Bastida J

References (36)

Title : The Anti-Cholinesterase Potential of Fifteen Different Species of Narcissus L. (Amaryllidaceae) Collected in Spain - Tallini_2024_Life.(Basel)_14_
Author(s) : Tallini LR , Manfredini G , Rodriguez-Escobar ML , Rios S , Martinez-Frances V , Feresin GE , Borges WS , Bastida J , Viladomat F , Torras-Claveria L
Ref : Life (Basel) , 14 : , 2024
Abstract : Narcissus L. is a renowned plant genus with a notable center of diversity and is primarily located in the Mediterranean region. These plants are widely recognized for their ornamental value, owing to the beauty of their flowers; nonetheless, they also hold pharmacological importance. In Europe, pharmaceutical companies usually use the bulbs of Narcissus pseudonarcissus cv. Carlton to extract galanthamine, which is one of the few medications approved by the FDA for the palliative treatment of mild-to-moderate symptoms of Alzheimer's disease. The purpose of this study was to evaluate the potential of these plants in Alzheimer's disease. The alkaloid extract from the leaves of different species of Narcissus was obtained by an acid-base extraction work-up -procedure. The biological potential of the samples was carried out by evaluating their ability to inhibit the enzymes acetyl- and butyrylcholinesterase (AChE and BuChE, respectively). The species N. jacetanus exhibited the best inhibition values against AChE, with IC(50) values of 0.75 +/- 0.03 microg.mL(-1), while N. jonquilla was the most active against BuChE, with IC(50) values of 11.72 +/- 1.15 microg.mL(-1).
ESTHER : Tallini_2024_Life.(Basel)_14_
PubMedSearch : Tallini_2024_Life.(Basel)_14_
PubMedID: 38672806

Title : Alkaloid Profile in Wild Autumn-Flowering Daffodils and Their Acetylcholinesterase Inhibitory Activity - Lisa-Molina_2023_Molecules_28_
Author(s) : Lisa-Molina J , Gomez-Murillo P , Arellano-Martin I , Jimenez C , Rodriguez-Escobar ML , Tallini LR , Viladomat F , Torras-Claveria L , Bastida J
Ref : Molecules , 28 : , 2023
Abstract : Amaryllidaceae alkaloids are secondary metabolites with interesting medicinal properties. Almost every Narcissus species can synthesize them and constitute an excellent source for their isolation and study. Several Amaryllidaceae alkaloids have shown acetylcholinesterase inhibitory activities and are a promising tool for treating cholinergic disorders such as Alzheimer's disease (AD). Indeed, three of the four palliative treatments approved for AD are acetylcholinesterase (AChE) inhibitors and one of them, galanthamine, is an Amaryllidaceae alkaloid itself. This molecule is currently isolated from natural sources. However, its production is insufficient to supply the increasing demand for the active principle. Our main aim is to discover tools to improve galanthamine production and to prospect for potential new and more efficient drugs for AD treatment. Furthermore, we seek to broaden the knowledge of plants of the genus Narcissus from a chemotaxonomic perspective. Hence, in this study, we evaluate the alkaloid content through GC-MS and the AChE inhibitory activity of ten autumn-flowering Narcissus, which have been less studied than their spring-flowering counterparts. A total of thirty Amaryllidaceae alkaloids have been found, twenty-eight properly identified. Two Narcissus contained galanthamine, and seven were able to inhibit AChE.
ESTHER : Lisa-Molina_2023_Molecules_28_
PubMedSearch : Lisa-Molina_2023_Molecules_28_
PubMedID: 36770905

Title : Antiparasitic Activity of Hippeastrum Species and Synergistic Interaction between Montanine and Benznidazole against Trypanosoma cruzi - Pineiro_2023_Microorganisms_11_
Author(s) : Pineiro M , Ortiz JE , Spina Zapata RM , Barrera PA , Sosa MA , Roitman G , Bastida J , Feresin GE
Ref : Microorganisms , 11 : , 2023
Abstract : BACKGROUND: Hippeastrum species have a wide range of biological properties. In Argentina, this genus comprises ten widely distributed species. PURPOSE: To evaluate the antiparasitic and anticholinesterase activities and chemical profiles of seven Argentinean Hippeastrum species and determine the synergism between the major isolated alkaloid-montanine-and benznidazole in anti-Trypanosoma cruzi activity. METHODS: The antiparasitic activity was evaluated through antiproliferative and viability assays against T. cruzi epimastigotes. Synergism assays were performed using the Chou-Talalay method. AChE and BuChE inhibitory activities were also assessed. The alkaloid composition was obtained using GC-MS analysis. RESULTS: All extracts showed strong growth inhibition of T. cruzi epimastigote proliferation. The extracts from H. aglaiae, H. aulicum, and H. hybrid stand out for their potent and total growth inhibition, which was comparable to benznidazole. The H. reticulatum extract showed strong Acetylcholinesterase (AChE) inhibitory activities, while five species showed moderate Butyrylcholinesterase (BuChE) inhibition. Fifteen alkaloids were identified by means of GC-MS. Regarding the synergism assessment, the highest synergistic effect was obtained from the combination of montanine and benznidazole. CONCLUSION: Hippeastrum species bulb extracts from Argentina were shown to be a good source of antiparasitic alkaloids and cholinesterase inhibitors. The synergism between montanine and benznidazole emerges as a potential combination for future studies to treat Chagas disease.
ESTHER : Pineiro_2023_Microorganisms_11_
PubMedSearch : Pineiro_2023_Microorganisms_11_
PubMedID: 36677436

Title : Acetylcholinesterase Inhibition Activity of Hippeastrum papilio (Ravenna) Van Scheepen (Amaryllidaceae) Using Zebrafish Brain Homogenates - Tallini_2023_Life.(Basel)_13_
Author(s) : Tallini LR , da Silva CR , Jung T , Alves EO , Baldin SL , Apel M , Timmers L , Rico EP , Bastida J , Zuanazzi JAS
Ref : Life (Basel) , 13 : , 2023
Abstract : The Amaryllidaceae family constitutes an interesting source of exclusive alkaloids with a broad spectrum of biological activity. Galanthamine, the most relevant one, has been commercialized for the palliative treatment of Alzheimer's disease symptoms since 2001 due to its potential as an acetylcholinesterase (AChE) inhibitor. In vitro screenings against AChE by applying different Amaryllidaceae species and alkaloids have been reported in the literature; however, they are usually carried out using purified market enzymes. The main goal of this work is to evaluate the AChE inhibitory potential of Hippeastrum papilio (Amaryllidaceae) extracts using zebrafish brain homogenates. The biological assays show that the H. papilio bulb extracts present an interesting AChE inhibitory activity in comparison with the positive reference control galanthamine (IC(50) values of 1.20 +/- 0.10 and 0.79 +/- 0.15 microg/mL, respectively). The chemical profile of H. papilio shows that this species has a high amount of galanthamine, which may contribute to the inhibitory effect on AChE activity of zebrafish brains. Computational experiments were used to build the model for zebrafish AChE and to evaluate the interactions between galanthamine and the enzymic active site. This work suggests that zebrafish could represent an important model in the search for bioactive molecules from the Amaryllidaceae family for the treatment of Alzheimer's disease.
ESTHER : Tallini_2023_Life.(Basel)_13_
PubMedSearch : Tallini_2023_Life.(Basel)_13_
PubMedID: 37629578

