Experimental and Molecular Medicine

Korean Society for Biochemistry and Molecular Biongy (생화학분자생물학회)
권호 표지

Methyl gallate and chemicals structurally related to methyl gallate protect human umbilical vein endothelial cells from oxidative stress

Whang, Wan-Kyunn;Park, Hyung-Soon;Ham, In-Hye;Oh, Mi-Hyun;NamKoong, Hong;Kim, Hyun-Kee;Hwang, Dong-Whi;Hur, Soo-Young;Kim, Tae-Eung;Park, Yong-Gyu;Kim, Jae-Ryong;Kim, Jin-Woo

  • Published : 2005.08.31
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Abstract

Methyl gallate (meGAL) is known as one of major antioxidants. To investigate whether meGAL pro - tects human cells from oxidative stress, meGAL extracted from Korean medicinal plant, Cercis chinensis leaves, was primarily screened using cell viability assay against oxidative stress. Human umbilical vein endothelial cells (HUVECs) were treated with three different concentrations of meGAL for indicated time. After or during meGAL treatment, H2O2 was added and incubated. meGAL showed free radical scavenging effect at low concentration (0.02 mM) and cell protective effect against H2O2-mediated oxidative stress. meGAL recovered viability of HUVECs damaged by H2O2-treatment, reduced the lipid peroxidation (LPO) and decreased the internal reactive oxygen species (ROS) level elevated by H2O2-treatment. Free radical scavenging effect of meGAL was proven to be very high. Differential display reverse transcription-PCR analysis showed that meGAL upregulated the levels of regulator of chromatin condensation 1, type 1 sigma receptor and phosphate carrier protein expressions, respectively. Based on structural similarity compared with meGAL, 14 chemicals were chosen and viability assay was performed. Four chemicals, haematom - mic acid (56.2% enhancement of viability), gallic acid (35.0%), methylorsellinic acid (23.7%), and syringic acid (20.8%), enhanced more potent cell viability than meGAL, which showed only 18.1% enhancement of cell viability. These results suggest that meGAL and four meGAL-related chemicals protect HUVECs from oxidative stress.

