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Planta Med 2010; 76(6): 607-610
DOI: 10.1055/s-0029-1240582
Pharmacology
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Triterpenoids with Acetylcholinesterase Inhibition from Chuquiraga erinacea D. Don. subsp. erinacea (Asteraceae)

María Soledad Vela Gurovic1 , María Julia Castro1 , Victoria Richmond2 , María Belén Faraoni1 , Marta S. Maier2 , Ana Paula Murray1
  • 1INQUISUR-CONICET, Departamento de Química, Universidad Nacional del Sur, Bahía Blanca, Argentina
  • 2UMYMFOR-Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina
Further Information

Publication History

received August 19, 2009 revised October 13, 2009

accepted October 18, 2009

Publication Date:
16 November 2009 (online)

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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 α-and β-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 0.5 mM. Looking forward to improve the water solubility of the active compounds, the sodium sulfate ester of 1 was prepared by reaction with the (CH3)3 N.SO3 complex. The semisynthetic derivative disodium calenduladiol disulfate (8) elicited higher AChE inhibition than 1 with 94.1 % of inhibition at 0.5 mM (IC50 = 0.190 ± 0.003 mM). 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.

Key words

acetylcholinesterase inhibitors - Chuquiraga erinacea - Asteraceae - pentacyclic triterpenes - Alzheimer's disease

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Prof. Dr. Ana P. Murray

INQUISUR – Departamento de Química
Universidad Nacional del Sur

Av. Alem 1253

B8000CPB Bahía Blanca

Argentina

Phone: + 54 29 14 59 51 01 ext. 35 38

Fax: + 54 29 14 59 51 87

Email: apmurray@uns.edu.ar

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