Oat Phenolics: Biochemistry and Biological Functionality

Oats: Chemistry and Technology: Second Edition

Volumn , Issue , 2011, Pages 157-217

  Collins, F W ^a  

^a AGRICULTURE AND AGRI FOOD CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOLICS;

EID: 84902738584     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-1-891127-64-9.50015-4     Document Type: Chapter

References (453)

1. Adam A., Crespy V., Levrat-Verny M.-A., Leenhardt F., Leuillet M., Demigne C., Remesy C. The bioavailability of ferulic acid is governed primarily by the food matrix rather than its metabolism in intestine and liver in rats. J. Nutr. 2002, 132:1962-1968.
2. Adams E.L., Kroon P.A., Williamson G., Morris V.J. AFM studies of water-soluble wheat arabinoxylans-Effects of esterase treatment. Carbohydr. Res. 2005, 340:1841-1845.
3. Adlercreutz H. Phyto-oestrogens and cancer. Lancet Oncol. 2002, 3:364-373.
4. Adlercreutz H. Phytoestrogens and breast cancer. J. Steroid Biochem. Mol. Biol. 2003, 1803:1-6.
5. Adlercreutz H., Fotsis T., Kurzer M.S., Wähälä K., Mäkelä T., Hase T. Isotope dilution gas chromatographic-mass spectrometric method for the determination of unconjugated lignans and isoflavonoids in human feces, with preliminary results in omnivorous and vegetarian women. Anal. Biochem. 1995, 225:101-106.
6. Adom K.K., Liu R.H. Antioxidant activity of grains. J. Agric. Food Chem. 2002, 50:6182-6187.
7. Allerdings E., Ralph J., Schatz P.F., Gniechwitz D., Steinhart H., Bunzel M. Isolation and structural identification of diarabinosyl 8-O-4-dehydrodiferulate from maize bran insoluble fiber. Phytochemistry 2005, 66:113-124.
8. Andreasen M.F., Christensen L.P., Meyer A.S., Hansen Å. Ferulic acid dehydrodimers in rye (Secale cereale L.). J. Cereal Sci. 2000, 31:303-307.
9. Andreasen M.F., Christensen L.P., Meyer A.S., Hansen Å. Content of phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties. J. Agric. Food Chem. 2000, 48:2837-2842.
10. Andreasen M.F., Landbo A.-K., Christensen L.P., Hansen Å., Meyer A.S. Antioxidant effects of phenolic rye (Secale cereale L.) extracts, monomeric hydroxycinnamates, and ferulic acid dehydrodimers on human low-density lipoproteins. J. Agric. Food Chem. 2001, 49:4090-4096.
11. Andreasen M.F., Kroon P.A., Williamson G., Garcia-Conesa M.-T. Esterase activity able to hydrolyze dietary antioxidant hydroxycinnamates is distributed along the intestine of mammals. J. Agric. Food Chem. 2001, 49:5679-5684.
12. Andreasen M.F., Kroon P.A., Williamson G., Garcia Conesa M.-T. Intestinal release and uptake of phenolic antioxidant diferulic acids. Free Radic. Biol. Med. 2001, 31:304-314.
13. Anselmi C., Centini M., Granata P., Sega A., Buonocore A., Bernini A., Facino R.M. Antioxidant activity of ferulic acid alkyl esters in a heterophasic system: A mechanistic insight. J. Agric. Food Chem. 2004, 52:6425-6432.
14. 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.
15. Arrieta-Baez D., Stark R.E. Modeling suberization with peroxidase-catalyzed polymerization of hydroxycinnamic acids: Cross-coupling and dimerization reactions. Phytochemistry 2006, 67:743-753.
16. Arts I.C.W., Hollman P.C.H. Polyphenols and disease risk in epidemiologic studies. Am. J. Clin. Nutr. 2005, 81(Suppl.):317S-325S.
17. Arts M.J.T.J., Haenen G.R.M.M., Voss H.-P., Bast A. Antioxidant capacity of reaction products limits the applicability of the Trolox equivalent antioxidant capacity (TEAC) assay. Food Chem. Toxicol. 2004, 42:45-49.
18. Auerbach R.T., Gray D.A. Oat antioxidant extraction and measurement-Towards a commercial process. J. Sci. Food Agric. 1999, 79:385-389.
19. Axelson M., Setchell K.D.R. Conjugation of lignans in human urine. FEBS Lett. 1980, 122:49-53.
20. Axelson M., Setchell K.D.R. The excretion of lignans in rats-Evidence for an intestinal bacterial source for this new group of compounds. FEBS Lett. 1981, 123:337-342.
21. Axelson M., Sjövall J., Gustafsson B.E., Setchell K.D.R. Origin of lignans in mammals and identification of a precursor from plants. Nature 1982, 298:659-660.
22. Ayyangar N.R., Lugade A.G., Sane M.G., Srinivasan K.V. Separation of 2-amino-3H-phenoxazin-3-one impurity from o-aminophenol. J. Chromatogr. 1981, 209:113-116.
23. Azuma K., Ippoushi K., Nakayama M., Ito H., Higashio H., Terao J. Absorption of chlorogenic acid and caffeic acid in rats after oral administration. J. Agric. Food Chem. 2000, 48:5496-5500.
24. Baeumker P.A., Arendt S., Wiermann R. The metabolism of ferulic acid sucrose esters in anthers of Tulipa cultivar Apeldoorn. I. The accumulation of esters and free sugars. Z. Naturforsch. Sect. C. Biosciences 1988, 43:641-646.
25. Baghestani A., Lemieux C., Leroux G.D., Baziramakenga R., Simard R.R. Determination of allelochemicals in spring cereals of different competitiveness. Weed Sci. 1999, 47:498-504.
26. Bartolomé B., Faulds C.B., Kroon P.A., Waldron K., Gilbert H.J., Hazelwood G., Williamson G. An Aspergillus niger esterase (ferulic acid esterase III) and a recombinant Pseudomonas fluorescens subsp. cellulosa esterase (XylD) release a 5-5 ferulic dehydrodimer (diferulic acid) from barley and wheat cell walls. Appl. Environ. Microbiol. 1997, 63:208-212.
27. Basset G.J.C., Quinlivan E.P., Ravanel S., Rebeille F., Nichols B.P., Shinozaki K., Seki M., Adams-Phillips L.C., Giovannoni J.J., Gregory J.F., Hanson A.D. Folate synthesis in plants: The p-aminobenzoate branch is initiated by a bifunctional PabA-PabB protein that is targeted to plastids. Proc. Natl. Acad. Sci. U.S.A. 2004, 101:1496-1501.
28. Basset G.J.C., Ravanel S., Quinlivan E.P., White R., Giovannoni J.J., Rebeille F., Nichols B.P., Shinozaki K., Seki M., Gregory J.F., Hanson A.D. Folate synthesis in plants: The last step of the p-aminobenzoate branch is catalyzed by a plastidial aminodeoxychorismate lyase. Plant J. 2004, 40:453-461.
29. Beaugrand J., Cronier D., Debeire P., Chabbert B. Arabinoxylan and hydroxycinnamate content of wheat bran in relation to endoxylanase susceptibility. J. Cereal Sci. 2004, 40:223-230.
30. Beaugrand J., Cronier D., Thiebeau P., Schreiber L., Debeire P., Chabbert B. Structure, chemical composition, and xylanase degradation of external layers isolated from developing wheat grain. J. Agric. Food Chem. 2004, 52:7108-7117.
31. Beaugrand J., Paës G., Reis D., Takahashi M., Debeire P., O'Donohue M., Chabbert B. Probing the cell wall heterogeneity of micro-dissected wheat caryopsis using both active and inactive forms of a GH11 xylanase. Planta 2005, 222:246-257.
32. Bellés J.M., Garro R., Fayos J., Navarro P., Primo J., Conejero V. Gentisic acid as a pathogen-inducible signal, additional to salicylic acid for activation of plant defenses in tomato. Mol. Plant-Microbe Interact. 1999, 12:227-235.
33. Bernards M.A. Demystifying suberin. Can. J. Bot. 2002, 80:227-240.
34. Bernards M.A., Lewis N.G. The macromolecular aromatic domain in suberized tissue: A changing paradigm. Phytochemistry 1998, 47:915-933.
35. Bernards M.A., Razem F.A. The poly(phenolic) domain of potato suberin: A non-lignin cell wall bio-polymer. Phytochemistry 2001, 57:1115-1122.
36. Bernards M.A., Lopez M.L., Zajicek J., Lewis N.G. Hydroxycinnamic acid-derived polymers constitute the polyaromatic domain of suberin. J. Biol. Chem. 1995, 270:7382-7386.
37. Bily A.C., Reid L.M., Taylor J.H., Johnston D., Malouin C., Burt A.J., Bakan B., Regnault-Roger C., Pauls K.P., Arnason J.T., Philogèn B.J.R. Dehydrodimers of ferulic acid in maize grain pericarp and aleurone: Resistance factors to Fusarium graminearum. Phytopathology 2003, 93:712-719.
38. Bingham S.A., Day N.E., Luben R., Ferrari P., Slimani N., Norat T., Clavel-Chapelon F., Kesse E., Nieters A., Boeing H., Tjonneland A., Overvad K., Martinez C., Dorronsoro M., Gonzalez C.A., Key T.J., Trichopoulou A., Naska A., Vineis P., Tumino R., Krogh V., Bueno-De-Mesquita H.B., Peeters P.H.M., Berglund G., Hallmans G., Lund E., Skeie G., Kaaks R., Riboli E. Dietary fibre in food and protection against colorectal cancer in the European Prospective Investigation into Cancer and Nutrition (EPIC): An observational study. Lancet 2003, 361:1491-1501.
39. Boccardo F., Punoti M., Guglielmini P., Rubagotti A. Enterolactone as a risk factor for breast cancer: A review of the published evidence. Clin. Chim. Acta 2006, 365:58-67.
40. Boerjan W., Ralph J., Baucher M. Lignin biosynthesis. Annu. Rev. Plant Biol. 2003, 54:519-546.
41. Borriello S.P., Setchell K.D., Axelson M., Lawson A.M. Production and metabolism of lignans by human faecal flora. J. Appl. Bacteriol. 1985, 58:37-43.
42. Bouaziz M., Simmonds M.S.J., Grayer R.J., Kite G.C., Damak M. Flavonoids from Hyparrhenia hirta Stapf. (Poaceae) growing in Tunisia. Biochem. Syst. Ecol. 2001, 29:849-851.
43. Bouaziz M., Veitch N.C., Grayer R.J., Simmonds M.S.J., Damak M. Flavonolignans from Hyparrhenia hirta. Phytochemistry 2002, 60:515-520.
44. Bourne L.C., Rice-Evans C. Bioavailability of ferulic acid. Biochem. Biophys. Res. Commun. 1998, 253:222-227.
45. Bowyer P., Clarke B.R., Lunness P., Daniels M.J., Osbourn A.E. Host range of a plant pathogenic fungus determined by a saponin detoxifying enzyme. Science 1995, 267:371-374.
46. Bratt K., Sunnerheim K., Bryngelsson S., Fagerlund A., Engman L., Andersson R.E., Dimberg L.H. Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships. J. Agric. Food Chem. 2003, 51:594-600.
47. Braune A., Gütschow M., Engst W., Blaut M. Degradation of quercetin and luteolin by Eubacterium ramulus. Appl. Environ. Microbiol. 2001, 67:5558-5567.
48. Brazier M., Cole D.J., Edwards R. Partial characterisation of a 2,4,5-trichlorophenol detoxifying O-glucosyltransferase from wheat. Phytochemistry 2003, 64:419-424.
49. Breinholt V.M., Offord E.A., Brouwer C., Nielsen S.E., Brøsen K., Friedberg T. In vitro investigation of cytochrome P450-mediated metabolism of dietary flavonoids. Food Chem. Toxicol. 2002, 40:609-616.
