Aconitic Acid is a weak organic acid, naturally found in some fruits and vegetables, that metabolizes to citric acid in the body and has been used in traditional medicine but can be toxic in high concentrations.

A novel selection regime for differentiation defects demonstrates an essential role for the stumpy form in the life cycle of the African trypanosome. (1/23)

A novel selection scheme has been developed to isolate bloodstream forms of Trypanosoma brucei, which are defective in their ability to differentiate to the procyclic stage. Detailed characterization of one selected cell line (defective in differentiation clone 1 [DiD-1]) has demonstrated that these cells are indistinguishable from the wild-type population in terms of their morphology, cell cycle progression, and biochemical characteristics but are defective in their ability to initiate differentiation to the procyclic form. Although a small proportion of DiD-1 cells remain able to transform, deletion of the genes for glycophosphatidyl inositol-phospholipase C demonstrated that this enzyme was not responsible for this inefficient differentiation. However, the attenuated growth of the Delta-glycophosphatidyl inositol-phospholipase C DiD-1 cells in mice permitted the expression of stumpy characteristics in this previously monomorphic cell line, and concomitantly their ability to differentiate efficiently was restored. Our results indicate that monomorphic cells retain expression of a characteristic of the stumpy form essential for differentiation, and that this is reduced in the defective cells. This approach provides a new route to dissection of the cytological and molecular basis of life cycle progression in the African trypanosome.  (+info)

Unexpected anthracycline-mediated alterations in iron-regulatory protein-RNA-binding activity: the iron and copper complexes of anthracyclines decrease RNA-binding activity. (2/23)

Anthracyclines are effective antineoplastic agents. However, the interaction of these drugs with iron (Fe) is an important cause of myocardial toxicity, limiting their therapeutic use (J Lab Clin Med 122:245-251, 1993). To overcome this limitation, it is crucial to understand how anthracyclines interact with the Fe metabolism of myocardial and neoplastic cells. Iron-regulatory proteins (IRPs) play vital roles in regulating cellular Fe metabolism via their mRNA-binding activity. We showed that doxorubicin (DOX) and its analogs interfere with tumor and myocardial cell Fe metabolism by affecting the RNA-binding activity of IRPs. Unexpectedly, experiments with the free radical scavengers, catalase, superoxide dismutase, ebselen, and Mn(III) tetrakis (4-benzoic acid) porphyrin complex, suggested that the effects of DOX on IRP-RNA-binding activity were not due to anthracycline-mediated free radical production. In contrast to previous studies, we showed that the DOX metabolite, doxorubicinol, had no effect on IRP-RNA-binding activity. Rather, the anthracycline-Fe and -copper (Cu) complexes decreased IRP-RNA-binding activity, indicating that formation of anthracycline-metal complexes may affect cellular Fe metabolism. In addition, anthracyclines prevented the response of IRPs to the depletion of intracellular Fe by chelators. This information may be useful in designing novel therapeutic strategies against tumor cells by combining chelators and anthracyclines. Interestingly, the effect of DOX on primary cultures of cardiomyocytes was similar to that observed using neoplastic cells, and particularly notable was the decrease in IRP2-RNA-binding activity. Our results add significant new information regarding the effects of anthracyclines on Fe metabolism that may lead to the design of more effective treatments.  (+info)

Cold shock and regulation of surface protein trafficking convey sensitization to inducers of stage differentiation in Trypanosoma brucei. (3/23)

Transmission of a protozoan parasite from a vertebrate to invertebrate host is accompanied by cellular differentiation. The signals from the environment that trigger the process are poorly understood. The model parasite Trypanosoma brucei proliferates in the mammalian bloodstream and in the tsetse fly. On ingestion by the tsetse, the trypanosome undergoes a rapid differentiation that is marked by replacement of the variant surface glycoprotein (VSG) coat with GPI-anchored EP and GPEET procyclins. Here we show that a cold shock of DeltaT > 15 degrees C is sufficient to reversibly induce high-level expression of the insect stage-specific EP gene in the mammalian bloodstream stages of T. brucei. The 3'-UTR of the EP mRNA is necessary and sufficient for the increased expression. During cold shock, EP protein accumulates in the endosomal compartment in the proliferating, slender, bloodstream stage, whereas the EP is present on the plasma membrane in the quiescent, stumpy, bloodstream stage. Thus, there is a novel developmentally regulated cell surface access control mechanism for a GPI-anchored protein. In addition to inducing EP expression, cold shock results in the acquisition of sensitivity to micromolar concentrations of cis-aconitate and citrate by stumpy but not slender bloodstream forms. The cis-aconitate and citrate commit stumpy bloodstream cells to differentiation to the procyclic stage along with rapid initial proliferation. We propose a hierarchical model of three events that regulate differentiation after transmission to the tsetse: sensing the temperature change, surface access of a putative receptor, and sensing of a chemical cue.  (+info)

