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PubMed1982

Effects of dietary cholesterol and type of dietary carbohydrate on hepatic and plasma glycerides and phospholipids in the gerbil.

The influence of dietary cholesterol at levels of 0.01-0.5% (by weight) and carbohydrate type (starch, sucrose or a starch-sucrose mixture) on levels and composition of hepatic and plasma glycerides in the male Mongolian gerbil (Meriones unguiculatus) was studied. Hepatic and plasma triglyceride (TG) levels were generally higher with dietary cholesterol supplementation (0.1 and 0.5%), and animals fed sucrose diets exhibited very low levels of hepatic and plasma TG. The mixed carbohydrate (starch-sucrose) did not affect glycerides in a way that could be interpolated from feeding starch or sucrose diets alone. The percent of 16:0 in liver TG was depressed with cholesterol-feeding (at the 0.5% level only), whereas the percent of 18:1 was elevated. Sucrose diets produced higher percentages of 18:0 in liver TG. Dietary cholesterol elevated concentrations of plasma but not liver phospholipid (PL). Percentages of 20:40 omega 6 and 22:6 omega 3 acids in liver and plasma PL were significantly depressed by cholesterol supplementation, whereas the percent of 18:2 in liver PL was higher when feeding cholesterol and starch (no sucrose). Dietary cholesterol produced higher levels of hepatic 1,2-diglyceride with lower percentages of 18:0 and 20:4 omega 6 and higher percentages of 18:1 and 18:2. Dietary cholesterol may possibly influence fatty acid elongation and desaturation reactions as well as transacylation reactions in phospholipid synthesis. In this regard, compositional data suggested a suppressing effect of dietary cholesterol on 22:6 omega 3 formation as exemplified by a 40% diminution in the docosahexaenate content of hepatic phosphatidylethanolamine in gerbils fed a 0.5% cholesterol diet for only 7 days.

Animals↗
PubMed1980

Purification and properties of partial glyceride hydrolase of Penicillium cyclopium M1.

A lipolytic enzyme which hydrolyzed monoacylglycerols more easily than triacylglycerols was found in the culture broth of Penicillium cyclopium M1. The enzyme was purified to homogeneity and its properties were investigated. Among various substrates used, monoacylglycerols, especially those of medium chain fatty acids, were hydrolyzed very rapidly. Although the rate was low, the enzyme hydrolyzed methyl esters of fatty acids, Span or triacylglycerols of medium chain fatty acids. Based on its substrate specificity, the enzyme was regarded as a partial glyceride hydrolase. When the partial glyceride hydrolase was used in conjunction with lipase on triacylglycerol, the degree of hydrolysis of triacylglycerol became extremely high.

Carboxylic Ester Hydrolases↗
PubMed1970

An AutoAnalyzer method for estimating serum glyceride glycerol using a glycerokinase procedure.

THE GLYCERIDE GLYCEROL ANALYSIS DEPENDS, AFTER SAPONIFICATION OF TRIGLYCERIDES, ON A LINKED ENZYMATIC PROCEDURE USING GLYCEROKINASE, PYRUVATE KINASE, AND LACTATE DEHYDROGENASE: the final conversion of NADH to NAD(+) is followed fluorimetrically. Twenty analyses can be performed per hour on the AutoAnalyzer; recoveries of added triglycerides ranged between 90 and 104%. In a mixed male and female group the normal range for glyceride glycerol was 2.5 to 15.5 mg/100 ml (0.2-1.4 mmol/l) fasting, and 2.5 to 18.0 mg/100 ml (0.2-1.6 mmol/l) postprandially using fresh serum. There was a significant rise postprandially in older men.

Adult↗
PubMed1980

Effect of heparin on the utilization in vitro of labelled glycerides from triglyceride-rich lipoproteins in rat adipose tissue.

