مجله علوم و صنایع غذایی ایران

مجله علوم و صنایع غذایی ایران

A Comparative Investigation of Synthesized Coumarin-Chalcone with Vitamin C for the Inhibition of Enzymatic Browning in Potato

نوع مقاله : مقاله پژوهشی

نویسندگان
Omar T Ali 1
Abdallah F Al-burgus 2
Omar Y Al-abbasy 3
Mohammed Fadhil H Haddad 4
1 Department of Chemistry, College of Education for Pure Science, University of Mosul, Mosul-Iraq
2 General Directorate of Education in Nineveh, Iraq
3 Chemistry Dept., College of education for pure science, University of Mosul, Mosul-Iraq
4 Department of Medical Lab Techniques, Northern Technical University, Mosul, Iraq
10.48311/fsct.2026.119085.83047
چکیده
The enzymatic browning reaction is one of the primary factors contributing to the deterioration of food products, such as fruits and vegetables, after harvest. This phenomenon is primarily caused by the enzyme polyphenol oxidase (PPO), which alters the organoleptic properties and nutritional value, ultimately leading to economic losses worldwide. The inhibition of PPO prevents this reaction and preserves food products. Coumarin chalcone bearing a hydroxyl group has shown promising antioxidant and enzyme-inhibitory activities. Here, a novel coumarin chalcone, 3-(3-(4-hydroxy-3-methoxyphenyl) acryloyl)-2H-chromen-2-one (CCh), was synthesized, characterized, and tested for its ability to inhibit enzymatic browning in potatoes. The compound was produced through a condensation reaction between 3-acetylcoumarin and vanillin. Its structure was confirmed using 1H, 13C-NMR, and FT-IR spectroscopy. The anti-browning effect of CCh, compared to the known antioxidant, vitamin C, was evaluated over five days of frozen storage. Results showed that CCh effectively inhibited PPO activity and slowed the browning process. Molecular docking simulations with PPO (PDB ID: 2P3X) confirmed CCh’s binding to amino acid residues GLN A331, LYS A61, LEU A53, PRO A89, and THR A136 through hydrogen bonds and hydrophobic interactions. The calculated binding energy of CCh was −4.71 kcal/mol, similar to vitamin C (−5.2 kcal/mol). These findings highlight CCh as a potential natural food preservative and capable of inhibiting enzymatic browning in potatoes, and could extend the shelf life of fruits and vegetables.
کلیدواژه‌ها
Food preservatives
Enzymatic browning
polyphenol oxidase
coumarin chalcone
Molecular docking
موضوعات

عنوان مقاله English

A Comparative Investigation of Synthesized Coumarin-Chalcone with Vitamin C for the Inhibition of Enzymatic Browning in Potato

نویسندگان English

Omar T Ali 1
Abdallah F Al-burgus 2
Omar Y Al-abbasy 3
Mohammed Fadhil H Haddad 4
1 Department of Chemistry, College of Education for Pure Science, University of Mosul, Mosul-Iraq
2 General Directorate of Education in Nineveh, Iraq
3 Chemistry Dept., College of education for pure science, University of Mosul, Mosul-Iraq
4 Department of Medical Lab Techniques, Northern Technical University, Mosul, Iraq
چکیده English

The enzymatic browning reaction is one of the primary factors contributing to the deterioration of food products, such as fruits and vegetables, after harvest. This phenomenon is primarily caused by the enzyme polyphenol oxidase (PPO), which alters the organoleptic properties and nutritional value, ultimately leading to economic losses worldwide. The inhibition of PPO prevents this reaction and preserves food products. Coumarin chalcone bearing a hydroxyl group has shown promising antioxidant and enzyme-inhibitory activities. Here, a novel coumarin chalcone, 3-(3-(4-hydroxy-3-methoxyphenyl) acryloyl)-2H-chromen-2-one (CCh), was synthesized, characterized, and tested for its ability to inhibit enzymatic browning in potatoes. The compound was produced through a condensation reaction between 3-acetylcoumarin and vanillin. Its structure was confirmed using 1H, 13C-NMR, and FT-IR spectroscopy. The anti-browning effect of CCh, compared to the known antioxidant, vitamin C, was evaluated over five days of frozen storage. Results showed that CCh effectively inhibited PPO activity and slowed the browning process. Molecular docking simulations with PPO (PDB ID: 2P3X) confirmed CCh’s binding to amino acid residues GLN A331, LYS A61, LEU A53, PRO A89, and THR A136 through hydrogen bonds and hydrophobic interactions. The calculated binding energy of CCh was −4.71 kcal/mol, similar to vitamin C (−5.2 kcal/mol). These findings highlight CCh as a potential natural food preservative and capable of inhibiting enzymatic browning in potatoes, and could extend the shelf life of fruits and vegetables.

