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PubMed1992

Inhibition of enoyl-CoA hydratase by long-chain L-3-hydroxyacyl-CoA and its possible effect on fatty acid oxidation.

The kinetics of bovine liver enoyl-CoA hydratase (EC 4.2.1.17) or crotonase with 2-trans-hexadecenoyl-CoA as a substrate were studied because different rates were obtained with two assay methods based on measurements of substrate utilization and product formation, respectively. L-3-Hydroxyhexadecanoyl-CoA, the product of the crotonase-catalyzed hydration of 2-trans-hexadecenoyl-CoA, was found to be a strong competitive inhibitor of the enzyme with a Ki of 0.35 microM. In contrast the short-chain product, L-3-hydroxybutyryl-CoA, is a weak competitive inhibitor with a Ki of 37 microM. L-3-Hydroxyhexadecanoyl-CoA is a much stronger inhibitor of crotonase than are other short-chain and long-chain intermediates of beta-oxidation and crotonase is more severely inhibited by this compound than are all beta-oxidation enzymes tested so far. Determination of true kinetic parameters for the crotonase-catalyzed hydration of long-chain substrates requires the removal of product in a coupled assay. When this was done, the Km for 2-trans-hexadecenoyl-CoA with bovine liver crotonase was found to be only 9 microM. It is suggested that under conditions of restricted beta-oxidation, when 3-hydroxyacyl-CoAs accumulate in mitochondria, the inhibition of crotonase by long-chain 3-hydroxyacyl-CoAs may limit the further degradation of medium-chain and short-chain intermediates of beta-oxidation.

Acyl Coenzyme A↗

PubMed1991

Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria.

Dicarboxylic aciduria occurs during increased mobilization or inhibited beta-oxidation of fatty acids. In these conditions, a number of 3-hydroxydicarboxylic acids are excreted in the urine. These 3-hydroxydicarboxylic acids include 3-hydroxyadipic (3OHDC6), 3-hydroxyoctanedioic (3OHDC8), 3-hydroxydecanedioic (3OHDC10), 3-hydroxydodecanedioic (3OHDC12), and a number of unsaturated homologues. The metabolic origin of these 3-hydroxydicarboxylic acids is from the omega-oxidation of 3-hydroxy fatty acids. Subsequent beta-oxidation of the dicarboxylates yields lower-chain 3-hydroxydicarboxylic acids. A new defect in fatty acid oxidation characterized by increased urinary ratios of 3OHDC6, 3OHDC12, and unsaturated 3OHDC14s relative to 3OHDC10 is described. This pattern is consistent with a defect in long-chain 3-hydroxyacyl-CoA dehydrogenase (LHAD), which was confirmed by enzyme assay in fibroblasts. In contrast, patients with medium-chain acyl-CoA dehydrogenase (MCAD) deficiency had lower ratios of 3OHDC6 and 3OHDC8 to 3OHDC10, consistent with a decreased activity of MCAD. Nonketotic dicarboxylic aciduria, other than MCAD and LHAD deficiencies, is shown to have a normal 3-hydroxydicarboxylic acid profile when compared with fasting normal controls. Since increased excretion of 3-hydroxydicarboxylic acids was observed in all patients with dicarboxylic aciduria, an increased excretion of these compounds is not an adequate criterion to suspect a defect in 3-hydroxyacyl-CoA dehydrogenases. The analysis of the metabolite ratios (3OHDC6 and 3OHDC12 relative to 3OHDC10) is a more useful indicator for defects in LHAD.

3-Hydroxyacyl CoA Dehydrogenases↗

PubMed1991

Characterization of the binding sites for dicarboxylic acids on bovine serum albumin.

Dicarboxylic acids are prominent features of several diseases, including Reye's syndrome and inborn errors of mitochondrial and peroxisomal fatty acid oxidation. Moreover, dicarboxylic acids are potentially toxic to cellular processes. Previous studies [Tonsgard, Mendelson & Meredith (1988) J. Clin. Invest. 82, 1567-1573] demonstrated that long-chain dicarboxylic acids have a single high-affinity binding site and between one and three lower-affinity sites on albumin. Medium-chain-length dicarboxylic acids have a single low-affinity site. We further characterized dicarboxylic acid binding to albumin in order to understand the potential effects of drugs and other ligands on dicarboxylic acid binding and toxicity. Progesterone and oleate competitively inhibit octadecanedioic acid binding to the single high-affinity site. Octanoate inhibits binding to the low-affinity sites. Dansylated probes for subdomain 2AB inhibit dodecanedioic acid binding whereas probes for subdomain 3AB do not. In contrast, low concentrations of octadecanedioic acid inhibit the binding of dansylated probes to subdomain 3AB and 2AB. L-Tryptophan, which binds in subdomain 3AB, inhibits hexadecanedioic acid binding but has no effect on dodecanedioic acid. Bilirubin and acetylsalicylic acid, which bind in subdomain 2AB, inhibit the binding of medium-chain and long-chain dicarboxylic acids. Our results suggest that long-chain dicarboxylic acids bind in subdomains 2C, 3AB and 2AB. The single low-affinity binding site for medium-chain dicarboxylic acids is in subdomain 2AB. These studies suggest that dicarboxylic acids are likely to be unbound in disease states and may be potentially toxic.

Acylation↗

PubMed1975

A disorder of muscle lipid metabolism and myoglobinuria. Absence of carnitine palmityl transferase.

Two brothers, 29 and 33 years of age, had recurrent myoglobinuria, renal failure and azotemia, but were otherwise normal, without apparent muscle weakness or exercise intolerance. Ischemic exercise resulted in normal lactate production. Muscle glycogen content and activities of phosphorylase and phosphofructokinase were normal. Plasma triglycerides were elevated (500 mg per deciliter) on a regular diet and rose during fasting. During a 72-hour fast, serum creatine phosphokinase rose more than 10 times, and myoglobin was detected in urine. Plasma ketone production was minimal during fasting, but prompt ketonemia ( a normal response) occurred after ingestion of medium-chain triglycerides. Carnitine palmityl transferase activity was virtually absent in crude muscle extracts and mitochondrial fractions. Lack of this enzyme impairs long-chain fatty acid utilization, reflected in increased content of plasma free fatty acids and plasma triglycerides. Depletion of ATP because of this metabolic block in muscle may account for the attacks of myoglobinuria.

Acute Kidney Injury↗

PubMed1978

Necessity of vitamin B12 for growth of rats fed on an odd- or even-carbon-number fat.

1. The effect of vitamin B12 on growth was studied in young male and female rats fed on diets sufficient (+B12) or deficient (-B12) in vitamin B12 containing 30% of the dietary energy as fat, either maize oil (CO) or triundecanoin (TUD). 2. Vitamin B12 deficiency severely depressed growth. After 6 weeks the weight gain of CO(-B12) rats was only 72% of that of CO(+B12) rats and the gain of TUD(-B12) rats was only 47% of TUD(+B12) rats. 3. After fasting 24 or 96 h TUD-fed rats, both +B12 and -B12, had greater glycogen reserves and higher plasma glucose levels than CO-fed rats. 4. It is concluded that vitamin B12 is required for the metabolism and utilization of both an odd-carbon-number medium-chain fat, TUD, and an even-C-number long-chain fat, CO, during growth in rats.

Animals↗

PubMed1991

Hematological and biochemical effects of parenteral nutrition with medium-chain triglycerides: comparison with long-chain triglycerides.

