Skip to main content
SpringerLink
Log in
Book cover

Topics in Dietary Fiber Research pp 59–103Cite as

The Chemical Structure of Lignin and Quantitative and Qualitative Methods of Analysis in Foodstuffs

  • Chapter

Abstract

The large polymeric molecules, cellulose, lignin, and hemicellulose, are the major components of plant cell walls. Taken in that order, they represent the three most abundant organic compounds on earth. Yet there are no known endogenous enzymes (as there are for starch or proteins) in the digestive system of vertebrates capable of converting them into smaller units that can be absorbed from the intestine. Digestion of the carbohydrates, cellulose, and hemicellulose, is by exogenous enzymes secreted by bacteria and protozoa living symbiotically in the gut of the animal. The absorbed end products are not the basic monomeric units of the molecule but volatile fatty acids, mainly acetic, propionic and butyric acids, with smaller amounts of branched-chain fatty acids. In ruminants, the site of this fermentation process is the rumen, which is an enlarged portion of the stomach. In monogastric herbivorous animals it occurs in a specially adapted cecum. Man and other monogastric nonherbivores do not have an extensively developed cecal fermentation system and are therefore incapable of digesting large amounts of vegetable fiber.

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   39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   54.99
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. Allinson, D. W., and Osbourne, D. F., 1970, The cellulose-lignin complex in forages and its relationship to ‘orage nutritive value, J. Agric. Sci., 74: 23.

    Article  Google Scholar 

  2. Association of Official Analytical Chemists, Official methods of analysis, edited by W. Horowitz, eleventh edition, 1970, p. 862.

    Google Scholar 

  3. Aulin-Erdtmann, G., 1952, Spectrographic contributions to lignin chemistry, II, Svensk Papperstindning, 55: 745.

    Google Scholar 

  4. Bjorkman, A., 1956, Studies on finely divided wood, I, Svensk Papperstidning, 59: 477.

    CAS  Google Scholar 

  5. Bjorkman, A., 1957, Studies on finely divided wood, III, Svensk Papperstidning, 60: 243.

    CAS  Google Scholar 

  6. Bolker, H. I., and Brenner, H. S., 1970, Polymeric structure of spruce lignin, Science, 170: 173.

    Article  CAS  Google Scholar 

  7. Bondi, A., and Meyer, H., 1948, Lignins in young plants, Biochem. J., 43: 248.

    CAS  Google Scholar 

  8. Brand, J. M., 1967, Studies on grass lignins, II. The estimation of lignin oxidation products by gas-liquid chromatography, J. Chromatog., 26: 373.

    Article  CAS  Google Scholar 

  9. Brauns, F. E., The Chemistry of Lignin ( New York: Academic Press, 1952 ).

    Google Scholar 

  10. Brauns, F. E., and Brauns, D. A., The Chemistry of Lignin, supplement volume ( New York: Academic, 1960 ).

    Google Scholar 

  11. Brown, S. A., Biochemistry of Phenolic Compounds, J. B. Harborne, editor (London: Academic, 1964), chapter 9, p. 361.

    Google Scholar 

  12. Brown, S. A., 1966, Lignins, Ann. Review of Plant Physiol., 17: 223.

    Article  CAS  Google Scholar 

  13. Brown, S. A., 1969, Biochemistry of lignin formation, BioScience, 19: 115.

    CAS  Google Scholar 

  14. Brownell, H. H., 1965, Isolation of milled wood lignin and lignin-carbohydrate complex, TAPPI, 48: 513.

    CAS  Google Scholar 

  15. Brownell, H. H., 1968, Improved ball milling in the isolation of milled wood lignin, TAPPI, 51: 298.

    Google Scholar 

  16. Chang, H. M., and Allan, G. G., “Oxidation,” in: Lignins, Occurrence, Formation, Structure and Reactions, K. V. Sarkanen and C. H. Ludwig, editors, New York: Wiley Interscience, 1971) chapter 11, p. 433.

