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PubMed2002

Isolation and characterization of a new succinic acid-producing bacterium, Mannheimia succiniciproducensMBEL55E, from bovine rumen.

A novel succinic acid-producing bacterium was isolated from bovine rumen. The bacterium is a non-motile, non-spore-forming, mesophilic and capnophilic gram-negative rod or coccobacillus. Phylogenetic analysis based on the 16S rRNA sequence and physiological analysis indicated that the strain belongs to the recently reclassified genus Mannheimia as a novel species, and has been named Mannheimia succiniciproducens MBEL55E. Under 100% CO(2) conditions, it grows well in the pH range of 6.0-7.5 and produces succinic acid, acetic acid and formic acid at a constant ratio of 2:1:1. When M. succiniciproducensMBEL55E was cultured anaerobically in medium containing 20 g l(-1) glucose as carbon source, 13.5 g l(-1) of succinic acid was produced.

Acetic Acid↗

PubMed1987

Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation.

In addition to the previously reported abnormalities, urine extracts from three cases of succinic semialdehyde dehydrogenase deficiency have shown consistently increased amounts of 2,4-dihydroxybutyric acid, and its lactone, and 3-hydroxypropionic acid, metabolites related to the alpha-oxidation of 4-hydroxybutyric acid. Threo- and erythro-4,5-dihydroxyhexanoic acids have also been identified for the first time and probably arise from the reaction of succinic semialdehyde with an intermediate in the pyruvate dehydrogenase pathway. Adipic acid excretion is also consistently raised, suggesting secondary interference with mitochondrial beta-oxidation. The presence of these metabolites could be a source of diagnostic confusion.

Adipates↗

PubMed2006

Effects of the tomato pathogen Fusarium oxysporum f. sp. radicis-lycopersici and of the biocontrol bacterium Pseudomonas fluorescens WCS365 on the composition of organic acids and sugars in tomato root exudate.

The effects of the pathogenic fungus Fusarium oxysporum f. sp. radicis-lycopersici and of the bacterial biocontrol strain Pseudomonas fluorescens WCS365, and of both microbes, on the amounts and composition of root exudate components of tomato plants grown in a gnotobiotic stonewool substrate system were studied. Conditions were selected under which introduction of F. oxysporum f. sp. radicis-lycopersici caused severe foot and root rot, whereas inoculation of the seed with P. fluorescens WCS365 decreased the percentage of diseased plants from 96 to 7%. This is a much better disease control level than was observed in potting soil. Analysis of root exudate revealed that the presence of F. oxysporum f. sp. radicis-lycopersici did not alter the total amount of organic acids, but that the amount of citric acid decreased and that of succinic acid increased compared with the nontreated control. In contrast, in the presence of the P. fluorescens biocontrol strain WCS365, the total amount of organic acid increased, mainly due to a strong increase of the amount of citric acid, whereas the amount of succinic acid decreased dramatically. Under biocontrol conditions, when both microbes are present, the content of succinic acid decreased and the level of citric acid was similar to that in the nontreated control. The amount of sugar was approximately half that of the control sample when either one of the microbes was present alone or when both were present. Analysis of the interactions between the two microbes grown together in sterile tomato root exudate showed that WCS365 inhibited multiplication of F. oxysporum f. sp. radicis-lycopersici, whereas the fungus did not affect the number of CFU of the bacterium.

Carbohydrate Metabolism↗

PubMed1987

Short-chain fatty acids and succinate in feces of healthy human volunteers and their correlation with anaerobe cultural counts.

Short-chain fatty acids (SCFA) and succinate in fresh feces from 10 healthy human volunteers were detected with gas-liquid chromatography and were correlated with their fecal cultural counts. The SCFA content of feces did not change significantly after freezing, but the cultural counts of total anaerobes and bifidobacteria showed significant changes (0.001 less than P less than 0.01). A significant negative correlation (r = -0.78; 0.01 less than P less than 0.02) was found between the bifidobacteria cultural counts and the succinic acid concentration in fresh feces, which disappeared after freezing of the samples. Because of the significant differences in cultural counts and the shift in significant correlations after freezing, it is important to use fresh fecal samples for these correlation studies. Lactic acid and i-caproic acid were not found in the fecal samples. The results show that SCFA and organic acid concentrations cannot replace (an)aerobe cultural counts in fecal flora studies of healthy human volunteers because of the low rate of significant correlations between these two.

