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PubMed1998

Increased in vivo collagen synthesis and in vitro cell proliferative effect of glycolic acid.

BACKGROUND: Glycolic acid treatment is believed to reverse the photoaging process by increasing collagen synthesis in the skin. However, this effect has not been clearly defined even though alpha hydroxy acid products are used extensively. OBJECTIVE: This study aimed to define the primary effect of glycolic acid on collagen synthesis that may be achieved by functional activation or proliferation of fibroblasts. METHODS: Glycolic acid treatment was compared in vivo with lactic acid (hairless mice) and in vitro to malic acid (normal human skin fibroblast culture) with controls. To find the functional activation of fibroblasts, Northern blot assay for type I collagen synthesis with histometric analysis (in vivo) was performed. Cell proliferation assay (MTT) with procollagen type I C-peptide (PICP) enzyme immunoassay and radioisotope ([3H]proline) incorporated collagen production from cultured fibroblasts were determined. RESULTS: The in vivo collagen mRNA expression with histometric analysis revealed greater collagen synthesis by glycolic acid compared with lactic acid and control. In vitro cell proliferative effect of glycolic and greater amount of collagen production showed a steady increase in a dose-dependent manner. CONCLUSION: Both in vivo and in vitro, glycolic acid treatment increased the production of collagen and fibroblast proliferation. These effects may be the mechanism by which glycolic acid reverses the process of photoaging.

Animals↗
PubMed1988

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↗
PubMed1978

[Biosynthesis of NADP-malate dehydrogenases in greening etiolated maize leaves].

The activities of NADP-dependent malate dehydrogenases in greening etiolated maize leaves were studied. "Malic" enzyme (EC 1.1.1.40) in bundle sheath cells developed slower as compared to NADP-malate dehydrogenase synthesizing malic acid in mesophyll chloroplasts. The increase in "malic" enzyme activity in the light was suppressed by protein synthesis inhibitors--chloramphenicol and cycloheximide. Possible localization of enzyme protein synthesis is discussed.

Chloramphenicol↗
PubMed1996

Ex-vivo in-vitro inhibition of lipopolysaccharide stimulated tumor necrosis factor-alpha and interleukin-1 beta secretion in human whole blood by extractum urticae dioicae foliorum.

An extract of Urtica dioica folium (IDS 23, Rheuma-Hek), monographed positively for adjuvant therapy of rheumatic diseases and with known effects in partial inhibition of prostaglandin and leukotriene synthesis in vitro, was investigated with respect to effects of the extract on the lipopolysaccharide (LPS) stimulated secretion of proinflammatory cytokines in human whole blood of healthy volunteers. In the assay system used, LPS stimulated human whole blood showed a straight increase of tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta) secretion reaching maximum concentrations within 24 h following a plateau and slight decrease up to 65 h, respectively. The concentrations of these cytokines was strongly positively correlated with the number of monocytes/macrophages of each volunteer. TNF-alpha and IL-1 beta concentration after LPS stimulation was significantly reduced by simultaneously given IDS 23 in a strictly dose dependent manner. At time 24 h these cytokine concentrations were reduced by 50.8% and 99.7%, respectively, using the highest test IDS 23 assay concentration of 5 mg/ml (p < 0.001). After 65 h the corresponding inhibition was 38.9% and 99.9%, respectively (p < 0.001). On the other hand IDS 23 showed no inhibition but stimulated IL-6 secretion in absence of LPS alone. Simultaneously given LPS and IDS 23 resulted in no further increase. In contrast to described effects on arachidonic acid cascade in vitro, tested Urtica dioica phenol carbon acid derivates and flavonoides such as caffeic malic acid, caffeic acid, chlorogenic acid, quercetin and rutin did not influence LPS stimulated TNF-alpha, IL-1 beta and IL-6 secretion in tested concentrations up to 5 x 10(-5) mol/l. These further findings on the pharmacological mechanism of action of Urticae dioica folia may explain the positive effects of this extract in the treatment of rheumatic diseases.

Adult↗
PubMedDate not supplied

Simultaneous determination of organic acids and vitamin C in green beans by liquid chromatography.

