Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/10918 |
Resumo: | Waltheria brachypetala Turcz (Malvaceae) is an endemic medicinal plant from brazilian northeast. This plant is commonly used on folk medicine as antifungal, antiinflamatory and to treatment of bronchitis and central nervous system disturbs. The aim of this work was the investigation of quinolone alkaloids produced by this plant. Through usual chromatographic methods of purification were isolated from hexane and diclorometane phases of roots and bark, nineteen quinolone alkaloids, being ten already reported on literature: antidesmone (1), N-methyl-antidesmone (2), desoxi-antidesmone (3), chamaedrone (4), hyeronimone (5), metil-hyeronimone (6), waltheriones A (7) and B (8), N-methyl-waltherione A (9), 4-O-methyl-waltherione A (10) and nine novel alkaloids: waltheriantidesmone (11), brachytelones A (12), B (13), C (14), D (15), waltheriones C (16) and D (17), N-methyl-waltherione B (18) and 10-hydroxi-waltherione D (19), along with common ciclycpeptides to Hermannieae. Were also isolated twocoumarinolignans cleomicine A (20) and acethylcleomicine A (21) as new to genus Waltheria, and other secondary metabolites common in plants. The hexane and dicloromethane phases of the bark were studied by HPLC-UV-MS/MS to make possible the identification of the probable biogenesis intermediates of the waltheriones: 9,10-epoxy-10-hydroxi-melochinone (22), 13-hydroxi-melochinone (23) e melochinone (24), along with vanessine (25) e waltheriahyeronimone (26), being 26 did not yet report on literature. The isolation of that alkaloids from W. brachypetala confirmes it as potential chemossistematic markers to Hermannieae tribe and it strengthens the hypothesisof chemossystematic to suggest possible evolutive similarity between Hermannieae (Malvaceae) and Antidesmeae (Phyllantaceae), as well as similarity of antidesomne biogenesis pathway with melochinone derivatives biogenesis pathway. The alkaloids11, 12 and 13 represent a new class of aryl-alkyl-quinolone alkaloids that are being reported by first time in this work. The biological potential of W. brachypetalawas evaluated on the inhibition of AChE enzime and fungitoxic assays against the citros phytopatogen Guignardia citricarpa. All quinolone alkaloids tested presented significant activity of inhibition of AChE in vitro detaching the aryl-alkyl-quinolone alkaloids: waltheriantidesmone, brachytelone A e brachytelone B, that inhibits AChE in 93%, 88,04% e 91,05%, respectively, on concentration of 100 μM and with low value of IC50. The alkaloids antidesmone, w-antidesmone, chamaedrone, brachytelone A and brachytelone B, apresentaram excelente fungitoxic activity against G. citricarpa, as much with regard to mycelial growth inhibition as to germination of spores and apressorium formation presenting low value ofIC50. It detaches that the alkaloids brachytelone A and waltheriantidesmone presented more potente than the commercial fungicide carbendazin at concentration of 5 μg/ml, being thus potential candidates to chemical control of the Black Spot of Citros. |
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Lima, Murilo Marinho de CastroSilva, Maria Fátima das Graças Fernandes dahttp://lattes.cnpq.br/0457632122660653http://lattes.cnpq.br/0473315948052236e3544e4b-348f-4b00-877b-c4f77f8682b12019-02-06T18:46:37Z2019-02-06T18:46:37Z2012-06-26LIMA, Murilo Marinho de Castro. Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase. 2012. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2012. Disponível em: https://repositorio.ufscar.br/handle/ufscar/10918.https://repositorio.ufscar.br/handle/ufscar/10918Waltheria brachypetala Turcz (Malvaceae) is an endemic medicinal plant from brazilian northeast. This plant is commonly used on folk medicine as antifungal, antiinflamatory and to treatment of bronchitis and central nervous system disturbs. The aim of this work was the investigation of quinolone alkaloids produced by this plant. Through usual chromatographic methods of purification were isolated from hexane and diclorometane phases of roots and bark, nineteen quinolone alkaloids, being ten already reported on literature: antidesmone (1), N-methyl-antidesmone (2), desoxi-antidesmone (3), chamaedrone (4), hyeronimone (5), metil-hyeronimone (6), waltheriones A (7) and B (8), N-methyl-waltherione