Twenty-four malnourished patients requiring total parenteral nutrition were randomly assigned to receive a daily infusion of either Lipofundin MCT-LCT [a new lipid preparation containing medium-chain triglycerides (MCTs)], or Lipofundin S [a long-chain triglyceride (LCT) preparation] for 6-28 d. No adverse clinical effects were apparent in patients receiving the new emulsion. Hematological indices were unchanged. Plasma urea concentrations rose less on MCT-LCT than on LCT and the plasma bilirubin concentration was lower. Plasma ketones were higher immediately after the MCT-LCT infusion but not at other times. Triglyceride and fatty acid concentrations were similar. Insulin concentrations were higher on MCT-LCT than on LCT. Daily nitrogen balance values were not significantly different between the two groups. Urinary carnitine excretion fell dramatically on both lipids.

Bilirubin↗

PubMed1991

Postprandial thermogenesis in lean and obese subjects after meals supplemented with medium-chain and long-chain triglycerides.

The thermic effect of medium-chain triglycerides (MCTs) was studied in six lean and six obese young males by evaluating postprandial thermogenesis (PPT) after the ingestion of mixed meals containing either 38 g long-chain triglycerides (LCTs) or 30 g MCTs plus 8 g LCTs. Postabsorptive resting metabolic rate (RMR) was higher (P less than 0.05) in the obese individuals than in the lean ones. PPT, evaluated as 6-h incremental areas above RMR, was greater (P less than 0.05) in both groups after meals containing MCTs. The thermic effect of MCTs was 119.7 +/- 33.9 and 144.7 +/- 48.8 kJ/6 h in the lean and the obese subjects, respectively. The postprandial response of glucose, insulin, and free fatty acids did not depend on the type of oil contained in the meal. Our study shows that PPT is enhanced in both lean and obese subjects when LCTs in a mixed meal are replaced with MCTs.

Adult↗

PubMed1991

Structured lipid made from fish oil and medium-chain triglycerides alters tumor and host metabolism in Yoshida-sarcoma-bearing rats.

The effects of structured lipid composed of fish oil and medium-chain triglycerides (Fish/MCT) on tumor and the host metabolism was compared with conventional long-chain triglycerides (LCTs) in Yoshida-sarcoma-bearing rats receiving TPN for 3 d. The two parenterally fed groups were divided into two treatments, saline or tumor necrosis factor (TNF), given intravenously at 20 micrograms/kg body wt. Changes in tumor volume, body weight, urinary nitrogen, whole-body and tissue protein kinetics, and fatty acid composition were measured. The study revealed that Fish/MCT feeding inhibited tumor growth, which could be attributed to decreased tumor protein synthesis. Body weight and nitrogen were better maintained by Fish/MCT feeding. In addition, the effects of Fish/MCT on tumor growth were synergistic with TNF treatment. The results demonstrate that dietary fat composition can influence fatty acid compositions of tumor tissue as well as tumor protein kinetics after a short period of TPN feeding.

Animals↗

PubMed1976

On the mechanism of malonyl-CoA-independent fatty-acid synthesis. Different properties of the mitochondrial chain elongation and enoylCoA reductase in various tissues.

1. NADPH-specific mitochondrial enoyl-CoA reductase can be assayed by a sensitive radioactive test, employing tritium-labelled NADPH, synthesized in a prefixed reaction from D-[1-3H]-glucose via the hexokinase and glucose-6-phosphate dehydrogenase reactions. 2. Liver, kidney cortex, heart muscle, skeletal muscle, brown adipose tissue, brain cortex, and aortic intimal tissue are investigated concerning chain lengths specificity of the chain elongation and the enoyl-CoA reductase. Medium-chain acyl-CoA compounds prove to be the best primers for the chain elongation. Enoyl-CoA reductases still show large incorporation rates with hexadecenoyl-CoA. 3. The differences in the chain lengths specificity of the chain elongation and enoyl-CoA reductase can be explained by the inhibitory effect of long-chain acyl-CoA derivatives on the 3-hydroxyacyl-CoA dehydrogenase. 4. The nucleotide specificity in the different tissues reveals two types of chain elongation: In addition to liver and kidney cortex, mitochondria of brown adipose tissue need NADH + NADPH for optimal chain elongation, whereas heart muscle, skeletal muscle and aortic intimal mitochondria only need NADH. 5. Different physiological roles are proposed for the two types. The "heart type" may be of importance in the conservation of reducing equivalents or acetate units in the anaerobic state, the "liver type" may play a role in the transfer of hydrogen from NADPH to the respiratory chain. In addition, the mitochondrial chain elongation may serve as bypass of the first part of the respiratory chain.

