Proteasome inhibitors from Neoboutonia melleri

Long, Christophe, Beck, Josephine, Cantagrel, Frederic, Marcourt, Laurence, Vendier, Laure, David, Bruno, Plisson, Fabien, Derguini, Fadila, Vandenberghe, Isabelle, Aussagues, Yannick, Ausseil, Frederic, Lavaud, Catherine, Sautel, Francois and Massiot, Georges (2012) Proteasome inhibitors from Neoboutonia melleri. Journal of Natural Products, 75 1: 34-47. doi:10.1021/np200441h


Author Long, Christophe
Beck, Josephine
Cantagrel, Frederic
Marcourt, Laurence
Vendier, Laure
David, Bruno
Plisson, Fabien
Derguini, Fadila
Vandenberghe, Isabelle
Aussagues, Yannick
Ausseil, Frederic
Lavaud, Catherine
Sautel, Francois
Massiot, Georges
Title Proteasome inhibitors from Neoboutonia melleri
Formatted title
Proteasome inhibitors from Neoboutonia melleri
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 0163-3864
1520-6025
Publication date 2012-01
Year available 2011
Sub-type Article (original research)
DOI 10.1021/np200441h
Open Access Status
Volume 75
Issue 1
Start page 34
End page 47
Total pages 14
Place of publication Washington, DC, United States
Publisher American Chemical Society
Collection year 2013
Language eng
Formatted abstract
Thirty new cycloartane derivatives (1–3, 5–12, 14–32) have been isolated from the leaves of Neoboutonia melleri. Their novelty stems from the loss of one of the C-4 methyl groups (1–3, 5–12, 14–25, and 32) and from the presence of an “extra” carbon atom in the side chain (1–3, 5–12, 14–20, 26–29, and 30–32). Furthermore, compound 32 possesses a rare triterpene skeleton with the cyclopropane ring fused onto C-1 and C-10, instead of C-9 and C-10. The structures were determined by spectrometric means, chemical correlations, and X-ray crystallography of derivative 1c. The substitution pattern in ring A, with a cyclopropyl ring conjugated with an α,β-unsaturated carbonyl moiety, confers to the molecule a particular reactivity, giving rise to a formal inversion of the stereochemistry of the cyclopropane ring under UV irradiation. These compounds showed an interesting level of activity on the proteasome pathway, thus motivating their evaluation as possible anticancer agents. The large number of isolated compounds permitted a structure–activity relationship analysis, which showed that the presence of the two enone functions was a requirement for the activity.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status Non-UQ
Additional Notes Publication Date (Web): December 14, 2011

Document type: Journal Article
Sub-type: Article (original research)
Collections: Non HERDC
Institute for Molecular Bioscience - Publications
 
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Created: Mon, 03 Sep 2012, 09:11:37 EST by Susan Allen on behalf of Institute for Molecular Bioscience