{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,23]],"date-time":"2026-10-23T21:03:30Z","timestamp":1792789410186,"version":"4.5.0"},"reference-count":106,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2020,10,20]],"date-time":"2020-10-20T00:00:00Z","timestamp":1603152000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Global Organization for EPA and DHA Omega-3s","award":["NA"],"award-info":[{"award-number":["NA"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Foods"],"abstract":"<jats:p>A recent study has reported that the administration during gestation of a highly rancid hoki liver oil, obtained by oxidation through sustained exposure to oxygen gas and incident light for 30 days, causes newborn mortality in rats. This effect was attributed to lipid hydroperoxides formed in the omega-3 long-chain polyunsaturated fatty acid-rich oil, while other chemical changes in the damaged oil were overlooked. In the present study, the oxidation condition employed to damage the hoki liver oil was replicated, and the extreme rancidity was confirmed. A detailed analysis of temporal chemical changes resulting from the sustained oxidative challenge involved measures of eicosapentaenoic acid\/docosahexaenoic acid (EPA\/DHA) omega-3 oil oxidative quality (peroxide value, para-anisidine value, total oxidation number, acid value, oligomers, antioxidant content, and induction time) as well as changes in fatty acid content, volatiles, isoprostanoids, and oxysterols. The chemical description was extended to refined anchovy oil, which is a more representative ingredient oil used in omega-3 finished products. The present study also analyzed the effects of a different oxidation method involving thermal exposure in the dark in contact with air, which is an oxidation condition that is more relevant to retail products. The two oils had different susceptibility to the oxidation conditions, resulting in distinct chemical oxidation signatures that were determined primarily by antioxidant protection as well as specific methodological aspects of the applied oxidative conditions. Unique isoprostanoids and oxysterols were formed in the over-oxidized fish oils, which are discussed in light of their potential biological activities.<\/jats:p>","DOI":"10.3390\/foods9101501","type":"journal-article","created":{"date-parts":[[2020,10,20]],"date-time":"2020-10-20T20:50:07Z","timestamp":1603227007000},"page":"1501","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":31,"title":["Chemical Compositional Changes in Over-Oxidized Fish Oils"],"prefix":"10.3390","volume":"9","author":[{"given":"Austin S.","family":"Phung","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of California, Davis, CA 95616, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7763-6224","authenticated-orcid":false,"given":"Gerard","family":"Bannenberg","sequence":"additional","affiliation":[{"name":"Global Organization for EPA and DHA Omega-3s (GOED), Salt Lake City, UT 84105, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1569-0425","authenticated-orcid":false,"given":"Claire","family":"Vigor","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron (IBMM), UMR 5247, CNRS, Universit\u00e9 de Montpellier, ENSCM, 34093 Montpellier, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guillaume","family":"Reversat","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron (IBMM), UMR 5247, CNRS, Universit\u00e9 de Montpellier, ENSCM, 34093 Montpellier, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5177-5792","authenticated-orcid":false,"given":"Camille","family":"Oger","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron (IBMM), UMR 5247, CNRS, Universit\u00e9 de Montpellier, ENSCM, 34093 Montpellier, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8915-795X","authenticated-orcid":false,"given":"Martin","family":"Roumain","sequence":"additional","affiliation":[{"name":"Louvain Drug Research Institute, Universit\u00e9 Catholique de Louvain, 1200 Brussels, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean-Marie","family":"Galano","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron (IBMM), UMR 5247, CNRS, Universit\u00e9 de Montpellier, ENSCM, 34093 Montpellier, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thierry","family":"Durand","sequence":"additional","affiliation":[{"name":"Institut des Biomol\u00e9cules Max Mousseron (IBMM), UMR 5247, CNRS, Universit\u00e9 de Montpellier, ENSCM, 34093 Montpellier, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1600-9259","authenticated-orcid":false,"given":"Giulio G.","family":"Muccioli","sequence":"additional","affiliation":[{"name":"Louvain Drug Research Institute, Universit\u00e9 Catholique de Louvain, 1200 Brussels, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0809-3809","authenticated-orcid":false,"given":"Adam","family":"Ismail","sequence":"additional","affiliation":[{"name":"Global Organization for EPA and DHA Omega-3s (GOED), Salt Lake City, UT 84105, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9030-837X","authenticated-orcid":false,"given":"Selina C.","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Food Science and Technology, University of California, Davis, CA 95616, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,10,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1111\/jhn.12493","article-title":"Eicosapentaenoic acid and docosahexaenoic acid containing supplements modulate risk factors for cardiovascular disease: A meta-analysis of randomised placebo-control human clinical trials","volume":"31","author":"AbuMweis","year":"2018","journal-title":"J. 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