Document Detail

Synergistic TRAIL sensitizers from Barleria alluaudii and Diospyros maritima.
MedLine Citation:
PMID:  22313254     Owner:  NLM     Status:  MEDLINE    
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.
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:
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:
Title:  Journal of natural products     Volume:  75     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2012 Mar 
Date Detail:
Created Date:  2012-03-23     Completed Date:  2012-05-22     Revised Date:  2013-06-26    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  United States    
Other Details:
Languages:  eng     Pagination:  394-9     Citation Subset:  IM    
Molecular Targets Laboratory, Molecular Discovery Program, Center for Cancer Research, NCI-Frederick, Frederick, Maryland 21702, United States.
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MeSH Terms
Acanthaceae / chemistry*
Anthraquinones / chemistry,  isolation & purification*,  pharmacology
Diospyros / chemistry*
Molecular Structure
Naphthoquinones / chemistry,  isolation & purification*,  pharmacology
TNF-Related Apoptosis-Inducing Ligand / drug effects*,  metabolism
Tumor Necrosis Factor-alpha
Grant Support
HHSN261200800001E//PHS HHS; Z99 CA999999/CA/NCI NIH HHS
Reg. No./Substance:
0/Anthraquinones; 0/Naphthoquinones; 0/TNF-Related Apoptosis-Inducing Ligand; 0/Tumor Necrosis Factor-alpha; 0/maritinone; Q9P233HWAJ/2-methylanthraquinone; YAS4TBQ4OQ/plumbagin

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