Examinando por Materia "Alkaloids"
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- PublicaciónSólo datosAlkaloids of Phaedranassa dubia (Kunth) J.F. Macbr. and Phaedranassa brevifolia Meerow (Amaryllidaceae) from Ecuador and its cholinesterase-inhibitory activity(South African Journal of Botany, 2021-08-04) Acosta León, Karen; Inca, Alexandra; Tallini, Luciana R.; Osorio, Edison H.; Robles, Jessica; Bastida, Jaume; Oleas, Nora H.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 (IC50 values of 25.48 ± 0.39 and 3.45 ± 0.29 μg.mL−1, respectively) and BuChE (IC50 values of 114.96 ± 4.94 and 58.89 ± 0.55 μg.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.
- PublicaciónAcceso abiertoAntileishmanial activity of Clinanthus milagroanthus S. Leiva & Meerow (Amaryllidaceae) collected in Peru(2023-01-10) Soto-Vásquez, Marilú Roxana; Alvarado-García, Paul Alan Arkin; Osorio, Edison H.; Tallini, Luciana R.; Bastida, JaumeLeishmaniasis is a worldwide infectious parasitic disease caused by different species of protozoa of the genus Leishmania, which are transmitted to animals and humans through the bite of insects of the Psychodidae family. In the present work, the antileishmanial activity of an alkaloid extract of the bulbs of Clinanthus milagroanthus S. Leiva & Meerow (Amaryllidaceae) was evaluated in vitro, in vivo, and in silico against the parasite Leishmania braziliensis, and the chemical profile of the sample was determined by GC-MS analysis. At concentrations of 1, 10, and 100 µg·mL−1, the alkaloid extract presented inhibition percentages of 8.7%, 23.1%, and 98.8%, respectively, against L. braziliensis with a p < 0.05, and IC50 values of 18.5 ± 0.3 µg·mL−1. Furthermore, at a dose of 1.0 mg·kg−1, a greater decrease in lesion size was observed (90%) for in vivo assays, as well as a decrease in infection (96%), finding no significant differences (p > 0.05) in comparison with amphotericin B (92% and 98%, respectively). Eleven alkaloids were identified in C. milagroanthus bulbs: galanthamine, vittatine/crinine, 8-O-demethylmaritidine, anhydrolycorine, 11,12-dehydroanhydrolycorine, hippamine, lycorine, 2-hydroxyanhydrolycorine, 7-hydroxyclivonine, 2α-hydroxyhomolycorine, and 7-hydroxyclivonine isomer. A molecular model of Leishmania braziliensis trypanothione reductase (TRLb) was built using computational experiments to evaluate in silico the potential of the Amaryllidaceae alkaloid identified in C. milagroanthus toward this enzyme. The structures galanthamine, 7-hydroxyclivonine isomer, and crinine showed better estimated free energy of binding than the reference compound, amphotericin B. In conclusion, this is the first in vitro, in vivo, and in silico report about the antileishmanial potential and alkaloid profiling of the extract of C. milagroanthus bulbs, which could become an interesting source of bioactive molecules
- PublicaciónSólo datosChemical Profiling and Cholinesterase Inhibitory Activity of Five Phaedranassa Herb. (Amaryllidaceae) Species from Ecuador(Molecules, 2020-04-30) Moreno, Raúl; Tallini, Luciana R.; Salazar, Cristina; Osorio, Edison; Montero, Evelin; Bastida, Jaume; Oleas, Nora H.; Acosta León, KarenIt 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.
- PublicaciónAcceso abiertoChemical survey of three species of the Genus rauhia traub (Amaryllidaceae)(2022-12-16) Tallini, Luciana R.; Osorio, Edison H.; Berkov, Strahil; Torras-Claveria, Laura; Rodríguez-Escobar, María L.; Viladomat, Francesc; Meerow, Alan W.; Bastida, JaumePlant 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 (IC50) values of 0.17 ± 0.02 μg·mL−1 in comparison with the IC50 values of 0.53 ± 0.12 μg·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
- PublicaciónSólo datosMicrosatellites, morphological, and alkaloids characterization of Zephyranthes fosteri and Z. alba (Amaryllidaceae): Allopatric populations(Biochemical Systematics and Ecology, 2022-03-15) Centeno-Betanzos, Lucia Y.; López-Caamal, Alfredo; Cortés Rendon, Natalie; León Santiago, Mayra; Osorio, Edison; Bastida Armengol, Jaume; Cano-Santana, Zenón; Reyes-Chilpa, Ricardo; Tovar-Sánchez, EfraínZephyranthes (Amaryllidaceae) is a taxonomically complex genus due to the frequent overlap of interspecific morphological variation. In Mexico, Z. alba and Z. fosteri are herbaceous plants that, when distributed in sympatry, generate individuals with complex patterns of morphological variation, leading to taxonomic confusion. Therefore, it is necessary to first characterize these species in allopatric populations. In this contribution, molecular, morphological, and alkaloid profiles were used to characterize both species in allopatric sites. Our results show that Z. alba and Z. fosteri allopatric populations are two well-defined genetic and morphological groups. Flower-related characters were the ones that best allowed us to distinguish between species. In a similar fashion, the alkaloid profile showed remarkable differences among species: four alkaloids were specific to Z. alba and five to Z. fosteri. Lycorine (43.3-88.8%) and galanthamine (87.7-91.4%) were the most abundant alkaloids for each species, respectively. In conclusion, Z. fosteri and Z. alba exhibit noticeable differences when distributed in allopatry. In addition, Z. fosteri has greater genetic and phenotypic plasticity compared to Z. alba, which could be related to the former's ability to colonize new habitats. Finally, the molecular, genetic and chemical markers developed here will provide a framework to further studies aiming to explore if hybridization among Z. alba and Z. fosteri occurs in sympatric populations.