Alcohol cross-coupling products in cereal grains

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 21, 2004, Pages 6496-6502

  Bunzel, Mirko ^a   Ralph, John ^b,c   Lu, Fachuang ^b,c   Hatfield, Ronald D ^b   Steinhart, Hans ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b U S DAIRY FORAGE RESEARCH CENTER   (United States)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Cereal dietary fiber; Coniferyl alcohol; Cross coupling; DFRC method; Ferulic acid; Lignin

Indexed keywords

CONIFERYL ALCOHOL; DIMER; FERULIC ACID; GLYCEROL; LIGNIN; POLYSACCHARIDE; COUMARIC ACID; PHENOL DERIVATIVE;

ARTICLE; CEREAL; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DERIVATIZATION; DIETARY FIBER; FOOD COMPOSITION; GRAIN; PRECURSOR; REDUCTION; CHEMISTRY; MASS FRAGMENTOGRAPHY;

CEREALS; COUMARIC ACIDS; DIETARY FIBER; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LIGNIN; PHENOLS;

EID: 6344284795     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf040204p     Document Type: Article

References (39)

1. Prosky, L. When is dietary fiber considered a functional food? Biofactors 2000, 12, 289-297.
2. Plaami, S. P. Content of dietary fiber in foods and its physiological effects. Food Rev. Int. 1997, 13, 29-76.
3. Harris, P. J.; Ferguson, L. R. Dietary fibres may protect or enhance carcinogenesis. Mutat. Res. 1999, 443, 95-110.
4. Glitso, L. V.; Jensen, B. B.; Knudsen, K. E. B. In vitro fermentation of rye carbohydrates including arabinoxylans of different structure. J. Sci. Food Agric. 2000, 80, 1211-1218.
5. Ryden, P.; Robertson, J. A. The effect of fibre source and fermentation on the apparent binding properties of wheat bran preparations for the mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx). Carcinogenesis 1995, 16, 209-216.
6. Manas, E.; Bravo, L.; Saura-Calixto, F. Sources of error in dietary fibre analysis. Food Chem. 1994, 50, 331-342.
7. Jin, Z.; Akiyama, T.; Chung, B. Y.; Matsumoto, Y.; Iiyama, K.; Watanabe, S. Changes in lignin content of leaf litters during mulching. Phytochemistry 2003, 64, 1023-1031.
8. Lam, T. B. T.; Iiyama, K.; Stone, B. A. Cinnamic acid bridges between cell-wall polymers in wheat and Phalaris internodes. Phytochemistry 1992, 31, 1179-1183.
9. Ishii, T. Structure and functions of feruloylated polysaccharides. Plant Sci. 1997, 127, 111-127.
10. Jacquet, G.; Pollet, B.; Lapierre, C.; Mhamdi, F.; Rolando, C. New ether-linked ferulic acid-coniferyl alcohol dimers identified in grass straws. J. Agric. Food Chem. 1995, 43, 2746-2751.
11. 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 1992, 2961-2969.
12. 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 1992, 2971-2980.
13. Ralph, J.; Grabber, J. H.; Hatfield, R. D. Lignin-ferulate cross-links in grasses: active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr. Res. 1995, 275, 167-178.
14. Grabber, J. H.; Hatfield, R. D.; Ralph, J.; Zon, J.; Amrhein, N. Ferulate cross-linking in cell-walls isolated from maize cell-suspensions. Phytochemistry 1995, 40, 1077-1082.
15. Quideau, S.; Ralph, J. Lignin-ferulate cross-links in grasses. Part 4. Incorporation of 5-5-coupled dehydrodiferulate into synthetic lignin. J. Chem. Soc., Perkin Trans. 1 1997, 2351-2358.
16. Grabber, J. H.; Ralph, J.; Hatfield, R. D. Model studies of ferulate-coniferyl alcohol cross-product formation in primary maize walls: Implications for lignification in grasses. J. Agric. Food Chem. 2002, 50, 6008-6016.
17. Bunzel, M.; Ralph, J.; Marita, J. M.; Hatfield, R. D.; Steinhart, H. Diferulates as structural components in soluble and insoluble cereal dietary fibre. J. Sci. Food Agric. 2001, 81, 653-660.
18. 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.
19. Grabber, J. H.; Ralph, J.; Hatfield, R. D. Modeling lignification in grasses with monolignol dehydropolymerisate-cell wall complexes. In Lignin and Lignan Biosynthesis; Lewis, N. G., Sarkanen, S., Eds.; American Chemical Society: Washington, DC, 1998; pp 163-171.
