Quantification of eicosapentaenoic and docosahexaenoic acid geometrical isomers formed during fish oil deodorization by gas–liquid chromatography

Fournier, Véronique; Destaillats, Frédéric; Hug, Bernadette; Golay, Pierre‐Alain; Joffre, Florent; Juanéda, Pierre; Sémon, Étienne; Dionisi, Fabiola; Lambelet, Pierre; Sébédio, Jean‐Louis; Berdeaux, Olivier

doi:10.1016/j.chroma.2007.03.099

Cited by 46 publications

(48 citation statements)

References 13 publications

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“…FA are labile molecules which, when exposed to heat treatment, can be lost through different chemical transformations (Berdeaux et al, 2007;Ceriane and Meirelless, 2007;Fournier et al, 2007). The initial content of trans PUFA in crude oils may increase in refined oils, due exclusively to deodorisation, since this reaction does not occur during preceding steps of the refinement process.…”

Section: Fatty Acids Profilesmentioning

confidence: 99%

Production and refinement of oil from carp (Cyprinus carpio) viscera

et al. 2010

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a b s t r a c tCarp viscera oil can be obtained by both ensilage and fishmeal processes. This study examined the refinement of carp (Cyprinus carpio) oils obtained by both processes, and compared crude, neutralised, bleached, winterised and deodorised oils' characteristics and lipid profiles. Refined oils obtained by the two processes did not present significant difference (p > 0.05) for Lovibond colour, free fatty acids, and thiobarbituric acid values. The major fatty acids identified in the carp crude, bleached and refined oils were oleic, palmitic, palmitoleic, linoleic and linolenic, constituting approximately 69.6% of the total fatty acids of the oils. The n À 3/n À 6 ratio was approximately 1.05 for refined oil. Therefore, carp viscera refined oil can be considered a rich source of essential fatty acids of the n À 3 and n À 6 series.

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Section: Fatty Acids Profilesmentioning

confidence: 99%

Production and refinement of oil from carp (Cyprinus carpio) viscera

et al. 2010

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“…The easiest and most commonly used method to determine the skeleton of molecule is total catalytic hydrogenation on PtO 2 in order to simplify the mixture by eliminating differences due to position and geometry of the double bonds. The skeletal structures are then determined by GC-MS (Potteau et al 1978;Sébédio et al 1987bSébédio et al , 1994Rojo and Perkins 1987b;Le Quéré et al 1989, 1991Meltzer et al 1981 Fournier et al (2007) than linolenic (Sébédio et al 1987a(Sébédio et al , b, 1989. Those formed from linoleic acid are mainly C18 monounsaturated acids having a five carbon α-disubstituted ring, whereas those arising from linolenic acid are a mixture of C18 diunsaturated fatty acids having a five or a six carbon α-disubstituted ring.…”

Section: Structure and Analysis Of Cfam In Processed Vegetable Oilsmentioning

confidence: 99%

“…The major isomer (more than 50% of total trans 18:1) is the vaccenic acid (Δ11t-18:1). Geometrical isomerization of polyunsaturated fatty acids is mainly taking place during the deodorization process and high temperatures (above 200°C) are usually required Fournier et al 2006aFournier et al , 2007. Trans monounsaturated fatty acids coming from the hydrogenation process have shown adverse effects in human especially on the risk factors of cardiovascular diseases by increasing the LDL cholesterol and decreasing the HDL cholesterol in some cases (Mensink and Zock 1998;Mozaffarian et al 2006).…”

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confidence: 98%

Analytical Methods for Quantification of Modified Fatty Acids and Sterols Formed as a Result of Processing

et al. 2008

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Fats and oils are often submitted to technological treatments before being consumed. Some treatments like refining, hydrogenation, and frying often lead to the formation of modified fatty acids such as cyclic fatty acid monomers (CFAM), geometrical fatty acid isomers, and/or oxidized fatty acids and sterols (cholesterol and phytosterols). Both cholesterol oxidation products (COP) and phytosterol oxidation products (POP), may be present in foods. As some of the newly formed components may present some adverse effects upon consumption, methods have been developed to analyze these compounds in food products and biological samples. Gas liquid chromatography (GC) on long polar columns (100m) is a good choice to quantify trans mono-and polyunsaturated fatty acids. In some cases a pre-fractionation step using silver nitrate thin layer chromatography (AgNO 3 -TLC) may be necessary to avoid GC overlapping of cis and trans isomers. Analysis of CFAM usually involves transformation of the sample in fatty acid methyl esters (FAME) which after addition of an internal standard (IS) are further hydrogenated. An enrichment step using reverse phase high performance liquid chromatography (RP-HPLC) permits to obtain a fraction which consists of a mixture of CFAM and the IS. This fraction is further analyzed by GC on a polar column. The analysis of oxidized triacylglycerol monomers (oxTG) as a group was feasible by a combination of adsorption and sizeexclusion chromatography. Quantification in used frying fats and oils around the limit of rejection for human consumption (25% polar compounds) has shown that the amount of oxTG range 5.9-9.4% expressed on fat or oil weight. In foods and biological tissues, the level of oxidized sterols (SOP) is often a very small fraction of their unoxidized forms. Analysis of SOP involved extraction of lipids, saponification or transesterification, enrichment, and subsequent qualitative and quantitative determination by GC and GC-MS, or HPLC and HPLC-MS. In addition, enrichment of SOP requires complete separation from the unoxidized sterols in order to separate these compounds even by high resolution GC capillary columns.

