Anthocyanins from red cabbage - stability to simulated gastrointestinal digestion

Phytochemistry

Volumn 68, Issue 9, 2007, Pages 1285-1294

  McDougall, Gordon J ^a   Fyffe, Stewart ^a   Dobson, Pat ^a   Stewart, Derek ^a  

^a Quality   (United Kingdom)

Author keywords

Acylation; Anthocyanins; Health benefits; Hydroxycinnamic acids; In vitro digestion; Polyphenols; Red cabbage; Stability

Indexed keywords

ANTHOCYANIN;

ARTICLE; BRASSICA; CHEMICAL STRUCTURE; CHEMISTRY; DIGESTION; ISOLATION AND PURIFICATION; METABOLISM; PH; PHYSIOLOGY;

ANTHOCYANINS; BRASSICA; DIGESTION; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE;

BRASSICA OLERACEA VAR. CAPITATA;

EID: 34247112344     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.02.004     Document Type: Article

References (48)

1. Aura A.-M., Martin-Lopez P., O'Leary K.A.O., Williamson G., Oksman-Caldentey M., Poutanen K., and Santos-Buelga C. In vitro metabolism of anthocyanins by human gut microflora. Eur. J. Nutr. 44 (2005) 1-10
2. Brennan R.M. Currants and gooseberries. In: Janick J., and Moore J.N. (Eds). Fruit Breeding. Small Fruits and Vine Crops vol. II (1996), John Wiley & Sons Inc., New York 191-295
3. Bridle P., and Timberlake C.F. Anthocyanins as natural food colors: Selected aspects. Food Chem. 58 (1997) 103-109
4. Bub A., Watzl B., Heeb D., Rechkemmer G., and Briviba K. Malvidin-3-glucoside bioavailability in humans after ingestion of red wine, de-alcoholised red wine and red grape juice. Eur. J. Nutr. 40 (2001) 113-120
5. Clifford M.N. Anthocyanins - nature, occurrence and dietary burden. J. Sci. Food Agric. 80 (2000) 1063-1072
6. Day A.J., Canada F.J., Diaz J.C., Kroon P.A., Mclauchlan R., Faulds C.B., Plumb G.W., Morgan M.R.A., and Williamson G. Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of the lactase phlorizin hydrolase. FEBS Lett. 468 (2000) 166-170
7. Frank T., Netzel M., Strass G., and Bitsch I. Bioavailability of anthocyanidin-3-glucosides following consumption of red wine and red grape juice. Can. J. Physiol. Pharmacol. 81 (2003) 423-435
8. Gee J.M., DuPont M.S., Rhodes M.J.C., and Johnson I.T. Quercetin glucosides interact with the intestinal glucose transport pathway. Free Rad. Biol. Med. 25 (1998) 19-25
9. Gil-Izquierdo A., Zafrilla P., and Tomas-Barberan F.A. An in vitro method to simulate phenolic compound release from the food matrix in the gastrointestinal tract. Eur. Food Res. Technol. 214 (2002) 155-159
10. Giusti M.M., and Wrolstad R.E. Acylated anthocyanins from edible sources and their application in food systems. Biochem. Eng. J. 14 (2003) 217-225
11. Giusti M.M., Rodri{dotless}guez-Saona L.E., Griffin D., and Wrolstad R.E. Electrospray and tandem mass spectroscopy as tools for anthocyanin characterization. J. Agric. Food Chem. 47 (1999) 4657-4664
12. Gonthier M.-P., Cheynier V., Donovan J.L., Manach C., Morand c., Mila I., Lapierre C., Remesy C., and Scalbert C. Microbial aromatic acid metabolites formed in the gut account for a major fraction of the polyphenols excreted in urine of rats fed red wine polyphenols. J. Nutr. 133 (2003) 461-467
