Chemical analysis of the Alphaproteobacterium strain MOLA1416 associated with the marine lichen Lichina pygmaea

Phytochemistry. 2018 Jan:145:57-67. doi: 10.1016/j.phytochem.2017.10.005. Epub 2017 Nov 5.

Abstract

Alphaproteobacterium strain MOLA1416, related to Mycoplana ramosa DSM 7292 and Chelativorans intermedius CC-MHSW-5 (93.6% 16S rRNA sequence identity) was isolated from the marine lichen, Lichina pygmaea and its chemical composition was characterized by a metabolomic network analysis using LC-MS/MS data. Twenty-five putative different compounds were revealed using a dereplication workflow based on MS/MS signatures available through GNPS (https://gnps.ucsd.edu/). In total, ten chemical families were highlighted including isocoumarins, macrolactones, erythrinan alkaloids, prodiginines, isoflavones, cyclohexane-diones, sterols, diketopiperazines, amino-acids and most likely glucocorticoids. Among those compounds, two known metabolites (13 and 26) were isolated and structurally identified and metabolite 26 showed a high cytotoxic activity against B16 melanoma cell lines with an IC50 0.6 ± 0.07 μg/mL.

Keywords: Alphaproteobacteria; Dereplication workflow; LC/MS(n); Lichen-associated bacteria; Lichina pygmaea; Molecular networking.

MeSH terms

  • Alphaproteobacteria / chemistry*
  • Alphaproteobacteria / isolation & purification
  • Alphaproteobacteria / metabolism
  • Animals
  • Cell Line
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Humans
  • Lichens / metabolism
  • Lichens / microbiology*
  • Melanoma, Experimental / drug therapy*
  • Melanoma, Experimental / pathology
  • Mice
  • Molecular Structure
  • Oligopeptides / chemistry*
  • Oligopeptides / isolation & purification
  • Prodigiosin / analogs & derivatives*
  • Prodigiosin / chemistry
  • Prodigiosin / isolation & purification
  • Prodigiosin / pharmacology
  • Structure-Activity Relationship

Substances

  • 6-methoxy-2-methyl-3-heptylprodiginin
  • Oligopeptides
  • Prodigiosin