NMR and structure review of some natural furoclerodanes

Maciel, Maria Aparecida Medeiros; Pinto, Ângelo C.; Kaiser, Carlos R.

doi:10.1002/mrc.1164

Cited by 20 publications

(32 citation statements)

References 21 publications

(21 reference statements)

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“…So the use of this compound should be used very carefully, until the study on the hepatic system in an in vivo test system has been done. On the other hand, Maciel et al (1998;2000;2003; through an extensive phytochemical research did not find any cytotoxic compound in the leaves or stem bark of Croton cajucara. According to Maciel et al (2000) ethnobotanical investigations, this Croton may not produce hepatotoxicity if used as a tea preparation to be taken at a dose of a cup twice a day during 2 to 4 weeks.…”

Section: Resultsmentioning

confidence: 90%

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Potential benefits of the 19-nor-clerodane trans-dehydrocrotonin on the central nervous system

Khan¹,

Ather²,

Pinto³

et al. 2009

Rev. bras. farmacogn.

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RESUMO: "Potenciais benefícios do 19-nor-clerodano trans-desidrocrotonina isolado deCroton cajucara sobre o sistema nervoso central". Neste estudo avaliou-se o efeito analgésico do diterpeno 19-nor-clerodano trans-desidrocrotonina (DCTN) isolado de Croton cajucara Benth (Euphorbiaceae), bem como seu efeito no sistema nervoso central utilizando-se diferentes tipos de modelos de animais roedores. A administração intraperitoneal deste diterpeno, no teste da placa quente, revelou sua atividade analgésica moderada. No entanto, no teste de contrações abdominais desencadeadas por ácido acético, a DCTN apresentou forte atividade antinociceptiva com DE 50 de 44,88 mg/kg. Doses elevadas de DCTN (100 mg/kg) apresentaram moderada atividade depressiva do sistema nervoso central (SNC), não tendo sido evidenciado ação antidepressiva. Após algumas considerações da ação de DCTN em algesia periférica, concluiu-se que esta substância pode ser utilizada como um potente agente analgésico, sem afetar o SNC. Unitermos:Croton cajucara, Euphorbiaceae, trans-desidrocrotonina, sistema nervoso central. ABSTRACT:This study examined the effect of trans-dehydrocrotonin (DCTN), a 19-norclerodane diterpene isolated from Croton cajucara Benth (Euphorbiaceae), as analgesic and its effect on the central nervous system (CNS) of rodents using different animal models. The DCTN intraperitoneally exhibited mild analgesic activity on hot-plate test, but exhibited strong antinociceptive activity against acetic acid-induced abdominal writhing and the ED 50 was calculated to be 44.88 mg/kg. At higher doses (100 mg/kg) it exhibited mild CNS depressant activities in laboratory animals. Moreover, it has negligible antidepressant activity. After taking consideration of the drug interaction, the DCTN can be used as a potent analgesic agent in case of peripheral algesia, without affecting the CNS.

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Section: Resultsmentioning

confidence: 90%

“…The pure DCTN was isolated according to previously published methodology (Maciel et al, 1998;Maciel et al, 2003), dissolved in 10% DMSO and diluted with normal saline (0.9% NaCl solution in distilled water). We used 25, 50 and 100 mg/kg doses of DCTN via the intraperitoneal (i.p.)…”

Section: The 19-nor-clerodane Dctn Doses and Route Of Administrationmentioning

confidence: 99%

Potential benefits of the 19-nor-clerodane trans-dehydrocrotonin on the central nervous system

Khan¹,

Ather²,

Pinto³

et al. 2009

Rev. bras. farmacogn.

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“…1,10,18 In addition, the common metabolites 4-hydroxy-3-methoxy-benzoic acid (vanillic acid) and 4-hydroxy-benzoic acid [0.005% in the ratio 87:13 (RMN), respectively] and an amino acid 2-methylamino-3-(4-hydroxyphenyl)-propanoic acid (0.014%, N-methyltyrosine) were isolated. The structures of vanillic acid, 4-hydroxy-benzoic acid and N-methyltyrosine were identified by spectroscopic analysis (including 300 MHz Two of the aromatic acids vanillic and 4-hydroxybenzoic acid have shown remarkable antioxidant activity in other species.…”

Section: Resultsmentioning

confidence: 99%

“…1,10,18 The semi-synthetic derivatives 6 and 7 were compared with authentic samples and shown to be identical. Aromatic acids (mixture of vanillic acid and 4-hydroxy-benzoic acid) and its derivatives 1 and 2, and also N-methyltyrosine were characterized by spectroscopic methods such as IR, UV, MS and NMR.…”

Section: Spectroscopic Data Of the Isolated And Semi-synthetic Compoundsmentioning

confidence: 99%

Natural and semi-synthetic clerodanes of Croton cajucara and their cytotoxic effects against ehrlich carcinoma and human K562 leukemia cells

