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Cytotoxic Alkylated Hydroquinone, Phenol, and Cyclohexenone Derivatives from Aspergillus violaceofuscus Gasperini

Myobatake, Yusuke, Takemoto, Kenji, Kamisuki, Shinji, Inoue, Natsuki, Takasaki, Ayato, Takeuchi, Toshifumi, Mizushina, Yoshiyuki, Sugawara, Fumio
Journal of natural products 2014 v.77 no.5 pp. 1236-1240
Aspergillus, culture media, cytotoxicity, humans, hydroquinone, lethal dose 50, macrophages, mice, mosses and liverworts, neoplasm cells, neoplasms, nuclear magnetic resonance spectroscopy, spectral analysis
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.