The Isolation and Structure Elucidation of Tasiamide B, a 4-Amino-3-hydroxy-5-phenylpentanoic Acid Containing Peptide from the Marine Cyanobacterium Symploca sp

• Published in: Journal of natural products (Washington, D.C.) Vol. 66; no. 7; pp. 1006 - 1009
• Main Authors: Williams, Philip G, Yoshida, Wesley Y, Moore, Richard E, Paul, Valerie J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.07.2003; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents; Applied microbiology; Biological and medical sciences; Chemistry, Medicinal; Chemotherapic agents; Chromatography, High Pressure Liquid; Cyanobacteria - chemistry; Fundamental and applied biological sciences. Psychology; Humans; Inhibitory Concentration 50; KB Cells; Life Sciences & Biomedicine; Microbiology; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Oligopeptides - chemistry; Oligopeptides - isolation & purification; Palau; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; Palau; SECONDARY ALCOHOLS; ABSOLUTE-CONFIGURATION; ESTERS; BETA-HYDROXY ACIDS; Antineoplastic agent; Aminoalcohol; Peptides; Cytotoxicity; Heptapeptide; Marine environment; Cell line; Microbial origin; KB cell line; Absolute configuration; Cyanobacteria; Bacteria; Isolation; Palau; Tumor cell; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np030114z

A new cytotoxic peptide, which displayed an IC50 value of 0.8 μM against KB cells, has been isolated from the marine cyanobacterium Symploca sp. The planar structure of tasiamide B (1), deduced by 2D NMR experiments, contains the unusual amino acid-derived residue 4-amino-3-hydroxy-5-phenylpentanoic acid (Ahppa). The configuration of 1 was deduced by HPLC analysis of degradation products.