Literature DB >> 27519721

A soy extract catalyzes formation of 9-oxo-trans-12,13-epoxy-trans-10-octadecenoic acid from 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid.

H W Gardner1, R Kleiman1.   

Abstract

In the presence of oxygen, a crude soy extract converted 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid into numerous products, from which 9-oxo-trans-12,13-epoxy-trans-10-octadecenoic acid was isolated. Additionally, the soy extract oxidized linoleic acid to the oxo-epoxyoctadecenoic acid, presumably via a sequential reaction involving lipoxygenase oxidation of linoleic acid followed by degradation of the resultant linoleic acid hydroperoxide. However, the linoleic acid substrate yielded two isomeric linoleic acid hydroperoxides and because of this, two isomeric oxoepoxyoctadecenoic acids.

Entities:  

Year:  1977        PMID: 27519721     DOI: 10.1007/BF02533315

Source DB:  PubMed          Journal:  Lipids        ISSN: 0024-4201            Impact factor:   1.880


  11 in total

1.  Decomposition of unsaturated fatty acid hydroperoxides by hemoglobin: Structures of major products of 13L-hydroperoxy-9,11-octadecadienoic acid.

Authors:  M Hamberg
Journal:  Lipids       Date:  1975-02       Impact factor: 1.880

2.  A lipoperoxidase factor in soya extracts.

Authors:  J A BLAIN; E C STYLES
Journal:  Nature       Date:  1959-10-10       Impact factor: 49.962

3.  Enzymic reactions of fatty acid hydroperoxides in extracts of potato tuber. II. Conversion of 9- and 13-hydroperoxy-octadecadienoic acids to monohydroxydienoic acid, epoxyhydroxy- and trihydroxymonoenoic acid derivatives.

Authors:  T Galliard; D R Phillips; J A Matthew
Journal:  Biochim Biophys Acta       Date:  1975-11-21

4.  Oxygenated fatty acid constituents of soybean phosphatidylcholines.

Authors:  D J Sessa; H W Gardner; R Kleiman; D Weisleder
Journal:  Lipids       Date:  1977-07       Impact factor: 1.880

Review 5.  Decomposition of linoleic acid hydroperoxides. Enzymic reactions compared with nonenzymic.

Authors:  H W Gardner
Journal:  J Agric Food Chem       Date:  1975 Mar-Apr       Impact factor: 5.279

6.  Soya-bean lipoxygenase: an iron-containing dioxygenase.

Authors:  H W Chan
Journal:  Biochim Biophys Acta       Date:  1973-11-15

7.  Isolation of a pure isomer of linoleic acid hydroperoxide.

Authors:  H W Gardner
Journal:  Lipids       Date:  1975-04       Impact factor: 1.880

8.  The origin and structures of dimeric fatty acids from the anaerobic reaction between soya-bean lipoxygenase, linoleic acid and its hydroperoxide.

Authors:  G J Garssen; J F Vliegenthart; J Boldingh
Journal:  Biochem J       Date:  1972-11       Impact factor: 3.857

9.  The formation of threo-11-hydroxy-trans-12: 13-epoxy-9-cis-octadecenoic acid by enzymic isomerisation of 13-L-hydroperoxy-9-cis, 11-transoctadecadienoic acid by soybean lipoxygenase-1.

Authors:  G J Garssen; G A Veldink; J F Vliegenthart; J Boldingh
Journal:  Eur J Biochem       Date:  1976-02-02

10.  An anaerobic reaction between lipoxygenase, linoleic acid and its hydroperoxides.

Authors:  G J Garssen; J F Vliegenthart; J Boldingh
Journal:  Biochem J       Date:  1971-04       Impact factor: 3.857

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  1 in total

1.  9-Hydroxy-traumatin, a new metabolite of the lipoxygenase pathway.

Authors:  H W Gardner
Journal:  Lipids       Date:  1998-08       Impact factor: 1.880

  1 in total

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