Skip to main content
SpringerLink
Log in
Book cover

The Structure, Biosynthesis, and Degradation of Wood pp 141–184Cite as

Biosynthesis of Lignin and Related Monomers

  • Chapter

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 11))

Abstract

After Payen’s fundamental discovery in 1838,103 that wood does not represent a uniform substance but rather consists, in addition to cellulose, of a “true lignous material,” more than a century of intensive research was required to establish the aromatic nature of this natural product and to elaborate the principles of its constitution. As a result of these investigations we know now that lignin is a complex polymer originating from the random oxidative polymerization of hydroxylated cinnamyl alcohols (Fig. 1) as principal constituents, as discussed in the previous chapter. About 20 years ago, when it became increasingly evident that lignin in fact is derived from substituted cinnamyl alcohols, interest was focussed in a variety of laboratories on the reactions leading to lignin and its precursors. The results obtained by a multitude of tracer experiments revealed the principal pathways from CO2 to lignin, 8, 36, 65 thus providing an ample basis for our understanding of the lignification process. However, there remained many questions which could not be answered satisfactorily by these techniques.

This is a preview of subscription content, log in via an institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Akazawa, T., E. E. Conn., 1958. The oxidation of reduced pyridine nucleotides by peroxidase. J. Biol. Chem. 232: 403–415.

    PubMed  CAS  Google Scholar 

  2. Alibert, G., R. Ranjeva., 1971. Recherches sur les enzymes catalysant la biosynthese des acides phenoliques chez Querous pedunoulata (Ehrh.): I. Formation des premiers termes des series cinnamique et benzoique. FEBS Lett. 19: 11–14.

    Article  PubMed  CAS  Google Scholar 

  3. Bartlett, D. J., J. E. Poulton, V. S. Butt., 1972. Hydroxylation of p-coumaric acid by illuminated chloroplasts from spinach beet leaves. FEBS Lett. 23: 265–267.

    Article  CAS  Google Scholar 

  4. Bergmann, L., 1964. Der einfluss von kinetin auf die ligninbildung und differenzierung in gewebekulturen von Niootiana tabaoum. Planta 62: 221–254.

    Article  CAS  Google Scholar 

  5. Bland, D. E., A Logan, M. Menshun, S. Sternhell., 1968. The lignin of Sphagnum. Phytoohemistry 7: 1373–1377.

    Article  CAS  Google Scholar 

  6. Boudet, A., R. Ranjeva, P. Gadal., 1971. Propriétés allostériques spécifiques des deux isoenzymes de la phénylalanine-ammoniaque lyase chez Querous pedunoulata. Phytoohemistry 10: 997–1005.

    Article  CAS  Google Scholar 

  7. Bowling, A. C., R. K. Crowden. 1973. Peroxidase activity and lignification in the pod membrane of Pisum sativum L. Aust. J. Biol. Sci. 26: 679–684.

    CAS  Google Scholar 

  8. Brown, S. A., 1966. Lignins. Ann. Rev. Plant Physiol. 17: 223–244.

    Article  CAS  Google Scholar 

  9. Brown, S. A., D. Wright, A. C. Neish., 1959. Studies of lignin biosynthesis using isotopic carbon. VII. The role of p-hydroxyphenylpyruvic acid. Can. J. Biochem. Physiol. 37: 25–34.

    Article  PubMed  CAS  Google Scholar 

  10. Büche, T., H. Sandermann., 1973. Lipid dependence of plant microsomal cinnamic acid 4-hydroxylase. Arch. Biochem. Biophys. 155: 445–447.

    Article  Google Scholar 

  11. Burton, R. M., E. R. Stadtman., 1953. The oxidation of acetaldehyde to acetyl coenzyme A. J. Biol. Chem. 202: 873–890.

    PubMed  CAS  Google Scholar 

  12. Camm, E. L., G. H. N. Towers., 1973. Phenylalanine ammonia lyase. Phytochemistry 12: 961–973.

    Article  CAS  Google Scholar 

  13. Charriere-Ladreix, Y., 1975. Sur la presence de deux 171 isoenzymes de la phenylalanine-ammoniac-lyase chez Aesoulus hippooastanum. Phytochemistry 14: 1727–1731.

    Article  CAS  Google Scholar 

  14. Cheng, C. K. C., H. V. Marsh., 1968. Gibberellic acid-promoted lignification and phenylalanine ammonialyase activity in a dwarf pea (Pisum sativum). Plant Physiol. 43: 1755–1759.

    Article  PubMed  CAS  Google Scholar 

  15. Creasy, L. L., M. Zucker., 1974. Phenylalanine ammonia-lyase and phenolic metabolism. Recent Adv. Phytochem. 8: 1–19.

    CAS  Google Scholar 

  16. Curtis, C. R., N. M. Barnett., 1974. Isoelectric focusing of peroxidases released from soybean hypocotyl cell walls by Sclerotium volfsii culture filtrate. Can. J. Bot. 52: 2037–2040.

    Article  Google Scholar 

  17. Czichi, U., H. Kindl., 1975. A model of closely assembled consecutive enzymes on membranes: Formation of hydroxycinnamic acids from L-phenylalanine on tylakoids of Dunaliella marina. Z. Physiol. Chem. 356: 475–485.

