DOI QR코드

DOI QR Code

Evidence for the association of peroxidases with the antioxidant effect of p-coumaric acid in endothelial cells exposed to high glucose plus arachidonic acid

  • Lee, Seung-Jin (Department of Molecular Medicine and Cell and Matrix Research Institute, BK21 Medical Education Program for Human Resources, Kyungpook National University School of Medicine) ;
  • Mun, Gyeong-In (Department of Molecular Medicine and Cell and Matrix Research Institute, BK21 Medical Education Program for Human Resources, Kyungpook National University School of Medicine) ;
  • An, Sang-Mi (Department of Molecular Medicine and Cell and Matrix Research Institute, BK21 Medical Education Program for Human Resources, Kyungpook National University School of Medicine) ;
  • Boo, Yong-Chool (Department of Molecular Medicine and Cell and Matrix Research Institute, BK21 Medical Education Program for Human Resources, Kyungpook National University School of Medicine)
  • Published : 2009.09.30

Abstract

Although many plant-derived phenolic compounds display antioxidant effects in biological systems, their mechanism of action remains controversial. In this study, the mechanism by which p-coumaric acid (p-CA) performs its antioxidant action was investigated in bovine aortic endothelial cells under oxidative stress due to high levels of glucose (HG) and arachidonic acid (AA), a free fatty acid. p-CA prevented lipid peroxidation and cell death due to HG+AA without affecting the production of reactive oxygen species. The antioxidant effect of p-CA was not decreased by buthionine-(S,R)-sulfoximine, an inhibitor of cellular GSH synthesis. In contrast, pretreatment with p-CA caused the induction of peroxidases that decomposed t-butyl hydroperoxide in a p-CA-dependent manner. Furthermore, the antioxidant effect of p-CA was significantly mitigated by methimazole, which was shown to inhibit the catalytic activity of 'p-CA peroxidases' in vitro. Therefore, it is suggested that the induction of these previously unidentified 'p-CA peroxidases' is responsible for the antioxidant effect of p-CA.

