Effects of canthin-6-one alkaloids from Zanthoxylum chiloperone on Trypanosoma cruzi-infected mice

Ferreira, Marı́a Elena; Nakayama, Héctor David; Arias, Antonieta Rojas de; Schinini, Alicia; Bilbao, Ninfa Vera de; Serna, Elva; Lagoutte, Delphine; Soriano-Agatón, Flor; Poupon, Erwan; Hocquemiller, Reynald; Fournet, Alain

doi:10.1016/j.jep.2006.07.028

Cited by 61 publications

(44 citation statements)

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“…In general, indole alkaloids are a class of compound having a range of biological activities, including antibacterial, trypanocidal, leishmanicidal and anticancer (Sakamoto-Hojo et al 1988, Delorenzi et al 2001, Ferreira et al 2006, Tanaka et al 2006). The antiplasmodial activity of monoterpene indole alkaloids has been investigated (Wright et al 1994, Iwu et al 1994).…”

Section: Discussionmentioning

confidence: 99%

In vitro inhibition of Plasmodium falciparum by substances isolated from Amazonian antimalarial plants

Andrade‐Neto

Pohlit

Pinto

et al. 2007

Mem. Inst. Oswaldo Cruz

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In the present study, a quassinoid, neosergeolide, isolated from the roots and stems of Picrolemma sprucei (Simaroubaceae), the indole alkaloids ellipticine and aspidocarpine, isolated from the bark of Aspidosperma vargasii and A. desmanthum (Apocynaceae), respectively, and 4-nerolidylcatechol, isolated from the roots of Pothomorphe peltata (Piperaceae), all presented significant in vitro inhibition (more active than quinine and chloroquine) of the multi-drug resistant K1 strain of Plasmodium falciparum. Neosergeolide presented activity in the nanomolar range. This is the first report on the antimalarial activity of these known, natural compounds. This is also the first report on the isolation of aspidocarpine from A. desmanthum. These compounds are good candidates for pre-clinical tests as novel lead structures with the aim of finding new antimalarial prototypes and lend support to the traditional use of the plants from which these compounds are derived.Key words: neosergeolide -ellipticine -aspidocarpine -4-nerolidylcatechol -Pothomorphe peltata -Picrolemma spruceiAspidosperma spp.Malaria is the main cause of economic loss and high morbidity in the world today and continues to be endemic to tropical regions such as the Amazon. In the Brazilian Amazon, 1.6 million positive plates (thick smears) in a total of 8 million diagnostic tests for malaria were registered from January 2004 to February 2007 (Ministério da Saúde, Sivep-Malaria 2007). The lack of an effective vaccine and the increasing expansion of strains of Plasmodium falciparum presenting resistance towards commonly used, low-cost antimalarials make control of this disease difficult (Olliaro & Bloland 2001, Wellens & Plowe 2001, Vieira et al. 2001, Gonzales et al. 2003, Alecrim et al. 2006. As a result, the World Health Organization (WHO 1978(WHO , 1995 has been promoting research on natural product based drugs for treatment of disease and many plant species have been evaluated for antimalarial activity (Weniger et al. 2004). In these studies, emphasis has been on the discovery of lead compounds for drug development (Gundidza & Chinyanganya 1999). The rational search for active substances in medicinal plants is a very promising and cost-effective strategy for antimalarial drug discovery. This approach benefits from the accumulated knowledge of the curing capacity of plants possessed by inhabitants of malaria endemic regions and permits the extensive evaluation of natural products derived from these sources (Campbell et al. 1997, 1998, Brandão et al. 1992, 1997, Krettli et al. 2001, Andrade-Neto et al. 2004a.This triage of useful and effective plants is at the heart of traditional medicinal knowledge and is an extremely important source of therapeutic compounds in use today. Important semi-synthetic, low-cost, highly effective antimalarial drugs such as the quinolines (chloroquine, mefloquine, primaquine, etc.) and artemisinin derivatives (sodium artesunate, arteether, artemether, etc.) owe their initial discovery to the isolation and structural identi...

