Identification of Plasma and Urinary Metabolites and Catabolites Derived from Orange Juice (Poly)phenols: Analysis by High-Performance Liquid Chromatography-High-Resolution Mass Spectrometry

Journal of Agricultural and Food Chemistry

Volumn 64, Issue 28, 2016, Pages 5724-5735

  Pereira Caro, Gema ^a   Ludwig, Iziar A ^b   Polyviou, Thelma ^c   Malkova, Dalia ^c   García, Ada ^c   Moreno Rojas, José Manuel ^a   Crozier, Alan ^d  

^a IFAPA CENTRO ALAMEDA DEL OBISPO   (Spain)

^b UNIVERSITY OF LLEIDA   (Spain)

^c UNIVERSITY OF GLASGOW   (United Kingdom)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

bioavailability; flavanones; HPLC HR MS identification; humans; orange juice; phenolic catabolites; urinary and plasma metabolites

Indexed keywords

BENZOIC ACID; BIOCHEMISTRY; BIOMOLECULES; BODY FLUIDS; CARDIOVASCULAR SYSTEM; CHROMATOGRAPHY; CITRUS FRUITS; FRUIT JUICES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; ORGANIC COMPOUNDS; PHENOLS; SPECTROMETRY; SULFUR COMPOUNDS;

BIOAVAILABILITY; FLAVANONES; HUMANS; ORANGE JUICE; PHENOLIC CATABOLITES; PLASMA METABOLITES;

FLAVONOIDS;

POLYPHENOL;

ADULT; ANALYSIS; BLOOD; EVALUATION STUDY; FRUIT AND VEGETABLE JUICE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; MALE; MASS SPECTROMETRY; METABOLISM; PROCEDURES; SWEET ORANGE; URINE;

ADULT; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CITRUS SINENSIS; FRUIT AND VEGETABLE JUICES; HUMANS; MALE; MASS SPECTROMETRY; POLYPHENOLS;

EID: 84979587647     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.6b02088     Document Type: Article

References (28)

