Isolation and structure of phakellistatin 14 from the Western Pacific marine sponge Phakellia sp.
A new cycloheptapeptide, phakellistatin 14, was isolated in 8.8 x 10(-7)% yield from Phakellia sp., a marine sponge from Chuuk, Federated States of Micronesia. The structure (1), cyclo-Phe-beta-OMe-Asp-Ala-Met(SO)-Ala-Ile-Pro, was elucidated by 1D and 2D NMR spectral analyses augmented by HRFABMS. The chirality of each amino acid unit was determined to be S using chiral HPLC methods. Phakellistatin 14 showed cancer cell growth inhibitory activity (ED(50) 5 microg/mL) against the murine lymphocytic leukemia P388 cell line.
Pettit
George R
GR
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 872404, Tempe, Arizona 85287-2404, USA. bpettit@asu.edu
Tan
Rui
R
D000595:Amino Acid Sequence; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004354:Drug Screening Assays, Antitumor; D007941:Leukemia P388; D051379:Mice; D008849:Micronesia; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*
D000970:Antineoplastic Agents; D010456:Peptides, Cyclic; C498128:phakellistatin 14