酸盐在C-3位进行氧化还原和差向异构化过程中的氢交换。
J Steroid Biochem. 1988 Jun;29(6):677-84. doi: 10.1016/0022-4731(88)90168-9.
3
Hydrogen transfer between C19 steroids during oxidoreduction at C-17 in vivo.体内C-17氧化还原过程中C19甾体之间的氢转移。
Biochim Biophys Acta. 1982 Apr 15;711(1):149-58. doi: 10.1016/0005-2760(82)90021-2.
4
Ethanol directly increases dihydrotestosterone conversion primarily to 5 alpha-androstan-3 beta, 17 beta-diol in rat Leydig cells.乙醇直接增加大鼠睾丸间质细胞中二氢睾酮的转化,主要转化为5α-雄甾烷-3β,17β-二醇。
Life Sci. 1985 Apr 8;36(14):1381-7. doi: 10.1016/0024-3205(85)90044-x.
5
Ethanol directly stimulates dihydrotestosterone conversion to 5 alpha-androstan-3 alpha, 17 beta-diol and 5 alpha-androstan-3 beta, 17 beta-diol in rat liver.乙醇直接刺激大鼠肝脏中双氢睾酮转化为5α-雄甾烷-3α,17β-二醇和5α-雄甾烷-3β,17β-二醇。
Life Sci. 1985 Mar 18;36(11):1117-24. doi: 10.1016/0024-3205(85)90497-7.
6
Ethanol directly increases dihydrotestosterone conversion to 5 alpha-androstan-3 beta,17 beta-diol and 5 alpha-androstan-3 alpha,17 beta-diol in rat Leydig cells.
Biochem Biophys Res Commun. 1984 Jun 15;121(2):558-65. doi: 10.1016/0006-291x(84)90218-3.
7
In vitro metabolism of testosterone to 17 beta-hydroxy-5 alpha-androstane-3-one and 5 alpha-androstane-3 alpha, 17 beta-diol by the rat intestine.
J Steroid Biochem. 1982 Oct;17(4):401-6. doi: 10.1016/0022-4731(82)90633-1.
8
Concentrations of unconjugated 5 alpha-androstane-3 alpha, 17 beta-diol and 5 alpha-androstane-3 beta, 17 beta-diol and their precursor in human testicular tissue. Comparison with testosterone, 5 alpha-dihydrotestosterone, estradiol-17 beta, and with steroid concentrations in human epididymis.人睾丸组织中未结合的5α-雄甾烷-3α,17β-二醇、5α-雄甾烷-3β,17β-二醇及其前体的浓度。与睾酮、5α-二氢睾酮、雌二醇-17β的比较,以及与人类附睾中甾体浓度的比较。
J Steroid Biochem. 1987 Mar;26(3):345-8. doi: 10.1016/0022-4731(87)90099-9.
9
[Metabolism of dihydrotestosterone in cultured skin fibroblasts: reduction to 5 alpha-androstane-3 alpha, 17 beta-diol].[培养的皮肤成纤维细胞中二氢睾酮的代谢:还原为5α-雄甾烷-3α,17β-二醇]
C R Seances Soc Biol Fil. 1983;177(1):83-92.
10
Hydrogen transfer between ethanol molecules during oxidoreduction in vivo.体内氧化还原过程中乙醇分子间的氢转移。
Biochem J. 1985 Jul 15;229(2):315-22. doi: 10.1042/bj2290315.