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J Nat Prod ; 77(5): 1236-40, 2014 May 23.
Artigo em Inglês | MEDLINE | ID: mdl-24786915

RESUMO

New alkylated hydroquinones violaceoid A (1), violaceoid B (2), and violaceoid C (3), an alkylated phenol violaceoid D (4), and a cyclohexenoid violaceoid E (5) were isolated from a culture broth of Aspergillus violaceofuscus Gasperini isolated from moss. The structures were identified by interpretation of spectroscopic data (1D and 2D NMR, MS, and IR). Two known compounds, the cyclohexenoid 6 and eupenoxide (7), were also isolated. Compound 6 was isolated for the first time as a natural product and named violaceoid F. Isolated compounds were tested for cytotoxic activity against five human cancer cell lines and a mouse macrophage cell line. Violaceoid A was the most potent of the seven compounds against all cell lines. Violaceoid C and D exhibited cytotoxicity against the leukemia cell lines with LD50 values 5.9-8.3 µM, while violaceoid F was found to be cytotoxic against HCT116 and RAW264.7 with LD50 values of 6.4 and 6.5 µM, respectively. These results demonstrate that violaceoid derivatives are a new class of cytotoxic hydroquinones with a hydroxymethyl and a linear alkyl substituent.


Assuntos
Aspergillus/química , Cicloexanonas/isolamento & purificação , Hidroquinonas/isolamento & purificação , Fenóis/isolamento & purificação , Alquilação , Animais , Cicloexanonas/química , Cicloexanonas/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Células HCT116 , Humanos , Hidroquinonas/química , Hidroquinonas/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Fenóis/química , Fenóis/farmacologia
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