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PhIP
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2021 · IF 5.279

Formation and Prediction of PhIP, Harman, and Norharman in Chemical Model Systems Containing Epicatechin under Various Reaction Conditions

Teng Hui,Yanlei Li,Ruixia Chen,Xiaoyue Yang,Huan Liu,Zhenyu Wang,Dequan Zhang

The aim of this study was to investigate the formation rules of 1-methyl-6-phenylimidazo[4,5-b]-pyridine (PhIP), 1-methyl-9H-pyrido[3,4-b]-indole (Harman), and 9H-pyrido[3,4-b]-indole (Norharman) in chemical model systems containing epicatechin under various reaction conditions and establish their prediction models. The results indicated that at 100–200 °C and pH 5.5–7.5 for 10–90 min, epicatechin inhibited the formation of PhIP, Harman, and Norharman by 32–100, 1–93, and 5–98%, respectively. The exponential growth equation in the growth model with R2 of 0.986–0.997, the second-order equation in the polynomial model with R2 of 0.900–0.949, and the trigonometric function equation in the Fourier model with R2 of 0.513–0.926 were well fitted for the formation of PhIP, Harman, and Norharman at various temperatures, times, and pHs, respectively. The calibration set (R2c) and the prediction set (R2p) of the optimal partial least squares regression prediction model was 0.74 and 0.70 for PhIP, 0.75 and 0.70 for Harman, and 0.90 and 0.91 for Norharman, respectively. The results provide theoretical support to develop technologies or equipment for the real-time synchronous monitoring of PhIP, Harman, and Norharman during meat processing.

CAS / MDL: 540-69-2
研究领域: 食品化学 · 分析化学 · 食品科学
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Food Chemistry-X · 2025 · IF 8.2

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)

Mantong Zhao,Zhongyuan Liu,Mengyin Zha,Ying Sun,Haohao Shi,Xueying Zhang,Chuan Li,Guanghua Xia

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.

研究领域: 食品科学 · 毒理学
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MOLECULES · 2025 ·Vol. 30 ·期 6 ·1254 · IF 4.6

Role of Furfural and 5-Methyl-2-furfural in Glucose-Induced Inhibition of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) Formation in Chemical Models and Pork Patties

Yuexia Qin,Zhuyu Zheng,Di Liu,Shuhua Sun,Xiaolei Zhao,Lei Lv,Dengyu Xie,Zhonghui Han,Jinxing He

The effects of furfural and 5-methyl-2-furfural produced by the Maillard reaction on PhIP formation were investigated in chemical models and roasted pork patties. In the chemical models, the results indicated that increasing levels of furfural (r = −0.7338, R2= 0.9557) and 5-methyl-2-furfural (r = −0.7959, R2= 0.9864) significantly reduced PhIP formation, displaying a strong linear correlation. The effects of furfural and 5-methyl-2-furfural on the precursors of phenylalanine (Phe) and phenylacetaldehyde showed a significant reduction in the Phe level, while the level of phenylacetaldehyde was not increased. In addition, neither furfural nor 5-methyl-2-furfural could significantly reduce creatinine or PhIP. Further mechanism studies showed that furfural (5-methyl-2-furfural) directly captured Phe to form the corresponding Schiff base compounds a (2-((furan-2-ylmethylene) amino)-3-phenylpropanoic acid) and b (2-(((5-methylfuran-2-yl)methylene)amino)-3-phenylpropanoic acid). This process reduced the production of phenylacetaldehyde, thereby inhibiting the PhIP formation pathway. More importantly, these two compounds were detected in roasted pork patties to which glucose was added. The above pathway was finally confirmed in roasted pork patties. These results revealed that furfural and 5-methyl-2-furfural, formed during the Maillard reaction, play a significant role in inhibiting the formation of PhIP by reacting with Phe.

