Abstract
One of the most prominent common features of vascular plants is their unique capacity to synthesize lignin. This substance is deposited in the cell walls of lignifying tissues, especially the xylem, thus providing rigidity to the otherwise elastic polysaccharide cell walls. Terrestrial plants can thus develop arborescent forms and, consequently, the acquisition of lignin is regarded as one of the essential factors in the evolution of higher plants. Lignin contributes about 20-30% of the dry weight of the woody of trees. This fact, together with the conspicuous predominance of vascular plants, indicates enormous quantities of lignin are produced; indeed, after cellulose, lignin represents the second most abundant natural product.
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References
Akazawa, T. and E. E. Conn. 1958. The Ooxidation of reduced pyridine nucleotides. J. Biol. Chem.232: 403–415.
Alibert, G. R. Ranjeva and A. M. Boudet. 1977. Organisation subcellulaire des voies de synthese des composes phenolique. Physiol. Veg.15(in press).
Amrhein, N. and M. H. Zenk. 1977. Metabolism of phenylpropanoid compounds. Physiol. Veg.15: 251–60.
Andersson, A., M. Erickson, H. Fridh and G. E. Miksche. 1973. Zur Struktur des Lignins der Rinde van Laubund Nadelholzern. Holzforschung27: 189–93.
Becker, H. and H. Nimz. 1974. Untersuchungen des Lignins der Mistel (Viscum Album L.) in Abhängigkeit von der jeweiligen Wirtspflanze. Z. Pflanzenphysiol. 72: 52–63.
Bergmann, L. 1964. Der Einfluss von Kinetin auf die Lignin-buildung und Differenzierung in Gewebekulturen von Nicotiana tabacum. Planta.62: 221–54.
Bland D.E. A. Logan M. Menshun and S Sternhell. 1968. The lignin of Sphagnum. Phytochemistry7: 1373–77.
Brown, S. A. 1966. Lignins. Ann. Rev. Plant Physiol.17: 223–44.
Cheng, C. K. C. and H. V. Marsh. 1968. Gibberellic acid-promoted lignification and phenylalanine ammonialyase activity in a dwarf pea (Pisum sativum). Plant Physiol.43: 1755–59.
Cramer, A. B., M. J. Hunter and H. Hibbert. 1939. Studies on lignin and related compounds. XXXV. The ethanolysis of spruce wood. J. Amer. Chem. Soc.61: 509–16.
El-Basyouni, S. Z., A. C. Neish and G. H. N. Towers. 1964. The phenolic acids in wheat. III. In soluble derivatives of phenolic cinnamic acids as natural intermediates in lignin biosynthesis. Phytochemistry3: 6127–39.
El-Basyouni, S. Z. and A. C. Neish. 1966. Occurrence of metabolically-active bound forms of cinnamic acid and its phenolic derivatives in acetone powders of wheat and barley plants in Phytochemistry5: 683–91.
Elstner, E. F. and A. Heupel. 1976. Formation of hydrogen peroxide by isolated cell walls from horseradish (Armoracia lapathifolia Gilib.) Planta.130: 175–80.
Erickson, M., S. Larsson and G. E. Miksche. 1973. Gaschromatographische Analyse von Ligninoxida- tionsprodukten. VII. Ein vergessertes Verfahren zur Charakterisierung von Ligninen durch Methylierung und oxydativen Abbau. Acta Chem. Scan.27: 127–40.
Erickson, M., S. Larsson and G. E. Miksche. 1973. VII. Zur Struktur des Lignins der Fichte. Acta Chem. Scand.27: 903–14.
Erickson, M. and G. E. Miksche. 1974. Charakterisierung der Lignine von Gymnospermen durch oxidativen Abbau. Holzforschung28:135–38.
Erickson, M. and G. E. Miksche. 1974. Charakterisierung der Lignine von Pteridophyten durch oxidativen Abbau. Holzforschung28:157–59.
Erickson, M. and G. E. Miksche. 1974. Two dibenzofurans obtained on oxidative degradation of the moss Polytrichum commune Hedw. Acta Chem. Scan. B.28: 109–13.
Erickson, M. and G. E. Miksche. 1974. On the occurrence of lignin or polyphenols in some mosses and liverworts. Phytochemistry13.: 2295–99.
Erickson, M., G. E. Miksche and I. Somfai. 1973. Charakterisierung der Lignine von Angiospermen durch oxydativen Abbau. I. Dikotylen. Holzforschung27: 113–17.
Erickson, M., G. E. Miksche and I. Somfai. 1973. II. Monokotylen. Holzforschung 27: 147–50.
