Catalytic Transformation of Phenolic Compounds in the Soils

Principles and Practices in Plant Ecology: Allelochemical Interactions

Volumn , Issue , 2023, Pages 287-306

  Huang, P M ^a   Wang, M C ^b   Wang, M K ^c  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

^b NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^c NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85168503207     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9780203742181-22     Document Type: Chapter

References (104)

1. Barnhisel, R. I. and Bertsch, P. M., Chlorites and hydroxy-interlayered verrniculite and smectite, in Minerals in Soil Environments, Dixon, J. B. and Weed, S. B., Eds., Soil Science Society of America, Madison, Wl, 1989, 729.
2. Batistic, L. and Mayaudon, J., Stabilisation biologique dans le sol de l'acide ferulique 14C, de l'acide vanillique 14C et de 1' acide p-coumaric 14C, Ann. Inst. Pasteur; 188, 199, 1970.
3. Bollag, J.-M., Cross-coupling of humus constituents and xenobiotic substances, in Aquatic and Terrestrial Humic Materials, Christman, F. R. and Gjessing, E. T., Eds., Ann Arbor Press, Ann Arbor, MI, 1983.
4. Bollag, J.-M., Decontaminating soil with enzymes, Environ. Sci. Technol., 26, 1876, 1992.
5. Bollag, J.-M., Dec, J., and Huang, P. M., Formation mechanisms of complex organic structures in soil habitats, Adv. Agron., 63, 237, 1998.
6. Bollag, J.-M., Liu, S.-Y., and Minard, R. D., Cross-coupling of phenolic humus constituents and 2, 4- dichlorophenol, Soil Sci. Soc. Am. J., 44, 52, 1980.
7. Borchardt, G. A., Montmorillonite and other smectite minerals, in Minerals in Soil Environments, Dixon, J. B. and Weed, S. B., Eds., Soil Science Society of America, Madison, WI, 1989, 675.
8. Bums, R. G., Interactions of enzymes with soil mineral and organic colloids, in Interactions of soil Minerals with Natural Organics and Microbes, Huang, P. M. and Schnitzer, M., Eds., Soil Science Society of America, Madison, Wl, 1986, 429.
9. Chang, H. M. and Allan, G. G., Oxidation, in Lignins, Sarkanen, K. V. and Ludwig, C. H., Eds., Wiley Interscience, New York, 1971, 433.
10. Chiang, H. C., Cheng, Y. W., Yang, J. H., Homg, F. W., and Wang, M. K., Iron oxides in p1acic horizons of alpine forest soils, J. Chin. Agri. Chem. Soc., 32, 666, 1994.
11. Chou, C.-H., Allelopathy and sustainable agriculture, in Allelopathy, Processes, and Applications, Inderjit, Dakshini, K. M. M., and Einhellig, F. A., Eds., ACS Symposium Series 582, American Chemical Society, Washington, D.C., 1995, 211.
12. Chou, C. H. and Young, C. C., Phytotoxic substances in twelve subtropical grasses, J. Chem. Ecol., 1, 183, 1975.
13. Claus, H. and Filip, Z. K., Behavior of phenoloxidases in the presence of clays and other soil-related adsorbents, Appl. Microbial. Biotechnol., 28, 506, 1988.
14. Claus, H. and Filip, Z. K., Effects of clays and other solids on the activity of phenoloxidases produced by some fungi and actinomycetes, Soil Bioi. Biochem., 22, 483, 1990.
15. Coughlin, R. W. and Matsui, I., Catalytic oxidation of aqueous Mn(II), J. Catalysis, 41, 108, 1976.
16. Dec, J. and Bollag, J.-M., Microbial release and degradation of catechol and chlorophenols bound to synthetic humic acid, Soil Sci. Soc. Am. J., 52, 1366, 1988.
17. Dinel, H., Schnitzer, M., and Mehuys, G. R., Soillipids: origin, nature, content, decomposition, and effect on soil physical properties, in Soil Biochemistry, Vol. 6, Bollag, J.-M. and Stotzky, G., Eds., Marcel Dekker, New York, 1990, 397.
18. Baton, D. G., Complexing of metal ions with semiquinones. An electron spin resonance study, lnorg. Chem., 3, 1268, 1964.
19. Einhellig, F. A., Allelopathy: current status and future goals, in Allelopathy: Organisms, Processes, and Applications, Inderjit, Dakshini, K. M. M., and Einhellig, F. A., Eds., ACS Symposium Series 582, American Chemical Society, Washington, D.C., 1995, I.
