{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,20]],"date-time":"2026-07-20T13:53:12Z","timestamp":1784555592502,"version":"3.55.0"},"reference-count":38,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2022,4,28]],"date-time":"2022-04-28T00:00:00Z","timestamp":1651104000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003453","name":"Natural Science Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2020A1515110453"],"award-info":[{"award-number":["2020A1515110453"]}],"id":[{"id":"10.13039\/501100003453","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003453","name":"Natural Science Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2021A1515010110"],"award-info":[{"award-number":["2021A1515010110"]}],"id":[{"id":"10.13039\/501100003453","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82003609"],"award-info":[{"award-number":["82003609"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002858","name":"China Postdoctoral Science Foundation","doi-asserted-by":"publisher","award":["2019M663403"],"award-info":[{"award-number":["2019M663403"]}],"id":[{"id":"10.13039\/501100002858","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100021171","name":"Basic and Applied Basic Research Foundation of Guangdong Province","doi-asserted-by":"publisher","award":["2021A1515110430"],"award-info":[{"award-number":["2021A1515110430"]}],"id":[{"id":"10.13039\/501100021171","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Nutr."],"abstract":"<jats:title>Graphical Abstract<\/jats:title><jats:p><jats:italic>In vitro<\/jats:italic>digestion of the adduct (HMZ) formed between zingerone and HMF, cytotoxicity against Caco-2 cells of HMZ, and absorption of HMZ by Caco-2 cells<\/jats:p>","DOI":"10.3389\/fnut.2022.893991","type":"journal-article","created":{"date-parts":[[2023,4,18]],"date-time":"2023-04-18T11:58:47Z","timestamp":1681819127000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":5,"title":["Formation and Identification of a 5-(Hydroxymethyl)-2-Furfural-Zingerone Condensate and Its Cytotoxicity in Caco-2 Cells"],"prefix":"10.3389","volume":"9","author":[{"given":"Yujing","family":"Ke","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhao","family":"Yin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nenghua","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peifang","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jie","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shiyi","family":"Ou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guoqiang","family":"Li","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2022,4,28]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"1941","DOI":"10.3390\/molecules25081941","article-title":"The toxicological aspects of the heat-borne toxicant 5-hydroxymethylfurfural in animals: a review","volume":"25","author":"Farag","year":"2020","journal-title":"Molecules."},{"key":"B2","doi-asserted-by":"publisher","first-page":"35","DOI":"10.1186\/s13065-018-0408-3","article-title":"5-Hydroxymethylfurfural (HMF) levels in honey and other food products: effects on bees and human health","volume":"12","author":"Shapla","year":"2018","journal-title":"Chem Cent J"},{"key":"B3","doi-asserted-by":"publisher","first-page":"1866","DOI":"10.1080\/10942912.2016.1222587","article-title":"Effect of brewing process and sugar content on 5-hydroxymethylfurfural and related substances from Turkish coffee","volume":"20","author":"Mortas","year":"2016","journal-title":"Int J Food Prop."},{"key":"B4","doi-asserted-by":"publisher","first-page":"63","DOI":"10.1016\/j.jcs.2005.05.001","article-title":"Analysis of heat-damage indices in breakfast cereals: influence of composition","volume":"43","author":"Rufi\u00e1n-Henares","year":"2006","journal-title":"J Cereal Sci."