Isorhapontigenin: a novel bioactive stilbene from wine grapes

Abstract

Stilbenes are a family of bioactive compounds found in plants. However, only a few stilbenes are present in the human diet. Grape and wine are the main dietary source of stilbenes, resveratrol and piceid being the most common ones. Ultraviolet C light (UVC) postharvest treatment was used to obtain significantly increased stilbene concentration in grapes. A new, previously undescribed-in-grapes stilbene was found after UVC treatment. The process followed to isolate and identify this unknown stilbene is described in the present work. This isolation involved several fractionation steps including counter current chromatography and semi-preparative HPLC due to its low concentration and the presence of structurally related compounds. The structure of the compound was unequivocally identified by NMR spectroscopy analyses including (1)H-NMR; COSY; ROESY; HSQC and HMBC. The compound was identified as isorhapontigenin (ISOR), a stilbene found in traditional Asian medicinal plants. To the best of our knowledge this is the first report of its occurrence in grapes.