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甾醇合成:14α-甲基-5α-胆甾-7-烯-3β-醇的代谢研究

Sterol synthesis: studies of the metabolism of 14 alpha-methyl-5 alpha-cholest-7-en-3 beta-ol.

作者信息

Chan J T, Spike T E, Trowbridge S T, Schroepfer G J

出版信息

J Lipid Res. 1979 Nov;20(8):1007-19.

PMID:533823
Abstract

[3 alpha-3H]14 alpha-Methyl-5 alpha-cholest-7-en-3 beta-ol has been prepared by chemical synthesis. The metabolism of this compound has been studied in the 10,000 g supernatant fraction of liver homogenates of female rats. Efficient conversion to cholesterol was observed. Other labeled compounds recovered after incubation of [3 alpha-3H]14 alpha-methyl-5 alpha-cholest-7-en-3 beta-ol with the enzyme preparations include the unreacted substrate, 5 alpha-cholesta-7,14-dien-3 beta-ol, 5 alpha-cholesta-8,14-dien-3 beta-ol, cholesta-5,7-dien-3 beta-ol, 5 alpha-cholest-8(14)-en-3 beta-ol, 5 alpha-cholest-8-en-3 beta-ol, and 5 alpha-cholest-7-en-3 beta-ol. In addition, significant amounts of incubated radioactivity were recovered in steryl esters. The steroidal components of these esters were found to contain labeled 14 alpha-methyl-5 alpha-cholest-7-en-3 beta-ol, 5 alpha-cholesta-8,14-dien-3 beta-ol, 5 alpha-cholesta-7,14-dien-3 beta-ol, 5 alpha-cholest-8-en-3 beta-ol, 5 alpha-cholest-7-en-3 beta-ol, and cholesterol.

摘要

[3α-³H]14α-甲基-5α-胆甾-7-烯-3β-醇已通过化学合成制备。该化合物在雌性大鼠肝脏匀浆10000g上清液部分中的代谢情况已得到研究。观察到其可高效转化为胆固醇。[3α-³H]14α-甲基-5α-胆甾-7-烯-3β-醇与酶制剂孵育后回收的其他标记化合物包括未反应的底物、5α-胆甾-7,14-二烯-3β-醇、5α-胆甾-8,14-二烯-3β-醇、胆甾-5,7-二烯-3β-醇、5α-胆甾-8(14)-烯-3β-醇、5α-胆甾-8-烯-3β-醇和5α-胆甾-7-烯-3β-醇。此外,在甾醇酯中回收了大量孵育后的放射性物质。发现这些酯的甾族成分含有标记的14α-甲基-5α-胆甾-7-烯-3β-醇、5α-胆甾-8,14-二烯-3β-醇、5α-胆甾-7,14-二烯-3β-醇、5α-胆甾-8-烯-3β-醇、5α-胆甾-7-烯-3β-醇和胆固醇。

相似文献

1
Sterol synthesis: studies of the metabolism of 14 alpha-methyl-5 alpha-cholest-7-en-3 beta-ol.甾醇合成:14α-甲基-5α-胆甾-7-烯-3β-醇的代谢研究
J Lipid Res. 1979 Nov;20(8):1007-19.
2
Inhibitors of cholesterol biosynthesis. Further studies of the metabolism of 5 alpha-cholest-8(14)-en-3 beta-ol-15-one in rat liver preparations.胆固醇生物合成抑制剂。大鼠肝脏制剂中5α-胆甾-8(14)-烯-3β-醇-15-酮代谢的进一步研究。
Chem Phys Lipids. 1988 May;47(1):21-46. doi: 10.1016/0009-3084(88)90030-8.
3
15-Oxygenated sterols with the unnatural cis-C-D ring junction. Studies of the metabolism of 5 alpha,14 beta-cholest-7-ene-3 beta,15 alpha-diol and 5 alpha,14 beta-cholest-7-ene-3 beta,15 beta-diol.具有非天然顺式C-D环连接的15-氧化甾醇。5α,14β-胆甾-7-烯-3β,15α-二醇和5α,14β-胆甾-7-烯-3β,15β-二醇的代谢研究。
J Biol Chem. 1980 Apr 25;255(8):3565-70.
4
15-Oxygenated sterols. Enzymatic conversion of [2,4]3H]5 alpha-cholest-8(14)-en-3 beta-ol-15-one to cholesterol in rat liver homogenate preparations.15-氧化甾醇。大鼠肝脏匀浆制剂中[2,4]³H]5α-胆甾-8(14)-烯-3β-醇-15-酮向胆固醇的酶促转化。
J Biol Chem. 1980 Dec 10;255(23):11122-9.
5
Inhibitors of sterol synthesis. Differential effects of 14 alpha-hydroxymethyl-5 alpha-cholest-7-ene-3 beta, 15 alpha-diol and 14 alpha-hydroxymethyl-5 alpha-cholest-6-ene-3 beta, 15 alpha-diol on sterol synthesis in cell-free homogenates of rat liver.固醇合成抑制剂。14α-羟甲基-5α-胆甾-7-烯-3β,15α-二醇和14α-羟甲基-5α-胆甾-6-烯-3β,15α-二醇对大鼠肝脏无细胞匀浆中固醇合成的不同影响。
J Biol Chem. 1981 Aug 10;256(15):8085-91.
6
Effect of trans-1,4-bis(2-chlorobenzylaminomethyl) cyclohexane dihydrochloride and carbon monoxide on hepatic cholesterol biosynthesis from 4,4,-dimethyl sterols in vitro.反式-1,4-双(2-氯苄氨基甲基)环己烷二盐酸盐与一氧化碳对体外4,4'-二甲基甾醇肝胆固醇生物合成的影响
Biochim Biophys Acta. 1975 Feb 20;380(2):270-81. doi: 10.1016/0005-2760(75)90013-2.
7
A novel olefinic rearrangement. The enzymic conversion of cholesta-7,9-dien-3 -ol into cholesta-8,14-dien-3 -ol.一种新型烯烃重排反应。胆甾-7,9-二烯-3-醇向胆甾-8,14-二烯-3-醇的酶促转化。
Biochem J. 1972 Sep;129(2):225-9. doi: 10.1042/bj1290225.
8
Further studies on the inhibition of sterol biosynthesis in animal cells by 15-oxygenated sterols.关于15-氧化固醇对动物细胞中固醇生物合成抑制作用的进一步研究。
Chem Phys Lipids. 1979 Nov;25(3):265-85. doi: 10.1016/0009-3084(79)90111-7.
9
Inhibitors of sterol synthesis. Spectral characterization of derivatives of 5 alpha-cholest-8(14)-en-3 beta-ol-15-one.
J Lipid Res. 1987 Nov;28(11):1296-307.
10
Inhibition of sterol synthesis by delta 5-sterols in a sterol auxotroph of yeast defective in oxidosqualene cyclase and cytochrome P-450.在氧化角鲨烯环化酶和细胞色素P-450缺陷的酵母甾醇营养缺陷型中,δ5-甾醇对甾醇合成的抑制作用
J Biol Chem. 1988 Aug 25;263(24):11844-50.