In vitro studies of the anthelmintic activity of Picrolemma sprucei Hook. f. (Simaroubaceae)

Nunomura, Rita de Cássia Saraiva; Silva, Ellen Cristina Costa da; Oliveira, Denilson F.; García, Adriana; Boeloni, Jankerle Neves; Nunomura, Sergio Massayoshi; Pohlit, Adrian Martin

doi:10.1590/s0044-59672006000300006

Cited by 22 publications

(17 citation statements)

References 9 publications

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“…The antiplasmodial activity described above, especially for 1, and anthelmintic activity previously described by us for 1 and 2 lend support to traditional medicinal practice and recent ethnobotanical and ethnopharmacological studies all of which indicate the efficacy of P. sprucei (Vigneron et al 2005, Nunomura et al 2006 In general, (di)acetylated semi-synthetic quassinoid derivatives 3 and 4 displayed less in vitro cytotoxic, antiplasmodial and larvicidal activity than the natural compounds from which they were derived. The effective larvicidal activity exhibited by quassinoids underscores the need for more specific tests for the possible effects on the peritrophic matrix structure, as antifeedants, and for effects of quassinoids on other larval stages.…”

Section: Resultssupporting

confidence: 68%

“…Our group has recently demonstrated the important antimalarial activity of 2 (Andrade-Neto et al 2007), the antihelminthic activity of 1 and 2 (Nunomura et al 2006) and has written a review in which the noteworthy antileukemic, antifeedant and leishmanicidal activities of 1 were discussed (Amorim & Pohlit 2006). Kupchan et al (1975) prepared the semisynthetic quassinoid 1,12-diacetylisobrucein B (3) by acetylation of 1, but no evaluation of its biological activity has been published to date.…”

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confidence: 99%

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Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)

Silva

Cavalcanti

Amorim

et al. 2009

Mem. Inst. Oswaldo Cruz

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Section: Resultssupporting

confidence: 68%

mentioning

confidence: 99%

Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)

Silva

Cavalcanti

Amorim

et al. 2009

Mem. Inst. Oswaldo Cruz

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“…Quassinoids are a group of degraded triterpenes found in the family Simaroubaceae, that show many biological activities such as antitumor (Fukamiya et al 2005), antifeedant (Daido et al 1995), phytotoxic (De Feo et al 2003), antiviral (Apers et al 2002, and antihelmintic (Nunomura et al 2006). The antimalarial activity of some quassinoids like brusatol, glaucarubinone and quassin has been demonstrated previously (Wright 2005).…”

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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“…For example, leaf and stem infusions and other extracts have been shown to possess in vitro antihelminthic activity. 8 Also, an ethnopharmacological study in French Guiana showed that alcohol extracts of P. sprucei root, stem and bark are used in local traditional medicine as a curative treatment for malaria in association with Geissospermum spp. (Apocynaceae) and Quassia amara (Simaroubaceae) or modern drugs.…”

Section: Introductionmentioning

confidence: 99%

LC-ESI-MS determination of quassinoids isobrucein B and neosergeolide in Picrolemma sprucei stem infusions

Pohlit

Jabor

Amorim

et al. 2009

J. Braz. Chem. Soc.

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Infusões dos caules de Picrolemma sprucei (pseudônimo: P. pseudocoffea) são principalmente utilizadas como antimaláricos em toda região amazônica. Desta espécie foram isolados os quassinoides isobruceína B e neosergeolida, os quais apresentam atividade antimalárica e citotóxica. Neste estudo, apresentamos o desenvolvimento de uma metodologia analítica por LC-(+)-ESI-MS/ MS visando a determinação dos principais quassinoides desta espécie. O método desenvolvido foi empregado para análise de uma formulação artesanal (infusão de 1 g de matéria seca -caules pulverizados de P. sprucei em 1 L de água fervente). Padrões previamente isolados de isobruceína B e neosergeolida foram utilizados para a determinação da linearidade na faixa de calibração entre 0,25 to 5 µg mL -1 e 0,5 a 10 µg mL -1 , respectivamente. Como padrão interno foi utilizada a substância fluoroglucinol na concentração de 4,0 µg mL -1 . Ambos os compostos apresentaram boa linearidade, precisão e exatidão e as concentrações de isobruceína B e neosergeolida obtidas nas infusões foram de 60,1 e 774 µg L -1 , respectivamente.Infusions of the stems of Picrolemma sprucei (pseudonym: P. pseudocoffea) are used in the Amazon regions of Peru, Brazil and French Guiana as antimalarials among other uses. They contain the bitter quassinoids isobrucein B (1) and neosergeolide (2) that have important antimalarial and toxic properties among others. In this study, an LC-(+)-ESI-MS/MS method was developed and applied to the determination of 1 and 2 in a common remedy prepared by infusing 1 g of dry, powdered stems of P. sprucei in 1 L of boiling water. Isolated 1 and 2 were used in calibration ranges of 0.25 to 5 µg mL -1 and 0.5 to 10 µg mL -1 , respectively, with the internal standard phloroglucinol at 4.0 µg mL -1 . Good linearity, precision and accuracy were observed for both compounds. The concentrations of 1 and 2 in the stem infusions were found to be 60.1 and 774 µg L -1 , respectively. Recently, P. sprucei has been the subject of several studies whose results in general lend support to its uses in traditional medicine. For example, leaf and stem infusions and other extracts have been shown to possess in vitro antihelminthic activity. 8 Also, an ethnopharmacological study in French Guiana showed that alcohol extracts of P. sprucei root, stem and bark are used in local traditional medicine as a curative treatment for malaria in association with Geissospermum spp. (Apocynaceae) and Quassia amara (Simaroubaceae) or modern drugs. 5 In a subsequent study, Bertani et al. 9 demonstrated that a P. sprucei water extract can inhibit hemozoin formation and in vitro assays demonstrated the antimalarial activity of this extract against the chloroquine-resistant Plasmodium falciparum strain W2. In the western Brazilian Amazon, dried stems are commonly commercialized in local marketplaces by traditional healers or raizeiros and are typically used in the preparation of infusions for oral ingestion. KeywordsInfusions of P. sprucei contain the quassinoids isobrucein B (1) and neos...

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In vitro studies of the anthelmintic activity of Picrolemma sprucei Hook. f. (Simaroubaceae)

Cited by 22 publications

References 9 publications

Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)

Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)

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

LC-ESI-MS determination of quassinoids isobrucein B and neosergeolide in Picrolemma sprucei stem infusions

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