Oligostilbenoids from the Heartwood of N. Heimii: Role of Non-Covalent Association in their Biogenesis
| Autor: | Nurhuda Manshoor, Patrick Trouillas, Imene Bayach, Muhammad Iqbal Choudhary, Jean-Frédéric F. Weber, Juan C. Sancho-García |
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| Přispěvatelé: | Universidad de Alicante. Departamento de Química Física, Química Cuántica |
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Magnetic Resonance Spectroscopy
Neobalanocarpus Heimii Stereochemistry Chemistry Non covalent Non-covalent interactions Organic Chemistry Molecular Conformation Density fucntional calculations Stereoisomerism General Chemistry Biosynthesis Biochemistry Dipterocarpaceae NMR spectroscopy Resveratrol Botany Stilbenes Thermodynamics Christian ministry Química Física Dimerization Oligostilbenes |
| Popis: | 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. I.B. and P.T. gratefully thank the ‘Association Djerbienne en France’ (ADF) for financial support. J.-F.F.W. gratefully acknowledges the Malaysian Ministry of Higher Education for the grant No. 600-RMI/ST/FRGS 5/3/Fst (4/2011). |
| Databáze: | OpenAIRE |
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