50. Brett C.T., Wende G., Smith A.C., Waldron K.W. Biosynthesis of cell-wall ferulate and diferulates. J. Sci. Food Agric. 1999, 79:421-424.
51. Bringmann G., Lang G. Full absolute stereostructures of natural products directly from crude extracts: The HPLC-MS/MS-NMR-CD "triad." Prog. Mol. Subcell. Biol. 2003, 37:89-116.
52. Broughton W.J., Jabbouri S., Perret X. Keys to symbiotic harmony. J. Bacteriol. 2000, 182:5641-5652.
53. Bruce R.J., West C.A. Elicitation of lignin biosynthesis and isoperoxidase activity by pectic fragments in suspension cultures of castor bean. Plant Physiol. 1989, 91:889-897.
54. Bryngelsson S., Mannerstedt-Fogelfors B., Kamal-Eldin A., Andersson R., Dimberg L.H. Lipids and antioxidants in groats and hulls of Swedish oats (Avena sativa L.). J. Sci. Food Agric. 2002, 82:606-614.
55. Bryngelsson S., Dimberg L.H., Kamal-Eldin A. Effects of commercial processing on levels of antioxidants in oats (Avena sativa L.). J. Agric. Food Chem. 2002, 50:1890-1896.
56. Bryngelsson S., Ishihara A., Dimberg L.H. Levels of avenanthramides and activity of hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyl transferase (HHT) in steeped or germinated oat samples. Cereal Chem. 2003, 80:356-360.
57. Bryngelsson S., Sunnerheim K., Holm C., Dimberg L.H. Tentative avenanthramide-modifying enzyme in oats. Cereal Chem. 2003, 80:361-364.
58. Bungenberg de Jong H.L., Klaar W.J., Vliegenthart J.A.A. A precursor of methoxy-parabenzoquinone in wheat germ. Nature (London) 1953, 172:402-403.
59. Bungenberg de Jong, H. L., Klaar, W. J., and Vliegenthart, J. A. A. 1955. Glycosides and their importance in the wheat germ. Proc. Int. Bread Congr., 3rd., Sec. I, 29-33. Arbeitsgemeinschaft Getreide Forschung, Detmold, Germany.
60. Bunzel M., Ralph J., Marita J.M., Steinhart H. Identification of 4-O-5-coupled diferulic acid from insoluble cereal fiber. J. Agric. Food Chem. 2000, 48:3166-3169.
61. Bunzel M., Ralph J., Marita J.M., Hatfield R.D., Steinhart H. Diferulates as structural components in soluble and insoluble cereal dietary fiber. J. Sci. Food Agric. 2001, 81:653-660.
62. Bunzel M., Allerdings E., Sinwell V., Ralph J., Steinhart H. Cell wall hydroxycinnamates in wild rice (Zizania aquatica L.) insoluble dietary fibre. Eur. Food Res. Technol. 2002, 214:482-488.
63. Bunzel M., Ralph J., Funk C., Steinhart H. Isolation and identification of a ferulic acid dehydrotrimer from saponified maize bran insoluble fiber. Eur. Food Res. Technol. 2003, 217:128-133.
64. Bunzel M., Ralph J., Kim H., Lu F., Ralph S.A., Marita J.M., Hatfield R.D., Steinhart H. Sinapate dehydrodimers and sinapate heterodimers in cereal dietary fiber. J. Agric. Food Chem. 2004, 51:1427-1434.
65. Bunzel M., Funk C., Steinhart H. Semipreparative isolation of dehydrodiferulic and dehydrotriferulic acids as standard substances from maize bran. J. Sep. Sci. 2004, 27:1080-1086.
66. Bunzel M., Ralph J., Lu F., Hatfield R.D., Steinhart H. Lignin and ferulate-coniferyl alcohol cross-coupling products in cereal grains. J. Agric. Food Chem. 2004, 52:6496-6502.
67. Buttery R.G., Orts W.J., Takeoka G.R., Nam Y. Volatile flavor components of rice cakes. J. Agric. Food Chem. 1999, 47:4353-4356.
68. Calhoun W.K., Hepburn F.N., Bradley W.B. The distribution of the vitamins of wheat in commercial mill products. Cereal. Chem. 1960, 37:755-761.
69. Carpita N.C. Structure and biogenesis of the cell walls of grasses. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1996, 47:445-476.
70. Carpita N.C., McCann M.C. The functions of cell wall polysaccharides in composition and architecture revealed through mutations. Plant Soil 2002, 247:71-80.
71. Carter J.P., Spink J., Cannon P.F., Daniels M.J., Osbourn A.E. Isolation, characterization, and avenacin sensitivity of a diverse collection of cereal-root-colonizing fungi. Appl. Environ. Microbiol. 1999, 65:3364-3372.
72. Cavaliere C., Foglia P., Pastorini E., Samperi R., Laganà A. Identification and mass spectrometric characterization of glycosylated flavonoids in Triticum durum plants by high-performance liquid chromatography with tandem mass spectrometry. Rapid Comm. Mass Spec. 2005, 19:3143-3158.
73. Chatonnet P., Dubourdieu D., Boidron J.N., Lavigne V. Synthesis of volatile phenols by Saccharomyces cerevisiae in wines. J. Sci. Food Agric. 1993, 62:191-202.
74. Chen C.-Y., Milbury P.E., Kwak H.-K., Collins F.W., Samuel P., Blumberg J.B. Avenanthramides and phenolic acids from oats are bioavailable and act synergistically with vitamin C to enhance hamster and human LDL resistance to oxidation. J. Nutr. 2004, 134:1459-1466.
75. Chen C.-Y., Milbury P.E., Collins F.W., Blumberg J. Avenanthramides are bioavailable and have antioxidant activity in humans after acute consumption of an enriched mixture from oats. J. Nutr. 2007, 137:1375-1382.
76. Chesson A., Provan G.J., Russell W.R., Scobbie L., Richardson A.J., Stewart C. Hydroxycinnamic acids in the digestive tract of livestock and humans. J. Sci. Food Agric. 1999, 79:373-378.
77. Cho S., Johnson G., Song W.O. Folate content of foods: Comparison between databases compiled before and after new FDA fortification requirements. J. Food Comp. Anal. 2002, 15:293-307.
78. Chong J., Baltz R., Schmitt C., Beffa R., Fritig B., Saindrenan P. Downregulation of a pathogen-responsive tobacco UDP-glc: Phenylpropanoid glucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance. Plant Cell 2002, 14:1093-1107.
79. Chopin J., Dellamonica G., Bouillant M.L., Besset A., Popovici G., Weissenbock G. C-glycosylflavones from Avena sativa. Phytochemistry 1977, 16:2041-2043.
80. Clifford M.N. Chlorogenic acids and other cinnamates-Nature, occurrence and dietary burden. J. Sci. Food Agric. 1999, 79:362-372.
81. Cochrane M.P. Morphology of the crease region in relation to assimilate uptake and water loss during caryopsis development in barley and wheat. Aust. J. Plant Physiol. 1983, 10:473-491.
82. Cochrane M.P., Paterson L., Gould E. Changes in chalazal cell walls and in the peroxidase enzymes of the crease region during grain development in barley. J. Exp. Bot. 2000, 51:507-520.
83. Coghe S., Benoot K., Delvaux F., Vanderhaegen B., Delvaux F.R. Ferulic acid release and 4-vinylguaiacol formation during brewing and fermentation: Indications for feruloyl esterase activity in Saccharomyces cerevisiae. J. Agric. Food Chem. 2004, 52:602-608.
84. Collins F.W. Oat phenolics: Isolation and structural elucidation of substituted benzoxazinones. Cereal Foods World 1983, 28:560.
85. Collins F.W. Oat phenolics: Structure, occurrence, and function. Oats: Chemistry and Technology 1986, 227-295. Am. Assoc. Cereal Chem., St. Paul, MN. 1st ed. F.H. Webster (Ed.).
86. Collins F.W. Oat phenolics: Avenanthramides, novel substituted N-cinnamoylanthranilate alkaloids from oat groats and hulls. J. Agric. Food Chem. 1989, 37:60-66.
87. Collins F.W. Advances in the preparative liquid chromatography of bioactive phytochemicals. J. Clin. Ligand Assay 2000, 23:273-282.
88. Collins F.W., Mullin W.J. High-performance liquid chromatographic determination of avenanthramides, N-aroylanthranilic acid alkaloids from oats. J. Chromatogr. 1988, 445:363-370.
89. Collins, F. W., and Paton, D. 1992. Methods of producing stable bran and flour products from cereal grains. U.S. patent 5,169,660.
90. Collins F.W., Mclachlan D.C., Blackwell B.A. Oat phenolics: Avenalumic acids, a new group of bound phenolic acids from oat groats and hulls. Cereal Chem. 1991, 68:184-189.
91. Conchie J., Moreno A., Cardini E.C. A trisaccharide glycoside from wheat germ. Arch. Biochem. Biophys. 1961, 94:342-343.
92. Correira S.J., David J.P., David J.M. Constituintes das cascas de Tapinira guianensi (Anacardiaceae). Quim. Nova 2003, 26:36-38.
93. Cortés-Cruz M., Snook M., McMullen M.D. The genetic basis of C-glycosyl flavone B-ring modification in maize (Zea mays L.) silks. Genome 2003, 46:182-194.
94. Crombie L., Crombie W.M., Whiting D.A. Isolation of Avenacins A-1, A-2, B-1, and B-2 from oat roots: Structures of their "aglycones," the avenestergens. J. Chem. Soc. Chem. Commun. 1984, 4:244-246.
95. Crombie L., Crombie W.M., Whiting D.A. Structures of the four avenacins, oat root resistance factors to "take-all" disease. J. Chem. Soc. Chem. Commun. 1984, 4:246-248.
96. Crombie L., Crombie W.M., Whiting D.A. Structures of the oat root resistance factors to "take-all" disease, avenacins A-1, A-2, B-1, and B-2 and their companion substances. J. Chem. Soc. Perkin Trans. 1986, 1:1917-1922.
97. Crombie W.M., Crombie L. Distribution of avenacins A-1, A-2, B-1, and B-2 in oat roots: Their fungicidal activity towards "take-all" fungus. Phytochemistry 1986, 25:2069-2073.
98. Crombie W.M.L., Crombie L., Green J.B., Lucas J.A. Pathogenicity of the take-all fungus to oats: Its relationship to the concentration and detoxification of the four avenacins. Phytochemistry 1986, 25:2075-2083.
99. Daniels D.G.H. The estimation and location of methoxyhydroquinone glycosides in the wheat grain. Cereal Chem. 1959, 36:32-41.
100. Daniels D.G.H., Martin H.F. Isolation of a new antioxidant from oats. Nature (London) 1961, 191:1302.
101. Daniels D.G.H., Martin H.F. Structures of two antioxidants isolated from oats. Chem. Ind. London 1964, 1964:2058.
102. Daniels D.G.H., Martin H.F. Antioxidants in oats: Diferulates of long-chain diols. Chem. Ind. London 1965, 1965:1763.
103. Daniels D.G.H., Martin H.F. Antioxidants in oats: Mono-esters of caffeic and ferulic acids. J. Sci. Food Agric. 1967, 18:385-390.
104. Daniels D.G.H., Martin H.F. Antioxidants in oats: Glyceryl-esters of caffeic and ferulic acids. J. Sci. Food Agric. 1968, 19:710-712.
105. Daniels D.G.H., King H.G.C., Martin H.F. Antioxidants in oats: Esters of phenolic acids. J. Sci. Food Agric. 1963, 14:385-390.
106. Davin L.D., Lewis N.G. Dirigent phenoxy radical coupling: Advances and challenges. Curr. Opin. Biotechnol. 2005, 16:398-406.
107. Day A.F., Dupont M.S., Ridley S., Rhodes M., Rhodes M.J.C., Morgan M.R.A., Williamson G. Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver β-glucosidase activity. FEBS Lett. 1998, 436:71-75.
