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Diversity of Antimicrobial Pyrenophorol Derivatives from an Endophytic Fungus, Phoma sp.
Author(s) -
Zhang Wen,
Krohn Karsten,
Egold Hans,
Draeger Siegfried,
Schulz Barbara
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800404
Subject(s) - chemistry , fungus , antimicrobial , bacillus megaterium , phoma , stereochemistry , bacteria , botany , organic chemistry , biology , genetics
Pyrenophorol ( 1 ) and (–)‐dihydropyrenophorin ( 3 ), two known macrodiolides, were isolated together with four new analogues ( 2 , 4 – 6 ) and three ring‐opened derivatives ( 7 – 9 ) from Phoma sp., an endophytic fungus isolated from Lycium intricatum from Gomera. The structures of the new compounds were elucidated by detailed spectroscopic analysis, comparison with reported data, and chemical interconversion. The absolute configurations were determined by chemical correlations and a modified Mosher's method. The diversity of these seven newly discovered metabolites not only extends the pyrenophorol macrocyclic family, but also gives insight into the biosynthetic interconnections, in particular by isolation of the open‐chain precursors. Preliminary studies showed antimicrobial activity of these compounds against the fungus Microbotryum violaceum , the alga Chlorellafusca , and the bacteria Escherichia coli and Bacillus megaterium. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)