Astaxanthin diferulate as a bifunctional antioxidant

Abstract Astaxanthin when esterified with ferulic acid is better singlet oxygen quencher with k2 = (1.58 ± 0.1) 1010 L mol− 1s− 1 in ethanol at 25°C compared with astaxanthin with k2 = (1.12 ± 0.01) 109 L mol− 1s− 1. The ferulate moiety in the astaxanthin diester is a better radical scavenger than free ferulic acid as seen from the rate constant of scavenging of 1-hydroxyethyl radicals in ethanol at 25°C with a second-order rate constant of (1.68 ± 0.1) 108 L mol− 1s− 1 compared with (1.60 ± 0.03) 107 L mol− 1s− 1 for the astaxanthin:ferulic acid mixture, 1:2 equivalents. The mutual enhancement of antioxidant activity for the newly synthetized astaxanthin diferulate becoming a bifunctional antioxidant is rationalized according to a two-dimensional classification plot for electron donation and electron acceptance capability.

[1]  L. Skibsted,et al.  Quercetin and daidzein β-apo-14’-carotenoic acid esters as membrane antioxidants , 2013, Free radical research.

[2]  Hern Kim,et al.  A Mild, Efficient, and Selective Deprotection of tert-Butyldimethylsilyl (TBDMS) Ethers Using Dicationic Ionic Liquid as a Catalyst. , 2012 .

[3]  M. Zeeshan,et al.  Electron uptake by classical electron donators: astaxanthin and carotenoid aldehydes , 2012 .

[4]  W. Stahl,et al.  UVA photoprotective properties of an artificial carotenylflavonoid hybrid molecule. , 2012, Chemical research in toxicology.

[5]  L. Skibsted.  Carotenoids in antioxidant networks. Colorants or radical scavengers. , 2012, Journal of agricultural and food chemistry.

[6]  F. Böhm,et al.  Interactions of dietary carotenoids with activated (singlet) oxygen and free radicals: potential effects for human health. , 2012, Molecular nutrition & food research.

[7]  D. de Keukeleire,et al.  Reactivity of beer bitter acids toward the 1-hydroxyethyl radical as probed by spin-trapping electron paramagnetic resonance (EPR) and electrospray ionization-tandem mass spectrometry (ESI-MS/MS). , 2011, Journal of agricultural and food chemistry.

[8]  L. Skibsted,et al.  Direct observation of the β-carotene reaction with hydroxyl radical. , 2011, The journal of physical chemistry. B.

[9]  L. Skibsted,et al.  Retinylisoflavonoid as a novel membrane antioxidant. , 2010, The journal of physical chemistry. B.

[10]  L. Skibsted,et al.  Thermodynamic versus kinetic control of antioxidant synergism between β-carotene and (iso)flavonoids and their glycosides in liposomes. , 2010, Journal of agricultural and food chemistry.

[11]  L. Skibsted,et al.  Fast regeneration of carotenoids from radical cations by isoflavonoid dianions: importance of the carotenoid keto group for electron transfer. , 2010, The journal of physical chemistry. A.

[12]  A. Galano,et al.  Carotenoids can act as antioxidants by oxidizing the superoxide radical anion. , 2010, Physical chemistry chemical physics : PCCP.

[13]  A. Galano,et al.  What is important to prevent oxidative stress? A theoretical study on electron-transfer reactions between carotenoids and free radicals. , 2009, The journal of physical chemistry. B.

[14]  Ana Martínez.  Donator-acceptor map and work function for linear polyene-conjugated molecules. A density functional approximation study. , 2009, The journal of physical chemistry. B.

[15]  W. Stahl,et al.  3,3'-Dihydroxyisorenieratene, a natural carotenoid with superior antioxidant and photoprotective properties. , 2009, Angewandte Chemie.

[16]  A. Barbosa,et al.  Donator acceptor map for carotenoids, melatonin and vitamins. , 2008, The journal of physical chemistry. A.

[17]  A. Cedillo,et al.  Electrodonating and electroaccepting powers. , 2007, The journal of physical chemistry. A.

[18]  W. Stahl,et al.  Carotenylflavonoids, a novel group of potent, dual-functional antioxidants , 2007 .

[19]  S. Santos,et al.  Glycerol-ω-hydroxyacid-ferulic acid oligomers in cork suberin structure , 2006 .

[20]  O. Piva,et al.  Total synthesis of cimiracemate B and analogs , 2005 .

[21]  P. Di Mascio,et al.  Lycopene as the most efficient biological carotenoid singlet oxygen quencher. , 1989, Archives of biochemistry and biophysics.