TY - JOUR
T1 - Musanahol
T2 - a new aureonitol-related metabolite from a Chaetomium sp.
AU - Marwah, Ruchi G.
AU - Fatope, Majekodunmi O.
AU - Deadman, Mike L.
AU - Al-Maqbali, Yousif Mohammed
AU - Husband, John
PY - 2007/8/20
Y1 - 2007/8/20
N2 - 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.
AB - 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.
KW - Absolute configuration
KW - Antibacterial
KW - Ascomycota
KW - Chaetomium sp
KW - Mosher ester
KW - Musanahol
KW - Polyketide
UR - http://www.scopus.com/inward/record.url?scp=34447289464&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34447289464&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.05.119
DO - 10.1016/j.tet.2007.05.119
M3 - Article
AN - SCOPUS:34447289464
SN - 0040-4020
VL - 63
SP - 8174
EP - 8180
JO - Tetrahedron
JF - Tetrahedron
IS - 34
ER -