Musanahol: a new aureonitol-related metabolite from a Chaetomium sp.

Ruchi G. Marwah, Majekodunmi O. Fatope, Mike L. Deadman, Yousif Mohammed Al-Maqbali, John Husband

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Two antibacterial furano-polyenes, (-)-musanahol (1) and 3-epi-aureonitol (5), and a fatty acid, linoleic acid (8) were isolated from the laboratory cultures of a Chaetomium sp. accessed from tomato fruits, and grown on YMG medium (yeast extract, glucose, malt extract and water) at pH 5.8-6.0. The structure of compound 1, a new furano-polyene, was elucidated by spectroscopic methods that include extensive 2D NMR experiments, double resonance experiments, Mosher's method and PM3 calculations. (-)-Musanahol (1) and 3-epi-aureonitol (5) were present in the culture filtrate of the fungus. 3-epi-Aureonitol (5) completely inhibited the growth of Streptococcus pyogenes at 15.63 μg/mL and Escherichia coli, Staphylococcus aureus, Salmonella choleraesuis and Corynebacterium diphtheriae at 31.25 μg/mL, whereas (-)-musanahol (1) lacked the antimicrobial potency of compound 5 in spite of the similarities in their structures. Linoleic acid (8) was isolated from the mycelia of the fungus; it inhibited the growth of S. aureus and Bacillus subtilis at a minimum concentration of 15.62 μg/mL.

Original languageEnglish
Pages (from-to)8174-8180
Number of pages7
JournalTetrahedron
Volume63
Issue number34
DOIs
Publication statusPublished - Aug 20 2007

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Keywords

  • Absolute configuration
  • Antibacterial
  • Ascomycota
  • Chaetomium sp
  • Mosher ester
  • Musanahol
  • Polyketide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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