    Google Scholar 

  17. Clark. E. P., 1932, The Vieböck and Schwappach method for the determination of methoxyl and ethoxyl groups, J. A. O. A. C., 15: 136.

    CAS  Google Scholar 

  18. Creighton, R. H. J., and Hibbert, H., 1944, Studies on lignin and related compounds, LXXVI. Alkaline nitrobenzene oxidation of corn stalks. Isolation of L-hydroxybenzaldehyde, J. Amer. Chem. Soc., 66: 37.

    Article  CAS  Google Scholar 

  19. Csonka, F. A., Phillips, M. and Jones, D. B., 1929, Studies on lignin metabolism, J. Biol. Chem., 85: 65.

    CAS  Google Scholar 

  20. Cymbaluk, N. F., Gordon, A. J., and Neudoerffer, T. S., 1973, The effect of the chemical composition of maize plant lignin on the digestibility of maize stalk in the rumen of cattle, Br. J. Nutr., 29: 1.

    Article  CAS  Google Scholar 

  21. Cymbaluk, N. F., and Neudoerffer, T. S., 1970, A quantitative gas-liquid chromatographic determination of aromatic aldehydes from nitrobenzene oxidation of lignin, J. Chromatog., 54: 167.

    Article  Google Scholar 

  22. Donnelly, E. D., and Wear, J. I., 1972, Acid detergent method for reduction of tannin interference in determining lignin of Sericea Lespediza, Agron. J., 64: 838.

    Article  CAS  Google Scholar 

  23. Edwards, C. S., 1973, Determination of lignin and cellulose in forages by extraction with triethylene glycol, J. Sci. Fd. Agric., 24: 381.

    Article  CAS  Google Scholar 

  24. El-Basyouni, S. Z., and Towers, G. H. N., 1964, The phenolic acids in wheat, I. Changes during growth and development, Can. J. Biochem., 42: 203.

    CAS  Google Scholar 

  25. Ellis, G. H., Matrone, G., and Maynard, L. A., 1946, A 72-percent H2SO4 method for the determination of lignin and its use in animal nutrition studies, J. Anim. Sci., 5: 285.

    CAS  Google Scholar 

  26. Fischer, H., 1961, Quantitative determination of lignin in hay, Acta Agrie. Scand., Supplementum Number 10, 43 p.

    Google Scholar 

  27. Freudenberg, K., 1964, Lignin: Its constitution and formation from p-hydroxycinnamyl alcohols, Science, 148: 595.

    Google Scholar 

  28. Freudenberg, K., in: Constitution and Biosynthesis of Lignin, by K. Freudenberg and A. C. Neish, ( New York: Springer, 1968 ) p. 47.

    Google Scholar 

  29. Gee, M., Nelson, O. E., and Kuc, J., 1968, Abnormal lignins produced by the Brown-Midrib Mutants of maize, II, Archs. Biochem. Biophys., 123: 403.

    Article  CAS  Google Scholar 

  30. Gierer, J., 1954, Die reaktion von Chinonmonochlorimid mit lignin, I. Spezifitat der reaktion auf 2–0xybenzylalkoholgruppen und der Bestimmung in verschiedenen Ligninprgparaten, Acta Chemica Scand., 8: 1319.

    Article  CAS  Google Scholar 

  31. Goldschmid, O., 1954, Determination of phenolic hydroxyl content of lignin preparations by ultraviolet spectrophotometry, Anal. Chem., 26: 1421.

    Article  CAS  Google Scholar 

  32. Gordon, A. J., A comparison of some chemical and physical properties of alkali ligning from grass and lucerne hays before and after digestion by sheep, J. Sci. Fd. Agric., in press.

    Google Scholar 

  33. Gordon, A. J., and Griffith, P. R., 1973, Chemical and in vivo evaluation of a Brown Midrib Mutant of Zea mays, II. Nuclear magnetic resonance spectra of digested and undigested alkali lignins and undigested dimethylformatide lignins, J. Sci. Fd. Agric., 24: 579.

