The C-glycosyl flavonoid, aspalathin, is absorbed, methylated and glucuronidated intact in humans

Molecular Nutrition and Food Research

Volumn 53, Issue 9, 2009, Pages 1104-1111

  Courts, Fraser L ^a   Williamson, Gary ^a,b  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

Absorption; Aspalathin; C glycoside; Flavonoid; Methylation

Indexed keywords

ASPALATHIN; CATECHOL METHYLTRANSFERASE; CHALCONE DERIVATIVE; GLUCURONIDE;

ABSORPTION; ADULT; ARTICLE; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; INTESTINE; LIVER; MALE; MASS SPECTROMETRY; METABOLISM; METHYLATION; PHYSIOLOGY;

ABSORPTION; ADULT; CATECHOL O-METHYLTRANSFERASE; CHALCONES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; GLUCURONIDES; HUMANS; INTESTINES; LIVER; MALE; MASS SPECTROMETRY; METHYLATION;

ASPALATHUS LINEARIS;

EID: 70349634169     PISSN: 16134125     EISSN: 16134133     Source Type: Journal    
DOI: 10.1002/mnfr.200800569     Document Type: Article

References (19)

1. Williamson, G., Manach, C., Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies, Am. J. Clin. Nutr. 2005, 81, 243-255.
2. Tomá Barberá, F. A., Clifford, M. N., Flavanones, chalcones and dihydrochalcones - nature, occurrence and dietary burden, J. Sci. Food Agric. 2000, 80, 1073-1080.
3. Koeppen, B. H., Roux, D. G., C-glycosyl flavonoids. The chemistry of aspalathin, Biochem. J. 1966, 99, 604-609.
4. Kreuz, S., Joubert, E., Waldmann, K.-H., Ternes, W., Aspala-thin, a flavonoid in Aspalathus linearis (rooibos), is absorbed by pig intestine as C-glycoside, Nutr. Res. 2008, 28, 690-701.
5. Gulliver, P. A., Tipton, K. F., The purification and properties of pig-liver catechol-O-methyl transferase, Eur. J. Biochem. 1978, 88, 439-444.
6. Bertocci, B., Garotta, G., Da Prada, M., Lahm, H. W., et al., Immunoaffinity purification and partial amino acid sequence analysis of catechol-O-methyltransferase from pig liver, Biochim. Biophys. Acta 1991, 1080, 103-109.
7. Kazuno, S., Yanagida, M., Shindo, N., Murayama, K., Mass spectrometric identification and quantification of glycosyl flavonoids, including dihydrochalcones with neutral loss scan mode, Anal. Biochem. 2005, 347, 182-192.
8. Creveling, C. R., Dalgard, N., Shimizu, H., Daly, J. W., Catechol O-methyltransferase III. m- and p-O-methylation of catecholamines and their metabolites, Mol. Pharmacol. 1970, 6, 691-696.
9. Creveling, C. R., Morris, N., Shimizu, H., Ong, H. H., Daly, J., Catechol O-methyltransferase IV. m- and p-methylation of substituted catechols, Mol. Pharmacol. 1972, 8, 398-409.
10. Lotta, T., Vidgren, J., Tilgmann, C., Ulmanen, I., et al., Kinetics of human soluble and membrane-bound catechol O-methyltransferase: a revised mechanism and description of the thermolabile variant of the enzyme. Biochemistry 1995, 34, 4202-4210.
11. van der Woude, H., Boersma, M. G., Vervoort, J., Rietjens, I. M. C. M., Identification of 14 quercetin phase II mono- and mixed conjugates and their formation by rat and human phase II in vitro model systems, Chem. Res. Toxicol. 2004, 17, 1520-1530.
12. Walgren, R. A., Walle, U. K., Walle, T., Transport of quercetin and its glucosides across human intestinal epithelial Caco-2 cells, Biochem. Pharmacol. 1998, 55, 1721-1727.
13. Murota, K., Shimizu, S., Chujo, H., Moon, J. H., Terao, J., Efficiency of absorption and metabolic conversion of quercetin and its glucosides in human intestinal cell line Caco-2, Arch. Biochem. Biophys. 2000, 384, 391-397.
14. Day, A. J., Cañada, F. J., Díaz, J. C., Kroon, P. A., et al., Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase, FEBS Lett. 2000, 468, 166-170.
15. Day, A. J., DuPont, M. S., Ridley, S., Rhodes, M., et al., Deglycosylation of flavonoid and isoflavonoid glycosides by human small intestine and liver b-glucosidase activity, FEBS Lett. 1998, 436, 71-75.
16. Walgren, R. A., Karnaky, K. J., Lindenmayer, G. E., Walle, T., Efflux of dietary flavonoid quercetin 49-β-glucoside across human intestinal Caco-2 cell monolayers by apical multidrug resistance-associated protein-2, J. Pharmacol. Exp. Ther. 2000, 294, 830-836.
17. Berrin, J.-G., Czjzek, M., Kroon, P. A., Mclauchlan, W. R., et al., Substrate (aglycone) specificity of human b-glucosidase, Biochem. J. 2003, 373, 41-48.
18. Huang, M., du Plessis, J., du Preez, J., Hamman, J., Viljoen, A., Transport of aspalathin, a rooibos tea flavonoid, across the skin and intestinal epithelium, Phytother. Res. 2008, 22, 699-704.
19. Palma, P. N., Bonifácio, M. J., Loureiro, A. I., Wright, L. C., et al., Molecular modeling and metabolic studies of the interaction of catechol-O-methyltransferase and a new nitrocatechol inhibitor, Drug Metab. Dispos. 2003, 31, 250-258.