{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T22:07:19Z","timestamp":1788991639509,"version":"build-2803163510"},"reference-count":43,"publisher":"American Chemical Society (ACS)","issue":"35","license":[{"start":{"date-parts":[[2026,8,29]],"date-time":"2026-08-29T00:00:00Z","timestamp":1787961600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/na","name":"Academy of Finland","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Finnish Cultural Foundation","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/na","name":"Niemi Foundation","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/na","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,9]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Omega-3 polyunsaturated fatty acids (n-3 PUFA), such as \u03b1-linolenic acid (ALA), are crucial for human health. Although n-3 PUFAs in food are mainly in triacylglycerol (TAG) form, they are often provided as ethyl esters (EE) in supplements. Previous research has demonstrated improved postprandial bioavailability of n-3 PUFAs in the EE form when coingested with fat, potentially due to transesterification during digestion. To shed light on the bioavailability improvement, this study investigated the influence of triolein and 2-monoolein on the digestion of ALA-EE using an in vitro model, employing 1H NMR spectroscopy and liquid chromatography combined with mass spectrometry. ALA-EE hydrolysis increased from 6.6 to 22\u201329% with acylglycerols, reaching 55.8% after longer incubation with 2-monoolein. Transesterification of ALA in acylglycerols was observed, especially after incubation with 2-monoolein, but its correlation with ALA-EE hydrolysis remained ambiguous. Therefore, the bioavailability improvements were attributed to the facilitating effect of TAG lipolysis products on ALA release.<\/jats:p>","DOI":"10.1021\/acs.jafc.6c03597","type":"journal-article","created":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T12:20:37Z","timestamp":1788351637000},"page":"27512-27520","source":"Crossref","is-referenced-by-count":0,"title":["<i>In Vitro<\/i>\n                    Evidence of \u03b1-Linolenic\nAcid Ethyl Ester Hydrolysis and Transesterification in the Gastrointestinal\nTract in the Presence of Acylglycerols"],"prefix":"10.1021","volume":"74","author":[{"given":"Gabriele","family":"Beltrame","sequence":"first","affiliation":[{"name":"University of Turku , , ,","place":["Turku, Finland, FI-20014"]},{"name":"Chalmers University of Technology , , ,","place":["Gothenburg, Sweden, SE-41296"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Iida","family":"Valta","sequence":"additional","affiliation":[{"name":"University of Turku , , ,","place":["Turku, Finland, FI-20014"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eija","family":"Ahonen","sequence":"additional","affiliation":[{"name":"University of Turku , , ,","place":["Turku, Finland, FI-20014"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Annelie","family":"Damerau","sequence":"additional","affiliation":[{"name":"University of Turku , , ,","place":["Turku, Finland, FI-20014"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1977-7322","authenticated-orcid":true,"given":"Kaisa M.","family":"Linderborg","sequence":"additional","affiliation":[{"name":"University of Turku , , ,","place":["Turku, Finland, FI-20014"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,29]]},"reference":[{"key":"2026090917070152900_cit1","doi-asserted-by":"publisher","first-page":"255","DOI":"10.1016\/j.lfs.2018.04.049","article-title":"Omega-3 and Omega-6 Polyunsaturated Fatty Acids: Dietary\nSources, Metabolism, and Significance \u2500 A Review","volume":"203","author":"Saini","year":"2018","journal-title":"Life Sci."