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1.
J Chromatogr A ; 1393: 1-7, 2015 May 08.
Article in English | MEDLINE | ID: mdl-25840660

ABSTRACT

Polymer monolith microextraction (PMME) based on capillary monolithic column is an effective and useful technique to preconcentrate trace analytes from environmental and biological samples. Here, we report the fabrication of a novel aluminum terephthalate metal-organic framework (MIL-53(Al)) incorporated capillary monolithic column via in situ polymerization for the PMME of non-steroidal anti-inflammatory drugs (NSAIDs) (ketoprofen, fenbufen and ibuprofen) in water and urine samples. The fabricated MIL-53(Al) incorporated monolith was characterized by X-ray powder diffractometry, scanning electron microscopy, Fourier transform infrared spectrometry, and nitrogen adsorption experiment. The MIL-53(Al) incorporated monolith gave larger surface area than the neat polymer monolith. A 2-cm long MIL-53(Al) incorporated capillary monolith was applied for PMME coupled with high-performance liquid chromatography for the determination of the NSAIDs. Potential factors affecting the PMME were studied in detail. Under the optimized conditions, the developed method gave the enhancement factors of 46-51, the linear range of 0.40-200µgL(-1), the detection limits (S/N=3) of 0.12-0.24µgL(-1), and the quantification limits (S/N=10) of 0.40-0.85µgL(-1). The recoveries for spiked NSAIDs (20µgL(-1)) in water and urine samples were in the range of 77.3-104%. Besides, the MIL-53(Al) incorporated monolith was stable enough for 120 extraction cycles without significant loss of extraction efficiency. The developed method was successfully applied to the determination of NSAIDs in water and urine samples.


Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Ibuprofen/isolation & purification , Ketoprofen/isolation & purification , Methacrylates , Phenylbutyrates/isolation & purification , Phthalic Acids , Solid Phase Extraction/instrumentation , Adsorption , Aluminum , Anti-Inflammatory Agents, Non-Steroidal/urine , Chromatography, High Pressure Liquid/methods , Ibuprofen/urine , Ketoprofen/urine , Limit of Detection , Phenylbutyrates/urine , Salts , Solid Phase Extraction/methods , Water/chemistry
2.
Fitoterapia ; 103: 113-21, 2015 Jun.
Article in English | MEDLINE | ID: mdl-25810314

ABSTRACT

Inhibitors of protein tyrosine phosphatase 1B (PTP1B) are promising agents for the treatment of type 2 diabetes and obesity. The bioactivity-guided isolation led to the separation of two new compounds, (±)-tradescantin (13) and tradescantoside (16), along with fourteen known compounds (1-12, 14, and 15) from the aerial parts of Tradescantia spathacea Sw. (Commelinaceae). Their chemical structures were elucidated by spectroscopic methods as well as by comparing with those reported in the literature. The isolated compounds (1-16) were then examined for their inhibitory activity toward PTP1B. The results indicated that compounds 2, 6, 8, and 12 possessed potent inhibition with IC50 values of 7.82±0.79, 6.80±0.89, 4.55±0.92, and 6.38±0.14 µM, respectively. Kinetic study of compounds 2, 6, 8, 12, 13, and 16 was conducted and the structure-activity relationships of the isolated compounds (1-16) were also discussed herein. To the best of our knowledge, all the isolates were separated for the first time from this plant.


Subject(s)
Enzyme Inhibitors/chemistry , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Tradescantia/chemistry , Caffeic Acids/chemistry , Caffeic Acids/isolation & purification , Enzyme Inhibitors/isolation & purification , Glucosides/chemistry , Glucosides/isolation & purification , Inhibitory Concentration 50 , Molecular Structure , Phenylbutyrates/chemistry , Phenylbutyrates/isolation & purification , Plant Components, Aerial/chemistry
3.
Anal Chim Acta ; 820: 76-83, 2014 Apr 11.
Article in English | MEDLINE | ID: mdl-24745740

