REVIEW OF METHODS FOR THE QUALITATIVE AND QUANTITATIVE ANALYSIS OF TANNINS IN PLANT MATERIALS
UDC 54.061,54.062
Abstract
Tannins are an extensive group of secondary metabolites widely used in medical practice and in human activities. They are characterized by a wide range of pharmacological activities, including antitumor, astringent, hemostatic, antioxidant and prooxidant, antimicrobial, antiviral, and others. The methods used for the chemical analysis of this group of compounds and for the standardization of tannin-containing types of plant materials have been improved with the development of analytical methods. Addressing the issues of standardization and application of hydrolysable and condensed tannins remain relevant today. This review reflects the main milestones in the historical development of tannin analysis: from using qualitative droplet reactions and physical properties, using the simplest physico-chemical analysis methods to establishing the structure of NMR spectroscopy, and from titrimetric methods using chemical and physico-chemical indicators to modern high-performance chromatography with various types of detectors, as well as the use of combinations of modern physicochemical methods of analysis with mathematical methods for assessing and predicting the qualitative and quantitative composition of tannins and their pharmacological effect. The main types of biological activity of hydrolysable and condensed tannins obtained from plant objects and their mechanisms of action are described.
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Holness H. Analytica Chimica Acta, 1949, no. 3, pp. 290–294, DOI: 10.1016/s0003-2670(00)87343-2(1949).
Mejbaum-Katzenellenbogen W. Acta Biochimica Polonica, 1955, vol. 2, pp. 279–296.
Watkins P.E., White T. Proceedings of the Second International Congress of Surface Activity. London: Butterworths. 1957, pp. 183–196.
Spiers C.W. The Journal Agricultural Science, 1914, vol. 6, no. 1, pp. 77–83.
Howard B.J. Bulletin of the Torrey Botanical Club, 1906, vol. 33, no. 11, pp. 567–576, DOI: 10.2307/2478934.
Lloyd F.E. The Plant World, 1911, vol. 14, no. 1, pp. 1–14.
Stitt R.E., Clarke I.D. American Society of Agronomy, 1941, no. 33, p. 739.
Kirby K.S., White T. Biochem Journal, 1955, no. 60(4), pp. 582–590.
Buchanan M.A., Lewis H.F., Kurth E.F. Journal of Industrial and Engineering Chemistry, 1944, no. 36(10), pp. 907–910.
Oshima Y. Bulletin of the Agricultural Chemical Society of Japan, 1936, no. 12(8), pp. 103–114, DOI: 10.1271/bbb1924.12.103.
Kirby K.S. British Journal of Cancer, 1960, no. 14(1), pp. 147–153.
Okuda T., Yoshida T., Hatano T. Journal of Natural Products, 1989, no. 52(1), pp. 1–31, DOI: 10.1021/np50061a001.
Ahmad P., Jaleel C.A., Salem M.A., Nabi G., Sharma S. Critical Reviews of Biotechnology, 2010, no. 30(3), pp. 161–175. DOI: 10.3109/07388550903524243.
Halliwell B. Biochemistry Society Transaction, 2007, no. 35(5), pp. 1147–1150, DOI: 10.1042/BST0351147.
Quideau S., Deffieux D., Douat-Casassus C., Pouységu L. Angewandte Chemie International Edition, 2011, no. 50, pp. 586–621, DOI: 10.1002/anie.201000044.
Leopoldini M., Russo N., Toscano M. Food Chemistry Journal, 2011, no. 125, pp. 288–306. DOI: 10.1016/j.foodchem.2010.08.012.
Pulido R., Bravo L., Saura-Calixto F. Journal Agricultural Food Chemistry, 2000, no. 48, pp. 3396–3402. DOI: 10.1021/jf9913458.
Pfundstein B., El Desouky S.K., Hull W.E., Haubner R., Erben G., Owen R.W. Phytochemistry, 2010, no. 71, pp. 1132–1148. DOI: 10.1016/j.phytochem.2010.03.018.
Wright J.S., Johnson E.R., DiLabio G.A. Journal of the American Chemistry Society, 2001, no. 123, pp. 1173–1183. DOI: 10.1021/ja002455u.
Galati G., O´Brien P.J. Free Radical Biology & Medicine, 2004, no. 37(3), pp. 287–303. DOI: 10.1016/j.freeradbiomed.2004.04.034.
Badhani B., Sharma N., Kakkar R. RSC Advances, 2015, no. 5(35), pp. 27540–27557. DOI: 10.1039/c5ra01911g.
