{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,19]],"date-time":"2025-12-19T15:51:30Z","timestamp":1766159490394,"version":"build-2065373602"},"reference-count":47,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2024,8,2]],"date-time":"2024-08-02T00:00:00Z","timestamp":1722556800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["scijournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["J Sci Food Agric"],"published-print":{"date-parts":[[2024,12]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:sec><jats:title>BACKGROUND<\/jats:title><jats:p>The Maillard reaction involves the interaction of various amino acids and reducing sugars, resulting in food browning. It often produces appealing aromas and flavors. The complexities of the reaction are such that it can be challenging to identify the often numerous and frequently volatile products formed by it. In the present study, we sought to identify and evaluate an unusual product with anti\u2010oxidant activity arising from a fructose\u2010histidine Maillard reaction model. The anti\u2010oxidant profile of this product was assessed by computational means.<\/jats:p><\/jats:sec><jats:sec><jats:title>RESULTS<\/jats:title><jats:p>The fructose\u2010histidine Maillard reaction products (FH\u2010MRPs) were generated by heating a 2:1 mixture of the sugar and the amino acid at 140\u2009\u00b0C for 2\u2009h. Chromatographically separable fractions, labelled DM\u20101 to DM\u20108, were obtained using silica gel as the stationary phase and dichloromethane\/methanol (DCM\/MeOH) mixtures as the mobile one. Fraction DM\u20105 exhibited the highest 2,2\u2010diphenyl\u20101\u2010picrylhydrazyl (DPPH) radical scavenging activity, and further bio\u2010assay guided fractionation led to isolation and identification of 1\u2010(1<jats:italic>H<\/jats:italic>\u2010imidazo[4,5\u2010<jats:italic>c<\/jats:italic>]pyridin\u20104\u2010yl)ethenone (IMPE) as the active principal, the structure of which was established by nuclear magnetic resonance (NMR) spectroscopic and mass spectral techniques. A mechanism for the formation of IMPE from its precursors is proposed. Density functional theory (DFT) calculations suggest this novel heterocyclic compound exerts its anti\u2010oxidant effects by interacting with DPPH and 2,2'\u2010Azino\u2010bis(3\u2010ethylbenzothiazoline\u20106\u2010sulfonic acid) (ABTS) radicals. Essentially, IMPE was non\u2010toxic below 300 ug mL<jats:sup>\u22121<\/jats:sup>, showing a concentration\u2010dependent free radical clearance capacity and reducing power within the 100\u20131000\u2009\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup> range, and moreover, exhibiting significant Fe<jats:sup>2+<\/jats:sup> chelating abilities wihin the 50\u2010200 \u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup> range.<\/jats:p><\/jats:sec><jats:sec><jats:title>CONCLUSION<\/jats:title><jats:p>This study identified the unique FH\u2010MRP, IMPE, and found that it acts as food antioxidant through the chelation of metal ions. \u00a9 2024 Society of Chemical Industry.<\/jats:p><\/jats:sec>","DOI":"10.1002\/jsfa.13779","type":"journal-article","created":{"date-parts":[[2024,8,2]],"date-time":"2024-08-02T08:13:16Z","timestamp":1722586396000},"page":"9548-9558","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Anti\u2010oxidant activity of 1\u2010(1<i>H<\/i>\u2010imidazo[4,5\u2010<i>c<\/i>]pyridin\u20104\u2010yl)ethenone, a <scp>Maillard<\/scp> reaction product derived from fructose and histidine"],"prefix":"10.1002","volume":"104","author":[{"given":"Kangyu","family":"Zhao","sequence":"first","affiliation":[{"name":"Guangdong Joint International Research Centre of Oilseed Biorefinery, Nutrition and Safety, Department of Food Science and Engineering Jinan University  Guangzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xin","family":"Long","sequence":"additional","affiliation":[{"name":"Guangdong Joint International Research Centre of Oilseed Biorefinery, Nutrition and Safety, Department of Food Science and Engineering Jinan University  Guangzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Junle","family":"Li","sequence":"additional","affiliation":[{"name":"Guangdong Joint International Research Centre of Oilseed Biorefinery, Nutrition and Safety, Department of Food Science and Engineering Jinan University  Guangzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ying","family":"Wang","sequence":"additional","affiliation":[{"name":"Guangdong Joint International Research Centre of Oilseed Biorefinery, Nutrition and Safety, Department of Food Science and Engineering Jinan University  Guangzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9285-3259","authenticated-orcid":false,"given":"Ping","family":"Lan","sequence":"additional","affiliation":[{"name":"Guangdong Joint International Research Centre of Oilseed Biorefinery, Nutrition and Safety, Department of Food Science and Engineering Jinan University  Guangzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7547-1542","authenticated-orcid":false,"given":"Yong","family":"Wang","sequence":"additional","affiliation":[{"name":"Guangdong