[Esterification of sterols with fatty acids and with succinic acid in mycobacteria].
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Bacteria↗
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Results for “SUCCINIC ACID”
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[Preparation of optically active succinic acid derivatives. III. Regioselective condensation reactions of optically active 2-substituted succinic acids with diimidazolide].
We investigated the large scale synthesis of monocalcium bis [(2S)-2-benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl) propionate] dihydrate (KAD-1229), which has a potent hypoglycemic effect, in a single reaction vessel. (2S)-2-Benzyl-3-(cis-hexahydroisoindolin-2-ylcarbonyl) propionic acid (7) was directly obtainable from (S)-2-benzylsuccinic acid (2) and cis-hexahydroisoindoline (4), without the isolation of intermediates by the method using thionyldiimidazole (9) and/or diimidazolide of the acid 2. Sequential reaction of imidazole with thionyl chloride, 2, and 4, followed by acid catalyzed hydrolysis gave amidecarboxylic acid 7 in 86% overall yield. The acid 7 was treated with 2 N NaOH, followed by the treatment with calcium chloride to give KAD-1229 in 91% yield.
Chemical Phenomena↗
[Detection of anion residues of surface-active compounds of the type sulfosuccinic acid salts and succinic acid monoesters on the surface of containers in contact with food].
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Chromatography, Thin Layer↗
[Activity of the lactic acid dehydrogenase and succinic acid dehydrogenase of the liver of guinea pigs infected with tubercle bacilli. Effect of immunization with BCG vaccine].
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Animals↗
[Identification and semiquantitative determination of succinic acid in chloramphenicolhydrogen succinate].
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Chloramphenicol↗
Production of fumaric acid using rice bran and subsequent conversion to succinic acid through a two-step process.
The fungal production of fumaric acid using rice bran and subsequent bacterial conversion of succinic acid using fungal culture broth were investigated. Since the rice bran contains abundant proteins, amino acids, vitamins, and minerals, it is suitable material that fungi use as a nitrogen source. The effective concentration of rice bran to produce fumaric acid was 5 g/L. A large amount of rice bran caused excessive fungal growth rather than enhance fumaric acid production. In addition, we could produce fumaric acid without the addition of zinc and iron. Fungal culture broth containing approx 25 g/L of fumaric acid was directly employed for succinic acid conversion. The amount of glycerol and yeast extract required for succinic acid conversion was reduced to 70 and 30%, respectively, compared with the amounts cited in previous studies.
Biochemistry↗
The Bacteroides by-product succinic acid inhibits neutrophil respiratory burst by reducing intracellular pH.
Short-chain fatty acids, particularly succinic acid, are major metabolic by-products of Bacteroides species. To determine their role as potential virulence factors in infections containing Bacteroides species, short-chain fatty acids were examined for their effect on the neutrophil respiratory burst. Succinate (30 to 50 mM) irreversibly impaired superoxide and hydrogen peroxide production in response to opsonized zymosan and phorbol myristate acetate when neutrophils were treated at pH 5.5 but not pH 6.0 or greater. Several other short-chain fatty acids tested produced similar inhibition. Reversible inhibition of oxygen consumption was found when neutrophils were incubated in succinate-containing medium (pH 6.0) as well as control medium (pH 6.0 and 5.5). Neutrophil cytoplasmic pH was measured by fluorimetric techniques to determine whether the inhibition was mediated via a reduction in intracellular pH. The intracellular pH of cells in control medium (pH 6.5 or less) was significantly reduced compared with pH 7.4. The addition of succinate (30 mM) to these media caused a further significant reduction in cytoplasmic pH at each pH level. The reduction in intracellular pH was sufficient to account for both the irreversible and reversible impairment of the neutrophil respiratory burst. Thus, short-chain fatty acids appear to exert their inhibition, at least in part, by reducing intracellular pH. These data also demonstrate the potential for interactions between Bacteroides species and their microenvironment to increase the virulence of an infection.
Bacteroides↗
Inhibition of mast cell-dependent anaphylaxis by succinic acid.
