Estudo fitoquímico e biológico de Aristolochia ridicula
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Data
2009-03-13
Autores
Machado, Marcos Batista [UNESP]
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Editor
Universidade Estadual Paulista (Unesp)
Resumo
O presente trabalho descreve o isolamento, a identificação e a elucidação estrutural dos constituintes químicos de Aristolochia ridicula H.B.K., bem como a avaliação das potenciais atividades inseticidas, antiplasmódicas e antimicobacterianas dos extratos e das substâncias isoladas dessa espécie. Os extratos acetônico de folhas e etanólico de caules foram fracionados por partição, lavagem e métodos cromatográficos, resultando em seis e quatorze substâncias, respectivamente. Dentre essas substâncias estão uma nova biflavona (ridiculuflavona D), uma nova chalcona-flavona (ridiculuflavonilchalcona B) e um tetraflavonóide com esqueleto carbônico inédito (ridiculuflavonilchalcona C), juntamente com a ridiculuflavona C e o proto-quercitol, os quais foram previamente isolados dessa espécie. Além desses compostos, isolou-se um flavonóide (luteolina), três alcalóides [()-coclaurina, (−)-cloreto de N-steponina e (−)-metilwarifteina], uma alcamida (N-trans-feruloi-tiramina), duas ribonolactonas [(+)-2-desoxi-D-ribono-1,4-lactona e seu derivado 3,5-bis(tripolifosfato)], um derivado glucosídico (etil--D-glucopiranosídio) e o ácido 2-butinodióico. Além disso, identificou-se os íons 3-hidroxipropanoato, acetato e formiato por RMN 1D e 2D, sugerindo que esses compostos são derivados do ácido 2-butinodióico, o qual não foi detectado por RMN de 1H. As estruturas de todos os compostos isolados foram determinadas por métodos espectrométricos (RMN 1D e 2D, EMAR, IV, UV e DC). Transformações químicas (metilações e/ou acetilações) dos flavonóides ridiculuflavona C e ridiculuflavonilchalcona B, bem como dos alcalóides cloreto de N-steponina e metilwarifteina e da alcamida N-trans-feruloil-tiramina também auxiliaram na elucidação estrutural dessas substâncias. A susceptibilidade do inseto Anticarsia gemmatalis às soluções de extratos e de flavonóides...
This work describes the isolation, identification, and structural elucidation of the chemical constituents of Aristolochia ridicula H.B.K., as well as the evaluation of insecticidal, antiplasmodial, and antimycobacterial activities of extracts and the chemical constituents from this species. The acetone extract of the leaves and ethanol extract of the stems were fractionated by partitions and washing, followed by chromatographic column, PTLC, and/or HPLC methods to give, respectively, six and fourteen compounds. These included a new biflavone (ridiculuflavone D), a new chalcone-flavone (ridiculuflavonylchalcone B), and a tetraflavonoid with a new carbon skeleton (ridiculuflavonylchalcone C), together with a biflavone (ridiculuflavone C) and a cyclitol (proto-quercitol), which were previously isolated from this species. In addition, a flavonoid (luteolin), three alkaloids [()-coclaurine, (−)-N-steponine chloride, and (−)-methylwarifteine], an alkylamide (N-trans-feruloyl tiramine), two ribonolactones [(+)-2-deoxy-D-ribono-1,4-lactone and its derivative 3,5-bis(tripolyphosphate)], a glucose derivative (ethyl -D-glucopyranoside), and 2-butynedioic acid were isolated. Moreover, 3-hydroxypropanoate, acetate, and formate were detected by NMR techniques, which suggests that they are derivatives from 2-butynedioic acid, which is not detected by 1H NMR. The structures of all isolated compounds were determined by spectrometric method (1D and 2D NMR, HRMS, IR, UV, and CD). Chemical transformations (methylations and/or acetylations) of ridiculuflavone C, ridiculuflavonylchalcone B, N-steponine chloride, methylwarifteine, and N-trans-feruloyl tiramine, also provide further evidences in the structural elucidations of these compounds. The susceptibility of Anticarsia gemmatalis to solutions of extracts and several flavonoids from A. ridicula were evaluated by topical... (Complete abstract click electronic access below)
This work describes the isolation, identification, and structural elucidation of the chemical constituents of Aristolochia ridicula H.B.K., as well as the evaluation of insecticidal, antiplasmodial, and antimycobacterial activities of extracts and the chemical constituents from this species. The acetone extract of the leaves and ethanol extract of the stems were fractionated by partitions and washing, followed by chromatographic column, PTLC, and/or HPLC methods to give, respectively, six and fourteen compounds. These included a new biflavone (ridiculuflavone D), a new chalcone-flavone (ridiculuflavonylchalcone B), and a tetraflavonoid with a new carbon skeleton (ridiculuflavonylchalcone C), together with a biflavone (ridiculuflavone C) and a cyclitol (proto-quercitol), which were previously isolated from this species. In addition, a flavonoid (luteolin), three alkaloids [()-coclaurine, (−)-N-steponine chloride, and (−)-methylwarifteine], an alkylamide (N-trans-feruloyl tiramine), two ribonolactones [(+)-2-deoxy-D-ribono-1,4-lactone and its derivative 3,5-bis(tripolyphosphate)], a glucose derivative (ethyl -D-glucopyranoside), and 2-butynedioic acid were isolated. Moreover, 3-hydroxypropanoate, acetate, and formate were detected by NMR techniques, which suggests that they are derivatives from 2-butynedioic acid, which is not detected by 1H NMR. The structures of all isolated compounds were determined by spectrometric method (1D and 2D NMR, HRMS, IR, UV, and CD). Chemical transformations (methylations and/or acetylations) of ridiculuflavone C, ridiculuflavonylchalcone B, N-steponine chloride, methylwarifteine, and N-trans-feruloyl tiramine, also provide further evidences in the structural elucidations of these compounds. The susceptibility of Anticarsia gemmatalis to solutions of extracts and several flavonoids from A. ridicula were evaluated by topical... (Complete abstract click electronic access below)
Descrição
Palavras-chave
Bioquímica, Flavonoides, Aristoloquiacea, Biochemistry
Como citar
MACHADO, Marcos Batista. Estudo fitoquímico e biológico de Aristolochia ridicula. 2009. 366 f. Tese (doutorado) - Universidade Estadual Paulista, Instituto de Química, 2009.