Faix, O. 1976. Zur ganzheitlichen Betrachtungsweise lignin-analytischer Kenndaten. Das Papier30: V1–10.
Faix, O., E. Gyzas, and W. Schweers. 1977. Vergleichende Untersuchungen an Ligninen verschiedener Pteridophyten-Arten. Holzforschung, (in press.)
Faix, O and W. Schweers. 1974. Vergleichende Untersuchungen and Polymermodellen des Lignins (DHP’s) verschiedener Zusammensetzungen. 2. Mitt. Darstellung von ligninanalytischen Daten in einem Dreieckskoordinatensystem. Holzforschung28: 45–50.
Faix, O. and W. Schweers. 1974. 3 Mitt. IR-spektroskopische Untersuchungen. Holzforschung28: 50–54.
Faix, O. and W. Schweers. 1974. 4 Mitt. UV-spektroskopische Untersuchungen. Holzforschung28: 94–98.
Faix, O. and W. Schweers. 1974. 6. Mitt. Athanolyse, Nitrobenzol-Oxidation and Hydrogenolyse. Holzforschung28: 179–85.
Freudenberg, K., W. Lautsch and K. Engler. 1940. Die Bildung von Vanillin aus Fichtenlignin. Ber. Deutsch. Chem Ges.73: 167–71.
Freudenberg, K. and A. C. Neish. 1968. Constitution and Biosynthesis of Lignin. Springer, Berlin, Heidelberg, New York.
Freudenberg, K. and G. S. Sidhu. 1961. Zur Kenntnis des Lignins der Buche und der Fichte. Holzforschung25: 33–39.
Glasser, W. G. and H. R. Glasser. 1974. Simulation of reactions with lignin by computer (Simrel). II. A model for softwood lignin. Holzforschung28: 5–11.
Grisebach, H., H. Wengenmayer and D. Wyrambik. 1977. Cinnamoyl-CoA: NADP oxidoreductase and cinnamyl alcohol dehydrogenase. Two enzymes of lignin monomer biosynthesis. 2nd International Symposium on Pyridine Nucleotide-Dependent Dehydrogenases. Konstanz (Germany),: 1–12.
Gross, G. G. 1977. Biosynthesis of lignin and related monomers. Ree. Adv. Phytochem.11: 141–84.
Gross, G. G. 1977. Cell wall-bound malate dehydrogenase from horseradish. Phytochemistry26: 319–21.
Gross, G. G. and C. Janse. 1977. Formation of NADH and hydrogen peroxide by cell wall-associated enzymes from Forsythia xylem. Z. Pflanzenphysiol. (in press).
Gross, G. G., C. Janse and E. F. Elstner. 1977. In volvement of malate, monophenols and the superoxide radical in hydrogen peroxide formation by isolated cell walls from horseradish. Planta, (in press).
Gross, G. G. and W. Kreiten. 1975. Reduction of coenzyme A thioesters of cinnamic acids with an enzyme preparation from lignifying tissue of Forsythia. FEBS Lett.54: 259–62.
Gross, G. G., R. L Hansell and M. H. Zenk. 1975. Hydroxycinnamate: coenzyme A ligase from lig- nifying tissue of higher plants. Some properties and taxonomic distribution. Biochem. Physiol Pflanzen. 168: 41–51.
Gross, G. G., J. Stockigt, R. L. Hansell and H. H. Zenk. 1973. Three novel enzymes involved in the reduction of ferulic acid to coniferyl alcohol in higher plants: ferulate: CoA ligase, feruloyl-CoA reductase and coniferyl alcohol oxidoreductase. FEES Lett.31: 283–8
Gross, G. G. and H. H. Zenk. 1974. Isolation and properties of hydroxycinnamate: CoA ligase from lignifying tissue of Forsythia. Eur. J. Biochem.42: 453–59.
Hahlbrock, K. 1977. Regulatory aspects of phenylpropanoid biosynthesis in cell cultures. In: Plant Tissue Culture and its Bio-Technological Application (W. Barz, E. Reinhard, and H. H. Zenk, eds.) pp. 95–111. Springer, Berlin-Heidelberg-New York.
Hahlbrock, K. and E. Wellmann. 1973. Light-independent induction of enzymes related to phenylpropanoid metabolism in cell suspension cultures from parsley. Biochim. Biophys. Acta304: 702–6.
Harkin, J. H. 1969 Hethods of attacking the problem of lignin structure. Ree. Adv. Phytochem.2: 35–73.
Harkin, J. H. and J. R. Obst. 1973. Lignification in trees: indication of exclusive peroxidase participation. 180: 296–98.
