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PubMedDate not supplied

Incorporation of acetate, propionate, and methionine into rapamycin by Streptomyces hygroscopicus.

Labelling experiments with 13C-labelled precursors demonstrated that the majority of the macrolide ring of rapamycin is formed from six acetate and seven propionate units. A two-carbon unit in the ring was not labelled by acetate, propionate, glycine, or methionine. Methionine and glycine did, however, label the three methoxy groups of rapamycin to a high degree. Results from the incorporation experiments demonstrated that there were errors in the published 13C-nmr spectral assignments for rapamycin; these have now been corrected.

Acetates↗
PubMed2002

Effect of propionic and methylmalonic acids on the high molecular weight neurofilament subunit (NF-H) in rat cerebral cortex.

Propionic and methylmalonic acidemias are inherited neurometabolic disorders biochemically characterized by tissue accumulation of propionic (PA) and methylmalonic (MMA) acids, respectively. Neurofilaments (NF) are important cytoskeletal proteins and phosphorylation/dephosphorylation of NF is important to stabilize the cytoskeleton. We investigated the effects of PA and MMA on the high molecular weight neurofilament subunit associated with the cytoskeletal fraction of rat cerebral cortex along development. Cortical slices from 9- to 60-day-old rats were incubated with 2.5 mM PA or MMA. The cytoskeletal fraction was extracted and the immunoreactivity for phosphorylated or total NF-H was analyzed by immunoblotting using specific antibodies. Results showed that treatment of tissue slices with the acids induced an increased Triton-insoluble phosphorylated NF-H immunoreactivity in up to 17-day-old rats. Furthermore, treatments significantly increased the total amount of NF-H in 12-day-old rats. These findings indicate that PA and MMA alter the dynamic regulation of NF-H assembly in the cytoskeletal fraction.

Animals↗
PubMed1968

A direct pathway for the metabolism of propionate in cell extracts from Moraxella lwoffi.

1. Extracts from Moraxella lwoffi oxidize propionate, but at a low rate when compared with whole cells. 2. This oxidative activity requires the formation of propionyl-CoA. 3. Enzymes catalysing the formation of propionyl phosphate and propionyl-CoA are present. The presence of a propionyl-CoA hydrolase is considered to be an artifact, but partly responsible for the low rates of oxidation. 4. Enzymes catalysing the reduction of NAD(+) and the formation of pyruvate with propionyl-CoA as substrate are also present. 5. That the only pathway for the metabolism of propionate in extracts is a direct one to acetate via pyruvate was confirmed by the use of (14)C-labelled materials. 6. A possible sequence of enzyme-catalysed reactions that will account for the experimental observations is described.

Acetates↗
PubMed1972

Identification of a group of tetracarboxylate porphyrins, containing one acetate and three propionate -substituents, in faeces from patients with symptomatic cutaneous hepatic porphyria and from rats with porphyria due to hexachlorobenzene.

1. Three tetracarboxylate porphyrins, apart from coproporphyrin, were isolated from the faeces of patients with symptomatic cutaneous hepatic porphyria and of rats with porphyria caused by hexachlorobenzene poisoning. The porphyrins were not present in the urine of the porphyric rats or in the faeces of control rats. 2. Two of the porphyrins were identified as tris-(2-carboxyethyl)-carboxymethyl ethyl trimethyl porphin (isocoproporphyrin) and tris-(2-carboxyethyl)-carboxymethyl trimethyl porphin (de-ethyliso-coproporphyrin). 3. The third porphyrin, previously reported to be an analogue of coproporphyrin in which one propionate group is replaced by an alpha- or beta-hydroxypropionate group, was shown to be tris-(2-carboxyethyl)-carboxymethyl-(1-hydroxyethyl)-trimethyl porphin (hydroxyisocoproporphyrin). 4. The order of beta-substituents around the porphin ring could not be determined for any of the compounds. 5. Evidence for the existence of a fourth porphyrin, tris-(2-carboxyethyl)-carboxymethyl trimethyl vinyl porphin (dehydroisocoproporphyrin), a postulated precursor of the others, is described. 6. It is suggested that dehydroisocoproporphyrinogen is produced by decarboxylation-dehydrogenation of one of the propionate groups of pentacarboxylate porphyrinogen III.

