| Synergistic TRAIL sensitizers from Barleria alluaudii and Diospyros maritima. | |
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MedLine Citation:
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PMID: 22313254 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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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Authors:
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Emily L Whitson; Han Sun; Cheryl L Thomas; Curtis J Henrich; Thomas J Sayers; James B McMahon; Christian Griesinger; Tawnya C McKee |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, N.I.H., Intramural; Research Support, Non-U.S. Gov't Date: 2012-02-07 |
Journal Detail:
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Title: Journal of natural products Volume: 75 ISSN: 1520-6025 ISO Abbreviation: J. Nat. Prod. Publication Date: 2012 Mar |
Date Detail:
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Created Date: 2012-03-23 Completed Date: 2012-05-22 Revised Date: 2013-04-18 |
Medline Journal Info:
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Nlm Unique ID: 7906882 Medline TA: J Nat Prod Country: United States |
Other Details:
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Languages: eng Pagination: 394-9 Citation Subset: IM |
Affiliation:
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Molecular Targets Laboratory, Molecular Discovery Program, Center for Cancer Research, NCI-Frederick, Frederick, Maryland 21702, United States. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acanthaceae
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chemistry* Anthraquinones / chemistry, isolation & purification*, pharmacology Diospyros / chemistry* Madagascar Molecular Structure Naphthoquinones / chemistry, isolation & purification*, pharmacology TNF-Related Apoptosis-Inducing Ligand / drug effects*, metabolism Tumor Necrosis Factor-alpha |
| Grant Support | |
ID/Acronym/Agency:
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HHSN261200800001E//PHS HHS; Z99 CA999999/CA/NCI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Anthraquinones; 0/Naphthoquinones; 0/TNF-Related Apoptosis-Inducing Ligand; 0/Tumor Necrosis Factor-alpha; 0/maritinone; Q9P233HWAJ/2-methylanthraquinone; YAS4TBQ4OQ/plumbagin |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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