We have examined the effect of succinic acid on anaphylaxis. Succinic acid (100 mM) significantly inhibited systemic anaphylaxis induced by compound 48/80 in mice and dose-dependently inhibited local anaphylaxis activated by anti-dinitrophenyl IgE. Further 10 and 100 mM significantly inhibited histamine release from rat peritoneal mast cells activated by compound 48/80 or anti-dinitrophenyl IgE. In addition succinic acid (0.1 and 1 mM) had a significant inhibitory effect on anti-dinitrophenyl IgE-induced tumour necrosis factor-alpha secretion from rat peritoneal mast cells. The level of cyclic AMP in rat peritoneal mast cells, when succinic acid (100 mM) was added, transiently and significantly increased about 4 times compared with that of basal cells. These results suggest a possible use of succinic acid in managing mast cell-dependent anaphylaxis.
Anaphylaxis↗
Insulinotropic action of the monoethyl ester of succinic acid.
1. Selected esters of succinic acid are currently under investigation as potential insulinotropic tools in the treatment of non-insulin-dependent diabetes. At variance with the methyl esters of succinic acid used in most of the work so far conducted from this perspective, the monoethyl ester of succinic acid (EMS) offers the advantage of avoiding the undesirable generation of methanol by intracellular hydrolysis. In the present study, the metabolism and functional effects of EMS were investigated, therefore, in rat pancreatic islets. 2. At a 10 mM concentration, EMS enhanced insulin release from islets stimulated by 7-17 mM D-glucose but failed to do so at lower concentrations of the hexose. EMS was efficiently metabolized, as judged from the generation of 14CO2 by islets exposed to the monoethyl ester of either [1,4-14C] or [2, 3-14C]succinic acid. D-Glucose (6 mM) failed to affect the metabolism of EMS (10 mM), which itself failed to affect the metabolism of D-[5-3H]glucose or D-[U-14C]glucose. EMS also stimulated biosynthetic activity in the islets. It inhibited 86Rb and 45Ca outflow from prelabeled islets perfused in the absence of D-glucose but enhanced the efflux of the two cationic tracers in the presence of the hexose (7 mM). 3. It is concluded that the insulinotropic action of EMS is attributable, to a large extent, to its capacity to act as a nutrient in islet cells.
Animals↗
Effect of process parameters on succinic acid production in Escherichia coli W3110 and enzymes involved in the reductive tricarboxylic acid cycle.
The effect of process optimization on succinic acid production by Escherichia coli W3110 and on enzymes involved in the reverse tricarboxylic acid cycle was studied. Approximately, 7.02 g L-1 of succinic acid was produced in 60 h at pH 7.0 in 500 mL anaerobic bottles containing 300 mL of the medium, wherein the sucrose concentration was 2.5%, the ratio of tryptone to ammonium hydrogen phosphate was 1:1, and the concentration of magnesium carbon ate was 1.5%. When these optimized fermentation conditions were employed in a 10 L bioreactor, 11.2 g L-1 of succinic acid was produced in 48 h. This is a 10-fold increase in succinic acid production from the initial titer of 0.94 g L-1. This clearly indicates the importance of process optimization, where by manipulating the media composition and production conditions, a remarkable increase in the production of the desired biomolecule can be obtained. The production of succinic acid is a multi-step reaction through the reverse tricarboxylic acid cycle. A linear relationship was observed between succinic acid production and the enzyme activities. The enzyme activities were found to increase in the order phospho-enol-pyruvate carboxylase<malate dehydrogenase<fumarase<fumarate reductase. The activity of phospho-enol-pyruvate carboxykinase was also estimated. Results indicate that this enzyme was not a very active participant in the production of succinic acid, since it catalyzes the phosphorylation of oxaloacetic acid to yield phospho-enol-pyruvate.
Anaerobiosis↗
Comparison between the insulinotropic potential of ten new esters of succinic acid.