Adult↗

PubMed1998

Hydroxypropyl-modified potato starch increases fecal bile acid excretion in rats.

The effects of hydroxypropyl potato starches (HPS) of three different degrees of substitution (DS) on concentration of plasma cholesterol, apparent digestibility of protein, fecal excretion of bile acids, fecal output and cecal pool of organic acids such as acetic, propionic, butyric, lactic and succinic acid were studied in rats in Experiment 1. In Experiment 2, the effects of hydroxypropyl distarch phosphate (HDP) of three different degrees of cross-linking (DC) on the same indexes were studied. Gelatinized potato starch that was not modified chemically (PS) was used as a control. Rats were fed a fiber-free, purified diet containing either HPS, HDP or PS (100 g/kg) for 21 d. In each experiment, fecal output was greater and fecal excretion of bile acids was higher in rats fed the HPS diets with higher DS and the HDP diets compared with control rats fed the PS diet. Apparent protein digestibility in rats fed the HPS diets with higher DS and the HDP diets with higher DC was lower than that in control rats fed the PS diet. The pool size of cecal organic acids was not affected by diet. In Experiment 1, apparent protein digestibility, fecal output and fecal bile acids excretion were significantly correlated with DS (r = -0.994, P = 0.0059; r = 0.976, P = 0.0236; and r = 0.899, P = 0.0077, respectively). The plasma cholesterol concentration was significantly lower in rats fed the HPS diets than in control rats fed the PS diet. The HPS diets resulted in higher proportions of propionic acid, lactic acid and succinic acid and a lower proportion of n-butyric acid than the PS diet. In Experiment 2, apparent protein digestibility was significantly correlated with DSP (r = 0.996, P = 0.0028), which was inversely related to DC. The HDP diets did not affect the plasma cholesterol concentration. The HDP diets resulted in higher proportions of acetic acid, lactic acid and succinic acid and a lower proportion of n-butyric acid than the PS diet. These results suggest that the physiological effects of chemically modified starches are affected by the type of modification.

Animals↗

PubMed2001

[Studies on chemical constituents of mycelium of fungus Cephalosporium sp. AL031(I)].

Five compounds were isolated from the mycelium of the fungus Cephalosporium sp. AL031 whose metabolites have been proven to possess antifungal and antibacterial activities. Based on the spectral data and elemental analysis, they were identified as ergosterol(I), 2,4,6-octatrienoic acid(II), succinic acid(III), uracil(IV), and D-mannitol(V). All of these compounds were obtained from the culture of this fungus for the first time.

Acremonium↗

PubMed1987

Biomphalaria glabrata: respiration, calcium and end products of carbohydrate metabolism.

1. Lactic acid and succinic acid (end products of anaerobiosis) also occur under aerobic conditions in the haemolymph and excretion products of Biomphalaria glabrata. This phenomenon has been investigated in more detail. 2. Experiments on oxygen uptake, and analyses of organic acid, amino acid and calcium were carried out under various aerating conditions, various temperatures and in various water qualities. 3. No differences were found in the concentrations of the organic acids and calcium in the haemolymph under different aerating conditions. 4. Neither snail-conditioned water, nor artificial crowding effects played a role in the initiation of anaerobic respiration. 5. A low exposure temperature (4 degrees C) initiated anaerobic respiration in spite of the aeration.

Aerobiosis↗

PubMed1990

[Studies of the chemical constituents of Ardisia pusilla A. DC].

Six chemical compounds isolated from the leaves and stems of Ardisia pusilla were identified as gallic acid (I), succinic acid (II), naringenin-6-C-glucoside (III), kaempferol-3-O-beta-D-galactoside (IV) by chemical and spectroscopic analysis. They were isolated from Ardisia plant for the first time.

Drugs, Chinese Herbal↗

PubMed2000

Anaerobic degradation of 2-methylnaphthalene by a sulfate-reducing enrichment culture.

