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PubMed1977

Organic acid and potassium accumulation in guard cells during stomatal opening.

Leaflets of Vicia faba L. with either open or closed stomata were quick-frozen and freeze-dried. Individual guard cell pairs and pure samples of palisade parenchyma, spongy parenchyma, and epidermis lacking guard cells were dissected from the leaflets, weighed, and assayed for organic acids or K(+).K(+) was measured by a new enzymatic method. In guard cells of open stomata, as compared to closed stomata, K(+) was 2- to 4-fold higher, malic acid 6-fold higher, and citric acid 3-fold higher. Both aspartic and glutamic acids were also higher, but the amounts present were low compared to malic and citric acids. Isocitric acid was significantly higher in one experiment, but not in another. Glyceric acid was not increased. Succinic acid was too low to detect by the method used; but in guard cells of open stomata the concentration must have been less than 2% of that of malic acid. Malic acid was higher in the palisade parenchyma from the leaflet with open stomata. The ion balance shows that malic and citric acids provide much of the counter ion for the K(+) taken up during stomatal opening.

Journal Article↗

PubMed1999

Control of flavor development in wine during and after malolactic fermentation by Oenococcus oeni.

During malolactic fermentation in wine by Oenococcus oeni, the degradation of citric acid was delayed compared to the degradation of malic acid. The maximum concentration of diacetyl, an intermediary compound in the citric acid metabolism with a buttery or nutty flavor, coincided with the exhaustion of malic acid in the wine. The maximum concentration of diacetyl obtained during malolactic fermentation was strongly dependent on the oxygen concentration and the redox potential of the wine and, to a lesser extent, on the initial citric acid concentration. The final diacetyl concentration in the wine was also dependent on the concentration of SO2. Diacetyl combines rather strongly with SO2 (Kf = 7.2 x 10(3) M(-1) in 0.1 M malate buffer [pH 3.5] at 30 degrees C). The reaction is exothermic and reversible. If the concentration of SO2 decreases during storage of the wine, the diacetyl concentration increases again.

Journal Article↗

PubMed1994

Counteractive Effects of ABA and GA3 on Extracellular and Intracellular pH and Malate in Barley Aleurone.

Barley (Hordeum vulgare L.) aleurone layers are known to constitutively acidify their surroundings, primarily by L-malic acid release (J. Mikola, M. Virtanen [1980] Plant Physiol 66: S-142). Here we demonstrate the antagonistic effects of the plant hormones gibberellic acid (GA3) and abscisic acid (ABA) on the regulation of extracellular pH (pHe) of barley aleurone layers. We observed a strong correlation between ABA-induced enhancement of extracellular acidification and an ABA-induced increase in L-malic acid release. In addition, ABA caused an increase in intracellular L-malate level. GA3 caused a slight decrease in intracellular L-malate level and was able to inhibit the ABA-induced increase in L-malate intracellular concentration and release. In addition, this ABA-induced L-malate release could be completely inhibited by GA3. The ABA-induced release of L-malic acid could not account for the total ABA-induced pHe decrease, suggesting the existence of an additional mechanism involved in the regulation of pHe. It has been reported that ABA induces an intracellular pH (pHi) increase, possibly due to the activation of plasma membrane proton pumps (R. Van der Veen, S. Heimovaara-Dijkstra, M. Wang [1992] Plant Physiol 100: 699-705). A pHi increase, such as that caused by ABA, might be correlated with the intracellular L-malate increase as suggested by the pH stat model of D.D. Davies ([1986] Physiol Plant 67: 702-706). We studied if the effects of GA3 on L-malate concentration were correlated with changes in pHi and found that GA3 caused a pHi decrease and that GA3 and ABA could interfere in the regulation of pHi. In addition, we were able to mimic the effect of both hormones on L-malate release by bringing about artifical pHi changes with the weak acid 5,5-dimethyl-2,4-oxazolidinedione and the weak base methylamine. The physiological meaning of the effects of GA3 and ABA on the regulation of both pHe and pHi during grain germination are discussed.

Journal Article↗

PubMed2004

Peroxomolybdate(VI)-citrate and -malate complex interconversions by pH-dependence. Synthetic, structural and spectroscopic studies.

The reaction of potassium molybdate(VI) with biologically relevant ligands, citric and malic acids, in the presence of H2O2 was investigated for the effect of pH variations on the product pattern. That with citric acid led to the formation of the monomeric complex K4[MoO(O2)2(cit)].4H2O (1) in the pH range 7-9, and dimer K5[MoO(O2)(2-)(Hcit)H(Hcit)(O2)2OMo].6H2O (2) (H4cit = citric acid) at pH 3-6 through carboxylate-carboxylic acid hydrogen bonding. The relation with the previously identified K4[MoO3(cit)].2H2O (4) and K4[Mo2O5(Hcit)2].4H2O (5) were shown. These and other intermediates were shown to react in the pH range 3-6 to give a more stable species 2; the reaction sequence was demonstrated either by the protonation from 1 or the deprotonation of [MoO(O2)2(H2cit)](2-) (8). Evidence that 2 exists as a dimer in solution is presented. The reaction with (S)-malic acid afforded Delta-K(2n)[MoO(O2)2((S)-Hmal)]n.nH2O (3) (H3mal = malic acid) that was oxidized further to oxalato molybdate (11) by H2O2. The three complexes 1-3 were characterized by elemental analysis, UV, IR and NMR spectroscopies, in addition to the X-ray structural studies that show citrate and malate being coordinated as bidentate ligands via alpha-alkoxyl and alpha-carboxylate groups. The formation of these complexes is dictated by pH and their thermal stabilities varied with the coordinated hydroxycarboxylate ligands.

Journal Article↗

PubMed1984

Carbon Assimilation Characteristics of the Aquatic CAM Plant, Isoetes howellii.

The relationship between malic acid production and carbon assimilation was examined in the submerged aquatic Crassulacean acid metabolism (CAM) plant, Isoetes howellii Engelmann. Under natural conditions free-CO(2) level in the water was highest at 0600 hours and (14)CO(2) assimilation rates in I. howellii were also highest at this time. After 0900 hours there was a similar pattern in (a) rate of free-CO(2) depletion from the water, (b) reduction of carbon assimilation rates, and (c) rate of deacidification in leaves. Rates of daytime deacidification increased under CO(2)-free conditions and as irradiance intensity increased. Nighttime CO(2) uptake was estimated to contribute one-third to one-half of the total daily gross carbon assimilation. CO(2) uptake, however, accounted for only one-third to one-half of the overnight malic acid accumulation. Internal respiratory CO(2) may be a substrate for a large portion of overnight acid accumulation as leaves incubated overnight without CO(2) accumulated substantial levels of malic acid. Loss of CAM occurred in emergent leaf tips even though submerged bases continued CAM. Associated with loss of CAM in aerial leaves was an increase in total chlorophyll, a/b ratio, and carotenoids, and a decrease in leaf succulence. delta(13)C values of I. howellii were not clearly distinguishable from those for associated non-CAM submerged macrophytes.

Journal Article↗

PubMed2002

Probing in vivo metabolism by stable isotope labeling of storage lipids and proteins in developing Brassica napus embryos.

