Biological Activity of Quinoline Alkaloids from Raulinoa echinata and X-ray Structure of Flindersiamine

Biavatti, Maique W.; Vieira, Paulo; Silva, M. Fátima das G. F. da; Fernandes, João B.; Victor, Sandra R.; Pagnocca, Fernando Carlos; Albuquerque, Sérgio de; Caracelli, Ignez; Zukerman-Schpector, Júlio

doi:10.1590/s0103-50532002000100010

Cited by 48 publications

(37 citation statements)

References 16 publications

(19 reference statements)

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“…16 Todas as substâncias foram identificadas através da análise dos seus dados espectroscópicos e comparação com os da literatura. A mistura de piranoflavonas (2) está sendo descrita pela primeira vez Adicionalmente, um singleto em 6,08 δ, integrado para um hidrogênio, revelou a identidade dessa substân-cia como um alcalóide 4-R-2-quinolônico, que é de ocorrência bastante ampla em plantas da família Rutaceae.…”

Section: Resultsunclassified

Piranoflavonas inéditas e atividades tripanocidas das substâncias isoladas de conchocarpus heterophyllus

Ambrozin¹,

Vieira²,

Fernandes³

et al. 2008

Quím. Nova

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. do Café, s/n, 14040-903 Ribeirão Preto -SP, BrasilRecebido em 18/5/07; aceito em 14/11/07; publicado na web em 19/3/08 NEW PYRANOFLAVONES AND TRYPANOCIDAL ACTIVITY OF COMPOUNDS ISOLATED FROM Conchocarpus heterophyllus. The phytochemical investigation of trypanocidal extracts from leaves and stems of Conchocarpus heterophyllus (A. St.-Hil.) Kallunki & Pirani (Rutaceae) afforded new pyranoflavones along with the known compounds flavone, 7-methoxyflavone, 5-hydroxyflavone, haplotusine, 1-methyl-2-phenyl-4-quinolone alkaloid, β-sitosterol, stigmasterol, and β-sitosteryl benzoate. Their structures were established based on their spectral data. NMR data for the alkaloid haplotusine and the new pyranoflavones are described for the first time herein. These compounds were assayed on the tripomastigote forms of Trypanosoma cruzi. Among them, haplotusine and 1-methyl-2-phenyl-4-quinolone showed moderate values of IC 50 136.9 and 144.9 µM, respectively.

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Section: Resultsunclassified

Piranoflavonas inéditas e atividades tripanocidas das substâncias isoladas de conchocarpus heterophyllus

Ambrozin¹,

Vieira²,

Fernandes³

et al. 2008

Quím. Nova

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“…16 Epoxy-fraxinellone showed not be toxic to the leafcutting ants, although limonexic acid displayed a significant reduction on lifetime (11 days) of leaf cutting ants, when compared with the control group (22 days) (Figure 3).…”

Section: Resultsmentioning

confidence: 92%

Leaf-cutting ants toxicity of limonexic acid and degraded limonoids from Raulinoa echinata.: X-ray structure of epoxy-fraxinellone

Biavatti¹,

Westerlon²,

Vieira³

et al. 2005

J. Braz. Chem. Soc.

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A investigação fitoquímica das raízes de Raulinoa echinata, planta endêmica do Vale do Itajaí/ SC, levou ao isolamento e identificação dos limonóides degradados: fraxinelona, fraxinelonona e epoxi-fraxinelona. O último foi anteriormente isolado dos caules, porém sua configuração relativa não foi resolvida por experimentos de RMN. Este trabalho apresenta a análise de difração de raios-X da epoxi-fraxinelona, descreve o isolamento da fraxinelonona e fraxinelona pela primeira vez em Raulinoa, e a atividade tóxica da primeira sobre formigas cortadeiras (Atta sexdens rubropilosa). Pouca atividade foi observada para o limonóide degradado testado; entretanto, o limonóide ácido limonéxico isolado dos caules, apresentou alta toxicidade contra as formigas cortadeiras, reduzindo consideravelmente a longevidade das mesmas, em comparação com o controle.Phytochemical survey of roots extracts of the South Brazilian endemic plant Raulinoa echinata Cowan, Rutaceae led to the isolation of known degraded limonoids: fraxinellone, fraxinellonone and epoxy-fraxinellone. The latter was previously isolated also from the stems, but the relative configuration could not be solved by NMR experiments. This paper deals with the X-ray diffraction analysis of epoxy-fraxinellone and its toxicity to leaf-cutting ants, describes the isolation of fraxinellonone and fraxinellone for the first time in Raulinoa. Epoxy-fraxinellone showed no toxicity to the leaf-cutting ants (Atta sexdens rubropilosa). The limonoid limonexic acid, isolated from stems, presented high toxicity to the leaf-cutting ants, diminishing considerably their longevity.Keywords: Raulinoa echinata, degraded limonoids, limonexic acid, Atta sexdens rubropilosa, X-ray structure IntroductionRaulinoa is a monospecific genus and the species Raulinoa echinata Cowan (Rutaceae) is endemic in the Itajaí Valley, SC, Brazil. 1 This endangered perennial woody shrub is characterized by the presence of spines (popularly know as Cutia-de-espinho) and has only been found in a short interval (1000 m) on the frequently inundated banks of Itajaí river in an approximate altitude of 100 m, showing a high degree of adaptation to the environment.We have previously reported the isolation and biological activities of some compounds of R. echinata. 2 In continuation of our search for compounds and natural products to be used in the control of leaf-cutting ants, we have investigated the hexane extracts of roots of R. echinata leading to the isolation of typical rutaceous degraded limonoids: fraxinellone (1), fraxinellonone (2) and new epoxy-fraxinellone (3). The extracts of the stems furnished the known limonin precursor, limonexic acid (4).Leaf-cutting ants are one of the most serious agricultural pests in South American countries and the biological control of these insects has been the aim of many studies. Their control can be achieved by means of intoxicating the leaf-cutting ants 3 or inhibiting the growth of their symbiotic fungus.In this paper we describe the isolation, structural determination and eva...

