Abstract
The inhibition of microorganisms by tannic compounds is due to hydrogen bonding with vital proteins such as enzymes. An important factor governing the toxicity of tannic compounds to microorganisms is the tannin polymer size. The strongest inhibition occurs with oligomers, since these are large enough for effective crossbridged hydrogen bonds with proteins, yet small enough for penetration to the sensitive sites within microorganisms. Tannins are particularly vulnerable to polymerization reactions in air; therefore, in practice, the toxicity of tannins is quite dynamic. Polymerization can result in the toxification of tannin monomers and in the detoxification of tannin oligomers.
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References
Tagari, H.; Henis, Y.; Tamir, M.; Volcani, R. The effect of carob pod extract on cellulolysis, proteolyisis, deamination and protein biosynthesis in an artificial rumen. Appl. Microbiol. 13:437 (1965).
Marquardt, R.R.; Ward, A.T.; Campbell, L.D.; Cansfield, P.E. Purification, identification and characterization of a growth inhibitor in faba beans (Vicia faba L. var.minor).J. Nutr. 107:1313 (1977).
Lewis, J.A.; Starkey, R.L. Vegetable tannins, their decomposition and effects on decomposition of some organic compounds. Soil Sci. 106:241 (1968).
Benoit, R.E.; Starkey, R.L.; Basaraba, J. Effect of purified plant tannin on decomposition of some organic compounds and plant materials. Soil Sci. 105:153 (1968).
Daiber, K. Enzyme inhibition by polyphenols of sorghum grain and malt. J. Sci.Food Agrie. 26:1399 (1975).
Verspuy, A.; Pilnik, W. Recovery of apple juice by pulp fermentation II: shortening the fermentation time. Flussiges Obst. 37:518 (1970).
Field, J.A.; Leyendeckers, M.J.H.; Sierra-Alvarez, R.; Lettinga, G.; Habets, L.H.A. The methanogenic toxicity of bark tannins and the anaerobic biodegradability of water soluble bark matter. Wat. Sci. Teeh. 20(1):219 (1988).
Field, J.A.; Lettinga, G. The methanogenic toxicity and anaerobic degradability of a hydrolyzable tannin. Wat. Res. 21:367 (1987).
Lyr, H. On the toxicity of oxidized polyphenols. Phytopath. Z. 52:229 (1965).
Benoit, R.E.; Starkey, R.L. Enzyme inactivation as a factor in the inhibition of decomposition of organic matter by tannins. Soil Sci. 105:203 (1968).
Porter, W.L.; Schwartz, J.H. Isolation and description of the pectinase-inhibiting tannins of grape leaves. J. Food Sci. 27:416 (1962).
Lyr, H. Hemmungsanalytische Untersuchungen an einigen ektoenzymen holzzerstorender Pilze. Enzymologia 23:231 (1961).
Williams, A.H. Enzyme inhibition by phenolic compounds. In: Enzyme chemistry of phenolic compounds. Pridham, J.B. (ed.) Pergamon Press, New York, pp. 87–95 (1963).
Hulmes, A.C.; Jones, J.D. Tannin inhibition of plant mitochondria. In: Enzyme chemistry of phenolic compounds. Pridham J.B. (ed.) Pergamon Press, New York, pp. 97–120 (1963).
Goldstein, J.L.; Swain, T. The inhibition of enzymes by tannins. Phytochemistry 4:185 (1965).
Tamir, M.; Alumot, E. Inhibition of digestive enzymes by condensed tannins from green and ripe tannins. J. Sci. Food Agric. 20:199 (1969).
Firenzuoli, A.M.; Vanni, P.; Mastronuzzi, E. The effect of some aromatic compounds on pure enzymes and their subsequent reactivation by PVP and Tween 80. Phytochemistry 8:61 (1969).
Boser, H. Modellversuche zur Beeinflussing des Zellstoffweschsel durch Pflanzeninhalt-stootoffe, insbesondere Flavonoide. Planta Med. 9:456 (1961).
Strumeyer, D.H.; Malin, M.J. Identification of the amylase inhibitor from seeds of Leoti sorghum. Biochim. Biophys. Acta. 184:643 (1969).
Hart, J.H.; Hillis, W.E. Inhibition of wood-rotting fungi by ellagitannins in the heartwood of Quercus alba. Phytopathology 62:620 (1972).
