Bioactive metabolites from the endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium

A. Debbab, A.H. Aly, P. Proksch, R. Edrada-Ebel, V. Wray, W.E.G. Müller, F. Totzke, U. Zirrgiebel, C. Schächtele, M.H.G. Kubbutat, H.L. Wen, M. Mosaddak, A. Hakiki, R. Ebel

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Abstract

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 EC 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 EC values between 0.64 and 1.4 µg/mL toward individual kinases.
Original languageEnglish
Pages (from-to)626-631
Number of pages6
JournalJournal of Natural Products
Volume72
Issue number4
Early online date9 Mar 2009
DOIs
Publication statusPublished - 24 Apr 2009

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Mentha pulegium
Metabolites
Fungi
Phosphotransferases
Cytotoxicity
Anthraquinones
Medicinal Plants
Dimers
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Assays
Mass Spectrometry
Magnetic Resonance Spectroscopy
Tissue

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Bioactive metabolites from the endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium. / Debbab, A.; Aly, A.H.; Proksch, P.; Edrada-Ebel, R.; Wray, V.; Müller, W.E.G.; Totzke, F.; Zirrgiebel, U.; Schächtele, C.; Kubbutat, M.H.G.; Wen, H.L.; Mosaddak, M.; Hakiki, A.; Ebel, R.

In: Journal of Natural Products, Vol. 72, No. 4, 24.04.2009, p. 626-631.

Research output: Contribution to journalArticle

Debbab, A, Aly, AH, Proksch, P, Edrada-Ebel, R, Wray, V, Müller, WEG, Totzke, F, Zirrgiebel, U, Schächtele, C, Kubbutat, MHG, Wen, HL, Mosaddak, M, Hakiki, A & Ebel, R 2009, 'Bioactive metabolites from the endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium', Journal of Natural Products, vol. 72, no. 4, pp. 626-631. https://doi.org/10.1021/np8004997
Debbab, A. ; Aly, A.H. ; Proksch, P. ; Edrada-Ebel, R. ; Wray, V. ; Müller, W.E.G. ; Totzke, F. ; Zirrgiebel, U. ; Schächtele, C. ; Kubbutat, M.H.G. ; Wen, H.L. ; Mosaddak, M. ; Hakiki, A. ; Ebel, R. / Bioactive metabolites from the endophytic fungus Stemphylium globuliferum isolated from Mentha pulegium. In: Journal of Natural Products. 2009 ; Vol. 72, No. 4. pp. 626-631.
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AU - Debbab, A.

AU - Aly, A.H.

AU - Proksch, P.

AU - Edrada-Ebel, R.

AU - Wray, V.

AU - Müller, W.E.G.

AU - Totzke, F.

AU - Zirrgiebel, U.

AU - Schächtele, C.

AU - Kubbutat, M.H.G.

AU - Wen, H.L.

AU - Mosaddak, M.

AU - Hakiki, A.

AU - Ebel, R.

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PY - 2009/4/24

Y1 - 2009/4/24

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 EC 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 EC 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 EC 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 EC values between 0.64 and 1.4 µg/mL toward individual kinases.

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