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植物甾醇以及α-和β-香树脂醇的立体特异性生物合成。

The stereospecific biosynthesis of plant sterols and alpha- and beta-amyrin.

作者信息

Rees H H, Mercer E I, Goodwin T W

出版信息

Biochem J. 1966 Jun;99(3):726-34. doi: 10.1042/bj0990726.

DOI:10.1042/bj0990726
PMID:5964969
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1265064/
Abstract
  1. A preparation of pea seedlings has been obtained that will incorporate [2-(14)C]mevalonate into squalene, alpha- and beta-amyrin and the phytosterols. 2. The (14)C/(3)H ratio in alpha- and beta-amyrin biosynthesized in the presence of [2-(14)C,4R-(3)H]-mevalonate is the same as in the starting material and in squalene; this gives experimental support to the mechanism for the cyclization of squalene proposed by Ruzicka for the formation of these pentacyclic triterpenoids. 3. The (14)C/(3)H ratio for beta-sitosterol was 5:3, the same as that in cholesterol in liver. 4. As the absence of (3)H from C-3 in beta-sitosterol was demonstrated (3)H must be present in the side chain and thus the H at C-24 is not lost during alkylation of the side chain; it probably migrates to C-25.
摘要
  1. 已获得一种豌豆幼苗制剂,它能将[2-(14)C]甲羟戊酸掺入角鲨烯、α-和β-香树脂醇以及植物甾醇中。2. 在[2-(14)C,4R-(3)H]-甲羟戊酸存在下生物合成的α-和β-香树脂醇中的(14)C/(3)H比值与起始原料和角鲨烯中的相同;这为鲁齐卡提出的角鲨烯环化形成这些五环三萜类化合物的机制提供了实验支持。3. β-谷甾醇的(14)C/(3)H比值为5:3,与肝脏中胆固醇的相同。4. 由于已证明β-谷甾醇的C-3位没有(3)H,(3)H必定存在于侧链中,因此在侧链烷基化过程中C-2位的H不会丢失;它可能迁移至C-25位。

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The stereospecific biosynthesis of plant sterols and alpha- and beta-amyrin.植物甾醇以及α-和β-香树脂醇的立体特异性生物合成。
Biochem J. 1966 Jun;99(3):726-34. doi: 10.1042/bj0990726.
2
The biosynthesis of beta-amyrin. Mechanism of squalene cyclization.β-香树脂醇的生物合成。角鲨烯环化机制。
Biochem J. 1968 Feb;106(3):659-65. doi: 10.1042/bj1060659.
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J Biol Chem. 1972 Oct 10;247(19):6243-6.
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引用本文的文献

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Genes (Basel). 2018 Jan 15;9(1):38. doi: 10.3390/genes9010038.
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Sterol biosynthesis in sub-cellular particles of higher plants.高等植物亚细胞颗粒中的甾醇生物合成。
Plant Physiol. 1969 Mar;44(3):442-6. doi: 10.1104/pp.44.3.442.
3
The biosynthesis of beta-amyrin. Mechanism of squalene cyclization.β-香树脂醇的生物合成。角鲨烯环化机制。
Biochem J. 1968 Feb;106(3):659-65. doi: 10.1042/bj1060659.
4
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Lipids. 1971 Apr;6(4):219-24. doi: 10.1007/BF02538391.
5
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6
Studies in phytosterol biosynthesis. Mechanism of biosynthesis of cycloartenol.植物甾醇生物合成的研究。环阿屯醇的生物合成机制。
Biochem J. 1968 Apr;107(3):417-26. doi: 10.1042/bj1070417.
7
The stereochemistry of hexahydroprenol, ubiquinone and ergosterol biosynthesis in the mycelium of Aspergillus fumigatus Fresenius.烟曲霉弗里斯菌菌丝体中六氢植醇、泛醌和麦角固醇生物合成的立体化学
Biochem J. 1967 Jul;104(1):43-56. doi: 10.1042/bj1040043.

本文引用的文献

1
Studies in carotenogenesis. 30. The problem of lycopersene formation in Neurospora crassa.类胡萝卜素生成的研究。30. 粗糙脉孢菌中番茄红素形成的问题。
Biochem J. 1963 May;87(2):326-9. doi: 10.1042/bj0870326.
2
Studies in carotenogenesis. 29. Attempts to detect lycopersene in higher plants.类胡萝卜素生成的研究。29. 检测高等植物中番茄红素的尝试。
Biochem J. 1963 May;87(2):317-25. doi: 10.1042/bj0870317.
3
THE MIGRATION AND ELIMINATION OF HYDROGEN DURING BIOSYNTHESIS OF CHOLESTEROL FROM SQUALENE.角鲨烯生物合成胆固醇过程中氢的迁移与消除
J Am Chem Soc. 1965 Jul 20;87:3224-8. doi: 10.1021/ja01092a038.
4
THIN-LAYER CHROMATOGRAPHY OF STEROLS AND STEROIDS.甾醇和类固醇的薄层色谱法
J Lipid Res. 1963 Jan;4:100-1.
5
Ketonic intermediates in the demethylation of lanosterol.羊毛甾醇去甲基化过程中的酮类中间体。
J Biol Chem. 1963 May;238:1661-4.
6
The biosynthesis of beta-amyrin and beta-sitosterol in germinating seeds of Pisum sativum.豌豆种子萌发过程中β-香树脂醇和β-谷甾醇的生物合成
Biochemistry. 1962 May 25;1:537-41. doi: 10.1021/bi00909a027.
7
Studies on the biosynthesis of cholesterol XIX. Steric course of hydrogen eliminations and of C-C bond formations in squalene biosynthesis.胆固醇生物合成的研究 XIX. 角鲨烯生物合成中氢消除和碳-碳键形成的立体化学过程。
Proc R Soc Lond B Biol Sci. 1966 Jan 18;163(993):492-514. doi: 10.1098/rspb.1966.0004.