},{"key":"B5","doi-asserted-by":"publisher","first-page":"842","DOI":"10.1002\/mnfr.200500262","article-title":"Analysis of 5-hydroxymethylfurfual in coffee, dried fruits and urine","volume":"50","author":"Murkovic","year":"2006","journal-title":"Mol Nutr Food Res."},{"key":"B6","doi-asserted-by":"publisher","first-page":"1135","DOI":"10.1080\/19440049.2020.1757162","article-title":"Evaluation of 5-hydroxymethylfurfural content in market milk products","volume":"37","author":"Czerwonka","year":"2020","journal-title":"Food Addit Contam Part A Chem Anal Control Expo Risk Assess."},{"key":"B7","doi-asserted-by":"publisher","first-page":"801","DOI":"10.1016\/S0278-6915(00)00070-3","article-title":"5-hydroxymethylfurfural: assessment of mutagenicity, dna-damaging potential and reactivity towards cellular glutathione","volume":"38","author":"Janzowski","year":"2000","journal-title":"Food Chem Toxicol"},{"key":"B8","doi-asserted-by":"publisher","first-page":"308","DOI":"10.1016\/j.foodres.2017.05.034","article-title":"Formation and elimination reactions of 5-hydroxymethylfurfural during in vitro digestion of biscuits","volume":"99","author":"Hamzalioglu","year":"2017","journal-title":"Food Res Int."},{"key":"B9","doi-asserted-by":"publisher","first-page":"164","DOI":"10.1016\/j.foodchem.2015.02.135","article-title":"Formation and reduction of 5-hydroxymethylfurfural at frying temperature in model system as a function of amino acid and sugar composition","volume":"182","author":"Kavousi","year":"2015","journal-title":"Food Chem."},{"key":"B10","doi-asserted-by":"publisher","first-page":"414","DOI":"10.1016\/j.bcp.2009.04.017","article-title":"Renal organic anion transporters OAT1 and OAT3 mediate the cellular accumulation of 5-sulfooxymethylfurfural, a reactive, nephrotoxic metabolite of the Maillard product 5-hydroxymethylfurfural","volume":"78","author":"Bakhiya","year":"2009","journal-title":"Biochem Pharmacol."},{"key":"B11","doi-asserted-by":"publisher","first-page":"701","DOI":"10.1007\/s00204-012-0807-5","article-title":"Toxicity studies with 5-hydroxymethylfurfural and its metabolite 5-sulphooxymethylfurfural in wild-type mice and transgenic mice expressing human sulphotransferases 1A1 and 1A2","volume":"86","author":"Bauer-Marinovic","year":"2012","journal-title":"Arch Toxicol."},{"key":"B12","doi-asserted-by":"publisher","first-page":"1","DOI":"10.2903\/j.efsa.2009.752","article-title":"Consideration of furfuryl alcohol and related flavouring substances evaluated by JECFA (55th meeting) structurally related to furfuryl and furan derivatives with and without additional side chain substituents and heteroatoms","volume":"752","year":"2009","journal-title":"EFSA J"},{"key":"B13","doi-asserted-by":"publisher","first-page":"167","DOI":"10.1016\/j.foodchem.2019.02.053","article-title":"Influences of stir-frying and baking on flavonoid profile, antioxidant property, and hydroxymethylfurfural formation during preparation of blueberry-filled pastries","volume":"287","author":"Yang","year":"2019","journal-title":"Food Chem."},{"key":"B14","doi-asserted-by":"publisher","first-page":"10214","DOI":"10.1021\/acs.jafc.9b04539","article-title":"Identification of a 5-hydroxymethylfurfural-lysine Schiff base and its cytotoxicity in three cell lines","volume":"67","author":"Wang","year":"2019","journal-title":"J Agric Food Chem."},{"key":"B15","doi-asserted-by":"publisher","first-page":"5571","DOI":"10.1021\/jf025503y","article-title":"Role of aldehydic derivatives in the condensation of phenolic compounds with emphasis on the sensorial properties of fruit-derived foods","volume":"50","author":"Es-Safi","year":"2002","journal-title":"J Agric Food Chem."