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PubMed1996

cobB function is required for catabolism of propionate in Salmonella typhimurium LT2: evidence for existence of a substitute function for CobB within the 1,2-propanediol utilization (pdu) operon.

The cobB function of Salmonella typhimurium LT2 was defined in vivo as an alternative activity for the nicotinic acid mononucleotide:5,6-dimethylbenzimidazole phosphoribosyltransferase enzyme (CobT), which is involved in the assembly of the nucleotide loop of cobalamin in this bacterium (J. R. Trzebiatowski, G. A. O'Toole, and J. C. Escalante-Semerena, J. Bacteriol. 176:3568-3575, 1994). In this paper we document that, independent of their inability to substitute for CobT function, cobB mutants are unable to use propionate as a carbon and energy source. A plasmid carrying only a wild-type copy of cobB complemented the cobalamin biosynthesis and propionate catabolism phenotypes of cobB mutants, indicating that a lack of CobB was responsible for both phenotypes. We demonstrate the existence of a function encoded by the 1,2-propanediol utilization (pdu) operon, which when induced by 1,2-propanediol compensated for the lack of CobB during propionate catabolism but failed to compensate for CobT in the assembly of the nucleotide loop of cobalamin in a cobB cobT double mutant.

Genes, Bacterial↗
PubMed1967

Carbohydrate metabolism in leukocytes. VII. Metabolism of glucose, acetate, and propionate by human plasma cells.

Plasma cells obtained from the peripheral blood of a patient with multiple myeloma was incubated in serum and Krebs-Ringer bicarbonate buffer with (14)C-labeled glucose, acetate, and propionate. Glucose utilization by these cells amounted to 0.5 mumole per hr per 10(8) cells and was mainly via the Embden-Meyerhof pathway, and only 6% or less traversed the hexose monophosphate shunt. The presence of Krebs cycle activity was demonstrated by direct isolation of several labeled intermediates after incubation with either (14)C-acetate or (14)C-propionate. The distribution of (14)C in lactate, succinate, fumarate, malate, aspartate, and glutamate indicate a complete Krebs cycle. Acetate was metabolized via the Krebs cycle to the extent of 0.15 mumoles per hr per 10(8) cells, and the rate of propionate utilization was 0.17 mumoles per hr per 10(8) cells.

Acetates↗
PubMed1968

Identification of propionate as an endogenous CO2 acceptor in Rhodospirillum rubrum and properties of purified propionyl-coenzyme A carboxylase.

A heat-stable endogenous CO(2) acceptor has been found in extracts of Rhodospirillum rubrum grown photoheterotrophically on acetate. Evidence is presented which suggests that this factor is propionic acid. Thus, paper and gas chromatographic analyses have indicated that propionic acid is present in boiled extracts prepared from R. rubrum cells. The products of (14)CO(2) fixation obtained with either the boiled extract or propionic acid as the CO(2) acceptor were identical and were identified as methylmalonic acid and succinic acid by paper chromatography. The enzyme which catalyzes the carboxylation of propionyl-coenzyme A (propionyl-CoA carboxylase) was purified from R. rubrum cells grown on acetate and its properties were studied. The enzyme is similar to propionyl-CoA carboxylases isolated from mammalian sources.

Butyrates↗
PubMed1984

Acetic, propionic, and oleic acid as the possible factors influencing the predominant residence of some species of Propionibacterium and coagulase-negative Staphylococcus on normal human skin.

The minimum inhibitory concentration (MIC) of acetic and propionic acid for resident bacteria on normal human skin, such as Propionibacterium acnes and Staphylococcus epidermidis, was 25 mg/mL or more at any pH tested (pH 5.5-6.8). While the MIC of these acids for most of the transient bacteria was markedly decreased by lowering the pH of the media and at pH 5.5, the mean pH value of the normal human skin, the MIC was 6.25 mg/mL or less. The MIC of oleic acid for some strains of Gram-positive transient bacteria of Streptococcus, Micrococcus, or Bacillus was 100 micrograms/mL or less at all pH's tested. Staphylococcus aureus was resistant to this acid at pH 6.8, but became as sensitive as Streptococcus when the pH was lowered. The growth of P. acnes, the most predominant resident bacterium, was enhanced markedly and reached a maximum level at 6.25 mg/mL of propionic acid, 12.5 mg/mL of acetic acid, and 50-100 micrograms/mL of oleic acid. On the basis of these results, we presumed that acetic, propionic, and oleic acids are factors influencing the predominant residence of some species of Propionibacterium and coagulase-negative Staphylococcus on normal human skin.

