The metabolome of [2-14C](-)-epicatechin in humans: Implications for the assessment of efficacy, safety, and mechanisms of action of polyphenolic bioactives

Scientific Reports

Volumn 6, Issue , 2016, Pages

  Ottaviani, Javier I ^a   Borges, Gina ^b   Momma, Tony Y ^b   Spencer, Jeremy P E ^c   Keen, Carl L ^b   Crozier, Alan ^b   Schroeter, Hagen ^a  

^a MARS INC   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CARBON-14; CATECHIN; POLYPHENOL;

ADULT; ANIMAL; BLOOD; C57BL MOUSE; CHEMISTRY; DIETARY SUPPLEMENT; HALF LIFE TIME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MALE; MASS SPECTROMETRY; METABOLISM; MOUSE; ORAL DRUG ADMINISTRATION; SPRAGUE DAWLEY RAT; STEREOISOMERISM; URINE;

ADMINISTRATION, ORAL; ADULT; ANIMALS; CARBON RADIOISOTOPES; CATECHIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIETARY SUPPLEMENTS; HALF-LIFE; HUMANS; MALE; MASS SPECTROMETRY; MICE; MICE, INBRED C57BL; POLYPHENOLS; RATS, SPRAGUE-DAWLEY; STEREOISOMERISM;

EID: 84976897467     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep29034     Document Type: Article

References (31)

