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 language | English |
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Pages (from-to) | 8174-8180 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 63 |
Issue number | 34 |
DOIs | |
Publication status | Published - Aug 20 2007 |
Keywords
- Absolute configuration
- Antibacterial
- Ascomycota
- Chaetomium sp
- Mosher ester
- Musanahol
- Polyketide
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry