Antineoplastic Agents. 556. Isolation and Structure of Coprinastatin 1 from Coprinus cinereus

Cancer cell line bioassay-guided Separation of an ethyl acetate extract prepared from a plant-associated fungus, Coprinus citiereus, led to the isolation of three new sesquiterpenes, coprinaslatin 1 (1), coprinol (2), and the epimer (4a), of the known sesquiterpene triol 4b. The previously described sesquiterpene 3 and oxazolinone 5 were also isolated. The structure and relative configuration Of coprinastatin 1 (1) were determined by HRMS and by 1D- and 2D-NMR spectroscopic analyses. The Structure of terpene 2 Was elucidated by single-crystal X-ray diffraction experiments. The remaining, Structures were similarly determined, Structure 3 by Spectroscopic analyses and both 4a and 5 by X-ray crystal structure determination. Coprinastatin 1 (1) Was found to inhibit growth of the murine P388 lymphocytic leukemia cell line and the pathogenic bacterium Neisseria gonorrhoeae.