Adipose Tissue, Brown↗

PubMed1979

Free fatty acid and glucose metabolism during hypothermic perfusion of canine kidneys.

Canine kidneys were subjected to continuous nonpulsatile perfusion using 200 ml of a perfusate containing 50 g/l albumin. When optimal oxygenation was achieved, perfusate K+ contents were unchanged for 24 h, indicating adequate membrane function but tended to increase thereafter. Lowered oxygen pressures resulted in significant cellular K+ loss during the first hours of perfusion. During oxygenated perfusion, glucose and free fatty acids (FFA) were oxidized in considerable amounts with a preferential consumption of octanoate. A capacity for long-chain FFA oxidation became obvious when the octanoate had been used up, but the amount of these FFA in the perfusate depended preferentially on FFA being liberated from tissue lipids during the 1st day of perfusion. Glucose consumption rates were highest during the first 2 days of perfusion but the subsequent reduction of the metabolic rate was not accompanied by an accumulation of lactate. Thus medium-chain FFA and glucose should be supplied to the continuously perfused kidney in hypothermia and optimal oxygenation of the perfusate should be guaranteed. However, it seems to be unnecessary to supply exogenous long-chain FFA.

Albumins↗

PubMed1990

Long-chain versus medium and long-chain triglyceride-based fat emulsion in parental nutrition of severe head trauma patients.

In order to assess the metabolic value of medium-chain triglycerides (MCT) in severely stressed intensive care unit patients, two fat emulsions containing either long-chain triglycerides (LCT), or a mixture of 50% MCT and 50% LCT were compared in 24 head trauma patients over a 10 day period. Variations of serum triglyceride, non-esterified fatty acid, glycerol and phospholipid concentrations remained comparable after both lipid infusions. Bilirubin, alkaline phosphatase and transaminase plasma levels were altered in both groups without any significant differences or clinical consequences. Cumulative nitrogen balance remained negative (-10 g N. day-1 i.e. -100 g N. 10 days-1) and comparable in both groups. However, thyroxin-binding prealbumin concentrations increased significantly in patients receiving the MCT/LCT mixture. It is concluded that MCT might have a beneficial effect on visceral protein metabolism after trauma.

Blood Proteins↗

PubMedDate not supplied

Lipid infusion with different triglyceride cores (long-chain vs medium-chain/long-chain triglycerides): effect on plasma lipids and bilirubin binding in premature infants.

The possible beneficial effects of infusing a lipid emulsion containing 50% by weight of medium-chain triglycerides (MCT) compared with a standard long-chain triglyceride (LCT) emulsion were studied in 18 premature neonates (gestational age less than 34 weeks) requiring parenteral nutrition. The infants were assigned in a double-blind manner to receive one of the two lipid emulsions over 17 hours a day as a supplemental regimen for total parenteral nutrition. A lipid load of 1 g/kg per day was initiated on the third day of life and was increased at the rate of 1 g/kg per day until a maximal dose of 3 g/kg per day was obtained on the fifth day of life and maintained thereafter. Both bound and unbound bilirubin decreased with both infusion regimens during the study period. Despite a marked increase in plasma free fatty acid levels (260% in the MCT/LCT group compared with 210% in the LCT group), the fraction of unbound (free) bilirubin was significantly lower in the MCT/LCT group (34% vs 13%). Free fatty acid levels, corrected to albumin, were positively correlated to the percentage of free bilirubin only for the LCT lipid infusion. The finding of a significant elevation of plasma cholesterol levels only in the MCT/LCT group is now under investigation. Use of the MCT-containing emulsion was not associated with a higher frequency of adverse effects than the commonly used LCT-containing emulsion.(ABSTRACT TRUNCATED AT 250 WORDS)

Bilirubin↗

PubMedDate not supplied

Metabolic clearance of a fat emulsion containing medium-chain triglycerides in cirrhotic patients.

