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

Autor(es):Mostrar menos -

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]

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: Phytochemistry; v. 97, p. 81-87, JAN 2014.
• Citações Web of Science: 4

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-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)

• Processo FAPESP: 09/51850-9 - Diversidade molecular em Angiospermas basais
• Beneficiário: Massuo Jorge Kato
• Modalidade de apoio: Auxílio à Pesquisa - Programa BIOEN - Temático
• Processo FAPESP: 11/22339-4 - Métodos quirópticos para caracterização de micro- e macromoléculas de origem natural
• Beneficiário: João Marcos Batista Junior
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado
• Processo FAPESP: 08/58717-0 - Estudos metabolômicos e genômicos em Piperaceae
• Beneficiário: Giovana Cássia de Freitas Lemeszenski
• Modalidade de apoio: Bolsas no Brasil - Doutorado Direto
• Processo FAPESP: 08/58658-3 - Estudo químico e biológico de benzopiranos naturais em espécies de Piperaceae e seus análogos
• Beneficiário: João Marcos Batista Junior
• Modalidade de apoio: Bolsas no Brasil - Doutorado Direto