Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)

A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE) inhibitory agents in the ethanolic extract of Chuquiraga erinacea D. Don. subsp. erinacea leaves using a bioautographic method. This permitted the isolation of the pentacyclic triterpenes calenduladiol (1), faradiol...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autor principal:	Maier, Marta Silvia
Publicado:	2010
Materias:	Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Cholinesterase Inhibitors Molecular Structure Triterpenes Erinacea
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00320943_v76_n6_p607_Gurovic http://hdl.handle.net/20.500.12110/paper_00320943_v76_n6_p607_Gurovic
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00320943_v76_n6_p607_Gurovic
record_format	dspace
spelling	paper:paper_00320943_v76_n6_p607_Gurovic2023-06-08T15:00:07Z Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae) Maier, Marta Silvia Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article Asteraceae Chuquiraga erinacea controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Asteraceae Cholinesterase Inhibitors Molecular Structure Triterpenes Asteraceae Chuquiraga erinacea Erinacea A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE) inhibitory agents in the ethanolic extract of Chuquiraga erinacea D. Don. subsp. erinacea leaves using a bioautographic method. This permitted the isolation of the pentacyclic triterpenes calenduladiol (1), faradiol (2), heliantriol B2 (3), lupeol (4), and a mixture of -and -amyrin (5a and 5b) as active constituents. Pseudotaraxasterol (6) and taraxasterol (7) were also isolated from this extract and showed no activity at the same analytical conditions. Compound 1 showed the highest AChE inhibitory activity with 31.2% of inhibition at 0.5mM. Looking forward to improve the water solubility of the active compounds, the sodium sulfate ester of 1 was prepared by reaction with the (CH3)3N.SO3 complex. The semisynthetic derivative disodium calenduladiol disulfate (8) elicited higher AChE inhibition than 1 with 94.1% of inhibition at 0.5mM (IC50=0. 1900.003mM). Compounds 1, 2, 3, 5, 6, and 7 are reported here for the first time in C. erinacea. This is the first report of AChE inhibition from calenduladiol (1) as well as from a sulfate derived from a natural product. © Georg Thieme Verlag KG Stuttgart - New York. Fil:Maier, M.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2010 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00320943_v76_n6_p607_Gurovic http://hdl.handle.net/20.500.12110/paper_00320943_v76_n6_p607_Gurovic
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article Asteraceae Chuquiraga erinacea controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Asteraceae Cholinesterase Inhibitors Molecular Structure Triterpenes Asteraceae Chuquiraga erinacea Erinacea
spellingShingle	Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article Asteraceae Chuquiraga erinacea controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Asteraceae Cholinesterase Inhibitors Molecular Structure Triterpenes Asteraceae Chuquiraga erinacea Erinacea Maier, Marta Silvia Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
topic_facet	Acetylcholinesterase inhibitors Alzheimer's disease Asteraceae Chuquiraga erinacea Pentacyclic triterpenes acetylcholinesterase alpha amyrin beta amyrin calenduladiol disodium calenduladiol disulfate faradiol heliantriol b2 lupeol pentacyclic triterpene pseudotaraxasterol acetate taraxasterol unclassified drug article Asteraceae Chuquiraga erinacea controlled study drug isolation drug solubility drug structure drug synthesis enzyme inhibition Asteraceae Cholinesterase Inhibitors Molecular Structure Triterpenes Asteraceae Chuquiraga erinacea Erinacea
description	A bioactivity-guided approach was taken to identify the acetylcholinesterase (AChE) inhibitory agents in the ethanolic extract of Chuquiraga erinacea D. Don. subsp. erinacea leaves using a bioautographic method. This permitted the isolation of the pentacyclic triterpenes calenduladiol (1), faradiol (2), heliantriol B2 (3), lupeol (4), and a mixture of -and -amyrin (5a and 5b) as active constituents. Pseudotaraxasterol (6) and taraxasterol (7) were also isolated from this extract and showed no activity at the same analytical conditions. Compound 1 showed the highest AChE inhibitory activity with 31.2% of inhibition at 0.5mM. Looking forward to improve the water solubility of the active compounds, the sodium sulfate ester of 1 was prepared by reaction with the (CH3)3N.SO3 complex. The semisynthetic derivative disodium calenduladiol disulfate (8) elicited higher AChE inhibition than 1 with 94.1% of inhibition at 0.5mM (IC50=0. 1900.003mM). Compounds 1, 2, 3, 5, 6, and 7 are reported here for the first time in C. erinacea. This is the first report of AChE inhibition from calenduladiol (1) as well as from a sulfate derived from a natural product. © Georg Thieme Verlag KG Stuttgart - New York.
author	Maier, Marta Silvia
author_facet	Maier, Marta Silvia
author_sort	Maier, Marta Silvia
title	Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
title_short	Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
title_full	Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
title_fullStr	Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
title_full_unstemmed	Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
title_sort	triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea d. don. subsp. erinacea (asteraceae)
publishDate	2010
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00320943_v76_n6_p607_Gurovic http://hdl.handle.net/20.500.12110/paper_00320943_v76_n6_p607_Gurovic
work_keys_str_mv	AT maiermartasilvia triterpenoidswithacetylcholinesteraseinhibitionfromchuquiragaerinaceaddonsubsperinaceaasteraceae
_version_	1768543409462575104

Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)

Ejemplares similares