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昆虫和植物中蜕皮激素生物合成过程中C-7位氢消除的立体化学。

The stereochemistry of hydrogen elimination from C-7 during biosynthesis of ecdysones in insects and plants.

作者信息

Cook I F, Lloyd-Jones J G, Rees H H, Goodwin T W

出版信息

Biochem J. 1973 Sep;136(1):135-45. doi: 10.1042/bj1360135.

DOI:10.1042/bj1360135
PMID:4772621
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1165933/
Abstract
  1. [7alpha-(3)H(1)]- and [7beta-(3)H(1)]-Cholesterol were synthesized by a modified method. 2. The stereochemistry of Delta(7)-bond formation during ecdysone and ecdysterone biosynthesis in the insect, Calliphora erythrocephala and the plants, Taxus baccata and Polypodium vulgare was investigated by using [4-(14)C,7alpha-(3)H(1)]cholesterol and [4-(14)C,7beta-(3)H(1)]cholesterol. 3. In each case, the 7beta hydrogen was stereospecifically eliminated. 4. The possible significance of the results is discussed in relation to double-bond formation in other systems and the stage at which the Delta(7) bond is introduced during ecdysone biosynthesis.
摘要
  1. 通过改良方法合成了[7α-(3)H(1)]-胆固醇和[7β-(3)H(1)]-胆固醇。2. 利用[4-(14)C,7α-(3)H(1)]胆固醇和[4-(14)C,7β-(3)H(1)]胆固醇,研究了红头丽蝇、欧洲红豆杉和普通水龙骨中蜕皮激素和蜕皮甾酮生物合成过程中Δ(7)键形成的立体化学。3. 在每种情况下,7β氢都被立体定向消除。4. 结合其他系统中的双键形成以及蜕皮激素生物合成过程中引入Δ(7)键的阶段,讨论了这些结果可能具有的意义。

相似文献

1
The stereochemistry of hydrogen elimination from C-7 during biosynthesis of ecdysones in insects and plants.昆虫和植物中蜕皮激素生物合成过程中C-7位氢消除的立体化学。
Biochem J. 1973 Sep;136(1):135-45. doi: 10.1042/bj1360135.
2
Mode of formulation of cholesta-5,7-dien-3beta-ol from Cholest-5-en-3beta-ol by Larvae of Calliphora erythrocephala.红头丽蝇幼虫将胆甾-5-烯-3β-醇转化为胆甾-5,7-二烯-3β-醇的方式。
Biochem J. 1975 Nov;152(2):303-11. doi: 10.1042/bj1520303.
3
Lobster molting hormones: isolation and biosynthesis of ecdysterone.
Experientia. 1974 Jul 15;30(7):723-4. doi: 10.1007/BF01924149.
4
Occurrence of a metabolite related to pupation of the blowfly Calliphora erythrocephala Meig.
Riv Parassitol. 1966 Sep;27(3):203-9.
5
Studies on insect moulting hormones: biosynthesis of ponasterone A and ecdysterone from [2-14C] mevalonate in Taxus baccata.昆虫蜕皮激素的研究:从红豆杉中[2-14C]甲羟戊酸生物合成波尼松龙A和蜕皮甾酮。
Biochem J. 1969 Oct;114(4):895-6. doi: 10.1042/bj1140895.
6
The stereochemistry of hydrogen elimination from C-7 in cholesterol and ergosterol biosynthesis.胆固醇和麦角固醇生物合成过程中从C-7位消除氢的立体化学。
Biochem J. 1970 Apr;117(3):539-42. doi: 10.1042/bj1170539.
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The stereochemistry of hydrogen elimination during 7,8-double bond formation by Tetrahymena pyriformis.梨形四膜虫在形成7,8-双键过程中氢消除的立体化学
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26-Hydroxyecdysone, 20,26-dihydroxyecdysone and inokosterone detected as metabolites of ecdysone in the blowfly Calliphora vicina by radiotracer experiments.
Hoppe Seylers Z Physiol Chem. 1979 Sep;360(9):1351-5.
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Mechanism of formation of the A/B cis ring junction of ecdysteroids in Polypodium vulgare.普通水龙骨中蜕皮甾体A/B顺式环连接的形成机制。
Biochem J. 1980 Sep 15;190(3):537-44. doi: 10.1042/bj1900537.
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Metabolism of some possible ecdysone precursors in Calliphora stygia.黑角绿蝇中一些可能的蜕皮激素前体的代谢
J Insect Physiol. 1974 Dec;20(12):2433-45. doi: 10.1016/0022-1910(74)90029-8.

