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Jaume Bastida - One of the best experts on this subject based on the ideXlab platform.
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alkaloid profile in pyrolirion albicans herb amaryllidaceae a peruvian endemic species
South African Journal of Botany, 2021Co-Authors: Hibert Huaylla, Laura Torrasclaveria, Olimpia Llalla, Jaume BastidaAbstract:Abstract The Amaryllidaceae family is widely distributed in different regions of the neotropics and temperate areas of the world. Species of the subfamily Amaryllidoideae are unique in producing the alkaloid Galanthamine, which inhibits the action of acetylcholinesterase and is used for the treatment of Alzheimer's disease. In Peru, 15 genera and 68 species belonging to the Amaryllidoideae have been reported in different types of forest, ranging from wet montane to dry, as well as the sandy biomes of the Pacific coastal region, with the greatest diversity in the south. In the tribe Eustephieae, the Andean genus Pyrolirion Herb has eight species, six of which are endemic to Peru. In this work, the leaves and bulbs of Pyrolirion albicans were analyzed for their alkaloid content for the first time, using gas chromatography (GC) coupled to mass spectrometry (MS). The alkaloids determined in the leaves were Galanthamine, chlidanthine, tazettine and lycorine and those in the bulbs were Galanthamine, N-demethylGalanthamine, vittatine/crinine, montanine, pancracine, sternbergine, lycorine and hippeastrine. Owing to their important bioactive properties, the high quantity of montanine and Galanthamine determined in the bulbs is of particular interest.
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analysis of bioactive amaryllidaceae alkaloid profiles in lycoris species by gc ms
Natural Product Communications, 2014Co-Authors: Ying Guo, Francesc Viladomat, Carles Codina, Jean Paulo De Andrade, Warley De Souza Borges, Natalia B Pigni, Yuhong Zheng, Laura Torrasclaveria, Jaume BastidaAbstract:The genus Lycoris, a group of Amaryllidaceae plants distributed in temperate regions of Eastern Asia, is already known for containing representative alkaloids typical of this botanical family with a wide range of biological activities (for example, lycorine and Galanthamine). In the present work, the alkaloid profiles of nine species, L. albiflora, L. aurea, L. chinensis, L. haywardii, L. incarnata, L. longituba, L. radiata, L. sprengeri, and L. squamigera, and one variety (L. radiata var. pumila) have been evaluated by GC-MS. Structures belonging to the lycorine-, homolycorine-, haemanthamine-, narciclasine-, tazettine-, montanine- and Galanthamine-series were identified and quantified, with Galanthamine- and lycorine-type alkaloids predominating and usually showing a high relative abundance in comparison with other alkaloids of the extracts. Interestingly, L. longituba revealed itself to be a potential commercial source of bioactive alkaloids. In general terms, our results are consistent with the alkaloid profiles reported in the literature for previously studied species.
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daffodils as potential crops of Galanthamine assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity
Industrial Crops and Products, 2013Co-Authors: Laura Torrasclaveria, Strahil Berkov, Francesc Viladomat, Carles Codina, Jaume BastidaAbstract:Abstract Many plant varieties of Narcissus (Amaryllidaceae) are cultivated on a large scale for ornamental purposes but they are also known to contain Galanthamine, a bioactive alkaloid used in antiacetylcholinesterasic therapy in Alzheimer's disease. More than 100 ornamental varieties of Narcissus , using leaves and bulbs separately, were screened for their Galanthamine content as well as their acetylcholinesterase inhibitory activity in the search for new potential sources of Galanthamine. GC–MS was used for the quantitative analysis of Galanthamine, and the biological activity was determined by an acetylcholinesterase in vitro assay. Galanthamine was found to occur in the leaves or bulbs of 97 ornamental varieties, the maximal amount being 0.46% referred to DW in the leaves of Narcissus hispanicus , and 0.14% in the bulbs of the cultivar ‘Yellow Wings’. Sanguinine, an even more powerful inhibitor of acetylcholinesterase than Galanthamine, was also found in the leaves and bulbs of 22 ornamental varieties of Narcissus , which exhibited a high acetylcholinesterase inhibitory activity.
