Enzymatic and chemical synthesis of 3-sulfinopropionic acid, an analog of succinic acid.
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Results for “SUCCINIC ACID”
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Production of succinic Acid from citric Acid and related acids by lactobacillus strains.
A number of Lactobacillus strains produced succinic acid in de Man-Rogosa-Sharpe broth to various extents. Among 86 fresh isolates from fermented cane molasses in Thailand, 30 strains (35%) produced succinic acid; namely, 23 of 39 Lactobacillus reuteri strains, 6 of 18 L. cellobiosus strains, and 1 of 6 unidentified strains. All of 10 L. casei subsp. casei strains, 5 L. casei subsp. rhamnosus strains, 6 L. mali strains, and 2 L. buchneri strains did not produce succinic acid. Among 58 known strains including 48 type strains of different Lactobacillus species, the strains of L. acidophilus, L. crispatus, L. jensenii, and L. parvus produced succinic acid to the same extent as the most active fresh isolates, and those of L. alimentarius, L. collinoides, L. farciminis, L. fructivorans (1 of 2 strains tested), L. malefermentans, and L. reuteri were also positive, to lesser extents. Diammonium citrate in de Man-Rogosa-Sharpe broth was determined as a precursor of the succinic acid produced. Production rates were about 70% on a molar basis with two fresh strains tested. Succinic acid was also produced from fumaric and malic acids but not from dl-isocitric, alpha-ketoglutaric, and pyruvic acids. The present study is considered to provide the first evidence on the production of succinic acid, an important flavoring substance in dairy products and fermented beverages, from citrate by lactobacilli.
Journal Article↗
Succinic acid production with reduced by-product formation in the fermentation of Anaerobiospirillum succiniciproducens using glycerol as a carbon source.
Succinic acid was produced by fermentation of Anaerobiospirillum succiniciproducens using glycerol as a carbon source. When cells were anaerobically cultured in a medium containing 6.5 g/L glycerol, a high succinic acid yield (133%) was obtained while avoiding the formation of by-product acetic acid. The gram ratio of succinic acid to acetic acid was 25.8:1, which is 6.5 times higher than that obtained using glucose (ca. 4:1) as a carbon source. Therefore, succinic acid can be produced with much less by-product formation by using glycerol as a carbon source, which will facilitate its purification. When glucose and glycerol were cofermented with the increasing ratio of glucose to glycerol, the gram ratio of succinic acid to acetic acid and succinic acid yield decreased, suggesting that glucose enhanced acetic acid formation irrespective of the presence of glycerol. Glycerol consumption by A. succiniciproducens required unidentified nutritional components present in yeast extract. By intermittently feeding yeast extract along with glycerol, a high succinic acid yield (160%) could be obtained while still avoiding acetic acid formation. This resulted in the highest ratio of succinic acid to acetic acid (31.7:1).
Acetic Acid↗
Metabolism of succinic acid methyl esters in neural cells.
The metabolism and metabolic effects of succinic acid methyl esters were examined in both NG108-15 mouse neuroblastoma x rat glioma hybrid cells and normal rat brain cells. The conversion of the dimethyl ester of 14C-labeled succinic acid (10 mM) to 14CO2 only represented 5% or less of that found at an equimolar concentration of D-[U- 14C]glucose. Neither the monomethyl nor the dimethyl ester of succinic acid exerted any significant effect upon the metabolism of D-glucose. Likewise, D-glucose (10 mM) failed to significantly affect the oxidation of the dimethyl ester of either [1,4- 14C]succinic acid or [2,3- 14C]succinic acid. It is concluded that, at variance with the situation recently documented in rat pancreatic islets and hepatocytes, the methyl esters of succinic acid are poorly metabolized in neural cells.
Animals↗
Metabolic engineering of Escherichia coli for enhanced production of succinic acid, based on genome comparison and in silico gene knockout simulation.
