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- Title
Oligostilbenoids from the Heartwood of N. Heimii: Role of Non- Covalent Association in their Biogenesis.
- Authors
Bayach, Imene; Manshoor, Nurhuda; Sancho ‐ García, Juan Carlo; Choudhary, Muhammad Iqbal; Trouillas, Patrick; Weber, Jean ‐ Frédéric Faizal
- 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.
- Subjects
HEARTWOOD; STILBENE; RESVERATROL; DENSITY functional theory; OLIGOMERIZATION; REARRANGEMENTS (Chemistry)
- Publication
Chemistry - An Asian Journal, 2015, Vol 10, Issue 1, p198
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201402673