Cytotoxic non-aromatic B-ring flavanones from Piper carniconnectivum C. DC.
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Data
2014-01-01
Autores
Freitas, Giovana C.
Batista, Joao M. [UNESP]
Franchi, Gilberto C.
Nowill, Alexandre E.
Yamaguchi, Lydia F.
Vilcachagua, Janaina D.
Favaro, Denize C.
Furlan, Maysa [UNESP]
Guimaraes, Elsie F.
Jeffrey, Christopher S.
Título da Revista
ISSN da Revista
Título de Volume
Editor
Elsevier B.V.
Resumo
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.
Descrição
Palavras-chave
Piper carniconnectivum, Piperaceae, Non-aromatic B-ring flavanone, Cytotoxic
Como citar
Phytochemistry. Oxford: Pergamon-elsevier Science Ltd, v. 97, p. 81-87, 2014.