13. Graham J., Smith K., MacKenzie K., Jorgensen L., Hackett C., and Powell W. The construction of a genetic linkage map of red raspberry (Rubus idaeus subsp. idaeus) based on AFLPs, genomic SSR and EST-SSR markers. Theor. Appl. Genet. 109 (2004) 740-749
14. Heo H.J., and Lee C.Y. Phenolic phytochemicals in cabbage inhibit amyloid beta protein-induced neurotoxicity. LWT - Food Sci. Technol. 39 (2006) 331-337
15. Hong V., and Wrolstad R.E. Use of HPLC separation/photodiode array detection for characterization of anthocyanins. J. Agric. Food. Chem. 38 (1990) 708-715
16. Hou D.X. Potential mechanism of cancer chemoprevention by anthocyanin. Curr. Mol. Med. 3 (2003) 149-159
17. Idaka E., Yamakita H., Ogawa T., Kondo T., Yamamoto M., and Goto T. Structure of three diacylated anthocyanins isolated from red cabbage, Brassica oleraceae. Chem. Lett. 6 (1987) 1213-1216
18. Idaka E., Suzuki K., Yamakita H., Ogawa T., Kondo T., and Goto T. Structure of monoacylated anthocyanins isolated from red cabbage, Brassica oleracea. Chem. Lett. 1 (1987) 145-148
19. Igarashi K., Kimura Y., and Takenake A. Preventive effects of dietary red cabbage acylated anthocyanins on paraquat-induced oxidative stress in rats. Biosci. Biotechnol. Biochem. 64 (2000) 1600-1607
20. Jayaprakasam B., Vareed S.K., Olson L.K., and Nair M.G. Insulin secretion by bioactive anthocyanins and anthocyanidins present in fruits. J. Agric. Food Chem. 53 (2005) 28-31
21. Kuhnle G., Spencer J.P.E., Schroeter H., Shenoy B., Dednam E.S., Srai K.S., Rice-Evans C., and Hahn U. Epicatechin and catechin are O-methylated and glucuronidated in the small intestine. Biochem. Biophys. Res. Commun. 277 (2000) 507-512
22. Lapidot T., Harel S., Granit R., and Kanner J. Bioavailability of red wine anthocyanins as detected in human urine. J. Agric. Food Chem. 46 (1998) 4297-4302
23. Lau F.C., Shukitt-Hale B., and Joseph J.A. Beneficial effects of berry fruit polyphenols on neuronal and behavioral aging. J. Sci. Food Agric. 86 (2006) 2251-2255
24. Lee K.J., Sok D.E., Kim Y.B., and Kim M.R. Protective effect of vegetable extracts on oxidative stress in brain of mice administered with NMDA. Food Res. Int. 35 (2002) 55-63
25. Markakis P. Stability of anthocyanins in foods. In: Markakis P. (Ed). Anthocyanins as Food Colours (1982), Academic Press, New York, USA 163-180
26. Maulien-Aubert C., Dangles O., and Amiot M.J. Colour stability of commercial anthocyanin-based extracts in relation to the phenolic composition. Protective effects by intramolecular and intermolecular copigmentation. J. Agric. Food Chem. 249 (2001) 170-176
27. Mazza G., Kay C.D., Cottrell T., and Holub B.J. Absorption of anthocyanins from blueberries and serum antioxidant status in human subjects. J. Agric. Food Chem. 50 (2002) 7731-7737
28. McDougall G.J., and Stewart D. The inhibitory effects of berry extracts on digestive enzymes. Biofactors 23 (2006) 189-195
29. McDougall G.J., Dobson P., Smith P., Blake A., and Stewart D. Assessing potential bioavailability of raspberry anthocyanins using an in vitro digestion system. J. Agric. Food Chem. 53 (2005) 5896-5904
30. McDougall G.J., Fyffe S., Dobson P., and Stewart D. Anthocyanins from red wine - their stability under simulated gastrointestinal digestion. Phytochemistry 66 (2005) 2540-2548
