Biotransformation of huperzine A by a fungal endophyte of Huperzia serrata furnished sesquiterpenoid-alkaloid hybrids

J Nat Prod. 2014 Sep 26;77(9):2054-9. doi: 10.1021/np500412f. Epub 2014 Sep 15.

Abstract

Biotransformation of huperzine A (hupA) by a fungal endophyte, Ceriporia lacerate HS-ZJUT-C13A, afforded compounds 1-5 and three tremulane sesquiterpenoids, 6-8. Huptremules A-D (1-4) feature unusual sesquiterpenoid-alkaloid hybrid structures that integrate the characteristics of fungal metabolites (tremulane sesquiterpenoids) and the exogenous substrate (hupA). These results support the use of fungal endophytes as biocatalysts for the biotransformation of natural products, particularly those originating from the host plant.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / metabolism*
  • Biological Products / chemistry
  • Biological Products / isolation & purification*
  • Biological Products / metabolism*
  • Biotransformation
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / isolation & purification*
  • Cholinesterase Inhibitors / metabolism*
  • Chromatography, High Pressure Liquid
  • Endophytes / chemistry*
  • Huperzia / microbiology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / metabolism*

Substances

  • Alkaloids
  • Biological Products
  • Cholinesterase Inhibitors
  • Sesquiterpenes
  • huperzine A