Acetates↗
PubMed1976

Effect of pent-4-enoic acid, propionic acid and other short-chain fatty acids on citrulline synthesis in rat liver mitochondria.

19 The effect of pent-4-enoic acid, propionic acid and several other short-chain fatty acids on citrulline synthesis in rat liver mitochondria was studied. 2.Pent-4-enoate at 1 mM inhibited mitochondrial citulline synthesis by about 80-90%. It is concluded that pent-4-enoate inhibits citrulline synthesis by interfering with some aspect of mitochondrial energy metabolism. This results in impairment of mitochondrial ornithine uptake or depletion of mitochondrial ATP, which, in turn, impairs carbamoyl phosphate synthesis or both. Evidence in support of this conclusion includes: pent-4-enoate has no effect on citrulline synthesis supported by succinate or exogenous ATP; pent-4-enoate lowers the medium plus mitochondrial ATP concentration; finally, when glutamate is the oxidizable substrate, pent-4-enoate decreases the carbamoyl phosphate concentration in mitochondria incubated without ornithine to minimize citrulline synthesis and impairs the mitochondrial uptake of ornithine, but it has neither effect when succinate is the oxidizable substrate. 4. Propionate, butyrate and crotonate also inhibit mitochondrial citrulline synthesis, but much less than pent-4-enoate. 5. Acetate, pentanoate, pent-2-enoate, hexanoate, octanoate, isovalerate, tiglylate and alpha-methylbutyrate have little or no effect on mitochondrial citrulline synthesis.

Adenosine Triphosphate↗
PubMed2003

Two W-containing formate dehydrogenases (CO2-reductases) involved in syntrophic propionate oxidation by Syntrophobacter fumaroxidans.

Two formate dehydrogenases (CO2-reductases) (FDH-1 and FDH-2) were isolated from the syntrophic propionate-oxidizing bacterium Syntrophobacter fumaroxidans. Both enzymes were produced in axenic fumarate-grown cells as well as in cells which were grown syntrophically on propionate with Methanospirillum hungatei as the H2 and formate scavenger. The purified enzymes exhibited extremely high formate-oxidation and CO2-reduction rates, and low Km values for formate. For the enzyme designated FDH-1, a specific formate oxidation rate of 700 U.mg-1 and a Km for formate of 0.04 mm were measured when benzyl viologen was used as an artificial electron acceptor. The enzyme designated FDH-2 oxidized formate with a specific activity of 2700 U.mg-1 and a Km of 0.01 mm for formate with benzyl viologen as electron acceptor. The specific CO2-reduction (to formate) rates measured for FDH-1 and FDH-2, using dithionite-reduced methyl viologen as the electron donor, were 900 U.mg-1 and 89 U.mg-1, respectively. From gel filtration and polyacrylamide gel electrophoresis it was concluded that FDH-1 is composed of three subunits (89 +/- 3, 56 +/- 2 and 19 +/- 1 kDa) and has a native molecular mass of approximately 350 kDa. FDH-2 appeared to be a heterodimer composed of a 92 +/- 3 kDa and a 33 +/- 2 kDa subunit. Both enzymes contained tungsten and selenium, while molybdenum was not detected. EPR spectroscopy suggested that FDH-1 contains at least four [2Fe-2S] clusters per molecule and additionally paramagnetically coupled [4Fe-4S] clusters. FDH-2 contains at least two [4Fe-4S] clusters per molecule. As both enzymes are produced under all growth conditions tested, but with differences in levels, expression may depend on unknown parameters.

Carbon Dioxide↗
PubMed2002

Influence of buffered propionic acid on the development of micro-organisms in hay.

