15-Hydroperoxyeicosapentaenoic acid, but not eicosapentaenoic acid, shifts arachidonic acid away from cyclooxygenase pathway into acyl-CoA synthetase pathway in rabbit kidney medulla microsomes

Prostaglandins Leukotrienes and Essential Fatty Acids

Volumn 75, Issue 2, 2006, Pages 69-74

  Sakuma, Satoru ^a   Usa, Kumiko ^a   Fujimoto, Yohko ^a  

^a OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

15 HYDROXYEICOSAPENTANOIC ACID; ARACHIDONIC ACID; FATTY ACID DERIVATIVE; GLUTATHIONE; HYDROCHLORIC ACID; HYDROQUINONE; ICOSAPENTAENOIC ACID; LONG CHAIN FATTY ACID COENZYME A LIGASE; PROSTAGLANDIN SYNTHASE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARACHIDONIC ACID METABOLISM; ARTICLE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ELECTRON SPIN RESONANCE; EXTRACTION; KIDNEY MEDULLA; KIDNEY MICROSOME; MALE; NONHUMAN; PH; PHYSIOLOGY; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS; RABBIT; SEPARATION TECHNIQUE;

ANIMALS; ARACHIDONIC ACID; COENZYME A LIGASES; EICOSAPENTAENOIC ACID; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN PEROXIDE; IRON; KIDNEY MEDULLA; MALE; MICROSOMES; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; RABBITS; SIGNAL TRANSDUCTION; TERT-BUTYLHYDROPEROXIDE;

ORYCTOLAGUS CUNICULUS;

EID: 33747832441     PISSN: 09523278     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.plefa.2006.06.003     Document Type: Article

References (39)

