Structure-function relationships of citrus limonoids on p38 MAP kinase activity in human aortic smooth muscle cells

European Journal of Pharmacology

Volumn 670, Issue 1, 2011, Pages 44-49

  Kim, Jinhee ^a   Jayaprakasha, Guddadarangavvanahally K ^a   Muthuchamy, Mariappan ^b   Patil, Bhimanagouda S ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b TEXAS A AND M HEALTH SCIENCE CENTER   (United States)

Author keywords

Citrus limonoids; HASMC; p38 MAPK; Structure function relationship; TNF

Indexed keywords

DEACETYLNOMILIN; DEFURAN LIMONIN; DEFURAN NOMILIN; LIMONIN; LIMONOID; METHYL NOMILINATE; MITOGEN ACTIVATED PROTEIN KINASE P38; NOMILIN; OBACUNONE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

AORTA MEDIA; ARTICLE; CHEMICAL MODIFICATION; CITRUS FRUIT; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME REGULATION; HUMAN; HUMAN CELL; INFLAMMATION; PRIORITY JOURNAL; SMOOTH MUSCLE FIBER; STRUCTURE ACTIVITY RELATION;

AORTA; CITRUS; FURANS; HUMANS; LIMONINS; MYOCYTES, SMOOTH MUSCLE; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PROTEIN KINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR NECROSIS FACTOR-ALPHA;

EID: 80054721435     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2011.08.035     Document Type: Article

References (53)

