{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T15:48:51Z","timestamp":1792511331272,"version":"4.5.0"},"reference-count":44,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T00:00:00Z","timestamp":1789948800000},"content-version":"vor","delay-in-days":20,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T00:00:00Z","timestamp":1788220800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001824","name":"Grantov\u00e1 Agentura \u010cesk\u00e9 Republiky","doi-asserted-by":"publisher","award":["23\u201004654S"],"award-info":[{"award-number":["23\u201004654S"]}],"id":[{"id":"10.13039\/501100001824","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001823","name":"Ministerstvo \u0160kolstv\u00ed, Ml\u00e1de\u017ee a T\u011blov\u00fdchovy","doi-asserted-by":"publisher","award":["CZ.02.01.01\/00\/22_008\/0004597"],"award-info":[{"award-number":["CZ.02.01.01\/00\/22_008\/0004597"]}],"id":[{"id":"10.13039\/501100001823","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001823","name":"Ministerstvo \u0160kolstv\u00ed, Ml\u00e1de\u017ee a T\u011blov\u00fdchovy","doi-asserted-by":"publisher","award":["LUC25026"],"award-info":[{"award-number":["LUC25026"]}],"id":[{"id":"10.13039\/501100001823","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Food Science &amp; Nutrition"],"published-print":{"date-parts":[[2026,9]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Dietary flavonoids undergo extensive Phase II metabolism, yet the functional consequences of sulfation for their biological activity remain poorly understood. In this study, we compared the physicochemical properties and cellular effects of nine structurally diverse flavonoids and their sulfated derivatives. Flavonoid 3\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010 or 4\u2032\u2010\n                    <jats:italic>O<\/jats:italic>\n                    \u2010sulfates were prepared enzymatically using bacterial aryl sulfotransferase, structurally confirmed, and evaluated as potential metabolites that can be formed by human cytosolic sulfotransferases (SULTs). The results showed that sulfation significantly increased the stability of otherwise labile flavonoids under physiologically relevant conditions, while generally reducing their antiradical capacity and cytotoxicity toward murine RAW264.7 macrophage cells. In contrast to nonsulfated flavonoids, particularly fisetin and quercetin, all tested flavonoid sulfates failed to activate the NRF2 (nuclear factor erythroid 2 p45\u2010related factor 2) pathway in RAW264.7 cells. On the other hand, some of the parent flavonoids as well as flavonoid sulfates partially attenuated lipopolysaccharide\u2010stimulated expression of cyclooxygenase\u20102 (COX\u20102) and inducible nitric oxide synthase (iNOS), indicating that sulfated metabolites retain modulatory effects on inflammatory responses. Using recombinant human sulfotransferases, we identified multiple enzymes responsible for the formation of the tested sulfates, confirming their relevance as plausible metabolites. Overall, our findings demonstrate that metabolic sulfation profoundly reshapes flavonoid stability and biological activity, underscoring the importance of considering conjugated metabolites when evaluating the health effects of dietary flavonoids.\n                  <\/jats:p>","DOI":"10.1002\/fsn3.72382","type":"journal-article","created":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T05:00:21Z","timestamp":1790053221000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Sulfation Rewrites the Biological Profile of Dietary Flavonoids: Implications for Stability, Redox Signaling, and Inflammation"],"prefix":"10.1002","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4337-4980","authenticated-orcid":false,"given":"Ji\u0159\u00ed","family":"Vrba","sequence":"first","affiliation":[{"name":"Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry Palack\u00fd University  Olomouc Czechia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Veronika","family":"Zapletalov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry Palack\u00fd University  Olomouc Czechia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jakub","family":"Havl\u00e1sek","sequence":"additional","affiliation":[{"name":"Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry Palack\u00fd University  Olomouc Czechia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Barbora","family":"Papou\u0161kov\u00e1","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, Faculty of Science Palack\u00fd University  Olomouc Czechia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Barbora","family":"Petr\u00e1nkov\u00e1","sequence":"additional","affiliation":[{"name":"Institute of Microbiology of the Czech Academy of Sciences, Laboratory of Biotransformation  Prague Czechia"},{"name":"Department of Genetics and Microbiology, Faculty of Science Charles University  Prague Czechia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Helena","family":"Pelantov\u00e1","sequence":"additional","affiliation":[{"name":"Institute of Microbiology of the Czech Academy of Sciences Laboratory of Molecular Structure Characterization  Prague Czechia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7714-5350","authenticated-orcid":false,"given":"Kate\u0159ina","family":"Valentov\u00e1","sequence":"additional","affiliation":[{"name":"Institute of Microbiology of the Czech Academy of Sciences, Laboratory of Biotransformation  Prague Czechia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,21]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1004104107"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6c01204"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.18632\/oncotarget.17683"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.21599"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2016.05.005"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2024.102425"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.2147\/Jir.S140188"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0053222"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms11020595"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tibs.2014.02.002"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00204\u2010012\u20100913\u20104"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2022.114078"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.0c03997"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.1093\/carcin\/20.10.1945"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2021.03.034"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.1124\/mol.104.006171"},{"key":"e_1_2_10_18_1","doi-asserted-by":"publisher","DOI":"10.3390\/nutraceuticals6030049"},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2024.1513422"},{"key":"e_1_2_10_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/emm.2013.97"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fitote.2011.01.018"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201500298"},{"key":"e_1_2_10_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10753\u2010016\u20100311\u20109"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.1124\/dmd.109.028399"},{"key":"e_1_2_10_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2016.10.015"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2015.07.055"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2025.116738"},{"key":"e_1_2_10_28_1","doi-asserted-by":"publisher","DOI":"10.3390\/antiox9100973"},{"key":"e_1_2_10_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.freeradbiomed.2007.02.017"},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.2c00720"},{"key":"e_1_2_10_31_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23020480"},{"key":"e_1_2_10_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biocel.2006.03.021"},{"key":"e_1_2_10_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm3013344"},{"key":"e_1_2_10_34_1","doi-asserted-by":"publisher","DOI":"10.3390\/metabo10080329"},{"key":"e_1_2_10_35_1","doi-asserted-by":"publisher","DOI":"10.3390\/antiox10060954"},{"key":"e_1_2_10_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.3c01087"},{"key":"e_1_2_10_37_1","doi-asserted-by":"publisher","DOI":"10.1111\/nbu.12278"},{"key":"e_1_2_10_38_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev\u2010food\u2010060721\u2010023817"},{"key":"e_1_2_10_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2012.05.011"},{"key":"e_1_2_10_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf505514d"},{"key":"e_1_2_10_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf500180u"},{"key":"e_1_2_10_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/mnfr.201200536"},{"key":"e_1_2_10_43_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24040708"},{"key":"e_1_2_10_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chmed.2021.03.002"},{"key":"e_1_2_10_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.crfs.2022.07.007"}],"container-title":["Food Science &amp; Nutrition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/fsn3.72382","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/fsn3.72382","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/fsn3.72382","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T15:18:59Z","timestamp":1792509539000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/fsn3.72382"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9]]},"references-count":44,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2026,9]]}},"alternative-id":["10.1002\/fsn3.72382"],"URL":"https:\/\/doi.org\/10.1002\/fsn3.72382","archive":["Portico"],"relation":{},"ISSN":["2048-7177","2048-7177"],"issn-type":[{"value":"2048-7177","type":"print"},{"value":"2048-7177","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9]]},"assertion":[{"value":"2026-03-02","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-11","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e72382"}}