Phomopsichin A-D; Four New Chromone Derivatives from Mangrove Endophytic Fungus Phomopsis sp. 33

Mar Drugs. 2016 Nov 22;14(11):215. doi: 10.3390/md14110215.

Abstract

Four new chromone derivatives, phomopsichins A-D (1-4), along with a known compound, phomoxanthone A (5), were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp. 33#. Their structures were elucidated based on comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction or theoretical calculations of electronic circular dichroism (ECD). They feature a tricyclic framework, in which a dihydropyran ring is fused with the chromone ring. Compounds 1-5 showed weak inhibitory activities on acetylcholinesterase as well as α-glucosidase, weak radical scavenging effects on 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as OH, and weak antimicrobial activities. Compounds 1-4 showed no cytotoxic activity against MDA-MB-435 breast cancer cells. Their other bioactivities are worthy of further study, considering their unique molecular structures.

Keywords: Phomopsis sp.; chromone derivatives; mangrove endophytic fungi; secondary metabolites.

MeSH terms

  • Acetylcholinesterase / metabolism
  • Biphenyl Compounds / metabolism
  • Breast Neoplasms / drug therapy
  • Cell Line, Tumor
  • Chromones / chemistry*
  • Chromones / pharmacology
  • Crystallography, X-Ray / methods
  • Endophytes / chemistry*
  • Fermentation / physiology
  • Fungi / chemistry*
  • Humans
  • Molecular Structure
  • Picrates / metabolism
  • X-Ray Diffraction / methods
  • Xanthones / chemistry
  • Xanthones / pharmacology
  • alpha-Glucosidases / metabolism

Substances

  • Biphenyl Compounds
  • Chromones
  • Picrates
  • Xanthones
  • phomoxanthone A
  • 1,1-diphenyl-2-picrylhydrazyl
  • Acetylcholinesterase
  • alpha-Glucosidases