Inhibition of the human chemokine receptor CCR5 by variecolin and variecolol and isolation of four new variecolin analogues, emericolins A−D, from Emericella aurantiobrunnea

Yoganathan, K., Rossant, Christine, Glover, Robert P., Cao, Shugeng, Vittal, Jagadese J., Ng, Siewbee, Huang, Yicun, Buss, Antony D. and Butler, Mark S. (2004) Inhibition of the human chemokine receptor CCR5 by variecolin and variecolol and isolation of four new variecolin analogues, emericolins A−D, from Emericella aurantiobrunnea. Journal of Natural Products, 67 10: 1681-1684. doi:10.1021/np049844c


Author Yoganathan, K.
Rossant, Christine
Glover, Robert P.
Cao, Shugeng
Vittal, Jagadese J.
Ng, Siewbee
Huang, Yicun
Buss, Antony D.
Butler, Mark S.
Title Inhibition of the human chemokine receptor CCR5 by variecolin and variecolol and isolation of four new variecolin analogues, emericolins A−D, from Emericella aurantiobrunnea
Formatted title
Inhibition of the human chemokine receptor CCR5 by variecolin and variecolol and isolation of four new variecolin analogues, emericolins A−D, from Emericella aurantiobrunnea
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 0163-3864
1520-6025
Publication date 2004-10-01
Sub-type Article (original research)
DOI 10.1021/np049844c
Volume 67
Issue 10
Start page 1681
End page 1684
Total pages 4
Editor A. Kinghorn Douglas
Place of publication Cincinnati, OH, U.S.A.
Publisher American Chemical Society
Language eng
Subject 0601 Biochemistry and Cell Biology
0607 Plant Biology
Formatted abstract
An extract from the fungus Emericella aurantiobrunnea was found to compete with macrophage inflammatory protein (MIP)-1α for binding to human CCR5 in a scintillation proximity assay (SPA). Bioassay-guided fractionation led to the isolation of variecolin (1) and variecolol (2), which had IC50 values of 9 and 32 μM, respectively. An X-ray crystal structure of variecolin (1) was obtained for the first time. Also isolated were four new inactive analogues, emericolin A (3), B (4), C (5), and D (6), and the relative stereochemistry of these compounds was determined by NMR methods using ROESY spectra and 1H/1H coupling constants.
© 2004 American Chemical Society and American Society of Pharmacognosy.

Keyword Emericella aurantiobrunnea
Macrophage inflammatory protein
Scintillation proximity assay
Variecolin
Variecolol
Emericolin A, B, C, and D
Q-Index Code C1

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
Institute for Molecular Bioscience - Publications
 
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Created: Tue, 23 Mar 2010, 00:18:42 EST by June Temby on behalf of Institute for Molecular Bioscience