Further diterpenoids isolated from Pterodon polygalaeflorus

Arriaga, Ângela M. C.; Castro, Maria Augusta B. de; Silveira, Edilberto R.; Braz-Filho, Raimundo

doi:10.1590/s0103-50532000000200015

Cited by 48 publications

(57 citation statements)

References 5 publications

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“…Amentoflavone (2), agathisflavone (4), podocarpusflavone A (5) and taxifolin (6) 15 were identify by spectrometric data analysis and direct comparison with literature.…”

Section: Resultsmentioning

confidence: 99%

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Bahia¹,

David²,

David³

2010

Quím. Nova

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Recebido em 17/9/09; aceito em 2/2/10; publicado na web em 18/6/10The chloroform partition of methanol extract of leaves of Caesalpinia pyramidalis was submitted to different chromatographic procedures which afforded besides agathisflavone and taxifolin, the minor biflavones loniflavone, amentoflavone, 5'-hydroxyamentoflavone and podocarpusflavone A. The structures of the compounds were established on the basis of NMR and MS data analysis. Besides, the content of biflavones of different specimens of C. pyramidalis, which are collected in different habitats of the Brazilian semi-arid region, was determinated by LC-APCI-MS analysis. These analysis demonstrated that only the specimens harvested in Bahia state showed collectively the presence of agathisflavone, amentoflavone, sequoiaflavone and podocarpusflavone A.Keywords: Caesalpinia pyramidalis; biflavones; flavonoid analysis. INTRODUCTIONCaesalpinia pyramidalis Tul. is a tree belonging to the family Leguminosae-Caesalpinoideae, which is endemic of Brazilian northeastern, especially in the caatinga. It is popularly known as "catingueira" or "pau-de-rato" and its leaves are used in the preparation of infusions and decocts, which are used by the local population as diuretic, antidispeptic, stomach aches and for fever. 1 Species of this genus are known to present different biological activities. For instance, the extract of seeds of C. bonducella showed antimicrobial activities 2 and they are also employed in the treatment of diabetes. 3 Extracts of C. volkensii and C. pluviosa presents antimalarial activity 4 and C. pulcherrima antiviral activity. 5 The extract of C. pyramidalis is responsible for antibacterial, 6 larvicidal and moluscicidal 7 activities.The presence of diterpenes and flavonoids besides other phenolics is characteristic of this genus as well as the subfamily. 8 From the previous studies regarding with C. pyramidalis were isolated phenylpropanoids, biflavonoids, lignan, flavonoids besides gallic acid. 9 In the present study it was reported the isolation and characterization of the minor biflavonoids loniflavone (1), amentoflavone (2), 5¢-hydroxyamentoflavone (3) and podocarpusflavone A (5), besides agathisflavone (4) and taxifolin (6) from the leaves of C. pyramidalis (Figure 1). It was also evaluated by LC-MS the composition of biflavonoids present in leaves of specimens of C. pyramidalis collected in different habitats of Brazilian semi-arid region. EXPERIMENTAL General proceduresThe NMR spectra were obtained in Varian Gemini 2000, Inova 500 and Bruker AMX500 spectrometers operating at 300 and 500 MHz ( 1 H) and, 75 and 125 MHz ( 13 C), employing CD 3 OD, C 5 D 5 N and (CD 3 ) 2 CO as solvents and TMS as internal standard. The MS and the LC-MS analysis were carried out in a Shimadzu chromatographer mod. Bahia et al. 1298 Quim. Nova LCMS-2310, with autosampler 5 mL loop. The detection of biflavonoids was obtained in positive and negative APCI mode. The chromatograms were obtained using a VP-ODS (RP18 -5 mm; 3.9 x 150 mm) column and as mobile pha...