Acetates↗
PubMed1998

13C NMR measurements of human gluconeogenic fluxes after ingestion of [U-13C]propionate, phenylacetate, and acetaminophen.

Anaplerotic, pyruvate recycling, and gluconeogenic fluxes were measured by 13C isotopomer analysis of plasma glucose, urinary phenylacetylglutamine, and urinary glucuronide in normal, 24-h-fasted individuals after ingestion of [U-13C]propionate, phenylacetate, and acetaminophen. Plasma glucose isotopomer analysis reported a total anaplerotic flux of 5.92 +/- 1.03 (SD) relative to citrate synthase. This was not significantly different from glucuronide and phenylacetylglutamine analyses (6.08 +/- 1.16 and 7. 14 +/- 1.94, respectively). Estimates of pyruvate recycling from glucose and glucuronide isotopomer distributions were almost identical (3.55 +/- 0.99 and 3.66 +/- 1.11, respectively), whereas phenylacetylglutamine reported a significantly higher estimate (5.74 +/- 2.13). As a consequence, net gluconeogenic flux reported by phenylacetylglutamine (1.41 +/- 0.28) was significantly less than that reported by glucose (2.37 +/- 0.64) and glucuronide (2.42 +/- 0. 76). This difference in fluxes detected by analysis of phenylacetylglutamine vs. hexose is likely due to compartmentation of hepatic metabolism of propionate. Net gluconeogenic flux estimates made by use of this stable isotope method are in good agreement with recent measurements in humans with [14C]propionate.

Acetaminophen↗
PubMed1995

Broiler chick responses to anorectic agents: dietary acetic and propionic acids and the blood metabolites.

The effects of dietary supplementation with acetic or propionic acid, given at a level of 3% of diets containing 2,500 or 2,750 kcal of metabolizable energy per kg, on levels of blood glucose, and on lipid, protein, and energy metabolisms were studied in female broiler chicks. Voluntary feed and energy intakes, as well as body weight gain, decreased significantly with the inclusion of the acids in either diet, in decreasing order of effect: propionate > acetate > nonsupplemented controls. The relative weight of the abdominal adipose tissue decreased significantly with the inclusion of either acid, but was unaffected by dietary energy level. In contrast, the weight of the liver was higher in birds fed the low-energy diet, but was unaffected by the anorectic agents. Inclusion of the acids increased the concentration of volatile fatty acids in the cecum and blood plasma. The rate of clearance of plasma propionate was greater than that of acetate. Anorectic agents and dietary energy density exhibited a synergistic effect on feed intake. These agents altered blood metabolites involved in lipid and energy metabolisms, but not in that of protein. Plasma metabolites and enzymes, particularly beta-hydroxybutyrate and alkaline phosphatase, reflected the degree of feed restriction, supporting the hypothesis that the hypophagic effect of these acids is due to metabolic intervention.

3-Hydroxybutyric Acid↗
PubMed1979

Inhibition by propionyl-coenzyme A of N-acetylglutamate synthetase in rat liver mitochondria. A possible explanation for hyperammonemia in propionic and methylmalonic acidemia.

In the search for the mechanism by which hyperammonemia complicates propionic and methylmalonic acidemia the effects of a series of acyl-coenzyme A (CoA) derivatives were studied on the activity of N-acetylglutamate synthetase in rat liver mitochondria using acetyl-CoA as substrate. Propionyl-CoA was found to be a competitive inhibitor. The inhibition constant of 0.71 mM is in the range of concentrations of propionate found in the serum of patients with propionic and methylmalonic acidemia. Propionyl-CoA was also found to be a substrate for N-acetylglutamate synthetase, forming N-propionylglutamate. This compound was a weak activator of rat liver carbamoylphosphate synthetase; the activation constant was 1.1 mM as compared with 0.12 mM for N-acetylglutamate. A decreased level of N-acetylglutamate in liver mitochondria that would follow inhibition of N-acetylglutamate synthetase by propionyl-CoA would be expected to lead to hyperammonemia. Methylmalonyl-CoA, tiglyl-CoA, and isovaleryl-CoA at a concentration of 3 mM caused 30-70% inhibition of N-acetylglutamate synthetase. 3the latter two compounds are readily detoxified by the formation of N-acylglycine conjugates in liver, which may prevent large accumulations and could explain why hyperammonemia is not characteristic of patients with beta-ketothiolase deficiency or isovaleric acidemia in whom these compounds would be expected to be elevated.

