{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,13]],"date-time":"2026-02-13T12:35:56Z","timestamp":1770986156792,"version":"3.50.1"},"reference-count":34,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2022,9,28]],"date-time":"2022-09-28T00:00:00Z","timestamp":1664323200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"\u201cBacchusTech\u2013Integrated Approach for the Valorization of Winemaking Residues\u201d","award":["POCI-01-0247-FEDER-069583"],"award-info":[{"award-number":["POCI-01-0247-FEDER-069583"]}]},{"name":"\u201cBacchusTech\u2013Integrated Approach for the Valorization of Winemaking Residues\u201d","award":["COMPETE 2020"],"award-info":[{"award-number":["COMPETE 2020"]}]},{"name":"Competitiveness and Internationalization Operational Program","award":["POCI-01-0247-FEDER-069583"],"award-info":[{"award-number":["POCI-01-0247-FEDER-069583"]}]},{"name":"Competitiveness and Internationalization Operational Program","award":["COMPETE 2020"],"award-info":[{"award-number":["COMPETE 2020"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Residual diatomaceous earth (RDE) from winemaking activities is a rich and currently underexploited source of phenolic compounds which ought to be recycled from the perspective of circular bioeconomy. In this work, we demonstrate the feasibility of molecularly imprinted polymers (MIPs) for the enrichment of quercetin, a flavonoid at a fairly high content in residual diatomaceous earth. These MIPs were synthesized through free radical polymerization. FTIR confirmed the integration of the functional monomers into the polymeric chains. Batch adsorption experiments were used to assess the retention and selectivity of those MIPs towards quercetin. Commercial resins were compared with the synthesized materials using the same procedures. These adsorption experiments allowed the selection of the best performing MIP for the valorization of RDE extract. This treatment consisted of saturating the selected MIP with the extract and then desorbing the retained compounds using solvents of selected compositions. The desorbed fractions were analyzed using liquid chromatography, and the results demonstrated an increase in quercetin\u2019s fractional area from 5% in the RDE extract to more than 40% in some fractions, which is roughly an eightfold enrichment of quercetin. Moreover, other flavonoids of close chemical structure to quercetin have been rather retained and enriched by the MIP.<\/jats:p>","DOI":"10.3390\/molecules27196406","type":"journal-article","created":{"date-parts":[[2022,9,28]],"date-time":"2022-09-28T22:53:19Z","timestamp":1664405599000},"page":"6406","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Enrichment of Quercetin from Winemaking Residual Diatomaceous Earth via a Tailor-Made Imprinted Adsorbent"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1835-1066","authenticated-orcid":false,"given":"Amir","family":"Bzainia","sequence":"first","affiliation":[{"name":"Polytechnic Institute of Bragan\u00e7a, Mountain Research Center (CIMO), 5300-253 Bragan\u00e7a, Portugal"},{"name":"LSRE-LCM-Laboratory of Separation and Reaction Engineering\u2014Laboratory of Catalysis and Materials, Faculty of Engineering, Department of Chemical Engineering, University of Porto, 4200-465 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7369-382X","authenticated-orcid":false,"given":"Rolando C. S.","family":"Dias","sequence":"additional","affiliation":[{"name":"Polytechnic Institute of Bragan\u00e7a, Mountain Research Center (CIMO), 5300-253 Bragan\u00e7a, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7807-4275","authenticated-orcid":false,"given":"M\u00e1rio Rui P. F. N.","family":"Costa","sequence":"additional","affiliation":[{"name":"LSRE-LCM-Laboratory of Separation and Reaction Engineering\u2014Laboratory of Catalysis and Materials, Faculty of Engineering, Department of Chemical Engineering, University of Porto, 4200-465 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,9,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"McGovern, P.E. (2019). Ancient Wine: The Search for the Origins of Viniculture, Princeton University Press.","DOI":"10.1515\/9780691198965"},{"key":"ref_2","unstructured":"(2022, July 03). OIV. Available online: https:\/\/www.oiv.int\/."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"46","DOI":"10.1186\/s40643-018-0232-6","article-title":"Novel application and industrial exploitation of winery by-products","volume":"5","author":"Kalli","year":"2018","journal-title":"Bioresour. Bioprocess"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1080\/07388551.2019.1573799","article-title":"Winery wastewater treatment: A critical overview of advanced biological processes","volume":"39","author":"Bolzonella","year":"2019","journal-title":"Crit. Rev. Biotechnol."