| Author | Costa, Emmanoel Vilaça | |
| Author | Soares, Liviane do N. | |
| Author | Chaar, Jamal da Silva | |
| Author | Silva, Valdenizia R. | |
| Author | Santos, Luciano de S. | |
| Author | Koolen, Hector Henrique Ferreira | |
| Author | Silva, Felipe Moura Araujo da | |
| Author | Tavares, Josean F. | |
| Author | Zengin, Gokhan | |
| Author | Soares, Milena Botelho Pereira | |
| Author | Bezerra, Daniel Pereira | |
| Access date | 2021-08-25T14:21:08Z | |
| Available date | 2021-08-25T14:21:08Z | |
| Document date | 2021 | |
| Citation | COSTA, Emmanoel Vilaça et al. Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities. Molecules, 2021. | pt_BR |
| ISSN | 1420-3049 | pt_BR |
| URI | https://www.arca.fiocruz.br/handle/icict/48736 | |
| Sponsorship | Conselho Nacional de Desenvolvimento Científico e Tecnológico
(CNPq: grant numbers 302445/2017-0 and 304577/2020-0) and Coordenação de Aperfeiçoamento
de Pessoal de Nível Superior (CAPES)—Code 001. | pt_BR |
| Language | eng | pt_BR |
| Publisher | MDPI | pt_BR |
| Rights | open access | pt_BR |
| Subject in Portuguese | Alcaloides | pt_BR |
| Subject in Portuguese | Annonaceae | pt_BR |
| Subject in Portuguese | Espectroscopia de Ressonância Magnética | pt_BR |
| Subject in Portuguese | Concentração Inibidora 50 | pt_BR |
| Title | Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities | pt_BR |
| Type | Article | pt_BR |
| DOI | 10.3390/molecules26123714 | |
| Abstract | Diclinanona calycina R. E. Fries popularly known as “envira”, is a species of the Annonaceae
family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon
plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded
thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in
the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis
using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified
as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine,
liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline
(3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5);
(+)-1S,2R-reticuline N -oxide (6); and (+)-1S,2S-reticuline N -oxide (7); tetrahydroprotoberberine,
coreximine (8); and pavine, bisnorargemonine (9). While the flavonoids belong to the benzylated
dihydroflavones, isochamanetin (10), dichamanetin (11), and a mixture of uvarinol (12) and isouvarinol
(13). Compound 5 is described for the first time in the literature as a natural product. The
cytotoxic activity of the main isolated compounds was evaluated against cancer and non-cancerous
cell lines. Among the tested compounds, the most promising results were found for the benzylated
dihydroflavones dichamanetin (10), and the mixture of uvarinol (12) and isouvarinol (13), which
presented moderate cytotoxic activity against the tested cancer cell lines (<20.0 g mL1) and low
cytotoxicity against the non-cancerous cell line MRC-5 (>25.0 g mL1). Dichamanetin (11) showed
cytotoxic activity against HL-60 and HCT116 with IC50 values of 15.78 g mL1 (33.70 mol L1)
and 18.99 g mL1 (40.56 mol L1), respectively while the mixture of uvarinol (12) and isouvarinol
(13) demonstrated cytotoxic activity against HL-60, with an IC50 value of 9.74 g mL1, and HCT116,
with an IC50 value of 17.31 g mL1. These cytotoxic activities can be attributed to the presence
of one or more hydroxybenzyl groups present in these molecules as well as the position in which
these groups are linked. The cytotoxic activities of reticuline, anonaine and liriodenine have been
previously established, with liriodenine being the most potent compound. | pt_BR |
| Affilliation | Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil. | pt_BR |
| Affilliation | Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil. | pt_BR |
| Affilliation | Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil. | pt_BR |
| Affilliation | Amazonas State University. Metabolomics and Mass Spectrometry Research Group. Manaus, AM, Brazil. | pt_BR |
| Affilliation | Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil. | pt_BR |
| Affilliation | Federal University of Paraíba. Health Sciences Center. Postgraduate Program in Natural and Synthetic Bioactive Products. João Pessoa, PA, Brazil. | pt_BR |
| Affilliation | Selcuk University. Science Faculty. Department of Biology. Konya, Turkey. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil. | pt_BR |
| Affilliation | Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil. | pt_BR |
| Subject | Diclinanona calycina | pt_BR |
| Subject | Alkaloids and benzylated dihydroflavones | pt_BR |
| Subject | Cytotoxic activity | pt_BR |
