New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.
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Date
2012
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Abstract
Leaves of Maytenus robusta (Celastraceae) were subjected to phytochemical
investigation mainly directed at the isolation of pentacyclic triterpenes. The compounds
friedelin (1), β-friedelinol (2), 3-oxo-21β-H-hop-22(29)-ene (7), 3,4-seco-friedelan-3,11β- olide (8), 3β-hydroxy-21β-H-hop-22(29)-ene (9), 3,4-seco-21β-H-hop-22(29)-en-3-oic acid (10), 3,4-seco-friedelan-3-oic acid (11), and sitosterol were identified in the hexane extract of M. robusta leaves. Compounds 8 and 9 are described herein for the first time. The structure and stereochemistry of both compounds were experimentally established by IR, HRLC-MS, and 1D (1H, 13C, and DEPT 135) and 2D (HSQC, HMBC and COSY) NMR data and supported by correlations with carbon chemical shifts calculated using the DFT method (BLYP/6-31G* level). Compounds 7 and 10 are also described for the first time, and their chemical structures were established by comparison with NMR data of similar structures described in the literature and correlations with BLYP/6-31G* calculated carbon chemical shifts. Compound 9, a mixture of 11 and sitosterol, and 3β,11β-dihydroxyfriedelane
(4) were evaluated by the Ellman’s method and all these compounds showed
acethylcholinesterase inhibitory properties.
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Keywords
Maytenus robusta, Pentacyclic triterpenes, Acetylcholinesterase inhibitory activity
Citation
SOUSA, G. F. de et al. New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations. Molecules, v. 17, p. 13439-13456, 2012. Disponível em: <http://www.mdpi.com/1420-3049/17/11/13439> Acesso em: 20 ago. 2014.