Keywords

References

  1. Adler V, Yin Z, Fuchs SY, Nenezra M, Rosario L, Tew KD, Pincus MR, Sardana M, Henderson CJ, Wolf CR, Davis RJ, Ronai, Z. Regulation of JNK signaling by GSTp. EMBO J 1999;18:1321-34 https://doi.org/10.1093/emboj/18.5.1321
  2. Aydar E, Palmer CP, Djamgoz MBA. Sigma receptors and cancer: possible involvement of ion channels. Cancer Res 2004;64: 5029-35 https://doi.org/10.1158/0008-5472.CAN-03-2329
  3. Beckman KB, Ames BN. The free radical theory of aging matures. Physiol Rev 1998;78:547-81
  4. Chen A, Zhang L. The antioxidant (-)-epigallocatechin-3- gallate inhibits rat hepatic stellate cell proliferation in vitro by blocking the tyrosine phosphorylation and reducing the gene expression of platelet-derived growth $factor-{\alpha}$ receptor. J Biol Chem 2003; 278:23381–9 https://doi.org/10.1074/jbc.M212042200
  5. Cho EJ, Yokozawa T, Rhyu DY, Kim SC, Shibahara N, Park JC. Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1-diphenyl-2-picrylhydrazyl radical. Phytomedicine 2003;10:544-51 https://doi.org/10.1078/094471103322331520
  6. Cho EJ, Yokozawa T, Kim HY, Shibahara N, Park JC. Rosa rugosa attenuates diabetic oxidative stress in rats with streptozotocin-induced diabetes. Am J Chinese Med 2004; 32:487-96 https://doi.org/10.1142/S0192415X04002132
  7. Curtin JF, Donovan M, Cotter T. Regulation and measurement of oxidative stress in apoptosis. J Immunol Methods 2002; 265:49-72 https://doi.org/10.1016/S0022-1759(02)00070-4
  8. Droge W. Free radicals in the physiological control of cell function. Physiol Rev 2002;82:47-95
  9. Estrada-Garcia L, Carrera-Rotllan J, Puig-Parellada P. Effects of oxidative stress and antioxidant treatments on eicosanoid synthesis and lipid peroxidation in long term humaan umbilical vein endotherial cells culture. Prostaglandins Other Lipid Mediat. 2002;67:13-25 https://doi.org/10.1016/S0090-6980(01)00167-8
  10. Finkel T, Holbrook NJ. Oxidants, oxidative stress and the biology of aging. Nature 2000;408:239-47 https://doi.org/10.1038/35041687
  11. Galati G, O'Brien PJ. Potential toxicity of flavonoids and other dietary phenolics: significance for their chemopreventive and anticancer properties. Free Radic Biol Med 2004;37:287-303 https://doi.org/10.1016/j.freeradbiomed.2004.04.034
  12. Galato D, Ckless K, Susin MF, Giacomelli C, Ribeirodo- Valle RM, Spinelli A. Antioxidant capacity of phenolic and related compounds: correlation among electrochemical, visible spectroscopy methods and structure-antioxidant activity. Redox Rep 2001;6:243-50 https://doi.org/10.1179/135100001101536391
  13. Hayashi T, Su T. Regulating ankyrin dynamics: Roles of sigma-1 receptors. Proc Natl Acad Sci USA 2001;98:491–6 https://doi.org/10.1073/pnas.021413698
  14. Hsieh T, Liu T, Chia Y, Chern C, Lue F, Chuang M, Mau S, Chen S, Syu Y, Chen C. Protective effect of methyl gallate from Toona sinensis (Meliaceae) against hydrogen peroxide- induced oxidative stress and DNA damage in MDCK cells. Food Chem Toxicol 2004;42:843-50 https://doi.org/10.1016/j.fct.2004.01.008
  15. Kalkan Yildirim H, Delen Akcay Y, Guvenc U, Yildirim Sozmen E. Protection capacity against low-density lipoprotein oxidation and antioxidant potential of some organic and non-organic wines. Int J Food Sci Nutr 2004;55:351-62 https://doi.org/10.1080/09637480412331319781
  16. Kizu H, Tomimori T. Phenolic constituents from the flowers of Nymphaea stellata. Natural Medicines 2003;57:118
  17. Larsson R, Cerutti P. Translocation and enhancement of phosphotransferase activity of protein kinase c following exposure in mouse epidermal cells to oxidants. Cancer Res 1989;49:5627-32
  18. Lee SE, Ju EM, Kim JH. Antioxidant activity of extracts from Euryale ferox seed. Exp Mol Med 2002;34:100-6
