Cernumidine and isocernumidine, new type of cyclic guanidine alkaloids from Solanum cernuum

• Published in: Tetrahedron letters Vol. 52; no. 48; pp. 6392 - 6395
• Main Authors: Lopes, Luciane C., Roman, Bianca, Medeiros, Maria A., Mukhopadhyay, Abhik, Utrilla, Pilar, Gálvez, Julio, Mauriño, Sofía García, Moltiva, Virginia, Lourenço, Ana, Feliciano, Arturo San
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.11.2011; Elsevier
• Subjects: Alkaloids; Cancer; Cernumidines; Chemistry; Chemistry, Organic; Colon; Ethanol; Ethyl alcohol; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Interleukin-8; Noncondensed benzenic compounds; Organic chemistry; Phenols; Physical Sciences; Preparations and properties; Science & Technology; Solanum cernnum Vell; Tetrahedrons; X-rays; Alkaloids; Cernumidines; Interleukin-8; Solanum cernnum Vell; ACID; METABOLISM; IDENTIFICATION; PROTEIN DEACETYLASE; CANCER; SIRT1; Carcinoma; Configuration; Molecular structure; Nitrogen heterocycle; NMR spectrometry; Pyrrolidine derivatives; Prevention; Alkaloid; Dicotyledones; Angiospermae; Solanaceae; Inhibition; Solanum; Acylation; Ethanol; Plant leaf; Guanidines; Malignant tumor; X ray diffraction; Cyclic compound; Cinnamic acid derivatives; Plant origin; Phenols; Benzenic compound; Spermatophyta; Cancer; Structural analysis
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.09.060

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.