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

Wu B, Wiese J, Labes A, Kramer A, Schmaljohann R, Imhoff JF - Mar Drugs (2015)

Bottom Line: In the new polyketide, two distinct domains, a bicyclic hydrocarbon and a tetramic acid, are connected by a bridging carbonyl.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.

View Article: PubMed Central - PubMed

Affiliation: GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, Germany. wubin@zju.edu.cn.

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.

No MeSH data available.


Related in: MedlinePlus

Lindgomycetaceae strain KF970, agar colony on WSP30 medium after 21 days of incubation at 22 °C.
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marinedrugs-13-04617-f001: Lindgomycetaceae strain KF970, agar colony on WSP30 medium after 21 days of incubation at 22 °C.

Mentions: Two fungal isolates, strains KF970 and LF327, which are members of the family Lindgomycetaceae, were isolated from different marine habitats. Both strains grew only as sterile mycelium on the media used, but did not produce conidia or ascomata on ten different media, e.g., on WSP30 (Figure 1). Thus, morphological criteria for identification of the strain were lacking. The sequences of the 18S rRNA genes comprised 1546 nucleotides for KF970 and 1065 nucleotides for LF327, respectively. Both sequences exhibited a similarity of 99.7% to each other. The highest sequence similarity (100%) was observed for the 18S RNA gene sequence to “Phyllosticta” flevolandica AFTOL-ID 1786. Nevertheless, the deposited sequence of the P.flevolandica strain comprises only approximately a fourth of the length of 18S rRNA gene (441 nucleotides) and Crous et al. [16] have shown that “Phyllosticta” flevolandica does not affiliate with all members of the genus Phyllosticta, which belong to the Botryosphaeriales.Therefore, the strains most closely related were taken into consideration for the phylogenetic classification. Among these, Massariosphaeria typhicola CBS 609.86 (acc. no. KF314118) showed similarities of 99.9% to KF970 and 99.5% to LF327, respectively. The 18S rDNA sequences of strains KF970 and LF327 showed 99.2%–99.5% and 99.0%–99.2% similarity to the type of strains of the seven known Lindgomyces species [10]. Clohesyomyces aquaticus MFLUCC11-0092 (acc. no. JX276949) was 99.0% similar to KF970 and 99.78% similar to LF327. A comparison with the genus Lolia was not possible because no 18S rRNA gene sequence was deposited.


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

Wu B, Wiese J, Labes A, Kramer A, Schmaljohann R, Imhoff JF - Mar Drugs (2015)

Lindgomycetaceae strain KF970, agar colony on WSP30 medium after 21 days of incubation at 22 °C.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4556996&req=5

marinedrugs-13-04617-f001: Lindgomycetaceae strain KF970, agar colony on WSP30 medium after 21 days of incubation at 22 °C.
Mentions: Two fungal isolates, strains KF970 and LF327, which are members of the family Lindgomycetaceae, were isolated from different marine habitats. Both strains grew only as sterile mycelium on the media used, but did not produce conidia or ascomata on ten different media, e.g., on WSP30 (Figure 1). Thus, morphological criteria for identification of the strain were lacking. The sequences of the 18S rRNA genes comprised 1546 nucleotides for KF970 and 1065 nucleotides for LF327, respectively. Both sequences exhibited a similarity of 99.7% to each other. The highest sequence similarity (100%) was observed for the 18S RNA gene sequence to “Phyllosticta” flevolandica AFTOL-ID 1786. Nevertheless, the deposited sequence of the P.flevolandica strain comprises only approximately a fourth of the length of 18S rRNA gene (441 nucleotides) and Crous et al. [16] have shown that “Phyllosticta” flevolandica does not affiliate with all members of the genus Phyllosticta, which belong to the Botryosphaeriales.Therefore, the strains most closely related were taken into consideration for the phylogenetic classification. Among these, Massariosphaeria typhicola CBS 609.86 (acc. no. KF314118) showed similarities of 99.9% to KF970 and 99.5% to LF327, respectively. The 18S rDNA sequences of strains KF970 and LF327 showed 99.2%–99.5% and 99.0%–99.2% similarity to the type of strains of the seven known Lindgomyces species [10]. Clohesyomyces aquaticus MFLUCC11-0092 (acc. no. JX276949) was 99.0% similar to KF970 and 99.78% similar to LF327. A comparison with the genus Lolia was not possible because no 18S rRNA gene sequence was deposited.

Bottom Line: In the new polyketide, two distinct domains, a bicyclic hydrocarbon and a tetramic acid, are connected by a bridging carbonyl.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.

View Article: PubMed Central - PubMed

Affiliation: GEOMAR Helmholtz Centre for Ocean Research Kiel, 24105 Kiel, Germany. wubin@zju.edu.cn.

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.

No MeSH data available.


Related in: MedlinePlus