The FAD-dependent tricarballylate dehydrogenase (TcuA) enzyme of Salmonella enterica converts tricarballylate into cis-aconitate. (4/23)

Tricarballylate is the causative agent of grass tetany, a ruminant disease characterized by acute magnesium deficiency. Tricarballylate toxicity has been attributed to its ability to chelate magnesium and to inhibit aconitase, a Krebs cycle enzyme. Neither the ruminant nor the normal rumen flora can catabolize tricarballylate to ameliorate its toxic effects. However, the gram-negative enterobacterium Salmonella enterica can use tricarballylate as a carbon and energy source, providing an opportunity to study the genes and enzymes required for tricarballylate catabolism. The tricarballylate utilization (tcu) genes are organized into two transcriptional units, i.e., tcuR and tcuABC. Here, we report the initial biochemical analysis of TcuA. TcuA catalyzed the oxidation of tricarballylate to cis-aconitate. The apparent K(m) of TcuA for tricarballylate was 3.8 +/- 0.4 mM, with a V(max) of 7.9 +/- 0.3 mM min(-1), turnover number (k(cat)) of 6.7 x 10(-2) s(-1), and a catalytic efficiency (k(cat)/K(m)) of 17.8 M(-1) s(-1). Optimal activity was measured at pH 7.5 and 30 degrees C. The enzyme was inactivated at 45 degrees C. One mole of FAD was present per mole of TcuA. We propose a role for TcuB as an electron shuttle protein responsible for oxidizing FADH(2) back to FAD in TcuA.  (+info)

The three-dimensional crystal structure of the PrpF protein of Shewanella oneidensis complexed with trans-aconitate: insights into its biological function. (5/23)

In bacteria, the dehydration of 2-methylcitrate to yield 2-methylaconitate in the 2-methylcitric acid cycle is catalyzed by a cofactor-less (PrpD) enzyme or by an aconitase-like (AcnD) enzyme. Bacteria that use AcnD also require the function of the PrpF protein, whose function was previously unknown. To gain insights into the function of PrpF, the three-dimensional crystal structure of the PrpF protein from the bacterium Shewanella oneidensis was solved at 2.0 A resolution. The protein fold of PrpF is strikingly similar to those of the non-PLP-dependent diaminopimelate epimerase from Haemophilus influenzae, a putative proline racemase from Brucella melitensis, and to a recently deposited structure of a hypothetical protein from Pseudomonas aeruginosa. Results from in vitro studies show that PrpF isomerizes trans-aconitate to cis-aconitate. It is proposed that PrpF catalysis of the cis-trans isomerization proceeds through a base-catalyzed proton abstraction coupled with a rotation about C2-C3 bond of 2-methylaconitate, and that residue Lys73 is critical for PrpF function. The newly identified function of PrpF as a non-PLP-dependent isomerase, together with the fact that PrpD-containing bacteria do not require PrpF, suggest that the isomer of 2-methylaconitate that serves as a substrate of aconitase must have the same stereochemistry as that synthesized by PrpD. From this, it follows that the 2-methylaconitate isomer generated by AcnD is not a substrate of aconitase, and that PrpF is required to generate the correct isomer. As a consequence, the isomerase activity of PrpF may now be viewed as an integral part of the 2-methylcitric acid cycle.  (+info)

A high-throughput method to measure NaCl and acid taste thresholds in mice. (6/23)

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A surface transporter family conveys the trypanosome differentiation signal. (7/23)

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Synthesis and properties of polycarboxylate-type green surfactants with S- or N-linkages. (8/23)

Polycarboxylate-type green surfactants with either sulfide- (S-) or imino- (N-) linkages were prepared in high yields by a single addition reaction of fatty mercaptan or fatty amine with unsaturated polycarboxylic acids such as fumaric, maleic, itaconic and aconitic acids. They exhibited surfactant properties and excellent biodegradabilities. Also, green surfactants with S-linkages showed better calcium ion sequestration abilities compared to the corresponding surfactant having an N-linkage. Among these surfactants, aconitic acid-derived polycarboxylate with an S-linkage exhibited calcium ion sequestration capacities similar to that of disodium 3-oxapentanedioate (ODA), a conventional calcium ion sequestrant on a molar basis of the surfactant.  (+info)

Aconitic acid is a type of organic acid that is found naturally in some plants, including Aconitum napellus (monkshood or wolf's bane). It is a white crystalline powder with a sour taste and is soluble in water. In the human body, aconitic acid is produced as a byproduct of energy metabolism and can be found in small amounts in various tissues.

Aconitic acid has three carboxylic acid groups, making it a triprotic acid, which means that it can donate three protons (hydrogen ions) in solution. It is a strong acid and is often used as a laboratory reagent for various chemical reactions. In the food industry, aconitic acid may be used as a food additive or preservative.

It's important to note that some species of Aconitum plants contain highly toxic compounds called aconitines, which can cause serious harm or even death if ingested. Therefore, these plants should not be consumed or handled without proper knowledge and precautions.

... is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis- ... Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid: (HO2CCH2)2C(OH)CO2H → HO2CCH=C(CO2H)CH2CO2H ... aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is ... "Aconitic Acid - Compound Summary (CID 309)". PubChem. Dawson, R. M. C.; Elliott, D. C.; Elliott, W. H. (1989). Data for ...
... aconitic acid, and propane-1,2,3-tricarboxylic acid (tricarballylic acid, carballylic acid) Acids in wine This still does not ... Aconitic acid can be synthesized by dehydration of citric acid using sulfuric acid: (HO2CCH2)2C(OH)CO2H → HO2CCH=C(CO2H)CH2CO2H ... Citric acid can be used as an alternative to nitric acid in passivation of stainless steel. Citric acid can be used as a lower- ... Citric acid is an alpha hydroxy acid and is an active ingredient in chemical skin peels. Citric acid is commonly used as a ...
The properties and reaction mechanism of cis-aconitic acid decarboxylase". J. Biol. Chem. 226 (2): 703-20. PMID 13438855. ... This enzyme participates in c5-branched dibasic acid metabolism. BENTLEY R, THIESSEN CP (1957). "Biosynthesis of itaconic acid ... Other names in common use include cis-aconitic decarboxylase, CAD, cis-aconitate carboxy-lyase, and cis-aconitate carboxy-lyase ...
ISBN 978-0-9678550-9-7. Martynov, A. V. (2005-12-06). "New Approach to the Synthesis of trans-Aconitic Acid Imides". ChemInform ... Most imides are cyclic compounds derived from dicarboxylic acids, and their names reflect the parent acid. Examples are ... The intramolecular reaction of a carboxylic acid with an amide is far faster than the intermolecular reaction, which is rarely ... One example is Kapton where the repeat unit consists of two imide groups derived from aromatic tetracarboxylic acids. Another ...
The plant is poisonous, containing cardiostimulant compounds, such as adonidin and aconitic acid. Infusions of the plant are ...
Homoaconitatic acid (homoaconitate) is related to aconitic acid but with one extra carbon. It is part of the α-aminoadipate ... Homoisocitric acid Murray Strassman and Louis N. Ceci (1966). "Enzymatic Formation of cis-Homoaconitic Acid, an Intermediate in ... Tricarboxylic acids, All stub articles, Organic compound stubs). ...
Effect of tricarballylic acid, a nonmetabolizable rumen fermentation product of trans-aconitic acid, on Mg, Ca and Zn ... Enrichment and isolation of rumen bacteria that reduce trans-aconitic acid to tricarballylic acid. Appl. Env. Microbiol. 49: ... Potassium fertilizer application results in increased concentration of aconitic acid in some grass species. Magnesium ... Potassium effects on minerals and organic acids in three cool-season grasses. J. Plant Nutr. 15: 1007-1025. Gustav Rosenberger ...
The name itaconic acid was devised as an anagram of aconitic acid, another derivative of citric acid. Since the 1960s, it is ... 2-methylmaleic acid). Partial hydrogenation of itaconic acid over Raney nickel affords 2-methylsuccinic acid. Itaconic acid is ... Itaconic acid, or methylidenesuccinic acid, is an organic compound. This dicarboxylic acid is a white solid that is soluble in ... Historically, itaconic acid was obtained by the distillation of citric acid, but currently it is produced by fermentation. ...
These intermediates were subsequently used for the generation of the Krebs cycle intermediates aconitic and isocitric acids. ... It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a ... Maleic acid is biodegradable under aerobic conditions in sewage sludge as well as in soil and water. Food starch for use in ... It hydrolyzes, producing maleic acid, cis-HOOC-CH=CH-COOH. With alcohols, the half-ester is generated, e.g., cis-HOOC-CH=CH- ...
The seed contains cis-aconitic anhydride ethyl ester and cis-2,4,5-trihydroxycinnamic acid. English Names for Korean Native ... Zhao M, Chen JY, Xu LJ, Goedecke T, Zhang XQ, Duan JA, Che CT (2012). "Cis-aconitic anhydride ethyl ester and phenolic ...
All parts of the plant contain alkaloids associated with aconitic acid (primarily aconitine), but their concentration depends ...
A. terreus is commonly used in industry to produce important organic acids, such as itaconic acid and cis-aconitic acid, as ... The polyketide synthase gene atX produces 6-Methylsalicylic acid in A. terreus. Aspergillus terreus is not as common as other ... Shimada, A; Kusano,M; Takeuchi,S; Fujioka,S; Inokuchi,T; Kimura, Y (2002). "Aspterric acid and 6-hydroxymellein, inhibitors of ... Its secondary metabolites, aspterric acid and 6-hydroxymellein, released from the fungus inhibit the production of pollen, the ...
Citric acid Aconitic acid Isocitric acid Aconitase normally catalyses, via the intermediate aconitic acid, the interconversion ... Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and β-carboxyglutaric acid, is a ... However, the hydroxide group is essential to proceed from citric acid to aconitic acid, therefore the enzyme is not able to ... such as actinoplanic acid. Propane-1,2,3-tricarboxylic acid can be synthesized in two steps from fumaric acid. ...
Acetic oxalic anhydride Aconitic acid Benzenehexol Dehydroascorbic acid (DHA) 1,2,3,4,5,6,-hexa hydroxy benzen This set index ...
Citric acid Aconitic acid Isocitric acid Aconitase, displayed in the structures in the right margin of this page, has two ... However, aconitase cannot bind this substrate and thus the citric acid cycle is halted. The iron sulfur cluster is highly ... Takusagawa F. "Chapter 16: Citric Acid Cycle" (PDF). Takusagawa's Note. The University of Kansas. Archived from the original ( ... Fluoroacetate, in the citric acid cycle, can innocently enter as fluorocitrate. ...
2-Acetyl-3-ethylpyrazine 2-Acetyl-5-methylfuran Acetylpyrazine 2-Acetylpyridine 3-Acetylpyridine 2-Acetylthiazole Aconitic acid ... acid alpha-Methylcinnamaldehyde Methylcyclopentenolone 2-Methylheptanoic acid 2-Methylhexanoic acid 3-Methylpentanoic acid 4- ... 12-Octadecadienoic acid (48%) and 9,12,15-octadecatrienoic acid (52%) delta-Octalactone gamma-Octalactone Octanal Octanoic acid ... Hexanal Hexanoic acid 2-Hexen-1-Ol 3-Hexen-1-Ol cis-3-Hexen-1-yl acetate 2-Hexenal 3-Hexenoic acid trans-2-Hexenoic acid cis-3- ...
"Cis-aconitic anhydride ethyl ester and phenolic compounds from the seeds of Alisma orientale". Natural Product Communications. ... 2,4,5-Trihydroxycinnamic acid is a hydroxycinnamic acid found in rooibos tea. cis-2,4,5-Trihydroxycinnamic acid can be isolated ... Hydroxycinnamic acids, Hydroxyquinols, Vinylogous carboxylic acids, All stub articles, Aromatic compound stubs). ...
... hexuronic acids MeSH D02.241.081.844.915.400.500 - iduronic acid MeSH D02.241.081.901.177 - aconitic acid MeSH D02.241.081.901. ... quinic acid MeSH D02.241.511.852 - shikimic acid MeSH D02.241.511.902 - sugar acids MeSH D02.241.511.902.107 - ascorbic acid ... edetic acid MeSH D02.241.081.038.455 - egtazic acid MeSH D02.241.081.038.581 - iodoacetic acid MeSH D02.241.081.038.581.400 - ... muramic acids MeSH D02.241.081.844.562 - neuraminic acids MeSH D02.241.081.844.562.668 - sialic acids MeSH D02.241.081.844. ...

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