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 cinereus, led to the isolation of three new sesquiterpenes, coprinastatin 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.