FEITOSA, C. R. S. Contribuição ao Conhecimento Químico - Farmacológico de Plantas do Nordeste do Brasil: Luffa operculata Cogn. 2011. 287 f. Tese (Doutorado em Química) - Centro de Ciências, Universidade Federal do Ceará, Fortaleza, 2011. / Submitted by José Jairo Viana de Sousa (jairo@ufc.br) on 2014-11-04T18:06:41Z No. of bitstreams: 1 2011_tese_crsfeitosa.pdf: 14700049 bytes, checksum: d9b543e17db1678a5942e5ae87fd255a (MD5) / Approved for entry into archive by José Jairo Viana de Sousa(jairo@ufc.br) on 2015-04-20T21:04:09Z (GMT) No. of bitstreams: 1 2011_tese_crsfeitosa.pdf: 14700049 bytes, checksum: d9b543e17db1678a5942e5ae87fd255a (MD5) / Made available in DSpace on 2015-04-20T21:04:09Z (GMT). No. of bitstreams: 1 2011_tese_crsfeitosa.pdf: 14700049 bytes, checksum: d9b543e17db1678a5942e5ae87fd255a (MD5) Previous issue date: 2011 / Luffa operculata (Cucurbitaceae) is a plant widely distributed in Northeastern Brazil, where is known as “cabacinha”. An aqueous solution from the fruit of “cabacinha” has been popularly used for the treatment of sinusitis as a bitter stomachic and purgative remedy. The broad spectrum of pharmacological effects reported in the literature and the abundance of this plant in rural Northeastern Brazil justified this study. The plant was subjected to phytochemical study with the objective of isolation and characterization of their secondary metabolites. The Cucurbitaceae are characteristically rich in cucurbitacins, which are oxidative modified triterpenes that together with their glycosides counterparts are considered the agents responsible for the potent toxicity observed in extracts of the fruit of Luffa operculata. Through various chromatographic steps the elements were purified and isolated. The ethanol extract of the fruit of Luffa operculata yielded the isolation of six triterpenoids (cucurbitacin D, isocucurbitacin D, 3-epi-isocucurbitacin D, cucurbitacin I, cucurbitacin B and arvenin I). The ethanol extract of the stems yielded two quinones (emodine and chrisophanol), as well as a mixture of aliphatic esters (hexadecanoic acid, ethyl ester and octadecanoic acid, ethyl ester) and one rare triterpene friedolenane type (bryonolic acid). Furthermore, a mixture of steroids [(22E, 24S)-ethyl-5α-cholest-7,22-dien-3β-ol and (22E,24R)-ethyl-5α-cholest-7,22,25-trien-3β-ol]; ceramides (1,3,4-trihydroxy-2-[2´-hydroxydocosanoylamino]-19-tetracasadecene and 1,3,4-tryhydroxy-2-[2´-hydroxyhenicosanoylamino]-19-tetracasadecene) were isolated from the ethanol extract of the fruit bark. Meanwhile, a mixture of steroids was isolated from the hexane extract of the leaves [(22E, 24S)-ethyl-5α-cholest-7,22-dien-3β-ol and (22E,24R)-ethyl-5α-cholest-7,22,25-trien-3β-ol), while the hexane extract of the stems yielded one steroid (spinasterol) and a mixture of ceramides [(N-(2-isopropoxy-ethyl)eicosamide, N-(2-isopropoxy-ethyl)nonadecanamide, N-(2-isopropoxy-ethyl)octadacanamide, N-(2-isopropoxy-ethyl)heptadacanamide, N-(2-isopropoxy-ethyl)hexadecanamide]. In order to provide training activities in the laboratory and to collect structural proof of the extracts, several derivatives were prepared by classical reactions such as oxidation, esterification, hydrolysis and methanolysis. In addition, crude extracts and a few of the isolated natural products were assessed for biological activities. Some of the compounds found were described for the first time from Luffa opeculata, while the ceramides isolated from the extract are new to the literature. The 1H and 13C NMR, IV and MS spectra and a comparison with previous spectral data allowed the research team to fully understand the chemical structure of all compounds.

