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PubMed1990

A simple plate-assay for the screening of L-malic acid producing microorganisms.

A simple plate-assay has been developed to screen microorganisms for L-malic acid production. Acid producing organisms were identified, after microbial colony growth on media containing glucose or fumaric acid as sole carbons sources, by formation of a dark halo of formazan. The halo was observed when the plate was covered with a soft agar overlay containing NAD(+)-malate dehydrogenase, NAD+, phenazine methosulfate (PMS) and 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT). The assay developed is simple, specific for L-malic acid and therefore can be used to identify L-malic acid producing filamentous fungi using glucose as carbon source (e.g. Aspergillus strains). The assay is also applicable for screening bacteria with high fumarase activity, able to convert fumaric acid to L-malic acid.

Aspergillus↗

PubMed2000

Heat inactivation of Escherichia coli O157:H7 in apple cider containing malic acid, sodium benzoate, and potassium sorbate.

The effect of pH modification and preservative addition in apple cider on the heat resistance of Escherichia coli O157:H7 was investigated. E. coli O157:H7 and various amounts of potassium sorbate (0 to 0.2%), sodium benzoate (0 to 0.2%), and malic acid (0 to 1%) were added to apple cider. Thermal inactivation experiments were performed at 47, 50, and 53 degrees C, and D- and z-values were calculated. In apple cider without additives, the D-value at 50 degrees C (D50) was about 65 min, but addition of preservatives and malic acid significantly (P < 0.01) decreased D-values. D50-values decreased to 13.9 min in cider with 0.5% malic acid, 13.2 min with 0.1% sorbate, and 7.0 min with 0.1% benzoate added. Addition of both sorbate and malic acid had similar effects as either one alone, thus additive effects were not present. However, addition of both 0.2% benzoate and 1% malic acid did show additive effects, lowering D50 to 0.3 min. Addition of all three components (0.2% sorbate, 0.2% benzoate, and 1% malic acid) resulted in a D50 = 18 s. The z-value of cider without additives was about 6 degrees C, whereas z-values of cider containing malic acid, benzoate, and/or sorbate ranged from about 6 degrees C to 26 degrees C. This increase may result in a longer 5-log reduction time at higher temperatures (i.e., 70 degrees C) in cider with benzoate as compared to cider without additives.

Animals↗

PubMed1987

L-malic-acid permeation in resting cells of anaerobically grown Saccharomyces cerevisiae.

The study of permeation of L-malic acid in cells of Saccharomyces cerevisiae at pH 3.0 was carried out with (U-14C)-labelled L-malic acid. Resting cells were used in these experiments. They were previously anaerobically grown on glucose. This study showed that this transport is the result of two competitive mechanisms, one for the uptake and one for the efflux. The uptake mechanism seems to be a simple diffusion of the L-malic acid in a non-dissociated form. The efflux mechanism seems to be an active transport of L-malic acid that is very dependent on the temperature. At the steady state, the result of uptake and efflux mechanisms leads to an intracellular concentration which is twice or three times the extracellular concentration.

2,4-Dinitrophenol↗

PubMed1998

Production of L-malic acid via biocatalysis employing wild-type and respiratory-deficient yeasts.

The yeast Saccharomyces cerevisiae has been used to efficiently produce L-malic acid from fumaric acid. Fumarase is responsible for the reversible conversion of fumaric and L-malic acids in the TCA cycle. To investigate the function of mitochondrial and cytoplasmic fumarase isoenzymes in L-malic acid bioconversion, a wild-type strain and a cytoplasmic respiratory-deficient mutant devoid of functional mitochondria were employed. The mutant strain, which only contained the cytoplasmic fumarase, was still functional in fumaric acid to L-malic acid bioconversion However, its specific conversion rate was much lower (0.20 g/g.h) than that of the wild-type strain (0.55 g/g.h).

Catalysis↗

PubMed1996

[Anti-inflammatory effect of Urtica dioica folia extract in comparison to caffeic malic acid].

