Determination of cyanidin 3-glucoside in rat brain, liver and kidneys by UPLC/MS-MS and its application to a short-term pharmacokinetic study

Scientific Reports

Volumn 6, Issue , 2016, Pages

  Fornasaro, Stefano ^a   Ziberna, Lovro ^a   Gasperotti, Mattia ^b   Tramer, Federica ^a   Vrhovšek, Urška ^b   Mattivi, Fulvio ^b   Passamonti, Sabina ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

^b RESEARCH AND INNOVATION CENTRE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHOCYANIN; CYANIDIN 3-O-GLUCOSIDE; GLUCOSIDE;

ANIMAL; BIOAVAILABILITY; BRAIN; CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KIDNEY; LIVER; MALE; METABOLISM; RAT; TANDEM MASS SPECTROMETRY; TISSUE DISTRIBUTION;

ANIMALS; ANTHOCYANINS; BIOLOGICAL AVAILABILITY; BRAIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSIDES; KIDNEY; LIVER; MALE; MOLECULAR STRUCTURE; RATS; TANDEM MASS SPECTROMETRY; TISSUE DISTRIBUTION;

EID: 84960861931     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep22815     Document Type: Article

References (44)

1. Wu, X., Beecher, G. R., Holden, J. M., Haytowitz, D. B. & Gebhardt, S. E. Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. J Agric Food Chem 54, 4069-4075 (2006).
2. Tarozzi, A. et al. Neuroprotective effects of cyanidin 3-O-glucopyranoside on amyloid beta (25-35) oligomer-induced toxicity. Neurosci Lett 473, 72-76, doi: 10.1016/j.neulet.2010.02.006 (2010).
3. Im, S. E. et al. Anthocyanins in the ripe fruits of Rubus coreanus Miquel and their protective effect on neuronal PC-12 cells. Food Chem 139, 604-610, doi: 10.1016/j.foodchem.2012.12.057 (2013).
4. Shih, P. H., Chan, Y. C., Liao, J. W., Wang, M. F. & Yen, G. C. Antioxidant and cognitive promotion effects of anthocyanin-rich mulberry (Morus atropurpurea L.) on senescence-accelerated mice and prevention of Alzheimer's disease. J Nutr Biochem 21, 598-605, doi: 10.1016/j.jnutbio.2009.03.008 (2010).
5. Kang, T. H., Hur, J. Y., Kim, H. B., Ryu, J. H. & Kim, S. Y. Neuroprotective effects of the cyanidin-3-O-beta-d-glucopyranoside isolated from mulberry fruit against cerebral ischemia. Neurosci Lett 391, 122-126 (2006).
6. Di Giacomo, C. et al. Effect of Treatment with Cyanidin-3-O-beta-D-Glucoside on Rat Ischemic/Reperfusion Brain Damage. Evid Based Complement Alternat Med 2012, 285750, doi: 10.1155/2012/285750 (2012).
7. Gao, X., Cassidy, A., Schwarzschild, M. A., Rimm, E. B. & Ascherio, A. Habitual intake of dietary flavonoids and risk of Parkinson disease. Neurology 78, 1138-1145, doi: 10.1212/WNL.0b013e31824f7fc4 (2012).
8. Krikorian, R. et al. Concord grape juice supplementation and neurocognitive function in human aging. J Agric Food Chem 60, 5736-5742, doi: 10.1021/jf300277g (2012).
9. Passamonti, S., Vrhovsek, U., Vanzo, A. & Mattivi, F. The stomach as a site for anthocyanins absorption from food. FEBS Lett 544, 210-213 (2003).
10. Cai, H. et al. Determination of anthocyanins in the urine of patients with colorectal liver metastases after administration of bilberry extract. Biomed Chromatogr 25, 660-663, doi: 10.1002/bmc.1499 (2011).
11. Talavera, S. et al. Anthocyanins are efficiently absorbed from the small intestine in rats. J Nutr 134, 2275-2279 (2004).
12. Kay, C. D., Mazza, G. J. & Holub, B. J. Anthocyanins exist in the circulation primarily as metabolites in adult men. J Nutr 135, 2582-2588, doi: 135/11/2582 (2005).
13. Fernandes, I., Faria, A., Calhau, C., de Freitas, V. & Mateus, N. Bioavailability of anthocyanins and derivatives. J Funct Foods 7, 54-66, doi: 10.1016/j.jff.2013.05.010 (2014).
14. de Ferrars, R. M. et al. The pharmacokinetics of anthocyanins and their metabolites in humans. Br J Pharmacol 171, 3268-3282, doi: 10.1111/bph.12676 (2014).
15. Czank, C. et al. Human metabolism and elimination of the anthocyanin, cyanidin-3-glucoside: a (13)C-tracer study. Am J Clin Nutr 97, 995-1003, doi: 10.3945/ajcn.112.049247 (2013).
16. rd, McKay, S. & Prior, R. L. Aglycones and sugar moieties alter anthocyanin absorption and metabolism after berry consumption in weanling pigs. J Nutr 135, 2417-2424 (2005).
17. Felgines, C. et al. Absorption and metabolism of red orange juice anthocyanins in rats. Br J Nutr 95, 898-904 (2006).
18. El Mohsen, M. A. et al. Absorption, tissue distribution and excretion of pelargonidin and its metabolites following oral administration to rats. Br J Nutr 95, 51, doi: 10.1079/BJN20051596 (2007).
19. Aqil, F. et al. Detection of anthocyanins/anthocyanidins in animal tissues. J Agric Food Chem 62, 3912-3918, doi: 10.1021/jf500467b (2014).