ABSTRACT

A new approach for the analysis of the cyanobacterial microcystins (MCs) in environmental water matrices has been developed. It offers a cost efficient alternative method for the fast quantification of total MCs using mass spectrometry. This approach permits the quantification of total MCs concentrations without requiring any derivatization or the use of a suite of MCs standards. The oxidation product 2-methyl-3-methoxy-4-phenylbutyric acid (MMPB) was formed through a Lemieux oxidation and represented the total concentration of free and bound MCs in water samples. MMPB was analyzed using laser diode thermal desorption-atmospheric pressure chemical ionization coupled to tandem mass spectrometry (LDTD-APCI-MS/MS). LDTD is a robust and reliable sample introduction method with ultra-fast analysis time (<15 s sample(-1)). Several oxidation and LDTD parameters were optimized to improve recoveries and signal intensity. MCs oxidation recovery yield was 103%, showing a complete reaction. Internal calibration with standard addition was achieved with the use of 4-phenylbutyric acid (4-PB) as internal standard and showed good linearity (R(2)>0.999). Limits of detection and quantification were 0.2 and 0.9 µg L(-1), respectively. These values are comparable with the WHO (World Health Organization) guideline of 1 µg L(-1) for total microcystin-LR congener in drinking water. Accuracy and interday/intraday variation coefficients were below 15%. Matrix effect was determined with a recovery of 91%, showing no significant signal suppression. This work demonstrates the use of the LDTD-APCI-MS/MS interface for the screening, detection and quantification of total MCs in complex environmental matrices.


Subject(s)
Atmospheric Pressure , Lasers , Microcystins/analysis , Tandem Mass Spectrometry/methods , Water Pollutants, Chemical/analysis , Water/chemistry , Limit of Detection , Microcystins/chemistry , Microcystins/isolation & purification , Oxidation-Reduction , Phenylbutyrates/chemistry , Phenylbutyrates/isolation & purification , Reproducibility of Results , Solvents/chemistry , Time Factors , Water Pollutants, Chemical/chemistry , Water Pollutants, Chemical/isolation & purification
5.
Anal Chim Acta ; 709: 66-72, 2012 Jan 04.
Article in English | MEDLINE | ID: mdl-22122933

ABSTRACT

The optimization of analytical procedures for the quantification of free and total microcystins (MCs) in natural sediments was systematically examined based on solvent extraction and Lemieux oxidation. In this optimized analytical procedure, a sequential solvent extraction using 50% (v/v) methanol and EDTA-sodium pyrophosphate was selected as the optimal extraction solvent for free MCs analysis, after which the purified extracts and sediment residuals were applied to the optimized Lemieux oxidation for determination of total MCs in lake sediments. The optimized procedures were shown to be efficient and reliable for the routine analysis of both free and total MCs in lake sediment samples, as indicated by the minimal adverse impact of sediment organic matter on the recovery of free MCs and yield of MMPB (2-methyl-3-methoxy-4-phenylbutyric acid). Finally, the developed procedures were applied to field sediment samples collected from Lake Dianchi during a bloom season and seven of thirty samples showed positive results.


Subject(s)
Chromatography, High Pressure Liquid , Geologic Sediments/chemistry , Microcystins/analysis , Soil Pollutants/analysis , Diphosphates/chemistry , Edetic Acid/chemistry , Lakes , Liquid-Liquid Extraction , Methanol/chemistry , Microcystins/isolation & purification , Oxidation-Reduction , Phenylbutyrates/analysis , Phenylbutyrates/isolation & purification , Soil Pollutants/isolation & purification
6.
Biofouling ; 27(5): 519-28, 2011 May.
Article in English | MEDLINE | ID: mdl-21614700

