Oligostilbenoids from the Heartwood of <i>N. Heimii</i>: Role of Non‐Covalent Association in their Biogenesis

Abstract

Abstract Four new oligostilbenes, including one dimer and three tetramers of resveratrol, that is, heimiols B–E ( 1 – 4 ) were isolated from the heartwood of Neobalanocarpus heimii (Dipterocarpaceae), together with thirteen known resveratrol oligomers ( 5 – 17 ). Examination of the structural diversity of the isolated oligostilbenes led to hypothesis of their biogenetic origin through a small number of versatile chemical pathways. These hypotheses are strongly supported by computational calculations (based on the density functional theory, DFT) that were performed to rationalize conformational re‐arrangements and thus provide insights into the mechanism of oligostilbenoid biosynthesis. Non‐covalent complexes are believed to drive the regio‐ and stereoselectivity of the oligomerization reactions.