Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina

J Nat Prod. 2015 Apr 24;78(4):901-8. doi: 10.1021/acs.jnatprod.5b00168. Epub 2015 Mar 13.

Abstract

Mebamamides A and B, new lipopeptides with four d-amino acid residues and a 3,8-dihydroxy-9-methyldecanoic acid residue, were isolated from the green alga Derbesia marina. Their gross structures were elucidated by spectroscopic and ESI-ITMS analyses. The absolute configurations except for the two leucines were revealed based on chiral-phase HPLC analyses of the acid hydrolysate and a modified Mosher's method. A distinction between D-Leu and L-Leu in the sequence was established by the application of a dansyl-Edman method to the partial acid hydrolysate. Mebamamide A did not exhibit any growth inhibitory activity against HeLa and HL60 cells at 10 μM, and mebamamide B did not exhibit any growth inhibitory activity against those cells at 100 μM. Additionally, it was suggested that mebamamide B induced the differentiation of HL60 cells into macrophage-like cells at 100 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Chlorophyta / chemistry*
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • HeLa Cells
  • Humans
  • Lipopeptides / chemistry
  • Lipopeptides / isolation & purification*
  • Lipopeptides / pharmacology
  • Macrophages / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology

Substances

  • Amino Acids
  • Lipopeptides
  • Peptides, Cyclic
  • mebamamide A
  • mebamamide B