کلیدواژه‌ها English

Food preservatives
Enzymatic browning
polyphenol oxidase
coumarin chalcone
Molecular docking
[1]           Küpeli Akkol, E., et al., Coumarins and coumarin-related compounds in pharmacotherapy of cancer. Cancers, 2020. 12(7): p. 1959.
[2]           Delcourt, M.-L., et al., 3D Coumarin systems based on [2.2] paracyclophane: Synthesis, spectroscopic characterization, and chiroptical properties. The Journal of Organic Chemistry, 2018. 84(2): p. 888-899.
[3]           Lončar, M., et al., Coumarins in food and methods of their determination. Foods, 2020. 9(5): p. 645.
[4]           AL-BURGUS, A.F., O. THANOON-ALI, and O.Y. AL-ABBASY, DESIGN, SYNTHESIS AND MOLECULAR DOCKING OF NEW SPIRO HETEROCYCLIC COUMARIN AS ANTIBACTERIAL AGENTS. Rev. Roum. Chim, 2024. 69(7-8): p. 399-404.
[5]           Ali, O.T., et al., The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids. Chemistry and Physics of Lipids, 2019. 221: p. 207-218.
[6]           Patil, S.A., et al., Comprehensive review on medicinal applications of coumarin-derived imine–metal complexes. Molecules, 2022. 27(16): p. 5220.
[7]           Önder, A., Anticancer activity of natural coumarins for biological targets. Studies in natural products chemistry, 2020. 64: p. 85-109.
[8]           Wilson, D.W., et al., The role of food antioxidants, benefits of functional foods, and influence of feeding habits on the health of the older person: An overview. Antioxidants, 2017. 6(4): p. 81.
[9]           AL-abbasy, O.Y., et al., Potato Enzymatic Browning, Mitigation and Prevention: Current Overview of Approaches and Findings. Journal of food science and technology(Iran), 2025. 22(164): p. 1-15.
[10]        Tinello, F. and A. Lante, Recent advances in controlling polyphenol oxidase activity of fruit and vegetable products. Innovative Food Science & Emerging Technologies, 2018. 50: p. 73-83.
[11]        Gupta, S., et al., Food Browning, Its Type and Controlling Measures: A Review Article. Chemical Science Review and Letters, 2022. 11(44): p. 417-424.
[12]        Paravisini, L. and D.G. Peterson, Mechanisms non-enzymatic browning in orange juice during storage. Food chemistry, 2019. 289: p. 320-327.
[13]        Younus, S.A., et al., Antioxidative effect of Maillard reaction products of spermine–sugar system on partially purified plum polyphenol oxidase. Journal of food science and technology(Iran), 2025. 22(160): p. 227-241.
[14]        Moon, K.M., et al., Recent trends in controlling the enzymatic browning of fruit and vegetable products. Molecules, 2020. 25(12): p. 2754.
[15]        Al-Abbasy, O.Y., et al., Purification, characterization, and inhibition of tyrosinase from jerusalem artichoke (Helianthus tuberosus L.) tuber. Reports of Biochemistry & Molecular Biology, 2021. 10(3): p. 495.
[16]        Levaj, B., et al., Maintaining the quality and safety of fresh-cut potatoes (Solanum tuberosum): Overview of recent findings and approaches. Agronomy, 2023. 13(8): p. 2002.
[17]        Nabeel, Z., Q.A.-H. Jaber, and N.A. Abdul-Rida, Novel benzo [f] coumarin derivatives as probable acetylcholinesterase inhibitors: synthesis, in vitro, and in silico studies for evaluation of their anti-AChE activity. Indonesian Journal of Chemistry, 2021. 22(1): p. 35-46.
[18]        Cuellar, J.E., et al., Coumaro-chalcones synthesized under solvent-free conditions as potential agents against malaria, leishmania and trypanosomiasis. Heliyon, 2022. 8(2).
[19]        Alrushdi, F.M.M., et al., In vitro: inhibition of partially purified pancreatic ovine lipase by willow bark extracts. Journal of Bioscience and Applied Research, 2025. 11(1): p. 168-179.
[20]        Rashan, A.I. and O.Y. Al-abbasy, Inhibitory and kinetic study of partially purified tyrosinase from Iraqi quince fruit. Plant Cell Biotech Mol Bio, 2021. 22(23-24): p. 1-14.
[21]        Tsai, P.-J., et al., Interactive role of color and antioxidant capacity in caramels. Food Research International, 2009. 42(3): p. 380-386.
