Effect of dose size on bioavailability of acylated and nonacylated anthocyanins from red cabbage (Brassica oleracea L. Var. capitata)

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 13, 2007, Pages 5354-5362

  Charron, Craig S ^a   Clevidence, Beverly A ^a   Britz, Steven J ^a   Novotny, Janet A ^a  

^a BELTSVILLE HUMAN NUTRITION RESEARCH CENTER   (United States)

Author keywords

Acylated; Anthocyanin; Bioavailability; Cabbage (Brassica oleracea L. var. capitata); Cyanidin

Indexed keywords

ANTHOCYANIN;

ACYLATION; ARTICLE; BIOAVAILABILITY; BRASSICA; CHEMISTRY; CLINICAL TRIAL; CONTROLLED CLINICAL TRIAL; CONTROLLED STUDY; CROSSOVER PROCEDURE; DOSE RESPONSE; FEMALE; HUMAN; MALE; MIDDLE AGED; RANDOMIZED CONTROLLED TRIAL; URINE;

ACYLATION; ANTHOCYANINS; BIOLOGICAL AVAILABILITY; BRASSICA; CROSS-OVER STUDIES; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; HUMANS; MALE; MIDDLE AGED;

BRASSICA OLERACEA; BRASSICA OLERACEA VAR. CAPITATA; CAPITATA;

EID: 34447330708     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0710736     Document Type: Article

References (49)

