Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2020 |
| Outros Autores: | , , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/45763 |
Resumo: | Analytical Center of the Multidisciplinary Support Center at the UFAM (CA/CAM/UFAM) for the NMR and MS analysis, and CNPq, CAPES, FINEP, FAPESB, and UFAM for financial support and fellowship. |
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Souza, César A. S. deNardellia, Victória B.Paza, Weider H. P.Pinheiro, Maria Lúcia B.Rodrigues, Ana Carolina Borges da CruzBomfim, Larissa MendesSoares, Milena Botelho PereiraBezerra, Daniel PereiraChaar, Jamal da S.Koolen, Hector Henrique FerreiraSilva, Felipe Moura Araujo daCosta, Emmanoel Vilaça2021-01-21T13:53:16Z2021-01-21T13:53:16Z2020SOUZA, César A. S. de et al. Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities. Quimica Nova, v. 15, p. 1-7, 2020.0100-4042https://www.arca.fiocruz.br/handle/icict/4576310.21577/0100-4042.20170617Analytical Center of the Multidisciplinary Support Center at the UFAM (CA/CAM/UFAM) for the NMR and MS analysis, and CNPq, CAPES, FINEP, FAPESB, and UFAM for financial support and fellowship.Universidade Federal do Amazonas. Instituto de Ciências Exatas. Departamento de Química. Manaus, AM, Brasil.Universidade Federal do Amazonas. Instituto de Ciências Exatas. Departamento de Química. Manaus, AM, Brasil.Universidade Federal do Amazonas. Instituto de Ciências Exatas. Departamento de Química. Manaus, AM, Brasil.Universidade Federal do Amazonas. Instituto de Ciências Exatas. Departamento de Química. Manaus, AM, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Universidade Federal do Amazonas. Instituto de Ciências Exatas. Departamento de Química. Manaus, AM, Brasil.Universidade do Estado do Amazonas. Escola Superior de Ciências da Saúde. Manaus, AM, Brasil.Universidade Federal do Amazonas. Centro de Apoio Multidisciplinar. Central Analítica. Manaus, AM, Brasil.Universidade Federal do Amazonas. Instituto de Ciências Exatas. Departamento de Química. Manaus, AM, Brasil.The phytochemical investigation of the hexane and methanol extracts from the bark of Duguetia pycnastera Sandwith (Annonaceae) afforded seven known compounds, two asarone-derived phenylpropanoids and five isoquinoline-derived alkaloids. The asarones, γ-asarone (1-allyl-2,4,5-trimethoxybenzene) and 2,4,5-trimethoxy-styrene were isolated of the hexane extract while the aporphine alkaloids, O-methylmoschatoline, lysicamine, nornuciferidine, and guatterine N-oxide, and the benzyltetrahydroisoquinoline alkaloid, (S)-reticuline were isolated of the alkaloid fraction of the methanol extract. This is the first report of these compounds in D. pycnastera. γ-Asarone is being reported for the first time in the Annonaceae. Nornuciferidine is described for the second time in the Annonaceae while guatterine N-oxide is the third register. The structures of the isolated compounds were established by extensive analyses using 1D and 2D NMR spectroscopy in combination with MS. The cytotoxic activity of the isolated compounds (except for nornuciferidine) was evaluated against cancer and non-cancerous cell lines, in which lysicamine was the most active compound, mainly against HL-60, HepG2, and K562 with IC50 values of 24.40, 28.86 and 38.75 μmol L-1, respectively.engPubliSBQAlcaloidesMetanolAnnonaceaeCancerDuguetia pycnasteraAsaronesAporphine alkaloidBenzyltetrahydroisoquinoline alkaloidCytotoxic activityAsarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-83097https://www.arca.fiocruz.br/bitstream/icict/45763/1/license.txt36b51ef91c52b5338d9d29ba0cc807bcMD51ORIGINALSouza, Cesar A de Asarone-Derived.pdfSouza, Cesar A de Asarone-Derived.pdfapplication/pdf1146330https://www.arca.fiocruz.br/bitstream/icict/45763/2/Souza%2c%20Cesar%20A%20de%20Asarone-Derived.pdfd8365345aac9fc934013c28efde901f1MD52TEXTSouza, Cesar A de Asarone-Derived.pdf.txtSouza, Cesar A de Asarone-Derived.pdf.txtExtracted texttext/plain36342https://www.arca.fiocruz.br/bitstream/icict/45763/3/Souza%2c%20Cesar%20A%20de%20Asarone-Derived.pdf.txteee03f87bcfbc4dfea502abed5e2f3ffMD53icict/457632023-03-15 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| dc.title.pt_BR.fl_str_mv |
Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities |
| title |
Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities |
| spellingShingle |
Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities Souza, César A. S. de Alcaloides Metanol Annonaceae Cancer Duguetia pycnastera Asarones Aporphine alkaloid Benzyltetrahydroisoquinoline alkaloid Cytotoxic activity |
| title_short |
Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities |
| title_full |
Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities |
| title_fullStr |
Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities |
| title_full_unstemmed |
Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities |
| title_sort |
Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities |
| author |
Souza, César A. S. de |
| author_facet |
Souza, César A. S. de Nardellia, Victória B. Paza, Weider H. P. Pinheiro, Maria Lúcia B. Rodrigues, Ana Carolina Borges da Cruz Bomfim, Larissa Mendes Soares, Milena Botelho Pereira Bezerra, Daniel Pereira Chaar, Jamal da S. Koolen, Hector Henrique Ferreira Silva, Felipe Moura Araujo da Costa, Emmanoel Vilaça |
| author_role |
author |
| author2 |
Nardellia, Victória B. Paza, Weider H. P. Pinheiro, Maria Lúcia B. Rodrigues, Ana Carolina Borges da Cruz Bomfim, Larissa Mendes Soares, Milena Botelho Pereira Bezerra, Daniel Pereira Chaar, Jamal da S. Koolen, Hector Henrique Ferreira Silva, Felipe Moura Araujo da Costa, Emmanoel Vilaça |
| author2_role |
author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Souza, César A. S. de Nardellia, Victória B. Paza, Weider H. P. Pinheiro, Maria Lúcia B. Rodrigues, Ana Carolina Borges da Cruz Bomfim, Larissa Mendes Soares, Milena Botelho Pereira Bezerra, Daniel Pereira Chaar, Jamal da S. Koolen, Hector Henrique Ferreira Silva, Felipe Moura Araujo da Costa, Emmanoel Vilaça |
| dc.subject.other.pt_BR.fl_str_mv |
Alcaloides Metanol Annonaceae Cancer |
| topic |
Alcaloides Metanol Annonaceae Cancer Duguetia pycnastera Asarones Aporphine alkaloid Benzyltetrahydroisoquinoline alkaloid Cytotoxic activity |
| dc.subject.en.pt_BR.fl_str_mv |
Duguetia pycnastera Asarones Aporphine alkaloid Benzyltetrahydroisoquinoline alkaloid Cytotoxic activity |
| description |
Analytical Center of the Multidisciplinary Support Center at the UFAM (CA/CAM/UFAM) for the NMR and MS analysis, and CNPq, CAPES, FINEP, FAPESB, and UFAM for financial support and fellowship. |
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2020 |
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2020 |
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2021-01-21T13:53:16Z |
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2021-01-21T13:53:16Z |
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info:eu-repo/semantics/article |
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SOUZA, César A. S. de et al. Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities. Quimica Nova, v. 15, p. 1-7, 2020. |
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https://www.arca.fiocruz.br/handle/icict/45763 |
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0100-4042 |
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10.21577/0100-4042.20170617 |
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SOUZA, César A. S. de et al. Asarone-derived Phenylpropanoids anda isoquinoline-derived alkaloids from the bark of Duguetia pycnastera (Annonaceae) and their cytotoxicities. Quimica Nova, v. 15, p. 1-7, 2020. 0100-4042 10.21577/0100-4042.20170617 |
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