Antiproliferative activity of Pterodon pubescens Benth. seed oil and its active principle on human melanoma cells

Vieira, Cíntia Ribeiro Manhães; Marques, M.F.; Soares, Paula Roberta Otaviano; Matuda, Larissa; Oliveira, Cecília Maria Alves de; Kato, Lucília; Silva, C.C. da; Guillo, Lidia Andreu

doi:10.1016/j.phymed.2007.08.003

Cited by 29 publications

(39 citation statements)

References 11 publications

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“…In this same study, the subfraction A (fractionation by gradient elution with hexane/ethyl acetate-80:20) caused morphological features and internucleosomal DNA fragmentation pattern of apoptosis (Vieira et al, 2008). These results have led authors to conclude that diterpenoids vouacapan-type skeleton could be used as a model to develop new anticancer agents.…”

Section: Introductionmentioning

confidence: 75%

“…A previous report showed the toxicity of seed's oil of a synonymy species P. pubescens on PBMC, and the authors found a cytotoxic effect with IC50 2.0 μg/mL for these cells (Sabino et al, 1999). Very recently, an interesting study conducted by Vieira et al (2008) has demonstrated the cytotoxicity, morphological and biochemical alterations on human melanoma cells (cell line SK MEL 37) induced by vouacapan-derived compound isolated from EO of P. pubescens seeds. These results have led authors to conclude that diterpenoids vouacapan could be used as a model to develop new anticancer agents.…”

Section: Resultsmentioning

confidence: 96%

“…Recently, Vieira et al (2008) showed the crude ethanolic extract and furane diterpene, isolated from P. pubescens seeds, inhibited human melanoma cell line SK MEL cell growth. In this same study, the subfraction A (fractionation by gradient elution with hexane/ethyl acetate-80:20) caused morphological features and internucleosomal DNA fragmentation pattern of apoptosis (Vieira et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

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Chemical composition and cytotoxicity activity of the essential oil of Pterodon emarginatus

Dutra¹,

Pittella²,

Dittz³

et al. 2012

Rev. bras. farmacogn.

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Pterodon emarginatus Vogel, Fabaceae, is a native aromatic tree distributed by central region of Brazil. Hydroalcoholic infusions of the seeds are used in folk medicine for their anti-rheumatic and anti-inflammatory properties. The objective of this work was identified the chemical components and verify the cytotoxic effect of the essential oil (EO) from P. emarginatus seeds. Thus, the EO of P. emarginatus seeds was analyzed by GC/MS analysis followed by brine shrimp lethality test and cytotoxic activity against tumor cell lines and human peripheral mononuclear blood cells (PBMC). The cancer cell lines tested were C 6 (rat glioma), MeWo (human melanoma), CT 26 .WT (mouse colon carcinoma), MDA (human breast cancer), A 549 (human lung carcinoma), B 16 -F 1 (mouse melanoma), CHO-K1 (hamster ovary cell) and BHK-21 (hamster kidney fibroblast). Eleven compounds were identified by GC and CG/MS analyses. The main compounds with concentrations higher than 5% were β-elemene (15.3%), trans-caryophyllene (35.9%), α-humulene (6.8%), germacrene-D (9.8%), bicyclo germacrene (5.5%) and spathulenol (5.9%). The EO of P. emarginatus seeds showed toxicity to Artemia salina (LC50 1.63 μg/mL) and was active against all the cell lines tested. The potent cytotoxic activity had IC50 values ranging from 24.9 to 47 μg/mL. However, EO (1-100 µg/mL) had less cytotoxicity in PBMCs isolated from a healthy subject. In summary, the present study showed the potential antiproliferative of the EO of P. emarginatus seeds.

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Section: Introductionmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

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Chemical composition and cytotoxicity activity of the essential oil of Pterodon emarginatus

Dutra¹,

Pittella²,

Dittz³

et al. 2012

Rev. bras. farmacogn.

