Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| 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/48736 |
Resumo: | 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. |
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Costa, Emmanoel VilaçaSoares, Liviane do N.Chaar, Jamal da SilvaSilva, Valdenizia R.Santos, Luciano de S.Koolen, Hector Henrique FerreiraSilva, Felipe Moura Araujo daTavares, Josean F.Zengin, GokhanSoares, Milena Botelho PereiraBezerra, Daniel Pereira2021-08-25T14:21:08Z2021-08-25T14:21:08Z2021COSTA, Emmanoel Vilaça et al. Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities. Molecules, 2021.1420-3049https://www.arca.fiocruz.br/handle/icict/4873610.3390/molecules26123714Conselho 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.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Amazonas State University. Metabolomics and Mass Spectrometry Research Group. Manaus, AM, Brazil.Federal University of Amazonas. Department of Chemistry. Manaus, AM, Brazil.Federal University of Paraíba. Health Sciences Center. Postgraduate Program in Natural and Synthetic Bioactive Products. João Pessoa, PA, Brazil.Selcuk University. Science Faculty. Department of Biology. Konya, Turkey.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Bahia, Brasil.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.engMDPIAlcaloidesAnnonaceaeEspectroscopia de Ressonância MagnéticaConcentração Inibidora 50Diclinanona calycinaAlkaloids and benzylated dihydroflavonesCytotoxic activityBenzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (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/48736/1/license.txt36b51ef91c52b5338d9d29ba0cc807bcMD51ORIGINALCosta, Emmanoel V. Benzylated....pdfCosta, Emmanoel V. 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Benzylated....pdf.txtExtracted texttext/plain55930https://www.arca.fiocruz.br/bitstream/icict/48736/3/Costa%2c%20Emmanoel%20V.%20Benzylated....pdf.txt44f6f9e77db91763455a855cd8058185MD53icict/487362023-03-15 14:34:27.595oai:www.arca.fiocruz.br:icict/48736Q0VTU8ODTyBOw4NPIEVYQ0xVU0lWQSBERSBESVJFSVRPUyBBVVRPUkFJUw0KDQpBbmEgTWFyaWEgRmlzY2luYSBTYW1wYWlvLCBDUEY6IDA2NS40MzEuMDM1LTE1LCB2aW5jdWxhZG8gYSBDUHFHTSAtIENlbnRybyBkZSBQZXNxdWlzYXMgR29uw6dhbG8gTW9uaXoKCkFvIGFjZWl0YXIgb3MgVEVSTU9TIGUgQ09OREnDh8OVRVMgZGVzdGEgQ0VTU8ODTywgbyBBVVRPUiBlL291IFRJVFVMQVIgZGUgZGlyZWl0b3MKYXV0b3JhaXMgc29icmUgYSBPQlJBIGRlIHF1ZSB0cmF0YSBlc3RlIGRvY3VtZW50bzoKCigxKSBDRURFIGUgVFJBTlNGRVJFLCB0b3RhbCBlIGdyYXR1aXRhbWVudGUsIMOgIEZJT0NSVVogLSBGVU5EQcOHw4NPIE9TV0FMRE8gQ1JVWiwgZW0KY2Fyw6F0ZXIgcGVybWFuZW50ZSwgaXJyZXZvZ8OhdmVsIGUgTsODTyBFWENMVVNJVk8sIHRvZG9zIG9zIGRpcmVpdG9zIHBhdHJpbW9uaWFpcyBOw4NPCkNPTUVSQ0lBSVMgZGUgdXRpbGl6YcOnw6NvIGRhIE9CUkEgYXJ0w61zdGljYSBlL291IGNpZW50w61maWNhIGluZGljYWRhIGFjaW1hLCBpbmNsdXNpdmUgb3MgZGlyZWl0b3MKZGUgdm96IGUgaW1hZ2VtIHZpbmN1bGFkb3Mgw6AgT0JSQSwgZHVyYW50ZSB0b2RvIG8gcHJhem8gZGUgZHVyYcOnw6NvIGRvcyBkaXJlaXRvcyBhdXRvcmFpcywgZW0KcXVhbHF1ZXIgaWRpb21hIGUgZW0gdG9kb3Mgb3MgcGHDrXNlczsKCigyKSBBQ0VJVEEgcXVlIGEgY2Vzc8OjbyB0b3RhbCBuw6NvIGV4Y2x1c2l2YSwgcGVybWFuZW50ZSBlIGlycmV2b2fDoXZlbCBkb3MgZGlyZWl0b3MgYXV0b3JhaXMKcGF0cmltb25pYWlzIG7Do28gY29tZXJjaWFpcyBkZSB1dGlsaXphw6fDo28gZGUgcXVlIHRyYXRhIGVzdGUgZG9jdW1lbnRvIGluY2x1aSwgZXhlbXBsaWZpY2F0aXZhbWVudGUsCm9zIGRpcmVpdG9zIGRlIGRpc3BvbmliaWxpemHDp8OjbyBlIGNvbXVuaWNhw6fDo28gcMO6YmxpY2EgZGEgT0JSQSwgZW0gcXVhbHF1ZXIgbWVpbyBvdSB2ZcOtY3VsbywKaW5jbHVzaXZlIGVtIFJlcG9zaXTDs3Jpb3MgRGlnaXRhaXMsIGJlbSBjb21vIG9zIGRpcmVpdG9zIGRlIHJlcHJvZHXDp8OjbywgZXhpYmnDp8OjbywgZXhlY3XDp8OjbywKZGVjbGFtYcOnw6NvLCByZWNpdGHDp8OjbywgZXhwb3Npw6fDo28sIGFycXVpdmFtZW50bywgaW5jbHVzw6NvIGVtIGJhbmNvIGRlIGRhZG9zLCBwcmVzZXJ2YcOnw6NvLCBkaWZ1c8OjbywKZGlzdHJpYnVpw6fDo28sIGRpdnVsZ2HDp8OjbywgZW1wcsOpc3RpbW8sIHRyYWR1w6fDo28sIGR1YmxhZ2VtLCBsZWdlbmRhZ2VtLCBpbmNsdXPDo28gZW0gbm92YXMgb2JyYXMgb3UKY29sZXTDom5lYXMsIHJldXRpbGl6YcOnw6NvLCBlZGnDp8OjbywgcHJvZHXDp8OjbyBkZSBtYXRlcmlhbCBkaWTDoXRpY28gZSBjdXJzb3Mgb3UgcXVhbHF1ZXIgZm9ybWEgZGUKdXRpbGl6YcOnw6NvIG7Do28gY29tZXJjaWFsOwoKKDMpIFJFQ09OSEVDRSBxdWUgYSBjZXNzw6NvIGFxdWkgZXNwZWNpZmljYWRhIGNvbmNlZGUgw6AgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETwpDUlVaIG8gZGlyZWl0byBkZSBhdXRvcml6YXIgcXVhbHF1ZXIgcGVzc29hIOKAkyBmw61zaWNhIG91IGp1csOtZGljYSwgcMO6YmxpY2Egb3UgcHJpdmFkYSwgbmFjaW9uYWwgb3UKZXN0cmFuZ2VpcmEg4oCTIGEgYWNlc3NhciBlIHV0aWxpemFyIGFtcGxhbWVudGUgYSBPQlJBLCBzZW0gZXhjbHVzaXZpZGFkZSwgcGFyYSBxdWFpc3F1ZXIKZmluYWxpZGFkZXMgbsOjbyBjb21lcmNpYWlzOwoKKDQpIERFQ0xBUkEgcXVlIGEgb2JyYSDDqSBjcmlhw6fDo28gb3JpZ2luYWwgZSBxdWUgw6kgbyB0aXR1bGFyIGRvcyBkaXJlaXRvcyBhcXVpIGNlZGlkb3MgZSBhdXRvcml6YWRvcywKcmVzcG9uc2FiaWxpemFuZG8tc2UgaW50ZWdyYWxtZW50ZSBwZWxvIGNvbnRlw7pkbyBlIG91dHJvcyBlbGVtZW50b3MgcXVlIGZhemVtIHBhcnRlIGRhIE9CUkEsCmluY2x1c2l2ZSBvcyBkaXJlaXRvcyBkZSB2b3ogZSBpbWFnZW0gdmluY3VsYWRvcyDDoCBPQlJBLCBvYnJpZ2FuZG8tc2UgYSBpbmRlbml6YXIgdGVyY2Vpcm9zIHBvcgpkYW5vcywgYmVtIGNvbW8gaW5kZW5pemFyIGUgcmVzc2FyY2lyIGEgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETyBDUlVaIGRlCmV2ZW50dWFpcyBkZXNwZXNhcyBxdWUgdmllcmVtIGEgc3Vwb3J0YXIsIGVtIHJhesOjbyBkZSBxdWFscXVlciBvZmVuc2EgYSBkaXJlaXRvcyBhdXRvcmFpcyBvdQpkaXJlaXRvcyBkZSB2b3ogb3UgaW1hZ2VtLCBwcmluY2lwYWxtZW50ZSBubyBxdWUgZGl6IHJlc3BlaXRvIGEgcGzDoWdpbyBlIHZpb2xhw6fDtWVzIGRlIGRpcmVpdG9zOwoKKDUpIEFGSVJNQSBxdWUgY29uaGVjZSBhIFBvbMOtdGljYSBJbnN0aXR1Y2lvbmFsIGRlIEFjZXNzbyBBYmVydG8gZGEgRklPQ1JVWiAtIEZVTkRBw4fDg08KT1NXQUxETyBDUlVaIGUgYXMgZGlyZXRyaXplcyBwYXJhIG8gZnVuY2lvbmFtZW50byBkbyByZXBvc2l0w7NyaW8gaW5zdGl0dWNpb25hbCBBUkNBLgoKQSBQb2zDrXRpY2EgSW5zdGl0dWNpb25hbCBkZSBBY2Vzc28gQWJlcnRvIGRhIEZJT0NSVVogLSBGVU5EQcOHw4NPIE9TV0FMRE8gQ1JVWiByZXNlcnZhCmV4Y2x1c2l2YW1lbnRlIGFvIEFVVE9SIG9zIGRpcmVpdG9zIG1vcmFpcyBlIG9zIHVzb3MgY29tZXJjaWFpcyBzb2JyZSBhcyBvYnJhcyBkZSBzdWEgYXV0b3JpYQplL291IHRpdHVsYXJpZGFkZSwgc2VuZG8gb3MgdGVyY2Vpcm9zIHVzdcOhcmlvcyByZXNwb25zw6F2ZWlzIHBlbGEgYXRyaWJ1acOnw6NvIGRlIGF1dG9yaWEgZSBtYW51dGVuw6fDo28KZGEgaW50ZWdyaWRhZGUgZGEgT0JSQSBlbSBxdWFscXVlciB1dGlsaXphw6fDo28uCgpBIFBvbMOtdGljYSBJbnN0aXR1Y2lvbmFsIGRlIEFjZXNzbyBBYmVydG8gZGEgRklPQ1JVWiAtIEZVTkRBw4fDg08gT1NXQUxETyBDUlVaCnJlc3BlaXRhIG9zIGNvbnRyYXRvcyBlIGFjb3Jkb3MgcHJlZXhpc3RlbnRlcyBkb3MgQXV0b3JlcyBjb20gdGVyY2Vpcm9zLCBjYWJlbmRvIGFvcyBBdXRvcmVzCmluZm9ybWFyIMOgIEluc3RpdHVpw6fDo28gYXMgY29uZGnDp8O1ZXMgZSBvdXRyYXMgcmVzdHJpw6fDtWVzIGltcG9zdGFzIHBvciBlc3RlcyBpbnN0cnVtZW50b3MuCg==Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-03-15T17:34:27Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities |
| title |
Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities |
| spellingShingle |
Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities Costa, Emmanoel Vilaça Alcaloides Annonaceae Espectroscopia de Ressonância Magnética Concentração Inibidora 50 Diclinanona calycina Alkaloids and benzylated dihydroflavones Cytotoxic activity |
| title_short |
Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities |
| title_full |
Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities |
| title_fullStr |
Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities |
| title_full_unstemmed |
Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities |
| title_sort |
Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities |
| author |
Costa, Emmanoel Vilaça |
| author_facet |
Costa, Emmanoel Vilaça Soares, Liviane do N. Chaar, Jamal da Silva Silva, Valdenizia R. Santos, Luciano de S. Koolen, Hector Henrique Ferreira Silva, Felipe Moura Araujo da Tavares, Josean F. Zengin, Gokhan Soares, Milena Botelho Pereira Bezerra, Daniel Pereira |
| author_role |
author |
| author2 |
Soares, Liviane do N. Chaar, Jamal da Silva Silva, Valdenizia R. Santos, Luciano de S. Koolen, Hector Henrique Ferreira Silva, Felipe Moura Araujo da Tavares, Josean F. Zengin, Gokhan Soares, Milena Botelho Pereira Bezerra, Daniel Pereira |
| author2_role |
author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Costa, Emmanoel Vilaça Soares, Liviane do N. Chaar, Jamal da Silva Silva, Valdenizia R. Santos, Luciano de S. Koolen, Hector Henrique Ferreira Silva, Felipe Moura Araujo da Tavares, Josean F. Zengin, Gokhan Soares, Milena Botelho Pereira Bezerra, Daniel Pereira |
| dc.subject.other.pt_BR.fl_str_mv |
Alcaloides Annonaceae Espectroscopia de Ressonância Magnética Concentração Inibidora 50 |
| topic |
Alcaloides Annonaceae Espectroscopia de Ressonância Magnética Concentração Inibidora 50 Diclinanona calycina Alkaloids and benzylated dihydroflavones Cytotoxic activity |
| dc.subject.en.pt_BR.fl_str_mv |
Diclinanona calycina Alkaloids and benzylated dihydroflavones Cytotoxic activity |
| description |
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. |
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2021 |
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2021-08-25T14:21:08Z |
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2021-08-25T14:21:08Z |
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2021 |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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COSTA, Emmanoel Vilaça et al. Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities. Molecules, 2021. |
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https://www.arca.fiocruz.br/handle/icict/48736 |
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1420-3049 |
| dc.identifier.doi.none.fl_str_mv |
10.3390/molecules26123714 |
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COSTA, Emmanoel Vilaça et al. Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities. Molecules, 2021. 1420-3049 10.3390/molecules26123714 |
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MDPI |
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