Thermodynamic versus kinetic control of antioxidant synergism between β-carotene and (ISO)flavonoids and their glycosides in liposomes

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 16, 2010, Pages 9221-9227

  Liang, Ran ^a   Chen, Chang Hui ^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

Carotene; Antioxidant synergism; Flavonoid; Isoflavonoid

Indexed keywords

ANTIOXIDANT SYNERGISM; BAICALEIN; BAICALIN; BIPHASIC KINETICS; BOND DISSOCIATION ENTHALPIES; CONJUGATED DIENES; DAIDZEIN; DENSITY FUNCTIONAL THEORY CALCULATIONS; FIRST-ORDER RATE CONSTANTS; FLAVONOID; FREE RADICAL INITIATORS; ISOFLAVONOIDS; KINETIC CONTROL; LASER FLASH PHOTOLYSIS; LIPID OXIDATION; LIPID PHASE; LUMO ENERGY; MONOANIONS; NON-ADDITIVE; O-H BOND; ONE-ELECTRON OXIDATION; PHOSPHATIDYLCHOLINE; PUERARIN; RADICAL CATIONS; TIME-SCALES;

CHEMICAL BONDS; DENSITY FUNCTIONAL THEORY; FATTY ACIDS; FREE RADICALS; LIPOSOMES; OLEFINS; ORGANIC POLYMERS; OXIDATION; PHENOLS; PHOSPHOLIPIDS; PHOTOLYSIS; RATE CONSTANTS; SUGARS;

FLAVONOIDS;

ANTIOXIDANT; BETA CAROTENE; FLAVONOID; GLYCOSIDE; LIPOSOME;

ARTICLE; KINETICS; OXIDATION REDUCTION REACTION; THERMODYNAMICS;

ANTIOXIDANTS; BETA CAROTENE; FLAVONOIDS; GLYCOSIDES; KINETICS; LIPOSOMES; OXIDATION-REDUCTION; THERMODYNAMICS;

EID: 77956543001     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1015413     Document Type: Article

References (29)

