Sampangine, a New Alkaloid from Cananga odorata

Rao, J.U.M.; Giri, G. S.; Hanumaiah, T.; Rao, K. V. J.

doi:10.1021/np50044a029

Cited by 69 publications

(39 citation statements)

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“…Fractionation of this extract by column chromatography gave the alkaloid liriodenine (1), which was identified by comparing its NMR and MS data with those previously reported in the literature. 13,[16][17][18] The alkaloid was evaluated and showed strong larvicidal activity against A. aegypti, with LC 50 3.6 ± 0.4 ppm. Although no similar investigation was found in the literature for oxoaporphine alkaloids, some nitrogenated compounds have been presented as promising larvicides.…”

Section: Resultsmentioning

confidence: 99%

“…Recrystallization of 1 was from MeOH and structural determination was performed by spectral analysis, including comparison with literature data. 16 1 H and 13 C NMR spectra were recorded on a Bruker Advance DRX 500 spectrometer and the mass spectrum was obtained from a VG Auto M Spec Fisions Instruments spectrometer.…”

Section: Extraction and Isolation Of Liriodenine (1)mentioning

confidence: 99%

“…9 The phytochemical investigation of Rollinia species has been reported in the literature revealing acetogenins, steroids, lignans and alkaloids, as secondary metabolites. [10][11][12][13] Previous studies on liriodenine showed prominent antibacterial and cytotoxic biological activities. 14,15 In this paper, the larvicidal activities of R. leptopetala and of the alkaloid liriodenine (1) against the larvae of Aedes aegypti are reported.…”

Section: Introductionmentioning

confidence: 99%

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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%

Section: Extraction and Isolation Of Liriodenine (1)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Feitosa

Arriaga

Conceição

et al. 2009

J. Braz. Chem. Soc.

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“…The production of sampangine is associated with species within the plant family Annonaceae (custard-apple family), including Duguetia hadrantha and Cananga odorata (51,57,60). Like other aporphine alkaloids, sampangine is of particular interest as a potential therapeutic agent, as it exhibits strong inhibitory activity against the human fungal pathogens Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus (51,57).…”

mentioning

confidence: 99%

“…A clearer answer could likely be obtained from transcription profiling studies using comparable heme-deficient mutants from both organisms. Given its essential role in numerous cellular processes, heme biosynthesis or heme signaling could serve as a highly effective target for inhibiting fungal growth and could contribute to a chemical defense strategy against fungal pathogens in aporphinoid-producing plant species of the Annonaceae family (10,27,28,39,44,51,57,60). However, due to the importance of heme in all eukaryotes, a therapeutic drug that targets heme metabolism could most likely lack specificity for the fungal pathogen.…”

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confidence: 99%

Role of Heme in the Antifungal Activity of the Azaoxoaporphine Alkaloid Sampangine

Agarwal¹,

Xu²,

Jacob³

et al. 2008

Eukaryot Cell

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Sampangine, a plant-derived alkaloid found in the Annonaceae family, exhibits strong inhibitory activity against the opportunistic fungal pathogens Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus. In the present study, transcriptional profiling experiments coupled with analyses of mutants were performed in an effort to elucidate its mechanism of action. Using Saccharomyces cerevisiae as a model organism, we show that sampangine produces a transcriptional response indicative of hypoxia, altering the expression of genes known to respond to low-oxygen conditions. Several additional lines of evidence obtained suggest that these responses could involve effects on heme. First, the hem1⌬ mutant lacking the first enzyme in the heme biosynthetic pathway showed increased sensitivity to sampangine, and exogenously supplied hemin partially rescued the inhibitory activity of sampangine in wild-type cells. In addition, heterozygous mutants with deletions in genes involved in five out of eight steps in the heme biosynthetic pathway showed increased susceptibility to sampangine. Furthermore, spectral analyses of pyridine extracts indicated significant accumulation of free porphyrins in sampangine-treated cells. Transcriptional profiling experiments were also performed with C. albicans to investigate the response of a pathogenic fungal species to sampangine. Taking into account the known differences in the physiological responses of C. albicans and S. cerevisiae to low oxygen, significant correlations were observed between the two transcription profiles, suggestive of heme-related defects. Our results indicate that the antifungal activity of the plant alkaloid sampangine is due, at least in part, to perturbations in the biosynthesis or metabolism of heme.

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Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

Koshvandi

Heravi

Momeni

2018

Applied Organom Chemis

165

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Suzuki‐Miyaura Coupling Reaction (SMCR) has been extensively used in the total synthesis of natural products. We underscored these achievements in a report published in Tetrahedron up to 2012. Since then, there has been tremendous growth in this field and numerous articles have been published after 2012. In this review, we tried to go insight and highlight the current developments in the applications of SMCR as a key and strategic step (steps) in the total synthesis of biologically active natural products accomplished and reported from 2012 till date.

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Sampangine, a New Alkaloid from Cananga odorata

Cited by 69 publications

References 1 publication

Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Chemical composition and larvicidal activity of Rollinia leptopetala (Annonaceae)

Role of Heme in the Antifungal Activity of the Azaoxoaporphine Alkaloid Sampangine

Current Applications of Suzuki–Miyaura Coupling Reaction in The Total Synthesis of Natural Products: An update

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