    Article  CAS  Google Scholar 

  18. Czichi, U., H. Kindl. 1975. Formation of p-coumaric acid and o-coumaric acid from L-phenylalanine by microsomal membrane fractions from potato: Evidence of membrane-bound enzyme complexes. Planta 125: 115–125.

    CAS  Google Scholar 

  19. Davies, D. D., A. Texeira, P. Kenworthy. 1972. The stereospecificity of nicotinamide-adenine dinucleotide-dependent oxidoreductases from plants. Biochem. J. 127: 335–343.

    PubMed  CAS  Google Scholar 

  20. Davies, D. D., E. N. Ugochukwu, K. D. Patil, G. H. N. Towers., 1973. Aromatic alcohol dehydrogenase from potato tubers. Phytochemistry 12: 531–536.

    Article  CAS  Google Scholar 

  21. DeJong, D. W., 1967. An investigation of the role of plant peroxidase in cell wall development by the histochemical method. J. Histochem. Cytochem. 15: 335–346.

    Article  PubMed  Google Scholar 

  22. Ebel, J., H. Grisebach., 1973. Reduction of cinnamic acids to cinnamyl alcohols with an enzyme preparation from cell suspension cultures of soybean (Glycine max). FEBS Lett. 30: 141–143.

    Article  PubMed  CAS  Google Scholar 

  23. Ebel, J., B. Schaller-Hekeler, K. H. Knobloch, E. Wellmann, H. Grisebach, K. Hahlbrock., 1974. Coordinated changes in enzyme activities of phenyl-propanoid metabolism during the growth of soybean cell suspension cultures. Biochim. Biophys. Acta 362: 417–424.

    Article  PubMed  CAS  Google Scholar 

  24. El-Basyouni, S. Z., A. C. Neish, G. H. N. Towers., 1964. The phenolic acids in wheat. III. Insoluble derivatives of phenolic cinnamic acids as natural intermediates in lignin biosynthesis. Phytochemistry 3: 627–639.

    Article  CAS  Google Scholar 

  25. El-Basyouni, S. Z., A. C. Neish., 1966. Occurrence of metabolically-active boujid forms of cinnamic acid and its phenolic derivatives in acetone powders of wheat and barley plants. Phytochemistry 5: 685–691.

    Article  Google Scholar 

  26. Ellis, B. E., M. H. Zenk, G. W. Kirby, J. Michael, H. G. Floss., 1973. Steric course of the tyrosine ammonia-lyase reaction. Phytochemistry 12: 1057–1058.

    Article  CAS  Google Scholar 

  27. Elstner, E. F., A. Heupel., 1976. Formation of hydrogen peroxide by isolated cell walls from horse-radish (Armoracia lapathifolia Gilib.). Planta 130: 175–180.

    Article  CAS  Google Scholar 

  28. Erdtman, H., 1933. Dehydrierungen in der coniferylreihe. I. Dehydrodi-eugenol und dehydrodiisoeugenol. Biochem. Z. 258: 172–180.

    CAS  Google Scholar 

  29. Erdtman, H., 1933. Dehydrierungen in der coniferylreihe. II. Dehydrodiisoeugenol. Liebigs Ann. Chem. 503: 283–294.

    CAS  Google Scholar 

  30. Erickson, M., G. E. Miksche., 1974. Charakterisierung der lignine von pteridophyten durch oxidativen abbau. Holzforschung 28: 157–159.

    Article  CAS  Google Scholar 

  31. Erickson, M., G. E. Miksche., 1974. Two dibenzofurans obtained on oxidative degradation of the moss Polytrichum commune Hedw. Acta Chem. Scand. B 28: 109–113.

    Article  CAS  Google Scholar 

  32. Erickson, M., G. E. Miksche., 1974. On the occurrence of lignin or polyphenols in some mosses and liverworts. Phytochemistry 13: 2295–2299.

    Article  CAS  Google Scholar 

  33. French, C. J., H. Smith., 1975. An inactivator of phenylalanine ammonia-lyase from gherkin hypocotyls. Phytochemistry 14: 963–966.

    Article  CAS  Google Scholar 

  34. Freudenberg, K., 1965. Lignin: Its constitution and formation from p-hydroxycinnamyl alcohols. Science 148: 595–600.

    Article  PubMed  CAS  Google Scholar 

  35. Freudenberg, K., C. L. Chen, J. M. Harkin, H. Nimz, H. Renner., 1965. Observations on lignin. Chem. Commun. 1: 224–225.

    Google Scholar 

  36. Freudenberg, K., A. C. Neish., 1968. Constitution and Biosynthesis of Lignin. Springer, Berlin.

    Google Scholar 

  37. Fritz, G. J., R. W. King, R. C. Dougherty., 1974. Incorporation of molecular oxygen into caffeic acid by green Helianthus annuus. Phytochemistry 13: 1473–1475.

    Article  CAS  Google Scholar 

  38. Gardiner, M. G., R. Cleland., 1974. Peroxidase isoenzymes of the Avena coleoptile. Phytochemistry 13: 1707–1711.

    Article  CAS  Google Scholar 

  39. Gestetner, B., E. E. Conn., 1974. The 2-hydroxylation of transcinnamic acid by chloroplasts from Melilotus alba Desr. Arch. Biochem. Biophys. 163: 617–624.

    Article  PubMed  CAS  Google Scholar 

  40. Goff, C. W., 1975. A light and electron microscopic study of peroxidase localization in the onion root tip. Amer. J. Bot. 62: 280–291.

