{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T17:28:45Z","timestamp":1790270925546,"version":"4.1.0"},"reference-count":44,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2024,10,21]],"date-time":"2024-10-21T00:00:00Z","timestamp":1729468800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Compounds of natural origin found in varying quantities in plant-based products constitute a highly significant category, possessing structural significance as well as the capacity to regulate oxidative processes. The activity of these compounds may be modulated by the composition of the biological environment in which they operate, the pH of the environment, or the presence of metal cations in plants or plant extracts. A successful complexation reaction was mainly confirmed by FT-IR, observing the shift from the original transmittance of catechin bonds, especially O-H ones. This work shows the synthetic methodology and the optimization process that took place to synthesize a catechin\u2013copper complex, which demonstrated antioxidant activity. It was tested for iron chelation ability, hydroxyl radicals, and the inhibition of lipoxygenase (15-LOX). An antidiabetic assay was performed by determining the inhibition of alpha-amylase and alpha-glucosidase, finding that the synthesized complex had similar inhibitory potential as pure catechin. The antibacterial tests showed results against Staphylococcus aureus and the antifungal properties of the complex against Candida albicans.<\/jats:p>","DOI":"10.3390\/molecules29204969","type":"journal-article","created":{"date-parts":[[2024,10,21]],"date-time":"2024-10-21T09:58:24Z","timestamp":1729504704000},"page":"4969","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Insights into Catechin\u2013Copper Complex Structure and Biologic Activity Modulation"],"prefix":"10.3390","volume":"29","author":[{"given":"Ionut I.","family":"Lungu","sequence":"first","affiliation":[{"name":"Faculty of Pharmacy, \u201cGrigore T. Popa\u201d University of Medicine and Pharmacy, 700115 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9173-4832","authenticated-orcid":false,"given":"Oana","family":"Cioanca","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, \u201cGrigore T. Popa\u201d University of Medicine and Pharmacy, 700115 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1981-8246","authenticated-orcid":false,"given":"Cornelia","family":"Mircea","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, \u201cGrigore T. Popa\u201d University of Medicine and Pharmacy, 700115 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cristina","family":"Tuchilus","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, \u201cGrigore T. Popa\u201d University of Medicine and Pharmacy, 700115 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alina","family":"Stefanache","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, \u201cGrigore T. Popa\u201d University of Medicine and Pharmacy, 700115 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Riana","family":"Huzum","sequence":"additional","affiliation":[{"name":"Faculty of Medicine, \u201cGrigore T. Popa\u201d University of Medicine and Pharmacy, 400347 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monica","family":"Hancianu","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy, \u201cGrigore T. Popa\u201d University of Medicine and Pharmacy, 700115 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,10,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"861","DOI":"10.31925\/farmacia.2021.5.5","article-title":"Comparative Chemical and Biological Activity of Selective Herbal Extracts","volume":"69","author":"Humulescu","year":"2021","journal-title":"Farmacia"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1002\/ptr.6208","article-title":"Antibacterial activity of flavonoids and their structure\u2013activity relationship: An update review","volume":"33","author":"Farhadi","year":"2019","journal-title":"Phytother. Res."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"327","DOI":"10.2165\/00007256-200636040-00004","article-title":"Oxidative Stress: Relationship with Exercise and Training","volume":"36","author":"Finaud","year":"2006","journal-title":"Sports Med."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Wang, K., and Chen, X. (2024). Protective effect of flavonoids on oxidative stress injury in Alzheimer\u2019s disease. Nat. Prod. Res., 1\u201328.","DOI":"10.1080\/14786419.2024.2345760"},{"key":"ref_5","first-page":"151","article-title":"Flavonoids as promising therapeutic and dietary agents","volume":"124","author":"Lungu","year":"2020","journal-title":"Med. Surg. J."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"e47","DOI":"10.1017\/jns.2016.41","article-title":"Flavonoids: An Overview","volume":"5","author":"Panche","year":"2016","journal-title":"J. Nutr. Sci."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"4078","DOI":"10.1021\/acs.jafc.6b01513","article-title":"Green Tea Catechin Prevents Hypoxia\/Reperfusion-Evoked Oxidative Stress-Regulated Autophagy-Activated Apoptosis and Cell Death in Microglial Cells","volume":"64","author":"Chen","year":"2016","journal-title":"J. Agric. Food. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1006\/abbi.2000.2118","article-title":"Influence of Metal Ions on Flavonoid Protection against Asbestos-Induced Cell Injury","volume":"385","author":"Kostyuk","year":"2001","journal-title":"Arch. Biochem. Biophys."