title: Antineoplastic agents. 556. Isolation and structure of Coprinastatin 1 from Coprinus cinereus.
abstract: 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.
authors.affiliation: Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona 85287-1604, USA. bpettit@asu.edu
authors.forename: George R
authors.initials: GR
authors.lastname: Pettit
authors.forename: Yanhui
authors.initials: Y
authors.lastname: Meng
authors.forename: Robin K
authors.initials: RK
authors.lastname: Pettit
authors.forename: Delbert L
authors.initials: DL
authors.lastname: Herald
authors.forename: Zbigniew A
authors.initials: ZA
authors.lastname: Cichacz
authors.forename: Dennis L
authors.initials: DL
authors.lastname: Doubek
authors.forename: Linda
authors.initials: L
authors.lastname: Richert
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D007941:Leukemia P388; D051379:Mice; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D009344:Neisseria gonorrhoeae / Q000187:drug effects*; D019906:Nuclear Magnetic Resonance, Biomolecular; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D012717:Sesquiterpenes; C548950:coprinastatin 1; C426845:coprinol