Research Article
Chlorogenic acid increased acrylamide formation through promotion of HMF formation and 3-aminopropionamide deamination

https://doi.org/10.1016/j.jhazmat.2013.12.067Get rights and content

Highlights

  • Chlorogenic acid increased the formation of acrylamide while its quinone one inhibited.

  • Chlorogenic acid increased acrylamide formation by enhancing HMF production.

  • It decreased the activation energy for conversion of 3-APA to acrylamide.

  • It kept high redox potential that may inhibited acrylamide elimination.

Abstract

This research was aimed to investigate why chlorogenic acid, presents at high concentrations in some food raw material, influences acrylamide formation. In the asparagine/glucose Maillard reaction system (pH = 6.8), addition of chlorogenic acid significantly increased acrylamide formation and inhibited its elimination. In contrast, the quinone derivative of chlorogenic acid decreased acrylamide formation. Three mechanisms may be involved for increasing acrylamide formation by chlorogenic acid. Firstly, it increased the formation of HMF, which acts as a more efficient precursor than glucose to form acrylamide. Secondly, it decreased activation energy for conversion of 3-aminopropionamide (3-APA) to acrylamide (from 173.2 to 136.6 kJ/mol), and enhances deamination from 3-APA. And thirdly, it prevented attack of the produced acrylamide from free radicals by keeping high redox potential during the Maillard reaction.

Introduction

Acrylamide is a food contaminant formed mainly through Maillard reaction during high-temperature processing. It has neurotoxic and genotoxic properties, and is known to act as a carcinogen in rodents [1]. The contents of acrylamide vary among different types of food. Fried potato chips, coffee and toasted chicory contain much higher levels of acrylamide than other high temperature-processed foods [1], [2], with the highest reported concentrations of 12,000, 539, and 4015 μg/kg, respectively [3], [4], [5].

Food ingredients play an important role in acrylamide formation. A considerable number of antioxidants, including vitamin C, vitamin E, ferulic acid, tert-butylhydroquinone, butylated hydroxyanisole, butylated hydroxytoluene, epigallocatechin gallate, sodium erythorbate, antioxidants from bamboo leaves, tea polyphenols, and spice extracts have all been reported to influence acrylamide formation [6], [7], [8], [9], [10], [11]. However, reports on relationships between antioxidants and acrylamide contents in food have been controversial [11].

Coffee beans and potato tubers contain high concentrations of chlorogenic acid (41,640 and 1481 mg/kg, respectively) [12], [13], which can be oxidized to quinone by polyphenol oxidase during processing steps such as peeling and cutting [14]. It was reported that addition of chlorogenic acid at low level (30 μmol/100 g) or at very high level (1 mmol/ml) decreased acrylamide formation both in biscuits and and asparagine/glucose reaction model [15], [16]. However, the mechanisms underlying this effect remain to be investigated. In the present study, we investigated the effects of chlorogenic acid at moderate concentration (50 μmol/ml) and its quinone derivative (prepared using polyphenol oxidase instead of hydrogen peroxide as we previously reported) [17], on the formation of acrylamide during high-temperature processing, focusing on the mechanism by which it promotes deamination of 3-APA and HMF formation.

Section snippets

Chemicals

Chlorogenic acid, HMF, asparagine, and glucose were purchased from Aladdin Reagents Database Inc. (Shanghai, China). Acrylamide standard (>99.8%) and 13C3-labeled acrylamide (99%) were obtained from Sigma-Aldrich Company (St. Louis, MO, USA) and Merck-Schuchardt (Hohenbrunn, Germany), respectively. 3-Aminopropionamide hydrochloride (β-alaninamide hydrochloride, 3-APA) was purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). High-performance liquid chromatography (HPLC)-grade

Effect of chlorogenic acid on acrylamide formation

Addition of 0.5 and 5 μmol/ml chlorogenic acid significantly increased acrylamide formation compared with the control (Table 1). However, when chlorogenic acid was converted to its quinone derivative, production of acrylamide was lower compared with control (Table 1). Moreover, chlorogenic acid significantly accelerated rates of acrylamide formation (P = 0.05) at the beginning of Maillard reaction (Fig. 1). These results verified our previous hypothesis that certain types of phenol antioxidants

Conclusion

Addition of chlorogenic acid to the asparagine/glucose Maillard reaction system significantly increased acrylamide formation and inhibited its elimination. In contrast, the quinone derivative of chlorogenic acid decreased acrylamide formation. Chlorogenic acid promoted acrylamide formation mainly through increasing HMF formation and decreasing the activation energy for conversion of 3-APA to acrylamide.

Acknowledgments

The authors gratefully acknowledge financial support from the National Natural Science Fund (31071596 and 31371745) and the Ministry of Science and Technology of China (No. 2012BAK01B03).

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