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Nanni, A., Parisi, M., and Colonna, M. (2021). Wine By-Products as Raw Materials for the Production of Biopolymers and of Natural Reinforcing Fillers: A Critical Review. Polymers, 13.","DOI":"10.3390\/polym13030381"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1007\/s10717-008-9005-6","article-title":"Diatomite and its applications","volume":"65","author":"Ivanov","year":"2008","journal-title":"Glas Ceram."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1515\/chem-2020-0049","article-title":"Diatomaceous Earth: Characterization, thermal modification, and application","volume":"19","author":"Reka","year":"2021","journal-title":"Open. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.wasman.2017.11.011","article-title":"Sustainable wineries through waste valorisation: A review of grape marc utilisation for value-added products","volume":"72","author":"Muhlack","year":"2018","journal-title":"Waste Manag."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1243","DOI":"10.1111\/1541-4337.12298","article-title":"Plant Polyphenols as Antioxidant and Antibacterial Agents for Shelf-Life Extension of Meat and Meat Products: Classification, Structures, Sources, and Action Mechanisms","volume":"16","author":"Papuc","year":"2017","journal-title":"Compr. Rev. Food. Sci. Food. Saf."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2221","DOI":"10.1002\/ptr.6419","article-title":"Polyphenols: A concise overview on the chemistry, occurrence, and human health","volume":"33","author":"Durazzo","year":"2019","journal-title":"Phyther. Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"S29","DOI":"10.1080\/10408398.2015.1067595","article-title":"Advance on the Flavonoid C-glycosides and Health Benefits","volume":"56","author":"Xiao","year":"2016","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"6876","DOI":"10.1038\/s41598-019-43345-w","article-title":"Quercetin conjugated with superparamagnetic iron oxide nanoparticles improves learning and memory better than free quercetin via interacting with proteins involved in LTP","volume":"9","author":"Amanzadeh","year":"2019","journal-title":"Sci. Rep."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.jnutbio.2015.09.027","article-title":"Treatment with kaempferol suppresses breast cancer cell growth caused by estrogen and triclosan in cellular and xenograft breast cancer models","volume":"28","author":"Kim","year":"2016","journal-title":"J. Nutr. Biochem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1016\/j.foodhyd.2019.06.004","article-title":"Packaging films formulated with gelatin and anthocyanins nanocomplexes: Physical properties, antioxidant activity and its application for olive oil protection","volume":"96","author":"Wang","year":"2019","journal-title":"Food Hydrocoll."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"100401","DOI":"10.1016\/j.fpsl.2019.100401","article-title":"Characterization of the physical properties and biological activity of chitosan films grafted with gallic acid and caffeic acid: A comparison study","volume":"22","author":"Wang","year":"2019","journal-title":"Food Packag. Shelf Life"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1806","DOI":"10.1177\/0040517516659378","article-title":"Dyeing characteristics and functionability of tussah silk fabric with oak bark extract","volume":"87","author":"Jia","year":"2017","journal-title":"Text Res. J."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1016\/j.tifs.2018.11.010","article-title":"Strategies for enrichment and purification of polyphenols from fruit-based materials","volume":"83","author":"Kelly","year":"2019","journal-title":"Trends Food Sci. Technol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1016\/j.seppur.2016.09.007","article-title":"Sequential pressure-driven membrane operations to recover and fractionate polyphenols and polysaccharides from second racking wine lees","volume":"173","author":"Giacobbo","year":"2017","journal-title":"Sep. Purif. Technol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"434","DOI":"10.1016\/j.fbp.2014.06.002","article-title":"Colloidal gas aphrons based separation process for the purification and fractionation of natural phenolic extracts","volume":"94","author":"Spigno","year":"2015","journal-title":"Food Bioprod. Process."