1. M.E. Anderson, L.S. Higgins, and H. Schulman Disease mechanisms and emerging therapies: protein kinases and their inhibitors in myocardial disease Nat. Clin. Pract. Cardiovasc. Med. 3 2006 437 445 (Pubitemid 44150961)
2. L. Bazzano, J. He, L.G. Ogden, C.M. Loria, S. Vupputuri, L. Myers, and P.K. Whelton Fruit and vegetable intake and risk of cardiovascular disease in US adults: the first national health and nutrition examination survey epidemiologic follow-up study Am. J. Clin. Nutr. 76 2002 93 99 (Pubitemid 34686554)
3. T.M. Behr, M. Berova, C.P. Doe, H. Ju, C.E. Angermann, J. Boehm, and R.N. Willette p38 mitogen-activated protein kinase inhibitors for the treatment of chronic cardiovascular disease Curr. Opin. Invest. Drugs 4 2003 1059 1064 (Pubitemid 37321399)
4. P.H.J. Carlsen, T. Katsuki, V.S. Martin, and K.B. Sharpless A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds J. Org. Chem. 46 1981 3936 3938
5. J.M. Cavaillon Cytokines and macrophages Biomed. Pharmacother. 48 1994 445 453
6. J. Dai, V.A. Yaylayan, G.S.V. Raghavan, and J.R. Pares Extraction and colorimetric determination of azadirachtin-related limonoids in neem seed kernel J. Agric. Food Chem. 47 1999 3738 3742 (Pubitemid 29449499)
7. L. Dauchet, M. Montaye, J.B. Ruidavets, D. Arveiler, F. Kee, A. Bingham, J. Ferrières, B. Haas, A. Evans, and P. Ducimetière Association between the frequency of fruit and vegetable consumption and cardiovascular disease in male smokers and non-smokers Eur. J. Clin. Nutr. 64 2010 578 586
8. M.Z. El-Readi, D. Hamdan, N. Farrag, A. El-Shazly, and M. Wink Inhibition of p-glycoprotein activity by limonin and other secondary metabolites from citrus species in human colon and leukaemia cell lines Eur. J. Pharmacol. 626 2010 139 145
9. T. Force, K. Kuida, M. Namchuk, K. Parang, and J.M. Kyriakis Inhibitors of protein kinase signaling pathways: emerging therapies for cardiovascular disease Circulation 109 2004 1196 1205 (Pubitemid 38372775)
10. N. Guthrie, K. Morley, S. Hasegawa, G.D. Manners, and T. Vandenberg Inhibition of human breast cancer cells by citrus limonoids G. Manners, M.B. S. Hasegawa, Citrus Limonoids 2000 American Chemical Society, Inc Washington, DC 164 174
11. J. Han, Y. Jiang, Z. Li, V.V. Kravchenko, and R.J. Ulevitch Activation of the transcription factor MEF2C by the MAP kinase p38 in inflammation Nature 386 1997 296 299 (Pubitemid 27142517)
12. Jayaprakasha, G.K.; Patil, B.S.; Bhat, N.G.; 2007. Process for the isolation of limonoid glucosides from citrus, US Patent # 2007/0237885 A1.
13. G.K. Jayaprakasha, K.K. Mandadi, S.M. Poulose, Y. Jadegoud, G. Nagana, and B.S. Patil Novel triterpenoid from Citrus aurantium L. possesses chemopreventive properties against human colon cancer cells Bioorg. Med. Chem. 16 2008 5939 5951 (Pubitemid 351758846)
14. G.K. Jayaprakasha, K.K. Mandadi, S.M. Poulose, Y. Jadegoud, G.A. Nagana Gowda, and B.S. Patil Novel triterpenoid from Citrus aurantium L. possesses chemopreventive properties against human colon cancer cells Bioorg. Med. Chem. 16 2008 5939 5951 (Pubitemid 351758846)
15. G.K. Jayaprakasha, Y. Jadegoud, G.A. Nagana Gowda, and B.S. Patil Bioactive compounds from sour orange inhibit colon cancer cell proliferation and induce cell cycle arrest J. Agric. Food Chem. 58 2010 180 186
16. G.K. Jayaprakasha, D.V. Dandekar, S.E. Tichy, and B.S. Patil Simultaneous separation and identification of limonoids from citrus using liquid chromatography collision induced dissociation mass spectra J. Sep. Sci. 34 2011 2 10
17. S. Jitpukdeebodintra, S. Chantachum, A. Ratanaphan, and K. Chantrapromma Stability of limonin from lime seeds J. Food Agric. Environ. 3 2005 99 100
18. M.K. Jones, H. Wang, B.M. Peskar, E. Levin, R.M. Itani, I.J. Sarfeh, and A.S. Tarnawski Inhibition of angiogenesis by nonsteroidal anti-inflammatory drugs: insight into mechanisms and implications for cancer growth and ulcer healing Nat. Med. 5 1999 1418 1423
19. A. Kotlyarov, A. Neininger, C. Schubert, R. Eckert, C. Birchmeier, H.D. Volk, and M. Gaestel MAPKAP kinase 2 is essential for LPS-induced TNF-alpha biosynthesis Nat. Cell Biol. 1 1999 94 97 (Pubitemid 129501950)
20. S. Kumar, J. Boehm, and J.C. Lee p38 MAP kinases: key signalling molecules as therapeutic targets for inflammatory diseases Nat. Rev. Drug Discov. 2 2003 717 726 (Pubitemid 37361787)
21. E.M. Kurowska, C. Banh, S. Hasegawa, and G.D. Manners Regulation of apo production in HepG2 cells by citrus limonoids M. Berhow, G.M. S. Hasegawa, Citrus Limonoids 2000 American Chemical Society, Inc. Washington, DC 175 184
22. E.M. Kurowska, N.M. Borradaile, J.D. Spence, and K.K. Carroll Hypocholesterolemic effects of dietary citrus juices in rabbits Nutr. Res. 20 2000 121 129 (Pubitemid 30020298)
23. J.M. Kyriakis, and J. Avruch Mammalian mitogen-activated protein kinase signal transduction pathways activated by stress and inflammation Physiol. Rev. 81 2001 807
24. L.K.T. Lam, and S. Hasegawa Inhibition of benzo [a] pyrene-induced forestomach neoplasia in mice by citrus limonoids Nutr. Cancer 12 1989 43 47 (Pubitemid 19055765)
25. L.K.T. Lam, V.L. Sparnins, and L.W. Wattenberg Isolation and identification of kahweol palmitate and cafestol palmitate as active constituents of green coffee beans that enhance glutathione S-transferase activity in the mouse Cancer Res. 42 1982 1193
26. L.K.T. Lam, Y. Li, and S. Hasegawa Effects of citrus limonoids on glutathione S-transferase activity in mice J. Agric. Food Chem. 37 1989 878 880
