| Full text | |
| Author(s): Show less - |
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 |