CAS / MDL: 105650-23-5
研究领域: 食品科学 · 营养学 · 毒理学
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Food Chemistry-X · 2022 · IF 6.443

Effect of acrolein, a lipid oxidation product, on the formation of the heterocyclic aromatic amine 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems and roasted tilapia fish patties

Meilin Jing,Qingqing Jiang,Yamin Zhu,Daming Fan,Mingfu Wang,Yueliang Zhao

The effect of acrolein on the formation of the 2-amino-1-methyl-6-phenylimidazo[4,5- b ]pyridine (PhIP) was investigated in a chemical model. Acrolein was found to increase PhIP formation at each tested addition level. 0–0.2 mmol of acrolein increased PhIP formation dose-dependently, while high levels of acrolein (>0.2 mmol) did not further increase PhIP formation. Mechanistic study showed that acrolein addition decreased the residue of phenylalanine and creatinine, but increased the content of some key intermediates. Further analysis indicated that acrolein can react with phenylalanine, creatinine, and PhIP to form adducts. These results suggested that acrolein was able to contribute to PhIP formation as a consequence of its comprehensive ability to facilitate Strecker degradation of phenylalanine and react with phenylalanine, creatinine, and PhIP. In addition, oxidation of the tilapia fish increased the PhIP formation in the roasted fish patties, further supporting the potential contribution role of lipid oxidation products to the formation of PhIP.

研究领域: 食品科学 · 化学毒理学 · 营养学
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Journal of Physical Chemistry C · 2021 · IF 4.126

Pairwise Stereoselective Hydrogenation of Propyne on Supported Pd–Ag Catalysts Investigated by Parahydrogen-Induced Polarization

Weiyu Wang,Qiang Wang,Yueying Chu,Guodong Qi,Shenhui Li,Jun Xu,Feng Deng

Alkyne semihydrogenation offers a key approach for the synthesis of stereodefined molecules. The stereoselective hydrogenation of propyne to propene over Al2O3-supported Pd–Ag bimetallic catalysts is studied by using parahydrogen-induced polarization (PHIP) NMR technique. The supported catalysts were prepared by an incipient-wetness impregnation method, and their properties were systemically tuned by altering Pd and Ag components. Structural characterization by X-ray diffraction, infrared spectra, and transmission electron microscope shows the formation of highly dispersed bimetallic Pd–Ag nanoparticles with random alloy structures on Al2O3 support. For the hydrogenation of propyne over Pd–Ag catalysts with higher Ag concentration, the adsorbed protons are mostly restricted on the active Pd ensembles, which favors a higher pairwise hydrogen addition to propyne, leading to a stronger PHIP effect. The product stereoselectivity measurements show that the pairwise syn-addition to propyne increases with Ag content in the Pd–Ag alloy. The reaction conditions impact the pairwise hydrogenation stereoselectivity. A lower H2/propyne ratio of reactant flow or a higher total reactant flow rate enhances the apparent pairwise syn-addition stereoselectivity, which can be accounted for by the suppressed cis–trans isomerization process and/or a higher intrinsic pairwise syn-addition selectivity.

研究领域: 催化化学 · 物理化学 · 材料科学
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FOOD CHEMISTRY · 2026 · IF 10.4

In vitro adsorption of 2-amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) by lactic acid bacteria X3-1B

Yuzhuo Wei,WenJing Guo,Shiqi Hao,Xueying Sun,Lina Sun,Erke Sun,Xiaotong Li,Ye Jin,Lihua Zhao

2-Amino-1-methyl-6-phenylimidazo [4,5-b] pyridine (PhIP) is a highly polar heterocyclic amine with elevated levels in high-temperature meat products and strong carcinogenicity. This study screened Pediococcus acidilactici X3-1B, achieving a PhIP adsorption rate of 74.30%. The stability of the complex formed between the strain and PhIP was highest at 0 h, 4 °C, and pH 7. Scanning electron microscopy (SEM) revealed significant morphological changes in the strain after PhIP adsorption. Fourier transform infrared spectroscopy (FTIR) results indicated that N H and C O groups on the bacterial surface played a primary role in adsorption. Zeta potential measurements revealed an increase in net negative charge on the bacterial surface following PhIP adsorption. Functional group chemical masking indicated that amino groups are one of the core functional groups influencing X3-1B's adsorption of PhIP. This study provides theoretical foundations and practical references for the application of lactic acid bacteria in food safety.

