A Structural Analysis of the Angucycline-Like Antibiotic Auricin from <i>Streptomyces lavendulae</i> Subsp. <i>Lavendulae</i> CCM 3239 Revealed Its High Similarity to Griseusins
We previously identified the <i>aur1</i> gene cluster in <i>Streptomyces lavendulae</i> subsp. <i>lavendulae</i> CCM 3239 (formerly <i>Streptomyces aureofaciens</i> CCM 3239), which is responsible for the production of the angucycline-like antibiotic a...
| Main Authors: | , , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2019-07-01
|
| Series: | Antibiotics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2079-6382/8/3/102 |
| _version_ | 1818953245561716736 |
|---|---|
| author | Maria Matulova Lubomira Feckova Renata Novakova Erik Mingyar Dominika Csolleiova Martina Zduriencikova Jan Sedlak Vladimir Patoprsty Vlasta Sasinkova Iveta Uhliarikova Beatrica Sevcikova Bronislava Rezuchova Dagmar Homerova Jan Kormanec |
| author_facet | Maria Matulova Lubomira Feckova Renata Novakova Erik Mingyar Dominika Csolleiova Martina Zduriencikova Jan Sedlak Vladimir Patoprsty Vlasta Sasinkova Iveta Uhliarikova Beatrica Sevcikova Bronislava Rezuchova Dagmar Homerova Jan Kormanec |
| author_sort | Maria Matulova |
| collection | DOAJ |
| description | We previously identified the <i>aur1</i> gene cluster in <i>Streptomyces lavendulae</i> subsp. <i>lavendulae</i> CCM 3239 (formerly <i>Streptomyces aureofaciens</i> CCM 3239), which is responsible for the production of the angucycline-like antibiotic auricin (<b>1</b>). Preliminary characterization of <b>1</b> revealed that it possesses an aminodeoxyhexose <span style="font-variant: small-caps;">d</span>-forosamine and is active against Gram-positive bacteria. Here we determined the structure of <b>1</b>, finding that it possesses intriguing structural features, which distinguish it from other known angucyclines. In addition to <span style="font-variant: small-caps;">d</span>-forosamine, compound <b>1</b> also contains a unique, highly oxygenated aglycone similar to those of spiroketal pyranonaphthoquinones griseusins. Like several other griseusins, <b>1</b> also undergoes methanolysis and displays modest cytotoxicity against several human tumor cell lines. Moreover, the central core of the <i>aur1</i> cluster is highly similar to the partial <i>gris</i> gene cluster responsible for the biosynthesis of griseusin A and B in both the nature of the encoded proteins and the gene organization. |
| first_indexed | 2024-12-20T10:03:13Z |
| format | Article |
| id | doaj.art-bfec10b9ee8e433b907c382ffa9b748c |
| institution | Directory Open Access Journal |
| issn | 2079-6382 |
| language | English |
| last_indexed | 2024-12-20T10:03:13Z |
| publishDate | 2019-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antibiotics |
| spelling | doaj.art-bfec10b9ee8e433b907c382ffa9b748c2022-12-21T19:44:18ZengMDPI AGAntibiotics2079-63822019-07-018310210.3390/antibiotics8030102antibiotics8030102A Structural Analysis of the Angucycline-Like Antibiotic Auricin from <i>Streptomyces lavendulae</i> Subsp. <i>Lavendulae</i> CCM 3239 Revealed Its High Similarity to GriseusinsMaria Matulova0Lubomira Feckova1Renata Novakova2Erik Mingyar3Dominika Csolleiova4Martina Zduriencikova5Jan Sedlak6Vladimir Patoprsty7Vlasta Sasinkova8Iveta Uhliarikova9Beatrica Sevcikova10Bronislava Rezuchova11Dagmar Homerova12Jan Kormanec13Institute of Chemistry, Slovak Academy of Sciences, 845 38 Bratislava, SlovakiaInstitute of Molecular Biology, Slovak Academy of Sciences, 845 51 Bratislava, SlovakiaInstitute of Molecular Biology, Slovak Academy of Sciences, 845 51 Bratislava, SlovakiaInstitute of Molecular Biology, Slovak Academy of Sciences, 845 51 Bratislava, SlovakiaInstitute of Molecular Biology, Slovak Academy of Sciences, 845 51 Bratislava, SlovakiaInstitute of Chemistry, Slovak Academy of Sciences, 845 38 Bratislava, SlovakiaCancer Research Institute BMC, Slovak Academy of Sciences, 845 05 Bratislava, SlovakiaInstitute of Chemistry, Slovak Academy of Sciences, 845 38 Bratislava, SlovakiaInstitute of Chemistry, Slovak Academy of Sciences, 845 38 Bratislava, SlovakiaInstitute of Chemistry, Slovak Academy of Sciences, 845 38 Bratislava, SlovakiaInstitute of Molecular Biology, Slovak Academy of Sciences, 845 51 Bratislava, SlovakiaInstitute of Molecular Biology, Slovak Academy of Sciences, 845 51 Bratislava, SlovakiaInstitute of Molecular Biology, Slovak Academy of Sciences, 845 51 Bratislava, SlovakiaInstitute of Molecular Biology, Slovak Academy of Sciences, 845 51 Bratislava, SlovakiaWe previously identified the <i>aur1</i> gene cluster in <i>Streptomyces lavendulae</i> subsp. <i>lavendulae</i> CCM 3239 (formerly <i>Streptomyces aureofaciens</i> CCM 3239), which is responsible for the production of the angucycline-like antibiotic auricin (<b>1</b>). Preliminary characterization of <b>1</b> revealed that it possesses an aminodeoxyhexose <span style="font-variant: small-caps;">d</span>-forosamine and is active against Gram-positive bacteria. Here we determined the