Acylglycerol structure of mustard seed oil and of cardiac lipids of rats during dietary lipidosis

1979 ◽  
Vol 57 (11) ◽  
pp. 1315-1327 ◽  
Author(s):  
J. J. Myher ◽  
A. Kuksis ◽  
S. C. Vasdev ◽  
K. J. Kako
Keyword(s):  
Fatty Acids ◽  
Seed Oil ◽  
Positional Distribution ◽  
Mustard Seed ◽  
Gradual Change ◽  
Glycerol Molecule ◽  
Caloric Requirement ◽  
Normal Rat ◽  
Rat Tissue ◽  
Long Chain

Stereospecific degradation and combined gas chromatographic – mass spectrometric (gc/ms) analysis were employed in a detailed investigation of the triacylglycerol structure of mustard seed oil and of the triacylglycerols transiently accumulating in the hearts of young rats receiving the oil in their diet. It was shown that feeding of mustard seed oil at 40% of the daily caloric requirement resulted in a deposition of cardiac triacylglycerols containing a high proportion of enantiomers of a positional distribution and molecular association of fatty acids which were closely similar to those found in the dietary oil. Complete structures were derived for a total of 88 species representing 75 to 85% of the triacylglycerols. About 90%, of the accumulated triacylglycerol contained at least one long-chain (C20–C22) monounsaturated fatty acid per molecule. The long-chain acids were confined mainly to the primary positions and preferentially to the sn-3-position of the glycerol molecule. The dietary lipidosis is, therefore, accompanied by little or no accumulation of the normal rat tissue triacylglycerols containing C16 and C18 fatty acids. It is suggested that the deposition and eventual clearance of the enantiomeric long-chain triacylglycerols in the rat heart during mustard seed oil feeding may be largely a result of a gradual change in specificity of the cardiac lipases.

THE FATTY ACIDS OF HARE'S-EAR MUSTARD SEED OIL

1946 ◽  
Vol 24b (5) ◽  
pp. 211-220 ◽  
Author(s):  
C. Y. Hopkins
Keyword(s):  
Fatty Acids ◽  
Methyl Ester ◽  
Erucic Acid ◽  
Seed Oil ◽  
Eicosenoic Acid ◽  
Mustard Seed ◽  
Seed Oils ◽  
Fatty Oil ◽  
Total Fatty Acids ◽  
Fractionation Method

The fatty oil of hare's-ear mustard seed (Conringia orientalis L.) was examined. Constants of the oil were determined and a partial separation of the fatty acids was carried out by the methyl ester fractionation method. Palmitic, oleic, linoleic, eicosenoic, erucic, and lignoceric acids were identified. Erucic acid was found to be present in largest amount. The oil resembles rapeseed and other Cruciferae seed oils in this respect. The content of eicosenoic acid is estimated to be not more than 12% of the total fatty acids.

Enantiomeric Diglycerides as Stereospecific Probes in Triglyceride Synthesis In Vitro

1972 ◽  
Vol 50 (8) ◽  
pp. 881-887 ◽  
Author(s):  
P. J. A. O'Doherty ◽  
A. Kuksis ◽  
D. Buchnea
Keyword(s):  
Fatty Acids ◽  
Thin Layer ◽  
Positional Distribution ◽  
Argentation Thin Layer Chromatography ◽  
Glycerol Molecule ◽  
Direct Acylation ◽  
Triglyceride Biosynthesis ◽  
Layer Chromatography ◽  
Single Enzyme

The stereospecificity of diglyceride acyltransferase (EC 2.3.1.20) was studied in the microsomes of rat intestine and liver using enantiomeric diglycerides as acceptors of labeled fatty acids. The diglyceride mixtures were prepared by combining equal amounts of synthetic 1,2- and 2,3-diglycerides of different degrees of unsaturation. The labeled triglycerides formed were resolved by argentation thin-layer chromatography, whereupon the products from each enantiomeric diglyceride moved to a different spot on the thin-layer plate.It was shown that both 1,2- and 2,3-diglycerides were utilized for direct acylation to triglycerides by both tissues. The diglyceride acyltransferase, if a single enzyme, showed a definite preference for the acylation of the 1,2-diglycerides. The intestine esterified more of the 2,3-isomer than did the liver. The yields of triglyceride depended upon the nature of the fatty acids involved, and their positional distribution on the glycerol molecule. The new method of stereospecific assessment of triglyceride biosynthesis in vitro is applicable to preparations of other subcellular fractions and to other suitable combinations of fatty acid and diglyceride precursors.

scholarly journals Patatin-Related Phospholipase pPLAIIIδ Increases Seed Oil Content with Long-Chain Fatty Acids in Arabidopsis

2013 ◽  
Vol 162 (1) ◽  
pp. 39-51 ◽  
Author(s):  
Maoyin Li ◽  
Sung Chul Bahn ◽  
Chuchuan Fan ◽  
Jia Li ◽  
Tien Phan ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oil Content ◽  
Seed Oil ◽  
Long Chain Fatty Acids ◽  
Seed Oil Content ◽  
Long Chain ◽  
Chain Fatty Acids

Lumenal hydrolysis of menhaden and rapeseed oils and their fatty acid methyl and ethyl esters in the rat

1989 ◽  
Vol 67 (4-5) ◽  
pp. 192-204 ◽  
Author(s):  
L.-Y. Yang ◽  
A. Kuksis ◽  
J. J. Myher
Keyword(s):  
Fatty Acids ◽  
Rapeseed Oil ◽  
Monounsaturated Fatty Acids ◽  
Ethyl Esters ◽  
Intestinal Lumen ◽  
Glycerol Molecule ◽  
A Chain ◽  
Layer Chromatography ◽  
Hydrolysis Of ◽  
Long Chain

