Antioxidant potential of hydroxycinnamic acid glycoside esters

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 12, 2008, Pages 4797-4805

  Kylli, Petri ^a   Nousiainen, Paula ^a   Biely, Peter ^b   Sipilä, Jussi ^a   Tenkanen, Maija ^a   Heinonen, Marina ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b INSTITUTE OF CHEMISTRY   (Slovakia)

Author keywords

Antioxidant activity; Conjugation; Ferulic acid; Glycoside ester; Hydroxycinnamic acid; Radical scavenging; Sinapic acid

Indexed keywords

ANTIOXIDANT; COUMARIC ACID; ESTER; GLYCOSIDE; LIPOSOME; SCAVENGER; SINAPIC ACID;

ARTICLE; CHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANTIOXIDANTS; COUMARIC ACIDS; ESTERS; FREE RADICAL SCAVENGERS; GLYCOSIDES; LIPOSOMES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 47349112690     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf800317v     Document Type: Article

References (50)

1. Winter, M.; Herrmann, K. Esters and glucosides of hydroxycinnamic acids in vegetables. J. Agric. Food Chem. 1986, 34, 616-620.
2. Chen, J. H.; Ho, C. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem. 1997, 45, 2374-2378.
3. Nyström, L.; Mäkinen, M.; Lampi, A.; Piironen, V. Antioxidant activity of steryl ferulate extracts from rye and wheat bran. J. Agric. Food Chem. 2005, 53, 2503-2510.
4. Levigne, S.; Ralet, M.; Quemener, B.; Thibault, J. Isolation of diferulic bridges ester-linked to arabinan in sugar beet cell walls. Carbohydr. Res. 2004, 339, 2315-2319.
5. Mattila, P.; Hellström, J.; Törrönen, R. Phenolic acids in berries, fruits, and beverages. J. Agric. Food Chem. 2006, 54, 7193-7199.
6. Renger, A.; Steinhart, H. Ferulic acid dehydrodimers as structural elements in cereal dietary fibre. Eur. Food Res. Technol. 2000, 211, 422-428.
7. Liukkonen, K.; Katina, K.; Wilhelmsson, A.; Myllymäki, O.; Lampi, A.; Kariluoto, S.; Piironen, V.; Heinonen, S.; Nurmi, T.; Adlercreutz, H.; Peltoketo, A.; Pihlava, J.; Hietaniemi, V.; Poutanen, K. Process-induced changes on bioactive compounds in whole grain rye. Proc. Nutr. Soc. 2003, 62, 117-122.
8. 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.
9. Ishii, T. Structure and functions of feruloylated polysaccharides. Plant Sci. 1997, 127, 111-127.
10. Ohashi, H.; Yamamoto, E.; Lewis, N. G.; Towers, G. H. N. 5-Hydroxyferulic acid in Zea mays and Hordeum vulgare cell walls. Phytochemistry 1987, 26, 1915-1916.
11. Saulnier, L.; Thibault, J. Ferulic acid and diferulic acids as components of sugar-beet pectins and maize bran heteroxylans. J. Sci. Food Agric. 1999, 79, 396-402.
12. Mathew, S.; Abraham, T. Ferulic acid: an antioxidant found naturally in plant cell walls and feruloyl esterases involved in its release and their applications. Crit. Rev. Biotechnol. 2004, 24, 59-83.
13. Bunzel, M.; Ralph, J.; Kim, H.; Lu, F.; Ralph, S. A.; Marita, J. M.; Hatfield, R. D.; Steinhart, H. Sinapate dehydrodimers and sinapate-ferulate heterodimers in cereal dietary fiber. J. Agric. Food Chem. 2003, 51, 1427-1434.
14. Mattila, P.; Kumpulainen, J. Determination of free and total phenolic acids in plant-derived foods by HPLC widi diode-array detection. J. Agric. Food Chem. 2002, 50, 3660-3667.