Title : Chemical and Biological Aspects of Different Species of the Genus Clinanthus Herb. (Amaryllidaceae) from South America - Rodriguez-Escobar_2023_Molecules_28_
Author(s) : Rodriguez-Escobar ML , Tallini LR , Lisa-Molina J , Berkov S , Viladomat F , Meerow A , Bastida J , Torras-Claveria L
Ref : Molecules , 28 : , 2023
Abstract : The genus Clinanthus Herb. is found in the Andes Region (South America), mainly in Peru, Ecuador, and Bolivia. These plants belong to the Amaryllidaceae family, specifically the Amaryllidoideae subfamily, which presents an exclusive group of alkaloids known as Amaryllidaceae alkaloids that show important structural diversity and pharmacological properties. It is possible to find some publications in the literature regarding the botanical aspects of Clinanthus species, although there is little information available about their chemical and biological activities. The aim of this work was to obtain the alkaloid profile and the anti-cholinesterase activity of four different samples of Clinanthus collected in South America: Clinanthus sp., Clinanthus incarnatus, and Clinanthus variegatus. The alkaloid extract of each sample was analyzed by gas chromatography coupled with mass spectrometry (GC-MS), and their potential against the enzymes acetyl- and butyrylcholinesterase were evaluated. Thirteen alkaloids have been identified among these species, while six unidentified structures have also been detected in these plants. The alkaloid extract of the C. variegatus samples showed the highest structural diversity as well as the best activity against AChE, which was likely due to the presence of the alkaloid sanguinine. The results suggest this genus as a possible interesting new source of Amaryllidaceae alkaloids, which could contribute to the development of new medicines.
ESTHER : Rodriguez-Escobar_2023_Molecules_28_
PubMedSearch : Rodriguez-Escobar_2023_Molecules_28_
PubMedID: 37513280

Title : In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase - Sierra_2022_Biomed.Pharmacother_150_113016
Author(s) : Sierra K , de Andrade JP , L RT , Osorio EH , Yanez O , Osorio MI , Oleas NH , Garcia-Beltran O , de SBW , Bastida J , Osorio E , Cortes N
Ref : Biomed Pharmacother , 150 :113016 , 2022
Abstract : Zephyranthes carinata Herb., a specie of the Amaryllidoideae subfamily, has been reported to have inhibitory activity against acetylcholinesterase. However, scientific evidence related to their bioactive alkaloids has been lacking. Thus, this study describes the isolation of the alkaloids of this plant, and their inhibition of the enzymes acetylcholinesterase (eeAChE) and butyrylcholinesterase (eqBuChE), being galanthine the main component. Additionally, haemanthamine, hamayne, lycoramine, lycorine, tazettine, trisphaeridine and vittatine/crinine were also isolated. The results showed that galanthine has significant activity at low micromolar concentrations for eeAChE (IC(50) = 1.96 microg/mL). The in-silico study allowed to establish at a molecular level the high affinity and the way galanthine interacts with the active site of the TcAChE enzyme, information that corroborates the result of the experimental IC(50). However, according to molecular dynamics (MD) analysis, it is also suggested that galanthine presents a different inhibition mode that the one observed for galanthamine, by presenting interaction with peripheral anionic binding site of the enzyme, which prevents the entrance and exit of molecules from the active site. Thus, in vitro screening assays plus rapid computer development play an essential role in the search for new cholinesterase inhibitors by identifying unknown bio-interactions between bioactive compounds and biological targets.
ESTHER : Sierra_2022_Biomed.Pharmacother_150_113016
PubMedSearch : Sierra_2022_Biomed.Pharmacother_150_113016
PubMedID: 35483192

Title : Chemical Survey of Three Species of the Genus Rauhia Traub (Amaryllidaceae) - Tallini_2022_Plants.(Basel)_11_
Author(s) : Tallini LR , Osorio EH , Berkov S , Torras-Claveria L , Rodriguez-Escobar ML , Viladomat F , Meerow AW , Bastida J
Ref : Plants (Basel) , 11 : , 2022
Abstract : Plant biodiversity is an important source of compounds with medicinal properties. The alkaloid galanthamine, first isolated from Galanthus woronowii (Amaryllidaceae), is approved by the FDA for the palliative treatment of mild to moderate Alzheimer's disease due to its acetylcholinesterase (AChE) inhibitory activity. Obtaining this active pharmaceutical ingredient, still sourced on an industrial scale from the Amaryllidaceae species, is a challenge for pharmaceutical companies due to its low natural yield and the high cost of its synthesis. The aim of this work was to determine the alkaloid profile of three different Rauhia (Amaryllidaceae) species collected in Peru, and to assess the potential application of their extracts for the treatment of Alzheimer's disease. The alkaloids were identified by gas chromatography coupled to mass spectrometry (GC-MS), and the AChE inhibitory activity of the extracts was analyzed. Thirty compounds were quantified from the Rauhia species, the R. multiflora extract being the most interesting due to its high diversity of galanthamine-type structures. The R. multiflora extract was also the most active against AChE, with the half maximal inhibitory concentration (IC(50)) values of 0.17 +/- 0.02 microg.mL(-1) in comparison with the IC(50) values of 0.53 +/- 0.12 microg.mL(-1) for galanthamine, used as a reference. Computational experiments were carried out on the activity of the galanthamine-type alkaloids identified in R. multiflora toward five different human AChE structures. The simulation of the molecules 3-O-acetylgalanthamine, 3-O-acetylsanguinine, narwedine, and lycoraminone on the 4EY6 crystal structure theoretically showed a higher inhibition of hAChE and different interactions with the active site compared to galanthamine. In conclusion, the results of this first alkaloid profiling of the Rauhia species indicate that R. multiflora is an important natural source of galanthamine-type structures and could be used as a model for the development of biotechnological tools necessary to advance the sustainable production of galanthamine.
ESTHER : Tallini_2022_Plants.(Basel)_11_
PubMedSearch : Tallini_2022_Plants.(Basel)_11_
PubMedID: 36559661

