Chromatographic and spectroscopic characterization of urolithins for their determination in biological samples after the intake of foods containing ellagitannins and ellagic acid

Journal of Chromatography A

Volumn 1428, Issue , 2016, Pages 162-175

  García Villalba, Rocío ^a   Espín, Juan Carlos ^a   Tomás Barberán, Francisco A ^a  

^a RESEARCH GROUP ON QUALITY   (Spain)

Author keywords

Biological samples; Ellagitannin containing foods; Mass spectrometry; Relative response factors; Urolithins; UV spectra

Indexed keywords

BIOMOLECULES; BODY FLUIDS; CHROMATOGRAPHY; FOOD PRODUCTS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETERS; MASS SPECTROMETRY; METABOLITES; SPECTROMETERS; ULTRAVIOLET SPECTROSCOPY;

BIOLOGICAL SAMPLES; ELLAGITANNIN; RELATIVE RESPONSE FACTORS; UROLITHINS; UV SPECTRUM;

ELLAGIC ACID;

ELLAGIC ACID; ELLAGITANNIN; MICROBIAL PRODUCTS NOT CLASSIFIED ELSEWHERE; UNCLASSIFIED DRUG; UROLITHIN; COUMARIN DERIVATIVE; TANNIN;

ADULT; ARTICLE; BLOOD ANALYSIS; CHROMATOGRAPHY; FECES ANALYSIS; HUMAN; HUMAN EXPERIMENT; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MEASUREMENT PRECISION; NORMAL HUMAN; POMEGRANATE; PRIORITY JOURNAL; SPECTROSCOPY; ULTRAVIOLET SPECTROSCOPY; URINALYSIS; WALNUT; BODY FLUID; CHEMICAL ANALYSIS; CHEMISTRY; DEVICES; FECES; METABOLISM; PROCEDURES;

BODY FLUIDS; CHEMISTRY TECHNIQUES, ANALYTICAL; CHROMATOGRAPHY, LIQUID; COUMARINS; ELLAGIC ACID; FECES; HUMANS; HYDROLYZABLE TANNINS; MASS SPECTROMETRY;

EID: 84959858829     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2015.08.044     Document Type: Article

References (36)

