Preparation and antitrypanosomal activity of secochiliolide acid derivatives

Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum bryoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochili...

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Autores principales:	Siless, G.E., Lozano, E., Sánchez, M., Mazzuca, M., Sosa, M.A., Palermo, J.A.
Formato:	JOUR
Materias:	Nardophyllum bryoides trypanocidal activity Secochiliolide acid Trypanosoma cruzi antitrypanosomal agent benznidazole carboxyl group exocyclic double bond furan secochiliolide acid derivative spironolactone unclassified drug article drug activity drug bioavailability drug synthesis epimastigote epoxidation high performance liquid chromatography IC 50 medicinal plant Nardophyllum bryoides nonhuman shrub trypanocidal activity Asteraceae Chagas Disease Diterpenes Humans Propionates Trypanocidal Agents
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_0960894X_v23_n17_p4964_Siless
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_0960894X_v23_n17_p4964_Siless
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spelling	todo:paper_0960894X_v23_n17_p4964_Siless2023-10-03T15:54:02Z Preparation and antitrypanosomal activity of secochiliolide acid derivatives Siless, G.E. Lozano, E. Sánchez, M. Mazzuca, M. Sosa, M.A. Palermo, J.A. Nardophyllum bryoides trypanocidal activity Secochiliolide acid Trypanosoma cruzi antitrypanosomal agent benznidazole carboxyl group exocyclic double bond furan secochiliolide acid derivative spironolactone unclassified drug article drug activity drug bioavailability drug synthesis epimastigote epoxidation high performance liquid chromatography IC 50 medicinal plant Nardophyllum bryoides nonhuman shrub Trypanosoma cruzi Nardophyllum bryoides Trypanosoma cruzi Nardophyllum bryoides Secochiliolide acid trypanocidal activity Trypanosoma cruzi Asteraceae Chagas Disease Diterpenes Humans Propionates Trypanocidal Agents Trypanosoma cruzi Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum bryoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 μg/mL. Six of the synthesized derivatives were also active with IC50's between 2 and 7 μg/mL which are comparable to that of the commercial drug benznidazole (2.5 μg/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule. © 2013 Elsevier Ltd. All rights reserved. Fil:Siless, G.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Palermo, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0960894X_v23_n17_p4964_Siless
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Nardophyllum bryoides trypanocidal activity Secochiliolide acid Trypanosoma cruzi antitrypanosomal agent benznidazole carboxyl group exocyclic double bond furan secochiliolide acid derivative spironolactone unclassified drug article drug activity drug bioavailability drug synthesis epimastigote epoxidation high performance liquid chromatography IC 50 medicinal plant Nardophyllum bryoides nonhuman shrub Trypanosoma cruzi Nardophyllum bryoides Trypanosoma cruzi Nardophyllum bryoides Secochiliolide acid trypanocidal activity Trypanosoma cruzi Asteraceae Chagas Disease Diterpenes Humans Propionates Trypanocidal Agents Trypanosoma cruzi
spellingShingle	Nardophyllum bryoides trypanocidal activity Secochiliolide acid Trypanosoma cruzi antitrypanosomal agent benznidazole carboxyl group exocyclic double bond furan secochiliolide acid derivative spironolactone unclassified drug article drug activity drug bioavailability drug synthesis epimastigote epoxidation high performance liquid chromatography IC 50 medicinal plant Nardophyllum bryoides nonhuman shrub Trypanosoma cruzi Nardophyllum bryoides Trypanosoma cruzi Nardophyllum bryoides Secochiliolide acid trypanocidal activity Trypanosoma cruzi Asteraceae Chagas Disease Diterpenes Humans Propionates Trypanocidal Agents Trypanosoma cruzi Siless, G.E. Lozano, E. Sánchez, M. Mazzuca, M. Sosa, M.A. Palermo, J.A. Preparation and antitrypanosomal activity of secochiliolide acid derivatives
topic_facet	Nardophyllum bryoides trypanocidal activity Secochiliolide acid Trypanosoma cruzi antitrypanosomal agent benznidazole carboxyl group exocyclic double bond furan secochiliolide acid derivative spironolactone unclassified drug article drug activity drug bioavailability drug synthesis epimastigote epoxidation high performance liquid chromatography IC 50 medicinal plant Nardophyllum bryoides nonhuman shrub Trypanosoma cruzi Nardophyllum bryoides Trypanosoma cruzi Nardophyllum bryoides Secochiliolide acid trypanocidal activity Trypanosoma cruzi Asteraceae Chagas Disease Diterpenes Humans Propionates Trypanocidal Agents Trypanosoma cruzi
description	Secochiliolide acid (1) isolated from the Patagonian shrub Nardophyllum bryoides, was used as a scaffold for the preparation of a series of nine derivatives. Compound 1 and its derivatives were tested against Trypanosoma cruzi epimastigotes grown in liquid media. It was first observed that secochiliolide acid (1) inhibited the proliferation of the parasites, with an IC50 of 2 μg/mL. Six of the synthesized derivatives were also active with IC50's between 2 and 7 μg/mL which are comparable to that of the commercial drug benznidazole (2.5 μg/mL). These results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important. Moreover, the presence of the furan and spirolactone rings is not essential for the bioactivity per se, but is important in combination with other structural fragments present in the molecule. © 2013 Elsevier Ltd. All rights reserved.
format	JOUR
author	Siless, G.E. Lozano, E. Sánchez, M. Mazzuca, M. Sosa, M.A. Palermo, J.A.
author_facet	Siless, G.E. Lozano, E. Sánchez, M. Mazzuca, M. Sosa, M.A. Palermo, J.A.
author_sort	Siless, G.E.
title	Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_short	Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_full	Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_fullStr	Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_full_unstemmed	Preparation and antitrypanosomal activity of secochiliolide acid derivatives
title_sort	preparation and antitrypanosomal activity of secochiliolide acid derivatives
url	http://hdl.handle.net/20.500.12110/paper_0960894X_v23_n17_p4964_Siless
work_keys_str_mv	AT silessge preparationandantitrypanosomalactivityofsecochiliolideacidderivatives AT lozanoe preparationandantitrypanosomalactivityofsecochiliolideacidderivatives AT sanchezm preparationandantitrypanosomalactivityofsecochiliolideacidderivatives AT mazzucam preparationandantitrypanosomalactivityofsecochiliolideacidderivatives AT sosama preparationandantitrypanosomalactivityofsecochiliolideacidderivatives AT palermoja preparationandantitrypanosomalactivityofsecochiliolideacidderivatives
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Preparation and antitrypanosomal activity of secochiliolide acid derivatives

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