Triterpenoids with Acetylcholinesterase Inhibition fromChuquiraga erinaceaD. Don. subsp.erinacea(Asteraceae)

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 alpha-and beta-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)3N.SO3 complex. The semisynthetic derivative disodium calenduladiol disulfate (8) elicited higher AChE inhibition than 1 with 94.1 % of inhibition at 0.5 mM (IC (50) = 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.

Cytotoxic effects induced by combination of heliantriol B2 and dequalinium against human leukemic cell lines

“…Calenduladiol (lup‐20(29)‐en‐3 β ,16 β ‐diol), faradiol (taraxast‐20‐ene‐3 β ,16 β ‐diol) and heliantriol B2 (HB2) (lup‐20(29)‐ene‐3 β ,16 β ,28‐triol) were isolated from Chuquiraga erinacea D. Don subsp. erinacea as described previously (Vela Gurovic et al ., 2010). These triterpenes were dissolved in DMSO at a concentration of 25 m m for both calenduladiol and faradiol and 20 m m for HB2, filter sterilized and stored at −80°C until used.…”

“…Many pentacyclic triterpene alcohols isolated from plants belonging to the Asteraceae family possess cytotoxic activity against human cancer cell lines (Ukiya et al ., 2002; García and Delgado, 2006). Chuquiraga erinacea D. Don (Asteraceae), an endemic species from Argentina, contains several pentacyclic triterpenes which possess a large number of biological activities including antiinflammatory and chemoprotective (Vela Gurovic et al ., 2010). The present work first evaluated the cytotoxic potential of the pentacyclic triterpenes, calenduladiol, faradiol and heliantriol B2 (HB2), isolated from C. erinacea (chemical structure shown in Fig.…”

Identification of Potential Herbal Inhibitor of Acetylcholinesterase Associated Alzheimer’s Disorders Using Molecular Docking and Molecular Dynamics Simulation

“…A number of phytochemicals, namely, alkaloids, pregnane glycosides (cynanchoides), stilbenes, triterpenes [12], ursane [13], and xanthones, have shown AChE inhibitory activity. However, tetrahydrocannabinol (THC) is a pharmacologically active secondary metabolite in Cannabis plant and is one of the oldest hallucinogenic drugs and found to inhibit AChE more effectively than commercially marketed drugs [14, 15].…”

Lupane Triterpenoids, Selective Butyrylcholinesterase Inhibitors

“…[5][6][7] Lupanes in particular, have attracted attention due to the broad range of biological and pharmacological properties that they exhibit such as anticancer, antitumor, anti-inflammatory, anti-HIV, anticholinesterase, insecticidal and antimalarial activities. 3,4,[8][9][10][11][12][13][14][15] Our interest in bioactive triterpenes, prompted us to synthesize a series of derivatives from natural lupeol (1) and calenduladiol (2), isolated from Chuquiraga erinacea D. Don. subsp.…”

“…erinacea (Asteraceae). [14][15][16] Lupeol (1) and calenduladiol (2) are pentacyclic triterpenes belonging to the lupane family. In a previous work, we observed the enhancement of the inhibitory activity against BChE of 2 by the introduction of keto groups at C-3, C-16 and C-30.…”