Title : Alkaloids of Phaedranassa dubia (Kunth) J.F. Macbr. and Phaedranassa brevifolia Meerow (Amaryllidaceae) from Ecuador and its cholinesterase-inhibitory activity - Leon_2021_S.Afr.J.Bot_136_91
Author(s) : Leon KA , Inca A , Tallini LR , Osorio EH , Robles J , Bastida J , Oleas NH
Ref : S Afr J Bot , 136 :91 , 2021
Abstract : Alzheimer's disease is considered the most common cause of dementia and, in an increasingly aging population worldwide, the quest for treatment is a priority. Amaryllidaceae alkaloids are of main interest because of their cholinesterase inhibition potential, which is the main palliative treatment available for this disease. We evaluated the alkaloidal profile and the in vitro inhibitory activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) of bulb alkaloid extract of Phaedranassa dubia and Phaedranassa brevifolia collected in Ecuador. Using gas chromatography coupled to mass spectrometry (GC-MS), we identified typical Amaryllidaceae alkaloids in these species, highlighting the presence of lycorine-type alkaloids in P. dubia and haemanthamine/crinine-type in P. brevifolia. The species P. dubia and P. brevifolia showed inhibitory activities against AChE (IC(50) values of 25.48 +/- 0.39 and 3.45 +/- 0.29 microg.mL(-1), respectively) and BuChE (IC(50) values of 114.96 +/- 4.94 and 58.89 +/- 0.55 microg.mL(-1), respectively). Computational experiments allowed us to understand the interactions of the alkaloids identified in these samples toward the active sites of AChE and BuChE. In silico, some alkaloids detected in these Amaryllidaceae species presented higher estimated binding free energy toward BuChE than galanthamine. This is the first study about the alkaloid profile and biological potential of P. brevifolia species.
ESTHER : Leon_2021_S.Afr.J.Bot_136_91
PubMedSearch : Leon_2021_S.Afr.J.Bot_136_91
PubMedID: 32982003

Title : Alkaloids Analysis of Habranthus cardenasianus (Amaryllidaceae), Anti-Cholinesterase Activity and Biomass Production by Propagation Strategies - Zaragoza-Puchol_2021_Molecules_26_
Author(s) : Zaragoza-Puchol D , Ortiz JE , Orden AA , Sanchez M , Palermo J , Tapia A , Bastida J , Feresin GE
Ref : Molecules , 26 : , 2021
Abstract : Plants in the Amaryllidaceae family synthesize a diversity of bioactive alkaloids. Some of these plant species are not abundant and have a low natural multiplication rate. The aims of this work were the alkaloids analysis of a Habranthus cardenasianus bulbs extract, the evaluation of its inhibitory activity against cholinesterases, and to test several propagation strategies for biomass production. Eleven compounds were characterized by GC-MS in the alkaloid extract, which showed a relatively high proportion of tazettine. The known alkaloids tazettine, haemanthamine, and the epimer mixture haemanthidine/6-epi-haemanthidine were isolated and identified by spectroscopic methods. Inhibitory cholinesterases activity was not detected. Three forms of propagation were performed: bulb propagation from seed, cut-induced bulb division, and micropropagated bulbs. Finally, different imbibition and post-collection times were evaluated in seed germination assays. The best propagation method was cut-induced bulb division with longitudinal cuts into quarters (T1) while the best conditions for seed germination were 0-day of post-collection and two days of imbibition. The alkaloids analyses of the H. cardenasianus bulbs showed that they are a source of anti-tumoral alkaloids, especially pretazettine (tazettine) and T1 is a sustainable strategy for its propagation and domestication to produce bioactive alkaloids.
ESTHER : Zaragoza-Puchol_2021_Molecules_26_
PubMedSearch : Zaragoza-Puchol_2021_Molecules_26_
PubMedID: 33401696

Title : Plants of the 'Libellus de Medicinalibus Indorum Herbis' from Mexico, 1552. Zephyranthes fosteri (Amaryllidaceae) Alkaloids - Centeno-Betanzos_2021_Chem.Biodivers__
Author(s) : Centeno-Betanzos LY , Reyes-Chilpa R , Pigni NB , Jankowski CK , Torras-Claveria L , Bastida J
Ref : Chem Biodivers , : , 2021
Abstract : The Libellus de Medicinalibus Indorum Herbis (Booklet of Indian Medicinal Plants) is the first book of medicinal plants written in the American continent. It was first published in 1939 as 'An Aztec Herbal'. One of the depicted plants is Huetzcanixochitl (laughing flower) interpreted as Zephyranthes fosteri (Amaryllidaceae). No chemical or pharmacological studies are reported for this species; so, we decide to investigate it. The GC/MS of the bulbs and aerial parts extracts indicated that they contain Amaryllidaceae alkaloids, among them: lycorine, 3-O-acetylpowelline, and norlycoramine. An unknown major alkaloid was isolated and identified by (1) H, (13) C-NMR and MS, as 3'-demethoxy-6-epimesembranol (1). The methanolic extract, the alkaloid fraction, and compound 1 inhibited acetylcholinesterase invitro. Mesembrine alkaloids are found in Sceletium species (Aizoaceae). Several are known as serotonin recapture inhibitors and have been proposed as potential antidepressant drugs. The presence of 1 suggests that Z. fosteri was probably used in pre-Columbian times in Mexico as a 'stimulant and euphoriant', alike Sceletium tortuosum by several ethnic groups in South Africa.
ESTHER : Centeno-Betanzos_2021_Chem.Biodivers__
PubMedSearch : Centeno-Betanzos_2021_Chem.Biodivers__
PubMedID: 33594810

Title : Alkaloid Profiling and Cholinesterase Inhibitory Potential of Crinum amabile Donn. (Amaryllidaceae) Collected in Ecuador - Tallini_2021_Plants.(Basel)_10_
Author(s) : Tallini LR , Carrasco A , Acosta Leon K , Vinueza D , Bastida J , Oleas NH
Ref : Plants (Basel) , 10 : , 2021
Abstract : Natural products are one of the main sources for developing new drugs. The alkaloids obtained from the plant family Amaryllidaceae have interesting structures and biological activities, such as acetylcholinesterase inhibition potential, which is one of the mechanisms used for the palliative treatment of Alzheimer's disease symptoms. Herein we report the alkaloidal profile of bulbs and leaves extracts of Crinum x amabile collected in Ecuador and their in vitro inhibitory activity on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes. Using Gas Chromatography coupled to Mass Spectrometry (GC-MS), we identified 12 Amaryllidaceae alkaloids out of 19 compounds detected in this species. The extracts from bulbs and leaves showed great inhibitory activity against AChE and BuChE, highlighting the potential of Amaryllidaceae family in the search of bioactive molecules.
ESTHER : Tallini_2021_Plants.(Basel)_10_
PubMedSearch : Tallini_2021_Plants.(Basel)_10_
PubMedID: 34961157

