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


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.

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    • "Montanine was isolated in an appreciable amount from H. vittatum and showed remarkable cytostatic and psychopharmacological effects (da Silva et al., 2006, 2008), along with the ability to inhibit the acetylcholinesterase enzyme and increase the protein phosphorylation of the MAPK signaling pathway, whose cascade of reactions is strongly related with the memory process (da Silva, 2005; Pagliosa et al., 2010). Very recently, six Amaryllidaceae alkaloids were characterized from Hippeastrum species for the first time (de Andrade et al., 2011, 2014; Giordani et al., 2011b). Herein is reported the complete spectroscopic data of a new lycosinine derivative, 9-O-demethyllycosinine B (2), from Hippeastrum breviflorum Herbert. "
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    ABSTRACT: A new lycosinine derivative, 9-O-demethyllycosinine B, was isolated from the native Brazilian Hippeas-trum breviflorum Herb., Amaryllidaceae, along with the well-known alkaloids lycosinine B and lycorine. The structure of the new compound was established by physical and spectroscopic methods. 9-O-demethyllycosinine B is the third lycosinine variant identified in the Amaryllidaceae family.
    Revista Brasileira de Farmacognosia 07/2015; 25(4). DOI:10.1016/j.bjp.2015.06.005 · 0.83 Impact Factor
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    • "Comparing their GC/MS spectra with a private library database represented an alternative identification of the alkaloids. This library has been regularly updated with alkaloids isolated and unequivocally identified based on physical and spectroscopic means [12] "
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    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 · 2.70 Impact Factor
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    • "An alternative method used to identify the alkaloids was to compare their GC/MS spectra with those in a private library database. This library has been regularly updated with data for alkaloids that were isolated and unequivocally identified using physical and spectroscopic assays [14]. The mass spectra were deconvoluted using AMDIS 2.64 software (NIST). "
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    ABSTRACT: Acetylcholinesterase (AChE) enzymatic inhibition is an important target for the management of Alzheimer disease (AD) and AChE inhibitors are the mainstay drugs for its treatment. In order to discover new sources of potent AChE inhibitors, a combined strategy is presented based on AChE-inhibitory activity and chemical profiles by GC/MS, together with in silico studies. The combined strategy was applied on alkaloid extracts of five Amaryllidaceae species that grow in Colombia. Fifty-seven alkaloids were detected using GC/MS, and 21 of them were identified by comparing their mass-spectral fragmentation patterns with standard reference spectra in commercial and private library databases. The alkaloid extracts of Zephyranthes carinata exhibited a high level of inhibitory activity (IC50=5.97±0.24μg/mL). Molecular modeling, which was performed using the structures of some of the alkaloids present in this extract and the three-dimensional crystal structures of AChE derived from Torpedo californica, disclosed their binding configuration in the active site of this AChE. The results suggested that the alkaloids 3-epimacronine and lycoramine might be of interest for AChE inhibition. Although the galanthamine group is known for its potential utility in treating AD, the tazettine-type alkaloids should be evaluated to find more selective compounds of potential benefit for AD.
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