Isolation and identification of phenolic compounds: A practical guide

Phenolic Compound Biochemistry

Volumn , Issue , 2006, Pages 151-196

  Vermerris, Wilfred ^a,b   Nicholson, Ralph ^b  

^a UNIVERSITY OF FLORIDA   (United States)

^b PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84900108187     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-1-4020-5164-7_4     Document Type: Chapter

References (94)

1. Adler, E., Björkqvist, K. J., and Häggroth, S., 1948, Über die Ursache der Farbreaktionen des Holzes, Acta Chem. Scand. 2:93-94.
2. Bate-Smith, E. C., 1977, Astringent tannins of Acer species, Phytochem. 16:1421-1426.
3. Boon, J. J., 1992, Analytical pyrolysis mass spectrometry: new vistas opened by temperature-resolved in-source PYMS. Int. J. Mass Spectrom. Ion Process. 118/119:755-787.
4. Boon, J. J., 1989, An introduction to pyrolysis mass spectroscopy of lignocellulosic material: case studis of barley straw, corn stem and Agropyron, in: Physico-chemical Characterisation of Plant Residues for Industrial and Feed Use, A. Chesson, and E. R. ørskov, eds., Elsevier Applied Science London, pp. 25-49.
5. Bout, S., and Vermerris, W., 2003, A candidate-gene approach to clone the sorghum Brown midrib gene encoding caffeic acid O-methyltransferase. Mol. Genet. Genomics 269:205-214.
6. Brinkmann, K., Blaschke, L., Polle, A., 2002, Comparison of different methods for lignin determination as a basis for calibration of nearinfrared reflectance spectroscopy and implications of lignoproteins, J. Chem. Ecol. 28:2483-2501.
7. Browning, B. L., 1967, Methods of Wood Chemistry, Vol. II, Wiley-Interscience, New York, pp. 785-793.
8. Bruce, R., and West, C., 1989, Elicitation of lignin biosynthesis and isoperoxidase activity by pectic fragments in suspension cultures of castor bean, Plant Physiol. 91:889-897.
9. Cadena-Gomez, G., and Nicholson, R. L., 1987, Papilla formation and associated peroxidase activity: A non-specific response to attempted fungal penetration of maize, Physiol. Mol. Plant Pathol. 31:51-67.
10. Chapple, C. C. S., Vogt, T., Ellis, B. E., and Sommerville, C. R., 1992, An Arabidopsis mutant defective in the general phenylpropanoid pathway, Plant Cell 4:1413-1424.
11. Chen, L., Carpita, N. C., Reiter, W.-D., Wislon, R. H., Jeffries, C., and McCann, M. C. 1998, A rapid method to screen for cell-wall mutants using discriminant analysis of Fourier transform infrared spectra, Plant J. 16:385-392.
12. De Neergaard, E., 1997, Methods in Botanical Histopathology, Danish Government Institute of Seed Pathology for Developing Countries, Copenhagen, pp. 216.
13. Deising, H., Nicholson, R. L., Haug, M., Howard, R. J., and Mendgen, K., 1992, Adhesion pad formation and the involvement of surface localized cutinase and esterase in the attachment of Uredospores to the host cuticle, Plant Cell 4:1101-1111.
14. Dias, A. P., and Grotewold, E. 2003 Manipulating the accumulation of phenolics in maize cultured cells using transcription factors, Biochem. Eng. J. 14:207-216.
15. Faix, O., 1992, Fourier-transform infrared spectroscopy, in: Methods in Lignin Chemistry, S. Y. Lin, and C. W. Dence, eds. Springer-Verlag, Berlin, pp. 81-109.
16. Folin, O., and Ciocalteu, V., 1927, On tyrosine and tryptophan determinations in proteins, J. Biol. Chem. 73:627-650.
17. Folin, O., and Denis, W., 1912a, On phosphotungstic-phospomolybdic compounds as color reagents, J. Biol. Chem. 12:239-243.
18. Folin, O., and Denis, W., 1912b, Tyrosine in proteins as determined by a new colorimetric method, J. Biol. Chem. 12:245-251.
19. Folin, O., and Denis, W., 1915, A colorimetric method for the determination of phenols (and phenol derivatives) in urine, J. Biol. Chem. 22:305-308.
