Counter-current chromatographic separation of polyunsaturated fatty acids

Bousquet, O.; Goffic, François Le

doi:10.1016/0021-9673(94)01233-5

Cited by 35 publications

(20 citation statements)

References 21 publications

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“…In accordance with the fractionation scheme, only short chain SFA and a few MUFA were additionally detected in these fractions, so that one-step HSCCC was suited to enrich PUFAs, but the isolation of pure 20:5n-3 (EPA) or 22:6n-3 (DHA) was not possible. This problem was previously solved by applying a two-step mode [20]. In contrast, isolation turned out to be within the bounds of possibility for the potential 16:4n-1 isomer.…”

Section: Resultsmentioning

confidence: 71%

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Isolation of 6,9,12,15-Hexadecatetraenoic Fatty Acid (16:4n-1) Methyl Ester from Transesterified Fish Oil by HSCCC

Schröder

Vetter

2011

Chromatographia

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Fish oil is considered a healthy food due to the presence of large amounts of polyunsaturated fatty acids (PUFAs), especially in the form of n-3 fatty acids 5,8,11,14, EPA) and 4,7,10,13,16, DHA). However, fish oil is known to contain many other PUFAs, some of which are uncommon and whose bioactivity is scarcely investigated. In this study, we isolated the rare PUFA 6,9,12,15-hexadecatetraenoic fatty acid (16:4n-1) which bears a double bond on the terminal carbon from fish oil in form of its methyl ester. We used high-speed countercurrent chromatography (HSCCC) for the fractionation of 500 mg-portions of fatty acid methyl esters prepared from a fish oil capsule and investigated the fractions by GC/MS. Twenty-eight 13-mL fractions were collected and fatty acid methyl esters were detected in fractions 11-23. The elution was carried out in normal phase mode, providing the longchained saturated and monoenoic fatty acids first. More than 100 fatty acids ranging from 10:0 to 26:0 could be identified in the HSCCC fractions, and most of them were polyunsaturated. The reproducibility of the HSCCC method was shown by repeated injection of the fish oil and the fractions containing 6,9,12,15-hexadecatetraenoic fatty acid (16:4n-1). The late eluting 16:4n-1 methyl ester was isolated in pure form and its structure was verified.

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Section: Resultsmentioning

confidence: 71%

“…This system benefits from both avoiding irreversible adsorption of the sample as well as from its high sample capacity in the high mg-range [15,17,18]. HSCCC has only occasionally been used for the enrichment and isolation of specific fatty acids [19,20]. Fractions were determined by gas chromatography coupled to mass spectrometry (GC/MS).…”

Section: Introductionmentioning

confidence: 99%

Isolation of 6,9,12,15-Hexadecatetraenoic Fatty Acid (16:4n-1) Methyl Ester from Transesterified Fish Oil by HSCCC

Schröder

Vetter

2011

Chromatographia

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“…This mixture was subjected to another separation using heptane as a stationary phase and methanolwater as the mobile phase (bi-phasic solvent system of heptane/methanol/water; 500:415:85, v/v/v). Under these conditions, a good separation was achieved and isolation of pure EPA and DHA resulted in an excellent yield [13]. The CPC may also be applied to separate EPA and DHA ethyl esters with a solvent system comprised of hexane/dichloromethane/acetonitrile (5:1:…”

Section: Counter-current Chromatographymentioning

confidence: 99%

Preparative and Industrial‐Scale Isolation and Purification of Omega‐3 Polyunsaturated Fatty Acids from Marine Sources

Wanasundara¹

2010

Handbook of Seafood Quality, Safety and Health Applications

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“…CCC can be considered favorable for purification purposes because of its unique advantages such as high recovery rates, no irreversible adsorption processes, and moderate solvent consumption in contrast to other liquid chromatography techniques [8]. Nevertheless, the purification of FAs and FA esters by liquid-liquid separation techniques proved to be laborious due to the equivalent-chain-length (ECL) rule [5] which implies that one double bond equals with two carbon atoms in the alkyl chain resulting in similar partitioning coefficients causing co-elutions of critical FA pairs [9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

“…Purification of selected FAs or FA esters on a preparative scale from various raw materials such as vegetable and fish oils has been accomplished by the solid support-free, liquidliquid separation technique countercurrent chromatography (CCC) [5][6][7]. CCC involves the distribution of analytes between a liquid stationary and a liquid mobile phase and their transport by the latter.…”

Section: Introductionmentioning

confidence: 99%

Overcoming the equivalent-chain-length rule with pH-zone-refining countercurrent chromatography for the preparative separation of fatty acids

Englert

Vetter

2015

Anal Bioanal Chem

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Purification of individual fatty acids from vegetable oils by preparative liquid chromatography techniques such as countercurrent chromatography (CCC) is a challenging task due to the equivalent-chain-length (ECL) rule. It implies that one double bond equals two carbon atoms in the alkyl chain of a fatty acid and therefore causes co-elutions of saturated and unsaturated fatty acids. Accordingly, existing methods for the purification of individual fatty acids are cumbersome and time-consuming as two or more steps with different conditions are required. To avoid additional purification steps, we report a method utilizing pH-zone-refining CCC which enabled the purification of all major fatty acids from sunflower oil (purities >95 %) in one step by circumventing co-elutions caused by the ECL rule. This method is based on the involvement of acid strength and hydrophobicity of fatty acids during the separation process. By exploiting the preparative character of the pH-zone-refining mode, a tenfold sample amount of free fatty acids from sunflower oil could be separated in comparison to regular CCC.

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Counter-current chromatographic separation of polyunsaturated fatty acids

Cited by 35 publications

References 21 publications

Isolation of 6,9,12,15-Hexadecatetraenoic Fatty Acid (16:4n-1) Methyl Ester from Transesterified Fish Oil by HSCCC

Isolation of 6,9,12,15-Hexadecatetraenoic Fatty Acid (16:4n-1) Methyl Ester from Transesterified Fish Oil by HSCCC

Preparative and Industrial‐Scale Isolation and Purification of Omega‐3 Polyunsaturated Fatty Acids from Marine Sources

Overcoming the equivalent-chain-length rule with pH-zone-refining countercurrent chromatography for the preparative separation of fatty acids

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