Tannin Extraction from Oak Gall and Evaluation of Anti-Oxidant Activity and Tannin Iron Chelation Compared with Deferoxamine Drug
In this study, tannins were extracted by two methods (soaking and Soxhlet) with three different solvents (water, methanol and aqueous methanol 50%) and the three kind plant (walnut shell, gall oak and walnut leaves), that the highest extraction efficiency (82.08%) was related to extraction with aqueous methanol by Soxhlet method from the oak galls. Although the results of soaking were nearly to the Soxhlet. One oak Gall extract was evaluated by Lowenthal method that the result was showed that reducing materials such as tannins are 26.14%. The extracted was evaluated by Folin-Ciocalteu method that suggests phenolic compounds in the extract was 15.27, (61.07± 7.12 mg compared to gallic acid). Result of evaluation of antioxidant activity of the extracted showed the high antioxidant properties of tannins compared to ascorbic acid at less than 100 ppm concentrations, but these properties comparable to ascorbic acid of the higher concentrations, so a lower dose of the extract was may be helpful. The chelation properties of the iron ions at low concentrations of iron (III), oak was showed better performance compared to Deferoxamine but Deferoxamine due to complex formation with higher stoichiometry (1: 6) at high concentrations of Fe (III), has performed better than the oak.
Mohammad Javad Chaichi,
Ome Leila Nazari,
Fatemeh Yousefnejad Maleki,
Tannin Extraction from Oak Gall and Evaluation of Anti-Oxidant Activity and Tannin Iron Chelation Compared with Deferoxamine Drug, Journal of Drug Design and Medicinal Chemistry.
Vol. 5, No. 2,
2019, pp. 18-25.
Haslam, E. Plant polyphenols. Vegetable Tannins Revisited; Cambridge University Press: Cambridge, U.K., 1989; pp 230.
Hagerman, A. E.; Carlson, D. M. Biological Responses to Tannins and Other Polyphenols. Recent Res. DeV. Agric. Food Chem. 1998, 2, 689-704.
Bi, J. L.; Felton, G. W.; Murphy, J. B.; Howles, P. A.; Dixon, R. A.; Lamb, C. J. Do Plant Phenolics Confer Resistance to Specialist and Generalist Insect Herbivores J. Agric. Food Chem. 1997, 45, 5 , 4500-4504.
Hagerman, A. E.; Butler, L. G. Tannins and Lignins. In HerbiVores: Their Interactions with Secondary Plant Metabolites [2nd edition] Volume I, The Chemical Participants; Rosenthal, G. A., Berenbaum, M. R., Eds.; Academic Press: New York, 1991; pp 355-388.
Velioglu, Y. S., Mazza, G., Gao, L., Oomah, B. D., 1998. Antioxidant activity and total phenolics in selected fruits, vegetables and grain products. Journal of Agricultural and Food Chemistry 46, 4113-4117
Sun, B., Fukuhara, M., 1997. Effects of co-administration of butylated hydroxytoluene, butylated hydroxyanisole and flavonoids on the activation of mutagens and drug metabolizing enzymes in mice. Toxicology 122, 61-72.
Wichi, H. P., 1988. Enhanced tumour development by butylated hydroxyanisole [BHA] from the prospective of effect on forestomach and oesophageal squamous epithelium. Food and Chemical Toxicology 26, 717-723.
Sherwin, E. R., 1990. In: Branen, A. L., Davidson, P. M., Salminen, S. [Eds.], Food Additives. Marcel Dekker Inc., New York, p. 139-193.
Shahidi, F., Wanasundara, P. D., 1992. Phenolic antioxidants. Critical Reviews in Food Sciences and Nutrition 32, 67-103.
Chen, C. H., Pearson, A. M., Gray, J. I., 1992. Effects of synthetic antioxidants [BHA, BHT and PG] on the mutagenicity of IQ-like compounds. Food Chemistry 43, 177-183.
Moure, A., Cruz, J. M., Franco, D., Dominguez, J. M., Sineiro, J., Dominguez, H., Nunez, M. J., Parajo, J. C., 2001. Natural antioxidants from residual sources. Food Chemistry 72, 145-171.
Gu¨ lc¸ in, _I., 2006a. Antioxidant activity of caffeic acid [3,4-dihydroxycinnamic acid]. Toxicology 217, 213-220.
Oktay, M., Gu¨lc¸ in, I., Ku freviog lu, O. I., 2003. Determination of in vitro antioxidant activity of fennel [Foeniculum vulgare] seed extracts. Lebensmittel Wissenchaft und-Technology 36, 263-271
Shahidi, F., 2000. Antioxidants in food and food antioxidants. Nahrung 44, 158-163.
Van Ruth, S. M., Shaker, E. S., Morrissey, P. A., 2001. Influence of methanolic extracts of soybean seeds and soybean oil, on lipid oxidation in linseed oil. Food Chemistry 75, 177-184.
Bryngelsson, S., Dimberg, LH., Kamal-Eldin, A., 2002. Effects of commercial processing on levels of antioxidants in oats [Avena sativa L.]. Journal of Agricultural and Food Chemistry 50, 1890-1896.
Cook, N. C., Samman, S., 1996. Flavonoids: chemistry, metabolism, cardioprotective effects and dietary sources. Journal of Nutritional Biochemistry 7, 66-76.
Rice-Evans, C., 1995. Plant polyphenols: free radical scavengers or chain breaking antioxidants? Biochemical Society Symposia 61, 103-116.