Urtica dioica extract is a traditionary used adjuvant therapeutic in rheumatoid arthritis. The antiphlogistic effects of the urtica dioica folia extract IDS 23 (Extractum Urticae dioicae foliorum) and the main phenolic ingredient caffeic malic acid were tested concerning the inhibitory potential on biosynthesis of arachidonic acid metabolites in vitro. The caffeic malic acid was isolated from Urtica folia extract using gel exclusion- and high performance liquid chromatography and identified by mass spectroscopy and nuclear magnetic resonance. Concerning the 5-lipoxygenase products IDS 23 showed a partial inhibitory effect. The isolated phenolic acid inhibited the synthesis of the leukotriene B4 in a concentration dependent manner. The concentration for halfmaximal inhibition (IC50) was 83 microns/ml in the used assay. IDS 23 showed a strong concentration dependent inhibition of the synthesis of cyclooxygenase derived reactions. The IC50 were 92 micrograms/ml for IDS 23 and 38 micrograms/ml for the caffeic malic acid. Calculating the content in IDS 23 the caffeic malic acid is a possible but not the only active ingredient of the plant extract in the tested assay systems. It is demonstrated that the phenolic component showed a different enzymatic target compared with IDS 23. The antiphlogistic effects observed in vitro may give an explanation for the pharmacological and clinical effects of IDS 23 in therapie of rheumatoid diseases.

Animals↗

PubMed1967

The effect of illumination of the malic acid content and anion/cation balance of mustard leaves (Sinapis alba).

1. Mustard plants have been grown under conditions in which the length of artificial day could be controlled. 2. Leaf samples were analysed for malic acid and citric acid, and for a number of inorganic anions and cations. A simple method is described by which sap was obtained from 0.5g. samples of leaves. 3. In days of 16hr. or more, malic acid was accumulated; the chief cation accumulated was calcium. 4. When the day-length was reduced the malic acid content decreased considerably but the calcium content remained the same. There was little change in the pH value of the sap, the balance of anions and cations having been maintained mainly by increases in citrate and nitrate contents. Analyses of the whole leaf still showed some deficiency in anion after sodium, potassium, calcium, magnesium, nitrate, sulphate, inorganic phosphate, chloride, malate and citrate had been accounted for. 5. Analyses at shorter intervals revealed a large diurnal variation in malic acid content, which increased during the first 5-6hr. of the light period, and fell during darkness. 6. The significance of these findings is discussed, and it is suggested that malic acid accumulation is a by-product of photosynthesis, calcium being taken up irreversibly to maintain anion/cation balance, and hence creating a continuing need for anions to balance it.

Calcium↗

PubMed2001

Enantioselective synthesis of (-)-wikstromol using a new approach via malic acid.

The total synthesis of (-)-wikstromol, a bioactive alpha-hydroxylated lactone lignan, from natural malic acid using a consecutive alkylation strategy is presented. First, alkylation of a malic acid ester provided the monobenzyl derivative, which was then converted to an alpha-substituted dioxolanone. This derivative was reacted in a second alkylation step to a double benzylated dioxolanone, which was transformed to bis-O-benzyl-protected (-)-wikstromol and subsequently to the natural product. Only six steps were required to produce wikstromol in 30% overall yield. A second approach from malic acid, the double alkylation of dienolates from 5-oxo-1,3-dioxolan-4-yl acetic acid derivatives, was not successful. No reaction conditions were found to afford the dienolates. Instead, rapid fragmentation of the dioxolanones to fumaric acid derivatives and pivalaldehyde occurred even at -105 degrees C, and aldol reaction products with good stereoselectivity were formed. The relative configuration of the major isomer was determined by X-ray structure analysis. By comparison of NMR data it is shown that a previous assignment of the configuration of one of the described aldol products was incorrect.

Alkylation↗

PubMed2003

Effect of feeding supplemental fibrolytic enzymes or soluble sugars with malic acid on milk production.

