Research Progress of Epoxyeicosatrienoic Acid and Its Role in Regulating Development of Cirrhotic Portal Hypertension_CHINESE JOURNAL OF BASES AND CLINICS IN GENERAL SURGERY

Authors：

 HUANGYi-jun , QINJun , LIHong-jie ,  LUOMeng

Department of General Surgery, The 9th Hospital, School of Medicine, Shanghai Jiaotong University, Shanghai 201900, China;

Corresponding author：

LUOMeng, Email: luoty@hotmail.com

Keywords：

Cirrhotic portal hypertension; Epoxyeicosatrienoic acid; Hyperdynamic circulation

DOI：

10.7507/1007-9424.20160263

Video：

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Objective To summarize research progress of vascular physiological function of epoxyeicosatrienoic acid and its impact on pathogenesis of cirrhotic portal hypertension. Method Literatures about recent studies on epoxyeicosatrienoic acid in different organs and different animal models including cirrhotic portal hypertension were reviewed according to the results searched from PubMed and Wanfang databases. Results Epoxyeicosatrienoic acid in the different organs and the different animal models showed the complex functions, and it might affect the development of cirrhosis portal hypertension disease through its vascular physiological function. Conclusion Increasing or decreasing epoxyeicosatrienoic acid might affect development of cirrhosis portal hypertension disease, which could provide a new method for treatment of cirrhosis portal hypertension.

Citation： HUANGYi-jun, QINJun, LIHong-jie, LUOMeng. Research Progress of Epoxyeicosatrienoic Acid and Its Role in Regulating Development of Cirrhotic Portal Hypertension. CHINESE JOURNAL OF BASES AND CLINICS IN GENERAL SURGERY, 2016, 23(8): 1005-1010. doi: 10.7507/1007-9424.20160263 Copy