20. Felix, C. C., Hyde, J. S., Sama, T., and Sealy, R. C., Interactions of melanins with metal ions. Electron spin resonance evidence for chelate samples of metal ions with free radicals, J. Am. Chem. Soc., 100, 3922, 1978.
21. Filip, Z. K. and Claus, H., Effect of soil minerals on the microbial formation of enzymes and their possible use in remediation of chemically polluted sites, in Environmental Impact of Soil Component Interactions, Vol. I, Natural and Anthropogenic Organics, Huang, P. M., Berthelin, J., Bollag, J.-M., McGill, W. B., and Page, A. L., Eds., CRC Press/Lewis, Boca Raton, FL, 1995, 409.
22. Filip, Z. K., Flaig, W., and Rietz, E., Oxidation of some phenolic substances as influenced by clay minerals, in sot. Radiat. Soil Org. Matter Studies, 11. International Atomic Energy Agency Bulletin, IAEA, Vienna, 1977, 91.
23. Filip, Z. K., Haider, K., and Martin, J. P., Influence of clay minerals on growth and metabolic activity of Epicoccum nigrum and Stachybotrys chartarum, Soil Bioi. Biochem., 4, 135, 1972.
24. Flaig, W., Beutelspacher, H., and Rietz, E., Chemical composition and physical properties of humic substances, in Soil Components, Vol. I, Organic Components, Gieseking, J. E., Ed., Springer-Verlag, New York, 1975, I.
25. Gianfreda, L. and Bollag, J.-M., Effect of soils on the behavior of immobilized enzymes, Soil Sci. Soc. Am. J., 58, 1672, 1994.
26. Haider, K., Filip, Z. K., and Martin, J. P., Einfluss von Montmorillonit auf die Bildung von Biomasse und Stoffwechseprodukten durch einige Mikroorganismen, Arch. Microbial., 73, 201, 1970.
27. Hayes, M. H. B. and Himes, F. L., Nature and properties of humus-mineral complexes, in Interactions of Soil Minerals with Natural Organics and Microbes, Huang, P. M. and Schnitzer, M., Eds., Soil Science Society of America, Madison, Wl, 1986, 103.
28. Ha yes, M. H. B. and Swift, R. S., The chemistry of soil organic colloids, in The Chemistry of Soil Constituents, Greenland, D. J. and Hayes, M. H. B., Eds., John Wiley & Sons, Chichester, 1978, 179.
29. Henderson, M. E. K., Release of aromatic compounds from birch and spruce sawdusts during decomposition by white-rot fungi, Nature (London), 175, 634, 1955.
30. Huang, P. M., Role of soil minerals in transformation of natural organics and xenobiotics in soil, in Soil Biochemistry, Vol. 6, Bollag, J.-M. and Stotzky, G., Eds., Marcel Dekker, New York, 1990, 29.
31. Huang, P. M., Ionic factors affecting the formation of short-range ordered aluminosilicates, Soil Sci. Soc. Am. J., 55, 1172, 1991.
32. Jackson, M. L., Soil Chemical Analysis-Advanced Course, published by the author, Department of Soil Science, University of Wisconsin, Madison, Wl, 1979.
33. Kononova, M. M., Soil Organic Matter, 2nd ed., Pergamon Press, New York, 1966.
34. Kumada, K., Absorption spectra of humic acids, Soil Plant Food, I, 29, 1955.
35. Kumada, K. and Kato, H., Browning of pyrogallol as affected by clay minerals, Soil Sci. Plant Nutr. (Tokyo), 16, 195, 1970.
36. Kyuma, K. and Kawaguchi, K., Oxidative changes of polyphenols as influenced by allophane, Soil Sci. Soc. Am. Proc., 28, 371, 1964.
37. Ladd, J. N. and Butler, J. H. A., Humus-enzyme systems and synthetic, organic polymer-enzyme analogs, in Soil Biochemistry, Vol. 4, Paul, E. A. and McLaren, A. D., Eds., Marcel Dekker, New York, 1975, 143.
38. Lehmann, B. G. and Cheng, H. H., Reactivity of phenolic acids in soil and formation of oxidation products, Soil Sci. Soc. Am. J., 52, 1304, 1988.
39. Leonowicz, A. and Bollag, J.-M., Laccases in soil and the feasibility of their extraction, Soil Bioi. Biochem., 19, 237, 1987.
