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  Synergistic TRAIL sensitizers from Barleria alluaudii and Diospyros maritima.

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.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-000F-8570-F Version Permalink: http://hdl.handle.net/11858/00-001M-0000-0027-CAF1-9
Genre: Journal Article

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 Creators:
Whitson, E. L., Author
Sun, H.1, Author              
Thomas, C. L., Author
Heinrich, C. J., Author
Sayers, T. J., Author
McMahon, J. B., Author
Griesinger, C.1, Author              
Mckee, T. C., Author
Affiliations:
1Department of NMR based Structural Biology, MPI for biophysical chemistry, Max Planck Society, ou_578567              

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 Abstract: 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.

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Language(s): eng - English
 Dates: 2012-02-072012-03
 Publication Status: Published in print
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 Rev. Method: Peer
 Identifiers: DOI: 10.1021/np200805z
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Title: Journal of Natural Products
Source Genre: Journal
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Pages: - Volume / Issue: 75 (3) Sequence Number: - Start / End Page: 394 - 399 Identifier: -