1.	中华外科学会门静脉高压症学组.肝硬化门静脉高压症消化道出血治疗共识(中华外科学会门静脉高压症学组讨论稿).外科理论与实践, 2009, 14(1):79-81.
2.	Kandhi S, Froogh G, Qin J, et al. EETs elicit direct increases in pulmonary arterial pressure in mice. Am J Hypertens, 2016, 29(5):598-604.
3.	Qin J, Sun D, Jiang H, et al. Inhibition of soluble epoxide hydrolase increases coronary perfusion in mice. Physiol Rep, 2015, 3(6):e12427.
4.	刘璐, 曹剑.环氧二十碳三烯酸防治心血管疾病的研究进展.中华老年心脑血管病杂志, 2014, 16(12):1329-1331.
5.	Imig JD. Epoxides and soluble epoxide hydrolase in cardiovascular physiology. Physiol Rev, 2012, 92(1):101-130.
6.	Fitzpatrick FA, Ennis MD, Baze ME, et al. Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosatrienoic acids. Influence of stereochemistry. J Biol Chem, 1986, 261(32):15334-15338.
7.	Breyer RM, Bagdassarian CK, Myers SA, et al. Prostanoid receptors:subtypes and signaling. Annu Rev Pharmacol Toxicol, 2001, 41:661-690.
8.	Capra V, Thompson MD, Sala A, et al. Cysteinyl-leukotrienes and their receptors in asthma and other inflammatory diseases:critical update and emerging trends. Med Res Rev, 2007, 27(4):469-527.
9.	Williams JM, Murphy S, Burke M, et al. 20-hydroxyeicosatetraeonic acid:a new target for the treatment of hypertension. J Cardiovasc Pharmacol, 2010, 56(4):336-344.
10.	Roman RJ. P-450 metabolites of arachidonic acid in the control of cardiovascular function. Physiol Rev, 2002, 82(1):131-185.
11.	Hanukoglu I. Electron transfer proteins of cytochrome P450 systems. Adv Mol Cell Bio, 1996, 14:29-56.
12.	Capdevila JH, Falck JR, Dishman E, et al. Cytochrome P-450 arachidonate oxygenase. Methods Enzymol, 1990, 187:385-394.
13.	Sun D, Cuevas AJ, Gotlinger K, et al. Soluble epoxide hydrolase-dependent regulation of myogenic response and blood pressure. Am J Physiol Heart Circ Physiol, 2014, 306(8):H1146-H1153.
14.	Liu X, Gebremedhin D, Harder DR, et al. Contribution of epoxyeicosatrienoic acids to the cerebral blood flow response to hypoxemia. J Appl Physiol (1985), 2015, 119(10):1202-1209.
15.	Imig JD, Falck JR, Inscho EW. Contribution of cytochrome P450 epoxygenase and hydroxylase pathways to afferent arteriolar autoregulatory responsiveness. Br J Pharmacol, 1999, 127(6):1399-1405.
16.	Imig JD, Pham BT, LeBlanc EA, et al. Cytochrome P450 and cyclooxygenase metabolites contribute to the endothelin-1 afferent arteriolar vasoconstrictor and calcium responses. Hypertension, 2000, 35(1 Pt 2):307-312.
17.	Kandhi S, Qin J, Froogh G, et al. EET-dependent potentiation of pulmonary arterial pressure:sex-different regulation of soluble epoxide hydrolase. Am J Physiol Lung Cell Mol Physiol, 2015, 309(12):L1478-L1486.
18.	Norwood S, Liao J, Hammock BD, et al. Epoxyeicosatrienoic acids and soluble epoxide hydrolase:potential therapeutic targets for inflammation and its induced carcinogenesis. Am J Transl Res, 2010, 2(4):447-457.
19.	Morisseau C, Hammock BD. Impact of soluble epoxide hydrolase and epoxyeicosanoids on human health. Annu Rev Pharmacol Toxicol, 2013, 53:37-58.
20.	Yu Z, Xu F, Huse LM, et al. Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ Res, 2000, 87(11):992-998.
21.	Earley S, Heppner TJ, Nelson MT, et al. TRPV4 forms a novel Ca²⁺ signaling complex with ryanodine receptors and BKCa channels. Circ Res, 2005, 97(12):1270-1279.
22.	Zhang P, Ma Y, Wang Y, et al. Nitric oxide and protein kinase G act on TRPC1 to inhibit 11, 12-EET-induced vascular relaxation. Cardiovasc Res, 2014, 104(1):138-146.
23.	Zou AP, Fleming JT, Falck JR, et al. Stereospecific effects of epoxyeicosatrienoic acids on renal vascular tone and K(+)-channel activity. Am J Physiol, 1996, 270(5 Pt 2):F822-F832.
24.	Imig JD, Falck JR, Wei S, et al. Epoxygenase metabolites contribute to nitric oxide-independent afferent arteriolar vasodilation in response to bradykinin. J Vasc Res, 2001, 38(3):247-255.