108. Dean B., Chang S., Doss G.A., King P.E., Thomas P.E. Glucuronidation, oxidative metabolism, and bioactivation of enterolactone in Rhesus monkeys. Arch. Biochem. Biophys. 2004, 429:244-251.
109. Deng Y.-R., Song A.-X., Wang H.-O. Chemical components of Seriphidium santolium Poljak. J. Chin. Chem. Soc. 2004, 51:629-636.
110. Dimberg L.H., Theander O., Lingnert H. Avenanthramides-A group of phenolic antioxidants in oats. Cereal Chem. 1993, 70:637-641.
111. Dimberg L.H., Molteberg E.L., Solheim R., Frølich W. Variation in oat groats due to variety, storage and heat treatment. I: Phenolic compounds. J. Cereal Sci. 1996, 24:263-272.
112. Dimberg L.H., Sunnerheim K., Sundberg B., Walsh K. Stability of oat avenanthramides. Cereal Chem. 2001, 78:278-281.
113. Dimberg L.H., Andersson R.E., Gohil S., Bryngelsson S., Lundgren L.N. Identification of a sucrose diester of a substituted α-truxinic acid in oats. Phytochemistry 2001, 56:843-847.
114. Dimberg L.H., Gissen C., Nilsson J. Phenolic compounds in oat grains (Avena sativa L.) grown in conventional and organic systems. Ambio 2005, 34:331-337.
115. Dixon R.A., Palva N.L. Stress-induced phenylpropanoid metabolism. Plant Cell 1995, 7:1085-1097.
116. Dixon R.A., Reddy M.S.S. Biosynthesis of monolignols. Genomic and reverse genetic approaches. Phytochem. Rev. 2003, 2:289-306.
117. Dixon R.A., Chen F., Guo D., Parvathi K. The biosynthesis of monolignols: A "metabolic grid," or independent pathways to guaiacyl and syringyl units?. Phytochemistry 2001, 57:1069-1084.
118. Dokuyucu T., Peterson D.M., Akkaya A. Content of antioxidant compounds in Turkish oats: Simple phenolics and avenanthramide concentrations. Cereal Chem. 2003, 80:542-543.
119. Donaldson L.A. Lignification, and lignin topochemistry-An ultrastructural view. Phytochemistry 2001, 57:859-873.
120. Douglas C.J. Phenylpropanoid metabolism and lignin synthesis: From weeds to trees. Trends Plant Sci. 1996, 1:171-178.
121. Dreyer D.L., Jones K.C. Feeding deterrency of flavonoids and related phenolics towards Schizaphus graminum and Myzus persicae: Aphid feeding deterrents in wheat. Phytochemistry 1981, 20:2489-2493.
122. Durkee A.B., Thivierge P.A. Ferulic acid and other phenolics in oat seeds (Avena sativa L. var. Hinoat). J. Food Sci. 1977, 42:551-552.
123. Emmons C.L., Peterson D.M. Antioxidant activity and phenolic contents of oat groats and hulls. Cereal Chem. 1999, 76:902-906.
124. Emmons C.L., Peterson D.M. Antioxidant activity and phenolic content as affected by cultivar and location. Crop Sci. 2001, 41:1676-1681.
125. Emmons C.L., Peterson D.M., Paul G.L. Antioxidant capacity of oat (Avena sativa L.) extracts. 2. In vitro antioxidant activity and contents of phenolic and tocol antioxidants. J. Agric. Food Chem. 1999, 47:4894-4898.
126. r apoplastic inhibitor. Planta 2005, 223:77-89.
127. Erkkilä A.T., Herrington D.M., Mozaffarian D., Lichtenstein A.H. Cereal fiber and whole-grain intake are associated with reduced progression of coronary-artery atherosclerosis in postmenopausal women with coronary artery disease. Am. Heart J. 2005, 150:94-101.
128. Facchini P.J., Hagel J., Zulak K.G. Hydroxycinnamic acid amide metabolism: Physiology and biochemistry. Can. J. Bot. 2002, 80:577-589.
129. Faulds C.B., Sancho A.I., Bartolomé B. Mono- and dimeric ferulic acid release from brewer's spent grain by fungal feruloyl esterases. Appl. Microbiol. Biotechnol. 2002, 60:489-493.
130. Faulds C.B., Zanichelli D., Crepin V.F., Connerton I.F., Juge N., Bhat M.K., Waldron K.W. Specificity of feruloyl esterases for water-extractable and water-unextractable feruloylated polysaccharides: Influence of xylanase. J. Cereal Sci. 2003, 38:281-288.
131. Fenech M., Noakes M., Clifton P., Topping D. Aleurone flour is a rich source of bioavailable folate in humans. J. Nutr. 1999, 129:1114-1119.
132. Fenech M., Noakes M., Clifton P., Topping D. Aleurone flour increases red-cell folate and lowers homocyst(e)ine substantially in man. Br. J. Nutr. 2005, 93:353-360.
133. Ferguson L.R., Lim I.F., Pearson A.E., Ralph J., Harris P.J. Bacterial antimutagenesis by hydroxycinnamic acids from plant cell walls. Mutat. Res. 2003, 542:49-58.
134. Fiddler W., Parker W.E., Wasserman A.E., Doerr R.C. Thermal decomposition of ferulic acid. J. Agric. Food Chem. 1967, 15:757-761.
135. Fomsgaard I.S., Mortensen A.G., Carlsen S.C.K. Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals-A review. Chemosphere 2004, 54:1025-1038.
136. Ford J.D., Huang K.-S., Wang H.-B., Davin L.B., Lewis N.G. Biosynthetic pathway to the cancer chemoprotective secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed. J. Nat. Prod. 2001, 64:1388-1397.
137. Fotsis T., Heikkinen R., Adlercreutz H., Axelson M., Setchell K.D. Capillary gas chromatographic method for the analysis of lignans in human urine. Clin. Chim. Acta 1982, 121:361-371.
138. Freisleben A., Schieberle P., Rychlik M. Specific and sensitive quantification of folate vitamers in foods by stable isotope dilution assays using high-performance liquid chromatography-tandem mass spectrometry. Anal. Bioanal. Chem. 2003, 376:149-156.
139. Friebe A., Vilich V., Hennig L., Kluge M., Sicker D. Detoxification of benzoxazolinone allelochemicals from wheat by Gaeumannomyces graminis var. tritici, G. graminis var. graminis, G. graminis var. avenae, and Fusarium culmorum. Appl. Environ. Microbiol. 1998, 64:2386-2391.
140. Fritsche J., Angoelal R., Dachtler M. On-line liquid-chromatography-nuclear magnetic resonance spectroscopy-mass spectrometry coupling for the separation and characterization of secoisolariciresinol diglucoside isomers in flaxseed. J. Chromatogr. A 2002, 972:195-203.
141. Fry S.C. Intracellular feruloylation of pectic polysaccharides. Planta 1987, 171:205-211.
142. Fry S.C. Oxidative coupling of tyrosine and ferulic acid residues: Intra- and extra-protoplasmic occurrence, predominance of trimers and larger products, and possible role in inter-polymeric cross-linking. Phytochem. Rev. 2004, 3:97-111.
143. Fry S.C., Willis S.C., Paterson A.E. Intraprotoplasmic and wall-localised formation of arabinoxylan-bound diferulates and larger ferulate coupling-products in maize cell-suspension cultures. Planta 2000, 211:679-692.
144. Fulcher R.G., O'Brien T.P., Wong S.I. Microchemical detection of niacin, aromatic amine, and phytin reserves in cereal bran. Cereal Chem. 1981, 58:130-135.
145. Funk C., Weber P., Thilker J., Grabber J.H., Steinhart H., Bunzel M. Influence of lignification and feruloylation of maize cell walls on the adsorption of heterocyclic aromatic amines. J. Agric. Food Chem. 2006, 54:1860-1867.
146. Fuss E. Lignans in plant cell and organ cultures: An overview. Phytochem. Rev. 2003, 2:307-320.
147. Gagliardo R.W., Chilton W.S. Soil transformation of 2(3H)-benzoxazolinone of rye into phytotoxic 2-amino-3H-phenoxazin-3-one. J. Chem. Ecol. 1992, 18:1683-1691.
148. Ganry O. Phytoestrogens and prostate cancer risk. Prev. Med. 2005, 41:1-6.
149. Garcia E.S., Azambuja P. Lignoids in insects: Chemical probes for the study of ecdysis, excretion and Tripanosoma cruzi-triatomine interactions. Toxicon 2004, 44:431-440.
150. Garcia-Conesa M.T., Plumb G.W., Kroon P.A., Wallace G., Williamson G. Antioxidant properties of ferulic acid dimers. Redox. Rep. 1997, 3:239-244.
151. Garcia-Conesa M.T., Plumb G.W., Waldron K.W., Ralph J., Williamson G. Ferulic acid dehydrodimers from wheat bran: Isolation, purification and antioxidant properties of 8-O-diferulic acid. Redox. Rep. 1997, 3:319-323.
152. Garcia-Conesa M.T., Kroon P.A., Ralph J., Mellon F.A., Colquhoun I.J., Saulnier L., Thibault J.-F., Williamson G. A cinnamoyl esterase from Aspergillus niger can break plant cell wall cross-links without release of free diferulic acids. Eur. J. Biochem. 1999, 266:644-652.
153. Gatford K., Eastwood R.F., Halloran G.M. Germination inhibitors in bracts surrounding the grain of Triticum tauschii. Funct. Plant Biol. 2002, 29:881-890.
154. Geissmann T., Neukom H. On the composition of the water-soluble wheat flour pentosans and their oxidative gelation. Lebensm. Wiss. Technol. 1973, 6:59-62.
155. Gerber N.N. Phenoxazinones by oxidative dimerization of aminophenols. Can. J. Chem. 1968, 46:790-792.
156. Gerhäuser C. Beer constituents as potential cancer chemopreventive agents. Eur. J. Cancer 2005, 41:1941-1954.
157. Gierl A., Frey M. Evolution of benzoxazinone biosynthesis and indole production in maize. Planta 2001, 213:493-498.
158. Glawischnig E., Grün S., Frey M., Gierl A. Cytochrome P450 monooxygenases of DIBOA biosynthesis: Specificity and conservation among the grasses. Phytochemistry 1999, 50:925-930.
159. Glitsø L.V., Mazur W.M., Adlercreutz H., Wähälä K., Mäkelä T., Sandström B., Bach Knudsen K.E. Intestinal metabolism of rye lignans in pigs. Br. J. Nutr. 2000, 84:429-437.
160. Glitsø L.V., Jensen B.B., Knudsen E.B. In vitro fermentation of rye carbohydrates including arabinoxylans of different structure. J. Sci. Food Agric. 2000, 80:1211-1218.
161. Gonthier M.-P., Verny M.A., Besson C., Remesy C., Scalbert A. Chlorogenic acid bioavailability largely depends on its metabolism by the gut microflora in rats. J. Nutr. 2003, 133:1853-1859.
162. González L.F., Rojas M.C., Perez F.J. Diferulate and lignin formation is related to biochemical differences of wall-bound peroxidases. Phytochemistry 1999, 49:711-717.
163. Goodey A.R., Tubb R.S. Genetic and biochemical analysis of the ability of Saccharomyces cerevisiae to decarboxylate cinnamic acids. J. Gen. Microbiol. 1982, 128:2615-2620.
164. Goodwin B.L., Ruthven C.R.J., Sandler M. Gut flora and the origin of some urinary aromatic phenolic compounds. Biochem. Pharmacol. 1994, 47:2294-2297.
165. Goodwin R.H., Pollock B.M. Studies on roots. I. Properties and distribution of fluorescent constituents in Avena roots. Am. J. Bot. 1954, 41:416-420.
166. Grabber J.H. How do lignin composition, structure, and cross-linking affect degradability? A review of cell wall models. Crop Sci. 2005, 45:820-831.
167. 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.