Two trials were conducted to evaluate effects of feeding supplemental fibrolytic enzymes or soluble sugars and malic acid on milk production. In trial 1, 257 cows at four sites were fed a basal diet consisting of no more than 60% of forage DM as corn silage and less than 40% as alfalfa hay. Cows were assigned randomly within site, parity, and two stages of lactation to: 1) control; 2) enzyme A; 3) enzyme B; and 4) soluble sugars and malic acid. There was a 14-d pretreatment and an 84-d treatment period. Enzyme solutions were sprayed on either the forage component or the TMR each day while mixing feed. Trial 2 was similar, except 122 cows at one site in the United Kingdom were fed diets containing forage that was 75% corn silage and 25% grass silage, and all cows began the study between 25 to 31 DIM. Mean milk productions for 233 cows that completed trial 1 were 32.9, 32.5, 32.4, and 32.9 kg/d for control, enzyme A, enzyme B, and soluble sugars and malic acid, respectively. Mean milk productions for 116 cows that completed trial 2 were 28.2, 27.9, 28.8, and 28.4 kg/d, respectively. In vitro analyses of the activities of enzyme solutions indicated that all major cellulose and hemicellulose degrading activities were present; however, the pH optima (approximate pH = 4 to 5) were more acidic, and the temperature optimum (approximately 50 degrees C) was greater than normal pH and temperature in the rumen. If fibrolytic activity in the rumen is a major mechanism of action of supplemental fibrolytic enzymes, it appears that considerable activity of these preparations was lost due to conditions in the rumen. In conclusion, feeding supplemental fibrolytic enzymes or malic acid with soluble sugars had no effect on milk production under the conditions used in this study.

Animal Nutritional Physiological Phenomena↗

PubMed2000

Effects of complexation between liposome and poly(malic acid) on aggregation and leakage behaviour.

The design and development of novel pH-sensitive liposomes were investigated to improve the release of liposome-encapsulated chemicals. Stable liposomes comprising of L-alpha-dipalmitoylphosphatidylcholine (DPPC) and poly(carboxylic acid) were prepared and characterized. Poly(malic acid) (PMLA) was chosen as a fusogen, because of its excellent biodegradability in physiological regions. Octyl groups introduced in the poly(malic acid) worked as anchors at the surface of the liposomes and made a remarkable contribution to complexing. The interaction between the liposomes and the polyacids was studied in terms of the change in size of the liposomes. The influences of molecular weight and amounts of polymer upon their characteristics, especially fusion, were discussed. The influences of pH change with respect to the association behavior of the liposomes such as aggregation and fusion were estimated by the particle size of the liposomes, turbidimetry of the solution and resonance energy transfer assay. From the results of these studies, it was shown that more tightly complexed liposomes aggregated and fused more positively with increasing acidity of the solution. The leakage of calcein entrapped in the inner aqueous phase of the liposomes increased with decreasing pH. The effect of pH on the liposome aggregation in a solution qualitatively paralleled that found in the leakage behavior.

Drug Carriers↗

PubMed1999

Influence of malic acid supplementation on ruminal pH, lactic acid utilization, and digestive function in steers fed high-concentrate finishing diets.

Two trials were conducted to evaluate the influence of malic acid supplementation on ruminal fermentation. In Trial 1, six Holstein steers (300 kg) with ruminal cannulas were used in a crossover design experiment to study the influence of malic acid (MA) on ruminal metabolism during glucose-induced lactic acidosis. Treatments consisted of a 77% steam-flaked barley-based finishing diet supplemented to provide 0 or 80 g/d of MA. After a 13-d dietary adjustment period, 1 kg of glucose was infused into the rumen 1 h after the morning feeding. Ruminal pH was closely associated (R2 = .70) with ruminal DL-lactate concentration. Malic acid supplementation increased (P < .01) ruminal pH 3 h after the glucose infusion. However, there were no treatment effects (P > .10) on ruminal VFA molar proportions or ruminal and plasma DL-lactate concentrations. In Trial 2, four Holstein steers (150 kg) with cannulas in the rumen and proximal duodenum were used in a crossover design experiment to evaluate the influence of MA supplementation on characteristics of digestion. Treatments consisted of an 81% steam-flaked barley-based finishing diet supplemented to provide 0 or 80 g/d of MA. There were no treatment effects (P > .10) on ruminal and total tract digestion of OM, ADF, starch, and feed N or on ruminal microbial efficiency. Malic acid supplementation increased (P < .05) ruminal pH 2 h after feeding. As with Trial 1, there were no treatment effects (P > .10) on ruminal VFA and DL-lactate concentrations. We conclude that supplementation of high-grain finishing diets with MA may be beneficial in promoting a higher ruminal pH during periods of peak acid production without detrimental effects on ruminal microbial efficiency or starch, fiber, and protein digestion. There were no detectable beneficial effects of MA supplementation on ruminal and plasma lactic acid concentrations in cattle fed high-grain diets.

