Toxicologically Relevant Aldehydes Produced during the Frying Process Are Trapped by Food Phenolics

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• 作者：Rosario Zamora ; Isabel Aguilar ; Michael Granvogl ; Francisco J. Hidalgo
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2016
• 出版时间：July 13, 2016
• 年：2016
• 卷：64
• 期：27
• 页码：5583-5589
• 全文大小：345K
• 年卷期：0
• ISSN：1520-5118

文摘

The lipid-derived carbonyl trapping ability of phenolic compounds under common food processing conditions was studied by determining the presence of carbonyl-phenol adducts in both onions fried in the laboratory and commercially crispy fried onions. Four carbonyl-phenol adducts produced between quercetin and acrolein, crotonaldehyde, or (E)-2-pentenal were prepared and characterized by ¹H and ¹³C nuclear magnetic resonance (NMR) spectroscopy and high performance liquid chromatography coupled to high resolution mass spectrometry (HPLC-HRMS). The synthesized compounds were 2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-9,10-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one (4), 2-(3,4-dihydroxyphenyl)-3,5,8-trihydroxy-10-methyl-9,10-dihydro-4H,8H-pyrano[2,3-f]chromen-4-one (5), 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-8-methyl-4H,8H-pyrano[2,3-f]chromen-4-one (9), and 2-(3,4-dihydroxyphenyl)-8-ethyl-3,5-dihydroxy-4H,8H-pyrano[2,3-f]chromen-4-one (10). When onions were fried in fresh rapeseed oil spiked with acrolein, crotonaldehyde, and (E)-2-pentenal (2.7 μmol/g of oil), adduct 10 was the major compound produced, and trace amounts of adducts 4 and 5, but not of adduct 9, were also detected. In contrast, compound 4 was the major adduct present in commercially crispy fried onions. Compound 10 was also present to a lower extent, and trace amounts of compound 5, but not of compound 9, were also detected. These data suggested that lipid-derived carbonyl-phenol adducts are formed in food products under standard cooking conditions. They also pointed to a possible protective role of food polyphenols, which might contribute to the removal of toxicologically relevant aldehydes produced during deep-frying, assuming that the formed products are stable during food consumption in the human organism.