    Article  CAS  Google Scholar 

  34. Gordon, A. J., and Neudoerffer, T. S., Chemical and in vivo evaluation of a Brown Midrib Mutant of Zea mays, I. Fibre, lignin and amino acid composition and digestibility for sheep, J. Sci. Fd. Agric., 24: 565, 1973.

    CAS  Google Scholar 

  35. Goring, D. A. I., “Polymer properties of lignin and lignin derivatives,” in: Lignins, Occurrence, Formation, Structure, and Reactions, K. V. Sarkanen and C. H. Ludwig, editors, (New York: Wiley Interscience, 1971) chapt. 17, p. 695.

    Google Scholar 

  36. Hall, F. K., 1974, Wood pulp, Scientific American, 230: 51.

    Google Scholar 

  37. Harkin, J. M., 1967, “Lignin - a natural polymeric product of phenol oxidation,” in: Oxidative Coupling of Phenols, edited by W. I. Taylor and A. R. Battersby, New York: Marcel Dekker, Inc., chapter 6, p. 243.

    Google Scholar 

  38. Hartley, R. D., 1971, Improved methods for the estimation by gas-liquid chromatography of lignin degradation products from plants, J. Chromatog., 54: 335.

    Article  CAS  Google Scholar 

  39. Hartley, R. D., 1972, P Coumaric and ferulic acid components of cell walls of ryegrass and their relationships with lignin and digestibility, J. Sci. Fd. Agric., 23: 1347.

    Google Scholar 

  40. Hartley, R. D., 1973, Carbohydrate esters of ferulic acid as components of cell walls of Lolium multiflorum, Phytochem., 12: 661.

    Article  CAS  Google Scholar 

  41. Higuchi, T., Ito, Y., and Kawamura, I., 1967, P-Hydroxyphenylpropane component of grass lignin and role of tryosine-ammonia lyase in its formation, Phytochem, 6: 875.

    Article  CAS  Google Scholar 

  42. Higuchi, T., Ito, Y., Shimada, M., and Kawamura, I., 1967, Chemical properties of milled wood lignin of grasses, Phytochem., 6: 1551.

    Article  CAS  Google Scholar 

  43. Higuchi, T., and Kawamura, I., 1966, Occurrence of L-hydroxyphenylglycerol-ß-aryl ether structure in lignins, Holzforschung, 20: 16.

    CAS  Google Scholar 

  44. Higuchi, T., Tanahashi, M., and Sato, A., 1972, Acidolysis of bamboo lignin, I. Gas-liquid chromatography and mass spectrometry of acidolysis monomers, Mokuzai Gakkaishi, 18: 183.

    CAS  Google Scholar 

  45. Johnson, D. B., Moore, W. E., and Zank, L. C., 1961, The spectrophotometric determination of lignin in small wood samples, TAPPI, 44: 793.

    CAS  Google Scholar 

  46. Kawamura, I. and Higuchi, T., 1964, Comparative studies of milled wood lignins from different taxonomical origins by infrared spectroscopy, in: Chimie et Biochimie de la lignine, de la cellulose et des hemicelluloses, Symp., Grenoble, p. 439.

    Google Scholar 

  47. Kirk, T. K., Brown, W., and Cowling, E. B., 1969, Preparative fractionation of lignin by gel-permeation chromatography, Biopolymers, 7: 135.

    Article  CAS  Google Scholar 

  48. Kosikova, B., and Polcin, J., 1973, Isolation of lignin from spruce by acidolysis in dioxane, Wood Science and Technology, 7: 308.

    Article  CAS  Google Scholar 

  49. Kué, J., and Nelson, O. E., 1964, The abnormal lignins produced by the brown-midrib mutants of maize, I, Archs. Biochem. Biophys., 105: 103.