Animal Feed↗

PubMed1999

Isolation of poly(beta-L-malic acid)-degrading bacteria and purification and characterization of the PMA hydrolase from Comamonas acidovorans strain 7789.

Several bacteria were isolated which were able to utilize poly(beta-L-malic acid) as sole carbon source for growth. The poly(beta-L-malic acid) hydrolyzing enzyme of Comamonas acidovorans strain 7789 was detected in the membrane fraction. The enzyme was purified by isolation of crude cell membranes by ultracentrifugation of disrupted cells, solubilization of the membrane fraction with octylglucoside, selective precipitation with 50% saturated ammonium sulfate and preparative isolectric focusing. SDS-PAGE analysis revealed a M(r) of 43,000. The pH optimum was 8.1 and the Km was 0.13 microM (in terms of monomeric units) and 0.0021 microM poly(beta-L-malic acid) at pH 8.1 (100 mM glycylglycine buffer). Addition of NaCl, KCl, CaCl2 or MgCl2 (from 25 to 100 mM) decreased the hydrolase activity, whereas EDTA or polymethane sulfonic acid fluoride had no influence on the enzyme. The depolymerization of poly(beta-L-malic acid) proceeded from the ends of the polyester resulting in the formation of L-malate. Esterase activity was not detectable with p-nitrophenyl acetate or p-nitrophenyl butyrate, which is used to determine for example poly(3-hydroxybutyric acid) depolymerase activity.

Biodegradation, Environmental↗

PubMedDate not supplied

Determination of D-malic acid in apple juice by liquid chromatography: collaborative study.

Eleven laboratories collaboratively studied a liquid chromatographic (LC) method for determination of D-malic acid in apple juice. The mobile phase consisted of mM L-valine and 8 mM copper acetate adjusted to pH 5.5 with NaOH. The UV detector was set at 330 nm, and a single reversed-phase LC column was used. Seven paired samples containing various amounts of D-malic acid ranging from 0 to 188 mg/100 mL of 12 Brix pasteurized apple juice were tested by each collaborator. Repeatability and reproducibility coefficients of variation ranged from 1.0 to 3.5% and 7.7 to 11.7%, respectively, within the range of 26 to 188 mg D-malic acid/100 mL of 12 Brix apple juice. The collaborative study results demonstrated that the method could quantitate the economic adulteration of apple juice with DL-malic acid at lower levels than those reported with previous methods. The LC method for determination of D-malic acid in apple juice has been adopted first action by AOAC INTERNATIONAL.

Beverages↗

PubMed1981

Nocturnal Accumulation of Malic Acid Occurs in Mesophyll Tissue without Proton Transport to Epidermal Tissue in the Inducible Crassulacean Acid Metabolism Plant Mesembryanthemum crystallinum: EVIDENCE AGAINST A PREVIOUS HYPOTHESIS.

The inducible Crassulacean acid metabolism plant, Mesembryanthemum crystallinum, accumulates malic acid, i.e. equivalent amounts of malate anions and protons in the mesophyll cells at night. Levels of malate and titratable acidity are low in the epidermal tissue and do not change significantly during the day/night cycle. This result is in contrast to a recent report (Bloom 1979 Plant Physiol 64: 919-923) that the synthesis of malic acid during dark CO(2) fixation is associated with an equivalent exchange of inorganic cations from epidermal tissue with protons in the mesophyll cells.

Journal Article↗

PubMed1980

Gamma-irradiation of malic acid in aqueous solutions.

The gamma-irradiation of malic acid in aqueous solutions was studied under initially oxygenated and oxygen-free conditions in an attempt to determine the possible interconversion of malic acid into other carboxylic acids, specifically those associated with Krebs cycle. The effect of dose on product formation of the system was investigated. Gas-liquid chromatography combined with mass spectrometry was used as the principal means of identification of the non-volatile products. Thin layer chromatography and direct probe mass spectroscopy were also employed. The findings show that a variety of carboxylic acids are formed, with malonic and succinic acids in greatest abundance. These products have all been identified as being formed in the gamma-irradiation of acetic acid, suggesting a common intermediary. Since these molecules fit into a metabolic cycle, it is strongly suggestive that prebiotic pathways provided the basis for biological systems.

