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The Brazilian Amaryllidaceae as a source of acetylcholinesterase inhibitory alkaloids

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Abstract

Nine Brazilian Amaryllidaceae species were studied for their alkaloid composition and acetylcholinesterase (AChE) inhibitory activity via GC–MS and a modified Ellman assay, respectively. A total of thirty-six alkaloids were identified in these plants, of which Hippeastrum papilio and H. glaucescens exhibited the highest galanthamine content and the best IC50 values against AChE. Furthermore, Hippeastrum vittatum and Rhodophiala bifida also showed notable AChE inhibitory effects. X-ray crystallographic data for four galanthamine-type compounds revealed significant differences in the orientation of the N-methyl group, which are shown to be related to AChE inhibition.

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Notes

  1. CCDC 1029491 contains the supplementary crystallographic data for compound 28. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/Community/Requestastructure/Pages/Requestastructure.aspx (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Tel: +44 (0)1223 336408; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).

  2. CCDC 1029490 contains the supplementary crystallographic data for compound 32. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/Community/Requestastructure/Pages/Requestastructure.aspx (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Tel: +44 (0)1223 336408; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).

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Authors and Affiliations

  1. Departament de Productes Naturals, Biologia Vegetal i Edafologia, Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal 643, 08028, Barcelona, Spain

    Jean Paulo de Andrade, Laura Torras-Claveria, Natalia Belén Pigni, Strahil Berkov, Francesc Viladomat, Jerald J. Nair & Jaume Bastida

  2. Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul, 2752 Ipiranga Av., Porto Alegre, 90610-000, Brazil

    Jean Paulo de Andrade, Raquel B. Giordani, Eduardo Konrath, Kelly Bueno, Liana G. Sachett, Amelia T. Henriques & José Angelo S. Zuanazzi

  3. AgroBioInstitute, 8 Dragan Tzankov blvd., 1164, Sofia, Bulgaria

    Strahil Berkov

  4. Centres Cientifics i Tecnologics, Universitat de Barcelona, Solé i Sabaris 1-3, 08028, Barcelona, Spain

    Mercè Font-Bardia

  5. Cristal.lografia, Mineralogia i Dipòsits Minerals, Facultat de Geologia, Universitat de Barcelona, Martí i Franquès s/n, 08028, Barcelona, Spain

    Teresa Calvet

  6. Departamento de Botânica, Universidade de Campinas, Cidade Universitária, Campinas, 13083-970, Brazil

    Julie H. Dutilh

  7. Departamento de Química, Universidade do Espírito Santo, Vitoria, ES, 29075-910, Brazil

    Jean Paulo de Andrade & Warley de Souza Borges

Authors
  1. Jean Paulo de Andrade
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  2. Raquel B. Giordani
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  3. Laura Torras-Claveria
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  4. Natalia Belén Pigni
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  5. Strahil Berkov
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  6. Mercè Font-Bardia
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  7. Teresa Calvet
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  8. Eduardo Konrath
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  9. Kelly Bueno
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  10. Liana G. Sachett
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  13. Francesc Viladomat
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  14. Amelia T. Henriques
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  15. Jerald J. Nair
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  16. José Angelo S. Zuanazzi
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  17. Jaume Bastida
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Correspondence to Jaume Bastida.

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de Andrade, J.P., Giordani, R.B., Torras-Claveria, L. et al. The Brazilian Amaryllidaceae as a source of acetylcholinesterase inhibitory alkaloids. Phytochem Rev 15, 147–160 (2016). https://doi.org/10.1007/s11101-015-9411-7

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  • DOI: https://doi.org/10.1007/s11101-015-9411-7

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