Triglyceride-rich lipoproteins from adult rat plasma were labelled in vivo with 3H in the esterified fatty acids and 14C in the labelled glyceride glycerol of neutral lipids by injecting i.v. sodium 9-10 (n)-[3H] palmitate and [U-14C] glycerol, after which the prelabelled lipoproteins were purified by ultracentrifugation and dialysis. The lipoproteins were incubated in vitro, in the presence or not of heparin, with pieces of epididymal fat pads or isolated adipocytes from fed rats. The disappearance of both [3H]- and [14C] lipids from the media was greater when incubations were performed with adipocytes than with fat-pad pieces and it increased with heparin in both preparations. More 3H-label than 14C was found in the tissue lipids, a higher percentage being present in adipocytes than in fat-pad pieces, and the amount of label in tissue lipids was always enhanced by heparin. Some 14C-label appeared as esterified fatty acids in both tissue preparations and it also was enhanced by the presence of heparin. These findings are in agreement with the recognized influence of heparin on the release of lipoprotein lipase and show the direct relationship between heparin action and tissue ability to take up products of lipoprotein triglyceride breakdown. They also demonstrate the ability of adipose tissue to metabolize glycerol coming from the hydrolysis of lipoprotein glycerides.

Adipose Tissue↗
PubMed1990

Stereoselectivity of lipases. I. Hydrolysis of enantiomeric glyceride analogues by gastric and pancreatic lipases, a kinetic study using the monomolecular film technique.

In the present study, porcine pancreatic lipase, rabbit gastric lipase, and human gastric lipase stereospecificity toward enantiomeric glyceride derivatives was kinetically investigated using the monomolecular film technique. Pseudoglycerides such as enantiomeric 1(3)-alkyl-2,3(1,2)-diacyl-sn-glycerol, enantiomeric 1(3)-alkyl-2-acyl-sn-glycerol, or enantiomeric 1(3)-acyl-2-acylamino-2-deoxy-sn-glycerol were synthesized in order to assess the lipase stereoselectivity during the hydrolysis of either the primary or the secondary ester position of these glycerides analogues. The cleaved acyl moiety was the same in both enantiomers, thereby excluding the possibility of effects occurring due to fatty acid specificity. We observed a porcine pancreatic lipase sn-3 stereoselectivity when using the enantiomeric 1(3)-alkyl-2-acylamino-2-deoxy-sn-glycerol (diglyceride analogue) which contrasted with the lack of stereoselectivity observed when using the enantiomeric 1(3)-alkyl-2,3(1,2)-diacyl-sn-glycerol (triglyceride analogue). The gastric lipases, in contrast to the pancreatic lipase, preferentially catalyze the hydrolysis of the primary sn-3 ester bond of the enantiomeric monoakyl-diacyl pair tested. From these kinetic data, high hydrolysis rates and no chiral discrimination were observed in the case of rabbit gastric lipase, whereas low rates and a clear chiral discrimination was noticed in the case of human gastric lipase during hydrolysis of the acyl chain from the secondary ester bond of 1(3)-alkyl-2-acyl enantiomers. It is particularly obvious that in the case of human gastric lipase decreasing the lipid packing increases the lipase sn-3 stereopreference during hydrolysis of the primary ester bond of the enantiomeric 2-acylamino derivatives (diglyceride analogue).

Animals↗
PubMed1986

Direct enzymic measurement of glycerides in serum and in lipoprotein fractions.

A simple two-step procedure is now available for directly measuring triglycerides in whole serum and in lipoprotein fractions. I tested the performance of the assay, using pooled serum stored frozen, freshly prepared lipoprotein fractions, and pure glyceride standards. A parabolic concentration-response curve ensured linearity well beyond total glycerol concentrations of 10 mmol/L, but gave rise to misleading results for massively lipemic samples. Within-day CVs averaged 2.2% for the stored-frozen serum pools; mean day-to-day variation was 2.4%. Analytical recoveries of triglycerides, after lipoprotein fractionation, ranged between 101.9 and 103.7%. Aqueous glyceride standards gave results equivalent to between 95 and 105% of their glycerol content.