Nienstaedt, H. Tannin as a factor in the resistance of chestnut, Castanea spp., to the chestnut blight fungus, Endothia parasitica. Phytopathology 43:32 (1953).
Lewis, J.A.; Papavizas, G.C. Effects of tannins on spore germination and growth of Fusarium solani, F. phaseoli, and Vertidllium albo-atrum. Can. J. Microbiol. 13:1655 (1967).
Kekos, D.; Macris, B.J. Effect of tannins on growth and amylase production by Calvatia gigantea. Enzyme Microb. Ttchnol. 9(2):54 (1987).
Yu, M.; Chang, S.T. Tolerance of tannin by shiitake mushroom, Lentinus edodes. MIRCEN J. 5:375 (1989).
Cowley, G.T.; Whittingham, W.F. The effect of tannin on the growth of selected soil microfungi in culture. Mycologia 53:539 (1961).
Basaraba, J. Effect of vegetable tannins on glucose oxidation by various microorganisms. Can. J. Microbiol. 12:787 (1966).
Basaraba, J. Influence of vegetable tannins on nitrification in soil. Plant and Soil 21:8 (1964).
Henis, Y.; Tagari, H.; Volcani, R. Effect of water extracts of carob pods, tannic acid, and their derivatives on the morphology and growth of microorganisms. Appl. Microbiol. 12:204 (1964).
Booth, G.H. A study of the effect of tannins on the growth of sulphate-reducing bacteria. J. Appl. Bact. 23:125 (1960).
Haslam, E. Polyphenol-protein interactions. Biochem J. 139:285 (1974).
Bate-Smith, E.C. Haemanalysis of tannins:the concept of relative astringency. Phytochemistry 12:907 (1973).
Allaux, M.M. Effets et biodégradation des composés phénoliques chez les microorganismes anaérobies. Thesis, Laboratoire de Biotechnologie de L’Environment des I.I.A., Institut National de la Recherche Agronomique, Narbonne, Cedex, France, (1989).
White, T. Tannins-their occurence and significance. J. Sci. Food Agric. 8:377 (1957).
Singleton, V.L. Common plant phenols other than anthocyanins contribution to coloration and discoloration. In: Chichester, C.O. (ed.) Advances in food research. Supplement 3. The chemistry of plant pigments. Academic Press, New York, pp. 143–191 (1972).
Martin, J.P.; Haider, K.; Bondeietti, E. Properties of model humic acids synthesized by phenoloxidase and autoxidation of phenols and other compounds formed by soil fungi. In: Povoledo, D; Golterman, H.L. (eds.) Humic substances: their structure and function in the biosphere. Proceedings of an International Meeting Held at Nieuwersluis, The Netherlands, May 29-31, 1972. PUDOC-Centre for Agricultural Publishing and Documentation, Wageningen, The Netherlands, pp. 171–186 (1975).
Haider, K.; Martin, J.P.; Filip, Z.; Fustec-Mathon, E. Contribution of soil microbes to the formation of humic compounds. In:Povoledo, D; Golterman, H.L. (eds.) Humic substances: their structure and function in the biosphere. Proceedings of an International Meeting Held at Nieuwersluis, The Netherlands, May 29–31, 1972. PUDOC Centre for Agricultural Publishing and Documentation, Wageningen, The Netherlands, pp.71–85 (1975).
Sjoblad, R.D.; Bollag, J.M. Oxidative coupling of aromatic compounds by enzymes from soil microorganisms. In: Paul, E.A.; Ladd, J.N. (eds.) Soil biochemistry. Vol. 5. Marcel Dekker, Inc., New York, pp. 113–152 (1981).
Mathew, A.G.; Parpia, H.A.B. Food browning as a polyphenol reaction. In: Chichester, CO.; Mrak, E.M.; Stewart, G.F. (eds.) Advances in food research.Vol 19, Academic Press, New York, pp. 75–145 (1971).
Haider, K.; Martin, J.P.; Filip, Z. Humus biochemistry. In: Paul, E.A.; McLaren, A.D. (eds.) Soil biochemistry. Vol. 4. Marcel Dekker, Inc., New York, pp. 196–244 (1975).
