Intracellular metabolism of 4-hydroxynonenal

Molecular Aspects of Medicine

Volumn 24, Issue 4-5, 2003, Pages 167-175

  Siems, Werner ^a   Grune, Tilman ^b  

^a Herzog Julius Klinik GmbH & Co KG   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

4 Hydroxynonenal (HNE); Glutathione; Hepatocytes; Lipid peroxidation; Oxidative stress; Protein oxidation

Indexed keywords

4 HYDROXYNONENAL;

CELL FUNCTION; CONFERENCE PAPER; CYTOTOXICITY; ENDOTHELIUM CELL; FIBROBLAST; HEART MUSCLE CELL; HUMAN; INTESTINE CELL; KIDNEY TUBULE CELL; LIPID PEROXIDATION; LIVER CELL; MAMMAL CELL; NEUTROPHIL; NONHUMAN; PATHOPHYSIOLOGY; SIGNAL TRANSDUCTION; THYMOCYTE; TUMOR CELL;

MAMMALIA;

EID: 0042170296     PISSN: 00982997     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0098-2997(03)00011-6     Document Type: Conference Paper

References (45)

1. Alary J., Bravais F., Cravedi J.-P., Debrauwer L., Rao D., Bories G. Mercapturic acid conjugates as urinary end metabolites of the lipid peroxidation product 4-hydroxy-2-nonenal in the rat. Chem. Res. Toxicol. 8:1995;34-39.
2. Alary J., Debrauwer L., Fernanadez Y., Cravedi J.P., Rao D., Bories G. 1,4-Dihydroxynonene mercapturic acid, the major end metabolite of exogenous 4-hydroxy-2-nonenal, is a physiological component of rat and human urine. Chem. Res. Toxicol. 11:1998;130-135.
3. Alary J., Debrauwer L., Fernandez Y., Paris A., Cravedi J.P., Dolo L., Rao D., Bories G. Identification of novel urinary metabolites of the lipid peroxidation product 4-hydroxy-2-nonenal in rats. Chem. Res. Toxicol. 11:1998;1368-1376.
4. Berhane K., Widersten M., Engström A., Kozarich J.W., Mannervik B. Detoxication of base propenals and other. α,β -unsaturated aldehyde products of radical reactions and lipid peroxidation by human glutathione transferases Proc. Natl. Acad. Sci. USA. 91:1994;1480-1484.
5. Canuto R.A., Muzio G., Maggiora M., Poli G., Biasi F., Dianzani M.U., Ferro M., Bassi A.M., Penco S., Marinari U.M. Ability of different hepatoma cells to metabolize 4-hydroxynonenal. Cell. Biochem. Funct. 11:1993;79-86.
6. Chiarpotto E., Biasi F., Scavezza A., Camandola S., Dianzani M.U., Poli G. Metabolism of 4-hydroxy-2-nonenal and aging. Biochem. Biophys. Res. Comm. 207:1995;477-484.
7. Comporti M. Lipid peroxidation and cellular damage in toxic liver injury. Lab. Invest. 53:1985;599-623.
8. Esterbauer H., Zollner H., Lang J. Metabolism of the lipid peroxidation product 4-hydroxynonenal by isolated hepatocytes and by liver cytosolic fractions. Biochem. J. 228:1985;363-373.
9. Esterbauer H., Zollner H., Schaur R.J. Hydroxyalkenals: cytotoxic products of lipid peroxidation. ISI Atlas Sci.: Biochem. 1:1988;311-317.
10. Esterbauer H., Zollner H., Schaur R.J. Chemistry and biochemistry of 4-hydroxynonenal, malondialdehyde and related aldehydes. Free Radic. Biol. Med. 11:1991;81-128.
11. Friguet B., Stadtman E.R., Szweda L.I. Modification of glucose-6-phosphate dehydrogenase by 4-hydroxynonenal. Formation of cross-linked protein that inhibits the multicatalytic protease. J. Biol. Chem. 269:1994;21639-21643.
