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J Biol Chem, Vol. 273, Issue 18, 10893-10900, May 1, 1998
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From the Departments of The metabolism of
4-hydroxy-trans-2-nonenal (HNE), an
Human Biological Chemistry
and Genetics and ¶ Physiology and Biophysics, University of Texas
Medical Branch, Galveston, Texas 77555-1067 and the
§ Analytical Chemistry Center, University of Texas Medical
School, Houston, Texas 77225
,
-unsaturated aldehyde generated during lipid peroxidation, was
studied in isolated perfused rat hearts. High performance liquid
chromatography separation of radioactive metabolites recovered
from [3H]HNE-treated hearts revealed four major peaks.
Based on the retention times of synthesized standards, peak I, which
accounted for 20% radioactivity administered to the heart, was
identified to be due to glutathione conjugates of HNE. Peaks II and
III, containing 2 and 37% radioactivity, were assigned to
1,4-dihydroxy-2-nonene (DHN) and 4-hydroxy-2-nonenoic acid,
respectively. Peak IV was due to unmetabolized HNE. The electrospray
ionization mass spectrum of peak I revealed two prominent metabolites
with m/z values corresponding to [M + H]+ of
HNE and DHN conjugates with glutathione. The presence of
4-hydroxy-2-nonenoic acid in peak III was substantiated using gas
chromatography-chemical ionization mass spectroscopy. When exposed to
sorbinil, an inhibitor of aldose reductase, no GS-DHN was recovered in
the coronary effluent, and treatment with cyanamide, an inhibitor of
aldehyde dehydrogenase, attenuated 4-hydroxy-2-nonenoic acid
formation. These results show that the major metabolic
transformations of HNE in rat heart involve conjugation with
glutathione and oxidation to 4-hydroxy-2-nonenoic acid. Further
metabolism of the GS-HNE conjugate involves aldose reductase-mediated reduction, a reaction catalyzed in
vitro by homogenous cardiac aldose reductase.
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