ISOQUINOLINE ALKALOIDS AND INVESTIGATION OF THE ANTIBACTERIAL AND ANTIPLASMODIAL ACTIVITIES OF<i>Guatteria citriodora</i>(Annonaceae)

Rabelo, Diego de Moura; Pinheiro, Maria Lúcia B.; Barison, Andersson; Salomé, Kahlil Schwanka; Costa, Emmanoel V.; Silva, Felipe M. Araujo da; Chaves, Yury Oliveira; Bastos, Ivanildes dos Santos

doi:10.5935/0100-4042.20140233

Cited by 8 publications

(6 citation statements)

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“…Additionally, the complete and unambiguous NMR assignments of 9-methoxyguadiscine ( 13 ) (Tables and ), as well as the IR, UV, and NMR data of guadiscine ( 15 ) and guadiscidine ( 16 ), are reported herein. All other known alkaloids, demethoxyguadiscine ( 14 ), 6,6a-dihydrodemethoxyguadisine ( 17 ), guatteriopsiscine ( 18 ), lysicamine ( 19 ), liriodenine ( 20 ), and isomoschatoline ( 21 ), were assigned by spectroscopic data comparison (NMR and MS) with literature values.…”

Section: Resultsmentioning

confidence: 99%

“…3 A comparison of the 13 C NMR resonances of the CH 3 -7 and C-7 carbons (Table 3) for 12 with those reported for dehydroguatteriopsiscine, 3 guattouregidine, 16 and guattouregin 16 suggested the β-orientation of the C-7-hydroxy group. Therefore, compound 12 (9-demethox- Additionally, the complete and unambiguous NMR assignments of 9-methoxyguadiscine ( 13) 17 (Tables 1 and 2), as well as the IR, UV, and NMR data of guadiscine (15) and guadiscidine (16), are reported herein. All other known alkaloids, demethoxyguadiscine ( 14), 8 6,6a-dihydrodemethoxyguadisine ( 17), 8 guatteriopsiscine (18), 8 lysicamine ( 19), 18 liriodenine (20), 19 and isomoschatoline (21), 4 were assigned by spectroscopic data comparison (NMR and MS) with literature values.…”

Section: Journal Of Natural Productsmentioning

confidence: 98%

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7,7-Dimethylaporphine and Other Alkaloids from the Bark of Guatteria friesiana

et al. 2016

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Section: Resultsmentioning

confidence: 99%

Section: Journal Of Natural Productsmentioning

confidence: 98%

7,7-Dimethylaporphine and Other Alkaloids from the Bark of Guatteria friesiana

et al. 2016

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“…The FRC3 P. falciparum strains were provided by Leônidas and Maria Deane Institute -FIOCRUZ-Amazônia. The parasites were cultivated according to Trager and Jensen (2005) and the tests carried out based on Rabelo et al (2014) and Bolson et al (2019). The samples were dissolved in Dimethylsulfoxide (DMSO), in a serial dilution (1:2), providing concentrations from 0.39 to 50 μg/mL, and added to the RPMI 1640 culture medium (Gibco, Waltham, USA).…”

Section: Evaluation Of Antiplasmodial Activitymentioning

confidence: 99%

Antiplasmodial activity and phenolic composition of Brazilian Salix humboldtiana Willd. extract and fractions

Ianna¹,

Uebem²,

Luciana³

et al. 2022

J. Med. Plants Res.

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Salix humboldtianaWilld. (Salicaceae) colonizes Brazilian riverine forests and, besides other congeneric species, is traditionally used to treat fever. In folk medicine, it is even used as a Quinine substitute to treat malaria fever. Although its occurrence worldwide was largely reduced between 2000-2015, in Brazil, the case numbers induced by Plasmodium falciparum have increased. Thus, new tools and strategies are necessary against malaria according to the World-Malaria-Report. In the present study the characterization of flavonoids, phenolic acids, phenolic glycosides, and salicylates detected in the ethanol extract of willow leaves, and the antiplasmodial activity of extract of S. humboldtiana and its fractions are firstly reported. Chromatography, UV-Visible spectroscopy, and mass spectrometry were used to characterize substances, and the antiplasmodial activity was accessed by cellular DNA fluorescence measurement with ethidium bromide on a flow cytometer. Kaempferol, apigenin, salicylic acid, and salicylates were found in the extract among other phenolics. The bioassays revealed that lyophilized extract of S. humboldtiana Willd showed antiplasmodial activity. Hexane, AcOEt, and Methanol fractions were active against P. falciparum at IC 50 of 0.655, 0.929 and 0.688 μg/mL, respectively. Quinine, used as a reference, showed an IC 50 of 0.147 μg/mL. The polyphenols -salicylates and flavonoids, especially kaempferol and catechin, detected in LESh, exhibit biochemical interference on the plasmodial metabolism, as already reported, and they could also promote the antiplasmodial activity detected. This alleged medicinal use has been already reported for some Salix species. Moreover, this work presents scientific evidence for the antiplasmodial activity of S. humboldtiana, which can be helpful in the development of antiplasmodial phytomedicine.

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“…Palmatine 3 is the most represented protoberberine alkaloid described in Menispermaceae family, being encountered in the Stephania [ 7 , 28 , 29 , 30 ], Tinospora [ 31 , 32 , 33 , 34 , 35 , 36 ], Coscinium [ 37 ], Abuta [ 38 ], and Arcangelisia [ 39 ] genera. Protoberberine alkaloids are well known for their neuroprotective, antioxidant, and cholinesterases (ChEs) inhibitory activities [ 40 , 41 ] among different other pharmacological properties [ 42 , 43 ].…”

Section: Introductionmentioning

confidence: 99%

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

et al. 2022

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Alkaloids are natural products known as ethnobotanicals that have attracted increasing attention due to a wide range of their pharmacological properties. In this study, cholinesterase inhibitors were obtained from branches of Abuta panurensis Eichler (Menispermaceae), an endemic species from the Amazonian rainforest. Five alkaloids were isolated, and their structure was elucidated by a combination of 1D and 2D 1H and 13C NMR spectroscopy, HPLC-MS, and high-resolution MS: Lindoldhamine isomer m/z 569.2674 (1), stepharine m/z 298.1461 (2), palmatine m/z 352.1616 (3), 5-N-methylmaytenine m/z 420.2669 (4) and the N-trans-feruloyltyramine m/z 314.1404 (5). The compounds 1, 3, and 5 were isolated from A. panurensis for the first time. Interaction of the above-mentioned alkaloids with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes was investigated in silico by molecular docking and molecular dynamics. The molecules under investigation were able to bind effectively with the active sites of the AChE and BChE enzymes. The compounds 1–4 demonstrated in vitro an inhibitory effect on acetylcholinesterase with IC50 values in the range of 19.55 µM to 61.24 µM. The data obtained in silico corroborate the results of AChE enzyme inhibition.

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ISOQUINOLINE ALKALOIDS AND INVESTIGATION OF THE ANTIBACTERIAL AND ANTIPLASMODIAL ACTIVITIES OFGuatteria citriodora(Annonaceae)

Cited by 8 publications

References 1 publication

7,7-Dimethylaporphine and Other Alkaloids from the Bark of Guatteria friesiana

7,7-Dimethylaporphine and Other Alkaloids from the Bark of Guatteria friesiana

Antiplasmodial activity and phenolic composition of Brazilian Salix humboldtiana Willd. extract and fractions

In Vitro and In Silico Evaluation of Cholinesterase Inhibition by Alkaloids Obtained from Branches of Abuta panurensis Eichler

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