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Molecules 2012, 17(11), 13439-13456; doi:10.3390/molecules171113439
Article

New Triterpenes from Maytenus robusta: Structural Elucidation Based on NMR Experimental Data and Theoretical Calculations

1, 1,* , 1, 1, 2, 1, 3 and 1
1 Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, 31270-901, Belo Horizonte, MG, Brazil 2 Escola de Farmácia, Universidade Federal de Ouro Preto, 35400-000, Ouro Preto, MG, Brazil 3 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 / Revised: 5 November 2012 / Accepted: 7 November 2012 / Published: 12 November 2012
(This article belongs to the Special Issue Triterpenes and Triterpenoids)
Download PDF [238 KB, 18 June 2014; original version 18 June 2014]

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 Maytenus robusta; pentacyclic triterpenes; NMR; DFT calculations; acetylcholinesterase inhibitory activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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