Antiprotozoal Sesquiterpene Pyridine Alkaloids from Maytenus ilicifolia

Santos, Vânia; Regasini, Luís Octávio; Nogueira, Cláudio Rodrigo; Passerini, Gabriela Duó; Martínez, Isabel; Bolzani, Vanderlan da Silva; Graminha, Márcia Aparecida Silva; Cicarelli, Regina Maria Barreto; Furlan, Maysa

doi:10.1021/np300077r

Cited by 76 publications

(36 citation statements)

References 30 publications

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“…The small coupling constant of J1,2 = 3.6 Hz between H-1 and H-2 indicated that the H-2 was equatorial. These data revealed that the relative configuration of the dihydro-β-agarofuran sesquiterpene core in 1 was identical to that of triptonine A [10] and the related compounds [12,27,28]. The relative configurations of the groups at two macrocyclic rings were determined by comparison of the NMR spectroscopic data with those of triptonine A [10], which was established by X-ray crystallography.…”

Section: Resultsmentioning

confidence: 85%

“…Its UV spectrum showed absorption bands at λmax 231 and 253 nm, indicating the presence of aromatic rings. In the 1 H-NMR spectroscopic data of 1 (Table 1) [23,[25][26][27][28]. An evoninic acid moiety [25][26][27][28][29] (Table 1) along with DEPT and HSQC spectra showed the presence of the units mentioned above in 1.…”

Section: Resultsmentioning

confidence: 94%

“…In the 1 H-NMR spectroscopic data of 1 (Table 1) [23,[25][26][27][28]. An evoninic acid moiety [25][26][27][28][29] (Table 1) along with DEPT and HSQC spectra showed the presence of the units mentioned above in 1. These characteristic NMR data suggested 1 to be a dimacrolide sesquiterpene pyridine alkaloid [5][6][7][8][9][10][11][12].…”

Section: Resultsmentioning

confidence: 94%

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Dimacrolide Sesquiterpene Pyridine Alkaloids from the Stems of Tripterygium regelii

Fan

Zhu

et al. 2016

Preprint

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Abstract:Two new dimacrolide sesquiterpene pyridine alkaloids (DMSPAs), dimacroregelines A (1) and B (2), were isolated from the stems of Tripterygium regelii. The structures of both compounds were characterized by extensive 1D and 2D NMR spectroscopic analyses, as well as HRESIMS data. Compounds 1 and 2 are two rare DMSPAs possessing unique 2-(3′-carboxybutyl)-3-furanoic acid units forming the second macrocyclic ring, representing the first example of DMSPAs bearing an extra furan ring in their second macrocyclic ring system. Compound 2 showed inhibitory effects on the proliferation of human rheumatoid arthritis synovial fibroblast cell (MH7A) at a concentration of 20 μM.

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Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 94%

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Dimacrolide Sesquiterpene Pyridine Alkaloids from the Stems of Tripterygium regelii

Fan

Zhu

et al. 2016

Preprint

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“…Absorbances were read at 490 nm. The drug concentration corresponding to 50% of parasite growth inhibition was expressed as the inhibitory concentration (IC50) in μM [10].…”

Section: Animalsmentioning

confidence: 99%

Synthesis, biological evaluation and bioavailability prediction of novel furoxan derivatives as leishmanicidal compounds

Pavan

Almeida

Passalacqua

et al. 2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

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Four novel furoxan derivatives were synthesized, characterized and evaluated for in vitro activity against promastigote form of Leishmania amazonensis and Leishmania infantum, and amastigote form of L. infantum. Compound 7 presented low cytotoxicity, being 30 times less toxic than pentamidine. All compounds were more active against L. infantum than L. amazonensis promastigote form, with IC50 reaching values around 8 µM.Regarding amastigote form of L. infantum, the compounds (3b and 7) have exhibited IC50 values around 60 µM. The in silico prediction of ADME properties has shown that all compounds demonstrated drugability according to 'Lipinski rules' and presented intestinal absorption ranging from 67 to 70%. In conclusion, the compounds presented here have demonstrated to be interesting prototypes against the visceral form of leishmaniasis.

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“…All the assays were performed in triplicate. Test samples concentrations corresponding to 50% of parasite growth inhibition (IC 50 ) were determined from non-linear regression (Muelas-Serrano et al 2000;Santos et al 2012).…”

Section: In Vitro Assay For Trypanocidal Activitymentioning

confidence: 99%

Oleanonic acid from Lippia lupulina (Verbenaceae) shows strong in vitro antileishmanial and antitrypanosomal activity

et al. 2016

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Leishmaniasis and Chagas disease affect millions of people in tropical and subtropical regions. Drugs used currently to treat such diseases often present undesirable side effects and low efficiency. The aim of this work was to identify extracts and isolated compounds from the genus Lippia with leishmanicidal and trypanocidal activity. , respectively). The triterpenoid oleanonic acid showed the strongest activity against these protozoans (IC 50 of 18.5 and 29.9 µM, respectively). Our results indicate that Lippia plants and their derivatives deserve further investigation in the search for new antiprotozoal drugs, particularly for the treatment of leishmaniasis and Chagas disease. KEYWORDS: Leishmanicidal, trypanocidal, triterpenoids, flavonoids, T. cruzi Ácido oleanônico isolado de Lippia lupulina (Verbenaceae) apresenta potentes atividades leishmanicida e tripanocida Leishmaniose e doença de Chagas afetam milhões de pessoas em regiões tropicais e subtropicais. As drogas atualmente usadas para tratar estas doenças frequentemente apresentam efeitos colaterais indesejáveis e baixa eficiência. Este trabalho teve como objetivo encontrar extratos, frações e compostos isolados de espécies do gênero Lippia com atividades leishmanicida e tripanocida. Quinze extratos de diferentes partes de plantas do gênero Lippia, com composições químicas parcialmente conhecidas, quatro frações de partição, seis substâncias e uma mistura de quatro flavanonas interconversíveis isolados de Lippia salviaefolia e Lippia lupulina foram testados, in vitro, frente a formas epimastigotas de Trypanosoma cruzi e promastigotas de Leishmania amazonensis. O extrato etanólico das raízes de L. lupulina apresentou atividade potente contra T. cruzi e L. amazonensis (IC 50 de 20,0 e 54,5 µg mL -1 , respectivamente), enquanto que o ácido oleanônico mostrou as atividades mais fortes contra estes protozoários, com IC 50 de 18,5 e 29,9 µM, respectivamente. Estes resultados indicam que espécies do gênero Lippia e seus derivados merecem investigações adicionais na busca por novas terapias antiprotozoárias, especialmente para o tratamento de leishmaniose e doença de Chagas.

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Antiprotozoal Sesquiterpene Pyridine Alkaloids from Maytenus ilicifolia

Cited by 76 publications

References 30 publications

Dimacrolide Sesquiterpene Pyridine Alkaloids from the Stems of <em>Tripterygium regelii</em>

Dimacrolide Sesquiterpene Pyridine Alkaloids from the Stems of <em>Tripterygium regelii</em>

Synthesis, biological evaluation and bioavailability prediction of novel furoxan derivatives as leishmanicidal compounds

Oleanonic acid from Lippia lupulina (Verbenaceae) shows strong in vitro antileishmanial and antitrypanosomal activity

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