Resveratrol tetramer vaticanol N with a tribenzobicyclo[3.3.2]decatriene skeleton isolated from the leaves of Vatica bantamensis

Vaticanol N (1) is a new resveratrol tetramer isolated from the acetone extract of Vatica bantamensis (Dipterocarpaceae) leaves. Spectroscopic analyses, including electrospray ionization–mass spectrometry and nuclear magnetic resonance, were used to analyze the structure of 1, and its absolute configuration was determined using circular dichroism data. Notably, 1 is the first 8–8′ resveratrol tetramer produced via the 8–8′ cross-coupling of two 8–10′-coupled dimeric precursors with C–C-connected fused ring systems, a dihydrobenzofuran and hexacyclic tribenzobicyclo[3.3.2]decatriene, each with two and six asymmetric carbons. Moreover, a plausible biosynthetic pathway for 1 was proposed. The isolation of 1 exhibited further diversification of the resveratrol tetramer within the considered family.