},{"key":"B16","doi-asserted-by":"publisher","first-page":"140","DOI":"10.1016\/j.semcancer.2019.08.009","article-title":"Ginger and its active compounds in cancer therapy: from folk uses to nano-therapeutic applications","volume":"69","author":"Mahomoodally","year":"2021","journal-title":"Semin Cancer Biol."},{"key":"B17","doi-asserted-by":"publisher","first-page":"7617","DOI":"10.1021\/jf051014x","article-title":"Zingerone as an antioxidant against peroxynitrite","volume":"53","author":"Shin","year":"2005","journal-title":"J Agric Food Chem."},{"key":"B18","doi-asserted-by":"publisher","first-page":"186","DOI":"10.1007\/s10753-020-01320-y","article-title":"Zingerone mitigates carrageenan-induced inflammation through antioxidant and anti-inflammatory activities","volume":"44","author":"Mehrzadi","year":"2021","journal-title":"J Inflamm."},{"key":"B19","doi-asserted-by":"publisher","first-page":"e22387","DOI":"10.1002\/jbt.22387","article-title":"Zingerone induced caspase-dependent apoptosis in MCF-7 cells and prevents 7,12-dimethylbenz(a)anthracene-induced mammary carcinogenesis in experimental rats","volume":"33","author":"Gan","year":"2019","journal-title":"J Biochem Mol Toxicol."},{"key":"B20","doi-asserted-by":"publisher","first-page":"182","DOI":"10.1002\/jbt.21683","article-title":"Antihyperlipidaemic, antihypertrophic, and reducing effects of zingerone on experimentally induced myocardial infarcted rats","volume":"29","author":"Hemalatha","year":"2015","journal-title":"J Biochem Mol Toxicol."},{"key":"B21","doi-asserted-by":"publisher","first-page":"650","DOI":"10.1016\/j.foodchem.2012.08.052","article-title":"Synthesis of quinoline derivatives of tetrahydrocurcumin and zingerone and evaluation of their antioxidant and antibacterial attributes","volume":"136","author":"Manjunatha","year":"2013","journal-title":"Food Chem."},{"key":"B22","doi-asserted-by":"publisher","first-page":"169","DOI":"10.1007\/s11010-016-2798-7","article-title":"Antioxidant and anti-inflammatory role of zingerone in ethanol-induced hepatotoxicity","volume":"421","author":"Mani","year":"2016","journal-title":"Mol Cell Biochem."},{"key":"B23","doi-asserted-by":"publisher","first-page":"573","DOI":"10.1021\/ol006976y","article-title":"Proline-catalyzed asymmetric aldol reactions between ketones and \u03b1-unsubstituted aldehydes","volume":"3","author":"List","year":"2001","journal-title":"Org Lett."},{"key":"B24","doi-asserted-by":"publisher","first-page":"1327","DOI":"10.1080\/00397911.2016.1206938","article-title":"Review of the aldol reaction","volume":"46","author":"Mandal","year":"2016","journal-title":"Synth Commun."},{"key":"B25","doi-asserted-by":"publisher","first-page":"5839","DOI":"10.1073\/pnas.0307979101","article-title":"New mechanistic studies on the proline-catalyzed aldol reaction","volume":"101","author":"List","year":"2004","journal-title":"Proc Natl Acad Sci USA."},{"key":"B26","doi-asserted-by":"publisher","first-page":"2395","DOI":"10.1021\/ja994280y","article-title":"Proline-catalyzed direct asymmetric aldol reactions","volume":"122","author":"List","year":"2000","journal-title":"J Am Chem Soc."},{"key":"B27","doi-asserted-by":"publisher","first-page":"87","DOI":"10.1016\/j.foodchem.2019.01.183","article-title":"Metabolomic analysis of energy regulated germination and sprouting of organic mung bean (Vigna radiata) using NMR spectroscopy","volume":"286","author":"Chen","year":"2019","journal-title":"Food Chem."},{"key":"B28","doi-asserted-by":"publisher","first-page":"107623","DOI":"10.1016\/j.foodhyd.2022.107623","article-title":"Konjac glucomannan decreases metabolite release of a plant-based fishball analogue during in vitro digestion by affecting amino acid and carbohydrate metabolic pathways","volume":"129","author":"Ran","year":"2022","journal-title":"Food Hydrocoll."