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黄粉虫中海绵甾醇脱烷基化的机制

Mechanism of dealkylation of clionasterol in the insect Tenebrio molitor.

作者信息

Pettler P J, Lockley W J, Rees H H, Goodwin T W

出版信息

Biochem J. 1978 Aug 15;174(2):397-404. doi: 10.1042/bj1740397.

DOI:10.1042/bj1740397
PMID:708391
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1185927/
Abstract
  1. 25-3H- and 26-14C-labelled (24S)-24-ethylcholest-5-en-3beta-ol (clionasterol) were synthesized from (24S)-24-ethylcholesta-5,25-dien-3beta-ol. 2. These labelled substrates were mixed and administered, together with the hypocholesterolemic agent, triparanol citrate, to Tenebrio molitor larvae. 3. The 3H label from the clionasterol substrate was retained in both the desmosterol and the cholesterol isolated from the larvae. 4. Location of this 3H label in the desmosterol showed that dealkylation of the clionasterol involved 3H migration from C-25 to C-24. A possible mechanism for dealkylation is presented.
摘要
  1. 由（24S）-24-乙基胆甾-5,25-二烯-3β-醇合成了25-³H-和26-¹⁴C-标记的（24S）-24-乙基胆甾-5-烯-3β-醇（麦角甾醇）。2. 将这些标记的底物与降胆固醇剂柠檬酸三苯乙醇胺混合后，给予黄粉虫幼虫。3. 麦角甾醇底物中的³H标记保留在从幼虫中分离出的脱氢胆固醇和胆固醇中。4. 该³H标记在脱氢胆固醇中的定位表明，麦角甾醇的脱烷基化涉及³H从C-25迁移至C-24。文中提出了一种可能的脱烷基化机制。

相似文献

1
Mechanism of dealkylation of clionasterol in the insect Tenebrio molitor.黄粉虫中海绵甾醇脱烷基化的机制
Biochem J. 1978 Aug 15;174(2):397-404. doi: 10.1042/bj1740397.
2
Role of 24- and 28-hydroxylated intermediates in the metabolism of beta-sitosterol in the insect Tenebrio molitor.24-羟基和28-羟基中间体在黄粉虫β-谷甾醇代谢中的作用。
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本文引用的文献

1
Desmosterol, an intermediate in dealkylation of beta-sitosterol in the tobacco hornworm.麦角甾醇，烟草天蛾中β-谷甾醇脱烷基化的中间体。
Life Sci. 1967 Feb 15;6(4):395-404. doi: 10.1016/0024-3205(67)90009-4.
2
Conversion of beta sitosterol to cholesterol blocked in an insect by hypocholesterolemic agents.在昆虫体内，β-谷甾醇向胆固醇的转化被降胆固醇药物阻断。
Science. 1967 Jun 23;156(3782):1637-8. doi: 10.1126/science.156.3782.1637.
3
Identification of fucosterol as a metabllite and probable intermediate in conversion of beta-sitosterol to cholesterol in the tobacco hornworm.鉴定岩藻甾醇作为烟草天蛾中β-谷甾醇转化为胆固醇的一种代谢物及可能的中间体。
Nat New Biol. 1971 Mar 10;230(10):57-8. doi: 10.1038/newbio230057a0.
4
Metabolism of steroids in insects.昆虫中类固醇的代谢
Adv Lipid Res. 1973;11:219-65. doi: 10.1016/b978-0-12-024911-4.50013-1.
5
Reaction of 24,28-epoxides of sterol side chain with boron trifluoride etherate.甾醇侧链的24,28-环氧化物与三氟化硼乙醚的反应。
J Org Chem. 1973 May 4;38(9):1688-91. doi: 10.1021/jo00949a015.
6
The relation of carnitine to the formation of phosphatidyl-beta-methylcholine by Tenebrio molitor L. larvae.肉碱与黄粉虫幼虫形成磷脂酰-β-甲基胆碱的关系。
Lipids. 1969 Jul;4(4):293-8. doi: 10.1007/BF02533189.
7
Letter: Stereospecificity in the conversion of fucosterol 24,28-epoxide to desmosterol in the silkworm, Bombyx mori.信函：家蚕中岩藻甾醇24,28-环氧化物向去甲胆甾醇转化过程中的立体特异性
J Am Chem Soc. 1975 Sep 3;97(18):5297-9. doi: 10.1021/ja00851a056.
8
Recent developments in insect steroid metabolism.昆虫类固醇代谢的最新进展。
Annu Rev Entomol. 1975;20:205-20. doi: 10.1146/annurev.en.20.010175.001225.