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wild argentinian amaryllidaceae a new renewable source of the acetylcholinesterase inhibitor Galanthamine and other alkaloids
Molecules, 2012Co-Authors: Javier E Ortiz, Strahil Berkov, Jaume Bastida, Natalia B Pigni, Cristina Theoduloz, German Roitman, Alejandro Tapia, Gabriela Egly FeresinAbstract:The Amaryllidaceae family is well known for its pharmacologically active alkaloids. An important approach to treat Alzheimer’s disease involves the inhibition of the enzyme acetylcholinesterase (AChE). Galanthamine, an Amaryllidaceae alkaloid, is an effective, selective, reversible, and competitive AchE inhibitor. This work was aimed at studying the alkaloid composition of four wild Argentinian Amarillydaceae species for the first time, as well as analyzing their inhibitory activity on acetylcholinesterase. Alkaloid content was characterized by means of GC-MS analysis. Chloroform basic extracts from Habranthus jamesonii, Phycella herbertiana, Rhodophiala mendocina and Zephyranthes filifolia collected in the Argentinian Andean region all contained Galanthamine, and showed a strong AChE inhibitory activity (IC50 between 1.2 and 2 µg/mL). To our knowledge, no previous reports on alkaloid profiles and AChEIs activity of wild Argentinian Amarillydaceae species have been publisihed. The demand for renewable sources of industrial products like Galanthamine and the need to protect plant biodiversity creates an opportunity for Argentinian farmers to produce such crops.
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gc ms of amaryllidaceous Galanthamine type alkaloids
Journal of Mass Spectrometry, 2012Co-Authors: Strahil Berkov, Francesc Viladomat, Carles Codina, Sergio Suarez, Angel Ravelo, Jaume BastidaAbstract:Galanthamine-type alkaloids produced by plants of the Amaryllidaceae family are potent acetylcholinesterase inhibitors. One of them, Galanthamine, has been marketed as a hydrobromide salt for the treatment of Alzheimer's disease. In the present work, gas chromatography with electron impact mass spectrometry (GC-EIMS) fragmentation of 12 reference compounds isolated from various amaryllidaceous plants and identified by spectroscopic methods (1D and 2D nuclear magnetic resonance, circular dichroism, high-resolution MS (HRMS) and EIMS) was studied by tandem mass spectrometry (GC-MS/MS) and accurate mass measurements (GC-HRMS). The studied compounds showed good peak shape and efficient GC separation with a GC-MS fragmentation pattern similar to that obtained by direct insertion probe. With the exception of Galanthamine-N-oxide and N-formylnorGalanthamine, the Galanthamine-type compounds showed abundant [M](+.) and [M-H](+) ions. A typical fragmentation pattern was also observed, depending on the substituents of the skeleton. Based on the fragmentation pathways of reference compounds, three other Galanthamine-type alkaloids, including 3-O-(2'-butenoyl)sanguinine, which possesses a previously unelucidated structure, were identified in Leucojum aestivum ssp. pulchelum, a species endemic to the Balearic islands. GC-MS can be successfully applied to Amaryllidaceae plant samples in the routine screening for potentially new or known bioactive molecules, chemotaxonomy, biodiversity and identification of impurities in pharmaceutical substances.
Strahil Berkov - One of the best experts on this subject based on the ideXlab platform.
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daffodils as potential crops of Galanthamine assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity
Industrial Crops and Products, 2013Co-Authors: Laura Torrasclaveria, Strahil Berkov, Francesc Viladomat, Carles Codina, Jaume BastidaAbstract:Abstract Many plant varieties of Narcissus (Amaryllidaceae) are cultivated on a large scale for ornamental purposes but they are also known to contain Galanthamine, a bioactive alkaloid used in antiacetylcholinesterasic therapy in Alzheimer's disease. More than 100 ornamental varieties of Narcissus , using leaves and bulbs separately, were screened for their Galanthamine content as well as their acetylcholinesterase inhibitory activity in the search for new potential sources of Galanthamine. GC–MS was used for the quantitative analysis of Galanthamine, and the biological activity was determined by an acetylcholinesterase in vitro assay. Galanthamine was found to occur in the leaves or bulbs of 97 ornamental varieties, the maximal amount being 0.46% referred to DW in the leaves of Narcissus hispanicus , and 0.14% in the bulbs of the cultivar ‘Yellow Wings’. Sanguinine, an even more powerful inhibitor of acetylcholinesterase than Galanthamine, was also found in the leaves and bulbs of 22 ornamental varieties of Narcissus , which exhibited a high acetylcholinesterase inhibitory activity.