1. Espin J.C., Larrosa M., Garcia-Conesa M.T., Tomas-Barberán F.A. Biological significance of urolithins, the gut microbial ellagic acid-derived metabolites: the evidence so far. Evid. Based Compl. Alt. Med. 2013, 270418.
2. García-Villalba R., Beltrán D., Espin J.C., Selma M.V., Tomás-Barberán F.A. Time course production of urolithins from ellagic acid by human gut microbiota. J. Agric. Food Chem. 2013, 61:8797-8806.
3. Bakkalbasi E., Mentes O., Artik N. Food ellagitannins-occurrence, effects of processing and storage. Crit. Rev. Food Sci. Nutr. 2009, 49:283-298.
4. Arapitsas P. Hydrolyzable tannin analysis in food. Food Chem. 2012, 135:1708-1717.
5. Bialonska D., Ramnani P., Kasimsetty S.G., Muntha K.R., Gibson G.R., Ferreira D. The influence of pomegranate by-product and punicalagins on selected groups of human intestinal microbiota. Int. J. Food Mic. 2010, 140:175-182.
6. Espín J.C., González Barrios B., Cerdá B., López-Bote C., Rey A.I., Tomás-Barberán F.A. The Iberian pig as a model to clarify obscure points in the bioavailability and metabolism of ellagitannins in humans. J. Agric. Food Chem. 2007, 55:10476-10485.
7. Pfundstein B., Haubner R., Würtele G., Gehres N., Ulrich C.M., Owen R.W. Pilot walnut intervention study of urolithin bioavailability in human volunteers. J. Agric. Food Chem. 2014, 62:10264-10273.
8. González-Barrios R., Truchado P., Ito H., Espín J.C., Tomás-Barberán F.A. UV and MS identification of urolithins and nasutins, the bioavailable metabolites of ellagitannins and ellagic acid in different mammals. J. Agric. Food Chem. 2011, 59:1152-1162.
9. Ito H., Iguchi A., Hatano T. Identification of urinary and intestinal bacterial metabolites of ellagitannin geraniin in rats. J. Agric. Food Chem. 2008, 56:393-400.
10. Cerdá B., Tomás-Barberán F.A., Espín J.C. Metabolism of chemopreventive and antioxidant ellagitannins from strawberries, raspberries, walnuts and oak-aged wines in humans: Identification of biomarkers and individual variability. J. Agric. Food Chem. 2005, 53:227-235.
11. García-Muñoz C., Hérnandez L., Pérez A., Vaillant F. Diversity of urinary excretion patterns of main ellagitannins' colonic metabolites after ingestion of tropical highland blackberry (Rubus adenotrichus) juice. Food Res. Int. 2014, 55:161-169.
12. Tulipani S., Urpi-Sarda M., García-Villalba R., Rabassa M., López-Uriarte P., Bulló M., Jáuregui O., Tomás-Barberán F.A., Salas-Salvadó J., Espín J.C., Andrés-Lacueva C. Urolithins are the main urinary microbial-derived phenolic metabolites discriminating a moderate consumption of nuts in free-living subjects with diagnosed metabolic syndrome. J. Agric. Food Chem. 2012, 60:8930-8940.
13. Nuñez-Sanchez M.A., García-Villalba R., Monedero-Saiz T., García-Talavera N.V., Gómez-Sánchez M.B., Sánchez-Álvarez C., García-Albert A.M., Rodríguez-Gil F.J., Ruiz-Marín M., Pastor-Quirante F.A., Martínez-Díaz F., Yáñez-Gascón M.J., González-Sarrías A., Tomás-Barberán F.A., Espín J.C. Targeted metabolic profiling of pomegranate polyphenols and urolithins in plasma, urine and colon tissues from colorectal cancer patients. Mol. Nutr. Food Res. 2014, 58:1199-1211.
14. González-Sarrías A., Giménez-Bastida J.A., García-Conesa M.T., Gómez-Sánchez M.B., García-Talavera N.V., Gil-Izquierdo A., Sánzchez-Álvarez C., Fontana-Compiano L.O., Morga-Egea J.P., Pastor-Quirante F.A., Martínez-Díaz F., Tomás-Barberán F.A., Espín J.C. Occurrence of urolithins, gut microbiota ellagic acid metabolites and proliferation markers expression response in the human prostate gland upon consumption of walnuts and pomegranate juice. Mol. Nutr. Food Res. 2010, 54:311-322.
15. González-Sarrías A., Giménez-Bastida J.A., Núñez-Sánchez M.A., Larrosa M., García-Conesa M.T., Tomás-Barberán F.A., Espín J.C. Phase-II metabolism limits the antiproliferative activity of urolithins in human colon cancer cells. Eur. J. Nutr. 2014, 53:853-864.
16. Larrosa M., González-Sarrías A., Yánez-Gascón M.J., Selma M.V., Azorín-Ortuño M., Toti S., Tomás-Barberán F., Dolara P., Espín J.C. Anti-inflammatory properties of a pomegranate extract and its metabolite urolithin-A in a colitis rat model and the effect of colon inflammation on phenolic metabolism. J. Nutr. Biochem. 2010, 21:717-725.
17. González-Sarrías A., Espín J.C., Tomás-Barberán F.A., García-Conesa M.T. Gene expression, cell cycle arrest and MAPK signalling regulation in Caco-2 cells exposed to ellagic acid and its metabolites, urolithins. Mol. Nutr. Food Res. 2009, 53:686-698.
18. González-Barrio R., Borges G., Mullen W., Crozier A. Bioavailability of anthocyanins and ellagitannins following consumption of raspberries by healthy humans and subjects with an ileostomy. J. Agric. Food Chem. 2010, 58:3933-3939.
