Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking

Tallini, Luciana R.; Osorio, Edison; Santos, Vanessa Dias dos; Borges, Warley de Souza; Kaiser, Marcel; Viladomat, Françesc; Zuanazzi, José Ângelo Silveira

doi:10.3390/molecules22122191

Cited by 27 publications

(34 citation statements)

References 41 publications

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“…On the other hand, crinine 3 and haemanthamine 4 are crinane-type alkaloids that belong to the βcrinane and α-crinane subgroups, respectively (27). Other studies evaluating the anti-parasitic potential of alkaloids have reported that the presence of a methylene-dioxi group seemed to favour a more potent anti-parasitic activity (28). This could be the explanation for the different anti-T. cruzi activities observed by us between these two crinane-type alkaloids.…”

Section: Anti-cruzi Activity Of the Alkaloids Extracted From Amaryllimentioning

confidence: 82%

Amaryllidaceae alkaloids with anti-Trypanosoma cruzi activity

Martínez-Peinado

Cortes-Serra

Torras-Claveria

et al. 2020

Preprint

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Background: Chagas disease, caused by the protozoan Trypanosoma cruzi, is a neglected disease that affects ~7 million people worldwide. Development of new drugs to treat the infection remains a priority since those currently available have frequent side effects and limited efficacy at the chronic stage. Natural products provide a pool of diversity structures to lead the chemical synthesis of novel molecules for this purpose. Herein we analyzed the anti- T. cruzi activity of 9 alkaloids derived from plants of the Amaryllidaceae family. Methods: the activity of each alkaloid was assessed by means of a newly developed anti- T. cruzi phenotypic assay. We further evaluated the compounds that inhibited the parasite growth on two distinct cytotoxicity assays to discard those that were toxic to host cells and assure parasite selectivity. Results: we identified a single compound (hippeastrine 2 ) that was selectively active against the parasite yielding selectivity indexes of 12.7 and 35.2 against Vero and HepG2 cells, respectively. Conclusions: results reported here suggest that natural products are an interesting source of new compounds for the development of drugs against Chagas disease.

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Section: Anti-cruzi Activity Of the Alkaloids Extracted From Amaryllimentioning

confidence: 82%

Amaryllidaceae alkaloids with anti-Trypanosoma cruzi activity

Martínez-Peinado

Cortes-Serra

Torras-Claveria

et al. 2020

Preprint

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“…Amaryllidaceae alkaloids occurring in the samples were identified by comparison of the Rt, fragmentation patterns and data interpretation of the spectra. The database used was built using single alkaloids previously isolated and identified by spectroscopic and spectrometric methods (NMR, UV, CD, IR, MS) in the Natural Products Laboratory, Universidad de Barcelona, the NIST 05 Database and literature data [ 37 , 38 , 39 , 40 , 41 , 42 ].…”

Section: Methodsmentioning

confidence: 99%

Cholinesterase Inhibition Activity, Alkaloid Profiling and Molecular Docking of Chilean Rhodophiala (Amaryllidaceae)

et al. 2018

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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.

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“…On the other hand, crinine 3 and haemanthamine 4 are crinane-type alkaloids that belong to the β-crinane and α-crinane subgroups, respectively (30). Other studies evaluating the anti-parasitic potential of alkaloids have reported that the presence of a methylene-dioxi group seemed to favour a more potent anti-parasitic activity (31). This could be the explanation for the different anti-T. cruzi activities observed by us between these two crinane-type alkaloids.…”

Section: Resultsmentioning

confidence: 81%

Amaryllidaceae alkaloids with anti-Trypanosoma cruzi activity

Martínez-Peinado

Cortes-Serra

Torras-Claveria

et al. 2020

Preprint

Self Cite

View full text Add to dashboard Cite

Background: Chagas disease, caused by the protozoan Trypanosoma cruzi, is a neglected disease that affects ~7 million people worldwide. Development of new drugs to treat the infection remains a priority since those currently available have frequent side effects and limited efficacy at the chronic stage. Natural products provide a pool of diversity structures to lead the chemical synthesis of novel molecules for this purpose. Herein we analyzed the anti- T. cruzi activity of 9 alkaloids derived from plants of the Amaryllidaceae family. Methods: the activity of each alkaloid was assessed by means of an anti- T. cruzi phenotypic assay. We further evaluated the compounds that inhibited the parasite growth on two distinct cytotoxicity assays to discard those that were toxic to host cells and assure parasite selectivity. Results: we identified a single compound (hippeastrine 2 ) that was selectively active against the parasite yielding selectivity indexes of 12.7 and 35.2 against Vero and HepG2 cells, respectively. Moreover, it showed specific activity against the amastigote stage (IC 50 = 3.31 μM). Conclusions: results reported here suggest that natural products are an interesting source of new compounds for the development of drugs against Chagas disease.

show abstract

Hippeastrum reticulatum (Amaryllidaceae): Alkaloid Profiling, Biological Activities and Molecular Docking

Cited by 27 publications

References 41 publications

Amaryllidaceae alkaloids with anti-Trypanosoma cruzi activity

Amaryllidaceae alkaloids with anti-Trypanosoma cruzi activity

Cholinesterase Inhibition Activity, Alkaloid Profiling and Molecular Docking of Chilean Rhodophiala (Amaryllidaceae)

Amaryllidaceae alkaloids with anti-Trypanosoma cruzi activity

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