Polyketides from the Deep-Sea-Derived Fungus Graphostroma sp. MCCC 3A00421 Showed Potent Antifood Allergic Activities

J Agric Food Chem. 2018 Feb 14;66(6):1369-1376. doi: 10.1021/acs.jafc.7b04383. Epub 2018 Feb 2.

Abstract

To discover antifood allergic components from deep-sea-derived microorganisms, we performed a systematic chemical investigation of the Atlantic hydrothermal fungus Graphostroma sp. MCCC 3A00421. Consequently, nine new (1-9) and 19 known (10-28) polyketides were isolated. The planar structures of the new compounds were elucidated mainly by detailed analysis of their nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry data, while the absolute configurations were established using the modified Mosher's method in association with electronic circular dichroism spectra. Graphostrin A (1) is a novel chlorinated polyketide derivate bearing an oxazole moiety. All isolates were tested for antifood allergic bioactivities in immunoglobulin E-mediated rat basophilic leukemia-2H3 cells. Reticulol (10) significantly decreased the rates of degranulation and histamine release with IC50 values of 13.5 and 13.7 μM, respectively, suggesting reticulol could be a potential antifood allergic medicine.

Keywords: deep-sea; food allergy; hydrothermal vents; marine microorganism; natural products.

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Ascomycota / classification
  • Ascomycota / genetics
  • Ascomycota / isolation & purification
  • Cell Degranulation / drug effects
  • Cell Line
  • Circular Dichroism
  • Food Hypersensitivity / drug therapy*
  • Food Hypersensitivity / immunology
  • Histamine / immunology
  • Humans
  • Immunoglobulin E / immunology
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Polyketides / chemistry
  • Polyketides / isolation & purification
  • Polyketides / pharmacology*
  • Rats
  • Seawater / microbiology*

Substances

  • Polyketides
  • Immunoglobulin E
  • Histamine