We tested the benefit of using buffered propionic acid (BPA) as a means of preventing farmer's lung disease (FLD). BPA, a new formulation of propionic acid, a hay preservative with no deleterious effect on farm machinery or cattle, reduces the development of micro-organisms in hay. Twenty pairs of round bales were analysed for concentration of micro-organisms measured in the winter following hay treatment. Each pair included one untreated bale and one bale treated with BPA during haymaking. Our results showed the following decreases in concentration in treated bales: total fungal species, 40% (P < 0.05); Eurotium amstelodami (the main species found), 65% (P < 0.01); and thermophilic actinomycetes, 60% (not significant), respectively. We conclude that BPA could be used to prevent FLD.

Actinomycetales↗
PubMed1979

Hydrazonopropionic acids, a class of hypoglycemic substances. 1. Hypoglycemic effect of 2-(phenylethylhydrazono)- and 2-(2-cyclohexyl-ethylhydrazono)-propionic acid.

The two hydrazone-compounds 2-(phenylethylhydrazono)-propionic acid (PEHP) and 2-(2-cyclohexyl-ethylhydrazono)-propionic acid (CHEHP) significantly lowered the blood glucose level in several laboratory animals fasted 48 hours (guinea pigs, mice, hamsters and rats). In the guinea pig, PEHP produced a three times stronger hypoglycemic effect than phenelzine, its corresponding hydrazine. Conversely both hydrazono compounds decreased the monoamine oxidase activity much less, than phenelzine. CHEHP (145 mumol/kg) inhibited this enzyme by less than 14%. After oral administration both hydrazones (200 mumol/kg) also produced a distinct hypoglycemic effect. The blood glucose lowering properties of the two hydrazones were most manifest in fasted guinea pigs, diabetic mice and rats with streptozotozin diabetes.

Animals↗
PubMed2006

Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl] acetic acids, 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]propionic acids and related derivatives.

The reaction of 3-(1-adamantyl)-4-substituted-1,2,4-triazoline-5-thiones 3a-g with sodium chloroacetate, in ethanolic sodium hydroxide yielded the corresponding N1-acetic acid derivatives 4a-g. The interaction of 3a-g with ethyl 2-bromopropionate in acetone, in the presence of potassium carbonate, yielded the corresponding N1-ethyl propionate derivatives 5a-g, which upon hydrolysis with aqueous sodium hydroxide afforded the corresponding propionic acid derivatives 6a-g. Similarly, the reaction of 3-(1-adamantyl)-4-amino-1,2,4-triazoline-5-thione 7 with sodium chloroacetate in ethanolic sodium hydroxide yielded the corresponding N1-acetic acid derivative 8. On the other hand, the reaction of 2-(1-adamantyl)-1,3,4-oxadiazoline-5-thione 9 with sodium chloroacetate yielded the corresponding S-acetic acid derivative 10. Compounds 4a-g, 5b, 5c, 5g, 6a-g, 8 and 10 were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several derivatives produced good or moderate activities particularly against Bacillus subtilis. In addition, the in vivo anti-inflammatory activities of these compounds were determined using the carrageenin-induced paw oedema method in rats. Compounds 4a, 4b, 4e, 4f, 6f, 6g and 10 produced good dose-dependent anti-inflammatory activities.

Algorithms↗
PubMed1980

Hydrazonopropionic acid, a new class of hypoglycemic substances. 2. Influence of 2-(phenylethylhydrazono)- and 2-(2-cyclohexyl-ethylhydrazono)-propionic acid on redox systems, acid base status and monoamino oxidase activity.

Phenylethylhydrazono-propionic acid (PEHP) and cyclohexyl-ethylhydrazono-propionic acid (CHEHP) has been shown to lower blood glucose concentrations in various laboratory animals after intraperitoneal or oral application. The present study has been conducted to investigate, if these hydrazones may induce lactic acidosis like the biguanides or may cause unwanted side reactions due to an inhibition of monoamino oxidase like the corresponding hydrazines. It was found that intramitochondrial and cytoplasmatic redox ratios were not influenced at a hypoglycemic effective dosage (145 mumol/kg body weight) of these substances in fasted guinea pigs. An effect on the acid base status was not observed. Both substances lowered the concentration of ketone bodies in fasted guinea pigs. In vitro the activity of monoamino oxidase purified from guinea pig liver was much less inhibited by the hydrazones than by one of the corresponding hydrazines (phenelzine). Furthermore CHEHP (145 mumol/kg body weight) did not influence the serum activity of various liver enzymes and the concentration of triglycerides, cholesterol and uric acid in plasma of fasted guinea pigs. It is concluded that CHEHP meets basic requirements for a potential oral antidiabetic agent.

