A predictive tool for assessing 13C NMR chemical shifts of flavonoids

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Abstract
Herein are presented the 1H and 13C 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‐β‐D‐glucoside, homoorientin; luteolin‐8C‐β‐D‐glucoside, vitexin; apigenin‐8C‐β‐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 13C chemical shifts, which is based on the cumulative differences between the monohydroxyflavones and flavone 13C chemical shifts, is demonstrated. The tool can be used to accurately predict 13C flavonoid chemical shifts and it is expected to be useful for rapid assessment of flavonoid 13C NMR spectra and for assigning substitution patterns in newly isolated flavonoids. Copyright © 2007 John Wiley & Sons, Ltd.

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