Anaerobic degradation of 2-methylnaphthalene was investigated with a sulfate-reducing enrichment culture. Metabolite analyses revealed two groups of degradation products. The first group comprised two succinic acid adducts which were identified as naphthyl-2-methyl-succinic acid and naphthyl-2-methylene-succinic acid by comparison with chemically synthesized reference compounds. Naphthyl-2-methyl-succinic acid accumulated to 0.5 microM in culture supernatants. Production of naphthyl-2-methyl-succinic acid was analyzed in enzyme assays with dense cell suspensions. The conversion of 2-methylnaphthalene to naphthyl-2-methyl-succinic acid was detected at a specific activity of 0.020 +/- 0.003 nmol min(-1) mg of protein(-1) only in the presence of cells and fumarate. We conclude that under anaerobic conditions 2-methylnaphthalene is activated by fumarate addition to the methyl group, as is the case in anaerobic toluene degradation. The second group of metabolites comprised 2-naphthoic acid and reduced 2-naphthoic acid derivatives, including 5,6,7,8-tetrahydro-2-naphthoic acid, octahydro-2-naphthoic acid, and decahydro-2-naphthoic acid. These compounds were also identified in an earlier study as products of anaerobic naphthalene degradation with the same enrichment culture. A pathway for anaerobic degradation of 2-methylnaphthalene analogous to that for anaerobic toluene degradation is proposed.

Anaerobiosis↗

PubMed2005

Combined efficacies of DL-alpha-lipoic acid and meso 2,3 dimercaptosuccinic acid against arsenic induced toxicity in antioxidant systems of rats.

Health hazards caused by heavy metals have become a great concern to the population. Arsenic as an environmental agent is considered to be a toxic substance due to its carcinogenic potential in humans. Since arsenic compounds might exert their toxicity by the generation of reactive oxygen species, we have evaluated the effect of both DL-alpha-lipoic acid (LA) and meso 2,3 dimercapto succinic acid (DMSA) on the antioxidants and lipid peroxidation in arsenic treated rats. The objective of the study was to determine whether DL-alpha-lipoic acid and meso 2,3 dimercapto succinic acid could rehabitate antioxidant depletion and damage to biomolecules in protection against oxidative insults. A significant increase in the levels of reactive oxygen species formation and lipid peroxidation and decrease in the activities of antioxidant enzymes were observed in arsenic exposed rats. Supplementation of DL-alpha-lipoic acid and meso 2,3 dimercapto succinic acid to arsenic fed rats significantly increased the activities of superoxide dismutase, catalase, glutathione peroxidase with elevation in the levels of reduced glutathione, total sulfhydryl, ascorbic acid and alpha-tocopherol. In addition, significant decrease in the levels of reactive oxygen species formation and lipid peroxidation was also observed in our study. From our results, we conclude that DL-alpha-lipoic acid and meso 2,3 dimercapto succinic acid play a synergistic role in decreasing arsenic induced oxidative damage by elevating the antioxidant status in liver and kidney.

Animals↗

PubMed2004

Crystal engineering approach to forming cocrystals of amine hydrochlorides with organic acids. Molecular complexes of fluoxetine hydrochloride with benzoic, succinic, and fumaric acids.

A crystal engineering strategy for designing cocrystals of pharmaceuticals is presented. The strategy increases the probability of discovering useful cocrystals and decreases the number of experiments that are needed by selecting API:guest combinations that have the greatest potential of forming energetically and structurally robust interactions. Our approach involves multicomponent cocrystallization of hydrochloride salts, wherein strong hydrogen bond donors are introduced to interact with chloride ions that are underutilized as hydrogen bond acceptors. The strategy is particularly effective in producing cocrystals of amine hydrochlorides with neutral organic acid guests. As an example of the approach, we report the discovery of three cocrystals containing fluoxetine hydrochloride (1), which is the active ingredient in the popular antidepressant Prozac. A 1:1 cocrystal was prepared with 1 and benzoic acid (2), while succinic acid and fumaric acid were each cocrystallized with 1 to provide 2:1 cocrystals of fluoxetine hydrochloride:succinic acid (3) and fluoxetine hydrochloride:fumaric acid (4). The presence of a guest molecule along with fluoxetine hydrochloride in the same crystal structure results in a solid phase with altered physical properties when compared to the known crystalline form of fluoxetine hydrochloride. On the basis of intrinsic dissolution rate experiments, cocrystals 2 and 4 dissolve more slowly than 1, and 3 dissolves more quickly than 1. Powder dissolution experiments demonstrated that the solid present at equilibrium corresponds to the cocrystal for 2 and 4, while 3 completely converted to 1 upon prolonged slurry in water.

Benzoic Acid↗

PubMed1998

The pH-independent release of fenoldopam from pellets with insoluble film coats.