ABSTRACT

Biofilm formation is a critical problem in nosocomial infections and in the aquaculture industries and biofilms show high resistance to antibiotics. The aim of the present study was to reveal a novel anti-biofilm compound from marine bacteria against antibiotic resistant gram-positive and gram-negative biofilms. The bacterial extract (50 µg ml(-1)) of S6-01 (Bacillus indicus = MTCC 5559) showed 80-90% biofilm inhibition against Escherichia coli, Shigella flexneri, Proteus mirabilis and S6-15 (Bacillus pumilus = MTCC 5560) showed 80-95% biofilm inhibition against all the 10 tested organisms. Furthermore, they also reduced the hydrophobicity index and extracellular polymeric substances (EPS) production. Structural elucidation of the active principle in S6-15 using GC-MS, (1)H NMR, and (13)C NMR spectral data revealed it to be 4-phenylbutanoic acid. This is the first report of 4-phenylbutanoic acid as a natural product. The purified compound (10-15 µg ml(-1)) showed potential activity against a wide range of biofilms. This study for the first time, reports a novel anti-biofilm compound from a marine bacterium with wide application in medicine and the aquaculture industry.


Subject(s)
Anti-Bacterial Agents , Bacillus/chemistry , Biofilms/drug effects , Phenylbutyrates , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Gas Chromatography-Mass Spectrometry , Gram-Negative Bacteria/chemistry , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/chemistry , Gram-Positive Bacteria/drug effects , Hydrophobic and Hydrophilic Interactions/drug effects , Magnetic Resonance Spectroscopy , Phenylbutyrates/chemistry , Phenylbutyrates/isolation & purification , Phenylbutyrates/pharmacology , Seawater/microbiology
7.
J Antibiot (Tokyo) ; 60(4): 285-8, 2007 Apr.
Article in English | MEDLINE | ID: mdl-17456981

ABSTRACT

A new phenolic compound serialynic acid was isolated from an agar culture of the basidiomycete Antrodia serialis, through bioactivity-guided fractionations. It showed weak growth inhibitory activity towards phytopathogenic fungi and a dose-independent anti-Pythium graminicola activity.


Subject(s)
Antifungal Agents/isolation & purification , Hydroquinones/isolation & purification , Phenylbutyrates/isolation & purification , Polyporales/metabolism , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Fermentation , Hydroquinones/chemistry , Hydroquinones/pharmacology , Phenols/chemistry , Phenols/isolation & purification , Phenols/pharmacology , Phenylbutyrates/chemistry , Phenylbutyrates/pharmacology
8.
Article in English | MEDLINE | ID: mdl-16723753

ABSTRACT

An impurity in the bulk drug lisinopril was detected by simple reversed-phase high-performance liquid chromatography (HPLC). This trace-level impurity was rapidly identified as 2-(2-oxo-azocan-3-ylamino)-4-phenyl- butyric acid on the basis of the on-line multi-stage mass spectrometric evidence, and the proposed structure was further confirmed by multi-stage mass spectrometry of lisinopril and three related compounds.


Subject(s)
Azepines/isolation & purification , Lisinopril/standards , Mass Spectrometry/methods , Phenylbutyrates/isolation & purification , Azepines/chemical synthesis , Chromatography, High Pressure Liquid , Phenylbutyrates/chemical synthesis , Spectrometry, Mass, Electrospray Ionization
9.
Chem Pharm Bull (Tokyo) ; 53(11): 1466-8, 2005 Nov.
Article in English | MEDLINE | ID: mdl-16272734

ABSTRACT

Phenylbutenoids isolated previously from the CHCl3 extracts of the rhizomes of Zingiber cassumunar, were evaluated for their cyclooxygenase-2 (COX-2) inhibitory activity along with a new isolate, from the n-BuOH extracts of this plant. The COX-2 inhibitory assay was performed by measuring prostaglandin E2 production in lipopolysaccharide-stimulated mouse macrophage RAW 264.7 cells. Two phenylbutenoid dimers, and, exhibited considerable activity with IC50 values of 2.71 and 3.64 microM. Two phenylbutenoid monomers, and, showed moderate activity (IC50 14.97, 20.68 microM, respectively). The other three phenylbutenoids, were found to be inactive. Compound was elucidated as a new phenylbutenoid glycoside, namely, (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-O-beta-D-glucopyranoside by spectral analysis including various 1D- and 2D-NMR experiments.