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“…Amentoflavone (2), agathisflavone (4), podocarpusflavone A (5) and taxifolin (6) 15 were identify by spectrometric data analysis and direct comparison with literature.…”

Section: Resultsmentioning

confidence: 99%

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Bahia¹,

David²,

David³

2010

Quím. Nova

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“…Dentre eles, podem ser citados os terpenóides (Yang & Liew, 1992;Camacho et al, 2000), aminoglicosteróides e aminosteróides (Kam et al, 1997), naftoquinonas (Fournet et al, 1992a;Kayser et al, 2000), chalconas (Chen et al, 1993), glicosídios iridóides (Mittal et al, 1998); flavonóides (Araújo et al, 1998), neolignanas (Barata et al, 2000) e os alcalóides (Queiroz et al, 1996;Akendengue et al, 1999;Rodríguez et al, 2008). Diversos autores identificaram alguns destes constituintes nas sementes de P. emarginatus (Braz-Filho & Gottlieb, 1971;Fascio et al, 1976;Torrenegra et al, 1989;Marques et al, 1998;Arriaga et al, 2000), por esta razão, acredita-se que a atividade leishmanicida demonstrada pelas FH e FB possa estar relacionada à presença destes compostos. …”

Section: Resultsunclassified

“…As sementes são comercializadas em mercados populares por suas propriedades farmacológicas (Leite de Almeida & Gottlieb, 1975;Arriaga et al, 2000;Agra et al, 2008).…”

Section: Introductionunclassified

“…Estudos fitoquímicos do gênero Pterodon têm demonstrado a presença de alcalóides nas cascas das árvores (Torrenegra et al, 1989), isoflavonas e alguns triterpenos (Marques et al, 1998) na madeira, e diterpenos (Fascio et al, 1976;Arriaga et al, 2000) e isoflavonas no óleo das sementes (Braz-Filho & Gottlieb, 1971). O diterpeno 14,15-epoxigeranilgeraniol e alguns derivados, isolados de P. pubenscens têm sido associado com atividade protetora contra a penetração de cercárias de S. mansoni, parasito responsável pela esquistossomose, doença tipicamente tropical (Dos Santos Filho et al, 1972).…”

Section: Introductionunclassified

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Atividades antimicrobiana e leishmanicida das sementes de Pterodon emarginatus Vogel

Dutra¹,

Braga²,

Coimbra³

et al. 2009

Rev. bras. farmacogn.

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"Antimicrobial and leishmanicidal activities of seeds of Pterodon emarginatus". The present work investigated the antimicrobial and leishmanicidal activities of seeds of Pterodon emarginatus. The tests of diffusion in agar (10, 25 and 50 mg) and determination of minimum inhibitory concentration (MIC) were performed using essential oil (EO) obtained from seeds using the standard microorganisms: Staphylococcus aureus ATCC 25923, Streptococcus mutans ATCC 25175, Pseudomonas aeruginosa ATCC 90271, Escherichia coli ATCC 10530 and Candida albicans ATCC 10231. Leishmanicidal activity of the EO and fractions (6.25 -100 μg/ml) obtained of seeds of P. emarginatus was evaluated in vitro using L. amazonensis and L. chagasi promastigote forms. The EO inhibited the growth of S. aureus (MIC = 2.5 mg/ml). The hexane (IC 50 = 50.06 µg/ ml) and butanol (IC 50 = 46.65 µg/ml) fractions showed activity against L. amazonensis promastigote forms, but did not against L. chagasi promastigote forms. The results indicate that the bioactive molecules present in the seeds of P. emarginatus can be used as prototype for the development of drug and/or as source pharmaceutical material.