    Article  Google Scholar 

  50. Kué, J., Nelson, O. E., and Flanagan, P., 1968, Degradation of abnormal lignins in the Brown-Midrib Mutants and Double Mutants of maize, Phytochem., 7: 1435.

    Article  Google Scholar 

  51. Kutscha, N. P., and Gray, J. R., 1970, The potential of lignin research, Technical Bulletin 41, Maine Agricultural Experiment Station, University of Maine, 20 pages.

    Google Scholar 

  52. Lai, Y. Z., and Sarkanen, K. V., “Isolation and structural studies,” in: Lignins, Occurrence, Formation, Structure and Reactions (New York: Wiley Interscience, 1971) chapter 5, p. 165.

    Google Scholar 

  53. Leary, G., 1971, The problem of lignin, J. N. Z. Inst. Chem., 35: 7.

    CAS  Google Scholar 

  54. Lenz, B. L., 1968, Application of nuclear magnetic resonance spectroscopy to characterization of lignin, TAPPI, 51: 511.

    CAS  Google Scholar 

  55. Lüdemann, H. D., and Nimz, H., 1973, Carbon-13 nuclear magnetic resonance spectra of lignins, Biochem. Biophys. Res. Comm., 52: 1162.

    Article  Google Scholar 

  56. Ludwig, C. G., Nist, B. J., and McCarthy, J. L., 1963, Lignin, XII and XIII, J. Am. Chem. Soc., 86:1186 and 1196.

    Google Scholar 

  57. Macdonald, A. M. G., “The oxygen-flash method,” in: Advances in Analytical Chemistry and Instrumentation, C. N. Reilley, editor (New York: John Wiley and Sons, Inc.,1965) vol. 4, p. 75.

    Google Scholar 

  58. McKenzie, A. W., McPherson, J. A., and Stewart, C. M., 1955, The estimation of acid-soluble lignin, Holzforshung, 9: 109.

    Article  CAS  Google Scholar 

  59. Manning, K. R., and DeLong, W. A., 1941, The lignin content of some common vegetables with observations on methods for the determination of lignin, Sci. Agric., 22: 69.

    CAS  Google Scholar 

  60. Martin, A. K., 1970, The urinary aromatic acids excreted by sheep given S24 perennial ryegrass cut at six stages of maturity, Br. J. Nutr., 24: 943.

    Article  CAS  Google Scholar 

  61. Mathers, A. P., and Pro, M. J., 1955, Spectrophotometric determination of methoxyl, Anal. Chem., 27: 1662.

    CAS  Google Scholar 

  62. Merewether, J. W. T., 1957, A lignin-carbohydrate complex in wood, Holzforschung, 11: 65.

    Article  Google Scholar 

  63. Meyer, H., and Bondi, A., 1952, Lignin in young plants, Biochem. J., 52: 95.

    CAS  Google Scholar 

  64. Miksche, G. E., 1973, Studies on the structure of gynmosperm and angiosperm lignins, Abstracts of Gothenburg Dissertations in Science, 31: 24 pages.

    Google Scholar 

  65. Moon, F. E., and Abou-Raya, A. K., 1954, The lignin fraction of animal feeding-stuffs, IV. The preparation of “Reference” lignin by extraction with ethyl acetoacetate, J. Sci. Fd. Agric., 5: 319.

    Article  CAS  Google Scholar 

  66. Morrison, I. M., 1972, Improvements in the acetyl bromide technique to determine lignin and digestibility and its application to legumes, J. Sci. Fd. Agric., 23: 1463.

    Article  CAS  Google Scholar 

  67. Morrison, I. M., 1974, Structural investigation on the lignin-carbohydrate complexes of Lolium perenne, Biochem. J., 139: 197.

    CAS  Google Scholar 

  68. Neish, A. C., “Monomeric intermediates in the biosynthesis of lignin,” in: Constitution and Biosynthesis of Lignin, by K. Freudenberg and A. C. Neish, ( New York: Springer, 1968 ) p. 1.

