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

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.

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Intestinal absorption of menhaden and rapeseed oils and their fatty acid methyl and ethyl esters in the rat

Biochemistry and Cell Biology ◽

10.1139/o90-068 ◽

1990 ◽

Vol 68 (2) ◽

pp. 480-491 ◽

Cited By ~ 29

Author(s):

L.-Y. Yang ◽

A. Kuksis ◽

J. J. Myher

Keyword(s):

Fatty Acids ◽

Phosphatidic Acid ◽

Cellular Uptake ◽

Rapeseed Oil ◽

Unsaturated Fatty Acids ◽

Ethyl Esters ◽

Menhaden Oil ◽

Lower Efficiency ◽

Acid Pathway ◽

Long Chain

The relative cellular uptake and incorporation into prechylomicrons and chylomicrons was investigated for the menhaden and rapeseed oil fatty acids, when given by stomach tube as the original oils or the corresponding methyl and ethyl esters. The intermediates and final products of cellular acylation were determined by chromatographic methods at various times over a period of 1–24 h. There was little selectivity in the uptake among the oligo- and poly-unsaturated fatty acids of menhaden oil, when either oil or esters were fed. In contrast, the long-chain saturated and monounsaturated fatty acids of rapeseed oil were discriminated against during both cellular uptake and reacylation (60% overall reduction in utilization). Also, there was detectable discrimination against the long-chain polyunsaturated monoacylglycerols of menhaden oil and against the long-chain saturated and monounsatured monoacylglycerols of rapeseed oil during both cellular uptake and reacylation (30% overall reduction in utilization). Evidence was obtained for an indiscriminate cellular uptake of variable amounts (4–22%) of intact dietary methyl and ethyl esters of fatty acids, which, however, appeared in the chylomicrons only to a very limited extent (0.1–1.0% of total lipid). During peak absorption the cellular and lymphatic appearance of fatty acids from the digestion and absorption of the alkyl esters was nearly 50% lower than that from the corresponding triacylglycerols. The slower absorption of the fatty acids from the alkyl ester feeding is hypothetically attributed to a lower efficiency of the phosphatidic acid pathway, which is required in the absence of dietary 2-monoacylglycerols, but other mechanisms cannot be excluded.Key words: villus cells, prechylomicrons, chylomicrons, triacylglycerol biosynthesis, monoacylglycerol pathway, phosphatidic acid pathway.

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THE HYDROLYSIS OF MONOPHOSPHOINOSITIDE BY EXTRACTS OF BRAIN

Canadian Journal of Biochemistry ◽

10.1139/o67-095 ◽

1967 ◽

Vol 45 (6) ◽

pp. 853-861 ◽

Cited By ~ 60

Author(s):

W. Thompson

Keyword(s):

Fatty Acids ◽

Enzyme Activity ◽

Calcium Ions ◽

Brain Extract ◽

Monovalent Cations ◽

High Concentration ◽

Diffusible Factor ◽

Hydrolysis Of ◽

The Brain ◽

Long Chain

The hydrolysis of monophosphoinositide by soluble extracts from rat brain is described. Diglyceride and inositol monophosphate are liberated along with a small amount of free fatty acids. Hydrolysis of the lipid is optimal at pH 5.4 in acetate buffer. The reaction is stimulated by calcium ions or by high concentration of monovalent cations and, to a less extent, by long-chain cationic amphipathic compounds. Enzyme activity is lost on dialysis of the brain extract and can be restored by diffusible factor(s). Some differences in the conditions for hydrolysis of mono- and tri-phosphoinositides are noted.

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Fat Malabsorption in Preterm and Term Neonates Is Not Due to Insufficient Lipolysis, but to Impaired Uptake of Long Chain Fatty Acids from the Intestinal Lumen

Pediatric Research ◽

10.1203/00006450-199904020-01723 ◽

1999 ◽

Vol 45 (4, Part 2 of 2) ◽

pp. 290A-290A ◽

Cited By ~ 1

Author(s):

Edmond H H M Rings ◽

Deanna M Minich ◽

Willem P F Fetter ◽

Frans Stellaard ◽

Roel J Vonk ◽

...

Keyword(s):

Fatty Acids ◽

Intestinal Lumen ◽

Long Chain Fatty Acids ◽

Term Neonates ◽

Fat Malabsorption ◽

Long Chain ◽

Chain Fatty Acids

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

Canadian Journal of Biochemistry ◽

10.1139/o79-175 ◽

1979 ◽

Vol 57 (11) ◽

pp. 1315-1327 ◽

Cited By ~ 5

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.

