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

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

doi:10.3390/molecules201018264

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

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

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

21 Downloads (Pure)

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.

Original language	English
Pages (from-to)	18264-18278
Number of pages	15
Journal	Molecules
Volume	20
Issue number	10
DOIs	https://doi.org/10.3390/molecules201018264
Publication status	Published - 7 Oct 2015

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

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

Access to Document

10.3390/molecules201018264Licence: CC BY

molecules-20-18264Final published version, 738 KBLicence: CC BY

Cite this

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title = "New non-toxic semi-synthetic derivatives from natural diterpenes displaying promising anti-tuberculosis activity",

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.",

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AU - Matos, Priscilla M.

AU - Mahoney, Brian

AU - Chan, Yohan

AU - Day, David

AU - Cabral, Mirela

AU - Martins, Carlos

AU - Santos, Raquel

AU - Bastos, Jairo

AU - Bulman Page, Philip

AU - Heleno, Vladimir

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N2 - 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.

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KW - copalic acid

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KW - diterpene derivatives

KW - anti-tuberculosis activity

KW - cytotoxicity

KW - Mycobacterium tuberculosis

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