UV/Visible spectra of natural polyphenols: A time-dependent density functional theory study

Abstract In addition to their numerous biological activities, natural and hemisynthetic polyphenols contribute to the large variety of colours (from red to violet) in nature (e.g., fruit, vegetables, leaves and petals). In order to understand the colour variation attributed to the multitude of chemical structures of this wide class of compounds, time-dependent density functional quantum-chemical calculations at the B3P86/6-311+G(d,p) level of theory appears as a relevant and efficient tool. The UV/Vis properties of 33 polyphenols were systematically investigated, including mainly flavonoids, isoflavonoids and flavonolignans. On the basis of molecular orbital analysis we established the structure–property relationship, inter alia showing the role of π orbital (de-)localisation, mesomeric (+M) effects of hydroxyl groups and structural modification of the molecular backbone. The results might help in the future, for example, for the prediction of novel hemisynthetic compounds.