Food and Fermentation Industries >

2026 , Vol. 52 >Issue 10: 249 - 257

DOI: https://doi.org/10.13995/j.cnki.11-1802/ts.045694

Study on mechanism of antioxidant activity change of flavonoids in simulated frying system

  • DONG Zhijie ,
  • LIU Junxin ,
  • LI Jun ,
  • DANG Liankui ,
  • FAN Zhenyu
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  • 1(Jiangsu College of Tourism, Yangzhou 225000, China)
    2(College of Smart Services, Shanghai Technology and Innovation Vocational College, Shanghai 201600, China)
    3(Qingdao Vocational and Technical College of Hotel Management, Qingdao 266000, China)
    4(Henan Anrui Biotechnology Co.Ltd., Zhengzhou 450000, China)

Received date: 2025-12-30

  Revised date: 2026-01-15

  Online published: 2026-06-15

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Abstract

In this study, a simulated frying system at 180 ℃ was established to investigate the mechanisms underlying the changes in the antioxidant activity of five flavonoids in high-temperature oil.The results showed that all five flavonoids exhibited thermal instability;both their content and the overall antioxidant activity of the system decreased with prolonged heating time, yet no cytotoxic substances were generated.Fourier transform infrared spectroscopy (FTIR) analysis revealed that the addition of quercetin and EGCG to linoleic acid effectively inhibited the cleavage of linoleic acid double bonds at 180 ℃.Furthermore, these flavonoids may suppress the generation of aldehydes and ketones by forming stable products containing C—O—C bonds through reactions with fatty acids or carbonyl compounds.Analysis of quercetin degradation products using UPLC-Q-TOF-MS/MS indicated that quercetin underwent a Michael addition reaction with an oxidation intermediate of linoleic acid (a C4 short-chain aldehyde/ketone with a molecular weight of 88) to form a carbonyl-phenol adduct with a molecular weight of approximately 390 (m/z 389 [M-H]-).In conclusion, flavonoids can serve as safe antioxidants for oils.The high-temperature-induced chemical loss and the formation of carbonyl-phenol adducts with low antioxidant activity are the primary mechanisms responsible for the attenuation of their antioxidant activity in frying systems.

Key words： flavonoids; antioxidant; Fourier transform infrared spectroscopy (FTIR); linoleic acid; quercetin

Cite this article

DONG Zhijie , LIU Junxin , LI Jun , DANG Liankui , FAN Zhenyu . Study on mechanism of antioxidant activity change of flavonoids in simulated frying system[J]. Food and Fermentation Industries, 2026 , 52(10) : 249 -257 . DOI: 10.13995/j.cnki.11-1802/ts.045694

