Análise comparativa dos efeitos alelopáticos das substâncias químicas titonina e titonina acetilada

Filho, A.P.S. Souza; Borges, Fábio; Santos, Lourivaldo S.

doi:10.1590/s0100-83582006000200001

Cited by 10 publications

(7 citation statements)

References 11 publications

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“…[8][9][10][11] There have been described 205 species of Pestalotiopsis, 12 some of these produce secondary metabolites with important activities, like phytotoxic, antifungic, antioxidant and anticancer activities.…”

Section: Introductionmentioning

confidence: 99%

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Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae)

Oliveira

Santos

et al. 2011

J. Braz. Chem. Soc.

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Um novo derivado de antraquinona, denominado guepinone (1), juntamente com as conhecidas substâncias isossulocrina (2) e cloroissosulocrina (3) foram isolados de uma cultura em arroz de Pestalotiopsis guepinii, um fungo endofitico de Virola michelii. Os compostos foram identificados pela análise de seus dados espectrométricos de RMN 1D e 2D e EM. A atividade antimicrobiana dos compostos isolados foi avaliada e a cloroisossulcrina (3) foi a mais ativa.A new anthraquinone derivative, named guepinone (1), along with the known substances isosulochrin (2) and chloroisosulochrin (3), were isolated from a rice culture of Pestalotiopsis guepinii, an endophytic fungus of Virola michelii. The compounds were identified by analysis of 1D and 2D NMR and MS spectral data. The antimicrobial activity of these compounds was evaluated and chloroisosulchrin (3) was the most active. Keywords: Virola michelii, Pestalotiopsis guepinii, anthraquinone derivatives, endophytic fungus IntroductionEndophytic fungi have been collected from nearly all plants studied. They colonize the plants without causing visible disease symptoms. The function of the host plant is not yet clear and is supposed to depend on the organ-fungus interaction of each plant indicating that there are no neutral interactions but a balanced antagonism between the plant and the endophytic fungi. Endophytic fungi are very useful in agriculture and industry. They can be used as a tool for introduction of genes of interest into the plants, 2,3 like plague and pathogen inhibitors. 4,5 They are also a source of primary and secondary metabolites of interest.In spite of the several reports concerning the production of substances by endophytic fungi that show biological activities, such as fungicide, herbicide and algicide, among others, 6 there are not many studies concerning the chemical composition of endophytic microorganisms, especially when we analize the wide fungic biodiversity and the specificity in the colonization of plants by fungi. This paper deals with the study of the metabolites produced by the fungus Pestalotiopsis guepinii isolated from Virola michelii.V. michelii belongs to the family Myristicaceae and it is used in folk medicine in the treatement of diseases caused by fungi and in the treatment of infections of the skin.7 Phytochemical study, anti-inflammatory and allelopathic activities of the leaves of the V. michelii were reported. [8][9][10][11] There have been described 205 species of Pestalotiopsis, 12 some of these produce secondary metabolites with important activities, like phytotoxic, antifungic, antioxidant and anticancer activities.13 Studies with P. guepinii lead Novel Anthraquinone Derivatives Produced by Pestalotiopsis guepinii J. Braz. Chem. Soc. 994 to the isolation of the diterpenoid taxol, an important anticancer drug.14 Pestalotiopsis also produce sesquiterpenes, other diterpenes, phenolic derivatives and anthraquinone derivatives. [14][15][16] This paper reports the isolation and structural elucidation of three anthraquinone derivat...

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Section: Introductionmentioning

confidence: 99%

“…7 Phytochemical study, anti-inflammatory and allelopathic activities of the leaves of the V. michelii were reported. [8][9][10][11] There have been described 205 species of Pestalotiopsis, Figure 1. In addition, this is the first report of P. guepinii as an endophyte from V. michelii and its production of anthraquinones derivatives.…”

Section: Introductionmentioning

confidence: 99%

Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae)

Oliveira

Santos

et al. 2011

J. Braz. Chem. Soc.

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“…Diversos autores também constataram efeito dose/dependente, ao analisar a alelopatia de outras espécies (Gatti et al 2004;Souza Filho et al 2006). Também influenciaram no aparecimento de plântulas anormais, com disparidades no tamanho estrutural, com raízes primárias atrofi adas e defeituosas e ausência de raízes secundárias, efeitos aparentemente comuns, segundo (Chon et al 2000), pelo fato de as raízes serem mais sensíveis às substâncias presentes nos extratos quando comparados às demais estruturas das plântulas.…”

Section: Resultsunclassified

“…Isto porque os benefícios da pesquisa alelopática podem ser utilizados para melhorar a sustentabilidade de nossos sistemas de produção e a conservação da vegetação natural ou seminatural (Chou 1999;Macías et al 1998;Olofsdotter & Mallik 2001;Smith & Martin 1994). Souza Filho et al (2006 sugerem que substâncias químicas com atividade alelopática podem ser utilizadas diretamente na formulação de bioerbicidas ou serem modifi cadas com vistas a aumentar sua atividade biológica.…”