Glycerol↗
PubMedDate not supplied

[Use of pancreatic lipase for determination of the glyceride composition of rice lipids].

The triglyceride composition of rice lipids was investigated, using methods of thin-layer chromatography, enzymic hydrolysis by pancreatic lipase and gas-liquid chromatography. The major portion of triglycerides were tri- and di-unsaturated glycerides. The content of trisaturated glycerides was not more than 0.86%. The data obtained allow the conclusion that unsaturated acids occupy 2-positions in the triglyceride molecule of rice oil and oil of other plants.

Chemical Phenomena↗
PubMed1990

Effect of medium-chain glycerides on the intestinal absorption of phenol red: studies on mechanisms of the promoting effect.

To elucidate the mechanisms of the promoting action of medium-chain glyceride (MCG) on the intestinal absorption of phenol red (PR), the effect of different MCG dose levels on PR absorption, the absorption kinetics of MCG itself, and the mucosal reduced glutathione (GSH) levels were investigated to determine whether or not they are related to the promoting action of MCG. The absorption of PR was found to be enhanced with an increase in MCG dose (as an emulsion in the range 0.5-4.0%). Urinary excretion of PR was reduced by absorbed MCG components, which also resulted in an increase in the AUC. Moment analysis of plasma PR concentrations after intraintestinal administration revealed a shorter mean absorption time (MAT) for the emulsion formulation than for the control. The mucosal GSH level was lowered by the administration of the MCG emulsion (2-10%) into the intestinal lumen. Pretreatment with a 4% MCG emulsion decreased GSH levels to one-half of the control. In these cases, the level of mucosal GSH seemed to remain constant to the end of the experiment after it had decreased during the initial period. On the other hand, results from the in situ loop or recirculation study showed that enhancement of PR absorption appeared in the earlier period and then gradually decreased. The time course of the PR absorption rate, estimated from plasma concentration data, was similar to that of the MCG absorption rate. These results suggest that the promotion of intestinal absorption is related to the absorption kinetics of MCG itself, but not directly to the level of mucosal GSH.

Animals↗
PubMed1988

The incorporation of intracranially injected glycerol into brain glycerides of young rats born to normal and alcohol-fed mothers.

Growth alters the ability of rat brain to incorporate [2-3H]glycerol into glycerides; indeed, 12 min after the intracranial administration of the precursor, diglyceride becomes more radioactive in newborn than in 19-day-old brain, the reverse being true for total glycerophospholipid and triglyceride. The ratio between the labeling of phospholipid and that of neutral lipid in the experimental conditions described in this paper is proposed as a marker of brain maturity. The distribution of labeling among phospholipid classes also varies with age, and the increase of labeling in total phospholipid occurring with increasing age is almost entirely due to phosphatidylethanolamine and phosphatidylcholine. The metabolism of myelin lipids might be responsible for these age-dependent variations. The administration of ethanol to dams during pregnancy and lactation alters the distribution of the label among neutral glycerolipid and total glycerophospholipid in an age-dependent manner. The labeling distribution among phospholipid classes is also affected.

Aging↗
PubMed1976

Effect of dietary fat supplementation on the composition and positional distribution of fatty acids in ruminant and porcine glycerides.

