Role of Phenylalanine in the Formation of Parent and Oxygenated Polycyclic Aromatic Hydrocarbons in Baking Systems.

IF 5.7 1区农林科学 Q1 AGRICULTURE, MULTIDISCIPLINARY

Journal of Agricultural and Food Chemistry Pub Date : 2025-07-18 DOI:10.1021/acs.jafc.5c04295

Xin Ma,Shimin Wu

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引用次数: 0

Abstract

Parent and oxygenated polycyclic aromatic hydrocarbons (PAHs and OPAHs) have gained increasing attention due to their toxicity. However, their formation mechanisms during baking remain unclear. This study aimed to elucidate their formation pathways from amino acids in baking systems. The effects of five amino acids on PAH24 and OPAH12 levels in bread were investigated. Phenylalanine addition (2%) caused the most significant 15-fold increase in the toxic equivalent quotient of PAH36. Stable isotope tracing technology revealed that both the phenyl ring and C3 atom of phenylalanine were incorporated into benzo[a]anthracene and 9-fluorenone, proving the transformation of phenylalanine into PAHs and OPAHs. By nontarget analysis and chemical reactivity analysis, styrene, (E)-stilbene, and benzophenone were identified as key intermediates in the formation of naphthalene, benzo[a]anthracene, and 9-fluorenone, respectively. Overall, this study first proposed the formation pathways of PAHs and OPAHs from phenylalanine, offering guidance for reducing their health risks during baking.

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苯丙氨酸在烘焙体系中母体和氧合多环芳烃形成中的作用。

母体和氧合多环芳烃（PAHs和OPAHs）因其毒性而受到越来越多的关注。然而，它们在烘烤过程中的形成机制尚不清楚。本研究旨在阐明它们在烘焙体系中由氨基酸形成的途径。研究了5种氨基酸对面包中PAH24和OPAH12含量的影响。苯丙氨酸（2%）的加入使PAH36毒性当量增加了15倍。稳定同位素示踪技术显示，苯丙氨酸的苯环和C3原子都被并入苯并[a]蒽和9-芴酮中，证明苯丙氨酸转化为多环芳烃和多环芳烃。通过非目标分析和化学反应性分析，确定了苯乙烯、(E)-二苯乙烯和二苯甲酮分别是形成萘、苯并[a]蒽和9-芴酮的关键中间体。总体而言，本研究首次提出了苯丙氨酸对多环芳烃和多环芳烃的形成途径，为降低烘焙过程中的健康风险提供了指导。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Agricultural and Food Chemistry 农林科学-农业综合

CiteScore

9.90

自引率

8.20%

发文量

1375

审稿时长

2.3 months

期刊介绍： The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.