Inhibitory effects of hyperoside and quercitrin from Zanthoxylum bungeanum Maxim. leaf on 2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine formation by trapping phenylacetaldehyde

Abstract2-amino-1-methyl-6-phenylimidazole[4,5-b]pyridine (PhIP) is one of the most abundant Heterocyclic amines (HAs) in meat products. Zanthoxylum bungeanum Maxim. leaf (ZML) extract has been shown to be rich in polyphenols, which are gaining increasing interest as efficient tools for inhibiting the formation of HAs. In the present work, the effects of ZML extract, major polyphenols, chlorogenic acid, hyperoside and quercitrin on the formation of PhIP in both roast beef patties and chemical model systems were investigated. UPLC-MS showed that ZML extract and those three polyphenols effectively inhibited PhIP formation. Additionally, GC-MS analysis showed that those three polyphenols significantly reduced the content of phenylacetaldehyde in the model systems, a key intermediate involved in PhIP formation. The subsequent UPLC-MS and TOF-MS/MS analysis found that hyperoside and quercitrin reacted with phenyacetaldehyde to form those four adducts, 8-C-(E-Phenylethenyl)hyperoside, 6-C-(E-Phenylethenyl)hyperoside, 8-C-(E-Phenylethenyl)quercitrin and 6-C-(E-Phenylethenyl)quercitrin, respectively. The results revealed that hyperoside and quercitrin could trap phenylacetaldehyde to form adducts, thereby, retarding the reaction of phenylacetaldehyde and creatinine, blocking the generation of PhIP.

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Inhibitory effects of Portulaca oleracea L. and selected flavonoid ingredients on heterocyclic amines in roast beef patties and Density Function Theory calculation of binding between heterocyclic amines intermediates and flavonoids

Food Chemistry ◽

10.1016/j.foodchem.2020.127551 ◽

2021 ◽

Vol 336 ◽

pp. 127551

Author(s):

Jing Jing ◽

Yonghui He ◽

Yali Wang ◽

Maomao Zeng

Keyword(s):

Density Function ◽

Function Theory ◽

Density Function Theory ◽

Portulaca Oleracea ◽

Heterocyclic Amines ◽

Inhibitory Effects ◽

Beef Patties ◽

Roast Beef ◽

Theory Calculation

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Inhibitory effects of selected dietary flavonoids on the formation of total heterocyclic amines and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in roast beef patties and in chemical models

Food & Function ◽

10.1039/c5fo01055a ◽

2016 ◽

Vol 7 (2) ◽

pp. 1057-1066 ◽

Cited By ~ 21

Author(s):

Qin Zhu ◽

Shuang Zhang ◽

Mingfu Wang ◽

Jie Chen ◽

Zong-Ping Zheng

Keyword(s):

Heterocyclic Amines ◽

Inhibitory Effects ◽

Chemical Models ◽

Beef Patties ◽

Roast Beef ◽

Dietary Flavonoids

Dietary flavonoids effectively inhibit total HAs and PhIP formation in roast beef patties through scavenging of intermediates in formation pathways.

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Inhibitory profiles of spices against free and protein-bound heterocyclic amines of roast beef patties as revealed by ultra-performance liquid chromatography–tandem mass spectrometry and principal component analysis

Food & Function ◽

10.1039/c7fo00935f ◽

2017 ◽

Vol 8 (11) ◽

pp. 3938-3950 ◽

Cited By ~ 5

Author(s):

Jing Chen ◽

Zhiyong He ◽

Fang Qin ◽

Jie Chen ◽

Dongsheng Cao ◽

...

Keyword(s):

Mass Spectrometry ◽

Principal Component ◽

Ultra Performance Liquid Chromatography ◽

Heterocyclic Amines ◽

Tandem Mass ◽

Inhibitory Effects ◽

Beef Patties ◽

Chromatography Tandem Mass Spectrometry ◽

Liquid Chromatography Tandem Mass ◽

Roast Beef

The inhibitory effects of spices on free and protein-bound heterocyclic amines as analysed by UPLC-MS/MS and PCA.

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Inhibitory effects of catechins on β-carbolines in tea leaves and chemical model systems

Food & Function ◽

10.1039/c7fo02053h ◽

2018 ◽

Vol 9 (6) ◽

pp. 3126-3133 ◽

Cited By ~ 2

Author(s):

Ye Jiao ◽

Yan Yan ◽

Zhiyong He ◽

Daming Gao ◽

Fang Qin ◽

...