✓ 已验证 DOI PubMed 高影响因子
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Applied Food Research · 2024 · IF 4.5

Effects of green tea and its polyphenols on the formation of heterocyclic aromatic amines, antioxidant capacity, and quality characteristics of roasted pork patties

Zhiyang Deng,Qing Zhang,Piaopiao Long,Mingchun Wen,Zisheng Han,Daniel Granato,Jun Qi,Liang Zhang,Mengting Zhu

Green tea (GT) and its polyphenols (TP) possess excellent antioxidant properties and have the potential to inhibit the formation of heterocyclic aromatic amines (HAAs) in thermally processed meat products. However, their effects on the formation HAAs in roasted pork remain unclear. The study investigated the effect of green tea (GT), TP, and epigallocatechin gallate (EGCG) at additive levels of 0.05%, 0.25%, and 0.5% on the formation of HAAs, antioxidant capacity and quality characteristics during the roasting of pork patties at 250°C. Low levels of GT (0.05%, and 0.25%) and EGCG (0.05%) slightly inhibited the formation of HAAs (MeIQx, 4,8-DiMeIQx, PhIP), with inhibition rates for MeIQx, 4,8-DiMeIQx, and PhIP ranging from 4.70%–8.32% (except for 0.05% GT), 6.15%–16.19%, and 5.69%–24.69%, respectively, while the other groups (0.5% GT, 0.05% TP, 0.25% TP, 0.5% TP, 0.25% EGCG, and 0.5% EGCG) promoted the formation of HAAs. Patties with higher levels of HAAs showed greater consumption of precursors (glucose, free amino acids, and creatine) and protein oxidation. Despite this, all three additives enhanced antioxidant activities (DPPH, ABTS, FRAP) and lipid oxidation stability dose-dependently. Additionally, the additives reduced the luminance ( L* ), redness ( a* ), and yellowness ( b* ) of roasted pork patties. TP and EGCG caused more weight loss in patties and negatively affected their texture, whereas GT had no significant effect on these parameters. Overall, EGCG (0.05%, and 0.25%) had the greatest impact on the formation of HAAs, antioxidant capacity, and quality characteristics of roasted pork patties, followed by TP (0.05%, and 0.25%) and GT (0.05%, and 0.25%). These findings suggest that the addition of low levels of GT (0.05%, and 0.25%) can inhibit HAAs formation, enhance antioxidant capacity, and maintain the quality characteristics of roasted pork patties, whereas the addition of TP and EGCG (0.05%, 0.25%, and 0.5%) is not an effective method for improving quality characteristics and inhibiting HAAs formation in roasted pork patties.

CAS / MDL: 57-00-1
研究领域: 食品科学 · 营养学 · 化学 · 毒理学
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FOOD CHEMISTRY · 2024 · IF 8.5

Novel hydrocolloids synthesized by polyphenols grafted onto chitosan: A promising coating to inhibit of PhIP formation during pan-frying of golden pompano fillets

Mantong Zhao,Zhongyuan Liu,Ying Sun,Haohao Shi,Yonghuan Yun,Meihui Zhao,Guanghua Xia,Xuanri Shen

