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

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

  • J Nat Prod. 2014 Dec 26;77(12):2711-5. doi: 10.1021/np500538c.
Allan Patrick G Macabeo 1,  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
Affiliations

Affiliation

  • 1 Phytochemistry and Organic Synthesis Laboratory, and ⊥Plant Sciences Laboratory, Research Center for the Natural and Applied Sciences, University of Santo Tomas , 1015 Manila, Philippines.
PMID: 25372601 DOI: 10.1021/np500538c
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.

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