40. Liu, S.-Y., Minard, R. D., and Bollag, J.-M., Oligomerization of syringic acid, a lignin derivative, by a phenoloxidase, Soil Sci. Soc. Am. J., 45, 1100, 1981.
41. Liu, S.-Y., Freyer, A. J., Minard, R. D., and Bollag, J.-M., Enzyme-catalyzed complex-formation of amino acid esters and phenolic humus constituents, Soil Sci. Soc. Am. J., 49, 337, 1985.
42. Maillard, L. C., Synthese des matieres humiques par action des acides amines sur les sucres reducteurs, Ann. Chim. Phys., 9(5), 258, 1916.
43. Martin, J. P. and Haider, K., Microbial activity in relation to soil humus formation, Soil Sci., Ill, 54, 1971.
44. Martin, J. P. and Haider, K., A comparison of the use of phenolase and peroxidase for the synthesis of model humic acid-type polymers, Soil Sci. Soc. Am. J., 44, 983, 1980a.
45. Martin, J. P. and Haider, K., Microbial degradation and stabilization of 14C-labeled lignins, phenols, and phenolic polymers in relation to soil humus formation, in Lignin Biodegradation: Microbiology, Chemistry, and Potential Applications, Vol. I, Kirk, T. K., Higuchi, T., and Cheng, H., Eds., CRC Press, Boca Raton, FL, 1980b, 77.
46. Martin, J. P., Filip, Z. K., and Haider, K., Effect of montmorillonite and hematite on growth and metabolic activity of some actinomycetes, Soil Bioi. Biochem., 8, 409, 1976.
47. Mathur, S. P. and Schnitzer, M., A chemical and spectroscopic characterization of some synthetic analogues of humic acid, Soil Sci. Soc. Am. J., 42, 591, 1978.
48. Mayaudon, J., Stabilization biologique des proteins 14-C dans le sol, in Isotopes and Radiation in Soil Organic Matter Studies, IAEA, Vienna, 1968, 177.
49. Mayaudon, J., El Halfawi, M., and Chalvignac, M. A., Propertes des diphenol oxydases exraits des sols, Soil Bioi. Biochem., 5, 369, 1973.
50. McKenzie, R. M., Manganese oxides and hydroxides, in Minerals in Soil Environments, Dixon, 1. B. and Weed, S. B., Eds., Soil Science Society of America, Madison, WI, 1989, 439.
51. Moore, J. W. and Pearson, R. G., Kinetics and Mechanisms, 3rd ed., John Wiley & Sons, New York, 1988.
52. Mortland, M. M. and Halloran, L. J., Polymerization of aromatic molecules on smectites, Soil Sci. Soc. Am. J., 40, 367, 1976.
53. Pal, S., Bollag, J.-M., and Huang, P. M., Role of abiotic and biotic catalysts in the transformation of phenolic compounds through oxidative coupling reactions, Soil Bioi. Biochem., 26, 813, 1994.
54. Pinnavaia, T. J., Hall, P. L., Cady, S. S., and Mortland, M. M., Aromatic radical cation formation on the intracrystal surfaces of transition metal layer lattice silicates, J. Phys. Chem., 78, 994, 1974.
55. Rice, E. L., Allelopathy, 2nd ed., Academic Press, New York, 1984.
56. Scheffer, F., Meyer, B., and Niederbudde, E. A., Huminstoffbildung unter katalyischer Einwirkung nathrlich vorkommender Eisenverbindungen im Modellversuch, Z. Pflanzenernaehr. Bodenkd., 87, 26, 1959.
57. Scheffer, F. and Ulrich, B., Humus und Humusduengung, Ferdinand Enke Verlag, Stuttgart, Germany, 1960.
58. Schnitzer, M., Humic substances: chemistry and reactions, in Soil Organic Matter, Schnitzer, M. and Khan, S. U., Eds., Elsevier, Amsterdam, 1978, 1.
59. Schnitzer, M., Quo vadis soil organic matter research. Panel discussion paper, in Whither soil research, Publications of the 12th Int. Congr. Soil Sci., New Delhi 5, 67, 1982.
60. Schnitzer, M. and Khan, S. U., Humic Substances in the Environment, Marcel Dekker, New York, 1972.
61. Shindo, H. and Huang, P. M., Role of Mn(IV) oxide in abiotic formation of humic substances in the environment, Nature (London), 298, 363, 1982.