A (9), 4-O-methyl-waltherione A (10) and nine novel alkaloids: waltheriantidesmone (11), brachytelones A (12), B (13), C (14), D (15), waltheriones C (16) and D (17), N-methyl-waltherione B (18) and 10-hydroxi-waltherione D (19), along with common ciclycpeptides to Hermannieae. Were also isolated twocoumarinolignans cleomicine A (20) and acethylcleomicine A (21) as new to genus Waltheria, and other secondary metabolites common in plants. The hexane and dicloromethane phases of the bark were studied by HPLC-UV-MS/MS to make possible the identification of the probable biogenesis intermediates of the waltheriones: 9,10-epoxy-10-hydroxi-melochinone (22), 13-hydroxi-melochinone (23) e melochinone (24), along with vanessine (25) e waltheriahyeronimone (26), being 26 did not yet report on literature. The isolation of that alkaloids from W. brachypetala confirmes it as potential chemossistematic markers to Hermannieae tribe and it strengthens the hypothesisof chemossystematic to suggest possible evolutive similarity between Hermannieae (Malvaceae) and Antidesmeae (Phyllantaceae), as well as similarity of antidesomne biogenesis pathway with melochinone derivatives biogenesis pathway. The alkaloids11, 12 and 13 represent a new class of aryl-alkyl-quinolone alkaloids that are being reported by first time in this work. The biological potential of W. brachypetalawas evaluated on the inhibition of AChE enzime and fungitoxic assays against the citros phytopatogen Guignardia citricarpa. All quinolone alkaloids tested presented significant activity of inhibition of AChE in vitro detaching the aryl-alkyl-quinolone alkaloids: waltheriantidesmone, brachytelone A e brachytelone B, that inhibits AChE in 93%, 88,04% e 91,05%, respectively, on concentration of 100 μM and with low value of IC50. The alkaloids antidesmone, w-antidesmone, chamaedrone, brachytelone A and brachytelone B, apresentaram excelente fungitoxic activity against G. citricarpa, as much with regard to mycelial growth inhibition as to germination of spores and apressorium formation presenting low value ofIC50. It detaches that the alkaloids brachytelone A and waltheriantidesmone presented more potente than the commercial fungicide carbendazin at concentration of 5 μg/ml, being thus potential candidates to chemical control of the Black Spot of Citros.Waltheria brachypetala Turcz (Malvaceae) é uma planta de ocorrência endêmica do nordeste brasileiro, sendo amplamente utilizada na medicina tradicional como agente anti-fúngico, anti-inflamatório, bem como para o tratamento de bronquite, laringite e distúrbios do sistema nervoso central. Neste trabalho de doutoramento objetivou-se a investigação dos alcaloides quinolônicos produzidos por esta planta. A partir de métodos cromatográficos usuais de purificação, foram isolados das fases hexânica e diclorometano do caule da raiz dezenove alcaloides quinolônicos, sendo dez anteriormente relatados na literatura: antidesmona (1), N-metil-antidesmona (2), desóxi-antidesmona (3), chamaedrona (4), hyeronimona (5), metil-hyeronimona (6), waltherionas A (7), e B (8), N-metil-waltheriona A (9), 4-O-metil-waltheriona A (10) e nove inéditos: waltheriantidesmona (11), brachytelonas A (12), B (13), C (14), D (15), waltherionas C (16) e D (17), N-metil-waltheriona B (18) e 10-hidróxi-waltheriona D (19), além de alcaloides ciclopeptídicos de ocorrência comum na tribo Hermannieae. Foram isoladas ainda duas cumarino-lignanas inéditas no gênero Waltheria cleomicina A (20) e acetilcleomicina A (21), além de outros metabólitos de ocorrência comum em plantas. As fases em hexano e diclorometano do caule foram também estudados via HPLC-UV-MS/MS possibilitando a identificação de possíveis intermediários de biogênese das waltherionas: 9,10-epóxi-10-hidróxi-melochinona (22), 13-hidróxi-melochinona (23) emelochinona (23), além da vanessina (28) e waltheriahyeronimona (29), este último não reportado ainda na literatura. O isolamento destes alcaloides quinolônicos a partir de W. brachypetala confirma a importância destes como marcadores quimiossitemáticos da tribo Hermannieae e reforça a hipótese por quimiossistemática de semelhança evolutiva entre esta tribo e a tribo Antidesmeae (Phyllantaceae), bem como da semelhança da rota de biogênese dos alcaloides derivados da antidesmona com aqueles derivados da melochinona. Os