Dietary fats which were protected from ruminal metabolism were fed to ruminants, and the constituent fatty acids subsequently appeared in the glycerides of tissues and secretory products. These dietary fat induced alterations in tissue lipid composition were particularly apparent when the fat source was enriched with linoleic acid. Similarly, when pigs were fed linoleic-enriched fats, the linoleic acid was incorporated into the adipose tissue triglycerides. Stereospecific analyses were carried out on triglycerides from various tissues and secretory products obtained from animals fed control or linoleate-enriched diets. The analysis of adipose tissue triglycerides showed that linoleate and oleate were preferentially esterified to positions 2 and 3 (cattle and sheep), and positions 1 and 3 (pigs). Of the other major adipose tissue fatty acids, palmitate was preferentially esterified at position 1 (ruminants) and position 2 (pigs), and stearate was preferentially esterified at positions 1 and 3 (ruminants), and position 1 (pigs). Stereospecific analysis of high mol wt milk triglycerides showed that linoleate was either evenly distributed on all three positions (goats), or predominantly on position 3 (cows). Furthermore, the incorporation of this linoleate did not markedly alter the positional specificity of the other major milk triglyceride fatty acids. Of these fatty acids, the short and medium chain length acids (butyratelaurate) were mainly on position 3, myristate and palmitate on positions 1 and 2, and stearate and oleate evenly distributed. Thoracic duct lymph triglycerides from sheep tended to show preferential incorporation of linoleate at position 3, palmitate at position 2, and stearate at position 1 and 3; oleate, on the other hand, tended to be evenly distributed on all three positions of the lymph triglyceride. The stereospecific arrangement of fatty acids in sheep liver triglycerides was similar to that of lymph triglycerides, and this may reflect the uptake of intact or partially hydrolysed chylomicron and/or very low density lipoprotein triglycerides by the liver. There were also some analogies in the stereospecific arrangement of fatty acids on ruminant lymph and milk triglycerides and this may reflect an incomplete hydrolysis of chylomicron and/or very low density lipoprotein triglycerides prior to uptake by the mammary gland. An unusual feature of lymph from sheep fed linoleate was the presence of phospholipids which contained large amounts of linoleate in ca. equal proportion at both positions 1 and 2 of the phospholipid molecule.

Adipose Tissue↗
PubMed1977

Glyceride metabolism in the myopathic hamster.

Analysis of plasma lipids of 30- and 185-day-old BIO 82.62 myopathic hamsters and age-matched normal controls revealed a decrease in only the concentration of cholesteryl esters of 185-day-old diseased animals. Measurement of lipoprotein lipase (LPL) activity in heart, muscle, and adipose tissue showed no difference between the activity of the enzyme in the heart and muscle of the cardiomyopathic hamsters and that of the age-matched controls. In adipose tissue, however, LPL activity was depressed in the diseased animals in both age groups. No difference was found in the activity of hormone sensitive lipase. Incorporation of sn[U-14C] glycerol-3-phosphate into total lipids was found to be depressed in homogenates of heart, muscle, and adipose tissue but unchanged in liver homogenates of diseased animals. It was concluded that the decrease in the capacity to synthesize glycerides, rather than limiting substrate concentrations, could be the cause of the decrease in the lipid content in some tissues of the cardiomyopathic hamster.

Adipose Tissue↗
PubMed1985

Influence of dietary cholesterol on the relative synthesis of hepatic glycerides and molecular classes of 1,2-diglycerides and phospholipids in the gerbil in vivo.

The influence of dietary cholesterol on the relative rates of synthesis of hepatic lipids in the male Mongolian gerbil, Meriones unguiculatus, was studied. The semi-purified starch-based diet used lard as the dietary fat and was fed with or without a 0.5% (by wt.) cholesterol supplement. Each animal received 300 microCi [2-3H]-glycerol i.p. after 3 or 7 days on the dietary regimens. Relative rates of [2-3H]-glycerol incorporation into the major hepatic glycerides in vivo was not affected significantly by dietary cholesterol (0.5% level), suggesting that alteration in the relative biosynthesis of these lipids could not readily account for the higher triglyceride (TG) to phospholipid (PL) mass ratio in liver with cholesterol feeding. However, there was evidence for an increased formation of 1,2-diglyceride (1,2-DG). The complement of molecular species of hepatic 1,2-DG, phosphatidylcholine (PC), and phosphatidylethanolamine (PE) formed de novo, as measured using isotopic glycerol, was not influenced greatly by dietary cholesterol, although lower mean rates of synthesis of tetraenoic relative to dienoic species of phospholipids were indicated in cholesterol-fed gerbils.

