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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Cytotoxic non-aromatic B-ring flavanones from Piper carniconnectivum C. DC.

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Author(s):
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Freitas, Giovana C. [1] ; Batista, Jr., Joao M. [2] ; Franchi, Jr., Gilberto C. [3] ; Nowill, Alexandre E. [3] ; Yamaguchi, Lydia F. [1] ; Vilcachagua, Janaina D. [1] ; Favaro, Denize C. [1] ; Furlan, Maysa [2] ; Guimaraes, Elsie F. [4] ; Jeffrey, Christopher S. [5] ; Kato, Massuo J. [1]
Total Authors: 11
Affiliation:
[1] Univ Sao Paulo, Inst Quim, Res Support Ctr Mol Divers Nat Prod, BR-05599970 Sao Paulo - Brazil
[2] Univ Estadual Paulista, UNESP, Inst Quim, NUBBE, BR-14800900 Araraquara, SP - Brazil
[3] Univ Estadual Campinas, Ctr Integrado Pesquisas Oncohematol Infancia, BR-13083970 Campinas, SP - Brazil
[4] Inst Pesquisas Jardim Bot Rio de Janeiro, BR-22460030 Rio De Janeiro, RJ - Brazil
[5] Univ Nevada, Dept Chem, Reno, NV 89557 - USA
Total Affiliations: 5
Document type: Journal article
Source: Phytochemistry; v. 97, p. 81-87, JAN 2014.
Web of Science Citations: 4
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-d ihydro-4H-chromen-4-one (1) and 5-hydroxy-2-(1',2'-dihydroxy-4'-oxo-cyclohexyl)-6,7-dimethoxy-2,3-dihydr o-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. (AU)

FAPESP's process: 11/22339-4 - Chiroptical methods for the characterization of micro- and macromolecules from natural sources
Grantee:João Marcos Batista Junior
Support Opportunities: Scholarships in Brazil - Post-Doctoral