The Pharmacological Activities of (−)-Anonaine

Li, Hsing-Tan; Wu, Huiming; Chen, Hsin‐Liang; Liu, Chi-Ming; Chen, Chung‐Yi

doi:10.3390/molecules18078257

Cited by 37 publications

(23 citation statements)

References 28 publications

(53 reference statements)

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Section: Resultsmentioning

confidence: 99%

“…Important biological activities such as antioxidant, antimicrobial and different pharmacological effects in cardiovascular system, besides significant activity in central nervous system acting in depressive disorders are also reported for anonaine. [34] Besides the antiplasmodial activity of anonaine to resistant chloroquine parasites, anonaine should be pointed out as a potential anticancer compound taking into account its cytotoxicity to HepG2. Indeed, it has been shown that anonaine induces apoptosis through Bax-and caspasedependent pathways in HeLa cells and might be considered a potent compound for chemotherapy against human cervical cancer, because of its effect killing specifically cancer cells, but being safe to normal cells.…”

Section: Identification Of the Alkaloids Isolatedmentioning

confidence: 99%

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Antiplasmodial activity and cytotoxicity, isolation of active alkaloids, and dereplication of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS

Gontijo

Brandão

Nascimento

et al. 2019

Journal of Pharmacy and Pharmacology

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Objectives To assess the antiplasmodial activity of the ethanol extract of Xylopia sericea leaves, Annonaceae, often associated with antimalarial use and to perform a bioguided isolation of active compounds. Methods Dereplication of ethanol extract by the UPLC‐DAD‐ESI‐MS/MS technique allowed the identification of the major constituents, isolation and identification of alkaloids. The antiplasmodial and cytotoxic activity of the extract, fractions and isolated compounds was evaluated against the chloroquine‐resistant W2 strain Plasmodium falciparum and HepG2 cells, respectively. Key findings Ethanol extract showed high reduction of parasitemia as well as moderate cytotoxicity (86.5 ± 3.0% growth inhibition at 50 μg/ml and CC50 72.1 ± 5.1 μg/ml, respectively). A total of eight flavonoids were identified, and two aporphine alkaloids, anonaine and O‐methylmoschatoline, were isolated. Anonaine disclosed significant antiplasmodial effect and moderate cytotoxicity (IC50 23.2 ± 2.7 μg/ml, CC50 38.3 ± 2.3 μg/ml, SI 1.6) while O‐methylmoschatoline was not active against P. falciparum and showed a low cytotoxicity (33.5 ± 1.9% growth inhibition at 50 μg/ml, CC50 274.4 ± 0.5 μg/ml). Conclusions Characterization of Xylopia sericea leaves ethanol extract by UPLC‐DAD‐ESI‐MS/MS as well as its antiplasmodial activity and the occurrence of anonaine and O‐methylmoschatoline in this Xylopia species are reported by the first time.

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Section: Resultsmentioning

confidence: 99%

Section: Identification Of the Alkaloids Isolatedmentioning

confidence: 99%

Antiplasmodial activity and cytotoxicity, isolation of active alkaloids, and dereplication of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS

Gontijo

Brandão

Nascimento

et al. 2019

Journal of Pharmacy and Pharmacology

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“…[40] The influence of season on phytochemical profile and thus bioactivity might be attributed to environments conditions as well as different phenology stages. [41] The low inhibitory activity of stems and leaves, which was null for extracts from some collections, would indicate that the tested fungi are quite resistant to the contained alkaloids or to the combination present in these organs. [37] Therefore, an inclusive analysis of environment and phenology is necessary to understand the modulation of secondary metabolism, with an alternative being the study of young plants wherein the phenological factors can be separated.…”

Section: Discussionmentioning

confidence: 99%

“…Anonaine has been reported to have strong antimicrobial activity. [41] The low inhibitory activity of stems and leaves, which was null for extracts from some collections, would indicate that the tested fungi are quite resistant to the contained alkaloids or to the combination present in these organs. This result shows the importance of the roots of this species in obtaining active molecules, as a consequence of the plant distribution of its chemical defenses.…”