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wild argentinian amaryllidaceae a new renewable source of the acetylcholinesterase inhibitor Galanthamine and other alkaloids
Molecules, 2012Co-Authors: Javier E Ortiz, Strahil Berkov, Jaume Bastida, Natalia B Pigni, Cristina Theoduloz, German Roitman, Alejandro Tapia, Gabriela Egly FeresinAbstract:The Amaryllidaceae family is well known for its pharmacologically active alkaloids. An important approach to treat Alzheimer’s disease involves the inhibition of the enzyme acetylcholinesterase (AChE). Galanthamine, an Amaryllidaceae alkaloid, is an effective, selective, reversible, and competitive AchE inhibitor. This work was aimed at studying the alkaloid composition of four wild Argentinian Amarillydaceae species for the first time, as well as analyzing their inhibitory activity on acetylcholinesterase. Alkaloid content was characterized by means of GC-MS analysis. Chloroform basic extracts from Habranthus jamesonii, Phycella herbertiana, Rhodophiala mendocina and Zephyranthes filifolia collected in the Argentinian Andean region all contained Galanthamine, and showed a strong AChE inhibitory activity (IC50 between 1.2 and 2 µg/mL). To our knowledge, no previous reports on alkaloid profiles and AChEIs activity of wild Argentinian Amarillydaceae species have been publisihed. The demand for renewable sources of industrial products like Galanthamine and the need to protect plant biodiversity creates an opportunity for Argentinian farmers to produce such crops.
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Galanthamine production by leucojum aestivum l shoot culture in a modified bubble column bioreactor with internal sections
Engineering in Life Sciences, 2012Co-Authors: Vasil Georgiev, Strahil Berkov, Ivan Ivanov, Mladenka Ilieva, Milen I Georgiev, Tatiana Gocheva, Atanas PavlovAbstract:Shoot culture of summer snowflake (Leucojum aestivum L.) was successfully cultivated in an advanced modified glass-column bioreactor with internal sections for production of Amaryllidaceae alkaloids. The highest amounts of dry biomass (20.8 g/L) and Galanthamine (1.7 mg/L) were achieved when shoots were cultured at 22°C and 18 L/(L·h) flow rate of inlet air. At these conditions, the L. aestivum shoot culture possessed mixotrophic-type nutrition, synthesizing the highest amounts of chlorophyll (0.24 mg/g DW (dry weight) chlorophyll A and 0.13 mg/g DW chlorophyll B). The alkaloids extract of shoot biomass showed high acetylcholinesterase inhibitory activity (IC50 = 4.6 mg). The gas chromatography–mass spectrometry (GC/MS) profiling of biosynthesized alkaloids revealed that Galanthamine and related compounds were presented in higher extracellular proportions while lycorine and hemanthamine-type compounds had higher intracellular proportions. The developed modified bubble-column bioreactor with internal sections provided conditions ensuring the growth and Galanthamine production by L. aestivum shoot culture.