},{"issue":"11","key":"2026090917070152900_cit2","doi-asserted-by":"publisher","first-page":"2433","DOI":"10.1016\/S0022-2275(20)39724-8","article-title":"Docosahexaenoic\nAcid Synthesis in Human Skin Fibroblasts Involves Peroxisomal Retroconversion\nof Tetracosahexaenoic Acid","volume":"36","author":"Moore","year":"1995","journal-title":"J. Lipid Res."},{"issue":"1","key":"2026090917070152900_cit3","doi-asserted-by":"publisher","first-page":"39","DOI":"10.1159\/000456723","article-title":"Systematic Review\non N-3 and N-6 Polyunsaturated Fatty Acid Intake in European Countries\nin Light of the Current Recommendations - Focus on Specific Population\nGroups","volume":"70","author":"Sioen","year":"2017","journal-title":"Ann. Nutr. 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Neurobiol."},{"issue":"4","key":"2026090917070152900_cit6","doi-asserted-by":"publisher","first-page":"783","DOI":"10.1093\/ajcn\/77.4.783","article-title":"Plant-\nand Marine-Derived\nN\u20133 Polyunsaturated Fatty Acids Have Differential Effects on\nFasting and Postprandial Blood Lipid Concentrations and on the Susceptibility\nof LDL to Oxidative Modification in Moderately Hyperlipidemic Subjects","volume":"77","author":"Finnegan","year":"2003","journal-title":"Am. J. Clin. Nutr."},{"issue":"6","key":"2026090917070152900_cit7","doi-asserted-by":"publisher","first-page":"1108","DOI":"10.1093\/advances\/nmz048","article-title":"Effects of Flaxseed\nInterventions on Circulating Inflammatory Biomarkers: A Systematic\nReview and Meta-Analysis of Randomized Controlled Trials","volume":"10","author":"Rahimlou","year":"2019","journal-title":"Adv. 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Lipid Sci.\nTechnol."},{"issue":"1","key":"2026090917070152900_cit27","doi-asserted-by":"publisher","first-page":"137","DOI":"10.1016\/S0022-2275(20)42768-3","article-title":"Lipopolysis of Menhaden Oil Triacylglycerols\nand the Corresponding Fatty Acid Alkyl Esters by Pancreatic Lipase\nin Vitro: A Reexamination","volume":"31","author":"Yang","year":"1990","journal-title":"J. Lipid Res."},{"key":"2026090917070152900_cit28","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2022.111633","article-title":"Addressing Criticalities in the INFOGEST Static in\nVitro Digestion Protocol for Oleogel Analysis","volume":"160","author":"Sabet","year":"2022","journal-title":"Food Res. Int."},{"issue":"8","key":"2026090917070152900_cit29","doi-asserted-by":"publisher","first-page":"7126","DOI":"10.1039\/D0FO01506G","article-title":"Factors\nImpacting Lipid Digestion and \u03b2-Carotene Bioaccessibility Assessed\nby Standardized Gastrointestinal Model (INFOGEST): Oil Droplet Concentration","volume":"11","author":"Tan","year":"2020","journal-title":"Food Funct."},{"key":"2026090917070152900_cit30","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2025.117501","article-title":"Online SPME-GC-MS Is a Feasible Method\nto Monitor Lipid Oxidation during Simulated Digestion of Oils Incorporated\nin a Meal","volume":"221","author":"Beltrame","year":"2025","journal-title":"Food Res. Int."},{"key":"2026090917070152900_cit31","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2026.149454","article-title":"Role of\nLipolysis and Tocopherols in the Formation of Primary and Secondary\nOxidation Products during Simulated Gastrointestinal Digestion of\nN-3 PUFA-Rich Oils","volume":"517","author":"Beltrame","year":"2026","journal-title":"Food Chem."},{"issue":"1","key":"2026090917070152900_cit32","doi-asserted-by":"publisher","first-page":"30","DOI":"10.1039\/C5FO00930H","article-title":"Relevant PH\nand Lipase for in Vitro Models of Gastric Digestion","volume":"7","author":"Sams","year":"2016","journal-title":"Food Funct."},{"issue":"8","key":"2026090917070152900_cit33","doi-asserted-by":"publisher","first-page":"1831","DOI":"10.1007\/s11095-010-0362-9","article-title":"Effects of Surfactants on Lipase Structure, Activity,\nand Inhibition","volume":"28","author":"Delorme","year":"2011","journal-title":"Pharm. Res."