Section: Seasonality and Foliar Phenologymentioning

confidence: 99%

Spatio‐Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity

De-la-Cruz-Chacón

Riley‐Saldaña

Arrollo‐Gómez

et al. 2019

Chemistry & Biodiversity

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Annona purpurea grows in the areas of low elevation in deciduous forests of Mexico, those areas have marked rainy and dry seasons. This species produces more than 30 bioactive alkaloids that could have potential in the control of phytopathogens. This research provides data on the variation of the content and number of alkaloids during an annual cycle and the associated inhibitory potential of the compounds against three phytopathogenic fungi. For one year, alkaloidal extracts of stems and leaves were obtained every two months. The extract profiles were determined by gas chromatography with tandem mass spectrometry and their antifungal activity was examined in vitro. The alkaloids, annomontine and oxopurpureine, obtained from the roots and leaves, respectively, were also evaluated individually. The yields, profiles and activities of the extracts, as well as the abundance of annomontine and oxopurpureine in the extracts, were contrasted with the seasonality and phenological phases of the plant. The data indicate that the alkaloid content was higher at the height of the dry season. High yields also occurred during flowering. The strongest inhibitory effect was obtained from the root extracts during the last month of dry season. This finding seems to be explained by the higher chemodiversity of alkaloids in extracts from this season. Annomontine and oxopurpureine inhibited all three phytopathogens; however, they were not solely responsible for the activity of A. purpurea.

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“…Alcaloides deste tipo já foram descritos em folhas de A. crassiflora Tsai et al, 1989;Li et al, 2013;).…”

Section: Atividade Antimicrobianaunclassified

Atividades biológicas dos alcaloides de Annona crassiflora Mart.

Hidalgo¹

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Nossa lealdade é para as espécies e para o planeta. Nossa obrigação de sobreviver não é apenas para nós, mas também para esse antigo e vasto cosmos a partir do qual derivamos Carl Sagan AgradecimentosA professora Déborah por me receber no Brasil, tanto orientadora como conselheira, sempre presente para escutar, guiar e compartilhar experiências.Ao Professor Marcelo Pena pelo conhecimento transmitido, o tempo dedicado nos fundamentos dos métodos espectrométricos e a boa atitude para resolver duvidas.À Paula Novaes pela ajuda no desenvolvimento dos ensaios fitotóxicos, além de estar preste a colaborar.À Mourisa que sempre está cuidando do laboratório e dos alunos que nele trabalham.À Aline pela ajuda no ajuste dos métodos desenvolvidos nos cromatógrafos.Ao Leandro por estar disposto a ajudar.Às queridas Priscila, que me ajudou bastante, em especial no uso do laboratório e no desenvolvimento de distintas metodologias usadas neste projeto, e Alice pelas dicas estatísticas, as conversas sobre espectrometria de massas e os momentos compartilhados.Aos meus amigos formados neste processo com os quais compartilhei trabalho e experiencias fora do laboratório Lucas, Wilton, Dalila, Cristiane, Cinthia, Carmen, Fernanda Anselmo, Janayna.Aos professores Antonio Salatino, Maria Luiza Salatino e Claudia Furlan, que estiveram abertos a ajudar quando fosse necessário.Ao Luís Doín pela amizade criada nestes anos no Brasil, as conversas, as músicas, as viagens e a paciência.A Natalia e Ricardo por me recever ao inicio deste processo na sua casa e me mostrar um pouco de como é São Paulo.Aos mis amigos de Piracicaba, em especial Amparo, Jake e Gaucho, com vocês compartilhei muitas experiências.A Camila Z, amiga de longo tempo com a qual sempre me sinto como em casa. E a Luana , uma grande amiga com um enorme coração.À querida Lina, minha luz no caminho, pela paciência nos días longos no laboratório, pelas palavras de ánimo, pelo carinho. Os dois aprendimos muito neste tempo no Brasil.Aos meus pais Edgar e Martha por dedicar a vida a minhãs irmãs e a mim, sempre dando carinho, sempre atentos, amo vocês e cada día sinto saudades.À minhas irmãs Ximena e Erika, meus cunhados Ignacio e Fabián e meus sobrinhos David, Isaac e Pablo porque dão a força para estar longe de casa e seguir superando barreiras culturais levando vocês no coração.Por ultimo e não menos importante, ao Brasil, a cada pessoa que encontrei nestes dois anos e fizeram desta experiência algo inesquescível Introdução geralAs plantas medicinais na história humana e seu metabolismo secundário Na busca de sustento e de suprir as necessidades de sobrevivência, os seres humanos têm usado a natureza como fonte de alimento, bem como uma fonte de produtos para curar ou aliviar doenças. Os primórdios do uso das plantas medicinais pelo homem foram instintivos como os animais, dado que na época não havia informações sobre quais plantas usar e para qual O conhecimento sobre as plantas específicas a serem utilizadas e os métodos de aplicação foram transmitidos através da história de f...

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The Pharmacological Activities of (−)-Anonaine

Cited by 37 publications

References 28 publications

Antiplasmodial activity and cytotoxicity, isolation of active alkaloids, and dereplication of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS

Antiplasmodial activity and cytotoxicity, isolation of active alkaloids, and dereplication of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS

Spatio‐Temporal Variation of Alkaloids in Annona purpurea and the Associated Influence on Their Antifungal Activity

Atividades biológicas dos alcaloides de Annona crassiflora Mart.

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