Title : Chemical Profiling and Cholinesterase Inhibitory Activity of Five Phaedranassa Herb. (Amaryllidaceae) Species from Ecuador - Moreno_2020_Molecules_25_
Author(s) : Moreno R , Tallini LR , Salazar C , Osorio EH , Montero E , Bastida J , Oleas NH , Acosta Leon K
Ref : Molecules , 25 : , 2020
Abstract : It is estimated that 50 million people in the world live with dementia, 60-70% of whom suffer from Alzheimer's disease (AD). Different factors are involved in the development of AD, including a reduction in the cholinergic neurotransmission level. The Amaryllidaceae plant family contains an exclusive, large, and still understudied alkaloid group characterized by a singular skeleton arrangement and a broad spectrum of biological activities. The chemistry and biodiversity of Ecuadorian representatives of the Phaedranassa genus (Amaryllidaceae) have not been widely studied. In this work, five Ecuadorian Phaedranassa species were examined in vitro for their activity towards the enzymes acetyl- (AChE) and butyrylcholinesterase (BuChE), and the alkaloid profile of bulb extracts was analyzed by GC-MS. The species Phaedranassa cuencana and Phaedranassa dubia showed the most AChE and BuChE inhibitory activity, respectively. To obtain insight into the potential role of the identified alkaloids in these inhibitory effects, docking experiments were carried out, and cantabricine showed in silico inhibitory activity against both cholinesterase structures. Our results show that Amaryllidaceae species from Ecuador are a potential source of new drugs for the palliative treatment of AD.
ESTHER : Moreno_2020_Molecules_25_
PubMedSearch : Moreno_2020_Molecules_25_
PubMedID: 32365796

Title : Development and economic evaluation of an eco-friendly biocatalytic synthesis of emollient esters - Serrano-Arnaldos_2020_Bioprocess.Biosyst.Eng_43_495
Author(s) : Serrano-Arnaldos M , Montiel MC , Ortega-Requena S , Maximo F , Bastida J
Ref : Bioprocess Biosyst Eng , 43 :495 , 2020
Abstract : During the past decades the understanding and prospects of enzyme-catalysed reactions have been massively widened and there are a number of implemented large-scale enzymatic processes mainly based in the use of commercial biocatalysts. As it might happen that the same process can be successfully carried out by different commercial lipases, the election of the biocatalyst must rely on productivity and economic considerations. This work presents productiveness and direct operation cost evaluation as a key tool for the selection between two commercial lipase catalysts, the versatile but expensive Novozym() 435 and a much more economical option, Lipozyme() TL IM, in the synthesis of spermaceti, a mixture of emollient esters with cosmetic applications. Proving that Novozym() 435 leads to minimum savings of 10% with respect to the cheapest immobilized derivative, biocatalyst cost does not appear to be the major contribution to the economics of the processes under study, due to their great capacity to be recovered and reused. At laboratory scale, the biggest economic investment is caused by substrates, which can be massively reduced at industrial scale by using bulk reagents. In such case, energy cost may be the major contribution to the process economy. This work proposes an optimized process ready to be scaled-up in order to accurately determine the energetic requirements of the possible industrial enzymatic synthesis.
ESTHER : Serrano-Arnaldos_2020_Bioprocess.Biosyst.Eng_43_495
PubMedSearch : Serrano-Arnaldos_2020_Bioprocess.Biosyst.Eng_43_495
PubMedID: 31701234

Title : Clinanthus microstephium, an Amaryllidaceae Species with Cholinesterase Inhibitor Alkaloids: Structure-Activity Analysis of Haemanthamine Skeleton Derivatives - Adessi_2019_Chem.Biodivers_16_e1800662
Author(s) : Adessi TG , Borioni JL , Pigni NB , Bastida J , Cavallaro V , Murray AP , Puiatti M , Oberti JC , Leiva S , Nicotra VE , Garcia ME
Ref : Chem Biodivers , 16 :e1800662 , 2019
Abstract : Plants of the Amaryllidaceae family are well-known (not only) for their ornamental value but also for the alkaloids that they produce. In this report, the first phytochemical study of Clinanthus genus was carried out. The chemical composition of alkaloid fractions from Clinanthus microstephium was analyzed by GC/MS and NMR. Seven known compounds belonging to three structural types of Amaryllidaceae alkaloids were identified. An epimeric mixture of a haemanthamine-type compound (6-hydroxymaritidine) was tested as an inhibitor against acetyl- and butyrylcholinesterase enzymes (AChE and BChE, respectively), two enzymes relevant in the treatment of Alzheimer's disease, with good results. Structure-activity relationships through molecular docking studies with this alkaloid and other structurally related compounds were discussed.
ESTHER : Adessi_2019_Chem.Biodivers_16_e1800662
PubMedSearch : Adessi_2019_Chem.Biodivers_16_e1800662
PubMedID: 30801949

Title : Cholinesterase-inhibitory effect and in silico analysis of alkaloids from bulbs of Hieronymiella species - Ortiz_2018_Phytomedicine_39_66
Author(s) : Ortiz JE , Garro A , Pigni NB , Aguero MB , Roitman G , Slanis A , Enriz RD , Feresin GE , Bastida J , Tapia A
Ref : Phytomedicine , 39 :66 , 2018
Abstract : BACKGROUND: In Argentina, the Amaryllidaceae family (59 species) comprises a wide variety of genera, only a few species have been investigated as a potential source of cholinesterases inhibitors to treat Alzheimer disease (AD). PURPOSE: To study the acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of the basic dichloromethane extracts (E) from Hieronymiella aurea, H. caletensis, H. clidanthoides, H. marginata, and H. speciosa species, as well as the isolated compounds from these plant extracts. STUDY DESIGN AND METHODS: AChE and BChE inhibitory activities were evaluated with the Ellman's spectrophotometric method. The alkaloids composition from the E was obtained by gas chromatography-mass spectrometry (GC-MS). The E were successively chromatographed on a silica gel column and permeated on Sephadex LH-20 column to afford the main alkaloids identified by means of spectroscopic data. Additionally, an in silico study was carried out. RESULTS: Nine known alkaloids were isolated from the E of five Hieronymiella species. Galanthamine was identified in all the species by GC-MS standing out H. caletensis with a relative abundance of 9.79% of the total ion current. Strong AChE (IC50=1.84 - 15.40microg/ml) and moderate BChE (IC50=23.74 - 136.40microg/ml) inhibitory activities were displayed by the extracts. Among the isolated alkaloids, only sanguinine and chlidanthine (galanthamine-type alkaloids) demonstrated inhibitory activity toward both enzymes. The QTAIM study suggests that sanguinine has the strongest affinity towards AChE, attributed to an additional interaction with Ser200 as well as stronger molecular interactions Glu199 and His440.These results allowed us to differentiate the molecular behavior in the active site among alkaloids possessing different in vitro inhibitory activities. CONCLUSION: Hieronymiella species growing in Argentina represent a rich and widespread source of galanthamine and others AChE and BChE inhibitors alkaloids. Additionally, the new trend towards the use of natural extracts as pharmaceuticals rather than pure drugs opens a pathway for the development of a phytomedicine derived from extracts of Hieronymiella spp.
ESTHER : Ortiz_2018_Phytomedicine_39_66
PubMedSearch : Ortiz_2018_Phytomedicine_39_66
PubMedID: 29433685