Medium-chain triglycerides (MCTs) may be advantageous in cirrhotic patients, but data on the clearing capacity are lacking. Intravenous fat tolerance test (IVFTT) was performed on 28 cirrhotic patients (Child's A, n = 9; Child's B, n = 13; Child's C, n = 6) to determine the clearance rate of Lipofundin MCT 20%, which contains a physical mixture of MCT and long-chain triglycerides (LCT). The mean fractional elimination rate (k2) of MCT/LCT physical blend in the cirrhotic patients (7.72%/min) was comparable with that of the healthy control subjects (n = 9, k2 = 5.43%/min). Significantly higher serum free fatty acid (FFA) levels were found in the cirrhotic patients during IVFTT. The difference could be accounted for by their higher basal levels. In all patients, serum FFA concentrations returned to basal value at the end of 1 hour. Prompt appearance of glycerol and beta-hydroxybutyrate was seen during IVFTT, indicating that hydrolysis of triglycerides and release of ketone bodies from the liver were rapid. It was concluded that the ability to eliminate MCT/LCT physical blend was not impaired in the cirrhotic patients.

3-Hydroxybutyric Acid↗

PubMed1978

Comparison of long term lipogenic effects of two different medium-chain triglycerides (tri C8: O and tri C12 : O) in the growing rat.

During the growth (35 g-340 g), and as compared to results obtained with a lipid-free diet or a diet containing long-chain fatty acids, high levels of Tri C8 : O or Tri C12 : O did not change the quantitative aspects of proteinogenesis and lipogenesis balances. The incorporation of Tri C8 : O into the diet did not change the fatty acid composition of body lipid stores while the incorporation of Tri C12 : O induced a lipogenesis characterized by the disappearance of about 50% of the n-9 and n-7 unsaturated fatty acids, the emergence of an equivalent amount of saturated fatty acids in C12 and C14, and the decrease of hexadecanoic or palmitic acid concentration. Titers of saturated fatty acids with a melting point higher than 40 degrees C increased from 34% to 64%. Results suggested an efficient inhibition of fatty acid biosynthesis de novo by C12 : O, associated with an impossibility for microsomal enzymes to assume the elongation of a sufficient amount of C12 : O to maintain C16 : O concentration and to furnish an important amount of substrate (C18 : O) to delta-9-stearoyl coenzyme A desaturase for oleic acid synthesis. Introducing dodecanoic acid into the diet of growing animals appears to be the most efficient method for increasing the degree of saturation of body lipids without changing the concentrations of long-chain saturated fatty acids.

Animals↗

PubMed1992

Composition and flavor of milk and butter from cows fed unsaturated dietary fat and receiving bovine somatotropin.

Composition and flavor of milk and butter were evaluated from cows divided into four treatments including a control, control with bST, added dietary fat from sunflower seeds with bST, or added dietary fat from safflower seeds with bST. Feeding added unsaturated dietary fat resulted in lower concentrations of short-and medium-chain and higher concentrations of long-chain fatty acids in milk fat and butter. Milk fat unsaturated fatty acid concentrations were 25.0, 28.4, 39.6, and 37.9%, and butter unsaturated fatty acid concentrations were 23.0, 26.9, 37.8, and 36.2% for control, control with bST, sunflower seeds with bST, and safflower seeds with bST, respectively. Sensory evaluations indicated that butters from the bST with sunflower seed and bST with safflower seed treatments were equal or superior in flavor to the control butter. Milk from cows receiving bST or fed added unsaturated dietary fat and receiving bST was no more susceptible to oxidized off-flavors than control milk. Butters from sunflower seed and safflower seed treatments with bST contained higher concentrations of unsaturated fatty acids, were softer at 4 and 20 degrees C, and possessed acceptable flavor and processing characteristics compared with butters from control and control with bST.