12. Grune T., Siems W., Kowalewski J., Zollner H., Esterbauer H. Identification of metabolic pathways of the lipid peroxidation product 4-hydroxynonenal by enterocytes of rat small intestine. Biochem. Internat. 25:1991;963-971.
13. Grune T., Siems W.G., Zollner H., Esterbauer H. Metabolism of 4-hydroxynonenal, a cytotoxic lipid peroxidation product, in Ehrlich mouse ascites cells at different proliferation stages. Cancer Res. 54:1994;5231-5235.
14. Grune T., Michel P., Sitte N., Eggert W., Albrecht-Nebe H., Esterbauer H., Siems W.G. Increased levels of 4-hydroxynonenal modified proteins in plasma of children with autoimmune diseases. Free Radical Biol. Med. 23:1997;357-360.
15. Grune T., Siems W.G., Petras P. Identification of metabolic pathways of the lipid peroxidation product 4-hydroxynonenal in in situ perfused rat kidney. J. Lipid Res. 38:1997;1660-1665.
16. Ji C., Amarnath V., Pietenpol J.A., Marnett L.J. 4-Hydroxynonenal induces apoptosis via caspase-3 activation and cytochrome c release. Chem. Res. Toxicol. 14:2001;1090-1096.
17. Laurent A., Alary J., Debrauwer L., Cravedi J.P. Analysis in the rat of 4-hydroxynonenal metabolites excreted in bile: evidence of enterohepatic circulation of these byproducts of lipid peroxidation. Chem. Res. Toxicol. 12:1999;887-894.
18. Luckey S.W., Petersen D.R. Metabolism of 4-hydroxynonenal by rat Kupffer cells. Arch. Biochem. Biophys. 389:2001;77-83.
19. Poli G., Albano E., Dianzani M.U. The role of lipid peroxidation in liver damage. Chem. Phys. Lipids. 45:1987;117-142.
20. Poli G., Schaur R.J. 4-Hydroxynonenal in the pathomechanisms of oxidative stress. Life. 50:2000;315-321.
21. Ruef J., Moser M., Bode C., Kubler W., Runge M.S. 4-Hydroxynonenal induces apoptosis, NF-kappaB-activation and formation of 8-isoprostane in vascular smooth muscle cells. Basic Res. Cardiol. 96:2001;143-150.
22. Siems W.G., Zollner H., Grune T., Esterbauer H. Qualitative and quantitative determination of metabolites of the lipid peroxidation product 4-hydroxynonenal from hepatocytes, enterocytes and tumor cells. Fres. J. Anal. Chem. 343:1992;75-76.
23. Siems W.G., Grune T., Beierl B., Zollner H., Esterbauer H. The metabolism of 4-hydroxynonenal, a lipid peroxidation product, is dependent on tumor age in Ehrlich mouse ascites cells. Emerit I., Chance B. Free Radicals and Aging. 1992;124-135 Birkhäuser Verlag AG, Basel, Boston, Berlin.
24. Siems W.G., Grune T., Esterbauer H. 4-Hydroxynonenal formation during ischemia and reperfusion of rat small intestine. Life Sci. 57:1995;785-789.
25. +-ATPase. Free Radic. Biol. Med. 20:1996;215-223.
26. 2 groups. Free Radic. Res. 27:1997;353-358.
27. Siems W., Zollner H., Grune T., Esterbauer H. Metabolic fate of 4-hydroxynonenal in hepatocytes: 1,4-dihydroxynonene is not the main product. J. Lipid Res. 38:1997;612-622.
28. Siems W., Pimenov A.M., Esterbauer H., Grune T. Metabolism of 4-hydroxynonenal, a cytotoxic lipid peroxidation product, in thymocytes as an effective secondary antioxidative defense mechanism. J. Biochem. 123:1998;534-539.
29. Siems W., Brenke R., Beier A., Grune T. Oxidative stress in chronic lymphedema. QJM. 95:2002;803-809.