168. Graça J., Schreiber L., Rodrigues J., Pereira H. Gylcerol and glyceryl esters of α-hydroxyacids in cutins. Phytochemistry 2002, 61:205-215.
169. Grace S.C., Logan B.A. Energy dissipation and radical scavenging by the plant phenylpropanoid pathway. Philos. Trans. R. Soc. London Biol. Sci. 2000, 355(1402):1499-1510.
170. Graf B.A., Milbury P.E., Blumberg J.B. Flavonols, flavones, flavanones, and human health: Epidemiological evidence. J. Med. Food 2005, 8:281-290.
171. Grayer R.J., Harborne J.B. A survey of antifungal compounds from higher plants, 1982-1993. Phytochemistry 1994, 37:19-42.
172. Grayer R.J., Harborne J.B., Kimmins E.M., Stevenson F.C., Wijayagunasekera H.N.P. Phenolics in rice phloem sap as sucking deterrents to the brown plant hopper Nilaparvata lugens. Acta Hort. 1994, 381:691-694.
173. Grün S., Frey M., Gierl A. Evolution of the indole alkaloid biosynthesis in the genus Hordeum: Distribution of gramine and DIBOA and isolation of the benzoxazinoid biosynthesis genes from Hordeum lechleri. Phytochemistry 2005, 66:1264-1272.
174. Gubler F., Ashford A.E., Basic A., Blakeney A.B., Stone B.A. Release of ferulic acid esters from barley aleurone. II. Characterization of the feruloyl compounds released in response to GA3. Aust. J. Plant Physiol. 1985, 12:307-317.
175. Hahlbrock K., Grisebach H. Biosynthesis of flavonoids. The Flavonoids 1975, 866-915. Academic Press, New York. J.B. Harborne, T.J. Mabry, H. Mabry (Eds.).
176. Halliwell B., Rafter J., Jenner A. Health promotion by flavonoids, tocopherols, tocotrienols, and other phenols: Direct or indirect effects? Antioxidant or not?. Am. J. Clin. Nutr. 2005, 81(Suppl.):268S-276S.
177. Hallmans G., Zhang J.-X., Lundin E., Stattin P., Johansson A., Johansson I., Hultén K., Winkvist A., Lenner P., Åman P., Adlercreutz H. Rye, lignans and human health. Proc. Nutr. Soc. 2003, 62:193-199.
178. Halls S.C., Davin L.B., Kramer D.M., Lewis N.G. Kinetic study of coniferyl alcohol radical binding to the (+)-pinoresinol forming dirigent protein. Biochemistry 2004, 43:2587-2595.
179. Handelman G.J., Cao G., Walter M.F., Nightingale Z.D., Paul G.L., Prior R.L., Blumberg J.B. Antioxidant capacity of oat (Avena sativa L.) extracts. 1. Inhibition of low-density lipoprotein oxidation and oxygen radical absorbance capacity. J. Agric. Food Chem. 1999, 47:4888-4893.
180. Hanson A.D., Gregory J.F. Synthesis and turnover of folates in plants. Curr. Opin. Plant Biol. 2002, 5:244-249.
181. Harborne J.B. Variation in and functional significance of phenolic conjugation in plants. Recent Adv. Phytochem. 1977, 12:457-474.
182. Harborne J.B., Grayer R.N. Flavonoids and insects. The Flavonoids: Advances in Research Since 1986 1993, 589-618. Chapman and Hall, London. J.B. Harborne (Ed.).
183. Harborne J.B., Hall E. Plant polyphenols. XII. The occurrence of tricin and of glycoflavones in grasses. Phytochemistry 1964, 3:421-428.
184. Harborne J.B., Williams C.A. Flavonoid patterns in leaves of the Gramineae. Biochem. Syst. Ecol. 1976, 4:267-280.
185. Harborne J.B., Williams C.A. Advances in flavonoid research since 1992. Phytochemistry 2000, 55:481-504.
186. Hargrove J.L., Greenspan P., Hartle D.K. Nutritional significance and metabolism of very long chain fatty alcohols and acids from dietary waxes. Exp. Biol. Med. 2004, 229:215-226.
187. Harmatha J., Dinan L. Biological activities of lignans and stilbenoids associated with plant-insect chemical interactions. Phytochem. Rev. 2003, 2:321-330.
188. Harris P.J., Chavan R.R., Ferguson L.R. Production and characterization of two wheat-bran fractions: An aleurone-rich and a pericarp-rich fraction. Mol. Nutr. Food Res. 2005, 49:536-545.
189. Hartley R.D., Jones E.C. Effect of ultraviolet light on substituted cinnamic acids and estimation of their cis and trans isomers by gas chromatography. J. Chromatogr. 1975, 107:213-218.
190. Hattori M., Shu Y.-Z., El-Sedawy A.I., Namba T., Kobashi K., Tomimora T. Metabolism of homoorientin by human intestinal bacteria. J. Nat. Prod. 1988, 51:874-878.
191. Heinonen S., Nurmi T., Liukkonen K., Poutanen K., Wähälä K., Deyama T., Nishibe S., Adlercreutz H. In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol. J. Agric. Food Chem. 2001, 49:3178-3186.
192. Heller W., Forkmann G. Biosynthesis of flavonoids. The Flavonoids: Advances in Research Since 1986 1993, 500-535. Chapman and Hall, London. J.B. Harborne (Ed.).
193. Herrmann K. Hydroxyzimtsauren und hydroxybenzosauren enhaltende Naturstoffe in Pflanzen. Fortschr. Chem. Org. Naturst. 1978, 35:73-132.
194. Herrmann K. Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods. Crit. Rev. Food Sci. Nutr. 1989, 28:315-347.
195. Hoikkala A.A., Schiavoni E., Wähälä K. Analysis of phyto-oestrogens in biological matrices. Br. J. Nutr. 2003, 89(Suppl. 1):S5-S18.
196. Hollman P.C.H., Arts I.C.W. Flavonols, flavones and flavanols-Nature, occurrence and dietary burden. J. Sci. Food Agric. 2000, 80:1081-1093.
197. Hollman P.C.H., Katan M.B. Dietary flavonoids: Intake, health effects and bioavailability. Food Chem. Toxicol. 1999, 37:937-942.
198. Hu M., Chen J., Lin H. Metabolism of flavonoids via enteric recycling: Mechanistic studies of disposition of apigenin in the Caco-2 cell culture model. J. Pharmacol. Exp. Ther. 2003, 307:314-321.
199. Huang Y.T., Lee L.T., Lee P.P., Lin Y.S., Lee M.T. Targeting of focal adhesion kinase by flavonoids and small-interfering RNAs reduces tumor cell migration ability. Anticancer Res. 2005, 25(3B):2017-2025.
200. Humphreys J.M., Chapple C. Rewriting the lignin roadmap. Curr. Opin. Plant Biol. 2002, 5:224-229.
201. Humphreys J.M., Hemm M.R., Chapple C. New routes for lignin biosynthesis defined by biochemical characterization of recombinant ferulate 5-hydroxylase, a multifunctional cytochrome P450-dependent monooxygenase. Proc. Natl. Acad. Sci. U.S.A. 1999, 96:10045-10050.
202. Hwang K.T., Weller C.L., Cuppett S.L., Hanna M.A. Policosanol contents and compositions of grain sorghum kernels and dried distillers grains. Cereal Chem. 2004, 81:345-349.
203. Hwang K.T., Weller C.L., Cuppett S.L., Hanna M.A. Policosanol contents and composition in wax-like materials extracted from selected cereals of Korean origin. Cereal Chem. 2005, 82:242-245.
204. Ikegawa T., Mayama S., Nakayashiki H., Kato H. Accumulation of diferulic acid during the hypersensitive response of oat leaves to Puccinia coronata f. sp. avenae and its role in the resistance of oat tissue to cell wall degrading enzymes. Physiol. Mol. Plant Pathol. 1996, 48:245-255.
205. Irmak S., Dunford N.T. Policosanol contents and compositions of wheat varieties. J. Agric. Food Chem. 2005, 53:5583-5586.
206. 2+ ion in phytoalexins induction in oats. Plant Sci. 1996, 115:9-19.
207. Ishihara A., Matsukawa T., Miyagawa H., Ueno T., Mayama S., Iwamura H. Induction of hydroxycinnamoyl-CoA: hydroxyanthranilate N-hydroxycinnamoyltransferase (HHT) activity in oat leaves by victorin C. Z. Naturforsch. 1997, 52c:756-760.
208. Ishihara A., Miyagawa H., Matsukawa T., Ueno T., Mayama S., Iwamura H. Induction of hydroxyanthranilate hydroxycinnamoyl transferase activity by oligo-N-acetylchito-oligosaccharides in oats. Phytochemistry 1998, 47:969-974.
209. Ishihara A., Ohtsu Y., Iwamura H. Biosynthesis of oat avenanthramide phytoalexins. Phytochemistry 1999, 50:237-242.
210. Ishihara A., Ohtsu Y., Iwamura H. Induction of biosynthetic enzymes for avenanthramides in elicitor-treated oat leaves. Planta 1999, 208:512-518.
211. Ishii T. Structure and functions of feruloylated polysaccharides. Plant Sci. 1997, 127:111-127.
212. Jacobs D.R., Marquart L., Slavin J.L., Kushi L.H. Whole-grain intake and cancer: An expanded review and meta-analysis. Nutr. Cancer 1998, 30:85-96.
213. Jacobs D., Pereira M., Slavin J., Marquart L. Defining the impact of whole-grain intake on chronic disease. Cereal Foods World 2000, 45:51-53.
214. Jansen G.H.E., Arts I.C.W., Nielen M.W.F., Müller M., Hollman P.C.H., Keijer J. Uptake and metabolism of enterolactone and enterodiol by human colon epithelial cells. Arch. Biochem. Biophys. 2005, 435:74-82.
215. Jay M., Ismaili A. Flavone and C-glycosylflavones from the leaves of some Arrenatherum species. Phytochemistry 1989, 28:3035-3037.
216. Jensen M.K., Koh-Banerjee P., Hu F.B., Franz M., Sampson L., Grønbæk M., Rimm E.B. Intakes of whole grains, bran, and germ and the risk of coronary heart disease in men. Am. J. Clin. Nutr. 2004, 80:1492-1499.
217. Ji L.L., Lay D., Chung E., Fu Y., Peterson D.M. Effects of avenanthramides on oxidant generation and antioxidant enzyme activity in exercised rats. Nutr. Res. 2003, 23:1579-1590.
218. Kanno T., Kasai K., Ikejiri-Kanno Y., Wakasa K., Tozawa Y. In vitro reconstitution of rice anthranilate synthase: Distinct functional properties of the α subunits OASA1 and OASA2. Plant Mol. Biol. 2004, 54:11-23.
219. Karakaya S. Bioavailability of phenolic compounds. Crit. Rev. Food Sci. Nutr. 2004, 44:453-464.
220. Kato Y., Yamanouchi H., Hinata K., Ohsumi C., Hayashi T. Involvement of phenolic esters in cell aggregation of suspension-cultured rice cells. Plant. Physiol. 1994, 104:147-152.
221. Kato T., Tomita N., Yagi J., Taniguchi K., Takahashi N. A chemical evaluation of the role of rice husk toward growth regulation of rice seedlings. Recent Res. Dev. Agric. Biol. Chem. 1999, 3:43-50.
222. Kato T., Saito N., Kashimura K., Shinohara M., Kurahashi T., Taniguchi K. Germination and growth inhibitors from wheat (Triticum aestivum L.) husks. J. Agric. Food Chem. 2002, 50:6307-6312.
223. Kawasaki T., Koita H., Nakatsuba T., Hasegawa K., Wakabayashi K., Takahashi H., Umemura K., Umezawa T., Shimamoto K. Cinnamoyl-CoA reductase, a key enzyme in lignin biosynthesis, is an effector of small GTPase Rac in defense signalling in rice. Proc. Natl. Acad. Sci. U.S.A. 2006, 103:230-235.