    Article  Google Scholar 

  41. Grisebach, H., 1962. Die biosynthese der flavonoide. Planta Medioa 10: 385–397.

    Article  CAS  Google Scholar 

  42. Grisebach, H., 1973. Comparative biosynthetic pathways in higher plants. Pure Appl. Chem. 34: 487–513.

    Article  CAS  Google Scholar 

  43. Grisebach, H., K. Hahlbrock., 1974. Enzymology and regulation of flavonoid and lignin biosynthesis in plants and plant cell suspension cultures. Recent Adv. Phytoohem. 8: 21–52.

    CAS  Google Scholar 

  44. Gross, G. G., 1972. Formation and reduction of intermediate acyladenylate by arylaldehyde: NADP oxidoreductase from Neurospora crassa. Eur. J. Biochem. 33: 585–592.

    Article  Google Scholar 

  45. Gross, G. G., 1976. Cell wall-bound malate dehydrogenase from horseradish. Phytochemistry, submitted for publication.

    Google Scholar 

  46. Gross, G. G., W. Kreiten., 1975. Reduction of coenzyme A thioesters of cinnamic acids with an enzyme preparation from lignifying tissue of Forsythia. FEBS Lett. 54: 259–262.

    Article  PubMed  CAS  Google Scholar 

  47. Gross, G. G., R. L. Mansell, M. H. Zenk., 1975. Hydroxycinnamate:coenzyme A ligase from lignifying tissue of higher plants. Some properties and taxonomic distribution. Biochem. Physiol. Pflanzen 168: 41–51.

    CAS  Google Scholar 

  48. Gross, G. G., J. Stöckigt, R. L. Mansell, M. 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. FEBS Lett. 31: 283–286.

    Article  CAS  Google Scholar 

  49. Gross, G. G., M. H. Zenk., 1966. Darstellung und eigenschaften von coenzyme A-thiolestern substituierter zimtsäuren. Z. Naturforsch. 21b: 683–690.

    Google Scholar 

  50. Gross, G. G., M. H. Zenk., 1969. Reduktion aromatischer säuren zu aldehyden und alkoholen im zellfreien system. I. Reinigung und eigenschaften von aryl-aldehyd:NADP-oxidoreductase aus Neurospora crassa. Eur. J. Biochem. 8: 413–419.

    Article  PubMed  CAS  Google Scholar 

  51. Gross, G. G., and M. H. Zenk., 1974. Isolation and properties of hydroxycinnamate:CoA ligase from lignifying tissue of Forsythia. Eur. J. Biochem. 42: 453–459.

    Article  PubMed  CAS  Google Scholar 

  52. Hagel, P., H. Kindl., 1975. p-Hydroxybenzoate syn thase: A complex associated with mitochondrial membranes of roots of Cuoumis sativus. FEBS Lett. 59: 123–124.

    Google Scholar 

  53. Hahlbrock, K., J. Ebel, R. Ortmann, A. Sutter, E. Wellmann, H. Grisebach., 1971. Regulation of enzyme activities related to the biosynthesis of flavone glycosides in cell suspension cultures of parsley (Petroselinum hortense). Biochim. Biophys. Acta 244: 7–15.

    Article  PubMed  CAS  Google Scholar 

  54. Hahlbrock, K., H. Grisebach., 1970. Formation of coenzyme A esters of cinnamic acids with an enzyme preparation from cell suspension cultures of parsley. FEBS Lett. 11: 62–64.

    Article  PubMed  CAS  Google Scholar 

  55. Hahlbrock, K., K. H. Knobloch, F. Kreuzaler, J. R. M. Potts, E. Wellmann., 1976. Coordinated induction and subsequent activity changes of two groups of metabolically interrelated enzymes. Light-induced synthesis of flavonoid glycosides in cell suspension cultures of Petroselinum hortense. Eur. J. Biochem. 61: 199–206.

    Article  PubMed  CAS  Google Scholar 

  56. Hahlbrock, K., E. Kuhlen, T. Lindl., 1971. Änderungen von enzymaktivitäten während des Wachstums von zell-suspensionskulturen von Glycine max: Phenylalanin ammonium-lyase und p-cumarat: CoA ligase. Planta 99: 311–318.

    Article  CAS  Google Scholar 

  57. Hahlbrock, K., J. Schröder., 1975. Specific effects on enzyme activities upon dilution of Petroselinum hortense cell cultures into water. Arch. Biochem. Biophys. 171: 500–506.

    Article  PubMed  CAS  Google Scholar 

  58. Halliwell, B., 1975. Hydroxylation of p-coumaric acid by illuminated chloroplasts. The role of superoxide. Eur. J. Biochem. 55: 355–360.

    Article  PubMed  CAS  Google Scholar 

  59. Halliwell, B., S. Ahluwalia., 1976. Hydroxylation of p-coumaric acid by horseradish peroxidase. The role of superoxide and hydroxyl radicals. Biochem. J. 153: 513–518.

    PubMed  CAS  Google Scholar 

  60. Hanson, K.R., R. H. Wightman, J. Staunton, A. R. Battersby., 1971. Stereochemical course of the deamination catalyzed by L-phenylalanine ammonia-lyase and the configuration of 2-benzamidocinnamic azlactone. Chem. Commun. 185–186.

    Google Scholar 

  61. Harkin, J. M., J. R. Obst., 1973. Lignification in trees: Indication of exclusive peroxidase participation. Science 180: 296–298.

