Occurrence of the insecticidal 16,17-didehydro-16(E)-stemofoline in Stemona collinsae

Jiwajinda, Suratwadee; Hirai, Nobuhiro; Watanabe, Keisuke; Santisopasri, Vilai; Chuengsamarnyart, Narong; Koshimįzu, Koichi; Ohigashi, Hajime

doi:10.1016/s0031-9422(00)00443-x

Cited by 68 publications

(80 citation statements)

References 4 publications

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“…Although no similar investigation was found in the literature for oxoaporphine alkaloids, some nitrogenated compounds have been presented as promising larvicides. [19][20][21][22] The chemical composition of the essential oils from the leaves and stems of R. leptopetala showed quantitative and qualitative variation. The leaf oil consisted mainly of oxygenated monoterpenes (47.7%), with linalool and 1,8-cineole as the major compounds.…”

Section: Resultsmentioning

confidence: 99%

Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Feitosa

Arriaga

Conceição

et al. 2009

J. Braz. Chem. Soc.

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No presente trabalho descreve-se a composição química dos óleos essenciais de Rollinia leptopetala R.E. Fries (Annonaceae) e as atividades larvicidas dos óleos essenciais, do extrato metanólico das raízes desta espécie e do alcalóide oxoaporfinico, liriodenina (1), frente às larvas no terceiro estágio do mosquito Aedes aegypti. O extrato metanólico mostrou-se ativo com CL 50 64,6 ± 1,5 ppm e uma forte atividade foi exibida para o composto (1), CL 50 3,6 ± 0,4 ppm. Os óleos essenciais das folhas e galhos também mostraram atividade com CL 50 104,7 ± 0,2 and 34,7 ± 0,3 ppm, respectivamente. Estes dados sugerem que R. leptopetala é fonte potencial de larvicidas naturais. A composição química do óleo essencial e as atividades descritas são comunicadas pela primeira vez.The aim of present study was to describe the chemical composition of the essential oils from the leaf and stem of Rollinia leptopetala R. E. Fries (Annonaceae) and to evaluate the larvicidal activities of these essential oils, of the methanol extract from roots of this plant and of the oxoaporphine alkaloid, liriodenine (1) against the third-instar of Aedes aegypti larvae. The methanol extract from the roots showed larvicidal activity with LC 50 64.6 ± 1.5 ppm. Higher activity was observed for the isolated alkaloid liriodenine (1), LC 50 3.6 ± 0.4 ppm. The essential oils from the leaves and stems, also exhibited larvicidal activity with LC 50 104.7 ± 0.2 and 34.7 ± 0.3 ppm, respectively. These results suggest R. leptopetala as a source of natural larvicidal compounds. This is the first report about the chemical composition and larvicidal activity of the leaf and stem essential oils of R. leptopetala. Keywords: Rollinia leptopetala, Annonaceae, essential oils, liriodenine, Aedes aegypti IntroductionAedes aegypti is the principal mosquito vector of dengue fever, including the hemorrhagic form, which is endemic to South East Asia, Central and South America, and West Africa.1 Between 50 and 100 million of cases are registered each year, causing thousands of deaths. 2The disease has high levels of mortality, and also inflicts great economic losses and social disruption in Brazil. Although some viral diseases, such as yellow fever, have been brought reasonably under control with a vaccine, no vaccine is so far available for dengue. Today, the only way of decreasing the incidence of this disease is by controlling the Aedes aegypti proliferation. This is not an easy task because the mosquitoes have developed resistance to the current synthetic insecticides that, in addition, are toxic to humans and the environment. The mosquito population control in the larval stage is much easier than in the adult Chemical Composition and Larvicidal Activity of Rollinia leptopetala (Annonaceae) J. Braz. Chem. Soc. 376 stage, and then new strategies are needed for controlling the proliferation of the larvae of A. aegypti. Several studies have focused on natural products as insecticides for controlling A. aegypti larvae. Alkaloids and essential oils from herbal plants have ...

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Section: Resultsmentioning

confidence: 99%

Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Feitosa

Arriaga

Conceição

et al. 2009

J. Braz. Chem. Soc.

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“…The parent compound of this class, (4Z)-stemofoline (1; Scheme 1) was isolated and characterized 1970 by Irie et al [4] and reported again in 2001 together with (11E)-and (11Z)-1',2'-didehydrostemofoline (2) from S. collinsae [5]. A compound of identical chemical constitution was described from Asparagus racemosus [6] [7] as asparagamine A ± whose relationship to 1',2'-didehydrostemofoline (2) is a major topic of this contribution.…”

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Two Pyrrolo[1,2‐a]azepine Type Alkaloids from Stemona collinsaeCraib: Structure Elucidations, Relationship to Asparagamine A, and a New Biogenetic Concept of Their Formation

Seger

Mereiter

Kaltenegger

et al. 2004

Chemistry & Biodiversity

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The alkaloids 1',2'-didehydrostemofoline (2) and 2'-hydroxystemofoline (3) from Stemona collinsae Craib (Stemonaceae) were studied by X-ray crystallography and NMR spectroscopy, and they are compared with the parent compound stemofoline (1). The X-ray analysis of the CH2Cl2 solvate of 2'-hydroxystemofoline (3) allowed the determination of the absolute configuration of this compound unequivocally, whereas optical rotation was used to infer the absolute configuration of 1',2'-didehydrostemofoline (2). Based on these results, it is shown that asparagamine A isolated from Asparagus racemosus Willd. (Asparagaceae) is identical to 1',2'-didehydrostemofoline obtained from S. collinsae Craib, and that the reported plant source of asparagamine A was most likely a Stemona species. In the context of the current investigations, a novel concept on the biosynthesis of Stemona alkaloids has been worked out and is presented here.

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“…2 A few of these alkaloids do not fit these five structural groups and have a more complex bridged structure or ring structures that most likely arises from initial oxidative cleavage of the pyrrolo [1,2-a] presence of the C-and D-ring system that is typically found in the stemoamide group of alkaloids, including stemofoline (1). 1,6,[9][10][11][12][13][14][15][16][17] The 13 C/DEPT NMR spectra of 2 indicated four methine carbons, and six methylene carbons and, unlike the other Stemona alkaloids, except 1 and its didehydro and 2'-hydroxy derivatives, 2 a quaternary carbon at  120.4 was apparent, indicative of a acetal-like structure (C-9).…”

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Stemocurtisine, the First Pyrido[1,2-a]azapine Stemona Alkaloid

et al. 2003

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Occurrence of the insecticidal 16,17-didehydro-16(E)-stemofoline in Stemona collinsae

Cited by 68 publications

References 4 publications

Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Two Pyrrolo[1,2‐a]azepine Type Alkaloids from Stemona collinsaeCraib: Structure Elucidations, Relationship to Asparagamine A, and a New Biogenetic Concept of Their Formation

Stemocurtisine, the First Pyrido[1,2-a]azapine Stemona Alkaloid

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