Oligostilbenoids from the heartwood of N. Heimii: Role of non-covalent association in their biogenesis

• Published in: Chemistry - An Asian Journal
• Main Author: Bayach I.; Manshoor N.; Sancho-García J.C.; Choudhary M.I.; Trouillas P.; Weber J.-F.F.
• Format: Article
• Language: English
• Published: John Wiley and Sons Ltd 2015
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84919663411&doi=10.1002%2fasia.201402673&partnerID=40&md5=7f327a8e882f42d7ded2c449c6d60289

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. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.