Naumann H.D., Tedeschi L.O., Zeller W.E., Huntley N.F. Revista Brasileira de Zootecnia, 2017, no. 46(12), pp. 929–949. DOI: 10.1590/s1806-92902017001200009.
Palanisamy U.D., Ling L.T., Manaharan T., Appleton D. Food Chemistry, 2011, no. 127, pp. 21–27. DOI: 10.1016/j.foodchem.2010.12.070.
Sergediené E., Jönsson K., Szymusiak H., Tyrakowska B., Rietjens I., Cénas N. FEBS Letters, 1999, no. 462, pp. 392–396. DOI: 10.1016/S0014-5793(99)01561-6.
Hada S., Hattori M., Namba T. Journal of Medical Pharmaceutical Wakan Yaku Society, 1989, no. 6, pp. 100–104.
Sakanaka S., Aizawa M., Kim M., Yamamoto T. Bioscience, Biotechnology and Biochemistry, 1996, no. 60(5), pp. 745–749. DOI: 10.1271/bbb.60.745.
Baldé A.M., Claeys M., Pieters L., Wray V., Vlietinck A. Planta Medica., 1991, no. 57, suppl. 2, pp. A42-A43.
Balde´ A.M. Biological and Phytochemical Investigations on Three Plants Widely Used in Guinean Traditional Med-icine: Ph.D. Thesis, University of Antwerp. Belgium, 1990.
Balde´ A.M., Van Hoof L., Pieters L.A., Vanden Berghe D.A., Vlietinck A.J. Phytotherapy Research, 1990, no. 45, pp. 182–188. DOI: 10.1002/ptr.2650040505.
Balde´ A.M., Pieters L.A., Wray V., Kolodziej H., Vanden Berghe D.A., Claevys M., Vlietinck A.J. Phytochemistry, 1991, no. 30, pp. 4129–4135.
Ozaki Y., Okashi T., Minami A., Nakamura S. American Society for Microbiology Journals, 1987, no. 55, pp. 1436–1440.
Takechi M., Tanaka Y., Takehara M., Nonaka G.-I., Nishioka I. Phytochemistry, 1985, no. 24(10), pp. 2245–2250. DOI: 10.1016/S0031-9422(00)83018-6.
Ubillas R., Jolad S., Bruening R., Kernan M., King S., Sesin D., Barrett M., Stoddart C., Flaster T., Kuo J., Ayala F., Meza E., Castanel M., McMeekin D., Rozhon E., Tempesta M., Barnard D., Huffman J., Smee D., Sidwell R., Soike K., Brazier A., Safrin S., Orlando R., Kenny P., Berova N., Nakanishi K. Phytomedecine, 1994, no. 1, pp. 77–106. DOI: 10.1016/S0944-7113(11)80026-7.
Kakiuchi N., Hattori M., Namba T. Journal of Natural Products, 1985, no. 48(4), pp. 614–621. DOI: 10.1021/np50040a016.
Kakiuchi N., Kusumoto I., Hattori M., Namba T., Hatano T., Okuda T. Phytotherapy Research, 1991, no. 5, pp. 270–272. DOI: 10.1002/ptr.2650050609.
Bruyne T D., Pieters L., Deelstra H., Vlietinck A. Biochemical Systematics and Ecology, 1999, no. 27(4), pp. 445–459. DOI: 10.1016/S0305-1978(98)00101-X.
Lim S.H., Darah I., Jain K. Journal of Tropical Forest Science, 2006, vol. 18, no. 1, pp. 59–65.
Mailoa M.N., Mahendradatta M., Laga A., Djide N. International Journal of Scientific & Technology Research, 2014, vol. 3, no. 1, pp. 236–241.
Wagner H., Elbl G., Lotter H., Guinea M. Pharmaceutical and Pharmacological Letters, 1991, no. 1, pp. 15–18.
Hatano T., Edamatsu R., Hiramatsu M., Mori A., Fujita Y., Yashuhara T., Yoshida T., Okuda T. Chemical and Pharmaceutical Bulletin, 1989, no. 37(8), pp. 2016–2021. DOI: 10.1248/cpb.37.2016.
Lesuisse M., Casteras-Simon M., Labbe P. Journal of Biological Chemistry, 1996, no. 271(23), pp. 13578–13583. DOI: 10.1074/jbc.271.23.13578.
Ducrey B., Marston A., Gohring S., Hartmann R.W., Hostettmann K. Pharmacology and Molecular Biology, 1997, no. 63(2), pp. 111–114. DOI: 10.1055/s-2006-957624.
