title: Antineoplastic agents 582. Part 1: Isolation and structure of a cyclobutane-type sesquiterpene cancer cell growth inhibitor from Coprinus cinereus (Coprinaceae).
abstract: Bioassay-guided (murine P388 lymphocytic leukemia and human cancer cell lines) separation of an ethyl acetate extract prepared from the inky cap fungus Coprinus cinereus led to the isolation of three new sesquiterpenes, 7,7a-diepicoprinastatin 1 (1), 14-hydroxy-5-desoxy-2S,3S,9R-illudosin (2), and 4,5-dehydro-5-deoxyarmillol (3), together with the known armillol (4). The structure and relative configuration of 1 was determined by single-crystal X-ray diffraction experiments. The structures of compounds 2, 3, and 4 were each deduced by a combination of HRMS and 1D and 2D NMR techniques. Cyclobutane 2 led to modest inhibition of the murine P388 leukemia cell line.
authors.affiliation: Cancer Research Institute, Department of Chemistry and Biochemistry, Arizona State University, PO Box 871604, Tempe, AZ 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: Fiona
authors.initials: F
authors.lastname: Hogan
authors.forename: Zbigniew A
authors.initials: ZA
authors.lastname: Cichacz
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003302:Coprinus / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003503:Cyclobutanes / Q000737:chemistry; D006801:Humans; D051379:Mice; D008958:Models, Molecular; D009369:Neoplasms / Q000188:drug therapy*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D003503:Cyclobutanes; D012717:Sesquiterpenes