Versixanthones A-F, Cytotoxic Xanthone-Chromanone Dimers from the Marine-Derived Fungus Aspergillus versicolor HDN1009

Guangwei Wu, Guihong Yu, Tibor Kurtán, Attila Mándi, Jixing Peng, Xiaomei Mo, Ming Liu, Hui Li, Xinhua Sun, Jing Li, Tianjiao Zhu, Qianqun Gu, Dehai Li

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

Six unusual xanthone-chromanone dimers, versixanthones A-F (1-6), 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 1-6, 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-chromanone dimers and supported the assignments of their absolute configurations. Compounds 1-6 exhibited cytotoxicities against the seven tested cancer cell lines, with the best IC50 value of 0.7 μM. Compound 5 showed further inhibitory activity against topoisomerase I.

Original languageEnglish
Pages (from-to)2691-2698
Number of pages8
JournalJournal of Natural Products
Volume78
Issue number11
DOIs
Publication statusPublished - Nov 25 2015

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Wu, G., Yu, G., Kurtán, T., Mándi, A., Peng, J., Mo, X., Liu, M., Li, H., Sun, X., Li, J., Zhu, T., Gu, Q., & Li, D. (2015). Versixanthones A-F, Cytotoxic Xanthone-Chromanone Dimers from the Marine-Derived Fungus Aspergillus versicolor HDN1009. Journal of Natural Products, 78(11), 2691-2698. https://doi.org/10.1021/acs.jnatprod.5b00636