Kujawski M., Zhang C., Herrmann A., Reckamp K., Scuto A., Jensen M., Deng J., Forman S., Figlin R., Yu H. Mi-croinviroment and Immunology, 2010, vol. 70, no. 23, pp. 9599–9610. DOI: 10.1158/0008-5472.CAN-10-1293.
Granica S., Piwowarski J.P., Czerwinska M.E., Kiss A.K. Journal of Ethnopharmacology, 2014, no. 156, pp. 316–346. DOI: 10.1016/j.jep.2014.08.036.
Tits M., Angenot L., Damas J., Dierckxsens Y., Poukens P. Planta Medica, 1991, no. 57, p. A134.
Amanlou M., Dadkhah F., Salehnia A., Farsam H., Dehpour A.R. Journal of Pharmacy & Pharmaceutical Sciences: a Publication of the Canadian Society for Pharmaceutical Sciences, Societe Canadienne des Sciences Pharmaceutiques, 2005, no. 8(1), pp. 102–106.
Fawole O.A., Ndhlala A.R., Amoo S.O., Finnie J.F., Van Staden J. Journal of Ethnopharmacology, 2009, no. 123(2), pp. 237–243. DOI: 10.1016/j.jep.2009.03.012.
Scalbert A. Plant polyphenols, Plenum Press, New York, 1992, pp. 259–280.
Barbehenn R.V., Martin M.M., Hagerman A.E. Journal of Chemistry Ecology, 1996, no. 22(10), pp. 1901–1919. DOI: 10.1007/BF02028511.
Arapitsas P., Menichetti S., Vincieri F.F., Romani A. Journal Agricultural and Food Chemistry, 2007, no. 55, pp. 48–55. DOI: 10.1021/jf0622329.
Tuominen A. Tannins and other polyphenols in Geranium sylvaticum: Identification, intraplant distribution and bio-logical activity, Turku, 2017, 241 p.
Buzuc G.N., Lovkova M.Y., Ershik O.A., Sokolova S.M. Doklady Biochemistry and Biophysics, 2008, no. 421(1), pp. 211–213. DOI: 10.1134/s1607672908040121.
Chen X-X., Shi Y., Chai W-M., Feng H-L., Zhuang J.-X., Chen Q-X. PLoS ONE, 2014, no. 9(3), pp. 1–12. DOI: 10.1371/journal.pone.0091809.
Moilanen J., Sinkkonen J., Salminen J-P. Chemoecology, 2013, no. 23, pp. 165–179. DOI: 10.1007/s00049-013-0132-3.
Okuda T., Yoshida T., Hatano T., Ikeda Y., Shingu T., Inoue T. Chemical and Pharmaceutical Bulletin, 1986, no. 34(10), pp. 4075–4082. DOI: 10.1248/cpb.34.4075.
Peng S., Jay-Allemand C. Journal of Chemistry Ecology, 1991, no. 17(5), pp. 887–896. DOI: 10.1007/BF01395597.
Moilanen J., Salminen J.-P. Chemoecology, 2008, no. 18, pp. 73–83. DOI: 10.1007/s00049-007-0395-7.
Karonen M., Loponen J., Ossipov V., Pihlaja K. Analitica Chimica Acta, 2004, vol. 522, no. 1, pp. 105–112. DOI: 10.1016/j.aca.2004.06.041.
Yanagida A., Shoji T., Shibusawa Y. Journal of Biochemical and Biophysical Methods, 2003, no. 56, pp. 311–322. DOI: 10.1016/S0165-022X(03)00068-X.
Skinner W.W. Official and Tentative Methods of Analysis of the Association of Official Agricultural Chemists, Min-neapolis, 1936, p. 196.
Shaw. Tannin Principles of Tea, Madras: United Planters' Association of South India, 1930.
Bottger W. Zeitschrift fur Physikalische Chemie, 1938, no. 24, p. 293.
Barua D.N., Houghton Roberts E.A. Biochem Journal, 1940, no. 34(12), pp.1524–1531.
Petricie I., Poljak Baresie N. Archiv der Pharmazie, 1979, no. 10, pp. 689–691.
Yermakov A.I. Metody biokhimicheskogo issledovaniya rasteniy. [Methods of biochemical research of plants]. Leningrad, 1972, 456 p. (in Russ.).
Tyul'kova Yu.A., Ryazanova T.V., Kremenko O.N. Journal of Siberian Federal University. Chemistry, 2014, no. 7, pp. 298–305. (in Russ.).
Grin'ko Ye.N. Farmatsiya, 2010, no. 5, pp. 49–53. (in Russ.).