Comparative analysis of the genomes of mixed-acid-fermenting Escherichia coli and succinic acid-overproducing Mannheimia succiniciproducens was carried out to identify candidate genes to be manipulated for overproducing succinic acid in E. coli. This resulted in the identification of five genes or operons, including ptsG, pykF, sdhA, mqo, and aceBA, which may drive metabolic fluxes away from succinic acid formation in the central metabolic pathway of E. coli. However, combinatorial disruption of these rationally selected genes did not allow enhanced succinic acid production in E. coli. Therefore, in silico metabolic analysis based on linear programming was carried out to evaluate the correlation between the maximum biomass and succinic acid production for various combinatorial knockout strains. This in silico analysis predicted that disrupting the genes for three pyruvate forming enzymes, ptsG, pykF, and pykA, allows enhanced succinic acid production. Indeed, this triple mutation increased the succinic acid production by more than sevenfold and the ratio of succinic acid to fermentation products by ninefold. It could be concluded that reducing the metabolic flux to pyruvate is crucial to achieve efficient succinic acid production in E. coli. These results suggest that the comparative genome analysis combined with in silico metabolic analysis can be an efficient way of developing strategies for strain improvement.
Base Sequence↗
A statistical method for enhancing the production of succinic acid from Escherichia coli under anaerobic conditions.
The most influential parameters for succinic acid production obtained through one at a time method were sucrose, tryptone, magnesium carbonate, inoculum size and incubation period. These resulted in the production of 7.0 g L(-1) of succinic acid in 60 h from Escherichia coli W3110 under anaerobic conditions. Based on these results, a statistical method, face centered central composite design (FCCCD) falling under response surface method (RSM) was employed for further enhancing the succinic acid production and to monitor the interactive effect of these parameters, which resulted in a twofold increase in yield (14.3 g L(-1) in 48 h). The analysis of variance (ANOVA) showed the adequacy of the model and the verification experiments confirmed its validity. On subsequent scale-up in a 10-L bioreactor using conditions optimized through RSM, 24.2 g L(-1) of succinic acid was obtained in 30 h. This clearly indicated that the model stood valid even on large-scale. Thus, the statistical optimization strategy led to a 3.5-fold increase in the yield of succinic acid. This is the first report on the use of FCCCD to improve succinic acid production from E. coli.
Algorithms↗
[Effects of succinic acid on the function of in vitro cultured human fibroblasts].
OBJECTIVE: To explore the mechanism of injurious effect of succinic acid on human fibroblast and it's role in bacteroides fragilis infection. METHODS: In vitro cultured human fibroblasts were challenged by succinic acid in concentrations of 5, 10, 20 and 30 mmol/L (pH5.5), respectively. The cellular activity, apoptosis rate, the collagen synthesis in the supernatant of the cell culture, and the activity of caspase-3 were determined 24 hours after challenge. Isotonic saline challenged fibroblast were employed as control and the changes in the indices before and after succinic acid challenge were observed. RESULTS: Along with the increase in the concentration of succinic acid, the fibroblast proliferation rate was decreased and so was the collagen synthesis. But the apoptosis rate and caspase-3 activity were increased. The activity of caspase-3 was markedly higher than that in normal control when the succinic acid concentration was 10-30 mmol/L. The cellular activity and collagen synthesis were significantly lower and the apoptosis rate was obviously higher than those in control group when the succinic acid concentration was 20 or 30 mmol/L (P < 0.05). CONCLUSION: The proliferation and collagen synthesis in fibroblast culture could be significantly inhibited and the cellular apoptosis could be promoted by succinic acid. The process of wound healing of the wounds infected by bacteroides fragilis would be delayed due to the production of succinic acid by the bacteria.
Apoptosis↗
Inhibitory effects of succinic acid on chemical kindling and amygdala electrical kindling in rats.
AIM: To investigate the effects and mechanism of succinic acid on pentylenetetrazol (PTZ) chemical kindling and amygdala electrical kindling in rats. METHODS: PTZ chemical kindling and amygdala electrical kindling models were established in rats. The effects of succinic acid on the behavior and afterdischarge of kindled rats were observed. The mice were pretreated with succinic acid, 30 min later, picrotoxin, a GABAA receptor antagonist was given by ip, then the effects of succinic acid on mice were observed. RESULTS: Succinic acid (100-400 mg/kg, ip) dose-dependently inhibited PTZ chemical and amygdala kindled seizure (P<0.05, P<0.01), elevated the afterdischarge threshold, and reduced the Racine's stage of amygdala kindling rats (P<0.05, P<0.01); succinic acid (200-400 mg/kg, ip) inhibited picrotoxin-convulsion in mice (P<0.05, P<0.01). CONCLUSION: Succinic acid inhibits PTZ chemical and amygdala electrical kindling in rats, and the inhibition mechanism may be related to the enhancement of GABAergic system action in the brain, especially through GABAA receptors.