    Google Scholar 

  69. Neth. J. Agric. Sci., 1966, 14: 215.

    Google Scholar 

  70. Nimz, H., 1973, Chemistry of potential chromophoric groups in beech lignin, TAPPI, 56: 124.

    CAS  Google Scholar 

  71. Pepper, J. M., and Wood, P. D. S., 1962, The isolation of a representative lignin fraction from wood and straw meals, Can. J. Chem., 40: 1026.

    CAS  Google Scholar 

  72. Pepper, J. M., Manolopoulo, M., and Burton, R., 1962, Gas-liquid chromatographic analysis of lignin oxidation products, Can. J. Chem., 40: 1976.

    Google Scholar 

  73. Pew, J. C., and Connors, W. J., 1969, New structures from enzymic dehydrogenation of lignin model 2-hydroxypropiophenones, J. Org. Chem., 34: 585.

    Article  CAS  Google Scholar 

  74. Phillips, M., Goss, M. J., Davis, B. L., and Stevens, H., 1939, Composition of the various parts of the oat plant at successive stages of growth, with special reference to the formation of lignin, Sci. Agric., 52: 319.

    Google Scholar 

  75. Pigden, W. J., and Stone, J. E., 1952, The effect of ruminant digestion on forage lignin, Sci. Agric., 32: 502.

    CAS  Google Scholar 

  76. Porter, P., and Singleton, A. G., 1971, The degradation of lignin and quantitative aspects of ruminant digestion, Br. J. Nutr., 25: 3.

    Article  CAS  Google Scholar 

  77. Quicke, G. V., and Bentley, O. G., 1959, Lignin and methoxyl as related to the decreased digestibility of mature forages, J. Anim. Sci., 18: 365.

    CAS  Google Scholar 

  78. Rezl, V., and Janâk, J., 1973, Elemental analysis by gas chromatography, J. Chromatog., 81: 233.

    Article  CAS  Google Scholar 

  79. Roadhouse, F. E. and MacDougall, D., 1956, A study of the nature of plant lignin by means of alkaline nitrobenzene oxidation, Biochem. J., 63:33

    Google Scholar 

  80. Sarkanen, K. V., and Ludwig, C. H., editors, Lignins, Occurrence, Formation, Structure and Reactions, ( New York: Wiley Interscience. 1971.

    Google Scholar 

  81. Sarkanen, K. V., “Precursors and their polymerization,” in: Lignins, Occurrence, Formation, Structure and Reactions, K. V. Sarkanen and C. H. Ludwig, editors, (New York: Wiley Interscience, 1971), chapter 4, p. 95.

    Google Scholar 

  82. Sato, A., Nishio, K., and Kitamura, T., 1972, On the ratio of syringaldehyde to vanillin (S/V value) of the lignin in peanuts (Arachis hypogaea L.), Ag. Chem. (Japan), 46: 603.

    CAS  Google Scholar 

  83. Shimada, M., 1972, Biochemical studies of bamboo lignin and methoxylation in hardwood and softwood lignins, Wood Research, 53: 19.

    Google Scholar 

  84. Siggia, S., 1966, Quantative Organic Analysis via Functional Groups, third edition, New York: John Wiley and Sons, Inc., chapter 4, p. 209.

    Google Scholar 

  85. Soundararajan, T. N., and Wayman, M., 1970, The determination of the molecular weight and molecular weight distribution of dehydrogenase polymers of coniferyl alcohol and lignins, J. Polymer Sci., 30: 521.

    Google Scholar 

  86. Stafford, H. A., 1960, Differences between lignin-like polymers formed by peroxidation of eugenol and ferulic acid in leaf sections of Phleum, Plant Physiol. 1: 108.

    Article  Google Scholar 

  87. Stafford, H. A., 1960, Comparison of lignin-like polymers produced peroxidatively by cinnamic acid derivatives in leaf sections of Phleum, Plant Physiol., 35: 612.