Acetoacetates↗
PubMed2002

The Orphan G protein-coupled receptors GPR41 and GPR43 are activated by propionate and other short chain carboxylic acids.

GPR41 and GPR43 are related members of a homologous family of orphan G protein-coupled receptors that are tandemly encoded at a single chromosomal locus in both humans and mice. We identified the acetate anion as an agonist of human GPR43 during routine ligand bank screening in yeast. This activity was confirmed after transient transfection of GPR43 into mammalian cells using Ca(2+) mobilization and [(35)S]guanosine 5'-O-(3-thiotriphosphate) binding assays and by coexpression with GIRK G protein-regulated potassium channels in Xenopus laevis oocytes. Other short chain carboxylic acid anions such as formate, propionate, butyrate, and pentanoate also had agonist activity. GPR41 is related to GPR43 (52% similarity; 43% identity) and was activated by similar ligands but with differing specificity for carbon chain length, with pentanoate being the most potent agonist. A third family member, GPR42, is most likely a recent gene duplication of GPR41 and may be a pseudogene. GPR41 was expressed primarily in adipose tissue, whereas the highest levels of GPR43 were found in immune cells. The identity of the cognate physiological ligands for these receptors is not clear, although propionate is known to occur in vivo at high concentrations under certain pathophysiological conditions.

Amino Acid Sequence↗
PubMed2000

Subchronic and developmental toxicity studies of n-butyl propionate vapor in rats.

Two inhalation studies were conducted to evaluate the possible subchronic and developmental toxic effects of n-butyl propionate. In the subchronic study, Sprague-Dawley rats (15/sex/group) were exposed to 0, 250, 750, or 1500 ppm vapor for 6 h/d, 5 d/wk for 13 wk. Five of the rats per sex per group were held after the final exposure for an 8-wk recovery period. Standard parameters of subchronic toxicity were measured throughout the study, and at the end of exposure and recovery periods, necropsies were performed, organs weighed, and tissues processed for microscopic examination. Exposure did not produce marked treatment-related deaths or adversely affect clinical signs, hematology, clinical chemistries, organ weights, or the histology of major visceral organs. The only systemic toxic effects were significant decreases in body weight, body weight gain, and feed consumption that occurred in 1500 ppm group rats. Morphologic changes were limited to the nasal cavity as evidenced by a concentration-related increased incidence and severity of olfactory epithelium degeneration in rats of the 750 and 1500 ppm groups. These degenerative microscopic alterations were primarily confined to the olfactory epithelium within the dorsal portion of the medial meatus, with lesser involvement of the olfactory mucosae overlying the tips of some of the adjacent ethmoturbinates. Both the systemic and nasal cavity effects appeared reversible after exposure ceased. In the developmental toxicity study, pregnant Sprague-Dawley rats (24/group) were exposed to 0, 500, 1000, or 2000 ppm vapor for 6 h/d on gestation d 6-15 and sacrificed on gestation d 20. All treatment-group dams exhibited significant reductions in body weight, body weight gain, and feed consumption. Gestational parameters were equivalent across all groups and there were no treatment-related developmental or teratogenic effects. The no-observed-adverse effects levels (NOAELs) determined for nbutyl propionate were 250 ppm for subchronic toxicity (based on the olfactory epithelium degeneration) and 22000 ppm for developmental toxicity (no developmental effects at top dose tested). Under the conditions of this study, a NOAEL was not determined for maternal toxicity.

Administration, Inhalation↗
PubMed1996

Comparison of official methods for 'readily oxidizable substances' in propionic acid as a food additive.