62. Shindo, H. and Huang, P. M., Significance of Mn(IV) oxide in abiotic formation of organic nitrogen complexes in natural environments, Nature (London), 308, 57, 1984a.
63. Shindo, H. and Huang, P. M., Catalytic effects of manganese (IV), iron (Ill), aluminum, and silicon oxides on the formation of phenolic polymers, Soil Sci. Soc. Am. J., 48, 927, 1984b.
64. Shindo, H. and Huang, P. M., Catalytic polymerization of hydroquinone by primary minerals, Soil Sci., 39, 505, 1985a.
65. Shindo, H. and Huang, P. M., The catalytic power of inorganic components in the abiotic synthesis of hydroquinone-derived humic polymers, Appl. Clay Sci., 1, 71, 1985b.
66. Shindo, H. and Huang, P. M., Comparison of the influence of Mn(IV) oxide and tyrosinase on the formation of humic substances in the environment, Sci. Total Environ., 1171118, 103, 1992.
67. Simmons, K. E., Minard, R. D., and Bollag, J.-M., Oxidative coupling and polymerization of guaiacol, a lignin derivative, Soil Sci. Soc. Am. J., 52, 1356, 1988.
68. Sjoblad, R. D. and Bollag, J.-M., Oxidative coupling of aromatic compounds by enzymes from microorganisms, in Soil Biochemistry, Vol. 5, Paul, E. A. and Ladd, J. N., Eds., Marcel Dekker, New York, 1981, 113.
69. Solomon, D. H., Clay minerals as electron acceptors and/or electron donors in organic reactions, Clays Clay Miner., 16, 31, 1968.
70. Stevenson, F. J., Humus Chemistry: Genesis Composition, Reactions, Wiley-Interscience, New York, 1994.
71. Stevenson, I. L. and Schnitzer, M., Transmission electron microscopy of extracted fu1vic and humic acids, Soil Sci., 133, 179, 1982.
72. Stone, A. T., Reduction dissolution of manganese (III/IV) oxides by substituted phenols, Environ. Sci. Technol., 21, 979, 1987.
73. Stone, A. T. and Morgan, J. J., Reduction and dissolution of manganese(III) and manganese(IV) oxides by organics: 2. Survey of the reactivity of organics, Environ. Sci. Technol., 18, 617, 1984.
74. Stotzky, G., Influence of soil mineral colloids on metabolic processes, growth, adhesion, and ecology of microbes and viruses, in Interactions of Soil Minerals with Natural Organics and Microbes, Huang, P. M. and Schnitzer, M., Eds., Soil Science Society of America, Madison, WI, 1986, 305.
75. Suflita, I. M. and Bollag, J.-M., Polymerization of phenolic compounds by a soil-enzyme complex, Soil Sci. Soc. Am. J., 45, 297, 1981.
76. Swain, T., Phenolics in the environment, in Rec. Adv. Phytochem., 12, 617, 1978.
77. Theng, B. K. G., Mechanisms of formation of colored clay-organic complexes. A review, Clays Clay Miner., 19, 383, 1971.
78. Theng, B. K. G., The Chemistry of Clay-Polymer Complexes, Elsevier, Amsterdam, 1974, 283.
79. Thomas, J. M. and Thomas, W. J., Introduction to the Principles of Heterogeneous Catalysis, Academic Press, New York, 1967.
80. Thompson, T. D. and Moll, W. F., Jr., Oxidative power of smectites measured by hydroquinone, Clays Clay Miner., 21, 337, 1973.
81. Verma, L., Martin, J. P., and Haider, K., Decomposition of carbon-14-Iabeled proteins, peptides, and amino acids: Free and complexed with humic polymers, Soil Sci. Soc. Am. Proc., 39, 279, 1975.
82. Wailer, G. R., Krenzer, E. G., McPherson, J. K., Jr., and McGown, S. R., Allelophatic compounds in soil from no tillage vs. conventional tillage in wheat production, Plant Soil, 98, 5, 1987.
83. Wang, M. C., Catalytic role of selected soil minerals in the abiotic formation of humic substances and the associated reactions, Ph. D. thesis, University of Saskatchewan, Saskatoon, Canada, 1987.
84. Wang, M. C., Influence of pyrogallol on the catalytic action of iron and manganese oxides in amino acid transformation, in Environmental Impact of Soil Component Interactions, Vol. I, Natural and Anthropogenic Organics, Huang, P. M., Berthelin, J., Bollag, J.-M., McGill, W. B., and Page, A. L., Eds., CRC Press/Lewis Publishers, Boca Raton, FL, 1995, 169.