Animals↗
PubMed1980

Studies on the substrate specificity of a carboxyl ester hydrolase from human pancreatic juice. I. Action on carboxyl esters, glycerides and phospholipids.

Purified carboxyl ester hydrolase (carboxylic-ester hydrolase, EC 3.1.1.1) from human pancreatic juice was found to hydrolyze triacetin, methyl butyrate and glycerides solubilized by bile salts. It has no activity on substrate presented as emulsoin or monomolecular films. The human enzyme was found to deacylate phospholipids and lysophospholipids at different rates. The hydrolysis of short-chain phosphatidylcholines was dependent of substrate solubility and dioctanoyl phosphatidylcholine was deacylated with the highest rate. Long-chain phosphatidylcholines and lysophosphatidylcholines present in microsomal membranes were deacylated with very low rates, only lysophosphatidylcholine deacylation was faster. Evidence is presented that human carboxyl ester hydrolase is the lyophosphatidyl-choline-hydrolyzing enzyme corresponding to bovine lysophospholipase. Bile salts play an important part on the activity of human carboxyl ester hydrolase, in addition to the role of detergent that they have on insoluble substrates.

Bile Acids and Salts↗
PubMed1984

Substrate specificity of two cationic lipases with high phospholipase A1 activity purified from guinea pig pancreas. I. Studies on neutral glycerides.

The substrate specificity of two cationic lipases with high phospholipase A1 activity purified from guinea pig pancreas has been tested towards various neutral glycerides. Triolein hydrolysis proceeded in the absence of di- and monoolein accumulation. Optimal conditions for di- and monoolein hydrolysis included an alkaline pH (9-10), a substrate concentration of 10 mM, and the presence of sodium deoxycholate (12 and 24 mM, respectively). Pancreatic colipase (bovine) had no effect on the activity of the two lipases. The comparison between the rates of hydrolysis of various substrates revealed the following order of decreasing enzyme activity: diolein greater than 1(3)-monoolein greater than tributyrin = triacetin greater than or equal to triolein = 2-monoolein. No hydrolysis of p-nitrophenylacetate and cholesteryloleate could be detected. Using 1-[3H]palmitoyl-2-[14C]linoleoyl-sn-glycerol, both enzymes displayed a strong preference for the 1-position, leading to the accumulation of 2-[14C]linoleoyl-sn-glycerol. Identical activities were found for the two lipases. It is concluded that the two cationic lipases from guinea pig pancreas represent a unique group of lipolytic enzymes different from other previously described enzymes, including classical pancreatic lipase, gastric and lingual enzymes, mold lipases and carboxylesterhydrolase.

Animals↗
PubMed1993

The relationship between the effect of biphenylcarboxylic acid analogs on glyceride synthesis and conformation.

The inhibition of biphenylcarboxylic acid analogs on glyceride synthesis was studied in association with conformation of the chemicals. Chemicals used were benzoic acid substituted with phenyl, benzoyl and phenoxy groups, phenylphenyloxyacetic acid and p-phenylacetic acid. Twist angles were calculated by a molecular orbital method. Following oral administration of p-phenylbenzoic acid to the rats for 7 days, the decrease of the triglyceride synthesized from [14C]oleic acid was observed in the adipose tissue. The in vitro inhibitions on the formation of fatty acyl-CoA thioester were examined from the influence on the hippuric acid formation from [14C]benzoic acid using the rat liver slices. In the homologous series, high inhibition was observed in para and meta substituents. None, or low inhibitions of ortho-substituted chemicals were related to the steric hindrance of the phenyl ring against carboxyl groups. This hinderance was associated with conformation and with the geometrical relationship between substituted phenyl rings and carbon atoms of carboxylic acid. In the in vitro inhibition on overall formation of diglyceride and triglyceride from [14C]glycerol, o-phenylbenzoic acid showing no inhibition on hippuric acid formation did not show inhibition. However, other ortho-substituted chemicals showed higher inhibition in comparison with the inhibition on hippuric acid formation. The inhibition of para- and meta-substituted chemicals were higher than the corresponding values of ortho substituted compounds.