引用本文的文献

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Formation of the A/B cis ring junction of ecdysteroids in the locust, Schistocerca gregaria.飞蝗(沙漠蝗)中蜕皮甾体A/B顺式环连接的形成
Biochem J. 1981 Jan 15;194(1):53-62. doi: 10.1042/bj1940053.
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Mechanism of hydroxylation at C-22 during the biosynthesis of ecdysteroids in the locust Schistocerca gregaria.沙漠蝗Schistocerca gregaria蜕皮甾体生物合成过程中C-22位羟基化的机制。
Biochem J. 1982 Dec 15;208(3):857-64. doi: 10.1042/bj2080857.
4
Mode of formulation of cholesta-5,7-dien-3beta-ol from Cholest-5-en-3beta-ol by Larvae of Calliphora erythrocephala.红头丽蝇幼虫将胆甾-5-烯-3β-醇转化为胆甾-5,7-二烯-3β-醇的方式。
Biochem J. 1975 Nov;152(2):303-11. doi: 10.1042/bj1520303.
5
The role of a 5alpha-hydroxylated intermediate in the formation of the 5, 6-double bond in cholesterol biosynthesis.5α-羟基化中间体在胆固醇生物合成中5,6-双键形成过程中的作用。
Biochem J. 1975 Feb;145(2):345-52. doi: 10.1042/bj1450345.

本文引用的文献

1
The conversion of cholest-7-en-3beta-ol into cholesterol. General comments on the mechanism of the introduction of double bonds in enzymic reactions.胆甾-7-烯-3β-醇转变为胆固醇。关于酶反应中双键引入机制的一般评述。
Biochem J. 1967 Dec;105(3):1187-94. doi: 10.1042/bj1051187.
2
Conversion of 5-alpha-cholestan-3-beta-ol to delta-7-5-alpha-cholesten-3-beta-ol in cockroaches.蟑螂体内5-α-胆甾烷-3-β-醇向Δ⁷-5-α-胆甾烯-3-β-醇的转化
J Biol Chem. 1963 Jun;238:1966-72.
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[On the biogenesis of ecdyson. I. Conversion of cholesterol into ecdyson].
Hoppe Seylers Z Physiol Chem. 1963 Mar;331:289-300.
4
Mechanism of microbial transformation of cholesterol into coprostanol.
Eur J Biochem. 1971 Aug 16;21(3):428-32. doi: 10.1111/j.1432-1033.1971.tb01488.x.
5
The stereospecificity of the cholesterol delta 22-dehydrogenase of Tetrahymena pyriformis and the origin of the C-22 protons of cholesterol.梨形四膜虫胆固醇δ22 -脱氢酶的立体特异性及胆固醇C - 22质子的来源
J Biol Chem. 1970 Apr 10;245(7):1682-7.
6
The stereochemistry of hydrogen elimination during 7,8-double bond formation by Tetrahymena pyriformis.梨形四膜虫在形成7,8-双键过程中氢消除的立体化学
Biochem J. 1970 Feb;116(3):337-9. doi: 10.1042/bj1160337.
7
The stereochemistry of hydrogen elimination at C-7,C-22 and C-23 during the conversion of cholesterol (cholest-5-en-3 beta-ol) into cholesta-5,7,22-trien-3 beta-ol by Tetrahymena pyriformis.嗜热四膜虫将胆固醇(胆甾-5-烯-3β-醇)转化为胆甾-5,7,22-三烯-3β-醇过程中,C-7、C-22和C-23处氢消除的立体化学。
Biochem J. 1969 Dec;115(4):857-8. doi: 10.1042/bj1150857.
8
Steroid metabolism in rats given (1- 2 H 2 )ethanol. Biliary metabolites of corticosterone and administered 4-androstene-3,17-dione.
Eur J Biochem. 1972 May;27(1):10-22. doi: 10.1111/j.1432-1033.1972.tb01804.x.
9
The ecdysones.蜕皮激素
Pure Appl Chem. 1971;25(1):167-95. doi: 10.1351/pac197125010167.
10
Metabolic pathways of steroids in insects.昆虫中类固醇的代谢途径。
Proc R Soc Lond B Biol Sci. 1972 Feb 15;180(1059):203-21. doi: 10.1098/rspb.1972.0015.