The role of the cytochrome P450-dependent metabolites of arachidonic acid in blood pressure regulation and renal function. A review

American Journal of Hypertension

Volumn 10, Issue 3, 1997, Pages 356-365

  Rahman, Mahboob ^a   Wright Jr , Jackson T ^a   Douglas, Janice G ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

arachidonic acid; cytochrome P450; hypertension

Indexed keywords

ARACHIDONIC ACID; CYTOCHROME P450;

ARACHIDONIC ACID METABOLISM; BLOOD PRESSURE REGULATION; ENZYME LOCALIZATION; HUMAN; HYPERTENSION; KIDNEY FUNCTION; NONHUMAN; PATHOGENESIS; PRIORITY JOURNAL; REVIEW;

ANIMALS; ARACHIDONIC ACID; BLOOD PRESSURE; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; HYPERTENSION; KIDNEY;

EID: 0030889716     PISSN: 08957061     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0895-7061(96)00381-0     Document Type: Review

References (104)

1. Schwartzman M, Carroll MA, Ibraham NG, et al. Renal arachidonic acid metabolism. The third pathway. Hypertension. 7:1985;I136-I144.
2. Ballou LR, Lam BK, Wong PY, Cheung WY. Formation of cis-14,15-oxido-5,8,11-icosatrienoic acid from phosphatidylinositol in human platelets. Proc Natl Acad Sci USA. 84:1987;6990-6994.
3. Capdevila JH, Kishore V, Dishman E. A novel pool of rat liver inositol and ethanolamine phospholipids contain EETs. Biochem Biophys Res Commun. 146:1987;638-644.
4. Falck JR, Scheuler VJ, Jacobson HR. Arachidonate epoxygenase: identification of EETs in rabbit kidney. J Lipid Res. 28:1987;840-846.
5. Toto R, Siddhanta A, Manna S, et al. Arachidonic acid epoxygenase: detection of epoxyeicosatrienoic acids in human urine. Biochim Biophys Acta. 919:1987;132-139.
6. Proctor KG, Capdevila JH, Falck JR, et al. Cardiovascular and renal actions of cytochrome P-450 metabolites of arachidonic acid. Blood Vessels. 26:1989;53-64.
7. Proctor KG, Falck JR, Capdevila J. Intestinal vasodilation by epoxyeicosatrienoic acids: arachidonic acid metabolites produced by a cytochrome P450 monooxygenase. Circ Res. 60:1987;50-59.
8. McGiff JC. Cytochrome P-450 metabolism of arachidonic acid. Annu Rev Pharmacol Toxicol. 31:1991;339-369.
9. Capdevila J, Gil L, Orellana M, et al. Inhibitors of cytochrome P-450-dependent arachidonic acid metabolism. Arch Biochem Biophys. 261:1988;257-263.
10. Capdevila JH, Karara A, Waxman DJ, et al. Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase. J Biol Chem. 265(19): 1990;10,865-10,871.
11. Thibonnier M, Bayer AL, Laethem CL, et al. Role of eicosanoids in vasopressin-induced calcium mobilization in A7r5 vascular smooth muscle cells. Am J Physiol. 265:1993;E108-E114.
12. Romero MF, Douglas JG, Hopfer U. P450 monoxygenase metabolite of arachidonic acid inhibits Na reabsorption in early S1 primary cultures. Kidney Int. 162A:1990.
13. Ribeiro CM, Dubay GR, Falck JR, Mandel LJ. Parathyroid hormone inhibits Na(+)-K(+)-ATPase through a cytochrome P-450 pathway. Am J Physiol. 266:1994;F497-505.
14. Hirt DL, Jacobson HR. Functional effects of cytochrome P450 arachidonate metabolites in the kidney. Semin Nephrol. 11:1991;148-155.
15. Sacerdoti D, Escalante B, Abraham NG, et al. Treatment with tin prevents the development of hypertension in spontaneously hypertensive rats. Science. 243:1989;388-390.
16. LaBella FS, Queen G. General anesthetics inhibit-cytochrome P450 monooxygenases and arachidonic acid metabolism. Can J Physiol Pharmacol. 71:1993;48-53.
17. Nakamura M, Imaoka S, Miura K, et al. Induction of cytochrome P450 isozymes in rat renal microsomes by cyclosporin A. Biochem Pharmacol. 48:1994;1743-1746.
18. Sacerdoti D, Borsato M, Rigotti P, et al. Increased renal production of cytochrome P450-dependent metabolites of arachidonic acid in cyclosporine-induced nephrotoxicity. Adv Prostaglandin Thromboxane Leukotriene Res. 21B:1991;689-692.
