Astaxanthin diferulate as a bifunctional antioxidant

T.B.R. Papa; V.D. Pinho; E.P. do Nascimento; W.G. Santos; A.C.B. Burtoloso; Leif Horsfelt Skibsted; D.R. Cardoso

doi:10.3109/10715762.2014.982112

Astaxanthin diferulate as a bifunctional antioxidant

T.B.R. Papa, V.D. Pinho, E.P. do Nascimento, W.G. Santos, A.C.B. Burtoloso, Leif Horsfelt Skibsted, D.R. Cardoso

Food Chemistry

12 Citations (Scopus)

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.

Original language	English
Journal	Free Radical Research
Volume	49
Issue number	1
Pages (from-to)	102-111
Number of pages	10
ISSN	1071-5762
DOIs	https://doi.org/10.3109/10715762.2014.982112
Publication status	Published - 1 Jan 2015

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title = "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.",

author = "T.B.R. Papa and V.D. Pinho and Nascimento, {E.P. do} and W.G. Santos and A.C.B. Burtoloso and Skibsted, {Leif Horsfelt} and D.R. Cardoso",

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T1 - Astaxanthin diferulate as a bifunctional antioxidant

AU - Papa, T.B.R.

AU - Pinho, V.D.

AU - Nascimento, E.P. do

AU - Santos, W.G.

AU - Burtoloso, A.C.B.

AU - Skibsted, Leif Horsfelt

AU - Cardoso, D.R.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - 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.

AB - 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.

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DO - 10.3109/10715762.2014.982112

M3 - Journal article

C2 - 25363553

SN - 1071-5762

VL - 49

SP - 102

EP - 111

JO - Free Radical Research

JF - Free Radical Research

IS - 1

ER -

Astaxanthin diferulate as a bifunctional antioxidant

Abstract

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