Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
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Wewakamide A and Guineamide G, Cyclic Depsipeptides from the Marine Cyanobacteria Lyngbya semiplena and Lyngbya majuscula

  • Han, Bingnan (Department of Ocean Science and Engineering, Zhejiang University) ;
  • Gross, Harald (Institute for Pharmaceutical Biology, University of Bonn) ;
  • Mcphail, Kerry L. (College of Pharmacy, Oregon State University) ;
  • Goeger, Doug (College of Pharmacy, Oregon State University) ;
  • Maier, Claudia S. (Department of Chemistry, Oregon State University) ;
  • Gerwick, William H. (Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California at San Diego)
  • Received : 2011.05.11
  • Accepted : 2011.06.03
  • Published : 2011.09.28
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Abstract

Two new cyclic depsipeptides wewakamide A (1) and guineamide G (2) have been isolated from the marine cyanobacterium Lyngbya semiplena and Lyngbya majuscula, respectively, collected from Papua New Guinea. The amino and hydroxy acid partial structures of wewakamide A and guineamide G were elucidated through extensive spectroscopic techniques, including HR-FABMS, 1D $^1H$ and $^{13}C$ NMR, as well as 2D COSY, HSQC, HSQC-TOCSY, and HMBC spectra. The sequence of the residues of wewakamide A was determined through a combination of ESI-MS/MS, HMBC, and ROESY. Wewakamide A possesses a ${\beta}$-amino acid, 3-amino-2-methylbutanoic acid (Maba) residue, which has only been previously identified in two natural products, guineamide B (3) and dolastatin D (4). Although both new compounds (1,2) showed potent brine shrimp toxicity, only guineamide G displayed significant cytotoxicity to a mouse neuroblastoma cell line with $LC_{50}$ values of 2.7 ${\mu}M$.

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