45Harris, P. J. and R. D. Hartley. 1976. Detection of bound ferulic acid in cell walls of the Gramineae by ultraviolet fluorescence microscopy. Nature 259: 508–10.
Harris, E. E., J. D’lanni and H. Adkins. 1938. Reaction of hardwood lignin with hydrogen. J. Amer. Chem. Soc.60: 1467–70.
Hartley, R. D. and E. C. Jones. 1976. Diferulic acid as a component of cell walls of Lolium multiflorum. Phytochemistry25: 1157–60.
Higuchi, T. and S. A. Brown. 1963. Studies of lignin biosynthesis sis using isotopic carbon. VIII. The phenylpropanoid system in lignification. Can. J. Biochem. Physiol.41: 621–28.
Ibrahim, R. K. and H. Grisebach. 1976. Purification and properties of UDP-glucose: eoniferyl alcohol glucosyltransferase from suspension cultures of Paul’s scarlet rose. Arch. Biochem. Biophys. 176: 700–08.
Joseleau, J. P., G. E. Miksche and S. Yasuda. 1976. Structural variation of Arundo donax lignin in relation to growth. Holzforschung31: 19–20.
Kalyanaraman, V. S., S. A. Kumar and S. Mahadevan. 1975. Oxidaseperoxidase enzymes of Datura innoxia. Oxidation of reduced nicotinamide- adenine dinucleotide in the presence of formylphenylacetic acid ethyl ester. Biochem. J. 149: 577–87.
Klischies, M., J. Stockigt and M. H. Zenk. 1977. Synthesis of stereospecifically labelled eoniferyl alcohol and stereospecificity of cinnamyl alcohol dehydrogenase. Phytochemisty, (in press).
Knobloch, K. H. and K. Hahlbrock. 1975. Isoenzymes of p-coumarate: CoA ligase from cell suspension cultures of Glycine max. Eur. J. Biochem. 53:311–20.
Kuroda, H. and T. Higuchi. 1976. Characterization and biosynthesis of mistletoe lignin. Phytochemistry15: 1511–14.
Lai, Y. Z. and K. V. Sarkanen. 1971. Isolation and structural studies. In: Lignins (K. V. Sarkanen and C. H. Ludwig, eds.). pp. 299–344. Wiley- Interscience, New York.
Ludemann, H. D. and H. Nimz. 1973. Carbon-13 nuclearmagnetic resonance spectra of lignins. Biochem. Biophys. Res.Commun.52: 1162–69.
Ludemann, H. D. and H. Nimz. 1974. C-Kernresonaz-spektren von Ligninen, 1. Chemische Verschiebungen bei monomeren und dimeren Modellsubstanzen. Makromol. Chem.175: 2393–2407.
Ludemann, H. D. and H. Nimz. 1974. 2. Buchen- und Fichten-Bjorkman-Lignin. Makromol. Chem. 175: 2409–22.
Ludwig, C. H. 1971. Magnetic resonance spectra. In: Lignins (K. V. Sarkanen and H. C. Ludwig, eds.). pp. 299–344. Wiley-Interscience, New York.
Mader, M. 1976. Die Lokalisation der Peroxidase-Isoenzymgruppe G in der Zellwand von Tabak-216 G.G. GROSS Geweben. Planta131: 11–15.
Mader, M., A. Nessel and M. Bopp. 1977. Uber die physiologische Bedeutung der Peroxidase-Iso enzymgruppen des Tabaks anhand einiger biochemischer Eigenschaften. II. pH-Optima, Michaelis-Konstanten, Maximale Oxidationsraten. Z. Pflanzenphysiol.82: 247–60.
Mansell, R. L., G. R. Babbel and M. H. Zenk. 1976. Multiple forms and specificity of conferyl alcohol dehydrogenase from cambial regions of higer plants. Phytochemistry15: 1849–53.
Mansell, R. L., G. G. Gross, J. Stockigt, H. Franke and M. H. Zenk. 1974. Purification and properties of cinnamyl alcohol dehydrogenase from higher plants involved in lignin biosynthesis. Phytochemistry, (in press).
Mansell, R. L., J. Stockigt and M. H. Zenk. 1972. Reduction of ferulic acid to coniferyl alcohol in a cell free system from a higher plant. Z. Pflanzenphysiol 68: 286–88.
Marcinowski, S. and H. Grisebach. 1977. Turnover of coniferin in pine seedlings. Phytochemistry, (in press).
Markwalder, H. K. and H. Neukom. 1976. Diferulic acid as a possible crosslink in hemicelluloses from wheat endosperm. Phytochemistyr175: 836–37.
