Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/57632
Type: Artigo de periódico
Title: Cytotoxic non-aromatic B-ring flavanones from Piper carniconnectivum C. DC.
Author: Freitas, GC
Batista, JM
Franchi, GC
Nowill, AE
Yamaguchi, LF
Vilcachagua, JD
Favaro, DC
Furlan, M
Guimaraes, EF
Jeffrey, CS
Kato, MJ
Abstract: 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.
Subject: Piper carniconnectivum
Piperaceae
Non-aromatic B-ring flavanone
Cytotoxic
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Rights: fechado
Identifier DOI: 10.1016/j.phytochem.2013.10.012
Date Issue: 2014
Appears in Collections:Unicamp - Artigos e Outros Documentos

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