FundaÃÃo Cearense de Apoio ao Desenvolvimento Cientifico e TecnolÃgico / Luffa operculata (Cucurbitaceae) is a plant widely distributed in Northeastern Brazil, where is known as âcabacinhaâ. An aqueous solution from the fruit of âcabacinhaâ has been popularly used for the treatment of sinusitis as a bitter stomachic and purgative remedy. The broad spectrum of pharmacological effects reported in the literature and the abundance of this plant in rural Northeastern Brazil justified this study. The plant was subjected to phytochemical study with the objective of isolation and characterization of their secondary metabolites. The Cucurbitaceae are characteristically rich in cucurbitacins, which are oxidative modified triterpenes that together with their glycosides counterparts are considered the agents responsible for the potent toxicity observed in extracts of the fruit of Luffa operculata. Through various chromatographic steps the elements were purified and isolated. The ethanol extract of the fruit of Luffa operculata yielded the isolation of six triterpenoids (cucurbitacin D, isocucurbitacin D, 3-epi-isocucurbitacin D, cucurbitacin I, cucurbitacin B and arvenin I). The ethanol extract of the stems yielded two quinones (emodine and chrisophanol), as well as a mixture of aliphatic esters (hexadecanoic acid, ethyl ester and octadecanoic acid, ethyl ester) and one rare triterpene friedolenane type (bryonolic acid). Furthermore, a mixture of steroids [(22E, 24S)-ethyl-5α-cholest-7,22-dien-3β-ol and (22E,24R)-ethyl-5α-cholest-7,22,25-trien-3β-ol]; ceramides (1,3,4-trihydroxy-2-[2Â-hydroxydocosanoylamino]-19-tetracasadecene and 1,3,4-tryhydroxy-2-[2Â-hydroxyhenicosanoylamino]-19-tetracasadecene) were isolated from the ethanol extract of the fruit bark. Meanwhile, a mixture of steroids was isolated from the hexane extract of the leaves [(22E, 24S)-ethyl-5α-cholest-7,22-dien-3β-ol and (22E,24R)-ethyl-5α-cholest-7,22,25-trien-3β-ol), while the hexane extract of the stems yielded one steroid (spinasterol) and a mixture of ceramides [(N-(2-isopropoxy-ethyl)eicosamide, N-(2-isopropoxy-ethyl)nonadecanamide, N-(2-isopropoxy-ethyl)octadacanamide, N-(2-isopropoxy-ethyl)heptadacanamide, N-(2-isopropoxy-ethyl)hexadecanamide]. In order to provide training activities in the laboratory and to collect structural proof of the extracts, several derivatives were prepared by classical reactions such as oxidation, esterification, hydrolysis and methanolysis. In addition, crude extracts and a few of the isolated natural products were assessed for biological activities. Some of the compounds found were described for the first time from Luffa opeculata, while the ceramides isolated from the extract are new to the literature. The 1H and 13C NMR, IV and MS spectra and a comparison with previous spectral data allowed the research team to fully understand the chemical structure of all compounds. / Luffa operculata(Cucurbitaceae) is a plant widely distributed in Northeastern Brazil, where is known as âcabacinhaâ. An aqueous solution from the fruit of âcabacinhaâ has been popularly used for the treatment of sinusitis as a bitter stomachic and purgative remedy. The broad spectrum of pharmacological effects reported in the literature and the abundance of this plant in rural Northeastern Brazil justified this study. The plant was subjected to phytochemical study with the objective of isolation and characterization of their secondary metabolites. The Cucurbitaceae are characteristically rich in cucurbitacins, which are oxidative modified triterpenes that together with their glycosides counterparts are considered the agents responsible for the potent toxicity observed in extracts of the fruit of Luffa operculata. Through various chromatographic steps the elements were purified and isolated. The ethanol extract of the fruit of Luffa operculata yielded the isolation of six triterpenoids (cucurbitacin D, isocucurbitacin D, 3-epi-isocucurbitacin D, cucurbitacin I, cucurbitacin B and arvenin I). The ethanol extract of the stems yielded two quinones (emodine and chrisophanol), as well as a mixture of aliphatic esters (hexadecanoic acid, ethyl ester and octadecanoic acid, ethyl ester) and one rare triterpene friedolenane type (bryonolic acid). Furthermore, a mixture of steroids [(22 E , 24S) - ethyl - 5 α - cholest - 7,22 - dien - 3 β - ol and (22 E ,24R) - ethyl - 5 α - cholest - 7,22,25 - trien - 3 β - ol]; ceramides (1,3,4-trihydroxy-2- [2 ́ - hydroxydocosanoylamino] - 19 - tetracasadecene and 1,3,4-tryhydroxy - 2 - [2 ́ - hydroxyhenicosanoylamino] - 19 - tetracasadecene) were isolated from the etha nol extract of the fruit bark. Meanwhile, a mixture of steroids was isolated from the hexane extract of the leaves [(22 E , 24S) - ethyl - 5 α - cholest - 7,22 - dien - 3 β - ol and (22 E ,24R) - ethyl - 5 α - cholest - 7,22,25 - trien - 3 β - ol), while the hexane extract of the stems yield ed one steroid (spinasterol) and a mixture of ceramides [(N-(2-isopropoxy-ethyl)eicosamide, N - (2 - isopropoxy - ethyl)nonadecanamide, N - (2 - isopropoxy - ethyl)octadacanamide, N-(2-isopropoxy - ethyl)heptadacanamide, N-(2-isopropoxy-ethyl)hexadecanamide]. In order to provide training activities in the laboratory and to collect structural proof of the extracts, several derivatives were prepared by classical reactions such as oxidation, esterification, hydrolysis and methanolysis. In addition, crude extracts and a few of the isolated natural products were assessed for biological activities. Some of the compounds found were described for the first time from Luffa opeculata, while the ceramides isolated from the extract are new to the literature. The1H and 13C NMR, IV an d MS spectra and a comparison with previous spectral data allowed the research team to fully understand the chemical structure of all compounds.

Made available in DSpace on 2014-06-12T16:28:51Z (GMT). No. of bitstreams: 2 arquivo2099_1.pdf: 1951167 bytes, checksum: 9614824fbab0545912a211d54ee0c730 (MD5) license.txt: 1748 bytes, checksum: 8a4605be74aa9ea9d79846c1fba20a33 (MD5) Previous issue date: 2008 / O uso de plantas no tratamento e na cura de enfermidades é tão antigo quanto à espécie humana. Luffa operculata Cogn. é nativa da América do Sul especialmente do Brasil, podendo ser encontrada amplamente distribuída em Pernambuco, Bahia, Minas Gerais , Rio de Janeiro e Ceará. Trata-se de uma planta angiosperma e dicotiledônea da família Cucurbitaceae, popularmente conhecida como buchinina, cabaçinha, purga-de-jalapa e purga-dos-paulistas. Sendo empregada na medicina popular tradicional principalmente para o tratamento de sinusite, rinite e com descongestionante nasal. O trabalho teve como objetivo avaliar a toxicidade aguda, atividade farmacológica (anti-tumoral em roedores) e microbiologia do extrato bruto de Luffa operculata Cogn. Foram realizados ensaios de toxicidade aguda por via intraperitoneal com observações comportamentais para cada dose administrada. Inicialmente foram observados efeitos estimulantes seguido de efeitos depressores do Sistema Nervoso Central. A DL50 determinada por via intraperitoneal foi de 3,3 mg/kg considerada muito tóxica. Na avaliação anti-tumoral de Luffa operculata Cogn. frente ao Sarcoma 180, células tumorais foram implantadas em camundongos Swiss (Mus musculus) fêmeas sadias. Os animais divididos em grupos de seis, foram tratados com solução fisiológica 0,9%, metotrexato (10 mg/kg) e do extrato bruto de Luffa operculata Cogn. nas doses de 0,3; 0,6 e 1,0 mg/kg. Os animais tratados coma maior dose do extrato obtiveram índice