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"135","DOI":"10.31925\/farmacia.2020.1.19","article-title":"The evaluation of normo-glycemic and cyto-regenerative effects of Pelargonium species extracts","volume":"68","author":"Iancu","year":"2020","journal-title":"Farmacia."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1009","DOI":"10.2174\/1568026622666220221110506","article-title":"The Antibacterial Activity of Natural-Derived Flavonoids","volume":"22","author":"Tan","year":"2022","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"755","DOI":"10.31925\/farmacia.2023.4.11","article-title":"Catechin-Zinc-Complex: Synthesis, Characterization and Biological Activity Assessment","volume":"71","author":"Lungu","year":"2023","journal-title":"Farmacia"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1271\/bbb.65.126","article-title":"Effects of pH and Metal Ions on Antioxidative Activities of Catechins","volume":"65","author":"Kumamoto","year":"2001","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1016\/0076-6879(90)86128-I","article-title":"Flavonoids as Antioxidants: Determination of Radical-Scavenging Efficiencies","volume":"186","author":"Bors","year":"1990","journal-title":"Methods Enzymol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1016\/S0014-5793(97)01182-4","article-title":"Protection against Oxidative Damage of Erythrocyte Membrane by the Flavonoid Quercetin and Its Relation to Iron Chelating Activity","volume":"416","author":"Ferrali","year":"1997","journal-title":"FEBS Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/j.meatsci.2011.05.027","article-title":"Total antioxidant capacities of raw and cooked meats","volume":"90","author":"Serpen","year":"2012","journal-title":"Meat Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1002\/biof.1219","article-title":"Screening Alpha-Glucosidase and Alpha-Amylase Inhibitors from Natural Compounds by Molecular Docking in Silico","volume":"41","author":"Jhong","year":"2015","journal-title":"Biofactors"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.phytochem.2013.12.003","article-title":"Alpha-Amylase and Alpha-Glucosidase Inhibition Is Differentially Modulated by Fucoidan Obtained from Fucus Vesiculosus and Ascophyllum Nodosum","volume":"98","author":"Kim","year":"2014","journal-title":"Phytochemistry"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3126","DOI":"10.1002\/jsfa.10347","article-title":"Black Tea Polyphenol Theaflavin as Promising Antioxidant and Potential Copper Chelator","volume":"100","author":"Sharma","year":"2020","journal-title":"J. Sci. Food Agric."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1517\/14728222.2012.664134","article-title":"Antidiabetic Effects of Natural Plant Extracts via Inhibition of Carbohydrate Hydrolysis Enzymes with Emphasis on Pancreatic Alpha Amylase","volume":"16","author":"Etxeberria","year":"2012","journal-title":"Expert. Opin. Ther. Targets"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"503","DOI":"10.1016\/j.ijbiomac.2021.01.070","article-title":"Three Flavanols Delay Starch Digestion by Inhibiting \u03b1-Amylase and Binding with Starch","volume":"172","author":"Jiang","year":"2021","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1515\/jbcpp-2011-0005","article-title":"Phenolic-Rich Extracts from Selected Tropical Underutilized Legumes Inhibit \u03b1-Amylase, \u03b1-Glucosidase, and Angiotensin I Converting Enzyme in Vitro","volume":"23","author":"Ademiluyi","year":"2012","journal-title":"J. Basic Clin. Physiol. Pharmacol."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Michalczyk, K., and Cymbaluk-P\u0142oska, A. (2020). The Role of Zinc and Copper in Gynecological Malignancies. Nutrients, 12.","DOI":"10.3390\/nu12123732"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4424","DOI":"10.1007\/s12010-022-03899-4","article-title":"Antioxidant, Antibacterial, and Anti-Diabetic Activity of Green Synthesized Copper Nanoparticles of Cocculus Hirsutus (Menispermaceae)","volume":"194","author":"Ameena","year":"2022","journal-title":"Appl. Biochem. Biotechnol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"e7506","DOI":"10.1002\/aoc.7506","article-title":"Application of antimicrobial properties of copper","volume":"38","author":"Yu","year":"2024","journal-title":"Appl. Organomet. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"035701","DOI":"10.1088\/1361-6528\/ac2e77","article-title":"Polyphenol stabilize copper nanoparticle formulations for rapid disinfection of bacteria and virus on diverse surfaces","volume":"33","author":"Sadani","year":"2021","journal-title":"Nanotechnology"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Wang, Z., and An, P. (2017). Characterization of copper complex nanoparticles synthesized by plant polyphenols. BioRxiv.","DOI":"10.1101\/134940"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"18179","DOI":"10.1039\/D1RA02149D","article-title":"Copper as an antimicrobial agent: Recent advances","volume":"11","author":"Salah","year":"2021","journal-title":"RSC Adv."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"32004","DOI":"10.1039\/C4RA03241A","article-title":"Antibacterial activity of copper (II) complexes against Staphylococcus aureus","volume":"4","author":"Rajalakshmi","year":"2014","journal-title":"RSC Adv."