27. L.K.T. Lam, J. Zhang, S. Hasegawa, and H.A.J. Schut Inhibition of chemically induced carcinogenesis by citrus limonoids M.T. Huang, T.O. C.T. Ho, R.T. Rosen, Food Phytochemicals for Cancer Prevention I 1994 American Chemical Society, Inc. Washington, DC 209 219
28. S. Liu, J.A.E. Manson, and I. Lee Fruit and vegetable intake and risk of cardiovascular disease: the Women's Health Study Am. J. Clin. Nutr. 72 2000 922 928
29. R. Maini, E.W. St Clair, F. Breedveld, D. Furst, J. Kalden, M. Weisman, J. Smolen, P. Emery, G. Harriman, and M. Feldmann Infliximab (chimeric anti-tumour necrosis factor [alpha] monoclonal antibody) versus placebo in rheumatoid arthritis patients receiving concomitant methotrexate: a randomised phase III trial Lancet 354 1999 1932 1939
30. K. Mandadi, G. Jayaprakasha, N. Bhat, and B. Patil Red Mexican grapefruit: a novel source for bioactive limonoids and their antioxidant activity Z. Naturforsch. C 62c 2007 179 188 (Pubitemid 47226714)
31. G.D. Manners Citrus limonoids: analysis, bioactivity, and biomedical prospects J. Agric. Food Chem. 55 2007 8285 8294 (Pubitemid 350013067)
32. V.C. Mehra, V.S. Ramgolam, and J.R. Bender Cytokines and cardiovascular disease J. Leukocyte Biol. 78 2005 805 818 (Pubitemid 41384397)
33. E.G. Miller, J.L. Porter, W.H. Binnie, I.Y. Guo, and S. Hasegawa Further studies on the anticancer activity of citrus limonoids J. Agric. Food Chem. 52 2004 4908 4912
34. O'Neil, M.J.; et al.; 2006. The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals (14th Edition - Version 14.7). Merck Sharp & Dohme Corp.; a subsidiary of Merck & Co.; Inc.
35. B.S. Patil, J.S. Brodbelt, E.G. Miller, and N.D. Turner Potential health benefits of citrus: an overview B.S. Patil, N.D.T. E.G. Miller, J.S. Brodbelt, Potential Health Benefits of Citrus 2006 American Chemical Society, Inc. Washington, DC 1 16
36. J.R. Patil, K.N.C. Murthy, G.K. Jayaprakasha, M.B. Chetti, and B.S. Patil Bioactive compounds from Mexican lime (Citrus aurantifolia) juice induce apoptosis in human pancreatic cells J. Agric. Food Chem. 57 2009 10933 10942
37. J. Patil, J. Kim, and G. Jayaprakasha Berberine induces apoptosis in breast cancer cells (MCF-7) through mitochondrial-dependent pathway Eur. J. Pharmacol. 645 2010 70 78
38. J.L. Perez, G.K. Jayaprakasha, V. Valdivia, D. Munoz, D.V. Dandekar, H. Ahmad, and B.S. Patil Limonin methoxylation influences the induction of glutathione S-transferase and quinone reductase J. Agric. Food Chem. 57 2009 5279 5286
39. J.L. Perez, G.K. Jayaprakasha, A. Cadena, E. Martinez, H. Ahmad, and B.S. Patil In vivo induction of phase II detoxifying enzymes, glutathione transferase and quinone reductase by citrus triterpenoids BMC Complement. Altern. Med. 10 2010 51
40. G.R. Pettit, D.H.R. Barton, C.L. Herald, J. Polonsky, J.M. Schmidt, and J.D. Connolly Evaluation of limonoids against the murine P388 lymphocytic leukemia cell line J. Nat. Prod. 46 1983 379 390 (Pubitemid 13031285)
41. S.M. Poulose, E.D. Harris, and B.S. Patil Antiproliferative effects of citrus limonoids against human neuroblastoma and colonic adenocarcinoma cells Nutr. Cancer 56 2006 103 112 (Pubitemid 46173420)
42. S. Poulose, G. Jayaprakasha, R. Mayer, B. Girennavar, and B. Patil Purification of citrus limonoids and their differential inhibitory effects on human cytochrome P450 enzymes J. Sci. Food Agric. 87 2007 1699 1709 (Pubitemid 46983824)
43. G. Raman, M. Cho, J. Brodbelt, and B. Patil Isolation and purification of closely related Citrus limonoid glucosides by flash chromatography Phytochem. Anal. 16 2005 155 160 (Pubitemid 40903219)
44. B. Ramanathan, K.Y. Jan, C.H. Chen, T.C. Hour, H.J. Yu, and Y.S. Pu Resistance to paclitaxel is proportional to cellular total antioxidant capacity Cancer Res. 65 2005 8455
45. J. Silalahi Anticancer and health protective properties of citrus fruit components Asia Pac. J. Clin. Nutr. 11 2002 79 84 (Pubitemid 34875161)
46. H. Tanaka, G. Sukhova, D. Schwartz, and P. Libby Proliferating arterial smooth muscle cells after balloon injury express TNF-{alpha} but not interleukin-1 or basic fibroblast growth factor Arterioscler. Thromb. Vasc. Biol. 16 1996 12
47. T. Tanaka, M. Maeda, H. Kohno, M. Murakami, S. Kagami, M. Miyake, and K. Wada Inhibition of azoxymethane-induced colon carcinogenesis in male F344 rats by the citrus limonoids obacunone and limonin Carcinogenesis 22 2001 193 198 (Pubitemid 32098162)
48. Q. Tian, and S.J. Schwartz Mass spectrometry and tandem mass spectrometry of citrus limonoids Anal. Chem. 75 2003 5451 5460 (Pubitemid 37280572)
49. Q. Tian, E.G. Miller, H. Ahmad, L. Tang, and B.S. Patil Differential inhibition of human cancer cell proliferation by citrus limonoids Nutr. Cancer 40 2001 180 184 (Pubitemid 34274925)
50. D. Trachootham, J. Alexandre, and P. Huang Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? Nat. Rev. Drug Discov. 8 2009 579 591
51. J. Vanamala, T. Leonardi, B.S. Patil, S.S. Taddeo, M.E. Murphy, L.M. Pike, R.S. Chapkin, J.R. Lupton, and N.D. Turner Suppression of colon carcinogenesis by bioactive compounds in grapefruit Carcinogenesis 27 2006 1257 1265 (Pubitemid 43994864)
52. C.J. Vlahos, S.A. McDowell, and A. Clerk Kinases as therapeutic targets for heart failure Nat. Rev. Drug Discov. 2 2003 99 113 (Pubitemid 37361642)
53. J. Yang, M. Boerm, M. McCarty, C. Bucana, I.J. Fidler, Y. ZJ, and B. Su Mekk3 is essential for early embryonic cardiovascular development Nat. Genet. 24 2000 309 313 (Pubitemid 30132205)