de inibição significativa de 61,7% quando comparado com o grupo controle. Para os animais tratados com metotrexato (10 mg/kg) a inibição foi de 95,4%. Na análise microbiológica foram realizadas avaliações das atividades antimicrobiana da Luffa operculata Cogn. contra espécimes bacterianas e fúngicas da origem clínica e de coleção. Os ensaios foram realizados, através do método de difusão em meio sólido, incubados em uma temperatura de 35±2º C durante 24-48 horas para espécimes bacterianas, e 28±30 durante 4-14 dias para espécies fônicas. Os resultados demonstraram que o extrato de Lufa operculata Cogn. apresenta a atividade antimicrobiana contra Staphylococcus aureus e Staphylococcus epidermidis, Candida albicans e Candida tropicalis. Embora seja considerada muito tóxica a Luffa operculata apresentou inibição tumoral em neoplasias maligna em tumor de tecido conjuntivo com perspectivas para novas investigações em outros processos neoplásicos

Luffa operculata é uma planta medicinal popularmente usada para tratamento de rinites e rinossinusites. A infusão de seu fruto seco é usada no nariz, liberando secreção mucosa profusa, mas pode causar irritação, epistaxe ou anosmia. Avaliamos os efeitos de diferentes concentrações da infusão do fruto seco da Luffa operculata na velocidade de transporte mucociliar (VTM), freqüência de batimento ciliar (FBC), diferença de potencial transepitelial (DPT) e morfologia do epitélio (microscopia de luz e eletrônica de transmissão), no modelo do palato isolado de rã. Os resultados apontam para dano epitelial dose-dependente no epitélio mucociliar, sugerindo que ela seja potencialmente nociva à mucosa nasal humana / Luffa operculata is a medicinal plant popularly used for treatment of rhinitis and rhinosinusitis. Its dry fruit infusion is used into the nose, delivering profuse mucous secretion, but may cause nasal mucosa irritation, epistaxis or anosmia. We evaluated the effects of different concentrations of Luffa operculata dry fruit infusion on mucociliary transport velocity (MTV), ciliary beat frequency (CBF), transepithelial potential difference (TPD) and epithelial morphology (light and electron transmission microscopy) of the isolated frog palate preparation. Results pointed to dose-dependent epithelial damage on mucociliary epithelium, suggesting that it is potentially noxious to the human nasal mucosa

Luffa operculata é uma planta medicinal popularmente usada para tratamento de rinites e rinossinusites. A infusão de seu fruto seco é usada no nariz, liberando secreção mucosa profusa, mas pode causar irritação, epistaxe ou anosmia. Avaliamos os efeitos de diferentes concentrações da infusão do fruto seco da Luffa operculata na velocidade de transporte mucociliar (VTM), freqüência de batimento ciliar (FBC), diferença de potencial transepitelial (DPT) e morfologia do epitélio (microscopia de luz e eletrônica de transmissão), no modelo do palato isolado de rã. Os resultados apontam para dano epitelial dose-dependente no epitélio mucociliar, sugerindo que ela seja potencialmente nociva à mucosa nasal humana / Luffa operculata is a medicinal plant popularly used for treatment of rhinitis and rhinosinusitis. Its dry fruit infusion is used into the nose, delivering profuse mucous secretion, but may cause nasal mucosa irritation, epistaxis or anosmia. We evaluated the effects of different concentrations of Luffa operculata dry fruit infusion on mucociliary transport velocity (MTV), ciliary beat frequency (CBF), transepithelial potential difference (TPD) and epithelial morphology (light and electron transmission microscopy) of the isolated frog palate preparation. Results pointed to dose-dependent epithelial damage on mucociliary epithelium, suggesting that it is potentially noxious to the human nasal mucosa