    Article  PubMed  CAS  Google Scholar 

  62. Hasegawa, S., V. P. Maier., 1972. Cinnamate hydroxylation and the enzymes leading from phenylpyruvate to p-coumarate synthesis in grapefruit tissues. Phytochemistry 11: 1365–1370.

    Google Scholar 

  63. Havir, E. A., K. R. Hanson., 1975. L-Phenylalanine ammonia-lyase (maize, potato and Rhodotorula glutinis). Studies of the prosthetic group with nitromethane. Biochemistry 14: 1620–1626.

    Article  PubMed  CAS  Google Scholar 

  64. Heber, U., 1974. Metabolite exchange between chloroplasts and cytoplasm. Ann. Rev. Plant Physiol. 25: 393–421.

    Article  CAS  Google Scholar 

  65. Higuchi, T., 1971. Formation and biological degradation of lignins. Adv. Enzymol. 34: 207–283.

    PubMed  CAS  Google Scholar 

  66. Higuchi, T., 1976. Biochemical aspects of lignification and heartwood formation. Wood Research 59 /60: 180–199.

    Google Scholar 

  67. Higuchi, T., S. A. Brown., 1963. Studies of lignin biosynthesis using isotopic carbon. VIII. The phenyl-propanoid system in lignification. Can. J. Biochem. Physiol. 41: 621–628.

    Article  PubMed  CAS  Google Scholar 

  68. Hill, A. C., M. J. C. Rhodes., 1975. The properties of cinnamic acid 4-hydroxylase of aged swede root disks. Phytochemistry 14: 2387–2391.

    Article  CAS  Google Scholar 

  69. Ife, R., E. Haslam., 1971. The shikimate pathway. Part III. The stereochemical course of the L-phenylalanine ammonia lyase reaction. J. Chem. Soc. 67: 2818–2821.

    Google Scholar 

  70. Johnson, M. J., 1960. Enzyme equilibria and thermodynamics. In The Enzymes ( P. P. Boyer, H. Lardy, K. Myrback, eds.) Vol. 3, pp. 407–441. Academic Press, New York.

    Google Scholar 

  71. Johnson, R. C., J. R. Gilbertson., 1972. Isolation, characterization, and partial purification of a fatty acyl coenzyme A reductase from bovine cardiac muscle. J. Biol. Chem. 247: 6991–6998.

    PubMed  CAS  Google Scholar 

  72. Kalyanaraman, V. S., S. A. Kumar, S. Mahadevan., 1975. Oxidase-peroxidase enzymes of Datura innoxia. Oxidation of reduced nicotinamide-adenine dinucleotide in the presence of formylphenylacetic acid ethyl ester. Biochem. J. 149: 577–584.

    PubMed  CAS  Google Scholar 

  73. Kindl, H., 1971. Aromatische aminosauren im stoffwechsel hoherer pflanzen. Naturwissenschaften 55: 554–563.

    Article  Google Scholar 

  74. Kindl, H., H. Ruis., 1971. Subcellular distribution of p-hydroxybenzoic acid formation in castor bean endosperm. Z. Naturforsch. 26b: 1379–1380.

    Google Scholar 

  75. Knobloch, K. H., K. Hahlbrock., 1975. Isoenzymes of p-coumarate:CoA ligase from cell suspension cultures of Glycine max. Eur. J. Biochem. 52: 311–320.

    Article  PubMed  CAS  Google Scholar 

  76. Knobloch, K. H., K. Hahlbrock., 1975. Isoenzyme der p-cumarat: CoA ligase aus zellsuspensionskulturen von Glycine max. Planta Medica, Suppl., pp. 102–106.

    Google Scholar 

  77. Kolattukudy, P. E., 1970. Reduction of fatty acids to alcohols by cell-free preparations of Euglena gracilis. Biochemistry 9: 1095–1102.

    Article  PubMed  CAS  Google Scholar 

  78. Kolattukudy, P. E., 1971. Enzymatic synthesis of fatty alcohols in Brassica oleracea. Arch. Biochem. Biophys. 142: 701–709.

    Article  PubMed  CAS  Google Scholar 

  79. Koukol, J., E. E. Conn., 1961. Purification and properties of the phenylalanine deaminase of Eordeum vulgare. J. Biol. Chem. 236: 2692–2698.

    Google Scholar 

  80. Kreuzaler, F., K. Hahlbrock., 1972. Enzymatic synthesis of aromatic compounds in higher plants: Formation of naringenin (5,7,4’-trihydroxyflavanone) from p-coumaryl coenzyme A and malonyl coenzyme A. FEBS Lett. 28: 69–72.

    Article  PubMed  CAS  Google Scholar 

  81. Kreuzaler, F., K. Hahlbrock., 1975. Enzymatic synthesis of an aromatic ring from acetate units. Partial purification and some properties of flavanone synthase from cell-syspension cultures of Petroselinum hortense. Eur. J. Biochem. 56: 205–213.

    Article  PubMed  CAS  Google Scholar 

  82. Kreuzaler, F., K. Hahlbrock., 1975. Enzymatic synthesis of aromatic compounds in higher plants. Formation of bis-noryangonin (4-hydroxy-6[4-hydroxystyryl]- 2-pyrone) from p-coumaroyl-CoA and malonyl-CoA. Arch. Biochem. Biophys. 169: 84–90.

