Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae

• Published in: Marine Drugs
• Main Authors: Wu, Bin, Wiese, Jutta, Labes, Antje, Kramer, Annemarie, Schmaljohann, Rolf, Imhoff, Johannes F.
• Format: Article in Journal/Newspaper
• Language: English
• Published: MDPI 2015
• Subjects: Antarctic; The Antarctic; Antarc*
• Online Access: https://oceanrep.geomar.de/id/eprint/29518/; https://oceanrep.geomar.de/id/eprint/29518/1/Wu_Lindgomycin_2015_marinedrugs-13-04617.pdf; https://doi.org/10.3390/md13084617

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.