19. Dong Z, Hong J, Qiang MA. Mechanism of induction of cytochrome p 45-ac (p450j) in chemically induced and spontaneously diabetic rats. Arch Biochem Biophys. 263:1988;29-35.
20. +)ATPase. Nature. 314:1985;620-622.
21. Doucet A, Barlet-Bas C, Siaume-Perez S, et al. Gluco and mineralocorticoids control adenylate cyclase in specific nephron segments. Am J Physiol. 258:1990;F812-F820.
22. Lapuerta L, Chacos N, Falck JR, et al. Renal microsomal cytochrome P-450 and the oxidative metabolism of arachidonic acid. Am J Med Sci. 295:1988;275-279.
23. Sessa WC, Lin L, Nasjletti A. Reciprocal effects of dexamethasone on vasodilatory responses to arachidonic acids and prostanoids in the isolated perfused rabbit kidney. Hypertension. 15:1990;I93-I96.
24. Van Voorhis BJ, Dunn MS, Falck JR, et al. Metabolism of arachidonic acid to epoxyeicosatrienoic acids by human granulosa cells may mediate steroidogenesis. J Clin Endocrinol Metab. 76:1993;1555-1559.
25. Ferreri NR, Schwartzman M, Ibraham NG, et al. Arachidonic acid metabolism in a cell suspension isolated from rabbit renal outer medulla. J Pharmacol Exp Ther. 231:1984;441-448.
26. Koop DR, Morrison AR, Douglas JG. Coexpression of cytochrome p450 and metabolism of arachidonic acid to novel products by proximal tubule epithelial cells. Kidney Int. 33:1988;62-70.
27. Madhun ZT, Goldthwait DA, McKay D, et al. An epoxygenase metabolite of arachidonic acid mediates angiotensin II-induced rises in cytosolic calcium in rabbit proximal tubule epithelial cells. J Clin Invest. 88:1981;456-461.
28. Hirt DL, Capdevila J, Falck JR, et al. Cytochrome P450 metabolites of arachidonic acid are potent inhibitors of vasopressin action on rabbit cortical collecting duct. J Clin Invest. 84:1989;1805-1812.
29. + exchange and are mitogenic in cultured glomerular mesangial cells. J Cell Physiol. 144:1990;429-437.
30. Sellmayer A, Uedelhoven WM, Weber PC, Bonventre JV. Endogenous non-cyclooxygenase metabolites of arachidonic acid modulate growth and mRNA levels of immediate-early response genes in rat mesangial cells. J Biol Chem. 266:1991;3800-3807.
31. Laniado Schwartzman M, Abraham NG. The renal cytochrome P-450 arachidonic acid system. Pediatr Nephrol. 6:1992;490-498.
32. Jacobson HR, Breyer J, Hussain H, et al. Urinary excretion of cytochrome P450 metabolites is elevated in human hypertension. J Am Soc Nephrol. 3:1992;455a.
33. Yamamoto S, Nishimura M, Conners MS, et al. Oxidation and keto reduction of 12-hydroxy-5,8,10,14-eicosatetraenoic acids in bovine corneal epithelial microsomes. Biochim Biophys Acta. 1210:1994;217-225.
34. Schwartzman ML, Masferrer J, Dunn MW, et al. Cytochrome P450, drug metabolizing enzymes and arachidonic acid metabolism in bovine ocular tissues. Curr Eye Res. 6:1987;623-630.
35. Hill E, Fitzpatrick F, Murphy RC. Biological activity and metabolism of 20-hydroxyeicosatetraenoic acid in the human platelet. Br J Pharmacol. 106:1992;267-274.
36. Imig JD, Zou AP, Ortiz de Montellano PR, et al. Cytochrome P-450 inhibitors alter afferent arteriolar responses to elevations in pressure. Am J Physiol. 266:1994;H1879-885.
37. Holtzman MJ, Turk J, Pentland A. A regiospecific monooxygenase with novel stereopreference is the major pathway for arachidonic acid oxygenation in isolated epidermal cells. J Clin Invest. 84:1989;1446-1453.
38. Turk J, Wolf BA, Comens PG, et al. Arachidonic acid metabolism in isolated pancreatic islets. IV. Negative ion-mass spectrometric quantitation of monooxygenase product synthesis by liver and islets. Biochim Biophys Acta. 835:1985;1-17.
39. Knickle LC, Bend JR. Bioactivation of arachidonic acid by the cytochrome P450 monooxygenases of guinea pig lung: the orthologue of cytochrome P450 2B4 is solely responsible for formation of epoxyeicosatrienoic acids. Mol Pharmacol. 45:1994;1273-1280.
