{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T11:13:01Z","timestamp":1788347581374,"version":"build-2803163510"},"reference-count":46,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2021,7,8]],"date-time":"2021-07-08T00:00:00Z","timestamp":1625702400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"MCIU\/AEI\/FEDER, UE","award":["RTI2018-094558-B-I00"],"award-info":[{"award-number":["RTI2018-094558-B-I00"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Foods"],"abstract":"<jats:p>In recent years, health authorities have become increasingly concerned about preventing consumer exposure to opium alkaloids present in Papaver somniferum L. poppy seeds. In this study, a simple, rapid and efficient method has been optimised to determine all main opioids in poppy seeds (morphine, codeine, thebaine, papaverine, noscapine and oripavine) by UHPLC-QqQ-MS\/MS. For this purpose, solid-liquid extraction (SLE) of samples was optimised and six magnetic adsorbent materials with a core of Fe3O4 coated with amorphous and mesostructured silica, both functionalised with octadecyl-silane or octyl-silane were characterised and evaluated for magnetic solid-phase extraction (MSPE). The material with the best results was non-functionalised mesostructured silica and, with it, the MSPE procedure was optimised. This method was validated and used to quantify six opioids in 14 edible seed samples (eleven poppy seeds and three seed mixes). Considerable amounts were found (1.5\u2013249.0 mg\/kg morphine, &lt;0.2 \u00b5g\/kg\u201345.8 mg\/kg codeine, &lt;2.4 \u00b5g\/kg\u2013136.2 mg\/kg thebaine, &lt;0.2 \u00b5g\/kg\u201327.1 mg\/kg papaverine, &lt;0.2 \u00b5g\/kg\u2013108.7 mg\/kg noscapine and &lt;240 \u00b5g\/kg\u201333.4 mg\/kg oripavine), exceeding maximum limits established in some EU countries and the reference level of morphine in the EU. Furthermore, in some commercial samples for human consumption, inadequate labelling was found because significant amounts of alkaloids were detected even though Papaver rhoeas L. seeds were declared on the product label.<\/jats:p>","DOI":"10.3390\/foods10071587","type":"journal-article","created":{"date-parts":[[2021,7,8]],"date-time":"2021-07-08T10:42:17Z","timestamp":1625740937000},"page":"1587","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["Mesostructured Silica-Coated Magnetic Nanoparticles to Extract Six Opium Alkaloids in Poppy Seeds Prior to Ultra-High-Performance Liquid Chromatography-Tandem Mass Spectrometry Analysis"],"prefix":"10.3390","volume":"10","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4823-4004","authenticated-orcid":false,"given":"Gema","family":"Casado-Hidalgo","sequence":"first","affiliation":[{"name":"Departamento de Tecnolog\u00eda Qu\u00edmica y Ambiental, E.S.C.E.T., Universidad Rey Juan Carlos, C\/Tulip\u00e1n s\/n, M\u00f3stoles, 28933 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7150-122X","authenticated-orcid":false,"given":"Dami\u00e1n","family":"P\u00e9rez-Quintanilla","sequence":"additional","affiliation":[{"name":"Departamento de Tecnolog\u00eda Qu\u00edmica y Ambiental, E.S.C.E.T., Universidad Rey Juan Carlos, C\/Tulip\u00e1n s\/n, M\u00f3stoles, 28933 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6448-2385","authenticated-orcid":false,"given":"Sonia","family":"Morante-Zarcero","sequence":"additional","affiliation":[{"name":"Departamento de Tecnolog\u00eda Qu\u00edmica y Ambiental, E.S.C.E.T., Universidad Rey Juan Carlos, C\/Tulip\u00e1n s\/n, M\u00f3stoles, 28933 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2091-6772","authenticated-orcid":false,"given":"Isabel","family":"Sierra","sequence":"additional","affiliation":[{"name":"Departamento de Tecnolog\u00eda Qu\u00edmica y Ambiental, E.S.C.E.T., Universidad Rey Juan Carlos, C\/Tulip\u00e1n s\/n, M\u00f3stoles, 28933 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,7,8]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"443","DOI":"10.1016\/j.foodchem.2017.08.045","article-title":"Straightforward analytical method to determine opium alkaloids in poppy seeds and bakery products","volume":"242","author":"Fauw","year":"2018","journal-title":"Food Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"34","DOI":"10.3176\/proc.2017.1.04","article-title":"Content of alkaloids in ornamental Papaver somniferum L. cultivars growing in Estonia","volume":"66","author":"Meos","year":"2017","journal-title":"Proc. Est. Acad. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1229","DOI":"10.1111\/1556-4029.13664","article-title":"Quantification of Morphine, Codeine, and Thebaine in Home-Brewed Poppy Seed Tea by LC-MS\/MS","volume":"63","author":"Powers","year":"2018","journal-title":"J. Forensic Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.tifs.2020.12.013","article-title":"Opium alkaloids in food products: Current and future perspectives","volume":"108","author":"Sierra","year":"2021","journal-title":"Trends Food Sci. Technol."},{"key":"ref_5","unstructured":"AESAN (2020, January 23). Spanish Food Safety and Nutrition Agency. Opium Alkaloids in Poppy Seeds. Available online: http:\/\/www.aecosan.msssi.gob.es\/AECOSAN\/docs\/documentos\/seguridad_alimentaria\/gestion_riesgos\/opio_semillas_adormidera.pdf."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5292","DOI":"10.1021\/jf0608975","article-title":"Optimized LC\/MS\/MS analysis of morphine and codeine in poppy seed and evaluation of their fate during food processing as a basis for risk analysis","volume":"54","author":"Sproll","year":"2006","journal-title":"J. Agric. Food Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1016\/j.forsciint.2004.03.027","article-title":"Poppy seed consumption and toxicological analysis of blood and urine samples","volume":"143","author":"Moeller","year":"2004","journal-title":"Forensic Sci. Int."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1007\/s11419-015-0266-9","article-title":"Simultaneous plasma and oral fluid morphine and codeine concentrations after controlled administration of poppy seeds with known opiate content","volume":"33","author":"Newmeyer","year":"2015","journal-title":"Forensic Toxicol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/j.forsciint.2018.11.026","article-title":"Morphine concentrations in human urine following poppy seed paste consumption","volume":"295","author":"Koruyucu","year":"2019","journal-title":"Forensic Sci. Int."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1093\/jat\/27.7.449","article-title":"The determination of morphine in urine and oral fluid following ingestion of poppy seeds","volume":"27","author":"Rohrig","year":"2003","journal-title":"J. Anal. Toxicol."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"European Food Safety Authority (2011). Scientific Opinion on the risks for public health related to the presence of opium alkaloids in poppy seeds, EFSA Panel on Contaminants in the Food Chain (CONTAM). EFSA J., 9, 150.","DOI":"10.2903\/j.efsa.2011.2405"},{"key":"ref_12","unstructured":"(2020, January 23). BfR Recommends Provisional Daily Upper Intake Level and Guidance Value for Morphine in Poppy Seeds, BfR Heath Assessment No. 0.12\/2006. Available online: https:\/\/mobil.bfr.bund.de\/cm\/349\/bfr_recommends_provisional_daily_upper_intake_level_and_a_guidance_value_for_morphine_in_poppy_seeds.pdf."},{"key":"ref_13","unstructured":"(2020, January 23). European Commision, Health and Food Safety Directorate-General, Summary Report of the Standing Committee on Plants, Animals, Food and Feed Held in Brussels on 25 November 2016. Available online: https:\/\/ec.europa.eu\/food\/sites\/food\/files\/safety\/docs\/reg-com_toxic_20161125_sum.pdf."},{"key":"ref_14","unstructured":"(2020, January 23). Commission Recommendation 2014\/662\/EU of 10 September 2014 on Good Practices to Prevent and to Reduce the Presence of Opium Alkaloids in Poppy Seeds and Poppy Seed Products, Brussels, Belgium, Official Journal of the European Union, L 271\/96 2014. Available online: https:\/\/eur-lex.europa.eu\/legal-content\/EN\/TXT\/PDF\/?uri=CELEX:32014H0662&from=SK."},{"key":"ref_15","unstructured":"European Food Safety Authority (2018). Update of the Scientific Opinion on opium alkaloids in poppy seeds, EFSA Panel on Contaminants in the Food Chain (CONTAM). EFSA J., 16, 5243."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1093\/jat\/27.1.53","article-title":"Urinary concentrations of morphine and codeine after consumption of poppy seeds","volume":"27","author":"Thevis","year":"2003","journal-title":"J. Anal. Toxicol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"399","DOI":"10.5740\/jaoacint.11-102","article-title":"Development and validation of a reversed-phase HPLC method for determination of alkaloids from Papaver somniferum L. (Papaveraceae)","volume":"95","author":"Acevska","year":"2012","journal-title":"J. AOAC Int."