20. Fontaine, A.-S., Bout, S., Barrière, Y., and Vermerris, W., 2003. Variation in cell wall composition among forage maize inbred lines and its impact on digestibility: Analysis of neutral detergent fiber composition by pyrolysis-gas chromatography-mass spectrometry, J. Agric. Food Chem. 51:8080-8087.
21. Freudenberg, K., 1939, Über lignin. Angew. Chem. 52:362-363.
22. Friebolin, H., 2004, Basic One- and Two-Dimensional NMR Spectroscopy, John Wiley & Sons, pp. 430.
23. Fukushima, R. S., and Hatfield, R. D., 2001, Extraction and isolation of lignin for utilization as a standard to determine lignin concentration using the acetyl bromide spectrophotometric method, J. Agric. Food Chem. 49:3133-3139.
24. Fukushima, R. S., and Hatfield, R. D., 2004, Comparison of the acetylbromide spectrophotometric method with other analytical lignin methods for the determination of lignin concentration in forage samples, J. Agric. Food Chem. 52:3713-3720.
25. Geiger, H., and Fuggerer, H., 1979, Über den Chemismus der Wiesner-Reaktion auf Lignin, Z. Naturforsch. 34b:1471-1472.
26. Hagerman, A., and Butler, L. G., 1989, Choosing appropriate methods and standards for assaying tannin, J. Chem. Ecol. 15:1795-1810.
27. Halpin, C., Holt, K., Chojecki, J., Oliver, D., Chabbert, B., Monties, B., Edwards, K., Barakate, A., and Foxon, G. A., 1998, Brown-midrib maize (bm1) - a mutation affecting the cinnamyl alcohol dehydrogenase gene, Plant J. 14:545-553.
28. Harkin J. M., and Obst, J. R., 1973, Lignification in trees: indication of exclusive peroxidase participation, Science 180:296-298.
29. Haslam, E., 1965, Galloyl esrers in the Aceraceae, Phytochem. 4:495-498.
30. Hatfield, R. D., Grabber, J., Ralph, J., and Brei, K., 1999, Using the acetyl bromide assay to determine lignin concentrations in herbaceous plants: some cautionary notes, J. Agric. Food Chem. 47:628-632.
31. Hatfield, R. D., Jung, H.-J. G., Ralph, J., Buxton, D. R., Weimer, P. J., 1994, A comparison of the insoluble residues produced by the Klason and acid detergent lignin procedures, J. Sci. Food Agric. 65:51-58.
32. Hatfield, R. D., and Fukushima, R. S., 2005, Can lignin be accurately measured, Crop Sci. 45:832-839.
33. Hinch, J. M., and Clarke, A. E., 1980, Callose formation in Zea mays as a response to infection with Phytophthora cinnamomi, Physiol. Plant Pathol. 21:113-124.
34. Hoffmann, L., Besseau, S., Geoffroy, P., Ritzenthaler, C., Meyer, D., Lapierre, C., Pollet, B., and Legrand, M., 2004, Silencing of hydroxycinnamoyl-coenzyme A shikimate/quinate hydroxyltransferase affects phenylpropanoid biosynthesis, Plant Cell 16:1446-1465.
35. Iiyama, K., and Wallis, A. F. A., 1990, Determination of lignin in herbaceous plants by an improved acetyl bromide procedure, J. Sci. Food Agric. 51:145-162.
36. Inoue, K. H., and Hagerman, A., 1988, Determination of gallotannin with rhodanine, Anal. Biochem. 169:363-369.
37. Johnson, D. B., Moore, W. E., and Zank, L. C., 1961, The spectrophotometric determination of lignin in small wood samples, Tappi 44:793-789.
38. Johnson, R. A., and Wichern, D. W., 1992, Applied Multivariate Statistical Analysis, Prentice Hall, Englewood Cliffs, NJ, pp. 767.
39. Jung, H. G., 1997, Analysis of forage fiber and cell walls in ruminant nutrition, J. Nutr. 127:810S-813S.
40. Jung, H. G., and Deetz, D. A., 1993, Cell wall lignification and degradability, in: Forage Cell Wall Structure and Digestibility, H. G. Jung, D. R. Buxton, R. D. Hatfield, and J. Ralph, eds., ASA, CSCA, SSSA, Madison, WI, pp. 315-346.
