Aurilides B and C, cancer cell toxins from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula

J Nat Prod. 2006 Apr;69(4):572-5. doi: 10.1021/np0503911.

Abstract

Cytotoxicity-guided fractionation of a strain of the marine cyanobacterium Lyngbya majuscula collected from Papua New Guinea led to the isolation of aurilides B (1) and C (2). The planar structures of 1 and 2 were established by spectroscopic analysis, including HR-FABMS, 1D (1)H and (13)C NMR, and 2D COSY, HSQC, HSQC-TOCSY, and HMBC spectra. The absolute configuration was determined by spectroscopic analysis and chiral HPLC analysis of acid hydrolysates of 1 and 2. Both aurilides B and C showed in vitro cytotoxicity toward NCI-H460 human lung tumor and the neuro-2a mouse neuroblastoma cell lines, with LC(50) values between 0.01 and 0.13 microM. Aurilide B (1) was evaluated in the NCI 60 cell line panel and found to exhibit a high level of cytotoxicity (the mean panel GI(50) concentration was less than 10 nM) and to be particularly active against leukemia, renal, and prostate cancer cell lines.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / isolation & purification
  • Antineoplastic Agents* / pharmacology
  • Drug Screening Assays, Antitumor
  • Lyngbya Toxins* / chemistry
  • Lyngbya Toxins* / isolation & purification
  • Lyngbya Toxins* / pharmacology
  • Marine Toxins* / chemistry
  • Marine Toxins* / isolation & purification
  • Marine Toxins* / pharmacology
  • Molecular Structure
  • Papua New Guinea
  • Peptides, Cyclic* / chemistry
  • Peptides, Cyclic* / isolation & purification
  • Peptides, Cyclic* / pharmacology
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Lyngbya Toxins
  • Marine Toxins
  • Peptides, Cyclic
  • aurilide A
  • aurilide B
  • aurilide C