Acetyl Coenzyme A↗
PubMed1984

L-carnitine enhances excretion of propionyl coenzyme A as propionylcarnitine in propionic acidemia.

Treatment with L-carnitine greatly enhanced the formation and excretion of short-chain acylcarnitines in three patients with propionic acidemia and in three normal controls. The use of fast atom bombardment mass spectrometry and linked scanning at constant magnetic (B) to electric (E) field ratio identified the acylcarnitine as propionylcarnitine in patients with propionic acidemia. The normal children excreted mostly acetylcarnitine. Propionic acidemia and other organic acidurias are characterized by the intramitochondrial accumulation of short-chain acyl-Coenzyme A (CoA) compounds. The substrate specificity of the carnitine acetyltransferase enzyme and its steady state nature appears to facilitate elimination of propionyl groups while restoring the acyl-CoA:free CoA ratio in the mitochondrion. We suggest that L-carnitine may be a useful therapeutic approach for elimination of toxic acyl CoA compounds in several of these disorders.

Acyl Coenzyme A↗
PubMed1988

The propionic acids. Gastrointestinal toxicity in various species.

The propionic acids represent the largest chemical class of nonsteroidal anti-inflammatory agents (NSAID). Several of them are widely used, both in the United States and internationally. This paper discusses observations made on fenoprofen, flurbiprofen, ibuprofen and naproxen. Of these compounds, three are racemates; the fourth, naproxen, is an enantiomer. As a group, the propionic acids, along with most members of the other classes of NSAID, produce gastrointestinal damage in most species. These lesions vary from erythema, hemorrhage and erosion to ulceration and peritonitis. As might be expected, the degree of gastrointestinal intolerance depends on many factors: the individual compound, the dose-level, the duration of the period of drug administration, and the pharmacokinetics and metabolism in a given species. For example, in our experience the rat is less tolerant of NSAID than is the monkey, and the dog is less tolerant than the rat. Gastrointestinal lesions have been seen following both parenteral and oral administration; these findings suggest that factors other than local irritation play a role in the development of lesions. Most NSAID inhibit prostaglandin cyclo-oxygenase activity, which results in a prostaglandin deficiency at the tissue level. The administration of relevant exogenous prostaglandins, such as 16,16-dimethyl PGE2, has been shown to inhibit the gastrointestinal toxicity accompanying the administration of several NSAID, including some of the propionic acids.

Animals↗
PubMed1977

Effect of valine on propionate metabolism in control and hyperglycinemic fibroblasts and in rat liver.

Measurement of methylmalonyl-CoA mutase and propionyl-CoA carboxylase activities in lysates from fibroblasts derived from control, nonketotic hyperglycinemia, propionic acidemia, and both vitamin B12-responsive and -nonresponsive variants of methylmalonic acidemia showed only one abnormality: a 59% decrease in carboxylase activity in the nonketotic hyperglycinemic lysates (P less than 0.01). When fibroblasts from all cell types were grown on valine-supplemented (24 mM) media, mutase activity was generally inhibited. As for carboxylase activity, control lines were inhibited 35% as compared to controls without valine and propionic acidemia activity was undetectable. On the other hand, carboxylase activity in both methylmalonic acidemia variants was increased 40% and nonketotic hyperglycinemia carboxylase activity was increased 80% (P less than 0.01) when grown on valine-supplemented media. Isoleucine could not substitute for valine in producing increased carboxylase activity in these mutants. Glycine cleavage activity in fresh rat liver homogenates (11.1 micronmol/gm protein/90 min) did not vary significantly when 24 mM valine was added to the reaction (9.9 micronmol/mg protein/90 min). Therefore, the hyperglycinemia observed in both ketotic and nonketotic forms is probably not caused by a direct effect of valine on the glycine cleavage reaction. These data suggest that the presence of increased amounts of propionic acid in serum or urine does not necessarily rule out the possibility of nonketotic hyperglycinemia due to the decreased activity of the carboxylase enzyme.

