Deconins A-E: Cuparenic and Mevalonic or Propionic Acid Conjugates from the Basidiomycete Deconica sp. 471

J Nat Prod. 2015 Apr 24;78(4):934-8. doi: 10.1021/np5010104. Epub 2015 Apr 14.

Abstract

Bioassay-guided fractionation of antibacterial extracts from cultures of a basidiomycete from Northern Thailand, which represents a new species of the genus Deconica, yielded the terpenoid deconin A (1), whose structure was elucidated by spectral methods (NMR, HRMS) as a cuparenic/mevalonic acid conjugate. The absolute configuration of 1 was determined after saponification and comparison of specific rotations of the resulting cuparenic acid and mevalonolactone with authentic standards and literature data. Six minor congeners (2-7) were isolated and identified, and their antimicrobial and cytotoxic effects are reported. Compounds 1-4 are the first natural products featuring an unmodified mevalonic acid residue as a building block.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Basidiomycota / chemistry*
  • Mevalonic Acid / analogs & derivatives
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Propionates / chemistry
  • Propionates / isolation & purification*
  • Stereoisomerism
  • Terpenes / chemistry
  • Terpenes / isolation & purification*
  • Terpenes / pharmacology
  • Thailand

Substances

  • Anti-Bacterial Agents
  • Propionates
  • Terpenes
  • deconin A
  • mevalonolactone
  • propionic acid
  • Mevalonic Acid