    Google Scholar 

  83. Kuroda, H., M. Shimada, T. Higuchi., 1975. Purification and properties of O-methyltransferase involved in the biosynthesis of gymnosperm lignin. Phytochemistry 14: 1759–1763.

    Article  CAS  Google Scholar 

  84. Lindl, T., F. Kreuzaler, K. Hahlbrock., 1973. Synthesis of p-coumaroyl coenzyme A with a partially purified p-coumarate: CoA ligase from cell suspension cultures of soybean (Glycine max). Biochim. Biophys. Acta 302: 457–464.

    PubMed  CAS  Google Scholar 

  85. Liu, E. H., D. T. A. Lamport., 1974. An accounting of horseradish peroxidase isoenzymes associated with the cell wall and evidence that peroxidase does not contain hydroxyproline. Plant Physiol. 54: 870–876.

    Article  PubMed  CAS  Google Scholar 

  86. Loffelhardt, W., H. Kindl., 1975. The conversion of L-phenylalanine into benzoic acid on the thylakoid membrane of higher plants. H-S. Z. Physiol. Chem. 356: 487–493.

    Article  CAS  Google Scholar 

  87. Mader, M., Y. Meyer, M. Bopp., 1975. Lokalisation der peroxidase-isoenzyme in protoplasten und zellwSnden von Nicotiana tabacum L. Planta 122: 259–268.

    Article  Google Scholar 

  88. Mansell, R. L., G. R. Babbel, M. H. Zenk., 1976. Multiple forms and specificity of coniferyl alcohol dehydrogenase from cambial regions of higher plants. Phytochemistry, in press.

    Google Scholar 

  89. Mansell, R. L., G. G. Gross, J. Stöckigt, H. Franke, M. H. Zenk., 1974. Purification and properties of cinnamyl alcohol dehydrogenase from higher plants involved in lignin biosynthesis. Phytochemistry 13: 2427–2435.

    Article  CAS  Google Scholar 

  90. Mansell, R. L., J. Stöckigt, M. H. Zenk., 1972. Reduction of ferulic acid to coniferyl alcohol in a cell free system from a higher plant. Z. Pflanzenphysiol. 68: 286–288.

    CAS  Google Scholar 

  91. McClure, J. W., G. G. Gross., 1975. Diverse photoinduction characteristics of hydroxycinnamate:co-enzyme A ligase and phenylalanine ammonia-lyase in dicotyledonous seedlings. Z. Pflanzenphysiol. 76: 51–55.

    CAS  Google Scholar 

  92. Mclntyre, R. J., P. F. T. Vaughan., 1975. Kinetic studies on the hydroxylation of p-coumaric acid to caffeic acid by spinach-beet phenolase. Biochem. J. 149: 447–461.

    Google Scholar 

  93. Meijer, A. J., K. van Dam., 1974. The metabolic significance of anion transport in mitochondria. Biochim. Biophys. Acta 346: 213–244.

    PubMed  CAS  Google Scholar 

  94. Nakamura, Y., H. Fushiki, T. Higuchi., 1974. Metabolic differences between gymnosperms and angiosperms in the formation of syringyl lignin. Phytochemistry 13: 1777–1784.

    Article  CAS  Google Scholar 

  95. Nambudiri, A. M. D., C. P. Vance, G. H. N. Towers., 1973. Effect of light on enzymes of phenylpropanoid metabolism and hispidin biosynthesis in Polyporus hispidus. Biochem. J. 134: 891–897.

    PubMed  CAS  Google Scholar 

  96. Nari, J., C. Mouttet, F. Fouchier, J. Ricard. 1974. Subunit interactions in enzyme catalysis. Kinetic analysis of subunit interactions in the enzyme L-phenylalanine ammonia-lyase. Eur. J. Biochem. 41: 499–515.

    Article  PubMed  CAS  Google Scholar 

  97. Neish, A. C., 1961. Formation of m- and p-coumaric acids by enzymatic desamination of the corresponding isomers of tyrosine. Phytochemistry 1: 1–24.

    Article  CAS  Google Scholar 

  98. Neish, A. C., 1964. Major pathways of biosynthesis of phenols. In Biochemistry of Phenolic Compounds ( J. B. Harborne, ed.), pp. 295–359. Academic Press, London.

    Google Scholar 

  99. Neish, A. C., 1964. Cinnamic acid derivatives as intermediates in the biosynthesis of lignin and related compounds. In The Formation of Wood in Forest Trees ( M. H. Zimmermann, ed.), pp. 219–239. Academic Press, New York.

    Google Scholar 

  100. Nimz, H., 1974. Beech lignin-proposal of a constitutional scheme. Angew. Chem. Internat. Edit. 13: 313–320.

    Article  Google Scholar 

  101. Nozu, Y., 1967. Studies on the biosynthesis of lignin. III. Dehydrogenative polymerization of coniferyl alcohol by peroxidase. J. Biochem. 62: 519–530.

    PubMed  CAS  Google Scholar 

  102. Parish, R. W., 1972. The intracellular location of phenol oxidases in the leaves of spinach beet (Beta vulgaris L. subspecies vulgaris). Eur. J. Biochem. 31: 446–455.

    Article  PubMed  CAS  Google Scholar 

  103. Payen, A., 1838. Mémoire sur la composition du tissue propre des plantes et du ligneux. Compt. Rend. 7: 1052–1056.

    Google Scholar 

  104. Potts, J. R. M., R. Weklych, E. E. Conn., 1974. The 4-hydroxylation of cinnamic acid by sorghum microsomes and the requirement for cytochrome P-450. J. Biol. Chem. 249: 5019–5026.