References

[1] GAO Y, XIA W, SHAO P, et al.Impact of thermal processing on dietary flavonoids[J].Current Opinion in Food Science, 2022, 48:100915.
[2] LANG Y X, GAO N X, ZANG Z H, et al.Classification and antioxidant assays of polyphenols:A review[J].Journal of Future Foods, 2024, 4(3):193-204.
[3] 付贵, 樊震宇, 孙亚婷, 等.烹饪油烟中醛类形成的影响因素以及防控技术研究进展[J].食品科学, 2024, 45(10):298-309.
FU G, FAN Z Y, SUN Y T, et al.Research progress on influential factors of and control technologies for aldehyde formation in cooking oil fume[J].Food Science, 2024, 45(10):298-309.
[4] FAN Z Y, WANG L, JIANG Q Q, et al.Effects of quercetin on emissions of aldehydes from heated docosahexaenoic acid (DHA)-fortified soybean oil[J].Journal of Hazardous Materials, 2023, 442:130134.
[5] XU X Q, LIU A M, HU S Y, et al.Synthetic phenolic antioxidants:Metabolism, hazards and mechanism of action[J].Food Chemistry, 2021, 353:129488.
[6] JIANG X Y, LV H F, LU Y, et al.Trapping of acrolein by curcumin and the synergistic inhibition effect of curcumin combined with quercetin[J].Journal of Agricultural and Food Chemistry, 2021, 69(1):294-301.
[7] FU G, LI Y F, FAN F Y, et al.Genistein-7-O-octanoate, a lipophilized genistein, exhibits antioxidant activity through activating the Nrf2 signaling pathway in Caco-2 cells[J].Journal of Functional Foods, 2024, 119:106338.
[8] LIU Y, WANG J H, PI Y M, et al.The chemical components and adhesion performance of the oil fume fouling sourced from cooking:Experimental investigation and molecular simulation[J].Journal of Industrial and Engineering Chemistry, 2025, 146:456-467.
[9] ANCUCEANU R, ANGHEL A I, HOVANET M V, et al.Antioxidant activity of essential oils from Pinaceae species[J].Antioxidants, 2024, 13(3):286.
[10] ZHANG D C, LIU J J, JIA L Z, et al.Speciation of VOCs in the cooking fumes from five edible oils and their corresponding health risk assessments[J].Atmospheric Environment, 2019, 211:6-17.
[11] ZHUANG Y, DONG J, HE X M, et al.Impact of heating temperature and fatty acid type on the formation of lipid oxidation products during thermal processing[J].Frontiers in Nutrition, 2022, 9:913297.
[12] ADENIRAN J A, YUSUF R O, ABDULKADIR M O, et al.Evaporation rates and pollutants emission from heated cooking oils and influencing factors[J].Environmental Pollution, 2020, 266:115169.
[13] ZHANG Q, SALEH A S M, SHEN Q.Monitoring of changes in composition of soybean oil during deep-fat frying with different food types[J].Journal of the American Oil Chemists’ Society, 2016, 93(1):69-81.
[14] XIAO J B.Recent advances on the stability of dietary polyphenols[J].eFood, 2022, 3(3):e21.
[15] ZHU Q, LIANG C P, CHENG K W, et al.Trapping effects of green and black tea extracts on peroxidation-derived carbonyl substances of seal blubber oil[J].Journal of Agricultural and Food Chemistry, 2009, 57(3):1065-1069.
[16] LIN S Y, ZHANG H L, SIMAL-GANDARA J, et al.Investigation of new products of quercetin formed in boiling water via UPLC-Q-TOF-MS-MS analysis[J].Food Chemistry, 2022, 386:132747.
[17] TROISE A D, FIORE A, COLANTUONO A, et al.Effect of olive mill wastewater phenol compounds on reactive carbonyl species and Maillard reaction end-products in ultrahigh-temperature-treated milk[J].Journal of Agricultural and Food Chemistry, 2014, 62(41):10092-10100.
[18] ZHANG X, NI L, ZHU Y M, et al.Quercetin inhibited the formation of lipid oxidation products in thermally treated soybean oil by trapping intermediates[J].Journal of Agricultural and Food Chemistry, 2021, 69(11):3479-3488.
[19] WANG R, TAO M R, ZHU Y M, et al.Puerarin inhibited 3-chloropropane-1, 2-diol fatty acid esters formation by reacting with glycidol and glycidyl esters[J].Food Chemistry, 2021, 358:129843.
[20] DAI F W, ZHUANG Q Y, HUANG G, et al.Infrared spectrum characteristics and quantification of OH groups in coal[J].ACS Omega, 2023, 8(19):17064-17076.
[21] OZULKU G, YILDIRIM R M, TOKER O S, et al.Rapid detection of adulteration of cold pressed sesame oil adultered with hazelnut, canola, and sunflower oils using ATR-FTIR spectroscopy combined with chemometric[J].Food Control, 2017, 82:212-216.
[22] ZHANG Y F, FAN Z Y, FAN D M, et al.The structure-activity relationship of flavonoids in inhibiting aldehyde emissions from heated soybean oil[J].ACS Food Science & Technology, 2025, 5(6):2362-2370.
[23] 姚磊,付贵,韩昕苑,等.茶多酚对加热大豆油油烟中醛类物质释放的影响[J].食品与发酵工业, 2025.https://doi.org/10.13995/j.cnki.11-1802/ts.045694.
YAO L, FU G, HAN X Y, et al.Effect of tea polyphenols on emission of aldehydes in soybean oil fumes during heating[J].Food and Fermentation Industries, 2025.https://doi.org/10.13995/j.cnki.11-1802/ts.045694.
[24] GEMINGNUER A, WANG H L, LIU Y, et al.Genistein nanopreparations:Recent advances in preparation, bioactivities, and applications[J].Journal of Cluster Science, 2025, 36(6):236.
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