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Molecules 2016, 21(9), 1237; doi:10.3390/molecules21091237

ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity

1
Institute of Pharmaceutical Biology and Phytochemistry (IPBP), University of Münster, PharmaCampus Corrensstraße 48, Münster D-48149, Germany
2
AsterBioChem Research Team, Laboratory of Pharmacognosy, School of Pharmaceutical Sciences of Ribeirão Preto, USP, Av. do Café s/n, Ribeirão Preto-SP 14040-903, Brazil
3
Swiss Tropical and Public Health Institute (Swiss TPH), Socinstr. 57, Basel CH-4051, Switzerland
4
University of Basel, Petersplatz 1, Basel CH-4003, Switzerland
This work is part of the doctoral thesis (Mauro Nogueira da Silva, University of Münster, 2016).
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 30 August 2016 / Revised: 12 September 2016 / Accepted: 13 September 2016 / Published: 15 September 2016
View Full-Text   |   Download PDF [1134 KB, uploaded 22 September 2016]   |  

Abstract

Aldama discolor (syn.Viguiera discolor) is an endemic Asteraceae from the Brazilian “Cerrado”, which has not previously been investigated for its chemical constituents and biological activity. Diterpenes are common secondary metabolites found in Aldama species, some of which have been reported to present potential antiprotozoal and antimicrobial activities. In this study, the known ent-3-α-hydroxy-kaur-16-en-18-ol (1), as well as three new diterpenes, namely, ent-7-oxo-pimara-8,15-diene-18-ol (2), ent-2S,4S-2-19-epoxy-pimara-8(3),15-diene-7β-ol (3) and ent-7-oxo-pimara-8,15-diene-3β-ol (4), were isolated from the dichloromethane extract of A. discolor leaves and identified by means of MS and NMR. The compounds were assayed in vitro against Trypanosoma brucei rhodesiense, T. cruzi and Leishmania donovani, Plasmodium falciparum and also tested for cytotoxicity against mammalian cells (L6 cell line). The ent-kaurane 1 showed significant in vitro activity against both P. falciparum (IC 50 = 3.5 μ M) and L. donovani (IC 50 = 2.5 μ M) and ent-pimarane 2 against P. falciparum (IC 50 = 3.8 μ M). Both compounds returned high selectivity indices (SI >10) in comparison with L6 cells, which makes them interesting candidates for in vivo tests. In addition to the diterpenes, the sesquiterpene lactone budlein A (5), which has been reported to possess a strong anti-T. b. rhodesiense activity, was identified as major compound in the A. discolor extract and explains its high activity against this parasite (100% growth inhibition at 2 μ g/mL). View Full-Text
Keywords: Aldama discolor; Viguiera discolor; Asteraceae; ent-pimarane; ent-kaurane; antiprotozoal activity; Trypanosoma brucei rhodesiense; Trypanosoma cruzi; Leishmania donovani; Plasmodium falciparum Aldama discolor; Viguiera discolor; Asteraceae; ent-pimarane; ent-kaurane; antiprotozoal activity; Trypanosoma brucei rhodesiense; Trypanosoma cruzi; Leishmania donovani; Plasmodium falciparum
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Nogueira, M.S.; Da Costa, F.B.; Brun, R.; Kaiser, M.; Schmidt, T.J. ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity. Molecules 2016, 21, 1237.

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