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“…The oil extracted from the fruit of the Pterodon sp. has been shown to have several pharmacological properties including anticancer, antinociceptive, and anti-inflammatory activity, and has been studied mainly for its effects on arthritis (Carvalho et al, 1999;Coelho et al, 2005;Vieira et al, 2008;Hoscheid et al, 2013). The raw oil extract is difficult to use in pharmaceutical preparations without protection of its lipophilic constituents, which are easily oxidized by exposure to air and light.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of microcapsules of Pterodon pubescens Benth. by using natural polymers

Reinas¹,

Hoscheid²,

Outuki³

et al. 2014

Braz. J. Pharm. Sci.

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An oleaginous fraction obtained from an alcohol extract of the fruit of Pterodon pubescens Benth. (FHPp) was microencapsulated in polymeric systems. These systems were developed using a complex coacervation method and consisted of alginate/medium-molecular-weight chitosan (F1-MC), alginate/ chitosan with greater than 75% deacetylation (F2-MC), and alginate/low-molecular-weight chitosan (F3-MC). These developed systems have the potential to both mask the taste of the extract, and to protect its constituents against possible chemical degradation. The influence of the formulation parameters and process were determined by chemical profiling and measurement of the microencapsulation efficiency of the oleaginous fraction, and by assessment of microcapsule morphology. The obtained formulations were slightly yellow, odorless, and had a pleasant taste. The average diameters of the microcapsules were 0.4679 µm (F2-MC), 0.5885 µm (F3-MC), and 0.9033 µm (F1-MC). The best formulation was F3-MC, with FHPp microencapsulation efficiency of 61.01 ± 2.00% and an in vitro release profile of 75.88 ± 0.45%; the content of vouacapans 3-4 was 99.49 ± 2.80%. The best model to describe the release kinetics for F1-MC and F3-MC was that proposed by Higuchi; however, F2-MC release displayed firstorder kinetics; the release mechanism was of the supercase II type for all formulations.Uniterms: Pterodon pubescens Benth./pharmacognosy. Sucupira. Microcapsules/preparation. Vouacapans. Alginate. Chitosan. Coacervation method. Natural polymers. Natural products.Uma fração oleaginosa obtida do extrato etanólico de frutos de Pterodon pubescens Benth (FHPp) foi microencapsulada em um sistema polimérico. Estes sistemas foram desenvolvidos utilizando o método de coacervação complexa, constituído de alginato/quitosana massa molecular média (F1-MC), alginato/ quitosana com desacetilação superior a 75% (F2-MC) e alginato/quitosana de massa molecular baixa (F3-MC). Estes sistemas desenvolvidos têm o potencial tanto de mascarar o sabor do extrato, quanto de protegê-lo de possível degradação química. A influência dos parâmetros de formulação e processo foram determinadas por caracterização química, determinação da eficiência de microencapsulação da fração oleaginosa e por avaliação morfológica da microcápsula. As formulações mostraram-se ligeiramente amareladas, inodoras e com sabor agradável. Os diâmetros médios das microcápsulas foram de 0,4679 µm (F2-MC), 0,5885 µm (F3-MC) e 0,9033 µm (F1-MC). A melhor formulação foi F3-MC, considerando-se que apresentou eficiência de encapsulação de 61,01 ± 2,00%, e perfil de liberação in vitro de 75,88 ± 0,45%; o conteúdo dos vouacapanos 3-4 foi 99,49 ± 2,80%. O melhor modelo para descrever a cinética de liberação foi o modelo proposto por Higuchi para F1-MC e F3-MC, entretanto, para F2-MC foi o modelo de primeira ordem, e o mecanismo de liberação foi do tipo super caso II para todas as formulações.Unitermos: Pterodon pubescens Benth./farmacognosia. Sucupira. Microcápsulas/preparação. Vouacapanos. Alginato. Quitosana. ...