Title : N-oxide alkaloids from Crinum amabile (Amaryllidaceae) - Tallini_2018_Molecules_23_1277
Author(s) : Tallini LR , Torras-Claveria L , Borges WS , Kaiser M , Viladomat F , Zuanazzi JAS , Bastida J
Ref : Molecules , 23 :1277 , 2018
Abstract : Natural products play an important role in the development of new drugs. In this context, the Amaryllidaceae alkaloids have attracted considerable attention in view of their unique structural features and various biological activities. In this study, twenty-three alkaloids were identified from Crinum amabile by GC-MS and two new structures (augustine N-oxide and buphanisine N-oxide) were structurally elucidated by NMR. Anti-parasitic and cholinesterase (AChE and BuChE) inhibitory activities of six alkaloids isolated from this species, including the two new compounds, are described herein. None of the alkaloids isolated from C. amabile gave better results than the reference drugs, so it was possible to conclude that the N-oxide group does not increase their therapeutic potential.
ESTHER : Tallini_2018_Molecules_23_1277
PubMedSearch : Tallini_2018_Molecules_23_1277
PubMedID: 29861456

Title : Cholinesterase Inhibition Activity, Alkaloid Profiling and Molecular Docking of Chilean Rhodophiala (Amaryllidaceae) - Tallini_2018_Molecules_23_1532
Author(s) : Tallini LR , Bastida J , Cortes N , Osorio EH , Theoduloz C , Schmeda-Hirschmann G
Ref : Molecules , 23 :1532 , 2018
Abstract : Amaryllidaceae plants are the commercial source of galanthamine, an alkaloid approved for the clinical treatment of Alzheimer’s disease. The chemistry and bioactivity of Chilean representatives of Rhodophiala genus from the family of Amaryllidaceae have not been widely studied so far. Ten collections of five different Chilean Rhodophiala were analyzed in vitro for activity against enzymes such as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) as well as for their alkaloid composition by GC-MS. To obtain an insight into the potential AChE and BuChE inhibitory activity of the alkaloids identified in the most active samples, docking experiments were carried out. Although galanthamine was found neither in aerial parts nor in bulbs of R. splendens, these plant materials were the most active inhibitors of AChE (IC50: 5.78 and 3.62 μg/mL, respectively) and BuChE (IC50: 16.26 and 14.37 μg/mL, respectively). Some 37 known alkaloids and 40 still unidentified compounds were detected in the samples, suggesting high potential in the Chilean Amaryllidaceae plants as sources of both novel bioactive agents and new alkaloids.
ESTHER : Tallini_2018_Molecules_23_1532
PubMedSearch : Tallini_2018_Molecules_23_1532
PubMedID: 29949847

Title : Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking - Tallini_2017_Molecules_22_
Author(s) : Tallini LR , Osorio EH , Santos VDD , Borges WS , Kaiser M , Viladomat F , Zuanazzi JAS , Bastida J
Ref : Molecules , 22 : , 2017
Abstract : The Amaryllidaceae family has proven to be a rich source of active compounds, which are characterized by unique skeleton arrangements and a broad spectrum of biological activities. The aim of this work was to perform the first detailed study of the alkaloid constituents of Hippeastrum reticulatum (Amaryllidaceae) and to determine the anti-parasitological and cholinesterase (AChE and BuChE) inhibitory activities of the epimers (6alpha-hydroxymaritidine and 6beta-hydroxymaritidine). Twelve alkaloids were identified in H. reticulatum: eight known alkaloids by GC-MS and four unknown (6alpha-hydroxymaritidine, 6beta-hydroxymaritidine, reticulinine and isoreticulinine) by NMR. The epimer mixture (6alpha-hydroxymaritidine and 6beta-hydroxymaritidine) showed low activity against all protozoan parasites tested and weak AChE-inhibitory activity. Finally, a molecular docking analysis of AChE and BuChE proteins showed that isoreticulinine may be classified as a potential inhibitory molecule since it can be stabilized in the active site through hydrogen bonds, pi-pi stacking and hydrophobic interactions.
ESTHER : Tallini_2017_Molecules_22_
PubMedSearch : Tallini_2017_Molecules_22_
PubMedID: 29232852

Title : Alkaloids from Hippeastrum argentinum and Their Cholinesterase-Inhibitory Activities: An in Vitro and in Silico Study - Ortiz_2016_J.Nat.Prod_79_1241
Author(s) : Ortiz JE , Pigni NB , Andujar SA , Roitman G , Suvire FD , Enriz RD , Tapia A , Bastida J , Feresin GE
Ref : Journal of Natural Products , 79 :1241 , 2016
Abstract : Two new alkaloids, 4-O-methylnangustine (1) and 7-hydroxyclivonine (2) (montanine and homolycorine types, respectively), and four known alkaloids were isolated from the bulbs of Hippeastrum argentinum, and their cholinesterase-inhibitory activities were evaluated. These compounds were identified using GC-MS, and their structures were defined by physical data analysis. Compound 2 showed weak butyrylcholinesterase (BuChE)-inhibitory activity, with a half-maximal inhibitory concentration (IC50) value of 67.3 +/- 0.09 muM. To better understand the experimental results, a molecular modeling study was also performed. The combination of a docking study, molecular dynamics simulations, and quantum theory of atoms in molecules calculations provides new insight into the molecular interactions of compound 2 with BuChE, which were compared to those of galantamine.
ESTHER : Ortiz_2016_J.Nat.Prod_79_1241
PubMedSearch : Ortiz_2016_J.Nat.Prod_79_1241
PubMedID: 27096334

Title : GC-MS investigation of Amaryllidaceae alkaloids in Galanthus xvalentinei nothosubsp. subplicatus - Sarikaya_2013_Nat.Prod.Commun_8_327
Author(s) : Sarikaya BB , Berkov S , Bastida J , Kaya GI , Onur MA , Somer NU
Ref : Nat Prod Commun , 8 :327 , 2013
Abstract : A GC-MS analysis of alkaloids in the aerial parts and bulbs of Galanthus xvalentinei nothosubsp. subplicatus was performed for the first time. Totally, twenty-six alkaloids were identified, of which tazettine and galanthindole were the major ones. Acetylcholinesterase inhibitory activity of the alkaloidal extracts was determined using modified in vitro Ellman's method. Significant anticholinesterase activity was observed in the tested samples (bulbs: IC50 = 21.3 microg/mL, aerial parts: IC50 = 16.3 microg/mL).
ESTHER : Sarikaya_2013_Nat.Prod.Commun_8_327
PubMedSearch : Sarikaya_2013_Nat.Prod.Commun_8_327
PubMedID: 23678802