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“…Furanditerpenes were identified and isolated from Pterodon fruits. [8][9][10][11] Some authors have suggested that furan-diterpenes possessing vouacapan skeleton are involved with antiinflammatory properties of Pterodon pubescens seeds´ oil. 5,12,13 Diterpenes 6α-hydroxyvouacapan-7β-17β-lactone and 6α, 7β-dihydroxyvouacapan-17β-oate methyl ester, present in P. emarginatus and P. polygalaeflorus seeds, respectively, were previously found to be associated with anti-inflammatory activity of these species.…”

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confidence: 99%

Furanoditerpenes from Pterodon pubescens benth with selective in vitro anticancer activity for prostate cell line

Spindola¹,

Carvalho²,

Ruiz³

et al. 2009

J. Braz. Chem. Soc.

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O fracionamento biomonitorado do extrato diclorometânico das sementes de Pterodon pubescens Benth forneceu o 6α-acetóxi-7β-hidróxi-vouacapano 1 (inédito), além de quatro diterpenos furânicos (2, 3, 4 e 5). A atividade antiproliferativa dos compostos foi avaliada in vitro contra as linhagens de células tumorais humanas UACC-62 (melanoma), MCF-7 (mama), NCI-H460 (pulmão), OVCAR-03 (ovário), PC-3 (próstata), HT-29 (colon), 786-0 (rim), K562 (leucemia) e NCI-ADR/RES (ovário com fenótipo de resistência a múltiplos fármacos). Os resultados foram expressos em três concentrações efetivas GI 50 (concentração para que ocorra 50% de inibição de crescimento), TGI (concentração que resulta em inibição total de crescimento) e LC 50 (concentração que resulta em 50% de morte celular). A citotoxicidade in vitro foi avaliada também frente a uma linhagem de célula murina normal (3T3). Este é o primeiro relato de atividade anticâncer para os compostos 1, 4 e 5, que apresentaram grande seletividade, dependente da concentração, para PC-3. O composto 1 foi 26 vezes mais potente para inibir 50% do crescimento (GI 50 ) de PC-3, 15 vezes mais citostático (TGI) e 6 vezes menos tóxico (LC 50 ) quando comparado com Doxorrubicina (controle).Activity guided fractionation of Pterodon pubescens Benth. methylene chloride-soluble fraction afforded novel 6α-acetoxi 7β-hydroxy-vouacapan 1 and four known diterpene furans 2, 3, 4, 5. The compounds were evaluated for in vitro cytotoxic activities against human normal cells and tumour cell lines UACC-62 (melanoma), MCF-7 (breast), NCI-H460 (lung, non-small cells), OVCAR-03 (ovarian), PC-3 (prostate), HT-29 (colon), 786-0 (renal), K562 (leukemia) and NCI-ADR/RES (ovarian expressing phenotype multiple drugs resistance). Results were expressed by three concentration dependent parameters GI 50 (concentration that produces 50% growth inhibition), TGI (concentration that produces total growth inhibition or cytostatic effect) and LC 50 (concentration that produces −50% growth, a cytotoxicity parameter). Also, in vitro cytotoxicity was evaluated against 3T3 cell line (mouse embryonic fibroblasts). Antiproliferative properties of compounds 1, 4 and 5 are herein reported for the first time. These compounds showed selectivity in a concentration-dependent way against human PC-3. Compound 1 demonstrated selectivity 26 fold more potent than the positive control, doxorubicin, for PC-3 (prostrate) cell line based on GI 50 values, causing cytostatic effect (TGI value) at a concentration fifteen times less than positive control. Moreover comparison of 50% lethal concentration (LC 50 value) with positive control (doxorubicin) suggested that compound 1 was less toxic.Keywords: Pterodon pubescens, leguminosae, furanoditerpenes, in vitro assay, prostate cell line, cytotoxicity IntoductionThroughout history, natural products have afforded a rich source of compounds that have found many applications in the fields of medicine, pharmacy and biology. Within the sphere of cancer, a number of important new commercialized drugs hav...

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Further diterpenoids isolated from Pterodon polygalaeflorus

Cited by 48 publications

References 5 publications

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Occurrence of biflavones in leaves of Caesalpinia pyramidalis specimens

Atividades antimicrobiana e leishmanicida das sementes de Pterodon emarginatus Vogel

Furanoditerpenes from Pterodon pubescens benth with selective in vitro anticancer activity for prostate cell line

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