Animals↗
PubMed1976

The synthesis of chiral glycerides starting from D- and L-serine.

A method for synthesizing chiral glycerides starting from L- or D-serine is described. Optically-active serine (both enantiomers are commerically available) was transformed into glyceric acid by stereospecific diazotization. The configuration at carbon atom 2 was maintained during the reaction. The glyceric acid was then converted into optically pure isopropylideneglycerol - which is an important intermediate in the synthesis of mono-, di- and triglyderides - by esterification followed by acetalization with acetone and reduction with lithium aluminium hydride. Reaction of this intermediate with triphenylphosphine in tetrachloromethane followed by acid-catalysed hydrolysis and dehydrohalogenation provided optically-active glycidol (2,3-epoxy-1-propanol). The epoxy ring of an ester of glycidol and a fatty acid was then opened stereospecifically with retention of configuration by heating the glycidol ester in the presence of a second fatty acid and a catalyst. This yielded a chiral 1,3-diglyceride which could be converted into a chiral triglyceride.

Diglycerides↗
PubMed1994

Interactions between beta-cyclodextrin and insoluble glyceride monomolecular films at the argon/water interface: application to lipase kinetics.

A study of the desorption rate of insoluble monomolecular films of oleic acid (OA), monoolein (MO), 1,2-diolein (1,2-DO), 1,3-diolein (1,3-DO) and triolein (TO) at the argon/water interface by water-soluble beta-cyclodextrin (beta-CD) is reported. The desorption of OA and MO involves probably the complexation of the single acyl chain with beta-CD and sequestering of the formed soluble OA/beta-CD and MO/beta-CD complexes from the argon/water interface. In the case of monolayers of multiple acyl chain molecules such as DO and TO, no detectable change in the surface pressure occurred after beta-CD injection. The surface rheological dilatational properties of the monolayers of DO and TO in the presence of beta-CD in the subphase were studied. The elasticity of the DO monolayer remained unchanged, whereas the decrease in the surface elasticity of the TO film was attributed to the formation of a water-insoluble TO/beta-CD complex. With the 'tuning fork' model, one acyl chain of TO can be included in the beta-CD cavity. The formed TO/beta-CD complex present at the interface retarded the propagation of the dilatational deformation along the plane of the monolayer. Schematic models have been proposed in an attempt to explain the different complexation of these lipids by beta-CD at the argon/water interface. In addition to the above results, the presence of beta-CD in the water subphase makes it possible for the first time to perform kinetic measurements of the lipase hydrolysis rates of long-chain glycerides forming monomolecular films.

Argon↗
PubMed1982

[A detailed lipidograph: enzymatic determination of cholesterol, phospholipids and glycerides in plasma lipoprotein after a cellulose acetate electrophoretic procedure (author's transl)].

The specific determination of cholesterol and its evaluation in lipoproteins separated by cellulose acetate electrophoresis is described. Using this technique, the authors extended the specific lipid determinations to phospholipids and glycerides. The precision, linearity, accuracy of the methods are satisfactory for fractions greater than 10%. Phospholipids and cholesterol values in alpha lipoproteins are compared with those obtained in the supernatant by concanavalin A precipitation; the differences between the two methods are not significant. We suggest using these three enzymatic determinations to produce a detailed lipidograph. For a selected population, the lipid values in each fraction (expressed in g/l and in mmol/l) were close to those given in the literature. We compared our lipidograph, expressed in SI units, with the Oil Red O stained lipidograph; the difference was not significant.

Adult↗