Structure elucidation of highly condensed stilbenoids: chiroptical properties and absolute configuration

Abstract

We investigated the potential roles of the skeleton-based comparative study of electronic circular dichroism (ECD) spectra for an application of absolute configuration (AC) determination of oligostilbenoids (OS). This approach was ultimately achieved followed by the isolation and elucidation of relative configuration (RC) of upunaphenol Q (1) (new compound) and vateriaphenol A (2), namely two octamers are dimeric tetramers of resveratrol (Res). The common building blocks (BB) provide further insight into how smaller OS are apparently conserved during downstream metabolites, as well as providing additional impetus to resolve AC of highly condensed stilbenoids (HCS). They also underline the importance of studies on determination of AC of common BB in the chemical library and to provide chiroptical properties.