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. 2015 Jul 27;13(8):4617-32.
doi: 10.3390/md13084617.

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

Bin Wu  1   2 , Jutta Wiese  3 , Antje Labes  4 , Annemarie Kramer  5 , Rolf Schmaljohann  6 , Johannes F Imhoff  7
Affiliations

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

Bin Wu et al. Mar Drugs. .

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.

Keywords: MRSA; antibiotic; lindgomycin; marine fungi; marine natural products.

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Figures

Figure 1
Figure 1
Lindgomycetaceae strain KF970, agar colony on WSP30 medium after 21 days of incubation at 22 °C.
Figure 2
Figure 2
Structures of compounds 1 and 2.
Figure 3
Figure 3
Key 1H–1H COSY and HMBC correlations of compound 1.
Figure 4
Figure 4
Key NOESY correlations of compound 1.
See this image and copyright information in PMC

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