{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T17:48:28Z","timestamp":1792259308912,"version":"4.4.0"},"reference-count":54,"publisher":"MDPI AG","issue":"16","license":[{"start":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T00:00:00Z","timestamp":1787184000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Foods"],"abstract":"<jats:p>Stearidonic acid (SDA) and \u03b3-linolenic acid (GLA) are recognized for their anti-inflammatory and cardiometabolic benefits, yet their natural dietary sources remain scarce. This study aimed to develop and optimize the enzymatic synthesis of lysophosphatidylcholine (LPC) enriched with GLA and SDA in a solvent-free system using Echium plantagineum seed oil as the source of GLA and SDA. Enzyme screening was conducted with three immobilized lipases, among which Lipozyme\u00ae 435 exhibited superior performance, achieving significantly higher proportions of both GLA and SDA into the LPC backbone compared with alternative lipases. Reaction optimization was performed using a Box\u2013Behnken response surface design, evaluating temperature, time, lipase load, and substrate molar ratio. The analysis identified lipase load as the most influential factor for both fatty acid proportion and LPC yield. At 50 \u00b0C for 24 h, with a substrate molar ratio of 1:15 and a 15 wt% lipase load, the synthesis yielded 92.0 \u00b1 4.1 mol%. Within the LPC fraction, GLA + SDA contributed 69.5 \u00b1 1.2% of total fatty acids. The resulting structured LPC combines the enhanced bioavailability of the lysophospholipid carrier with the complementary metabolic activities of GLA and SDA, supporting its potential for the development of functional foods and nutraceutical formulations.<\/jats:p>","DOI":"10.3390\/foods15162914","type":"journal-article","created":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T09:48:31Z","timestamp":1787219311000},"page":"2914","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Enzymatic Synthesis of Lysophosphatidylcholine Containing \u03b3-Linolenic and Stearidonic Acids in a Solvent-Free System"],"prefix":"10.3390","volume":"15","author":[{"given":"Mat\u00edas","family":"Rivera-B\u00e1ez","sequence":"first","affiliation":[{"name":"Institute of Nutrition and Food Technology, University of Chile, Santiago 7830490, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6455-6778","authenticated-orcid":false,"given":"Fabrizzio","family":"Vald\u00e9s-Rebolledo","sequence":"additional","affiliation":[{"name":"Institute of Nutrition and Food Technology, University of Chile, Santiago 7830490, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5049-2144","authenticated-orcid":false,"given":"Miguel \u00c1ngel","family":"Rinc\u00f3n-Cervera","sequence":"additional","affiliation":[{"name":"Institute of Nutrition and Food Technology, University of Chile, Santiago 7830490, Chile"},{"name":"Food Technology Division, ceiA3, University of Almer\u00eda, 04120 Almer\u00eda, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,8,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1007\/s13668-021-00363-3","article-title":"Dietary polyunsaturated fatty acids (PUFAs): Uses and potential health benefits","volume":"10","author":"Kapoor","year":"2021","journal-title":"Curr. Nutr. Rep."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Harwood, J.L. (2023). Polyunsaturated fatty acids: Conversion to lipid mediators, roles in inflammatory diseases and dietary sources. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24108838"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.ejphar.2016.04.020","article-title":"Gamma-linolenic acid, dihomo-gamma-linolenic acid, eicosanoids and inflammatory processes","volume":"785","author":"Sergeant","year":"2016","journal-title":"Eur. J. Pharmacol."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Mustonen, A.-M., and Nieminen, P. (2023). Dihomo-\u03b3-linolenic acid (20:3 n-6): Metabolism, derivatives and significance in chronic inflammation. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24032116"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"319","DOI":"10.1002\/aocs.12328","article-title":"Fatty acid profile and bioactive compound extraction in purple viper\u2019s bugloss seed oil using green solvents","volume":"97","author":"Valenzuela","year":"2020","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1725","DOI":"10.1080\/10408398.2020.1765137","article-title":"Plant-based stearidonic acid as a sustainable source of omega-3 fatty acids with functional outcomes on human health","volume":"61","author":"Prasad","year":"2021","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"114894","DOI":"10.1016\/j.jep.2021.114894","article-title":"Comparative