Title : GC-MS investigation and acetylcholinesterase inhibitory activity of Galanthus rizehensis - Sarikaya_2013_Z.Naturforsch.C_68_118
Author(s) : Sarikaya BB , Somer NU , Kaya GI , Onur MA , Bastida J , Berkov S
Ref : Z Naturforsch C , 68 :118 , 2013
Abstract : GC-MS (gas chromatography-mass spectrometry) analyses of alkaloids in the aerial parts and bulbs of Galanthus rizehensis Stern (Amaryllidaceae), collected during two different vegetation periods, was performed. Twenty three alkaloids were identified in four different alkaloid extracts. Acetylcholinesterase (AChE) inhibitory activities of the alkaloid extracts were tested. Both the highest alkaloid diversity and the most potent inhibitory activity (IC50 12.94 microg/ml) were obtained in extracts from the bulbs of G. rizehensis collected during the fruiting period.
ESTHER : Sarikaya_2013_Z.Naturforsch.C_68_118
PubMedSearch : Sarikaya_2013_Z.Naturforsch.C_68_118
PubMedID: 23819307

Title : A potent acetylcholinesterase inhibitor from Pancratium illyricum L - Iannello_2013_Fitoterapia_92C_163
Author(s) : Iannello C , Pigni NB , Antognoni F , Poli F , Maxia A , de Andrade JP , Bastida J
Ref : Fitoterapia , 92C :163 , 2013
Abstract : Plants belonging to the Amaryllidaceae contain an exclusive group of alkaloids, known as sources of important biological activities. In the present work, Pancratium illyricum L., a species belonging to this family and endemic of Sardinia (Italy), was investigated for its alkaloid content. Fresh bulbs and leaves were processed separately. Standard extraction and purification procedures were applied to obtain fractions and compounds for GC-MS and NMR analysis. In addition to eight already known alkaloids (1-8), 11alpha-hydroxy-O-methylleucotamine (9) was isolated for the first time and its structure completely determined by one and two-dimensional 1H and 13C NMR spectroscopy. This new galanthamine-type compound exhibited a pronounced in vitro acetylcholinesterase (AChE) inhibitory activity (IC50=3.5+/-1.1muM) in comparison to the reference standard galanthamine hydrobromide (IC50=1.5+/-0.2muM).
ESTHER : Iannello_2013_Fitoterapia_92C_163
PubMedSearch : Iannello_2013_Fitoterapia_92C_163
PubMedID: 24257197

Title : Alkaloids of the South African Amaryllidaceae: a review - Nair_2013_Nat.Prod.Commun_8_1335
Author(s) : Nair JJ , Bastida J , Codina C , Viladomat F , Van Staden J
Ref : Nat Prod Commun , 8 :1335 , 2013
Abstract : The plant family Amaryllidaceae is known for its horticultural and ornamental appeal as well as its medicinal value. In relation to these characteristics, trade in Amaryllid flower varieties (especially daffodils) is a multi-million dollar revenue generator for the floriculture industry. Of greater significance are the medicinal attributes of the family, which has already spawned the Alzheimer's prescription drug galanthamine, a potent and selective inhibitor of the enzyme acetylcholinesterase, of significance in the progression of neurodegeneration associated with motor neuron diseases, with annual global sales of around $150 million . Furthermore, it is anticipated that an anticancer drug target related to the Amaryllidaceae alkaloid pancratistatin, presently under advanced clinical evaluation, will enter commercial circulation within the next decade. Members of the Amaryllidaceae are distributed through both tropical and subtropical regions of the globe, but are of prominence within three distinct geographical locations, including Andean South America, the Mediterranean basin, and southern Africa. The southern African zone is known to harbor at least a third of the worldwide complement of around 1000 species, many of which are widely utilized in the traditional medicinal practices of the indigenous people of the region. Given its therapeutic and economic value, its natural abundance in the southern African region, coupled to its widespread usage in ethnic medicine, the family Amaryllidaceae provides a diverse and accessible platform for phytochemical based drug discovery. A consolidation of its traditional usage as well as its chemical and pharmacological profiles will thus guide efforts aimed at maximizing this potential. In undertaking this survey of the Amaryllidaceae of southern African, we aimed to achieve these goals.
ESTHER : Nair_2013_Nat.Prod.Commun_8_1335
PubMedSearch : Nair_2013_Nat.Prod.Commun_8_1335
PubMedID: 24273880

Title : Bioactive alkaloid extracts from Narcissus broussonetii: Mass spectral studies - de Andrade_2012_J.Pharm.Biomed.Anal_70_13
Author(s) : de Andrade JP , Pigni NB , Torras-Claveria L , Berkov S , Codina C , Viladomat F , Bastida J
Ref : J Pharm Biomed Anal , 70 :13 , 2012
Abstract : Plants of the Amaryllidaceae family are a well-known source of tetrahydroisoquinoline alkaloids with a wide range of biological activities including antiviral antitumoral antiparasitic psychopharmacological and acetylcholinesterase inhibitory among others Recent advances in the use of GC or LC coupled to MS have allowed a chemically guided isolation of uncommon and bioactive alkaloids In the present work analytical methods were applied to study the alkaloid profile of Narcissus broussonetii a plant endemic to North Africa Using the GC-MS technique and an in-home mass fragmentation database twenty-three alkaloids were identified including the very rare dinitrogenous alkaloids obliquine plicamine and secoplicamine Applying LC-ESI-LTQ-Orbitrap-MS fragmentation profiles were found to be similar for obliquine and plicamine but different for secoplicamine Pretazettine a potent cytotoxic alkaloid was also isolated from N broussonetii although its identification by GC-MS was only possible after a BSTFA-derivatization The silylated crude methanolic extract only showed the presence of pretazettine-TMS confirming that tazettine was formed after the alkaloid extraction The same observation was made in Narcissus cultivars in which tazettine had been detected as the major alkaloid As part of an ongoing project on MS of Amaryllidaceae alkaloids the silylated tazettine and pretazettine were studied by GC-MS/MS and found to differ in their fragmentation routes Finally the EtOAc extract of N broussonetii showed notable in vitro activity against Trypanosoma cruzi with an IC(50 value of 1.77mug/ml.
ESTHER : de Andrade_2012_J.Pharm.Biomed.Anal_70_13
PubMedSearch : de Andrade_2012_J.Pharm.Biomed.Anal_70_13
PubMedID: 22673940

Title : GC-MS of amaryllidaceous galanthamine-type alkaloids - Berkov_2012_J.Mass.Spectrom_47_1065
Author(s) : Berkov S , Viladomat F , Codina C , Suarez S , Ravelo A , Bastida J
Ref : J Mass Spectrom , 47 :1065 , 2012
Abstract : 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.
ESTHER : Berkov_2012_J.Mass.Spectrom_47_1065
PubMedSearch : Berkov_2012_J.Mass.Spectrom_47_1065
PubMedID: 22899516

Title : Wild Argentinian Amaryllidaceae, a New Renewable Source of the Acetylcholinesterase Inhibitor Galanthamine and Other Alkaloids - Ortiz_2012_Molecules_17_13473
Author(s) : Ortiz JE , Berkov S , Pigni NB , Theoduloz C , Roitman G , Tapia A , Bastida J , Feresin GE
Ref : Molecules , 17 :13473 , 2012
Abstract : 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 IC(50 between 1.2 and 2 181;g/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.
ESTHER : Ortiz_2012_Molecules_17_13473
PubMedSearch : Ortiz_2012_Molecules_17_13473
PubMedID: 23149565