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“…Several epidemiological and clinical studies on the health effects of TFA published in the last few years indicate that TFA intake may be a risk factor for cardiovascular disease (Mozaffarian et al, 2006;Valenzuela et al, 2011). Analysis of trans isomers of fatty acids has taken on more importance, since the world health organization recommended that the intake of trans fat should be limited to < 1% of the overall energy intake (Fournier et al, 2007). In 2003, the U.S. food and drug administration (FDA) also passed a labeling requirement for trans fat in packaged food products, effective January1, 2006, requiring it to be reported on the nutrition label if present at ≥0.5g/serving, but allowed for it to be declared zero if the product contained <0.5g/serving.…”

Section: Introductionmentioning

confidence: 99%

Separation of <i>cis/trans</i> fatty acid isomers on gas chromatography compared to the Ag-TLC method

Kiran¹,

Reshma²,

Sundaresan³

2013

Grasas y Aceites

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RESUMENSeparación de isómeros cis/trans de ácidos grasos mediante cromatografía de gases, comparación con el método Ag-TLC.El presente estudio investiga la separación de isómeros cis/trans de ácidos grasos mediante cromatografía de gases (GC) utilizando una columna de SP2560 de 75 m y diferentes condiciones que incluyen un programa isotérmico y una programación temperatura-tiempo. La programación temperatura-tiempo mostró una mejor separación de isómeros cis / trans de los ácidos grasos C 14:1 , C 16:1 , C 18:1 , C 18:2 y C 18:3 con los ácidos grasos de cadena corta en comparación con el programa isotermo. La separación de los isómeros trans/trans de los ácidos grasos C 18:1 incluyendo ácido elaídico (C 18:1 Δ9t) y ácido vaccénico (C 18:1 Δ11t) fué difícil mediante programación temperatura-tiempo. La cromatografía en capa fina impregnada con nitrato de plata (Ag-TLC) se realizó para separar fracciones cis/trans y el análisis de la fracciones se llevó a cabo mediante GC. El análisis GC mostró co-elución de los isómeros trans del ácido graso C 18:1 . Así, el estudio muestra que una programación temperatura-tiempo en GC con columna de cianopropilo altamente polar es suficiente para resolver los ácidos grasos trans, junto con los ácidos grasos de cadena corta cuando un gran número de muestras tiene que ser analizado. PALABRAS CLAVE: Ácidos grasos trans -Cromatografía de gases -Fraccionamiento Ag-TLC -Resolución SUMMARY Separation of cis/trans fatty acids isomers on gas chromatography compared to the Ag-TLC methodThe present study investigates the separation of the cis/ trans isomers of fatty acids on the 75 m SP2560 column under different gas chromatographic (GC) conditions including an isothermal program and a time-temperature program. The time-temperature program showed improved separation of cis/trans isomers of C 14:1 , C 16:1 , C 18:1 , C 18:2 and C 18:3 fatty acids along with short chain fatty acids compared to the isothermal program. The separation of trans/trans isomers of C 18:1 fatty acids including elaidic acid (C 18:1 Δ9t) and vaccenic acid (C 18:1 Δ11t) was difficult with the time-temperature program. The thin layer chromatography impregnated with silver nitrate (Ag-TLC) method was performed to separate cis/trans fractions and GC analysis was carried out with the trans fraction. But GC analysis showed a co-elution of trans isomers of C 18:1 fatty acid. Thus the study shows that a time-temperature programmed GC method with the highly polar cyanopropyl column is sufficient to resolve trans fatty acids along with short chain fatty acids when a large number of samples has to be analyzed.

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Quantification of eicosapentaenoic and docosahexaenoic acid geometrical isomers formed during fish oil deodorization by gas–liquid chromatography

Cited by 46 publications

References 13 publications

Production and refinement of oil from carp (Cyprinus carpio) viscera

Production and refinement of oil from carp (Cyprinus carpio) viscera

Analytical Methods for Quantification of Modified Fatty Acids and Sterols Formed as a Result of Processing

Separation of <i>cis/trans</i> fatty acid isomers on gas chromatography compared to the Ag-TLC method

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