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Abstract:

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.

Registro:

Documento: Artículo
Título:Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)
Autor:Gurovic, M.S.V.; Castro, M.J.; Richmond, V.; Faraoni, M.B.; Maier, M.S.; Murray, A.P.
Filiación:INQUISUR-CONICET, Departamento de Química, Universidad Nacional Del sur, Av. Alem 1253, B8000CPB Bahía Blanca, Argentina
UMYMFOR-Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Palabras clave: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
Año:2010
Volumen:76
Número:6
Página de inicio:607
Página de fin:610
DOI: http://dx.doi.org/10.1055/s-0029-1240582
Título revista:Planta Medica
Título revista abreviado:Planta Med.
ISSN:00320943
CODEN:PLMEA
CAS:acetylcholinesterase, 9000-81-1; alpha amyrin, 638-95-9; beta amyrin, 559-70-6; lupeol, 545-47-1; pseudotaraxasterol acetate, 4586-65-6; taraxasterol, 1059-14-9; Cholinesterase Inhibitors; Triterpenes
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00320943_v76_n6_p607_Gurovic

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Citas:

---------- APA ----------
Gurovic, M.S.V., Castro, M.J., Richmond, V., Faraoni, M.B., Maier, M.S. & Murray, A.P. (2010) . Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae). Planta Medica, 76(6), 607-610.
http://dx.doi.org/10.1055/s-0029-1240582
---------- CHICAGO ----------
Gurovic, M.S.V., Castro, M.J., Richmond, V., Faraoni, M.B., Maier, M.S., Murray, A.P. "Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)" . Planta Medica 76, no. 6 (2010) : 607-610.
http://dx.doi.org/10.1055/s-0029-1240582
---------- MLA ----------
Gurovic, M.S.V., Castro, M.J., Richmond, V., Faraoni, M.B., Maier, M.S., Murray, A.P. "Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)" . Planta Medica, vol. 76, no. 6, 2010, pp. 607-610.
http://dx.doi.org/10.1055/s-0029-1240582
---------- VANCOUVER ----------
Gurovic, M.S.V., Castro, M.J., Richmond, V., Faraoni, M.B., Maier, M.S., Murray, A.P. Triterpenoids with acetylcholinesterase inhibition from chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae). Planta Med. 2010;76(6):607-610.
http://dx.doi.org/10.1055/s-0029-1240582