    Article  CAS  Google Scholar 

  88. Stafford, H. A., 1962, Histochemical and biochemical differences between lignin-like materials in Phleum pratense L., Plant Physiol., 37: 643.

    Article  CAS  Google Scholar 

  89. Stafford, H. A., 1964, Comparison of lignin-like products found naturally or induced in tissues of Phleum Elodea and Coleus and in a paper peroxidase system, Plant Physiol., 12: 350.

    Article  Google Scholar 

  90. Stafford, H. A., 1974, The metabolism of aromatic compounds, Ann. Review of Plant Physiol., 25: 460.

    Google Scholar 

  91. Stone, J. E., Blundell, M. J., and Tanner, K. G., 1951, The formation of lignin in wheat plants, Can. J. Chem., 72: 734.

    Google Scholar 

  92. Streeter, C. H., 1969, A review of techniques used to estimate the in vivo digestibility of grazed forage, J. Anim. Sci., 29: 757.

    Google Scholar 

  93. Talmadge, K. W., Keegstra, K., Bauer, W. D., and Albersheim, P., 1973, The structure of plant cell walls, I, Plant Physiol., 51: 158.

    Article  CAS  Google Scholar 

  94. Thomas, B., and Armstrong, D. G., 1949, A study of some methods at present used for the determination of lignin, J. Agric. Sci., 39: 335.

    Article  CAS  Google Scholar 

  95. Van Soest, P. J., 1973, Use of detergents in the analysis of fibrous feeds, II. A rapid method for the determination of fiber and lignin, J. A. O. A. C., 46: 829.

    Google Scholar 

  96. Van Soest, P. J., 1964, Symposium on nutrition and forage and pastures: New chemical procedures for evaluating forages, J. Anim. Sci, 23: 838.

    Google Scholar 

  97. Van Soest, P. J., 1967, Development of a comprehensive system of feed analyses and its application to forages, J. Anim. Sci., 26: 119.

    Google Scholar 

  98. Van Soest, P. J., and McQueen, R. W., 1973, The chemistry and estimation of fibre, Proc. Nutr. Soc., 32: 123.

    Article  Google Scholar 

  99. Van Soest, P. J., and Wine, R. H., 1967, Use of detergents in the analysis of fibrous feeds, IV. Determination of plant cell-wall constituents, J. A. O. A. C., 50: 50.

    Google Scholar 

  100. Van Soest, P. J. and Wine, R. H., 1968, Determination of lignin and cellulose in acid-detergent fiber with permanganate, J. A. 0. A. C., 51: 780.

    Google Scholar 

  101. Wardrop, A. B., “Occurrence and formation in plants,” in: Lignins, Occurrence, Formation, Structure and Reactions, K. V. Sarkanen and C. H. Ludwig, editors, (New York: Wiley Interscience, 1971) chapter 2, p. 79.

    Google Scholar 

  102. Wexler, A. 5.,1964, Characterization of lignosulfonates by ultraviolet spectrometry, Anal. Chem., 36: 213.

    Google Scholar 

  103. Whitehead, D. L., and Quicke, G. V., 1960, The nitrogen content of grass lignin, J. Sci. Fd. Agric., 11: 151.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Animal Physiology, University of Wageningen, The Netherlands

    Anthony J. Gordon

Authors
  1. Anthony J. Gordon
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Syntex Research, Palo Alto, California, USA

    Gene A. Spiller

Rights and permissions

Reprints and permissions

Copyright information

© 1978 Plenum Press, New York

About this chapter

Cite this chapter

Gordon, A.J. (1978). The Chemical Structure of Lignin and Quantitative and Qualitative Methods of Analysis in Foodstuffs. In: Spiller, G.A. (eds) Topics in Dietary Fiber Research. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-2481-2_3

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-2481-2_3

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-2483-6

  • Online ISBN: 978-1-4684-2481-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation