Phytochemical and Larvicidal Studies on Stemona curtisii:  Structure of a New Pyrido[1,2-a]azepine Stemona Alkaloid

Mungkornasawakul, Pitchaya; Pyne, Stephen G.; Jatisatienr, Araya; Supyen, Damrat; Jatisatienr, C.; Lie, Wilford; Ung, Alison T.; Skelton, Brian W.; White, Allan H.

doi:10.1021/np034066u

Cited by 59 publications

(60 citation statements)

References 8 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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“…Some of the pure alkaloids derived from the extracts of the leaves and roots of Stemona species have been shown to have significant antitussive activity in guinea pigs after cough induction [15] as well as insect toxicity, antifeedant, and repellent activities [13,16]. We found that compounds 11, 12, and 14 had significant larvicidal activity on malaria-carrying mosquito larvae (Anopheles minimus HO) [14].…”

Section: Stemona Alkaloidsmentioning

confidence: 81%

“…The pyrrolo[1,2-a]azepine (5,7-bicyclic A,B-ring system) nucleus is common to all compounds in these groups (e.g., croomine 10). In 2003, we [12] and then Greger [13] reported the structures of Stemona alkaloids with a pyrido[1,2-a]azepine A,B-ring system (that is, a 6,7-bicyclic A,B-ring system), including stemocurtisine 11 and oxystemokerrin 12, and in 2004 we disclosed the structure of another pyrido[1,2-a]azepine Stemona alkaloid, stemocurtisinol 13 [14]. These alkaloids comprise a new and sixth structural group.…”

Section: Stemona Alkaloidsmentioning

confidence: 99%

Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

Pyne

Davis

et al. 2008

Pure and Applied Chemistry

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Abstract:We have demonstrated that the borono-Mannich reaction is a versatile and efficient reaction for the diastereoselective preparation of chiral 1,2-amino alcohols. These Mannich products are valuable starting materials as shown in this report by the synthesis of bioactive polyhydroxylated pyrrolizidine and indolizidine alkaloids. Initial studies, directed at the more complex Stemona alkaloids and using the borono-Mannich reaction on cyclic N-acyliminium ions, are encouraging, as demonstrated by the synthesis of the pyrido[1,2-a]azepine core structure of stemocurtisinol.

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“…In 2003, we reported the first pyrido[1,2-a]azepine based Stemona alkaloid, stemocurtisine 1 (Scheme 1), which was isolated from the roots of Stemona curtisii found in Trang Province, Thailand [Mungkornasawakul et al, 2003]. Other Stemona alkaloids with a pyrido[1,2-a]azepine structure were later reported by us [Mungkornasawakul et al, 2004;Pyne et al, 2007]], Greger [Kaltenegger et al, 2003] and Ye [Wang et al, 2007]. Pilli has classified these natural products as Stemocurtisine-type alkaloids [Pilli et al, 2010].…”

Section: Introductionmentioning

confidence: 99%

6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-type alkaloid

Mungkornasawakul

Pyne

Willis

et al. 2013

Phytochemistry Letters

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Lie, W. (2013). 6-Hydroxy-5,6-seco-stemocurtisine: a novel seco-stemocurtisine-type alkaloid. Phytochemistry Letters, 6 (4), 602-605.6-Hydroxy-5,6-seco-stemocurtisine: a novel seco-stemocurtisine-type alkaloid AbstractA novel seco-stemocurtisine-type alkaloid, 6-hydroxy-5,6-seco-stemocurtisine was isolated from the aerial parts of Stemona curtisii (Stemonaceae) collected from Trang Province in Thailand. The unprecedented 5,6-seco-pyrido[1,2-a] azepine structure was elucidated by 2D NMR analysis and a single crystal X-ray crystallographic analysis. (C) 2013 Phytochemical Society of Europe. The unprecedented 5,6-seco-pyrido[1,2-a]azepine structure was elucidated by 2D NMR analysis and a single crystal X-ray crystallographic analysis. 6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-

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Phytochemical and Larvicidal Studies on Stemona curtisii: Structure of a New Pyrido[1,2-a]azepine Stemona Alkaloid

Cited by 59 publications

References 8 publications

Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-type alkaloid

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