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gc ms of amaryllidaceous Galanthamine type alkaloids
Journal of Mass Spectrometry, 2012Co-Authors: Strahil Berkov, Francesc Viladomat, Carles Codina, Sergio Suarez, Angel Ravelo, Jaume BastidaAbstract:Galanthamine-type alkaloids produced by plants of the Amaryllidaceae family are potent acetylcholinesterase inhibitors. One of them, Galanthamine, has been marketed as a hydrobromide salt for the treatment of Alzheimer's disease. In the present work, gas chromatography with electron impact mass spectrometry (GC-EIMS) fragmentation of 12 reference compounds isolated from various amaryllidaceous plants and identified by spectroscopic methods (1D and 2D nuclear magnetic resonance, circular dichroism, high-resolution MS (HRMS) and EIMS) was studied by tandem mass spectrometry (GC-MS/MS) and accurate mass measurements (GC-HRMS). The studied compounds showed good peak shape and efficient GC separation with a GC-MS fragmentation pattern similar to that obtained by direct insertion probe. With the exception of Galanthamine-N-oxide and N-formylnorGalanthamine, the Galanthamine-type compounds showed abundant [M](+.) and [M-H](+) ions. A typical fragmentation pattern was also observed, depending on the substituents of the skeleton. Based on the fragmentation pathways of reference compounds, three other Galanthamine-type alkaloids, including 3-O-(2'-butenoyl)sanguinine, which possesses a previously unelucidated structure, were identified in Leucojum aestivum ssp. pulchelum, a species endemic to the Balearic islands. GC-MS can be successfully applied to Amaryllidaceae plant samples in the routine screening for potentially new or known bioactive molecules, chemotaxonomy, biodiversity and identification of impurities in pharmaceutical substances.
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production of Galanthamine by leucojum aestivum shoots grown in different bioreactor systems
Applied Biochemistry and Biotechnology, 2012Co-Authors: Anika Schumann, Strahil Berkov, Jaume Bastida, Diana Claus, Andre Gerth, Carles CodinaAbstract:The production of Galanthamine by shoots of Leucojum aestivum grown in different bioreactor systems (shaking and nonshaking batch culture, temporary immersion system, bubble bioreactor, continuous and discontinuous gassing bioreactor) under different culture conditions was studied. The influence of the nutrient medium, weight of inoculum, and size of bioreactor on both growth and Galanthamine production was studied. The maximal yield of Galanthamine (19.416 mg) was achieved by cultivating the L. aestivum shoots (10 g of fresh inoculum) in a temporary immersion system in a 1-L bioreactor vessel which was used as an airlift culture vessel, gassing 12 times per day (5 min).
Carles Codina - One of the best experts on this subject based on the ideXlab platform.
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analysis of bioactive amaryllidaceae alkaloid profiles in lycoris species by gc ms
Natural Product Communications, 2014Co-Authors: Ying Guo, Francesc Viladomat, Carles Codina, Jean Paulo De Andrade, Warley De Souza Borges, Natalia B Pigni, Yuhong Zheng, Laura Torrasclaveria, Jaume BastidaAbstract:The genus Lycoris, a group of Amaryllidaceae plants distributed in temperate regions of Eastern Asia, is already known for containing representative alkaloids typical of this botanical family with a wide range of biological activities (for example, lycorine and Galanthamine). In the present work, the alkaloid profiles of nine species, L. albiflora, L. aurea, L. chinensis, L. haywardii, L. incarnata, L. longituba, L. radiata, L. sprengeri, and L. squamigera, and one variety (L. radiata var. pumila) have been evaluated by GC-MS. Structures belonging to the lycorine-, homolycorine-, haemanthamine-, narciclasine-, tazettine-, montanine- and Galanthamine-series were identified and quantified, with Galanthamine- and lycorine-type alkaloids predominating and usually showing a high relative abundance in comparison with other alkaloids of the extracts. Interestingly, L. longituba revealed itself to be a potential commercial source of bioactive alkaloids. In general terms, our results are consistent with the alkaloid profiles reported in the literature for previously studied species.
