Profiling a gut microbiota-generated catechin metabolite's fate in human blood cells using a metabolomic approach

Journal of Pharmaceutical and Biomedical Analysis

Volumn 114, Issue , 2015, Pages 71-81

  Mülek, Melanie ^a   Fekete, Agnes ^b   Wiest, Johannes ^a   Holzgrabe, Ulrike ^a   Mueller, Martin J ^b   Högger, Petra ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

LC MS MS; Metabolism; NMR; Pine bark extract; Polyphenols

Indexed keywords

( 3,4 DIHYDROXYPHENYL) GAMMA VALEROLACTONE; CATECHIN; CYSTEINE; ESTER; FLAVONOID; GLUTATHIONE; GLUTATHIONE DISULFIDE; ORGANOSULFUR DERIVATIVE; PYCNOGENOL; UNCLASSIFIED DRUG; GAMMA-VALEROLACTONE; LACTONE; PLANT EXTRACT; POLYPHENOL; PYCNOGENOLS;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; BARK; BLOOD CELL; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DETERMINATION; DRUG METABOLISM; DRUG TRANSFORMATION; HUMAN; HUMAN CELL; HUMAN EXPERIMENT; IN VITRO STUDY; IN VIVO STUDY; INGESTION; INTESTINE FLORA; ISOMER; METABOLITE; METABOLOMICS; NORMAL HUMAN; PINE; PRIORITY JOURNAL; BIOTRANSFORMATION; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROCEDURES; REFERENCE VALUE;

BIOTRANSFORMATION; BLOOD CELLS; CATECHIN; FLAVONOIDS; GASTROINTESTINAL MICROBIOME; GLUTATHIONE; HUMANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; METABOLOMICS; PINUS; PLANT BARK; PLANT EXTRACTS; POLYPHENOLS; REFERENCE VALUES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84930960311     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2015.04.042     Document Type: Article

References (27)