1. Key, T. J. A.; Thorogood, M.; Appleby, P. N.; Burr, M. L. Dietary habits and mortality in 11 000 vegetarians and health conscious people: results of a 17 year follow up. Br. Med. J. 1996, 313, 775-779.
2. Becker, E. M.; Nissen, L. R.; Skibsted, L. H. Antioxidant evaluation protocols: food quality or health effects. Eur. Food Res. Technol. 2004, 219, 561-571.
3. Han, R. M.; Tian, Y. X.; Becker, E. M.; Andersen, M. L.; Zhang, J. P.; Skibsted, L. H. Puerarin and conjugate bases as radical scavengers and antioxidants: molecular mechanism and synergism with β-carotene. J. Agric. Food Chem. 2007, 55, 2384-2391.
4. Zhou, B.; Wu, L. M.; Yang, L.; Liu, Z. L. Evidence for R-tocopherol regeneration reaction of green tea polyphenols in SDS micelles. Free Radical Biol. Med. 2005, 38, 78-84.
5. Omenn, G. S.; Goodman, G. E.; Thornquist, M. D.; Balmes, J.; Cullen, M. R.; Glass, A.; Reogh, J. P.; Meyskens, F. L.; Valanis, B.; Williams, J. H.; Barnhart, S.; Hammar, S. Effects of a combination of beta carotene and vitamin A on lung cancer and cardiovascular disease. New Engl. J. Med. 1996, 334, 1150-1155.
6. Hollman, P. C. H.; Katan, M. B. Dietary flavonoids: intake, health effects and bioavailability. Food Chem. Toxicol. 1999, 37, 937-942.
7. Wu, X.; Beecher, G. R.; Holden, J. M.; Haytowitz, D. B.; Gebhardt, S. E.; Prior, R. L. Lipophilic and hydrophilic antioxidant capacities of common foods in the United States. J. Agric. Food Chem. 2004, 52, 4026-4037.
8. Uri, N. Mechanism of antioxidation. In Autoxidation and Antioxidants; Lundberg, W. O., Ed.; Wiley: New York, 1961; pp 133-169.
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. Schroeder, M. T.; Becker, E. M.; Skibsted, L. H. Molecular mechanism of antioxidant synergism of tocotrienols and carotenoids in palm oil. J. Agric. Food Chem. 2006, 54, 3445-3453.
11. Martinez, A.; Barbosa, A. Antiradical power of carotenoids and vitamin E: testing the hydrogen atom transfer mechanism. J. Phys. Chem. B 2008, 112, 16945-16951.
12. Martinez, 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.
13. Galano, A.; Vargas, R.; Martinez, A. Carotenoids can act as antioxidants by oxidizing the superoxide radical anion. Phys. Chem. Chem. Phys. 2010, 12, 193-200.
14. Martinez, A. Donator acceptor map of psittacofulvins and anthocyanins: are they good antioxidant substances? J. Phys. Chem. B 2009, 113, 4915-4921.
15. 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.
16. Hu, C.; Zhang, Y.; Kitts, D. D. Evaluation of antioxidant and prooxidant activities of bamboo Phyllostachys nigra var. Henonis leaf extract in vitro. J. Agric. Food Chem. 2000, 48, 3170-3176.
17. Roberts, W. G.; Gordon, M. H. Determination of the total antioxidant activity of fruits and vegetables by a liposome assay. J. Agric. Food Chem. 2003, 51, 1486-1493.
18. Hwang, J.; Sevanian, A.; Hodis, H. N.; Ursini, F. Synergistic inhibition of LDL oxidation by phytoestrogens and ascorbic acid. Free Radical Biol. Med. 2000, 29, 79-89.
19. Han, R.-M.; Tian, Y.-X.; Wu, Y.-S.; Wang, P.; Ai, X.-C.; Zhang, J.-P.; Skibsted, L. H. Mechanism of radical cation formation from the excited states of zeaxanthin and astaxanthin in chloroform. Photochem. Photobiol. 2006, 82, 538-546.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T., Jr.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.;Fukuda, R.; Hasegawa, J.; Ishida M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S ; Cioslowski, J.; Stefanov, B. B.; Liu, G.;Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez C.; Pople, J. A. Gaussian 03W, revision E.01; Gaussian Inc.: Pittsburgh, PA. 2003.
21. Han, R.-M.; Tian, Y.-X.; Liu, Y.; Chen, C.-H.; Ai, X.-C.; Zhang, J.-P.; Skibsted, L. H. A comparison of flavonoids and isoflavonoidsas antioxidants. J. Agric. Food Chem. 2009, 57, 3780-3785.
22. Musialik, M.; Kuzmicz, R.; Pawlowski, T. S.; Litwinienko, G. Acidity of hydroxyl groups: an overlooked influence on antiradical properties of flavonoids. J. Org. Chem. 2009, 74, 2699-2709.
23. Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.; Simic, M. G. Flavonoids as antioxidants. J. Am. Chem. Soc. 1994, 116,4846-4851.
24. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice- Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free RadicalBiol. Med. 1999, 26, 1232-1237.
25. Arts, M. J. T. J.; Dallinga, J. S.; Voss, H. P.; Haenen, G. R. M. M.; Bast, A. A new approach to assess the total antioxidant capacity using the TEAC assay. Food Chem. 2004, 88, 567-570.
26. Liang, R.; Han, R.-M.; Fu, L.-M.; Ai, X.-C.; Zhang, J.-P.; Skibsted, L. H. Baicalin in radical scavenging and its synergistic effect with β-carotene in antilipoxidation. J. Agric. Food Chem. 2009, 57, 7118-7124.
27. Ishige, K.; Schubert, D.; Sagara, Y. Flavonoids protect neuronal cells from oxidative stress by three distinct mechanisms. Free Radical Biol. Med. 2001, 30, 433-446.
28. Guo, J.-J.; Hsieh, H.-Y.; Hu, C.-H. Chain-breaking activity of carotenes in lipid peroxidation: a theoretical study. J. Phys. Chem. B 2009, 113, 15699-15708.
29. Tian, Y.-X.; Han, R.-M.; Fu, L.-M.; Zhang, J.-P.; Skibsted, L. H. Radical dynamics of puerarin as revealed by laser flash photolysis and spin density analysis. J. Phys. Chem. B 2008, 112, 2273-2280