Quinones as Strecker degradation reagents in wine oxidation processes

Carla Maria Oliveira; Sónia A. O. Santos; Armando J. D. Silvestre; António S. Barros; António César Silva Ferreira; Artur M. S. Silva

doi:10.1016/j.foodchem.2017.02.034

Quinones as Strecker degradation reagents in wine oxidation processes

Carla Maria Oliveira^*, Sónia A. O. Santos, Armando J. D. Silvestre, António S. Barros, António César Silva Ferreira, Artur M. S. Silva

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

The Strecker aldehydes formed during the reaction between α-amino acids (phenylalanine or methionine) and either gallic acid, caffeic acid or (+)-catechin ortho-quinones were evaluated in wine-model systems. It was demonstrated that phenylacetaldehyde was formed by quinone intermediates at wine pH. The highest amounts of phenylacetaldehyde during the 10 days of experiment (69 ± 5 µg/L/day; 7x > Control) were obtained from (+) catechin, followed by gallic acid (61 ± 4 µg/L/day; 6x > Control) and caffeic acid (41 ± 4 µg/L/day; 4x > Control). The intermediate structures delivered from the reaction of ortho-quinones with α-amino acids were demonstrated by MSⁿ.

Original language	English
Pages (from-to)	618-624
Number of pages	7
Journal	Food Chemistry
Volume	228
DOIs	https://doi.org/10.1016/j.foodchem.2017.02.034
Publication status	Published - 1 Aug 2017

Keywords

Amino acids
Oxidation
Oxygen
Phenolics
Quinones
Strecker aldehydes
Wine

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10.1016/j.foodchem.2017.02.034

http://hdl.handle.net/10400.14/23735

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title = "Quinones as Strecker degradation reagents in wine oxidation processes",

abstract = "The Strecker aldehydes formed during the reaction between α-amino acids (phenylalanine or methionine) and either gallic acid, caffeic acid or (+)-catechin ortho-quinones were evaluated in wine-model systems. It was demonstrated that phenylacetaldehyde was formed by quinone intermediates at wine pH. The highest amounts of phenylacetaldehyde during the 10 days of experiment (69 ± 5 µg/L/day; 7x > Control) were obtained from (+) catechin, followed by gallic acid (61 ± 4 µg/L/day; 6x > Control) and caffeic acid (41 ± 4 µg/L/day; 4x > Control). The intermediate structures delivered from the reaction of ortho-quinones with α-amino acids were demonstrated by MSn.",

keywords = "Amino acids, Oxidation, Oxygen, Phenolics, Quinones, Strecker aldehydes, Wine",

author = "Oliveira, {Carla Maria} and Santos, {S{\'o}nia A. O.} and Silvestre, {Armando J. D.} and Barros, {Ant{\'o}nio S.} and Ferreira, {Ant{\'o}nio C{\'e}sar Silva} and Silva, {Artur M. S.}",

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doi = "10.1016/j.foodchem.2017.02.034",

language = "English",

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journal = "Food Chemistry",

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TY - JOUR

T1 - Quinones as Strecker degradation reagents in wine oxidation processes

AU - Oliveira, Carla Maria

AU - Santos, Sónia A. O.

AU - Silvestre, Armando J. D.

AU - Barros, António S.

AU - Ferreira, António César Silva

AU - Silva, Artur M. S.

PY - 2017/8/1

Y1 - 2017/8/1

N2 - The Strecker aldehydes formed during the reaction between α-amino acids (phenylalanine or methionine) and either gallic acid, caffeic acid or (+)-catechin ortho-quinones were evaluated in wine-model systems. It was demonstrated that phenylacetaldehyde was formed by quinone intermediates at wine pH. The highest amounts of phenylacetaldehyde during the 10 days of experiment (69 ± 5 µg/L/day; 7x > Control) were obtained from (+) catechin, followed by gallic acid (61 ± 4 µg/L/day; 6x > Control) and caffeic acid (41 ± 4 µg/L/day; 4x > Control). The intermediate structures delivered from the reaction of ortho-quinones with α-amino acids were demonstrated by MSn.

AB - The Strecker aldehydes formed during the reaction between α-amino acids (phenylalanine or methionine) and either gallic acid, caffeic acid or (+)-catechin ortho-quinones were evaluated in wine-model systems. It was demonstrated that phenylacetaldehyde was formed by quinone intermediates at wine pH. The highest amounts of phenylacetaldehyde during the 10 days of experiment (69 ± 5 µg/L/day; 7x > Control) were obtained from (+) catechin, followed by gallic acid (61 ± 4 µg/L/day; 6x > Control) and caffeic acid (41 ± 4 µg/L/day; 4x > Control). The intermediate structures delivered from the reaction of ortho-quinones with α-amino acids were demonstrated by MSn.

KW - Amino acids

KW - Oxidation

KW - Oxygen

KW - Phenolics

KW - Quinones

KW - Strecker aldehydes

KW - Wine

UR - http://www.scopus.com/inward/record.url?scp=85012982122&partnerID=8YFLogxK

U2 - 10.1016/j.foodchem.2017.02.034

DO - 10.1016/j.foodchem.2017.02.034

M3 - Article

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AN - SCOPUS:85012982122

SN - 0308-8146

VL - 228

SP - 618

EP - 624

JO - Food Chemistry

JF - Food Chemistry

ER -

Quinones as Strecker degradation reagents in wine oxidation processes

Abstract

Keywords

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