Article

Alkaloids from Hippeastrum papilio

Departament de Products Naturals, Biologia Vegetal i Edafologia, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, E-08028 Barcelona, Spain.
Molecules (Impact Factor: 2.42). 12/2011; 16(8):7097-104. DOI: 10.3390/molecules16087097
Source: PubMed

ABSTRACT Galanthamine, an acetylcholinesterase inhibitor marketed as a hydrobromide salt (Razadyne®, Reminyl®) for the treatment of Alzheimer's disease (AD), is obtained from Amaryllidaceae plants, especially those belonging to the genera Leucojum, Narcissus, Lycoris and Ungernia. The growing demand for galanthamine has prompted searches for new sources of this compound, as well as other bioactive alkaloids for the treatment of AD. In this paper we report the isolation of the new alkaloid 11β-hydroxygalanthamine, an epimer of the previously isolated alkaloid habranthine, which was identified using NMR techniques. It has been shown that 11β-hydroxygalanthamine has an important in vitro acetylcholinesterase inhibitory activity. Additionally, Hippeastrum papilio yielded substantial quantities of galanthamine.

Download full-text

Full-text

Available from: Jaume Bastida, Jul 05, 2015
1 Follower
 · 
420 Views
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Amaryllidaceae alkaloids exhibit a wide range of physiological effects, of which the acetylcholinesterase (AChE) inhibitory activity is the most relevant. However, scientific evidence related to their neuroprotective effectiveness against glutamate-induced toxicity has been lacking. Thus, the purpose of this study was to conduct a comparative study of the neuroprotective activity and the AChE inhibitory activity of species of Amaryllidaceae. The neuroprotective activity against glutamate-induced toxicity was measured in rat cortical neurons and the Ellman method was employed for the quantification of acetylcholinesterase inhibitory activity of alkaloidal extracts of five species of Amaryllidaceae (Crinum jagus, C. bulbispermum, Hippeastrun barbatum, H. puniceum and Zephyrantes carinata). The alkaloid Amaryllidaceae patterns based on GC/MS analyses were also investigated. The results showed that the alkaloidal extract from C. jagus presented high neuroprotective activity in both pre and post treatment against a glutamate excitotoxic stimulus. Furthermore, the alkaloid extracts from C. jagus and Z. carinata revealed an inhibitory activity of AChE from the electric eel with IC50 values of 18.28 ± 0.29 and 17.96 ± 1.22 μg/mL, respectively. In addition, 46 alkaloids were detected by GC/MS, and 20 of them were identified based on their mass spectra and retention index. The results suggest that the neuroprotective effects might be associated with lycorine and crinine-type alkaloids, whereas the acetylcholinesterase enzyme inhibitory activity could be related to galanthamine and lycorine-type alkaloids, although not based on synergistic processes. In summary, Amaryllidaceae species are sources of alkaloids with potential use for Alzheimer's disease. Copyright © 2014. Published by Elsevier Inc.
    Life sciences 12/2014; DOI:10.1016/j.lfs.2014.12.011 · 2.30 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: An ongoing search for alkaloids in the Amaryllidaceae species using GC-MS resulted in the identification of two crinine-type alkaloids, aulicine (1) and 3-O-methyl-epimacowine, (2) from the indigenous Brazilian species Hippeastrum aulicum and Hippeastrum calyptratum, respectively. In addition, two alkaloids, 11-oxohaemanthamine (3) and 7-methoxy-O-methyllycorenine (4) were both isolated from H. aulicum. Furthermore, we provide here complete NMR spectroscopic data for the homolycorine analogues nerinine (5) and albomaculine (6). The absolute stereochemistry of the 5,10b-ethano bridge in the crinine variants was determined by circular dichroism and X-ray crystallographic analysis, thus presenting the first direct evidence for the presence of crinine-type alkaloids in the genus Hippeastrum.
    Phytochemistry 04/2014; 103. DOI:10.1016/j.phytochem.2014.03.007 · 3.35 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Crinine-, haemanthamine- and homolycorine-type alkaloids are described from the genus Hippeastrum by means of NMR, X-ray crystallography and CD spectroscopy. Crinine alkaloids are reported for the first time in this genus.
    Phytochemistry 01/2014; · 3.35 Impact Factor