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daffodils as potential crops of Galanthamine assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity
Industrial Crops and Products, 2013Co-Authors: Laura Torrasclaveria, Strahil Berkov, Francesc Viladomat, Carles Codina, Jaume BastidaAbstract:Abstract Many plant varieties of Narcissus (Amaryllidaceae) are cultivated on a large scale for ornamental purposes but they are also known to contain Galanthamine, a bioactive alkaloid used in antiacetylcholinesterasic therapy in Alzheimer's disease. More than 100 ornamental varieties of Narcissus , using leaves and bulbs separately, were screened for their Galanthamine content as well as their acetylcholinesterase inhibitory activity in the search for new potential sources of Galanthamine. GC–MS was used for the quantitative analysis of Galanthamine, and the biological activity was determined by an acetylcholinesterase in vitro assay. Galanthamine was found to occur in the leaves or bulbs of 97 ornamental varieties, the maximal amount being 0.46% referred to DW in the leaves of Narcissus hispanicus , and 0.14% in the bulbs of the cultivar ‘Yellow Wings’. Sanguinine, an even more powerful inhibitor of acetylcholinesterase than Galanthamine, was also found in the leaves and bulbs of 22 ornamental varieties of Narcissus , which exhibited a high acetylcholinesterase inhibitory activity.
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gc ms of amaryllidaceous Galanthamine type alkaloids
Journal of Mass Spectrometry, 2012Co-Authors: Strahil Berkov, Francesc Viladomat, Carles Codina, Sergio Suarez, Angel Ravelo, Jaume BastidaAbstract:Galanthamine-type alkaloids produced by plants of the Amaryllidaceae family are potent acetylcholinesterase inhibitors. One of them, Galanthamine, has been marketed as a hydrobromide salt for the treatment of Alzheimer's disease. In the present work, gas chromatography with electron impact mass spectrometry (GC-EIMS) fragmentation of 12 reference compounds isolated from various amaryllidaceous plants and identified by spectroscopic methods (1D and 2D nuclear magnetic resonance, circular dichroism, high-resolution MS (HRMS) and EIMS) was studied by tandem mass spectrometry (GC-MS/MS) and accurate mass measurements (GC-HRMS). The studied compounds showed good peak shape and efficient GC separation with a GC-MS fragmentation pattern similar to that obtained by direct insertion probe. With the exception of Galanthamine-N-oxide and N-formylnorGalanthamine, the Galanthamine-type compounds showed abundant [M](+.) and [M-H](+) ions. A typical fragmentation pattern was also observed, depending on the substituents of the skeleton. Based on the fragmentation pathways of reference compounds, three other Galanthamine-type alkaloids, including 3-O-(2'-butenoyl)sanguinine, which possesses a previously unelucidated structure, were identified in Leucojum aestivum ssp. pulchelum, a species endemic to the Balearic islands. GC-MS can be successfully applied to Amaryllidaceae plant samples in the routine screening for potentially new or known bioactive molecules, chemotaxonomy, biodiversity and identification of impurities in pharmaceutical substances.
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production of Galanthamine by leucojum aestivum shoots grown in different bioreactor systems
Applied Biochemistry and Biotechnology, 2012Co-Authors: Anika Schumann, Strahil Berkov, Jaume Bastida, Diana Claus, Andre Gerth, Carles CodinaAbstract:The production of Galanthamine by shoots of Leucojum aestivum grown in different bioreactor systems (shaking and nonshaking batch culture, temporary immersion system, bubble bioreactor, continuous and discontinuous gassing bioreactor) under different culture conditions was studied. The influence of the nutrient medium, weight of inoculum, and size of bioreactor on both growth and Galanthamine production was studied. The maximal yield of Galanthamine (19.416 mg) was achieved by cultivating the L. aestivum shoots (10 g of fresh inoculum) in a temporary immersion system in a 1-L bioreactor vessel which was used as an airlift culture vessel, gassing 12 times per day (5 min).
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alkaloids from hippeastrum papilio
Molecules, 2011Co-Authors: Jean Paulo De Andrade, Strahil Berkov, Francesc Viladomat, Carles Codina, Jose Angelo S Zuanazzi, Jaume BastidaAbstract: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.
Manuela G Lopez - One of the best experts on this subject based on the ideXlab platform.
