TY - JOUR
T1 - Bioactive metabolites from the endophytic fungus stemphylium globuliferum isolated from mentha pulegium
AU - Debbab, Adbessamad
AU - Aly, Amal H.
AU - Edrada-Ebel, RuAngelie
AU - Wray, Victor
AU - Muller, Werner E.G.
AU - Totzke, Frank
AU - Zirrgiebel, Ute
AU - Schachtele, Christoph
AU - Kubbutat, Michael H.G.
AU - Lin, Wenhan
AU - Mosaddak, Mahjouba
AU - Hakikj, Adbelhak
AU - Proksch, Peter
AU - Ebel, Rainer
PY - 2009/3
Y1 - 2009/3
N2 - The endophytic fungus Stemphylium globuliferum was isolated from stem tissues of the Moroccan medicinal plant Mentha pulegium. Extracts of the fungus, which was grown on solid rice medium, exhibited considerable cytotoxicity when tested in vitro against L5178Y cells. Chemical investigation yielded five new secondary metabolites, alterporriol G (4) and its atropisomer alterporriol H (5), altersolanol K (11), altersolanol L (12), stemphypyrone (13), and the known compounds 6-O-methylalaternin (1), macrosporin (2), altersolanol A (3), alterporriol E (6), alterporriol D (7), alterporriol A (8), alterporriol B (9), and altersolanol J (10). The structures were determined on the basis of one- and two-dimensional NMR spectroscopy and mass spectrometry. Among the alterporriol-type anthranoid dimers, the mixture of alterporriols G and H (4/5) exhibited considerable cytotoxicity against L5178Y cells with an EC50 value of 2.7 μg/mL, whereas the other congeners showed only modest activity. The compounds were also tested for kinase inhibitory activity in an assay involving 24 different kinases. Compounds 1, 2, 3, and the mixture of 4 and 5 were the most potent inhibitors, displaying EC50 values between 0.64 and 1.4 μg/mL toward individual kinases.
AB - The endophytic fungus Stemphylium globuliferum was isolated from stem tissues of the Moroccan medicinal plant Mentha pulegium. Extracts of the fungus, which was grown on solid rice medium, exhibited considerable cytotoxicity when tested in vitro against L5178Y cells. Chemical investigation yielded five new secondary metabolites, alterporriol G (4) and its atropisomer alterporriol H (5), altersolanol K (11), altersolanol L (12), stemphypyrone (13), and the known compounds 6-O-methylalaternin (1), macrosporin (2), altersolanol A (3), alterporriol E (6), alterporriol D (7), alterporriol A (8), alterporriol B (9), and altersolanol J (10). The structures were determined on the basis of one- and two-dimensional NMR spectroscopy and mass spectrometry. Among the alterporriol-type anthranoid dimers, the mixture of alterporriols G and H (4/5) exhibited considerable cytotoxicity against L5178Y cells with an EC50 value of 2.7 μg/mL, whereas the other congeners showed only modest activity. The compounds were also tested for kinase inhibitory activity in an assay involving 24 different kinases. Compounds 1, 2, 3, and the mixture of 4 and 5 were the most potent inhibitors, displaying EC50 values between 0.64 and 1.4 μg/mL toward individual kinases.
KW - bioactive metabolites
KW - endophytic fungus
KW - stemphylium globuliferum
KW - mentha pulegium
KW - pharmacology
UR - http://dx.doi.org/10.1021/np8004997
U2 - 10.1021/np8004997
DO - 10.1021/np8004997
M3 - Article
SN - 0163-3864
VL - 72
SP - 626
EP - 631
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 4
ER -