New highly in vitro antioxidative 3,8″-linked Biflav(an)ones and Flavanone-C-glycosides from Garcinia buchananii stem bark. 2013

Timo D Stark, and Daniel Germann, and Onesmo B Balemba, and Junichiro Wakamatsu, and Thomas Hofmann
Lehrstuhl für Lebensmittelchemie und Molekulare Sensorik, Technische Universität München , Lise-Meitner Strasse 34, D-85354 Freising, Germany.

Very recently, we described highly antioxidative polyphenols isolated from the stem bark extract of the Garcinia buchananii tree. In this study, we describe additional antioxidants from Garcinia buchananii bark extract using hydrogen peroxide scavenging, oxygen radical absorbance capacity (ORAC), and trolox equivalent antioxidant capacity (TEAC) assays. UPLC-HR-ESI-TOF-MS(e) analysis, 1- and 2D-NMR, and circular dichroism (CD) spectroscopy led to the unequivocal identification of the antioxidative molecules as a series of five 3,8″-linked biflav(an)ones and two flavanone-C-glycosides. (2S,3R)-Taxifolin-6-C-β-d-glucopyranoside (2), (2R,3S,2″S,3″S)-manniflavanone (3), (2R,3S)-buchananiflavonol (4), and (2S,3R,2″R,3″R)-GB-1 (6) are new compounds, and (2S,3S)-taxifolin-6-C-β-d-glucopyranoside (1) was described so far only in one other plant. The structure of (2R,3S,2″R,3″R)-GB-1 (5) and (2R,3S,2″S)-GB2a (7) were confirmed. The H2O2 scavenging, TEAC, and the ORAC assays demonstrated that these natural products have an extraordinarily high antioxidative power, especially (2R,3S,2″S,3″S)-manniflavanone (3) with an EC50 value of 3.0 μM, 4.00 mmol TE/mmol, and 10.30 μmol TE/ μmol.

UI MeSH Term Description Entries
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
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
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
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
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D044950 Flavanones A group of FLAVONOIDS characterized with a 4-ketone. 2-Phenyl-Benzopyran-4-Ones,2 Phenyl Benzopyran 4 Ones
D024301 Plant Bark The outer layer of the woody parts of plants. Bark, Plant,Bark, Tree,Tree Bark,Barks, Plant,Barks, Tree,Plant Barks,Tree Barks
D029760 Garcinia A plant genus of the family CLUSIACEAE. Members contain XANTHONES. Gamboge,Gamboges,Garcinias

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