Digital Database of Absorption Spectra of Diverse Flavonoids Enables Structural Comparisons and Quantitative Evaluations.

Abstract

Flavonoids play diverse roles in plants, comprise a non-negligible fraction of net primary photosynthetic production, and impart beneficial effects in human health from a plant-based diet. Absorption spectroscopy is an essential tool for quantitation of flavonoids isolated from complex plant extracts. The absorption spectra of flavonoids typically consist of two major bands, band I (300-380 nm) and band II (240-295 nm), where the former engenders a yellow color; in some flavonoids the absorption tails to 400-450 nm. The absorption spectra of 177 flavonoids and analogues of natural or synthetic origin have been assembled, including molar absorption coefficients (109 from the literature, 68 measured here). The spectral data are in digital form and can be viewed and accessed at http://www.photochemcad.com. The database enables comparison of the absorption spectral features of 12 distinct types of flavonoids including flavan-3-ols (e.g., catechin, epigallocatechin), flavanones (e.g., hesperidin, naringin), 3-hydroxyflavanones (e.g., taxifolin, silybin), isoflavones (e.g., daidzein, genistein), flavones (e.g., diosmin, luteolin), and flavonols (e.g., fisetin, myricetin). The structural features that give rise to shifts in wavelength and intensity are delineated. The availability of digital absorption spectra for diverse flavonoids facilitates analysis and quantitation of these valuable plant secondary metabolites. Four examples are provided of calculations─multicomponent analysis, solar ultraviolet photoprotection, sun protection factor (SPF), and Förster resonance energy transfer (FRET)─for which the spectra and accompanying molar absorption coefficients are sine qua non.