1. Dyerberg J., and Bang H.O. Haemostatic function and platelet polyunsaturated fatty acids in Eskimos. Lancet 2 (1979) 433-435
2. Holub B.J. Dietary fish oils containing eicosapentaenoic acid and the prevention of atherosclerosis and thrombosis. CMAJ 139 (1988) 377-381
3. Needleman P., Raz A., Minkes M.S., Ferrendelli J.A., and Sprecher H. Triene prostaglandins: prostacyclin and thromboxane biosynthesis and unique biological properties. Proc. Natl. Acad. Sci. USA 76 (1979) 944-948
4. Powell W.S., and Gravelle F. Metabolism of eicosapentaenoic acid by aorta: formation of a novel 13-hydroxylated prostaglandin. Biochim. Biophys. Acta 835 (1985) 201-211
5. Ardaillou R., Baud L., and Sraer J. Leukotrienes and other lipoxygenase products of arachidonic acid synthesized in the kidney. Am. J. Med. 81 (1986) 12-22
6. Lam B.K., and Wong P.Y. Biosynthesis and biological activities of lipoxin A5 and B5 from eicosapentaenoic acid. Adv. Exp. Med. Biol. 229 (1988) 51-59
7. Edenius C., Stenke L., and Lindgren J.A. On the mechanism of transcellular lipoxin formation in human platelets and granulocytes. Eur. J. Biochem. 199 (1991) 401-409
8. Tsunomori M., Fujimoto Y., Muta E., Nishida H., Sakuma S., and Fujita T. 15-Hydroperoxyeicosapentaenoic acid inhibits arachidonic acid metabolism in rabbit platelets more potently than eicosapentaenoic acid. Biochim. Biophys. Acta 1300 (1996) 171-176
9. Hunter S.A., Burstein S., and Sedor C. Stimulation of prostaglandin synthesis in WI-38 human lung fibroblasts following inhibition of phospholipid acylation by p-hydroxymercuribenzoate. Biochim. Biophys. Acta 793 (1984) 202-212
10. Fuse I., Iwanaga T., and Tai H.H. Phorbol ester, 1,2-diacylglycerol, and collagen induce inhibition of arachidonic acid incorporation into phospholipids in human platelets. J. Biol. Chem. 264 (1989) 3890-3895
11. Hornberger W., and Patscheke H. Primary stimuli of icosanoid release inhibit arachidonoyl-CoA synthetase and lysophospholipid acyltransferase. Mechanism of action of hydrogen peroxide and methyl mercury in platelets. Eur. J. Biochem. 187 (1990) 175-181
12. Reichman M., Nen W., and Hokin L.E. Delta 9-tetrahydrocannabinol inhibits arachidonic acid acylation of phospholipids and triacylglycerols in guinea pig cerebral cortex slices. Mol. Pharmacol. 40 (1991) 547-555
13. Oh-ishi S., Yamaki K., Abe M., Tomoda H., and Omura S. The acyl-CoA synthetase inhibitor triacsin C enhanced eicosanoid release in leukocytes. Jpn. J. Pharmacol. 59 (1992) 417-418
14. 2+ as modulators of formation of the two products. Prostaglandins Leukot. Essent. Fatty Acids 61 (1999) 105-112
15. Sakuma S., Fujimoto Y., Katoh Y., Kitao A., and Fujita T. The regulation of prostaglandin and arachidonoyl-CoA formation from arachidonic acid in rabbit kidney medulla microsomes by palmitoyl-CoA. Life Sci. 66 (2000) 1147-1153
16. Sakuma S., Fujimoto Y., Katoh Y., Kitao A., and Fujita T. The effects of fatty acyl CoA esters on the formation of prostaglandin and arachidonoyl-CoA formed from arachidonic acid in rabbit kidney medulla microsomes. Prostaglandins Leukot. Essent. Fatty Acids 64 (2001) 61-65
17. Sakuma S., Fujimoto Y., Katoh Y., and Fujita T. The effects of nitric oxide and peroxynitrite on the formation of prostaglandin and arachidonoyl-CoA formed from arachidonic acid in rabbit kidney medulla microsomes. Prostaglandins Leukot. Essent. Fatty Acids 68 (2003) 343-349
18. Fujimoto Y., Usa K., and Sakuma S. Effects of endocrine disruptors on the formation of prostaglandin and arachidonoyl-CoA formed from arachidonic acid in rabbit kidney medulla microsomes. Prostaglandins Leukot. Essent. Fatty Acids 73 (2005) 447-452
19. Tai H.H., Tai C.L., and Hollander C.S. Biosynthesis of prostaglandins in rabbit kidney medulla. Properties of prostaglandin synthase. Biochem. J. 154 (1976) 257-264
20. Lowry H., Rosebrough N.J., Farr A., and Randall R.J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193 (1951) 265-275
21. Tomoda H., Igarashi K., and Omura S. Inhibition of acyl-CoA synthetase by triacsins. Biochim. Biophys. Acta 921 (1987) 595-598
22. Hartman E.J., Omura S., and Laposata M. Triacsin C: a differential inhibitor of arachidonoyl-CoA synthetase and nonspecific long chain acyl-CoA synthetase. Prostaglandins 37 (1989) 655-671
23. Halliwell B., and Gutteridge J.M.C. Oxygen toxicity, oxygen radicals, transition metals and disease. Biochem. J. 219 (1984) 1-14
24. Yagi K., Ishida N., Komura S., Ohishi N., Kusai M., and Kohno M. Generation of hydroxyl radical from linoleic acid hydroperoxide in the presence of epinephrine and iron. Biochem. Biophys. Res. Commun. 183 (1992) 945-951
25. Harris R.C., and Breyer M.D. Physiological regulation of cyclooxygenase-2 in the kidney. Am. J. Physiol. 281 (2001) F1-F11
26. Fujimoto Y., Sakuma S., Inoue T., Uno E., and Fujita T. The endocrine disruptor nonylphenol preferentially blocks cyclooxygenase-1. Life Sci. 70 (2002) 2209-2214
27. Fujimoto Y., Sakuma S., Nishiwaki Y., Ikeda M., and Fujita T. Effects of endocrine disruptors on arachidonic acid metabolism in rabbit platelets. Toxicol. Appl. Pharmacol. 189 (2003) 96-99
28. Bourre J.M., Piciotti M., Dumont O., Pasccal G., and Durand G. Dietary linoleic acid and polyunsaturated fatty acids in rat brain and other organs. Minimal requirements of linoleic acid. Lipids 25 (1990) 465-472
29. Clandinin M.T. Brain development and assessing the supply of polyunsaturated fatty acid. Lipids 34 (1999) 131-137
30. Horrobin D.F. Low prevalences of coronary heart disease (CHD), psoriasis, asthma and rheumatoid arthritis in Eskimos: are they caused by high dietary intake of eicosapentaenoic acid (EPA), a genetic variation of essential fatty acid (EFA) metabolism or a combination of both?. Med. Hypotheses 22 (1987) 421-428
31. Otsuji S., Shibata N., Hirota H., Akagami H., and Wada A. Highly purified eicosapentaenoic acid attenuates tissue damage in experimental myocardial infarction. Jpn. Circ. J. 57 (1993) 335-343
32. Torras J., Soto K., Riera M., Herrero I., Valles J., Cruzado J.M., Alsina J., and Grinyo J.M. Changes in renal hemodynamics and physiology after normothermic ischemia in animals supplemented with eicosapentaenoic acid. Transpl. Int. 9 (1996) S455-S459
33. Plantinga E.A., Hovenier R., and Beynen A.C. Qualitative risk assessment of chronic renal failure development in healthy, female cats as based on the content of eicosapentaenoic acid in adipose tissue and that of arachidonic acid in plasma cholesteryl esters. Vet. Res. Commun. 29 (2005) 281-286
34. Konturek S.J., Mikos E., Pawlik W., and Walus K. Direct inhibition of gastric secretion and mucosal blood flow by arachidonic acid. J. Physiol. 286 (1979) 15-28
35. Karmazyn M., and Moffat M.P. Toxic properties of arachidonic acid on normal, ischemic and reperfused hearts. Indirect evidence for free radical involvement. Prostaglandins Leukot. Med. 17 (1985) 251-264
36. Kigoshi T., Uchida K., Kaneko M., Iwasaki R., Nakano S., Azukizawa S., and Morimoto S. Direct inhibition of smooth muscle myosin light chain kinase by arachidonic acid in a purified system. Biochem. Biophys. Res. Commun. 171 (1990) 369-374
37. Tebbey P.W., McGowan K.M., Stephens J.M., Buttke T.M., and Pekala P.H. Arachidonic acid down-regulates the insulin-dependent glucose transporter gene (GLUT4) in 3T3-L1 adipocytes by inhibiting transcription and enhancing mRNA turnover. J. Biol. Chem. 269 (1994) 639-644
38. Knutson K.L., and Hoenig M. Arachidonic acid-induced down-regulation of protein kinase C delta in beta-cells. J. Cell Biochem. 62 (1996) 543-552
39. Hartfield P.J., and Robinson J.M. Arachidonic acid activates NADPH oxidase by a direct, calmodulin-dependent mechanism. Prostaglandins Other Lipid Mediat. 56 (1998) 1-6