structure of <b>1</b>, finding that it possesses intriguing structural features, which distinguish it from other known angucyclines. In addition to <span style="font-variant: small-caps;">d</span>-forosamine, compound <b>1</b> also contains a unique, highly oxygenated aglycone similar to those of spiroketal pyranonaphthoquinones griseusins. Like several other griseusins, <b>1</b> also undergoes methanolysis and displays modest cytotoxicity against several human tumor cell lines. Moreover, the central core of the <i>aur1</i> cluster is highly similar to the partial <i>gris</i> gene cluster responsible for the biosynthesis of griseusin A and B in both the nature of the encoded proteins and the gene organization.https://www.mdpi.com/2079-6382/8/3/102antibioticangucyclineauricinbiosynthesisgriseusinpolyketidepyronaphthoquiononeregulationsecondary metabolism<i>Streptomyces</i>structure elucidation |
| spellingShingle | Maria Matulova Lubomira Feckova Renata Novakova Erik Mingyar Dominika Csolleiova Martina Zduriencikova Jan Sedlak Vladimir Patoprsty Vlasta Sasinkova Iveta Uhliarikova Beatrica Sevcikova Bronislava Rezuchova Dagmar Homerova Jan Kormanec A Structural Analysis of the Angucycline-Like Antibiotic Auricin from <i>Streptomyces lavendulae</i> Subsp. <i>Lavendulae</i> CCM 3239 Revealed Its High Similarity to Griseusins Antibiotics antibiotic angucycline auricin biosynthesis griseusin polyketide pyronaphthoquionone regulation secondary metabolism <i>Streptomyces</i> structure elucidation |
| title | A Structural Analysis of the Angucycline-Like Antibiotic Auricin from <i>Streptomyces lavendulae</i> Subsp. <i>Lavendulae</i> CCM 3239 Revealed Its High Similarity to Griseusins |
| title_full | A Structural Analysis of the Angucycline-Like Antibiotic Auricin from <i>Streptomyces lavendulae</i> Subsp. <i>Lavendulae</i> CCM 3239 Revealed Its High Similarity to Griseusins |
| title_fullStr | A Structural Analysis of the Angucycline-Like Antibiotic Auricin from <i>Streptomyces lavendulae</i> Subsp. <i>Lavendulae</i> CCM 3239 Revealed Its High Similarity to Griseusins |
| title_full_unstemmed | A Structural Analysis of the Angucycline-Like Antibiotic Auricin from <i>Streptomyces lavendulae</i> Subsp. <i>Lavendulae</i> CCM 3239 Revealed Its High Similarity to Griseusins |
| title_short | A Structural Analysis of the Angucycline-Like Antibiotic Auricin from <i>Streptomyces lavendulae</i> Subsp. <i>Lavendulae</i> CCM 3239 Revealed Its High Similarity to Griseusins |
| title_sort | structural analysis of the angucycline like antibiotic auricin from i streptomyces lavendulae i subsp i lavendulae i ccm 3239 revealed its high similarity to griseusins |
| topic | antibiotic angucycline auricin biosynthesis griseusin polyketide pyronaphthoquionone regulation secondary metabolism <i>Streptomyces</i> structure elucidation |
| url | https://www.mdpi.com/2079-6382/8/3/102 |
| work_keys_str_mv | AT mariamatulova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT lubomirafeckova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT renatanovakova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT erikmingyar astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT dominikacsolleiova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT martinazduriencikova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT jansedlak astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT vladimirpatoprsty astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT vlastasasinkova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT ivetauhliarikova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT beatricasevcikova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT bronislavarezuchova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT dagmarhomerova astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT jankormanec astructuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT mariamatulova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT lubomirafeckova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT renatanovakova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT erikmingyar structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT dominikacsolleiova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT martinazduriencikova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT jansedlak structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT vladimirpatoprsty structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT vlastasasinkova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT ivetauhliarikova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT beatricasevcikova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT bronislavarezuchova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT dagmarhomerova structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins AT jankormanec structuralanalysisoftheangucyclinelikeantibioticauricinfromistreptomyceslavendulaeisubspilavendulaeiccm3239revealeditshighsimilaritytogriseusins |