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Cernumidine and isocernumidine, new type of cyclic guanidine alkaloids from Solanum cernuum |
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| Authors: | Luciane C LopesBianca Roman Maria A MedeirosAbhik Mukhopadhyay Pilar UtrillaJulio Gálvez Sofía García MauriñoVirginia Moltiva Ana Lourenço Arturo San Feliciano |
| Institution: | a Universidade de Sorocaba-UNISO, Programa de Pós-Graduação Strictu Senso em Ciências Farmacêuticas, Rodovia Raposo Tavares, KM 92.5, Cep 18023-000, Sorocaba, SP, Brazil b Laboratório Nacional de Energia e Geologia, I.P., Unidade de Energia Solar, Eólica e dos Oceanos UESEO, Estrada do Paço do Lumiar, 22, 1649-038 Lisboa, Portugal c REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, FCT, Universidade Nova de Lisboa, 2829-516 Caparica, Portugal d CIBER-EHD, Department of Pharmacology, Center for Biomedical Research (CIBM), University of Granada, 18100 Armilla, Ganada, Spain e Departamento de Fisiología Vegetal y Ecología, Facultad de Biología, Universidad de Sevilla, 41012 Sevilla, Spain f Departamento de Farmacología, Facultad de Farmacia, Universidad de Sevilla, 41012 Sevilla, Spain g Departamento de Química Farmacéutica, Facultad de Farmacia-CIETUS, Universidad de Salamanca, 37007-Salamanca, Spain |
| Abstract: | Cernumidine and isocernumidine were identified in the ethanol extract of the leaves of Solanum cernuum Vell. together with four known phenolic compounds. The alkaloids have a natural (2-aminopyrrolidin-1-yl)carboxamidine alkaloidal base acylated with isoferulic (3-hydroxy-4-methoxycinnamic) acid with Z and E configurations, respectively. The structures were elucidated on the basis of 1D- and 2D-NMR data and the structure of cernumidine was confirmed by X-ray analysis. Cernumidine displayed inhibition of interleukin-8 production by HT-29 colon carcinoma cells. This fact could orient further research in gastric cancer prevention and treatment. |
| Keywords: | Alkaloids Cernumidines Solanum cernnum Vell Interleukin-8 |
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