1. Lewandowska U., Szewczyk K., Hrabec E., Janecka A., Gorlach S. Overview of metabolism and bioavailability enhancement of polyphenols. J. Agric. Food Chem. 2013, 61:12183-12199.
2. Hollman P.C. Unravelling of the health effects of polyphenols is a complex puzzle complicated by metabolism. Arch. Biochem. Biophys. 2014, 559:100-105.
3. Rohdewald P. A review of the French maritime pine bark extract (Pycnogenol), a herbal medication with a diverse clinical pharmacology. Int. J. Clin. Pharmacol. Ther. 2002, 40:158-168.
4. Maimoona A., Naeem I., Saddiqe Z., Jameel K. A review on biological, nutraceutical and clinical aspects of French maritime pine bark extract. J. Ethnopharmacol. 2011, 133:261-277.
5. Grimm T., Skrabala R., Chovanova Z., Muchova J., Sumegova K., Liptakova A., Durackova Z., Högger P. Single and multiple dose pharmacokinetics of maritime pine bark extract (pycnogenol) after oral administration to healthy volunteers. BMC Clin. Pharmacol. 2006, 6:4.
6. Düweler K.G., Rohdewald P. Urinary metabolites of French maritime pine bark extract in humans. Pharmazie 2000, 55:364-368.
7. Meng X.F., Sang S.M., Zhu N.Q., Lu H., Sheng S.Q., Lee M.J., Ho C.T., Yang C.S. Identification and characterization of methylated and ring-fission metabolites of tea catechins formed in humans, mice, and rats. Chem. Res. Toxicol. 2002, 15:1042-1050.
8. Sanchez-Patan F., Chioua M., Garrido I., Cueva C., Samadi A., Marco-Contelles J., Moreno-Arribas M.V., Bartolome B., Monagas M. Synthesis, analytical features, and biological relevance of 5-(3',4'-dihydroxyphenyl)-gamma-valerolactone, a microbial metabolite derived from the catabolism of dietary flavan-3-ols. J. Agric. Food Chem. 2011, 59:7083-7091.
9. Uhlenhut K., Högger P. Facilitated cellular uptake and suppression of inducible nitric oxide synthase by a metabolite of maritime pine bark extract (Pycnogenol). Free Radic. Biol. Med. 2012, 53:305-313.
10. Kurlbaum M., Mülek M., Högger P. Facilitated uptake of a bioactive metabolite of maritime pine bark extract (Pycnogenol) into human erythrocytes. PLoS ONE 2013, 8:e63197.
11. Mülek M., Högger P. Highly sensitive analysis of polyphenols and their metabolites in human blood cells using dispersive SPE extraction and LC-MS/MS. Anal. Bioanal. Chem. 2015, 407:1885-1899.
12. Polepally A.R., Kumar V.V.P., Bhamidipati R., Kota J., Naveed S.A., Reddy K.H., Mamidi R., Selvakumar N., Mullangi R., Srinivas N.R. Assessing the issue of instability due to Michael adduct formation in novel chemical entities possessing a carbon-carbon double bond during early drug development-applicability of common laboratory analytical protocols. Biomed. Chromatogr. 2008, 22:960-976.
13. Roowi S., Stalmach A., Mullen W., Lean M.E., Edwards C.A., Crozier A. Green tea flavan-3-ols: colonic degradation and urinary excretion of catabolites by humans. J. Agric. Food Chem. 2010, 58:1296-1304.
14. Stoupi S., Williamson G., Drynan J.W., Barron D., Clifford M.N. Procyanidin B2 catabolism by human fecal microflora: partial characterization of 'dimeric' intermediates. Arch. Biochem. Biophys. 2010, 501:73-78.
15. Catalan U., Rodriguez M.A., Ras M.R., Macia A., Mallol R., Vinaixa M., Fernandez-Castillejo S., Valls R.M., Pedret A., Griffin J.L., Salek R., Correig X., Motilva M.J., Sola R. Biomarkers of food intake and metabolite differences between plasma and red blood cell matrices; a human metabolomic profile approach. Mol. Biosyst. 2013, 9:1411-1422.
16. Zhu M., Zhang H., Humphreys W.G. Drug metabolite profiling and identification by high-resolution mass spectrometry. J. Biol. Chem. 2011, 286:25419-25425.
17. M. Rappold, Synthese von d-(3',4'-dihydroxyphenyl)-y-valerolacton und Derivaten sowie die Enantiomerentrennung der Zwischenstufen an chiraler Phase und Synthese des Azodianillin-8-azidoadenosintriphosphat-Lithiumsalzes, Institut für Pharmazie und Lebensmittelchemie, Universität Würzburg, 2010, pp. 11-21.
18. Xiao J., Högger P. Stability of dietary polyphenols under the cell culture conditions. J. Agric. Food Chem. 2015, 63:1547-1557.
19. Wrona T., Mauriala T., Bateman K.P., Mortishire-Smith R.J., O'Connor D. 'All-in-one' analysis for metabolite identification using liquid chromatography/hybrid quadrupole time-of-flight mass spectrometry with collision energy switching. Rapid Commun. Mass Spectrom. 2005, 19:2597-2602.
20. Sumner L.W., Amberg A., Barrett D., Beale M.H., Beger R., Daykin C.A., Fan T.W., Fiehn O., Goodacre R., Griffin J.L., Hankemeier T., Hardy N., Harnly J., Higashi R., Kopka J., Lane A.N., Lindon J.C., Marriott P., Nicholls A.W., Reily M.D., Thaden J.J., Viant M.R. Proposed minimum reporting standards for chemical analysis Chemical Analysis Working Group (CAWG) Metabolomics Standards Initiative (MSI). Metabolomics 2007, 3:211-221.
21. Mali'n T.J., Lindberg S., Astot C. Novel glutathione conjugates of phenyl isocyanate identified by ultra-performance liquid chromatography/electrospray ionization mass spectrometry and nuclear magnetic resonance. J. Mass Spectrom. 2014, 49:68-79.
22. Hopkinson R.J., Barlow P.S., Schofield C.J., Claridge T.D. Studies on the reaction of glutathione and formaldehyde using NMR. Org. Biomol. Chem. 2010, 8:4915-4920.
23. Satoh K. The high non-enzymatic conjugation rates of some glutathione S-transferase (GST) substrates at high glutathione concentrations. Carcinogenesis 1995, 16:869-874.
24. Zhang Y. Molecular mechanism of rapid cellular accumulation of anticarcinogenic isothiocyanates. Carcinogenesis 2001, 22:425-431.
25. Zhang G., Parkin K.L. A tissue homogenate method to prepare gram-scale Allium thiosulfinates and their disulfide conjugates with cysteine and glutathione. J. Agric. Food Chem. 2013, 61:3030-3038.
26. Monagas M., Urpi-Sarda M., Sanchez-Patan F., Llorach R., Garrido I., Gomez-Cordoves C., Andres-Lacueva C., Bartolome B. Insights into the metabolism and microbial biotransformation of dietary flavan-3-ols and the bioactivity of their metabolites. Food Funct. 2010, 1:233-253.
27. Anastassiades M., Lehotay S.J., Stajnbaher D., Schenck F.J. Fast and easy multiresidue method employing acetonitrile extraction/partitioning and dispersive solid-phase extraction for the determination of pesticide residues in produce. J. AOAC Int. 2003, 86:412-431.