title: Trans fatty acids: chemical synthesis of eicosapentaenoic acid isomers and detection in rats fed a deodorized fish oil diet.
abstract: Eicosapentaenoic acid (EPA) is a polyunsaturated fatty acid present in fish oils used for omega-3 enriched diets. The natural cis double bond geometry can be transformed to the trans configuration during the deodorization process utilized in the food industry. The analytical discrimination of the possible five monotrans regioisomers represents a limiting step for the recognition and structure-activity relationship in connection with the harmful effects of trans fatty acids in health. We carried out a dual synthetic strategy, providing new access to monotrans EPA isomers and valuable information on GC and NMR characteristics for further applications in metabolomics and lipidomics. This small library was used as an analytical reference for isomer determination in deodorized fish oils and the follow-up of rats fed fish oil diets, evidencing for the first time that monotrans EPA isomers are incorporated in liver mitochondrial membranes after dietary intake.
authors.affiliation: ISOF, Consiglio Nazionale delle Ricerche, Via P. Gobetti 101, 40129 Bologna, Italy. cferreri@isof.cnr.it
authors.forename: Carla
authors.initials: C
authors.lastname: Ferreri
authors.forename: Stanislav A
authors.initials: SA
authors.lastname: Grabovskiy
authors.forename: Manar
authors.initials: M
authors.lastname: Aoun
authors.forename: Michele
authors.initials: M
authors.lastname: Melchiorre
authors.forename: Natalia
authors.initials: N
authors.lastname: Kabal'nova
authors.forename: Christine
authors.initials: C
authors.lastname: Feillet-Coudray
authors.forename: Gilles
authors.initials: G
authors.lastname: Fouret
authors.forename: Charles
authors.initials: C
authors.lastname: Coudray
authors.forename: Chryssostomos
authors.initials: C
authors.lastname: Chatgilialoglu
mesh_terms: D000818:Animals; D004032:Diet; D015118:Eicosapentaenoic Acid / Q000737:chemistry* / Q000493:pharmacokinetics; D005395:Fish Oils / Q000737:chemistry* / Q000493:pharmacokinetics; D007536:Isomerism; D008930:Mitochondria, Liver / Q000378:metabolism; D010743:Phospholipids / Q000378:metabolism; D051381:Rats; D044242:Trans Fatty Acids / Q000737:chemistry* / Q000493:pharmacokinetics; D014413:Tuna
chemical_list: D005395:Fish Oils; D010743:Phospholipids; D044242:Trans Fatty Acids; D015118:Eicosapentaenoic Acid