20. Vanzo, A., Vrhovsek, U., Tramer, F., Mattivi, F. & Passamonti, S. Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver. J Nat Prod 74, 1049-1054, doi: 10.1021/np100948a (2011).
21. Talavera, S. et al. Anthocyanin metabolism in rats and their distribution to digestive area, kidney, and brain. J Agric Food Chem 53, 3902-3908 (2005).
22. Kalt, W. et al. Identification of anthocyanins in the liver, eye, and brain of blueberry-fed pigs. J Agric Food Chem 56, 705-712, doi: 10.1021/jf071998l (2008).
23. Andres-Lacueva, C. et al. Anthocyanins in aged blueberry-fed rats are found centrally and may enhance memory. Nutr Neurosci 8, 111-120 (2005).
24. Passamonti, S., Vrhovsek, U., Vanzo, A. & Mattivi, F. Fast access of some grape pigments to the brain. J Agric Food Chem 53, 7029-7034, doi: 10.1021/jf050565k (2005).
25. Ali Shah, S., Ullah, I., Lee, H. Y. & Kim, M. O. Anthocyanins protect against ethanol-induced neuronal apoptosis via GABAB1 receptors intracellular signaling in prenatal rat hippocampal neurons. Mol Neurobiol 48, 257-269, doi: 10.1007/s12035-013-8458-y (2013).
26. Milbury, P. E. & Kalt, W. Xenobiotic Metabolism and Berry Flavonoid Transport across the Blood-Brain Barrier. J Agric Food Chem 58, 3950-3956, doi: 10.1021/jf903529m (2010).
27. Faria, A. et al. Flavonoid transport across RBE4 cells: A blood-brain barrier model. Cell Mol Biol Lett 15, 234-241, doi: 10.2478/s11658-010-0006-4 (2010).
28. Gasperotti, M. et al. Fate of Microbial Metabolites of Dietary Polyphenols in Rats: Is the Brain Their Target Destination? ACS chem Neurosci 6, 1341-1352, doi: 10.1021/acschemneuro.5b00051 (2015).
29. Krasieva, T. B., Ehren, J., O'Sullivan, T., Tromberg, B. J. & Maher, P. Cell and brain tissue imaging of the flavonoid fisetin using labelfree two-photon microscopy. Neurochem Int 89, 243-248, doi: 10.1016/j.neuint.2015.08.003 (2015).
30. Ichiyanagi, T. et al. Metabolic pathway of cyanidin 3-O-beta-D-glucopyranoside in rats. J Agric Food Chem 53, 145-150 (2005).
31. Vanzo, A. et al. Metabonomic investigation of rat tissues following intravenous administration of cyanidin 3-glucoside at a physiologically relevant dose. Metabolomics 9, 88-100, doi: 10.1007/s11306-012-0430-8 (2012).
32. Marczylo, T. H., Cooke, D., Brown, K., Steward, W. P. & Gescher, A. J. Pharmacokinetics and metabolism of the putative cancer chemopreventive agent cyanidin-3-glucoside in mice. Cancer Chemother Pharmacol 64, 1261-1268, doi: 10.1007/s00280-009-0996-7 (2009).
33. Fleschhut, J., Kratzer, F., Rechkemmer, G. & Kulling, S. E. Stability and biotransformation of various dietary anthocyanins in vitro. Eur J Nutr 45, 7-18, doi: 10.1007/S00394-005-0557-8 (2006).
34. Benet, L. Z. & Massoud, N. In Pharmacokinetic basis for drug treatment xiii, 466 p. (Raven Press, 1984).
35. Brown, R. P., Delp, M. D., Lindstedt, S. L., Rhomberg, L. R. & Beliles, R. P. Physiological parameter values for physiologically based pharmacokinetic models. Toxicol Ind Health 13, 407-484 (1997).
36. McNamara, P. J., Fleishaker, J. C. & Hayden, T. L. Mean residence time in peripheral tissue. J Pharmacokinet Biopharm 15, 439-450 (1987).
37. Pojer, E., Mattivi, F., Johnson, D. & Stockley, C. S. The Case for Anthocyanin Consumption to Promote Human Health: A Review. CRFSFS 12, 483-508, doi: 10.1111/1541-4337.12024 (2013).
38. Ziberna, L. et al. Transport and bioactivity of cyanidin 3-glucoside into the vascular endothelium. Free Radic Biol Med 52, 1750-1759, doi: 10.1016/j.freeradbiomed.2012.02.027 (2012).
39. Hartung, T. Comparative analysis of the revised Directive 2010/63/EU for the protection of laboratory animals with its predecessor 86/609/EEC-a t4 report. ALTEX 27, 285-303 (2010).
40. Waynforth, H. B. & Flecknell, P. A. In Experimental and surgical technique in the rat Ch. 1, 8-42 (Academic Press, 1992).
41. Fridén, M., Ljungqvist, H., Middleton, B., Bredberg, U. & Hammarlund-Udenaes, M. Improved measurement of drug exposure in the brain using drug-specific correction for residual blood. J Cereb Blood Flow Metab 30, 150-161, doi: 10.1038/jcbfm.2009.200 (2010).
42. Zhang, Y., Huo, M., Zhou, J. & Xie, S. PKSolver: An add-in program for pharmacokinetic and pharmacodynamic data analysis in Microsoft Excel. Computer methods and programs in biomedicine 99, 306-314, doi: 10.1016/j.cmpb.2010.01.007 (2010).
43. Veng-Pedersen, P. Mean time parameters dealing with the tissue distribution of drugs: limitations and extensions. J Pharm Sci 78, 264-266 (1989).
44. Kong, A. N. & Jusko, W. J. Definitions and applications of mean transit and residence times in reference to the two-compartment mammillary plasma clearance model. J Pharm Sci 77, 157-165 (1988).