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Molecules 2015, 20(10), 18264-18278; doi:10.3390/molecules201018264

New Non-Toxic Semi-Synthetic Derivatives from Natural Diterpenes Displaying Anti-Tuberculosis Activity

1
Pesquisas em Ciências Exatas e Tecnológicas, Universidade de Franca, Franca 14404-600, Brazil
2
School of Chemistry, University of East Anglia, Norwich Research Park, Norwich, NR4 7TJ, UK
3
Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto 14040-903, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 25 August 2015 / Revised: 30 September 2015 / Accepted: 30 September 2015 / Published: 7 October 2015
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [742 KB, uploaded 7 October 2015]   |  

Abstract

We report herein the synthesis of six diterpene derivatives, three of which are new, generated through known organic chemistry reactions that allowed structural modification of the existing natural products kaurenoic acid (1) and copalic acid (2). The new compounds were fully characterized using high resolution mass spectrometry, infrared spectroscopy, 1H- and 13C-NMR experiments. We also report the evaluation of the anti-tuberculosis potential for all compounds, which showed some promising results for Micobacterium tuberculosis inhibition. Moreover, the toxicity for each of the most active compounds was also assessed. View Full-Text
Keywords: kaurenoic acid; copalic acid; structural modification; diterpene derivatives; anti-tuberculosis activity; cytotoxicity; Mycobacterium tuberculosis kaurenoic acid; copalic acid; structural modification; diterpene derivatives; anti-tuberculosis activity; cytotoxicity; Mycobacterium tuberculosis
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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. (CC BY 4.0).

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MDPI and ACS Style

Matos, P.M.; Mahoney, B.; Chan, Y.; Day, D.P.; Cabral, M.M.W.; Martins, C.H.G.; Santos, R.A.; Bastos, J.K.; Page, P.C.B.; Heleno, V.C.G. New Non-Toxic Semi-Synthetic Derivatives from Natural Diterpenes Displaying Anti-Tuberculosis Activity. Molecules 2015, 20, 18264-18278.

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