植物甾醇生物合成的研究。环阿屯醇的生物合成机制。
Studies in phytosterol biosynthesis. Mechanism of biosynthesis of cycloartenol.
作者信息
Rees H H, Goad L J, Goodwin T W
出版信息
Biochem J. 1968 Apr;107(3):417-26. doi: 10.1042/bj1070417.
Abstract
- The mechanism of cycloartenol biosynthesis in leaves of Solanum tuberosum was investigated with the use of [2-(14)C,(4R)-4-(3)H(1)]mevalonic acid. 2. The (3)H/(14)C atomic ratio in cycloartenol was 6:6, the same as that in squalene; this eliminates lanosterol as a possible biosynthetic precursor of cycloartenol, and indicates that a hydrogen migration from C-9 to C-8 occurs. 3. Chemical isomerization of the cycloartenol to lanosterol ((3)H/(14)C ratio 5:6) and parkeol ((3)H/(14)C ratio 6:6) confirms the hydrogen migration from C-9 to C-8. 4. Possible mechanisms for the biosynthesis of cycloartenol and parkeol are discussed. 5. The (3)H/(14)C ratio for 24-methylenecycloartanol was 6:6, demonstrating that the hydrogen atom at C-24 is retained during alkylation of the cycloartenol side chain.
摘要
- 利用[2-(14)C,(4R)-4-(3)H(1)]甲羟戊酸对马铃薯叶片中环阿屯醇的生物合成机制进行了研究。2. 环阿屯醇中(3)H/(14)C原子比为6:6，与角鲨烯中的相同；这排除了羊毛甾醇作为环阿屯醇可能的生物合成前体，并表明发生了从C-9到C-8的氢迁移。3. 环阿屯醇化学异构化为羊毛甾醇((3)H/(14)C比为5:6)和帕克醇((3)H/(14)C比为6:6)证实了从C-9到C-8的氢迁移。4. 讨论了环阿屯醇和帕克醇生物合成的可能机制。5. 24-亚甲基环阿屯醇的(3)H/(14)C比为6:6，表明在环阿屯醇侧链烷基化过程中C-24处的氢原子得以保留。
相似文献
1
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.
2
The biosynthesis of sterols in higher plants.高等植物中甾醇的生物合成。
Biochem J. 1966 Jun;99(3):735-46. doi: 10.1042/bj0990735.
3
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.
4
Studies in phytosterol biosynthesis: observations on the biosynthesis of fucosterol in the marine brown alga Fucus spiralis.植物甾醇生物合成的研究：对海洋褐藻螺旋藻中岩藻甾醇生物合成的观察。
Eur J Biochem. 1969 Feb;7(4):502-8. doi: 10.1111/j.1432-1033.1969.tb19636.x.
5
Concerning the role of lanosterol and cycloartenol in steroid biosynthesis.关于羊毛甾醇和环阿屯醇在类固醇生物合成中的作用。
J Biol Chem. 1971 Jun 25;246(12):3967-76.
6
Incorporation of (2-14C, (5r)-5-3H1) mevalonic acid into cholesterol by a rat liver homogenate and into beta-sitosterol and 28-isofucosterol by larix decidua leaves.大鼠肝脏匀浆将（2-¹⁴C，（5r）-5-³H¹）甲羟戊酸掺入胆固醇中，落叶松叶片将其掺入β-谷甾醇和28-异岩藻甾醇中。
Biochem J. 1969 Oct;114(4):885-92. doi: 10.1042/bj1140885.
7
Regulation of the sequencing in sterol biosynthesis.固醇生物合成中测序的调控。
Lipids. 1971 Apr;6(4):219-24. doi: 10.1007/BF02538391.
8
The conversion of [14C]cycloartenol and [14C)lanosterol into phytosterols by cultures of Nicotiana tabacum.烟草培养物将[14C]环阿屯醇和[14C]羊毛甾醇转化为植物甾醇的过程。
Eur J Biochem. 1969 Mar;8(2):184-8. doi: 10.1111/j.1432-1033.1969.tb00513.x.
9
The conversion of mevalonate to 24-methylenecycloartanol by a cell-free enzyme preparation from nonphotosynthetic tissue.通过非光合组织的无细胞酶制剂将甲羟戊酸转化为24-亚甲基环阿尔廷醇。
J Biol Chem. 1972 Oct 10;247(19):6243-6.
10
[Anerobic cyclization of squalen-2,3-epoxide to cycloartenol in Nicotiana tabacum L. tissue cultures].[烟草组织培养中角鲨烯-2,3-环氧化物厌氧环化生成环阿屯醇]
Eur J Biochem. 1969 Mar;8(2):180-3. doi: 10.1111/j.1432-1033.1969.tb00512.x.
