Food Science and Biotechnology

Korean Society of Food Science and Technology (한국식품과학회)
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Antioxidant Properties of Tannic Acid and its Inhibitory Effects on Paraquat-Induced Oxidative Stress in Mice

  • Choi, Je-Min (Department of Biotechnology, College of Engineering, Yonsei University) ;
  • Han, Jin (1st R&D Center, Honda B/D, Samhwa F&F) ;
  • Yoon, Byoung-Seok (Department of Biotechnology, College of Engineering, Yonsei University) ;
  • Chung, Jae-Hwan (Social Research and Data Analysis, World Research Corporation) ;
  • Shin, Dong-Bum (Department of Food Science and Nutrition, Cheju National University) ;
  • Lee, Sang-Kyou (Department of Biotechnology, College of Engineering, Yonsei University) ;
  • Hwang, Jae-Kwan (Department of Biotechnology, College of Engineering, Yonsei University) ;
  • Ryang, Ryung (Department of Biotechnology, College of Engineering, Yonsei University)
  • Published : 2006.10.30
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Abstract

The tannins represent a highly heterogeneous group of water-soluble plant polyphenols that may play an important role in antimutagenic and antioxidant properties. We investigated the antioxidant function of tannic acid in comparison to other phenolic compounds including catechin, chlorogenic acid, cinnamic acid, ellagic acid, and gallic acid for their ability to scavenge several stable radicals and reactive oxygen species (ROS) such as ${\bullet}DPPH^+$, ${\bullet}ABTS^+$, hydrogen peroxide, hydroxyl radical, and superoxide radical. The ability of tannic acid to decrease paraquat-induced lipid oxidation in mouse liver and lung through its antioxidant properties was also assessed. The results showed that almost all the tested compounds have stable radical scavenging activity except cinnamic acid. Tannic acid, gallic acid, and ellagic acid demonstrated remarkable ROS scavenging properties toward $H_2O_2$, ${\bullet}OH^-$, ${\bullet}O_2^-$ and especially only tannic acid could inhibit paraquat-induced lipid peroxidation effectively in mouse liver and lung. Based on these results, it appears that increased number of galloyl and ortho-hydroxyl groups enhances the antioxidant activity of phenolic compounds and tannic acid is evaluated as the most effective antioxidant among all the tested compounds. These results suggest that the tannins, especially tannic acid, can be used as therapeutic agent for various diseases caused by ROS.

