Source:http://linkedlifedata.com/resource/pubmed/id/20399443
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
21
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pubmed:dateCreated |
2010-5-3
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pubmed:abstractText |
In this study, the racemization kinetic parameters of R-(-)-synephrine, the active phenethylamine alkaloid of Citrus aurantium L., were determined by means of an off-column HPLC method. Enantioseparation was carried out in different buffer solutions and solvents on a chiral stationary phase (CSP) with cellobiohydrolase as the chiral selector (Chiral-CBH, 100 mm x 4.0 mm i.d., 5 microm). The mobile phase was 10 mM sodium phosphate buffer (pH 6.0)-2-propanol (95:5, w/w), with 50 microM disodium EDTA, at 0.8 mL/min. The column was thermostatted at 20 degrees C and detection was set at 225 nm. The influence of pH value, ionic strength, temperature and addition of organic modifier on the rate constant, the half-life of racemization and the free energy barrier of racemization of R-(-)-synephrine were determined. Among the different chemical and physical parameters evaluated as affecting the racemization of naturally occurring R-(-)-synephrine, pH, temperature and addition of an organic co-solvent appear to have the strongest effect, while ionic strength does not exert a significant influence on the racemization rate. The results of the present study indicated that synephrine racemization is possible at high temperature at both acidic and basic pH values; therefore, the extraction procedure of R-(-)-synephrine from the plant material should be carried out under specific conditions to preserve the stereochemical integrity and the biological activity of this secondary metabolite.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
May
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pubmed:issn |
1873-3778
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pubmed:author | |
pubmed:copyrightInfo |
2010 Elsevier B.V. All rights reserved.
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pubmed:issnType |
Electronic
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pubmed:day |
21
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pubmed:volume |
1217
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
3503-10
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pubmed:meshHeading |
pubmed-meshheading:20399443-Cellulose 1,4-beta-Cellobiosidase,
pubmed-meshheading:20399443-Chromatography, High Pressure Liquid,
pubmed-meshheading:20399443-Citrus,
pubmed-meshheading:20399443-Ethanol,
pubmed-meshheading:20399443-Hydrogen-Ion Concentration,
pubmed-meshheading:20399443-Kinetics,
pubmed-meshheading:20399443-Osmolar Concentration,
pubmed-meshheading:20399443-Stereoisomerism,
pubmed-meshheading:20399443-Synephrine,
pubmed-meshheading:20399443-Temperature,
pubmed-meshheading:20399443-Thermodynamics
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pubmed:year |
2010
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pubmed:articleTitle |
Study on the racemization of synephrine by off-column chiral high-performance liquid chromatography.
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pubmed:affiliation |
Department of Pharmaceutical Sciences, University of Modena and Reggio Emilia, Via G. Campi 183, 41100 Modena, Italy. federica.pellati@unimore.it
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pubmed:publicationType |
Journal Article
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