Various ratios of succinic acid to fenoldopam mesylate, ranging from 0:1 to 18:1 were incorporated in pellets and coated with 1.5-12% w/w Surelease. Even though the coating level did influence the rate and amount of fenoldopam release, the influence of the succinic acid to drug ratio was much more important and evident at all coating levels. Being a weakly basic drug, fenoldopam release ceased when testing in SIF for succinic acid to drug ratios of 0:1-4:1, with the end of release being more abrupt for the 0:1 than for the 4:1 ratio. Only for a succinic acid to drug ratio of > or =5 was fenoldopam release constant for 6-8 h and independent of the pH-value of dissolution media. For a thin coat of about 2.5% w/w Surelease, those pellets showed an ideal controlled release behaviour with release rates of about 5-10%/h and a total release of almost 80% in 8 h. The dissolution profiles of Surelease coated pellets with high succinic acid to drug ratios (> or =5) and different coating levels, were evaluated for best fits to commonly used kinetic models. Sustained release mechanisms are discussed according to best fit models. The quantification of the pH-adjuster succinic acid, released from pellets with an acid to drug ratio of < or =1 showed, that despite their failure as a controlled release system for fenoldopam, the investigated coats could control the release of succinic acid effectively at optimized coating levels. For increasing succinic acid to drug ratios (< or =4) succinic acid was released at an ever more constant rate and release rates, though still faster than the release rates of fenoldopam, decreased steadily for increasing ratios. At a 5:1 ratio finally release rates of succinic acid and fenoldopam were almost identical. Therefore those pellet cores were almost completely emptied during dissolution testing, with both fenoldopam and succinic acid leaving at a constant rate and a total release of about 80% each for a 2.5% Surelease coat, while lower succinic acid to drug ratios had failed to show any sustained release for such thin Surelease coats. A similar formulation with fumaric acid instead of succinic acid failed to show the desired release pattern, indicating that it is the presence of a sufficiently high amount of succinic acid rather than the presence of an acidic compound in general, that ensures fenoldopam solubility at higher pH-values.

Chemistry, Pharmaceutical↗

PubMed1992

Nutritional interactions between two suspected periodontopathogens, Treponema denticola and Porphyromonas gingivalis.

A mutual symbiotic enhancement of growth of Porphyromonas gingivalis and Treponema denticola is described in this report. Brain heart infusion broth supplemented with vitamin K did not support the individual growth of P. gingivalis or T. denticola. However, when inoculated as a mixture, both bacterial species did grow significantly. The growth-stimulating factors produced by P. gingivalis and T. denticola were dialyzable and heat stable and were further identified as isobutyric acid and succinic acid, respectively. Since some forms of periodontal disease are associated with the presence, in affected sites, of high numbers of P. gingivalis and spirochetes, it is suggested that the bacterial interaction described in this report might be of utmost importance in the initiation and progression of the disease.

Butyrates↗

PubMed2005

Synthesis and aqueous aggregation properties of amphiphilic surface-block dendrimers.

[reaction: see text] A family of dendritic amphiphiles were synthesized from the natural metabolites of glycerol, succinic acid, and myristic acid. The surfaces of these dendrimers display different numbers of alkyl chains and carboxylic acids, varying the hydrophobic-to-hydrophilic ratio over a relatively broad range. In solution these dendritic amphiphiles form supramolecular structures, and these aggregates have been characterized by light microscopy, transmission electron microscopy, and tensiometry. These aggregates can entrap the hydrophobic species pyrene.

Dendrimers↗

PubMed2005

X-ray studies on crystalline complexes involving amino acids and peptides. XLII. Adipic acid complexes of L- and DL-arginine and supramolecular association in arginine-dicarboxylic acid complexes.

The adipic acid complexes of DL-arginine and L-arginine are made up of zwitterionic, singularly positively charged arginium ions and doubly negatively charged adipate ions, with a 2:1 stoichiometry. One of the two crystallographically independent arginium ions in the L-arginine complex has a conformation hitherto unobserved in crystal structures containing the amino acid. In the present study the structural data on arginine complexes of saturated dicarboxylic acids with 0-5 C atoms separating the two carboxyl functions are given. In terms of molecular aggregation, formic and acetic acid complexes behave in a similar way to those involving fairly long carboxylic acids such as adipic acid. By and large, the supramolecular assembly in complexes involving dicarboxylic acids with 3 or more C atoms separating the carboxyl groups (glutaric, adipic and pimelic acids), and those involving formic and acetic acids, have common features. The aggregation patterns in complexes involving oxalic, malonic and maleic acids do not share striking features among themselves (except for the mode of hydrogen-bonded dimerization of arginium ions) or with those involving larger dicarboxylic acids. Complexes of succinic acid, the shortest linear dicarboxylic acid, share features with those involving shorter as well as longer dicarboxylic acids. The difference in the behaviour of long and short dicarboxylic acids and the ambiguous behaviour of succinic acid can be broadly related to their lengths.

