1H and 13C-NMR Data of the Simplest Plumeran Indole Alkaloids Isolated from Aspidosperma Species

Guimarães, Heloisa Alves; Braz-Filho, Raimundo; Vieira, Ivo José Curcino

doi:10.3390/molecules17033025

Cited by 22 publications

(17 citation statements)

References 46 publications

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“…Compound 16 (aspidospermine or 1-((3a R ,5a R ,10b R ,12b R )-3a-Ethyl-7-methoxy-2,3,3a,5,5a,11,12,12b-octahydro-1 H ,4 H -6,12a-diaza-indeno[7,1- cd ]fluoren-6-yl)-ethanone) showed NMR spectra identical to those reported in the literature [28].…”

Section: Methodsmentioning

confidence: 61%

Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections

Casciaro

Calcaterra

Cappiello

et al. 2019

Toxins

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Staphylococcus aureus is a major human pathogen causing a wide range of nosocomial infections including pulmonary, urinary, and skin infections. Notably, the emergence of bacterial strains resistant to conventional antibiotics has prompted researchers to find new compounds capable of killing these pathogens. Nature is undoubtedly an invaluable source of bioactive molecules characterized by an ample chemical diversity. They can act as unique platform providing new scaffolds for further chemical modifications in order to obtain compounds with optimized biological activity. A class of natural compounds with a variety of biological activities is represented by alkaloids, important secondary metabolites produced by a large number of organisms including bacteria, fungi, plants, and animals. In this work, starting from the screening of 39 alkaloids retrieved from a unique in-house library, we identified a heterodimer -carboline alkaloid, nigritanine, with a potent anti-Staphylococcus action. Nigritanine, isolated from Strychnos nigritana, was characterized for its antimicrobial activity against a reference and three clinical isolates of S. aureus. Its potential cytotoxicity was also evaluated at short and long term against mammalian red blood cells and human keratinocytes, respectively. Nigritanine showed a remarkable antimicrobial activity (minimum inhibitory concentration of 128 µM) without being toxic in vitro to both tested cells. The analysis of the antibacterial activity related to the nigritanine scaffold furnished new insights in the structure–activity relationships (SARs) of -carboline, confirming that dimerization improves its antibacterial activity. Taking into account these interesting results, nigritanine can be considered as a promising candidate for the development of new antimicrobial molecules for the treatment of S. aureus-induced infections.

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Section: Methodsmentioning

confidence: 61%

Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections

Casciaro

Calcaterra

Cappiello

et al. 2019

Toxins

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“…Also, evident from this spectrum were correlations of signals at δ H 3.93 (H-3b) and δ H 4.25 (H-5b), at δ H 4.68 (H-2) and δ H 1.81 (H-17b), and at δ H 6.78 (H-9) and δ H 4.43 (H-5a) in compound 13 , as shown in Figure 2. A structural similarity search allowed for models to be obtained for comparison of data [39] together with 1 H and 13 C data from the literature [40].…”

Section: Resultsmentioning

confidence: 99%

Chemical Composition of Aspidosperma ulei Markgr. and Antiplasmodial Activity of Selected Indole Alkaloids

et al. 2013

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Abstract:A new indole alkaloid, 12-hydroxy-N-acetyl-21(N)-dehydroplumeran-18-oic acid (13), and 11 known indole alkaloids: 3,4,5,6-tetradehydro-β-yohimbine (3), 19(E)-hunteracine (4), β-yohimbine (5), yohimbine (6), 19,20-dehydro-17-α-yohimbine (7), uleine (10), 20-epi-dasycarpidone (11), olivacine (8), 20-epi-N-nor-dasycarpidone (14), N-demethyluleine (15) and 20(E)-nor-subincanadine E (12) and a boonein δ-lactone 9, ursolic acid (1) and 1D,1O-methyl-chiro-inositol (2) were isolated from the EtOH extracts of different parts of Aspidosperma ulei Markgr. (Apocynaceae). Identification and structural elucidation were based on IR, MS, 6282Plasmodium falciparum. IC 50 values of 14.0 (39.9), 4.5 (16.7) and 14.5 (54.3) μg/mL (μM) were determined for 3, 11 and 12, respectively. Inhibitory activity of 3, 4, 11, 12 and 13 was evaluated against NIH3T3 murine fibroblasts. None of these compounds exhibited toxicity to fibroblasts (IC 50 > 50 μg/mL). Of the five compounds screened for in vitro antiplasmodial activity, only 11 was active.

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“…Reviews on the chemistry of Aspidosperma plants cite indole alkaloids ( Pereira et al 2007 , Guimarães et al 2012 ) and a new alkaloid, braznitidumine, from A. nitidum was described, isolated and characterised by one of the present authors ( Meneses-Pereira et al 2006 ). In this study, we verify the biological activity of wood bark extracts and fractions in vitro against chloroquine-resistant (CQR) P. falciparum parasites and in a Plasmodium berghei -infected mouse malaria model .…”

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confidence: 79%

Aspidosperma (Apocynaceae) plant cytotoxicity and activity towards malaria parasites. Part I: Aspidosperma nitidum (Benth) used as a remedy to treat fever and malaria in the Amazon

Coutinho

Aguiar

Santos

et al. 2013

Mem. Inst. Oswaldo Cruz

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Infusions of Aspidosperma nitidum (Apocynaceae) wood bark are used to treat fever and malaria in the Amazon Region. Several species of this family are known to possess indole alkaloids and other classes of secondary metabolites, whereas terpenoids, an inositol and the indole alkaloids harmane-3 acid and braznitidumine have been described in A. nitidum . In the present study, extracts from the wood bark, leaves and branches of this species were prepared for assays against malaria parasites and cytotoxicity testing using human hepatoma and normal monkey kidney cells. The wood bark extracts were active against Plasmodium falciparum and showed a low cytotoxicity in vitro, whereas the leaf and branch extracts and the pure alkaloid braznitidumine were inactive. A crude methanol extract was subjected to acid-base fractionation aimed at obtaining alkaloid-rich fractions, which were active at low concentrations against P. falciparum and in mice infected with and sensitive Plasmodium berghei parasites. Our data validate the antimalarial usefulness of A. nitidum wood bark, a remedy that can most likely help to control malaria. However, the molecules responsible for this antimalarial activity have not yet been identified. Considering their high selectivity index, the alkaloid-rich fractions from the plant bark might be useful in the development of new antimalarials.

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1H and 13C-NMR Data of the Simplest Plumeran Indole Alkaloids Isolated from Aspidosperma Species

Cited by 22 publications

References 46 publications

Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections

Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections

Chemical Composition of Aspidosperma ulei Markgr. and Antiplasmodial Activity of Selected Indole Alkaloids

Aspidosperma (Apocynaceae) plant cytotoxicity and activity towards malaria parasites. Part I: Aspidosperma nitidum (Benth) used as a remedy to treat fever and malaria in the Amazon

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