Estudo dos alcaloides quinolônicos de Waltheria brachypetala Turcz: isolamento, determinação estrutural, biogênese, atividades fungitóxica e anticolinesterase

Detalhes bibliográficos
Autor(a) principal: Lima, Murilo Marinho de Castro
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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spelling 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
dc.language.iso.fl_str_mv por
language por
dc.relation.confidence.fl_str_mv 600
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