McClure, J. W. and G. G. Gross. 1975. Diverse photoinduction characteristics of hydroxycinna- coenzyme A ligase and phenylalanine ammonia lyase in dicotyledonous seedlings. Z. Pflanzanphysiol.76: 51–55.
Miksche, G. E. and S. Yasuda. 1976. Zur Struktur des Lignins der Buche (Fagus silvatica L.). Liebig’s Ann. Chem.28 : 1323–32.
Miksche, G. E. and S. Yasuda. 1977. On the occurence of lignin in “giant” mosses and some related species. Phytochemistry, (in press).
Nakamura, Y., H. Fushiki and T. Higuchi. 1974. Metabolic differences between gynosperms and angiosperms in the formation of syringyl lignin. Phytochemistry13: 1777–84.
Nakamura, Y. and T. Higuchi. 1976. Ester linkage of 2-coumaric acid in bamboo lignin. Holzforschung30: 187–91.
Nessel, A. and M. Mader. 1977. über die physiologische Bedeutung der Peroxidase-Isoenzymgruppendes Tabaks anhand einiger biochemischer Eigenschaften. I. Trennung, Reinigung, chemische und physikalische Daten. Z. Pflanzenphysiol.82:235–46.
Nimz, H. 1974. Beech lignin-Proposal of a constitutional scheme. Angew. Chem. Internat. Edit.13: 313–20.
Nimz, H., I. Mogharab and H. D. Ludemann. 1974.13C-Kernresonanzspektren von Ligninen, 3. Vergleich von Fichten-lignin mit kunstlichem Lignin nach Freudenberg. Makromol. Chem. 175: 2536–75.
Nimz, H., H. D. Ludemann and H. Becker. 1974. Kohlenstoff-13–13-Kernresonanzspektren von Ligninen, 4. Die Lignine der europaischen Mistel (Viscum album L.). Z Pflanzenphysiol.73: 226–33.
Nimz, H. H. and H. D. Ludemann. 1976. Kohlenstoff- 13-NMR-Spektren von Ligninen, 6. Lignin- und DHP-Acetate. Holzforschung30: 33–40.
Parameswaran, N., O. Faix and W. Schweers. 1975. Zur Charakterisierung des Sklereiden-und Holzlignins von Entando-phragma candollei. Holzforschung19: 1–4.
Payen, A. 1838. Memoire sur la composition dutissu propre des plantes et du ligneux. Compt. Rend.7: 1052–56.
Ranjeva, R., G. Alibert and A. M. Boudet. 1977. Metabolisme des composes phenoliques chez le Petunia. V. Utilization de la phenylalanine par des chloroplastes isoles. Plant Sei. Lett, (in press).
Ranjeva, R., A. M. Boudet and G. Alibert. 1977. Autoregulation cellulaire du metabolisme des phenylpropanoides. Physiol. Veg. 15: in press.
Ranjeva, R., A. M. Boudet and R. Faggion. 1976. Phenolic metabolism in Petunia tissue. IV. Properties of p-coumarate: coenzyme A ligase isoenzymes. Biochimie58:1255–62.
Rhodes, M. J. C., A. C. R. Hill and L. S. C. Wooltorton. 1976. Activity of enzymes involved in lignin biosynthesis in swede root disks. Phytochemistry15:707–10.
Rhodes, M. J. C. and L. S. C. Wooltorton. 1973. Formation of CoA esters of cinnamic acid derivatives by extracts of Brassica napo-brassica root tissue. Phytochemistry12: 2381–87.
Rhodes, M. J. C. and L. S. C. Wooltorton. 1975. The 2-coumaryl CoA ligase of potato tubers. Phytochemistry14: 2161–64.
Rhodes, M. J. C. and L. S. C. Wooltorton. 1976. The enzymic conversion of hydroxycinnamic acids to p-coumaroylquinic and chlorogenic acids in tomato fruits. Phytochemistry15: 947–51.
Rubery, P. H. and D. E. Fosket. 1969. Changes in phenylalanine ammonia-lyase activity during xylem differentiation in Coleus and soybean. Planta87: 54–62.
Rubery, P. H. and D. H.N. Northcote. 1968. Site of phenylalanine lanine ammonialyase activity and synthesis of lignin during xylem differentiation. Nature219: 1230–34.
Sarkanen, K. V. and H. L. Hergert. 1971. Classification and distribution. In: Lignins (K. V. Sarkanen and C. H. Ludwig, eds.). pp. 43–94. Wiley Interscience, New York.
