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

Ana Maria Ferreira da Costa Lourenço

doi:10.1016/j.tetlet.2011.09.060

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

Ana Maria Ferreira da Costa Lourenço

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

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. (C) 2011 Elsevier Ltd. All rights reserved.

Original language	Unknown
Pages (from-to)	6392-6395
Journal	Tetrahedron Letters
Volume	52
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2011.09.060
Publication status	Published - 1 Jan 2011

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10.1016/j.tetlet.2011.09.060

Cite this

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

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. (C) 2011 Elsevier Ltd. All rights reserved.",

keywords = "Alkaloids, Cernumidines, Interleukin-8, Solanum cernnum Vell.",

author = "Louren{\c c}o, {Ana Maria Ferreira da Costa}",

year = "2011",

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doi = "10.1016/j.tetlet.2011.09.060",

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volume = "52",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Cernumidine and isocernumidine, new type of cyclic guanidine alkaloids from Solanum cernuum

AU - Lourenço, Ana Maria Ferreira da Costa

PY - 2011/1/1

Y1 - 2011/1/1

N2 - 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. (C) 2011 Elsevier Ltd. All rights reserved.

AB - 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. (C) 2011 Elsevier Ltd. All rights reserved.

KW - Alkaloids

KW - Cernumidines

KW - Interleukin-8

KW - Solanum cernnum Vell.

U2 - 10.1016/j.tetlet.2011.09.060

DO - 10.1016/j.tetlet.2011.09.060

M3 - Article

SN - 0040-4039

VL - 52

SP - 6392

EP - 6395

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -