Discovery of soluble epoxide hydrolase inhibitors from natural products

Food and Chemical Toxicology

Volumn 64, Issue , 2014, Pages 225-230

  Lee, Gwan Ho ^a   Oh, Soo Jin ^b   Lee, Sang Yoon ^a   Lee, Ji Yoon ^a   Ma, Jin Yeul ^c   Kim, Young Ho ^a   Kim, Sang Kyum ^a  

^a Chungnam National University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^c Korea Institute of Oriental Medicine (KIOM)   (South Korea)

Author keywords

Honokiol; Selectivity; Soluble epoxide hydrolase; Amyrin acetate

Indexed keywords

14,15 EPOXY 5,8,11 ICOSATRIENOIC ACID; 3 PHENYL CYANO(6 METHOXY 2 NAPHTHALENYL)METHYL ESTER 2 OXIRANEACETIC; BETA AMYRIN; EPOXIDE HYDROLASE; HONOKIOL; NATURAL PRODUCT; REAGENT; UNCLASSIFIED DRUG; VALPROMIDE;

ACER; ACER MANDSHURICUM; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SELECTIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MAGNOLIA OFFICINALIS; MAGNOLIACEAE; MASS SPECTROMETRY; NONHUMAN;

ACER MANDSHURICUM; MAGNOLIA OFFICINALIS;

HONOKIOL; SELECTIVITY; SOLUBLE EPOXIDE HYDROLASE; Β-AMYRIN ACETATE;

BIOLOGICAL PRODUCTS; BIPHENYL COMPOUNDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME INHIBITORS; EPOXIDE HYDROLASES; FLUOROMETRY; LIGNANS; OLEANOLIC ACID; SPECTROPHOTOMETRY, ULTRAVIOLET; TANDEM MASS SPECTROMETRY;

EID: 84890706211     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2013.11.042     Document Type: Article

References (58)

1. Akihisa T., Kojima N., Kikuchi T., Yasukawa K., Tokuda H., Masters E.T., Manosroi A., Manosroi J. Anti-inflammatory and chemopreventive effects of triterpenecinnamates and acetates from shea fat. J. Oleo Sci. 2010, 59:273-280.
2. Arima S., Endo Y., Yaoita H., Omata K., Ogawa S., Tsunoda K., Abe M., Takeuchi K., Abe K., Ito S. Possible role of P-450 metabolite of arachidonic acid in vasodilator mechanism of angiotensin II type 2 receptor in the isolated microperfused rabbit afferent arteriole. J. Clin. Invest. 1997, 100:2816-2823.
3. Bae K.H., Oh H.R. Synergistic effect of lysozyme on bactericidal activity of magnolol and honokiol against a cariogenic bacterium, Streptococcus mutans OMZ 176. Arch. Pharm. Res. 1990, 13:117-119.
4. Baxter S.W., Choong D.Y., Campbell I.G. Microsomal epoxide hydrolase polymorphism and susceptibility to ovarian cancer. Cancer Lett. 2002, 177:75-81.
5. Böhmdorfer M., Maier-Salamon A., Taferner B., Reznicek G., Thalhammer T., Hering S., Hüfner A., Schühly W., Jäger W. In vitro metabolism and disposition of honokiol in rat and human livers. J. Pharm. Sci. 2011, 100:3506-3516.
6. Chiamvimonvat N., Ho C.M., Tsai H.J., Hammock B.D. The soluble epoxide hydrolase as a pharmaceutical target for hypertension. J. Cardiovasc. Pharmacol. 2007, 50:225-237.
7. Ching J., Lin H.S., Tanb C.H., Koh H.L. Quantification of α- and β-amyrin in rat plasma by gas chromatography-mass spectrometry: application to preclinical pharmacokinetic study. J. Mass Spectrom. 2011, 46:457-464.
8. Cuong N.M., Hung T.Q., Sung T.V., Taylor W.C. A new dimeric carbazole alkaloid from Glycosmis stenocarpa roots. Chem. Pharm. Bullet. 2004, 52:1175-1178.
9. Cuong N.M., Tai B.H., Hoan D.H., Huong T.T., Kim Y.H., Hyun J.H., Kang H.K. Inhibitory effects of indirubin derivatives on the growth of HL-60 leukemia cells. Nat. Prod. Commun. 2010, 5:103-106.
10. Deng Y., Theken K.N., Lee C.R. Cytochrome P450 epoxygenases, soluble epoxide hydrolase, and the regulation of cardiovascular inflammation. J. Mol. Cell. Cardiol. 2010, 48:331-341.
11. Ding Y., Liang C., Kim J.H., Lee Y.M., Hyun J.H., Kang H.K., Kim J.A., Min B.S., Kim Y.H. Triterpene compounds isolated from Acer mandshuricum and their anti-inflammatory activity. Bioorg. Med. Chem. Lett. 2010, 20:1528-1531.
12. Fitzpatrick F.A., Murphy R.C. Cytochrome P-450 metabolism of arachidonic acid: formation and biological actions of "epoxygenase"-derived eicosanoids. Pharmacol. Rev. 1988, 40:229-241.
13. Fulton D., Mahboubi K., McGiff J.C., Quilley J. Cytochrome P450-dependent effects of bradykinin in the rat heart. Brit. J. Pharmacol. 1995, 114:99-102.
14. Hwang S.H., Tsai H.J., Liu J.Y., Morisseau C., Hammock B.D. Orally bioavailable potent soluble epoxide hydrolase inhibitors. J. Med. Chem. 2007, 50:3825-3840.
15. Hwang C.J., Park M.H., Jung H.W., Park Y.K., Kim Y.H., Kang J.S., Cho C.W. A stable fixed-dose combination tablet of pseudoephedrine and KOB extracts for the extended release. Drug Res. (Stuttg) 2013, 63:572-578.
16. Imig J.D., Hammock B.D. Soluble epoxide hydrolase as a therapeutic target for cardiovascular diseases. Nat. Rev. Drug Discov. 2009, 8:794-805.
17. Kang H.S., Kim Y.H., Lee C.S., Lee J.J., Choi I., Pyun K.H. Suppression of interleukin-1 and tumor necrosis factor-alpha production by acanthoic acid, (-)-pimara-9(11),15-dien-19-oic acid, and it antifibrotic effects in vivo. Cell. Immunol. 1996, 170:212-221.
18. Kim J.H., Han Y.N. Dammarane-type saponins from Gynostemma pentaphyllum. Phytochemistry 2011, 72:1453-1459.
19. Kim Y.H., Chung B.S., Kim H.J. Studies on the constituents of acanthopanax koreanum. Kor. J. Pharmacogn. 1985, 16:151-154.
20. Kim I.H., Morisseau C., Watanabe T., Hammock B.D. Design, synthesis, and biological activity of 1,3-disubstituted ureas as potent inhibitors of the soluble epoxide hydrolase of increased water solubility. J. Med. Chem. 2004, 47:2110-2122.
