Abstract
Covalent lignin-carbohydrate (LC) linkages exist in lignocellulose from wood and groups herbaceous plants. In wood, they consist of ester and ether linkages through sugar hydroxyl to the α-carbanol of phenylpropane subunits in lignin. In grasses, ferulic and p-coumaric acids are esterified to hemicelluloses and lignin, respectively. Hemicelluloses also contain substituents and side groups that restrict enzymatic attack. Water-soluble lignin-carbohydrate complexes (LCCs) often precipitate during digestion with polysaccharidases, and the residual sugars are more diverse than the bulk hemicellulose. A number of microbial esterases and hemicellulose polysaccharidases including acetyl xylan esterase, ferulic acid esterase, and p-coumaric esterase attack hemicellulose side chains. Accessory hemicellulases include α-L-arabinofuranosidase and α-methyl-glucuranosidase. Both of these side chains are involved in LC bonds. β-Glucosidase will attach sugar residues to lignin degradation products and when carbohydrate is attached to lignin, lignin peroxidase will depolymerize the lignin more readily.
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References
Adhi TP, Korus RA & Crawford DL (1989) Production of major extracellular enzymes during lignocellulose degradation by two Streptomyces in agitated submerged culture. Appl. Environ. Microbiol. 55: 1165–1168.
Akin DE, & Rigsby LL (1985) Influence of phenolic acids on rumen fungi. Agronomy J. 77: 180–182.
Atushi K, Azuma J-I & Koshijima T (1984) Lignin-carbohydrate complexes and phenolic acids in bagasse. Holzforschung 38: 141–149.
Azuma J-I & Koshijima T (1988) Lignin-carbohydrate complexes from various sources. Methods Enzymology 161:12–18
Azuma J-I, Takahashi N & Koshijima T (1981) Isolation and characterization of lignin-carbohydrate complexes from the milled-wood lignin fraction of Pinus densiflora Sieb et Zucc. Carbohyd. Res. 93: 91–104.
Biely P, Krátky Z & Vrsanská M (1981) Substrate-binding site of endo-1,4-β-xylanase of the yeast Cryptococcus albidus. Eur. J. Biochem. 119: 559–564.
Biely P, Puls J & Schneider H (1985) Acetyl xylan esterases in fungal xylanolytic systems. FEBS 186: 80–84.
Biely P, MacKenzie CR, Puls J & Schneider H (1986) Cooper-ativity of esterases and xylanases in the enzymatic degradation of acetyl xylan. Bio/Technology 4: 731–733.
Borneman WS, Hartley RD, Morrison WH, Akin DE & Ljungdahl LG (1990) Feruloyl and p-coumaroyl esterase from anaerobic fungi in relation to plant cell wall degradation. Appl. Microbiol. Biotechnol. 33: 345–351.
Brice RE & Morrison IM (1982) The degradation of isolated hemicelluloses and lignin-hemicellulose complexes by cell-free rumen hemicellulases. Carbohyd. Res. 101: 93–100.
Broda PMA, Mason JC & Zimmerman WK (1987) Decomposition of lignocellulose. International Patent WO 87/0660
Chauvet J-M, Comtat J & Noe P (1987) Assistance in bleaching of never-dried pulps by the use of xylanases: Consequences on pulp properties. 4th Intl. Symp. Wood Pulping Chem. (Paris), Poster Presentations Vol 2: 325–327.
Chesson A (1988) Lignin-polysaccharide complexes of the plant cell wall and their effect on microbial degradation in the rumen. Animal Feed Sci. Technol. 21: 219–228.
Chesson A, Gordon AH & Lomax JA (1983) Substituent groups linked by alkali-labile bonds to arabinose and xylose residues of legume, grass and cereal straw cell walls and their fate during digestion by rumen microorganisms. J. Sci. Food. Agric. 34: 1330–1340.
Comtat J, Joseleau J-P, Bosso C & Barnoud (1974) Characterization of structurally similar neutral and acidic tetrasaccharides obtained from the enzymic hydrolysate of a 4-O-methyl-D-glucurono-D-xylan. Carbohyd. Res. 38:217–224.
Conchie J, Hay AJ & Lomax JA (1988) Soluble lignin-carbohydrate complexes from sheep rumen fluid: Their composition and structural features. Carbohyd. Res. 177: 127–151.
Crawford D (1978) Lignocellulose decomposition by selected Streptomyces strains. Appl. Environ. Microbiol. 35: 1041–1045.
Crawford DL, Pometto AL & Crawford RL (1983) Lignin degradation by Streptomyces viridosporus: Isolation and characterization of a new polymeric lignin degradation intermediate. Appl. Environ. Microbiol. 45: 898–904.