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Rapid in vivo hydrolysis of fatty acid ethyl esters, toxic nonoxidative ethanol metabolites

AJP Gastrointestinal and Liver Physiology ◽

10.1152/ajpgi.1997.273.1.g184 ◽

1997 ◽

Vol 273 (1) ◽

pp. G184-G190 ◽

Cited By ~ 7

Author(s):

M. Saghir ◽

J. Werner ◽

M. Laposata

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Free Fatty Acids ◽

Fatty Acid Ethyl Esters ◽

Ethyl Esters ◽

Ethanol Ingestion ◽

Gi Tract ◽

Apparent Lack ◽

Hydrolysis Of

Fatty acid ethyl esters (FAEE), esterification products of fatty acids and ethanol, are in use as fatty acid supplements, but they also have been implicated as toxic mediators of ethanol ingestion. We hypothesized that hydrolysis of orally ingested FAEE occurs in the gastrointestinal (GI) tract and in the blood to explain their apparent lack of toxicity. To study the in vivo inactivation of FAEE by hydrolysis to free fatty acids and ethanol, we assessed the hydrolysis of FAEE administered as an oil directly into the rat stomach and when injected within the core of low-density lipoprotein particles into the circulation of rats. Our studies demonstrate that FAEE are rapidly degraded to free fatty acids and ethanol in the GI tract at the level of the duodenum with limited hydrolysis in the stomach. In addition, FAEE are rapidly degraded in the circulation, with a half-life of only 58 s. Thus the degradation of FAEE in the GI tract and in the blood provides an explanation for the apparent lack of toxicity of orally ingested FAEE.

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Bacterial precursors and unsaturated long-chain fatty acids are biomarkers of North-Atlantic demosponges

10.1101/2020.10.09.332833 ◽

2020 ◽

Cited By ~ 1

Author(s):

Anna de Kluijver ◽

Klaas G.J. Nierop ◽

Teresa M. Morganti ◽

Martijn C. Bart ◽

Beate M. Slaby ◽

...

Keyword(s):

Fatty Acids ◽

North Atlantic ◽

Deep Sea ◽

North Atlantic Ocean ◽

Carbon Isotopic Composition ◽

Building Blocks ◽

Functional Ecology ◽

The North ◽

A Chain ◽

Long Chain

AbstractSponges produce distinct fatty acids (FAs) that (potentially) can be used as chemotaxonomic and ecological biomarkers to study endosymbiont-host interactions and the functional ecology of sponges. Here, we present FA profiles of five common habitat-building deep-sea sponges (class Demospongiae, order Tetractinellida), which are classified as high microbial abundance (HMA) species. Geodia hentscheli, G. parva, G. atlantica, G. barretti, and Stelletta rhaphidiophora were collected from boreal and Arctic sponge grounds in the North-Atlantic Ocean. Bacterial FAs dominated in all five species and particularly isomeric mixtures of mid-chain branched FAs (MBFAs, 8- and 9-Me-C16:0 and 10 and 11-Me-C18:0) were found in high abundance (together ≥ 20% of total FAs) aside more common bacterial markers. In addition, the sponges produced long-chain linear, mid- and a(i)-branched unsaturated FAs (LCFAs) with a chain length of 24‒28 C atoms and had predominantly the typical Δ5,9 unsaturation, although also Δ9,19 and (yet undescribed) Δ11,21 unsaturations were identified. G. parva and S. rhaphidiophora each produced distinct LCFAs, while G. atlantica, G. barretti, and G. hentscheli produced similar LCFAs, but in different ratios. The different bacterial precursors varied in carbon isotopic composition (δ13C), with MBFAs being more enriched compared to other bacterial (linear and a(i)-branched) FAs. We propose biosynthetic pathways for different LCFAs from their bacterial precursors, that are consistent with small isotopic differences found in LCFAs. Indeed, FA profiles of deep-sea sponges can serve as chemotaxonomic markers and support the conception that sponges acquire building blocks from their endosymbiotic bacteria.