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/j.aca.2007.03.050","article-title":"Extraction and determination of papaverin in pericarpium papaveris using aqueous two-phase system of poly(ethyleneglycol)\u2013(NH4)2SO4 coupled with high-performance liquid chromatography","volume":"590","author":"Cao","year":"2007","journal-title":"Anal. Chim. Acta"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"698","DOI":"10.1007\/s12161-012-9479-2","article-title":"Determination of five alkaloids of pericarpium papaveris in hot pot broth using ultra-performance liquid chromatography coupled to triple quadruple mass spectrometry","volume":"6","author":"Guo","year":"2013","journal-title":"Food Anal. Methods"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.indcrop.2012.04.018","article-title":"Analysis of selected poppy (Papaver somniferum L.) cultivars: Pharmaceutically important alkaloids","volume":"41","author":"Stranska","year":"2013","journal-title":"Ind. Crop. Prod."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Casado, N., Ga\u00f1\u00e1n, J., Morante-Zarcero, S., and Sierra, I. (2020). New advanced materials and sorbent-based microextraction techniques as strategies in sample preparation to improve the determination of natural toxins in food samples. Molecules, 25.","DOI":"10.3390\/molecules25030702"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"484","DOI":"10.1002\/jccs.201800310","article-title":"Amantadine-functionalized magnetic microspheres and stable isotope labeled internal standards for reducing matrix effect in determination of five opium alkaloids by liquid chromatography-quadrupole linear ion trap mass spectrometry","volume":"66","author":"Xu","year":"2019","journal-title":"J. Chin. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1016\/j.ijbiomac.2019.12.259","article-title":"Chitosan functionalized magnetic graphene oxide nanocomposite for the sensitive and effective determination of alkaloids in hotpot","volume":"146","author":"Tang","year":"2020","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1251","DOI":"10.1007\/s10337-019-03721-0","article-title":"Recent Applications of Magnetic Solid-phase Extraction for Sample Preparation","volume":"82","author":"Capriotti","year":"2019","journal-title":"Chromatographia"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"7028","DOI":"10.1039\/C7NJ00776K","article-title":"Supercritical fluid extraction of papaverine and noscapine from poppy capsules followed by preconcentration with magnetic nano Fe3O4@Cu@diphenylthiocarbazone particles","volume":"41","author":"Tajik","year":"2017","journal-title":"New J. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1021\/ja0777584","article-title":"Superparamagnetic high-magnetization microspheres with an Fe3O4@SiO2 core and perpendicularly aligned mesoporous SiO2 shell for removal of microcystins","volume":"130","author":"Deng","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1016\/j.foodchem.2019.05.031","article-title":"Reversed-phase\/weak anion Exchange magnetic mesoporous microspheres for removal of matrix effects in lipophilic marine biotoxins analysis by ultrahigh-performance liquid chromatography coupled to tandem mass spectrometry","volume":"294","author":"Xu","year":"2019","journal-title":"Food Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"910","DOI":"10.1039\/C1AN15873B","article-title":"Magnetic retrieval of chitosan: Extraction of bioactive constituents from green tea beverage samples","volume":"137","author":"Zhang","year":"2011","journal-title":"Analyst"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2503","DOI":"10.1039\/c2an35259a","article-title":"Preparation of magnetic molecularly imprinted polymers for separating rutin from Chinese medicinal plants","volume":"137","author":"Zeng","year":"2012","journal-title":"Analyst"},{"key":"ref_30","first-page":"1","article-title":"About the theory of so-called adsorption of soluble substances","volume":"24","author":"Lagergren","year":"1898","journal-title":"K. Sven. Vetenskapsakad. Handl."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1016\/S0032-9592(98)00112-5","article-title":"Pseudo-second order model for sorption processes","volume":"34","author":"Ho","year":"1999","journal-title":"Process. Biochem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1061\/JSEDAI.0000430","article-title":"Kinetics of adsorption on carbon from solution","volume":"89","author":"Weber","year":"1963","journal-title":"J. San. Eng. Div."