    PubMed  CAS  Google Scholar 

  105. Poulton, J. E., V. S. Butt., 1975. Purification and properties of β-adenosyl-L-methionine:caffeic acid O-methyltransferase from leaves of spinach beet (Beta vulgaris L.). Biochim. Biophys. Acta 403: 301–314.

    PubMed  CAS  Google Scholar 

  106. Poulton, J. E., V. S. Butt., 1976. Purification and properties of β-adenosyl-L-homocysteine hydrolase from leaves of spinach beet. Arch. Biochem. Biophys. 172: 135–142.

    Article  PubMed  CAS  Google Scholar 

  107. Poulton, J. E., H. Grisebach, J. Ebel, B. Schaller-Hekeler, K. Hahlbrock., 1976. Two distinct S-adenosyl-L-methionine: 3,4-dihydric phenol 3-O-methyltransferases of phenylpropanoid metabolism in soybean cell suspension cultures. Arch. Biochem. Biophys. 173: 301–305.

    Article  PubMed  CAS  Google Scholar 

  108. Quayle, J. R., 1966. Glyoxalate dehydrogenase. Methods Enzymol. 9: 342–346.

    Article  CAS  Google Scholar 

  109. Ranjeva, R., A. M. Boudet, H. Harada, G. Marigo., 1975. Phenolic metabolism in Fetunia tissues. I. Characteristic responses of enzymes involved in different steps of polyphenol synthesis to different hormonal influences. Biochim. Biophys. Acta 399: 23–30.

    Article  PubMed  CAS  Google Scholar 

  110. Ranjeva, R., R. Faggion, A. M. Boudet., 1975. Metabolisme des composés phénoliques des tissus de Pétunia. II. Étude de système enzymatique deactivation des acides cinnamiques. Mise en évidence de deux formes de la “cinnamoyl-coenzyme A ligase.” Physiol. Veg. 13: 725–734.

    Google Scholar 

  111. Rétey, J., E. von Stetten, U. Coy, F. Lynen., 1970. A probable intermediate in the enzymatic reduction of β-hydroxy- β -methylglutaryl coenzyme A. Eur. J. Biochem. 15: 72–76.

    Article  PubMed  Google Scholar 

  112. Rhodes, M. J. C., A. C. R. Hill, L. S. C. Wooltorton., 1976. Activity of enzymes involved in lignin biosynthesis in swede root disks. Phytochemistry 15: 707–710.

    Article  CAS  Google Scholar 

  113. Rhodes, M. J. C., L. S. C. Wooltorton., 1973. Stimulation of phenolic acid and lignin biosynthesis in swede root tissue by ethylene. Phytochemistry 12: 101–118.

    Google Scholar 

  114. Rhodes, M. J. C., L. S. C. Wooltorton., 1973. Changes in phenolic acid and lignin biosynthesis in response to treatment of root tissue of the Swedish turnip (Brassioa napobrassioa) with ethylene. Qualitas Plant. 23: 145–155.

    Article  CAS  Google Scholar 

  115. Rhodes, M. J. C., L. S. C. Wooltorton., 1973. Formation of CoA esters of cinnamic acid derivatives by extracts of Brassioa napobrassioa root tissue. Phytochemistry 75: 2381–2387.

    Article  Google Scholar 

  116. Rhodes, M. J. C., L. S. C. Wooltorton., 1974. Reduction of the CoA thioesters of p-coumaric and ferulic acids by extracts of aged Brassioa napobrassioa root tissue. Phytochemistry 13: 107–110.

    Article  CAS  Google Scholar 

  117. Rhodes, M. J. C., L. S. C. Wooltorton., 1975. p-Coumaryl-CoA ligase of potato tubers. Phytochemistry 14: 2161–2164.

    Google Scholar 

  118. Rhodes, M. J. C., L. S. C. Wooltorton., 1975. Enzymes involved in the reduction of ferulic acid to coniferyl alcohol during the aging of disks of swede root tissue. Phytochemistry 14: 1235–1240.

    Article  CAS  Google Scholar 

  119. Rhodes, M. J. C., L. S. C. Wooltorton., 1976. The enzymic conversion of hydroxycinnamic acids to p-coumaroylquinic and chlorogenic acids in tomato fruits. Phytochemistry 15, in press.

    Google Scholar 

  120. Rubery, P. H., D. E. Fosket., 1969. Changes in phenyl alanine ammonia-lyase activity during xylem differentiation in Coleus and soybean. Planta 87: 54–62.

    Article  CAS  Google Scholar 

  121. Rubery, P. H., D. H. Northcote., 1968. Site of phenylalanine ammonia-lyase activity and synthesis of lignin during xylem differentiation. Nature 219: 1230–1234.

    Article  PubMed  CAS  Google Scholar 

  122. Sagisaka, S., 1976. The occurrence of peroxide in a perennial plant, Populus gelriea. Plant Physiol. 57: 308–309.

    Article  PubMed  CAS  Google Scholar 

  123. Sagisaka, S., K. Shimura., 1962. Studies in lysine biosynthesis. IV. Mechanism of activation and reduction of a-aminoadipic acid. J. Biochem. (Tokyo) 52: 155–161.