30. Siems W., Carluccio F., Grune T., Jakstadt M., Quast S., Hampl H., Sommerburg O. Elevated serum concentration of cardiotoxic lipid peroxidation products in chronic renal failure in relation to the degree of renal anaemia. Clin. Nephrol. 58(Suppl 1):2002;20-25.
31. Singhal S.S., Zimniak P., Awasthi S., Piper J.T., He N., Teng J.I., Petersen D.R., Awasthi Y.C. Several closely related glutathione S-transferase isozymes catalyzing conjugation of 4-hydroxynonenal are differentially expressed in human tissues. Arch. Biochem. Biophys. 311:1994;242-250.
32. Spitz D.R., Sullivan S.J., Malcolm R.R., Roberts R.J. Glutathione dependent metabolism and detoxification of 4-hydroxy-2-nonenal. Free Radic. Biol. Med. 11:1991;415-423.
33. Spycher S.E., Tabataba-Vakili S., O'Donnell V.B., Palomba L., Azzi A. Aldose reductase induction: a novel response to oxidative stress of smooth muscle cells. ASEB J. 11:1997;181-188.
34. Srivastava S.K., Ansari N.H., Hair G.A., Das B. Aldose and aldehyde reductases in human tissues. Biochim. Biophys. Acta. 800:1984;220-227.
35. Srivastava S., Chandra A., Wang L.-F., Seifert W.E., DaGue B.B., Ansari N.H., Srivastava S.K., Bhatnagar A. Metabolism of the lipid peroxidation product, 4-hydroxy-trans-2-nonenal, in isolated perfused rat heart. J. Biol. Chem. 273:1998;10893-10900.
36. Stadtman E.R. Protein oxidation and aging. Science. 257:1992;1220-1224.
37. Tjalkens R.B., Cook L.W., Petersen D.R. Formation and export of the glutathione conjugate of 4-hydroxy-2,3-E-nonenal (4-HNE) in hepatoma cells. Arch. Biochem. Biophys. 361:1999;113-119.
38. Toyokuni S., Uchida K., Okamoto K., Hattori-Nakakuki Y., Hiai H., Stadtman E.R. Formation of 4-hydroxy-2-nonenal-modified proteins in the renal proximal tubules of rats treated with a renal carcinogen, ferric nitrilotriacetate. Proc. Natl. Acad. Sci. USA. 91:1994;2616-2620.
39. Uchida K., Stadtman E.R. Selective cleavage of thioether linkage in proteins modified with 4-hydroxynonenal. Proc. Natl. Acad. Sci. USA. 89:1992;5611-5615.
40. Uchida K., Stadtman E.R. Covalent attachment of 4-hydroxynonenal to glyceraldehyde-3-phosphate dehydrogenase. A possible involvement of intra- and intermolecular cross-linking reaction. J. Biol. Chem. 268:1993;6388-6393.
41. Uchida K., Szweda L.K., Chae H.-Z., Stadtman E.R. Immunochemical detection of 4-hydroxynonenal protein adducts in oxidized hepatocytes. Proc. Natl. Acad. Sci. USA. 90:1993;8742-8746.
42. Uchida K., Toyokuni S., Nishikawa K., Kawakishi S., Oda H., Hiai H., Stadtman E.R. Michael addition-type 4-hydroxy-2-nonenal adducts in modified low-density lipoproteins: markers for atherosclerosis. Biochemistry. 33:1994;12487-12494.
43. Uchida K., Shiraishi M., Naito Y., Torii Y., Nakamura Y., Osawa T. Activation of stress signalling pathways by the end product of lipid peroxidation. J. Biol. Chem. 274:1999;2234-2242.
44. Ullrich O., Grune T., Henke W., Esterbauer H., Siems W.G. Identification of metabolic pathways of the lipid peroxidation product 4-hydroxynonenal by mitochondria isolated from rat kidney cortex. FEBS Lett. 352:1994;84-86.
45. Ullrich O., Huser H., Ehrlich W., Grune T. Intracellular metabolism of 4-hydroxynonenal in primary cultures of rabbit synovial fibroblasts. Free Radic. Biol. Med. 22:1997;1153-1157.