20. Quideau, S.; Ralph, J. Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol. J. Agric. Food Chem. 1992, 40, 1108-1110.
21. Lu, F.; Ralph, J. The DFRC method for lignin analysis. Part 1. A new method for β-aryl ether cleavage: Lignin model studies. J. Agric. Food Chem. 1997, 45, 4655-4660.
22. Bunzel, M.; Ralph, J.; Marita, J.; Steinhart, H. Identification of 4-O-5′-coupled diferulic acid from insoluble cereal fiber. J. Agric. Food Chem. 2000, 48, 3166-3169.
23. Lu, F.; Ralph, J. Derivatization followed by reductive cleavage (DFRC method), a new method for lignin analysis: Protocol for analysis of DFRC monomers. J. Agric. Food Chem. 1997, 45, 2590-2592.
24. Brunow, G.; Lundquist, K. On the acid-catalyzed alkylation of lignins. Holzforschung 1991, 45, 37-40.
25. Fukushima, R. S.; Hatfield, R. D. Extraction and isolation of lignin for utilization as a standard to determine lignin concentration using the acetyl bromide spectrophotometric method. J. Agric. Food Chem. 2001, 49, 3133-3139.
26. Lam, T. B. T.; Iiyama, K.; Stone, B. A. Changes in phenolic-acids from internode walls of wheat and phalaris during maturation. Phytochemistry 1992, 31, 2655-2658.
27. Ralph, J.; Hatfield, R. D.; Grabber, J. H.; Jung, H. G.; Quideau, S.; Helm, R. F. Cell wall cross-linking in grasses by ferulates and diferulates. In Lignin and Lignan Biosynthesis; Lewis, N. G., Sarkanen, S., Eds.; American Chemical Society: Washington, DC, 1998; pp 209-236.
28. Ralph, J.; Helm, R. F. Lignin/hydroxycinnamic acid/polysaccharide complexes: Synthetic models for regiochemical characterization. In Forage Cell Wall Structure and Digestibility, International Symposium; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 201-246.
29. Scalbert, A.; Monties, B.; Rolando, C.; Sierra-Escudero, A. Formation of ether linkage between phenolic acids and Gramineae lignin: a possible mechanism involving quinone methides. Holzforschung 1986, 40, 191-195.
30. Ralph, J.; Quideau, S.; Grabber, J. H.; Hatfield, R. D. Identification and synthesis of new ferulic acid dehydrodimers present in grass cell-walls. J. Chem. Soc., Perkin Trans. 1 1994, 3485-3498.
31. Lam, T. B. T.; Kadoya, K.; Iiyama, K. Bonding of hydroxycinnamic acids to lignin: ferulic and p-coumaric acids are predominantly linked at the benzyl position of lignin, not the β-position, in grass cell walls. Phytochemistry 2001, 57, 987-992.
32. Terashima, N.; Fukushima, K.; He, L.-F.; Takabe, K. Comprehensive model of the lignified plant cell wall. In Forage Cell Wall Structure and Digestibility; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 247-270.
33. Lapierre, C. Application of new methods for the investigation of lignin structure. In Forage Cell Wall Structure and Digestibility; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 133-166.
34. Antoine, C.; Peyron, S.; Mabille, F.; Lapierre, C.; Bouchet, B.; Abecassis, J.; Rouau, X. Individual contribution of grain outer layers and their cell wall structure to the mechanical properties of wheat bran. J. Agric. Food Chem. 2003, 51, 2026-2033.
35. Begum, A. N.; Nicolle, C.; Mila, I.; Lapierre, C.; Nagano, K.; Fukushima, K.; Heinonen, S.-M.; Adlercreutz, H.; Remesy, C.; Scalbert, A. Dietary lignins are precursors of mammalian lignans in rats. J. Nutr. 2004, 134, 120-127.
36. Lu, F.; Ralph, J. The DFRC method for lignin analysis. Part 2. Monomers from isolated lignins. J. Agric. Food Chem. 1998, 46, 547-552.
37. Johnson, D. B.; Moore, W. E.; Zank, L. C. The spectrophotometric determination of lignin in small wood samples. Tappi 1961, 44, 793-798.
38. Hatfield, R. D.; Grabber, J. H.; Ralph, J.; Brei, K. Using the acetyl bromide assay to determine lignin concentrations in herbaceous plants: Some cautionary notes. J. Agric. Food Chem. 1999, 47, 628-632.
39. Lapierre, C.; Pollet, B.; Ralet, M. C.; Saulnier, L. The phenolic fraction of maize bran: Evidence for lignin - heteroxylan association. Phytochemistry 2001, 57, 765-772.