Title : Acetylcholinesterase-inhibiting alkaloids from Zephyranthes concolor - Reyes-Chilpa_2011_Molecules_16_9520
Author(s) : Reyes-Chilpa R , Berkov S , Hernandez-Ortega S , Jankowski CK , Arseneau S , Clotet-Codina I , Este JA , Codina C , Viladomat F , Bastida J
Ref : Molecules , 16 :9520 , 2011
Abstract : The bulbs and aerial parts of Zephyranthes concolor (Lindl.) Benth. & Hook. f. (Amaryllidaceae), an endemic species to Mexico, were found to contain the alkaloids chlidanthine, galanthamine, galanthamine N-oxide, lycorine, galwesine, and epinorgalanthamine. Since currently only partial and low resolution (1)H-NMR data for chlidanthine acetate are available, and none for chlidanthine, its 1D and 2D high resolution (1)H- and (13)C-NMR spectra were recorded. Unambiguous assignations were achieved with HMBC, and HSQC experiments, and its structure was corroborated by X-ray diffraction. Minimum energy conformation for structures of chlidanthine, and its positional isomer galanthamine, were calculated by molecular modelling. Galanthamine is a well known acetylcholinesterase inhibitor; therefore, the isolated alkaloids were tested for this activity. Chlidanthine and galanthamine N-oxide inhibited electric eel acetylcholinesterase (2.4 and 2.6 x 10(-5) M, respectively), indicating they are about five times less potent than galanthamine, while galwesine was inactive at 10(-3) M. Inhibitory activity of HIV-1 replication, and cytotoxicity of the isolated alkaloids were evaluated in human MT-4 cells; however, the alkaloids showed poor activity as compared with standard anti-HIV drugs, but most of them were not cytotoxic.
ESTHER : Reyes-Chilpa_2011_Molecules_16_9520
PubMedSearch : Reyes-Chilpa_2011_Molecules_16_9520
PubMedID: 22086403

Title : Development and validation of a GC-MS method for rapid determination of galanthamine in Leucojum aestivum and Narcissus ssp.: a metabolomic approach - Berkov_2011_Talanta_83_1455
Author(s) : Berkov S , Bastida J , Viladomat F , Codina C
Ref : Talanta , 83 :1455 , 2011
Abstract : Galanthamine, an acetylcholinesterase inhibitor marketed as a hydrobromide salt for the treatment of Alzheimer's disease, is obtained from some Amaryllidaceae plants. A new method was developed and validated for its quantification by GC-MS in different plant sources: bulbs and leaves from Narcissus confusus; bulbs from N. pseudonarcissus cv. Carlton; and leaves and in vitro cultures from L. aestivum. Samples (50 mg) were extracted with methanol (1 mL) for 2 h, then aliquots of the extracts were silylated and analyzed by GC-MS. The calibration line was linear over a range of 15-800 mug galanthamine/sample, ensuring an analysis of samples with a content of 0.03-1.54% analyte referred to dry weight. The recovery was generally more than 95%. Good inter- and intra assay precision was observed (RSD<3%). Principal component analysis of GC-MS chromatograms allowed discrimination of the plant raw material with respect to species, organs and geographical regions. The analytical method developed in this study proved to be simple, sensitive and far more informative than the routine analytical methods (GC, HPLC, CE and NMR), so it may be useful for quality control of plant raw materials in the pharmaceutical industry.
ESTHER : Berkov_2011_Talanta_83_1455
PubMedSearch : Berkov_2011_Talanta_83_1455
PubMedID: 21238736

Title : Alkaloids from Hippeastrum papilio - de Andrade_2011_Molecules_16_7097
Author(s) : de Andrade JP , Berkov S , Viladomat F , Codina C , Zuanazzi JA , Bastida J
Ref : Molecules , 16 :7097 , 2011
Abstract : Galanthamine, an acetylcholinesterase inhibitor marketed as a hydrobromide salt (Razadyne(R), Reminyl(R)) 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 11beta-hydroxygalanthamine, an epimer of the previously isolated alkaloid habranthine, which was identified using NMR techniques. It has been shown that 11beta-hydroxygalanthamine has an important in vitro acetylcholinesterase inhibitory activity. Additionally, Hippeastrum papilio yielded substantial quantities of galanthamine.
ESTHER : de Andrade_2011_Molecules_16_7097
PubMedSearch : de Andrade_2011_Molecules_16_7097
PubMedID: 21852767

Title : Effect of isoquinoline alkaloids from two Hippeastrum species on in vitro acetylcholinesterase activity - Pagliosa_2010_Phytomedicine_17_698
Author(s) : Pagliosa LB , Monteiro SC , Silva KB , de Andrade JP , Dutilh J , Bastida J , Cammarota M , Zuanazzi JA
Ref : Phytomedicine , 17 :698 , 2010
Abstract : The treatment of neurological disorders and neurodegenerative diseases is related to the levels of acetylcholine (ACh) through the inhibition of acetylcholinesterase (AChE). Galanthamine, an important alkaloid isolated from the Amaryllidaceae family, is approved for the pharmacological treatment of Alzheimer's disease (AD) and acts by inhibiting the acetylcholinesterase (AChE) activity. In the present study, Ellman's method was used to verify the inhibition of AChE activity of some isoquinolines alkaloids such as galanthamine, montanine, hippeastrine and pretazettine. At the concentrations 1mM, 500 microm and 100 microm, galanthamine presented an AChE inhibition higher than 90%. Montanine inhibited, in a dose-dependent manner, more than 50% of the enzyme at 1mM concentration. With the concentrations 500 microm and 100 microm, 30-45% of AChE activity inhibition was detected. The alkaloids hippeastrine and pretazettine presented no significant inhibition of the AChE activity. The results demonstrate that montanine significantly inhibits AChE activity at the tested concentrations, suggesting the necessity of further investigations on this alkaloid use in treating neurological disorders.
ESTHER : Pagliosa_2010_Phytomedicine_17_698
PubMedSearch : Pagliosa_2010_Phytomedicine_17_698
PubMedID: 19969445