19. Seeram N.V., Henninng S.M., Zhang Y., Suchard M., Li Z., Heber D. Pomegranate juice ellagitannin metabolites are present in human plasma and some persist in urine for up to 48hours. J. Nutr. 2006, 136:2481-2485.
20. Cerdá B., Espín J.C., Parra S., Martínez P., Tomás-Barberán F.A. The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolized into bioavailable but poor antioxidant hydroxyl-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans. Eur. J. Nutr. 2004, 43:205-220.
21. Seeram N.P., Zhang Y., McKeever R., Henning S.M., Lee R., Suchard M.A., Li Z., Chen S., Thames G., Zerlin A., Nguyen M., Wang D., Dreher M., Heber D. Pomegranate juice and extracts provide similar levels of plasma and urinary ellagitannin metabolites in human subjects. J. Med. Food 2008, 11:390-394.
22. González-Barrio R., Truchado P., García-Villalba R., Hervás G., Frutos P., Espín J.C., Tomás-Barberán F.A. Metabolism of oak leaf ellagitanins and urolithin production in beef cattle. J. Agric. Food Chem. 2012, 60:3068-3077.
23. Kosmala M., Zdunczyk Z., Juskiewicz J., Jurgonski A., Karlinska E., Macierzynski J., Janczak R., Roj E. Chemical composition of defatted strawberry and raspberry seeds and the effect of these dietary ingredients on polyphenol metabolites, intestinal function, and selected serum parameters in rats. J. Agric. Food Chem. 2015, 63:2989-2996.
24. Truchado P., Larrosa M., García-Conesa M.T., Cerdá B., Vidal-Guevara M.L., Tomás-Barberán F.A., Espín J.C. Strawberry processing does not affect the production and urinary excretion of urolithins, ellagic acid metabolites, in humans. J. Agric. Food Chem. 2012, 60:5749-5754.
25. Seeram N.P., Aronson W.J., Zhang Y., Henning S.M., Moro A., Lee R., Sartippour M., Harris D.M., Retting M., Suchard M.A., Pantuck A.J., Belldegrun A., Heber D. Pomegranate ellagitannin-derived metabolites inhibit prostate cancer growth and localize to the mouse prostate gland. J. Agric. Food Chem. 2007, 55:7732-7737.
26. Mertens-Talcott S.U., Jilma-Stohlawetz P., Rios J., Hingorani L., Derendorf H. Absorption, metabolism, and antioxidant effects of pomegranate (Punica granatum L.) polyphenols after ingestion of a standardized extract in healthy human volunteers. J. Agric. Food Chem. 2006, 54:8956-8961.
27. Natella F., Leoni G., Maldini M., Natarelli L., Comitato R., Schonlau F., Virgili F., Canali R. Absorption, metabolism, and effects at transcriptome level of a standardized french oak Wood extract, robuvit, in healthy volunteers: pilot study. J. Agric. Food Chem. 2014, 62:443-453.
28. González-Sarrías A., Miguel V., Merino G., Lucas R., Morales J.C., Tomás-Barberán F.A., Alvarez A.I., Espín J.C. The gut microbiota ellagic acid-derived metabolite urolithin A and its sulfate conjugate are substrates for the drug efflux transporter breast cancer resistance protein (ABCG2/BCRP). J. Agric. Food Chem. 2013, 61:4352-4359.
29. Svoboda P., Vlcková H., Nováková L. Development and validation of UHPLC-MS/MS method for determination of eight naturally occurring catechin derivatives in various tea samples and the role of matrix effects. J. Pharm. Biomed. Anal. 2015, 114:62-70.
30. González-Ruiz V., Olives A.I., Martín M.A. Core-shell particles lead the way to renewing high-performance liquid chromatography. TrAC Trend. Anal. Chem. 2015, 64:17-28.
31. Prencipe F.P., Brighenti V., Rodolfi M., Mongelli A., Dall'Asta C., Ganino T., Bruni R., Pellati F. Development of a new high-performance liquid chromatography method with diode array and electrospray ionization-mass spectrometry detection for the metabolite fingerprinting of bioactive compounds in Humulus lupulus L. J. Chromatogr. A 2014, 1349:50-59.
32. Wu Z., Gao W., Phelps M.A., Wu D., Miller D.D., Dalton J.T. Favorable effects of weak acids on negative-ion electrospray ionization mass spectrometry. Anal. Chem. 2014, 76:839-847.
33. Tomás-Barberán F.A., García-Villalba R., González-Sarrías A., Selma M.V., Espín J.C. Ellagic acid metabolism by human gut microbiota: consistent observation of three urolithin phenotypes in intervention trials, independent of food source, age, and health status. J. Agric. Food Chem. 2014, 62:6535-6538.
34. Sun P., Wang X., Alquier L., Maryanoff C.A. Determination of relative response factors of impurities in paclitaxel with high performance liquid chromatography equipped with ultraviolet and charged aerosol detectors. J. Chromatogr. A 2008, 1177:87-91.
35. Varga E., Glauner T., Köppen R., Mayer K., Sulyok M., Schuhmacher R., Krska R., Berthiller F. Stable isotope dilution assay for the accurate determination of mycotoxins in maize by UHPLC-MS/MS. Anal. Bioanal. Chem. 2012, 402:2675-2686.
36. Caban M., Migowska N., Stepnowski P., Kwiatkowski M., Kumirska J. Matrix effects and recovery calculations in analyses of pharmaceuticals based on the determination of β-blockers and β-agonists in environmental samples. J. Chromatogr. A 2012, 1258:117-127.