Selected esters of succinic acid are currently under investigation as insulinotropic tools for the treatment of non-insulin-dependent diabetes mellitus. The aim of the present study was to investigate, in isolated rat pancreatic islets, the insulin secretory response to ten novel esters of succinic acid. According to six different methods of comparison, the following hierarchy in insulinotropic potential was established: 4-tert-butyl-succinate < or = glycerol-1,2-dimethylsuccinate-3-hydrogenosuccinate < or = threitol-3-succinoyl-1,2,4-trimethylsuccinate < or = ethanediol-1,2-diethylsuccinate < or = glycerol-1,2-dimethylsuccinate < or = glycerol-3-hydroxy-1,2-dimethylsuccinate < or = arabitol-5-hydroxy-1,2,3,4-tetramethylsuccinate < or = threitol-1,2,4-trimethylsuccinate < or = ethanediol-1,2-dimethylsuccinate < propanediol-1,2-dimethylsuccinate. There was a close correlation (r = 0.823) between the insulinotropic potential and the minimal effective concentration, which ranged between the extreme values of 10 microM and 2.5 mM. In the presence of the esters, the concentration-response relationship for glucose-stimulated insulin release was changed from its typically sigmoidal shape to a hyperbolic pattern, with most agents enhancing insulin output at a low hexose concentration (2.8 mM) but failing to do so at a high glucose level (16.7 mM). Highly potent insulinotropic esters have several advantages over other antidiabetic agents in clinical use.
Animals↗
In vivo stimulation of insulin release by the monoethyl, monopropyl, monoisopropyl, monoallyl and diallyl esters of succinic acid.
The methyl esters of succinic acid are potent insulin secretagogues, currently under investigation as possible tools in the treatment of non-insulin-dependent diabetes. The in vivo administration of these esters may result, however, in the undesirable generation of methanol. The present study reveals that other esters of succinic acid, such as the monoethyl, monopropyl, monoisopropyl, monoallyl and diallyl esters, stimulate insulin release when administered intravenously in a dose of 2 mumol/g body weight to anaesthetized fed rats. This indicates that several succinic acid esters, that are not susceptible to lead, through their intracellular hydrolysis, to the production of methanol remain efficient in vivo as insulin secretagogues.
Animals↗
Uptake and efflux of succinic acid by uninduced mycelium of Claviceps purpurea.
Claviceps purpurea PRL 1980 grew on partially dissociated succinic acid (pH 4) but not on fully dissociated succinic acid (pH 7.2). Myeclium suspended in 42 mM solution of partially ionized succinic acid (pH 4; 60.1% nonionized, 39% monoanion, and 0.9% dianion, K+ salt) over a period of 25 min accumulated more succinic acid carbon than mycelium suspended in highly ionized solution (pH 6.8; 0.01% nonionized, 4.8% monoanion, and 95% dianion). The greater accumulation from partially ionized solution was not attributable solely to metabolism of succinic acid nor to the lower external concentration of potassium ion. Rate of uptake by sodium azide and iodoacetate-treated mycelium was proportional to external concentration at least up to 200 mumol/ml. External potassium or sodium ion was not required for uptake by inhibited or uninhibited mycelium and external sodium ion and glucose did not allow concentration of succinic acid. The internal concentrations of succinic acid carbon expressed as succinic acid in cell water were about the same as the external concentrations. Uptake was not appreciably affected by extent of ionization of external succinic acid but accumulation was markedly affected. A plot of accumulated succinic acid carbon against external pH produced a bimodal curve with the two maxima corresponding to the maximal concentrations of nonionized and monoanion succinic acid. The bimodal curve probably results from overlapping of two separate curves; the nonionized form accumulating efficiently because of one interaction with the cell and the monoanion form accumulating efficiently because of another interaction. Uptake from concentrated solution is by diffusion and efflux is rapid but not complete. Efflux is not retarded by presence of phosphate in the external solution.
Azides↗
[The role of succinic acid in the biosynthesis of levorin].
The influence of succinic acid as a component of media for biosynthesis of levorin, a polyenic antibiotic was studied. It was shown that with the use of the soybean-corn medium supplemented with succinic acid (0.05-0.4 per cent) the antibiotic content in the fermentation broth was higher than that in the control. The highest stimulating effect (135 per cent) was observed with addition of 0.1 per cent of succinic acid. For providing optimal antibiotic production in the synthetic medium supplemented with succinic acid (0.4 per cent) addition of acetic acid (0.05 per cent) was required. Studies with the soybean-corn medium with and without succinic acid revealed differences in the level of p-aminoacetophenone, an aromatic fragment of the levorin molecule. Under the conditions of the medium with succinic acid the content of p-aminoacetophenone in the mycelium was higher by 10 to 18 per cent as compared to that in the control and depended on the fermentation period. The role of succinic acid in biosynthesis of levorin is discussed.