Liyana-Pathirana, C. M., Shahidi, F., 2006. Antioxidant properties of commercial soft and hard winter wheats [Triticum aestivum L.] and their milling fractions. Journal of Sciences Food and Agriculture 86, 477-485.
Chung, K. T., Wong, T. Y., Wei, C. I., Huang, Y. W., Lin, Y., 1998a. Tannins and human health: a review. Critical Review in Food Sciences and Nutrition 38, 421-464.
King, A., Young, G., 1999. Characteristics and occurrence of phenolic phytochemicals. Journal of the American Dietetic Association 99, 213-218.
Ferguson, L. R., 2001. Role of plant polyphenols in genomic stability. Mutation Research 75, 89-111.
Wu, L. T., Chu, C. C., Chung, J. G., Chen, C. H., Hsu, L. S., Liu, J. K., Chen, S. C., 2004. Effects of tannic acid and its related compounds on food mutagens or hydrogen peroxide-induced DNA strands breaks in human lymphocytes. Mutation Research 556, 75-86.
Andrade, R. G., Dalvi, L. T., Silva, J. M. C., Lopes, G. K. B., Alonso, A., Hermes-Lima, M., 2005. The antioxidant effect of tannic acid on the in vitro copper-mediated formation of free radicals. Archive of Biochemistry and Biophysics 437, 1-9.
Chen, S. C., Chung, K. T., 2000. Mutagenicity and antimutagenicity of tannic acid and its related compounds. Food and Chemical Toxicology 38, 1-5.
Lopes, G. K. B., Schulman, H. M., Hermes-Lima, M., 1999. Polyphenol tannic acid inhibits hydroxyl radical formation from Fenton reaction by complexing ferrous ions. Biochimica Biophysica Acta 1472, 142-152.
Nepka, C., Sivridis, E., Antonoglou, O., Kortsaris, A., Georgellis, A., Taitzoglou, I., Hytiroglou, P., Papadimitrou, C., Zintzaras, I., Kouretas, D., 1999. Chemopreventive activity of very low dose dietary tannic acid administration in hepatoma bearing C3H male mice. Cancer Letters 141, 57-62.
Gali, H. U., Perchellet, E. M., Klish, D. S., Johnson, J. M., Perchellet, J. P., 1992. Hydrolyzable tannins: potent inhibitors of hydroperoxide production and tumor promotion in mouse skin treated with 12-O-tetradecanoylphobol-13-acetate in vivo. International Journal of Cancer 51, 425-436.
Athar, M., Khan, W. A., Mukhtar, H., 1989. Effect of dietary tannic acid on epidermal, lung, and forestomach polycyclic aromatic hydrocarbon metabolism and tumorigenicity in Sencar mice. Cancer Research 49, 5784-5788.
Horikawa, K., Mohri, T., Tanaka, Y., Tokiwa, H., 1994. Moderate inhibition of mutagenicity and carcinogenicity of benzo[a]pyrene, 1,6-dinitropyrene and 3,9-dinitrofluoranthene by Chinese Medicinal Herbs. Mutagenesis 9, 523-526.
Khan, N. S., Hadi, S. M., 1998. Structural features of tannic acid important for DNA degradation in the presence of Cu [II]. Mutagenesis 13, 271-274.
Khan, N. S., Ahmad, A., Hadi, S. M., 2000. Anti-oxidant, pro-oxidant properties of tannic acid and its binding to DNA. Chemical and Biological Interactions 125, 177-189.
Bezkorovainy A The iron-sulpher proteins, in Biochemistry of Nonheme Iron. Plenum Press, New York, NY, 1980, p 343-347.
Scheibel LW, Sherman I W Metabolism and organellar function during various stages of the life cycle: Proteins, lipids, nucleic acids and vitamins, in Wernsdorfer W, McGregor I [eds]: Malaria: Principles and Practice of Malariology. New York, NY, Churchil Livingstone, 1988, p 219-242.
Wrigglesworth JM, Baum H: The biochemical features of iron, in Jacobs A, Worwood M [eds]: Iron in Biochemistry and Medicine San Diego, CA, Academic, 1980, p 29-86.
Scheibel LW Plasmodial parasite biology: Carbohydrate metabolism and related organellar function during various stages of the life cycle, in Wernsdorfer W, McGregor I [eds]: Malaria: Principles and Practice of Malariology. New York, NY, Churchil Livingstone, 1988, p 171.
Wernsdorfer WH, Trig PI: Recent progress of malaria research: Chemotherapy, in Wernsdorfer W, McGregor I [eds]: Malaria: Principles and Practice of Malariology. New York, NY, Churchill Livingstone, 1988, p 1569-1573.
Disler, P. B., Lynch, S. R., Torrance, J. D., Sayers, M. H., Bothwell, T. H. and Charlton, R. W. [1975b] The mechanism of the inhibition of iron absorption by tea. South African Journal of Medical Sciences 40, 109-l 16.
Brune, M., Hallberg, L. and Skanberg, A.  Determination of iron binding by phenolic groups in foods. Journal of Food Science 56, 128-167.
Mejbaum-Katzenellenbogen, W. and Kudrewicz-Hubicka, Z.  Application of urea, ferric ammonium sulfate and casein for determination of tanning substances in plants. Acta Biochimica Polonica 13, 57-67.
Modell B, Berdoukas V Deferoxamine, in The Clinical Approach to Thalassemia. Philadelphia, PA, Grune and Stratton, 1984, p 216.
Brittenham GM: Iron chelating agents, in Brian MC, McCulloch PB [eds]: Current Therapy in Hematology Oncology 3. St Louis, MO, Mosby, 1987, p 149.