ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity
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 pr...
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doaj-beaf7a1f40d14702a08827ea45e422b72020-11-24T22:33:44ZengMDPI AGMolecules1420-30492016-09-01219123710.3390/molecules21091237molecules21091237ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal ActivityMauro S. Nogueira0Fernando B. Da Costa1Reto Brun2Marcel Kaiser3Thomas J. Schmidt4Institute of Pharmaceutical Biology and Phytochemistry (IPBP), University of Münster, PharmaCampus Corrensstraße 48, Münster D-48149, GermanyAsterBioChem Research Team, Laboratory of Pharmacognosy, School of Pharmaceutical Sciences of Ribeirão Preto, USP, Av. do Café s/n, Ribeirão Preto-SP 14040-903, BrazilSwiss Tropical and Public Health Institute (Swiss TPH), Socinstr. 57, Basel CH-4051, SwitzerlandSwiss Tropical and Public Health Institute (Swiss TPH), Socinstr. 57, Basel CH-4051, SwitzerlandInstitute of Pharmaceutical Biology and Phytochemistry (IPBP), University of Münster, PharmaCampus Corrensstraße 48, Münster D-48149, GermanyAldama 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).http://www.mdpi.com/1420-3049/21/9/1237Aldama discolorViguiera discolorAsteraceaeent-pimaraneent-kauraneantiprotozoal activityTrypanosoma brucei rhodesienseTrypanosoma cruziLeishmania donovaniPlasmodium falciparum |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Mauro S. Nogueira Fernando B. Da Costa Reto Brun Marcel Kaiser Thomas J. Schmidt |
spellingShingle |
Mauro S. Nogueira Fernando B. Da Costa Reto Brun Marcel Kaiser Thomas J. Schmidt ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity Molecules Aldama discolor Viguiera discolor Asteraceae ent-pimarane ent-kaurane antiprotozoal activity Trypanosoma brucei rhodesiense Trypanosoma cruzi Leishmania donovani Plasmodium falciparum |
author_facet |
Mauro S. Nogueira Fernando B. Da Costa Reto Brun Marcel Kaiser Thomas J. Schmidt |
author_sort |
Mauro S. Nogueira |
title |
ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity |
title_short |
ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity |
title_full |
ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity |
title_fullStr |
ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity |
title_full_unstemmed |
ent-Pimarane and ent-Kaurane Diterpenes from Aldama discolor (Asteraceae) and Their Antiprotozoal Activity |
title_sort |
ent-pimarane and ent-kaurane diterpenes from aldama discolor (asteraceae) and their antiprotozoal activity |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2016-09-01 |
description |
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). |
topic |
Aldama discolor Viguiera discolor Asteraceae ent-pimarane ent-kaurane antiprotozoal activity Trypanosoma brucei rhodesiense Trypanosoma cruzi Leishmania donovani Plasmodium falciparum |
url |
http://www.mdpi.com/1420-3049/21/9/1237 |
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