Cytotoxic Microcolin Lipopeptides from the Marine Cyanobacterium Moorea producens

Hao Bing Yu, Evgenia Glukhov, Yueying Li, Arihiro Iwasaki, Lena Gerwick, Pieter C. Dorrestein, Bing Hua Jiao, William H. Gerwick

研究成果: Article査読

4 被引用数 (Scopus)

抄録

Nine new linear lipopeptides, microcolins E-M (1-9), together with four known related compounds, microcolins A-D (10-13), were isolated from the marine cyanobacterium Moorea producens using bioassay-guided and LC-MS/MS molecular networking approaches. Catalytic hydrogenation of microcolins A-D (10-13) yielded two known compounds, 3,4-dihydromicrocolins A and B (14, 15), and two new derivatives, 3,4-dihydromicrocolins C and D (16, 17), respectively. The structures of these new compounds were determined by a combination of spectroscopic and advanced Marfey's analysis. Structurally unusual amino acid units, 4-methyl-2-(methylamino)pent-3-enoic (Mpe) acid and 2-amino-4-methylhexanoic acid (N-Me-homoisoleucine), in compounds 1-3 and 8, respectively, are rare residues in naturally occurring peptides. These metabolites showed significant cytotoxic activity against H-460 human lung cancer cells with IC50 values ranging from 6 nM to 5.0 μM. The variations in structure and attendant biological activities provided fresh insights concerning structure-activity relationships for the microcolin class of lipopeptides.

本文言語English
ページ(範囲)2608-2619
ページ数12
ジャーナルJournal of Natural Products
82
9
DOI
出版ステータスPublished - 2019 9 27

ASJC Scopus subject areas

  • 分析化学
  • 分子医療
  • 薬理学
  • 薬科学
  • 創薬
  • 補完代替医療
  • 有機化学

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