Schweers, W. and O. Faix. 1973. Vergleichende Untersuchungen an Polymermodellen des Lignins (DHP’s) verschiedener Zusammensetzungen. 1. Mitt. Herstellung von Lignin-Polymer-modellen verschiedener Zusammensetzung aus den Monolignolen p-Coumaral- kohol, Coniferylalkohol und Sinapinalkohol. Holzforschung 27: 208–13.
Seitz, U. and U. Heinzmann. 1977. GA directed regution processes in carrot tissues. Abstracts of the International Conference on Regulation of Developmental Processes in Plants, Halle (Saale), p. 101.
Shimada, M., T. Fukuzuka and T. Higuchi. 1971. Esterlinkages of p-coumaric acid in bamboo and grass lignins. Tappi 54: 72–78.
Shimada, M., H. Fushiki and T. Higuchi. 1972.O-methyltransferase activity from Japanese black pine Phytochemistry175: 2657–62.
Shimada, M., H. Fushiki and T. Higuchi. 1973. Mechanism of biochemical formation of the methoxyl groups in softwood and hardwood lignins. Mokuzai Gakkaishi19: 13–21.
Siegel, S. M. 1969. Evidence for the presence of lignin in moss gametophytes. Amer. J. Bot.56: 175–79.
Srivastava, L. M. 1966. Histochemical studies on lignin Tappi49:173–83.
Stafford, H. A. 1974. The metabolism of aromatic compounds. Ann. Rev. Plant Physiol.25: 459–86.
Stafford, H. A. 1974. Possible mutienzyme complexes regulating the formation of C6-C6phenolic compounds and lignins in higher plants. Ree. Adv. Phytochem.8: 53–79.
Stafford, H. A. and M. A. Brown. 1976. Oxidative dimerization of ferulic acid by extracts from Sorghum. Phytochemistry15: 465–69.
Stewart, C. M. 1957. Status of cambial chemistry. Tappi.40: 244–56.
Tanaka, K., F. Nakatsubo and T. Higuchi. 1976. Reac tions of guaiacylglycerolguaiacyl ether with several sugars. I. Reaction of quinonemethide with D-glucuronic acid. Mokuzai Gakkaishi22: 589–90.
Tütschek, R. 1975. Isolierung und Charakterisierung der 2-Hydroxy- -(carboxymethyl)-zimtsaure (Sphagnumsaure) aus der Zellwand von Sphagnum magellanicum Brid. Z. Pflanzenphysiol.76: 353–65.
Tutschek, R., B. Engmann and H. H. Nimz. 1977. Kohlenstoff- 13-NMR-Spektren von Ligninen. 7. Zur Frage des Ligningehalts von Moosen (Sphagnum magellanicum Brid.). Holzforschung, (in press).
Vieitez, A. M., A. Ballester and E. Vieitez. 1975. Coniferyl alcohol from callus of Castanea sativa cultured vitro. Experientia31: 1163.
Wardrop, A. B. 1957. The phase of lignification in the differentiation of wood fibers. Tappi40: 225–43.
Wardrop A. B. 1971. Occurrence and formation in plants. In: Lignins (K. V. Sarkanen and C. H. Ludwig, eds.). pp. 19–41. Wiley-Interscience, New York.
Wengenmayer, H., J. Ebel and H. Grisebach. 1976. Enzymic synthesis of lignin precursors. Purification and properties of a cinnamoyl-CoA: NADPH reductase from cell suspension cultures of soybean (Glycine max). Eur. J. Biochem.65: 529–36.
Whitmore, F. W. 1976. Binding of ferulic acid to cell walls by peroxidases of Pinus elliottii. Phytochemistry15: 375–78.
Wyrambik, D. and H. Grisebach. 1975. Purification and properties of isoenzymes of cinnamyl-alcohol dehydrogenase from soybean-cell-suspension cultures. Eur. J. Biochem.59:9–15.
Yamada, Y. and T. Kuboi. 1976. Significance of caffeic acid 0-methyltransferase in lignification of cultured tobacco cells. Phytochemistry15: 395–96.
Yamasaki, T., K. Hata and T. Higuchi. 1976. Dehydrogenation polymer of sinapyl alcohol by peroxidase and hydrogen peroxide. Mokuzai Gakkaishi22: 582–88
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Gross, G.G. (1979). Recent Advances in the Chemistry and Biochemistry of Lignin. In: Swain, T., Harbone, J.B., Van Sumere, C.F. (eds) Biochemistry of Plant Phenolics. Recent Advances in Phytochemistry, vol 12. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-3372-2_6
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