The official methods for 'readily oxidizable substances (ROS)' in propionic acid as a food additive were compared. The methods examined were those adopted in the Compendium of Food Additive Specifications (CFAS) by the Joint FAO-WHO Expert Committee on Food Additives, FAO, The Japanese Standards for Food Additives (JSFA) by the Ministry of Health and Welfare, Japan, and the Food Chemicals Codex (FCC) by the National Research Council, USA. The methods given in CFAS and JSFA are the same (potassium permanganate consumption). However, by this method, manganese (VII) in potassium permanganate was readily reduced to colourless manganese(II) with some substances contained in the propionic acid before reacting with aldehydes, which are generally considered as 'readily oxidizable substances', to form brown manganese (IV) oxide. The FCC method (bromine consumption) for 'ROS' could be recommended because it was able to obtain quantitative results of 'ROS', including aldehydes.

Aldehydes↗
PubMed1982

The effects of spacing protein intake on nitrogen balance and plasma amino acids in a child with propionic acidemia.

The effect of protein distribution on nitrogen balance and the plasma aminogram was studied in a 34-month-old male child with propionic acidemia. Protein provided 4.8% of energy of which high biological value protein was given either as a bolus or evenly distributed in three meals per day. Analysis of nitrogen balance including estimated sweat nitrogen losses revealed no major difference between the two diets. No marked differences in the fasting plasma concentrations of essential amino acids were noted with protein distribution. A generalized increase in concentration of all nonessential amino acids except taurine and ornithine was noted when protein was evenly distributed throughout the day. The ratio of nonessential to essential amino acids was higher after even protein distribution than when protein was given as a bolus. The data suggests that a low protein diet (206 mg nitrogen/kg/day) with adequate energy intake used in managing this child with propionic acidemia provided adequate amounts of total nitrogen and essential amino acids for normal growth regardless of protein distribution.

Amino Acid Metabolism, Inborn Errors↗
PubMed1980

Influence of ration physical form, ruminal degradable nitrogen and age on rumen epithelial propionate and acetate transport and some enzymatic activities.

Holstein bull calves were used to determine the influence of degradable nitrogen and ration physical form on rumen epithelial transport and enzymic activity. Rations contained 30, 45 and 60% ruminal degradable nitrogen (RDN), each with three forms (ground hay, GR; chopped hay, CH; and all concentrate, CONC). Rumen tissue samples were obtained by biopsy (8 weeks) and at slaughter (20 weeks). Acetate transport across rumen epithelium increased between 8 and 20 weeks in calves fed GR and CH, but not in calves fed CONC. Propionate transport was highest in calves fed GR and lowest in calves fed CONC at both 8 and 20 weeks. Transport of acetate and propionate was incresed with increasing RDN at 20 weeks. There were no differences in ruminal tissue lactate production. Rumen papillae of calves fed CONC were abnormal in morphology and at 20 weeks dry mucosal weights (mg/cm2) were highest. Lactate dehydrogenase and NADP-malic dehydrogenase activities were not different. Propionyl CoA synthetase activity was higher in 20-week calves fed CONC, compared to GR to CH. Glutamate dehydrogenase and aspartate aminotransferase activities were highest in 20-week calves fed 60% RDN rations, regardless of physical form.

Acetates↗
PubMed1989

Fermentable dietary fibers elevate urinary methylmalonate and decrease propionate oxidation in rats deprived of vitamin B-12.

This study examines the effect of dietary fiber supplements of different degrees of bacterial fermentability on biochemical indicators of vitamin B-12 deficiency in rats. Groups of rats were fed a fiber-free diet deficient in vitamin B-12 or the fiber-free diet diluted with 5% of a poorly fermentable dietary fiber (cellulose, lignin or alginic acid) or a highly fermentable fiber (pectin, guar gum or xylan). Poorly fermentable fibers had no significant effect on apparent B-12 status, whereas the highly fermentable fibers significantly increased urinary methylmalonic acid and depressed oxidation of [14C]propionate to 14CO2. Pectin consistently induced significantly greater effects than did xylan or guar gum. The data are consistent with the hypothesis that fermentable fibers stimulate bacterial propionate production and exaggerate certain biochemical indicators of B-12 deficiency. Since pectin had a more pronounced effect than did other fermentable fibers, the possibility that pectin may also interfere with B-12 absorption requires further study.

