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1.
Eur J Pharmacol ; 547(1-3): 31-6, 2006 Oct 10.
Article in English | MEDLINE | ID: mdl-16945365

ABSTRACT

Iron-induced oxidative stress has been implicated in several pathological processes. In the present work we provide evidence for the formation of a mangiferin:Fe(III) complex (2:1), shown by means of either iron-induced changes in the UV/visible spectrum of mangiferin or by reduction of the anodic current peak in the voltammogram of that compound; we demonstrate, in addition, that the ferric complex is more effective than mangiferin itself in scavenging superoxide radicals generated by pyrogallol autoxidation, as well as in protecting hepatocytes from reactive oxygen species mediated hypoxia/reoxygenation injury. Moreover, we found that the mangiferin:Fe(III) complex reacts more readily with horseradish peroxidase/H(2)O(2) than does mangiferin by itself. We postulate that mangiferin could afford protection against iron/reactive oxygen species-mediated pathological processes by means of both iron chelating and iron-stimulated superoxide radical scavenging activity.


Subject(s)
Antioxidants/pharmacology , Ferric Compounds/pharmacology , Hepatocytes/drug effects , Xanthones/pharmacology , Animals , Cell Hypoxia , Cell Survival/drug effects , Cells, Cultured , Drug Synergism , Electrochemistry , Ferric Compounds/chemistry , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Hepatocytes/metabolism , Hepatocytes/pathology , Male , Molecular Structure , Oxygen/pharmacology , Rats , Rats, Wistar , Reactive Oxygen Species/metabolism , Spectrophotometry, Ultraviolet , Superoxides/antagonists & inhibitors , Superoxides/metabolism , Xanthones/chemistry
2.
Pharmacol Res ; 54(5): 389-95, 2006 Nov.
Article in English | MEDLINE | ID: mdl-17000117

ABSTRACT

A standard aqueous stem bark extract from selected species of Mangifera indica L. (Anacardiaceae)--Vimang, whose major polyphenolic component is mangiferin, displays potent in vitro and in vivo antioxidant activity. The present study provides evidence that the Vimang-Fe(III) mixture is more effective at scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide radicals, as well as in protecting against t-butyl hydroperoxide-induced mitochondrial lipid peroxidation and hypoxia/reoxygenation-induced hepatocytes injury, compared to Vimang alone. Voltammetric assays demonstrated that Vimang, in line with the high mangiferin content of the extract, behaves electrochemically like mangiferin, as well as interacts with Fe(III) in close similarity with mangiferin's interaction with the cation. These results justify the high efficiency of Vimang as an agent protecting from iron-induced oxidative damage. We propose Vimang as a potential therapy against the deleterious action of reactive oxygen species generated during iron-overload, such as that occurring in diseases like beta-thalassemia, Friedreich's ataxia and haemochromatosis.


Subject(s)
Free Radical Scavengers/pharmacology , Hepatocytes/drug effects , Iron/pharmacology , Plant Extracts/pharmacology , Animals , Antimycin A/pharmacology , Biphenyl Compounds/metabolism , Cell Hypoxia/drug effects , Cell Survival/drug effects , Cells, Cultured , Hepatocytes/metabolism , Hydrazines/metabolism , Male , Mangifera , Mitochondria, Liver/drug effects , Mitochondria, Liver/metabolism , Oxygen Consumption/drug effects , Picrates , Pyrogallol/pharmacology , Rats , Rats, Wistar , Superoxides/metabolism
3.
J Biosci Bioeng ; 100(4): 423-8, 2005 Oct.
Article in English | MEDLINE | ID: mdl-16310732

ABSTRACT

A simple method for the preparation of S-propranolol catalyzed by a Rhizopus niveus lipase in an aqueous medium is described. Hydroxypropyl-beta-cyclodextrin was used for the first time to increase the solubility of (R,S)-O-butyryl propranolol thus permitting the reaction to be carried out in water. The formation of an inclusion complex between (R,S)-O-butyryl propranolol and hydroxypropyl-beta-cyclodextrin was studied and a stoichiometry of 1:1 was determined. The influences of the hydroxypropyl-beta-cyclodextrin concentration, pH and percentage of ethanol on the enzymatic activity were also investigated. Under the conditions presented in this paper, values of ee(s) of 90% and E=48 were obtained.


