Abstract
When various lignin-related para-phenolic benzoic acids, para-phenolic cinnamic acids, para-phenolic phenylpropionic acids, the corresponding unsubstituted and 4-O-methylated derivatives, and 4-hydroxyl substituted benzaldehydes were tested on the growth of eight white-rot fungi, methylation of the 4-hydroxy substituent resulted, in most cases, in increased inhibition of fungal growth. This effect was most notable with monomethoxylated compounds. When the aromatic ring contained additional methoxyl substituents, the toxicity of the 4-O-methylated derivative was less pronounced. Marked inhibition of fungal growth was also observed with aromatic compounds lacking a para-substituent. Higher concentrations of aromatic aldehydes were manifestly more toxic than the corresponding carboxylic acid.
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References
Akin, D.E. & Rigsby, L.L. 1985 Influence of phenolic acids on rumen fungi. Agronomy Journal 77, 180–182.
Ander, P. & Eriksson, K.E. 1976 The importance of phenol oxidase activity in lignin degradation by the white-rot fungus Sporotrichum pulverulentum. Archives of Microbiology 109, 1–8.
Ander, P., Hatakka, A. & Eriksson, K.E. 1980 Vanillic acid metabolism by the white-rot fungus Sporotrichum pulverulentum. Archives of Microbiology 125, 189–202.
Birkinshaw, J.H. & Findlay, W.P.K. 1940 Biochemistry of wood-rotting fungi. I. Metabolic products of Lentinus lepideus Fr. Biochemical Journal 34, 82–88.
Borneman, W.S., Akin, D.E. & Van Eseltine, W.P. 1986 Effect of phenolic monomers on ruminal bacteria. Applied and Environmental Microbiology 52, 1331–1339.
Buswell, J.A. 1991 Fungal degradation of lignin. In Handbook of Applied Mycology, Vol 1, Soil and Plants, eds Arora, A.K., Rai, B., Mukerji, G. & Knudsen, G. pp. 425–480. New York: Marcel Dekker.
Buswell, J.A., Ander, P., Pettersson, B. & Eriksson, K.E. 1979 Oxidative decarboxylation of vanillic acid by Sporotrichum pulverulentum. FEBS Letters 103, 98–101.
Buswell, J.A., Eriksson, K.E., Gupta, J.K., Hamp, S. & Nordh, I. 1982 Vanillic acid metabolism by selected soft-rot, brown-rot and white-rot fungi. Archives of Microbiology 131, 366–374.
Buswell, J.A., Mollet, B. & Odier, E. 1984 Ligninolytic enzyme production by Phanerochaete chrysosporium under conditions of nitrogen sufficiency. FEMS Microbiology Letters 25, 295–299.
Cherney, J.H., Anliker, K.S., Albrecht, K.A. & Wood, K.V. 1989 Soluble phenolic monomers in forage crops. Journal of Agricultural and Food Chemistry 37, 345–350.
Eriksson, K.E., Gupta, J.K., Nishida, A. & Rao, M. 1984 Syringic acid metabolism by some white-rot, soft-rot and brown-rot fungi. Journal of General Microbiology 130, 2457–2464.
Eriksson, K.E., Kolar, M-C, Ljungquist, P.O. & Kringstad, K.P. 1985 Studies on microbial conversions of chlorolignins. Environmental Science and Technology 19, 1219–1224.
Gupta, J.K., Hamp, S.G., Buswell, J.A. & Eriksson, K.-E. 1981 Metabolism of trans-ferulic acid by the white-rot fungus Sporotrichum pulverulentum. Archives of Microbiology 128, 349–354.
Johnsrud, S.C. & Eriksson, K.E. 1985 Cross-breeding of selected and mutated homokaryotic strains of Phanerochaete chrysosporium K-3. New cellulase deficient strains with increased ability to degrade lignin. Applied Microbiology and Biotechnology 21, 320–327.
Long, A. & Ward, O.P. 1989 Biotransformation of benzaldehyde by Saccharomyces cerevisiae: characterization of the fermentation and toxicity effects of substrates and products. Biotechnology and Bioengineering 34, 933–941.
Martin, S.A. & Akin, D.E. 1988 Effect of phenolic monomers on the growth and β-glucosidase of Bacteroides ruminocola and on the carboxymethylcellulase, β-glucosidase and xylanase from Bacteroides succinogenes. Applied and Environmental Microbiology 54, 3019–3022.
Mueller-Harvey, I., Hartley, R.D., Harris, P.J. & Curzon, E.H. 1986 Linkage of p-coumaryl and feruloyl groups to cell-wall polysaccharides of barley straw. Carbohydrate Research 148, 71–85.
Muheim, A., Waldner, R., Sanglard, D., Reiser, J., Schoemaker, H.E. & Leisola, M.S.A. 1991 Purification and properties of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium. European Journal of Biochemistry 195, 369–375.
Shea, S.K. & Buswell, J.A. 1992 Effect of lignin-derived phenols and their methylated derivatives on the growth of Lentinus spp. Letters in Applied Microbiology 15, 12–14.
Shimazono, H. 1959 Investigations on lignins and lignification. XXI. Identification of phenolic esters in the culture medium of Lentinus lepideus and the O-methylation of methyl p-coumarate to methyl p-methoxycinnamate in vivo. Archives of Biochemistry and Biophysics 83, 206–215.
Valli, K. & Gold, M.H. 1990 Degradation of 2,4-dichlorophenol by the lignin-degrading fungus Phanerochaete chrysosporium. Journal of Bacteriology 173, 345–352.
Wat, C.K. & Towers, G.H.N. 1975 Phenolic O-methyltransferase from Lentinus lepideus (Basidiomycete). Phytochemistry 14, 663–666.
Yajima, Y., Enoki, A., Mayfield, M.B. & Gold, M.H. 1979 Vanillate hydroxylase from the white-rot basidiomycete Phanerochaete chrysosporium. Archives of Microbiology 123, 319–321.
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J.A. Buswell is with the Department of Biology, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong. K.-E.L. Eriksson is with the Department of Biochemistry, The University of Georgia, Athens, Georgia, 30602, USA.
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Buswell, J.A., Eriksson, K.E.L. Effect of lignin-related phenols and their methylated derivatives on the growth of eight white-rot fungi. World Journal of Microbiology & Biotechnology 10, 169–174 (1994). https://doi.org/10.1007/BF00360880
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DOI: https://doi.org/10.1007/BF00360880