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

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• 作者：Yusuke Myobatake ; Kenji Takemoto ; Shinji Kamisuki ; Natsuki Inoue ; Ayato Takasaki ; Toshifumi Takeuchi ; Yoshiyuki Mizushina ; Fumio Sugawara
• 刊名：Journal of Natural Products
• 出版年：2014
• 出版时间：May 23, 2014
• 年：2014
• 卷：77
• 期：5
• 页码：1236-1240
• 全文大小：228K
• 年卷期：v.77,no.5(May 23, 2014)
• ISSN：1520-6025

文摘

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鈥?.3 渭M, while violaceoid F was found to be cytotoxic against HCT116 and RAW264.7 with LD₅₀ values of 6.4 and 6.5 渭M, respectively. These results demonstrate that violaceoid derivatives are a new class of cytotoxic hydroquinones with a hydroxymethyl and a linear alkyl substituent.