Gram-scale isolation of isobrucein B and neosergeolide from Picrolemma sprucei Hook. f.

Silva, Ellen Cristina Costa da; Amorim, Rodrigo César das Neves; Tadei, Wanderli Pedro; Pohlit, Adrian Martin

doi:10.1590/s0044-59672009000100026

Cited by 7 publications

(6 citation statements)

References 11 publications

(10 reference statements)

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“…A detailed procedure for extraction and isolation of 1 on a gram scale has been previously published. 44 Briefly, this procedure consists of pilot-scale degreasing by Soxhlet extraction with hexanes of the dried, ground roots and stems of P. sprucei. The plant materials were further extracted with water in a Soxhlet apparatus.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

The Quassinoid Isobrucein B Reduces Inflammatory Hyperalgesia and Cytokine Production by Post-transcriptional Modulation

et al. 2015

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Isobrucein B (1) is a quassinoid isolated from the Amazonian medicinal plant Picrolemma sprucei. Herein we investigate the anti-inflammatory and antihyperalgesic effects of this quassinoid. Isobrucein B (1) (0.5-5 mg/kg) inhibited carrageenan-induced inflammatory hyperalgesia in mice in a dose-dependent manner. Reduced hyperalgesia was associated with reduction in both neutrophil migration and pronociceptive cytokine production. Pretreatment with 1 inhibited in vitro production/release of cytokines TNF, IL-1β, and KC/CXCL1 by lipopolysaccharide-stimulated macrophages. To investigate its molecular mechanism, RAW 264.7 macrophages with a luciferase reporter gene controlled by the NF-κB promoter were used (RAW 264.7-Luc). Quassinoid 1 reduced the luminescence emission by RAW 264.7-Luc stimulated by different compounds. Unexpectedly, NF-κB translocation to macrophage nuclei was not inhibited by 1 when evaluated by Western blotting and immunofluorescence. Furthermore, quassinoid 1 did not change the levels of TNF mRNA transcription in stimulated macrophages, suggesting post-transcriptional modulation. In addition, constitutive expression of luciferase in RAW 264.7 cells transiently transfected with a plasmid containing a universal promoter was inhibited by 1. Thus, isobrucein B (1) displays anti-inflammatory and antihyperalgesic activities by nonselective post-transcriptional modulation, resulting in decreased production/release of pro-inflammatory cytokines and neutrophil migration.

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Section: ■ Results and Discussionmentioning

confidence: 99%

The Quassinoid Isobrucein B Reduces Inflammatory Hyperalgesia and Cytokine Production by Post-transcriptional Modulation

et al. 2015

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“…Ultrapure water, obtained from a Milli-Q Plus System (Millipore, Bedford, MA, USA), was used in all analyses. 1 and 2 were isolated from P. sprucei as described previously 11,19 and used as reference standards. Their identity and purity were established based on 1D and 2D NMR, IR, HR-ESI-TOF-MS, HPLC-DAD and LC-ESI-MS analyses and comparison to literature data.…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

“…These compounds have been isolated previously from the stems and roots of P. sprucei on a milligram scale 10 and more recently on a gram-scale. 11 Also, 1 has been isolated from the leaves of this plant. 12 Recently, the antimalarial, antileukemic, antifeedant and leishmanicidal activities of 1 were the subject of a review.…”

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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“…Several studies show promising results for the antiplasmodial activity of the family Simaroubaceae against P. falciparum species . More specifically, it was found that the quasinoides simalikalactone E and D, eurycomanone, isobrucein B, among others, are the most active metabolites present in these plants [ 38 , 39 , 42 – 44 ]. This group of active metabolites is considered a taxonomic marker of this plant family, since it is the most abundant group of natural metabolites that they possess and their synthesis is almost exclusive compared to other plant families.…”

Section: Discussionmentioning

confidence: 99%

“…Numerous compounds have been isolated from this family, such as quassinoids, alkaloids, triterpenes, steroids, coumarins, anthraquinones, flavonoids and other metabolites [ 55 – 58 ]. Most of the studies reported for the Simaroubaceae family show antiplasmodial activity for the quassinoids extracted from these plants [ 35 , 38 – 40 , 42 , 44 ], with characteristics of highly active compounds [ 20 ]. Quassinoids such as isobrucein B and sergolides isolated from P. huberi extracts have only been evaluated in a melanoma cell line, and in colon and lung cell lines, with sergolide having a higher cytotoxicity CC 50 in a range of 10 −7 –10 −8 M [ 45 ].…”

Section: Discussionmentioning

confidence: 99%

Anti-plasmodial effect of plant extracts from Picrolemma huberi and Picramnia latifolia

Berthi

González

Ríos

et al. 2018

Malar J

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BackgroundMalaria is an infectious disease caused by parasites of the genus Plasmodium, of which Plasmodium vivax and Plasmodium falciparum are the major species that cause the disease in humans. As there are relatively few alternatives for malaria treatment, it is necessary to search for new chemotherapeutic options. Colombia possesses a great diversity of plants, which are potential sources of new compounds of medical interest. Thus, in this study the antiplasmodial effect of extracts from two species of plants from the families Simaroubaceae and Picramniaceae (Picramnia latifolia and Picrolemma huberi) was evaluated in vitro and in vivo. These plants were chosen because they contain secondary metabolites with interesting medicinal effects.ResultsThe ethanolic extracts of both species were highly active with IC50: 1.2 ± 0.19 µg/mL for P. latifolia and IC50: 0.05 ± 0.005 µg/mL for P. huberi. The P. latifolia extract had a stage specific effect on trophozoites and inhibited parasite growth in vivo by 52.1 ± 3.4%, evaluated at 1000 mg/kg in Balb/c mice infected with Plasmodium berghei. On the other hand, evaluated at 150 mg/kg body weight in the same murine model, the ethanolic extract from P. huberi had an antiplasmodial effect in all the asexual intraerythrocytic stages of P. falciparum FCR3 and inhibited the parasitic growth in 93 ± 32.9%.ConclusionsThis is the first report of anti-malarial activity for these two species of plants. Thus, P. latifolia and P. huberi are potential candidates for the development of new drugs for treating malaria.

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Gram-scale isolation of isobrucein B and neosergeolide from Picrolemma sprucei Hook. f.

Cited by 7 publications

References 11 publications

The Quassinoid Isobrucein B Reduces Inflammatory Hyperalgesia and Cytokine Production by Post-transcriptional Modulation

The Quassinoid Isobrucein B Reduces Inflammatory Hyperalgesia and Cytokine Production by Post-transcriptional Modulation

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

Anti-plasmodial effect of plant extracts from Picrolemma huberi and Picramnia latifolia

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