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Embellicines A and B: Absolute Configuration and NF-κB Transcriptional Inhibitory Activity

Authors
Type
Published Article
Journal
Journal of Medicinal Chemistry
Publisher
American Chemical Society
Publication Date
Aug 20, 2013
Volume
79
Issue
13
Pages
2991–2999
Identifiers
DOI: 10.1021/jm400034b
Source
LBMCC
Keywords
License
Blue

Abstract

Two new metabolites, embellicines A and B (1 and 2), were isolated from the EtOAc extract of the fungus Embellisia eureka, an endophyte of the Moroccan plant Cladanthus arabicus (Asteraceae). The structures of these new compounds were determined on the basis of extensive one- and two-dimensional NMR spectroscopy as well as by high-resolution mass spectrometry. The absolute configuration of embellicine A (1) was determined by TDDFT ECD calculations of solution conformers, whereas that of embellicine B (2) was deduced based on ROESY correlations and on biogenetic considerations in comparison to 1. Both embellicines (1 and 2) are cytostatic, cytotoxic and inhibit NF-κB transcriptional activity, indicating that inhibition of NF-κB may be a possible mechanism of action of these compounds. Embellicine B (2), was the most active compound encountered in this study and acts at nanomolar concentrations without affecting tumor microenvironment.

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