Bioactive Molecular Networking for Mapping the Antimicrobial Constituents of the Baltic Brown Alga <i>Fucus vesiculosus</i>
The brown alga <i>Fucus vesiculosus</i> is common to the intertidal zones of the Baltic Sea, where it is exposed to high fouling pressures by microorganisms. Our previous studies showed, repeatedly, the consistent antimicrobial activity of <i>F. vesiculosus</i> crude extracts...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-06-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/6/311 |
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| author | Larissa Buedenbender Francesca Anna Astone Deniz Tasdemir |
| author_facet | Larissa Buedenbender Francesca Anna Astone Deniz Tasdemir |
| author_sort | Larissa Buedenbender |
| collection | DOAJ |
| description | The brown alga <i>Fucus vesiculosus</i> is common to the intertidal zones of the Baltic Sea, where it is exposed to high fouling pressures by microorganisms. Our previous studies showed, repeatedly, the consistent antimicrobial activity of <i>F. vesiculosus</i> crude extracts against human pathogens, while untargeted metabolomics analyses have revealed a variety of metabolites. In this study, we applied the UPLC-QToF-MS/MS-based “bioactive molecular networking” (BMN) concept on the most bioactive <i>n-</i>hexane and <i>n</i>-butanol subextracts of Baltic <i>F. vesiculosus</i> coupled with in silico dereplication tools to identify the compounds responsible for antimicrobial activity. The first antimicrobial cluster identified by BMN was galactolipids. Our targeted isolation efforts for this class led to the isolation of six monogalactosyldiacylglycerol (MGDG) derivatives (<b>1</b>–<b>6</b>) and one digalactosyldiacylglycerol (DGDG, <b>7</b>). The MGDGs <b>5</b> and <b>6</b> and the DGDG <b>7</b> exhibited activity against <i>Staphylococcus aureus.</i> The second compound class with high bioactivity was phlorotannins. In particular, phlorethol-type phlorotannins showed high correlations with antimicrobial activity based on the BMN approach, and two phlorotannins (<b>8</b>–<b>9</b>) were isolated. This study shows that antimicrobial components of <i>F. vesiculosus</i> reside in the algal cell walls and membranes and that BMN provides a complementary tool for the targeted isolation of bioactive metabolites. |
| first_indexed | 2024-03-10T19:12:35Z |
| format | Article |
| id | doaj.art-ee2a725acc9f4ed79ac1e597059680fb |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T19:12:35Z |
| publishDate | 2020-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-ee2a725acc9f4ed79ac1e597059680fb2023-11-20T03:44:56ZengMDPI AGMarine Drugs1660-33972020-06-0118631110.3390/md18060311Bioactive Molecular Networking for Mapping the Antimicrobial Constituents of the Baltic Brown Alga <i>Fucus vesiculosus</i>Larissa Buedenbender0Francesca Anna Astone1Deniz Tasdemir2GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, GermanyGEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, GermanyGEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, GermanyThe brown alga <i>Fucus vesiculosus</i> is common to the intertidal zones of the Baltic Sea, where it is exposed to high fouling pressures by microorganisms. Our previous studies showed, repeatedly, the consistent antimicrobial activity of <i>F. vesiculosus</i> crude extracts against human pathogens, while untargeted metabolomics analyses have revealed a variety of metabolites. In this study, we applied the UPLC-QToF-MS/MS-based “bioactive molecular networking” (BMN) concept on the most bioactive <i>n-</i>hexane and <i>n</i>-butanol subextracts of Baltic <i>F. vesiculosus</i> coupled with in silico dereplication tools to identify the compounds responsible for antimicrobial activity. The first antimicrobial cluster identified by BMN was galactolipids. Our targeted isolation efforts for this class led to the isolation of six monogalactosyldiacylglycerol (MGDG) derivatives (<b>1</b>–<b>6</b>) and one digalactosyldiacylglycerol (DGDG, <b>7</b>). The MGDGs <b>5</b> and <b>6</b> and the DGDG <b>7</b> exhibited activity against <i>Staphylococcus aureus.</i> The second compound class with high bioactivity was phlorotannins. In particular, phlorethol-type phlorotannins showed high correlations with antimicrobial activity based on the BMN approach, and two phlorotannins (<b>8</b>–<b>9</b>) were isolated. This study shows that antimicrobial components of <i>F. vesiculosus</i> reside in the algal cell walls and membranes and that BMN provides a complementary tool for the targeted isolation of bioactive metabolites.https://www.mdpi.com/1660-3397/18/6/311<i>Fucus vesiculosus</i>brown algabioactive molecular networkingin silico dereplicationmetabolomicsantimicrobial |
| spellingShingle | Larissa Buedenbender Francesca Anna Astone Deniz Tasdemir Bioactive Molecular Networking for Mapping the Antimicrobial Constituents of the Baltic Brown Alga <i>Fucus vesiculosus</i> Marine Drugs <i>Fucus vesiculosus</i> brown alga bioactive molecular networking in silico dereplication metabolomics antimicrobial |
| title | Bioactive Molecular Networking for Mapping the Antimicrobial Constituents of the Baltic Brown Alga <i>Fucus vesiculosus</i> |
| title_full | Bioactive Molecular Networking for Mapping the Antimicrobial Constituents of the Baltic Brown Alga <i>Fucus vesiculosus</i> |
| title_fullStr | Bioactive Molecular Networking for Mapping the Antimicrobial Constituents of the Baltic Brown Alga <i>Fucus vesiculosus</i> |
| title_full_unstemmed | Bioactive Molecular Networking for Mapping the Antimicrobial Constituents of the Baltic Brown Alga <i>Fucus vesiculosus</i> |
| title_short | Bioactive Molecular Networking for Mapping the Antimicrobial Constituents of the Baltic Brown Alga <i>Fucus vesiculosus</i> |
| title_sort | bioactive molecular networking for mapping the antimicrobial constituents of the baltic brown alga i fucus vesiculosus i |
| topic | <i>Fucus vesiculosus</i> brown alga bioactive molecular networking in silico dereplication metabolomics antimicrobial |
| url | https://www.mdpi.com/1660-3397/18/6/311 |
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