},{"issue":"8","key":"2026090917070152900_cit34","doi-asserted-by":"publisher","DOI":"10.2460\/ajvr.22.03.0048","article-title":"Lipases: It\u2019s\nNot Just Pancreatic\nLipase!","volume":"83","author":"Lim","year":"2022","journal-title":"Am. J. Vet. Res."},{"issue":"2","key":"2026090917070152900_cit35","doi-asserted-by":"publisher","first-page":"480","DOI":"10.1139\/o90-068","article-title":"Intestinal Absorption\nof Menhaden\nand Rapeseed Oils and Their Fatty Acid Methyl and Ethyl Esters in\nthe Rat","volume":"68","author":"Yang","year":"1990","journal-title":"Biochem. Cell Biol."},{"key":"2026090917070152900_cit36","doi-asserted-by":"publisher","DOI":"10.1016\/j.fbio.2025.106756","article-title":"Influence of Molecular Form of Eicosapentaenoic\nAcid (EPA) on Its\nin Vitro Digestion and in Vivo Pharmacokinetics: Monoacylglycerol,\nTriacylglycerol, and Ethyl Ester Forms","volume":"68","author":"Cao","year":"2025","journal-title":"Food\nBiosci."},{"key":"2026090917070152900_cit37","first-page":"105","article-title":"Understanding\nthe Lipid-Digestion Processes in the GI Tract before Designing Lipid-Based\nDrug-Delivery Systems","volume-title":"Therapeutic Delivery","author":"N\u2019Goma","year":"2012"},{"issue":"3","key":"2026090917070152900_cit38","doi-asserted-by":"publisher","first-page":"576","DOI":"10.1016\/j.bbrc.2018.03.081","article-title":"Applications of Mass Spectrometry-Based Targeted and\nNon-Targeted Lipidomics","volume":"504","author":"Lee","year":"2018","journal-title":"Biochem. Biophys. 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Lipids"},{"issue":"7","key":"2026090917070152900_cit41","doi-asserted-by":"publisher","DOI":"10.1002\/ejlt.201800063","article-title":"Enzymatic Interesterification of\nHeterotrophic Microalgal\nOil with Rapeseed Oil to Decrease the Levels of Tripalmitin","volume":"120","author":"Bogevik","year":"2018","journal-title":"Eur. J. Lipid Sci. Technol."},{"issue":"3","key":"2026090917070152900_cit42","doi-asserted-by":"publisher","first-page":"226","DOI":"10.1016\/0141-0229(95)00239-1","article-title":"An Investigation\nof Crude Lipases for Hydrolysis, Esterification, and Transesterification","volume":"19","author":"Wu","year":"1996","journal-title":"Enzyme Microb. Technol."},{"issue":"12","key":"2026090917070152900_cit43","doi-asserted-by":"publisher","first-page":"2065","DOI":"10.1016\/j.clinthera.2018.10.014","article-title":"Effects of a Self\u2013Micro-Emulsifying\nDelivery\nSystem Formulation Versus a Standard \u03c9-3 Acid Ethyl Ester Product\non the Bioavailability of Eicosapentaenoic Acid and Docosahexaenoic\nAcid: A Study in Healthy Men and Women in a Fasted State","volume":"40","author":"Maki","year":"2018","journal-title":"Clin. Ther."}],"container-title":["Journal of Agricultural\nand Food Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jafc.6c03597","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/35\/27512\/67739482\/acs.jafc.6c03597.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/35\/27512\/67739482\/acs.jafc.6c03597.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,9]],"date-time":"2026-09-09T21:17:01Z","timestamp":1788988621000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jafcau\/article\/74\/35\/27512\/5361408\/In-Vitro-Evidence-of-Linolenic-Acid-Ethyl-Ester"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,29]]},"references-count":43,"journal-issue":{"issue":"35","published-online":{"date-parts":[[2026,8,29]]},"published-print":{"date-parts":[[2026,9,9]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jafc.6c03597","relation":{},"ISSN":["0021-8561","1520-5118"],"issn-type":[{"value":"0021-8561","type":"print"},{"value":"1520-5118","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,29]]}}}