Aerobiosis↗

PubMedDate not supplied

[Study on L-malic acid catabolism by "Lactobacillus casei" cells immobilized into polyacrylamide gel lattice (author's transl)].

Study on L-malic acid catabolism by Lactobacillus casei cells immobilized into polyacrylamide gel lattice has shown that the pH profil of malic acid decarboxylase activity does not differ significantly from that of free cells. The apparent enzymatic constant value as determined by the Warburg manometric method is 5 X 10(-3) M for free cells and 1.25 X 10(-2) M for immobilized cells. Malic acid decarboxylase activity can be preserved in immobilized cells over a 12 month period when the reaction vessel is fed continuously with the growth medium. It is noteworthy that the reaction vessel is similar to a constant activity reactor whose apparent enzymatic constant value, of 6,25 X 10(-3) M, does not differ significantly from that of free cells. Labelling of the cells with 14C-glycin has shown that the immobilized cells released 14 per cent of the radioactivity over a 65 hour period, indicating that the cells are possibly in a non proliferating state. After 9 months of working, a large fraction of viable bacterial cells can be isolated again. The use of such a reactor for producing metabolites is proposed.

Acrylamides↗

PubMed1977

Changes in Metabolite Levels in Kalanchoë daigremontiana and the Regulation of Malic Acid Accumulation in Crassulacean Acid Metabolism.

Changes in glucose-6-P, fructose-6-P, fructose-1,6-diP, 6-phospho-gluconate, phosphoenolpyruvate, 3-phosphoglycerate, and pyruvate levels in the leaves of the Crassulacean plant Kalanchoë daigremontiana Hammet et Perrier were measured enzymically during transitions from CO(2)-free air to air, air to CO(2)-free air, and throughout the course of acid accumulation in darkness. The data are discussed in terms of the involvement of phosphoenolpyruvate carboxylase in malic acid synthesis and in terms of the regulation of the commencement of malic acid synthesis and accumulation through the effects of CO(2) on storage carbohydrate mobilization and its termination through the effects of malic acid on phosphoenolpyruvate carboxylase activity.

Journal Article↗

PubMedDate not supplied

[Enzymatic synthesis of L-malic acid from fumaric acid using immobilized Escherichia coli cells].

Optimal conditions were chosen for cultivation of Escherichia coli 85 cells with a rather high fumarate-hydratase activity on a cheap medium containing no edible raw material. An active biocatalyst for the synthesis of L-malic acid from fumaric acid was obtained based on E. coli 85 cells immobilized in carrageenan. The enzymatic synthesis of L-malic acid from potassium fumarate was kinetically studied and optimized. Some thermodynamic parameters of fumaric acid hydration into malic acid were determined. A technique for assaying the reaction mixture was developed that involved high performance liquid chromatography.

Escherichia coli↗

PubMed2007

Fluorescent sensing layer for the determination of L-malic acid in wine.

An enzymatic method for determining L-malic acid in wine based on an L-malate sensing layer with nicotinamide adenine dinucleotide (NAD+), L-malate dehydrogenase (L-MDH) and diaphorase (DI), immobilized by sol-gel technology, was constructed and evaluated. The sol-gel glass was prepared with tetramethoxysilane (TMOS), water and HCl. L-MDH catalyzes the reaction between L-malate and NAD+, producing NADH, whose fluorescence (lambdaexc=340 nm, lambdaem=430 nm) could be directly related to the amount of L-malate. NADH is converted to NAD+ by applying hexacyanoferrate(III) as oxidant in the presence of DI. Some parameters affecting sol-gel encapsulation and the pH of the enzymatic reaction were studied. The sensing layer has a dynamic range of 0.1-1.0 g/L of L-malate and a long-term storage stability of 25 days. It exhibits acceptable reproducibility [sr(%) approximately 10] and allows six regenerations. The content of L-malic acid was determined for different types of wine, and polyvinylpolypyrrolidone (PVPP) was used as a bleaching agent with red wine. The results obtained for the wine samples using the sensing layer are comparable to those obtained from a reference method based on UV-vis molecular absorption spectrometry, if the matrix effect is corrected for.

Glycine↗