41. Keeler, J., 2005, Understanding NMR Spectroscopy, John Wiley & Sons, pp. 476.
42. Kemsley, E. K., 1998, Discriminant Analysis and Class Modelling of Spectroscopic Data, John Wiley & Sons Ltd, Chichester, UK, pp. 179.
43. Lapierre, C., 1993, Application of new methods for the investigation of lignin structure, in: Forage Cell Wall Structure and Digestibility, H. G. Jung, D. R. Buxton, R. D. Hatfield, and J. Ralph, eds., ASA, CSCA, SSSA, Madison, WI, pp. 133-166.
44. Lewis, N. G., and Yamamoto, E., 1990, Lignin: occurrence, biogenesis and biodegradation, Ann. Rev. Plant Phys. Plant Mol. Biol. 41:455-496.
45. Lin, S. Y., and Dence, C. W., 1992, Methods in Lignin Chemistry, Springer-Verlag, Berlin, pp. 578.
46. Lu, F., and Ralph, J., 1997, Derivatization followed by reductive cleavage (DFRC method), a new method for lignin analysis: protocol for analysis of DFRC monomers, J. Agr. Food Chem. 45:2590-2592.
47. Lu, F., and Ralph, J., 2003, Non-degradative dissolution and acetylation of ball-milled cell walls: high-resolution solution-state NMR, Plant J. 35:535-544.
48. Maehly, A. C., and Chance, B., 1954, The assay of catalases and peroxidase, in: Methods of Biochemical Analysis, Vol. 1, D. Glick, ed., Interscience Publishers, New York, pp. 357-408.
49. Marita, J. M., Ralph, J., Hatfield, R. D., and Chapple, C., 1999, NMR characterization of lignins in Arabidopsis altered in the activity of ferulate 5-hydroxylase, Proc. Natl. Sci. Acad. USA 96:12328-12332
50. Marita, J., Vermerris, W., Ralph, J., and Hatfield, R. D., 2003, Variations in the cell wall composition of maize brown midrib mutants, J. Agric. Food Chem. 51:1313-1321.
51. Meier, D., and Faix, O., 1992, Pyrolysis-gas chromatography-mass spectroscopy, in: Methods in Lignin Chemistry, S. Y. Lin and C. W. Dence, eds., Springer-Verlag, Berlin, pp. 177-199.
52. Mendgen, K., 1975, Ultrastructural demonstration of different peroxidase activities during the bean rust infection process, Physiol. Plant Pathol. 6:2275-2282.
53. Meyer, K., Shirley, A. M., Cusumano, J. C., Bell-Lelong, D. A., and Chapple, C., 1998, Lignin monomer composition is determined by the expression of a cytochrome P450-dependent monooxygenase in Arabidopsis, Proc. Natl. Acad. Sci. USA 95:6619-6623.
54. Monties, B., 1989, Lignins, in: Methods in Plant Biochemistry, Vol. 1 Plant Phenolics, J. B. Harborne, ed., Academic Press, London, pp. 113-157.
55. Morreel, K., Ralph, J., Lu, F., Goeminne, G., Busson, R., Herdewijn, P., Goeman, J. L., Van der Eycken, J., Boerjan, W., and Messens, E. 2004, Phenolic profiling of caffeic acid O-methyltransferase-deficient poplar reveals novel benzodioxane oligolignols., Plant Physiol. 136:4023-4036.
56. Mouille, G., Robin S., Lecomte, M., Pagant S., and Höfte, H., 2003, Classification and identification of Arabidopsis cell wall mutants using Fourier-Transform InfraRed (FT-IR) microspectroscopy, Plant J. 35:393-404.
57. Mueller, W. C., and Beckman, C. H., 1978, Ultrastructural localization of polyphenoloxidase and peroxidase in roots and hypocotyls of cotton seedlings, Can. J. Bot. 56:1579-1587.
58. Mulder, M. M., Van der Hage, E. R. E., and Boon, J. J., 1992, Analytical in source pyrolytic methylation electron impact mass spectroscopy of phenolic acids in biological matrices, Phytochem. Anal. 3:165-172.
59. O'Connell, A., Holt, K., Piquemal, J., Grima-Pettenati, J., Boudet, A., Pollet, B., Lapierre, C., Petit-Conil, M., Schuch, W., and Halpin, C. 2002, Improved paper pulp from plants with suppressed cinnamoyl-CoA reductase or cinnamyl alcohol dehydrogenase, Transgen. Res. 11:495-503.