Subject(s)
Lipase/chemistry , Propranolol/metabolism , Rhizopus/enzymology , beta-Cyclodextrins/chemistry , 2-Hydroxypropyl-beta-cyclodextrin , Catalysis , Ethanol , Hydrogen-Ion Concentration , Isomerism , Lipase/metabolism
4.
J Agric Food Chem ; 53(14): 5754-9, 2005 Jul 13.
Article in English | MEDLINE | ID: mdl-15998144

ABSTRACT

An esterase activity from Terfezia claveryi Chatin ascocarps, a mycorrhizal hypogeous fungus, is described for the first time. The enzyme was partially purified using phase partitioning in Triton X-114 (TX-114), achieving a reduction of 87% in the triglyceride content and the removal of 63% of phenols. The enzyme showed maximum activity toward short-chain p-nitrophenyl esters, and no interfacial activation was observed, indicating that the enzyme responsible for this activity is an esterase and not a lipase. This esterase presented its maximum activity at pH 7.4 and 60 degrees C. The values obtained for Km at pH 7.4 were 0.3 mM for p-nitrophenyl butyrate and 0.6 mM for p-nitrophenyl acetate with catalytic efficiencies (Vmax/Km) of 0.23 and 0.32, respectively. T. claveryi esterase was inhibited by phenylboric acid, indicating that serine residues were involved in the enzyme activity. This activity was localized only in the hypothecium and was absent from the peridium and gleba.


Subject(s)
Ascomycota/enzymology , Esterases/analysis , Enzyme Inhibitors/pharmacology , Esterases/antagonists & inhibitors , Esterases/metabolism , Histocytochemistry , Hydrogen-Ion Concentration , Kinetics , Substrate Specificity , Temperature
5.
Biotechnol Prog ; 21(2): 338-42, 2005.
Article in English | MEDLINE | ID: mdl-15801768

ABSTRACT

In the present paper, a novel enzymatic reaction between (R,S)-O-butyryl propranolol (O-BP) and lipase from Candida rugosa in the presence of hydroxypropyl-beta-cyclodextrin (HP-beta-CD) is described. Under the used condition, lipase catalyzed the intramolecular transacylation of O-BP into N-butyryl propranolol (N-BP). Propranolol, the product of the expected hydrolysis reaction, was not detected in the reaction medium. A chiral analysis of the reaction product indicated that lipase showed a preference for (R)-O-butyryl propranolol since it first transformed the (R)-enantiomer and then the corresponding (S)-enantiomer. The influence of different reaction conditions on the initial rate is also studied.


Subject(s)
Candida/enzymology , Cyclodextrins/metabolism , Lipase/metabolism , Propranolol/analogs & derivatives , Propranolol/metabolism , Acylation , Catalysis , Chromatography, High Pressure Liquid , Hydrogen-Ion Concentration , Mass Spectrometry , Temperature
6.
Rev. cuba. farm ; 32(2): 130-9, 1998. graf
Article in Spanish | LILACS | ID: lil-228112

ABSTRACT

Se realizó una revisión bibliográfica sobre el racemato del clorhidrato de propranolol y sus ésteres, con el objetivo de recopilar los métodos más actuales para su detección y la resolución de su mezcla racémica, de forma que se mantengan informados los farmacéuticos, químicos sintetizadores y otros profesionales relacionados con la temática. Se consultaron las bases de datos MEDLINE (1986-1992), Analytical Abstracts (1985-1994), Chemicals Abstracts (1990-1992) y los Current Contents (Life Science y Physical, Chemical & Earth Sciences) desde 1990-1996. Se reportan como técnicas de análisis para su detección: espectrfluorometría, colorimetría, cromatografía de placa delgada y cromatografía líquida de alta resolución. Se reflejan diferentes métodos de resolución de enantiómeros, como: cromatografía de fluido supercrítico, electroforesis capilar, cromatografía de placa delgada y cromatografía líquida de alta resolución utilizando fases y/o aditivos quirales, empleados estos 2 últimos tanto para la detección como para la resolución del clorhidrato de propanolol y sus ésteres


Subject(s)
Colorimetry , Chromatography, Thin Layer/methods , Chromatography, High Pressure Liquid/methods , Spectrometry, Fluorescence/methods , Propranolol/analogs & derivatives
7.
Rev. cuba. farm ; 32(2): 130-9, 1998. graf
Article in Spanish | CUMED | ID: cum-13436

ABSTRACT

Se realizó una revisión bibliográfica sobre el racemato del clorhidrato de propranolol y sus ésteres, con el objetivo de recopilar los métodos más actuales para su detección y la resolución de su mezcla racémica, de forma que se mantengan informados los farmacéuticos, químicos sintetizadores y otros profesionales relacionados con la temática. Se consultaron las bases de datos MEDLINE (1986-1992), Analytical Abstracts (1985-1994), Chemicals Abstracts (1990-1992) y los Current Contents (Life Science y Physical, Chemical & Earth Sciences) desde 1990-1996. Se reportan como técnicas de análisis para su detección: espectrfluorometría, colorimetría, cromatografía de placa delgada y cromatografía líquida de alta resolución. Se reflejan diferentes métodos de resolución de enantiómeros, como: cromatografía de fluido supercrítico, electroforesis capilar, cromatografía de placa delgada y cromatografía líquida de alta resolución utilizando fases y/o aditivos quirales, empleados estos 2 últimos tanto para la detección como para la resolución del clorhidrato de propanolol y sus ésteres(AU)


Subject(s)
Propranolol/analogs & derivatives , Chromatography, Thin Layer/methods , Chromatography, High Pressure Liquid/methods , Spectrometry, Fluorescence/methods , Colorimetry/methods
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