40. Macica C, Balazy M, Falck JR, et al. Characterization of cytochrome P-450-dependent arachidonic acid metabolism in rabbit intestine. Am J Physiol. 265:1993;G735-G741.
41. Laethem RM, Laethem CL, Ding X, Koop DR. P-450-dependent arachidonic acid metabolism in rabbit olfactory microsomes. J Pharmacol Exp Ther. 262:1992;433-438.
42. Amruthesh SC, Falck JR, Ellis EF. Brain synthesis and cerebrovascular action of epoxygenase metabolites of arachidonic acid. J Neurochem. 58:1992;503-510.
43. Ellis EF, Amruthesh SC, Police RJ, Yancey LM. Brain synthesis and cerebrovascular action of cytochrome P-450/monooxygenase metabolites of arachidonic acid. Adv Prostaglandin Thromboxane Leukotriene Res. 21A:1991;201-204.
44. Abraham NG, Feldman E, Falck JR, et al. Modulation of erythropoiesis by novel human bone marrow cytochrome P450-dependent metabolites of arachidonic acid. Blood. 78:1991;1461-1466.
45. Lutton JD, Schwartzman ML, Abraham NG. Cytochrome P450 dependent arachidonic acid metabolism in hemopoietic cells. Adv Exp Med Biol. 271:1989;115-121.
46. Fitzpatrick FA, Ennis MD, Baze MD, et al. Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosa trienoic acids. J Biol Chem. 261:1986;15,334-15,338.
47. Smyde G, Capdevila J, Chacos N, et al. Action of luteinising hormone-releasing hormone. Involvement of novel arachidonic acid metabolites. Proc Natl Acad Sci USA. 80:1983;3504-3507.
48. Capaderich J, Capdevila J, Chacos N, et al. Novel hypothalamic arachidonate products stimulate somatostatin release from median eminence. Endocrinology. 113:1995;421-423.
49. Oyekan AO, McGiff JC, Quilley J. Cytochrome P-450-dependent vasodilation of rat kidney by arachidonic acid. Am J Physiol. 261:1991;H714-H719.
50. Pinto A, Abraham NG, Mullane KM. Cytochrome P-450-dependent monooxygenase activity and endothelial-dependent relaxations induced by arachidonic acid. J Pharmacol Exp Ther. 236:1986;445-451.
51. Pinto A, Abraham NG, Mullane KM. Arachidonic acid-induced endothelial-dependent relaxations of canine coronary arteries: contribution of a cytochrome P-450-dependent pathway. J Pharmacol Exp Ther. 240:1987;856-863.
52. 2 and epoxyeicosatrienoic acids in relaxation of bovine coronary arteries to arachidonic acid. Am J Physiol. 264:1993;H327-H335.
53. Carroll MA, Schwartzman M, Capdevila J, et al. Vasoactivity of arachidonic acid epoxides. Eur J Pharmacol. 138:1987;281-283.
54. Fulton D, McGiff JC, Quilley J. Contribution of NO and cytochrome P450 to the vasodilator effect of bradykinin in the rat kidney. Br J Pharmacol. 107:1992;722-725.
55. Carroll MA, Escalante B, McGiff JC. Cytochrome P-450 metabolites of arachidonic acid: implications for blood pressure regulation. Pol J Pharmacol Pharm. 42:1990;191-201.
56. Hu S, Kim HS. Activation of K+ channel in vascular smooth muscles by cytochrome P450 metabolites of arachidonic acid. Eur J Pharmacol. 230:1993;215-221.
57. + channels to arachidonic acid-induced endothelium-dependent vasodilation in rat isolated perfused mesenteric arteries. J Pharmacol Exp Ther. 258:1991;452-458.
58. Escalante BA, Sessa WC, Falck JR, et al. Vasoactivity of 20 HETE is dependent on metabolism by cyclooxygenase. J Pharmacol Exp Ther. 248:1989;229-232.
59. Schwartzman ML. Modification of arachidonic acid metabolism via the cytochrome P450-related monooxygenase system. Adv Prostaglandin Thromboxane Leukotriene Res. 20:1990;241-249.
60. Schwartzman M, Falck JR, Yadagiri P, Escalante BA. Metabolism of 20 HETE by cyclooxygenase, formation and identification of novel endothelium dependent vasoconstrictor metabolites. J Biol Chem. 264:1989;1165-1172.