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Scattareggia Marchese, A., Destro, E., Boselli, C., Barbero, F., Malandrino, M., Cardeti, G., Fenoglio, I., and Lanni, L. (2022). Inhibitory Effect against Listeria monocytogenes of Carbon Nanoparticles Loaded with Copper as Precursors of Food Active Packaging. Foods, 11.","DOI":"10.3390\/foods11192941"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1179\/135100004225003897","article-title":"Antioxidant Properties of Complexes of Flavonoids with Metal Ions","volume":"9","author":"Souza","year":"2004","journal-title":"Redox Rep."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Sarker, U., and Oba, S. (2019). Nutraceuticals, Antioxidant Pigments, and Phytochemicals in the Leaves of Amaranthus spinosus and Amaranthus viridis Weedy Species. Sci. Rep., 9.","DOI":"10.1038\/s41598-019-50977-5"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1901","DOI":"10.1016\/j.saa.2008.07.030","article-title":"Synthesis, Characterization and Antioxidant Activity Copper\u2013Quercetin Complex","volume":"71","author":"Bukhari","year":"2009","journal-title":"Spectrochim. Acta. A Mol. Biomol. Spectrosc."},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Szczepanik, J., Podg\u00f3rski, T., and Domaszewska, K. (2021). The Level of Zinc, Copper and Antioxidant Status in the Blood Serum of Women with Hashimoto\u2019s Thyroiditis. Int. J. Environ. Res. Public Health, 18.","DOI":"10.3390\/ijerph18157805"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1016\/j.jep.2006.04.004","article-title":"Alpha-Amylase Inhibitory Activity of Some Malaysian Plants Used to Treat Diabetes; with Particular Reference to Phyllanthus Amarus","volume":"107","author":"Ali","year":"2006","journal-title":"J. Ethnopharmacol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"H97","DOI":"10.1111\/j.1750-3841.2010.01544.x","article-title":"In Vitro Potential of Ascophyllum Nodosum Phenolic Antioxidant-Mediated Alpha-Glucosidase and Alpha-Amylase Inhibition","volume":"75","author":"Apostolidis","year":"2010","journal-title":"J. Food. Sci."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1080\/10826068.2019.1679171","article-title":"Characterization, Inhibitory Activity and Mechanism of Polyphenols from Faba Bean (Gallic-Acid and Catechin) on \u03b1-Glucosidase: Insights from Molecular Docking and Simulation Study","volume":"50","author":"Choudhary","year":"2020","journal-title":"Prep. Biochem. Biotechnol."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Rajeshkumar, S., Menon, S., Venkat Kumar, S., Tambuwala, M.M., Bakshi, H.A., Mehta, M., Satija, S., Gupta, G., Chellappan, D.K., and Thangavelu, L. (2019). Antibacterial and Antioxidant Potential of Biosynthesized Copper Nanoparticles Mediated through Cissus Arnotiana Plant Extract. J. Photochem. Photobiol. B, 197.","DOI":"10.1016\/j.jphotobiol.2019.111531"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3923\/ijds.2020.1.9","article-title":"Antioxidant Properties of Milk: Effect of Milk Species, Milk Fractions and Heat Treatments","volume":"15","author":"Azzam","year":"2019","journal-title":"Int. J. Dairy Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2099","DOI":"10.1007\/s12011-021-02812-0","article-title":"Ecofriendly Synthesis of Biosynthesized Copper Nanoparticles with Starch-Based Nanocomposite: Antimicrobial, Antioxidant, and Anticancer Activities","volume":"200","author":"Hasanin","year":"2022","journal-title":"Biol. Trace Elem. Res."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"47","DOI":"10.5530\/fra.2020.2.9","article-title":"Importance of Epigallocatechin and Its Health Benefits","volume":"10","author":"Shahrajabian","year":"2021","journal-title":"Free Radic. Antioxid."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Maftei, N.-M., Bogdan, R.E., Boev, M., Marin, D.B., Ramos-Villarroel, A.Y., and Iancu, A.-V. (2023). Innovative Fermented Soy Drink with the Sea Buckthorn Syrup and the Probiotics Co-Culture of Lactobacillus Paracasei ssp. Paracasei (L. Casei\u00ae 431) and Bifidobacterium Animalis ssp. Lactis (Bb-12\u00ae). Fermentation, 9.","DOI":"10.3390\/fermentation9090806"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Wang, J., Wang, X., He, Y., Jia, L., Yang, C.S., Reiter, R.J., and Zhang, J. (2019). Antioxidant and Pro-Oxidant Activities of Melatonin in the Presence of Copper and Polyphenols In Vitro and In Vivo. Cells, 8.","DOI":"10.3390\/cells8080903"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2060","DOI":"10.37358\/RC.17.9.5822","article-title":"The synergistic antioxidant effect and antimicrobial efficacity of propolis, myrrh and chlorhexidine as beneficial toothpaste components","volume":"68","author":"Lisa","year":"2017","journal-title":"Rev. Chim.-Buchar."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2519","DOI":"10.37358\/RC.19.7.7372","article-title":"The Comparative Study of Equisetum pratense, E. sylvaticum, E. telmateia: Accumulation of silicon, antioxidant and antimicrobial screening","volume":"70","author":"Marin","year":"2019","journal-title":"Rev. Chim."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/20\/4969\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:17:25Z","timestamp":1760113045000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/20\/4969"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,10,21]]},"references-count":44,"journal-issue":{"issue":"20","published-online":{"date-parts":[[2024,10]]}},"alternative-id":["molecules29204969"],"URL":"https:\/\/doi.org\/10.3390\/molecules29204969","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,10,21]]}}}