Berkov S

References (17)

Title : Artemisia santonicum L. and Artemisia lerchiana Web. Essential Oils and Exudates as Sources of Compounds with Pesticidal Action - Nikolova_2023_Plants.(Basel)_12_
Author(s) : Nikolova M , Lyubenova A , Yankova-Tsvetkova E , Georgiev B , Berkov S , Aneva I , Trendafilova A
Ref : Plants (Basel) , 12 : , 2023
Abstract : The application of natural products for pest control is important in modern farming. In the present study, Artemisia santonicum L. and Artemisia lerchiana Weber essential oil and exudate profiles were determined, and their potential as inhibitors of seed germination, acetylcholinesterase, and phytopathogenic mycelium growth were evaluated. Essential oils (EO) were obtained via hydrodistillation and exudates (AE) by washing aerial parts of the species with acetone. EO and AE's composition was identified using GC/MS. Eucalyptol (1,8-cineole) and camphor were found to be the main components of A. lerchiana EO, while beta-pinene, trans-pinocarveol, alpha-pinene, alpha-terpineol, and spathulenol were established as major compounds of A. santonicum EO. Strong inhibition on Lolium perenne seed germination was found at 2 microL/mL and 5 mg/mL using aqueous solutions of EO and AE, respectively. An inhibitory effect on acetylcholinesterase was established, with an IC(50) value of 64.42 and 14.60 microg/mL for EO and 0.961, >1 mg/mL for the AE of A. lerchiana and A. santonicum, respectively. The low inhibition on the mycelium growth of studied phytopathogenic fungi was established by applying 2 microL of EO and 15 microL of 100 mg/mL of AE, with the exception of A. lerchiana AE against Botrytis cinerea. These results show that the studied EO and AE exhibited strong phytotoxic and AChE inhibitory activities, providing new data for these species.
ESTHER : Nikolova_2023_Plants.(Basel)_12_
PubMedSearch : Nikolova_2023_Plants.(Basel)_12_
PubMedID: 37836231

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 : Virtual Screening and Hit Selection of Natural Compounds as Acetylcholinesterase Inhibitors - Atanasova_2022_Molecules_27_
Author(s) : Atanasova M , Dimitrov I , Ivanov S , Georgiev B , Berkov S , Zheleva-Dimitrova D , Doytchinova I
Ref : Molecules , 27 : , 2022
Abstract : Acetylcholinesterase (AChE) is one of the classical targets in the treatment of Alzheimer's disease (AD). Inhibition of AChE slows down the hydrolysis of acetycholine and increases choline levels, improving the cognitive function. The achieved success of plant-based natural drugs acting as AChE inhibitors, such as galantamine (GAL) from Galanthus genus and huperzine A from Huperzia serrate (approved drug in China), in the treatment of AD, and the fact that natural compounds (NCs) are considered as safer and less toxic compared to synthetic drugs, led us to screen the available NCs (almost 150,000) in the ZINC12 database for AChE inhibitory activity. The compounds were screened virtually by molecular docking, filtered for suitable ADME properties, and 32 ligands from 23 structural groups were selected. The stability of the complexes was estimated via 1 micros molecular dynamics simulation. Ten compounds formed stable complexes with the enzyme and had a vendor and a reasonable price per mg. They were tested for AChE inhibitory and antioxidant activity. Five compounds showed weak AChE inhibition and three of them exhibited high antioxidant activity.
ESTHER : Atanasova_2022_Molecules_27_
PubMedSearch : Atanasova_2022_Molecules_27_
PubMedID: 35630613

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 : Neuroprotective activity and acetylcholinesterase inhibition of five Amaryllidaceae species: a comparative study - Cortes_2015_Life.Sci_122_42
Author(s) : Cortes N , Posada-Duque RA , Alvarez R , Alzate F , Berkov S , Cardona-Gomez GP , Osorio E
Ref : Life Sciences , 122 :42 , 2015
Abstract : AIMS: Amaryllidaceae alkaloids exhibit a wide range of physiological effects, of which the acetylcholinesterase (AChE) inhibitory activity is the most relevant. However, scientific evidence related to their neuroprotective effectiveness against glutamate-induced toxicity has been lacking. Thus, the purpose of this study was to conduct a comparative study of the neuroprotective activity and the AChE inhibitory activity of species of Amaryllidaceae. MAIN
METHODS: The neuroprotective activity against glutamate-induced toxicity was measured in rat cortical neurons and the Ellman method was employed for the quantification of acetylcholinesterase inhibitory activity of alkaloidal extracts of five species of Amaryllidaceae (Crinum jagus, Crinum bulbispermum, Hippeastrum barbatum, Hippeastrum puniceum and Zephyranthes carinata). The alkaloid Amaryllidaceae patterns based on GC/MS analyses were also investigated. KEY FINDINGS: The results showed that the alkaloidal extract from C. jagus presented a high neuroprotective activity in both pre- and post-treatments against a glutamate excitotoxic stimulus. Furthermore, the alkaloid extracts from C. jagus and Z. carinata revealed an inhibitory activity of AChE from the electric eel with IC50 values of 18.28+/-0.29 and 17.96+/-1.22mug/mL, respectively. In addition, 46 alkaloids were detected by GC/MS, and 20 of them were identified based on their mass spectra and retention index. The results suggest that the neuroprotective effects might be associated with lycorine and crinine-type alkaloids, whereas the acetylcholinesterase enzyme inhibitory activity could be related to galanthamine and lycorine-type alkaloids, although not based on synergistic processes. SIGNIFICANCE: In summary, Amaryllidaceae species are sources of alkaloids with potential use for Alzheimer's disease.
ESTHER : Cortes_2015_Life.Sci_122_42
PubMedSearch : Cortes_2015_Life.Sci_122_42
PubMedID: 25529145

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 : 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 : 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