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岩芹酸,一种存在于鳕鱼和其他海鱼鱼卵中的环己烷 -1,3 - 二酮烯醇衍生物。与抗坏血酸相比的分离、性质及存在情况。

Gadusol, an enolic derivative of cyclohexane-1,3-dione present in the roes of cod and other marine fish. Isolation, properties and occurrence compared with ascorbic acid.

作者信息

Plack P A, Fraser N W, Grant P T, Middleton C, Mitchell A I, Thomson R H

出版信息

Biochem J. 1981 Dec 1;199(3):741-7. doi: 10.1042/bj1990741.

Abstract

Gadusol, C8H12O6, has been isolated from roes of the cod (Gadus morhua L.), i.e., ovaries that contain ripe eggs just before spawning. The concentration is about 4 g/kg dry wt. It has been identified as 1,4,5-trihydroxy-5-hydroxymethyl-2-methoxycyclo-hex-1-en-3-one and this structure was confirmed by synthesis of the anhydro tetra-acetate derivative from methyl 3,5-diacetoxy-4-methoxybenzoate. Concentrations of gadusol in the roes of other marine teleost fish examined are of the same order as in cod roes. Gadusol has some properties similar to ascorbic acid and both compounds, after oxidation, react with 2,4-dinitrophenylhydrazine in the commonly-used assay procedure for ascorbic acid. Specific assays showed that the concentrations of gadusol in the roes of marine fish are severalfold greater than those of ascorbic acid. Gadusol is structurally related to the mycosporines previously reported from a number of different organisms.

摘要

鳕醇(C8H12O6)是从鳕鱼(Gadus morhua L.)的鱼卵中分离出来的,即产卵前含有成熟卵子的卵巢。其含量约为4克/千克干重。它已被鉴定为1,4,5-三羟基-5-羟甲基-2-甲氧基环己-1-烯-3-酮,并且通过从3,5-二乙酰氧基-4-甲氧基苯甲酸甲酯合成脱水四乙酸衍生物证实了该结构。在检测的其他海洋硬骨鱼的鱼卵中,鳕醇的含量与鳕鱼鱼卵中的含量处于同一水平。鳕醇具有一些与抗坏血酸相似的特性,并且在氧化后,这两种化合物在常用的抗坏血酸检测方法中都能与2,4-二硝基苯肼发生反应。特定检测表明,海洋鱼类鱼卵中鳕醇的含量比抗坏血酸的含量高几倍。鳕醇在结构上与先前从许多不同生物体中报道的霉菌色素有关。

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