25.	Stephenson AH, Sprague RS, Weintraub NL, et al. Inhibition of cytochrome P-450 attenuates hypoxemia of acute lung injury in dogs. Am J Physiol, 1996, 270(4 Pt 2):H1355-H1362.
26.	Stephenson AH, Sprague RS, Lonigro AJ. 5, 6-epoxyeicosatrienoic acid reduces increases in pulmonary vascular resistance in the dog. Am J Physiol, 1998, 275(1 Pt 2):H100-H109.
27.	Tan JZ, Kaley G, Gurtner GH. Nitric oxide and prostaglandins mediate vasodilation to 5, 6-EET in rabbit lung. Adv Exp Med Biol, 1997, 407:561-566.
28.	Fleming I. Cytochrome p450 and vascular homeostasis. Circ Res, 2001, 89(9):753-762.
29.	Zhu D, Bousamra MN, Zeldin DC, et al. Epoxyeicosatrienoic acids constrict isolated pressurized rabbit pulmonary arteries. Am J Physiol Lung Cell Mol Physiol, 2000, 278(2):L335-L343.
30.	Iwakiri Y. Pathophysiology of portal hypertension. Clin Liver Dis, 2014, 18(2):281-291.
31.	Cichoz-Lach H, Celiński K, Słomka M, et al. Pathophysiology of portal hypertension. J Physiol Pharmacol, 2008, 59 Suppl 2:231-238.
32.	Sacerdoti D, Pesce P, Di Pascoli M, et al. Arachidonic acid metabolites and endothelial dysfunction of portal hypertension. Prostaglandins Other Lipid Mediat, 2015, 120:80-90.
33.	Gracia-Sancho J, Maeso-Díaz R, Fernández-Iglesias A, et al. New cellular and molecular targets for the treatment of portal hypertension. Hepatol Int, 2015, 9(2):183-191.
34.	Sacerdoti D, Jiang H, Gaiani S, et al. 11, 12-EET increases porto-sinusoidal resistance and may play a role in endothelial dysfunction of portal hypertension. Prostaglandins Other Lipid Mediat, 2011, 96(1-4):72-75.
35.	Harris TR, Bettaieb A, Kodani S, et al. Inhibition of soluble epoxide hydrolase attenuates hepatic fibrosis and endoplasmic reticulum stress induced by carbon tetrachloride in mice. Toxicol Appl Pharmacol, 2015, 286(2):102-111.
36.	Yang YL, Di L, Duan YY, et al. A prospective experimental study of liver fibrosis with ultrasound and its correlation with hepatic reserve function and hemodynamics. BMC Gastroenterol, 2012, 12:168.
37.	Folkman J. Tumor angiogenesis:therapeutic implications. N Engl J Med, 1971, 285(21):1182-1186.
38.	Nagy JA, Morgan ES, Herzberg KT, et al. Pathogenesis of ascites tumor growth:angiogenesis, vascular remodeling, and stroma formation in the peritoneal lining. Cancer Res, 1995, 55(2):376-385.
39.	Chen R, Jiang J, Xiao X, et al. Effects of epoxyeicosatrienoic acids on levels of eNOS phosphorylation and relevant signaling transduction pathways involved. Sci China C Life Sci, 2005, 48(5):495-505.
40.	Wang H, Lin L, Jiang J, et al. Up-regulation of endothelial nitric-oxide synthase by endothelium-derived hyperpolarizing factor involves mitogen-activated protein kinase and protein kinase C signaling pathways. J Pharmacol Exp Ther, 2003, 307(2):753-764.
41.	罗蒙.内皮源性一氧化氮对肝硬化门静脉高压症内脏动脉RhoA/ROCK信号通路影响机制的研究.苏州大学, 2013.
42.	Hercule HC, Schunck WH, Gross V, et al. Interaction between P450 eicosanoids and nitric oxide in the control of arterial tone in mice. Arterioscler Thromb Vasc Biol, 2009, 29(1):54-60.
43.	Chen D, Whitcomb R, MacIntyre E, et al. Pharmacokinetics and pharmacodynamics of AR9281, an inhibitor of soluble epoxide hydrolase, in singleand multiple-dose studies in healthy human subjects. J Clin Pharmacol, 2012, 52(3):319-328.
44.	Van de Voorde J, Vanheel B. Influence of cytochrome P-450 inhibitors on endothelium-dependent nitro-L-arginine-resistant relaxation and cromakalim-induced relaxation in rat mesenteric arteries. J Cardiovasc Pharmacol, 1997, 29(6):827-832.
45.	Di Pascoli M, Turato C, Zampieri F, et al. Changes in gene expression of cytochrome P-450 in liver, kidney and aorta of cirrhotic rats. Prostaglandins Other Lipid Mediat, 2015, 120:134-138.