References

  1. Simini, B. (2000) Serge Renaud: from French paradox to Cretan miracle. Lancet 355, 48 https://doi.org/10.1016/S0140-6736(05)71990-5
  2. Lopez-Velez, M., Martinez-Martinez, F. and Del Valle-Ribes, C. (2003) The study of phenolic compounds as natural antioxidants in wine. Crit. Rev. Food Sci. Nutr. 43, 233-244 https://doi.org/10.1080/10408690390826509
  3. Fremont, L. (2000) Biological effects of resveratrol. Life Sci. 66, 663-673 https://doi.org/10.1016/S0024-3205(99)00410-5
  4. Laranjinha, J., Vierira, O., Almeida, L. and Madeira, V. (1996) Inhibition of metmyoglobin/H2O2-dependent low density lipoprotein lipid peroxidation by naturally occurring phenolic acids. Biochem Pharmacol 51, 395-402 https://doi.org/10.1016/0006-2952(95)02171-X
  5. Yeh, C. T., Ching, L. C. and Yen, G. C. (2008) Inducing gene expression of cardiac antioxidant enzymes by dietary phenolic acids in rats. J. Nutr. Biochem. 20, 163-171 https://doi.org/10.1016/j.jnutbio.2008.01.005
  6. Chen, C., Yu, R., Owuor, E. D. and Kong, A. N. (2000) Activation of antioxidant-response element (ARE), mitogen-activated protein kinases (MAPKs) and caspases by major green tea polyphenol components during cell survival and death. Arch. Pharm. Res. 23, 605-612 https://doi.org/10.1007/BF02975249
  7. Roden, M., Price, T. B., Perseghin, G., Petersen, K. F., Rothman, D. L., Cline, G. W. and Shulman, G. I. (1996) Mechanism of free fatty acid-induced insulin resistance in humans. J. Clin. Invest 97, 2859-2865 https://doi.org/10.1172/JCI118742
  8. Nishikawa, T., Edelstein, D., Du, X. L., Yamagishi, S., Matsumura, T., Kaneda, Y., Yorek, M. A., Beebe, D., Oates, P. J., Hammes, H. P., Giardino, I. and Brownlee, M. (2000) Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage. Nature 404, 787-790 https://doi.org/10.1038/35008121
  9. Goldman, R., Claycamp, G. H., Sweetland, M. A., Sedlov, A. V., Tyurin, V. A., Kisin, E. R., Tyurina, Y. Y., Ritov, V. B., Wenger, S. L., Grant, S. G. and Kagan, V. E. (1999) Myeloperoxidase-catalyzed redox-cycling of phenol promotes lipid peroxidation and thiol oxidation in HL-60 cells. Free Radic. Biol. Med. 27, 1050-1063 https://doi.org/10.1016/S0891-5849(99)00140-9
  10. Denizot, F. and Lang, R. (1986) Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 89, 271-277 https://doi.org/10.1016/0022-1759(86)90368-6
  11. Montilla, P., Barcos, M., Munoz, M. C., Bujalance, I., Munoz-Castaneda, J. R. and Tunez, I. (2005) Red wine prevents brain oxidative stress and nephropathy in streptozotocin-induced diabetic rats. J. Biochem. Mol. Biol. 38, 539-544 https://doi.org/10.5483/BMBRep.2005.38.5.539
  12. Mun, G. I., An, S. M., Park, H., Jo, H. and Boo, Y. C. (2008) Laminar shear stress inhibits lipid peroxidation induced by high glucose plus arachidonic acid in endothelial cells. Am. J. Physiol. Heart. Circ. Physiol. 295, H1966-1973 https://doi.org/10.1152/ajpheart.00727.2008
  13. Laranjinha, J., Vieira, O., Madeira, V. and Almeida, L. (1995) Two related phenolic antioxidants with opposite effects on vitamin E content in low density lipoproteins oxidized by ferrylmyoglobin: consumption vs regeneration. Arch. Biochem. Biophys. 323, 373-381 https://doi.org/10.1006/abbi.1995.0057
  14. Hjelte, L. E. and Nilsson, A. (2005) Arachidonic acid and ischemic heart disease. J. Nutr. 135, 2271-2273 https://doi.org/10.1093/jn/135.9.2271
  15. An, S. M., Koh, J. S. and Boo, Y. C. (2009) Inhibition of melanogenesis by tyrosinase siRNA in human melanocytes. BMB Rep. 42, 178-183
  16. Ceriello, A. (2006) Effects of macronutrient excess and composition on oxidative stress: relevance to diabetes and cardiovascular disease. Curr. Atheroscler. Rep. 8, 472-476 https://doi.org/10.1007/s11883-006-0022-z
  17. Chan, T. S., Galati, G., Pannala, A. S., Rice-Evans, C. and O'Brien, P. J. (2003) Simultaneous detection of the antioxidant and pro-oxidant activity of dietary polyphenolics in a peroxidase system. Free Radic. Res. 37, 787-794 https://doi.org/10.1080/1071576031000094899
  18. Galati, G., Sabzevari, O., Wilson, J. X. and O'Brien, P. J. (2002) Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics. Toxicology 177, 91-104 https://doi.org/10.1016/S0300-483X(02)00198-1
  19. Abdel-Wahab, M. H., El-Mahdy, M. A., Abd-Ellah, M. F., Helal, G. K., Khalifa, F. and Hamada, F. M. (2003) Influence of p-coumaric acid on doxorubicin-induced oxidative stress in rat's heart. Pharmacol Res. 48, 461-465 https://doi.org/10.1016/S1043-6618(03)00214-7
  20. Leverve, X. (2003) Hyperglycemia and oxidative stress: complex relationships with attractive prospects. Intensive Care Med. 29, 511-514 https://doi.org/10.1007/s00134-002-1629-3
  21. Heinecke, J. W., Li, W., Francis, G. A. and Goldstein, J. A (1993) Tyrosyl radical generated by myeloperoxidase catalyzes the oxidative cross-linking of proteins. J. Clin. Invest 91, 2866-2872 https://doi.org/10.1172/JCI116531
  22. Morton, L. W., Abu-Amsha Caccetta, R., Puddey, I. B. and Croft, K. D. (2000) Chemistry and biological effects of dietary phenolic compounds: relevance to cardiovascular disease. Clin. Exp. Pharmacol Physiol. 27, 152-159 https://doi.org/10.1046/j.1440-1681.2000.03214.x
  23. Zang, L. Y., Cosma, G., Gardner, H., Shi, X., Castranova, V. and Vallyathan, V. (2000) Effect of antioxidant protection by p-coumaric acid on low-density lipoprotein cholesterol oxidation. Am. J. Physiol. Cell. Physiol. 279, C954-960 https://doi.org/10.1152/ajpcell.2000.279.4.C954
  24. Harder, S., Bente, M., Isermann, K. and Bruchhaus, I. (2006) Expression of a mitochondrial peroxiredoxin prevents programmed cell death in Leishmania donovani. Eukaryot Cell 5, 861-870 https://doi.org/10.1128/EC.5.5.861-870.2006
  25. Inoguchi, T., Li, P., Umeda, F., Yu, H. Y., Kakimoto, M., Imamura, M., Aoki, T., Etoh, T., Hashimoto, T., Naruse, M., Sano, H., Utsumi, H. and Nawata, H. (2000) High glucose level and free fatty acid stimulate reactive oxygen species production through protein kinase C--dependent activation of NAD(P)H oxidase in cultured vascular cells. Diabetes 49, 1939-1945 https://doi.org/10.2337/diabetes.49.11.1939
  26. Leaf, A. (2001) Plasma nonesterified fatty acid concentration as a risk factor for sudden cardiac death: the Paris Prospective Study. Circulation 104, 744-745 https://doi.org/10.1161/01.CIR.104.7.744
  27. Kong, A. N., Owuor, E., Yu, R., Hebbar, V., Chen, C., Hu, R. and Mandlekar, S. (2001) Induction of xenobiotic enzymes by the MAP kinase pathway and the antioxidant or electrophile response element (ARE/EpRE). Drug. Metab. Rev. 33, 255-271 https://doi.org/10.1081/DMR-120000652

