Isolation and structure of the marine sponge cell growth inhibitory cyclic peptide phakellistatin 1.
A new cell growth inhibitory (P-388 murine leukemia ED50 7.5 micrograms/ml) cycloheptapeptide designated phakellistatin 1 was isolated from two Indo-Pacific sponges, Phakellia costata and Stylotella aurantium. Structural elucidation was accomplished utilizing high field nmr, amino acid analyses, and mass spectral techniques (fab, tandem ms/ms), followed by chiral gas chromatographic procedures for absolute configuration assignments (all S-amino acid units). By these methods phakellistatin 1 [1] was found to be cyclo (Pro-Ile-Pro-Ile-Phe-Pro-Tyr), and this assignment was finally confirmed by an X-ray crystal structure determination.
Pettit
G R
GR
Department of Chemistry, Arizona State University, Tempe 85287-1604.
Cichacz
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Barkoczy
J
J
Dorsaz
A C
AC
Herald
D L
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Williams
M D
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Doubek
D L
DL
Schmidt
J M
JM
Tackett
L P
LP
Brune
D C
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D000595:Amino Acid Sequence; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D003460:Crystallization; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D008969:Molecular Sequence Data; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D017433:Protein Structure, Secondary; D014961:X-Ray Diffraction
D000970:Antineoplastic Agents; D010456:Peptides, Cyclic; C080583:phakellistatin 1