A comprehensive evaluation of the [2-14C](–)-epicatechin metabolome in rats

Free Radical Biology and Medicine

Volumn 99, Issue , 2016, Pages 128-138

  Borges, Gina ^a   van der Hooft, Justin J J ^a,b   Crozier, Alan ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

Absorption; Acute ingestion; Disposition; Excretion; Metabolism; Rats; 2 14C ( ) Epicatechin

Indexed keywords

EPICATECHIN; GLUCURONIDE; HIPPURIC ACID; LACTONE DERIVATIVE; CARBON; CATECHIN; EPICATECHIN-GLUCURONIDE; GAMMA-VALEROLACTONE; HIPPURIC ACID DERIVATIVE; LACTONE;

ANIMAL TISSUE; ARTICLE; BLOOD LEVEL; BODY FLUID; CARDIOVASCULAR SYSTEM; CECUM; COLON; CONTROLLED STUDY; DUODENUM; ERYTHROCYTE; FECES; GASTROINTESTINAL TRACT; GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ILEUM; INGESTION; ISOTOPE LABELING; JEJUNUM; MALE; MASS SPECTROMETRY; METABOLOME; METHYLATION; NONHUMAN; PLASMA; PRIORITY JOURNAL; RADIOACTIVITY; RAT; STOMACH; URINARY EXCRETION; URINE; ANALOGS AND DERIVATIVES; ANIMAL; BIOTRANSFORMATION; BLOOD; CHEMISTRY; HUMAN; METABOLISM; SPECIES DIFFERENCE; SPRAGUE DAWLEY RAT;

ANIMALS; BIOTRANSFORMATION; CARBON RADIOISOTOPES; CATECHIN; DUODENUM; FECES; GLUCURONIDES; HIPPURATES; HUMANS; ILEUM; JEJUNUM; LACTONES; MALE; METABOLOME; METHYLATION; RATS; RATS, SPRAGUE-DAWLEY; SPECIES SPECIFICITY;

EID: 84981166140     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2016.08.001     Document Type: Article

References (43)

