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

33 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

Fingerprint

Chaetomium
Metabolites
Polyenes
Linoleic Acid
Fungi
Staphylococcus aureus
Corynebacterium diphtheriae
Salmonella
Streptococcus pyogenes
Mycelium
Bacilli
Lycopersicon esculentum
Growth
Fruits
Bacillus subtilis
Yeast
Escherichia coli
Fruit
Fatty Acids
Yeasts

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Musanahol : a new aureonitol-related metabolite from a Chaetomium sp. / Marwah, Ruchi G.; Fatope, Majekodunmi O.; Deadman, Mike L.; Al-Maqbali, Yousif Mohammed; Husband, John.

In: Tetrahedron, Vol. 63, No. 34, 20.08.2007, p. 8174-8180.

Research output: Contribution to journalArticle

Marwah, Ruchi G. ; Fatope, Majekodunmi O. ; Deadman, Mike L. ; Al-Maqbali, Yousif Mohammed ; Husband, John. / Musanahol : a new aureonitol-related metabolite from a Chaetomium sp. In: Tetrahedron. 2007 ; Vol. 63, No. 34. pp. 8174-8180.
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