Cited by

  1. Synthesis of a “clickable” Angiopep-conjugated p-coumaric acid for brain-targeted delivery vol.49, pp.23, 2014, https://doi.org/10.1007/s10853-014-8529-0
  2. Mechanisms of endothelial cell protection by hydroxycinnamic acids vol.63, pp.3, 2014, https://doi.org/10.1016/j.vph.2014.10.006
  3. Effect of Phenolic Acid on Antioxidant Activity of Wine and Inhibition of Pectin Methyl Esterase vol.115, pp.4, 2009, https://doi.org/10.1002/j.2050-0416.2009.tb00388.x
  4. p-Coumaric Acid Attenuates UVB-Induced Release of Stratifin from Keratinocytes and Indirectly Regulates Matrix Metalloproteinase 1 Release from Fibroblasts vol.19, pp.3, 2015, https://doi.org/10.4196/kjpp.2015.19.3.241
  5. Comparison of the antimelanogenic effects of p-coumaric acid and its methyl ester and their skin permeabilities vol.63, pp.1, 2011, https://doi.org/10.1016/j.jdermsci.2011.03.012
  6. Antiperoxidative potential of p-coumaric acid, a common dietary phenol, in adjuvant-induced arthritis in rats 2012, https://doi.org/10.3736/jcim20120815
  7. Virgin olive oil rich in phenolic compounds modulates the expression of atherosclerosis-related genes in vascular endothelium vol.55, pp.2, 2016, https://doi.org/10.1007/s00394-015-0868-3
  8. Effect of honey on purified equine myeloperoxidase activity and superoxide radical production in activated Polymorphonuclear neutrophils vol.8, pp.4, 2015, https://doi.org/10.1080/21553769.2015.1044131
  9. UVB-Shielding Effects of para-Coumaric Acid vol.38, pp.3, 2012, https://doi.org/10.15230/SCSK.2012.38.3.263