Polyprenylated benzophenone derivatives from Clusia burle-marxii and their chemotaxonomic significance

Abstract Six polyprenylated benzophenone derivatives (1–6) with the central bicyclo[3.3.1]nonane-2,4,9-trione core were isolated from Clusia burle-marxii trunks. Despite their highly conserved structural characteristics, this is the very first time that these polyprenylated benzophenone derivatives are isolated from a single plant species, highlighting the biochemical plasticity of Clusia burle-marxii to produce such unique class of bioactive compounds. Compounds 1, 2, and 6 are reported for the first time in Clusia burle-marxii, whereas compounds 3, 4 and 5 are reported for the first time in the Clusiaceae family. Their structures were established by careful analysis of spectroscopic data, including 1H NMR, 13C NMR, and 2D-NMR (COSY, NOESY, HSQC, HMBC). These polyprenylated benzophenone derivatives have the potential to be used as chemosystematics biomarkers for the family Clusiaceae. Their putative biosynthesis pathway is also discussed.