A method is described for determining and quantitating organic acids (oxalic, malic, citric, and fumaric) and vitamin C by liquid chromatography with a UV-visible detector that allows simultaneous monitoring at 2 wavelengths. The method was applied to samples of green beans (Phaseolus vulgaris L.). Recoveries were 97.8% for oxalic acid, 98.9% for malic acid, 98.7% for citric acid, 99.2% for fumaric acid, and 98.5% for vitamin C. Method precisions (coefficients of variation) were 1.7% for oxalic acid, 0.8% for malic acid, 0.9% for citric acid, 1.5% for fumaric acid, and 1.2% for vitamin C. Measurement precisions (coefficients of variation) were 1.32% for oxalic acid, 0.33% for malic acid, 0.62% for citric acid, 1.01% for fumaric acid, and 0.39% for vitamin C. Limits of detection were 0.025 mg/mL for oxalic acid, 0.022 mg/mL for malic acid, 0.024 mg/mL for citric acid, 1.0 x 10(-4) mg/mL for fumaric acid, and 2.7 x 10(-4) mg/mL for vitamin C.

Acids↗
PubMed1985

[Organic acids in vegetables. I. Brassica, leaf and bulb vegetables as well as carrots and celery].

18 German vegetable species were analyzed for their organic acid content. Organic acids were isolated by methanol extraction followed by ion exchange. After derivatisation with BSA the trimethylsilyl derivatives were analyzed by gas chromatography using SE-52 and OV-1701 glass capillaries. The predominate acids are malic and citric acid, and in most cases malic acid was the most abundant. Succinic, fumaric, and quinic acids are wide spread, tartaric acid was found in carrots, lettuce, endives, chicory, and celery. Other acids such as malonic, shikimic, and t-aconitic acids occurred sporadically. Lactic acid which was determined by two other methods was not detected in any vegetable species.

Acids↗
PubMed1970

Effect of Oxygen on the Light-enhanced Dark Carbon Dioxide Fixation in Chlorella Cells.

With Chlorella ellipsoidea cells, the effect of oxygen was investigated on the products of enhanced dark (14)CO(2) fixation immediately following preillumination in the absence of CO(2). When the reaction mixture was made aerobic by bubbling air (CO(2)-free) throughout preillumination and the following dark (14)CO(2) fixation periods, the initial fixation product was mainly 3-phosphoglyceric acid. When nitrogen gas had been used instead of air, only about one-half of the total radioactivity in the initial fixation products was in 3-phosphoglyceric acid and the rest in aspartic, phosphoenolpyruvic, and malic acids. The percentage distribution of radioactivity incorporated in these initial products rapidly decreased during the rest of the dark period. Concurrent with the decrease in the initial (14)CO(2) fixation products, some increase was observed in the radioactivities of the sugar phosphates. The maximal radioactivity incorporated in sugar mono- and diphosphates accounted for only 10% of total (14)C, under either the aerobic or anaerobic conditions. Under anaerobic conditions most of the (14)C incorporated was eventually transferred to alanine, whereas the main end products under aerobic conditions were aspartate and glutamate. The pattern of (14)CO(2) fixation products was unaffected by the atmospheric condition during the period of preillumination. The preferential flow of the fixed carbon atom to alanine or aspartate depended on the presence or absence of oxygen during the period of dark CO(2) fixation.

Journal Article↗
PubMed1988

Ecophysiological Significance of CO(2)-Recycling via Crassulacean Acid Metabolism in Talinum calycinum Engelm. (Portulacaceae).