Keyword(s):

Mass Spectrometry ◽

Liquid Chromatography ◽

Black Tea ◽

Heterocyclic Amines ◽

Model Systems ◽

Tandem Mass ◽

Inhibitory Effects ◽

Tea Leaves ◽

Ultrahigh Performance Liquid Chromatography ◽

Green And Black Tea

The profile of 18 heterocyclic amines from seven categories (including β-carbolines) in tea leaves during green and black tea processing procedures, as well as commercial tea products was screened by ultrahigh-performance liquid chromatography with tandem mass spectrometry.

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Oilseed Protein Ingredients as Antioxidant for Meat in Foodservice1

Journal of Food Protection ◽

10.4315/0362-028x-44.4.254 ◽

1981 ◽

Vol 44 (4) ◽

pp. 254-256 ◽

Cited By ~ 16

Author(s):

KI SOON RHEE ◽

YOLANDA A. ZIPRIN

Keyword(s):

Soy Protein ◽

Meat Products ◽

Thiobarbituric Acid ◽

Hot Water ◽

Oxidative Rancidity ◽

Oilseed Protein ◽

Thiobarbituric Acid Test ◽

Beef Patties ◽

Roast Beef ◽

Acid Test

This study indicates that glandless cottonseed, peanut or soy protein ingredients may be incorporated in gravy or sauce for precooked meat products to retard development of oxidative rancidity. The oilseed protein ingredients were incorporated in the gravy in which cooked ground beef patties (100% beef) were stored; also, hot-water extracts of the protein ingredients were used as a cover liquid for refrigerated roast beef slices. Oxidative rancidity in the beef patties or in the roast beef slices after 3 and 6 days of storage at 4 C was determined by the thiobarbituric acid test.

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Inhibitory effects of Sichuan pepper (Zanthoxylum bungeanum) and sanshoamide extract on heterocyclic amine formation in grilled ground beef patties

Food Chemistry ◽

10.1016/j.foodchem.2017.06.097 ◽

2018 ◽

Vol 239 ◽

pp. 111-118 ◽

Cited By ~ 29

Author(s):

Maomao Zeng ◽

Junhui Wang ◽

Mengru Zhang ◽

Jing Chen ◽

Zhiyong He ◽

...

Keyword(s):

Ground Beef ◽

Heterocyclic Amine ◽

Inhibitory Effects ◽

Beef Patties ◽

Zanthoxylum Bungeanum

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Inhibitory effects of apple peel polyphenol extract on the formation of heterocyclic amines in pan fried beef patties

Meat Science ◽

10.1016/j.meatsci.2016.02.040 ◽

2016 ◽

Vol 117 ◽

pp. 57-62 ◽

Cited By ~ 24

Author(s):

Kebba Sabally ◽

Lekha Sleno ◽

Julie-Anne Jauffrit ◽

Michèle M. Iskandar ◽

Stan Kubow

Keyword(s):

Heterocyclic Amines ◽

Inhibitory Effects ◽

Beef Patties ◽

Apple Peel

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Modelling the Effects of Roselle Extract, Potato Peel Flour, and Beef Fat on the Sensory Properties and Heterocyclic Amines Formation of Beef Patties Studied by Using Response Surface Methodology

Foods ◽

10.3390/foods10061184 ◽

2021 ◽

Vol 10 (6) ◽

pp. 1184

Author(s):

Anna Judith Pérez-Báez ◽

Martin Valenzuela-Melendres ◽

Juan Pedro Camou ◽

Gustavo González-Aguilar ◽

Orlando Tortoledo-Ortiz ◽

...

Keyword(s):

Response Surface Methodology ◽

Response Surface ◽

Meat Products ◽

Sensory Properties ◽

Heterocyclic Amines ◽

Potato Peel ◽

Linear Effect ◽

Beef Patties ◽

Carcinogenic Potential ◽

Maximum Inhibition

Heterocyclic amines (HCAs) are compounds with carcinogenic potential formed during high-temperature processing of meat and meat products. Vegetables or their extracts with high antioxidant capacity can be incorporated into the meat matrix to reduce their formation, but it is necessary to find the optimal levels to achieve maximum inhibition without affecting the sensory properties. The objective of this study was to evaluate the effects of roselle extract (RE, 0–1%), potato peel flour (PP, 0–2%), and beef fat (BF, 0–15%) on the sensory properties and formation of HCAs in beef patties using response surface methodology. IQx, IQ, MeIQx, MeIQ, 4,8-DiMeIQx, and PhIP were identified and quantified by HPLC. Regression models were developed to predict sensory properties and HCAs’ formation. All models were significant (p < 0.05) and showed a R2 > 0.70. Roselle extract and beef fat had a negative linear effect on the formation of the total HCAs, while PP had a positive linear effect. The optimal formula that minimizes the formation of HCAs included 0.63% RE, 0.99% PP, and 11.96% BF. RE and PP are foods that can be used as ingredients in low-fat beef patties to minimize the formation of HCAs without affecting their sensory properties.

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