1. n analysis of phenolic compounds and purine alkaloids in green and black tea. J. Agric. Food Chem. 52 (2002), 2807–2815.
2. [2] Crozier, A., Clifford, M.N., Del Rio, D., Bioavailability of dietary monomeric and polymeric flavan-3-ols. Spencer, J.P.E., Crozier, A., (eds.) Flavonoids and related Compounds: Bioavailability and Function, 2012, CRC Press, Boca Raton, 45–78.
3. [3] Tomás-Barbéran, F., Borges, G., Crozier, A., Phytochemicals in cocoa and the bioavailability of flavan-3-ols. Crozier, A., Ashihara, H., Tomás-Barbéran, F., (eds.) Teas, Cocoa and Coffee: Plant Secondary Metabolites and Health, 2012, Blackwell Publishing, Oxford, 193–217.
4. [4] Del Rio, D., Rodriguez-Mateos, A.M., Spencer, J.P.E., Tognolini, M., Borges, G., Crozier, A., Dietary (poly)phenolics in human health and disease: structures, bioavailability, evidence of protective effects and potential mechanisms. Antioxid. Redox Signal. 18 (2013), 1818–1892.
5. [5] Rodriguez-Mateos, A.M., Vauzour, D., Kreuger, C.G., Shanmuganayagam, D., Reed, D., Canali, L., Mena, P., Del Rio, D., Crozier, A., Flavonoids and related compounds, bioavailability bioactivity and impact on human health: an update. Arch. Toxicol. 88 (2014), 1803–1853.
6. [6] Schroeter, H., Heiss, C., Spencer, J.P., Keen, C.L., Lupton, J.R., Schmitz, H.H., Recommending flavanols and procyanidins for cardioovascular health: current knowledge and future needs. Mol. Asp. Med. 31 (2010), 546–5557.
7. [7] Sansone, R., Rodriguez-Mateos, A., Heuel, J., Falk, D., Schuler, D., Wagstaff, R., Kuhnle, G.G., Spencer, J.P., Schroeter, H., Merx, M.W., Kelm, M., Heiss, C., Cocao flavonol 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. 114 (2015), 1246–1255.
8. [8] Brickman, A.M., Khan, U.A., Provenzano, F.A., Yeung, L.K., Suzuki, W., Schroeter, H., Wall, M., Sloan, R.P., Small, S.A., Enhancing dentate gyrus function with dietary flavanols improves cognition in older adults. Nat. Neurosci. 17 (2014), 1798–1803.
9. [9] Mastroiacovo, D., Kwik-Uribe, C., Grassi, D., Necozione, S., Raffaele, A., Pistacchio, L., Righetti, R., Bocale, R., Lechiara, M.C., Marini, C., Desideri, G., Cocoa flavonol consumption improves cognitive function, blood ressure control, and metabolic profile in elderly subjects: the Cocoa Recognition and Aging (C0CoA) Study – a randomized control trial. Am. J. Clin. Nutr. 101 (2015), 538–548.
10. [10] Kroon, P.A., Clifford, M.N., Crozier, A., Day, A.J., Donovan, J.L., Monach, C., Williamson, G., Based on in vivo data, how do we assess the effects of exposure to dietary polyphenols in vitro ?. Am. J. Clin. Nutr. 80 (2004), 15–21.
11. [11] Crozier, A., Absorption metabolism and excretion of (–)-epicatechin in humans: an evaluation of recent findings. Am. J. Clin. Nutr. 98 (2013), 861–862.
12. 14C](–)-epicatechin in humans: wider nutritional implications for the biomedical assessment of efficacy, safety, and mechanisms of action of polyphenolic bioactives. Sci. Rep., 6, 2016, 29034 10:1038/srep29024.
13. [13] 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 (2012), 1403–1412.
14. [14] Actis-Goretta, L., Lévèques, A., Giuffrida, F., Romanov-Michailidis, F., Viton, F., Barron, D., Duenas-Paton, M., Gonzalez-Manzano, S., Santos-Buelga, C., Williamson, G., Dionisi, F., Elucidation of (–)-epicatechin metabolites after ingestion of chocolate by healthy humans. Free Radic. Biol. Med. 53 (2012), 787–795.
15. [15] Natsume, M., Osaka, N., Oyama, M., Sasaki, M., Baba, S., Nakamura, Y., Osawa, T., Terao, J., Structures of (–)-epicatechin glucuronide identified from plasma and urine after oral ingestion of (–)-epicatechin: differences between human and rat. Free Radic. Biol. Med. 34 (2003), 840–849.
16. [16] Reeve, D.R., Crozier, A., Radioactivity monitor for high-performance liquid chromatography. J. Chromatogr. 137 (1977), 271–281.
17. 13C]-(2R,3R)-Epicatechin. J. Label. Comp. Radiopharm 45 (2010), 605–612.
18. [18] Sharma, P.K., He, M., Jurayj, J., Gou, D.M., Lombardy, R., Romanczyk, L.J. Jr., Schroeter, H., Enantioselctive syntheses of sulfur analogues of flavan-3-ols. Molecules 15 (2010), 5595–5619.
19. [19] Mull, E.S., van Zandt, M., Golebiowski, A., Beckett, R.P., Sharma, P.K., Schroeter, H., A versatile approach to the regioselective synthesis of diverse (–)-epicatechin-β-D-glucuronides. Tetrahed. Lett. 53 (2012), 1501–1503.
20. [20] Zhang, M., Jagdmann, E.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. Tetrahed. Asymmetry 24 (2013), 362–373.
21. [21] Stalmach, A., Troufflard, S., Serafini, M., Crozier, A., Absorption, metabolism, and excretion of choladi green tea flavan–3-ols by humans. Mol. Nutr. Food Res. 53:Suppl. 1 (2009), S44–S53.
22. [22] Borges, G., Mullen, W., Mullan, A., Lean, M.E.J., Roberts, S.A., Crozier, A., Bioavailability of multiple components following acute ingestion of a polyphenol-rich juice drink. Mol. Nutr. Food Res. 54:Suppl. 2 (2010), S268–S277.
