title: New bhimamycins from Streptomyces sp. AK 671.
abstract: From the wild-type strain Steptomyces sp. AK 671, three nitrogen-containing octaketides were isolated, bhimamycins F, H and I, besides the known azaanthraquinone utahmycin A and polyketide shunt products SEK 4, SEK 4b, mutactin, dehydromutactin and EM18. The structures were characterized by MS and NMR experiments. The hitherto unknown absolute configuration of the two enantiomers of EM18 was determined by online-CD spectroscopy and quantum-chemical CD calculations. Bhimamycins H and I show weak antibacterial activities, whereas the enzyme phosphodiesterase 4 is strongly inhibited by bhimamycins H and I, which has never been reported for nitrogen-containing octaketides. In addition, bhimamycin H inhibits the enzyme glycogen synthase kinase-3β.
authors.affiliation: Mikrobiologisches Institut, Universität Tübingen, Tübingen, Germany.
authors.forename: Philipp
authors.initials: P
authors.lastname: Jetter
authors.affiliation: Institut für Organische Chemie, Universität Würzburg, Würzburg, Germany.
authors.forename: Claudia
authors.initials: C
authors.lastname: Steinert
authors.affiliation: Institut für Organische Chemie, Universität Würzburg, Würzburg, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Knauer
authors.affiliation: Institut für Organische Chemie, Universität Würzburg, Würzburg, Germany.
authors.forename: Guoliang
authors.initials: G
authors.lastname: Zhang
authors.affiliation: Institut für Organische Chemie, Universität Würzburg, Würzburg, Germany.
authors.forename: Torsten
authors.initials: T
authors.lastname: Bruhn
authors.affiliation: Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz-Zentrum für Ozeanforschung, Kiel, Germany.
authors.forename: Jutta
authors.initials: J
authors.lastname: Wiese
authors.affiliation: Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz-Zentrum für Ozeanforschung, Kiel, Germany.
authors.forename: Johannes F
authors.initials: JF
authors.lastname: Imhoff
authors.affiliation: Mikrobiologisches Institut, Universität Tübingen, Tübingen, Germany.
authors.forename: Hans-Peter
authors.initials: HP
authors.lastname: Fiedler
authors.affiliation: Institut für Organische Chemie, Universität Würzburg, Würzburg, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Bringmann
mesh_terms: D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000737:chemistry* / Q000494:pharmacology; D005285:Fermentation; D009682:Magnetic Resonance Spectroscopy; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D015394:Molecular Structure; D048630:Polyketide Synthases / Q000378:metabolism; D061065:Polyketides / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D011758:Pyrroles / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D011809:Quinones / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013212:Staphylococcus epidermidis / Q000187:drug effects; D013237:Stereoisomerism; D013302:Streptomyces / Q000378:metabolism*
chemical_list: D000900:Anti-Bacterial Agents; D061065:Polyketides; D011758:Pyrroles; D011809:Quinones; C586478:bhimamycin F; C586479:bhimamycin H; C586480:bhimamycin I; D048630:Polyketide Synthases