224. Kern S.M., Bennett R.N., Mellon F.A., Kroon P.A., Garcia-Conesa M.-T. Absorption of hydroxycinnamates in humans after high-bran cereal consumption. J. Agric. Food Chem. 2003, 51:6050-6055.
225. Kern S.M., Bennett R.N., Needs P.W., Mellon F.A., Kroon P.A., Garcia-Conesa M.-T. Characterization of metabolites of hydroxycinnamates in the in vitro model of human small intestinal epithelium Caco-2 cells. J. Agric. Food Chem. 2003, 51:7884-7891.
226. Kerr E.M., Fry S.C. Pre-formed xyloglucans and xylans increase in molecular weight in three distinct compartments of a maize cell-suspension culture. Planta 2003, 217:327-339.
227. Kerr E.M., Fry S.C. Extracellular cross-linking of xylan and xyloglucan in maize cell-suspension cultures: The role of oxidative phenolic coupling. Planta 2004, 219:73-83.
228. Khant G. Trans-cis-equilibrium of hydroxycinnamic acids during irradiation of aqueous solutions at different pH. Phytochemistry 1967, 6:755-758.
229. Kikuzaki H., Hisamoto M., Hirose K., Akiyama K., Taniguchi H. Antioxidant properties of ferulic acid and its related compounds. J. Agric. Food Chem. 2002, 50:2161-2168.
230. Knogge W., Weissenböck G. Purification, characterization, and kinetic mechanism of S-adenosyl-L-methionine: Vitexin 2-O-rhamnoside 7-O-methyltransferase of Avena sativa L. Eur. J. Biochem. 1984, 140:113-118.
231. Knudsen K.E.B., Serena A., Kjaer A.K.B., Tetens I., Heinonen S.-M., Nurmi T., Adlercreutz H. Rye bread in the diets of pigs enhances the formation of enterolactone and increases its level in plasma, urine and feces. J. Nutr. 2003, 133:1368-1375.
232. Kodicek E., Wilson P.W. The isolation of niacytin, the bound form of nicotinic acid. Biochem. J. 1960, 76:27-28.
233. Koetz R., Amado R., Neukom H. Nature of bound nicotinic acid in wheat bran. Lebensm. Wiss. Technol. 1979, 12:346-349.
234. Kolattukudy P.E. Polyesters in higher plants. Adv. Biochem. Eng. Biotechnol. 2001, 71:1-19.
235. Konishi Y., Kobayashi S. Microbial metabolites of ingested caffeic acid are absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers. J. Agric. Food Chem. 2004, 52:6418-6424.
236. Konishi Y., Shimizu M. Transepithelial transport of ferulic acid by monocarboxylic acid transporter in Caco-2 cell monolayers. Biosci. Biotechnol. Biochem. 2003, 67:856-862.
237. Konishi Y., Kobayashi S., Shimizu M. Transepithelial transport of p-coumaric acid and gallic acid in Caco-2 cell monolayers. Biosci. Biotechnol. Biochem. 2003, 67:2317-2324.
238. Konishi Y., Hitomi Y., Yoshioka E. Intestinal absorption of p-coumaric acid in rats after oral administration. J. Agric. Food Chem. 2004, 52:2527-2532.
239. Konishi Y., Hitomi Y., Yoshida M., Yoshioka E. Pharmacokinetic study of caffeic and rosmarinic acids in rats after oral administration. J. Agric. Food Chem. 2005, 53:4740-4746.
240. Koshihara Y., Neichi T., Murota S., Lao A., Fujimoto Y., Tatsuno T. Caffeic acid is a selective inhibitor for leukotriene biosynthesis. Biochem. Biophys. Acta 1984, 792:92-97.
241. Kota P., Guo D., Zubieta C., Noel J., Dixon R.A. O-Methylation of benzaldehyde derivatives by "lignin specific" caffeic acid 3-O-methyltransferase. Phytochemistry 2004, 65:837-846.
242. Kristensen B.K., Burhenne K., Rasmussen S.K. Peroxidases and the metabolism of hydroxycinnamic acid amides in Poaceae. Phytochem. Rev. 2004, 3:127-140.
243. Kuijsten A., Arts I.C.W., Vree T.B., Hollman P.C.H. Pharmacokinetics of enterolignans in healthy men and women consuming a single dose of secoisolariciresinol diglucoside. J. Nutr. 2005, 135:795-801.
244. Kunst L., Samuels A.L. Biosynthesis and secretion of plant cuticular wax. Prog. Lipid Res. 2003, 42:51-81.
245. Laberge M.A., Moore K.J., Freeman M.W. Atherosclerosis and innate immune signalling. Ann. Med. 2005, 37:130-140.
246. Labib S., Hummel S., Richling E., Humpf H.-U., Schreier P. Use of the pig caecum to mimic the human intestinal metabolism of hispidulin and related compounds. Mol. Nutr. Food Res. 2006, 50:78-86.
247. 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.
248. Lam T.B.T., Iiyama K., Stone B.A. Hot alkali-labile linkages in the walls of the forage grass Phalaris aquatica and Lolium perenne and their relation to the in vitro wall digestibility. Phytochemistry 2003, 64:603-607.
249. Lampe J.W. Isoflavonoid and lignan phytoestrogens as dietary markers. J. Nutr. 2003, 133(Suppl.):S956-S964.
250. 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.
251. Lequart C., Nuzillard J.-M., Kurek B., Debeire P. Hydrolysis of wheat bran and straw by an endoxylanase: Production and structural characterization of cinnamoyl-oligosaccharides. Carbohydr. Res. 1999, 319:102-111.
252. Lin Y.-T., Hsiu S.-L., Hou Y.-C., Chen H.-Y., Chao P.-D.L. Degradation of flavonoid aglycones by rabbit, rat and human fecal flora. Biol. Pharm. Bull. 2003, 26:747-751.
253. Liu L., Zubik L., Collins F.W., Marko M., Meydani M. The atherogenic potential of oat phenolic compounds. Atherosclerosis 2004, 175:39-49.
254. Liukkonen K.-H., Katina K., Wilhelmsson A., Myllymäki O., Lampi A.-M., Kariluoto S., Piironen V., Heinonen S.-M., Nurmi T., Adlercreutz H., Peltoketo A., Pihlava J.-M., Hietaniemi V., Poutanen K. Process-induced changes on bioactive compounds in whole rye. Proc. Nutr. Soc. 2003, 62:117-122.
255. Lofty S., Negrel J., Javelle F. Formation of β-feruloyloxypalmitic acid by an enzyme from wound-healing potato tuber discs. Phytochemistry 1994, 35:1419-1424.
256. Lofty S., Javelle F., Negrel J. Distribution of hydroxycinnamoyl-CoA: β-hydroxypalmitic acid O-hydroxycinnamoyl-transferase in higher plants. Phytochemistry 1995, 40:389-391.
257. Lozovaya V.V., Lygin A.V., Li S., Hartman G.L., Widholm J.M. Biochemical response of soybean roots to Fusarium solani f. sp. glycines infection. Crop Sci. 2004, 44:819-826.
258. Ma Y. Allelopathic studies of common wheat (Triticum aestivum L.). Weed Biol. Manage. 2005, 5:93-104.
259. Mabry T.J., Markham K.R., Thomas M.B. The Systematic Identification of Flavonoids 1970, Springer-Verlag, Berlin.
260. Mace M.E., Hebert T.T. Naturally occurring quinones in wheat and barley and their toxicity to loose smut fungi. Phytopathology 1963, 53:692-700.
261. Maggi-Capeyron M.-F., Ceballos P., Cristol J.-P., Delbosc S., Le Doucen C., Pons M., Léger C.L., Descomps B. Wine phenolic antioxidants inhibit AP-1 transcriptional activity. J. Agric. Food Chem. 2001, 49:5646-5652.
262. Manach C., Williamson G., Morand C., Scalbert A., Remesy C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr. 2005, 81(Suppl.):230S-242S.
263. Manju V., Balasubramaniyan V., Nalini N. Rat colonic lipid peroxidation and antioxidant status: The effects of dietary luteolin on 1,2-dimethylhydrazine challenge. Cell. Mol. Biol. Lett. 2005, 10:535-551.
264. Markham K.R., Tanner G.J., Caasi-Lit M., Whitecross M.I., Nayudu M., Mitchell K.A. Possible protective role for 34-dihydroxyflavones induced by enhanced UV-B in a UV-tolerant rice cultivar. Phytochemistry 1998, 49:1913-1919.
265. Martin-Tanguy J., Cabanne F., Perdrizet E., Martin C. The distribution of hydroxycinnamic acid amides in flowering plants. Phytochemistry 1978, 17:1927-1928.
266. Martin-Tanguy J., Perdrizet E., Prevost J., Martin C. Hydroxycinnamic acid amides in fertile and cytoplasmic male sterile lines of maize. Phytochemistry 1982, 21:1939-1945.
267. Mason J.B., Kodicek E. The identification of o-aminophenol and o-aminophenyl glucoside in wheat bran. Cereal Chem. 1973, 50:646-654.
268. Mason J.B., Gibson N., Kodicek E. The chemical nature of the bound nicotinic acid of wheat bran: Studies of nicotinic acid-containing macromolecules. Br. J. Nutr. 1973, 30:297-311.
269. Matsukawa T., Isobe T., Ishihara A., Iwamura H. Occurrence of avenanthramides and hydroxycinnamoyl-CoA: hydroxyanthranilate N-hydroxycinnamoyltransferase activity in oat seeds. Z. Naturforsch. 2000, 55c:30-36.
270. Matsukawa T., Ishihara A., Iwamura H. Induction of anthranilate synthase activity by elicitors in oats. Z. Naturforsch. [C] 2002, 57:121-128.
271. Mayama S., Tani T. Microspectrophotometric analysis of the location of avenalumin accumulation in oat Avena sativa cult. SHOKAN-1 leaves in response to fungal infection. Physiol. Plant Pathol. 1982, 21:141-150.
272. Mayama S., Tani T., Matsuura Y., Ueno T. The production of phytoalexins by oat Avena sativa in response to crown rust Puccinia coronata f. sp. avenae. Physiol. Plant Pathol. 1981, 19:217-226.
273. Mayama S., Matsuura Y., Iida H., Tani T. The role of avenalumins in the resistance of oat to crown rust Puccinia coronata f. sp. avenae. Physiol. Plant Pathol. 1982, 20:189-200.
274. Mayama S., Bordin A.P.A., Morikawa T., Tanpo H., Kato H. Association between avenalumin accumulation, infection hypha length and infection type in oat crosses segregating for resistance to Puccinia coronata f. sp. avenae race 226. Physiol. Mol. Plant Pathol. 1995, 46:255-261.
275. Mayama S., Bordin A.P.A., Morikawa T., Tanpo H., Kato H. Association of avenalumin accumulation with co-segregation of victorin sensitivity and crown rust resistance in oats carrying the Pc-2 gene. Physiol. Mol. Plant Pathol. 1995, 46:263-274.
276. Mazur W., Adlercreutz H. Natural and anthropogenic environmental oestrogens: The scientific basis for risk assessment. Naturally occurring oestrogens in food. Pure Appl. Chem. 1998, 70:1759-1776.
277. Mazur W., Fotsis T., Wähälä K., Ojala S., Salakka A., Adlercreutz H. Isotope dilution gas chromatographic-mass spectrometric method for the determination of isoflavonoids, coumestrol, and lignans in food samples. Anal. Biochem. 1996, 233:169-180.
278. McCallum J.A., Taylor I.A.P., Towers G.H.N. Spectrophotometric assay and electrophoretic detection of trans-feruloyl esterase activity. Anal. Biochem. 1991, 196:360-366.
279. McKeehen J.D., Busch R.H., Fulcher R.G. Evaluation of wheat (Triticum aestivum L.) phenolic acids during grain development and their contribution to Fusarium resistance. J. Agric. Food Chem. 1999, 47:1476-1482.