Animals↗
PubMed2000

Fermentation of resistant rice starch produces propionate reducing serum and hepatic cholesterol in rats.

This study was designed to investigate the effects of different proportions of rice starch and cornstarch on lipid metabolism in rats fed high dietary cholesterol. Male Wistar rats were fed a 10 g/100 g fat diet containing 1 g/100 g cholesterol with 0 (control diet), 15, 30, 45 or 63 g/100 g rice starch with an enzyme resistant starch concentration of 1.26, 1.39, 1.52, 1.65 or 1.80 g/100 g, respectively, for 4 wk. Groups fed diets with < 63 g/100 g rice starch were supplemented with cornstarch to 63 g/100 g. The two kinds of starch had different structures as seen using scanning electron microscopy (SEM). The rice starch was an aggregation (n = 20-60) of smaller granules (3-8 microm in diameter), whereas the cornstarch was composed of larger (5-15 microm in diameter), single granules. The compound rice starch (0.99 kg/L) was larger in size and denser in structure than cornstarch (0.63 kg/L). Serum total cholesterol concentrations in rats fed both the 45 and 63 g/100 g rice starch diets were significantly lower than in all other groups (P < 0.05). The serum propionate concentration in the rats fed 63 g/100 g rice starch diets was significantly higher than that of other groups. Hepatic triglyceride and total cholesterol concentrations in rats fed 63 g/100 g rice starch diets were significantly lower than in the control group. These results suggest that, because the compound rice starch was an aggregation of smaller granules, larger in size and denser in structure than cornstarch, it was digested more slowly and altered lipid metabolism. Resistant rice starch may be fermented to produce propionate, which reduces serum and hepatic cholesterol.

Animals↗
PubMed1994

Metabolic effects of propionate, hexanoate and propionylcarnitine in normoxia, ischaemia and reperfusion. Does an anaplerotic substrate protect the ischaemic myocardium?

It has been suggested that propionyl-L-carnitine administration to ischaemic hearts facilitates the restoration of cardiac function upon reperfusion, but it is still a matter of dispute whether its effect is conveyed via the metabolic effect of the propionyl moiety, the carnitine moiety or other mechanisms involving membrane receptor interactions. The metabolism of propionylcarnitine involves the formation of succinyl-CoA, which causes an increase in the total amount of tricarboxylic acid cycle intermediates. According to the current paradigm, anaplerosis ensures rapid restoration of tricarboxylic acid cycle activity during reperfusion. To evaluate the contribution of anaplerosis to the protective effect of propionylcarnitine during ischaemia and reperfusion, isolated rat hearts were perfused with Krebs-Henseleit bicarbonate buffer containing 5 mM glucose+insulin (12 IU per litre), to which 1 mM propionate, 0.8 mM hexanoate or 1 mM propionylcarnitine were added. Global 20 or 24 min no-flow ischaemia was followed by 10 min reperfusion. The flavoprotein redox state, myoglobin oxygenation, oxygen consumption and mechanical functioning of the heart were recorded and metabolites determined in freeze-trapped tissue. In parallel experiments, the cellular energy state was studied with phosphorus nuclear magnetic resonance spectrometry. The addition of 1 mM propionylcarnitine failed to cause an anaplerotic effect, but did bring about an oxidation of flavins, probably due to citrate synthase inhibition. Propionate showed similar but stronger effects and a marked anaplerosis, but still failed to improve the recovery of the heart upon reperfusion. The addition of hexanoate caused marked anaplerosis upon reperfusion and flavin reduction. The results failed to demonstrate that propionylcarnitine had any beneficial effect on the ischaemic myocardium.

Animals↗