Hase T. Tables for organic spectrometry. 8th edition, Otatieto, Helsinki, 1999, pp. 20–39.
Kaur H. Spectroscopy, Meerut: Pragati Prakashan, 2009, pp. 258–321.
Santos-Buelga C., Garcίa-Viguera C., Tomás-Barberán F.A. Methods in polyphenol analysis, Cambridge: The Royal Society of Chemistry, 2003, pp. 92–127.
Loponen E., Pihlaja K. Journal of Chromatography A, 1999, vol. 864, no. 2, pp. 283–291. DOI: 10.1016/S0021-9673(99)01036-5.
Akdemir Z.Ş., Tath İ.İ., Saracoğlu İ., İsmailoğlu U.B., Şahin-Erdemli İ., Caliş İ. Phytochemistry, 2001, vol. 56, no. 2, pp. 189–193. DOI: 10.1016/S0031-9422(00)00367-8.
Karonen M., Liimatainen J., Sinkkonen J. Journal of Separation Science, 2011, vol. 34, no. 22, pp. 3158–3165. DOI: 10.1002/jssc.201100569.
Valls J., Millán S., Martí M.P., Borràs E., Arola L. Journal of Chromatography A, 2009, vol. 1216, no. 43, pp. 7143–7172. DOI: 10.1016/j.chroma.2009.07.030.
Watson J.T., Sparkman O.D. Introduction to mass spectrometry: Instrumentation, applications, and strategies for data interpretation. 4th Edition, John Wiley & Sons, 2007, 841 p.
Self R., Eagles J., Galletti G.C., Mueller-Harvey I., Hartley R.D., Lea A.G.H., Magnolato D., Richli U., Gujer R., Haslam E. Biomedical & Environmental Mass Spectrometry, 1986, vol. 13, no. 9, pp. 449–468. DOI: 10.1002/bms.1200130902.
Okuda T., Nayeshiro H., Seno K. Tetrahedron Letters, 1977, vol. 18, no. 50, pp. 4421–4424. DOI: 10.1016/S0040-4039(01)83525-5.
Okuda T., Hatano T., Nitta H., Fujii R. Tetrahedron Letters, 1980, vol. 21, no. 45, pp. 4361–4364. DOI: 10.1016/S0040-4039(00)77858-0.
Sutar R.C., Gangwar S.S., Thakur R.N., Sharma R., Krishnan S P. Journal of Pharmacognosy and Phytochemistry, 2016, no. 5(6), pp. 199–204.
Harborne J.B. Phytochemical Methods. A Guide to Modern Techniques of Plant Analysis. Third edition, London: Chapman and Hall, 1998, 302 рр.
Wagner H, Baldt S. Plant drug analysis: A Thin Layer Chromatography Atlas. Second Edition, Berlin: Springer; 1996, 384 pp. DOI: 10.1007/978-3-642-00574-9.
Grasel F.d.S., Ferrao M.F., Wolf C.R. Industrial Crops and Products, 2016, no. 91, pp. 279–285. DOI: 10.1016/j.indcrop.2016.07.022.
Montoya L.F., Contreras D., Jaramillo A.F., Carrasco C., Fernández K., Schwederski B., Rojas D., Melendrez M.F. Progress in Organic Coating, 2019, no. 127, pp. 100–109. DOI: 10.1016/j.porgcoat.2018.11.010.
Matamala G., Smeltzer W., Droguett G. Corrosion Science, 1994, vol. 50, no. 4, pp. 271–275. DOI: 10.5006/1.3294333.
Xua W., Hana E-H., Wang Z. Journal of Materials Science & Technology, 2019, no. 35, pp. 64–75. DOI: 10.1016/j.jmst.2018.09.001.
Mazurek S., Fecka I., Węglińska M., Szostak R. Talanta, 2018, vol. 189, pp. 308–314. DOI: 10.1016/j.talanta.2018.07.012.
Mignolet A., Wood B.R., Goormaghtigh E. The Royal Society of Chemistry, 2018, no. 143, pp. 258–269. DOI: 10.1039/C7AN01460K.
British Pharmacopoeia, Health & Medicine, 2017, vol. IV, 15455 p.
European Pharmacopoeia 9.0, 2017, vol. I, pp. 1431–1436.
United States Pharmacopeia 40 – the National Formulary 35, United Book Press, 2017, vol. 1, 2389 p.
Gosudarstvennaya Farmakopeya Rossiyskoy Federatsii. XIV izdaniye. [The State Pharmacopoeia of the Russian Fed-eration. XIV edition]. Moscow, 2018. URL: http://www.femb.ru/feml (in Russ.).
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