280. McMullen M.D., Kross H., Snook M.E., Cortes-Cruz M., Houchins K.E., Musket T.A., Coe E.H. Salmon silk genes contribute to the elucidation of the flavone pathway in maize (Zea mays L.). J. Hered. 2004, 95:225-233.
281. Meilgaard M.C. Flavor chemistry of beer: Part II: Flavor and threshold of 239 aroma volatiles. Tech. Q. Master Brew. Assoc. Am. 1975, 12:151-168.
282. Meyer K., Cucumano J.C., Somerville C., Chapple C.C.S. Ferulate-5-hydroxylase from Arabidopsis thaliana defines a new family of cytochrome P450-dependent monooxygenases. Proc. Natl. Acad. Sci. U.S.A. 1996, 93:6869-6874.
283. Michela P., Lorenz K. The vitamins of triticale, wheat, and rye. Cereal Chem. 1976, 53:853-861.
284. Middleton E., Kandaswami C. The impact of plant flavonoids on mammalian biology: Implications for immunity, inflammation and cancer. The Flavonoids: Advances in Research Since 1986 1993, 619-652. Chapman and Hall, London. J.B. Harborne (Ed.).
285. Milder I.E.J., Arts I.C.W., Venema D.P., Lasaroms J.J.P., Wähälä K., Hollman P.C.H. Optimization of a liquid chromatography-tandem mass spectrometry method for quantification of the plant lignans secoisolariciresinol, matairesinol, lariciresinol and pinoresinol in foods. J. Agric. Food Chem. 2004, 52:4643-4651.
286. Milder I.E.J., Feskens E.J.M., Arts I.C.W., Bueno De Mesquita H.B., Hollman P.C.H., Kromhout D. Intake of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in Dutch men and women. J. Nutr. 2005, 135:1202-1207.
287. Milder I.E.J., Arts I.C.W., Van De Putte B., Venema D.P., Hollman P.C.H. Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. Br. J. Nutr. 2005, 95:393-402.
288. Miyagawa H., Ishihara A., Nishimoto T., Ueno T., Mayama S. Induction of avenanthramides in oat leaves inoculated with crown rust fungus, Puccinia coronata f. sp. avenae. Biosci. Biotechnol. Biochem. 1995, 59:2305-2306.
289. Miyagawa H., Ishihara A., Kuwahara Y., Ueno T., Mayama S. A stress compound in oats induced by victorin, a host-specific toxin from Helminthosporium victoriae. Phytochemistry 1996, 41:1473-1475.
290. Miyamoto K., Ueda J., Takeda S., Ida K., Hoson T., Masuda Y., Kamisaka S. Light-induced increase in the contents of ferulic and diferulic acids in cell-walls of Avena coleoptiles-Its relationship to growth inhibition by light. Physiol. Planta. 1994, 92:350-355.
291. Moyna P., Dellacassa E. Seed epicuticular wax of Avena sativa. Phytochemistry 1985, 24:179-180.
292. Mueller S.O., Simon S., Chae K., Metzler M., Korach K.S. Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor α (ERα) and ERα in human cells. Toxicol. Sci. 2004, 2004:14-25.
293. Murota K., Shimizu S., Miyamoto S., Izumi T., Obata A., Kikuchi M., Terao J. Unique uptake and transport of isoflavone aglycones by human intestinal Caco-2 cells: Comparison of isoflavones and flavonoids. J. Nutr. 2002, 132:1956-1961.
294. Murray R.D.H. Coumarins. Nat. Prod. Rep. 1989, 6:591-624.
295. Myton K.E., Fry S.C. Intraprotoplasmic feruloylation of arabinoxylans in Festuca arundinacea cell cultures. Planta 1994, 193:326-330.
296. Nabeta K., Kadota G., Tani T. O-rhamnosylisoswertisin from oats (Avena sativa). Phytochemistry 1977, 16:1112-1113.
297. Nagasawa H.T., Gutman H.R., Morgan M.A. The oxidation of o-aminophenols by cytochrome c and cytochrome oxidase. II. Synthesis and identification of oxidation products. J. Biol. Chem. 1959, 234:1600-1604.
298. Nair P.M., Vaidyanathan C.S. Isophenoxazine synthase. Biochem. Biophys. Acta 1964, 81:507-516.
299. Namazi M.R., Soma J. Tranilast: A novel weapon against insulin resistance. Med. Hypotheses 2005, 64:1135-1137.
300. Neudörffer A., Bonnefont-Rousselot D., Legrand A., Fleury M.-B., Largeron M.J. 4-Hydroxycinnamic ethyl ester derivatives and related dehydrodimers: Relationship between oxidation potential and protective effects against oxidation of low-density lipoproteins. J. Agric. Food Chem. 2004, 52:2084-2091.
301. Neukom H., Markwalder H.U. Oxidative gelation of wheat flour pentosans: A new way of cross-linking polymers. Cereal Foods World 1978, 23:374-376.
302. Ng C.H., Leung K.Y., Huang Y., Chen Z.Y. Policosanol has no antioxidant activity in human low-density lipoprotein but increases excretion of bile acids in hamsters. J. Agric. Food Chem. 2005, 53:6289-6293.
303. Ng S.P., Wong K.Y., Zhang L., Zuo Z. Evaluation of the first-pass glucuronidation of selected flavones in gut by Caco-2 monolayer model. J. Pharm. Pharmaceut. Sci. 2005, 8:1-9.
304. Nie L., Wise M.L., Peterson D.M., Meydani M. Avenanthramide, a polyphenol from oats, inhibits vascular smooth muscle cell proliferation and enhances nitric oxide production. Atherosclerosis 2006, 186:260-266.
305. Niemann G. The anthranilamide phytoalexins of the Caryophyllaceae and related compounds. Phytochemistry 1993, 34:319-328.
306. Niemeyer H.M. Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the Gramineae. Phytochemistry 1988, 27:3349-3358.
307. Niemeyer H., Honig D.M., Kulling S.E., Metzler M. Studies on the metabolism of the plant lignans secoisolariciresinol and matairesinol. J. Agric. Food Chem. 2003, 51:6317-6325.
308. Nilsson M., Åman P., Härkönen H., Hallmans G., Bach Knudsen K.E., Mazur W., Aclercreutz H. Content of nutrients and lignans in roller milled fractions of rye. J. Sci. Food Agric. 1997, 73:143-148.
309. Noel J.P., Austin M.B., Bomati E.K. Structure-function relationships in plant phenylpropanoid biosynthesis. Curr. Opin. Plant Biol. 2005, 8:249-253.
310. Nomura T., Ishihara A., Imaishi H., Ohkawa H., Endo T.R., Iwamura H. Rearrangement of the genes for the biosynthesis of benzoxazinones in the evolution of Triticeae species. Planta 2003, 217:776-782.
311. Nomura T., Ishihara A., Yanagita R.C., Endo T.R., Iwamura H. Three genomes differentially contribute to the biosynthesis of benzoxazinones in hexaploid wheat. Proc. Natl. Acad. Sci. U.S.A. 2005, 102:16490-16495.
312. Obel N., Porchia A.C., Scheller H.V. Intracellular feruloylation of arabinoxylan in wheat: Evidence for feruloyl-glucose as precursor. Planta 2003, 216:620-629.
313. Ohta T., Yamasaki S., Egashira Y., Sanada H. Antioxidative activity of corn bran hemicellulose fragments. J. Agric. Food Chem. 1994, 42:653-656.
314. Okazaki Y., Ishihara A., Nishioka T., Iwamura H. Identification of a dehydrodimer of avenanthramide phytoalexin in oats. Tetrahedron 2004, 60:4765-4771.
315. Okazaki Y., Isobe T., Iwata Y., Matsukawa T., Matsuda H., Ishihara A., Nishioka T., Iwamura H. Metabolism of avenanthramide phytoalexins in oats. Plant J. 2004, 39:560-572.
316. O'Leary K.A., Day A.J., Needs P.W., Sly W.S., O'Brien N.M., Williamson G. Flavonoid glucuronides are substrates for human liver β-glucuronidase. FEBS Lett. 2001, 503:103-106.
317. Olsen R.A. Methoxyhydroquinone, a growth inhibitor of Ophiobolus graminis in leaves of oat seedlings. Physiol. Plant. 1971, 24:34-39.
318. Olthof M.R., Hollman P.C.H., Katan M.B. Chlorogenic acid and caffeic acid are absorbed in humans. J. Nutr. 2001, 131:66-71.
319. Osada M., Imaoka S., Funae Y. Apigenin suppresses the expression of VEGF, an important factor for angiogenesis, in endothelial cells via degradation of HIF-1alpha protein. FEBS Lett. 2004, 575:59-63.
320. Osbourn A.E. Preformed antimicrobial compounds and plant defense against fungal attack. Plant Cell 1996, 8:1821-1831.
321. Osbourn A.E., Clarke B.R., Lunness P., Scott P.R., Daniels M.J. An oat species lacking avenacin is susceptible to infection by Gaeumannomyces graminis var. tritici. Physiol. Mol. Plant Pathol. 1994, 45:457-467.
322. Ososki A.L., Kennelly E.J. Phytoestrogens: A review of the present state of research. Phytother. Res. 2003, 17:845-869.
323. Ou S., Kwok K.-C. Ferulic acid: Pharmaceutical functions, preparation and applications in foods. J. Sci. Food Agric. 2004, 84:1261-1269.
324. Papadopoulou K., Melton R.E., Leggett M., Daniels M.J., Osbourn A.E. Compromised disease resistance in saponin-deficient plants. Proc. Natl. Acad. Sci. U.S.A. 1999, 96:12923-12928.
325. Peeters P.H.M., Keinan-Boker L., Van Der Schouw Y.T., Grobbee D.E. Phytoestrogens and breast cancer risk. Breast Cancer Res. Treat. 2003, 77:171-183.
326. Peñalvo J.L., Haajanen K.M., Botting N., Adlercreutz H. Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry. J. Agric. Food Chem. 2005, 53:9342-9347.
327. Peppercorn M.A., Goldman P. Caffeic acid metabolism by gnotobiotic rats and their intestinal bacteria. Proc. Natl. Acad. Sci. U.S.A. 1972, 69:1413.
328. Peters N.K., Frost J.W., Long S.R. A plant flavone, luteolin, induces expression of Rhizobium meliloti nodulation genes. Science 1986, 233:977-980.
329. Peters U., Sinha R., Chatterjee N., Subar A.F., Ziegler R.G., Kulldorff M., Bresalier R., Weissfeld J.L., Flood A., Schatzkin A., Hayes R.B. Dietary fibre and colorectal adenoma in a colorectal cancer early detection programme. Lancet 2003, 361:1491-1495.
330. Peterson D.M. Oat antioxidants. J. Cereal Sci. 2001, 33:115-129.
331. Peterson D.M., Emmons C.L., Hibbs A.H. Phenolic antioxidants and antioxidant activity in pearling fractions of oat groats. J. Cereal Sci. 2001, 33:97-103.
332. Peterson D.M., Hahn M.J., Emmons C.L. Oat avenanthramides exhibit antioxidant activities in vitro. Food Chem. 2002, 79:473-478.
333. Peterson D.M., Wesenberg D.M., Burrup D.E., Erikson C.A. Relationship among agronomic traits and grain composition in oat genotypes grown in different environments. Crop Sci. 2005, 45:1249-1255.
334. Pietta P.-G. Flavonoids as antioxidants. J. Nat. Prod. 2000, 63:1035-1042.
335. Pomillio A.B., Leicach S.R., Grass M.Y., Ghersa C.M., Santoro M., Vitale A.A. Constituents of the root exudates of Avena fatua grown under far-red-enriched light. Phytochem. Anal. 2000, 11:304-308.
336. Popovici G., Weissenbock G. Changes in the flavonoid pattern during the development of the oat plant (Avena sativa L.). Ber. Dtsch. Bot. Ges. 1976, 89:483-489.