1. Neill, S. O.; Gould, K. S. Anthocyanins in leaves: light attenuators or antioxidants? Funct. Plant Biol. 2003, 30, 865-873.
2. Gould, K. S. Nature's Swiss army knife: the diverse protective roles of anthocyanins in leaves. J. Biomed. Biotechnol. 2004, 5, 314-320.
3. Mazza, G.; Miniati, E. Introduction. In Anthocyanins in Fruits, Vegetables, and Grains; CRC Press: Boca Raton, FL, 1993; pp 1-23.
4. Wu, X.; Prior, R. L. Identification and characterization of anthocyanins by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry in common foods in the United States: vegetables, nuts, and grains. J. Agric. Food Chem. 2005, 53, 3101-3113.
5. Galli, R. L.; Bielinski, D. F.; Szprengiel, A.; Shukitt-Hale, B.; Joseph, J. A. Blueberry supplemented diet reverses age-related decline in hippocampal HSP70 neuroprotection. Neurobiol. Aging 2006, 27, 344-350.
6. Lau, F. C.; Shukitt-Hale, B.; Joseph, J. A. The beneficial effects of fruit polyphenols on brain aging. Neurobiol. Aging 2005, 26, S129-S132.
7. Hagiwara, A.; Yoshino, H.; Ichihara, T.; Kawabe, M.; Tamano, S.; Aoki, H.; Koda, T.; Nakamura, M.; Imaida, K.; Ito, N.; Shirai, T. Prevention by natural food anthocyanins, purple sweet potato color and red cabbage color, of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-associated colorectal carcinogenesis in rats initiated with 1,2-dimethylhydrazine. J. Toxicol. Sci. 2002, 27, 57-68.
8. Martin, S.; Favot, L.; Matz, R.; Lugnier, C.; Andriantsitohaina, R. Delphinidin inhibits endothelial cell proliferation and cell cycle progression through a transient activation of ERK-1/-2. Biochem. Pharmacol. 2003, 65, 669-675.
9. Hou, D.-X.; Fujii, M.; Terahara, N.; Yoshimoto, M. Molecular mechanisms behind the chemopreventive effects of anthocyanidins. J. Biomed. Biotechnol. 2004, 5, 321-325.
10. Yi, W.; Fischer, J.; Krewer, G.; Akoh, C. C. Phenolic compounds from blueberries can inhibit colon cancer cell proliferation and induce apoptosis. J. Agric. Food Chem. 2005, 53, 7320-7329.
11. Ding, M.; Feng, R.; Wang, S. Y.; Bowman, L.; Lu, Y.; Qian, Y.; Castranova, V.; Jiang, B.-H.; Shi, X. Cyanidin-3-glucoside, a natural product derived from blackberry, exhibits chemopreventive and chemotherapeutic activity. J. Biol. Chem. 2006, 281, 17359-17368.
12. Hecht, S. S.; Huang, C.; Stoner, G. D.; Li, J.; Kenney, P. M. J.; Sturla, S. J.; Carmella, S. G. Identification of cyanidin glycosides as constituents of freeze-dried black raspberries which inhibit anti-benzo[a]pyrene-7,8- diol-9,10-epoxide induced NF/κB and AP-1 activity. Carcinogenesis 2006, 27, 1617-1626.
13. Lala, G.; Malik, M.; Zhao, C.; He, J.; Kwon, Y.; Giusti, M. M.; Magnuson, B. A. Anthocyanin-rich extracts inhibit multiple biomarkers of colon cancer in rats. Nutr. Cancer 2006, 54, 84-93.
14. Rechner, A. R.; Kroner, C. Anthocyanins and colonic metabolites of dietary polyphenols inhibit platelet function. Thromb. Res. 2005, 116, 327-334.
15. Bell, D. R.; Gochenaur, K. Direct vasoactive and vasoprotective properties of anthocyanin rich extracts. J. Appl. Physiol. 2006, 100, 1164-1170.
16. Jayaprakasam, B.; Vareed, S. K.; Olson, L. K.; Nair, M. G. Insulin secretion by bioactive anthocyanins and anthocyanidins present in fruits. J. Agric. Food Chem. 2005, 53, 28-31.
17. Jayaprakasam, B.; Olson, L. K.; Schutzki, R. E.; Tai, M.-H.; Nair, M. G. Amelioration of obesity and glucose intolerance in high-fat-fed C57BL/6 mice by anthocyanins and ursolic acid in Cornelian cherry (Cornus mas). J. Agric. Food Chem. 2006, 54, 243-248.
18. Igarashi, K.; Kimura, Y.; Takenaka, A. Preventive effects of dietary cabbage acylated anthocyanins on paraquat-induced oxidative stress in rats. Biosci., Biotechnol., Biochem. 2000, 64, 1600-1607.
19. Youdim, K. A.; McDonald, J.; Kalt, W.; Joseph, J. A. Potential role of dietary flavonoids in reducing microvascular endothelium vulnerability to oxidative and inflammatory insults. J. Nutr. Biochem. 2002, 13, 282-288.
20. Kim, D. O.; Heo, H. J.; Kim, Y. J.; Yang, H. S.; Lee, C. Y. Sweet and sour cherry phenolics and their protective effects on neuronal cells. J. Agric. Food Chem. 2005, 53, 9921-9927.
21. Nielsen, I. L. F.; Dragsted, L. O.; Ravn-Haren, G.; Freese, R.; Rasmussen, S. E. Absorption and excretion of black currant anthocyanins in humans and Watanabe heritable hyperlipidemic rabbits. J. Agric. Food Chem. 2003, 51, 2813-2820.
22. Walton, M. C.; Lentle, R. G.; Reynolds, G. W.; Kruger, M. C.; McGhie, T. K. Anthocyanin absorption and antioxidant status in pigs. J. Agric. Food Chem. 2006, 54, 7940-7946.
23. Miyazawa, T.; Nakagawa, K.; Kudo, M.; Muraishi, K.; Someya, K. Direct intestinal absorption of red fruit anthocyanins, cyanidin-3-glucoside and cyanidin-3,5-diglucoside, into rats and humans. J. Agric. Food Chem. 1999, 47, 1083-1091.
24. Wu, X.; Cao, G.; Prior, R. L. Absorption and metabolism of anthocyanins in elderly women after consumption of elderberry or blueberry. J. Nutr. 2002, 132, 1865-1871.
