Electron transfer from plant phenolates to carotenoid radical cations. antioxidant interaction entering the marcus theory inverted region

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 4, 2014, Pages 942-949

  Cheng, Hong ^a   Han, Rui Min ^a   Zhang, Jian Ping ^a   Skibsted, Leif H ^b  

^a RENMIN UNIVERSITY OF CHINA   (China)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

carotenoid regeneration; electron transfer; inverted region; photobleaching; plant phenolate

Indexed keywords

CAROTENOID REGENERATION; ELECTRON TRANSFER; INVERTED REGION; LASER FLASH PHOTOLYSIS; PLANT PHENOLATE; RADICAL CATIONS; REDUCTION POTENTIAL; REORGANIZATION ENERGIES; HYDROXYBENZOIC ACIDS;

ELECTRON TRANSITIONS; LASER THEORY; PHENOLS; PHOTOBLEACHING; PIGMENTS; POSITIVE IONS; PHOTOLYSIS;

FREE RADICAL REACTIONS;

ANTIOXIDANT; BETA CAROTENE; CAROTENOID; CATION; FREE RADICAL; HYDROXYBENZOIC ACID DERIVATIVE; LYCOPENE; PHENOLIC ACID; XANTHOPHYLL; ZEAXANTHIN;

ARTICLE; CHEMISTRY; ELECTRON TRANSPORT; PHOTOLYSIS; PHYSICAL CHEMISTRY; PLANT;

ANTIOXIDANTS; BETA CAROTENE; CAROTENOIDS; CATIONS; ELECTRON TRANSPORT; FREE RADICALS; HYDROXYBENZOATES; PHOTOLYSIS; PHYSICOCHEMICAL PHENOMENA; PLANTS; XANTHOPHYLLS;

EID: 84893501990     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf404725v     Document Type: Article

References (24)

1. Skibsted, L. H. Carotenoids in antioxidant networks. Colorants or radical scavengers J. Agric. Food Chem. 2012, 60, 2409-2417
2. Liang, R.; Chen, C. H.; Han, R. M.; Zhang, J. P.; Skibsted, L. H. Thermodynamic versus kinetic control of antioxidant synergism between β-carotene and (iso)flavonoids and their glycosides in liposomes J. Agric. Food Chem. 2010, 58, 9221-9227
3. Martínez, A.; Vargas, R.; Galano, A. What is important to prevent oxidative stress? A theoretical study on electron-transfer reactions between carotenoids and free radicals J. Phys. Chem. B 2009, 113, 12113-12120
4. Martínez, A.; Vargas, R.; Galano, A. Theoretical study study of the chemical fate of adducts formed through free radical addition reactions to carotenoids Theor. Chem. Acc. 2010, 127, 595-603
5. Böhm, F.; Edge, R.; Truscott, G. Interactions of dietary carotenoids with activated (singlet) oxygen and free radicals: potential effects for human health Mol. Nutr. Food Res. 2012, 56, 205-216
6. Chen, C. H.; Han, R. M.; Liang, R.; Fu, L. M.; Zhang, J. P.; Skibsted, L. H. Direct observation of the β-carotene reaction with hydroxyl radical J. Phys. Chem. B 2011, 115, 2082-2089
7. Han, R. M.; Chen, C. H.; Tian, Y. X.; Zhang, J. P.; Skibsted, L. H. Fast regeneration of carotenoids from radical cations by isoflavonoid dianions: importance of the carotenoid keto group for electron transfer J. Phys. Chem. A 2010, 114, 126-132
8. Song, L. L.; Liang, R.; Li, D. D.; Xing, Y. D.; Han, R. M.; Zhang, J. P.; Skibsted, L. H. β-Carotene radical cation addition to green tea polyphenols. Mechanism of antioxidant antagonism in peroxidizing liposomes J. Agric. Food Chem. 2011, 59, 12643-12651
9. Marcus, R. A. Electron transfer reactions in chemistry. Theory and experiment Rev. Mod. Phys. 1993, 65, 599-610
10. Turró, C.; M. Zaleski, J.; M. Karabatsos, Y.; G. Nocera, D. Bimolecular electron transfer in the Marcus inverted region J. Am. Chem. Soc. 1996, 118, 6060-6067
11. Thanasekaran, P.; Rajendran, T.; Rajagopal, S.; Srinivasan, C.; Ramaraj, R.; Ramamurthy, P.; Venkatachalapathy, B. Marcus inverted region in the photoinduced electron transfer reactions of ruthenium(II)-polypyridine complexes with phenolate ions J. Phys. Chem. A 1997, 101, 8195-8199
12. Weng, Y. X.; Chan, K. C.; Tzeng, B. C.; Che, C. M. Effect of laser intensity on the determination of intermolecular electron transfer rate constants-observation of Marcus inverted region in photoinduced back electron transfer reactions J. Chem. Phys. 1998, 109, 5948-5956
13. Fukuzumi, S.; Ohkubo, K.; Imahori, H.; M. Guldi, D. Driving force dependence of intermolecular electron-transfer reactions of fullerenes Chem.-Eur. J. 2003, 9, 1585-1593
14. I metalloprotein undergoes collisional electron transfer in the inverted Marcus region Angew. Chem., Int. Ed. 2006, 45, 6137-6140
15. Liang, J.; Tian, Y.-X.; Yang, F.; Zhang, J. P.; Skibsted, L. H. Antioxidant synergism between carotenoids in membranes. Astaxanthin as a radical transfer bridge Food Chem. 2009, 115, 1437-1442
16. Simić, A.; Manojlović, D.; Šegan, D.; Todorović, M. Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics Molecules 2007, 12, 2327-2340
17. Burke, M.; Edge, R.; Land, E. J.; Mcgarvey, D. J; Truscott, T. G. One-electron reduction potentials of dietary carotenoid radical cations in aqueous micellar environment FEBS Lett. 2001, 500, 132-136
18. 2 in chloroform ChemPhysChem 2009, 10, 1789-1793
19. Imahori, H.; Yamada, H.; Guldi, D. M.; Endo, Y.; Shimomura, A.; Kundu, S.; Yamada, K.; Okada, T.; Sakata, Y.; Fukuzumi, S. Comparison of reorganization energies for intra- and intermolecular electron transfer Angew. Chem., Int. Ed. 2002, 41, 2344-2347
20. Shahidi, F.; Zhong, Y. Lipophilised epigallocatechin gallate (EGCG) derivatives and their antioxidant potential in food and biological systems Food Chem. 2012, 131, 22-30
21. Shahidi, F.; Zhong, Y. Revisiting the polar paradox theory: a critical overview J. Agric. Food Chem. 2011, 59, 3499-3504
22. - state of all-trans -lycopene as revealed by picosecond time-resolved absorption spectroscopy J. Phys. Chem. B 1998, 102, 1632-1640
23. Zhang, W.; Wang, Y. W.; Hu, R.; Ai, X. C.; Zhang, J. P.; Hou, J. H. Mechanism of primary charge photogeneration in polyfluorene copolymer/fullerene blends and influence of the donor/acceptor lowest unoccupied molecular orbital level offset J. Phys. Chem. C 2013, 117, 735-749
24. Tian, Y. X; Han, R. M.; Zhang, J. P.; Skibsted, L. H. Effect of polar solvents on β-carotene radical precursor Free Radical Res. 2008, 42, 281-286