15. Silva, F. A. M.; Borges, F.; Guimaraes, C.; Lima, J. L. F. C.; Matos, C.; Reis, S. Phenolic acids and derivatives: studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. J. Agric. Food Chem. 2000, 48, 2122-2126.
16. Faulds, C. B.; Mandalari, G.; LoCurto, R.; Bisignano, G.; Waldron, K. W. Arabinoxylan and mono- and dimeric ferulic acid release from brewer's grain and wheat bran by feruloyl esterases and glycosyl hydrolases from Humicola insolens. Appl. Microbiol. Biotechnol. 2004, 64, 644-650.
17. Amorati, R.; Pedulli, G. F.; Cabrini, L.; Zambonin, L.; Landi, L. Solvent and pH effects on the antioxidant activity of caffeic and other phenolic acids. J. Agric. Food Chem. 2006, 54, 2932-2937.
18. Foley, S.; Navaratnam, S.; McGarvey, D. J.; Land, E. J.; Truscott, T. G.; Rice-Evans, C. A. Singlet oxygen quenching and the redox properties of hydroxycinnamic acids. Free Radical Biol. Med. 1999, 26, 1202-1208.
19. 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.
20. Andreasen, M. F.; Kroon, P. A.; Williamson, G.; Garcia-Conesa, M. Intestinal release and uptake of phenolic antioxidant diferulic acids. Free Radical Biol. Med. 2001, 31, 304-314.
21. Garcia-Conesa, M. T.; Wilson, P. D.; Plumb, G. W.; Ralph, J.; Williamson, G. Antioxidant properties of 4,4′-dihydroxy-3,3′-dimethoxy-β, β′-bicinnamic acid (8,8-diferulic acid, non-cyclic form). J. Sci. Food Agric. 1999, 79, 379-384.
22. Lampi, A.; Kamal-Eldin, A. Effect of α- and γ-tocopherols on thermal polymerization of purified high-oleic sunflower triacylglycerols. J. Am. Oil Chem. Soc. 1998, 75, 1699-1703.
23. Mastihubova, M.; Szemesova, J.; Biely, P. Two efficient ways to 2-O- and 5-O-feruloylated 4-nitrophenyl α-arabinofuranosides as substrates for differentiation of feruloyl esterases. Tetrahedron Lett. 2003, 44, 1671-1673.
24. Helm, R. F.; Ralph, J.; Hatfield, R. D. Synthesis of feruloylated and p-coumaroylated methyl glycosides. Carbohydr. Res. 1992, 229, 183-194.
25. Breitinger, H. Synthesis and characterization of 2,3-di-O-alkylated amyloses: hydrophobic substitution destabilizes helical conformation. Biopolymers 2003, 69, 301-310.
26. Klemer, A.; Bieber, M.; Wilbers, H. Eine neue Methode zur Spaltung von Kohlenhydrat-triphenylmethyl und -bentzylethern. Liebigs Ann. Chem. 1983, 14, 1416-1421.
27. Hanessian, S.; Kagotani, M. Novel methods for the preparation of partially acetylated carbohydrates. Carbohydr. Res. 1990, 202, 67-79.
28. 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.
29. Ellis, J. E.; Lenger, S. R. A convenient syndiesis of 3,4-dimethoxy-5-hydroxybenzaldehyde. Synth. Commun. 1998, 28, 1517-1524.
30. Lam, T. B. T.; Iiyama, K.; Stone, B. A. Caffeic acid:O-methyltransferases and the biosynthesis of ferulic acid in primary cell walls of wheat seedings. Phytochemistry 1996, 41, 1507-1510.
31. Vuorela, S.; Meyer, A.; Heinonen, M. E. Quantitative analysis of the main phenolics in rapeseed meal and oils processed differently using enzymatic hydrolysis and HPLC. Eur. Food Res. Technol. 2003, 217, 517-523.
32. Koski, A.; Pekkarinen, S.; Hopia, A.; Wähälä, K.; Heinonen, M. Processing of rapeseed oil: effects on sinapic acid derivative content and oxidative stability. Eur. Food Res. Technol. 2003, 217, 110-114.
