Phenolic compounds from Hypericum calycinum and their antioxidant activity. 2009

Hasan Kirmizibekmez, and Carla Bassarello, and Sonia Piacente, and Engin Celep, and Irem Atay, and Güldem Mercanoğlu, and Erdem Yeşilada
Department of Pharmacognosy, Faculty of Pharmacy, Yeditepe University, TR-34755, Kayişdaği, Istanbul, Turkey. hasankbekmez@yahoo.com

From the MeOH extract of Hypericum calycinum, two caffeoylquinic acid derivatives, butyl chlorogenate (1), and chlorogenic acid (2), seven flavonoids, quercetin (3), quercitrin (4), hyperoside (5), isoquercitrin (6), miquelianin (7), rutin (8) and I3,II8-biapigenin (9) and two flavanols, (+)-catechin (10) and (-)-epicatechin (11) were isolated. Identification of the isolates was carried out by spectroscopic analysis including 1D and 2D NMR experiments as well as mass spectrometry. Free radical scavenging activities of the isolated compounds were determined in in-vitro 1,1-diphenyl-2-picrylhydrazyl (DPPH) and nitric oxide (NO) scavenging models. The compounds showed strong DPPH and moderate NO scavenging activities in a concentration dependent manner. (+)-Catechin and (-)-epicatechin were found to be the most active compounds with IC50 values of 4.16 and 4.67 microM for DPPH and 190 and 170 microM for NO scavenging activities, respectively.

UI MeSH Term Description Entries
D009569 Nitric Oxide A free radical gas produced endogenously by a variety of mammalian cells, synthesized from ARGININE by NITRIC OXIDE SYNTHASE. Nitric oxide is one of the ENDOTHELIUM-DEPENDENT RELAXING FACTORS released by the vascular endothelium and mediates VASODILATION. It also inhibits platelet aggregation, induces disaggregation of aggregated platelets, and inhibits platelet adhesion to the vascular endothelium. Nitric oxide activates cytosolic GUANYLATE CYCLASE and thus elevates intracellular levels of CYCLIC GMP. Endogenous Nitrate Vasodilator,Mononitrogen Monoxide,Nitric Oxide, Endothelium-Derived,Nitrogen Monoxide,Endothelium-Derived Nitric Oxide,Monoxide, Mononitrogen,Monoxide, Nitrogen,Nitrate Vasodilator, Endogenous,Nitric Oxide, Endothelium Derived,Oxide, Nitric,Vasodilator, Endogenous Nitrate
D010636 Phenols Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D010851 Picrates Salts or esters of PICRIC ACID.
D010936 Plant Extracts Concentrated pharmaceutical preparations of plants obtained by removing active constituents with a suitable solvent, which is evaporated away, and adjusting the residue to a prescribed standard. Herbal Medicines,Plant Extract,Extract, Plant,Extracts, Plant,Medicines, Herbal
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D001713 Biphenyl Compounds Whitish aromatic crystalline organic compounds made up of two conjoined BENZENE rings. Compounds, Biphenyl
D019906 Nuclear Magnetic Resonance, Biomolecular NMR spectroscopy on small- to medium-size biological macromolecules. This is often used for structural investigation of proteins and nucleic acids, and often involves more than one isotope. Biomolecular Nuclear Magnetic Resonance,Heteronuclear Nuclear Magnetic Resonance,NMR Spectroscopy, Protein,NMR, Biomolecular,NMR, Heteronuclear,NMR, Multinuclear,Nuclear Magnetic Resonance, Heteronuclear,Protein NMR Spectroscopy,Biomolecular NMR,Heteronuclear NMR,Multinuclear NMR,NMR Spectroscopies, Protein,Protein NMR Spectroscopies,Spectroscopies, Protein NMR,Spectroscopy, Protein NMR
D020902 Hypericum Genus of perennial plants in the family CLUSIACEAE (sometimes classified as Hypericaceae). Herbal and homeopathic preparations are used for depression, neuralgias, and a variety of other conditions. Hypericum contains flavonoids; GLYCOSIDES; mucilage, TANNINS; volatile oils (OILS, ESSENTIAL), hypericin and hyperforin. Hypericum perforatum,Saint Johns Wort,St. Johns Wort,Saint John's Wort,Saint Johnswort,St. John's Wort,St. Johnswort,Hypericum perforatums,Hypericums,John's Wort, Saint,John's Wort, St.,Johns Wort, Saint,Johns Wort, St.,Johnswort, Saint,Johnswort, St.,Saint John Wort,St. John Wort,Wort, Saint John's,Wort, Saint Johns,Wort, St. John's,Wort, St. Johns,perforatums, Hypericum

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