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/j.fbp.2018.04.007","article-title":"Colloidal Gas Aphrons separation to obtain polyphenol rich fractions from artichoke agro-industrial discards","volume":"110","author":"Noriega","year":"2018","journal-title":"Food Bioprod. Process."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2016\/9349627","article-title":"Batch and Continuous Flow Adsorption of Phenolic Compounds from Olive Mill Wastewater: A Comparison between Nonionic and Ion Exchange Resins","volume":"2016","author":"Pinelli","year":"2016","journal-title":"Int. J. Chem. Eng."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3710","DOI":"10.1021\/acssensors.0c01634","article-title":"Oriented Immobilization of Protein Templates: A New Trend in Surface Imprinting","volume":"5","author":"Kalecki","year":"2020","journal-title":"ACS Sens."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"893","DOI":"10.1007\/s10337-019-03728-7","article-title":"Preparation of Molecularly Imprinted Adsorbents with Improved Retention Capability of Polyphenols and Their Application in Continuous Separation Processes","volume":"82","author":"Gomes","year":"2019","journal-title":"Chromatographia"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1021\/acs.chemrev.8b00171","article-title":"Molecularly Imprinted Polymers","volume":"119","author":"BelBruno","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Mora-Granados, M., Gonz\u00e1lez-G\u00f3mez, D., Jeong, J.S., and Gallego-Pic\u00f3, A. (2021). A Molecularly Imprinted Polymer for Selective Extraction of Phenolic Acids from Human Urine. Appl. Sci., 11.","DOI":"10.3390\/app11041577"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"13763","DOI":"10.1007\/s13277-016-5280-y","article-title":"Different expression levels of glycans on leukemic cells\u2014a novel screening method with molecularly imprinted polymers (MIP) targeting sialic acid","volume":"37","author":"Abdullah","year":"2016","journal-title":"Tumor. Biol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3116","DOI":"10.1039\/C7GC00912G","article-title":"Valorisation of agricultural waste with an adsorption\/nanofiltration hybrid process: From materials to sustainable process design","volume":"19","author":"Didaskalou","year":"2017","journal-title":"Green Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/j.bej.2016.03.009","article-title":"Development of high performance and facile to pack molecularly imprinted particles for aqueous applications","volume":"111","author":"Oliveira","year":"2016","journal-title":"Biochem. Eng. J."},{"key":"ref_29","unstructured":"(2022, July 12). Sigma Aldrich. Available online: https:\/\/www.sigmaaldrich.com\/PT\/en."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1539","DOI":"10.1007\/s10337-020-03958-0","article-title":"Processing of Onion Skin Extracts with Quercetin-Molecularly Imprinted Adsorbents Working at a Wide Range of Water Content","volume":"83","author":"Gomes","year":"2020","journal-title":"Chromatographia"},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Gomes, C., Sadoyan, G., Dias, R., and Costa, M. (2017). Development of Molecularly Imprinted Polymers to Target Polyphenols Present in Plant Extracts. Processes, 5.","DOI":"10.3390\/pr5040072"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"208","DOI":"10.1016\/j.jfoodeng.2010.04.001","article-title":"Solubility and solution thermodynamic properties of quercetin and quercetin dihydrate in subcritical water","volume":"100","author":"Srinivas","year":"2010","journal-title":"J. Food Eng."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1732","DOI":"10.1021\/jo048470p","article-title":"Urea Host Monomers for Stoichiometric Molecular Imprinting of Oxyanions","volume":"70","author":"Hall","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1016\/j.indcrop.2016.04.065","article-title":"Phenolic profile and antioxidant activity of Coleostephus myconis (L.) Rchb.f.: An underexploited and highly disseminated species","volume":"89","author":"Bessada","year":"2016","journal-title":"Ind. Crops Prod."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/19\/6406\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:41:08Z","timestamp":1760143268000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/19\/6406"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,9,28]]},"references-count":34,"journal-issue":{"issue":"19","published-online":{"date-parts":[[2022,10]]}},"alternative-id":["molecules27196406"],"URL":"https:\/\/doi.org\/10.3390\/molecules27196406","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,9,28]]}}}