    CAS  Google Scholar 

  124. Sarkanen, K. V., 1971. Precursors and their polymerization. In Lignins ( K. V. Sarkanen and C. H. Ludwig, eds.), pp. 95–163. Wiley-Interscience, New York.

    Google Scholar 

  125. Sarkanen, K. V., H. L. Hergert. 1971. Classification and distribution. In Lignins ( K. V. Sarkanen and C. H. Ludwig, eds.), pp. 43–94. Wiley-Interscience, New York.

    Google Scholar 

  126. Sarkanen, K. V., C. H. Ludwig., 1971. Lignins. Occurrence, Formation, Structure and Reactions. Wiley-Interscience, New York, London, Sydney, Toronto.

    Google Scholar 

  127. Shimada, M., H. Fushiki, T. Higuchi., 1972. 6-Methyl-transferase activity from Japanese black pine. Phytochemistry 11: 2657–2662.

    Google Scholar 

  128. Shimada, M., H. Fushiki, T. Higuchi., 1973. Mechanism of biochemical formation of the methoxyl groups in softwood and hardwood lignins. Mokuzai Gakkaishi 19: 13–21.

    CAS  Google Scholar 

  129. Shimada, M., H. Kuroda, T. Higuchi., 1973. Evidence for the formation of methoxyl groups of ferulic and sinapic acids in Bambusa by the same (O-methyl-transferase. Phytochemistry 12: 2873–2875.

    Article  CAS  Google Scholar 

  130. Shimada, M., H. Ohashi, T. Higuchi., 1970. O-Methyl-transferase involved in the biosynthesis of lignins. Phytochemistry 9: 2463–2470.

    CAS  Google Scholar 

  131. Siegel, S. M., 1969. Evidence for the presence of lignin in moss gametophytes. Amer. J. Bot 54: 175–179.

    Article  Google Scholar 

  132. Sinha, A. K., J. K. Bhattacharjee., 1971. Lysine biosynthesis in Saocharomyoes. Conversion of α-aminoadipate into α-aminoadipic α-semialdehyde. Biochem. J. 125: 143–749.

    Google Scholar 

  133. Smith, H. 1973. Regulatory mechanisms in the photocontrol of flavonoid biosynthesis. In Biosynthesis and its Control in Plants ( B. V. Milborrow, ed.), pp. 303–321. Academic Press, London, New York.

    Google Scholar 

  134. Smith, G. J., I. J. Miller., 1975. Free radicals of coniferyl alcohol and isoeugenol. Aust. J. Chem. 25: 193–196.

    Article  Google Scholar 

  135. Snyder, F., B. Malone., 1970. Enzymic interconversion of fatty alcohols and fatty acids. Biochem. Biophys. Res. Comrnun. 41: 1382–1387.

    Article  CAS  Google Scholar 

  136. Stafford, H. A. 1974. The metabolism of aromatic com pounds. Ann. Rev. Plant Physiol. 25: 459–486.

    Article  CAS  Google Scholar 

  137. Stafford, H. A., 1974. Possible multienzyme complexes regulating the formation of C5-C3 phenolic compounds and lignins in higher plants. Recent Adv. Phytoehem. 5: 53–79.

    Google Scholar 

  138. Steelink, C., 1972. Biological oxidation of lignin phenols. Recent Adv. Phytoehem. 4: 239–271.

    CAS  Google Scholar 

  139. Stephens, G. J., R. K. S. Wood., 1974. Release of enzymes from cell walls by an endopectate-transeliminase. Nature 251: 358.

    Article  PubMed  CAS  Google Scholar 

  140. Stöckigt, J., R. L. Mansell, G. G. Gross, M. H. Zenk., 1973. Enzymic reduction of p-coumaric acid via p-coumaroyl-CoA to p-coumaryl alcohol by a cell-free system from Forsythia sp. Z. Pflanzenphysiol. 70: 305–307.

    Google Scholar 

  141. Stöckigt, J. and M. H. Zenk. 1974. Enzymatic synthesis of chlorogenie acid from caffeoyl coenzyme A and quinic acid. FEBS Lett. 42:131–134.

    Article  PubMed  Google Scholar 

  142. Sütfeld, R., R. Wiermann., 1974. Die bildung von coenzym A-thiolestern verschieden substituierter zimtsäuren durch enzymextrakte aus antheren. Z. Pflanzenphysiol. 72: 163–171.

    Google Scholar 

  143. Tanaka, Y., M. Kojima, I. Uritani., 1974. Properties, development and cellular-localization of cinnamic acid 4-hydroxylase in cut-injured sweet potato. Plant Cell Physiol. 15: 843–854.

    CAS  Google Scholar 

  144. Tedeschi, H., 1976. Mitochondria: Structure, Biogenesis and Transducing Functions. Cell Biology Monographs, Vol. 4, p. 102. Springer, Wien, New York.

    Book  Google Scholar 

  145. Tutschek, R., 1975. Isolierung und Charakterisierung der p-hydroxy-β-(carboxymethyl)-zimtsäure (sphagnumsäure) aus der zellwand von Sphagnum magellanicum Brid. Z. Pflanzenphysiol. 76: 353–365.

    CAS  Google Scholar 

  146. Uotila, L., M. Koivusalo., 1974. Formaldehyde dehyrogenase from human liver. Purification, properties, and evidence for the formation of glutathione thiolesters by the enzyme. J. Biol. Chem. 249: 7653–7663.

