Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)

The effect of aldehydes from lipid oxidation on the generation of heterocyclic amine 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) during pan-frying of golden pompano fillets was investigated. It was observed the aldehydes that contribute to thiobarbituric acid reactive substances (TBARS)...

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Main Authors: Mantong Zhao, Zhongyuan Liu, Mengyin Zha, Ying Sun, Haohao Shi, Xueying Zhang, Chuan Li, Guanghua Xia
Format: Article
Language:English
Published: Elsevier 2025-01-01
Series:Food Chemistry: X
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Online Access:http://www.sciencedirect.com/science/article/pii/S2590157525000914
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author Mantong Zhao
Zhongyuan Liu
Mengyin Zha
Ying Sun
Haohao Shi
Xueying Zhang
Chuan Li
Guanghua Xia
author_facet Mantong Zhao
Zhongyuan Liu
Mengyin Zha
Ying Sun
Haohao Shi
Xueying Zhang
Chuan Li
Guanghua Xia
author_sort Mantong Zhao
collection DOAJ
description The effect of aldehydes from lipid oxidation on the generation of heterocyclic amine 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) during pan-frying of golden pompano fillets was investigated. It was observed the aldehydes that contribute to thiobarbituric acid reactive substances (TBARS) value significantly promoted PhIP generation (p < 0.05). The defat treatment of fresh fish tissue significantly reduced the PhIP formation in pan-fried products (p < 0.05). During pan-frying, massive aldehydes were generated in a time-dependent manner with acrolein, propanal, hexanal, 4-hydroxy-nonenal (HNE), and 2,4-decadienal (DDE) as the abundant species. In the established chemical model, these aldehydes congruously promoted PhIP formation with the increased concentration, especially acrolein, HNE and DDE. Therefore, aldehydes could significantly enhance the PhIP generation under processing. However, except for propanal and hexanal, the promoting effect was slightly decreased with high levels of aldehydes addition due to the strong electrophilic properties and participation of reaction with the amino group of phenylacetaldehyde, creatinine, even PhIP.
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issn 2590-1575
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publishDate 2025-01-01
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series Food Chemistry: X
spelling doaj-art-8a8bbd4d116d438da8c1e559079c95662025-02-12T05:32:42ZengElsevierFood Chemistry: X2590-15752025-01-0125102244Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)Mantong Zhao0Zhongyuan Liu1Mengyin Zha2Ying Sun3Haohao Shi4Xueying Zhang5Chuan Li6Guanghua Xia7Hainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, College of Food Science and Technology, Hainan University, Haikou, 570228, ChinaHainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, College of Food Science and Technology, Hainan University, Haikou, 570228, China; Collaborative Innovation Centre of Seafood Deep Processing, Dalian Polytechnic University, Dalian 116034, ChinaHainan Sky-Blue Ocean Foods Co., Ltd. Guilinyang Economical Development District, Haikou 571127, ChinaHainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, College of Food Science and Technology, Hainan University, Haikou, 570228, ChinaHainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, College of Food Science and Technology, Hainan University, Haikou, 570228, ChinaHainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, College of Food Science and Technology, Hainan University, Haikou, 570228, ChinaHainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, College of Food Science and Technology, Hainan University, Haikou, 570228, China; Collaborative Innovation Centre of Seafood Deep Processing, Dalian Polytechnic University, Dalian 116034, ChinaHainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, College of Food Science and Technology, Hainan University, Haikou, 570228, China; Collaborative Innovation Centre of Seafood Deep Processing, Dalian Polytechnic University, Dalian 116034, China; Corresponding author at: Hainan Engineering Research Center of Aquatic Resources Efficient Utilization in South China Sea, Key Laboratory of Seafood Processing of Haikou, College of Food Science and Technology, Hainan University, Haikou, 570228, China.The effect of aldehydes from lipid oxidation on the generation of heterocyclic amine 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) during pan-frying of golden pompano fillets was investigated. It was observed the aldehydes that contribute to thiobarbituric acid reactive substances (TBARS) value significantly promoted PhIP generation (p < 0.05). The defat treatment of fresh fish tissue significantly reduced the PhIP formation in pan-fried products (p < 0.05). During pan-frying, massive aldehydes were generated in a time-dependent manner with acrolein, propanal, hexanal, 4-hydroxy-nonenal (HNE), and 2,4-decadienal (DDE) as the abundant species. In the established chemical model, these aldehydes congruously promoted PhIP formation with the increased concentration, especially acrolein, HNE and DDE. Therefore, aldehydes could significantly enhance the PhIP generation under processing. However, except for propanal and hexanal, the promoting effect was slightly decreased with high levels of aldehydes addition due to the strong electrophilic properties and participation of reaction with the amino group of phenylacetaldehyde, creatinine, even PhIP.http://www.sciencedirect.com/science/article/pii/S2590157525000914Golden pompano filletsLipid oxidationAldehydesHeterocyclic aromatic amines
spellingShingle Mantong Zhao
Zhongyuan Liu
Mengyin Zha
Ying Sun
Haohao Shi
Xueying Zhang
Chuan Li
Guanghua Xia
Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)
Food Chemistry: X
Golden pompano fillets
Lipid oxidation
Aldehydes
Heterocyclic aromatic amines
title Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)
title_full Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)
title_fullStr Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)
title_full_unstemmed Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)
title_short Investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines: A case study of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP)
title_sort investigation of the dose and structure effects of lipid oxidation products aldehydes on the generation of heterocyclic amines a case study of 2 amino 1 methyl 6 phenylimidazo 4 5 b pyridine phip
topic Golden pompano fillets
Lipid oxidation
Aldehydes
Heterocyclic aromatic amines
url http://www.sciencedirect.com/science/article/pii/S2590157525000914
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