},{"key":"B29","doi-asserted-by":"publisher","first-page":"110355","DOI":"10.1016\/j.foodres.2021.110355","article-title":"Metabolite release and rheological properties of sponge cake after in vitro digestion and the influence of a flour replacer rich in dietary fibre","volume":"144","author":"Huang","year":"2021","journal-title":"Food Res Int."},{"key":"B30","doi-asserted-by":"publisher","first-page":"288","DOI":"10.1016\/j.foodchem.2014.08.070","article-title":"Identification of bioaccessible and uptaken phenolic compounds from strawberry fruits in in vitro digestion\/Caco-2 absorption model","volume":"170","author":"Kosi\u0144ska-Cagnazzo","year":"2015","journal-title":"Food Chem."},{"key":"B31","doi-asserted-by":"publisher","first-page":"9902","DOI":"10.1021\/acs.jafc.7b03938","article-title":"Formation of a hydroxymethylfurfural-cysteine adduct and its absorption and cytotoxicity in Caco-2 cells","volume":"65","author":"Zhao","year":"2017","journal-title":"J Agric Food Chem."},{"key":"B32","doi-asserted-by":"publisher","first-page":"125443","DOI":"10.1016\/j.foodchem.2019.125443","article-title":"Thermal disruption of the food matrix of biofortified lettuce varieties modifies absorption of carotenoids by Caco-2 cells","volume":"308","author":"de Oliveira","year":"2019","journal-title":"Food Chem."},{"key":"B33","doi-asserted-by":"publisher","first-page":"289","DOI":"10.1002\/ps.263","article-title":"Insect growth inhibition, antifeedant and antifungal activity of compounds isolated\/derived from Zingiber officinale Roscoe (ginger) rhizomes","volume":"57","author":"Agarwal","year":"2001","journal-title":"Pest Manag Sci."},{"key":"B34","doi-asserted-by":"publisher","first-page":"4194","DOI":"10.1039\/C3RA45632C","article-title":"Efficient production of 5-hydroxymethylfurfural and alkyl levulinate from biomass carbohydrate using ionic liquid-based polyoxometalate salts","volume":"4","author":"Chen","year":"2014","journal-title":"RSC Adv."},{"key":"B35","doi-asserted-by":"publisher","first-page":"132523","DOI":"10.1016\/j.foodchem.2022.132523","article-title":"Effect of food processing on reduction and degradation pathway of pyrethroid pesticides in mackerel fillet (Scomberomorus commerson)","volume":"384","author":"Wongmaneepratip","year":"2022","journal-title":"Food Chem."},{"key":"B36","doi-asserted-by":"publisher","first-page":"1458","DOI":"10.1038\/nprot.2006.238","article-title":"Analysis of apoptosis by propidium iodide staining and flow cytometry","volume":"1","author":"Riccardi","year":"2006","journal-title":"Nat Protoc."},{"key":"B37","doi-asserted-by":"publisher","first-page":"893","DOI":"10.2174\/138920008786485119","article-title":"Permeability for intestinal absorption: caco-2 assay and related issues","volume":"9","author":"Press","year":"2008","journal-title":"Curr Drug Metab."},{"key":"B38","doi-asserted-by":"publisher","first-page":"109240","DOI":"10.1016\/j.foodres.2020.109240","article-title":"Transport, metabolism and remedial potential of functional food extracts (FFEs) in Caco-2 cells monolayer: a review","volume":"136","author":"Iftikhar","year":"2020","journal-title":"Food Res Int."}],"container-title":["Frontiers in Nutrition"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fnut.2022.893991\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,18]],"date-time":"2023-04-18T11:58:52Z","timestamp":1681819132000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fnut.2022.893991\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,28]]},"references-count":38,"alternative-id":["10.3389\/fnut.2022.893991"],"URL":"https:\/\/doi.org\/10.3389\/fnut.2022.893991","relation":{},"ISSN":["2296-861X"],"issn-type":[{"value":"2296-861X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,4,28]]},"article-number":"893991"}}