Disease relevance of quinic acid

• Beyond establishing a fundamentally new route to an important chemical building block, oxidation of microbe-synthesized quinic acid provides an example of how the toxicity of aromatics toward microbes can be circumvented by interfacing chemical catalysis with biocatalysis [1].
• The positively acting regulator gene QUTA from Aspergillus nidulans has been identified and located within a cluster of quinic acid utilisation (QUT) genes isolated within a recombinant phage lambda (lambda Q1) [2].
• Acinetobacter Iwoffi RAG-1 produced a quinoprotein QDH apoenzyme since growth on quinic acid only occurred in the presence of PQQ [3].
• A new caffeoyl quinic acid from aster scaber and its inhibitory activity against human immunodeficiency virus-1 (HIV-1) integrase [4].
• These analogues were synthesized from quinic acid, and were assayed against type I (Salmonella typhi) and type II (S. coelicolor) dehydroquinases [5].

Psychiatry related information on quinic acid

• The results suggest that quinic acid derivatives from A. scaber might potentially be used as a therapeutic agent in Alzheimer disease [6].

High impact information on quinic acid

• This method was successful in identifying a model ensemble fitting available RNA profiling data on the qa gene cluster [7].
• Transcriptional activation of the Neurospora crassa qa genes normally requires the positive regulatory gene, qa-1F+, whose function is controlled by the inducer quinic acid and by the product of the negative regulatory gene, qa-1S+ [8].
• The qa-1 regulatory region controls the expression of the three structural genes required for the early reactions in quinic acid catabolism in Neurospora crassa [9].
• Purification and characterization of 3-dehydroshikimate dehydratase, an enzyme in the inducible quinic acid catabolic pathway of Neurospora crassa [10].
• Glucose is first converted into quinic acid using microbial catalysis [1].

Biological context of quinic acid

• Conditions suitable for oxidative decarboxylation of quinic acid with catalytic amounts of metal oxidant were also identified [1].
• QUTR (qutR-encoded transcription-repressing protein) is a multi-domain repressor protein active in the signal-transduction pathway that regulates transcription of the quinic acid utilization (qut) gene cluster in Aspergillus nidulans [11].
• On the basis of amino acid sequence alignments and the properties of mutants unable to utilize quinic acid as a carbon source, the AROM protein has been proposed to be homologous throughout its length with the proteins regulating transcription of the genes necessary for quinate catabolism [12].
• Cloning the quinic acid (aq) gene cluster from Neurospora crassa: identification of recombinant plasmids containing both qa-2+ and qa-3+ [13].
• Catabolic dehydroquinase assays indicated that qa-2 gene expression in the homothallic species is subject to induction by quinic acid, as is the case in N. crassa [14].

Anatomical context of quinic acid

• Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei [15].
• The caffeoyl conjugates of prenylhydroquinone glucoside and of quinic acid, either in the carboxyl-free or carboxymethyl forms, isolated from Phagnalon rupestre (Asteraceae), showed inhibitory activity on lipid peroxidation induced by Fe 2+/ascorbate and by CCl4/NADPH in rat liver microsomes, with IC50 values ranging from 3 to 11 microM [16].
• 3. In five experiments phenolic compounds, quinic acid or casein were infused into the rumen or abomasum of sheep and increments in urinary outputs of phenolic acids and phenols determined by thin-layer and gas-liquid chromatography [17].
• Although caffeic acid is easily absorbed in the small intestine, its esterification with quinic acid, as in chlorogenic acid, decreases its gut absorption and increases the quantities reaching the colon and its microbiota [18].
• Four quinic acid derivatives from A. scaber promoted neurite outgrowth in PC12 cells [6].

Associations of quinic acid with other chemical compounds

• Caffeic acid (3,4-dihydroxycinnamic acid), one of the most common phenolic acids, frequently occurs in fruits, grains and dietary supplements for human consumption as simple esters with quinic acid or saccharides, and are also found in traditional Chinese herbs [19].
• The quinic acid ulitization (qut) pathway in Aspergillus nidulans is a dispensable carbon utilization pathway that catabolizes quinate to protocatechuate via dehydroquinate and dehydroshikimate(DHS) [20].
• During May 1994, when the demand for sucrose was greatest, dogwood accumulated small amounts of glucose, quinic acid and Mg2+, offsetting a decline in nitrate concentration [21].
• 1'-O-Chlorogenoylchlorogenic acid and 1'-O-chlorogenoylneochlorogenic acid, a new type of quinic acid esters, have been isolated, in addition to six known quinic acid esters, rutin, and a mixture of saponins, from the methanol extract of Cussonia barteri Seemann (Araliaceae) leaves collected in Cameroon [22].
• The quinic acid-induced hypovirulence in Rhs 1AP cannot be overturned by the end-product of the shikimic acid pathway, chorismic acid, which enhances the virulence of Rhs 1AP dramatically when used alone [23].

Gene context of quinic acid

• At Wyeth we solved the first cocrystal structure of a small molecule, quinic acid, with E-selectin [24].
• The X-ray structure, together with structure based computational methods, was used to design quinic acid based libraries that were synthesized and evaluated for their ability to block the interaction of sLex with P-selectin [24].
• These genes code for 3-dehydroquinase enzymes of type II, involved in the catabolism of quinic acid [25].
• In this study, we report that in the virulent, M2-lacking isolate Rhs 1AP, which is isogenic to Rhs 1A1, quinic acid reduces virulence dramatically and induces synthesis of an M2-encoded polypeptide and its respective mRNA [23].
• Antioxidant activity of caffeoyl quinic acid derivatives from the roots of Dipsacus asper Wall [26].

Analytical, diagnostic and therapeutic context of quinic acid

• Analysis of the hydrophilic fraction of cranberry juice by reversed-phase HPLC using an Aqua LUNA column with diode array or MS detection revealed the presence of quinic acid, malic acid, shikimic acid, and citric acid [27].

References