337. Popravko S.A., Sokolov I.V., Torgov I.V. New natural phenolic triglycerides. Khim. Prir. Soedin. 1982, 18:169-173.
338. Post-Beittenmiller D. Biochemistry and molecular biology of wax production in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1996, 47:405-430.
339. Price K.R., Johnson I.T., Fenwick G.R. The chemistry and biological significance of saponins in food and feedingstuffs. Crit. Rev. Food Sci. Nutr. 1987, 26:27-133.
340. Pyysalo T., Torkkeli H., Honkanen E. The thermal decarboxylation of some substituted cinnamic acids. Lebensm. Wiss. Technol. 1977, 10:145-147.
341. Qi X., Bakht S., Leggett M., Maxwell C., Melton R., Osbourn A. A gene cluster for secondary metabolism in oat: Implications for evolution in metabolic diversity in plants. Proc. Natl. Acad. Sci. U.S.A. 2004, 101:8233-8238.
342. Qu H., Madl R.L., Takemoto D.J., Baybutt R.C., Wang W. Lignans are involved in the antitumor activity of wheat bran in colon cancer SW480 cells. J. Nutr. 2005, 135:598-602.
343. Quideau S., Ralph J. Lignin-ferulate cross-links in grasses. Part 4. 1-3 Incorporation of 5-5-coupled dehydrodiferulate into synthetic lignin. J. Chem. Soc. Perkin Trans. 1997, 1:2351-2358.
344. Quinlivan E.O., Roje S., Basset G., Shachar-Hill Y., Gregory J.F., Hanson A.D. The folate precursor p-aminobenzoate is reversibly converted to its glucose ester in plant cytosol. J. Biol. Chem. 2003, 278:20731-20737.
345. Raffaelli B., Koikkala A., Leppälä E., Wähälä K. Enterolignans. J. Chromatogr. B 2002, 777:29-43.
346. Ralet M.-C., Faulds C.B., Williamson G., Thibault J.-F. Degradation of feruloylated oligosaccharides from sugar beet pulp and wheat bran by ferulic acid esterases from Aspergillus niger. Carbohydr. Res. 1994, 263:257-269.
347. 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. 1994, 1:3485-3498.
348. 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.
349. 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. Lignin and Lignan Biosynthesis. (ACS Symp. Ser. 697.) 1998, 209-236. American Chemical Society, Washington, DC. N.G. Lewis, S. Sarkanen (Eds.).
350. Ralph J., Lundquist K., Brunow G., Lu F., Kim H., Schatz P.F., Marita J.M., Hatfield R.D., Ralph S.A., Christensen J.H., Boerjan W. Lignins: Natural polymers from oxidative coupling of 4-hydroxyphenylpropanoids. Phytochem. Rev. 2004, 3:29-60.
351. Renger A., Steinhart H. Ferulic acid dehydrodimers as structural elements in cereal dietary fibre. Eur. Food Res. Technol. 2000, 211:422-428.
352. Reuber S., Bornman J.F., Weissenbock G. A flavonoid mutant in barley exhibits increased sensitivity to UV-B radiation in primary leaves. Plant Cell Environ. 1996, 19:593-599.
353. Rhodes D.I., Sadek M., Stone B.A. Hydroxycinnamic acids in walls of wheat aleurone cells. J. Cereal Sci. 2002, 36:67-81.
354. Rice-Evans C. Flavonoid antioxidants. Curr. Med. Chem. 2001, 8:797-807.
355. Romero R.M., Roberts M.F., Phillipson J.D. Anthranilate synthase in microorganisms and plants. Phytochemistry 1995, 39:263-276.
356. Rondini L., Peyrat-Maillard M.-N., Marsset-Baglieri M., Berset C. Sulfated ferulic acid is the main in vivo metabolite found after short-term ingestion of free ferulic acid in rats. J. Agric. Food Chem. 2002, 50:3037-3041.
357. Rondini L., Peyrat-Maillard M.-N., Marsset-Baglieri A., Fromentin G., Durand P., Tomé D., Prost M., Berset C. Bound ferulic acid from bran is more bioavailable than the free compound in rat. J. Agric. Food Chem. 2004, 52:4338-4343.
358. Rösler J., Krekel F., Amrhein N., Schmid J. Maize phenylalanine ammonia-lyase has tyrosine ammonia-lyase activity. Plant Physiol. 1997, 113:175-179.
359. Ross A.B., Shepperd M.J., Schüpphaus M., Sinclair V., Alfaro B., Kamal-Eldin A., Åman P. Alkylresorcinols in cereals and cereal products. J. Agric. Food Chem. 2003, 51:4111-4118.
360. Ross J.A., Kasum C.M. Dietary flavonoids: Bioavailability, metabolic effects, and safety. Annu. Rev. Nutr. 2002, 22:19-34.
361. Rowe J.B., Crosbie G.B. The digestibility of grain of two cultivars of oats differing in lignin content. Aust. J. Agric. Res. 1988, 39:639-644.
362. Rowland I., Faughnan M., Hoey L., Wähälä K., Williamson G., Cassidy A. Bioavailability of phyto-oestrogens. Br. J. Nutr. 2003, 89(suppl. 1):S45-S58.
363. Saleem M., Kim H.J., Ali M.S., Lee Y.S. An update on bioactive plant lignans. Nat. Prod. Rep. 2005, 22:696-716.
364. Saleh N.A.M., Nozzolillo C., Altosaar I. Flavonoid variation in Avena species. Biochem. Syst. Ecol. 1988, 16:597-599.
365. Saulnier L., Vigouroux J., Thibault J.-F. Isolation and partial characterization of feruloylated oligosaccharides from maize bran. Carbohydr. Res. 1995, 272:241-253.
366. Saulnier L., Crépeau M.-J., Lahaye M., Thibault J.-F., Garcia-Conesa M.T., Kroon P.A., Williamson G. Isolation and structural determination of two 5-5-diferuloyl oligosaccharides indicate that maize heteroxylans are covalently cross-linked by oxidatively coupled ferulates. Carbohydr. Res. 1999, 320:82-92.
367. Scalbert A., Manach C., Morand C., Remesy C., Jimenez L. Dietary polyphenols and prevention of disease. Crit. Rev. Food Sci. Nutr. 2005, 45:287-306.
368. Schabath M.B., Hernandez L.M., Wu X., Pillow P.C., Spitz M.R. Dietary phytoestrogens and lung cancer. J. Am. Med. Assoc. 2005, 294:1493-1504.
369. Scheline R.R., Midtvedt T. Absence of dehydroxylation of caffeic acid in germ-free rats. Experientia 1970, 26:1068-1069.
370. Schmitz-Hoerner R., Weissenbock G. Contribution of phenolic compounds to the UV-B screening capacity of developing barley primary leaves in relation to DNA damage and repair under elevated UV-B levels. Phytochemistry 2003, 64:243-255.
371. Schoefer L., Mohan R., Schwiertz A., Braune A., Blaut M. Anaerobic degradation of flavonoids by Clostridium orbiscindens. Appl. Environ. Microbiol. 2003, 69:5849-5854.
372. Seal C.J. Whole grains and CVD risk. Proc. Nutr. Soc. 2006, 65:24-34.
373. Setchell K.D.R. Discovery and potential clinical importance of mammalian lignans. Flaxseed in Human Nutrition 1995, 82-98. American Oilseed Chemists Society Press, Champaign, IL. S.C. Cunnane, L.U. Thompson (Eds.).
374. Setchell K.D., Lawson A.M., Mitchell F.L., Adlercreutz H., Kirk D.N., Axelson M. Lignans in man and in animal species. Nature 1980, 287:740-742.
375. Setchell K.D., Lawson A.M., Conway E., Taylor N.F., Kirk D.N., Cooley G., Farrant R.D., Wynn S., Axelson M. The definitive identification of lignans trans-2,3-bis(3-hydroxybenzyl)-gamma-butyrolactone and 2,3-bis(hydroxybenzyl)burane-1,4-diol in human and animal urine. Biochem. J. 1981, 197:447-458.
376. Shimoi K., Okada H., Furugori M., Goda T., Takase S., Suzuki M., Hara Y., Yamamoto H., Kinae N. Intestinal absorption of luteolin and luteolin 7-O-β-glucoside in rats and humans. FEBS Lett. 1998, 438:220-224.
377. Shimoi K., Saka N., Kaji K., Nozawa R., Kinae N. Metabolic fate of luteolin and its functional activity at focal site. Biofactors 2000, 12:181-186.
378. Sicker D., Frey M., Schulz M., Gierl A. Role of natural benzoxazinones in the survival of plants. Int. Rev. Cytol. 2000, 198:319-346.
379. Simmonds M.S.J. Flavonoid-insect interactions: Recent advances in our knowledge. Phytochemistry 2003, 64:21-30.
380. Simons A.L., Reneuf M., Hendrich S., Murphy P.A. Human gut microbial degradation of flavonoids: Structure-function relationships. J. Agric. Food Chem. 2005, 53:4258-4263.
381. Slavin J.L., Jacobs D., Marquart L., Wiemer K. The role of whole grains in disease prevention. J. Am. Diet. Assoc. 2001, 101:780-785.
382. Smith M.M., Hartley R.D. Occurrence and nature of ferulic acid substitution of cell-wall polysaccharides in graminaceous plants. Carbohydr. Res. 1983, 118:65-80.
383. Soma J., Sugawara T., Huang Y.D., Nakajima J., Kawamura M. Tranilast slows the progression of advanced diabetic nephropathy. Nephron 2002, 92:693-698.
384. Soriano I.R., Asenstorfer R.E., Schmidt O., Riley I.T. Inducible flavone in oats (Avena sativa) is a novel defense against plant-parasitic nematodes. Phytopathology 2004, 94:1207-1214.
385. Sosulski F., Krygier K., Hogge L. Free, esterified and insoluble-bound phenolic acids. 3. Composition of phenolic acids in cereal and potato flours. J. Agric. Food Chem. 1982, 30:337-340.
386. Spencer J.P.E., Chowrimootoo G., Choudhury R., Debnab E.S., Srai S.K., Rice-Evans C. The small intestine can both absorb and glucuronidate luminal flavonoids. FEBS Lett. 1999, 458:224-230.
387. Spieker M., Lorenz I., Marx N., Darius H. Tranilast inhibits cytokine-induced nuclear factor kappa-B activation in vascular endothelial cells. Mol. Pharmacol. 2002, 62:856-863.
388. Stapleton A.E., Walbot V. Flavonoids can protect maize DNA from the induction of ultraviolet radiation damage. Plant Physiol. 1994, 105:881-889.
389. Stattin P., Adlercreutz H., Tenkanen L., Jellum E., Lumme S., Hallmans G. Circulating enterolactone and prostate cancer risk: A Nordic nested case-controlled study. Int. J. Cancer 2002, 99:124-129.
390. Steinke R.D., Paulson M.C. The production of steam-volatile phenols during cooking and alcoholic fermentation of grain. J. Agric. Food Chem. 1964, 12:381-387.
391. Stitch S.R., Toumba J.K., Groen M.B., Funke C.W., Leemhuis J., Vink J., Wood G.F. Excretion, isolation and structure of a new phenolic constituent of female urine. Nature 1980, 287:738-740.
392. Suzawa H., Kikuchi S., Ichikawa K., Koda A. Inhibitory action of Tranilast, an anti-allergic drug, on the release of cytokines and PGE2 from human monocytes-macrophages. Jpn. J. Pharmacol. 1992, 60:85-90.
393. Suzuki H., Matsumoto T., Noguchi M. Identification of p-aminophenyl-β-d-glucose from Hydrangea macrophylla. Phytochemistry 1976, 15:555.
394. Tamai H., Katoh O., Suzuki S., Fujii K., Aizawa T., Takase S., Kurogane H., Nishikawa H., Sone T., Sakai K. Impact of Tranilast on restenosis after coronary angioplasty: Tranilast restenosis following angioplasty trial (TREAT). Am. Heart J. 1999, 138:968-975.