Adipates↗

PubMed1999

Inhibition and stimulation of long-chain fatty acid oxidation by chloroacetaldehyde and methylene blue in rats.

The effects of chloroacetaldehyde (CAA) and methylene blue, both alone and together, on mitochondrial metabolism, hepatic glutathione content, and bile flow were investigated in rats. Oxidation of [1-14C]palmitic acid, [1-14C]octanoic acid, and [1,4-14C]succinic acid allowed for the differentiation between carnitine-dependent long-chain fatty acid metabolism, medium chain fatty acid oxidation, and citric acid cycle activity, respectively. CAA, a metabolite of the anticancer drug ifosfamide, which may be responsible for ifosfamide-induced encephalopathy, inhibited palmitic acid metabolism but not octanoic or succinic acid oxidation, depleted hepatic glutathione, and stimulated bile flow. Methylene blue, which is clinically used to either prevent or reverse ifosfamide-associated encephalopathy, markedly stimulated palmitic acid oxidation either in the presence or absence of CAA, but did not affect the oxidation of octanoic and succinic acid or hepatic glutathione. Taken together, this study demonstrates that CAA inhibits palmitic acid metabolism. Methylene blue stimulates long-chain fatty acid oxidation, most likely by facilitating the translocation of fatty acids into mitochondria, and compensates for the CAA effect in vivo.

Acetaldehyde↗

PubMed2005

Characterization of organic compounds collected during southeastern aerosol and visibility study: water-soluble organic species.

As part of the Southeastern Aerosol and Visibility Study (SEAVS), water-soluble organic species (WSOS) in fine aerosols collected from July 15 to August 25, 1995, at the Great Smoky Mountain National Park, Tennessee (USA), were chemically classified into seven groups, with concentrations ranging from around 1 to >200 ng/m3. Dicarboxylic acids represented the dominant identified compound class, and succinic acid was the most abundant dicarboxylic acid. The trends in data suggest that most WSOS collected in the SEAVS samples were mainly generated from secondary photochemical reactions, especially during the first (cleaner) half of the sampling campaign. High relative humidity at the sampling site resulted in substantial water uptake by the aerosols, which may have enhanced the levels of succinic acid by reducing its rate of photooxidation. Concurrent trends in malic and malonic acid concentrations suggest these were generated from the oxidation of succinic acid. Consistent with the conversion of 3-hydroxypropanoic acid to malonic acid, it appears that 4-hydroxybutanoic acid served as a major precursor contributing to high levels of succinic acid in the daytime. Nocturnal WSOS generally followed the trend of diurnal WSOS, but they exhibited different chemical compositions and lower concentrations, unlike what has been reported for an urban site. A nocturnal-to-diurnal ratio of succinic acid larger than 0.25 may indicate an atmosphere dominated by photochemical reactions, rather than by primary emissions.

Aerosols↗

PubMed2002

Determination of malic acid and other C4 dicarboxylic acids in atmospheric aerosol samples.

An ion chromatographic method was developed which is able to separate five unsubstituted and hydroxy C4 dicarboxylic acids, succinic, malic, tartaric, maleic and fumaric acid, besides the other unsubstituted C2-C5 dicarboxylic acids, oxalic, malonic and glutaric acids, as well as inorganic ions in samples extracted from atmospheric particulate matter. By the application of this method it was found for both rural and urban sites and for various types of air masses that in the summer-time malic acid is the most prominent C4 diacid (64 ng m(-3) by average), exceeding succinic acid concentration (28 ng m(-3) by average) considerably. In winter-time considerably less, a factor of 4-15, C4 acids occurred and succinic acid was more concentrated than malic acid. Tartaric, fumaric and maleic acids were less concentrated (5.1, 5.0 and 4.5 ng m(-3) by average, respectively). Tartaric acid was observed for the first time in ambient air. The results indicate that in particular anthropogenic sources are important for the precursors of succinic, maleic and fumaric acids. Biogenic sources seem to influence the occurrence of malic acid significantly.

Aerosols↗