25. Suda, I.; Oki, T.; Masuda, M.; Nishiba, Y.; Furuta, S.; Matsugano, K.; Sugita, K.; Terahara, N. Direct absorption of acylated anthocyanin in purple-fleshed sweet potato into rats. J. Agric. Food Chem. 2002, 50, 1672-1676.
26. Harada, K.; Kano, M.; Takayanagi, T.; Yamakawa, O.; Ishikawa, F. Absorption of acylated anthocyanins in rats and humans after ingesting an extract of Ipomoea batatas purple sweet potato tuber. Biosci., Biotechnol., Biochem. 2004, 68, 1500-1507.
27. Wolffram, S.; Block, M.; Ader, P. Quercetin-3-glucoside is transported by the glucose carrier SGLT1 across the brush border membrane of rat small intestine. J. Nutr. 2002, 132, 630-635.
28. Passamonti, S.; Vrhovsek, U.; Mattivi, F. The interaction of anthocyanins with bilitranslocase. Biochem. Biophys. Res. Commun. 2002, 296, 631-636.
29. Yi, W.; Akoh, C. C.; Fischer, J.; Krewer, G. Absorption of anthocyanins from blueberry extracts by Caco-2 human intestinal cell monolayers. J. Agric. Food Chem. 2006, 54, 5651-5658.
30. Kurilich, A. C.; Clevidence, B. A.; Britz, S. J.; Simon, P. W.; Novotny, J. A. Plasma and urine responses are lower for acylated vs nonacylated anthocyanins from raw and cooked purple carrots. J. Agric. Food Chem. 2005, 53, 6537-6542.
31. Wu, X.; Beecher, G. R.; Holden, J. M.; Haytowitz, D. B.; Gebhardt, S. E.; Prior, R. L. Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. J. Agric. Food Chem. 2006, 54, 4069-4075.
32. Verhoeven, D.; Goldbohm, R.; van Poppel, G.; Verhagen, H.; van den Brandt, P. Epidemiological studies on Brassica vegetables and cancer risk. Cancer Epidemiol. Biomarkers Prev. 1996, 5, 733-748.
33. Lucier, G.; Plummer, C. Commodity highlight: fresh-market cabbage. Vegetables Melons Outlook 2002, 12.
34. Lanzarini, G.; Morselli, L. Anthocyanins of red cabbage. Ind. Conserve 1974, 49, 16-20.
35. Ikeda, K.; Kikuzaki, H.; Nakamura, M.; Nakatani, N. Structure of two acylated anthocyanins from red cabbage (Brassica oleracea). Chem. Express 1987, 2, 563-566.
36. Idaka, E.; Yamakita, H.; Ogawa, T.; Kondo, T.; Yamamoto, M.; Goto, T. Structure of 3 diacylated anthocyanins isolated from red cabbage, Brassica oleracea. Chem. Lett. 1987, 6, 1213-1216.
37. Idaka, E.; Suzuki, K.; Yamakita, H.; Ogawa, T.; Kondo, T.; Goto, T. Structure of monoacylated anthocyanins isolated from red cabbage, Brassica oleracea. Chem. Lett. 1987, 1, 145-148.
38. Shimizu, T.; Muroi, T.; Ichi, T.; Nakamura, M.; Yoshihira, K. Analysis of red cabbage colors in commercial foods using high performance liquid chromatography with photodiode array detection mass spectrophotometry. J. Food Hyg. Soc. Jpn. 1997, 38, 34-38.
39. Giusti, M. M.; Rodriguez-Saona, L. E.; Griffin, D.; Wrolstad, R. E. Electrospray and tandem mass spectroscopy as tools for anthocyanin characterization. J. Agric. Food Chem. 1999, 47, 4657-4664.
40. Tian, Q.; Konczak, I.; Schwartz, S. J. Probing anthocyanin profiles in purple sweet potato cell line (Ipomoea batatas L. Cv. Ayamurasaki) by high-performance liquid chromatography and electrospray ionization tandem mass spectrometry. J. Agric. Food Chem. 2005, 53, 6503-6509.
41. Matsumoto, H.; Inaba, H.; Kishi, M.; Tominaga, S.; Hirayama, M.; Tsuda, T. Orally administered delphinidin 3-rutinoside and cyanidin 3-rutinoside are directly absorbed in rats and humans and appear in the blood as the intact forms. J. Agric. Food Chem. 2001, 49, 1546-1551.
42. Cao, G.; Muccitelli, H. U.; Sanchez-Moreno, C.; Prior, R. L. Anthocyanins are absorbed in glycated forms in elderly women: a pharmacokinetic study. Am. J. Clin. Nutr. 2001, 73, 920-926.
43. Kay, C. D.; Mazza, G.; Holub, B. J.; Wang, J. Anthocyanin metabolites in human urine and serum. Br. J. Nutr. 2004, 91, 933-942.
44. Wu, X.; Pittman, H. E. III.; Prior, R. L. Pelargonidin is absorbed and metabolized differently than cyanidin after marionberry consumption in pigs. J. Nutr. 2004, 134, 2603-2610.
45. Aura, A. M.; Martin-Lopez, P.; O'Leary, K. A.; Williamson, G.; Oksman-Caldentey, K. M.; Poutanen, K.; Santos-Buelga, C. In vitro metabolism of anthocyanins by human gut microflora. Eur. J. Nutr. 2005, 44, 133-142.
46. Prior, R. L.; Wu, X. Anthocyanins: structural characteristics that result in unique metabolic patterns and biological activities. Free Radical Res. 2006, 40, 1014-1028.
47. Tsuda, T.; Horio, F.; Osawa, T. Absorption and metabolism of cyanidin 3-O-β-glucoside in rats. FEBS Lett. 1999, 449, 179-182.
48. Wu, X.; Pittman, H. E.; Prior, R. L. Fate of anthocyanins and antioxidant capacity in contents of the gastrointestinal tract of weanling pigs following black raspberry consumption. J. Agric. Food Chem. 2006, 54, 583-589.
49. Wu, X.; Pittman, H. E., III; Mckay, S.; Prior, R. L. Aglycones and sugar moieties alter anthocyanin absorption and metabolism after berry consumption in weanling pigs. J. Nutr. 2005, 135, 2417-2424.