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用硼氢化钠还原氧化脂质过程中不可避免地会生成伯醇。

Inevitable generation of primary alcohols during reduction of oxidized lipids with sodium borohydride.

作者信息

Nakamura T, Maeda H, Takahashi Y, Hama Y

机构信息

Laboratory of Fisheries Technology, Faculty of Agriculture, Kyushu University, 6-10-1, Hakozaki, 812, Fukuoka, Japan.

出版信息

Lipids. 1990 Sep;25(9):578-80. doi: 10.1007/BF02537169.

DOI:10.1007/BF02537169
PMID:27520800
Abstract

This report deals with the fluorometric determination of fatty alcohols generated by the reduction of the ester linkage of lipids with NaBH4, and with the limitations of the reduction method for assaying oxidized lipids. Optimum conditions for the fluorometric analysis of primary and secondary alcohols using 1-anthroyl nitrile were obtained. After reduction with NaBH4 in MeOH or in MeOH/benzene (8∶2, v/v), the formation of 1-hexadecanol from a variety of palmitic acid esters was measured fluorometrically by reverse-phase high-performance liquid chromatography (HPLC): From glycerides and methyl palmitate, 1-3% (w/w) 1-hexadecanol was produced and a trace was produced from cholesteryl palmitate (10 min, 21°C). 1-Hexadecanol was never generated from palmitic acid. Although considerable improvement occurred with the choice of the solvent for the NaBH4 reduction, the generation of primary alcohols from ester lipids usually seems inevitable.

摘要

本报告涉及用荧光法测定用硼氢化钠还原脂质酯键所生成的脂肪醇,以及该还原法在分析氧化脂质时的局限性。获得了使用1-蒽腈对伯醇和仲醇进行荧光分析的最佳条件。在甲醇或甲醇/苯(8∶2,v/v)中用硼氢化钠还原后,通过反相高效液相色谱(HPLC)荧光法测定了多种棕榈酸酯生成1-十六醇的情况:从甘油酯和棕榈酸甲酯中产生了1-3%(w/w)的1-十六醇,而从棕榈酸胆固醇酯中产生了微量的1-十六醇(10分钟,21°C)。棕榈酸从未生成1-十六醇。尽管在选择硼氢化钠还原的溶剂方面有了相当大的改进,但从酯类脂质中生成伯醇似乎通常是不可避免的。

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本文引用的文献

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On the specificity of the oxygenation of unsaturated fatty acids catalyzed by soybean lipoxidase.关于大豆脂氧化酶催化的不饱和脂肪酸氧化作用的特异性
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Isolation and structure of two prostaglandin endoperoxides that cause platelet aggregation.两种引起血小板聚集的前列腺素内过氧化物的分离与结构
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7
Autoxidation of polyunsaturated fatty acids: II. A suggested mechanism for the formation of TBA-reactive materials from prostaglandin-like endoperoxides.多不饱和脂肪酸的自动氧化:II. 一种由前列腺素样内过氧化物形成TBA反应性物质的推测机制。
Lipids. 1976 May;11(5):370-9. doi: 10.1007/BF02532843.
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Lipids. 1977 Nov;12(11):901-7. doi: 10.1007/BF02533309.
9
Autoxidation of methyl linoleate. Separation and analysis of isomeric mixtures of methyl linoleate hydroperoxides and methyl hydroxylinoleates.亚油酸甲酯的自动氧化。亚油酸甲酯氢过氧化物和羟基亚油酸甲酯异构体混合物的分离与分析。
Lipids. 1977 Jan;12(1):99-104. doi: 10.1007/BF02532979.
10
Cyclic peroxides from a soya lipoxygenase-catalysed oxygenation of methyl linolenate.来自大豆脂氧合酶催化的亚麻酸甲酯氧化反应的环状过氧化物。
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