analysis of medicinal substances and applications of Echium species","volume":"285","author":"Wang","year":"2022","journal-title":"J. Ethnopharmacol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"112635","DOI":"10.1016\/j.lwt.2021.112635","article-title":"Enzymatic preparation of lysophosphatidylserine containing DHA in a solvent-free system","volume":"154","author":"Zhang","year":"2022","journal-title":"LWT"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"144359","DOI":"10.1016\/j.foodchem.2025.144359","article-title":"Enzymatic biosynthesis, characterization and antioxidant properties of \u03c9-3 structured phospholipids","volume":"484","author":"Wu","year":"2025","journal-title":"Food Chem."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Zhou, J., Lee, Y.Y., Mao, Y., Wang, Y., and Zhang, Z. (2022). Future of structured lipids: Enzymatic synthesis and applications in food systems. Foods, 11.","DOI":"10.3390\/foods11162400"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"305","DOI":"10.17113\/ftb.57.03.19.6025","article-title":"Lipase-catalyzed interesterification for structured lipids synthesis: A review","volume":"57","author":"Utama","year":"2019","journal-title":"Food Technol. Biotechnol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"145393","DOI":"10.1016\/j.foodchem.2025.145393","article-title":"Enhanced Pickering interfacial biocatalysis in phosphatidylserine synthesis via phospholipase D immobilization with optimized bifunctional strategy","volume":"492","author":"Liu","year":"2025","journal-title":"Food Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"144969","DOI":"10.1016\/j.foodchem.2025.144969","article-title":"Enzymatic preparation of structured phospholipids from soybean phosphatidylcholine and investigation of their phase behavior","volume":"489","author":"Sun","year":"2025","journal-title":"Food Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1016\/j.tifs.2019.04.005","article-title":"Preparation and functionality of lipase-catalysed structured phospholipid: A review","volume":"88","author":"Ang","year":"2019","journal-title":"Trends Food Sci. Technol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"115296","DOI":"10.1016\/j.bcp.2022.115296","article-title":"Regulation of membrane phospholipid biosynthesis in mammalian cells","volume":"206","author":"Morita","year":"2022","journal-title":"Biochem. Pharmacol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"460","DOI":"10.1016\/j.jconrel.2022.07.014","article-title":"Tailoring multifunctional properties of phospholipids for self-assemblies","volume":"349","author":"Waghule","year":"2022","journal-title":"J. Control. Release"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1186\/1476-511X-11-3","article-title":"Health effects of dietary phospholipids","volume":"11","author":"Taylor","year":"2012","journal-title":"Lipids Health Dis."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"101633","DOI":"10.1016\/j.bcab.2020.101633","article-title":"Digestion and absorption of dietary glycerophospholipids in the small intestine: Significance as carriers of choline and n-3 polyunsaturated fatty acids","volume":"26","author":"Murota","year":"2020","journal-title":"Biocatal. Agric. Biotechnol."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Sandoval, G. (2012). Lipases as biocatalysts for the synthesis of structured lipids. Lipases and Phospholipases: Methods and Protocols, Humana Press.","DOI":"10.1007\/978-1-61779-600-5"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Sugasini, D., Yalagala, P.C.R., and Subbaiah, P.V. (2020). Efficient enrichment of retinal DHA with dietary lysophosphatidylcholine-DHA. Nutrients, 12.","DOI":"10.3390\/nu12103114"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1","DOI":"10.5650\/jos.ess24253","article-title":"Health benefits of dietary docosahexaenoic acid and eicosapentaenoic acid-enriched glycerophospholipids from marine sources","volume":"74","author":"Hosomi","year":"2025","journal-title":"J. Oleo Sci."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"100293","DOI":"10.1016\/j.fochx.2022.100293","article-title":"Dietary lysophosphatidylcholine regulates lipid composition in turbot fillet","volume":"14","author":"Xu","year":"2022","journal-title":"Food Chem. X"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2921","DOI":"10.1093\/jn\/131.11.2921","article-title":"Lysophosphatidylcholine enhances carotenoid uptake from mixed micelles by Caco-2 cells","volume":"131","author":"Sugawara","year":"2001","journal-title":"J. Nutr."