1. Del Rio, D.; Rodriguez-Mateos, A.; Spencer, J. P.; Tognolini, M.; Borges, G.; Crozier, A. Dietary (poly) phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases Antioxid. Redox Signaling 2013, 18, 1818-1892 10.1089/ars.2012.4581
2. Rodriguez-Mateos, A.; Vauzour, D.; Krueger, C.; Shanmuganayagam, D.; Reed, J.; Calani, L.; Mena, P.; Del Rio, D.; Crozier, A. Bioavailability, bioactivity and impact on health of dietary flavonoids and related compounds: an update Arch. Toxicol. 2014, 88, 1803-1853 10.1007/s00204-014-1330-7
3. Abad-García, B.; Garmón-Lobato, S.; Berrueta, L. A.; Gallo, B.; Vicente, F. On line characterization of 58 phenolic compounds in citrus fruit juices from Spanish cultivars by high-performance liquid chromatography with photodiode-array detection coupled to electrospay ionization triple quadrupole mass spectrometry Talanta 2012, 99, 213-224 10.1016/j.talanta.2012.05.042
4. Palli, D.; Russo, A.; Ottini, L.; Masala, G.; Saieva, C.; Amorosi, A.; Cama, A.; D'Amico, C.; Falchetti, M.; Palmirotta, R. Red meat, family history, and increased risk of gastric cancer with microsatellite instability Cancer Res. 2001, 61, 5415-5419
5. McCullough, M. L.; Robertson, A. S.; Jacobs, E. J.; Chao, A.; Calle, E. E.; Thun, M. J. A prospective study of diet and stomach cancer mortality in United States men and women Cancer Epidemiol. Biomarkers Prevent. 2001, 10, 1201-1205
6. Al-Zalabani, A. H.; Stewart, K. F.; Wesselius, A.; Schols, A. M.; Zeegers, M. P. Modified risk factors for the prevention of bladder cancer: a systematic review of meta-analyses Eur. J. Epidemiol. 2016, 10.1007/s10654-016-0138-6
7. Morand, C.; Dubray, C.; Milenkovic, D.; Lioger, D.; Martin, J. F.; Scalbert, A.; Mazur, A. Hesperidin contributes to the vascular protective effects of orange juice: a randomized crossover study in healthy volunteers Am. J. Clin. Nutr. 2011, 93, 73-80 10.3945/ajcn.110.004945
8. Vallejo, F.; Larrosa, M.; Escudero, E.; Zafrilla, M. P.; Cerdá, B.; Boza, J.; García-Conesa, M. T.; Espín, J. C.; Tomás-Barberán, F. A. Concentration and solubility of flavanones in orange beverages affect their bioavailability in humans J. Agric. Food Chem. 2010, 58, 6516-6524 10.1021/jf100752j
9. Silveira, J. Q.; Cesar, T. B.; Manthey, J. A.; Baldwin, E. A.; Bai, J.; Raithore, S. Pharmacokinetics of flavanone glycosides after ingestion of single doses of fresh-squeezed orange juice versus commercially processed orange juice in healthy humans J. Agric. Food Chem. 2014, 62, 12576-12584 10.1021/jf5038163
10. Pereira-Caro, G.; Borges, G.; Van Der Hooft, J.; Clifford, M. N.; Del Rio, D.; Lean, M. E.; Roberts, S. A.; Kellerhals, M. B.; Crozier, A. Orange juice (poly)phenols are highly bioavailable in humans Am. J. Clin. Nutr. 2014, 100, 1378-1384 10.3945/ajcn.114.090282
11. Roowi, S.; Mullen, W.; Edwards, C. A.; Crozier, A. Yoghurt impacts on the excretion of phenolic acids derived from colonic breakdown of orange juice flavanones in humans Mol. Nutr. Food Res. 2009, 53 (S1) S68-S75 10.1002/mnfr.200800287
12. Mullen, W.; Archeveque, M.-A.; Edwards, C. A.; Matsumoto, H.; Crozier, A. Bioavailability and metabolism of orange juice flavanones in humans: Impact of a full-fat yogurt J. Agric. Food Chem. 2008, 56, 11157-11164 10.1021/jf801974v
13. Pereira-Caro, G.; Oliver, C. M.; Weerakkody, R.; Singh, T.; Conlon, M.; Borges, G.; Sanguansri, L.; Lockett, T.; Roberts, S. A.; Crozier, A.; Augustin, M. A. Chronic administration of a microencapsulated probiotic enhances the bioavailability of orange juice flavanones in humans Free Radical Biol. Med. 2015, 84, 206-214 10.1016/j.freeradbiomed.2015.03.010
14. Borges, G.; Lean, M. E. J.; Roberts, S. A.; Crozier, A. Bioavailability of dietary (poly)phenols: a study with ileostomists to discriminate between absorption in small and large intestine Food Funct. 2013, 4, 754-762 10.1039/c3fo60024f
15. Bredsdorff, L.; Nielsen, I. L. F.; Rasmussen, S. E.; Cornett, C.; Barron, D.; Bouisset, F.; Offord, E.; Williamson, G. Absorption, conjugation and excretion of the flavanones, naringenin and hesperetin from α-rhamnosidase-treated orange juice in human subjects Br. J. Nutr. 2010, 103, 1602-1609 10.1017/S0007114509993679
16. Tomás-Navarro, M.; Vallejo, F.; Sentandreu, E.; Navarro, J. L.; Tomás-Barberán, F. A. Volunteer stratification is more relevant than technological treatment in orange juice flavanone bioavailability J. Agric. Food Chem. 2014, 62, 24-27 10.1021/jf4048989
17. Ludwig, I. A.; Mena, P.; Calani, L.; Borges, G.; Pereira-Caro, G.; Bresciani, L.; Del Rio, D.; Lean, M. E.; Crozier, A. New insights into the bioavailability of red raspberry anthocyanins and ellagitannins Free Radical Biol. Med. 2015, 89, 758-769 10.1016/j.freeradbiomed.2015.10.400
18. 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. et al. Proposed minimum reporting standards for chemical analysis. Chemical Analysis Working Group (CAWG) Metabolomics Standards Initiative (MSI) Metabolomics 2007, 3, 211-221 10.1007/s11306-007-0082-2
19. Orrego-Lagarón, N.; Vallverdú-Queralt, A.; Martínez-Huélamo, M.; Lamuela-Raventos, R. M.; Escribano-Ferrer, E. Metabolic profile of naringenin in the stomach and colon using liquid chromatography/electrospray ionization linear ion trap quadrupole-Orbitrap-mass spectrometry (LC-ESI-LTQ-Orbitrap-MS) and LC-ESI-MS/MS J. Pharm. Biomed. Anal. 2016, 120, 38-45 10.1016/j.jpba.2015.10.040
20. Actis-Goretta, L.; Dew, T. P.; Léveques, A.; Pereira-Caro, G.; Rein, M.; Teml, A.; Schafer, C.; Hofmann, U.; Schwab, M.; Eichelbaum, M.; Crozier, A.; Williamson, G. Gastrointestinal absorption and metabolism of hesperetin-7-O-rutinoside and hesperetin-7-O-glucoside in healthy humans Mol. Nutr. Food Res. 2015, 59, 1651-1662 10.1002/mnfr.201500202
21. Day, A. J.; Cañada, F. J.; Díaz, J.; Kroon, P. A.; Mclauchlan, R.; Faulds, C. B.; Plumb, G. W.; Morgan, M. R. A.; Williamson, G. Dietary flavonoid and isoflavone glycosides are hydrolysed by the lactase site of lactase phlorizin hydrolase FEBS Lett. 2000, 468, 166-170 10.1016/S0014-5793(00)01211-4
22. Gee, J. M.; Dupont, M. S.; Day, A. J.; Plumb, G. W.; Williamson, G.; Johnson, I. T. Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway J. Nutr. 2000, 130, 2765-2771
23. Pereira-Caro, G.; Borges, G.; Ky, I.; Ribas, A.; Calani, L.; Del Rio, D.; Clifford, M. N.; Roberts, S. A.; Crozier, A. In vitro colonic catabolism of orange juice (poly)phenols Mol. Nutr. Food Res. 2015, 59, 465-475 10.1002/mnfr.201400779
24. Das, N. P. Studies on flavonoid metabolism: absorption and metabolism of (+)-catechin in man Biochem. Pharmacol. 1971, 20, 3435-3445 10.1016/0006-2952(71)90449-7
25. 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 10.1021/jf9032975
26. van Dorsten, F. A.; Grun, C. H.; van Velzen, E. J.; Jacobs, D. M.; Draijer, R.; van Duynhoven, J. P. The metabolic fate of red wine and grape juice polyphenols in humans assessed by metabolomics Mol. Nutr. Food Res. 2010, 54, 897-908 10.1002/mnfr.200900212
27. Jacobs, D. M.; Spiesser, L.; Garnier, M.; de Roo, N.; van Dorsten, F.; Hollebrands, B.; van Velzen, E.; Draijer, R.; van Duynhoven, J. SPE-NMR metabolite sub-profiling of urine Anal. Bioanal. Chem. 2012, 404, 2349-2361 10.1007/s00216-012-6339-2
28. 3 Arzneim. Forsch. 1978, 28, 2326-2331