Electrochemical study of astaxanthin and astaxanthin n-octanoic monoester and diester: Tendency to form radicals

Journal of Physical Chemistry B

Volumn 118, Issue 9, 2014, Pages 2331-2339

  Focsan, A Ligia ^a   Pan, Shanlin ^b   Kispert, Lowell D ^b  

^a VALDOSTA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSITIONS; EQUILIBRIUM CONSTANTS; ESTERIFICATION; ESTERS; ORGANOMETALLICS; OXIDATION; PIGMENTS; POSITIVE IONS; REDOX REACTIONS; SCAVENGING;

ANTI-OXIDANT ACTIVITIES; CYCLIC VOLTAMMOGRAMS; ELECTROCHEMICAL STUDIES; OXIDATION POTENTIALS; PRECISE SIMULATION; PROTON ABSTRACTION; REDUCTION POTENTIAL; TWO-ELECTRON TRANSFER;

FREE RADICAL REACTIONS;

ASTAXANTHIN; FERROCENE; FERROUS ION; FREE RADICAL; XANTHOPHYLL;

ARTICLE; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; OXIDATION REDUCTION REACTION;

ELECTROCHEMICAL TECHNIQUES; FERROUS COMPOUNDS; FREE RADICALS; OXIDATION-REDUCTION; XANTHOPHYLLS;

EID: 84897696470     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp4121436     Document Type: Article

References (45)

