New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

Ambrozin, Alessandra Regina Pepe; Mafezoli, Jair; Vieira, Paulo; Fernandes, João B.; Fátima, M.; Silva, G. F. da; Ellena, Javier

doi:10.1590/s0103-50532005000300018

Cited by 20 publications

(14 citation statements)

References 12 publications

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“…Similar studies involving the trypanocidal activity of Meliaceae and Rutaceae species have been reported by our group (Mafezoli et al, 2000;Vieira et al, 2001;Ambrozin et al, 2004Ambrozin et al, , 2005aAmbrozin et al, , 2008 showing that these plants can be considered a promising source of active compounds against trypomastigote forms of T. cruzi. Thus, the significant results obtained from the extracts of C. fruticosa are consistent with those previously reported for this family.…”

Section: Resultssupporting

confidence: 87%

Trypanocidal activity of flavonoids and limonoids isolated from Myrsinaceae and Meliaceae active plant extracts

Leite¹,

Neto²,

Ambrozin³

et al. 2010

Rev. bras. farmacogn.

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RESUMO: "Atividade tripanocida de flavonoides e limonoides isolados de extratos ativos de plantas de Myrsinaceae e Meliaceae". A atividade de extratos brutos de três espécies de Rapanea (Myrsinaceae) e de Cipadessa fruticosa (Meliaceae) foi avaliada in vitro contra formas tripomastigotas de Trypanosoma cruzi. Foram obtidos 33 extratos de diferentes órgãos das espécies estudadas, sendo que onze deles apresentaram atividades significantes (% de lise > 50) nos ensaios realizados. O fracionamento de um extrato ativo dos galhos de R. lancifolia (99,5%) resultou no isolamento de dois flavonoides (quercetina e taxifolina), que apresentaram baixa atividade tripanocida. De um extrato ativo dos frutos de C. fruticosa (97,7%) foram isolados os limonoides mexicanolídeos cipadesina, mexicanolídeo, febrifugina e cipadesina A, que foram moderadamente ativos sobre T. cruzi. Além disso, outros dois flavonoides (flavona e 7-metoxiflavona), previamente ensaiados contra T. cruzi, foram isolados do extrato hexânico dos galhos de C. fruticosa (100%). Os resultados obtidos aqui sugerem que as plantas avaliadas podem constituir fontes de novas substâncias ativas sobre o T. cruzi.Unitermos: Myrsinaceae, Meliaceae, atividade tripanocida, flavonoides, limonoides. ABSTRACT:The activity of crude extracts of three Rapanea species (Myrsinaceae) and Cipadessa fruticosa (Meliaceae) was evaluated in vitro against the trypomastigote forms of Trypanosoma cruzi. Thirty-three extracts from different organs of these species were assayed and eleven of them showed significant activity (lysis % >50). The fractionation of an active extract from branches of R. lancifolia (99.5%) led to the isolation of two flavonoids: quercetin and taxifolin, which have weak trypanocidal activity. Additionally, one active extract from fruits of C. fruticosa (97.7%) afforded mexicanolide limonoids: cipadesin, mexicanolide, febrifugin and cipadesin A, that were slightly active on T. cruzi. Moreover, other two flavonoids (flavone and 7-methoxyflavone), previously assayed against T. cruzi, were isolated from the hexane extract from branches of C. fruticosa (100%). The results presented here suggest that the plants evaluated could be a source of new active compounds against T. cruzi.

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Section: Resultssupporting

confidence: 87%

Trypanocidal activity of flavonoids and limonoids isolated from Myrsinaceae and Meliaceae active plant extracts

Leite¹,

Neto²,

Ambrozin³

et al. 2010

Rev. bras. farmacogn.

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“…This finding indicates that a methoxy group at C-7 is important for AChE inhibition. It has been reported that skimmianine (1), a furoquinoline alkaloid which is abundant in the Rutaceae, has various pharmacological activities such as antiviral and antifungal activities , trypanocidal activity (Ambrozin et al, 2005), antiplatelet aggregation activity (Chen et al, 2000), spontaneous motor activity (Cheng, 1986), cytotoxic activity (Chaturvedula et al, 2003). In this study, we first demonstrated that the total alkaloidal extract from the root of Z. nitidum possessed potent AChE inhibitory activity and skimmianine (1) was responsible compound for this activity.…”

Section: Resultsmentioning

confidence: 65%

Skimmianine, a furoquinoline alkaloid from Zanthoxylum nitidum as a potential acetylcholinesterase inhibitor

et al. 2011

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Skimmianine (1), a newly discovered strong acetylcholinesterase (AChE) inhibitor, along with nine weakly or no active compounds, toddalolactone (2), dictamnine (3), c-fagarine (4), magnolone (5), (-)-(S)-edulinine (6), zanthodioline (7), edulitine (8), 5,6,7-trimethoxycoumarin (9), and haplopine (10) have been isolated from Zanthoxylum nitidum (Z. nitidum). Skimmianine (1) inhibited 50% of AChE activity at the concentrations of 8.6 ± 0.7 lg/ml when the IC 50 value of Physostigmine as a standard was 0.013 ± 0.002 lg/ml. Antiacetylcholinesterase activity of skimmianine (1) was also supported by TLC bioautographic assay. The structure activity relationship on the anti-acetylcholinesterase activity of the quinoline moiety is also discussed in this article.

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“…Kokusaginine ( 37 ) (IC 50 0.560 mM), 34 (IC 50 1.46 mM), and rel ‐(7 R ,8 R )‐8‐[( E )‐3‐hydroxy‐3‐methyl‐1‐butenyl]‐4,8‐dimethoxy‐5,6,7,8‐tetrahydrofuro [2,3‐ b ]quinolin‐7‐yl acetate ( 140 ) (Fig. ) (IC 50 0.977 mM) from Almeidea rubra exhibited moderate in vitro trypanocidal activity against the trypomastigote forms of T. cruzi . Dictamnine ( 40 ) and evolitrine ( 36 , 8‐methoxydictamnine) exhibited antifeedant activity against fourth instar larvae of the tobacco caterpillar Spodoptera litura .…”

Section: Bioactivities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part I

Shang

Morris‐Natschke

Liu

et al. 2017

Medicinal Research Reviews

317

166

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Quinoline and quinazoline alkaloids, two important classes of N-based heterocyclic compounds, have attracted tremendous attention from researchers worldwide since the 19th century. Over the past 200 years, many compounds from these two classes were isolated from natural sources, and most of them and their modified analogs possess significant bioactivities. Quinine and camptothecin are two of the most famous and important quinoline alkaloids, and their discoveries opened new areas in antimalarial and anticancer drug development, respectively. In this review, we survey the literature on bioactive alkaloids from these two classes and highlight research achievements prior to the year 2008 (Part I). Over 200 molecules with a broad range of bioactivities, including antitumor, antimalarial, antibacterial and antifungal, antiparasitic and insecticidal, antiviral, antiplatelet, anti-inflammatory, herbicidal, antioxidant and other activities, were reviewed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.

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New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

Cited by 20 publications

References 12 publications

Trypanocidal activity of flavonoids and limonoids isolated from Myrsinaceae and Meliaceae active plant extracts

Trypanocidal activity of flavonoids and limonoids isolated from Myrsinaceae and Meliaceae active plant extracts

Skimmianine, a furoquinoline alkaloid from Zanthoxylum nitidum as a potential acetylcholinesterase inhibitor

Biologically active quinoline and quinazoline alkaloids part I

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