Lignin-Hydrolyzable Tannin Interactions in Wood

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 8, 1997, Pages 3100-3106

  Helm, Richard F ^a   Ranatunga, Thilini D ^a   Chandra, Mudit ^a  

^a Fralin Life Science Institute   (United States)

Author keywords

Chestnut; DHP; Ellagic acid; Ellagitannins; Gallic acid; Lignin; NMR; Oak

Indexed keywords

CASTANEA DENTATA; QUERCUS; QUERCUS ALBA;

EID: 0001548690     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970083b     Document Type: Article

References (35)

1. Antus, S.; Baitz-Gács, E.; Bauer, R.; Gottsegen, A.; Seligmann, O.; Wagner, H. Regioselective Synthesis of 2- and 3-Aryl-1,4-benzodioxanes. Liebigs Ann. Chem. 1989, 1147-1151.
2. Armitage, R.; Bayliss, G. S.; Gramshaw, J. W.; Haslam, E.; Haworth, R. D.; Jones, K.; Rogers, H. J.; Searle, T. Gallotannins. Part III. The Constitution of Chinese, Turkish, Sumach and Tara Tannins. J. Chem. Soc. 1961, 1842-1853.
3. Boden, E. P.; Keck, G. E. Proton-Transfer Steps in Steglich Esterification: A Very Practical New Method for Macrolactonization. J. Org. Chem. 1985, 50, 2394-2395.
4. Ebermann, R.; Stich, K. Peroxidase and Amylase Isoenzymes in the Sapwood and Heartwood of Trees. Phytochemistry 1982, 21, 2401-2402.
5. Glasser, W. G.; Barnett, C. A.; Sano, Y. Classification of Lignins with Different Genetic and Industrial Origins. J. Appl. Polym. Sci: Appl. Polym. Symp. 1983, 37, 441-460.
6. Goyal, S.; Narula, P. K.; Sharma, P.; Parthasarathy, M. R. Synthetic Approach to Eusiderin Type Neolignans. Indian J. Chem. 1993, 32B, 435-439.
7. Haslam, E.; Cai, Y. Plant Polyphenols (Vegetable Tannins): Gallic Acid Metabolism. Nat. Prod. Rep. 1994, 41-46.
8. Helm, R. F.; Ralph, J. Lignin-Hydroxycinnamyl Model Compounds Related to Forage Cell Wall Structure. 1. Ether-Linked Structures. J. Agric. Food Chem. 1992, 40, 2167-2175.
9. Helm, R. F.; Ralph, J. Stereospecificity for the Zinc Borohydride Reduction of α-Aryloxy-β-hydroxy Ketones. J. Wood Chem. Technol. 1993, 13, 593-601.
10. Hillis, W. E. Heartwood and Tree Exudates; Springer-Verlag: Berlin, 1987; 268 pp.
11. Jurd, L. Plant Polyphenols. VI. Experiments on the Synthesis of 3,3- and 4,4-Di-O-methylellagic Acid. J. Am. Chem. Soc. 1959, 81, 4606-4610.
12. 14C]Lignins. Proc. Natl. Acad. Sci. USA 1975, 72, 2515-2519.
13. Mumpers, J.; Scalbert, A.; Janin, G. Ellagitannins in European Oak Wood: Polymerization During Wood Ageing. Phytochemistry 1994, 36, 1249-1252.
14. Kodera, M.; Tanahashi, M.; Higuchi, T. Dehydrogenative Copolymerization of D-Catechin and Coniferyl Alcohol. Wood Res. 1979, 65, 1-10.
15. 14C Labeled 3-Methoxy-4-hydroxy-α-(2-methoxyphenoxy)-β-hydroxypropiophenone, a Lignin Model Compound. Holzforschung 1981, 35, 66-69.
16. Loehle, C. Tree Life History Strategies: The Role of Defenses. Can. J. For. Res. 1988, 18, 209-222.
17. Luck, G.; Liao, H.; Murray, N. J.; Grimmer, H. R.; Warminski, E. E.; Williamson, M. P.; Lilley, T. H.; Haslam, E. Polyphenols, Astrigency and Proline-Rich Proteins. Phytochemistry 1994, 37, 357-371.
18. Masson, G.; Puech, J.-L.; Moutounet, M. Localization of the Ellagitannins in the Tissues of Quercus robur and Quercus petraea Woods. Phytochemistry 1994, 37, 1245-1249.
