Carotenoids: Experimental Ionization Energies and Capacity at Inhibiting Lipid Peroxidation in a Chemical Model of Dietary Oxidative Stress

Journal of Physical Chemistry B

Volumn 122, Issue 22, 2018, Pages 5860-5869

  Goupy, Pascale ^a,b   Carail, Michel ^a,b   Giuliani, Alexandre ^c,d   Duflot, Denis ^e   Dangles, Olivier ^a,b   Caris Veyrat, Catherine ^a,b  

^a UMR A 408 INRA University of Avignon   (France)

^b UNIVERSITY OF AVIGNON   (France)

^c SYNCHROTRON SOLEIL   (France)

^d CEMAGREF   (France)

^e UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANTS; ATMOSPHERIC IONIZATION; ATMOSPHERIC PRESSURE; CARBON; CHAINS; CHEMICAL BONDS; DRUG PRODUCTS; FREE RADICALS; KINETIC PARAMETERS; LINOLEIC ACID; MASS SPECTROMETRY; ORGANIC COMPOUNDS; OXIDATION; OXIDATIVE STRESS; SYNCHROTRONS;

ANTI-OXIDANT ACTIVITIES; ATMOSPHERIC PRESSURE PHOTO IONIZATION; CARBON-CARBON DOUBLE BONDS; EXPERIMENTAL DETERMINATION; LIPID HYDROPEROXIDE; LIPID PEROXIDATION; RADICAL SCAVENGING; SIX-MEMBERED RINGS;

PIGMENTS;

BETA CAROTENE; HEME; ION; LINOLEIC ACID; METMYOGLOBIN; UNSATURATED FATTY ACID; XANTHOPHYLL;

ATMOSPHERIC PRESSURE; CHEMICAL MODEL; CHEMISTRY; LIPID PEROXIDATION; MASS SPECTROMETRY; METABOLISM; QUANTUM THEORY; ULTRAVIOLET RADIATION;

ATMOSPHERIC PRESSURE; BETA CAROTENE; FATTY ACIDS, UNSATURATED; HEME; IONS; LINOLEIC ACID; LIPID PEROXIDATION; MASS SPECTROMETRY; METMYOGLOBIN; MODELS, CHEMICAL; QUANTUM THEORY; ULTRAVIOLET RAYS; XANTHOPHYLLS;

EID: 85047432280     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.8b03447     Document Type: Article

References (28)

