The synthesis and electrochemical studies of chalcones and flavanones: an investigation of their antioxidant activity

dc.contributor.advisorGreen, Ivan
dc.contributor.advisorJahed, Nazeem
dc.contributor.authorBaugaard, Carlo
dc.date.accessioned2014-06-11T10:25:44Z
dc.date.accessioned2024-05-09T10:50:14Z
dc.date.available2014-06-11T10:25:44Z
dc.date.available2024-05-09T10:50:14Z
dc.date.issued2013
dc.description>Magister Scientiae - MScen_US
dc.description.abstractFlavonoids, one of the biggest classes of secondary metabolites, are found abundantly in nature in a broad range of fruits, vegetables and beverages such as tea, coffee, beer, wine and fruit drinks. Flavonoids have been reported to exert multiple biological functions as well as tremendous pharmacological activity, including anticancer activity, protection, antioxidant activity, cardiovascular protection, antibacterial, antifungal and antiviral activity. The antioxidant activity of flavones is reported to be associated with those bearing hydroxyl functions. In the present study, several reaction steps have been carried out to synthesize three sub classes of flavonoids namely; chalcones, dihydrochalcones and flavanones with various substituents attached. The first step involved protection of hydroxyl groups of acetophenone and benaldehyde as starting materials. Thereafter the Clasien Schmidt condensation reaction, under basic conditions, was performed to afford chalcone intermediates. Treatment of these chalcones with sodium acetate, under reflux, afforded flavanones as a single product in high yields. Thereafter all protecting groups where removed to yield the final products. All products and intermediates where purified by column chromatography and were characterized by Nuclear Magnetic Resonance Spectroscopy (NMR) (1H NMR and 13C NMR). An electrochemical analysis on all flavonoid compounds was performed by Cyclic Voltammetry (CV) and Square Wave Voltammetry (SWV) to give information on the accessible redox couples identified by their oxidation potentials. Oxidation potentials, which gave valuable information about reducing ability and hence the antioxidant activity, where used to compare all compounds. The antioxidant activity was observed to increase with the addition of hydroxyl groups on the B-ring. Compounds with a combination of hydroxyl groups on the A-ring and methoxy groups on the B-ring showed increased antioxidant activity when compared to those with only hydroxyl groups on the base structure. 2, 5, 4’-trihydroxy dihydrochalcone showed moderate antioxidant ability. However the 2, 5, 4’-trihydroxychalcone, containing the α, β unsaturated double bond, proved to have the greatest antioxidant ability.en_US
dc.identifier.urihttps://hdl.handle.net/10566/14497
dc.language.isoenen_US
dc.publisherUniversity of Western Capeen_US
dc.rights.holderUniversity of Western Capeen_US
dc.subjectSynthesis of chalcones and flavanonesen_US
dc.subjectAntioxidant activity of Flavonoidsen_US
dc.subjectElectrochemistry of Flavonoidsen_US
dc.subjectFlavonoidsen_US
dc.titleThe synthesis and electrochemical studies of chalcones and flavanones: an investigation of their antioxidant activityen_US
dc.typeThesisen_US

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