Simple alkyl (ethyl) esters of polyunsaturated fish oil fatty acids have been proposed as dietary supplements, but their relative efficiency of digestion and absorption have not been determined. Using stomach tubes, we gave rats menhaden or rapeseed oils, or the corresponding methyl and ethyl esters, and determined by chromatographic methods the lipid classes and molecular species recovered from the lumen of the jejunum during the first 1 to 2.5 h of digestion. Hydrolysis of menhaden oil resulted in a preferential retention of a high proportion of the polyunsaturated long chain acids in the sn-2-monoacylglycerols and in the residual triacylglycerols, while digestion of rapeseed oil led to a preferential release of free long chain monounsaturated fatty acids. In contrast, hydrolysis of the alkyl (methyl and ethyl) esters of the fatty acids of either menhaden or rapeseed oil resulted in a composition of free fatty acids which was much more representative of the original esters. It was therefore concluded that the differential lumenal liberation of the long chain and polyunsaturated (three or more double bonds) fatty acids from fish and rapeseed oil is largely due to their characteristic distribution between the primary and secondary positions in the glycerol molecule, and to a much lesser extent to a chain length discrimination by pancreatic lipase. This study also shows that the methyl and ethyl esters are hydrolyzed about 4 times more slowly than the corresponding triacylglycerols, which is sufficient to maintain a saturated micellar solution of fatty acids in the intestinal lumen during absorption.Key words: gas chromatography, thin-layer chromatography, total lipid profiles, micellar and oil phases.

FATTY ACIDS OF THE SEED OIL OF CARDIOSPERMUM HALICACABUM

1958 ◽  
Vol 36 (11) ◽  
pp. 1537-1540 ◽  
Author(s):  
Mary J. Chisholm ◽  
C. Y. Hopkins
Keyword(s):  
Fatty Acids ◽  
Molecular Weight ◽  
Gas Chromatography ◽  
Seed Oil ◽  
Methyl Esters ◽  
Eicosenoic Acid ◽  
Major Fatty Acid ◽  
Low Molecular Weight ◽  
Long Chain Fatty Acids ◽  
Long Chain

The seed oil of Cardiospermumhalicacabum L., family Sapindaceae, was found to have 11-eicosenoic acid as the major fatty acid in its glycerides. In this respect it is unique among the true natural fats. The amount of eicosenoic acid in the sample examined was 42% of the total long-chain fatty acids. The identity and amounts of the principal fatty acids of the oil were determined by gas chromatography and by distillation of the methyl esters. The estimated percentages were: palmitic 3, linolenic 8, linoleic 8, oleic 22, stearic 2, eicosenoic 42, arachidic 10. In addition, there was evidence of small proportions (1–2%) of a low-molecular-weight acid and of C22 acids.

Stereochemical course of intestinal absorption and transport of mustard-seed oil triacylglycerols in the rat

1987 ◽  
Vol 65 (9) ◽  
pp. 811-821 ◽  
Author(s):  
J. J. Myher ◽  
A. Kuksis ◽  
L.-Y. Yang ◽  
L. Marai
Keyword(s):  
Fatty Acid ◽  
Seed Oil ◽  
Methyl Esters ◽  
Low Density Lipoprotein ◽  
Positional Distribution ◽  
Density Lipoprotein ◽  
Male Rats ◽  
Mustard Seed ◽  
Fatty Acid Chain ◽  
Wide Range

Male rats with thoracic duct cannulae were intubated with mustard-seed oil or the corresponding fatty acid methyl esters and the lymph was collected over 0–24 h. The chylomicron and very low density lipoprotein fractions were obtained by conventional ultracentrifugation. The triacylglycerols and glycerophospholipids were isolated and the positional distribution and molecular association of fatty acids were determined by stereospecific and chromatographic methods. The oleic, linoleic, and linolenic acids were recovered in the lymph in the proportion in which they occurred in the fat fed, while eicosenoic, erucic, and lignoceric acids were rejected to about the same extent by the two pathways of intestinal triacylglycerol biosynthesis. It is shown that the lymph triacylglycerols arising via the monoacylglycerol or the phosphatidic acid pathway possess structures that are closely similar to each other and to that of the original mustard-seed oil. It is proposed that this is a result of comparable fatty acid and positional specificity of the acyltransferases associated with the acylglycerol synthesis in the animal and plant tissues and the wide range of fatty acid chain lengths in the mustard-seed oil.

Hexacosanoic acid and other very long-chain fatty acids in peanut seed oil

2009 ◽  
Vol 7 (03) ◽  
pp. 252-256 ◽  
Author(s):  
Lisa L. Dean ◽  
Timothy H. Sanders
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Seed Oil ◽  
Germplasm Collection ◽  
Long Chain Fatty Acids ◽  
Peanut Seed ◽  
Hexacosanoic Acid ◽  
The Core ◽  
Long Chain ◽  
Chain Fatty Acids

The fatty acid composition of peanut seed oil from a range of samples included in the core of the core or the ‘mini core’ of the US peanut germplasm collection was determined using gas chromatography. Oil contents of the seeds ranged from 31.4 to 47.9%. Very long-chain fatty acids are defined as those having more than 22 carbons in chain length. Although it has been reported in peanuts seed previously, the presence of hexacosanoic acid (C26:0) was quantified in a large variety of samples here for the first time along with docosanoic (C22:0) and tetracosanoic acids (C24:0) to demonstrate the potential of peanut seed as a source of very long-chain fatty acids that have been associated with widely varying effects such as the metabolism of the dietary fatty acids and physical properties of the oils themselves. Use of representative samples from the peanut germplasm collection allowed for comparison of very long-chain fatty acid content among seeds of different origins, and showed, although values overlapped, the seeds did cluster according to area of origin.

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