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

鳕鱼卵素(Gadusol)是环己烷-1,3-二酮的烯醇衍生物,存在于鳕鱼卵和其他海洋鱼类中。本文对其分离、性质和存在情况进行了研究,并与抗坏血酸进行了比较。

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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.

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