New Hydroxydecanoic Acid Derivatives Produced by an Dndophytic Yeast Aureobasidium pullulans AJF1 from Flowers of Aconitum carmichaeli

Molecules. 2019 Nov 8;24(22):4051. doi: 10.3390/molecules24224051.

Abstract

Endophytes have been recognized as a source for structurally novel and biologically active secondary metabolites. Among the host plants for endophytes, some medicinal plants that produce pharmaceuticals have been reported to carry endophytes, which could also produce bioactive secondary metabolites. In this study, the medicinal plant Aconitum carmichaeli was selected as a potential source for endophytes. An endophytic microorganism, Aureobasidium pullulans AJF1, harbored in the flower of Aconitum carmichaeli, was cultured on a large scale and extracted with an organic solvent. Extensive chemical investigation of the extracts resulted in isolation of three lipid type compounds (1-3), which were identified to be (3R,5R)-3,5-dihydroxydecanoic acid (1), (3R,5R)-3-(((3R,5R)-3,5-dihydroxydecanoyl)oxy)-5-hydroxydecanoic acid (2), and (3R,5R)-3-(((3R,5R)-5-(((3R,5R)-3,5-dihydroxydecanoyl)oxy)-3-hydroxydecanoyl)oxy)-5-hydroxydecanoic acid (3) by chemical methods in combination with spectral analysis. Compounds 2 and 3 had new structures. Absolute configurations of the isolated compounds (1-3) were established using modified Mosher's method together with analysis of NMR data for their acetonide derivatives. All the isolates (1-3) were evaluated for antibiotic activities against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and their cytotoxicities against MCF-7 cancer cells. Unfortunately, they showed low antibiotic activities and cytotoxic activities.

Keywords: Aconitum carmichaeli; Aureobasidium pullulans; endophyte; hydroxydecanoic acid.

MeSH terms

  • Aconitum / genetics
  • Aconitum / metabolism
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Ascomycota / genetics
  • Ascomycota / metabolism*
  • Bacteria / drug effects
  • Decanoic Acids / chemical synthesis
  • Decanoic Acids / chemistry*
  • Decanoic Acids / metabolism*
  • Decanoic Acids / pharmacology
  • Humans
  • Hydroxy Acids / chemical synthesis
  • Hydroxy Acids / chemistry*
  • Hydroxy Acids / metabolism*
  • Hydroxy Acids / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure

Substances

  • Anti-Bacterial Agents
  • Decanoic Acids
  • Hydroxy Acids
  • 5-hydroxydecanoic acid