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Formation of phenylacetic acid and benzaldehyde by degradation of phenylalanine in the presence of lipid hydroperoxides: New routes in the amino acid degradation pathways initiated by lipid oxidation products.
Food Chem X 2019; 2:100037FC

Abstract

Lipid oxidation is a main source of reactive carbonyls, and these compounds have been shown both to degrade amino acids by carbonyl-amine reactions and to produce important food flavors. However, reactive carbonyls are not the only products of the lipid oxidation pathway. Lipid oxidation also produces free radicals. Nevertheless, the contribution of these lipid radicals to the production of food flavors by degradation of amino acid derivatives is mostly unknown. In an attempt to investigate new routes of flavor formation, this study describes the degradation of phenylalanine, phenylpyruvic acid, phenylacetaldehyde, and β-phenylethylamine in the presence of the 13-hydroperoxide of linoleic acid, 4-oxononenal (a reactive carbonyl derived from this hydroperoxide), and the mixture of both of them. The obtained results show the formation of phenylacetic acid and benzaldehyde in these reactions as a consequence of the combined action of carbonyl-amine and free radical reactions for amino acid degradation.

Authors+Show Affiliations

Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31432020

Citation

Hidalgo, Francisco J., and Rosario Zamora. "Formation of Phenylacetic Acid and Benzaldehyde By Degradation of Phenylalanine in the Presence of Lipid Hydroperoxides: New Routes in the Amino Acid Degradation Pathways Initiated By Lipid Oxidation Products." Food Chemistry: X, vol. 2, 2019, p. 100037.
Hidalgo FJ, Zamora R. Formation of phenylacetic acid and benzaldehyde by degradation of phenylalanine in the presence of lipid hydroperoxides: New routes in the amino acid degradation pathways initiated by lipid oxidation products. Food Chem X. 2019;2:100037.
Hidalgo, F. J., & Zamora, R. (2019). Formation of phenylacetic acid and benzaldehyde by degradation of phenylalanine in the presence of lipid hydroperoxides: New routes in the amino acid degradation pathways initiated by lipid oxidation products. Food Chemistry: X, 2, p. 100037. doi:10.1016/j.fochx.2019.100037.
Hidalgo FJ, Zamora R. Formation of Phenylacetic Acid and Benzaldehyde By Degradation of Phenylalanine in the Presence of Lipid Hydroperoxides: New Routes in the Amino Acid Degradation Pathways Initiated By Lipid Oxidation Products. Food Chem X. 2019 Jun 30;2:100037. PubMed PMID: 31432020.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Formation of phenylacetic acid and benzaldehyde by degradation of phenylalanine in the presence of lipid hydroperoxides: New routes in the amino acid degradation pathways initiated by lipid oxidation products. AU - Hidalgo,Francisco J, AU - Zamora,Rosario, Y1 - 2019/06/07/ PY - 2019/02/18/received PY - 2019/06/03/revised PY - 2019/06/04/accepted PY - 2019/8/22/entrez PY - 2019/8/23/pubmed PY - 2019/8/23/medline KW - 13-Hydroperoxy-9Z,11E-octadecadienoic acid (PubChem ID: 5280720) KW - 4-Oxo-2-nonenal (PubChem ID: 6445537) KW - Benzaldehyde (PubChem ID: 240) KW - Carbonyl-amine reactions KW - Food flavors KW - Free radicals KW - Lipid oxidation KW - Maillard reaction KW - Phenylacetaldehyde (PubChem ID: 998) KW - Phenylacetic acid (PubChem ID: 999) KW - Phenylalanine (PubChem ID: 6140) KW - Phenylpyruvic acid (PubChem ID: 997) KW - Reactive carbonyls KW - β-Phenylethylamine (PubChem ID: 1001) SP - 100037 EP - 100037 JF - Food chemistry: X JO - Food Chem X VL - 2 N2 - Lipid oxidation is a main source of reactive carbonyls, and these compounds have been shown both to degrade amino acids by carbonyl-amine reactions and to produce important food flavors. However, reactive carbonyls are not the only products of the lipid oxidation pathway. Lipid oxidation also produces free radicals. Nevertheless, the contribution of these lipid radicals to the production of food flavors by degradation of amino acid derivatives is mostly unknown. In an attempt to investigate new routes of flavor formation, this study describes the degradation of phenylalanine, phenylpyruvic acid, phenylacetaldehyde, and β-phenylethylamine in the presence of the 13-hydroperoxide of linoleic acid, 4-oxononenal (a reactive carbonyl derived from this hydroperoxide), and the mixture of both of them. The obtained results show the formation of phenylacetic acid and benzaldehyde in these reactions as a consequence of the combined action of carbonyl-amine and free radical reactions for amino acid degradation. SN - 2590-1575 UR - https://www.unboundmedicine.com/medline/citation/31432020/Formation_of_phenylacetic_acid_and_benzaldehyde_by_degradation_of_phenylalanine_in_the_presence_of_lipid_hydroperoxides:_New_routes_in_the_amino_acid_degradation_pathways_initiated_by_lipid_oxidation_products L2 - https://linkinghub.elsevier.com/retrieve/pii/S2590-1575(19)30039-2 DB - PRIME DP - Unbound Medicine ER -