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Novel branched-chain fatty acids in certain fish oils

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Lipids

Abstract

Methyl-branched fatty acids, which are usually minor components (≤0.1%) in fish oils, were concentrated in the non-urea-complexing fraction along with polyunsaturated fatty acids during the enrichment of omega-3 fatty acids from certain fish oils via the urea complexation process. The methyl-branched fatty acids in the omega-3 polyunsaturated fatty acid concentrates, which were prepared from three fish body oils, were characterized by gas chromatography and gas chromatography/mass spectrometry. Among the major branched-chain fatty acids expected and identified were the known isoprenoid acids—mainly 4,8,12-trimethyltridecanoic, pristanic, and phytanic—and the well-known iso and anteiso structures. Two novel phytol-derived multimethyl-branched fatty acids, 2,2,6,10,14-pentamethylpentadecanoic and 2,3,7,11,15-pentamethylhexadecanoic, were identified in redfish (Sebastes sp.) oil. These two fatty acids were absent in oils from menhaden (Brevoortia tyrannus) and Pacific salmon (mixed, but mostly from sockeye,Oncorhynchus nerka). The major branched-chain fatty acid in the salmon oil, 7-methyl-7-hexadecenoic acid, was also present to a moderate extent in menhaden oil. A novel vicinal dimethyl-branched fatty acid, 7,8-dimethyl-7-hexadecenoic was detected in all of the fish oils examined, but was most important in the salmon oil. Three monomethyl-branched fatty acids, 11-methyltetradecanoic acid, and 11- and 13-methylhexadecanoic, hitherto undescribed in fish lipids, were also detected in salmon, redfish and menhaden oils.

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Abbreviations

AgNO3-TLC:

silver nitrate-thin layer chromatography

BCFA:

branched-chain fatty acid

DHA:

docosahexaenoic acid

DMHD:

dimethylhexadecanoic acid

ECL:

equivalent chain length

EPA:

eicosapentaenoic acid

FID:

flame ionization detector

GC/MS:

gas chromatography/mass-spectrometry

GLC:

gas-liquid chromatography

ITD:

Ion Trap Detector

MHD:

methylhexadecanoic

MTD:

methyltetradecanoic

NUCF:

non-urea-complexing fraction

PMHD:

pentamethylhexadecanoic

PMPD:

pentamethylpentadecanoic

PUFA:

polyunsaturated fatty acid

TMHD:

tetramethylhexadecanoic or phytanic

TMPD:

tetramethylpentadecanoic acid or pristanic

TMTD:

trimethyltridecanoic acid

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Ratnayake, W.M.N., Olsson, B. & Ackman, R.G. Novel branched-chain fatty acids in certain fish oils. Lipids 24, 630–637 (1989). https://doi.org/10.1007/BF02535080

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  • DOI: https://doi.org/10.1007/BF02535080

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