Donnelly PK & Crawford DL (1988) Production by Streptomyces viridosporus T7A of an enzyme which cleaves aromatic acids from lignocellulose. Appl. Environ. Microbiol. 54: 2237–2244.
Deobald LE & Crawford DL (1987) Activities of cellulase and other extracellular enzymes during lignin solubilization by Streptomyces viridosporus. Appl. Microbiol. Biotechnol. 26: 158–163.
Ericksson Ö, Goring DAI & Lindgren BO (1980) Structural studies on the chemical bonds between lignins and carbohydrates in spruce wood. Wood Sci. Technol. 14: 267–279..
Ford CW (1989) A feruloylated arabinoxylan liberated from cell walls of Digitaria decumbens (pangola grass) by treatment with borohydride. Carbohyd. Res. 190: 137–144.
Gaillard BDE & Richards GN (1975) Presence of soluble lignin-carbohydrate complexes in the bovine rumen. Carbohyd. Res. 42: 135–145.
Higuchi T, Ioto Y, Shimada M & Kawamura I (1967) Chemical properties of milled wood lignin of grasses. Phytochemistry 6: 1551–1556.
Ishihara M & Shimizu K (1988) α-(1 → 2)-glucuronidase in the enzymatic saccharification of hardwood xylan I. Screening of α-glucuronidase producing fungi. Mokuzai Gakkaishi 34: 58–64.
Ishii T & Hiroi T (1990) Isolation and characterization of feruloylated arabinoxylan oligosaccharides from bamboo shoot cell-walls. Carbohyd. Res. 196: 175–183.
Iversen T, Westermark U & Samuelsson B (1987) Some comments on the isolation of galactose-containing lignin-carbohydrate complexes. Holzforschung 41: 119–121.
Jeffries TW, Choi S & Kirk TK (1981) Nutritional regulation of lignin degradation by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 42: 290–296.
Johnson KG, Harrison BA, Schneider H, MacKenzie CR & Fontana JD (1988) Xylan-hydrolyzing enzymes from Streptomyces spp. Enzyme Microb. Technol. 10: 403–409.
Joseleau J-P, & Gancet C (1981) Selective degradations of the lignin-carbohydrate complex from aspen wood. Svensk Papperstidning 84: R123–R127
Jurasek L & Paice MG (1988) Biological beaching of pulp (pp 11–13). Tappi Internat. Pulp Bleach. Conf., Orlando, Florida
Kaji A (1984) L-Arabinosidases. Advan. Carbohyd. Chem. Biochem. 42: 383–394.
Kantelinen A, Rättö M, Sundquist J, Ranua M, Viikari L & Linko M (1988) Hemicellulases and their potential role in bleaching (pp 1–9). Tappi Internat. Pulp Bleaching Conf., Orlando, Florida
Kato A, Azuma JI & Koshijima T (1987) Isolation and identification of a new feruloylated tetrasaccharide from bagasse lignin-carbohydrate complex containing phenolic acid. Agric. Biol. Chem. 51: 1691–1693.
Khan AW, Lanm KA & Overend RP (1990) Comparison of natural hemicellulose and chemically acetylated xylan as substrates for the determination of acetyl-xylan esterase activity in Aspergilli. Enzyme Microb. Technol. 12: 127–131.
Kirk TK, Connors WJ, Bleam RD, Hackett WF & Zeikus JG (1975) Preparation and microbial decomposition of synthetic [14C] lignins. Proc. Natl. Acad. Sci. U.S.A. 72: 2515–2519.
Kirk TK, Connors WJ & Zeikus JG (1976) Requirement for a growth substrate during lignin decomposition by two wood-rotting fungi. Appl. Environ. Microbiol. 32: 192–194.
Kivaisi AK, Op den Camp HJM, Lubberding HJ, Boon JJ & Vogels GD (1990) Generation of soluble lignin-derived compounds during degradation of barley straw in an artificial rumen reactor. Appl. Microbiol. Biotechnol. 33: 93–98.
Kondo R & Imamura H (1987) The formation of model glyco-sides by wood-rotting fungi. Lignin enzymatic and microbial degradation. INRA, Paris
Kondo R & Imamura H (1989a) Formation of lignin model xyloside in polysaccharides media by wood-rotting fungi. Mokuzai Gakkaishi 35: 1001–1007.
Kondo R & Imamura H (1989b) Model study on the role of the formation of glycosides in the degradation of lignin by wood-rotting fungi. Mokuzai Gakkaishi 35: 1008–1013.
Kondo R, Imori T & Imamura H (1988) Enzymatic synthesis of glucosides of monomeric lignin compounds with commercial β-glucosidase. Mokuzai Gakkaishi 34: 724–731.
