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.
Abstract
- [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
- 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.
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.
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.
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.
Biochem J. 1970 Apr;117(3):539-42. doi: 10.1042/bj1170539.
7
The stereochemistry of hydrogen elimination during 7,8-double bond formation by Tetrahymena pyriformis.
Biochem J. 1970 Feb;116(3):337-9. doi: 10.1042/bj1160337.
8
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.
9
Mechanism of formation of the A/B cis ring junction of ecdysteroids in Polypodium vulgare.
Biochem J. 1980 Sep 15;190(3):537-44. doi: 10.1042/bj1900537.
10
Metabolism of some possible ecdysone precursors in Calliphora stygia.
J Insect Physiol. 1974 Dec;20(12):2433-45. doi: 10.1016/0022-1910(74)90029-8.
引用本文的文献
1
The phytochemical, biological, and medicinal attributes of phytoecdysteroids: An updated review.
Acta Pharm Sin B. 2021 Jul;11(7):1740-1766. doi: 10.1016/j.apsb.2020.10.012. Epub 2020 Oct 16.
2
Formation of the A/B cis ring junction of ecdysteroids in the locust, Schistocerca gregaria.
Biochem J. 1981 Jan 15;194(1):53-62. doi: 10.1042/bj1940053.
3
Mechanism of hydroxylation at C-22 during the biosynthesis of ecdysteroids in the locust Schistocerca gregaria.
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.
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.
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.
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.
J Biol Chem. 1963 Jun;238:1966-72.
3
[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.
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.
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.
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.
Pure Appl Chem. 1971;25(1):167-95. doi: 10.1351/pac197125010167.
10
Metabolic pathways of steroids in insects.
Proc R Soc Lond B Biol Sci. 1972 Feb 15;180(1059):203-21. doi: 10.1098/rspb.1972.0015.
Zotero 插件