1. 中华外科学会门静脉高压症学组.肝硬化门静脉高压症消化道出血治疗共识(中华外科学会门静脉高压症学组讨论稿).外科理论与实践, 2009, 14(1):79-81.
2. Kandhi S, Froogh G, Qin J, et al. EETs elicit direct increases in pulmonary arterial pressure in mice. Am J Hypertens, 2016, 29(5):598-604.
3. Qin J, Sun D, Jiang H, et al. Inhibition of soluble epoxide hydrolase increases coronary perfusion in mice. Physiol Rep, 2015, 3(6):e12427.
4. 刘璐, 曹剑.环氧二十碳三烯酸防治心血管疾病的研究进展.中华老年心脑血管病杂志, 2014, 16(12):1329-1331.
5. Imig JD. Epoxides and soluble epoxide hydrolase in cardiovascular physiology. Physiol Rev, 2012, 92(1):101-130.
6. Fitzpatrick FA, Ennis MD, Baze ME, et al. Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosatrienoic acids. Influence of stereochemistry. J Biol Chem, 1986, 261(32):15334-15338.
7. Breyer RM, Bagdassarian CK, Myers SA, et al. Prostanoid receptors:subtypes and signaling. Annu Rev Pharmacol Toxicol, 2001, 41:661-690.
8. Capra V, Thompson MD, Sala A, et al. Cysteinyl-leukotrienes and their receptors in asthma and other inflammatory diseases:critical update and emerging trends. Med Res Rev, 2007, 27(4):469-527.
9. Williams JM, Murphy S, Burke M, et al. 20-hydroxyeicosatetraeonic acid:a new target for the treatment of hypertension. J Cardiovasc Pharmacol, 2010, 56(4):336-344.
10. Roman RJ. P-450 metabolites of arachidonic acid in the control of cardiovascular function. Physiol Rev, 2002, 82(1):131-185.
11. Hanukoglu I. Electron transfer proteins of cytochrome P450 systems. Adv Mol Cell Bio, 1996, 14:29-56.
12. Capdevila JH, Falck JR, Dishman E, et al. Cytochrome P-450 arachidonate oxygenase. Methods Enzymol, 1990, 187:385-394.
13. Sun D, Cuevas AJ, Gotlinger K, et al. Soluble epoxide hydrolase-dependent regulation of myogenic response and blood pressure. Am J Physiol Heart Circ Physiol, 2014, 306(8):H1146-H1153.
14. Liu X, Gebremedhin D, Harder DR, et al. Contribution of epoxyeicosatrienoic acids to the cerebral blood flow response to hypoxemia. J Appl Physiol (1985), 2015, 119(10):1202-1209.
15. Imig JD, Falck JR, Inscho EW. Contribution of cytochrome P450 epoxygenase and hydroxylase pathways to afferent arteriolar autoregulatory responsiveness. Br J Pharmacol, 1999, 127(6):1399-1405.
16. Imig JD, Pham BT, LeBlanc EA, et al. Cytochrome P450 and cyclooxygenase metabolites contribute to the endothelin-1 afferent arteriolar vasoconstrictor and calcium responses. Hypertension, 2000, 35(1 Pt 2):307-312.
17. Kandhi S, Qin J, Froogh G, et al. EET-dependent potentiation of pulmonary arterial pressure:sex-different regulation of soluble epoxide hydrolase. Am J Physiol Lung Cell Mol Physiol, 2015, 309(12):L1478-L1486.
18. Norwood S, Liao J, Hammock BD, et al. Epoxyeicosatrienoic acids and soluble epoxide hydrolase:potential therapeutic targets for inflammation and its induced carcinogenesis. Am J Transl Res, 2010, 2(4):447-457.
19. Morisseau C, Hammock BD. Impact of soluble epoxide hydrolase and epoxyeicosanoids on human health. Annu Rev Pharmacol Toxicol, 2013, 53:37-58.
20. Yu Z, Xu F, Huse LM, et al. Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ Res, 2000, 87(11):992-998.
21. Earley S, Heppner TJ, Nelson MT, et al. TRPV4 forms a novel Ca²⁺ signaling complex with ryanodine receptors and BKCa channels. Circ Res, 2005, 97(12):1270-1279.
22. Zhang P, Ma Y, Wang Y, et al. Nitric oxide and protein kinase G act on TRPC1 to inhibit 11, 12-EET-induced vascular relaxation. Cardiovasc Res, 2014, 104(1):138-146.
23. Zou AP, Fleming JT, Falck JR, et al. Stereospecific effects of epoxyeicosatrienoic acids on renal vascular tone and K(+)-channel activity. Am J Physiol, 1996, 270(5 Pt 2):F822-F832.
24. Imig JD, Falck JR, Wei S, et al. Epoxygenase metabolites contribute to nitric oxide-independent afferent arteriolar vasodilation in response to bradykinin. J Vasc Res, 2001, 38(3):247-255.