Kondo R, Imori T, Imamura H & Kishida T (1990) Polymerization of DHP and depolymerization of DHP glucoside by lignin oxidizing enzymes. J. Biotechnol. 13: 181–188.
Koshijima T, Watanabe T & Yaku T (1989) Structure and properties of the lignin-carbohydrate complex polymer as an amphipathic substance. In: Glasser WG & Sarkanen S (Eds) Lignin Properties and Materials. ACS Symposium Ser. 397 (pp 11–28). American Chemical Society, Washington, D.C.
Lee H, To RJB, Latta RK, Biely P & Schneider H (1987) Some properties of extracellular acetylxylan esterase produced by the yeast Rhodotorula mucilaginosa. Appl. Environ. Microbiol. 53: 2831–2834.
MacKenzie CR & Bilous D (1988) Ferulic acid esterase activity from Schizophyllum commune. Appl. Environ. Microbiol. 54: 1170–1173.
MacKenzie CR, Bilous D, Schneider H & Johnson KG (1987) Induction of cellulolytic and xylanolytic enzyme systems in Streptomyces spp. Appl. Environ. Microbiol. 53: 2835–2839.
Markwalder HU & Neukom H (1976) Diferulic acid as a possible crosslink in hemicelluloses from wheat germ. Phytochemistry 15: 836–837.
Mason JC, Richards M, Zimmerman W & Broda P (1988) Identification of extracellular proteins from actinomycetes responsible for the solubilization of lignocellulose. Appl. Microbiol. Biotechnol. 28: 276–280.
Mason JC, Birch OM & Broda P (1990) Preparation of 14C-radiolabelled lignocelluloses from spring barley of differing maturities and their solubilization by Phanerochaete chrysosporium and Streptomyces cyanus. J. Gen. Microbiol. 136: 227–232.
McCarthy AJ, MacDonald MJ, Paterson A & Broda P (1984) Degradation of [14C] lignin-labelled wheat lignocellulose by white-rot fungi. J. Gen. Microbiol. 130: 1023–1030.
McCarthy AJ, Paterson A & Broda P (1986) Lignin solubilization by Thermonospora mesophila. Appl. Microbiol. Biotechnol. 24: 347–352.
McDermid KP, MacKenzie CR & Forsberg CW (1990) Esterase activities of Fibrobacter succinogenes subsp Succinogenes S85. Appl. Environ. Microbiol. 56: 127–132.
Meshitsuka G, Lee ZZ, Nakano J & Eda S (1983) Contribution of pectic substances to lignin-carbohydrate bonding. Int. Symp. Wood Pulping Chem. 1: 149–152.
Minor JL (1982) Chemical linkage of pine polysaccharides to lignin. J. Wood Chem. Technol. 2(1): 1–16
Morison IM (1974) Structural investigation on the lignin-carbohydrate complexes of Lolium perene. Biochem J. 139: 197–204.
Mukoyoshi SI, Azuma JI and Koshijima T (1981) Lignin-carbohydrate complexes from compression wood of Pinus densiflora Sieb et. Zucc. Holzforschung 35: 233–240.
Neilson MJ & Richards GN (1982) Chemical structures in a lignin-carbohydrate complex isolated from bovine rumen. Carbohyd. Chem. 104: 121–138.
Obst JR (1982) Frequency and alkali resistance of lignin-carbohydrate bonds in wood. Tappi 65(4): 109–112
Odier E, Mozuch M, Kalyanaraman B & Kirk TK (1987) Cellobiose: quinone oxidoreductase does not prevent oxidative coupling of phenols or polymerization of lignin by ligninase. Les Colloques de l’INRA, No. 40. Dekker 131–136
Paice MG, Bernier R & Jurasek L (1988a) Viscosity-enhancing bleaching of hardwood kraft pulp with xylanase from a cloned gene. Biotechnol. Bioeng. 32: 235–239.
Paice MG, Bernier R & Jurasek L (1988b) Bleaching hardwood kraft with enzymes from cloned systems. CPPA Ann. Mtg. (Montreal) preprints 74A: 133–136
Paszczynski A, Huynh V-B & Crawford R (1985) Enzymatic activities of an extracellular manganese-dependent peroxidase from Phanerochaete chrysosporium. FEMS Microbiol. Lett. 29: 37–41.
Pometto AL & Crawford DL (1986) Catabolic fate of Streptomyces viridosporus T7A-produced, acid-precipitable polymeric lignin upon incubation with ligninolytic Streptomyces species and Phanerochaete chrysosporium. Appl. Environ. Microbiol. 51: 171–179.
Poutanen K & Sundberg M (1988) An acetyl esterase of Trichoderma reesei and its role in the hydrolysis of acetyl xylans. Appl. Microbiol. Biotechnol. 28: 419–424.