395. Tan K.S., Hoson T., Masuda Y., Kamisaka S. Correlation between cell wall extensibility and the content of diferulic and ferulic acids in cell walls of Oryza sativa coleoptiles grown under water and in air. Physiol. Plant. 1991, 83:397-403.
396. Tan K.S., Hoson T., Masuda Y., Kamisaka S. Involvement of cell wall-bound diferulic acid in light-induced decrease in growth rate and cell wall extensibility of Oryza sativa coleoptiles. Plant Cell Physiol. 1992, 33:103-108.
397. Tang C.-S., Chang S.H., Hoo D., Yanagihara K.H. Gas chromatographic determination of 2(3)-benzoxazolinones from cereal plants. Phytochemistry 1975, 14:2077-2079.
398. Tani T., Mayama S. Evaluation of phytoalexins and preformed antifungal substances in relation to fungal infection. Plant Infection: The Physiological and Biochemical Basis 1982, 301-314. Springer-Verlag, Berlin. Y. Asada, W.R. Bushnell, S. Ouchi, C.P. Vance (Eds.).
399. Thompson L.U., Robb P., Serraino M., Cheung F. Mammalian lignan production from various foods. Nutr. Cancer 1991, 16:43-52.
400. Tiong A.Y., Brieger D. Inflammation and coronary heart disease. Am. Heart J. 2005, 150:11-18.
401. Tomás-Barberán F.A., Clifford M.N. Dietary hydroxybenzoic acid derivatives-Nature, occurrence and dietary burden. J. Sci. Food Agric. 2000, 80:1024-1032.
402. Towers G.H.N. Metabolism of phenolics in higher plants and microorganisms. Biochemistry of Phenolic Compounds 1964, 249-294. Academic Press, New York. J.B. Harborne (Ed.).
403. Tressl R., Kossa T., Renner R., Koppler H. Gas chromatographic-mass spectroscopic investigations on the formation of phenolic and aromatic hydrocarbons in food. Z. Lebensm. Unters. Forsch. 1976, 162:123-130.
404. Trojanowska M.R., Osbourn A.E., Daniels M.J., Threlfall D.R. Investigation of avenacin-deficient mutants of Avena strigosa. Phytochemistry 2001, 56:121-129.
405. Türk M., Egesel C.ö., Gül M.K. Avenacin A-1 content of some local oat genotypes and the in vitro effect of avenacins on several soil-borne fungal pathogens of cereals. Turk. J. Agric. For. 2005, 29:157-164.
406. Turner E.M.C. The nature of the resistance of oats to the take-all fungus. III. Distribution of the inhibitors in oat seedlings. J. Exp. Bot. 1960, 11:403-412.
407. Turner L.B., Mueller-Harvey I., McAllan A.B. Light-induced isomerization and dimerization of cinnamic acid derivatives in cell walls. Phytochemistry 1993, 33:791-796.
408. Umezawa T. Diversity of lignan biosynthesis. Phytochem. Rev. 2003, 2:371-390.
409. Van Beek S., Priest F.G. Decarboxylation of substituted cinnamic acids by lactic acid bacteria isolated during malt whisky fermentation. Appl. Environ. Microbiol. 2000, 66:5322-5328.
410. Van Sumere C., Cottenie J., De Greef J., Kint J. Biochemical studies in relation to the possible germination regulatory role of naturally occurring coumarin and phenolics. Recent Adv. Phytochem. 1972, 4:166-221.
411. Van Sumere C.F., De Pooter H., Ali H., Degrauer-Van Bussel M. N-feruloylglycyl-L-phenylalanine. A sequence in barley proteins. Phytochemistry 1973, 12:407-411.
412. Varady K.A., Wang Y., Jones P.J. Role of policosanols in the prevention and treatment of cardiovascular disease. Nutr. Rev. 2003, 61:376-383.
413. Vogel J.J. Studies on the diet in relation to dental caries in the cotton rat. Ph.D. thesis 1961, University of Wisconsin, Madison.
414. Vogt T., Jones P. Glycosyltransferases in plant natural product synthesis: Characterization of a supergene family. Trends Plant Sci. 2000, 5:380-386.
415. Von Heimendahl C.B.I., Schäfer K.M., Eklund P., Sjöholm R., Schmidt T.J., Fuss E. Pinoresinol-lariciresinol reductases with different stereospecificity from Linum album and Linum usitatissimum. Phytochemistry 2005, 66:1254-1263.
416. Von Röpenack E., Parr A., Schulze-Lefert P. Structural analyses and dynamics of soluble and cell wall-bound phenolics in a broad spectrum resistance to the powdery mildew fungus in barley. J. Biol. Chem. 1998, 273:9013-9022.
417. Wakabayashi K., Soga K., Kamisaka S., Hoson T. Increase in the level of arabinoxylan-hydroxycinnamate network in the cell walls of wheat coleoptiles grown under continuous hypergravity conditions. Physiol. Plant. 2005, 125:127-134.
418. Wallace J.W., Grisebach H. The in vivo incorporation of a flavanone into C-glycosylflavones. Biochim. Biophys. Acta 1973, 304:837-841.
419. Wallerstein J.S., Hale M.G., Alba R.T. Oxidizing enzymes in brewing materials. IV. O-phenylenediamine oxidase in rice, wheat and corn. Wallerstein Lab. Commun. 1948, 11:221-226.
420. Walters D.R. Polyamines and plant disease. Phytochemistry 2003, 64:97-107.
421. Walton N.J., Mayer M.J., Narbad A. Vanillin. Phytochemistry 2003, 63:505-515.
422. Wang L.-Q. Mammalian phytoestrogens: Enterodiol and enterolactone. J. Chromatogr. B 2002, 777:289-309.
423. Wang L.-Q., Meselhy M.R., Li Y., Qin G.W., Hattori M. Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone. Chem. Pharm. Bull. 2000, 48:1606-1610.
424. Ward R.S. Lignans, neolignans and related compounds. Nat. Prod. Rep. 1997, 14:43-74.
425. Ward R.S. Lignans, neolignans and related compounds. Nat. Prod. Rep. 1999, 16:75-96.
426. Weidner S., Paprocka J., Kamieniecka B., Zadernowski R. The role of phenolic acids in dormancy of barley caryopses. Pre-Harvest Sprouting of Cereals 1992, 200-211. Am. Assoc. Cereal Chem., St. Paul, MN. M.K. Walker-Simmonds, J.L. Reid (Eds.).
427. Wende G., Fry S.C. O-feruloylated, O-acetylated oligosaccharides as side chains of grass xylans. Phytochemistry 1997, 44:1011-1018.
428. Wende G., Fry S.C. 2-O-β-D-xylopyranosyl-(5-O-feruloyl)-L-arabinose, a widespread component of grass cell walls. Phytochemistry 1997, 44:1019-1030.
429. Wende G., Fry S.C. Digestion by fungal glycanases of arabinoxylans with different feruloylated side-chains. Phytochemistry 1997, 45:1123-1129.
430. Wenzig E., Kunert O., Ferreira D., Schmid M., Schühly W., Bauer R., Hiermann A. Flavonolignans from Avena sativa. J. Nat. Prod. 2005, 68:289-292.
431. Westcott N.D., Muir A.D. Flax seed lignan in disease prevention and health promotion. Phytochem. Rev. 2003, 2:401-417.
432. Willför, S. M., Smeds, A. I., and Holmbom, B. R. 2006. Chromatographic analysis of lignans. J. Chromatogr. A 1112:64-77. (E-publication).
433. Williams R.J., Spencer J.P., Rice-Evans C. Flavonoids: Antioxidants or signaling molecules?. Free Radic. Biol. Med. 2004, 36:838-849.
434. Wollenweber E. Flavones and flavonols. The Flavonoids: Advances in Research Since 1986 1993, 259-335. Chapman and Hall, St. Paul, MN. J.B. Harborne (Ed.).
435. Wu Q., Wang M., Simon J.E. Analytical methods to determine phytoestrogenic compounds. J. Chromatogr. B 2004, 812:325-355.
436. Xia Z.-Q., Costa M.A., Pélissier H.C., Davin L.B., Lewis N.G. Secoisolariciresinol dehydrogenase purification, cloning and functional expression: Implications for human health protection. J. Biol. Chem. 2001, 276:12614-12623.
437. Xie L.-H., Ahn E.-M., Akao T., Abdel-Hafez A.A.-M., Nakamura N., Hattori M. Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria. Chem. Pharm. Bull. 2003, 51:378-384.
438. Xie L.-H., Akao T., Hamasaki K., Deyama T., Hattori M. Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol. Chem. Pharm. Bull. 2003, 51:508-515.
439. Xing Y., White P.J. Identification and function of antioxidants from oat groats and hulls. J. Am. Oil Chem. Soc. 1997, 74:303-307.
440. Yamada H., Tajima S., Nishikawa T., Murad S., Pinnell S.R. Tranilast, a selective inhibitor of collagen synthesis in human skin fibroblasts. J. Biochem. 1994, 116:892-897.
441. Yamaha T., Cardini C.E. The biosynthesis of plant glycosides. I. Monoglycosides. Arch. Biochem. Biophys. 1960, 86:127-132.
442. Yamaha T., Cardini C.E. The biosynthesis of plant glycosides. II. Gentiobiosides. Arch. Biochem. Biophys. 1960, 86:133-137.
443. Yang Q., Trinh H.X., Imai S., Ishihara A., Zhang L., Nakayashiki H., Tosa Y., Mayama S. Analysis of the involvement of hydroxyanthranilate hydroxycinnamoyltransferase and caffeoyl-CoA 3-O-methyltransferase in phytoalexins biosynthesis in oat. Mol. Plant-Microbe Interact. 2004, 17:81-89.
444. Yoshida-Shimokawa T., Yoshida S., Kakegawa K., Ishii T. Enzymatic feruloylation of arabinoxylan-trisaccharide by feruloyl-CoA:arabinoxylan-trisaccharide O-hydroxycinnamoyl transferase from Oryza sativa. Planta 2001, 212:470-474.
445. Yu P. Application of advanced synchrotron radiation-based Fourier transform infrared (SR-FTIR) microspectroscopy to animal and feed science: A novel approach. Br. J. Nutr. 2004, 92:869-885.
446. Zenk M.H. Untersuchengen zum Phototropismus der Avena-koleoptile: II. Pigmente. Z. Pflanzenphysiol. 1967, 56:122-140.
447. Zhang L., Robbins M.P., Carver T.L.W., Zeyen R.J. Induction of phenylpropanoid gene transcripts in oat attacked by Erysiphe graminis at 20°C and 10°C. Physiol. Mol. Plant Pathol. 1997, 51:15-33.
448. Zhao Z., Egashira Y., Sanada H. Ferulic acid sugar esters are recovered in rat plasma and urine mainly as the sulfoglucuronide of ferulic acid. J. Nutr. 2003, 133:1355-1361.
449. Zhao Z., Egashira Y., Sanada H. Digestion and absorption of ferulic acid sugar esters in rat gastrointestinal tract. J. Agric. Food Chem. 2003, 51:5534-5539.
450. Zhao Z., Egashira Y., Sanada H. Ferulic acid is quickly absorbed from rat stomach as the free form and then conjugated mainly in the liver. J. Nutr. 2004, 134:3083-3088.
451. Zhao Z., Egashira Y., Sanada H. Phenolic antioxidants richly contained in corn bran are slightly bioavailable in rats. J. Agric. Food Chem. 2005, 53:5030-5035.
452. Zieliński H., Kozlowska H. Antioxidant activity and total phenolics in selected cereal grains and their different morphological fractions. J. Agric. Food Chem. 2000, 48:2008-2016.
453. Zieliński H., Kozlowska H., Luwczuk B. Bioactive compounds in the cereal grains before and after hydrothermal processing. Inn. Food Sci. Emerg. Technol. 2001, 2:159-169.