Developing embryos of Brassica napus accumulate both triacylglycerols and proteins as major storage reserves. To evaluate metabolic fluxes during embryo development, we have established conditions for stable isotope labeling of cultured embryos under steady-state conditions. Sucrose supplied via the endosperm is considered to be the main carbon and energy source for seed metabolism. However, in addition to 220 to 270 mM carbohydrates (sucrose, glucose, and fructose), analysis of endosperm liquid revealed up to 70 mM amino acids as well as 6 to 15 mM malic acid. Therefore, a labeling approach with multiple carbon sources is a precondition to quantitatively reflect fluxes of central carbon metabolism in developing embryos. Mid-cotyledon stage B. napus embryos were dissected from plants and cultured for 15 d on a complex liquid medium containing (13)C-labeled carbohydrates. The (13)C enrichment of fatty acids and amino acids (after hydrolysis of the seed proteins) was determined by gas chromatography/mass spectrometry. Analysis of (13)C isotope isomers of labeled fatty acids and plastid-derived amino acids indicated that direct glycolysis provides at least 90% of precursors of plastid acetyl-coenzyme A (CoA). Unlabeled amino acids, when added to the growth medium, did not reduce incorporation of (13)C label into plastid-formed fatty acids, but substantially diluted (13)C label in seed protein. Approximately 30% of carbon in seed protein was derived from exogenous amino acids and as a consequence, the use of amino acids as a carbon source may have significant influence on the total carbon and energy balance in seed metabolism. (13)C label in the terminal acetate units of C(20) and C(22) fatty acids that derive from cytosolic acetyl-CoA was also significantly diluted by unlabeled amino acids. We conclude that cytosolic acetyl-CoA has a more complex biogenetic origin than plastidic acetyl-CoA. Malic acid in the growth medium did not dilute (13)C label incorporation into fatty acids or proteins and can be ruled out as a source of carbon for the major storage components of B. napus embryos.

Acetyl Coenzyme A↗

PubMed1988

Root excision decreases nutrient absorption and gas fluxes.

The roots of barley plants (Hordeum vulgare L. cv Steptoe) were monitored before and after excision for net uptake of carbon dioxide, oxygen, ammonium, potassium, nitrate, and chloride and for their content of sucrose, glucose, fructose, and malic acid. All fluxes began to attenuate within 2 hours after excision. Net potassium uptake returned to control levels 6 hours after excision, but carbon dioxide, oxygen, ammonium, and nitrate fluxes continued to diminish for the remainder of the observation period. The addition of 0.1 molar glucose or 0.1 molar sucrose to excision medium had no significant effect on these changes in ion and gas fluxes. Net chloride uptake was negligible for all treatments. Sugar and malic acid content of the root declined after excision. Sucrose and glucose levels remained depressed for the entire observation period, whereas fructose and malic acid returned to control levels after 9 hours. These results indicate that excision has profound, adverse effects on root respiration and the absorption of mineral nitrogen.

Journal Article↗

PubMed2000

Phenylpropanoids from Ballota nigra L. inhibit in vitro LDL peroxidation.

From the European plant Ballota nigra L. various polyphenols including phenylpropanoid derivatives were isolated. There is increasing evidence that oxidized low-density lipoproteins (Ox-LDL) might be involved in the pathogenesis of atherosclerosis and it has been reported that polyphenols inhibit LDL peroxidation and atherogenesis. The goal of this study was to test whether the major polyphenolic compounds extracted from Ballota nigra, four phenylpropanoid glycosides, verbascoside, forsythoside B, arenarioside, and ballotetroside and one non-glycosidic phenylpropanoid, caffeoyl-L-malic acid, inhibit Cu(2+)-induced LDL peroxidation. The effectiveness of these compounds was compared to the activity of quercetin, a well-known polyphenol inhibitor of Cu(2+)-induced LDL oxidation. Antioxidant efficacious doses (ED 50) of arenarioside and ballotetroside were 1.8 microM and 7.5 microM respectively, while in the same conditions, the ED 50 of forsythoside B and verbascoside were similar (1 microM) and those of quercetin and of caffeoyl-L-malic acid were 2.3 microM and 9.5 microM respectively. Spectrophotometric studies show that quercetin is a Cu(2+) chelator while phenylpropanoid glycosides and caffeoyl-L-malic acid are not Cu(2+) chelators. Therefore, phenylpropanoid glycosides are strong inhibitors of Cu(2+)-induced LDL oxidation, independent of any capacity to act as Cu(2+) chelators.

Caffeic Acids↗

PubMed2004

Responses of eucalypt species to aluminum: the possible involvement of low molecular weight organic acids in the Al tolerance mechanism.

Aluminum (Al) tolerance mechanisms in crop plants have been extensively researched, but our understanding of the physiological mechanisms underlying Al tolerance in trees is still limited. To investigate Al tolerance in eucalypts, seedlings of six species (Eucalyptus globulus Labill., Eucalyptus urophylla S.T. Blake, Eucalyptus dunnii Maiden, Eucalyptus saligna Sm., Eucalyptus cloeziana F. J. Muell. and Eucalyptus grandis w. Hill ex Maiden) and seedlings of six clones of Eucalyptus species were grown for 10 days in nutrient solutions containing Al concentrations varying from 0 to 2.5 microM (0 to 648 microM Al3+ activities). Root elongation of most species was inhibited only by high Al3+ activities. Low to intermediate Al3+ activities were beneficial to root elongation of all species and clones. Among the species tested, E. globulus and E. urophylla were more tolerant to Al toxicity, whereas E. grandis and E. cloeziana were more susceptible to Al-induced damage. Although E. globulus seedlings were tolerant to Al toxicity, they were highly sensitive to lanthanum (La), indicating that the tolerance mechanism is specific for Al. Fine roots accumulated more Al and their elongation was inhibited more than that of thick roots. In E. globulus, accumulation of Al in root tips increased linearly with increasing Al concentration in the nutrient solution. The majority of Al taken up was retained in the root system, and the small amounts of Al translocated to the shoot system were found mainly in older leaves. No more than 60% of the Al in the thick root tip was in an exchangeable form in the apoplast that could be removed by sequential citrate rinses. Gas chromatography/mass spectrometry and ion chromatography analyses indicated that root exposure to Al led to a greater than 200% increase in malic acid concentration in the root tips of all eucalypt species. The increase in malate concentration in response to Al treatment correlated with the degree of Al tolerance of the species. A small increase in citric acid concentration was also observed in all species, but there were no consistent changes in the concentrations of other organic acids in response to Al treatment. In all eucalypt species, Al treatment induced the secretion of citric and malic acid in root exudates, but no trend with respect to Al tolerance was observed. Thus, although malate and citrate exudation by roots may partially account for the overall high Al tolerance of these eucalypt species, it appears that tolerance is mainly derived from the internal detoxification of Al by complexation with malic acid.

Aluminum↗

PubMed1966

Effects of additives on the survival of lactic streptococci in frozen storage.

Three single-strain cultures, Streptococcus lactis C(2), S. cremoris R(1), and S. diacetilactis DRC(2), were frozen and stored in skim milk, in skim milk containing apple juice, and in skim milk containing one of the following additives: glycerol (10%, v/v), dimethyl sulfoxide (10%, v/v), l-malic acid (0.5 and 2.0%, w/v), acetamide (0.5 and 2.0%, w/v), or succinimide (0.5 and 2.0%, w/v). Cultures were frozen and stored at -23.3 C, frozen and stored at -196 C in liquid nitrogen, or frozen at -196 C and stored at -23.3 C. Cultures frozen and stored at -196 C in liquid nitrogen gave the greatest recovery of viable cells. The number of cells surviving after storage at -23.3 C was greater when the cells had been frozen in liquid N(2) than when they had been frozen at -23.3 C. All strains stored at -23.3 C showed a decrease in numbers of surviving cells; additives, particularly l-malic acid and apple juice, were advantageous in preserving the viability of the S. lactis C(2) and S. cremoris R(1) strains, but had little or no effect on the survival of S. diacetilactis DRC(2). l-Malic acid and apple juice stimulated acid production for all cultures in activity tests following incubation after thawing, whereas glycerol and dimethyl sulfoxide retarded its development.

Acetates↗

PubMed1996

Syntheses of (-)-Isocitric Acid Lactone and (-)-Homoisocitric Acid. A New Method of Conversion of Alkynylsilanes into the Alkynyl Thioether and Corresponding Carboxylic Acids.

A simple, stereoselective synthesis of natural isocitric and homoisocitric acids from a common alkynylsilane correlates the stereochemistry of these acids. Starting with dimethyl D-malate dianion, methyl 2-hydroxy-3-carbomethoxy-6-(trimethylsilyl)-5-hexynoate (6a) was prepared with a good stereoselectivity (threo/erythro 90/10). Oxidative cleavage of the triple bond provided isocitric acid lactone (8') in 15% overall yield starting from D-malic acid diester 1. The synthesis of homoisocitric acid relied on a new method of conversion of alkynylsilane to alkynyl thioether, which is converted to the carboxylic acid of the same chain length. Addition of benzenesulfenyl chloride to (trimethylsilyl)alkyne 6b and elimination of trimethylsilyl chloride gave the corresponding thioether 10, which by acid hydrolysis gave homoisocitric acid (11) in a 24% yield from D-malic acid ester. This novel method of conversion of alkynylsilane to the corresponding acid was illustrated with several other alkynyltrimethylsilanes.

Journal Article↗

PubMed1973

Organic acids and iron translocation in maize genotypes.

Translocation of Fe was studied in WF9 (Fe-efficient) and ys(1)/ys(1) (Fe-inefficient) maize (Zea mays L.) genotypes. Iron-deficient WF9 translocated more Fe to the tops than Fe-deficient ys(1)/ys(1). Malate and citrate contents of root saps increased nearly 2-fold and aconitate increased over 4-fold in both genotypes as Fe of nutrient solutions increased from 0.1 to 3 milligrams per liter. Relative acid contents in root saps were as follows: malate > aconitate > citrate. Citric acid concentrations in stem exudates were nearly the same as in root sap. Malic acid concentrations were considerably lower in exudates than in root saps, and only a trace of aconitic acid was detected in the exudates. The concentration of Fe was 7-fold higher in exudate of WF9 than in exudate of ys(1)/ys(1) and the concentration of exudate P was about the same for both genotypes.Electropherograms of WF9 stem exudates showed that (59)Fe moved toward the anode as (59)Fe-citrate. Exudates of ys(1)/ys(1) contained insufficient (59)Fe to produce radiographs. When (59)Fe was added in vitro to ys(1)/ys(1) stem exudate, the (59)Fe moved as (59)Fe-citrate, indicating that sufficient citric acid was present in the exudate to chelate the Fe. Effectiveness of citric, isocitric, trans-aconitic, and malic acids in moving (59)Fe electrophoretically in acetate, citrate, isocitrate, trans-aconitate, and malate buffers was studied. Malic, acetic, and trans-aconitic acids were ineffective in moving Fe from the origin. Citric acid moved Fe anodically whenever present on the electropherogram and successfully competed with the other acids for Fe.Results with ys(1)/ys(1) roots indicate an absence of an efficient mechanism for transporting Fe from cortical cells to the xylem. If Fe can reach the xylem stream, the ys(1)/ys(1) genotype should be as efficient as WF9 in moving Fe to the leaves.

Journal Article↗

PubMed1991

Progression and surface ultrastructure of in vitro caused erosive lesions in human and bovine enamel.

Surface prismatic and aprismatic human enamel and unpolished or diamond-polished specimens of bovine enamel, with test and control surfaces on each studied block, were immersed in phosphoric acid containing cola beverage (pH 2.6) and citric or malic acid containing sports drinks (pH 2.8 and 3.4, respectively) for 15-180 min. The specimens were then prepared and studied in a JEOL 35C scanning electron microscope. In human aprismatic surface enamel an irregular type of dissolution was observed, with severely affected areas adjacent to less affected ones. Prismatic human and bovine specimens showed a characteristic dissolution where initial erosion after 15 min immersion was seen to affect specifically the prism sheath areas. Longer immersion caused dissolution of enamel prism cores followed by interprismatic areas. In bovine enamel malic acid affected least the surface ultrastructure when compared with citric and phosphoric acids after 15-30 min of immersion, but thereafter no difference was observed between the acids in causing erosion. Diamond-polished enamel was found more liable to erosion than non-polished enamel. Thus, the structure of enamel greatly modified the progression of in vitro caused erosion, in particular in human tooth specimens.

Animals↗

PubMed1984

A study of the maloalcoholic fermentation pathway in Schizosaccharomyces pombe.

The pathway of the maloalcoholic fermentation in Schizosaccharomyces pombe was investigated by a 1H-, 2H- and 13C-n.m.r.-spectroscopic study of hydrogen and deuterium distribution on the ethanol produced by S. pombe from L-malic acid in 2H2O and from L-[2-2H]malic acid. Our findings rule out a double-decarboxylation mechanism and agree with a pathway that involves acetaldehyde as intermediate.

Ascomycota↗

PubMed1975

The pathway of carbon dioxide fixation in crassulacean plants.

Combined gas chromatography-mass spectrometry of malic acid derivatives has been used to show unequivocally that malic acid, synthesized during active acid accumulation in the dark by Kalanchoë daigremontiana Hammet et Perrier in the presence of (13)CO(2) is produced by a pathway involving a single carboxylation. The significance of the finding that crassulacean malate synthesized in the dark and in the presence of (14)CO(2) often contains 66% of the total carboxyl label in carbon atom 4, which has previously been taken to indicate the operation of a double carboxylation pathway or has been dismissed as an artefact, is discussed.

Journal Article↗

PubMed1977

Effect of aminoethoxy analog of rhizobitoxine on ripening of pears.

Ripening reactions in pears (Pyrus communis L.) were differentially affected by an aminoethoxy analog of rhizobitoxine (l-2-amino-4-[2-aminoethoxy]-trans-3-butenoic acid) (AAR). Ethylene production of both ;Anjou' and ;Bartlett' pears was inhibited by AAR. Decrease in firmness, increase in protein N and soluble pectin were delayed by AAR in ;Anjou' but not in ;Bartlett' pears. While loss in malic acid was retarded in ;Anjou' pears, rates of citric acid accumulation and malic acid reduction were not affected by AAR in ;Bartlett' pears.

Journal Article↗

PubMed2004

Malolactic bioconversion using a Oenococcus oeni strain for cider production: effect of yeast extract supplementation.

Yeast extract addition to reconstituted apple juice had a positive impact on the development of the malolactic starter culture used to ensure malolactic fermentation in cider, using active but non-proliferating cells. In this work, the reuse of fermentation lees from cider is proposed as an alternative to the use of commercial yeast extract products. Malolactic enzymatic assays, both in whole cells and cell-free extracts, were carried out to determine the best time to harvest cells for use as an inoculum in cider. Cells harvested at the late exponential phase, the physiological stage of growth corresponding to the maximum values of specific malolactic activity, achieved a good rate of malic acid degradation in controlled cider fermentation. Under the laboratory conditions used, malic acid degradation rates in the fermentation media turned out to be near 2.0 and 2.5 times lower, compared with the rates obtained in whole-cell enzymatic assays, as useful data applicable to industrial cider production.

Beverages↗

PubMed2006

Effect of low molecular weight organic acids on adsorption and desorption of fluoride on variable charge soils.

The effect of four low molecular weight organic acids on F(-) adsorption by two variable charge soils was investigated using a batch method. The organic acids reduced F(-) adsorption through competition by the acids with F(-) for sorption sites. Oxalic and malonic acids, both of which have simpler chemical structures, were more effective than citric or malic acid. The effect of organic acids on F(-) adsorption was more prominent at higher pH values and with larger amounts of the organic acids. The desorption study showed that the organic acids enhanced the desorption of F(-) adsorbed by the soils. In the control and malic acid systems, desorption increased sharply with decreasing pH, while in the oxalic acid system, desorption rose slightly with decreasing pH. Desorption also increased with increasing amount of organic acid added. There are two possible mechanisms for the effect of the organic acids on F(-) adsorption and desorption: (1) competition of the organic acids with F(-) for adsorption sites and (2) dissolution of the adsorbents, especially dissolution of soil Al.

Adsorption↗