1. USDA and USDHHS. Dietary Guidelines for Americans. Ch. 4 (Washignton DC, 2010).
2. IOM. Dietary Reference Intakes: The Essential Guide to Nutrient Requirements (eds. Otten, J. J. Pitzi Hellwig, J., Meyers, L. D., Washignton DC, 2006).
3. Lupton, J. R. et al. Exploring the benefits and challenges of establishing a DRI-like process for bioactives. Eur J Nutr 53 Suppl 1, 1-9, doi: 10.1007/s00394-014-0666-3 (2014).
4. Schroeter, H. et al. Recommending flavanols and procyanidins for cardiovascular health: current knowledge and future needs. Mol Aspects Med 31, 546-557, doi: 10.1016/j.mam.2010.09.008 (2010).
5. Del Rio, D. et al. Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases. Antioxid Redox Signal 18, 1818-1892, doi: 10.1089/ars.2012.4581 (2013).
6. Crozier, A., Clifford, M. N., Del Rio, D. Flavonoids and Related Compounds: Bioavailaiblity and Funciton (eds.Spencer, J. P. E., Crozier, A.) Ch. 2, 45-78 (Boca Raton, CRC Press, 2012).
7. Balzer, J. et al. Sustained benefits in vascular function through flavanol-containing cocoa in medicated diabetic patients a doublemasked, randomized, controlled trial. J Am Coll Cardiol 51, 2141-2149, doi: 10.1016/j.jacc.2008.01.059 (2008).
8. Heiss, C. et al. Improvement of endothelial function with dietary flavanols is associated with mobilization of circulating angiogenic cells in patients with coronary artery disease. J Am Coll Cardiol 56, 218-224, doi: 10.1016/j.jacc.2010.03.039 (2010).
9. Curtis, P. J. et al. Chronic ingestion of flavan-3-ols and isoflavones improves insulin sensitivity and lipoprotein status and attenuates estimated 10-year CVD risk in medicated postmenopausal women with type 2 diabetes: a 1-year, double-blind, randomized, controlled trial. Diabetes Care 35, 226-232, doi: 10.2337/dc11-1443 (2012).
10. Desideri, G. et al. Benefits in cognitive function, blood pressure, and insulin resistance through cocoa flavanol consumption in elderly subjects with mild cognitive impairment: the Cocoa, Cognition, and Aging (CoCoA) study. Hypertension 60, 794-801, doi: 10.1161/hypertensionaha.112.193060 (2012).
11. Sansone, R. et al. Cocoa flavanol intake improves endothelial function and Framingham Risk Score in healthy men and women: a randomised, controlled, double-masked trial: the Flaviola Health Study. Br J Nutr 1-10, doi: 10.1017/S0007114515002822 (2015).
12. Schroeter, H. et al. (? )-Epicatechin mediates beneficial effects of flavanol-rich cocoa on vascular function in humans. Proc Natl Acad Sci USA 103, 1024-1029, doi: 10.1073/pnas.0510168103 (2006).
13. Loke, W. M. et al. Pure dietary flavonoids quercetin and (? )-epicatechin augment nitric oxide products and reduce endothelin-1 acutely in healthy men. Am J Clin Nutr 88, 1018-1025 (2008).
14. Mull, E. S. et al. A versatile approach to the regioselective synthesis of diverse (? )-epicatechin-?-d-glucuronides. Tetrahedron Letters 53, 1501-1503, doi: 10.1016/j.tetlet.2012.01.054 (2012).
15. Zhang, M., Erik Jagdmann, G. Jr., Van Zandt, M., Beckett, P., Schroeter, H. Enantioselective synthesis of orthogonally protected (2R,3R)-(? )-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (? )-epicatechin glucuronides and sulfates. Tetrahedron: Asymmetry 24, 362-373, doi: 10.1016/j.tetasy.2013.02.012 (2013).
16. Zhang, M. et al. Chemical synthesis and characterization of epicatechin glucuronides and sulfates: bioanalytical standards for epicatechin metabolite identification. J Nat Prod 76, 157-169, doi: 10.1021/np300568m (2013).
17. Natsume, M. et al. Structures of (? )-epicatechin glucuronide identified from plasma and urine after oral ingestion of (? )-epicatechin: differences between human and rat. Free Radic Biol Med 34, 840-849, doi: 10.1016/S0891-5849(02)01434-X (2003).
18. Ottaviani, J. I., Momma, T. Y., Kuhnle, G. K., Keen, C. L., Schroeter, H. Structurally related (? )-epicatechin metabolites in humans: assessment using de novo chemically synthesized authentic standards. Free Radic Biol Med 52, 1403-1412, doi: 10.1016/j. freeradbiomed.2011.12.010 (2012).
19. Ottaviani, J. I., Kwik-Uribe, C., Keen, C. L., Schroeter, H. Intake of dietary procyanidins does not contribute to the pool of circulating flavanols in humans. Am J Clin Nutr 95, 851-858, doi: 10.3945/ajcn.111.028340 (2012).
20. Actis-Goretta, L. et al. Elucidation of (? )-epicatechin metabolites after ingestion of chocolate by healthy humans. Free Radic Biol Med 53, 787-795, doi: 10.1016/j.freeradbiomed.2012.05.023 (2012).
21. van Duynhoven, J. et al. Metabolic fate of polyphenols in the human superorganism. Proc Natl Acad Sci USA 108 Suppl 1, 4531-4538, doi: 10.1073/pnas.1000098107 (2011).
22. Vogiatzoglou, A. et al. Assessment of the dietary intake of total flavan-3-ols, monomeric flavan-3-ols, proanthocyanidins and theaflavins in the European Union. Br J Nutr 111, 1463-1473, doi: 10.1017/S0007114513003930 (2014).
23. Vogiatzoglou, A. et al. Associations between flavan-3-ol intake and CVD risk in the Norfolk cohort of the European Prospective Investigation into Cancer (EPIC-Norfolk). Free Radic Biol Med 84, 1-10, doi: 10.1016/j.freeradbiomed.2015.03.005 (2015).
24. Kurlbaum, M., Mulek, M., Hogger, P. Facilitated uptake of a bioactive metabolite of maritime pine bark extract (pycnogenol) into human erythrocytes. PLoS One 8, e63197, doi: 10.1371/journal.pone.0063197 (2013).
25. Bors, W., Michel, C., Stettmaier, K. Electron paramagnetic resonance studies of radical species of proanthocyanidins and gallate esters. Arch Biochem Biophys 374, 347-355, doi: 10.1006/abbi.1999.1606 (2000).
26. Sang, S., Yang, I., Buckley, B., Ho, C. T., Yang, C. S. Autoxidative quinone formation in vitro and metabolite formation in vivo from tea polyphenol (? )-epigallocatechin-3-gallate: studied by real-time mass spectrometry combined with tandem mass ion mapping. Free Radic Biol Med 43, 362-371, doi: 10.1016/j.freeradbiomed.2007.04.008 (2007).
27. Das, N. P. Studies on flavonoid metabolism. Absorption and metabolism of (+ )-catechin in man. Biochem Pharmacol 20, 3435-3445, doi: 10.1016/0006-2952(71)90449-7 (1971).
28. Hackett, A. M., Griffiths, L. A., Broillet, A., Wermeille, M. The metabolism and excretion of (+ )-[14C]cyanidanol-3 in man following oral administration. Xenobiotica 13, 279-286, doi: 10.3109/00498258309052265 (1983).
29. IOM. Consensus Report: Evaluation of Biomarkers and Surrogate Endpoints in Chronic Disease (National Academies Press, Washignton DC).
30. Reichenbach, S., Juni, P. Medical food and food supplements: not always as safe as generally assumed. Ann Intern Med 156, 894-895, W314, doi: 10.7326/0003-4819-156-12-201206190-00012 (2012).
31. Sharma, P. K., He, M., Romanczyk, L. J., Schroeter, H. Synthesis of [2-C-13, 4-C-13]-(2R,3S)-catechin and [2-C-13, 4-C-13]-(2R,3R)-epicatechin. J. Label Compd. Radiopharm 53, 605-612, doi: 10.1002/jlcr.1791 (2010).