33. Folin-Ciocalteau index. Off. J. Eur. Communities 1992, 178-179.
34. Kähkönen, M. P.; Heinonen, M. Antioxidant activity of anthocyanins and their aglycons. J. Agric. Food Chem. 2003, 51, 628-633.
35. Huang, S.; Frankel, E. N. Antioxidant activity of tea catechins in different lipid systems. J. Agric. Food Chem. 1997, 45, 3033-3038.
36. Viljanen, K.; Kylli, P.; Kivikari, R.; Heinonen, M. Inhibition of protein and lipid oxidation in liposomes by berry phenolics. J. Agric. Food Chem. 2004, 52, 7419-7424.
37. Frankel, E. N.; Huang, S.; Kanner, J.; German, J. B. Interfacial phenomena in the evaluation of antioxidants: bulk oils vs emulsions. J. Agric. Food Chem. 1994, 42, 1054-1059.
38. Zhang, J.; Stanley, R. A.; Melton, L. D. Lipid peroxidation inhibition capacity assay for antioxidants based on liposomal membranes. Mol. Nutr. Food Res. 2006, 50, 714-724.
39. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biol. Med. 1996, 20, 933-956.
40. Pekkarinen, S. S.; Stöckmann, H.; Schwarz, K.; Heinonen, I. M.; Hopia, A. I. Antioxidant activity and partitioning of phenolic acids in bulk and emulsified methyl linoleate. J. Agric. Food Chem. 1999, 47, 3036-3043.
41. Tominaga, H.; Kobayashi, Y.; Goto, T.; Kasemura, K.; Nomura, M. DPPH radical-scavenging effect of several phenylpropanoid compounds and their glycoside derivatives. Yakugaku Zasshi 2005, 125, 371-375.
42. Cos, P.; Rajan, P.; Vedernikova, I.; Calomme, M.; Pieters, L.; Vlietinck, A. J.; Augustyns, K.; Haemers, A.; Vanden Berghe, D. In vitro antioxidant profile of phenolic acid derivatives. Free Radical Res. 2002, 36, 711-716.
43. Materska, M.; Perucka, I. Antioxidant activity of the main phenolic compounds isolated from hot pepper fruit (Capsicum annuum L.). J. Agric. Food Chem. 2005, 53, 1750-1756.
44. Katapodis, P.; Vardakou, M.; Kalogeris, E.; Kekos, D.; Macris, B. J.; Christakopoulos, P. E. Enzymic production of a feruloylated oligosaccharide with antioxidant activity from wheat flour arabinoxylan. Eur. J. Nutr. 2003, 42, 55-60.
45. Yuan, X.; Wang, J.; Yao, H. Antioxidant activity of feruloylated oligosaccharides from wheat bran. Food Chem. 2005, 90, 759-764.
46. Huang, S.; Frankel, E. N.; Aeschbach, R.; German, J. B. Partition of selected antioxidants in corn oil-water model systems. J. Agric. Food Chem. 1997, 45, 1991-1994.
47. Stöckmann, H.; Schwarz, K.; Huynh-Ba, T. The influence of various emulsifiers on the partitioning and antioxidant activity of hydroxybenzoic acids and their derivatives in oil-in-water emulsions. JAOCS 2000, 77, 535-542.
48. Schwarz, K.; Frankel, E. N.; German, J. B. Partition behaviour of antioxidative phenolic compounds in heterophasic systems. Fett/Lipid 1996, 98, 115-121.
49. Zhou, B.; Miao, Q.; Yang, L.; Liu, Z. Antioxidative effects of flavonols and their glycosides against the free-radical-induced peroxidation of linoleic acid in solution and in micelles. Chem. Eur. J. 2005, 11, 680-691.
50. Paiva-Martins, F.; Gordon, M. H.; Gameiro, P. Activity and location of olive oil phenolic antioxidants in liposomes. Chem. Phys. Lipids 2003, 124, 23-36.