Identification of a new antifungal oligoacetal derivative produced by Streptomyces toxytricini against Candida albicans

Nat Prod Res. 2016 Aug;30(16):1816-23. doi: 10.1080/14786419.2015.1081199. Epub 2015 Sep 4.

Abstract

Thirty actinomycete isolates were isolated from soil and tested against Candida albicans in vitro. The active isolate was identified by 16s-rRNA gene sequencing method as Streptomyces toxytricini. The antifungal compound was extracted with ethyl acetate followed by diethyl ether. Both HPLC and GC-MS analysis confirmed presence of one pure compound in the diethyl ether extract. The compound is a yellow liquid has a maximum absorbance at 240 nm in methanol. The chemical structure was elucidated by 1D and 2D-NMR and IR analyses. The elucidated molecular formula was C36H54O14. The compound is a polyacetal tricyclononane derivative, composed of a tricyclononane ring attached from the carbon atom number four with an oligo-acetal chain (six acetal groups in chain) and from the carbon atom number seven with a methoxy carbonyl benzene-1,3-dicarboxylic acid. The purposed name is: 4- {[tricycle(3.2.1.1(1,3))non-8-yl] methoxy carbonyl benzene-1,3-dicarboxylic acid} (2,4,5,6,7,8,9 heptaoxa, 3-ethoxy, 5,6,7,9-tetramethyl unidecane).

Keywords: Antifungal; Candida albicans; Streptomyces toxytricini; tricyclononane.

MeSH terms

  • Actinobacteria / chemistry
  • Alkanes
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Candida albicans / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Streptomyces / chemistry*

Substances

  • Alkanes
  • Antifungal Agents
  • nonane