Hantupeptins B and C, cytotoxic cyclodepsipeptides from the marine cyanobacterium Lyngbya majuscula

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• 作者：Ashootosh Tripathi ; Jonathan Puddick ; Michele R. Prinsep ; Peter Peng Foo Lee ; Lik Tong Tan
• 关键词：Lyngbya majuscula ; Oscillatoriaceae ; Marine cyanobacteria ; Brine shrimp toxicity ; Cytotoxicity ; Cyclic depsipeptide
• 刊名：Phytochemistry
• 出版年：2010
• 出版时间：February 2010
• 年：2010
• 卷：71
• 期：2-3
• 页码：307-311
• 全文大小：229 K

文摘

Hantupeptins B (2) and C (3) were isolated, along with the previously reported hantupeptin A (1), from the marine cyanobacterium, Lyngbya majuscula, collected from Pulau Hantu Besar, Singapore. Their structures were elucidated by interpretation of extensive 1D and 2D NMR spectroscopic data. Compounds 2 and 3 are cyclic depsipeptides consisting of five α-amino/hydroxy acid residues, including phenyllactic acid, proline, N-methyl-valine, valine, N-methyl-isoleucine, and a β-hydroxy acid unit with different degrees of unsaturation at the terminal end of each molecule. The absolute configurations of the common amino acids and phenyllactic acid were determined by the advanced Marfey’s and chiral HPLC analyses, respectively. The complete stereochemistry of 3-hydroxy-2-methyl-7-octynoic acid moiety in hantupeptin A was elucidated by a combination of homonuclear J-resolved 2D NMR experiments and by Mosher’s method. Hantupeptins B and C showed moderate in vitro cytotoxicity when tested against MOLT-4 (leukemic) and MCF-7 (breast cancer) cell lines.