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effects of memantine and galantamine given separately or in association on memory and hippocampal neuronal loss after transient global cerebral ischemia in gerbils
Brain Research, 2009Co-Authors: Silvia Lorrio, Pilar Negredo, J M Roda, Antonio G Garcia, Manuela G LopezAbstract:Abstract Galantamine is an acetylcholinesterase inhibitor and memantine is a non competitive antagonist of NMDA receptors that are being used to treat Alzheimer's disease (AD) patients. The fact that drugs with different mechanisms of action are available to treat AD introduces the prospect of prescribing drug combinations to amplify drug efficacy. This study was planed to evaluate the potential neuroprotective effects of galantamine combined with memantine in a transient global cerebral ischemia model in gerbils. Animal groups included in the study were: sham, ischemia, and ischemia plus galantamine (1 mg/kg and 10 mg/kg), memantine (10 mg/kg and 20 mg/kg), 1 mg/kg galantamine plus 10 mg/kg memantine, and 10 mg/kg galantamine plus 10 mg/kg memantine, respectively. Surviving pyramidal neurons in the CA1 subfield of the hippocampus, TUNEL, caspase-3 and SOD-2 immunohistochemistries, and the object placement test were evaluated 72 h after reperfusion. Memantine did not exert a clear neuroprotective effect, nor did it prevent spatial memory loss. In a previous study using the same experimental model, galantamine was neuroprotective and improved spatial memory. In this study, the association of 10 mg/kg memantine with 10 mg/kg galantamine increased the number of living pyramidal neurons, reduced TUNEL, active caspase-3 and SOD-2 immunoreactivity, and preserved spatial memory after ischemia-reperfusion injury; however, the effects of the combination were not statistically different from those observed in animals treated with galantamine alone. We believe these results are of interest from a clinical point of view because the association of both drugs is being used in clinical practice and in clinical trials to treat Alzheimer's disease and vascular dementia.
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galantamine postischemia provides neuroprotection and memory recovery against transient global cerebral ischemia in gerbils
Journal of Pharmacology and Experimental Therapeutics, 2007Co-Authors: Silvia Lorrio, J M Roda, Antonio G Garcia, Monica Sobrado, Esperanza Arias, Manuela G LopezAbstract:Galantamine, currently used in Alzheimer9s patients, has shown neuroprotection in hippocampal slices subjected to oxygenglucose deprivation. Here, we present an in vivo study to evaluate the potential neuroprotective effects of galantamine in a transient global cerebral ischemia model in gerbils. Three treatment protocols were used. In the pretreatment protocol, gerbils were treated before ischemia and for 3 consecutive days thereafter. Eight groups of animals were included: sham operation plus placebo, 10 mg/kg mecamylamine and 10 mg/kg galantamine, respectively; and ischemia plus placebo, 10 mg/kg mecamylamine, 1 mg/kg galantamine, and 10 mg/kg galantamine and 10 mg/kg mecamylamine plus galantamine, respectively. Postischemia protocols included three groups of animals: sham operation, ischemia plus placebo, and ischemia plus 10 mg/kg galantamine; substances were administered 3 or 6 h after ischemia and for 2 consecutive days thereafter. Pyramidal neurons surviving in the cornus ammonis 1 region of the hippocampus were evaluated 72 h after reperfusion, terminal deoxynucleotidyl transferase dUTP nick-end labeling (TUNEL) histochemistry, caspase-3 and superoxide dismutase (SOD)-2 immunohistochemistries, and Western blottings were performed, and object placement tests were carried out. Galantamine significantly increased the number of living pyramidal neurons after ischemia-reperfusion injury. Galantamine significantly reduced TUNEL, active caspase-3, and SOD-2 immunoreactivity. The nicotinic antagonist mecamylamine blocked the protective effects of galantamine. The neuroprotective effects of galantamine were preserved even when first administered at 3 h postischemia. These results correlated with the performance in the object placement test. This study shows that galantamine provides in vivo neuroprotection and memory recovery against global cerebral ischemia, even when administration begins 3 h postischemia.
