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

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12 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Free Radical Research
Vol/bind	49
Udgave nummer	1
Sider (fra-til)	102-111
Antal sider	10
ISSN	1071-5762
DOI	https://doi.org/10.3109/10715762.2014.982112
Status	Udgivet - 1 jan. 2015

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10.3109/10715762.2014.982112

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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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doi = "10.3109/10715762.2014.982112",

language = "English",

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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.

U2 - 10.3109/10715762.2014.982112

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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