EPR study of the astaxanthin n -octanoic acid monoester and diester radicals on silica-alumina

Journal of Physical Chemistry B

Volumn 116, Issue 44, 2012, Pages 13200-13210

  Focsan, A Ligia ^a,b   Bowman, Michael K ^b   Shamshina, Julia ^b   Krzyaniak, Matthew D ^b   Magyar, Adam ^b   Polyakov, Nikolay E ^c   Kispert, Lowell D ^b  

^a VALDOSTA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF ALABAMA   (United States)

^c INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ASTAXANTHIN; CARBONYL GROUPS; CYCLOHEXENES; DENSITY FUNCTIONAL THEORY CALCULATIONS; DFT CALCULATION; DIESTERS; EPR STUDIES; ESTER GROUPS; HYDROXYL GROUPS; METHYL GROUP; MONOESTERS; NEUTRAL RADICAL; OCTANOIC ACIDS; POLYENE CHAINS; PROTON LOSS; PULSED EPR; RADICAL ANIONS; RADICAL CATIONS; RESONANCE STABILIZATION; SILICA-ALUMINA;

DENSITY FUNCTIONAL THEORY; ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; OLEFINS;

PROTONS;

ALUMINUM OXIDE; ASTAXANTHIN; ESTER; FREE RADICAL; OCTANOIC ACID; OCTANOIC ACID DERIVATIVE; PROTON; SILICON DIOXIDE; XANTHOPHYLL;

ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY; ELECTRON SPIN RESONANCE; THERMODYNAMICS; ULTRAVIOLET RADIATION;

ALUMINUM OXIDE; CAPRYLATES; ELECTRON SPIN RESONANCE SPECTROSCOPY; ESTERS; FREE RADICALS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; PROTONS; SILICON DIOXIDE; THERMODYNAMICS; ULTRAVIOLET RAYS; XANTHOPHYLLS;

EID: 84868556869     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp307421e     Document Type: Article

References (26)