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Mode of action of choline. III. Metabolism of nonessential fatty acids in choline-deficient rats

Canadian Journal of Biochemistry ◽

10.1139/o69-097 ◽

1969 ◽

Vol 47 (6) ◽

pp. 619-630 ◽

Cited By ~ 2

Author(s):

A. Chalvardjian

Keyword(s):

Fatty Acids ◽

Thin Layer ◽

Saturated Fatty Acids ◽

Monounsaturated Fatty Acids ◽

Serum Triglycerides ◽

Hepatic Lipids ◽

Layer Chromatography ◽

Serum Phospholipids ◽

Early Alteration ◽

Initial Change

To investigate the increase in ratio of C16 to C18 nonessential fatty acids in hepatic triglycerides of choline-deficient rats, two groups of rats fed, respectively, a choline-deficient and a choline-supplemented diet for 3–4 days were injected either with 1-14C-acetate intraperitoneally or with a mixture of 9,10-3H-palmitate and 18-14C-stearate intravenously. The choline-deficient and choline-supplemented rats were killed 3 h after labelled acetate injection. Further groups of choline-deficient and choline-supplemented rats were killed at intervals of 1 min to 6 h after injection with labelled palmitate and stearate. Extracts of lipids from livers and sera were analyzed by gas–liquid and thin-layer chromatography. In the choline-deficient rats injected with 1-14C-acetate the ratio of C16 to C18 labelled fatty acids incorporated into hepatic and serum triglycerides was increased and the ratio of those incorporated into hepatic and serum phospholipids was decreased. The ratio of monounsaturated fatty acids to saturated fatty acids incorporated into the triglycerides and phospholipids of liver and serum of the choline-deficient rats was decreased compared to that of the choline-supplemented rats. Similar differences between the two groups of rats were evident in the hepatic lipids of animals injected with 3H-palmitate and 14C-stearate. The early alteration of the ratios of hepatic nonessential fatty acids suggests that the initial change is a decreased desaturation of fatty acids.

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Heparin-released lipolytic and esterolytic activities of human and rabbit plasmas

American Journal of Physiology-Legacy Content ◽

10.1152/ajplegacy.1961.201.5.915 ◽

1961 ◽

Vol 201 (5) ◽

pp. 915-922 ◽

Cited By ~ 60

Author(s):

B. Shore ◽

V. Shore

Keyword(s):

Fatty Acids ◽

Lipoprotein Lipase ◽

Lipase Activity ◽

Ethyl Esters ◽

Lipoprotein Lipase Activity ◽

Hydrolysis Of

The enzymes released into both human and rabbit plasmas by heparin injection hydrolyzed, in addition to triglyceride moieties of lipoproteins, a number of mono- and diglycerides of C16 and C18 fatty acids after in vitro addition of the unemulsified glycerides to the plasma. In human postheparin plasma, these enzymes also hydrolyzed glycerides of butyric and caproic acids. The pure triglycerides and methyl or ethyl esters of C16 and C18 fatty acids were not substrates. The heparin-released activities for the hydrolysis of glycerides added in vitro persisted after all activity for the lipolysis of lipoproteins had been destroyed by heat. These activities also differed from lipoprotein lipase activity with respect to the effects of 1 m NaCl, dialysis, and aging the plasma at 4 C. It appears that heparin releases into the blood more than one enzyme or more than one form of an enzyme which may be involved in a stepwise degradation to fatty acids and glycerol of the triglyceride moieties of lipoproteins of density less than 1.007 g/ml.

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Characterization of the oils present in acid and fermented silages produced from Tilapia filleting residue

Revista Brasileira de Zootecnia ◽

10.1590/s1516-35982011000200002 ◽

2011 ◽

Vol 40 (2) ◽

pp. 240-244 ◽

Cited By ~ 6

Author(s):

Rose Meire Vidotti ◽

Maria Teresa Bertoldo Pacheco ◽

Giovani Sampaio Gonçalves

Keyword(s):

Fatty Acids ◽

Fatty Acid ◽

Nutritional Value ◽

Lipid Fraction ◽

Monounsaturated Fatty Acids ◽

Degree Of Saturation ◽

Degree Of Hydrolysis ◽

Animal Feeding ◽

Hydrolysis Of

The objective of this study was to determine the quality and composition of fatty acid in the lipid fraction of silages obtained from the residue of tilapia processing. Stratification of the lipid layer of the silages occurred at different times among the two types of silage (acid and fermented) and the greatest volume of oil was observed in acid silage (8.67% p/p). Although acid silage was more oxidized, it showed lower contents of free fatty acids probably because the degree of hydrolysis of its components is lower than that of fermented silage. Fatty acid composition did not differ among processes inasmuch as level of ϖ-3 was slightly higher in fermented silage. According to the degree of saturation, monounsaturated fatty acids stood out as the predominant category in acid and fermented silages with values of 39.69% and 33.39%, respectively. The use of antioxidants in the silage is needed because the process of production is carried out at temperatures higher than room temperature. The oil in the silages has excellent nutritional value and contains fatty acids essential for animal feeding.

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