61. Harder DR, Gebremedhin D, Narayanan J, et al. Formation and action of a P-450 4A metabolite of arachidonic acid in cat cerebral microvessels. Am J Physiol. 266:1994;H2098-H2107.
62. Rifkind AB, Kanetoshi A, Orlinick J, et al. Purification and biochemical characterization of two major cytochrome P-450 isoforms induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in chick embryo liver. J Biol Chem. 269:1994;3387-3396.
63. Pfister SL, Falck JR, Campbell WB. Enhanced synthesis of epoxyeicosatrienoic acids by cholesterol-fed rabbit aorta. Am J Physiol. 261:1991;H843-H852.
64. Carroll MA, Balazy M, Margiotta P, et al. Renal vasodilator activity of 5,6-epoxyeicosatrienoic acid depends upon conversion by cyclooxygenase and release of prostaglandins. J Biol Chem. 268:1993;12,260-12,266.
65. Katoh T, Takahashi K, Capdevila J, et al. Glomerular stereospecific synthesis and hemodynamic actions of 8,9-epoxyeicosatrienoic acid in rat kidney. Am J Physiol. 261:1991;F578-F586.
66. Zou AP, Imig JD, Kaldunski M, et al. Inhibition of renal vascular 20-HETE production impairs autoregulation of renal blood flow. Am J Physiol. 266:1994;F275-F282.
67. Zou AP, Ma YH, Sui ZH, et al. Effects of 17-octadecynoic acid, a suicide-substrate inhibitor of cytochrome P450 fatty acid omega-hydroxylase, on renal function in rats. J Pharmacol Exp Ther. 268:1994;474-481.
68. Takahashi K, Harris RC, Capdevila JH, et al. Induction of renal arachidonate cytochrome P-450 epoxygenase after uninephrectomy: counterregulation of hyperfiltration. J Am Soc Nephrol. 3:1993;1496-1500.
69. Takahashi K, Capdevila J, Karara A, et al. Cytochrome P-450 arachidonate metabolites in rat kidney: characterization and hemodynamic responses. Am J Physiol. 258:1990;F781-F789.
70. Zeldin DC, Plitman JD, Kobayashi J, et al. The rabbit pulmonary cytochrome P450 arachidonic acid metabolic pathway: characterization and significance. J Clin Invest. 95:1995;2150-2160.
71. Cashman JR, Snowdowne KW. Prolactin secretion in anterior pituitary cells: effect of eicosanoids. Eicosanoids. 5:1992;153-161.
72. Graier WF, Simecek S, Sturek M. Cytochrome P450 mono-oxygenase-regulated signalling of Ca2+ entry in human and bovine endothelial cells. J Physiol Lond. 482:1995;259-274.
73. 2+ entry into platelets stimulated by thapsigargin and thrombin. J Biol Chem. 267:1992;19,854-19,858.
74. Moffat MP, Ward CA, Bend JR, et al. Effects of epoxyeicosatrienoic acids on isolated hearts and ventricular myocytes. Am J Physiol. 264:1993;H1154-H1160.
75. Jacobson HR, et al. Prostagandins and Membrane Ion Transport. 1987;311-318 Raven Press, New York.
76. Schlondorff D, Petty E, Oates JA, et al. Epoxygenase metabolites of arachidonic acid inhibit vasopressin response in toad bladder. Am J Physiol. 253:1987;F464-F470.
77. +-ATPase in the cornea. Proc Natl Acad Sci USA. 84:1987;8125-8129.
78. Henrich WL, Falck JR, Campbell WB. Inhibition of renin secretion from rat renal cortical slices by (R)-12-HETE. Am J Physiol. 263:1992;F665-F670.
79. Escalante BA, Falck JR, Yadagiri P, et al. 19(S) Hydroxy eicosa tetraenoic acid is a potent stimulator of renal Na,K-ATPase. Biochem Biophys Res Commun. 152:1988;1269-1274.
80. Carroll MA, Sala A, Dunn CE, et al. Structural identification of cytochrome P450-dependent arachidonate metabolites formed by rabbit medullary thick ascending limb cells. J Biol Chem. 266:1991;12,306-12,312.
81. Zou AP, Imig JD, Ortiz de Montellano PR, et al. Effect of P-450 omega-hydroxylase metabolites of arachidonic acid on tubuloglomerular feedback. Am J Physiol. 266:1994;F934-F941.
82. Satoh T, Cohen HT, Katz AI. Intracellular signaling in the regulation of renal Na-K-ATPase. II. Role of eicosanoids. J Clin Invest. 91:1993;409-415.
