title: Antineoplastic agents. 587. Isolation and structure of 3-epipancratistatin from Narcissus cv. Ice Follies.
abstract: Bioassay-guided (cancer cell line) separation of an extract prepared from Narcissus cv. Ice Follies (from The Netherlands) led to the isolation of a new Amaryllidaceae isocarbostiryl, 3-epipancratistatin (1b), as well as narciclasine (2). This Narcissus cultivar was found to be a good source of narciclasine. The structure of 1b was established by high-resolution mass and high-field 2D NMR spectroscopic analyses. Against a panel of murine and human cancer cell lines, 3-epipancratistatin (1b) led to cell growth inhibition (GI(50) 2.2-0.69 μg/mL) some 100× less than that found for pancratistatin (1a) and narciclasine (2), thereby revealing an important configurational requirement in 1a for strong cancer cell growth inhibition.
authors.affiliation: Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, PO Box 871604, Tempe, Arizona 85287-1604, USA. bpettit@asu.edu
authors.forename: George R
authors.initials: GR
authors.lastname: Pettit
authors.forename: Rui
authors.initials: R
authors.lastname: Tan
authors.forename: Guan-Hu
authors.initials: GH
authors.lastname: Bao
authors.forename: Noeleen
authors.initials: N
authors.lastname: Melody
authors.forename: Dennis L
authors.initials: DL
authors.lastname: Doubek
authors.forename: Song
authors.initials: S
authors.lastname: Gao
authors.forename: Jean-Charles
authors.initials: JC
authors.lastname: Chapuis
authors.forename: Lee
authors.initials: L
authors.lastname: Williams
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007941:Leukemia P388; D051379:Mice; D015394:Molecular Structure; D031427:Narcissus / Q000737:chemistry*; D010617:Phenanthridines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: C573383:3-epipancratistatin; D047151:Amaryllidaceae Alkaloids; D000970:Antineoplastic Agents; D010617:Phenanthridines; C010753:narciclasine