[22]        Anesini, C., G.E. Ferraro, and R. Filip, Total polyphenol content and antioxidant capacity of commercially available tea (Camellia sinensis) in Argentina. Journal of agricultural and food chemistry, 2008. 56(19): p. 9225-9229.
[23]        Oktay, M., et al., Polyphenoloxidase from Amasya apple. Journal of Food Science, 1995. 60(3): p. 494-496.
[24]        Al-burgus, A.F., A. Ali, and O.Y. Al-abbasy, New spiro-heterocyclic coumarin derivatives as antibacterial agents: design, synthesis and molecular docking. Chimica Techno Acta. 2024. Vol. 11.№ 3, 2024. 11(3).
[25]        Dewan, M.F., M.N. Islam, and M.S. Azam, 10 Food and Their Additives/Implications Preservatives. Food Safety: Contaminants and Risk Assessment, 2024: p. 155.
[26]        Cuchet, A., et al., Authentication of Tonka beans extracts (Dipteryx odorata) using LC-UV/MS, GC-MS and multi element (13C, 2H and 18O) bulk specific isotope analysis. Industrial Crops and Products, 2024. 209: p. 118038.
[27]        Almeida-Neto, F.W., et al., Structural, spectroscopical, electronic, non-linear optical characterization and antioxidant activity of 2-hidroxychalcones para-derivatives: An experimental and theoretical approach. Journal of Molecular Structure, 2024. 1303: p. 137327.
[28]        Costa, T.M., L.B.B. Tavares, and D. de Oliveira, Fungi as a source of natural coumarins production. Applied Microbiology and Biotechnology, 2016. 100: p. 6571-6584.
[29]        García Procaccini, L.M., et al., Ascorbic Acid and Citric Acid Treatments Increase the Shelf Life of Fresh-Cut Potato: Cultivar Effect. Potato Research, 2024: p. 1-23.
[30]        Laurila, E., R. Kervinen, and R. Ahvenainen, The inhibition of enzymatic browning in minimally processed vegetables and fruits. Postharvest news and information, 1998. 9(4): p. 53-66.
[31]        Kalogianni, A.I., et al., Natural phenolic compounds for the control of oxidation, bacterial spoilage, and foodborne pathogens in meat. Foods, 2020. 9(6): p. 794.
[32]        AYÓN-REYNA, L.E., et al., Changes in ascorbic acid and total phenolics contents associated with browning inhibition of pineapple slices. Food Science and Technology, 2019. 39: p. 531-537.
[33]        Duan, X., G. Wu, and Y. Jiang, Evaluation of the antioxidant properties of litchi fruit phenolics in relation to pericarp browning prevention. Molecules, 2007. 12(4): p. 759-771.
[34]        Luo, S., Y. Hou, and S.-Q. Hu, Enhancement of preference, catalytic activity and thermostability of polyphenol oxidase from Rosa Chinensis by semi-rational engineering. Molecular Catalysis, 2024. 559: p. 114059.
[35]        Ali, A., et al., Potential of ascorbic acid in human health against different diseases: an updated narrative review. International Journal of Food Properties, 2024. 27(1): p. 493-515.
[36]        ., T. and et al., Improvement of a Novel Purification Method of Phycocyanin Pigment from the Microalga Nostoc Minutum and Evaluation of Its Anticancer Activity. Egyptian Journal of Aquatic Biology and Fisheries, 2025. 29(3): p. 2181-2202.
[37]        Wang, H., et al., Inhibition of ascorbic acid on Lotus Rhizome polyphenol oxidase: Inhibition kinetics and computational simulation. Food Sci. Qual. Manag, 2014. 34: p. 103-112.
[38]        Song, Z., et al., Glutamic acid can prevent the browning of fresh-cut potatoes by inhibiting PPO activity and regulating amino acid metabolism. LWT, 2023. 180: p. 114735.
[39]        Jiang, H., et al., Polyphenol oxidase inhibited by 4-hydroxycinnamic acid and naringenin: Multi-spectroscopic analyses and molecular docking simulation at different pH. Food Chemistry, 2022. 396: p. 133662.
[40]        Han, Q.-Y., et al., Kinetic, spectroscopic, and molecular docking studies on the inhibition of membrane-bound polyphenol oxidase from Granny Smith apples (Malus domestica Borkh.). Food chemistry, 2021. 338: p. 127928.