Carboxy-Lyases↗
PubMed1984

Effect of sodium propionate on the contractile response of the rat ileum in situ.

Effects of short-chain fatty acids (SCFA) on the contractile response of rat ileum were studied in vivo. The contractile response was estimated by means of changes in the intraluminal pressure under the isometric condition. Intravenous administration of sodium salts of propionate, butyrate, valerate or caproate produced biphasic contractions: an initial phasic contraction and a subsequent tonic contraction. The effect of propionate was studied in detail. A sigmoid dose-response curve was obtained for the phasic contraction. Atropine, hexamethonium and tetrodotoxin inhibited the phasic contraction, while neostigmine vigorously enhanced it. On the other hand, the tonic contraction was not inhibited by atropine, hexamethonium or tetrodotoxin. Repeated administration of propionate at intervals of less than 3 min led to tachyphylaxis, and this tachyphylaxis disappeared by about 10 min. These results suggest that SCFA induced the biphasic contraction of the rat ileum, probably by neurogenic and myogenic mechanisms.

Animals↗
PubMed2006

Enhancement of ethyl propionate synthesis by poly (AAc-co-HPMA-cl-MBAm)-immobilized Pseudomonas aeruginosa MTCC-4713, exposed to Hg2+ and NH4+ ions.

A purified alkaline thermo-tolerant bacterial lipase from Pseudomonas aeruginosa MTCC-4713 was immobilized on a poly (AAc-co-HPMA-cl-MBAm) hydrogel. The hydrogel-bound lipase achieved 93.6% esterification of ethanol and propionic acid (300 mM: 100 mM) into ethyl propionate at temperature 65 degrees C in 3 h in the presence of a molecular sieve (3 angstroms). In contrast, hydrogel-immobilized lipase pre-exposed to 5 mM of HgCl2 orNH4Cl resulted in approximately 97% conversion of reactants in 3 h into ethyl propionate under identical conditions. The salt-exposed hydrogel was relatively more efficient in repetitive esterification than the hydrogel-bound lipase not exposed to any of the cations. Moreover, bound lipase exposed Hg2+ or NH4+ ions showed altered specificity towards p-nitrophenyl esters and was more hydrolytic towards higher C-chain p-nitrophenyl esters (p-nitrophenyl laurate and p-nitrophenyl palmitate with C 12 and C 16 chain) than the immobilized lipase not exposed to any of the salts. The later showed greater specificity towards p-nitrophenyl caprylate (C 8).

Acrylamides↗
PubMed1996

Effects of propionate and ammonium on contractions produced by sodium removal in human internal mammary artery and saphenous vein.

Effects of propionate and ammonium on contractions produced by Na+ removal (0-Na+ contraction, replaced with N-methyl-D-glucamine) were studied and compared with those produced by 60 mM K+ in muscle strips isolated from human internal mammary artery (IMA) and saphenous vein (SV), clinically used as bypass vessels. Contractions induced by 60 mM K+ (60-K+ contractions) were similar in both vessels. 0-Na+ contraction was significantly larger in the vein than in the artery. Neither 60-K+ nor 0-Na+ contractions were significantly affected by NG-nitro-L-arginine (30 microM) or phenoxybenzamine (1 microM). Ouabain (2 microM) slowly potentiated 0-Na+ contractions and the 3rd contraction produced 60 min after ouabain application was 291 +/- 36% in the artery and 184 +/- 41% of the control (n = 10) in the vein. Propionate (20 mM) potentiated 60-K+ contraction more strongly in the vein than in the artery, but potentiation of 0-Na+ contraction was greater in the artery than in the vein. On the other hand, ammonium (20 mM) inhibited 60-K+ contractions more strongly in the artery than the vein, whereas inhibition of 0-Na+ contraction was stronger in the vein. 0-Na+ contraction is likely to be produced by an Na(+)-Ca2+ exchange mechanism, and the effects of propionate and ammonium are considered to be mediated by intracellular acidification and alkalinization, respectively. It is speculated that an Na(+)-H+ exchange may also be involved in 0-Na+ contraction and that SV has slightly lower pHi than IMA.