    PubMed  CAS  Google Scholar 

  147. Vance, C. P., A. M. D. Nambudiri, C. K. Wat, G. H. N. Towers., 1975. Isolation and properties of hydroxy-cinnamate:CoA ligase from Polyporus hispidus. Phytochemistry 14: 967–969.

    Article  CAS  Google Scholar 

  148. Vaughan, P. F. T., R. Eason, J. Y. Paton, G. A. Ritchie., 1975. Molecular weight and amino acid com-position of purified spinach beet phenolase. Phytochemistry 14: 2383–2386.

    Article  CAS  Google Scholar 

  149. Vaughan, P. F. T., R. J. Mclntyre., 1975. The action of hydroxygen peroxide on the hydroxylation of p-coumaric acid by spinach-beet phenolase. Biochem. J. 151: 759–762.

    PubMed  CAS  Google Scholar 

  150. Vieitez, A. M., A. Ballester, E. Vieitez., 1975. Coniferyl alcohol from callus of Castanea sativa cultured in vitro. Experientia 31: 1163.

    Article  CAS  Google Scholar 

  151. Vollmer, K. O., H. J. Reisener, and H. Grisebach. 1965. The formation of acetic acid from p-hydroxycinnamic acid during its degradation to p-hydroxybenzoic acid in wheat shoots. Biochem. Biophys. Res. Commun. 21: 221–225.

    Article  PubMed  CAS  Google Scholar 

  152. Wang, L., K. Takayama, D. S. Goldman, H. K. Schnoes., 1972. Synthesis of alcohol and wax ester by a cell-free system in Mycobacterium tuberculosis. Biochim. Biophys. Acta 260: 41–48.

    PubMed  CAS  Google Scholar 

  153. Walton, E., V. S. Butt., 1970. The activation of cinnamate by an enzyme from leaves of spinach beet (Beta vulgaris L. spp. vulgaris). J. Exptl. Bot 21: 887–891.

    Article  CAS  Google Scholar 

  154. Walton, E., V. S. Butt., 1971. The demonstration of cinnamyl-CoA synthetase activity in leaf extracts. Phytochemistry 10: 295–304.

    Article  CAS  Google Scholar 

  155. 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.

    Google Scholar 

  156. Wat, C. K., G. H. N. Towers., 1975. Phenolic O-methyltransferase from Lentinus lepideus Basidiomycete). Phytochemistry 14: 663–666.

    Article  CAS  Google Scholar 

  157. Wengenmayer, H., J. Ebel, 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: 529–536.

    Article  PubMed  CAS  Google Scholar 

  158. Whitmore, F. W., 1976. Binding of ferulic acid to cell walls by peroxidases of Pinus elliottii. Phytochemistry 15: 375–378.

    Article  CAS  Google Scholar 

  159. Wyrambik, D., H. Grisebach., 1975. Purification and properties of isoenzymes of cinnamyl-alcohol dehydrogenase from soybean-cell-suspension cultures. Eur. J. Biochem. 59: 9–15.

    Article  PubMed  CAS  Google Scholar 

  160. Yamada, Y., T. Kuboi., 1976. Significance of caffeic acid O-methyltransferase in lignification of cultured tobacco cells. Phytochemistry 15: 395–396.

    Article  CAS  Google Scholar 

  161. Yoshida, S., 1969. Biosynthesis and conversion of aromatic amino acids in plants. Ann. Rev. Plant Physiol. 20: 40–62.

    Article  Google Scholar 

  162. Yoshida, S., K. Tazaki, T. Minamikawa., 1975. Occurrence of shikimic and quinic acids in angiosperms. Phytochemistry 74: 195–197.

    Article  Google Scholar 

  163. Zenk, M. H., 1966. Biosynthesis of Cg-Ci-compounds. In Biosynthesis of Aromatic Compounds ( G. Billek, ed.), pp. 45–60. Pergamon, Oxford.

    Google Scholar 

  164. Zenk, M. H., 1971. Metabolism of prearomatic and aromatic compounds in plants. In Pharmacognosy and Phytochemistry (H. Wagner and L. Herhammer, eds.), pp. 314–346. Springer, Berlin, Heidelberg, New York.

    Chapter  Google Scholar 

  165. Zenk, M. H., G. G. Gross., 1972. The enzymic reduction of cinnamic acids. Recent Adv. Phytochem. 4: 87–106.

    CAS  Google Scholar 

  166. Zucker, M., 1972. Light and enzymes. Ann. Rev. Plant Physiol. 23: 133–156.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lehrstuhl für Pflanzenphysiologie, Ruhr-Universität, 4630, Bochum, Germany

    Georg G. Gross

Authors
  1. Georg G. Gross
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Washington State University, Pullman, Washington, USA

    Frank A. Loewus

  2. The University of British Columbia, Vancouver, British Columbia, Canada

    V. C. Runeckles

Rights and permissions

Reprints and permissions

Copyright information

© 1977 Plenum Press, New York

About this chapter

Cite this chapter

Gross, G.G. (1977). Biosynthesis of Lignin and Related Monomers. In: Loewus, F.A., Runeckles, V.C. (eds) The Structure, Biosynthesis, and Degradation of Wood. Recent Advances in Phytochemistry, vol 11. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-8873-3_5

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-8873-3_5

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4615-8875-7

  • Online ISBN: 978-1-4615-8873-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation