A concise enantio- and diastereo-controlled synthesis of (−)-quinic acid and (−)-shikimic acid

1998 ◽  
pp. 2033-2034 ◽  
Author(s):  
Kou Hiroya ◽  
Kunio Ogasawara
Keyword(s):  
Shikimic Acid ◽  
Quinic Acid ◽  
Controlled Synthesis

scholarly journals Integrated Analysis of the Transcriptome and Metabolome of Cecropia obtusifolia: A Plant with High Chlorogenic Acid Content Traditionally Used to Treat Diabetes Mellitus

2020 ◽  
Vol 21 (20) ◽  
pp. 7572
Author(s):  
Jorge David Cadena-Zamudio ◽  
Pilar Nicasio-Torres ◽  
Juan Luis Monribot-Villanueva ◽  
José Antonio Guerrero-Analco ◽  
Enrique Ibarra-Laclette
Keyword(s):  
Diabetes Mellitus ◽  
Chlorogenic Acid ◽  
High Performance ◽  
Time Course ◽  
Shikimic Acid ◽  
Quinic Acid ◽  
Integrated Analysis ◽  
Cecropia Obtusifolia ◽  
Key Enzyme

This investigation cultured Cecropia obtusifolia cells in suspension to evaluate the effect of nitrate deficiency on the growth and production of chlorogenic acid (CGA), a secondary metabolite with hypoglycemic and hypolipidemic activity that acts directly on type 2 diabetes mellitus. Using cell cultures in suspension, a kinetics time course was established with six time points and four total nitrate concentrations. The metabolites of interest were quantified by high-performance liquid chromatography (HPLC), and the metabolome was analyzed using directed and nondirected approaches. Finally, using RNA-seq methodology, the first transcript collection for C. obtusifolia was generated. HPLC analysis detected CGA at all sampling points, while metabolomic analysis confirmed the identity of CGA and of precursors involved in its biosynthesis. Transcriptome analysis identified differentially expressed genes and enzymes involved in the biosynthetic pathway of CGA. C. obtusifolia probably expresses a key enzyme with bifunctional activity, the hydroxycinnamoyl-CoA quinate hydroxycinnamoyl transferase and hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase (HQT/HCT), which recognizes shikimic acid or quinic acid as a substrate and incorporates either into one of the two routes responsible for CGA biosynthesis.

scholarly journals Extraction and Simultaneous Determination of Glyphosate, AMPA and Compounds of the Shikimic Acid Pathway in Plants

2015 ◽  
Vol 33 (2) ◽  
pp. 295-304 ◽  
Author(s):  
G.L.G.C. Gomes ◽  
C.A. Carbonari ◽  
E.D. Velini ◽  
M.L.B. Trindade ◽  
J.R.M. Silva
Keyword(s):  
Mass Spectrometry ◽  
Shikimic Acid ◽  
Quinic Acid ◽  
Saccharum Officinarum ◽  
Joint Analysis ◽  
Aminomethylphosphonic Acid ◽  
Water Ph ◽  
Acid Pathway ◽  
Forced Air ◽  
Air Circulation

This study has aimed to develop a method for simultaneous extraction and determination by liquid chromatography and mass spectrometry (LC-MS/MS) of glyphosate, aminomethylphosphonic acid (AMPA), shikimic acid, quinic acid, phenylalanine, tyrosine and tryptophan. For the joint analysis of these compounds the best conditions of ionization in mass spectrometry and for chromatographic separation of the compounds were selected. Calibration curves and linearity ranges were also determined for each compound. Different extraction systems of the compounds were tested from plant tissues collected from sugarcane (Saccharum officinarum) and eucalyptus (Eucalyptus urophylla platiphylla) plants two days after the glyphosate application at the dose of 720 g a.e. ha-1. The plant material was dried in a forced air circulation drying oven and in a lyophilizer, and subsequently the extractions with acidified water (pH 2.5), acetonitrile-water (50:50) [v/v] and methanol-water (50:50) [v/v] were tested. To verify the recovery of the compounds in the plant matrix with acidified water as an extracting solution, the samples were fortified with a solution containing the mixture of the different analytical standards present so that this one presented the same levels of 50 and 100 μg L-1 of each compound. All experiments were conducted with three replicates. The analytical method developed was efficient for compounds quantifications. The extraction from the samples dried in an oven and using acidified water allowed better extraction levels for all compounds. The recovery levels of the compounds in the fortified samples with known amounts of each compound for both plants samples were rather satisfactory.

The Role of the ydiB Gene, Which Encodes Quinate/Shikimate Dehydrogenase, in the Production of Quinic, Dehydroshikimic and Shikimic Acids in a PTS- Strain of Escherichia coli

2016 ◽  
Vol 27 (1) ◽  
pp. 11-21 ◽  
Author(s):  
Sofía García ◽  
Noemí Flores ◽  
Ramón De Anda ◽  
Georgina Hernández ◽  
Guillermo Gosset ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Shikimic Acid ◽  
Sharp Decrease ◽  
Quinic Acid ◽  
Shikimate Dehydrogenase ◽  
Molar Yield ◽  
E Coli ◽  
Downstream Processes ◽  
Precise Role

The culture of engineered <i>Escherichia coli</i> for shikimic acid (SA) production results in the synthesis of quinic acid (QA) and dehydroshikimic acid (DHS), reducing SA yield and impairing downstream processes. The synthesis of QA by quinate/shikimate dehydrogenase (YdiB, <i>ydiB</i>) has been previously proposed; however, the precise role for this enzyme in the production of QA in engineered strains of <i>E. coli</i> for SA production remains unclear. We report the effect of the inactivation or the overexpression of <i>ydiB</i> in <i>E. coli</i> strain PB12.SA22 on SA, QA, and DHS production in batch fermentor cultures. The results showed that the inactivation of <i>ydiB </i>resulted in a 75% decrease in the molar yield of QA and a 6.17% reduction in the yield of QA (mol/mol) relative to SA with respect to the parental strain. The overexpression of <i>ydiB</i> caused a 500% increase in the molar yield of QA and resulted in a 152% increase in QA (mol/mol) relative to SA, with a sharp decrease in SA production. Production of SA, QA, and DHS in parental and derivative <i>ydiB </i>strains suggests that the synthesis of QA results from the reduction of 3-dehydroquinate by YdiB before its conversion to DHS.

scholarly journals Species differences in the aromatization of quinic acid in vivo and the role of gut bacteria

1970 ◽  
Vol 116 (3) ◽  
pp. 437-443 ◽  
Author(s):  
R. H. Adamson ◽  
J. W. Bridges ◽  
M. E. Evans ◽  
R. T. Williams
Keyword(s):  
Rhesus Monkey ◽  
Rhesus Monkeys ◽  
Hippuric Acid ◽  
Shikimic Acid ◽  
Tree Shrew ◽  
Quinic Acid ◽  
New World Monkeys ◽  
Old World Monkeys ◽  
Gut Flora ◽  
Old World

1. The fate of (-)-quinic acid has been investigated in 22 species of animals including man. 2. In man and three species of Old World monkeys, i.e. rhesus monkey, baboon and green monkey, oral quinic acid was extensively aromatized (20–60%) and excreted in the urine as hippuric acid, which was determined fluorimetrically. 3. In three species of New World monkeys, i.e. squirrel monkey, spider monkey and capuchin, in three species of lemurs, i.e. bushbaby, slow loris and tree shrew, in the dog, cat, ferret, rabbit, rat, mouse, guinea pig, hamster, lemming, fruit bat, hedgehog and pigeon, oral quinic acid was not extensively aromatized (0–5%). 4. In the rhesus monkey, injected quinic acid was not aromatized, but largely excreted unchanged. 5. In rhesus monkeys pretreated with neomycin to suppress gut flora, the aromatization of oral quinic acid was considerably suppressed. 6. In rats and rhesus monkeys [14C]quinic acid was used and this confirmed its low aromatization in rats and its high aromatization in the monkeys. 7. Shikimic acid given orally was excreted as hippuric acid (26–56%) in rhesus monkeys, but not in rats. 8. The results support the view that quinic acid and shikimic acid are aromatized by the gut flora in man and the Old World monkeys.

scholarly journals Biochemical Markers of Contact with the Organic Pollutants of Urban Atmosphere in the Leaves of Woody Plants

2020 ◽  
Vol 24 ◽  
pp. 00089
Author(s):  
Natalya Tsybulya ◽  
Lyudmila Chindyaeva ◽  
Galina Dultseva
Keyword(s):  
Chemical Composition ◽  
Organic Pollutants ◽  
Acid Content ◽  
Woody Plants ◽  
Shikimic Acid ◽  
Quinic Acid ◽  
Atmospheric Pollutants ◽  
Urban Atmosphere ◽  
Formaldehyde Concentration ◽  
High Concentration

Changes caused by contact with typical organic pollutants of urban atmosphere (formaldehyde, benzaldehyde, hydroperoxides) in the chemical composition of the leaves and shoots of woody plants are investigated. A decrease in quinic acid content and an increase in shikimic acid content were detected in the young shoots of Picea obovata Ledeb. and Picea pungens Engelm.. Investigation of changes in the chemical composition of shoots in contact with pollutants under laboratory conditions revealed that the contact with formaldehyde and hydroperoxide affects the biochemical cycle of quinic acid. High concentration of gaseous formaldehyde was found to cause an increase in the content of lactic acid in the leaves of Padus maackii (Rupr.) Kom.. In the leaves of Tilia cordata Mill. and Syringa josikaea Jacq. fil., high formaldehyde concentration caused a decrease in glycolic acid content and an increase in oxalic acid content, while after the contact with gaseous benzaldehyde this compound was detected in the leaves in rather high concentration, Analysis of the ligneous parts of plants from the territories with heavy air pollution revealed increased content of syringaldehyde, which may be a consequence of the oxidative degradation of lignin under the action of atmospheric pollutants.

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