E. H. 1958. The polyphenolase of tobacco and its participation in amino acid metabolism. 1. Manometric studies. Arch. Bioehem. Biophys. 74:198 (1975).
Jackson, H.; Kendal, L.P. The oxidation of catechol and homocatechol by tyrosinase in the presence of amino acids. Biochem. J. 44:477 (1949).
Loomis, W.D.; Battaile, J. Plant phenolic compounds and the isolation of plant enzymes. Phytochemistry, 5:423 (1966).
Mason, H.S.; Peterson, E.W. Melanoproteins:1.Reactions between enzyme generated quinones and amino acids. Biochem. Biophys. Acta 111:134 (1965).
Stevenson, F.J. Biochemistry of the formation of humic substances. Chapter 8 In: Humus chemistry: genesis, composition, reactions. John Wiley and Sons, New York, pp. 195–220 (1982).
Bollag, J-M.; Minard, R.D.; Liu, S-Y. Cross-linkage between anilines and phenolic humus constituents. Environ. Sci. Technol. 17:72 (1983).
Bollag, J-M.; Liu, S-Y. Copolymerization of halogenated phenols and syringic acid. Pesticide Biochem. Physiol. 23:261 (1985).
Hathway, D.E.; Seakins, J.W.T. Autoxidation of catechin. Nature 176:218 (1955).
Hathway, D.E.; Seakins, J.W.T. Enzymatic oxidation of catechin to a polymer structurally related to some phlobatannins. Biochem. J. 67:239 (1957).
Field, J.A.; Kortekaas, S.; Lettinga, G. The tannin theory of methanogenic toxicity. Biological Wastes 29:241 (1989).
Weinges, K.; Ebert, W.; Huthwelker, D.; Mattauch, H.; Perner, J. Oxydative kupplung von phenolen, 2.Konstitution und bildungsmechanismus des dehydro-dicatechins A. Liebigs Ann. Chem. 726:114 (1969).
Baruah, P.; Swain, T. The action of potato phenolase on flavanoid compounds. J. Sci. Food Agric. 10:125 (1959).
Updegraff, D.M.; Grant, W.D. Microbial utilization of Pinus radiata bark. Appl. Microbiol. 30:722 (1975).
Field, J. A.; Lettinga, G.; Habets, L.H.A. Oxidative detoxification of aqueous bark extracts. Part I: autoxidation. J. Chem. Technol. Biotechnol. 49:15 (1990).
Field, J.A.; Lettinga, G. Treatment and detoxification of aqueous spruce bark extracts by Aspergillus niger. Wat. Sci. Tech. 24(3/4):127 (1991).
Forss, K.; Jokinen, K.; Savolainen, M.; Williamson, H. Utilization of enzymes for effluent treatment in the pulp and paper industry. Paper ja Pun — Paper and Timber 10:1108 (1989).
Lea, G.H.A. Reversed-phase high performance liquid chromatography of procyanidins and other phenolics in fresh and oxidising apple juices using a pH shift technique. J. Chromatogr. 238:253 (1982).
Stahmann, M.A. The biochemistry of proteins of the host and parasite in some plant diseases. Tagungs Berichte: Deutsche Demokratische Republik Deutsche Akademie Der Landwirtschaftswissenschaften Zu Berlin, 74:9 (1965).
Oku, H. Biochemical studies on Cochliobolus miyabeanus: 4. Fungicidal action of polyphenols and the role of polyphenoloxidase of the fungus. Phytopath. 2. 38:343 (1960).
Harrison, B.D.; Pierpoint, W.S. The relation of polyphenoloxidase in leaf extracts to the instability of cucumber mosaic and other plant viruses. J. Gen. Microbiol. 32:417 (1963).
Field, J.A.; Lettinga, G. The effect of oxidative coloration on the methanogenic toxicity and anaerobic biodegradability of phenols. Biological Wastes 29:161 (1989).
Field, J. A.; Kortekaas, S.; Lettinga, G. The effect of autoxidation on the methanogenic toxicity and anaerobic biodegradability of pyrogallol. Biological Wastes 30:111 (1989).
Rudman, P. The causes of natural durability in timber: 8. The causes of decay resistance in tallowwood (Eucalyptus microccryt F. Meull.), white mahogany (Eucalyptus triantha Link.) and mountain ash (Eucalyptus regnans F. Muell.). Holzforschung 16(2):56 (1962).
