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

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 b...

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Published in:Biochemical Journal
Main Authors: Plack, P A, Fraser, N W, Grant, P T, Middleton, C, Mitchell, A I, Thomson, R H
Format: Article in Journal/Newspaper
Language:English
Published: Portland Press Ltd. 1981
Subjects:
Gadus morhua
Online Access:http://dx.doi.org/10.1042/bj1990741
https://portlandpress.com/biochemj/article-pdf/199/3/741/623266/bj1990741.pdf
id crportlandpress:10.1042/bj1990741
record_format openpolar
spelling crportlandpress:10.1042/bj1990741 2024-09-09T19:40:54+00:00 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 Plack, P A Fraser, N W Grant, P T Middleton, C Mitchell, A I Thomson, R H 1981 http://dx.doi.org/10.1042/bj1990741 https://portlandpress.com/biochemj/article-pdf/199/3/741/623266/bj1990741.pdf en eng Portland Press Ltd. Biochemical Journal volume 199, issue 3, page 741-747 ISSN 0264-6021 journal-article 1981 crportlandpress https://doi.org/10.1042/bj1990741 2024-08-08T04:25:07Z 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. Article in Journal/Newspaper Gadus morhua Portland Press Biochemical Journal 199 3 741 747
institution Open Polar
collection Portland Press
op_collection_id crportlandpress
language English
description 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.
format Article in Journal/Newspaper
author Plack, P A
Fraser, N W
Grant, P T
Middleton, C
Mitchell, A I
Thomson, R H
spellingShingle Plack, P A
Fraser, N W
Grant, P T
Middleton, C
Mitchell, A I
Thomson, R H
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
author_facet Plack, P A
Fraser, N W
Grant, P T
Middleton, C
Mitchell, A I
Thomson, R H
author_sort Plack, P A
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publisher Portland Press Ltd.
publishDate 1981
url http://dx.doi.org/10.1042/bj1990741
https://portlandpress.com/biochemj/article-pdf/199/3/741/623266/bj1990741.pdf
genre Gadus morhua
genre_facet Gadus morhua
op_source Biochemical Journal
volume 199, issue 3, page 741-747
ISSN 0264-6021
op_doi https://doi.org/10.1042/bj1990741
container_title Biochemical Journal
container_volume 199
container_issue 3
container_start_page 741
op_container_end_page 747
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