title: Oligostilbenoids from the heartwood of N. Heimii: role of non-covalent association in their biogenesis.
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.
authors.affiliation: LCSN-Faculté de Pharmacie, Université de Limoges, 2 rue du Dr. Marcland, 87000 Limoges (France).
authors.forename: Imene
authors.initials: I
authors.lastname: Bayach
authors.forename: Nurhuda
authors.initials: N
authors.lastname: Manshoor
authors.forename: Juan Carlo
authors.initials: JC
authors.lastname: Sancho-García
authors.forename: Muhammad Iqbal
authors.initials: MI
authors.lastname: Choudhary
authors.forename: Patrick
authors.initials: P
authors.lastname: Trouillas
authors.forename: Jean-Frédéric Faizal
authors.initials: JF
authors.lastname: Weber
mesh_terms: D019281:Dimerization; D053958:Dipterocarpaceae / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D000077185:Resveratrol; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D013816:Thermodynamics
chemical_list: D013267:Stilbenes; D000077185:Resveratrol
keywords: NMR spectroscopy; Neobalanocarpus Heimii; biosynthesis; density fucntional calculations; non-covalent interactions; oligostilbenes