Tetrahydroxanthene-1,3(2 H)-dione derivatives from Uvaria valderramensis

Allan Patrick G. Macabeo, Franze Perry A. Martinez, Tibor Kurtán, László Tóth, Attila Mándi, Sebastian Schmidt, Jörg Heilmann, Grecebio Jonathan D. Alejandro, Matthias Knorn, Hans Martin Dahse, Scott G. Franzblau

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18 Citations (Scopus)

Abstract

Two tetrahydroxanthene-1,3(2H)-dione metabolites, valderramenols A (1) and B (2), were isolated from the Philippine endemic Annonaceous species Uvaria valderramensis. Planar structures of the rac-xanthene-1,3-(2H)-diones 1 and 2 were established by MS and NMR measurements. Their enantiomers were separated by chiral HPLC, and the absolute configurations of the separated enantiomers were determined by comparison of the HPLC-ECD spectra with computed TDDFT-generated spectra. A TDDFT-ECD study of the known grandiuvarone (3) allowed the revision of its absolute configuration as S. Compound 1 showed antitubercular activity (MIC 10 μg/mL), while 3 and 4 had weaker activities (MIC 32 μg/mL). Oxepinone 3 exhibited cytotoxic activity against KB-562, a chronic myeloid leukemia cell line.

Original languageEnglish
Pages (from-to)2711-2715
Number of pages5
JournalJournal of Natural Products
Volume77
Issue number12
DOIs
Publication statusPublished - Dec 26 2014

ASJC Scopus subject areas

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

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  • Cite this

    Macabeo, A. P. G., Martinez, F. P. A., Kurtán, T., Tóth, L., Mándi, A., Schmidt, S., Heilmann, J., Alejandro, G. J. D., Knorn, M., Dahse, H. M., & Franzblau, S. G. (2014). Tetrahydroxanthene-1,3(2 H)-dione derivatives from Uvaria valderramensis. Journal of Natural Products, 77(12), 2711-2715. https://doi.org/10.1021/np500538c