Saccharopolytide A, a new cyclic tetrapeptide with rare 4-hydroxy-proline moieties from the deep-sea derived actinomycete Saccharopolyspora cebuensis MCCC 1A09850

Nat Prod Res. 2018 Jul;32(14):1627-1631. doi: 10.1080/14786419.2017.1392956. Epub 2017 Oct 24.

Abstract

A genome mining analysis on the deep-sea derived actinomycete Saccharopolyspora cebuensis MCCC 1A09850 indicated its potential to produce polypeptides. Accordingly, a systematic chemical investigation was conducted, which resulted in the isolation of one new cyclic tetrapeptide (saccharopolytide A, 1) and two known polyketides (2, 3) along with six other miscellaneous compounds (4‒9). Mainly by analysis of the 1D, 2D NMR and MS data, the chemical structure of saccharopolytide A was established as cyclo-(l-Leu-4-hydroxy-l-Pro-l-Phe-4-hydroxy-l-Pro). All isolates were evaluated for anti-allergic and anti-tumor bioactivities. Indol-3-carbaldehyde (4) showed weak anti-allergic effect with IC50 value of 55.75 μg/mL. And 2 showed weak anti-proliferative activity against Hela and H1299 tumor cell lines. Our results consolidate the potential of deep-sea-derived microorganisms to produce structurally interesting compounds.

Keywords: Actinomycetes; Saccharopolyspora cebuensis; anti-allergy; anti-tumor; deep-sea; secondary metabolites.

MeSH terms

  • Anti-Allergic Agents / chemistry
  • Anti-Allergic Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Aquatic Organisms
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Evaluation, Preclinical
  • HeLa Cells
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / pharmacology
  • Proline / chemistry
  • Saccharopolyspora / chemistry*
  • Saccharopolyspora / metabolism
  • Secondary Metabolism

Substances

  • Anti-Allergic Agents
  • Antineoplastic Agents
  • Peptides, Cyclic
  • Proline