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"947","DOI":"10.5650\/jos.ess21069","article-title":"Combined effects of lysophospholipids on inflammation and oxidative stress","volume":"70","author":"Tsukahara","year":"2021","journal-title":"J. Oleo Sci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1126","DOI":"10.1016\/j.clnu.2023.05.011","article-title":"Metabolic profiles reflect weight loss maintenance and diet composition","volume":"42","author":"Mikkonen","year":"2023","journal-title":"Clin. Nutr."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.clnu.2024.09.020","article-title":"Lipidomic perturbations of adiposity phenotypes and diet associations","volume":"43","author":"Xu","year":"2024","journal-title":"Clin. Nutr."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1038\/s41591-024-03279-x","article-title":"Lipid profiling identifies modifiable signatures of cardiometabolic risk in children and adolescents with obesity","volume":"31","author":"Huang","year":"2025","journal-title":"Nat. Med."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1800208","DOI":"10.1002\/ejlt.201800208","article-title":"Concentration of gamma-linolenic and stearidonic acids from viper\u2019s bugloss seed oil by urea complexation","volume":"120","author":"Valenzuela","year":"2018","journal-title":"Eur. J. Lipid Sci. Technol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/j.cofs.2017.06.007","article-title":"Advances in phospholipid quantification methods","volume":"16","author":"Wang","year":"2017","journal-title":"Curr. Opin. Food Sci."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1007\/s10068-023-01337-7","article-title":"Immobilized Candida antarctica lipase B as an sn-1,3 regiospecific biocatalyst for the interesterification of triacylglycerols with fatty acid ethyl esters","volume":"33","author":"Hwang","year":"2024","journal-title":"Food Sci. Biotechnol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"e00505","DOI":"10.1016\/j.btre.2020.e00505","article-title":"Highly efficient preparation of 1-lysophosphatidylcholine via high proportion of Novozym\u00ae 435 (lipase B from Candida antarctica)-catalyzed ethanolysis","volume":"27","author":"Yasuda","year":"2020","journal-title":"Biotechnol. Rep."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1016\/j.foodchem.2017.01.066","article-title":"Enzymatic synthesis of lysophosphatidylcholine with n-3 polyunsaturated fatty acid from sn-glycero-3-phosphatidylcholine in a solvent-free system","volume":"226","author":"Liu","year":"2017","journal-title":"Food Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1624","DOI":"10.1016\/j.ijbiomac.2020.09.021","article-title":"Lipase immobilization with support materials, preparation techniques, and applications: Present and future aspects","volume":"163","author":"Ismail","year":"2020","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Okulus, M., Rychlicka, M., and Gliszczy\u0144ska, A. (2022). Enzymatic production of biologically active lysophosphatidylcholine via regioselective lipase-catalyzed acidolysis. Foods, 11.","DOI":"10.3390\/foods11010007"},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Garcia-Quinto, E., Guisan, J.M., and Fernandez-Lorente, G. (2025). Use of ionic liquids in the enzymatic synthesis of structured docosahexaenoic acid lyso-phospholipids. Molecules, 30.","DOI":"10.3390\/molecules30030728"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1021\/acs.jafc.9b05177","article-title":"Efficient synthesis of lysophosphatidylcholine enriched with n-3 polyunsaturated fatty acids","volume":"68","author":"Wang","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"114107","DOI":"10.1016\/j.lwt.2022.114107","article-title":"Lipase-catalyzed synthesis of 1,3-diacylglycerols containing stearidonic, \u03b3-linolenic and \u03b1-linolenic acids in a solvent-free system","volume":"170","author":"Akoh","year":"2022","journal-title":"LWT"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1380","DOI":"10.1007\/BF02679607","article-title":"Study on the oxidative rate and prooxidant activity of free fatty acids","volume":"63","author":"Miyashita","year":"1986","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1002\/jsfa.7320","article-title":"Phospholipids in foods: Prooxidants or antioxidants?","volume":"96","author":"Cui","year":"2016","journal-title":"J. Sci. Food Agric."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"101985","DOI":"10.1016\/j.cdnut.2023.101985","article-title":"Lysophosphatidylcholine-rich nutrition therapy increased gut absorption of coingested dietary fat: A randomized controlled trial","volume":"7","author":"Tindall","year":"2023","journal-title":"Curr. Dev. Nutr."