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New Triterpenes from Maytenus robusta: Structural Elucidation Based on NMR Experimental Data and Theoretical Calculations
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, 31270-901, Belo Horizonte, MG, Brazil
Escola de Farmácia, Universidade Federal de Ouro Preto, 35400-000, Ouro Preto, MG, Brazil
Departamento de Química e Exatas, Universidade Estadual do Sudoeste da Bahia, 45206-191, Jequié, BA, Brazil
* Author to whom correspondence should be addressed.
Received: 12 September 2012; in revised form: 5 November 2012 / Accepted: 7 November 2012 / Published: 12 November 2012
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.
Keywords: Maytenus robusta; pentacyclic triterpenes; NMR; DFT calculations; acetylcholinesterase inhibitory activity
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Sousa, G.F.; Duarte, L.P.; Alcântara, A.F.C.; Silva, G.D.F.; Vieira-Filho, S.A.; Silva, R.R.; Oliveira, D.M.; Takahashi, J.A. New Triterpenes from Maytenus robusta: Structural Elucidation Based on NMR Experimental Data and Theoretical Calculations. Molecules 2012, 17, 13439-13456.
Sousa GF, Duarte LP, Alcântara AFC, Silva GDF, Vieira-Filho SA, Silva RR, Oliveira DM, Takahashi JA. New Triterpenes from Maytenus robusta: Structural Elucidation Based on NMR Experimental Data and Theoretical Calculations. Molecules. 2012; 17(11):13439-13456.
Sousa, Grasiely F.; Duarte, Lucienir P.; Alcântara, Antônio F.C.; Silva, Grácia D.F.; Vieira-Filho, Sidney A.; Silva, Roqueline R.; Oliveira, Djalma M.; Takahashi, Jacqueline A. 2012. "New Triterpenes from Maytenus robusta: Structural Elucidation Based on NMR Experimental Data and Theoretical Calculations." Molecules 17, no. 11: 13439-13456.