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Section: Discussionmentioning

confidence: 99%

In vitro inhibition of Plasmodium falciparum by substances isolated from Amazonian antimalarial plants

Andrade‐Neto

Pohlit

Pinto

et al. 2007

Mem. Inst. Oswaldo Cruz

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“…1 Chemically, this genus is characterized by alkaloids, [2][3][4][5][6][7] cumarins, 5,6,8 lignans, 4,9,10 amides 11,12 and terpenes. 5,6,13,14 Ongoing studies have shown that Zanthoxylum exhibit a range of biological activities such as antichagas, 2 tripanocidal, 9 antiplasmodial, 7 anti-HIV 13 and antiinflammatory, 8,10 as well as antihelmintic.…”

Section: Introductionmentioning

confidence: 99%

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

Fernandes¹,

Vieira²,

Silva³

et al. 2009

J. Braz. Chem. Soc.

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Um novo alcalóide benzofenantridínico, 6-acetonil-N-metil-diidrodecarina foi isolado das raízes de Zanthoxylum riedelianum juntamente com lupeol, 6-acetonildiidroqueleritrina e 6-acetonildiidroavicina. As estruturas dessas substâncias foram estabelecidas com base na análise dos dados espectrométricos de IV, EM e RMN incluindo experimentos 2D.A new benzophenanthridine alkaloid, 6-acetonyl-N-methyl-dihydrodecarine was isolated from Zanthoxylum riedelianum roots together with lupeol, 6-acetonyldihydrochelerythrine and 6-acetonyldihydroavicine. The structures were established from the IR, MS and NMR spectral data, including 2D-NMR experiments. Keywords: Zanthoxylum riedelianum, Rutaceae, benzophenanthridine alkaloids IntroductionThe Zanthoxylum genus (Rutaceae) is composed by more than 200 species and largely distributed around the world. 1 Chemically, this genus is characterized by alkaloids, 2-7 cumarins, 5,6,8 lignans, 4,9,10 amides 11,12 and terpenes. 5,6,13,14 Ongoing studies have shown that Zanthoxylum exhibit a range of biological activities such as antichagas, 2 tripanocidal, 9 antiplasmodial, 7 anti-HIV 13 and antiinflammatory, 8,10 as well as antihelmintic. 12 Z. riedelianum is used in folk medicine as a decoction against different types of inflammations, rheumatism and skin stains. 15 Previous works reported the identification of terpenes from the essential oil 14 and lignans from the leaves and the stem bark. 10 In this work we report the isolation and structural elucidation of a novel benzophenanthridine alkaloid, namely, 6-acetonyl-N-methyl-dihydrodecarine (1), together with two known alkaloids 6-acetonyldihydrochelerythrine (2) and 6-acetonyldihydroavicine (3) from the roots of Z. riedelianum. Experimental General proceduresMelting points were uncorrected. IR spectra were recorded on FTIR-Bomem-MB/100 model spectrophotometer using NaCl film. NMR spectra in CDCl 3 , were recorded on Bruker ARX-400 (400 MHz for 1 H and 100 MHz for 13 C); Bruker AC-200 (200 MHz for 1 H and 50 MHZ for 13 C) and Varian-Mercury 300 (300 MHz for 1 H and 75 MHz for 13 C) spectrometers, using tetramethylsilane (TMS) as internal standard. Electron Ionization Mass Spectra (ESI-MS) was undertaken employing a Quatro LC-Micromass UK model spectrometer. Optical rotations were determined on a Perkin-Elmer 341 polarimeter. CC: silica gel (Merck 70-230 mesh ASTM); TLC: silica gel G 60 and silica gel 60 PF 254 (Merck) were used to analyze the fractions collected from column chromatography (CC) with visualization by UV (254 and 366 nm), Dragendorff´s reagent and exposure to iodine vapor. Plant materialZanthoxylum riedelianum (Engl.) was collected in Rio Manso Highway, km 22, Chapada dos Guimarães, Mato 6-Acetonyl-N-methyl-dihydrodecarine, a New Alkaloid from Zanthoxylum riedelianum J. Braz. Chem. Soc. 380 Grosso State, Brazil. A voucher specimen (No. 24.080) was deposited at Universidade Federal de Mato Grosso Central Herbarium. Extraction and isolationDried roots (3.0 kg) were powdered and extracted with hexane and methanol by mac...