25. Stephenson AH, Sprague RS, Weintraub NL, et al. Inhibition of cytochrome P-450 attenuates hypoxemia of acute lung injury in dogs. Am J Physiol, 1996, 270(4 Pt 2):H1355-H1362.
26. Stephenson AH, Sprague RS, Lonigro AJ. 5, 6-epoxyeicosatrienoic acid reduces increases in pulmonary vascular resistance in the dog. Am J Physiol, 1998, 275(1 Pt 2):H100-H109.
27. Tan JZ, Kaley G, Gurtner GH. Nitric oxide and prostaglandins mediate vasodilation to 5, 6-EET in rabbit lung. Adv Exp Med Biol, 1997, 407:561-566.
28. Fleming I. Cytochrome p450 and vascular homeostasis. Circ Res, 2001, 89(9):753-762.
29. Zhu D, Bousamra MN, Zeldin DC, et al. Epoxyeicosatrienoic acids constrict isolated pressurized rabbit pulmonary arteries. Am J Physiol Lung Cell Mol Physiol, 2000, 278(2):L335-L343.
30. Iwakiri Y. Pathophysiology of portal hypertension. Clin Liver Dis, 2014, 18(2):281-291.
31. Cichoz-Lach H, Celiński K, Słomka M, et al. Pathophysiology of portal hypertension. J Physiol Pharmacol, 2008, 59 Suppl 2:231-238.
32. Sacerdoti D, Pesce P, Di Pascoli M, et al. Arachidonic acid metabolites and endothelial dysfunction of portal hypertension. Prostaglandins Other Lipid Mediat, 2015, 120:80-90.
33. Gracia-Sancho J, Maeso-Díaz R, Fernández-Iglesias A, et al. New cellular and molecular targets for the treatment of portal hypertension. Hepatol Int, 2015, 9(2):183-191.
34. Sacerdoti D, Jiang H, Gaiani S, et al. 11, 12-EET increases porto-sinusoidal resistance and may play a role in endothelial dysfunction of portal hypertension. Prostaglandins Other Lipid Mediat, 2011, 96(1-4):72-75.
35. Harris TR, Bettaieb A, Kodani S, et al. Inhibition of soluble epoxide hydrolase attenuates hepatic fibrosis and endoplasmic reticulum stress induced by carbon tetrachloride in mice. Toxicol Appl Pharmacol, 2015, 286(2):102-111.
36. Yang YL, Di L, Duan YY, et al. A prospective experimental study of liver fibrosis with ultrasound and its correlation with hepatic reserve function and hemodynamics. BMC Gastroenterol, 2012, 12:168.
37. Folkman J. Tumor angiogenesis:therapeutic implications. N Engl J Med, 1971, 285(21):1182-1186.
38. Nagy JA, Morgan ES, Herzberg KT, et al. Pathogenesis of ascites tumor growth:angiogenesis, vascular remodeling, and stroma formation in the peritoneal lining. Cancer Res, 1995, 55(2):376-385.
39. Chen R, Jiang J, Xiao X, et al. Effects of epoxyeicosatrienoic acids on levels of eNOS phosphorylation and relevant signaling transduction pathways involved. Sci China C Life Sci, 2005, 48(5):495-505.
40. Wang H, Lin L, Jiang J, et al. Up-regulation of endothelial nitric-oxide synthase by endothelium-derived hyperpolarizing factor involves mitogen-activated protein kinase and protein kinase C signaling pathways. J Pharmacol Exp Ther, 2003, 307(2):753-764.
41. 罗蒙.内皮源性一氧化氮对肝硬化门静脉高压症内脏动脉RhoA/ROCK信号通路影响机制的研究.苏州大学, 2013.
42. Hercule HC, Schunck WH, Gross V, et al. Interaction between P450 eicosanoids and nitric oxide in the control of arterial tone in mice. Arterioscler Thromb Vasc Biol, 2009, 29(1):54-60.
43. Chen D, Whitcomb R, MacIntyre E, et al. Pharmacokinetics and pharmacodynamics of AR9281, an inhibitor of soluble epoxide hydrolase, in singleand multiple-dose studies in healthy human subjects. J Clin Pharmacol, 2012, 52(3):319-328.
44. Van de Voorde J, Vanheel B. Influence of cytochrome P-450 inhibitors on endothelium-dependent nitro-L-arginine-resistant relaxation and cromakalim-induced relaxation in rat mesenteric arteries. J Cardiovasc Pharmacol, 1997, 29(6):827-832.
45. Di Pascoli M, Turato C, Zampieri F, et al. Changes in gene expression of cytochrome P-450 in liver, kidney and aorta of cirrhotic rats. Prostaglandins Other Lipid Mediat, 2015, 120:134-138.

CHINESE JOURNAL OF BASES AND CLINICS IN GENERAL SURGERY

Research Progress of Epoxyeicosatrienoic Acid and Its Role in Regulating Development of Cirrhotic Portal Hypertension

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