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Synergistic TRAIL sensitizers from Barleria alluaudii and Diospyros maritima.

MPG-Autoren
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Sun,  H.
Department of NMR based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Griesinger,  C.
Department of NMR based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

Externe Ressourcen

http://pubs.acs.org/doi/pdfplus/10.1021/np200805z
(Verlagsversion)

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1452594_si_001.pdf
(Ergänzendes Material), 602KB

Zitation

Whitson, E. L., Sun, H., Thomas, C. L., Heinrich, C. J., Sayers, T. J., McMahon, J. B., et al. (2012). Synergistic TRAIL sensitizers from Barleria alluaudii and Diospyros maritima. Journal of Natural Products, 75(3), 394-399. doi:10.1021/np200805z.


Zitierlink: https://hdl.handle.net/11858/00-001M-0000-000F-8570-F
Zusammenfassung
Barleria alluaudii and Diospyros maritima were both investigated as part of an ongoing search for synergistic TRAIL (tumor necrosis factor-α-related apoptosis-inducing ligand) sensitizers. As a result of this study, two naphthoquinone epoxides, 2,3-epoxy-2,3-dihydrolapachol (1) and 2,3-epoxy-2,3-dihydro-8-hydroxylapachol (2), both not previously isolated from natural sources, and the known 2-methylanthraquinone (3) were identified from B. alluaudii. Time-dependent density functional theory (TD-DFT) calculations of electronic circular dichroism (ECD) spectra were utilized to establish the absolute configuration of 1 and 2. Additionally, five known naphthoquinone derivatives, maritinone (4), elliptinone (5), plumbagin (6), (+)-cis-isoshinanolone (7), and ethylidene-6,6′-biplumbagin (8), were isolated from D. maritima. Compounds 1, 2, and 4–6 showed varying levels of synergy with TRAIL. Maritinone (4) and elliptinone (5) showed the highest synergistic effect, with more than a 3-fold increase in activity observed with TRAIL than with compound alone.