Determination of the absolute configuration of chaetoviridins and other bioactive azaphilones from the endophytic fungus Chaetomium globosum. Issue 21 (1st November 2015)

• Record Type: Journal Article
• 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
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 25:Issue 21(2015)
• Page Start: 4719
• Page End: 4723
• Publication Date: 2015-11-01
• Subjects: Chaetomium globosum -- Wikstroemia uva-ursi -- Azaphilone -- X-ray crystallography -- Anti-inflammatory activity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2015.08.063
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: 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 and3 ), along with five known derivatives (2 and4 –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-α)-induced nuclear factor-kappa B (NF-κB). Compounds4, 5, 7, and synthetic8 and9 inhibit nitric oxide (NO) production with IC50 values in the range of 0.3–5.8 μM. Compounds4, 5, and9 also displayed (TNF-α)-induced NF-κB activity with IC50 values in the range of 0.9–5.1 μM.