  19. Liang P, Pardee AB. Differential display of eukaryotic messenger RNA by means of the polymerase chain reaction. Science 1992;257:967-71 https://doi.org/10.1126/science.1354393
  20. Lim MY, Park YH, Son DJ, Kim MK, Lee HS. Antiplatelet activity of gallic acid and methyl gallate. Food Sci Biot 2004;13:806-9
  21. Nakamura H, Matuda M, Furuke K, Iwata S, Toda K, Inamoto T, Yamaoka Y, Ozawa K, Yodoi J. Adult T cell leukemia-derived factor/human thioredoxin protects endotherial F-2 cell injury caused by activated neorophils or hydrogen peroxide. Immunol Lett 1994;42:75-80 https://doi.org/10.1016/0165-2478(94)90038-8
  22. Nishijima H, Nishitani H, Saito N, Nishimoto T. Caffeine mimics adenine and 2′-deoxyadenosine, both of which inhibit the guanine-nucleotide exchange activity of RCC1 and the kinase activity of ATR. Genes Cells 2003;8:423–35 https://doi.org/10.1046/j.1365-2443.2003.00644.x
  23. Puel O, Tadrist S, Galtier P, Oswald IP, Delaforge M. Byssochlamys nivea as a source of mycophenolic acid. Appl Environ Microbiol 2005;71:550-3 https://doi.org/10.1128/AEM.71.1.550-553.2005
  24. Sciuto AM, Moran TS. Effect of dietary treatment with n-propyl gallate or vitamin E on the survival of mice exposed to phosgene. J Appl Toxicol 2001;21:33-9 https://doi.org/10.1002/jat.729
  25. Shuli S, Heintz NH, Periasamy M, Manohar M, Janssen YM, Marsh JP, Mossaman BT. Differential regulation of antioxidant enzymes in response to oxidants. J Biol Chem 1991;266: 24398-403
  26. Sies H. Strategies of antioxidant defense. Eur J Biochem 1993;215:213-9 https://doi.org/10.1111/j.1432-1033.1993.tb18025.x
  27. Sohi KK, Mittal N, Hundal MK, Khanduja KL. Gallic acid, an antioxidant, exhibits antiapoptotic potential in normal human lymphocytes: A Bcl-2 independent mechanism. J Nutr Sci Vitaminol 2003;49:221-7
  28. Spruce BA, Campbell LA, McTavish N, Cooper MA, Appleyard VL, O'Neill M, Howie J, Samson J, Watt S, Murray K, McLean D, Leslie NR, Safrany ST, Ferguson MJ, Peters JA, Prescott AR, Box G, Hayes A, Nutley B, Raynaud F, Downes CP, Lambert JJ, Thompson AM, Eccles S. Small molecule antagonists of the ${\sigma}-1$ receptor cause selective release of the death program in tumor and self-reliant cells and inhibit tumor growth in vitro and in vivo. Cancer Res 2004;64:4875-86 https://doi.org/10.1158/0008-5472.CAN-03-3180
  29. Toledo Marante FJ, Garcia Castellano A, Estevez Rosas F, Quintana Aguiar J, Bermejo Barrera J. Identification and quantitation of allelochemicals from the lichen Lethariella canariensis: phytotoxicity and antioxidative activity. J Chem Ecol 2003;29:2049-71 https://doi.org/10.1023/A:1025682318001
  30. Valen G, Sonden A, Vaage J, Malm E, Kjellstrom T. Hydrogen peroxide induces endotherial cell atypia and cytoskeleton deplymerization. Free Radic Biol Med 1999;26: 1480-8 https://doi.org/10.1016/S0891-5849(99)00009-X
  31. Waxman A, Mahboubi K, Knickelbein RG, Mantell LL, Manzo N, Pober JS, Elias JA. Interleukin-11 and interleukin-6 protect cultured human endothelial cells from $H_2O_2$-induced cell death. Am J Respir Cell Mol Biol 2003;29:513-22 https://doi.org/10.1165/rcmb.2002-0044OC
  32. Westenburg HE, Lee KJ, Lee SK, Fong HH, van Breemen RB, Pezzuto JM, Kinghorn AD. Activity-guided isolation of antioxidative constituents of Cotinus coggygria. J Nat Prod 2000;63:1696-8 https://doi.org/10.1021/np000292h
  33. Zapolska-Downar D, Zapolska-Downar A, Bukowska H, Galka H, Naruszewicz M. Ibuprofen protects low density lipoproteins against oxidative modification. Life Sci 1999;65: 2289- 303 https://doi.org/10.1016/S0024-3205(99)00496-8
  34. Zhang M, Storz G. Redox sensing by prokaryotic transcription factors. Biochem Pharmacol 2000;59:1-6 https://doi.org/10.1016/S0006-2952(99)00289-0
  35. Zheng Y. G protein control of microtubule assembly. Annu Rev Cell Dev Biol 2004;20:867-94 https://doi.org/10.1146/annurev.cellbio.20.012103.094648