Versixanthones A鈥揊, Cytotoxic Xanthone鈥揅hromanone Dimers from the Marine-Derived Fungus Aspergillus versicolor HDN1009

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• 作者：Guangwei Wu ; Guihong Yu ; Tibor Kurt谩n ; Attila M谩ndi ; Jixing Peng ; Xiaomei Mo ; Ming Liu ; Hui Li ; Xinhua Sun ; Jing Li ; Tianjiao Zhu ; Qianqun Gu ; Dehai Li
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：November 25, 2015
• 年：2015
• 卷：78
• 期：11
• 页码：2691-2698
• 全文大小：486K
• ISSN：1520-6025

文摘

Six unusual xanthone鈥揷hromanone dimers, versixanthones A鈥揊 (1鈥?b>6), featuring different formal linkages of tetrahydroxanthone and 2,2-disubstituted chroman-4-one monomers, were isolated from a culture of the mangrove-derived fungus Aspergillus versicolor HDN1009. The absolute configurations of 1鈥?b>6, representing the central and axial chirality elements or preferred helicities, were established by a combination of X-ray diffraction analysis, chemical conversions, and TDDFT-ECD calculations. The interconversion of different biaryl linkages between 1 and 4 and between 2 and 3 in DMSO by a retro-oxa-Michael mechanism provided insight into the formation of the xanthone鈥揷hromanone dimers and supported the assignments of their absolute configurations. Compounds 1鈥?b>6 exhibited cytotoxicities against the seven tested cancer cell lines, with the best IC₅₀ value of 0.7 渭M. Compound 5 showed further inhibitory activity against topoisomerase I.