New Bis-Alkenoic Acid Derivatives from a Marine-Derived Fungus Fusarium solani H915

Mar Drugs. 2018 Dec 3;16(12):483. doi: 10.3390/md16120483.

Abstract

Fusarium solani H915 is a fungus derived from mangrove sediments. From its ethyl acetate extract, a new alkenoic acid, fusaridioic acid A (1), three new bis-alkenoic acid esters, namely, fusariumester A₁ (2), A₂ (3) and B (4), together with three known compounds (5⁻7), were isolated. The structures of the new compounds were comprehensively characterized by high resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). Additionally, the antifungal activities against tea pathogenic fungi Pestalotiopsis theae and Colletotrichum gloeosporioides were studied. The new compound, 4, containing a β-lactone ring, exhibited moderate inhibitory activity against P. theae, with an MIC of 50 μg/disc. Hymeglusin (6), a typical β-lactone antibiotic and a terpenoid alkaloid, equisetin (7), exhibited potent inhibitory activities against both fungal species. The isolated compounds were evaluated for their effects on zebrafish embryo development. Equisetin clearly imparted toxic effect on zebrafish even at low concentrations. However, none of the alkenoic acid derivatives exhibited significant toxicity to zebrafish eggs, embryos, or larvae. Thus, the β-lactone containing alkenoic acid derivatives from F. solani H915 are low in toxicity and are potent antifungal agents against tea pathogenic fungi.

Keywords: A2; B; Fusarium solani H915; bis-alkenoic acid esters; fusaridioic acid A; fusariumester A1; tea pathogenic fungi inhibitory effect.

MeSH terms

  • Alkenes / chemistry
  • Alkenes / isolation & purification
  • Alkenes / pharmacology*
  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Camellia sinensis / microbiology*
  • Colletotrichum / drug effects
  • Embryo, Nonmammalian
  • Fusarium / chemistry*
  • Geologic Sediments / microbiology
  • Microbial Sensitivity Tests
  • Plant Diseases / microbiology
  • Plant Diseases / prevention & control*
  • Pyrrolidinones / chemistry
  • Pyrrolidinones / isolation & purification
  • Pyrrolidinones / pharmacology
  • Spectrometry, Mass, Electrospray Ionization
  • Tetrahydronaphthalenes / chemistry
  • Tetrahydronaphthalenes / isolation & purification
  • Tetrahydronaphthalenes / pharmacology
  • Toxicity Tests
  • Wetlands
  • Zebrafish

Substances

  • Alkenes
  • Antifungal Agents
  • Pyrrolidinones
  • Tetrahydronaphthalenes
  • equisetin