83. Bidard JN, Rossi B, Renaud JF, Lazunski M. A search for a ouabain like substance from the electric organ of Electrophorus electricus which led to arachidonic acid and related fatty acids. Biochim Biophys Acta. 769:1984;245-252.
84. Escalante B, Erlij D, Falck JR, McGiff JC. Effect of cytochrome P450 arachidonate metabolites on ion transport in rabbit kidney loop of Henle. Science. 251:1991;799-802.
85. 86Rb uptake in renal epithelial cells. J Cell Physiol. 160:1994;69-74.
86. Capdevila JH, Wei S, Yan J, et al. Cytochrome P-450 arachidonic acid epoxygenase. Regulatory control of the renal epoxygenase by dietary salt loading. J Biol Chem. 267:1992;21,720-21,726.
87. Makita K, Takahashi K, Karara A, et al. Experimental and/or genetically controlled alterations of the renal microsomal cytochrome P450 epoxygenase induce hypertension in rats fed a high salt diet. J Clin Invest. 94:1994;2414-2420.
88. Rettig R, Folberth C, Kopf D, et al. Role of the kidney in the pathogenesis of primary hypertension. Clin Exp Hypertens A. 12:1990;957-1002.
89. Sacerdoti D, Abraham NG, McGiff JC, Schwartzman ML. Renal cytochrome P-450-dependent metabolism of arachidonic acid in spontaneously hypertensive rats. Biochem Pharmacol. 37:1988;521-527.
90. Omata K, Abraham NG, Escalante B, Schwartzman ML. Age-related changes in renal cytochrome P-450 arachidonic acid metabolism in spontaneously hypertensive rats. Am J Physiol. 262:1992;F8-F16.
91. Da Silva JL, Tiefenthaler M, Park E, et al. Tin-mediated heme oxygenase gene activation and cytochrome P450 arachidonate hydroxylase inhibition in spontaneously hypertensive rats. (Published erratum appears in Am J Med Sci 1994 Aug;308(2): 138). Am J Med Sci. 307:1994;173-181.
92. Levere RD, Martasek P, Escalante B, et al. Effect of heme arginate administration on blood pressure in spontaneously hypertensive rats. J Clin Invest. 86:1990;213-219.
93. Neil TK, Stoltz RA, Jiang S, et al. Modulation of corneal heme oxygenase expression by oxidative stress agents. J Ocul Pharmacol-Ther. Fall 11:((3)):1995;455-468.
94. Roman RJ. Altered pressure natriuresis relationship in young spontaneously hypertensive rats. Hypertension. 9:1987;III131-III136.
95. Gebremedhin D, Fenoy FJ, Harder DR, Roman RJ. Enhanced vascular tone in the renal vasculature of spontaneously hypertensive rats. Hypertension. 16:1990;648-654.
96. Imig JD, Falck JR, Gebremedhin D, et al. Elevated renovascular tone in young spontaneously hypertensive rats. Role of cytochrome P-450. Hypertension. 22:1993;357-364.
97. Gebremedhin D, Ma YH, Imig JD, et al. Role of cytochrome P-450 in elevating renal vascular tone in spontaneously hypertensive rats. J Vasc Res. 30:1993;53-60.
98. Ma YH, Schwatzman ML, Roman FJ. Altered renal P-450 metabolism in Dahl salt sensitive rats. Am J Physiol. 267:((2 Pt 2)):1994;R575-R589.
99. Carroll MA, Schwartzman M, Baba M, et al. Renal cytochrome P-450-related arachidonate metabolism in rabbit aortic coarctation. Am J Physiol. 255:1988;F151-F157.
100. Nelson JL, Kulkarni AP. Partial purification and characterization of a peroxidase activity from human placenta. Biochem J. 268:1990;739-743.
101. Schwartzman ML, Martasek P, Rios AR, et al. Cytochrome P450-dependent arachidonic acid metabolism in human kidney. Kidney Int. 37:1990;94-99.
102. Abraham NG, Martasek P, Ben Ari J, et al. Cytochrome p 450 arachidonic acid metabolism in hypernephroma. Kidney Int. 37:1990;344.
103. Catella F, Lawson J, Fitzgerald DJ, FitzGerald GA. Endogenous biosynthesis of arachidonic acid epoxides in humans: increased formation in pregnancy-induced hypertension. Proc Natl Acad Sci USA. 87:1990;5893-5897.
104. McGiff JC, Carroll MA. Cytochrome P450-dependent arachidonate metabolites, renal function and blood pressure regulation. Adv Prostaglandin Thromboxane Leukotriene Res. 21B:1991;675-682.