alcaloides 11, 12 e 13representam uma nova classe de alcaloides aril-alquil-quinolonicos que está sendo reportada pela primeira vez. O potencial biológico de W. brachypetala foi avaliado frente à inibição da enzima acetilcolinesterase e com relação a atividade fungitóxica sobre o fitopatógeno de citros Guignardia citricarpa. Todos os alcaloides quinolônicos apresentaram resultados relevantes com relação à inibição da AChE, destacando-se os aril-alquil-quinolonas: waltheriantidesmona, brachytelona A e brachytelona B, que inibiram a enzima em 93%, 88,04% e 91,05%, respectivamente, na concentração de 100 μM e com baixos valores de IC50. Os alcaloides antidesmona, waltheriantidesmona, chamaedrona, brachytelona A e brachytelona B, apresentaram excelente atividade fungitóxica sobre G. citricarpa, tanto com relação à inibição do crescimento micelial, quanto da inibição da germinação de esporos e da formação de apressórios, apresentando baixos valores de IC50. Destaca-se os alcaloides brachytelona A e w-antidesmona que apresentaram-se mais potentes que o fungicida comercial carbendazin na concentração de 5 μg/ml, sendo assim potenciais candidatos ao controle da Mancha Preta do Citros.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)porUniversidade Federal de São CarlosCâmpus São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarProdutos naturaisAlcalóidesBiogêneseQuimiossistemáticaAtividades biológicasNatural productsAlkaloidsBiogenesisCIENCIAS EXATAS E DA TERRA::QUIMICAEstudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesteraseStudy of quinolone alkaloids from Waltheria brachypetala Turcz. 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dc.title.por.fl_str_mv |
Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase |
dc.title.alternative.eng.fl_str_mv |
Study of quinolone alkaloids from Waltheria brachypetala Turcz. (Malvaceae): isolation, structural elucidation, biogenesis and fungitoxical and anticholinesterase activities |
title |
Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase |
spellingShingle |
Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase Lima, Murilo Marinho de Castro Produtos naturais Alcalóides Biogênese Quimiossistemática Atividades biológicas Natural products Alkaloids Biogenesis CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase |
title_full |
Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase |
title_fullStr |
Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase |
title_full_unstemmed |
Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase |
title_sort |
Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase |
author |
Lima, Murilo Marinho de Castro |
author_facet |
Lima, Murilo Marinho de Castro |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/0473315948052236 |
dc.contributor.author.fl_str_mv |
Lima, Murilo Marinho de Castro |
dc.contributor.advisor1.fl_str_mv |
Silva, Maria Fátima das Graças Fernandes da |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0457632122660653 |
dc.contributor.authorID.fl_str_mv |
e3544e4b-348f-4b00-877b-c4f77f8682b1 |
contributor_str_mv |
Silva, Maria Fátima das Graças Fernandes da |
dc.subject.por.fl_str_mv |
Produtos naturais Alcalóides Biogênese Quimiossistemática Atividades biológicas |
topic |
Produtos naturais Alcalóides Biogênese Quimiossistemática Atividades biológicas Natural products Alkaloids Biogenesis CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Natural products Alkaloids Biogenesis |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Waltheria brachypetala Turcz (Malvaceae) is an endemic medicinal plant from brazilian northeast. This plant is commonly used on folk medicine as antifungal, antiinflamatory and to treatment of bronchitis and central nervous system disturbs. The aim of this work was the investigation of quinolone alkaloids produced by this plant. Through usual chromatographic methods of purification were isolated from hexane and diclorometane phases of roots and bark, nineteen quinolone alkaloids, being ten already reported on literature: antidesmone (1), N-methyl-antidesmone (2), desoxi-antidesmone (3), chamaedrone (4), hyeronimone (5), metil-hyeronimone (6), waltheriones A (7) and B (8), N-methyl-waltherione A (9), 4-O-methyl-waltherione A (10) and nine novel alkaloids: waltheriantidesmone (11), brachytelones A (12), B (13), C (14), D (15), waltheriones C (16) and D (17), N-methyl-waltherione B (18) and 10-hydroxi-waltherione D (19), along with common ciclycpeptides to Hermannieae. Were also isolated twocoumarinolignans cleomicine A (20) and acethylcleomicine A (21) as new to genus Waltheria, and other secondary metabolites common in plants. The hexane and dicloromethane phases of the bark were studied by HPLC-UV-MS/MS to make possible the identification of the probable biogenesis intermediates of the waltheriones: 9,10-epoxy-10-hydroxi-melochinone (22), 13-hydroxi-melochinone (23) e melochinone (24), along with vanessine (25) e waltheriahyeronimone (26), being 26 did not yet report on literature. The isolation of that alkaloids from W. brachypetala confirmes it as potential chemossistematic markers to Hermannieae tribe and it strengthens the hypothesisof chemossystematic to suggest possible evolutive similarity between Hermannieae (Malvaceae) and Antidesmeae (Phyllantaceae), as well as similarity of antidesomne biogenesis pathway with melochinone derivatives biogenesis pathway. The alkaloids11, 12 and 13 represent a new class of aryl-alkyl-quinolone alkaloids that are being reported by first time in this work. The biological potential of W. brachypetalawas evaluated on the inhibition of AChE enzime and fungitoxic assays against the citros phytopatogen Guignardia citricarpa. All quinolone alkaloids tested presented significant activity of inhibition of AChE in vitro detaching the aryl-alkyl-quinolone alkaloids: waltheriantidesmone, brachytelone A e brachytelone B, that inhibits AChE in 93%, 88,04% e 91,05%, respectively, on concentration of 100 μM and with low value of IC50. The alkaloids antidesmone, w-antidesmone, chamaedrone, brachytelone A and brachytelone B, apresentaram excelente fungitoxic activity against G. citricarpa, as much with regard to mycelial growth inhibition as to germination of spores and apressorium formation presenting low value ofIC50. It detaches that the alkaloids brachytelone A and waltheriantidesmone presented more potente than the commercial fungicide carbendazin at concentration of 5 μg/ml, being thus potential candidates to chemical control of the Black Spot of Citros. |
publishDate |
2012 |
dc.date.issued.fl_str_mv |
2012-06-26 |
dc.date.accessioned.fl_str_mv |
2019-02-06T18:46:37Z |
dc.date.available.fl_str_mv |
2019-02-06T18:46:37Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
LIMA, Murilo Marinho de Castro. Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase. 2012. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2012. Disponível em: https://repositorio.ufscar.br/handle/ufscar/10918. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/10918 |
identifier_str_mv |
LIMA, Murilo Marinho de Castro. Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase. 2012. Tese (Doutorado em Química) – Universidade Federal de São Carlos, São Carlos, 2012. Disponível em: https://repositorio.ufscar.br/handle/ufscar/10918. |
url |
https://repositorio.ufscar.br/handle/ufscar/10918 |
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por |
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por |
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600 600 |
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info:eu-repo/semantics/openAccess |
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openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de São Carlos Câmpus São Carlos |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química - PPGQ |
dc.publisher.initials.fl_str_mv |
UFSCar |
publisher.none.fl_str_mv |
Universidade Federal de São Carlos Câmpus São Carlos |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UFSCAR instname:Universidade Federal de São Carlos (UFSCAR) instacron:UFSCAR |
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Universidade Federal de São Carlos (UFSCAR) |
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UFSCAR |
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UFSCAR |
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Repositório Institucional da UFSCAR |
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Repositório Institucional da UFSCAR |
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Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR) |
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1813715599616901120 |