1. Britton, G.; Liaaen-Jensen, S.; Pfander, H. Carotenoids. Handbook; Birkhauser Verlag: Basel, Boston, Berlin, 2004.
2. Hapiot, P.; Kispert, L. D.; Konovalov, V. V.; Saveant, J. Single Two-Electron Transfers vs Successive One-Electron Transfers in Polyconjugated Systems Illustrated by the Electrochemical Oxidation and Reduction of Carotenoids J. Am. Chem. Soc. 2001, 123, 6669-6677
3. Liu, D.; Gao, Y.; Kispert, L. D. Electrochemical Properties of Natural Carotenoids J. Electroanal. Chem. 2000, 488, 140-150
4. Liu, D.; Kispert, L. D. Electrochemical Aspects of Carotenoids Recent Res. Dev. Electrochem. 1999, 2, 139-157
5. Jeevarajan, J. A.; Kispert, L. D. Electrochemical Oxidation of Carotenoids Containing Donor/Acceptor Substituents J. Electroanal. Chem. 1996, 411, 57-66
6. Lorenz, R. T. A Technical Review of Haematococcus Algae.
7. 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
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. Biot. 1997, 48, 351-356
9. Kobayashi, M.; Sakamoto, Y. Singlet Oxygen Quenching Ability of Astaxanthin Esters from the Green Alga Haematococcus Pluvialis Biotechnol. Lett. 1999, 21, 265-269
10. Lotocka, M.; Styczynska-Jurewicz, E. Astaxanthin, Canthaxanthin and Astaxanthin Esters in the Copepod Acartia Bifilosa (Copepoda, Calanoida) during Ontogenetic Development Oceanologia 2001, 487-497
11. Mordi, R. C. Carotenoids-Function and Degradation Chem. Ind. 1993, 110, 79-83
12. Woodall, A. A.; Lee, S. W.; Weesie, R. J.; Jackson, M. J.; Britton, G. Oxidation of Carotenoids by Free Radicals: Relationship Between Structure and Reactivity Biochim. Biophys. Acta 1997, 1336, 33-42
13. Mortensen, A.; Skibsted, L. H.; Sampson, J.; Rice-Evans, C.; Everett, S. A. Comparative Mechanisms and Rates of Free Radical Scavenging by Carotenoid Antioxidants FEBS Lett. 1997, 418, 91-97
14. Edge, R.; McGarvey, D. J.; Truscott, T. G. The Carotenoids as Anti-oxidants-A Review J. Photochem. Photobiol., B 1997, 41, 189-200R
15. Polyakov, N. E.; Leshina, T. V.; Konovalova, T. A.; Kispert, L. D. Carotenoids as Scavengers of Free Radicals in a Fenton Reaction: Antioxidants or Pro-Oxidants? Free Radical Biol. Med. 2001, 31, 398-404
16. 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
17. 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 D.01; Gaussian, Inc.: Wallingford, CT, 2009.
18. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
19. 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
20. Gao, Y. L.; Focsan, A. L.; Kispert, L. D.; Dixon, D. A. Density Functional Theory Study of the β-Carotene Radical Cation and Deprotonated Radicals J. Phys. Chem. B 2006, 110, 24750-24756
21. Deng, Y. Carotenoid Radical Cations and Dications Studied by Electrochemical, Optical and Flow Injection Analysis: Lifetime, Extended Chain Conjugation, and Isomerization Properties. Ph.D. Dissertation, The University of Alabama, Tuscaloosa, AL, 1999.
22. He, Z.; Kispert, L. D. Effect of Electrolytes and Temperature on Dications and Radical Cations of Carotenoids: Electrochemical, Optical Absorption, and High-Performance Liquid Chromatography Studies J. Phys. Chem. B 1999, 103, 10524-10531
23. Grant, J. L.; Kramer, V. J.; Ding, R.; Kispert, L. D. Carotenoid Cation Radicals: Electrochemical, Optical, and EPR Study J. Am. Chem. Soc. 1988, 110, 2151-2157
24. Gao, G.; Wurm, D. B.; Kim, Y.-T.; Kispert, L. D. Electrochemical Quartz Crystal Microbalance, Voltammetry, Spectroelectrochemical, and Microscopic Studies of Adsorption Behavior for (7E,7′Z)-Diphenyl-7,7′- Diapocarotene Electrochemical Oxidation Product J. Phys. Chem. B 1997, 101, 2038-2045
25. Gao, G.; Jeevarajan, J. A.; Kispert, L. D. Cyclic Voltammetry and Spectroelectrochemical Studies of Cation Radical and Dication Adsorption Behavior for 7,7′-Diphenyl-7,7′-Diapocarotene J. Electroanal. Chem. 1996, 411, 51-56
26. Gao, G. Electrochemical, Optical, Photochemical and Chromatographic Studies of Carotenoid Cation Radicals and Dications: Adsorption, Polymerization and Isomerization Properties. Ph.D. Dissertation, The University of Alabama, Tuscaloosa, AL, 1997.
27. Han, R.-M.; Tian, Y.-X.; Wu, Y.-S.; Wang, P.; Ail, 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
28. 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
29. Hideg, E.; Barta, C.; Kalai, T.; Vass, I.; Hideg, K.; Asada, K. Detection of Singlet Oxygen and Superoxide with Fluorescent Sensors in Leaves Under Stress by Photoinhibition or UV Irradiation Plant Cell Physiol. 2002, 43, 1154-1164
30. 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 (6) 1806-1819
31. 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
32. Magyar, A.; Bowman, M. K.; Molnár, P.; Kispert, L. Neutral Carotenoid Radicals in Photoprotection of Wild-Type Arabidopsis thaliana J. Phys. Chem. B 2013, 117, 2239-2246
33. Zigman, M.; Dubinsky, Z.; Iluz, D. The Xanthophyll Cycle in Aquatic Phototrophs and Its Role in the Mitigation of Photoinhibition and Photodynamic Damage. In Applied Photosynthesis; Najafpour, M., Ed.; InTech: 2012.
34. Gao, Z.; Meng, C.; Zhang, X.; Xu, D.; Zhao, Y.; Wang, Y.; Lv, H.; Yang, L.; Chen, L.; Ye, N. Differential Expression of Carotenogenic Genes, Associated Changes on Astaxanthin Production and Photosynthesis Features Induced by JA in H. pluvialis PLoS One 2012, 7, 1-7
35. Goto, S.; Kogure, K.; Abe, K.; Kimata, Y.; Kitahama, K.; Yamashita, E.; Terada, H. Efficient Radical Trapping at The Surface and Inside the Phospholipid Membrane Is Responsible For Highly Potent Antiperoxidative Activity of the Carotenoid Astaxanthin Biochim. Biophys. Acta 2001, 1512, 251-258
36. Hideg, E.; Barta, C.; Kalai, T.; Vass, I.; Hideg, K.; Asada, K. Detection of Singlet Oxygen and Superoxide with Fluorescent Sensors in Leaves under Stress by Photoinhibition or UV Radiation Plant Cell Physiol. 2002, 43, 1154-1164
37. Focsan, A. L.; Bowman, M. K.; Molnár, P.; Deli, J.; Kispert, L. D. Carotenoid Radical Formation: Dependence on Conjugation Length J. Phys. Chem. B 2011, 115, 9495-9506
38. Focsan, A. L.; Bowman, M. K.; Shamshina, J.; Krzyaniak, M. D.; Magyar, A.; Polyakov, N. E.; Kispert, L. D. EPR Study of the Astaxanthin n-Octanoic Acid Monoester and Diester Radicals on Silica-Alumina J. Phys. Chem. B 2012, 116, 13200-13210
39. Nishida, Y.; Yamashita, E.; Miki, W. Quenching Activities of Common Hydrophilic and Lipophilic Antioxidants Against Singlet Oxygen Using Chemiluminescence Detection System Carotenoid Sci. 2007, 11, 16-20
40. Hama, S.; Uenishi, S.; Yamada, A.; Ohgita, T.; Tsuchiya, H.; Yamashita, E.; Kogure, K. Scavenging of hydroxyl radicals in aqueous solution by astaxanthin encapsulated in liposomes Biol. Pharm. Bull. 2012, 35, 2238-2242
41. Naguib, Y. M. Antioxidant Activities of Astaxanthin and Related Carotenoids J. Agric. Food Chem. 2000, 48, 1150-1154
42. Polyakov, N. E.; Magyar, A.; Kispert, L. Photochemical and Optical Properties of Water-Soluble Xanthophyll Antioxidants: Aggregation vs Complexation J. Phys. Chem. B 2013, 117, 10173-10182
43. Martin, H. D.; Ruck, C.; Schmidt, M.; Sell, S.; Beutner, S.; Mayer, B.; Walsh, R. Chemistry of Carotenoid Oxidation and Free Radical Reactions Pure Appl. Chem. 1999, 71, 2253-2262
44. Yamashita, E. Astaxanthin as a Medical Food Funct. Foods Health Dis. 2013, 3, 254-258
45. Deng, Y.; Gao, G.; He, Z.; Kispert, L. D. Effects of Polyene Chain Length and Acceptor Substituents on The Stability of Carotenoid Radical Cations J. Phys. Chem. B 2000, 104, 5651-5656