Scytalidamides A and B, new cytotoxic cyclic heptapeptides from a marine fungus of the genus Scytalidium

J Org Chem. 2003 Nov 14;68(23):8767-73. doi: 10.1021/jo030191z.

Abstract

Two new cyclic heptapeptides have been isolated from the culture broth of a marine fungus, Scytalidium sp., collected from the Bahamas. The planar structures of scytalidamides A (1) and B (2) were assigned on the basis of 1D and 2D NMR spectroscopic techniques, while the absolute configuration of the amino acid residues in both molecules was determined by application of the advanced Marfey's method. The absolute stereochemistry of the uncommon 3-methylproline moiety in scytalidamide B (2) was confirmed by isolation and CD measurements, as well as application of the advanced Marfey's method. Scytalidamides A (1) and B (2) showed moderate in vitro cytotoxicity toward HCT-116 human colon adenocarcinoma with IC(50) values of 2.7 and 11.0 microM, respectively.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Cell Line, Tumor
  • Circular Dichroism
  • Drug Screening Assays, Antitumor
  • Fungi / chemistry*
  • Humans
  • Marine Biology
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / pharmacology
  • Stereoisomerism

Substances

  • Antineoplastic Agents
  • Peptides, Cyclic
  • Scytalidamide A
  • scytalidamide B