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1361","DOI":"10.1021\/ja02242a004","article-title":"The adsorption of gases on plane surfaces of glass, mica and platinum","volume":"40","author":"Langmuir","year":"1918","journal-title":"J. Am. Chem. Soc."},{"key":"ref_34","first-page":"385","article-title":"Over the adsorption in solution","volume":"57","author":"Freundlich","year":"1906","journal-title":"Am. J. Phys. Chem."},{"key":"ref_35","unstructured":"European Commission SANTE\/11813\/2017 (2021, April 09). Guidance Document on Analytical Quality Control and Method Validation Procedures for Pesticide Residues and Analysis in Food and Feed. Available online: https:\/\/www.eurl-pesticides.eu\/userfiles\/file\/EurlALL\/AqcGuidance_SANTE_2019_12682.pdf."},{"key":"ref_36","unstructured":"Commission Regulation (EC) No 401\/2006 (2021, April 09). Laying Down the Methods of Sampling and Analysis for the Official Control of the Levels of Mycotoxins in Foodstuffs. Available online: https:\/\/eur-lex.europa.eu\/legal-content\/EN\/TXT\/PDF\/?uri=CELEX:32006R0401&from=ES."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1016\/j.chroma.2013.02.018","article-title":"Preparation of magnetic imprinted polymer for selective recognition of resveratrol in wine","volume":"1300","author":"Chen","year":"2013","journal-title":"J. Chromatogr. A"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"16152","DOI":"10.1039\/D0NJ01634A","article-title":"Simultaneous extraction of permethrin diastereomers and deltamethrin in environmental water samples based on aperture regulated magnetic mesoporous silica","volume":"44","author":"Zhang","year":"2020","journal-title":"New J. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1351\/pac198557040603","article-title":"Reporting physisorption data for gas\/solid systems with special reference to the determination of Surface area and porosity","volume":"57","author":"Sing","year":"1984","journal-title":"IUPAC Pure Appl. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"376","DOI":"10.1093\/jat\/21.5.376","article-title":"The analysis of thebaine in urine for the detection of poppy seed consumption","volume":"21","author":"Cassella","year":"1997","journal-title":"J. Anal. Toxicol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1117","DOI":"10.1007\/s00216-012-5716-1","article-title":"Chemometric approach for development, optimization, and validation of different chromatographic methods for separation of opium alkaloids","volume":"403","author":"Acevska","year":"2012","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"884","DOI":"10.1021\/acs.jafc.9b05153","article-title":"Matrix free laser desorption ionization mass spectrometry as an efficient tool for the rapid detection of opiates in crude extracts of Papaver somniferum","volume":"68","author":"Skopikova","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/19440049.2011.636762","article-title":"Exposure of consumers to morphine from poppy seeds in Hungary","volume":"29","author":"Zentai","year":"2011","journal-title":"Food Addit. Contam. Part A"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"737","DOI":"10.3389\/fchem.2020.00737","article-title":"Opium alkaloids in harvested and thermally processed poppy seeds","volume":"8","author":"Carlin","year":"2020","journal-title":"Front. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"798","DOI":"10.1111\/j.2042-7158.1982.tb06228.x","article-title":"Morphine intake from poppy seed food","volume":"34","author":"Bjerver","year":"2011","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"806","DOI":"10.1093\/clinchem\/33.6.806","article-title":"Concentrations of morphine and codeine in serum and urine after ingestion of poppy seeds","volume":"33","author":"Hayes","year":"1987","journal-title":"Clin. Chem."}],"container-title":["Foods"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2304-8158\/10\/7\/1587\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T06:27:43Z","timestamp":1760164063000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2304-8158\/10\/7\/1587"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,7,8]]},"references-count":46,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2021,7]]}},"alternative-id":["foods10071587"],"URL":"https:\/\/doi.org\/10.3390\/foods10071587","relation":{},"ISSN":["2304-8158"],"issn-type":[{"value":"2304-8158","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,7,8]]}}}