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Academia Brasileira de Ciências, Anais da Academia Brasileira de Ciências, 3(85), p. 881-889, 2013

DOI: 10.1590/s0001-37652013000300004

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Flavonoids from leaves of Derris urucu: assessment of potential effects on seed germination and development of weeds

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Em estudos anteriores descrevemos o isolamento de nove subst?ncias, a partir das folhas de Derris urucu, uma esp?cie encontrada amplamente na floresta Amaz?nica, as quais foram identificadas como cinco estilbenos e quatro diidroflavon?is. Neste trabalho, tr?s desses diidroflavon?is [urucuol A (1), urucuol B (2) e isotirumalina (3)] foram avaliados para identificar seus potenciais como aleloqu?micos. Estamos relatando tamb?m, o isolamento e a determina??o estrutural de um novo flavon?ide [5,3?-diidroxi-4?-metoxi-(7,6:5?,6?)-2?,2?-dimetilpiranoflavanona (4)]. Investigamos os efeitos dos diidroflavon?is 1-3 sobre a germina??o de sementes e desenvolvimento da rad?cula e do hipoc?tilo da planta daninha Mimosa pudica, usando solu??es a 150 mg.L ?1 . Urucuol B, isoladamente, foi quem apresentou o maior potencial para inibir a germina??o de sementes (26%), por sua vez, isotirulamina exibiu maior capacidade para reduzir o desenvolvimento do hipoc?tilo (25%), por?m nenhuma das tr?s subst?ncias mostrou potencial para inibir o desenvolvimento da rad?cula. Quando combinadas aos pares, as subst?ncias mostraram sinergismo ao desenvolvimento da rad?cula e do hipoc?tilo e efeitos, na germina??o de sementes, que poderiam ser atribu?dos a antagonismo. Quando testadas separadamente, as subst?ncias apresentaram maior tend?ncia para inibir a germina??o de sementes, enquanto que, quando testadas aos pares, observou-se aumento no efeito de inibi??o do desenvolvimento da planta daninha. ; ABSTRACT: In some previous studies, we described the isolation of nine compounds from leaves of Derris urucu, a species found widely in the Amazon rainforest, identified as five stilbenes and four dihydroflavonols. In this work, three of these dihydroflavonols [urucuol A (1), urucuol B (2) and isotirumalin (3)] were evaluated to identify their potential as allelochemicals, and we are also reporting the isolation and structural determination of a new flavonoid [5,3?-dihydroxy-4?-methoxy-(7,6:5?,6?)-2?,2?-dimethylpyranoflavanone (4)]. We investigated the effects of the dihydroflavonols 1-3 on seed germination and radicle and hypocotyl growth of the weed Mimosa pudica, using solutions at 150 mg.L ?1 . Urucuol B, alone, was the substance with the greatest potential to inhibit seed germination (26%), while isotirumalin showed greater ability to reduce the development of the hypocotyl (25%), but none of the three substances showed the potential to inhibit radicle. When combined in pairs, the substances showed synergism for the development of root and hypocotyl and effects on seed germination that could be attributed to antagonism. When tested separately, the trend has become more intense effects on seed germination, while for the substances tested in pairs, the intensity of the effect was greater on development of weed.