Subject(s)
Cyclooxygenase 2 , Cyclooxygenase Inhibitors/isolation & purification , Cyclooxygenase Inhibitors/pharmacology , Phenylbutyrates/isolation & purification , Phenylbutyrates/pharmacology , Zingiber officinale/chemistry , Animals , Celecoxib , Cell Line , Dinoprostone/metabolism , Macrophages/drug effects , Macrophages/metabolism , Molecular Conformation , Plant Roots/chemistry , Pyrazoles/pharmacology , Rats , Structure-Activity Relationship , Sulfonamides/pharmacology
10.
J Chromatogr A ; 1095(1-2): 50-9, 2005 Nov 18.
Article in English | MEDLINE | ID: mdl-16275282

ABSTRACT

The adsorption behaviour of the enantiomers of 2-phenylbutyric acid on the chiral stationary phase (CSP) Kromasil CHI-TBB was studied using hexane/MTBE (90/10) as eluent. Adsorption isotherms were acquired at 40 different enantiomer concentrations in the interval between 7.6 microM and 305 mM, an approximately 40,000-fold dynamic range. The adsorption data fitted well to the bi-Langmuir model, indicating a heterogeneous surface with two different types of adsorption sites having different equilibrium constants and capacities; namely one chiral site and one non-chiral site. A comparison with earlier adsorption studies on modern CSPs revealed that the capacity value of the "true" chiral site of Kromasil CHI-TBB is the largest reported so far. The elution profiles simulated with these parameters show excellent agreement with the corresponding experimental profiles. Guidelines for comparisons of loading capacities of CSPs are presented.


Subject(s)
Chromatography, High Pressure Liquid/methods , Phenylbutyrates/isolation & purification , Adsorption , Chromatography, High Pressure Liquid/instrumentation , Models, Chemical , Silicon Dioxide , Stereoisomerism
11.
Biotechnol Bioeng ; 92(2): 137-46, 2005 Oct 20.
Article in English | MEDLINE | ID: mdl-16037987

ABSTRACT

R-2-hydroxy-4-phenylbutyric acid (R-HPBA) is an important intermediate in the manufacture of angiotensin converting enzyme inhibitors. In this work, a recombinant D-lactate dehydrogenase (LDH) was used to transform 2-oxo-4-phenylbutyric acid (OPBA) to R-HPBA, with concomitant oxidation of beta-nicotinamide adenine dinucleotide (NADH) to NAD(+). The cofactor NADH was regenerated by formate dehydrogenase (FDH) present in whole cells of Candida boidinii, which were pre-treated with toluene to make them permeable. The whole cells used in the process were more stable and easier to prepare as compared with the isolated FDH from the cells. Kinetic study showed that the reaction rate was dependent on the concentration of cofactor, NAD(+), and that both R-HPBA and OPBA inhibited the reaction. A novel method for co-immobilization of whole cells and LDH enzyme on cotton cloth was developed using polyethyleneimine (PEI), which induced the formation of PEI-enzyme-cell aggregates and their adsorption onto cotton cloth, leading to multilayer co-immobilization of cells and enzyme with high loading (0.5 g cell and 8 mg LDH per gram of cotton cloth) and activity yield ( > 95%). A fibrous bed bioreactor with co-immobilized cells and enzyme on the cotton cloth was then evaluated for R-HPBA production in fed-batch and repeated batch modes, which gave relatively stable reactor productivity of 9 g/L . h and product yield of 0.95 mol/mol OPBA when the concentrations of OPBA and R-HPBA were less than 10 g/L.