Joint International Research Centre of Oilseed Biorefinery, Nutrition and Safety, Department of Food Science and Engineering Jinan University  Guangzhou China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,8,2]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-019-41824-8"},{"key":"e_1_2_9_3_1","first-page":"1","article-title":"Food polyphenols and Maillard reaction: regulation effect and chemical mechanism","volume":"0","author":"Han Z","year":"2022","journal-title":"Crit Rev Food Sci Nutr"},{"key":"e_1_2_9_4_1","first-page":"76","volume-title":"Effect of Emerging Processing Technologies on Maillard Reactions, in the Encyclopedia of Food Chemistry","author":"Koubaa M","year":"2019"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2023.136655"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2023.113226"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1111\/1541-4337.12780"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.8b01561"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7FO01438D"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2018.09.083"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1080\/10408398.2021.1937509"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/jsfa.8295"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2021.129488"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fmre.2021.06.022"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2020.126974"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2022.133416"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1111\/1750-3841.14579"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1111\/ijfs.14881"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6b03398"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.2c00104"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2020.127678"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2023.137137"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2023.137465"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2020.127934"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules27248857"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.lwt.2022.113343"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6b00157"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2010.12.099"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.lwt.2021.111151"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13197-017-2982-0"},{"key":"e_1_2_9_31_1","unstructured":"FrischMJ TrucksGW SchlegelHB ScuseriaGE RobbMA CheesemanJRet al. Gaussian~16 Revision A.03(2016)."},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.22885"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2020.127167"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.3390\/antiox10111840"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.lwt.2021.111833"},{"key":"e_1_2_9_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2022.134318"},{"key":"e_1_2_9_37_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13197-020-04615-y"},{"key":"e_1_2_9_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2012.09.030"},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2013.09.034"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf00028a026"},{"first-page":"106","volume-title":"Maillard Reactions in Chemistry, Food and Health","author":"Gi US","key":"e_1_2_9_41_1"},{"volume-title":"Encyclopedia of Food and Health","author":"Rufi\u00e1n\u2010Henares JA","key":"e_1_2_9_42_1"},{"key":"e_1_2_9_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biochi.2010.06.012"},{"key":"e_1_2_9_44_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21081020"},{"key":"e_1_2_9_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2021.131567"},{"key":"e_1_2_9_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2021.130432"},{"key":"e_1_2_9_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2018.11.028"},{"key":"e_1_2_9_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2014.10.513"}],"container-title":["Journal of the Science of Food and Agriculture"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/scijournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jsfa.13779","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T11:55:20Z","timestamp":1760874920000},"score":1,"resource":{"primary":{"URL":"https:\/\/scijournals.onlinelibrary.wiley.com\/doi\/10.1002\/jsfa.13779"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,8,2]]},"references-count":47,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2024,12]]}},"alternative-id":["10.1002\/jsfa.13779"],"URL":"https:\/\/doi.org\/10.1002\/jsfa.13779","archive":["Portico"],"relation":{},"ISSN":["0022-5142","1097-0010"],"issn-type":[{"type":"print","value":"0022-5142"},{"type":"electronic","value":"1097-0010"}],"subject":[],"published":{"date-parts":[[2024,8,2]]},"assertion":[{"value":"2024-04-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-07-13","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-08-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}