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“…Se ha reportado que el extracto de la hoja de B. dracunculifolia, a una concentración de 3 mg/mL, produjo 100% de lisis de formas tripomastigotes de T. cruzi (13) ; los extractos y fracciones de A. amazonicus mostraron lisis de las formas tripomasigotes de T. cruzi in vitro (14) ; otros investigadores también han demostrado el efecto tripanocida de diversos extractos vegetales (10,15,16) , así como de diversas estructuras terpénicas contra uno o todos los estadíos de T. cruzi (17)(18)(19)(20) . También han mostrado efecto tripanocida algunos alcaloides (21)(22)(23) , flavonoides (24)(25)(26) , lignanos (27) y artemisininas (28) .…”

Section: Discussionunclassified

Evaluación in vitro de la actividad anti Trypanosoma cruzi de aceites esenciales de diez plantas medicinales

2011

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Objetivos: Determinar la actividad anti Trypanosoma cruzi in vitro de los aceites esenciales de 10 plantas medicinales. Además, determinar la actividad citotóxica de los aceites contra células de mamíferos y la actividad modulatoria de los aceites sobre el óxido nítrico. Diseño: Estudio experimental in vitro. Institución: Instituto de Investigaciones Clínicas e Instituto de Medicina Tropical, Facultad de Medicina, Universidad Nacional Mayor de San Marcos, Lima, Perú. Material biológico: Epimastigotes de Trypanosoma cruzi, células Raw 264.7, aceites esenciales de Mentha X piperita L (menta), Rosmarinus officinalis L (romero), Chenopodium ambrosioides L (paico), Eucaliptus globulus Labill (eucalipto), Artemisia absinthium L (ajenjo), Melissa officinalis L (toronjil), Minthostachys setosa Brig (muña), Cimbopogon citratus (hierba luisa), Aloysia triphylla (cedrón) y Mentha spicata L (hierba buena). Método: La actividad tripanocida se evaluó contra epimastigotes cultivados en medio LIT, incubados por 48 horas a 37ºC en incubador humidificado con CO2 al 5%. El cristal violeta se utilizó como control positivo. La actividad citotóxica de los productos contra células mamíferas se evaluó en células RAW 264.7 y la actividad modulatoria de los compuestos sobre óxido nítrico también se determinó en los cultivos de células RAW 264.7. Principales medidas de resultados: Porcentaje de inhibición de viabilidad y CI50. Resultados: Los aceites esenciales de Cymbopogon citratus (hierba luisa) y Aloysia triphylla (cedrón) inhibieron significativamente el crecimiento de la forma epimastigote de T. cruzi, con una CI50 de 63,09 y 96,49 μg/mL, respectivamente. No hubo variación significativa de la concentración de óxido nítrico y tampoco se evidenció citotoxicidad. Conclusiones: Los aceites esenciales de Cymbopogon citratus y Aloysia triphylla mostraron actividad anti-Trypanosoma cruzi in vitro y no fueron citotóxicas para las células mamíferas.

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Effects of canthin-6-one alkaloids from Zanthoxylum chiloperone on Trypanosoma cruzi-infected mice

Cited by 61 publications

References 14 publications

In vitro inhibition of Plasmodium falciparum by substances isolated from Amazonian antimalarial plants

In vitro inhibition of Plasmodium falciparum by substances isolated from Amazonian antimalarial plants

6-acetonyl-N-methyl-dihydrodecarine, a new alkaloid from Zanthoxylum riedelianum

Evaluación in vitro de la actividad anti Trypanosoma cruzi de aceites esenciales de diez plantas medicinales

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