Unveiling the Chemical Diversity of the Deep-Sea Sponge <i>Characella pachastrelloides</i>
Sponges are at the forefront of marine natural product research. In the deep sea, extreme conditions have driven secondary metabolite pathway evolution such that we might expect deep-sea sponges to yield a broad range of unique natural products. Here, we investigate the chemodiversity of a deep-sea...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-01-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/1/52 |
| _version_ | 1797492566797582336 |
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| author | Sam Afoullouss Anthony R. Sanchez Laurence K. Jennings Younghoon Kee A. Louise Allcock Olivier P. Thomas |
| author_facet | Sam Afoullouss Anthony R. Sanchez Laurence K. Jennings Younghoon Kee A. Louise Allcock Olivier P. Thomas |
| author_sort | Sam Afoullouss |
| collection | DOAJ |
| description | Sponges are at the forefront of marine natural product research. In the deep sea, extreme conditions have driven secondary metabolite pathway evolution such that we might expect deep-sea sponges to yield a broad range of unique natural products. Here, we investigate the chemodiversity of a deep-sea tetractinellid sponge, <i>Characella pachastrelloides</i>, collected from ~800 m depth in Irish waters. First, we analyzed the MS/MS data obtained from fractions of this sponge on the GNPS public online platform to guide our exploration of its chemodiversity. Novel glycolipopeptides named characellides were previously isolated from the sponge and herein cyanocobalamin, a manufactured form of vitamin B<sub>12</sub>, not previously found in nature, was isolated in a large amount. We also identified several poecillastrins from the molecular network, a class of polyketide known to exhibit cytotoxicity. Light sensitivity prevented the isolation and characterization of these polyketides, but their presence was confirmed by characteristic NMR and MS signals. Finally, we isolated the new betaine 6-methylhercynine, which contains a unique methylation at C-2 of the imidazole ring. This compound showed potent cytotoxicity towards against HeLa (cervical cancer) cells. |
| first_indexed | 2024-03-10T01:05:32Z |
| format | Article |
| id | doaj.art-86f8f5d28621468dbd784ad2281e8af4 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T01:05:32Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-86f8f5d28621468dbd784ad2281e8af42023-11-23T14:28:00ZengMDPI AGMarine Drugs1660-33972022-01-012015210.3390/md20010052Unveiling the Chemical Diversity of the Deep-Sea Sponge <i>Characella pachastrelloides</i>Sam Afoullouss0Anthony R. Sanchez1Laurence K. Jennings2Younghoon Kee3A. Louise Allcock4Olivier P. Thomas5Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91TK33 Galway, IrelandDepartment of Cell Biology, Microbiology, and Molecular Biology, University of South Florida, 4202 E. Fowler Ave., Tampa, FL 33620, USAMarine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91TK33 Galway, IrelandDepartment of Cell Biology, Microbiology, and Molecular Biology, University of South Florida, 4202 E. Fowler Ave., Tampa, FL 33620, USASchool of Natural Sciences and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91TK33 Galway, IrelandMarine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91TK33 Galway, IrelandSponges are at the forefront of marine natural product research. In the deep sea, extreme conditions have driven secondary metabolite pathway evolution such that we might expect deep-sea sponges to yield a broad range of unique natural products. Here, we investigate the chemodiversity of a deep-sea tetractinellid sponge, <i>Characella pachastrelloides</i>, collected from ~800 m depth in Irish waters. First, we analyzed the MS/MS data obtained from fractions of this sponge on the GNPS public online platform to guide our exploration of its chemodiversity. Novel glycolipopeptides named characellides were previously isolated from the sponge and herein cyanocobalamin, a manufactured form of vitamin B<sub>12</sub>, not previously found in nature, was isolated in a large amount. We also identified several poecillastrins from the molecular network, a class of polyketide known to exhibit cytotoxicity. Light sensitivity prevented the isolation and characterization of these polyketides, but their presence was confirmed by characteristic NMR and MS signals. Finally, we isolated the new betaine 6-methylhercynine, which contains a unique methylation at C-2 of the imidazole ring. This compound showed potent cytotoxicity towards against HeLa (cervical cancer) cells.https://www.mdpi.com/1660-3397/20/1/52deep-seaspongecyanocobalaminmolecular networkingpoecillastrinshercynine |
| spellingShingle | Sam Afoullouss Anthony R. Sanchez Laurence K. Jennings Younghoon Kee A. Louise Allcock Olivier P. Thomas Unveiling the Chemical Diversity of the Deep-Sea Sponge <i>Characella pachastrelloides</i> Marine Drugs deep-sea sponge cyanocobalamin molecular networking poecillastrins hercynine |
| title | Unveiling the Chemical Diversity of the Deep-Sea Sponge <i>Characella pachastrelloides</i> |
| title_full | Unveiling the Chemical Diversity of the Deep-Sea Sponge <i>Characella pachastrelloides</i> |
| title_fullStr | Unveiling the Chemical Diversity of the Deep-Sea Sponge <i>Characella pachastrelloides</i> |
| title_full_unstemmed | Unveiling the Chemical Diversity of the Deep-Sea Sponge <i>Characella pachastrelloides</i> |
| title_short | Unveiling the Chemical Diversity of the Deep-Sea Sponge <i>Characella pachastrelloides</i> |
| title_sort | unveiling the chemical diversity of the deep sea sponge i characella pachastrelloides i |
| topic | deep-sea sponge cyanocobalamin molecular networking poecillastrins hercynine |
| url | https://www.mdpi.com/1660-3397/20/1/52 |
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