High levels of variability in gas exchange characteristics and degree of CAM-cycling were found in the same and different individuals of Talinum calycinum Engelm. collected from rock outcrops in Missouri. Differences in CO(2) assimilation were mostly correlated with differences in shoot conductance to CO(2) not shoot internal CO(2) concentration. As found previously, CAM acid fluctuations were evident in well-watered plants exhibiting C(3) gas exchange patterns (CAM-cycling) and also in drought-stressed plants with stomata closed, or nearly so, day and night (CAM-idling). Drought stress also resulted in rapid stomatal closure, conserving water during droughts. Maximal CO(2) uptake rates occurred below 35 degrees C; higher temperatures induced decreases in CO(2) assimilation and conductance while shoot internal CO(2) concentrations remained similar. Plant water-use-efficiency was severely curtailed at temperatures above 30 degrees C. Tissue acid fluctuations were the result of changes in malic acid concentrations. Calculations of the amount of water potentially conserved by CAM-cycling yielded values of approximately 5 to 44% of daytime water loss. Thus, CAM-cycling may be an important adaptation minimizing water loss by perennial succulents growing in shallow soil on rock outcrops.

Journal Article↗
PubMed1990

Bacterial siderophores: structures of pyoverdins Pt, siderophores of Pseudomonas tolaasii NCPPB 2192, and pyoverdins Pf, siderophores of Pseudomonas fluorescens CCM 2798. Identification of an unusual natural amino acid.

Pyoverdins were isolated and characterized respectively from the cultures of Pseudomonas tolaasii NCPPB 2192 (pyoverdins Pt, Pt A, and Pt B) and Pseudomonas fluorescens CCM 2798 (Pyoverdins Pf/1, Pf/2, Pf, Pf/3/1, and Pf/3/2) each grown in iron-deficient conditions. Their structures were established by using FAB-MS, NMR, and CD techniques. These siderophores are chromopeptides, and all but one (pyoverdin Pf/3/3) possess at the N-terminal end of their peptide chain the same chromophore that has been reported in pyoverdin Pa from Pseudomonas aeruginosa ATCC 15692 [Wendenbaum, S., Demange, P., Dell, A., Meyer, J. M., & Abdallah, M. A. (1983) Tetrahedron Lett. 24, 4877-4880] and pseudobactin B 10 from Pseudomonas B10 [Teintze, M., Hossain, M. B., Barnes, C. L., Leong, J., & Van der Helm, D. (1981) Biochemistry 20, 6446-6457] which is derived from 2,3-diamino-6,7-dihydroxyquinoline. In pyoverdins Pt this chromophore is bound to a linear peptide chain D-Ser-L-Lys-L-Ser-D-Ser-L-Thr-D-Ser-L-OHOrn-L-Thr-D-Ser-D-OHOrn (cyclic) which has its C-terminal end blocked by cyclic D-N delta-hydroxyornithine. In pyoverdins Pf, the peptide chain is also linear, SerCTHPMD-Gly-L-Ser-D-threo-OHAsp-L-Ala-Gly-D-Ala-Gly-L-O HOrn(cyclic), and contains an unusual natural amino acid which is the result of the condensation of 1 mol of serine and 1 mol of 2,4-diaminobutyric acid, forming a cyclic amidine. The pyoverdins Pt differ only in substituent bound to the nitrogen on C-3 of the chromophore, which is succinic acid in pyoverdin Pt A, succinamide in pyoverdin Pt, and alpha-ketoglutaric acid bound to the chromophore by its C-5 carbon atom in pyoverdin Pt B. Similarly, pyoverdin Pf/1, pyoverdin Pf/2, pyoverdin Pf (the major compound), and pyoverdin Pf/3/2 are substituted respectively by L-malic acid, succinic acid, L-malic amide, and succinamide. Pyoverdin Pf/3/3 has the same chromophore as azotobactin, the peptidic siderophore of Azotobacter vinelandii. These pyoverdins are very similar to pseudobactin B 10, the siderophore of Pseudomonas B10: they are linear peptides containing three bidentate groups strongly chelating Fe(III) and blocked at their N-terminal end by the catecholic chromophore and at their C-terminal end by cyclic N delta-hydroxyornithine. They differ therefore from other pyoverdins such as those from P. aeruginosa ATCC 15692 which contain a partly cyclic peptide [Briskot, G., Taraz, K., & Budzikiewicz, H. (1989) Liebigs Ann. Chem., 375-384].

Amino Acid Sequence↗
PubMed1978

Biochemical differences between serotypes of Cryptococcus neoformans.

Prior studies have shown that C. neoformans isolates belonging to serotypes B and C differed from serotype A and D isolates in respect to the morphology of the perfect state, geographic distribution within the U.S.A. and frequency of isolation from avian droppings. The current study found that uptake of radiolabeled l-malic acid was approximately tenfold greater in serotype B and C than in A and D isolates. Assimilation of l-malic, fumaric and succinic acids also distinguished serotypes B and C from A and D. Greening of Guizotia seed agar occurred with 18 of 32 serotype B and C but in none of 91 serotype A or D isolates. The one property not following the same line of division was relatively slow creatinine assimilation, which distinguished type A alone.

Creatinine↗
PubMed2003

A stereoselective and short total synthesis of the polyhydroxylated gamma-amino acid (-)-detoxinine, based on stereoselective preparation of dihydropyrrole derivatives from lithiated alkoxyallenes.

Based on our earlier results employing lithiated methoxyallene 2 as C(3) building block and imines 3 for the synthesis of dihydropyrrole derivatives 5, we have investigated chiral imines 6, 10, and 15 as electrophilic components. Combined with lithiated alkoxyallenes, these imines provide the corresponding primary adducts and finally the dihydropyrrole derivatives 8, 12, 17, 20, and 22 in good yields and with high to excellent syn selectivities. This stereochemical outcome is interpreted as a result of alpha-chelate control. Treatment with hydrochloric acid converted syn-8 and syn-12 into bicyclic compounds 9 and 13, whereas under more mildly acidic conditions adduct syn-17 was transformed into diol syn-18. The total synthesis of the uncommon gamma-amino acid (-)-detoxinine could be achieved by starting from (S)-malic acid, which was converted into imine 15 in four steps. Lithiated benzyloxyallene added to imine 15 and efficiently furnished the crucial dihydropyrrole derivative syn-22. The hydrogenolysis of this compound did not directly provide the protected triol 29 as anticipated, but a stepwise protocol made the triol available in a fairly satisfactory manner. A second crucial step of the synthesis was the selective oxidation of 29, which could be achieved by employing platinum dioxide and oxygen. The resulting bicyclic lactone 30 was smoothly transformed into enantiopure (-)-detoxinine. Thus, a fairly short synthesis of this natural product based on a lithiated alkoxyallene could be performed, demonstrating the potential of these intermediates for syntheses of interesting functionalized heterocyclic compounds.

Alkanes↗
PubMed2003

Turkish Tombul hazelnut (Corylus avellana L.). 1. Compositional characteristics.

The quality of Tombul (Round) hazelnut, grown in the Giresun province of Turkey, was determined by measuring proximate composition, minerals, vitamins, dietary fiber, amino acids, and taste active components (free amino acids, sugars, and organic acids). Fat was the predominant component in Tombul hazelnut (approximately 61%). The major minerals were potassium, phosphorus, calcium, magnesium, and selenium. Hazelnut was also found to serve as an excellent source of vitamin E (24 mg/100 g) and a good source of water soluble (B complex) vitamins and dietary fiber. The major amino acids were glutamic acid, arginine, and aspartic acid. The three nonessential amino acids and the essential amino acids contributed 44.9 and 30.9% to the total amino acids present, respectively, while lysine and tryptophan were the limiting amino acids in Tombul hazelnut. Twenty-one free amino acids, six sugars, and six organic acids were positively identified; among these, arginine, sucrose, and malic acid predominated, respectively. These taste active components may play a significant role in the taste and flavor characteristics of hazelnut. Thus, the present results suggest that Tombul hazelnut serves as a good source of vital nutrients and taste active components.

Amino Acids↗
PubMed2005

Potential application of a glucose-transport-deficient mutant of Schizosaccharomyces pombe for removing gluconic acid from grape must.

Musts from rotten grapes typically contain high levels of gluconic acid, which can raise severe problems in winemaking processes. In this work, the ability of the glucose-transport-deficient mutant YGS-5 of Schizosaccharomyces pombe to completely or partly remove gluconic acid from a synthetic glucose-containing medium and the potential use of this yeast strain for the same purpose in musts and wines were examined. Surprisingly, the S. pombe YGS-5 strain successfully removed 93% of the initial gluconic acid (2.5 gL(-1)) and 80% of the initial malic acid (1.0 gL(-1)) within 30 h after inoculation. Also, the yeast strain produced no volatile compounds other than those obtained in fermentations conducted with the wine yeast Saccharomyces cerevisiae. S. pombe YGS-5 could thus be used to remove gluconic acid present in musts from rotten grapes. On the basis of these results, various ways of using S. pombe YGS-5 to treat musts containing gluconic acid in order to solve the problems due to the high gluconic acid concentrations in botrytized grape must are proposed.

Fermentation↗
PubMed2003

Synthesis of (R)-2-methyl-4-deoxy and (R)-2-methyl-4,5-dideoxy analogues of 6-phosphogluconate as potential inhibitors of 6-phosphogluconate dehydrogenase.

The synthesis of (2R)-2-methyl-4,5-dideoxy and (2R)-2-methyl-4-deoxy analogues of 6-phosphogluconate is described. The synthetic strategy relies on the Evans aldol reaction for the installation of the chiral centres in the 2- and 3-positions. The selective phosphorylation at the primary alcohol function of (2R,3S)-3,6-dihydroxy-2-methylhexanoic acid benzyl ester (5) and (2R,3S,5S)-3,5,6-trihydroxy-2-methylhexanoic acid benzyl ester (20) was achieved with dibenzyl phosphochloridate and dibenzyl phosphoiodinate respectively, working at low temperature. (2R,3S)-3-Hydroxy-2-methyl-6-phosphonoxyhexanoic acid (9) was obtained in 25% overall yield from 4-benzyloxybutanol and (2R,3S,5S)-3,5-dihydroxy-2-methyl-6-phosphonoxyhexanoic acid (28) in 10% overall yield from L-malic acid.

Animals↗
PubMed1993

Hydroxycinnamic Acid Derivatives, Caffeoylmalic and New Caffeoylaldonic Acid Esters, from Chelidonium majus*,1.

HPLC analysis of a hydrolyzed extract obtained from the aerial parts of CHELIDONIUM MAJUS yielded 0.4% caffeic, 0.06% P-coumaric, and 0.02% ferulic acids; gentisic and P-hydroxybenzoic acids were below 0.01%. The caffeic acid derivatives occur as esters of which four were isolated using gel permeation chromatography, centrifugal partition chromatography and HPLC; they were assigned on the basis of their spectroscopic data ( (1)H-, (13)C-NMR, UV, MS) as the new (-)-2-( E)-caffeoyl- D-glyceric acid, (-)-4-( E)-caffeoyl- L-threonic acid, (-)-2-( E)-caffeoyl- L-threonic acid lactone, and the known (+)-( E)-caffeoyl- L-malic acid.

Journal Article↗
PubMed1980

Malioxamycin, a new antibiotic with spheroplast-forming activity. II. Structural elucidation and total synthesis.

Malioxamycin (1) is a new antibiotic produced by Streptomyces lydicus No. 15748. The structure of malioxamycin has been determined by nmr and mass spectra to possess a hydroxamic acid bond between L-valine and D-malic acid. This structure was confirmed by total synthesis of the antibiotic with (R)-aminooxysuccinic acid and the active ester of L-valine.

Anti-Bacterial Agents↗
PubMed2001

CJ-15,183, a new inhibitor of squalene synthase produced by a fungus, Aspergillus aculeatus.

A new squalene synthase (SSase) inhibitor, CJ-15,183 (I) was isolated from the fermentation broth of a fungus, Aspergillus aculeatus CL38916. The compound potently inhibited rat liver and Candida albicans microsomal SSases and also inhibited the human enzyme. It also showed antifungal activities against filamentous fungi and a yeast. The structure was determined to be an aliphatic tetracarboxylic acid compound consisting of an alkyl gamma-lactone, malic acid and isocitric acid moieties by spectroscopic studies.

Alkenes↗