60. Politis, D. J., and Wheeler, H., 1973, Ultrastructural study of penetration of maize leaves by Colletotrichum graminicola, Physiol. Plant Pathol. 3:465-471.
61. Pomar, F., Merino, F., and Ros Barceló, A., 2002, O-linked coniferyl and sinapyl aldehydes in lignifying cell walls are the main targets of the Wiesner (phloroglucinol-HCl) reaction, Protoplasma 220:17-28.
62. Ralph, J., and Helm, R. F., 1993, Lignin/hydroxycinnamic acid/polysaccharide complexes: synthetic models for regiochemical characterization, in: Forage Cell Wall Structure and Digestibility, H. G. Jung, D. R. Buxton, R. D. Hatfield, and J. Ralph, eds., ASA, CSCA, SSSA, Madison, WI, pp. 201-246.
63. Ralph, J., Lapierre, C., Marita, J. M., Kim, H., Lu, F., Hatfield, R. D., Ralph, S., Chapple, C., Franke, R., Hemm, M. R., Van Doorsselaere, J., Sederoff, R. R., O'Malley, D. M., Scott, J. T., Mackay, J. J., Yahiaoui, N., Boudet, A. M., Pean, M., Pilate, G., Jouanin, L., and Boerjan, W., 2001, Elucidation of new structures in lignins of CAD- and COMT-deficient plants by NMR, Phytochem. 57:993-1003.
64. Ralph, J., MacKay, J. J., Hatfield, R. D., O'Malley, D. M., Whetten, R. W., and Sederoff, R. R., 1997, Abnormal lignin in a loblolly pine mutant, Science 277:235-238.
65. Ralph, J., Marita, J. M., Ralph, S. A., Hatfield, R. D., Lu, F., Ede, R. M., Peng, J., Quideau, S., Helm, R. F., Grabber, J. H., Kim, H., Jimenez-Monteon, G., Zhang, Y., Jung, H.-J. G., Landucci, L. L., MacKay, J. J., Sederoff, R. R., Chapple, C., and Boudet, A.-M., 1999, Solution-state NMR of lignins, in: Advances in Lignocellulosics Characterization, Argyropoulos, D. S. and Rials, T., eds., Technical Association of the Pulp and Paper Industry, Atlanta, GA, pp. 55-108.
66. Scalbert, A., Monties, B., and Janin, G., 1989, Tannins in wood: comparison of different estimation methods, J. Agric. Food Chem. 37:1324-1329.
67. Schultz, J. C., and Baldwin, I. T., 1982, Oak leaf quality declines in response to defoliation by gypsy moth larvae, Science 217:149-151.
68. Sené, C. F. B., McCann, M. C., Wilson, R. H., Grinter, R., 1994, Fouriertransform Raman and Fourier-transform infrared spectroscopy, Plant Physiol. 106:1623-1631.
69. Shiraishi, T., Yamada, T., Nicholson, R. L., and Kunoh, H., 1995, Phenylalanine ammonia-lyase in barley: Activity enhancement in response to Erysiphe graminis f.sp. hordei (race 1) a pathogen, and pisi, a non-pathogen, Physiol. Mol. Plant Pathol. 46:153-162.
70. Sherwood, R. T., 1985, Papilla formation in isolated root-cap cells of maize inoculated with Colletotrichum graminicola, Phytopathol. 75:1313-1314.
71. Siesler, H. W., Ozaki, Y., Kawata, S., and Heise, H. M., 2002, Near Infrared Spectroscopy. Principles, Instruments, Applications, Wiley-VCH, Weinheim, Germany, pp. 348.
72. Sjöström, E., and Alen, R., 1999, Analytical Methods in Wood Chemistry, Pulping and Papermaking, Springer-Verlag, Berlin, pp. 316.
73. Smith, M. M., and O'Brian, T. P., 1979, Distribution of auto fluorescence and esterase and peroxidase activities in the epidermis of wheat roots, Austr. J. Plant Physiol. 6:201-219.
74. Swain, T., and Hillis, W. E., 1959, The phenolic constituents of Prunus domestica. I. The quantitative analysis of phenolic constituents, J. Sci. Food Agric. 10:63-68.
