Antifungal Monoterpene Derivatives from the Plant Endophytic Fungus Pestalotiopsis foedan

Chem Biodivers. 2016 Oct;13(10):1422-1425. doi: 10.1002/cbdv.201600114.

Abstract

A new monoterpene lactone, (1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one (1), along with one related known compound, (2R)-2-[(1R)-4-methylcyclohex-3-en-1-yl]propanoic acid (2), were isolated from the liquid culture of the plant endophytic fungus Pestalotiopsis foedan obtained from the branch of Bruguiera sexangula. The structure and absolute configuration of 1 were determined on the basis of extensive analysis of NMR spectra combined with computational methods via calculation of the optical rotation (OR) and 13 C-NMR. Both compounds exhibited strong antifungal activities against Botrytis cinerea and Phytophthora nicotianae with MIC values of 3.1 and 6.3 μg/ml, respectively, which are comparable to those of the known antifungal drug ketoconazole. Compound 2 also showed modest antifungal activity against Candida albicans with a MIC value of 50 μg/ml.

Keywords: Bruguiera sexangula; Pestalotiopsis foedan; Antifungal activities; Endophytic fungi; Monoterpene.

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Botrytis / drug effects*
  • Candida albicans / drug effects*
  • Dose-Response Relationship, Drug
  • Endophytes / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Monoterpenes / chemistry
  • Monoterpenes / isolation & purification
  • Monoterpenes / pharmacology*
  • Phytophthora / drug effects*
  • Structure-Activity Relationship
  • Xylariales / chemistry*

Substances

  • Antifungal Agents
  • Monoterpenes