Synthesis and quantitative analysis of plasma-targeted metabolites of catechin and epicatechin

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 8, 2015, Pages 2233-2240

  Blount, Jack W ^a   Redan, Benjamin W ^b   Ferruzzi, Mario G ^b,c   Reuhs, Bradley L ^b   Cooper, Bruce R ^c   Harwood, John S ^c   Shulaev, Vladimir ^a   Pasinetti, Giulio ^d,e   Dixon, Richard A ^a  

^a UNIVERSITY OF NORTH TEXAS   (United States)

^b PURDUE UNIVERSITY   (United States)

^c PURDUE UNIVERSITY   (United States)

^d MOUNT SINAI SCHOOL OF MEDICINE   (United States)

^e VETERANS AFFAIRS MEDICAL CENTER   (United States)

Author keywords

catechin; glucuronosylation; O methylation; phase II metabolites; semisynthesis; structure determination; two site validation

Indexed keywords

ALKYLATION; BIOCHEMISTRY; BIOMOLECULES; CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; METHYLATION; NEURODEGENERATIVE DISEASES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; PHASE SEPARATION; PHENOLS; SYNTHESIS (CHEMICAL);

CATECHIN; GLUCURONOSYLATION; O-METHYLATION; PHASE II; SEMISYNTHESIS; STRUCTURE DETERMINATION; TWO-SITE VALIDATION;

FLAVONOIDS;

ANIMALIA; VITACEAE;

CATECHIN; GRAPE SEED EXTRACT;

ANIMAL; BLOOD; METABOLISM; RAT; SYNTHESIS;

ANIMALS; CATECHIN; GRAPE SEED EXTRACT; RATS;

EID: 84924266566     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf505922b     Document Type: Article

References (27)

