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

Author:
Myobatake, Yusuke, Takemoto, Kenji, Kamisuki, Shinji, Inoue, Natsuki, Takasaki, Ayato, Takeuchi, Toshifumi, Mizushina, Yoshiyuki, Sugawara, Fumio
Source:
Journal of natural products 2014 v.77 no.5 pp. 1236-1240
ISSN:
1520-6025
Subject:
Aspergillus, culture media, cytotoxicity, humans, hydroquinone, lethal dose 50, macrophages, mice, mosses and liverworts, neoplasm cells, neoplasms, nuclear magnetic resonance spectroscopy, spectral analysis
Abstract:
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.
Agid:
5494381