19. Masson, G.; Moutounet, M.; Puech, J.-L. Ellagitannin Content of Oak Wood as a Function of Species and of Sampling Position in the Tree. Am. J. Enol. Vitic. 1995, 46, 262-268.
20. Mayer, W.; Hoffmann, E. H.; Lösch, N.; Wolf, H.; Wolter, B.; Schilling, G. Dehydrierungsreaktionen mit Gallussäureestern. Leibigs Ann. Chem. 1984, 929-938.
21. Mila, I.; Scalbert, A.; Expert, D. Iron Withholding by Plant Polyphenols and Resistance to Pathogens and Rots. Phytochemistry 1996, 42, 1551-1555.
22. Okuda, T.; Yoshida, T.; Hatano, T. New Methods of Analyzing Tannins. J. Nat. Prod. 1989, 52, 1-31.
23. Peng, S.; Scalbert, A.; Monties, B. Insoluble Ellagitannins in Castanea sativa and Quercus petraea Woods. Phytochemistry 1991, 30, 775-778.
24. Pospisil, F.; Cvikrová, M.; Hrubcová, M. Oxidation of Gallic Acid by an Enzyme Preparation Isolated from the Culture of Medium of Nicotiana tabacum Cell Suspension. Biol. Plant. 1983, 25, 373-377.
25. Quideau, S.; Ralph, J. Facile Large Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol. J. Agric. Food Chem. 1992, 40, 1108-1110.
26. Ralph, J.; Helm, R. F. Rapid Proton NMR Method for Determination of Threo:Erythro Ratios in Lignin Model Compounds and Examination of Reduction Stereochemistry. J. Agric. Food Chem. 1991, 39, 705-709.
27. Ralph, J.; Helm, R. F.; Quideau, S.; Hatfield, R. D. Lignin-Feruloyl Ester Cross Links in Grasses. Part 1. Incorporation of Feruloyl Esters into Coniferyl Alcohol Dehydrogenation Polymers. J. Chem. Soc., Perkin Trans, 1, 1992a, 2961-2969.
28. Ralph, J.; Helm, R. F.; Quideau, S. Lignin-Feruloyl Ester Cross Links in Grasses. Part 2. Model Compound Syntheses. J Chem. Soc., Perkin Trans, 1, 1992b, 2971-2980.
29. Scalbert, A. Tannins in Woods and Their Contribution to Microbial Decay Prevention. In Plant Polyphenols; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 935-952.
30. Stewart, C. M. Excretion and Heartwood Formation in Living Trees. Science 1966, 153, 1068-1074.
31. Stich, V. K.; Ebermann, R. Peroxidase- und Polyphenoloxidaseisoenzyme im Splint- und Kernholz der Eiche. Holzforschung 1984, 38, 239-242.
32. Viriot, C.; Scalbert, A.; Herve du Penhoat, C. L. M.; Moutounet, M. Ellagitannins in Woods of Sessile Oak and Sweet Chestnut, Dimerization and Hydrolysis During Wood Ageing, Phytochemistry 1994, 36, 1253-1260.
33. Vivas, N.; Laguerre, M.; Glories, Y.; Bourgeois, G.; Vitry, C. Structure Simulation of Two Ellagitannins from Quercus robur L. Phytochemistry 1995, 39, 1193-1199.
34. Yoshizawa, S.; Horiuchi, T.; Suganuma, M.; Nishiwaki, S.; Yatsunami, J.; Okabe, S.; Okuda, T.; Muto, Y.; Frenkel, K.; Troll, W.; Fujiki, H. Penta-O-galloyl β-D-Glucose and (-)-Epigallocatechin Gallate, Cancer Preventative Agents. In Phenolic Compounds in Food and Their Effects on Health; Huang, M.-T., Ho, C.-T., Lee, C. Y., Eds.; ACS Symposium Series 507; American Chemical Society; Washington, DC, 1992; Vol. 2, pp 316-325.
35. Zucker, W. V. Tannins; Does Structure Determine Function? An Ecological Perspective. Am. Nat. 1983, 121, 335-365.