Acetates↗
The effect of the bacterial product, succinic acid, on neutrophil bactericidal activity.
We investigated the effect of succinic acid on neutrophil bactericidal activity in a model of intra-abdominal abscess induced in mice by the peritoneal inoculation of 5 x 10(6) cfu ml-1 E. coli and 5 x 10(8) cfu ml-1 B. fragilis plus 1 mg of bran as faecal fibre analogue. The mean pH of the induced abscesses at week 1 was 6.7, higher than the pH associated with succinic acid inhibitory activity. We therefore determined the effect of succinic acid (0-100 mM) at pH 6.7 on the bactericidal activity of mouse bone marrow-derived neutrophils. Phagocytic killing of Proteus mirabilis by neutrophils was significantly inhibited by 30-100 mM succinic acid at pH 6.7 but there was no significant effect of succinic acid on engulfment of bacteria at this pH. However, significant inhibition of intracellular killing (assayed by adding succinic acid to suspensions of neutrophils which had engulfed bacteria in low serum concentrations but in the absence of succinic acid) was noted at 70 and 100 mM. These results indicate that succinic acid inhibits neutrophil bactericidal activity at a physiological pH, principally through inhibition of intracellular killing mechanisms and therefore contributing to bacterial persistence in this model of abscess formation.
Abdominal Abscess↗
Importance of redox balance on the production of succinic acid by metabolically engineered Escherichia coli.
We had previously shown that succinic acid production in a pfl ldhA double mutant strain of Escherichia coli could be enhanced by amplifying the malic enzyme activity. However, recombinant E. coli NZN111 (F- Apfl::Cam ldhA::Kan) harboring pTrcML, a plasmid containing the E. coli malic enzyme gene, produced a considerable amount of malic acid along with the desired product, succinic acid. To have an insight into the intracellular metabolism, metabolic control analysis was carried out. From the results of a simulation, it was predicted that supplying additional reducing power could enhance succinic acid production. More reduced carbon substrate sorbitol was thus examined for the possibility of matching the potential during succinic acid production. When NZN111 (pTrcML) was cultured in LB medium containing 20 g sorbitol/l under a CO2 atmosphere, 10 g succinic acid/l was produced. The apparent yield of succinic acid was 1.1 g succinic acid/g sorbitol, which is 85% of the maximum theoretical yield. Therefore, it was found that redox balancing was important for the enhanced production of succinic acid in metabolically engineered E. coli.
Carbon Dioxide↗
Anxiolytic-like effect of succinic acid in mice.
The putative anxiolytic activity of succinic acid was examined in male mice by using a number of experimental paradigms of anxiety and compared with that of the known anxiolytic compound diazepam. Use of the elevated plus-maze test revealed that diazepam (1.0, 2.0 and 4.0 mg/kg, PO) or succinic acid (3.0 or 6.0 mg/kg, PO) increased the percentage of entries into open arms and of time spent on open arms. In novel food consumption test, succinic acid (3.0, 6.0, and 12.0 mg/kg, IP) caused significant increases in food intake during 5 min when compared with the vehicle. In the stress-induced hyperthermia test, 40 min after drug administration rectal temperature was measured, succinic acid at dose of 1.5 mg/kg, inhibited stress-induced hyperthermia. Thus, these findings indicated that, in contrast with diazepam, succinic acid exhibits anxiolytic-like effect.
Animals↗
Prophylaxis of encephalopathies and risk factors of atherogenesis development in the postresuscitation period in rats by means of succinic acid.
The effect of oral administration of succinic acid was studied in 66 rats exposed to 10 min cardiac arrest with further resuscitation. A total of 30 mg/kg of the drug were administered daily for 5 days starting with day 3 up to day 7 after resuscitation. The experiments have revealed that treatment with succinic acid caused normalization of the orienting behavior in an 'open field' test, decrease of the intensity of response to electric shock, normalization of free radical formation in the brain and serum and reduced cerebral morphological changes. The succinic acid prevented the increase of cholesterol, triglyceride and low density lipoproteins in the blood. The data suggested that after additional trials the succinic acid could be used to prevent development of postresuscitation encephalopathies (3 months after reanimation).
Animals↗