Hydrocolloids synthesized by gallic acid (GA) and ferulic acid (FA) grafting onto chitosan (CS) were characterized, and their effects on PhIP formation in pan-fried golden pompano were investigated. Spectrograms including nuclear magnetic resonance, Fourier transform infrared spectroscopy and ultraviolet-visible confirmed that GA and FA were successfully grafted onto CS via covalent bonds, with grafting degree of 97.06 ± 2.56 mg GA/g and 93.56 ± 2.76 mg FA/g, respectively. The CS-g-GA and CS-g-FA exerted better solubility and antioxidant activities than CS. For the 8-min pan-fried golden pompano fillets, CS-g-GA and CS-g-FA (0.5%, m/v) significantly reduced the PhIP formation by 61.71% and 81.64%, respectively. Chemical models revealed that CS-g-GA and CS-g-FA inhibited PhIP formation mainly by decreasing the phenylacetaldehyde contents from Maillard reaction and competing with creatinine to react with phenylacetaldehyde. Therefore, it was suggested that CS-g-phenolic acids emerge as novel coating for aquatic products during processing and inhibit heterocyclic amines generation.

研究领域: 食品科学 · 生物化学
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Materials · 2025 ·Vol. 18 ·期 15 ·3573 · IF 3.2

Microstructural, Mechanical, and Thermal Properties of Textured Si3N4/BN Composite Ceramics Prepared Using Two-Step Sintering

Dexiang Gong,Yi Zhou,Yunwei Shi,Qianglong He

Textured Si3N4/BN composite ceramics were successfully fabricated using two-step sintering, combining pseudo-hot isostatic pressing (PHIP) and gas pressure sintering. The grain size of h-BN platelets had a significant influence on densification and mechanical and thermal properties. With an increase in h-BN grain size, the volume density of the composite ceramics gradually decreased, while flexural strength gradually increased. Meanwhile, larger h-BN platelets were more likely to trigger toughening mechanisms like large-angle deflection and greatly increase fracture toughness. Through proper selection of h-BN grain size, textured ceramics, with the addition of h-BN platelets of 1–2 μm, showed high thermal conductivity (∼92 W∙m−1∙K−1) and reliable mechanical properties (∼540 MPa, ∼7.5 MPa∙m1/2, ∼11.1 GPa). Therefore, texture control is an effective means of improving the overall performance of ceramic materials. Novel textured composite ceramics thus have great potential in large-scale fabrication and directional heat dissipation applications.

研究领域: 材料科学 · 陶瓷 · 热管理材料 · 机械工程 · 复合材料
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FOOD HYDROCOLLOIDS · 2022 · IF 11.504

Inhibitory effects of hydrocolloids on the formation of heterocyclic aromatic amines in smoked chicken drumsticks and the underlying mechanism

Lang Zhang,Xiufang Xia,Fangda Sun,Haotian Liu,Qian Chen,Baohua Kong

This study aims to investigate the inhibitory effects of hydrocolloids on heterocyclic aromatic amine (HAA) formation in chemical model systems and smoked chicken drumsticks. In chemical model systems I and II, xanthan gum (XG) and carboxymethyl cellulose sodium (CMC-Na) effectively inhibited the 2-amino-1-methyl-6-phenylimidazo[4,5- b ]pyridine (PhIP), 1-methyl-9H-pyrido[3,4- b ]indole (Harman), and 9H-pyrido[3,4- b ]indole (Norharman) formation in comparison with the control sample ( P  < 0.05). Arabic gum (AG) inhibited the PhIP and Harman formation ( P  < 0.05), but its inhibitory action against Norharman formation was not significant ( P  > 0.05). Further mechanism investigation of chemical model system I showed that the formation of PhIP was mainly inhibited via trapping phenylalanine and creatinine by glyoxal and methyglyoxal. A mechanistic investigation of chemical model system II suggested the inhibition of Harman and Norharman formation by XG and CMC-Na could be through trapping tryptophan by glyoxal and methyglyoxal. In smoked chicken drumsticks, CMC-Na had a dose-dependent inhibitory effect against the PhIP, Harman, and Norharman formation in comparison with the control sample ( P  < 0.05), and 2.0% CMC-Na had the highest inhibitory rates of 45.83%, 21.82%, and 30.92%, respectively. Moreover, CMC-Na effectively inhibited the formation of PhIP, Harman, and Norharman precursors and intermediates in smoked chicken drumsticks, which further confirmed the above inhibition mechanism of CMC-Na. These results could provide an effective approach to reduce HAA formation in smoked meat products by incorporating hydrocolloids.

