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Determination of the absolute configuration of chaetoviridins and other bioactive azaphilones from the endophytic fungus Chaetomium globosum

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Title
Determination of the absolute configuration of chaetoviridins and other bioactive azaphilones from the endophytic fungus Chaetomium globosum
Authors
Youn, Ui Joung
Sripisut, Tawanun
Park, Eun-Jung
Kondratyuk, Tamara P.
Fatima, Nighat
Simmons, Charles J.
Wall, Marisa M.
Sun, Dianqing
Pezzuto, John M.
Chang, Leng Chee
Subject
Pharmacology & Pharmacy; Chemistry
Keywords
Chaetomium globosum; Wikstroemia uva-ursi; Azaphilone; X-ray crystallography; Anti-inflammatory activity
Issue Date
2015
Citation
Youn, Ui Joung, et al. 2015. "Determination of the absolute configuration of chaetoviridins and other bioactive azaphilones from the endophytic fungus Chaetomium globosum". Bioorganic & Medicinal Chemistry Letters, 25: 4719-4723.
Abstract
Chemical investigation of an endophytic fungus Chaetomium globosum isolated from leaves of Wikstroemia uva-ursi led to the isolation of two new azaphilones, chaetoviridins J and K (1 and 3), along with five known derivatives (2 and 4-7). The structures of azaphilones were determined by NMR, X-ray diffraction, Mosher’s method, and CD analysis. The isolated compounds were evaluated for their cancer chemopreventive-potential based on their abilities to inhibit tumor necrosis factor alpha (TNF-a)-induced nuclear factor-kappa B (NF-jB). Compounds 4, 5, 7, and synthetic 8 and 9 inhibit nitric oxide (NO) production with IC50 values in the range of 0.3-5.8 lM. Compounds 4, 5, and 9 also displayed (TNF-a)-induced NF-jB activity with IC50 values in the range of 0.9-5.1 lM.
DOI
http://dx.doi.org/10.1016/j.bmcl.2015.08.063
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