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ARS Home Pacific West Area Hilo, Hawaii Daniel K. Inouye U.S. Pacific Basin Agricultural Research Center Tropical Plant Genetic Resources and Disease Research Research Publications at this Location





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Title:   Author  item
                                            YOUN, UI JOUNG - University Of Hawaiiitem
                                            SRIPISUT, TAWANUN - University Of Hawaiiitem
                                            PARK, EUN-JUNG - University Of Hawaiiitem
                                            KONDRATYUK, TAMARA - University Of Hawaiiitem
                                            FATIMA, NIGHAT - University Of Hawaiiitem
                                            SIMMONS, CHARLES - University Of Hawaiiitem
                                            Wall, Marisaitem
                                            SUN, DIANQING - University Of Hawaiiitem
                                            PEZZUTO, JOHN - University Of Hawaiiitem
                                            CHANG, LENG CHEE - University Of Hawaii
  Submitted to: Bioorganic and Medicinal Chemistry Letters
                                    Publication Type: Peer Reviewed Journal
                                    Publication Acceptance Date: 8/24/2015
                                    Publication  Date: 11/1/2015
                                    Citation: Youn, U., Sripisut, T., Park, E., Kondratyuk, T.P., Fatima, N., Simmons, C.J., Wall, M.M., Sun, D., Pezzuto, J.M., Chang, L. 2015. Determination of the absolute configuration of Chaetoviridins and other bioactive Azaphilones from the endophytic fungus Chaetomium globosum. Bioorganic and Medicinal Chemistry Letters. 25:4719-4723.Interpretive Summary: Chemical extracts of an endophytic fungus, Chaetomium globosum, found in the Hawaiian native plant Wikstroemia uva-ursi (Akia), demonstrated anti-cancer activity in bioassays. Bioassay-guided fractionation of the extract resulted in the isolation of two new chaetoviridins, together with four known compounds. This paper reports the isolation and chemical structure of the new chaetoviridins and the biological activity of all compounds. Three of the compounds demonstrated cancer chemopreventive potential based on their ability to inhibit tumor necrosis factor alpha (TNF-a)-induced NF-'B activity and nitric oxide (NO) production.
                                Technical Abstract: Chemical investigation of an endophytic fungus Chaetomium globosum isolated from leaves of Wikstroemia uva-ursi led to the isolation of a new azaphilone, chaetoviridin J (1), and a new stereoisomer, chaetoviridin K (2), along with four known derivatives (3–6). The structures of azaphilones were determined by NMR, Mosher’s method, and CD analysis. The absolute configuration of chaetoviridin K (2) was also determined by chemical transformation and X-ray diffraction analysis. Compounds 3, 4, and 8 inhibited TNF-a-induced NF-'B activity with IC50 values in the range of 0.9-5.1 uM. Compounds 3, 4, and 6–8 also displayed nitric oxide (NO) inhibitory activity with IC50 values in the range of 0.3-5.8 uM.


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