Amygdala↗
Comparison of growth and primary shunt product formation by Claviceps purpurea cultured on succinic acid and glucose as carbon sources.
Growth on a medium containing succinic acid as the sole carbon source produced 1 g (dry weight) of mycelium per liter of medium by 50 days of incubation, whereas 25 g of mycelium was produced in 10 days when glucose was also present in the medium. Primary shunt metabolism took place during growth on succinic acid in spite of the extremely slow growth. Mycelia grown on succinic acid contained a higher percentage of residual mycelium and phosphate, but a lower percentage of mannitol, carbohydrate, lipid, and water-soluble nitrogen, than mycelia grown on a mixture of glucose and succinic acid. Thus, although primary shunt metabolism is favored by rapid growth on a rich, balanced sugar medium, it can also take place during extremely restricted growth in a medium containing succinic acid as the sole carbon source.
Carbohydrate Metabolism↗
Hydrolysis of succinic acid dimethyl ester in rat pancreatic islets.
The hydrolysis of the dimethyl ester of [1,4-14C]succinic acid and/or [2,3-14C]succinic acid was measured in homogenates of rat pancreatic islets, liver, jejunum, brain, BC3H1 mouse myocytes, NG108-19 mouse neuroblastoma x rat glioma hybrid cells, and Caco-2 human colon adenocarcinoma cells. The specific activity of the enzyme was much higher in liver, jejunum, and Caco-2 cells than in the other cell types. The affinity of the enzyme for succinic acid dimethyl ester (SAD) was also much higher in liver than in islet homogenates. In the latter case, both particulate and cytosolic activity were observed upon subcellular fractionation. The activity found in islet homogenates was commensurate with the rate of SAD hydrolysis in intact cells. While the intracellular pool of acidic metabolites generated from SAD remained fairly stable over a 15- to 120-min incubation and was mainly located in the cytosolic compartment, the amount of acidic metabolites released in the extracellular milieu progressively increased with the length of incubation. Such metabolites included both monocarboxylic and dicarboxylic acids, the latter consisting mainly of succinic acid and, to a much lesser extent, of fumaric acid and malic acid. However, at variance with SAD, succinic acid failed to be taken up by intact islets. There was no close parallelism between the specific activity of the SAD esterase and the extent of SAD utilization in distinct cell types.
Animals↗
[Diabetes mellitus in the elderly: succinic acid compounds in treating diabetic neuropathies].
To investigate the influence of the succinic acid treatment on geriatric patients with type 2 diabetes. Succinic Acid has some positive biological properties. One of its is a neglecting of an aerobic glycolysis. In this study we evaluated the efficacy of the combination of the succinic acid ("MITOMIN") on treating of diabetic neuropathy of geriatric patients with type 2 diabetes. The analysis was carried out using 26 patients (aged 60-76 years). The duration of diabetes was 9.15 +/- 1.43 years. Biomedical parameters were measured by standard methods; microalbuminuria was measured by "Micral-Test". Quality of life (psychosocial disorders) was estimated with the help of "SANDOZ"-scale for geriatric assessment. The therapy was assigned 1.5 g of mitomin per day during a month. All patients were examined on having late diabetic complications: 7.69%--had diabetic retinopathy; 11.54%--diabetic nephropathy; 73.08%--diabetic neuropathy; 46.15%--chronic failure of brain vessels; 11.5%--macroangiopathy of lower extremities and 100%--had ischeamic heart disease of different levels. Mitomin therapy improved basal and postprandial glycemic control (NS), variance of pallesthesia (p < 0.001), parameters of quality of life, i.e. depression (p < 0.001), anxiety (p < 0.01), short memory (p < 0.05) and emotionality (p < 0.001). Mitomin therapy plays a positive role in management of elderly patients with type 2 diabetes. It improves glycemic control, pallestesia and quality of life. Combination of succinic acid renders central and peripheral neuropathy protective efficacy.