引用本文的文献
1
Antidiabetes constituents, cycloartenol and 24-methylenecycloartanol, from Ficus krishnae.从诃子 Ficus krishnae 中分离得到的抗糖尿病成分：环阿尔廷醇和 24-亚甲基环阿尔廷醇。
PLoS One. 2020 Jun 25;15(6):e0235221. doi: 10.1371/journal.pone.0235221. eCollection 2020.
2
Drug strategies targeting CYP51 in neglected tropical diseases.针对被忽视热带病中细胞色素P450 51（CYP51）的药物策略。
Chem Rev. 2014 Nov 26;114(22):11242-71. doi: 10.1021/cr5003134. Epub 2014 Oct 22.
3
Biosynthesis of cholesterol and other sterols.胆固醇及其他甾醇的生物合成。
Chem Rev. 2011 Oct 12;111(10):6423-51. doi: 10.1021/cr200021m. Epub 2011 Sep 8.
4
Stereochemical aspects of the biosynthesis of the side chain of 9beta, 19-cyclopropyl sterols in maize seedlings treated with tridemorph.用十三吗啉处理的玉米幼苗中9β,19-环丙基甾醇侧链生物合成的立体化学方面
Plant Physiol. 1985 Dec;79(4):1098-106. doi: 10.1104/pp.79.4.1098.
5
Conformational analysis of 9beta,19-cyclopropyl sterols: Detection of the pseudoplanar conformer by nuclear Overhauser effects and its functional implications.9β,19-环丙基甾体的构象分析：通过核Overhauser 效应检测到拟平面构象及其功能意义。
Proc Natl Acad Sci U S A. 1988 Aug;85(16):5759-63. doi: 10.1073/pnas.85.16.5759.
6
Biosynthesis of 24-ethylcholesta-5,22,25-trien-3-beta-ol, a new sterol from Clerodendrum campbellii.24-乙基胆甾-5,22,25-三烯-3-β-醇的生物合成，一种来自灯笼树的新甾醇。
Biochem J. 1970 Jun;118(1):197-200. doi: 10.1042/bj1180197.
7
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.
8
Incorporation of (2-14C, (5r)-5-3H1) mevalonic acid into cholesterol by a rat liver homogenate and into beta-sitosterol and 28-isofucosterol by larix decidua leaves.大鼠肝脏匀浆将（2-¹⁴C，（5r）-5-³H¹）甲羟戊酸掺入胆固醇中，落叶松叶片将其掺入β-谷甾醇和28-异岩藻甾醇中。
Biochem J. 1969 Oct;114(4):885-92. doi: 10.1042/bj1140885.
9
The incorporation of a hydrogen atom at C-15 of cholesterol biosynthesized from squalene.在由角鲨烯生物合成的胆固醇的C-15位引入一个氢原子。
Biochem J. 1969 Oct;114(4):801-6. doi: 10.1042/bj1140801.
10
Optical-rotatory-dispersion studies of compounds related to cholesterol in liposomes and the membranes of erythrocyte 'ghosts'.脂质体和红细胞“血影”膜中与胆固醇相关化合物的旋光色散研究。
Biochem J. 1973 Sep;135(1):63-71. doi: 10.1042/bj1350063.
本文引用的文献
1
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.
2
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.
3
The isoprene rule and the biogenesis of terpenic compounds.异戊二烯规则与萜类化合物的生物合成
Experientia. 1953 Oct 15;9(10):357-67. doi: 10.1007/BF02167631.
4
The transfer of hydrogen from C-24 to C-25 in ergosterol biosynthesis.麦角固醇生物合成过程中氢从C-24向C-25的转移。
Biochem J. 1967 Jun;103(3):616-22. doi: 10.1042/bj1030616.
5
Enzymic synthesis of beta-amyrin from 2,3-oxidosqualene.从2,3-氧化角鲨烯酶促合成β-香树脂醇。
J Am Chem Soc. 1967 Jun 21;89(13):3362-3. doi: 10.1021/ja00989a055.
6
A soluble 2,3-oxidosqualene sterol cyclase.一种可溶性2,3-氧化角鲨烯甾醇环化酶。
J Biol Chem. 1967 Jun 25;242(12):3014-5.
7
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.
8
Biosynthesis of the phytosterol side chain.植物甾醇侧链的生物合成。
Nature. 1966 Jun 25;210(5043):1322-4. doi: 10.1038/2101322a0.
9
Enzymic conversion of squalene 2,3-oxide to lanosterol and cholesterol.角鲨烯2,3-氧化物向羊毛甾醇和胆固醇的酶促转化。
J Am Chem Soc. 1966 Oct 20;88(20):4752-4. doi: 10.1021/ja00972a058.
10
2,3-oxidosqualene, an intermediate in the biological synthesis of sterols from squalene.2,3-氧化角鲨烯，一种从角鲨烯生物合成甾醇过程中的中间体。
J Am Chem Soc. 1966 Oct 20;88(20):4750-1. doi: 10.1021/ja00972a056.
Zotero 插件