{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:31:37Z","timestamp":1760315497444,"version":"build-2065373602"},"reference-count":70,"publisher":"Wiley","issue":"37","license":[{"start":{"date-parts":[[2021,5,29]],"date-time":"2021-05-29T00:00:00Z","timestamp":1622246400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100010099","name":"\u00dastav organick\u00e9 chemie a biochemie Akademie v\u011bd \u010cesk\u00e9 republiky","doi-asserted-by":"publisher","award":["RVO:61388963"],"award-info":[{"award-number":["RVO:61388963"]}],"id":[{"id":"10.13039\/501100010099","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2021,7,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Phytoprostanes (PhytoP) are natural products, which form in plants under oxidative stress conditions from \u03b1\u2010linolenic acid. However, their epimers with relative prostaglandin configuration termed phytoglandins (PhytoG) have never been detected in Nature, likely because of the lack of synthetic reference material. Here, the first asymmetric total synthesis of such compounds, namely of PhytoGF<jats:sub>1\u03b1<\/jats:sub> (9\u2010<jats:italic>epi<\/jats:italic>\u201016\u2010F<jats:sub>1t<\/jats:sub>\u2010PhytoP) and its diastereomer <jats:italic>ent<\/jats:italic>\u201016\u2010<jats:italic>epi<\/jats:italic>\u2010PhytoGF<jats:sub>1\u03b1<\/jats:sub> (<jats:italic>ent<\/jats:italic>\u20109,16\u2010<jats:italic>diepi<\/jats:italic>\u201016\u2010F<jats:sub>1t<\/jats:sub>\u2010PhytoP), has been accomplished. The synthetic strategy is based on radical anion oxidative cyclization, copper(I)\u2010mediated alkyl\u2010alkyl coupling and enantioselective reduction reactions. A UHPLC\u2010MS\/MS study using the synthesized compounds as standards indicates PhytoG formation at significant levels during autoxidation of \u03b1\u2010linolenic acid in edible vegetable oils. Initial testing of synthetic PhytoGs together with F<jats:sub>1<\/jats:sub>\u2010PhytoP and 15\u2010F<jats:sub>2t<\/jats:sub>\u2010IsoP derivatives for potential interactions with the PGF<jats:sub>2\u03b1<\/jats:sub> (FP) receptor did not reveal significant activity. The notion that PUFA\u2010derived oxidatively formed cyclic metabolites with prostaglandin configuration do not form to a significant extent in biological or food matrices has to be corrected. Strong evidence is provided that oxidatively formed PhytoG metabolites may be ingested with plant\u2010derived food, which necessitates further investigation of their biological profile.<\/jats:p>","DOI":"10.1002\/chem.202100872","type":"journal-article","created":{"date-parts":[[2021,4,27]],"date-time":"2021-04-27T05:09:12Z","timestamp":1619500152000},"page":"9556-9562","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["First Total Synthesis of Phytoprostanes with Prostaglandin\u2010Like Configuration, Evidence for Their Formation in Edible Vegetable Oils and Orienting Study of Their Biological Activity"],"prefix":"10.1002","volume":"27","author":[{"given":"Jakub","family":"Smr\u010dek","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences  Flemingovo n\u00e1m\u011bst\u00ed 2 16610 Prague 6 Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miroslav","family":"H\u00e1jek","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences  Flemingovo n\u00e1m\u011bst\u00ed 2 16610 Prague 6 Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ond\u0159ej","family":"Hodek","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences  Flemingovo n\u00e1m\u011bst\u00ed 2 16610 Prague 6 Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Karel","family":"\u010c\u00ed\u017eek","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences  Flemingovo n\u00e1m\u011bst\u00ed 2 16610 Prague 6 Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7898-946X","authenticated-orcid":false,"given":"Radek","family":"Pohl","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences  Flemingovo n\u00e1m\u011bst\u00ed 2 16610 Prague 6 Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emanuela","family":"Jahn","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences  Flemingovo n\u00e1m\u011bst\u00ed 2 16610 Prague 6 Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jean\u2010Marie","family":"Galano","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron IBMM CNRS ENSCM Facult\u00e9 de Pharmacie Universit\u00e9 de Montpellier  15 Av. Charles Flahault CS14491, 34093 Montpellier Cedex 05 France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Camille","family":"Oger","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron IBMM CNRS ENSCM Facult\u00e9 de Pharmacie Universit\u00e9 de Montpellier  15 Av. Charles Flahault CS14491, 34093 Montpellier Cedex 05 France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thierry","family":"Durand","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron IBMM CNRS ENSCM Facult\u00e9 de Pharmacie Universit\u00e9 de Montpellier  15 Av. Charles Flahault CS14491, 34093 Montpellier Cedex 05 France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Josef","family":"Cva\u010dka","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences  Flemingovo n\u00e1m\u011bst\u00ed 2 16610 Prague 6 Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8386-1348","authenticated-orcid":false,"given":"Ullrich","family":"Jahn","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences  Flemingovo n\u00e1m\u011bst\u00ed 2 16610 Prague 6 Czech Republic"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,5,29]]},"reference":[{"volume-title":"Prostaglandins: Biochemistry, Functions, Types, and Roles","year":"2010","author":"Goodwin