Adult↗
PubMed2006

Effects of supplements that contain increasing amounts of metabolizable protein with or without Ca-propionate salt on postpartum interval and nutrient partitioning in young beef cows.

Cattle grazing winter range forages exhibit interannual variation in response to supplementation. This variation may be mediated by circulating concentrations and subsequent metabolism of glucose, which are influenced by forage quality and availability. A study conducted at the Corona Range and Livestock Research Center during 2 dry years evaluated responses of young postpartum beef cows (n = 51, initial BW = 408 +/- 3 kg, and BCS = 5.1 +/- 0.04 in year 1; n = 36, initial BW = 393 +/- 4 kg, and BCS = 4.5 +/- 0.05 in year 2) to supplements that met or exceeded metabolizable protein (MP) requirements. Supplements were fed at 908 g/d per cow and provided 327 g of CP, 118 g of ruminally undegradable protein (RUP), and 261 g of MP from RUP (RMP), calculated to meet the MP requirement; 327 g of CP, 175 g of RUP, and 292 g of MP from RUP (RMP+), which supplied 31 g of excess MP; or 327 g of CP, 180 g of RUP, 297 g of MP from RUP, and 100 g of propionate salt (NutroCal, Kemin Industries, Inc., Des Moines, IA; (RMP+)P), which supplied 36 g of excess MP. Body weights were recorded once every 2 wk, and blood samples were collected 1x/wk in year 1 and 2x/wk in year 2 for 100 d postpartum. Postpartum anestrous was evaluated by progesterone from weekly blood samples, and pregnancy was confirmed by rectal palpation at weaning. As MP from RUP with or without propionate increased, a decrease (P = 0.03) was observed in postpartum interval; however, differences in pregnancy percentage (P = 0.54) were not influenced by treatments. We hypothesized that additional AA from RUP along with propionate would increase supply of glucogenic precursors and, therefore, glucogenic potential of the diet. Therefore, a postpartum glucose tolerance test was conducted near the nadir of cow BW to evaluate the rate of glucose clearance. Glucose tolerance tests showed that (RMP+)- or (RMP+)P-supplemented cows had greater (P = 0.03) rates of glucose clearance, which might have influenced the observed abbreviation of the postpartum interval. A glucose tolerance test conducted at the end of supplemental treatments revealed no differences in glucose clearance (P = 0.47) among previously supplemented cows. These data suggest that not only vegetative quality, duration of lactation, and season of grazing, but also type of supplementation may play a pivotal role in the young postpartum beef cow's ability to respond and incorporate nutrients into insulin-sensitive tissues.

Animal Feed↗
PubMed1978

Human urinary metabolites of 3-(2',4',5'-triethoxybenzoyl)propionic acid, a new biliary smooth muscle relaxant with choleretic activity.

Biotransformation of 3-(2',4',5'-triethoxybenzoyl)propionic acid (tri-, ethoxybenzoylpropionate) was studied in man using isotopic cluster technique. From the 24 h urine of a male volunteer given an equimolar mixture of non-labelled and pentadeuterium-labelled triethoxybenzoylpropionate (1 mg/kg) orally, the parent drug, 3-(2',5'-diethoxy-4'-hydroxybenzoyl)propionic acid (4'-phenol) and 3-(2',4'-diethoxy-5'-hydroxybenzoyl)propionic acid (5'-phenol) were isolated and identified by g.l.c.-mass spectrometry. 2. Urinary components were also quantified by mass chromatography: the parent drug (67.4% of dose) and 4'- and 5'-phenols in a mixture (20.3%). More than 80% of urinary triethoxybenzoylpropionate was present as its glucuronic acid ester, as evidenced by using beta-glucuronidase and saccharo-1,4-lactone, a specific inhibitor of the enzyme. Almost all of 4'- and 5'-phenols appeared as conjugates with glucuronic acid and/or sulphuric acid. These findings indicated that in man triethoxybenzoylpropionate was largely conjugated with glucuronic acid and in part underwent deethylation followed by conjugation for elimination mainly in urine.

Benzoates↗
PubMed1998

Effect of chemical structure on the release of certain propionic acid derivatives from their dosage forms.