1. Ishikawa, T.; Suzukawa, M.; Ito, T.; Yoshida, H.; Ayaori, M.; Nishiwaki, M.; Yonemura, A.; Hara, Y.; Nakamura, H. Effect of tea flavonoid supplementation on the susceptibility of low-density lipoprotein to oxidative modification Am. J. Clin. Nutr. 1997, 66, 261-266
2. Guo, W.; Kong, E.; Meydani, M. Dietary polyphenols, inflammation, and cancer Nutr. Cancer 2009, 61, 807-810
3. Dixon, R. A. Natural products and disease resistance Nature 2001, 411, 843-847
4. Wang, J.; Ferruzzi, M. G.; Ho, L.; Blount, J.; Janle, E.; Arrieta-Cruz, I.; Sharma, V.; Cooper, B.; Lobo, J.; Simon, J. E.; Zhang, C.; Cheng, A.; Qian, X.; Pavlides, C.; Dixon, R. A.; Pasinetti, G. M. Brain-targeted proanthocyanidin metabolites for Alzheimers disease treatment J. Neurosci. 2012, 32, 5144-5150
5. Wang, J.; Ho, L.; Zhao, W.; Ono, K.; Rosensweig, C.; Chen, L.; Humala, N.; Teplow, D. B.; Pasinetti, G. M. Grape-derived polyphenolics prevent Aβ oligomerization and attenuate cognitive deterioration in a mouse model of Alzheimers disease J. Neurosci. 2008, 28, 6388-6392
6. Sharma, V.; Zhang, C.; Pasinetti, G. M.; Dixon, R. A. Fractionation of grape seed proanthocyanidins for bioactivity assessment. In Recent Advances in Phytochemistry: Biological Activity of Phytochemicals; Gang, D. R., Ed.; Springer: New York, 2010; Vol. 41, pp 33-46.
7. Blount, J. W.; Ferruzzi, M. G.; Raftery, D.; Pasinetti, G. M.; Dixon, R. A. Enzymatic synthesis of substituted epicatechins for bioactivity studies in neurological disorders Biochem. Biophys. Res. Commun. 2011, 417, 457-461
8. Ćirić, A.; Prosen, H.; Jelikić-Stankov, M.; Aurłević, P. Evaluation of matrix effect in determination of some bioflavonoids in food samples by LC-MS/MS method Talanta 2012, 99, 780-790
9. Gonzalez-Manzano, S.; Gonzalez-Paramas, A.; Santos-Buelga, C.; Duenas, M. Preparation and characterization of catechin sulfates, glucuronides, and methylethers with metabolic interest J. Agric. Food Chem. 2009, 57, 1231-1238
10. Baba, S.; Osakabe, N.; Natsume, M.; Muto, Y.; Takizawa, T.; Terao, J. In vivo comparison of the bioavailability of (+)-catechin, (-)-epicatechin and their mixture in orally administered rats J. Nutr. 2001, 131, 2885-2891
11. Baba, S.; Osakabe, N.; Natsume, M.; Yasuda, A.; Takizawa, T. Cocoa powder enhances the level of antioxidative activity in rat plasma Br. J. Nutr. 2000, 84, 673-680
12. Feng, W. Metabolism of green tea catechins: an overview Curr. Drug Metab. 2006, 7, 755-809
13. Spencer, J.; Schroeter, H.; Rechner, A.; Rice-Evans, C. Bioavailability of flavan-3-ols and procyanidins: Gastrointestinal tract influences and their relevance to bioactive forms in vivo Antioxid. Redox Signaling 2001, 3, 1023-1039
14. Abd-el-Mohsen, M.; Kuhnle, G.; Rechner, A.; Schroeter, H.; Rose, S.; Jenner, P.; Rice-Evans, C. Uptake and metabolism of epicatechin and its access to the brain after oral ingestion Free Radical Biol. Med. 2002, 33, 1693-1702
15. Piskula, M.; Terao, J. Accumulation of (-)-epicatechin metabolites in rat plasma after oral administration and distribution of conjugation enzymes in rat tissues J. Nutr. 1998, 128, 1172-1178
16. Spencer, J. Role of flavonoids in the diet metabolism of tea flavonoids in the gastrointestinal tract. Proceedings of the third international scientific symposium on tea and human health J. Nutr. 2003, 133, 3255S-3261S
17. Tsang, C.; Auger, C.; Mullen, W.; Bornet, A.; Rouanet, J. M.; Crozier, A.; Teissedre, P. L. The absorption, metabolism and excretion of flavan-3-ols and procyanidins following the ingestion of a grape seed extract by rats Br. J. Nutr. 2005, 94, 170-81
18. Urpi-Sarda, M.; Monagas, M.; Khana, N.; Lloracha, L.; Lamuela-Raventósa, R. M.; Jáureguib, O.; Estruch, R.; Izquierdo-Pulidoa, M.; Andrés-Lacueva, C. Targeted metabolic profiling of phenolics in urine and plasma after regular consumption of cocoa by liquid chromatography-tandem mass spectrometry J. Chromatogr. A 2009, 1216.43, 7258-7267
19. Roura, E.; Andres-Lacueva, C.; Estruch, R.; Lourdes Mata Bilbao, M.; Izquierdo-Pulido, M.; Lamuela-Raventos, R. M. The effects of milk as a food matrix for polyphenols on the excretion profile of cocoa (-)-epicatechin metabolites in healthy human subjects Br. J. Nutr. 2008, 100, 846-51
20. Matuszewski, B. K.; Constanzer, M. L.; Chavez-Eng, C. M. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS Anal. Chem. 2003, 75, 3019-3030
21. Li, L.; Liang, S.; Du, F.; Li, C. Simultaneous quantification of multiple licorice flavonoids in rat plasma J. Am. Soc. Mass Spectrom. 2007, 18, 778-782
22. Gardana, C.; Guarnieri, S.; Riso, P.; Simonetti, P.; Porrini, M. Flavanone plasma pharmacokinetics from blood orange juice in human subjects Br. J. Nutr. 2007, 98, 165-172
23. Horwitz, W.; Albert, R. The Horwitz ratio (HorRat): A useful index of method performance with respect to precision J. AOAC Int. 2006, 89, 1095-109
24. Zhang, M.; Jagdmann, G. E., Jr.; Van Zandt, M.; Sheeler, R.; Beckett, P.; Schroeter, H. Chemical synthesis and characterization of epicatechin glucuronides and sulfates: bioanalytical standards for epicatechin metabolite identification J. Nat. Prod. 2013, 76, 157-69
25. Natsume, M.; Osakabe, 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 Radical Biol. Med. 2003, 34, 840-849
26. He, X.-Z.; Li, W.-S.; Blount, J. W.; Dixon, R. A. Regioselective synthesis of plant flavonoid glycosides in E. coli Appl. Microbiol. Biotechnol. 2008, 80, 253-260
27. 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 Radical Biol. Med. 2012, 52, 1403-1412