Subject(s)
Bioreactors/microbiology , Candida/metabolism , Cell Culture Techniques/methods , Lactate Dehydrogenases/metabolism , Phenylbutyrates/metabolism , Biotransformation , Candida/genetics , Cells, Immobilized/metabolism , Enzyme Activation , Enzyme Stability , Enzymes, Immobilized , Feasibility Studies , Lactate Dehydrogenases/genetics , Phenylbutyrates/isolation & purification , Protein Engineering/methods , Recombinant Proteins/metabolism
12.
J Chromatogr A ; 1032(1-2): 219-25, 2004 Apr 02.
Article in English | MEDLINE | ID: mdl-15065799

ABSTRACT

A direct and stereospecific method was worked out to quantify indobufen enantiomers in human serum using capillary zone electrophoresis (CZE). The indobufen enantiomers and (+)-S-ketoprofen (internal standard, IS) were separated in a fused silica capillary, filled with heptakis 2,3,6-tri-O-methyl-beta-cyclodextrin as a chiral selector in a buffer of pH 5.0. Indobufen enantiomers and other non-steroidal anti-inflammatory drugs: flurbiprofen, ketoprofen and (+)-S-naproxen were also separated during one analytical run. UV absorbances of indobufen enantiomers were measured at 282 nm. Influence of temperature on resolution of the enantiomers, and the electrophoretic parameters: electrophoretic (muep) and electroosmotic (muEOF) mobilities were also determined. Validation of the method was carried out. Calibration curves of indobufen enantiomers were linear in the range of 0.2-20.0 microg/ml. Percent recovery of both enantiomers from acidified serum was calculated after extraction with methylene chloride. Intra- and inter-day measurement precision and accuracy were below 15.0%. Limits of quantitation and detection were also estimated. The elaborated method was tested in vivo after administration of a single dose of 200 mg rac-indobufen tablets to healthy volunteers. Calculated parameters confirmed usefulness of the method in human pharmacokinetic studies on indobufen enantiomers. The direct CZE method can provide an alternative to HPLC, where enantiomers used to be derivatised before determination.


Subject(s)
Cyclooxygenase Inhibitors/isolation & purification , Electrophoresis, Capillary/methods , Phenylbutyrates/isolation & purification , Cyclooxygenase Inhibitors/blood , Cyclooxygenase Inhibitors/pharmacokinetics , Humans , Isoindoles , Phenylbutyrates/blood , Phenylbutyrates/pharmacokinetics , Reproducibility of Results , Sensitivity and Specificity , Spectrophotometry, Ultraviolet , Temperature
13.
Electrophoresis ; 22(3): 484-90, 2001 Feb.
Article in English | MEDLINE | ID: mdl-11258759

ABSTRACT

A new, automatic method for the clean-up, preconcentration, separation, and quantitation of nonsteroidal anti-inflammatory drugs (NSAIDs) in biological samples (human urine and serum) using solid-phase extraction coupled on-line to capillary electrophoresis is proposed. Automatic pretreatment is carried out by using a continuous flow system operating simultaneously with the capillary electrophoresis equipment, to which it is linked via a laboratory-made mechanical arm. This integrated system is controlled by an electronic interface governed via a program developed in GWBasic. Capillary electrophoresis is conducted by using a separation buffer consisting of 20 mM NaHPO4, 20 mM beta-cyclodextrin and 50 mM SDS at pH 9.0, an applied potential of 20 kV and a temperature of 20 degrees C. The analysis time is 10 min and the detection limits were between 0.88 and 1.71 microg mL(-1). Automatic clean-up and preconcentration is accomplished by using a C-18 minicolumn and 75% methanol as eluent. The limit of detection of NSAIDs can be up to 400-fold improved when using sample clean-up. The extraction efficiency for these compounds is between 71.1 and 109.7 microg mL(-1) (RSD 2.0-7.7%) for urine samples and from 77.2 to 107.1 microg mL(-1) (RSD 3.5-7.1%) for serum samples.


Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Chromatography, Micellar Electrokinetic Capillary/methods , Anti-Inflammatory Agents, Non-Steroidal/blood , Anti-Inflammatory Agents, Non-Steroidal/urine , Automation , Humans , Ibuprofen/blood , Ibuprofen/isolation & purification , Ibuprofen/urine , Indomethacin/blood , Indomethacin/isolation & purification , Indomethacin/urine , Ketoprofen/blood , Ketoprofen/isolation & purification , Ketoprofen/urine , Phenylbutyrates/blood , Phenylbutyrates/isolation & purification , Phenylbutyrates/urine , Tolmetin/blood , Tolmetin/isolation & purification , Tolmetin/urine
14.
Enantiomer ; 5(1): 37-45, 2000.
Article in English | MEDLINE | ID: mdl-10763868

ABSTRACT

HPLC chiral stationary phases based on human plasma alpha1-acid glycoprotein (AGP) and partially deglycosylated AGP (pd-AGP) were prepared to investigate the effects of sugar moiety of AGP on chiral discrimination of various solutes. Removal of a sugar moiety of AGP by treatment with N-glycosidase was confirmed by high-performance capillary electrophoresis, reversed-phase HPLC and matrix-assisted laser desorption-time of flight (MALDI-TOF) mass spectrometry. The average molecular weights of AGP and pd-AGP were estimated to be ca. 33,000 and 30,600, respectively, by MALDI-TOF mass spectrometry. Next, AGP and pd-AGP were bound to aminopropyl-silica gels activated with N,N '-disuccinimidylcarbonate. The retentivity+ and enantioselectivity of the neutral, acidic and basic solutes tested on the pd-AGP column were significantly or not significantly larger in most solutes than those on the AGP column. This is ascribable to that by cleavage of a sugar chain(s) by N-glycosidase, pd-AGP could become more hydrophobic than AGP, and/ or that a solute could be easily accessible to the specific and/or non-specific binding sites of pd-AGP. It is interesting that warfarin enantiomers are not resolved on the pd-AGP column, but resolved on the AGP column. A sugar chain(s) of AGP cleaved by N-glycosidase might be involved in the enantioselective binding of warfarin enantiomers.


Subject(s)
Carbohydrates/chemistry , Chromatography, High Pressure Liquid/methods , Orosomucoid/chemistry , Alprenolol/chemistry , Alprenolol/isolation & purification , Benzoin/chemistry , Benzoin/isolation & purification , Bupivacaine/chemistry , Bupivacaine/isolation & purification , Chromatography, Gel , Electrophoresis, Capillary , Glycoside Hydrolases/pharmacology , Glycosylation , Humans , Hydantoins/chemistry , Hydantoins/isolation & purification , Hydrogen-Ion Concentration , Molecular Weight , Orosomucoid/drug effects , Orosomucoid/metabolism , Oxprenolol/chemistry , Oxprenolol/isolation & purification , Phenylbutyrates/chemistry , Phenylbutyrates/isolation & purification , Propionates/chemistry , Propionates/isolation & purification , Propranolol/chemistry , Propranolol/isolation & purification , Protein Binding , Silicon Dioxide , Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization , Stereoisomerism , Structure-Activity Relationship , Warfarin/chemistry , Warfarin/isolation & purification
15.
J Pharm Pharmacol ; 51(10): 1201-5, 1999 Oct.
Article in English | MEDLINE | ID: mdl-10579692

ABSTRACT

Enantiomeric resolution of butibufen has been achieved on a cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase with hexane-isopropanol-trifluoroacetic acid, 100:1.2:0.02 (v/v/v) as mobile phase at a flow rate of 1.0 mL min(-1). Semi-preparative isolation of the enantiomers then chiroptical characterization indicated that the order of elution was (-)-R- before (+)-S-butibufen. When tested for their effects on the cyclooxygenase and 5-lipoxygenase pathways of eicosanoid metabolism in calcium ionophore-activated rat peritoneal leukocytes it was found that (+)-S-butibufen inhibited generation of thromboxane B2 (TXB2) and prostaglandin E2 (PGE2) (cyclooxygenase pathway), with an IC50 of 1.5 microM (approx.), whereas the (-)-R enantiomer was essentially inactive. Neither enantiomer inhibited the 5-lipoxygenase pathway. In this regard, (+)-S-butibufen was approximately five times less potent as a cyclooxygenase inhibitor than (+)-S-ibuprofen. These results show the enantiomeric specificity and pathway selectivity of this novel non-steroidal anti-inflammatory drug.


