Eutypoids B-E produced by a Penicillium sp. strain from the North Sea.
Crude extracts of the Penicillium sp. strain KF620 isolated from the North Sea showed antimicrobial activities against Xanthomonas campestris and Candida glabrata. Purification of the extracts led to the isolation of the new aromatic butenolides eutypoids B (1), C (2), D (3), and E (4). Their structures were elucidated by NMR spectroscopy and supported by HRESIMS and UV data. The antibacterial activity of the crude extracts was due to the presence of the known diketopiperazine fellutanine (cyclo(Trp-Trp)). The eutypoids were neither cytotoxic nor antibacterial, but inhibited the activity of glycogen synthase kinase-3β.
Kieler Wirkstoff-Zentrum at the Leibniz-Institute of Marine Sciences (IFM-GEOMAR), Am Kiel-Kanal 44, 24106 Kiel, Germany.
Dirk
D
Schulz
Birgit
B
Ohlendorf
Heidi
H
Zinecker
Rolf
R
Schmaljohann
Johannes F
JF
Imhoff
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000627:Aminophenols / Q000737:chemistry; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D041221:Candida glabrata / Q000187:drug effects; D004151:Dipeptides / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D038341:Glycogen Synthase Kinases / Q000037:antagonists & inhibitors; D019073:HT29 Cells; D056945:Hep G2 Cells; D006801:Humans; D008301:Maleimides / Q000737:chemistry; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D041681:NIH 3T3 Cells; D009659:North Sea; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000494:pharmacology; D016959:Xanthomonas campestris / Q000187:drug effects
C417520:3-(3-chloro-4-hydroxyphenylamino)-4-(4-nitrophenyl)-1H-pyrrole-2,5-dione; D000627:Aminophenols; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D004151:Dipeptides; D008301:Maleimides; D010456:Peptides, Cyclic; C118538:cyclo(tryptophyl-tryptophyl); C004511:butenolide; D038341:Glycogen Synthase Kinases; D015107:4-Butyrolactone