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Characterization of branched chain fatty acids from subcutaneous triacyglycerols of barley‐fed lambs
Author(s) -
Duncan W. R. H.,
Lough A. K.,
Garton G. A.,
Brooks P.
Publication year - 1974
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02532173
Subject(s) - substituent , chemistry , homologous series , adduct , fatty acid , gas chromatography , carbon chain , amino acid , mass spectrometry , organic chemistry , stereochemistry , chromatography , biochemistry
Abstract The fatty acids of subcutaneous triacylglycerols (containing ca. 11% of branched chain components) from lambs fed on barley‐rich diets were fractionated by treatment with mercuric acetate and by urea adduct formation to yield concentrates rich in the branched chain components, all of which were saturated. The concentrates were subjected to analysis by high resolution gas liquid chromatography in conjunction with mass spectrometry. The branched chain fatty acids consisted of a complex mixture of mono‐, di‐, and trimethyl substituted components. The greater part of the mixture comprised monomethyl substituted acids of chain length 10–17 carbon atoms. Within each of these molecular species, a number of positional isomers was identified, notably in respect of methyltetradecanoic acid (methyl substituent on carbon 2, 4, 6, 8, 10, and 12) and methylhexadecanoic acid (methyl substituent on carbon 2, 4, 6, 8, 12, and 14). Homologous series also could be recognized of one of which all eight members from 4‐methyldecanoic acid to 4‐methylheptadecanoic acid were identified; together they accounted for ca. 39% of the branched chain fatty acids which were sampled for mass spectrometry. The dibranched acids identified consisted of five members of a homologous series, ranging in chain length from 11–15 carbon atoms and with substituent methyl groups at positions 4 and 8. Though the identity of only one tribranched acid (2,6,10‐trimethyltetradecanoic acid) was established, others also apparently were present in the mixture. The probable involvement of methylmalonate in the biosynthesis of these branched chain acids is discussed briefly, with particular reference to the availability of vitamin B 12 in relation to the activity of methylmalonyl coenzyme A mutase.