Cytotoxic non-aromatic B-ring flavanones from Piper carniconnectivum C. DC.
Contribuinte(s) |
Universidade Estadual Paulista (UNESP) |
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Data(s) |
03/12/2014
03/12/2014
01/01/2014
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Resumo |
Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) Processo FAPESP: 09/51850-9 The EtOAc extract from the leaves of Piper carniconnectivum C. DC. was subjected to chromatographic separation to afford two non-aromatic B-ring flavanone compounds: 5-hydroxy-2-(1'-hydroxy-4'-oxo-cyclohex-2'-en-1'-yl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one (1) and 5-hydroxy-2-(1',2'-dihydroxy-4'-oxo-cyclohexyl)-6,7-dimethoxy-2,3-dihydro-4H-chromen-4-one (2). The absolute configuration of (+)-1 was unambiguously determined as 2S,1'R by electronic circular dichroism (ECD) spectroscopy and comparison to simulated spectra that were calculated using time-dependent density functional theory (TDDFT). This methodology allowed the assignment of the absolute configuration of (+)-2 also as 2S,1'R, except for the stereogenic center at C-2', which was assigned as R because of the evidence drawn from high resolution NMR experiments. The cytotoxic activity of both compounds and 3 (hydrogenated B-ring derivative of 1) was evaluated on twelve human leukemia cell lines, and the IC50 values (<10 mu M) indicated the activity of 1 against seven cell lines. (C) 2013 Elsevier Ltd. All rights reserved. |
Formato |
81-87 |
Identificador |
http://dx.doi.org/10.1016/j.phytochem.2013.10.012 Phytochemistry. Oxford: Pergamon-elsevier Science Ltd, v. 97, p. 81-87, 2014. 0031-9422 http://hdl.handle.net/11449/111458 10.1016/j.phytochem.2013.10.012 WOS:000330144600010 |
Idioma(s) |
eng |
Publicador |
Elsevier B.V. |
Relação |
Phytochemistry |
Direitos |
closedAccess |
Palavras-Chave | #Piper carniconnectivum #Piperaceae #Non-aromatic B-ring flavanone #Cytotoxic |
Tipo |
info:eu-repo/semantics/article |