Section: Introductionunclassified

Atividade alelopática de folhas e pseudofrutos de Hovenia dulcis Thunb. (Rhamnaceae) sobre a germinação de Lactuca sativa L. (Asteraceae)

et al. 2011

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ABSTRACT(Allelopathic activity of Hovenia dulcis Th unb. (Rhamnaceae) leaves and pseudofruits on the germination of Lactuca sativa L. (Asteraceae)). Th is paper aims to evaluate the allelopathic eff ect of dry leaves and pseudofruits of Hovenia dulcis Th unb. on lettuce seeds. Th erefore, aqueous extracts of leaves and pseudofruits were prepared in 1%, 2% and 4% (m/v) concentrations. Four replicates were done of 25 lettuce seeds distributed in Petri dishes lined with Germitest paper and humidifi ed with the extracts, maintained in germination chamber at 25 °C, constant photoperiod and light presence for fi ve days, the control being distilled water. Th e percentage, speed, germination rate index, root length and aerial-part length of the seedlings were calculated, as well as the seeds eff ect in the presence of diff erent pH solutions. It was observed that the seedlings were signifi cantly aff ected in the presence of aqueous extracts of dry leaves and pseudofruits at 2% and 4% concentrations. Th e eff ects were not linked to pH and osmotic potential, indicating, therefore, allelopathic interference of Hovenia dulcis extracts.

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“…[19][20][21][22][23][24] Small differences in the chemical structure of certain substances may be favorable for an increase in allelopathic activity. 25 Compounds 1 and 2 showed more structural similarities to each other when compared to 4. Those variations were not sufficient to promote differences in the inhibiting activity of seed germination.…”

Section: Phytotoxicity Of Ethanolic Extract and Purified Compoundsmentioning

confidence: 93%

Stilbenes from Deguelia rufescens var. urucu (Ducke) A. M. G. Azevedo leaves: effects on seed germination and plant growth

Lôbo¹,

Silva²,

Freitas³

et al. 2010

J. Braz. Chem. Soc.

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A biodiversidade Amazônica pode ser uma fonte de substâncias capazes de serem utilizadas no controle de plantas daninhas. Neste estudo relatamos o isolamento e a identificação de cinco estilbenos a partir das folhas do "timbó vermelho" (Deguelia rufescens var. urucu): 4-metoxilonchocarpeno (1); 3,5-dimetoxi-4′-hidroxi-3′-prenil-trans-estilbeno (2), lonchocarpeno (3), 3,5-dimetoxi-4′-O-prenil-trans-estilbeno (4) e pteroestilbeno (5). As substâncias 2 e 4 são novos produtos naturais, porém 2 já havia sido citada como produto de síntese. Foi avaliada a potencial atividade alelopática de 1, 2 e 4 sobre a germinação de sementes e o crescimento da planta daninha Mimosa pudica. Os efeitos observados sobre a germinação das sementes de M. pudica não variaram significantemente (p > 0,05) quando a análise da fitotoxidade foi realizada com as substâncias isoladamente, cuja inibição máxima não ultrapassou 20%. A inibição mais intensa, quanto ao desenvolvimento da radícula e do hipocótilo, foi encontrada para o composto 4 (p < 0,05). Isoladamente, 4 causou efeito inibitório significativamente maior (p < 0,05) no desenvolvimento da radícula e do hipocótilo, do que 1 e 2. Quando testados aos pares, apresentaram antagonismo para a germinação de sementes e sinergismo para o desenvolvimento da radícula e hipocótilo.The Amazon biodiversity may provide plants whose chemical substances are capable of controlling weeds. In this study we report the isolation and identification of five stilbenes from the leaves of "timbó vermelho" (Deguelia rufescens var. urucu): 4-methoxylonchocarpene (1); 3,5-dimethoxy-4′-hydroxy-3′-prenyl-trans-stilbene (2), lonchocarpene (3), 3,5-dimethoxy-4′-Oprenyl-trans-stilbene (4) and pterostilbene (5). Compounds 2 and 4 are new natural products although 2 has been previously cited as synthesis product. Potential allelopathic activity for 1, 2 and 4 was evaluated over seed germination and plant growth of Mimosa pudica weed. The observed effects on seed germination did not vary significantly (p > 0.05) when the analysis of phytotoxicity was performed with the substances alone, the maximum inhibition did not exceed 20%. The most intense inhibitions on radicle and hypocotyl development were found for compound 4 (p < 0.05). When tested in pairs, showed antagonism for seed germination and synergism for radicle and hypocotyl development.

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Análise comparativa dos efeitos alelopáticos das substâncias químicas titonina e titonina acetilada

Cited by 10 publications

References 11 publications

Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae)

Novel anthraquinone derivatives produced by Pestalotiopsis guepinii, an endophytic of the medicinal plant Virola michelii (Myristicaceae)

Atividade alelopática de folhas e pseudofrutos de Hovenia dulcis Thunb. (Rhamnaceae) sobre a germinação de Lactuca sativa L. (Asteraceae)

Stilbenes from Deguelia rufescens var. urucu (Ducke) A. M. G. Azevedo leaves: effects on seed germination and plant growth

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