New triterpenes from Maytenus robusta : structural elucidation based on NMR experimental data and theoretical calculations.

• Autor(a) principal: Sousa, Grasiely Faria de
• Data de Publicação: 2012
• Outros Autores: Duarte, Lucienir Pains, Alcântara, Antônio Flávio de Carvalho, Silva, Grácia Divina de Fátima, Vieira Filho, Sidney Augusto, Miranda, Roqueline Rodrigues Silva de, Oliveira, Djalma Menezes de, Takahashi, Jacqueline Aparecida
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional da UFOP
• Texto Completo: http://www.repositorio.ufop.br/handle/123456789/3853; https://doi.org/10.3390/molecules171113439
• topic: Maytenus robusta; Pentacyclic triterpenes; Acetylcholinesterase inhibitory activity

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.