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“…[3][4][5][6][7] Authors have reported that furanoditerpenes possessing vouacapan skeleton are involved with the anti-inflammatory, antinociceptive and antiproliferative properties of Pterodon pubescens seed crude extract. [7][8][9][10][11][12] We previously reported the antinociceptive properties of geranylgeraniol and 6α,7β-dihydroxy-vouacapan-17β-oate methyl ester, compounds isolated from Pterodon pubescens Vol. 23, No.…”

Section: Introductionmentioning

confidence: 99%

Pterodon pubescens Benth: Stability study of microencapsulated extract and isolated compounds monitored by antinociceptive assays

Servat¹,

Spindola²,

Rodrigues³

et al. 2012

Planta Med

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As sementes de Pterodon pubescens Benth. (Pp), disponíveis comercialmente no Brasil, são utilizadas na medicina popular em preparações anti-inflamatórias, analgésicas e anti-reumáticas. O presente estudo demonstrou as propriedades antinociceptivas da mistura de isômeros 6α-hidroxi-7β-acetoxi-vouacapano-17β-oato de metila e 6α-acetoxi-7β-hidroxi-vouacapano-17β-oato de metila (C1) isolada de Pp, empregando modelos experimentais diferentes. Um estudo de estabilidade foi realizado para investigar a relação da microencapsulação por "spray-drying" na manutenção do efeito antinociceptivo. Para isso, amostras de C1 e extrato de Pp foram monitorados no estudo de estabilidade acelerada, avaliando tanto amostras microencapsuladas como não microencapsuladas. Foi observado que a amostra C1 possui atividade antinociceptiva, revelada pelos ensaios das contorções abdominais e de formalina; foi observada também atividade significativa antialodínica, mas não efeito anti-hiperalgésico. A microencapsulação manteve a atividade e integridade de C1 e do extrato bruto de Pp, demonstrando que a microencapsulação por "spray drying" é uma alternativa útil para aumentar o tempo de prateleira.Pterodon pubescens Benth. (Pp) seeds, commercially available in Brazil, are used in folk medicine in anti-inflammatory, analgesic, and anti-rheumatic preparations. The present study demonstrated the antinociceptive properties of isomers 6α-hydroxy-7β-acetoxy-vouacapan-17β-oate methyl ester and 6α-acetoxy-7β-hydroxy-vouacapan-17β-oate methyl ester (C1), isolated from (Pp), employing different experimental models. A stability study was performed to investigate the relationship of microencapsulation by spray-drying on the maintenance of antinociceptive action. Therefore, C1 and Pp extract samples were monitored in accelerated stability study, evaluating both microencapsulated and non-microencapsulated samples. It was observed that sample C1 possess antinociceptive activity revealed by writhing and formalin tests; C1 showed significantly anti-allodynic, but not antihyperalgesic effect; the microencapsulation maintained the activity and integrity of both, sample C1 and Pp crude extract; microencapsulation by spray drying is a useful alternative to increase shelf life. Keywords: microcapsules, stability, spray-drying, antinociceptive, Pterodon pubescens IntroductionPterodon pubescens Benth. (Leguminosae) seeds are commercially available in Brazil. The plant's crude alcoholic extract is used in folk medicine in antiinflammatory, analgesic, and anti-rheumatic preparations. 1,2 Phytochemical studies of Pterodon genus have revealed the presence of alkaloids, isoflavones and diterpenes. Furan diterpenes were identified and isolated from Pterodon species. [3][4][5][6][7] Authors have reported that furanoditerpenes possessing vouacapan skeleton are involved with the anti-inflammatory, antinociceptive and antiproliferative properties of Pterodon pubescens seed crude extract. [7][8][9][10][11][12] We previously reported the antinociceptive properties of geranylgerani...

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Antiproliferative activity of Pterodon pubescens Benth. seed oil and its active principle on human melanoma cells

Cited by 29 publications

References 11 publications

Chemical composition and cytotoxicity activity of the essential oil of Pterodon emarginatus

Chemical composition and cytotoxicity activity of the essential oil of Pterodon emarginatus

Preparation and characterization of microcapsules of Pterodon pubescens Benth. by using natural polymers

Pterodon pubescens Benth: Stability study of microencapsulated extract and isolated compounds monitored by antinociceptive assays

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