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New non-toxic semi-synthetic derivatives from natural diterpenes displaying promising anti-tuberculosis activity

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Authors

  • Priscilla M. Matos
  • Brian Mahoney
  • Yohan Chan
  • David Day
  • Mirela Cabral
  • Carlos Martins
  • Raquel Santos
  • Jairo Bastos
  • Philip Bulman Page
  • Vladimir Heleno

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Abstract

We herein report the synthesis of six diterpene derivatives, three of which are 23 new, generated through known organic chemistry reactions that allowed structural 24 modification of the existing natural products kaurenoic acid (1) and copalic acid (2). The 25 new compounds were fully characterized using high resolution mass spectrometry, infra-26 red spectroscopy, 1H and 13C NMR experiments. We also report the evaluation of the anti-27 tuberculosis potential for all compounds, which showed some promising results for 28 Micobacterium tuberculosis inhibition. Moreover, the toxicity for each of the most active 29 compounds was also assessed.

Details

Original languageEnglish
Pages (from-to)18264-18278
Number of pages15
JournalMolecules
Volume20
Issue number10
DOIs
Publication statusPublished - 7 Oct 2015
Peer-reviewedYes

Keywords

    Research areas

  • kaurenoic acid, copalic acid, structural modification, diterpene derivatives, anti-tuberculosis activity, cytotoxicity, Mycobacterium tuberculosis

Bibliographic note

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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