23. [23] Sang, S., Yang, C.S., Structural identification of novel glucoside and glucuronide metabolites of (–)-epigallocatechin-3-gallate in mouse urine using liquid chromatography/ electrospray ionization tandem mass spectrometry. Rapid Commun. Mass Spectrom. 22 (2008), 3693–3699.
24. [24] Llorach, R., Garrido, I., Monagas, M., Urpi-Sarda, M., Tulipani, S., Bartolome, B., Andres-Lacueva, C., Metabolomics study of human urinary metabolome modifications after intake of almond (Prunus dulcis (Mill.) D.A. Webb) Skin polyphenols. J. Prot. Res 9 (2010), 859–5867.
25. [25] van der Hoooft, J.J.J., de Vos, R.C., Mihaleva, V., Bino, R.J., Ridder, L., Jacobs, D.M., van Duynhoven, J.P., Vervoort, J., Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal. Chem. 84 (2012), 7263–7271.
26. [26] West, G.B., Brown, J.H., The origin of allometric scaling laws from genomes to ecosystems: towards a quantitative unifying theory of biological structure and organization. J. Exp. Biol. 208 (2005), 1575–1592.
27. [27] Heiss, C., Sansome, R., Krabbe, M., Schuler, D., Rodrigues-Mateos, A., Ktaemer, T., Cortese-Krott, M.M., Kuhnle, G.G., Spencer, J.P., Schroeter, H., Merx, M.W., Kelm, M., Impact of cocoa flavanol intake on age dependent vascular stiffness in healthy men: a randomized, controlled, double-masked trial. Age, 37, 2015, 974, 10.1007/s11357-015-9794-9.
28. [28] Vogiatzoglou, A., Heuer, T., Mulligan, A.A., Lentjes, M.A., Luben, R.N., Kuhnle, G.G., Estimated dietary intake so flavanols in the German population (German National Nutrition Survey II). Eur. J. Nutr. 53 (2014), 635–643.
29. [29] Vogiatzoglou, A., Mulligan, A.A., Luben, R.N., Lentjes, M.A., Heiss, C., Kelm, M., Merx, M.W., Spencer, J.P., Schroeter, H., Kuhnle, G.G., 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 (2014), 1463–1473.
30. [30] Vogiatzoglou, A., Mulligan, A.A., Bhaniani, A., Lentjes, M.A., McTaggart, A., Luben, R.N., Heiss, C., Kelm, M., Merx, M.W., Spencer, J.P., Schroeter, H., Khaw, K.T., Kuhnle, G.G., 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 (2015), 1–10.
31. 14C]catechin in the rat and guinea pig. Biochem. J. 115 (1969), 831–836.
32. [32] Shaw, I.C., Griffiths, L.A., Identification of the major biliary metabolite of (+)-catechin in the rat. Xenobiotica 10 (1980), 905–911.
33. [33] Piskula, M.K., Terao, J., Accumulation of (–)-epicatechin metabolites in rat plasma after oral administraion and distribution of conjugation enzumes in rat tissues. J. Nutr. 128 (1998), 1171–1178.
34. [34] Okushio, K., Suuuki, M., Matsumoto, N., Nanjo, F., Hara, Y., Identification of (–)-epicatechin metabolites and their metabolic fate in the rat. Drug Metab. Disp. 57 (1999), 309–316.
35. [35] Kuhnle, G.G., Spencer, J.P.E., Schroeter, H., Shenoy, B., Debham, E.S., Kaila, S., Srai, S., Rice-Evans, C., Hahn, U., Epicatechin and catechin are O-methylated and glucuronidated in the small intestine. Biochem. Biophys. Res. Commun. 277 (2000), 507–512.
36. [36] Actis-Goetta, L., Lévèques, A., Rein, M., Teml, A., Schäfer, C., Hofmann, U., Li, H., Schwab, M., Eichelbaum, M., Williamson, G., Intestinal absorption, metabolism and excretion of (–)-epicatechin in healthy humans assessed using an intestinal perfusion technique. Am. J. Clin. Nutr. 98 (2013), 924–933.
37. 14C]catechin. Biochem. J. 125 (1971), 417–423.
38. 3H-labelled tea antioxidants (+)-catechin and (–)-epicatechin in rat. Xenobiotica 33 (2003), 743–753.
39. [39] Donovan, J.L., Crespy, V., Manach, C., Morand, C., Besson, C., Scalbert, A., Rémésy, C., Catechin is metabolized in both the small intestine and liver of rats. J. Nutr. 131 (2001), 1753–1757.
40. [40] Cordero-Herrera, I., Martin, M.A., Goya, L., Ramos, S., Cocoa flavonoids protect hepatic cells against high glucose-induced oxiative strees: relevance of MAPKs. Mol. Nutr. Food Res. 59 (2015), 597–609.
41. [41] Faria, A., Pestana, D., Teixeira, D., Couraud, P.O., Romero, J., Weksler, B., de Freitas, V., Mateus, N., Calhau, C., Insights into the putative catechin and epicatechin transport across the blood-brain barrier. Food Funct. 2 (2011), 39–44.
42. [42] Martin, M.A., Fernández-Millán, E., Ramos, S., Bravo, L., Goya, L., Cocoa flavonoid epicatechin protects pancreatic beta cell viability and function against oxidative stress. Mol. Nutr. Food Res. 58 (2014), 447–456.
43. [43] Wang, J., Ferruz, M.G., Ho, L., Blount, J., Janie, E.M., Gong, B., Pan, Y., Gowda, G.A., Raftery, D., Arrieta-Cruz, I., Sharma, V., Cooper, B., Lobo, J., Simon, J.E., Zhang, C., Cheng, A., Qian, X., Ono, K., Teplow, D.B., Pavlides, C., Dixon, R.A., Pasinetti, G.M., Brain-targeted proanthocyanidin metabolites for Alzheimer's disease treatment. J. Neurosci. 32 (2012), 5144–5150.