研究领域: 食品科学 · 化学 · 毒理学
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FOOD CHEMISTRY · 2026 · IF 10.4

Bidirectional regulation of heterocyclic amines by flavonoids: insights from flavonoid amination using dihydromyricetin and baicalein

Jingjing Zhang,Hui Cao,Bing Li,Fuying Wang,Qin Duan,Yaru Li,Jinjin Pei,Hui Wang,Juan Carlos Mejuto,Jesús Simal-Gándara,Haolin Zhang

Heterocyclic amines (HCAs) are carcinogenic contaminants formed during meat thermal processing, and the traditionally recognized inhibitory effects of flavonoids on HCA formation remain controversial. Dihydromyricetin (DMY) and baicalein (BAI) both exhibited dose-dependent bidirectional effects on PhIP formation in a PhIP chemical model. At low concentrations (DMY 125–250 μM, BAI 125–1000 μM), PhIP levels gradually increased to nearly 210% and 300% of control, respectively, mainly driven by amination-related reactions of flavonoid thermal degradation products that promoted phenylacetaldehyde accumulation. At high concentrations (≥2000 μM), PhIP was suppressed to <50% (DMY) and <20% (BAI) of control via potent radical scavenging and phenylacetaldehyde trapping. The bidirectional regulation may be governed by a dynamic balance between amination-driven promotion and the dual inhibitory pathways for PhIP formation. This study explains how flavonoids lead to contradictory effects on HCA formation in cooked meat and provides a mechanistic foundation for their application.

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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2026 · IF 4.8

Analyte-induced enhancement of oxidase-like activity of cerium-based metal-organic frameworks for “turn-on” detection of 2-amino-3-methylimidazo[4,5-f]quinoline

Xueer Lin,Jiahui Zou,Guancheng Zhu,Linfeng Pang,Yuqi Chen,Yanyan Huang

Heterocyclic aromatic amines (HAAs), formed during the thermal processing of meat, are a group of carcinogenic and mutagenic compounds that pose significant risks to food safety and human health. Among them, 2-amino-3-methylimidazo[4,5- f ]quinoline (IQ) is considered one of the most hazardous substances, making its monitoring critically important. However, conventional detection techniques are often limited by sophisticated and costly instruments, complex operation process, and highly trained personnel. In this study, we proposed a “turn-on” colorimetric sensing strategy for the detection of IQ based on the analyte-triggered enhancement of oxidase-like activity of Ce-UiO-66 nanozyme. Ce-UiO-66 was synthesized using a simple solvothermal method via the self-assembly of terephthalic acid and Ce 4+ ions. The resulting Ce-UiO-66 exhibited excellent oxidase-like activity, catalyzing the oxidation of 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) via the generation of superoxide anions from oxygen. In the presence of IQ, electrostatic interactions facilitated the rapid adsorption of IQ onto the negatively charged Ce-UiO-66 surface, reversing the surface charge to positive. This charge shift enhanced the affinity of Ce-UiO-66 for negatively charged ABTS, significantly accelerating its oxidation. Based on this principle, we established a “turn-on” colorimetric sensing strategy for the detection of IQ, achieving a detection limit of 5.41 μM. This Ce-UiO-66 nanozyme-based detection method demonstrated high selectivity and anti-interference performance and could efficiently distinguish its analog 2-amino-1-methyl-6-phenylimidazo[4,5- b ]pyridine (PhIP) in complex food matrices. Further experimental data illustrated that this strategy was successfully applied to the detection of IQ in roasted meat samples. This work might offer a simple, cost-effective, and robust approach for rapid screening of IQ in highly contaminated processed meats.

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