Maciel¹,

Martins²,

Pinto³

et al. 2007

J. Braz. Chem. Soc.

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O diterpeno clerodano trans-desidrocrotonina (1), constituinte majoritário de Croton cajucara, tem sua ocorrência correlacionada com o uso dessa planta na medicina popular. Investigações fitoquímicas levaram ao isolamento dos metabólitos 1, cajucarinolida (6), isocajucarinolida (7), trans-crotonina (2), trans-cajucarina B (3), cis-cajucarina B (4), transcajucarina A (5), N-metiltirosina, ácido vanílico e ácido 4-hidróxi-benzóico. 6 e 7 foram sintetizados em bons rendimentos através da oxidação de 1 com oxigênio-singlete. Todos os clerodanos foram ensaiados frente a células da leucemia humana K562 e do carcinoma de Ehrlich. Os efeitos inibitórios do crescimento celular foram dependentes da dose para os ensaios com o carcinoma de Ehrlich com IC 50 = 166 μM (1), 164 μM (2), 65 μM (6) e 10 μM (7). Além disso, atividade citotóxica moderada foi observada contra as células da leucemia K562 com IC 50 = 38 μM (3), 33 μM (5), 36 μM (6) e 43 μM (7). Os 6 e 7 semi-sintéticos mostraram resultados semelhantes quando comparados com os correspondentes clerodanos naturais.The clerodane-type diterpene, trans-dehydrocrotonin (1) the major component of Croton cajucara has shown striking correlation with its therapeutic use in traditional folk medicine. Phytochemical investigations led to the isolation of the metabolites 1, cajucarinolide (6), isocajucarinolide (7), trans-crotonin (2), trans-cajucarin B (3), cis-cajucarin B (4), trans-cajucarin A (5), N-methyltyrosine, vanillic acid and 4-hydroxy-benzoic acid. 6 and 7 were synthesized in good yield by regiospecific oxidation of 1 using singlet-oxygen. All clerodanes were studied for their cytotoxic effects against human K562 leukemia and Ehrlich carcinoma cells. Ehrlich carcinoma assays with IC 50 = 166 μM (1), 164 μM (2), 65 μM (6) and 10 μM (7) related to cell growth inhibitory effects were dose dependent. Furthermore, moderate cytotoxic activity against K562 leukemia cells was observed with IC 50 = 38 μM (3), 33 μM (5), 36 μM (6) and 43 μM (7). The semi-synthetic 2, 6 and 7 showed similar results when compared to the corresponding natural clerodanes.

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“…Estes estudos mostraram que as cascas do caule são ricas em diterpenos do tipo clerodano, tendo sido isolados: trans-desidrocrotonina (DCTN), transcrotonina (CTN), cis-cajucarina B, trans-cajucarina B, cajucarina A, cajucarinolida, isocajucarinolida, isosacacarina e o triterpeno ácido acetilaleuritólico (AAA) (Maciel et al, 1998b;Maciel et al, 2003).…”

Section: Introductionunclassified

Uma revisão das atividades biológicas da trans-desidrocrotonina, um produto natural obtido de Croton cajucara

Costa¹,

Magalhães²,

Gomes³

et al. 2007

Rev. bras. farmacogn.

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RESUMO:Croton cajucara Beth (Euphorbiaceae) uma espécie medicinal nativa da região Amazônica do Brasil, onde é vulgarmente conhecida como 'sacaca', representa um recurso terapêutico efi caz no tratamento e cura de várias doenças. O metabólito majoritário transdesidrocrotonina (DCTN), isolado das cascas do caule desta planta, encontra-se correlacionado com grande parte das propriedades medicinais da sacaca. Este artigo de revisão, descreve os resultados fi toquímicos e farmacológicos que foram realizados com o diterpeno do tipo clerodano DCTN, bem como seus derivados semi-sintéticos. Adicionalmente, apresenta perspectivas para a biodisponibilização deste protótipo de fármaco em nanosistemas. Unitermos:Croton cajucara, trans-desidrocrotonina, DCTN, fi toquímica, atividade biológica, nanobiotecnologia.ABSTRACT: "A review of the biologic activities of trans-dehydrocrotonin, a natural product obtained from Croton cajucara". Croton cajucara Beth (Euphorbiaceae) is a plant found in the Amazonian Region of North Brazil, where it is popularly known as sacaca. The major secondary metabolite, trans-dehydrocrotonin (DCTN) a clerodane-type diterpene, isolated from the stem bark is a chief bioactive compound of Croton cajucara. This review describes results of extensive pharmacological studies of DCTN, as well as its semi-synthetic derivatives, and also presents insights into the use of DCTN as a therapeutic agent and some potential advantages of its incorporation in drug delivery systems.

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NMR and structure review of some natural furoclerodanes

Cited by 20 publications

References 21 publications

Potential benefits of the 19-nor-clerodane trans-dehydrocrotonin on the central nervous system

Potential benefits of the 19-nor-clerodane trans-dehydrocrotonin on the central nervous system

Natural and semi-synthetic clerodanes of Croton cajucara and their cytotoxic effects against ehrlich carcinoma and human K562 leukemia cells

Uma revisão das atividades biológicas da trans-desidrocrotonina, um produto natural obtido de Croton cajucara

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