Antineoplastic Agents. 587. Isolation and Structure of 3-Epipancratistatin from Narcissus cv. Ice Follies

George R. Pettit*, Rui Tan, Guan-Hu Bao, Noeleen Melody, Dennis L. Doubek, Song Gao, Jean-Charles Chapuis, and Lee Williams
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, PO Box 871604, Tempe, Arizona 85287-1604, United States
J. Nat. Prod., Article ASAP
DOI: 10.1021/np200862y
Publication Date (Web): March 13, 2012

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 (GI50 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.

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