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KMID : 0545120110210090930
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Journal of Microbiology and Biotechnology
2011 Volume.21 No. 9 p.930 ~ p.936
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Wewakamide A and Guineamide G, Cyclic Depsipeptides from the Marine Cyanobacteria Lyngbya semiplena and Lyngbya majuscula
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Bingnan Han
Harald Gross
Kerry L. McPhail
Doug Goeger
Claudia S. Maier
William H. Gerwick
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Abstract
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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 13C NMR, as well as 2D COSY, HSQC, HSQCTOCSY, 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 β-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 LC50 values of 2.7 μM.
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KEYWORD
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Lyngbya semiplena, Lyngbya majuscula, cyclic depsipeptides, wewakamide A, guineamide G
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