Keywords

References

  1. Burapadaja S, Bunchoo A. Antimicrobial activity of tannins from Terminalia citrine. Planta. Med. 61: 365-366 (1995) https://doi.org/10.1055/s-2006-958103
  2. Nakashima H, Murakami T, Yamamoto N, Sakagami H, Tanuma S, Hatano T, Yoshida T, Okuda T. Inhibition of human immunodeficiency viral replication by tannins and related compounds. Antivir. Res. 18: 91-103 (1992) https://doi.org/10.1016/0166-3542(92)90008-S
  3. Satoh K, Sakagami H. Ascorbyl radical scavenging activity of polyphenols. Anticancer Res. 16: 2885-2890 (1996)
  4. Gali HU, Perchellet EM, Klish DS, Johnson JM, Perchellet JP. Antitumor-promoting activities of hydrolyzable tannins in mouse skin. Carcinogenesis 13: 715-718 (1992) https://doi.org/10.1093/carcin/13.4.715
  5. Mukhtar H, Das M, Khan WA, Wang ZY, Bik DP, Bickers DR. Exceptional activity of tannic acid among naturally occurring plant phenols in protecting against 7,12-dimethylbenz(${\alpha}$)anthracene-, benzo(${\alpha}$)pyrene-, 3-methylcholanthrene-, and N-methyl-N-nitrosourea-induced skin tumorigenesis in mice. Cancer Res. 48: 2361-2365 (1988)
  6. Miyamoto K, Nomura M, Murayama T, Furukawa T, Hatano T, Yoshida T, Koshiura R, Okuda T. Antitumor activities of ellagitannins against sarcoma-180 in mice. Biol. Pharm. Bull. 16: 379-387 (1993) https://doi.org/10.1248/bpb.16.379
  7. Teissedre PL, Frankel EN, Waterhouse AL, Peleg H, German JB. Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J. Sci. Food Agric. 70: 55-63 (1996) https://doi.org/10.1002/(SICI)1097-0010(199601)70:1<55::AID-JSFA471>3.0.CO;2-X
  8. Andrade RG, Dalvi LT, Silva JM Jr, Lopes GK, Alonso A, Hermes-Lima M. The antioxidant effect of tannic acid on the in vitro coppermediated formation of free radicals. Arch. Biochem. Biophys. 437: 1-9 (2005) https://doi.org/10.1016/j.abb.2005.02.016
  9. Chung KT, Wong TY, Wei CI, Huang YW, Lin Y. Tannins and human health: a review. Crit. Rev. Food Sci. Nutr. 38: 421-464 (1998) https://doi.org/10.1080/10408699891274273
  10. King A, Young G. Characteristics and occurrence of phenolic phytochemicals. J. Am. Diet. Assoc. 99: 213-218 (1999) https://doi.org/10.1016/S0002-8223(99)00051-6
  11. Okamura H, Mimura A, Yakou Y, Niwano M, Takahara Y. Antioxidant activity of tannins and flavonoids in Eucalyptus rostrata. Phytochemistry 33: 557-561 (1993) https://doi.org/10.1016/0031-9422(93)85448-Z
  12. Halliwel B, Gutteridge JMC. Free Radicals in Biology and Medicine, 3rd ed. Oxford Press, London, UK. p.11 (1998)
  13. Enrique C, Kelvin JAD. Mitochondrial free radical generation, oxidative stress and aging. Free Radical Bio. Med. 29: 222-230 (2000) https://doi.org/10.1016/S0891-5849(00)00317-8
  14. Fruest EP, Norman MN. Interactions of herbicide with photosynthetic electron transport. Weed Sci. 39: 458-464 (1991)
  15. Scandalios JG. Oxygen stress and superoxide dismutases. Plant Physiol. 101: 7-12 (1993)
  16. Lannelli MA, Breusegem F, Montagu MV, Inze D, Massacci A. Tolerance to low temperature and paraquat-mediated oxidative stress in two maize genotypes. J. Exp. Bot. 50: 523-532 (1999) https://doi.org/10.1093/jexbot/50.333.523
  17. Kwon SY, Jeong YT, Lee HS, Kim JS, Cho KY, Allen RD, Kwak SS. Enhanced tolerances of transgenic tobacco plants expressing both superoxide dismutase and ascorbate peroxidase in chloroplasts against methyl viologen-mediated oxidative stress. Plant Cell Environ. 25: 873-882 (2002) https://doi.org/10.1046/j.1365-3040.2002.00870.x
  18. Casano LM, Martin M, Zapata JM, Sabater B. Leaf age- and paraquat concentration-dependent effects on the levels of enzymes protecting against photooxidative stress. Plant Sci. 149: 13-22 (1999) https://doi.org/10.1016/S0168-9452(99)00138-7
  19. Moradas-Ferreira P, Costa V, Piper P, Mager W. The molecular defenses against reactive oxygen species in yeast. Mol. Microbiol. 19: 651-658 (1996) https://doi.org/10.1046/j.1365-2958.1996.403940.x
  20. Haly TJ. Review of the toxicity of paraquat. Clin. Toxicol. 14: 1-46 (1979) https://doi.org/10.3109/15563657909030112
