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Synergistic TRAIL Sensitizers from Barleria alluaudii and Diospyros maritima

  1. Author:
    Whitson, E. L.
    Sun, H.
    Thomas, C. L.
    Henrich, C. J.
    Sayers, T. J.
    McMahon, J. B.
    Griesinger, C.
    McKee, T. C.

  2. Author Address

    [Whitson, Emily L.; Thomas, Cheryl L.; Henrich, Curtis J.; McMahon, James B.; McKee, Tawnya C.] NCI Frederick, Mol Targets Lab, Mol Discovery Program, Ctr Canc Res, Frederick, MD 21702 USA. [Sun, Han; Griesinger, Christian] Max Planck Inst Biophys Chem, Dept NMR Based Struct Biol, D-37077 Gottingen, Germany. [Henrich, Curtis J.; Sayers, Thomas J.] SAIC Frederick Inc, Frederick, MD 21702 USA. [Sayers, Thomas J.] NCI Frederick, Expt Immunol Lab, Canc & Inflammat Program, Ctr Canc Res, Frederick, MD 21702 USA.;Mckee, TC (reprint author), NCI Frederick, Mol Targets Lab, Mol Discovery Program, Ctr Canc Res, Frederick, MD 21702 USA;mckeeta@mail.nih.gov
    1. Year: 2012
    2. Date: Mar
  2. Journal: Journal of Natural Products
    1. 75
    2. 3
    3. Pages: 394-399
  4. Type of Article: Article
  5. ISSN: 0163-3864
  1. Abstract:

    Barleria alluaudii and Diospyros maritima were both investigated as part of an ongoing search for synergistic TRAIL (tumor necrosis factor-alpha-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.

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External Sources

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  2. DOI: 10.1021/np200805z
  3. View record in Web of Science®
  4. WOS: 000301810700010

Library Notes

  1. Fiscal Year: FY2011-2012
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