TY - JOUR
T1 - Dibenzofurans from the marine sponge-derived ascomycete Super1F1-09
AU - Rateb, Mostafa E.
AU - Houssen, Wael E.
AU - Legrave, Nathalie M.
AU - Clements, Carol
AU - Jaspars, Marcel
AU - Ebel, Rainer
N1 - Funding Information:
M.E.R. wishes to thank the Egyptian Government for a Ph.D. scholarship. We are indebted to A. Raab for accurate mass measurements, J. Plater and M.H. Abdelrahman (Department of Chemistry, University of Aberdeen, Aberdeen, UK) for advice on organic synthesis, and A. Crossman (Department of Chemistry, University of Dundee) for determination of optical activity. We thank DNA Sequencing & Services (MRCPPU, College of Life Sciences, University of Dundee, Dundee, UK) for DNA sequencing. M.J. is the recipient of a Biotechnology and Biological Sciences Research Council (BBSRC) Research Development Fellowship.
PY - 2010/12/1
Y1 - 2010/12/1
N2 - Three dibenzofurans hitherto undescribed from nature and one known butyrolactone were isolated from the extract of the ascomycete Super1F1-09 isolated from the Fijian marine sponge Acanthella cavernosa. The isolated compounds were identified as 3,9-dimethyldibenzo[b,d]furan-1,7-diol (1), 3-(hydroxymethyl)-9-methyldibenzo[b,d]furan-1,7-diol (2), 1,7-dihydroxy-9- methyldibenzo[b,d]furan-3-carboxylic acid (3), and the known butyrolactone I (4) using different NMR spectroscopic techniques and accurate mass spectrometric analysis. 1 was synthesized together with structurally related dibenzofurans 6-8. 1 and 4 had moderate antibacterial activity toward Mycobacterium marinum and Staphylococcus aureus, whereas 2 and 3 proved inactive. In addition, all compounds had moderate inhibitory properties against epidermal growth factor receptor tyrosine kinase.
AB - Three dibenzofurans hitherto undescribed from nature and one known butyrolactone were isolated from the extract of the ascomycete Super1F1-09 isolated from the Fijian marine sponge Acanthella cavernosa. The isolated compounds were identified as 3,9-dimethyldibenzo[b,d]furan-1,7-diol (1), 3-(hydroxymethyl)-9-methyldibenzo[b,d]furan-1,7-diol (2), 1,7-dihydroxy-9- methyldibenzo[b,d]furan-3-carboxylic acid (3), and the known butyrolactone I (4) using different NMR spectroscopic techniques and accurate mass spectrometric analysis. 1 was synthesized together with structurally related dibenzofurans 6-8. 1 and 4 had moderate antibacterial activity toward Mycobacterium marinum and Staphylococcus aureus, whereas 2 and 3 proved inactive. In addition, all compounds had moderate inhibitory properties against epidermal growth factor receptor tyrosine kinase.
KW - Acanthella cavernosa
KW - antibacterial activity
KW - ascomycete
KW - dibenzofurans
KW - sponge-derived fungal metabolites
KW - tyrosine kinase inhibition
UR - http://www.scopus.com/inward/record.url?scp=78649886555&partnerID=8YFLogxK
U2 - 10.1515/BOT.2010.064
DO - 10.1515/BOT.2010.064
M3 - Article
AN - SCOPUS:78649886555
SN - 0006-8055
VL - 53
SP - 499
EP - 506
JO - Botanica Marina
JF - Botanica Marina
IS - 6
ER -