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.

Chromatography with silver nitrate: part 2

“…For example, exposing all cis 13 to the thiyl radical and obtaining 14 after SNIS purification (Scheme 1). [20][21][22][23][24][25][26][27] M A N U S C R I P T Braun, 29 in a continuing study of Western Australian sandalwood oil, required SNIS to resolve three isomers of acoren-11-ol (16)(17)(18). In the same year Braun et al 30 described the use of SNIS to separately purify (Z)-γ-curcumen-l2-ol (19) and (Z)-β-curcumen-l2-ol (20), with the former requiring the SNIS to be stabilized with BHT to prevent oxidation of the conjugated diene.…”

The mitochondrial-targeted antioxidant, MitoQ, increases liver mitochondrial cardiolipin content in obesogenic diet-fed rats

“…The present study was designed 26 to determine the effect of MitoQ, a mitochondrial-targeted antioxidant, on the content of liver mitochondrial 27 membrane phospholipids, in particular CL, and its fatty acid composition in obesogenic diet-fed rats. 28 To do this, twenty-four 6 week old male Sprague Dawley rats were randomized into three groups of 8 animals 29 and fed for 8 weeks with either a control diet, a high fat diet (HF), or a HF diet with MitoQ (HF + MitoQ). 30 Phospholipid classes and fatty acid composition were assayed by chromatographic methods in liver and liver 31 mitochondria.…”

Free-Radical-Mediated Formation of Trans-Cardiolipin Isomers, Analytical Approaches for Lipidomics and Consequences of the Structural Organization of Membranes

“…Afterwards, we focused on the separation of the trans CL isomers from the reaction crude. The crude mixtures at 4 and 20 min of photolysis were purified employing preparative TLC plates pre-treated with 5% AgNO 3 solution in acetonitrile, with a previously reported protocol (Ag-TLC) [ 44 ]. The desired spots were scratched off and the silica was suspended in absolute EtOH and filtered, thus affording the ethanolic extract.…”

“…Preparative TLC glass plates were pre-treated with 5% AgNO 3 solution in acetonitrile for 15 min and then dried at 120 °C for 1 h [ 44 ]. Eluent for separation: CHCl 3 /MeOH/H 2 O 5: 2: 0.2, R f (CL) = 0.52, R f (mix MT-CL) = 0.6, R f (T-CL) = 0.66.…”