31. Miller D.D., Schricker B.R., Rasmussen R.R., and Van Campen D. An in vitro method for the estimation of iron from meals. Am. J. Clin. Nutr. 34 (1981) 2248-2256
32. Natella F., Nardini M., Di Felice M., and Scaccini C. Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation. J. Agric. Food Chem. 47 (1999) 1453-1459
33. Nemeth K., Plumb G.W., Berrin J.G., Juge N., Jacob R., Naim H.Y., Williamson G., Swallow D.M., and Kroon P.A. Deglycosylation by small intestinal cell beta-glucosidases is a critical step in the absorption and metabolism of dietary flavonoids in humans. Eur. J. Nutr. 42 (2003) 29-42
34. Passamonti S., Vrhovsel U., Vanzo A., and Mattivi F. The stomach as a site for anthocyanins absorption from food. FEBS Lett. 544 (2003) 210-213
35. Perez-Vicente A., Gil-Izquierdo A., and Garcia-Viguera C. In vitro gastrointestinal digestion study of pomegranate juice - phenolic compounds, anthocyanins, and vitamin C. J. Agric. Food Chem. 50 (2002) 2308-2312
36. Ramirez-Tortosa C., Andersen O.M., Gardner P.T., Morrice P.C., Wood S.G., Duthie S.J., Collins A.R., and Duthie G.G. Anthocyanin-rich extract decreases indices of lipid peroxidation and DNA damage in vitamin E-depleted rats. Free Radical Biol. Med. 31 (2001) 1033-1037
37. Ribereau-Gayon P., and Stonestreet E. Determination of anthocyanins in red wine. Bull. Soc. Chim. Fr. (1965) 2649-2652
38. Serafini M., Maiani G., and Ferro-Luzzi A. Alcohol-free red wine enhances plasma antioxidant capacity in humans. J. Nutr. 128 (1998) 1003-1007
39. Singleton V.L., and Rossi Jr. J.A. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. Am. J. Enol. Viticult. 16 (1965) 144-158
40. Stintzing F.C., and Carle R. Functional properties of anthocyanins and betalains in plants, food, and in human nutrition. Trends Food Sci. Technol. 15 (2004) 19-38
41. Stintzing F.C., Stinzing A.S., Carle R., Frei R., and Wrolstad R.E. Colour and antioxidant properties of cyanidin-based anthocyanin pigments. J. Agric. Food Chem. 50 (2002) 6172-6181
42. Strack D., and Wray V. Anthocyanins. Methods in Plant Biochemistry. Plant Phenolics vol. 1 (1993), Academic Press, London 325-356
43. Talavera S., Felgines C., Texier O., Besson C., Mazur A., Lamaison J.-L., and Remesy C. Bioavailability of bilberry anthocyanin extract and its impact on plasma antioxidant capacity in rats. J. Sci. Food. Agric. 86 (2006) 90-97
44. Tall J.M., Seeram N.P., Zhao C.S., Nair M.G., Meyer R.A., and Raja S.N. Tart cherry anthocyanins suppress inflammation-induced pain behavior in rat. Behav. Brain Res. 153 (2004) 181-192
45. Tanchev S.S., and Timberlake C.F. The anthocyanins of red cabbage (Brassica oleracea). Phytochemistry 8 (1969) 1825-1827
46. Walton M.C., McGhie T.K., Reynolds G.W., and Hendriks W.H. The flavonol quercetin-3-glucoside inhibits cyanidin-3-glucoside absorption in vitro. J. Agric. Food Chem. 13 (2006) 4913-4920
47. Wu X., and Prior R.L. Systematic identification and characterization of anthocyanins by HPLC-ESI-MS/MS in common foods in the United States: vegetables and nuts. J. Agric. Food Chem. 53 (2005) 3101-3113
48. Wu X., Beecher G.R., Holden J.M., Haytowitz D.B., Gebhardt S.E., and Prior R.L. Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. J. Agric. Food Chem. 54 (2006) 4069-4075