ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES
The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nucife...
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
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| Series: | Química Nova |
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| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422018000800884&lng=en&tlng=en |
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| author | Maria de Fátima C. Santos José Eraldo N. Fontes Lívia M. Dutra Larissa M. Bomfim Cinara O. D. Costa Valéria R. S. Moraes Andersson Barison Milena B. P. Soares Felipe Moura A. da Silva Jackson R. G. da Silva Almeida Héctor H. F. Koolen Daniel P. Bezerra Emmanoel Vilaça Costa |
| author_facet | Maria de Fátima C. Santos José Eraldo N. Fontes Lívia M. Dutra Larissa M. Bomfim Cinara O. D. Costa Valéria R. S. Moraes Andersson Barison Milena B. P. Soares Felipe Moura A. da Silva Jackson R. G. da Silva Almeida Héctor H. F. Koolen Daniel P. Bezerra Emmanoel Vilaça Costa |
| author_sort | Maria de Fátima C. Santos |
| collection | DOAJ |
| description | The phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (-)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC50 values of 3.41 an 8.50 µmol L-1, respectively. |
| first_indexed | 2024-04-14T01:33:58Z |
| format | Article |
| id | doaj.art-6f3ed30152ba417282f3f601b4001115 |
| institution | Directory Open Access Journal |
| issn | 1678-7064 |
| language | English |
| last_indexed | 2024-04-14T01:33:58Z |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Química Nova |
| spelling | doaj.art-6f3ed30152ba417282f3f601b40011152022-12-22T02:20:04ZengSociedade Brasileira de QuímicaQuímica Nova1678-706441888489010.21577/0100-4042.20170258S0100-40422018000800884ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIESMaria de Fátima C. SantosJosé Eraldo N. FontesLívia M. DutraLarissa M. BomfimCinara O. D. CostaValéria R. S. MoraesAndersson BarisonMilena B. P. SoaresFelipe Moura A. da SilvaJackson R. G. da Silva AlmeidaHéctor H. F. KoolenDaniel P. BezerraEmmanoel Vilaça CostaThe phytochemical investigation of the alkaloid-rich fraction obtained from the leaves of Guatteria pogonopus Mart. (Annonaceae) allowed the isolation and identification for the first time in this species of: (+)-nornuciferine (1), a mixture of 1 and (+)-anonaine (2), (+)-isocorydine (3), (+)-nuciferine (4), (+)-roemerine (5), (-)-tetrahydropseudocolumbamine (6), a mixture of 6, liriodenine (9) and lysicamine (10), a mixture of 1,2,9-trimethoxy-10-hydroxyaporphine (7) and bulbocapnine (8), 9, 10, and (+)-N-methyllindicarpine (11). Compounds 6, 7, 8, and 11 have not been previously reported in the family Annonaceae. Furthermore, the formerly synthetic 1,2,9-trimethoxyaporfin-10-ol (7) is described for the first time as a natural aporphine alkaloid herein. The chemical structures were established by 1D and 2D NMR as well as in comparison with data previously reported in the literature. The cytotoxic activity of the alkaloids was evaluated against tumor (B16-F10, HepG2, HL-60, and K562) and non-tumor (PBMC) cell lines. Alkaloid 1 presented significant activity against HepG2 cell lines with IC50 of 9.60 µmol L-1 while the mixture of 6, 9 and 10 displayed strong cytotoxic activity against HL-60 and K562 cell lines with IC50 values of 3.41 an 8.50 µmol L-1, respectively.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422018000800884&lng=en&tlng=enalkaloidsGuatteria pogonopusleavesAnnonaceaeNMRcytotoxicity |
| spellingShingle | Maria de Fátima C. Santos José Eraldo N. Fontes Lívia M. Dutra Larissa M. Bomfim Cinara O. D. Costa Valéria R. S. Moraes Andersson Barison Milena B. P. Soares Felipe Moura A. da Silva Jackson R. G. da Silva Almeida Héctor H. F. Koolen Daniel P. Bezerra Emmanoel Vilaça Costa ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES Química Nova alkaloids Guatteria pogonopus leaves Annonaceae NMR cytotoxicity |
| title | ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES |
| title_full | ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES |
| title_fullStr | ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES |
| title_full_unstemmed | ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES |
| title_short | ALKALOIDS FROM LEAVES OF GUATTERIA POGONOPUS (ANNONACEAE) AND THEIR CYTOTOXICITIES |
| title_sort | alkaloids from leaves of guatteria pogonopus annonaceae and their cytotoxicities |
| topic | alkaloids Guatteria pogonopus leaves Annonaceae NMR cytotoxicity |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422018000800884&lng=en&tlng=en |
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