75. Tamagnone, L., Merida, A., Parr, A., Mackay, S., Culianez-Macia, F. A., Roberts, K., and Martin, C. 1998, The AmMYB308 and AmMYB330 transcription factor from Antirrhinum regulate phenylpropanoid and lignin biosynthesis in transgenic tobacco, Plant Cell 10:135-154.
76. Theander, O., and Westerlund, A., 1986, Studies on dietary fiber. 3. Improved analysis of dietary fiber, J. Agric. Food Chem. 34:330-336.
77. Thorpe, J. R., and Hall, J. L., 1984, Chronology and elicitation of changes in peroxidase and phenylalanine ammonia-lyase activities in wounded wheat leaves in response to inoculation with Botrytis cinerea, Physiol. Plant Pathol. 25:363-379.
78. Van Soest P. J., 1963, Use of detergents in analysis of fibrous feeds. 2. A rapid method for the determination of fiber and lignin, J. Assoc. Off. Agr. Chem. 46:829-835.
79. Van Soest, P. J., 1967, Development of a comprehensive system of feed analyses and its application to forages, J. Anim. Sci. 26:119-128.
80. Van Soest P. J., Wine R. H., 1967, Use of detergents in analysis of fibrous feeds. Determination of plant cell-wall constituents, J. Assoc. Off. Agr. Chem. 50:50-55.
81. Vance, C. P., and Sherwood, R. T., 1976, Cyclohexamide treatments implicate papilla formation in reed canarygrass to fungi, Phytopathol. 66:498-502.
82. Vermerris, W., and Boon, J. J., 2001, Tissue-specific patterns of lignification are disturbed in the brown midrib2 mutant of maize (Zea mays L.), J. Agric. Food Chem. 49:721-728.
83. Vermerris, W., Thompson, K. J., and McIntyre, L. M., 2002, The maize Brown midrib1 locus affects cell wall composition and plant development in a dose-dependent manner, Heredity 88:450-457.
84. Viriot, C., Scalbert, A., Lapierre, C., and Moutounet, M. 1993, Ellagitannins and lignins in aging of spirits in oak barrels, J. Agric. Food Chem. 41:1872-1879.
85. Wilson, T. C., and Hagerman, A. E., 1990, Quantitative determination of ellagic acid, J. Agric. Food Chem. 38:1678-1683.
86. Yong, W., Link, B., O'Malley, R., Tewari, J., Hunter, C. T., III, Lu, C.-A., Li, X., Bleecker, A. B., Koch, K. E., McCann, M. C., McCarty, D. R., Patterson, S. E., Reiter, W.-D., Staiger, C., Thomas, S. R., Vermerris, W., and Carpita, N. C., 2005, Genomics of plant cell wall biogenesis, Planta 221:745-751.
87. Zhang, K., Qian, Q., Huang, Z., Wang, Y., Li, M., Hong, L., Zeng, D., Gu, M., Chu, C., and Cheng, Z., 2006, GOLD HULL AND INTERNODE2 encodes a primarily multifunctional cinnamyl-alcohol dehydrogenase in rice, Plant Physiol. 140:972-983.
88. De Neergaard, E., 1997, Methods in Botanical Histopathology, Danish Government Institute of Seed Pathology for Developing Countries, Copenhagen, pp. 216.
89. Friebolin, H., 2004, Basic One- and Two-Dimensional NMR Spectroscopy, John Wiley & Sons, pp. 430.
90. Johnson, R. A., and Wichern, D. W., 1992, Applied Multivariate Statistical Analysis, Prentice Hall, Englewood Cliffs, NJ, pp. 767.
91. Keeler, J., 2005, Understanding NMR Spectroscopy, John Wiley & Sons, pp. 476.
92. Kemsley, E. K., 1998, Discriminant Analysis and Class Modelling of Spectroscopic Data, John Wiley & Sons Ltd, Chichester, UK, pp. 179.
93. Siesler, H. W., Ozaki, Y., Kawata, S., and Heise, H. M., 2002, Near Infrared Spectroscopy. Principles, Instruments, Applications, Wiley-VCH, Weinheim, Germany, pp. 348.
94. Sjöström, E., and Alen, R., 1999, Analytical Methods in Wood Chemistry, Pulping and Papermaking, Springer-Verlag, Berlin, pp. 316.