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

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Lipids

Abstract

9-Hydroxy-traumatin, 9-hydroxy-12-oxo-10E-dodecenoic acid, was isolated as a product of 13S-hydroperoxy-9Z, 11E-octadecadienoic acid as catalyzed by enzyme preparations of both soybean and alfalfa seedlings. This suggested that 9Z-traumatin, 12-oxo-9Z-dodecenoic acid, was being converted into 9-hydroxy-traumatin in an analogous manner to the previously identified enzymic conversion of 3Z-nonenal and 3Z-hexenal into 4-hydroxy-2E-nonenal and 4-hydroxy-2E-hexenal, respectively. Other metabolites of 13S-hydroperoxy-9Z,11E-octadecadienoic acid were similar for both soybean and alfalfa seedling preparations, and they are briefly described.

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Abbreviations

EIMS:

Electron impact-mass spectrum

GC-MS:

gas chromatography-mass spectrometry

1H NMR:

proton nuclear magnetic resonance spectrometry

13S-HPODE:

13S-hydroperoxy-9Z,11E-octadecadienoic acid

9:

hydroxy-traumatin, 9-hydroxy-12-oxo-10E-dodecenoic acid

OTMS:

trimethylsilyloxy ether

TLC:

thin-layer chromatography

traumatic acid:

2E-dodecendioic acid; 9Z-traumatin, 12-oxo-9Z-dodecenoic acid

10E :

traumatin, 12-oxo-10E-dodecenoic acid

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Authors and Affiliations

  1. Bioactive Research, National Center for Agricultural Utilization Research, ARS, USDA, 1815 N. University St., 61604, Peoria, Illinois

    Harold W. Gardner

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  1. Harold W. Gardner
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Correspondence to Harold W. Gardner.

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Gardner, H.W. 9-Hydroxy-traumatin, a new metabolite of the lipoxygenase pathway. Lipids 33, 745–749 (1998). https://doi.org/10.1007/s11745-998-0265-z

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  • DOI: https://doi.org/10.1007/s11745-998-0265-z

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