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“…On the other hand, andiroba oil showed lower effect on the tested ant workers. In other study, andiroba oil (Morini et al, 1997) and citrus seed oil (Fernandes et al, 2002) present toxic effects to grass-cutting ants. Essential oil of cinnamon tree (C. zeylanicum) has been showed toxic effectives on adults of Bruchidius incarnatus, Sitophilus granarius, S. zeamais, R. dominica and T. castaneum (Salvadores et al, 2007;Shayesteh and Ashouri, 2010;Fouad, 2013).…”

Section: Insect Speciesmentioning

confidence: 86%

“…Baits with plant extracts were effective in the field as a control measure, stopping ant activity (Zanetti et al, 2008). Some of these substances can act directly against the ant, leading to its death, such as citrus seed oils; Citrus sinensis (L.) Osbeck, Citrus limon (L.) Burm or Citrus reticulate Blanco (Rutaceae) (Fernandes et al, 2002). Other Plants can be toxic to leaf-cutting ants, such as Tithonia diversifolia (Asteraceae), Ricinus communis (Euphorbiaceae), Eucalyptus maculate (Myrtaceae), Hymenaea courbaril (Fabaceae) (North et al, 2000;Marinho et al, 2005;Marinho et al, 2008;Alonso et al, 2013;Castaño-Quintana et al, 2013) and/or to their fungus, such as Piper piresii (Piperaceae), Simarouba versicolor (Simaroubaceae), Raulinoa echinata Coffea spp.…”

Section: Ingestion With a Treated Leavesmentioning

confidence: 99%

“…Other Plants can be toxic to leaf-cutting ants, such as Tithonia diversifolia (Asteraceae), Ricinus communis (Euphorbiaceae), Eucalyptus maculate (Myrtaceae), Hymenaea courbaril (Fabaceae) (North et al, 2000;Marinho et al, 2005;Marinho et al, 2008;Alonso et al, 2013;Castaño-Quintana et al, 2013) and/or to their fungus, such as Piper piresii (Piperaceae), Simarouba versicolor (Simaroubaceae), Raulinoa echinata Coffea spp. (Rutaceae) (Biavatti et al, 2002;Pagnocca et al, 2006;Peñaflor et al, 2009) …”

Section: Ingestion With a Treated Leavesmentioning

confidence: 99%

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Potential use of essential oils to control the leaf-cutting ants; Atta sexdens rubropilosa and Acromyrmex subterraneus molestans (Hymenoptera: Formicidae)

Ribeiro¹,

Fouad²

2016

International Journal of Industrial Entomology

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The present study was developed in order to evaluate the effect of five essential oils on the workers of the leaf-cutting ants; Atta sexdens rubropilosa and Acromyrmex subterraneus molestans by contact with a treated surface and ingestion with a treated leaves.. The essential oils of cinnamon, clove and mustard had generally more effective with 5, 10 and 15% concentrations after 24, 48, 72 and 96 h against workers of A. sexdens rubropilosa and A. subterraneus molestans in contact bioassay, but mustard was the most effective in ingestion bioassay on both species. On the other hand, there was no significant difference among the essential oils with 1% concentration and control after 24, 48 and 72 h of treatment in contact and ingestion bioassays against workers of A. sexdens rubropilosa. However, Andiroba oil had less efficiency values in all concentrations been used. Therefore, the essential oils of mustard, cinnamon and clove have contact and ingestion effects on workers of A. sexdens rubropilosa and A. subterraneus molestans, and may be promising on the leaf-cutting ant control. The bioassays were performed with workers of Atta sexdens rubropilosa and Acromyrmex subterraneus molestans. The workers were caught incolonies located around the Campus of the Universidade Federal de Viçosa (UFV), Viçosa, Minas Gerais State, Brazil. Than these colonies were maintained at a temperature of 25 ± 5°C, RH of 75 ± 5% in 24 h scotophase, and fed with leaves of different vegetables, changed daily, as well as a water supply (Della Lucia et al., 1993). The volumes of the fungus gardens were at least three liters per colony.

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Biological Activity of Quinoline Alkaloids from Raulinoa echinata and X-ray Structure of Flindersiamine

Cited by 48 publications

References 16 publications

Piranoflavonas inéditas e atividades tripanocidas das substâncias isoladas de conchocarpus heterophyllus

Piranoflavonas inéditas e atividades tripanocidas das substâncias isoladas de conchocarpus heterophyllus

Leaf-cutting ants toxicity of limonexic acid and degraded limonoids from Raulinoa echinata.: X-ray structure of epoxy-fraxinellone

Potential use of essential oils to control the leaf-cutting ants; Atta sexdens rubropilosa and Acromyrmex subterraneus molestans (Hymenoptera: Formicidae)

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