The aim of this study was to investigate the relationship between the chemical structure and release properties of certain drug products. Propionic acid derivatives were used as a model. These include ibuprofen (I), ketoprofen (K), tiaprofenic acid (T), flurbiprofen (F), and naproxen (N). They are all aryl derivatives of propionic acid and differ only in the aryl group. Such an aryl group may be either isobutylphenyl, benzoylphenyl, benzoylthienyl, fluorobiphenyl, or methoxynaphthyl group in I, K, T, F, and N, respectively. Three dosage forms were selected for this study: capsules, suppositories, and creams. The release of propionic acid derivatives from the capsules and suppositories decreased in the order ibuprofen > tiaprofenic acid > ketoprofen > flurbiprofen > naproxen, and for the creams the release decreased in the order ibuprofen > tiaprofenic acid > flurbiprofen > ketoprofen > naproxen. The difference in drug release in the first case was attributed to the difference in the chain length, and in the creams which are composed of two phases, the partition coefficient was found to affect the drug release. The molecular weight of the drug had no effect on the release. The drug release from different dosage forms was not affected after 1 month storage.

Capsules↗
PubMed2003

Rates of production of acetate, propionate, and butyrate in the rumen of lactating dairy cows given normal and low-roughage diets.

Five lactating dairy cows with a permanent cannula in the rumen were given (kg DM/d) a normal diet (7.8 concentrates, 5.1 hay) or a low-roughage (LR) diet (11.5 concentrates, 1.2 hay) in two meals daily in a two-period crossover design. Milk fat (g/kg) was severely reduced on diet LR. To measure rates of production of individual volatile fatty acids (VFA) in the rumen, 0.5 mCi 1-(14)C-acetic acid, 2-(14)C-propionic acid, or 1-(14)C-n-butyric acid were infused into the rumen for 22 h at intervals of 2 to 6 d; rumen samples were taken over the last 12 h. To measure rumen volume, we infused Cr-EDTA into the rumen continuously, and polyethylene glycol was injected 2 h before the morning feed. Results were very variable, so volumes measured by rumen emptying were used instead. Net production of propionic acid more than doubled on LR, but acetate and butyrate production was only numerically lower. Net production rates pooled across both diets were significantly related to concentrations for each VFA. Molar proportions of net production were only slightly higher than molar proportions of concentrations for acetate and propionate but were lower for butyrate. The net energy value (MJ/d) of production of the three VFA increased from 89.5 on normal to 109.1 on LR, equivalent to 55 and 64% of digestible energy, respectively. Fully interchanging, three-pool models of VFA C fluxes are presented. It is concluded that net production rates of VFA can be measured in non-steady states without the need to measure rumen volumes.

Acetates↗
PubMed2004

The effects of buffered propionic acid-based additives alone or combined with microbial inoculation on the fermentation of high moisture corn and whole-crop barley.

Buffered propionic acid-based additives (BP) alone or in combination with a microbial inoculant containing lactic acid bacteria (MI) were mixed with ground, high moisture corn or whole-crop barley and ensiled in triplicate laboratory silos to investigate their effects on silage fermentation and aerobic stability. The inoculant and chemicals were applied separately for treatments that included both additives. The addition of MI alone had no effect on DM recovery, fermentation end products, or aerobic stability of high moisture corn. However, treatments with 0.1 and 0.2% BP (alone and the combination) had more than 10- and 100-fold fewer yeasts, respectively, and they also had greater concentrations of propionic acid than did untreated corn. Corn treated with only 0.1 (161 h) and 0.2% (218 h) BP tended to be more stable when exposed to air than untreated corn (122 h). Treatment with MI + 0.2% BP markedly improved the aerobic stability (>400 h) of high moisture corn. With whole-crop barley, the addition of MI alone, BP alone, and combinations of MI and BP prevented the production of butyric acid that was found in untreated silage (0.48%). All barley silages that had MI in their treatments underwent a more efficient fermentation than treatments without MI, as evident by a greater ratio of lactic:acetic acid and more DM recovery than in untreated silage. Increasing levels (0.1 to 0.2%) of BP added together with MI improved the aerobic stability of barley (190 and 429 h) over the addition of MI alone (50 h). These data show that buffered propionic acid-based products are compatible with microbial inoculants and, in some circumstances when used together, they can improve the fermentation and aerobic stability of silages.

Acetic Acid↗