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Title: Trans Lipid Library: Synthesis of Docosahexaenoic Acid (DHA) Monotrans Isomers and Regioisomer Identification in DHA-Containing Supplements
Authors: Menounou, Georgia; Giacometti, Giorgia; Scanferlato, Roberta and Dambruoso, Paolo; Sansone, Anna; Tueros, Itziar; Amezaga, Javier; Chatgilialoglu, Chryssostomos; Ferreri, Carla
Citation: CHEMICAL RESEARCH IN TOXICOLOGY, 2018, 31, 191-200
Abstract: Docosahexaenoic acid (DHA) is a semiessential polyunsaturated fatty acid (PUFA) for eukaryotic cells that is found in natural sources such as fish and algal oils and widely used as an ingredient for omega-3 containing foods or supplements. DHA effects are connected to its natural structure with six cis double bonds, but geometrical monotrans isomers can be formed during distillation or deodorization processes, as an unwanted event that alters molecular characteristics and annihilates health benefits. The characterization of the six monotrans DHA regioisomers is an open issue to address for analytical, biological, and nutraceutical applications. Here we report the preparation, separation, and first identification of each isomer by a dual approach consisting of the following: (i) the direct thiyl radical-catalyzed isomerization of cis-DHA methyl ester and (ii) the two-step synthesis from cis-DHA methyl ester via monoepoxides as intermediates, which are separated and identified by nuclear magnetic resonance spectroscopy, followed by elimination for the unequivocal assignment of the double bond position. This monotrans DHA isomer library with NMR and GC analytical characterization was also used to examine the products of thiyl-radical-catalyzed isomerization of a fish oil sample and to evaluate the trans isomer content in omega-3 containing supplements commercially available in Italy and Spain.
Issue Date: 2018
Type: Article
Language: English
DOI: 10.1021/acs.chemrestox.8b00021
ISSN: 0893-228X
E-ISSN: 1520-5010
Funder: MSCA-ITN-ETN - Marie Sklodowska-Curie ITN project CLICKGENE [642023]
Di Bella Foundation
Basque Country Government (Department of the Environment, Regional Planning, Agriculture and Fisheries)
Appears in Publication types:Artículos científicos

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