1. Namitha, K. K.; Negi, P. S. Chemistry and biotechnology of carotenoids. Crit. Rev. Food Sci. Nutr. 2010, 50, 728-760, 10.1080/10408398.2010.499811
2. Desmarchelier, C.; Borel, P. Overview of carotenoid bioavailability determinants: From dietary factors to host genetic variations. Trends Food Sci. Technol. 2017, 69, 270-280, 10.1016/j.tifs.2017.03.002
3. Fernández-García, E.; Carvajal-Lerida, I.; Jaren-Galan, M.; Garrido-Fernandez, J.; Perez-Galvez, A.; Hornero-Mendez, D. Carotenoids bioavailability from foods: From plant pigments to efficient biological activities. Food Res. Int. 2012, 46, 438-450, 10.1016/j.foodres.2011.06.007
4. Bernstein, P. S.; Li, B.; Vachali, P. P.; Gorusupudi, A.; Shyam, R.; Henriksen, B. S.; Nolan, J. M. Lutein, zeaxanthin, and meso-zeaxanthin: The basic and clinical science underlying carotenoid-based nutritional interventions against ocular disease. Prog. Retinal Eye Res. 2016, 50, 34-66, 10.1016/j.preteyeres.2015.10.003
5. Kaulmann, A.; Bohn, T. Carotenoids, inflammation, and oxidative stress-implications of cellular signaling pathways and relation to chronic disease prevention. Nutr. Res. 2014, 34, 907-929, 10.1016/j.nutres.2014.07.010
6. Skibsted, L. H. Carotenoids in antioxidant networks. Colorants or radical scavengers. J. Agric. Food Chem. 2012, 60, 2409-2417, 10.1021/jf2051416
7. Müller, L.; Fröhlich, K.; Böhm, V. Comparative antioxidant activities of carotenoids measured by ferric reducing antioxidant power (FRAP), ABTS bleaching assay (TEAC), DPPH assay and peroxyl radical scavenging assay. Food Chem. 2011, 129, 139-148, 10.1016/j.foodchem.2011.04.045
8. Bauerfeind, J.; Hintze, V.; Kschonsek, J.; Killenberg, M.; Böhm, V. Use of photochemiluminescence for the determination of antioxidant activities of carotenoids and antioxidant capacities of selected tomato products. J. Agric. Food Chem. 2014, 62, 7452-7459, 10.1021/jf502019r
9. Galano, A. Relative antioxidant efficiency of a large series of carotenoids in terms of one electron transfer reactions. J. Phys. Chem. B 2007, 111, 12898-12908, 10.1021/jp074358u
10. El-Agamey, A.; Lowe, G. M.; McGarvey, D. J.; Mortensen, A.; Phillip, D. M.; Truscott, T. G.; Young, A. J. Carotenoid radical chemistry and antioxidant/pro-oxidant properties. Arch. Biochem. Biophys. 2004, 430, 37-48, 10.1016/j.abb.2004.03.007
11. Martínez, A.; Rodriguez-Girones, M. A.; Barbosa, A.; Costas, M. Donator acceptor map for carotenoids, melatonin and vitamins. J. Phys. Chem. A 2008, 112, 9037-9042, 10.1021/jp803218e
12. Dougherty, D.; Younathan, E. S.; Voll, R.; Abdulnur, S.; McGlynn, S. P. Photoelectron-spectroscopy of some biological molecules. J. Electron Spectrosc. Relat. Phenom. 1978, 13, 379-393, 10.1016/0368-2048(78)85042-7
13. Giuliani, A.; Giorgetta, J. L.; Ricaud, J. P.; Jamme, F.; Rouam, V.; Wien, F.; Laprevote, O.; Refregiers, M. Atmospheric pressure photoionization using tunable VUV synchrotron radiation. Nucl. Instrum. Methods Phys. Res., Sect. B 2012, 279, 114-117, 10.1016/j.nimb.2011.10.038
14. Giuliani, A.; Jamme, F.; Rouam, V.; Wien, F.; Giorgetta, J.-L.; Lagarde, B.; Chubar, O.; Bac, S.; Yao, I.; Rey, S. et al. DISCO: a low-energy multipurpose beamline at synchrotron SOLEIL. J. Synchrotron Radiat. 2009, 16, 835-841, 10.1107/S0909049509034049
15. Giuliani, A.; Yao, I.; Lagarde, B.; Rey, S.; Duval, J.-P.; Rommeluere, P.; Jamme, F.; Rouam, V.; Wein, F.; De Oliveira, C. et al. A differential pumping system to deliver windowless VUV photons at atmospheric pressure. J. Synchrotron Radiat. 2011, 18, 546-549, 10.1107/S0909049511016517
16. Vulcain, E.; Goupy, P.; Caris-Veyrat, C.; Dangles, O. Inhibition of the metmyoglobin-induced peroxidation of linoleic acid by dietary antioxidants: Action in the aqueous vs lipid phase. Free Radic. Res. 2005, 39, 547-563, 10.1080/10715760500073865
17. Goupy, P.; Reynaud, E.; Dangles, O.; Caris-Veyrat, C. Antioxidant activity of (all-E)-lycopene and synthetic apo-lycopenoids in a chemical model of oxidative stress in the gastro-intestinal tract. New J. Chem. 2012, 36, 575-587, 10.1039/C1NJ20437H
18. Sy, C.; Caris-Veyrat, C.; Dufour, C.; Boutaleb, M.; Borel, P.; Dangles, O. Inhibition of iron-induced lipid peroxidation by newly identified bacterial carotenoids in model gastric conditions. Comparison with common carotenoids. Food Funct. 2013, 4, 698-712, 10.1039/c3fo30334a
19. Szabo, A.; Ostlund, N. S. Modern Quantum Chemistry: Introduction to Advanced Electronic Structure Theory; Courier Corporation: New York, 1996.
20. Martínez, A.; Vargas, R.; Galano, A. Theoretical study of the chemical fate of adducts formed through free radical addition reactions to carotenoids. Theor. Chem. Acc. 2010, 127, 595-603, 10.1007/s00214-010-0753-3
21. Martínez, A.; Stinco, C. M.; Melendez-Martinez, A. J. Free radical scavenging properties of phytofluene and phytoene isomers as compared to lycopene: a combined experimental and theoretical study. J. Phys. Chem. B 2014, 118, 9819-9825, 10.1021/jp503227j
22. Gobert, M.; Remond, D.; Loonis, M.; Buffiere, C.; Sante-Lhoutellier, V.; Dufour, C. Fruits, vegetables and their polyphenols protect dietary lipids from oxidation during gastric digestion. Food Funct. 2014, 5, 2166-2174, 10.1039/C4FO00269E
23. Achat, S.; Rakotomanomana, N.; Madani, K.; Dangles, O. Antioxidant activity of olive phenols and other dietary phenols in model gastric conditions: scavenging of the free radical DPPH and inhibition of the haem-induced peroxidation of linoleic acid. Food Chem. 2016, 213, 135-142, 10.1016/j.foodchem.2016.06.076
24. Miller, N. J.; Sampson, J.; Candeias, L. P.; Bramley, P. M.; Rice-Evans, C. A. Antioxidant activities of carotenes and xanthophylls. FEBS Lett. 1996, 384, 240-242, 10.1016/0014-5793(96)00323-7
25. Mortensen, A.; Skibsted, L. H. Importance of carotenoid structure in radical-scavenging reactions. J. Agric. Food Chem. 1997, 45, 2970-2977, 10.1021/jf970010s
26. Rodrigues, E.; Mariutti, L. R. B.; Chiste, R. C.; Mercadante, A. Z. Development of a novel micro-assay for evaluation of peroxyl radical scavenger capacity: Application to carotenoids and structure-activity relationship. Food Chem. 2012, 135, 2103-2111, 10.1016/j.foodchem.2012.06.074
27. Jørgensen, L. V.; Andersen, H. J.; Skibsted, L. H. Kinetics of reduction of hypervalent iron in myoglobin by crocin in aqueous solution. Free Radical Res. 1997, 27, 73-87, 10.3109/10715769709097840
28. Liebler, D. C.; McClure, T. D. Antioxidant reactions of β-carotene: identification of carotenoid-radical adducts. Chem. Res. Toxicol. 1996, 9, 8-11, 10.1021/tx950151t