Subject(s)
Ibuprofen/pharmacology , Phenylbutyrates/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Arachidonate 5-Lipoxygenase/drug effects , Arachidonate 5-Lipoxygenase/metabolism , Arachidonic Acids/metabolism , Ascitic Fluid/cytology , Chromatography, High Pressure Liquid , Circular Dichroism , Cyclooxygenase Inhibitors/pharmacology , Eicosanoids/metabolism , Enzyme Inhibitors/pharmacology , Ibuprofen/chemistry , Ibuprofen/isolation & purification , Leukocytes/drug effects , Leukocytes/enzymology , Leukocytes/metabolism , Male , Phenylbutyrates/chemistry , Phenylbutyrates/isolation & purification , Prostaglandin-Endoperoxide Synthases/drug effects , Prostaglandin-Endoperoxide Synthases/metabolism , Rats , Rats, Wistar , Stereoisomerism
16.
Zhongguo Zhong Yao Za Zhi ; 24(9): 551-2, 575, 1999 Sep.
Article in Chinese | MEDLINE | ID: mdl-12205900

ABSTRACT

OBJECTIVE: To study the effective components in the root of Pimpinella thellungiana METHOD: Column chromatography with silica gel and ODS was employed for the isolation and purification of ingredients. Their structures were elucidated by spectral analysis. RESULT: Three compounds were obtained and identified as 2-(1',2'-epoxy)-4-methoxy pheryl-2-methyl-butyrate(I),4-(1'-propenyl) phenol(II) and 2-methyl butyric acid(III). CONCLUSION: Compound I is a new compound and named thellungianin G. Compounds II and III were separated from P. Thellungiana for the first time.


Subject(s)
Phenylbutyrates/isolation & purification , Pimpinella/chemistry , Plants, Medicinal/chemistry , Phenylbutyrates/chemistry , Plant Roots/chemistry
17.
FEBS Lett ; 348(2): 173-6, 1994 Jul 11.
Article in English | MEDLINE | ID: mdl-8034036

ABSTRACT

A new UV-filter compound, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside, has been identified in human lenses. The structure suggests that it is derived biosynthetically from tryptophan. Quantification studies on the new compound show that it is the second-most abundant UV-filter compound in the lens with an absorption and fluorescence spectrum similar to that of 3-hydroxykynurenine glucoside.


Subject(s)
Crystallins/isolation & purification , Glucosides/isolation & purification , Lens, Crystalline/chemistry , Phenylbutyrates/isolation & purification , Ultraviolet Rays , Chromatography, High Pressure Liquid , Chromatography, Thin Layer , Crystallins/chemistry , Filtration , Glucosides/chemistry , Humans , Molecular Structure , Phenylbutyrates/chemistry , Spectrometry, Fluorescence , Spectrophotometry, Ultraviolet
18.
Chirality ; 5(7): 513-5, 1993.
Article in English | MEDLINE | ID: mdl-8240928

ABSTRACT

On a column with bovine serum albumin (BSA) immobilized covalently to silica, the adsorption isotherms of the enantiomers of mandelic acid, tryptophan, 2-phenylbutyric acid, and N-benzoylalanine are measured using a buffered mobile phase. Knowing the amount of BSA immobilized on the column (36 mg), the ratio of the number of enantiomer molecules needed to saturate the enantioselective retention mechanism to the number of BSA molecules is determined. The mean of the set of eight enantiomers is 0.28. These data confirm that at most one enantioselective site exists for each BSA molecule for the kind of enantiomers studied.


Subject(s)
Alanine/analogs & derivatives , Mandelic Acids/chemistry , Phenylbutyrates/chemistry , Serum Albumin, Bovine , Stereoisomerism , Tryptophan/chemistry , Adsorption , Alanine/chemistry , Alanine/isolation & purification , Binding Sites , Chromatography, Affinity/methods , Mandelic Acids/isolation & purification , Phenylbutyrates/isolation & purification , Structure-Activity Relationship , Tryptophan/isolation & purification
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