1. Mozzo, M.; Dall′Osto, L.; Hienerwadel, R.; Bassi, R.; Croce, R. Photoprotection in the Antenna Complexes of Photosystem II-Role of Individual Xanthophylls in Chlorophyll Triplet Quenching J. Biol. Chem. 2008, 283, 6184-6192
2. Holt, N. E.; Zigmantas, D.; Valkunas, L.; Li, X. P.; Niyogi, K. K.; Fleming, G. R. Carotenoid Cation Formation and the Regulation of Photosynthetic Light Harvesting Science 2005, 307, 433-436
3. Ahn, T. K.; Avenson, T. J.; Ballottari, M.; Cheng, Y. C.; Niyogi, K. K.; Bassi, R.; Fleming, G. R. Architecture of a Charge-Transfer State Regulating Light Harvesting in a Plant Antenna Protein Science 2008, 320, 794-797
4. Avenson, T. J.; Ahn, T. K.; Zigmantas, D.; Niyogi, K. K.; Li, Z.; Ballottari, M.; Bassi, R.; Fleming, G. R. Zeaxanthin Radical Cation Formation in Minor Light-Harvesting Complexes of Higher Plant Antenna J. Biol. Chem. 2008, 283, 3550-3558
5. Avenson, T. J.; Ahn, T. K.; Niyogi, K. K.; Ballottari, M.; Bassi, R.; Fleming, G. R. Lutein Can Act as a Switchable Charge Transfer Quencher in the CP26 Light-Harvesting Complex J. Biol. Chem. 2009, 284, 2830-2835
6. Focsan, A. L.; Bowman, M. K.; Konovalova, T. A.; Molnar, P.; Deli, J.; Dixon, D. A.; Kispert, L. D. Pulsed EPR and DFT Characterization of Radicals Produced by Photo-Oxidation of Zeaxanthin and Violaxanthin on Silica-Alumina J. Phys. Chem. B 2008, 112, 1806-1819
7. Focsan, A. L.; Molnár, P.; Deli, J.; Kispert, L. Structure and Properties of 9′- Cis Neoxanthin Carotenoid Radicals by Electron Paramagnetic Resonance Measurements and Density Functional Theory Calculations: Present in LHC II? J. Phys. Chem. B 2009, 113, 6087-6096
8. Kobayashi, M.; Kakizono, T.; Nishio, N.; Nagai, S.; Kurimura, Y.; Tsuji, Y. Antioxidant Role of Astaxanthin in the Green Alga Haematococcus Pluvialis Appl. Microbiol. Biotechnol. 1997, 48, 351-356
9. Eom, H.; Lee, C. G.; Jin, E. Gene Expression Profile Analysis in Astaxanthin-Induced Haematococcus Pluvialis Using a cDNA Microarray Planta 2006, 223, 1231-1242
10. Wang, B.; Zarka, A.; Trebst, A.; Boussiba, S. Astaxanthin Accumulation in Haematococcus Pluvialis (Chlorophyceae) as an Active Photoprotective Process Under High Irradiance J. Phycol. 2003, 39, 1116-1124
11. Hu, Z. Y.; Li, Y. T.; Sommerfeld, M.; Chen, F.; Hu, Q. Enhanced Protection Against Oxidative Stress in an Astaxanthin-Overproduction Haematococcus Mutant (Chlorophyceae) Eur. J. Phycol. 2008, 43, 365-376
12. Guerin, M.; Huntley, M. E.; Olaizola, M. Haematococcus Astaxanthin: Applications for Human Health and Nutrition Trends Biotechnol. 2003, 21, 210-216
13. Lorenz, T. A Technical Review of Haematococcus Algae, Cyanotech Corporation; http://www.cyanotech.com/pdfs/bioastin/axbul60.pdf (accessed Oct 1, 2012).
14. Polyakov, N. E.; Focsan, A. L.; Bowman, M. K.; Kispert, L. D. Free Radical Formation in Novel Carotenoid Metal Ion Complexes of Astaxanthin J. Phys. Chem. B 2010, 114, 16968-16977
15. Fukami, H.; Namikawa, K.; Tomimori, N.; Sumida, M.; Katano, K.; Nakao, M. Chemical Synthesis of Astaxanthin n-Octanoic Acid Monoester and Diester and Evaluation of Their Oral Absorbability J. Oleo Sci 2006, 55, 653-656
16. Mims, W. B. Proc. R. Soc. London, Ser. A 1965, 283, 452-457
17. Astashkin, A. University of Arizona, http://quiz2.chem.arizona.edu/epr/ epr-000006.htm (accessed Oct 1, 2012).
18. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Gaussian 03, revision B.02; Gaussian, Inc.: Pittsburgh, PA, 2003.
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, revision B.1; Gaussian, Inc.: Wallingford, CT, 2009.
20. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
21. Lee, C. T.; Yang, W. T.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron-Density Phys. Rev. B 1988, 37, 785-789
22. Gao, Y. L.; Focsan, A. L.; Kispert, L. D.; Dixon, D. A. Density Functional Theory Study of the Beta-Carotene Radical Cation and Deprotonated Radicals J. Phys. Chem. B 2006, 110, 24750-24756
23. Schafer, A.; Horn, H.; Ahlrichs, R. Fully Optimized Contracted Gaussian-Basis Sets for Atoms Li To Kr J. Chem. Phys. 1992, 97, 2571-2577
24. Cho, H.; Felmy, A. R.; Craciun, R.; Keenum, J. P.; Shah, N.; Dixon, D. A. Solution State Structure Determination of Silicate Oligomers by Si-29 NMR Spectroscopy and Molecular Modeling J. Am. Chem. Soc. 2006, 128, 2324-2335
25. http://www.semichem.com/ampac/ampacgui-features.php (accessed Oct 1, 2012).
26. Jeevarajan, A. S.; Kispert, L. D.; Piekara-Sady, L. An ENDOR Study of Carotenoid Cation Radicals on Silica-Alumina Solid Supports Chem. Phys. Lett. 1993, 209, 269-274