Emulsifier-phenol bioconjugates as antioxidants. Molecular descriptors based on density functional theory in quantitative structure-activity relationship

Marianne Lund Lametsch; Ran Liang; Jian-Ping Zhang; Rui-Min Han; Yu-Xi Tian; Thure F. Skovsgaard; John Nielsen; Leif Horsfelt Skibsted

doi:10.1016/j.foodres.2013.07.014

Emulsifier-phenol bioconjugates as antioxidants. Molecular descriptors based on density functional theory in quantitative structure-activity relationship

Marianne Lund Lametsch, Ran Liang, Jian-Ping Zhang, Rui-Min Han, Yu-Xi Tian, Thure F. Skovsgaard, John Nielsen, Leif Horsfelt Skibsted

Food Chemistry

2 Citations (Scopus)

Abstract

For 27 members of a combinatorial library of antioxidant bioconjugates of Trolox, dihydroferulic acid, dihydrocaffeic acid and gallic acid combined with serine ethyl ester, serine lauryl ester, lauroyl serine, serine capryl ester, and N-capryl serine, including the parent phenols and their non-reduced forms, bond dissociation enthalpy (BDE), energy of highest occupied orbital (E_HOMO), energy of lowest unoccupied orbital (E_LUMO) and dipole moment (μ) were calculated according to density functional theory (DFT) as molecular descriptors. For each series of parent phenols, the lag phase for formation of conjugated dienes in unilamellar phosphatidylcholine liposomes with radical initiation from the aqueous phase was found to correlate with BDE. Rate of scavenging of the beta-carotene radical cation was found to correlate with μ for the Trolox bioconjugates in homogeneous solution. Rate of scavenging of the semi-stable radical DPPH by the bioconjugates was found to increase with hydrophobicity in aqueous micelles. The difference in structure-activity relationship reflects changes in antioxidant mechanism.

Original language	English
Journal	Food Research International
Volume	54
Issue number	1
Pages (from-to)	230-238
Number of pages	9
ISSN	0963-9969
DOIs	https://doi.org/10.1016/j.foodres.2013.07.014
Publication status	Published - Nov 2013

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Emulsifier-phenol bioconjugates as antioxidants. Molecular descriptors based on density functional theory in quantitative structure-activity relationship. / Lametsch, Marianne Lund; Liang, Ran; Zhang, Jian-Ping et al.

In: Food Research International, Vol. 54, No. 1, 11.2013, p. 230-238.

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title = "Emulsifier-phenol bioconjugates as antioxidants. Molecular descriptors based on density functional theory in quantitative structure-activity relationship",

abstract = "For 27 members of a combinatorial library of antioxidant bioconjugates of Trolox, dihydroferulic acid, dihydrocaffeic acid and gallic acid combined with serine ethyl ester, serine lauryl ester, lauroyl serine, serine capryl ester, and N-capryl serine, including the parent phenols and their non-reduced forms, bond dissociation enthalpy (BDE), energy of highest occupied orbital (EHOMO), energy of lowest unoccupied orbital (ELUMO) and dipole moment (μ) were calculated according to density functional theory (DFT) as molecular descriptors. For each series of parent phenols, the lag phase for formation of conjugated dienes in unilamellar phosphatidylcholine liposomes with radical initiation from the aqueous phase was found to correlate with BDE. Rate of scavenging of the beta-carotene radical cation was found to correlate with μ for the Trolox bioconjugates in homogeneous solution. Rate of scavenging of the semi-stable radical DPPH by the bioconjugates was found to increase with hydrophobicity in aqueous micelles. The difference in structure-activity relationship reflects changes in antioxidant mechanism.",

author = "Lametsch, {Marianne Lund} and Ran Liang and Jian-Ping Zhang and Rui-Min Han and Yu-Xi Tian and Skovsgaard, {Thure F.} and John Nielsen and Skibsted, {Leif Horsfelt}",

year = "2013",

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AU - Lametsch, Marianne Lund

AU - Liang, Ran

AU - Zhang, Jian-Ping

AU - Han, Rui-Min

AU - Tian, Yu-Xi

AU - Skovsgaard, Thure F.

AU - Nielsen, John

AU - Skibsted, Leif Horsfelt

PY - 2013/11

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N2 - For 27 members of a combinatorial library of antioxidant bioconjugates of Trolox, dihydroferulic acid, dihydrocaffeic acid and gallic acid combined with serine ethyl ester, serine lauryl ester, lauroyl serine, serine capryl ester, and N-capryl serine, including the parent phenols and their non-reduced forms, bond dissociation enthalpy (BDE), energy of highest occupied orbital (EHOMO), energy of lowest unoccupied orbital (ELUMO) and dipole moment (μ) were calculated according to density functional theory (DFT) as molecular descriptors. For each series of parent phenols, the lag phase for formation of conjugated dienes in unilamellar phosphatidylcholine liposomes with radical initiation from the aqueous phase was found to correlate with BDE. Rate of scavenging of the beta-carotene radical cation was found to correlate with μ for the Trolox bioconjugates in homogeneous solution. Rate of scavenging of the semi-stable radical DPPH by the bioconjugates was found to increase with hydrophobicity in aqueous micelles. The difference in structure-activity relationship reflects changes in antioxidant mechanism.

AB - For 27 members of a combinatorial library of antioxidant bioconjugates of Trolox, dihydroferulic acid, dihydrocaffeic acid and gallic acid combined with serine ethyl ester, serine lauryl ester, lauroyl serine, serine capryl ester, and N-capryl serine, including the parent phenols and their non-reduced forms, bond dissociation enthalpy (BDE), energy of highest occupied orbital (EHOMO), energy of lowest unoccupied orbital (ELUMO) and dipole moment (μ) were calculated according to density functional theory (DFT) as molecular descriptors. For each series of parent phenols, the lag phase for formation of conjugated dienes in unilamellar phosphatidylcholine liposomes with radical initiation from the aqueous phase was found to correlate with BDE. Rate of scavenging of the beta-carotene radical cation was found to correlate with μ for the Trolox bioconjugates in homogeneous solution. Rate of scavenging of the semi-stable radical DPPH by the bioconjugates was found to increase with hydrophobicity in aqueous micelles. The difference in structure-activity relationship reflects changes in antioxidant mechanism.

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DO - 10.1016/j.foodres.2013.07.014

M3 - Journal article

SN - 0963-9969

VL - 54

SP - 230

EP - 238

JO - Food Research International

JF - Food Research International

IS - 1

ER -

Emulsifier-phenol bioconjugates as antioxidants. Molecular descriptors based on density functional theory in quantitative structure-activity relationship

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