Puls J, Schmidt O & Granzow C (1987) α-Glucuronidase in two microbial xylanolytic systems. Enzyme Microb. Technol. 9: 83–88.
Ramachandra M, Crawford DL & Pometto AL (1987) Extracellular enzyme activities during lignocellulose degradation by Streptomyces spp.: A comparative study of wild-type and genetically manipulated strains. Appl. Environ. Microbiol. 53: 2754–2760.
Ramachandra M, Crawford DL & Hertel G (1988) Characterization of an extracellular lignin peroxidase of the lignocellulolytic actinomycete Streptomyces viridosporus. Appl. Environ. Microbiol. 54: 3057–3063.
Reid ID, Abrams GD & Pepper JM (1982) Water soluble products from the degradation of aspen lignin by Phanerochaete chrysosporium Can. J. Bot. 60: 2357–2364.
Renganathan V, Usha SN, & Lindenburg F (1990) Cellobioseoxidizing enzymes from the lignocellulose-degrading basidiomycete Phanerochaete chrysosporium: Interaction with microcrystalline cellulose. Appl. Microbiol. Biotechnol. 32: 609–613.
Roberts JC, McCarthy AJ, Flynn NJ & Broda P (1990) Modification of paper properties by the pretreatment of pulp with Saccharomonospora viridis xylanase. Enzyme Microb. Technol. 12: 210–213.
Scalbert A, Monties B, Lallemand JY, Guittet E & Rolando C (1985) Ether linkage between phenolic acids and lignin fractions from wheat straw. Phytochemistry 24: 1359–1362.
Shimada M, Fukuzuka T & Higuchi T (1971) Ester linkages of p-coumaric acid in bamboo and grass lignins. Tappi 54: 72–78.
Smith DCC (1955) Ester groups in lignin. Nature 176: 267–268.
Takahaski N & Koshijima T (1988) Ester linkages between lignin and glucuronoxylan in a lignin-carbohydrate complex from beech (Fagus crenata) wood. Wood Sci. Technol. 22: 231–241.
Tanabe H & Kobayashi Y (1986) Enzymatic maceration mechanism in biochemical pulping of mitsumata (Edgeworthia papyrifera Sieb, et Zucc.) bast. Agric. Biol. Chem. 50: 2779–2784.
Tanabe H & Kobayashi Y (1987) Effect of lignin-carbohydrate complex on maceration of mitsumata (Edgeworthia papyrifera Sieb, et Zucc.) bast by pectinolytic enzymes from Erwinia carotovora. Holzforschung 41: 395–399.
Tanabe H & Kobayashi Y (1988) Aggregate of pectic substances and lignin-carbohydrate complex in mitsumata (Edgeworthia papyrifera Sieb, et Zucc.) bast and its degradation by pectinolytic enzymes from Erwinia cartovora. Holzforschung 42: 47–52.
Tien M & Kirk TK (1983) Lignin-degrading enzyme from hymenomycete Phanerochaete chrysosporium Burds. Science 221: 661–663.
Tien M & Kirk TK (1984) Lignin-degrading enzyme from Phanerochaete chrysosporium: Purification, characterization, and catalytic properties of a unique H2O2-requiring oxygenase. Proc. Natl. Acad. Sci. U.S.A. 81: 2280–2284.
Timell TE (1962) Enzymatic hydrolysis of a 4-O-methylglucuronoxylan from the wood of white birch. Holzforschung 11: 436–447.
Wang PY, Bolker HI & Purves CB (1967) Uronic acid ester groups in some softwoods and hardwoods. Tappi 50(3): 123–124
Watanabe T & Koshijima T (1988) Evidence for an ester linkage between lignin and glucuronic acid in lignin-carbohydrate complexes by DDQ-oxidation. Agric. Biol. Chem. 52: 2953–2955.
Watanabe TJ, Ohnishi Y, Kaizu YS & Koshijima T (1989) Binding site analysis of the ether linkages between lignin and hemicelluloses in lignin-carbohydrate complexes by DDQ-oxidation. Agric. Biol. Chem. 53: 2233–2252.
Westermark U & Ericksson KE (1974a) Carbohydrate-dependent enzymic quinone reduction during lignin degradation. Acta Chem. Scand. B 28: 204–208.
Westermark U & Ericksson KE (1974b) Cellobiose-quinone oxidoreductase, a new wood-degrading enzyme from whiterot fungi. Acta Chem. Scand. B 28: 209–214.
Zimmerman W & Broda P (1989) Utilization of lignocellulose from barley straw by actinomycetes. Appl. Microbiol. Biotechnol. 30: 103–109.
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Jeffries, T.W. (1991). Biodegradation of lignin-carbohydrate complexes. In: Ratledge, C. (eds) Physiology of Biodegradative Microorganisms. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-3452-1_7
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