title: A predictive tool for assessing (13)C NMR chemical shifts of flavonoids.
abstract: Herein are presented the (1)H and (13)C NMR data for seven monohydroxyflavones (3-, 5-, 6-, 7-, 2'-, 3'-, and 4'-hydroxyflavone), five dihydroxyflavones (3,2'-, 3,3'-, 3,4'-, 3,6-, 2',3'-dihydroxyflavone), a trihydroxyflavone (apigenin; 5,7,4'-trihydroxyflavone), a tetrahydroxyflavone (luteolin; 5,7,3',4'-tetrahydroxyflavone), and three glycosylated hydroxyflavones (orientin; luteolin-6C-beta-D-glucoside, homoorientin; luteolin-8C-beta-D-glucoside, vitexin; apigenin-8C-beta-D-glucoside). When these NMR spectra are compared, it is possible to assess the impact of flavone modification and to elucidate detailed structural and electronic information for these flavonoids. A simple predictive tool for assigning flavonoid (13)C chemical shifts, which is based on the cumulative differences between the monohydroxyflavones and flavone (13)C chemical shifts, is demonstrated. The tool can be used to accurately predict (13)C flavonoid chemical shifts and it is expected to be useful for rapid assessment of flavonoid (13)C NMR spectra and for assigning substitution patterns in newly isolated flavonoids.
authors.affiliation: Department of Chemistry, Trent University, 1600 West Bank Drive, Peterborough, ON K9J 7B8, Canada.
authors.forename: Darcy C
authors.initials: DC
authors.lastname: Burns
authors.forename: David A
authors.initials: DA
authors.lastname: Ellis
authors.forename: Raymond E
authors.initials: RE
authors.lastname: March
mesh_terms: D002247:Carbon Isotopes; D005419:Flavonoids / Q000737:chemistry*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure
chemical_list: D002247:Carbon Isotopes; D005419:Flavonoids