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Ahmmed, M.K., Hachem, M., Ahmmed, F., Rashidinejad, A., Oz, F., Bekhit, A.A., Carne, A., and Bekhit, A.D.A. (2023). Marine fish-derived lysophosphatidylcholine: Properties, extraction, quantification, and brain health application. Molecules, 28.","DOI":"10.3390\/molecules28073088"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"8194","DOI":"10.1021\/acs.joc.2c00335","article-title":"Synthesis of lysophosphatidylcholine and mixed phosphatidylcoline","volume":"87","author":"Papangelis","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_43","unstructured":"Nishinari, K., and Doi, E. (1994). Enhanced emulsifying ability of food surfactants by addition of lysophospholipids. Food Hydrocolloids, Springer. [1st ed.]."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3346","DOI":"10.1039\/C7FO00933J","article-title":"Preparation, characterization and bioavailability by oral administration of O\/W curcumin nanoemulsions stabilized with lysophosphatidylcholine","volume":"8","year":"2017","journal-title":"Food Funct."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1016\/j.anifeedsci.2010.10.004","article-title":"Effect of fat type and lysophosphatidylcholine addition to broiler diets on performance, apparent digestibility of fatty acids, and apparent metabolizable energy content","volume":"163","author":"Zhang","year":"2011","journal-title":"Anim. Feed Sci. Technol."},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Liu, R., Liu, X., Wei, Y., Liu, W., Li, T., Yuan, X., Jiang, S., Yang, W., and Jiao, N. (2026). Low energy diets supplemented with lysophos-phatidylcholine improve production performance and lipid metabolism in broilers. Front. Vet. Sci., 13.","DOI":"10.3389\/fvets.2026.1753429"},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Li, Y., Dai, L., Liu, D., and Du, W. (2022). Progress & prospect of enzyme-mediated structured phospholipids preparation. Catalysts, 12.","DOI":"10.3390\/catal12070795"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"5696","DOI":"10.1039\/D1CY00696G","article-title":"Solvent-free esterifications mediated by immobilized lipases: A review from thermodynamic and kinetic perspectives","volume":"11","author":"Sousa","year":"2021","journal-title":"Catal. Sci. Technol."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1187","DOI":"10.1007\/s11746-998-0310-6","article-title":"Production of specific-structured triacylglycerols by lipase-catalyzed interesterification in a laboratory-scale continuous reactor","volume":"75","author":"Mu","year":"1998","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1009","DOI":"10.5650\/jos.ess17046","article-title":"Lipase-catalyzed synthesis of oleoyl-lysophosphatidylcholine by direct esterification in solvent-free medium without water removal","volume":"66","author":"Mnasri","year":"2017","journal-title":"J. Oleo Sci."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"921","DOI":"10.1016\/S1381-1177(00)00159-4","article-title":"Kinetic characterisation of enzymatic esterification in a solvent system: Adsorptive control of water with molecular sieves","volume":"11","author":"Giacometti","year":"2001","journal-title":"J. Mol. Catal. B Enzym."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"e71175","DOI":"10.1111\/1750-3841.71175","article-title":"Lipase stability in structured lipid synthesis: The interplay of substrate characteristics and strategies to improve its operational performance\u2014A critical review","volume":"91","author":"Lee","year":"2026","journal-title":"J. Food Sci."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1044","DOI":"10.1016\/j.copbio.2013.02.028","article-title":"Microbial production of fatty acid-derived fuels and chemicals","volume":"24","author":"Lennen","year":"2013","journal-title":"Curr. Opin. Biotechnol."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"108275","DOI":"10.1016\/j.biotechadv.2023.108275","article-title":"Has the time finally come for green oleochemicals and biodiesel production using large-scale enzyme technologies? Current status and new developments","volume":"28","author":"Mustafa","year":"2023","journal-title":"Biotechnol. Adv."}],"container-title":["Foods"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2304-8158\/15\/16\/2914\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,22]],"date-time":"2026-08-22T04:19:13Z","timestamp":1787372353000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2304-8158\/15\/16\/2914"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,20]]},"references-count":54,"journal-issue":{"issue":"16","published-online":{"date-parts":[[2026,8]]}},"alternative-id":["foods15162914"],"URL":"https:\/\/doi.org\/10.3390\/foods15162914","relation":{},"ISSN":["2304-8158"],"issn-type":[{"value":"2304-8158","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,20]]}}}