Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae
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. The...
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MDPI AG
2015-07-01
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| Series: | Marine Drugs |
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| Online Access: | http://www.mdpi.com/1660-3397/13/8/4617 |
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doaj-b81371ec482c423ebe5a018125d8b55d2020-11-24T21:45:12ZengMDPI AGMarine Drugs1660-33972015-07-011384617463210.3390/md13084617md13084617Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the LindgomycetaceaeBin Wu0Jutta Wiese1Antje Labes2Annemarie Kramer3Rolf Schmaljohann4Johannes F. Imhoff5GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, GermanyGEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, GermanyGEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, GermanyGEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, GermanyGEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, GermanyGEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, GermanyAn 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.http://www.mdpi.com/1660-3397/13/8/4617marine fungilindgomycinantibioticMRSAmarine natural products |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Bin Wu Jutta Wiese Antje Labes Annemarie Kramer Rolf Schmaljohann Johannes F. Imhoff |
| spellingShingle |
Bin Wu Jutta Wiese Antje Labes Annemarie Kramer Rolf Schmaljohann Johannes F. Imhoff Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae Marine Drugs marine fungi lindgomycin antibiotic MRSA marine natural products |
| author_facet |
Bin Wu Jutta Wiese Antje Labes Annemarie Kramer Rolf Schmaljohann Johannes F. Imhoff |
| author_sort |
Bin Wu |
| title |
Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae |
| title_short |
Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae |
| title_full |
Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae |
| title_fullStr |
Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae |
| title_full_unstemmed |
Lindgomycin, an Unusual Antibiotic Polyketide from a Marine Fungus of the Lindgomycetaceae |
| title_sort |
lindgomycin, an unusual antibiotic polyketide from a marine fungus of the lindgomycetaceae |
| publisher |
MDPI AG |
| series |
Marine Drugs |
| issn |
1660-3397 |
| publishDate |
2015-07-01 |
| description |
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. |
| topic |
marine fungi lindgomycin antibiotic MRSA marine natural products |
| url |
http://www.mdpi.com/1660-3397/13/8/4617 |
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