title: Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae.
abstract: An unusual polyketide with a new carbon skeleton, lindgomycin (1), and the recently described ascosetin (2) were extracted from mycelia and culture broth of different Lindgomycetaceae strains, which were isolated from a sponge of the Kiel Fjord in the Baltic Sea (Germany) and from the Antarctic. Their structures were established by spectroscopic means. In the new polyketide, two distinct domains, a bicyclic hydrocarbon and a tetramic acid, are connected by a bridging carbonyl. The tetramic acid substructure of compound 1 was proved to possess a unique 5-benzylpyrrolidine-2,4-dione unit. The combination of 5-benzylpyrrolidine-2,4-dione of compound 1 in its tetramic acid half and 3-methylbut-3-enoic acid pendant in its decalin half allow the assignment of a new carbon skeleton. The new compound 1 and ascosetin showed antibiotic activities with IC50 value of 5.1 (±0.2) µM and 3.2 (±0.4) μM, respectively, against methicillin-resistant Staphylococcus aureus.
authors.affiliation: GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, Germany. wubin@zju.edu.cn.|Ocean College, Zhejiang University, Hangzhou 310058, China. wubin@zju.edu.cn.
authors.forename: Bin
authors.initials: B
authors.lastname: Wu
authors.affiliation: GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, Germany. jwiese@geomar.de.
authors.forename: Jutta
authors.initials: J
authors.lastname: Wiese
authors.affiliation: GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, Germany. alabes@geomar.de.
authors.forename: Antje
authors.initials: A
authors.lastname: Labes
authors.affiliation: GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, Germany. akramer@geomar.de.
authors.forename: Annemarie
authors.initials: A
authors.lastname: Kramer
authors.affiliation: GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, Germany. rschmaljohann@geomar.de.
authors.forename: Rolf
authors.initials: R
authors.lastname: Schmaljohann
authors.affiliation: GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, Germany. jimhoff@geomar.de.
authors.forename: Johannes F
authors.initials: JF
authors.lastname: Imhoff
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000378:metabolism* / Q000494:pharmacology; D059001:Aquatic Organisms / Q000378:metabolism*; D005658:Fungi / Q000378:metabolism*; D006838:Hydrocarbons / Q000378:metabolism; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D025282:Mycelium / Q000378:metabolism; D009281:Naphthalenes / Q000378:metabolism; D061065:Polyketides / Q000378:metabolism*; D011161:Porifera / Q000378:metabolism*; D011760:Pyrrolidinones / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D006838:Hydrocarbons; D009281:Naphthalenes; D061065:Polyketides; D011760:Pyrrolidinones; C009435:tetramic acid; C007229:decalin
keywords: MRSA; antibiotic; lindgomycin; marine fungi; marine natural products