G. M.","key":"e_1_2_6_1_1"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr068365a"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527613625"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1105\/tpc.000679"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1093\/aob\/mcm079"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1093\/aob\/mct067"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.nbt.2015.11.001"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-319-25979-6_16"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1093\/jxb\/erw495"},{"volume-title":"Oxidative Stress in Vertebrates and Invertebrates: Molecular Aspects on Cell Signaling","year":"2012","author":"Farooqui T.","key":"e_1_2_6_10_1"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/bk-2011-1083"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.87.23.9383"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M601035200"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1006\/bbrc.1997.6869"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705122"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200705122"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.plefa.2009.10.005"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.273.22.13605"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1194\/jlr.R800037-JLR200"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200160h"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)97174-1"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00382a001"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biochi.2010.05.014"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1186\/1423-0127-17-24"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms11114631"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.plipres.2017.09.004"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M608975200"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M303984200"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.273.49.32650"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pbi.2004.04.001"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/lite.201500020"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.3945\/jn.109.108316"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1080\/10715760600939734"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1084\/jem.20041065"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jaci.2007.03.017"},{"key":"e_1_2_6_35_1","volume":"3","author":"Blume C.","year":"2015","journal-title":"Tissue Antigens"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1111\/all.12707"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.3389\/fimmu.2019.00974"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2017.02.049"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.lwt.2015.07.005"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.7b03482"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA07803B"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2016.05.132"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA90022D"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1080\/10715762.2017.1288909"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6b03011"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02505J"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c02553"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbalip.2014.10.007"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbalip.2014.11.004"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.272.43.27147"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-319-03979-4_69"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja027154u"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201600540"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB00200A"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0690(200202)2002:4<718::AID-EJOC718>3.0.CO;2-6"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200802139"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo1006569"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1016\/0090-6980(77)90157-5"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01263a071"},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)00171-0"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo035638i"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00324a028"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2015.01.097"},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0891-5849(00)00154-4"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1300\/J133v02n04_04"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.4172\/2155-9600.1000582"},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.3389\/fnut.2019.00094"},{"key":"e_1_2_6_68_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms160612871"},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf0478354"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202100872","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202100872","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202100872","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T11:25:14Z","timestamp":1760268314000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202100872"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,29]]},"references-count":70,"journal-issue":{"issue":"37","published-print":{"date-parts":[[2021,7,2]]}},"alternative-id":["10.1002\/chem.202100872"],"URL":"https:\/\/doi.org\/10.1002\/chem.202100872","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2021,5,29]]},"assertion":[{"value":"2021-03-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-05-29","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}