  21. Braca A, De Tommasi N, Di Bari L, Pizza C, Politi M, Morelli I. Antioxidant principles from Bauhinia tarapotensis. J. Nat. Prod. 64: 892-895 (2001) https://doi.org/10.1021/np0100845
  22. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation declorization assay. Free Radical Bio. Med. 26: 1231-1237 (1999) https://doi.org/10.1016/S0891-5849(98)00315-3
  23. Aruoma OI, Halliwell B, Hoey BM, Butler J. The antioxidant action of taurine, hypotaurine, and therimetabolic precursors. Biochem. J. 256: 251-255 (1998)
  24. Fernandes E, Costa D, Toste SA, Lima JL, Reis S. In vitro scavenging activity for reactive oxygen and nitrogen species by nonsteroidal anti-inflammatory indole, pyrrole, and oxazole derivative drugs. Free Radical Bio. Med. 37: 1895-1905 (2004) https://doi.org/10.1016/j.freeradbiomed.2004.09.001
  25. McCord JM, Fridovich I. Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). J. Biol. Chem. 244: 6049-6055 (1969)
  26. Ohkawa H, Ohishi N, Yagi Y. Assay of lipid peroxides in animal tissue by thiobarbituric acid reaction. Anal. Biochem. 95: 351-358 (1979) https://doi.org/10.1016/0003-2697(79)90738-3
  27. Ellman G. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 82: 70-77 (1959) https://doi.org/10.1016/0003-9861(59)90090-6
  28. Choi JM, Ryu HJ, Chung JH, Park JC, Hwang JK, Shin DB, Lee SK, Ryang R. Antioxidant property of genistein: Inhibitory effect on HOCI induced protein degradation, DNA cleavage, and cell death. Food Sci. Biotechnol. 14: 399-404 (2005)
  29. Catherine AR, Nicholas JM, George P. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Bio. Med. 20: 933-956 (1996) https://doi.org/10.1016/0891-5849(95)02227-9
  30. Casalini C, Lodovici M, Briani C, Paganelli G, Remy S, Cheynier V, Dolara P. Effect of complex polyphenols and tannins from red wine (WCPTP) on chemically induced oxidative DNA damage in the rat. Eur. J. Nutri. 38: 190-195 (1999) https://doi.org/10.1007/s003940050061
  31. Giovannelli L, Testa G, De Filippo C, Cheynier V, Clifford MN, Dolara P. Effect of complex polyphenols and tannins from red wine on DNA oxidative damage of rat mucosa in vivo. Eur. J. Nutr. 39: 207-212 (2000) https://doi.org/10.1007/s003940070013
  32. Andrade RG, Ginani JS, Lopes GK, Dutra F, Alonso A, Hermes-Lima M. Tannic acid inhibits in vitro iron-dependent free radical formation. Biochimie 88: 1287-1296 (2006) https://doi.org/10.1016/j.biochi.2006.02.006
  33. Tampo Y, Tsukamoto M, Yonaha M. Superoxide production from paraquat evoked by exogenous NADPH in pulmonary endothelial cells. Free Radical Bio. Med. 27: 588-595 (1999) https://doi.org/10.1016/S0891-5849(99)00110-0
  34. Minakata K, Suzuki O, Horio F, Saito S, Harada N. Increase in production of ascorbate radical in tissues of rat treated with paraquat. Free Radical Res. 33: 179-185 (2000) https://doi.org/10.1080/10715760000300731
  35. Miguez MP, Soler F, Garcia-Rubio L. Accentuation of paraquat-induced toxicity by L-carnitine in mice. Biofactors 8: 73-78 (1998) https://doi.org/10.1002/biof.5520080113
  36. Tsukamoto M, Tampo Y, Sawada M, Yonaha M. Paraquat-induced membrane dysfunction in pulmonary microvascular endothelial cells. Pharmacol. Toxicol. 86: 102-109 (2000) https://doi.org/10.1034/j.1600-0773.2000.d01-19.x
  37. Venkatesan N. Pulmonary protective effects of curcumin against paraquat toxicity. Life Sci. 66: 21-28 (2000)
  38. Autor AP. Biochemical mechanisms of paraquat toxicity. Life Sci. 14: 1309-1319 (1977) https://doi.org/10.1016/0024-3205(74)90439-1
  39. Gram TE. Chemically reactive intermediates and pulmonary xenobiotic toxicity. Pharmacol. Rev. 49: 297-341 (1997)
  40. Rahman Q, Abidi P, Afaq F, Schiffinann D, Mossman BT, Kamp DW, Athar M. Glutathione redox system in oxidative lung injury. Crit. Rev. Toxicol. 29: 543-568 (1999) https://doi.org/10.1080/10408449991349276
  41. Nam HY, Min SG, Shin HC, Kim HY, Fukushima M, Han KH, Park WJ, Choi KD, Lee CH. The protective effects of isoflavone extracted from soybean paste in free radical initiator treated rats. Food Sci. Biotechnol. 14: 586-592 (2005)