Aged↗
Succinic acid production from Bacteroides fragilis: process optimization and scale up in a bioreactor.
We report the effect of different physiological and nutritional parameters on succinic acid production from Bacteroides fragilis. This strain initially produced 0.70gL(-1) of succinic acid in 60h. However, when process optimization was employed, 5.4gL(-1) of succinic acid was produced in medium consisting of glucose (1.5%); tryptone (2.5%); Na(2)CO(3) (1.5%), at pH 7.0, when inoculated with 4% inoculum and incubated at 37 degrees C, 100rpm for 48h. A marked enhancement in succinic acid production was observed when the optimized conditions were employed in a 10L bioreactor. A total of 12.5gL(-1) of succinic acid was produced in 30h. This is approximately 12-fold increase in succinic acid production when compared to the initial un-optimized medium production. This enhancement in succinic acid production may be due to the control of CO(2) supply and the impeller speed. This is also resulted in the reduction of the production time. The present study provides useful information to the industrialists seeking environmentally benign technology for the production of bulk biomolecules through manipulation of various chemical parameters.
Anaerobiosis↗
In vivo stimulation of insulin release by succinic acid methyl esters.
Both the monomethyl and dimethyl esters of succinic acid, administered intravenously to fasted and anesthetized rats, caused a rapid increase in plasma insulin. A positive insulin secretory response to succinic acid monomethyl ester was also observed after intraperitoneal injection to fed and conscious rats. On a molar basis, stimulation of the insulin release, evoked by succinic acid esters, represented about twice that caused by D-glucose. It is speculated that succinic acid esters may be efficient insulin secretagogues even in those models of noninsulin-dependent diabetes characterized by a site-specific defect in the transport of D-glucose or in the early steps of its catabolism in the pancreatic B-cell.
Anesthesia↗
Enhanced production of succinic acid by overexpression of phosphoenolpyruvate carboxylase in Escherichia coli.
Fermentative production of succinic acid from glucose by Escherichia coli was significantly increased by overexpression of phosphoenolpyruvate carboxylase. In contrast, overexpression of phosphoenolpyruvate carboxykinase had no effect. Under optimized conditions, induction of the carboxylase resulted in a 3.5-fold increase in the concentration of succinic acid, making succinic acid the major fermentation product by weight.
Escherichia coli↗
Improved viability and metabolic behavior of hepatocytes after liver storage in the presence of a succinic acid ester.
BACKGROUND: Selected esters of succinic acid were recently proposed as novel nutrients to support ATP generation in cells endangered by an imbalance between the formation and breakdown of this adenine nucleotide. In the present study, a new ester, glycerol-1,2,3-trimethylsuccinate, was examined for its potential beneficial effect in the procedures preceding liver transplantation. METHODS: The viability and metabolic behavior of hepatocytes were examined after perfusion and storage of rat livers for 20 hr at 4 degrees C with a Belzer UW-CSS solution in the absence or presence or 2 mM glycerol-1,2,3-trimethylsuccinate. RESULTS: Although it failed to affect significantly the release of cellular enzymes during storage and the protein or glycogen content of the liver, and was unable to prevent the storage-induced decrease in both biosynthetic activity and D-[U-14C]glucose incorporation into glycogen in isolated hepatocytes, the ester restored to a close-to-normal value the viability of the hepatocytes and opposed the starvation-like effects of liver storage upon both the conversion of D-[U-14C]glucose to 14CO2 and radioactive amino acids and the de novo generation of 14C-labeled D-glucose from [2-14C]pyruvate. CONCLUSIONS: Because succinic acid esters are efficiently metabolized in several cell types, the present results suggest that such esters may have a wide field of application in transplantation procedures.
Animals↗
Lactic and succinic acid formation by Endamoeba histolytica in vitro.
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Entamoeba histolytica↗
Synthesis of ureido[14C] succinic acid and orotic[2-14C] acid from urea [14C].
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Orotic Acid↗
Comparative pharmacological study of the mono and dicholine esters of succinic acid.
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Choline↗