Cytotoxic alkylated hydroquinone, phenol, and cyclohexenone derivatives from Aspergillus violaceofuscus Gasperini.
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.
Department of Applied Biological Science, Tokyo University of Science , Noda, Chiba 278-8510, Japan.
Yusuke
Y
Myobatake
Kenji
K
Takemoto
Shinji
S
Kamisuki
Natsuki
N
Inoue
Ayato
A
Takasaki
Toshifumi
T
Takeuchi
Yoshiyuki
Y
Mizushina
Fumio
F
Sugawara
D000478:Alkylation; D000818:Animals; D001230:Aspergillus / Q000737:chemistry*; D003512:Cyclohexanones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D045325:HCT116 Cells; D006801:Humans; D006873:Hydroquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D003512:Cyclohexanones; D006873:Hydroquinones; D010636:Phenols