21. Kim J.A., Yang S.Y., Koo J.E., Koh Y.S., Kim Y.H. Lupane-type triterpenoids from the steamed leaves of Acanthopanax koreanum and their inhibitory effects on the LPS-stimulated pro-inflammatory cytokine production in bone marrow-derived dendritic cells. Bioorg. Med. Chem. Lett. 2010, 20:6703-6707.
22. Kim Y.H., Lee Y.S., Choi E.M. Chrysoeriol isolated from Eurya cilliata leaves protects MC3T3-E1 cells against hydrogen peroxide-induced inhibition of osteoblastic differentiation. J. Appl. Toxicol. 2010, 30:666-673.
23. Kim J.A., Song S.B., Yang S.Y., Kim Y.H. Components from the steamed leaves of Acanthopanax koreanum and their effects on PPAR activity in HepG2 cells. Nat. Prod. Commun. 2011, 6:1233-1236.
24. Kiyohara C., Otsu A., Shirakawa T., Fukuda S., Hopkin J.M. Genetic polymorphisms and lung cancer susceptibility: a review. Lung Cancer 2002, 37:241-256.
25. Kuribara H., Kishi E., Hattori N., Yuzurihara M., Maruyama Y. Application of the elevated plus-maze test in mice for evaluation of the content of honokiol in water extracts of magnolia. Phytother. Res. 1999, 13:593-596.
26. Liou K.T., Lin S.M., Huang S.S., Chih C.L., Tsai S.K. Honokiol ameliorates cerebral infarction from ischemia-reperfusion injury in rats. Planta Med. 2003, 69:130-134.
27. Lo Y.C., Teng C.M., Chen C.F., Chen C.C., Hong C.Y. Magnolol and honokiol isolated from Magnolia officinalis protect rat heart mitochondria against lipid peroxidation. Biochem. Pharmacol. 1994, 47:549-553.
28. Min B.S., Gao J.J., Nakamura N., Kim Y.H., Hattori M. Cytotoxic alkaloids and a flavan from the bulbs of Crinum asiaticum var. japonicum. Biol. Pharm. Bullet. 2001, 49:1217-1219.
29. Miura H., Gutterman D.D. Human coronary arteriolar dilation to arachidonic acid depends on cytochrome P-450 monooxygenase and Ca2+-activated K+ channels. Circ. Res. 1998, 83:501-507.
30. Morisseau C., Hammock B.D. Epoxide hydrolases: mechanisms, inhibitor designs, and biological roles. Ann. Rev. Pharmacol. Toxicol. 2005, 45:311-333.
31. Morisseau C., Goodrow M.H., Dowdy D., Zheng J., Greene J.F., Sanborn J.R., Hammock B.D. Potent urea and carbamate inhibitors of soluble epoxide hydrolases. Proc. Natl. Acad. Sci. USA 1999, 96:8849-8854.
32. Newman J.W., Watanabe T., Hammock B.D. The simultaneous quantification of cytochrome P450 dependent linoleate and arachidonate metabolites in urine by HPLC-MS/MS. J. Lipid Res. 2002, 43:1563-1578.
33. Node K., Huo Y., Ruan X., Yang B., Spiecker M., Ley K., Zeldin D.C., Liao J.K. Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science 1999, 285:1276-1279.
34. Norwood S., Liao J., Hammock B.D., Yang G.Y. Epoxyeicosatrienoic acids and soluble epoxide hydrolase: potential therapeutic targets for inflammation and its induced carcinogenesis. Am. J. Transl. Res. 2010, 2:447-457.
35. Oesch F. Mammalian epoxide hydrases: inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic compounds. Xenobiotica 1973, 3:305-340.
36. Oliveira F.A., Lima-Junior R.C., Cordeiro W.M., Vieira-Junior G.M., Chaves M.H., Almeida F.R., Silva R.M., Santos F.A., Rao V.S. Pentacyclictriterpenoids, alpha, beta-amyrins, suppress the scratching behavior in a mouse model of pruritus. Pharmacol. Biochem. Behav. 2004, 78:719-725.
37. Pfister S.L., Gauthier K.M., Campbell W.B. Vascular pharmacology of epoxyeicosatrienoic acids. Adv. Pharmacol. 2010, 60:27-59.
38. Rosamond W., Flegal K., Friday G., Furie K., Go A., Greenlund K., Haase N., Ho M., Howard V., Kissela B., Kittner S., Lloyd-Jones D., McDermott M., Meigs J., Moy C., Nichol G., O'Donnell C.J., Roger V., Rumsfeld J., Sorlie P., Steinberger J., Thom T., Wasserthiel-Smoller S., Hong Y., American Heart Association Statistics C., Stroke Statistics S. Heart disease and stroke statistics-2007 update: a report from the American Heart Association Statistics Committee and Stroke Statistics Subcommittee. Circulation 2007, 115:69-171.
39. Rose T.E., Morisseau C., Liu J.Y., Inceoglu B., Jones P.D., Sanborn J.R., Hammock B.D. 1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain. J. Med. Chem. 2010, 53:7067-7075.
40. Shen H.C., Ding F.X., Wang S., Xu S., Chen H.S., Tong X., Tong V., Mitra K., Kumar S., Zhang X., Chen Y., Zhou G., Pai L.Y., Alonso-Galicia M., Chen X., Zhang B., Tata J.R., Berger J.P., Colletti S.L. Discovery of spirocyclic secondary amine-derived tertiary ureas as highly potent, selective and bioavailable soluble epoxide hydrolase inhibitors. Bioorg. Med. Chem. Lett. 2009, 19:3398-3404.
41. Simon S.R., Black H.R., Moser M., Berland W.E. Cough and ACE inhibitors. Arch. Internal Med. 1992, 152:1698-1700.
42. Sinal C.J., Miyata M., Tohkin M., Nagata K., Bend J.R., Gonzalez F.J. Targeted disruption of soluble epoxide hydrolase reveals a role in blood pressure regulation. J. Biol. Chem. 2000, 275:40504-40510.
43. Smith C.A., Harrison D.J. Association between polymorphism in gene for microsomal epoxide hydrolase and susceptibility to emphysema. Lancet 1997, 350:630-633.
44. Son M.J., Kim H.K., Huong, do T.T., Kim Y.H., Van Sung T., Cuong N.M., Woo S.H. Chrysosplenol C increases contraction in rat ventricular myocytes. J. Cardiovasc. Pharmacol. 2011, 57:259-262.
45. Sudhahar V., Shaw S., Imig J.D. Epoxyeicosatrienoic acid analogs and vascular function. Curr. Med. Chem. 2010, 17:1181-1190.
46. Tai B.H., Jung B.Y., Cuong N.M., Linh P.T., Tung N.H., Nhiem N.X., Huong T.T., Anh N.T., Kim J.A., Kim S.K., Kim Y.H. Total peroxynitrite scavenging capacity of phenylethanoid and flavonoid glycosides from the flowers of Buddleja officinalis. Biol. Pharm. Bullet. 2009, 32:1952-1956.
47. Teng C.M., Chen C.C., Ko F.N., Lee L.G., Huang T.F., Chen Y.P., Hsu H.Y. Two antiplatelet agents from Magnolia officinalis. Thromb. Res. 1988, 50:757-765.
48. To-Figueras J., Gene M., Gomez-Catalan J., Pique E., Borrego N., Caballero M., Cruellas F., Raya A., Dicenta M., Corbella J. Microsomal epoxide hydrolase and glutathione S-transferase polymorphisms in relation to laryngeal carcinoma risk. Cancer Lett. 2002, 187:95-101.
49. Tsai T.H., Chou C.J., Cheng F.C., Chen C.F. Pharmacokinetics of honokiol after intravenous administration in rats assessed using high-performance liquid chromatography. J. Chromatogr. B: Biomed. Sci. Appl. 1994, 655:41-45.
50. Tung N.H., Cho K.W., Kim J.A., Song G.Y., Kim Y.H. Dammarane-Type glycosides from the steamed flower-buds of Panax ginseng. Bullet. Kor. Chem. Soc. 2010, 31:1381-1384.
51. Tung N.H., Kim S.K., Ra J.C., Zhao Y.Z., Sohn D.H., Kim Y.H. Antioxidative and hepatoprotective diarylheptanoids from the bark of Alnus japonica. Planta Med. 2010, 76:626-629.
52. Tung N.H., Song G.Y., Nhiem N.X., Ding Y., Tai B.H., Jin L.G., Lim C.M., Hyun J.W., Park C.J., Kang H.K., Kim Y.H. Dammarane-type saponins from the flower buds of Panax ginseng and their intracellular radical scavenging capacity. J. Agric. Food Chem. 2010, 58:868-874.
53. van Rijnsoever E.W., Kwee-Zuiderwijk W.J., Feenstra J. Angioneurotic edema attributed to the use of losartan. Arch. Int. Med. 1998, 158:2063-2065.
54. Vitor C.E., Figueiredo C.P., Hara D.B., Bento A.F., Mazzuco T.L., Calixto J.B. Therapeutic action and underlying mechanisms of a combination of two pentacyclic triterpenes, α- and β-amyrin, in a mouse model of colitis. Brit. J. Pharmacol. 2009, 157:1034-1044.
55. Watanabe T., Hammock B.D. Rapid determination of soluble epoxide hydrolase inhibitors in rat hepatic microsomes by high-performance liquid chromatography with electrospray tandem mass spectrometry. Anal. Biochem. 2001, 299:227-234.
56. Wolf N.M., Morisseau C., Jones P.D., Hock B., Hammock B.D. Development of a high-throughput screen for soluble epoxide hydrolase inhibition. Anal. Biochem. 2006, 355:71-80.
57. Yu Z., Xu F., Huse L.M., Morisseau C., Draper A.J., Newman J.W., Parker C., Graham L., Engler M.M., Hammock B.D., Zeldin D.C., Kroetz D.L. Soluble epoxide hydrolase regulates hydrolysis of vasoactive epoxyeicosatrienoic acids. Circ. Res. 2000, 87:992-998.
58. Zhang G.S., Wang R.J., Zhang H.N., Zhang G.P., Luo M.S., Luo J.D. Effects of chronic treatment with honokiol in spontaneously hypertensive rats. Biol. Pharm. Bullet. 2010, 33:427-431.