Animals↗

PubMedDate not supplied

Medium-chain triglycerides and long-term parenteral nutrition in children.

There are no data concerning long-term utilization of medium-chain triglycerides (MCTs) in parenteral nutrition (PN) in children. Our study included 12 children, aged 1.5-17 yr, on total PN at home, supplying a daily intake of 214 +/- 92 mg/kg nitrogen and 47 +/- 17 kcal/kg nonprotein energy (NPE). NPE included 10-32% long-chain triglycerides (LCTs) (Intralipid 20%). After switching to emulsion containing 50% MCT and 50% LCT (Medialipide) at the same dosage regimen and infusion rate as before, the subjects were monitored at 1, 3, and 6 mo. No signs of clinical intolerance were observed. Among the laboratory parameters evaluated, the only significant (p < 0.05) changes were 1) an increase in apolipoproteins A-I and A-II at 1, 3, and 6 mo and 2) a decrease in gamma-glutamyltransferase (gamma-GT) at 6 mo. There were no changes in the status of essential fatty acids in plasma or in phospholipids (in erythrocyte membranes). Moderate urinary excretion of dicarboxylic acids (adipic, suberic, and sebacic) was evidence of peroxysomal omega-oxidation. The results support the proposal for use of MCT-rich emulsion in long-term PN, given its metabolic advantages relative to LCT.

Adolescent↗

PubMedDate not supplied

[Fatty acids: their biochemical and functional classification].

Fatty acids (FA) constitute the main component of phospholipids, triglycerides and cholesterol esters. FA are acidic, monocarboxylic linear chains of variable length: short-chain FA (2-4 carbon atoms), medium-chain FA (6-12 carbon atoms), long-chain FA (14-18 carbon atoms), very long-chain FA (derived from parental 18-carbon molecules). They can be further subdivided into saturated (no double bond), monounsaturated (one double bond) and polyunsaturated (two or more double bonds). They are all involved in energetic, metabolic and structural activities. Short-chain FA act as growth factors; medium chain FA are readily available as energy source; saturated long-chain FA constitute a source of energy but may be implicated in the development of the atherosclerotic process; unsaturated long-chain FA include oleic acid and the essential fatty acids (linoleate and linolenate), and are all implicated in fundamental metabolic processes; very-long chain FA are the most characteristic molecules in biologic membranes. From recent works it is clearly established that the physiological role of FA depends on the chain length, and that the very-long chain molecules could determine the quality of human development. A functional classification of FA today must be based not only on the rate of unsaturation, but also (and most importantly) on the chain length.

Biochemical Phenomena↗

PubMedDate not supplied

[Dietary sources of fatty acids in childhood].

The first oral supply of fatty acids (FA) is provided by human milk. It contains a large variety of FA, perfectly adequate to the newborn's metabolic needs. Saturated and monounsaturated chains derive from the local mammary gland synthesis, while polyunsaturated very long-chains come from the hydrolysis of circulating lipoproteins and are more dependent on the maternal dietary habits. Trans FA have been shown in human milk too. The fat content of human milk progressively increases during the breast-feeding period; it varies during the day and from feed to feed. Infant formulas contain a very narrow range of FA. No commercially available formula contains the very long-chain polyunsaturated FA. Formulas for pre-term babies enriched with these molecules have been recently studied. The role of medium-chain FA in the early diet of the pre-term infant must still be defined. With weaning, green leafy vegetables become a balanced source of essential FA, while animal foods (both meat and fish) supply not only saturated but also polyunsaturated very long-chain FA. Analogously, vegetal oils are a fundamental source of monounsaturated and essential FA, animal fats (butter, lard) are a rich source of saturated fats and fish oils contain a mixture of n-3 polyunsaturated very long-chain FA. Correct dietary habits for children should provide a rich variety of foods, to reach a balanced supply of all the families of FA. Oleic acid should represent the main FA in the diet.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