Temmink, J. H. M.; Field, J.A.; van Haastrecht, J.C.; Merckelbach, R.C.M. Acute and sub-acute toxicity of bark tannins to carp (Cyprinus carpio L). Wat. Res. 23:341 (1989).
Field, J. A.; Lettinga, G.; Habets, L.H.A. Measurement of low molecular weight tannins: Indicators of methanogenic toxic tannins. J. Fermentation Bioengineer. 69:148 (1990).
Field, J.A.; Leyendeckers, M.J.H.; Sierra-Alvarez, R.; Lettinga, G.; Habets, L.H.A. Continuous anaerobic treatment of autoxidized bark extracts in laboratory-scale columns. Biotechnol. Bioengineer. 37:247 (1991).
Vachon, V.; Darwin, D.J.; Coulton, J.W. Transmembrane permeability channels across the outer membrane of Haemophilus influenzae type b. J. Bacteriol. 162:918 (1985).
Hancock, R.E.; Nikaido, H. Outer membranes of gram-negative bacteria: 19. Isolation from Pseudomonas aeruginosa PAO1 and use in reconstitution and definition of permeability barrier. J. Bacteriol. 136:381 (1978).
Vachon, V.; Kristjanson, D.N.; Coulton, J.W. Outer membrane porin protein of Haemophilus influenzae type b: Pore size and subunit structure. Can. J. Microbiol. 34:134 (1988).
Jones, W.T.; Broadhurst, R.B.; Lyttleton, J.W. The condensed tannins of pasture legume species. Phytochemistry 15:1407 (1976).
Rudman, P. The causes of natural durability in timber: 12. The deterioration in antifungal activity of heartwood extractives during the life of trees of Eucalyptus marginata Sm. Holzforschung 17(3):86 (1963).
Lewis, J.A.; Starkey, R.L. Decomposition of plant tannins by some soil microorganisms. Soil Sci. 107:235 (1969).
Yamada, H.; Adachi, O.; Watanabe, M.; Sato, N. Studies on fungal tannase:Part 1. Formation, purification and catalytic properties of tannase of Aspergillus flavus. Agr. Biol. Chem. 32:1070 (1968).
Jacob, F.H.; Pignal, M.C. Interactions levures-tannins.II. Etude en milieu tannant de quelques levures hydrolysant l’acide tannique. Mycopathol. Mycol. Appl. 48:121 (1972).
Deschamps, A.M.; Otuk, G.; Lebeault, J-M. Production of tannase and degradation of chestnut tannin by bacteria. J. Ferment. Technol. 61:55 (1983).
Field, J.A.; Lettinga, G. Biodegradation of tannins. In: Sigel. H. (ed.) Metal Ions in biological systems. Volume 28: Degradation of environmental pollutants by microorganisms and their metalloenzymes. Marcel Dekker, Inc., New York, (in press).
Broderick, A.J.; Sinclair, E.S. Microbial biomass production by continuous fermentation of bark hydrolysate. Appl. Microbiol. Biotechnol. 20:384 (1984).
Deschamps, A.M.; Leulliette, L. Tannin degradation by yeasts from decaying bark. International Biodeterioration 20:237 (1984).
Hamdi, M.; Khadir, A.; Garcia, J-L. The use of Aspergillus niger for the bioconversion of olive mill waste-water. Appl. Microbiol. Biotechnol. 34:828 (1991).
Bollen, W.B.; Lu, K.C. Douglas-fir bark tannin decomposition in two forest soils. USDA Forest Service, Pacific Northwest Forest Range Experiment Station, Research Paper PNW 85, Portland, OR, pp. 1-12 (1969).
Grant, W.D. Microbial degradation of condensed tannins. Science 17:1137 (1976).
Chandra, T.; Krishnamurty, V.; Madhavakrishna, W.; Nayudamma, Y. Astringency in fruits—5: Microbial degradation of wood apple (Feronia elephanturn) tannin. Leather Sci. 20:269 (1973).
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Field, J.A., Lettinga, G. (1992). Toxicity of Tannic Compounds to Microorganisms. In: Hemingway, R.W., Laks, P.E. (eds) Plant Polyphenols. Basic Life Sciences, vol 59. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3476-1_39
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