85. Wang, M. C. and Huang, P. M., Humic macromolecule interlayering in nontronite through interaction with phenol monomers, Nature (London), 323, 529, 1986.
86. Wang, M. C. and Huang, P. M., Polycondensation of pyrogallol and glycine and the associated reactions as catalyzed by bimessite, Sci. Total Environ., 62, 435, 1987.
87. Wang, M. C. and Huang, P. M., Catalytic power of nontronite, kaolinite, and quartz and their reaction sites in the formation of hydroquinone-derived polymers, Appl. Clay Sci., 4, 43, 1988.
88. Wang, M. C. and Huang, P. M., Nontronite catalysis in polycondensation of pyrogallol and glycine and the associated reactions, Soil Sci. Soc. Am. J., 55, 1156, 1991.
89. Wang, M. C. and Huang, P. M., Structural role of polyphenols in influencing the ring cleavage and related chemical reactions as catalyzed by nontronite, in Humic Substances in the Global Environment and Implications on Human Health, Senesi, N. and Miano, T. M., Eds., Elsevier, Amsterdam, 1994, 173.
90. Wang, M. C. and Lin, C. H., Enhanced mineralization of amino acids by bimessite as influenced by pyrogallol, Soil Sci. Soc. Am. J., 51, 88, 1993.
91. Wang, T. S. C., Chen, J.-H., and Hsiang, W.-M., Catalytic synthesis of humic acids containing various amino acids and dipeptides, Soil Sci., 140, 3, 1985.
92. Wang, T. S. C., Huang, P. M., Chou, C.-H., and Chen, J.-H., The role of soil minerals in the abiotic polymerization of phenolic compounds and formation of humic substances, in Interactions of Soil Minerals with Natural Organics and Microbes, Huang, P. M. and Schnitzer, M., Eds., Soil Science Society of America, Madison, WI, 1986, 251.
93. Wang, T. S. C., Kao, M.-M., and Li, S. W., A new proposed mechanism of formation of soil humic substance, in Studies and Essays in Commemoration of the Golden Jubilee of Academia Sinica, Academia Sinica, Taipei, Taiwan, 1978b.
94. Wang, T. S. C., Kao, M.-M., and Huang, P. M., The effect of pH on the catalytic synthesis of humic substances by illite, Soil Sci., 129, 333, 1980.
95. Wang, T. S. C. and Li, S. W., Clay minerals as heterogeneous catalysts in preparation of model humic substances, Z. Pflanzenemaehr. Bodenkd., 140, 669, 1977.
96. Wang, T. S. C., Li, S. W., and Femg, Y. L., Catalytic polymerization of phenolic compounds by clay minerals, Soil Sci., 126, 15, 1978a.
97. Wang, T. S. C., Wang, M. C., and Huang, P. M., Catalytic synthesis of humic substances by using aluminas as catalysts, Soil Sci., 136, 226, 1983.
98. Wang, T. S. C., Yang, T., and Chuang, T., Soil phenolic acids as plant growth inhibitors, Soil Sci., 103, 239, 1967.
99. Wang, T. S. C., Yeh, K. L., Cheng, S. Y., and Yang, T. K., Behavior of soil phenolic acids, in Biochemical Interaction Among Plants, National Academy of Sciences, Washington, D.C., 1971, 113.
100. Welte, E., Zur Konzentrationsmessung von Huminsauren, Z. Pflanzenemaehr. Dhng. Bodenk, 14, 219, 1956.
101. Whitehead, D. C., Identification of p-hydroxybenzoic, vanillic, p-coumaric and ferulic acids in soils, Nature (London), 202, 417, 1964.
102. Whitehead, D. C., Dibb, H., and Hartley, R. D., Bound phenolic compounds in water extracts of soils, plant roots and leaf litter, Soil Bioi. Biochem., 15, 133, 1983.
103. Young, C. C. and Chou, T. C., Autointoxication of residues of Asparagus officinalis L., Plant Soil, 85, 385, 1985.
104. Young, C. C., Tsai, C. S., and Chen, S. H., Allelochemicals in rhizosphere soils of Dendrocalamus latijlorus Munro and Asparagus officinalis L., in Phytochemical Ecology: Allelochemicals, Mycotoxins and Insect Pheromones and Allomones, Chou, C. H. and Waller, G. R., Eds., Institute of Botany, Academia Sinica, Monograph 9, Taipei, ROC, 1989, 227.