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Type: Artigo de periódico
Title: Cytotoxic Non-aromatic B-ring Flavanones From Piper Carniconnectivum C. Dc.
Author: Freitas G.C.
Batista Jr. J.M.
Franchi Jr. G.C.
Nowill A.E.
Yamaguchi L.F.
Vilcachagua J.D.
Favaro D.C.
Furlan M.
Guimaraes E.F.
Jeffrey C.S.
Kato M.J.
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 μM) indicated the activity of 1 against seven cell lines. © 2013 Elsevier Ltd. All rights reserved.
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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