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unequal neuroprotection afforded by the acetylcholinesterase inhibitors galantamine donepezil and rivastigmine in sh sy5y neuroblastoma cells role of nicotinic receptors
Journal of Pharmacology and Experimental Therapeutics, 2005Co-Authors: Esperanza Arias, Antonio G Garcia, Mercedes Villarroya, Sonia Gallegosandin, Manuela G LopezAbstract:Donepezil, rivastigmine, and galantamine are three drugs with acetylcholinesterase (AChE)-inhibiting activity that are currently being used to treat patients suffering from Alzheimer's disease. We have studied the neuroprotective effects of these drugs, in comparison with nicotine, on cell death caused by beta-amyloid (Abeta) and okadaic acid, two models that are relevant to Alzheimer's pathology, in the human neuroblastoma cell line SH-SY5Y. Galantamine and donepezil showed a U-shaped neuroprotective curve against okadaic acid toxicity; maximum protection was achieved at 0.3 microM galantamine and at 1 microM donepezil; at higher concentrations, protection was diminished. Rivastigmine showed a concentration-dependent effect; maximum protection was achieved at 3 microM. When apoptosis was induced by Abeta25-35, galantamine, donepezil, and rivastigmine showed maximum protection at the same concentrations: 0.3, 1, and 3 microM, respectively. Nicotine also afforded protection against Abeta- and okadaic acid-induced toxicity. The neuroprotective effects of galantamine, donepezil, and nicotine were reversed by the alpha7 nicotinic antagonist methyllycaconitine but not by the alpha4beta2 nicotinic antagonist dihydro-beta-erythroidine. The phosphoinositide 3-kinase (PI3K)-Akt blocker 2-(4-morpholinyl)-8-phenyl-1(4H)-benzopyran-4-one hydrochloride (LY294002) reversed the protective effects of galantamine, donepezil, and nicotine but not that of rivastigmine. In contrast, the bcl-2 antagonist ethyl[2-amino-6-bromo-4-(1-cyano-2-ethoxy-2-oxoethyl)]-4H-chromene-3-carboxylate (HA 14-1) reversed the protective effects of the three AChE inhibitors and that of nicotine. Our results show that galantamine, donepezil, and rivastigmine afford neuroprotection through a mechanism that is likely unrelated to AChE inhibition. Such neuroprotection seemed to be linked to alpha7 nicotinic receptors and the PI3K-Akt pathway in the case of galantamine and donepezil but not for rivastigmine.
Francesc Viladomat - One of the best experts on this subject based on the ideXlab platform.
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analysis of bioactive amaryllidaceae alkaloid profiles in lycoris species by gc ms
Natural Product Communications, 2014Co-Authors: Ying Guo, Francesc Viladomat, Carles Codina, Jean Paulo De Andrade, Warley De Souza Borges, Natalia B Pigni, Yuhong Zheng, Laura Torrasclaveria, Jaume BastidaAbstract:The genus Lycoris, a group of Amaryllidaceae plants distributed in temperate regions of Eastern Asia, is already known for containing representative alkaloids typical of this botanical family with a wide range of biological activities (for example, lycorine and Galanthamine). In the present work, the alkaloid profiles of nine species, L. albiflora, L. aurea, L. chinensis, L. haywardii, L. incarnata, L. longituba, L. radiata, L. sprengeri, and L. squamigera, and one variety (L. radiata var. pumila) have been evaluated by GC-MS. Structures belonging to the lycorine-, homolycorine-, haemanthamine-, narciclasine-, tazettine-, montanine- and Galanthamine-series were identified and quantified, with Galanthamine- and lycorine-type alkaloids predominating and usually showing a high relative abundance in comparison with other alkaloids of the extracts. Interestingly, L. longituba revealed itself to be a potential commercial source of bioactive alkaloids. In general terms, our results are consistent with the alkaloid profiles reported in the literature for previously studied species.
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daffodils as potential crops of Galanthamine assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity
Industrial Crops and Products, 2013Co-Authors: Laura Torrasclaveria, Strahil Berkov, Francesc Viladomat, Carles Codina, Jaume BastidaAbstract:Abstract Many plant varieties of Narcissus (Amaryllidaceae) are cultivated on a large scale for ornamental purposes but they are also known to contain Galanthamine, a bioactive alkaloid used in antiacetylcholinesterasic therapy in Alzheimer's disease. More than 100 ornamental varieties of Narcissus , using leaves and bulbs separately, were screened for their Galanthamine content as well as their acetylcholinesterase inhibitory activity in the search for new potential sources of Galanthamine. GC–MS was used for the quantitative analysis of Galanthamine, and the biological activity was determined by an acetylcholinesterase in vitro assay. Galanthamine was found to occur in the leaves or bulbs of 97 ornamental varieties, the maximal amount being 0.46% referred to DW in the leaves of Narcissus hispanicus , and 0.14% in the bulbs of the cultivar ‘Yellow Wings’. Sanguinine, an even more powerful inhibitor of acetylcholinesterase than Galanthamine, was also found in the leaves and bulbs of 22 ornamental varieties of Narcissus , which exhibited a high acetylcholinesterase inhibitory activity.
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gc ms of amaryllidaceous Galanthamine type alkaloids
Journal of Mass Spectrometry, 2012Co-Authors: Strahil Berkov, Francesc Viladomat, Carles Codina, Sergio Suarez, Angel Ravelo, Jaume BastidaAbstract:Galanthamine-type alkaloids produced by plants of the Amaryllidaceae family are potent acetylcholinesterase inhibitors. One of them, Galanthamine, has been marketed as a hydrobromide salt for the treatment of Alzheimer's disease. In the present work, gas chromatography with electron impact mass spectrometry (GC-EIMS) fragmentation of 12 reference compounds isolated from various amaryllidaceous plants and identified by spectroscopic methods (1D and 2D nuclear magnetic resonance, circular dichroism, high-resolution MS (HRMS) and EIMS) was studied by tandem mass spectrometry (GC-MS/MS) and accurate mass measurements (GC-HRMS). The studied compounds showed good peak shape and efficient GC separation with a GC-MS fragmentation pattern similar to that obtained by direct insertion probe. With the exception of Galanthamine-N-oxide and N-formylnorGalanthamine, the Galanthamine-type compounds showed abundant [M](+.) and [M-H](+) ions. A typical fragmentation pattern was also observed, depending on the substituents of the skeleton. Based on the fragmentation pathways of reference compounds, three other Galanthamine-type alkaloids, including 3-O-(2'-butenoyl)sanguinine, which possesses a previously unelucidated structure, were identified in Leucojum aestivum ssp. pulchelum, a species endemic to the Balearic islands. GC-MS can be successfully applied to Amaryllidaceae plant samples in the routine screening for potentially new or known bioactive molecules, chemotaxonomy, biodiversity and identification of impurities in pharmaceutical substances.
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alkaloids from hippeastrum papilio
Molecules, 2011Co-Authors: Jean Paulo De Andrade, Strahil Berkov, Francesc Viladomat, Carles Codina, Jose Angelo S Zuanazzi, Jaume BastidaAbstract: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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Alkaloid diversity in Galanthus elwesii and Galanthus nivalis.
Chemistry & Biodiversity, 2011Co-Authors: Strahil Berkov, Francesc Viladomat, Jaume Bastida, Borjana Sidjimova, Carles CodinaAbstract:Seventy alkaloids of Galanthamine, lycorine, homolycorine, tazettine, haemanthamine, narciclasine, and tyramine types were detected by GC/MS in 25 Galanthus elwesii and seven Galanthus nivalis populations, collected from different locations in Bulgaria. Intraspecies diversity in the alkaloid profiles regarding the main alkaloid types (chemotypes) was observed. Tyramine-type protoalkaloids (namely, hordenine and its derivatives) were dominant in 19 populations of G. elwesii. In other populations of G. elwesii, the plants accumulated mainly homolycorine-, lycorine-, and Galanthamine-type alkaloids. The alkaloid profiles of G. nivalis were dominated by narciclasine-, Galanthamine-, lycorine-, haemanthamine-, or tazettine-type compounds. Geographical distribution of chemotypes indicated a relationship between populations, since adjacent populations often displayed similar alkaloid profiles. The results from year-to-year sampling and transplantation experiments imply genetic determination of alkaloid synthesis in the two studied species of Galanthus.