Title : Rapid TLC\/GC-MS identification of acetylcholinesterase inhibitors in alkaloid extracts - Berkov_2008_Phytochem.Anal_19_411
Author(s) : Berkov S , Bastida J , Nikolova M , Viladomat F , Codina C
Ref : Phytochem Anal , 19 :411 , 2008
Abstract : Alkaloid extracts from 12 plant species of the families Amaryllidaceae, Fumariacae and Papaveraceae were studied with respect to their acetylcholinesterase inhibitory activity and alkaloid patterns. Fifty-three alkaloids were identified by GC-MS, including known acetylcholinesterase (AChE) inhibitors such as galanthamine, epigalanthamine, sanguinine and epinorgalanthamine in extracts of Amaryllidaceae plants and protopine in extracts of Fumariaceae and Papaveraceae plants. The galanthamine-containing extracts of the amaryllidaceous plants were found to be the most active while the extract of Corydalis bulbosa was the most active among the extracts of the tested plants from the Fumariaceae and Papaveraceae plants. TLC bioautographic assay, preparative TLC and GC-MS analysis were combined to identify the active compounds in the studied extracts. Galanthamine was isolated from the known AChE inhibitors in the extracts of Amaryllidaceae plants. Corydaline, bulbocapnine and stylopine were found to be active in the extracts of plant species of the families Fumariaceae and Papaveraceae. Available standards of deshydrocorydaline--a precursor of corydaline, corydaline and stylopine--were tested for AChE inhibitory activity. Deshydrocorydaline and corydaline showed potent inhibitory activity comparable with that of the positive control galanthamine.
ESTHER : Berkov_2008_Phytochem.Anal_19_411
PubMedSearch : Berkov_2008_Phytochem.Anal_19_411
PubMedID: 18446766

Title : Analysis of galanthamine-type alkaloids by capillary gas chromatography-mass spectrometry in plants - Berkov_2008_Phytochem.Anal_19_285
Author(s) : Berkov S , Bastida J , Viladomat F , Codina C
Ref : Phytochem Anal , 19 :285 , 2008
Abstract : Galanthamine, an acetylcholinesterase inhibitor used for the treatment of Alzheimer's disease, and galanthamine-type alkaloids are synthesised in different plants of the family Amaryllidaceae. A capillary gas chromatographic-mass spectroscopic (CGC-MS) method for the separation of 7 galanthamine type alkaloids, including galanthamine and epigalanthamine, is described in the present paper. A simple method for the routine quantification of galanthamine in plants was developed using pre-packed columns with diatomaceous earth (Isolute HM-N), allowing simultaneous preparation of a large number of samples. Galanthamine showed excellent linearity in the range from 50 to 1000 microg/mL and the limit of quantification was 5 microg/mL in total ion current mode and 1.6 ng/mL in selected ion monitoring mode. The recovery of galanthamine was more than 90%. Interday reproducibility (RSD) of the extraction was 2.74%. A method to find and to microextract Amaryllidaceae alkaloids in low-mass plant samples is also described.
ESTHER : Berkov_2008_Phytochem.Anal_19_285
PubMedSearch : Berkov_2008_Phytochem.Anal_19_285
PubMedID: 18438759

Title : N-Alkylated galanthamine derivatives: Potent acetylcholinesterase inhibitors from Leucojum aestivum - Berkov_2008_Bioorg.Med.Chem.Lett_18_2263
Author(s) : Berkov S , Codina C , Viladomat F , Bastida J
Ref : Bioorganic & Medicinal Chemistry Lett , 18 :2263 , 2008
Abstract : N-(14-Methylallyl)norgalanthamine, a new natural compound, together with five known alkaloids: N-allylnorgalanthamine, galanthamine, epinorgalanthamine, narwedine, and lycorine were isolated from mother liquors (waste material) obtained after industrial production of galanthamine hydrobromide from Leucojum aestivum leaves. The structures of N-allylnorgalanthamine and N-(14-methylallyl)norgalanthamine were completely determined by (1)H and (13)C NMR spectroscopy and two-dimensional experiments. N-allylnorgalanthamine (IC(50)=0.18microM) and N-(14-methylallyl)norgalanthamine (IC(50)=0.16microM) inhibit AChE considerably more than the approved drug galanthamine (IC(50)=1.82microM).
ESTHER : Berkov_2008_Bioorg.Med.Chem.Lett_18_2263
PubMedSearch : Berkov_2008_Bioorg.Med.Chem.Lett_18_2263
PubMedID: 18356045

Title : Alkaloid variability in Leucojum aestivum from wild populations - Georgieva_2007_Z.Naturforsch.C_62_627
Author(s) : Georgieva L , Berkov S , Kondakova V , Bastida J , Viladomat F , Atanassov A , Codina C
Ref : Z Naturforsch C , 62 :627 , 2007
Abstract : Leucojum aestivum (summer snowflake) is a plant species used for the extraction of galanthamine, an acetylcholinesterase inhibitor for the treatment of Alzheimer's disease. Extracts from bulbs collected from 18 Bulgarian populations and from shoot-clumps obtained in vitro from 8 different populations showed variations in their alkaloid composition. Nineteen alkaloids were detected in the studied samples by GC-MS. Typically, the alkaloid fractions of L. aestivum bulbs were dominated by galanthamine type compounds, but lycorine, haemanthamine and homolycorine type alkaloids were also found as dominant compounds in some of the samples. Extracts from the shoot-clumps obtained in vitro were found to contain galanthamine or lycorine as main alkaloids. The galanthamine content ranged from 28 to 2104 microg/g dry weight in the bulbs, and from traces to 454 microg/g dry weight in the shoot-clumps.
ESTHER : Georgieva_2007_Z.Naturforsch.C_62_627
PubMedSearch : Georgieva_2007_Z.Naturforsch.C_62_627
PubMedID: 18069233

Title : Galanthamine pattern in Narcissus confusus plants - Lopez_2003_Planta.Med_69_1166
Author(s) : Lopez S , Bastida J , Viladomat F , Codina C
Ref : Planta Med , 69 :1166 , 2003
Abstract : Galanthamine is an Amaryllidaceae-type alkaloid with acetylcholinesterase inhibitory activity which is used in the treatment of Alzheimer's disease. The distribution of galanthamine and four other alkaloids in different organs of Narcissus confusus plants, as well as the variations occurring during the ontogenic cycle of this plant species, was studied. The five alkaloids were found to be present in all the organs at every stage, with the exception of haemanthamine in senescent flowers. The highest amount of alkaloids occurred in the bulb at the emerging stage, galanthamine being the most abundant, reaching a concentration of up to 2.5 % referred to dry weight.
ESTHER : Lopez_2003_Planta.Med_69_1166
PubMedSearch : Lopez_2003_Planta.Med_69_1166
PubMedID: 14750039

Title : Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts - Lopez_2002_Life.Sci_71_2521
Author(s) : Lopez S , Bastida J , Viladomat F , Codina C
Ref : Life Sciences , 71 :2521 , 2002
Abstract : Amaryllidaceous plants produce pharmacologically active alkaloids, galanthamine being the most interesting for its use in the treatment of Alzheimer's disease as a cholinesterase inhibitor. The aim of this work was to test 23 pure Amaryllidaceae alkaloids and 26 extracts from different species of the genus Narcissus for their acetylcholinesterase inhibitory activity using galanthamine as a reference. Only seven alkaloids, belonging to the galanthamine and lycorine skeleton types, exhibited such an effect, sanguinine being the most active, even more than galanthamine. All the extracts with the highest acetylcholinesterase inhibitory activity contained galanthamine except that of N. assoanus, a lycorine type alkaloid-bearing species.
ESTHER : Lopez_2002_Life.Sci_71_2521
PubMedSearch : Lopez_2002_Life.Sci_71_2521
PubMedID: 12270757