New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from <i>Stylissa caribica</i>
Feature-based molecular networking was used to re-examine the secondary metabolites in extracts of a very well studied marine sponge, <i>Stylissa caribica</i>, known to contain a large array of cyclic peptides and brominated alkaloids. The analysis revealed the presence of 13 cyclic pept...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-08-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/9/443 |
| _version_ | 1827707438651932672 |
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| author | Silvia Scarpato Roberta Teta Gerardo Della Sala Joseph R. Pawlik Valeria Costantino Alfonso Mangoni |
| author_facet | Silvia Scarpato Roberta Teta Gerardo Della Sala Joseph R. Pawlik Valeria Costantino Alfonso Mangoni |
| author_sort | Silvia Scarpato |
| collection | DOAJ |
| description | Feature-based molecular networking was used to re-examine the secondary metabolites in extracts of a very well studied marine sponge, <i>Stylissa caribica</i>, known to contain a large array of cyclic peptides and brominated alkaloids. The analysis revealed the presence of 13 cyclic peptides in the sponge that had never been detected in previous work and appeared to be new compounds. The most abundant one was isolated and shown to be a new proline-rich cyclic heptapetide that was called stylissamide L (<b>1</b>). Structure of compound <b>1</b>, including the cis/trans geometry of the three proline residues, was determined by extensive NMR studies; the <span style="font-variant: small-caps;">l</span> configuration of the seven amino acid residues was determined using Marfey’s method. Stylissamide L was tested for activity as a cell growth inhibitor and cell migration inhibitor on two cancer cell lines but, unlike other members of the stylissamide family, it showed no significant activity. This approach showed that even a thoroughly studied species such as <i>S. caribica</i> may contain new chemistry that can be revealed if studied with the right tools. |
| first_indexed | 2024-03-10T16:46:41Z |
| format | Article |
| id | doaj.art-33c3531289ac482d879c3e6b8bb9a4a4 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T16:46:41Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-33c3531289ac482d879c3e6b8bb9a4a42023-11-20T11:31:42ZengMDPI AGMarine Drugs1660-33972020-08-0118944310.3390/md18090443New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from <i>Stylissa caribica</i>Silvia Scarpato0Roberta Teta1Gerardo Della Sala2Joseph R. Pawlik3Valeria Costantino4Alfonso Mangoni5Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via Domenico Montesano 49, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, via Domenico Montesano 49, 80131 Napoli, ItalyLaboratory of Pre-Clinical and Translational Research, IRCCS-CROB, Referral Cancer Center of Basilicata, 85028 Rionero in Vulture, ItalyDepartment of Biology and Marine Biology, University of North Carolina Wilmington, Center for Marine Science, 5600 Marvin K Moss Lane, Wilmington, NC 28409, USADipartimento di Farmacia, Università degli Studi di Napoli Federico II, via Domenico Montesano 49, 80131 Napoli, ItalyDipartimento di Farmacia, Università degli Studi di Napoli Federico II, via Domenico Montesano 49, 80131 Napoli, ItalyFeature-based molecular networking was used to re-examine the secondary metabolites in extracts of a very well studied marine sponge, <i>Stylissa caribica</i>, known to contain a large array of cyclic peptides and brominated alkaloids. The analysis revealed the presence of 13 cyclic peptides in the sponge that had never been detected in previous work and appeared to be new compounds. The most abundant one was isolated and shown to be a new proline-rich cyclic heptapetide that was called stylissamide L (<b>1</b>). Structure of compound <b>1</b>, including the cis/trans geometry of the three proline residues, was determined by extensive NMR studies; the <span style="font-variant: small-caps;">l</span> configuration of the seven amino acid residues was determined using Marfey’s method. Stylissamide L was tested for activity as a cell growth inhibitor and cell migration inhibitor on two cancer cell lines but, unlike other members of the stylissamide family, it showed no significant activity. This approach showed that even a thoroughly studied species such as <i>S. caribica</i> may contain new chemistry that can be revealed if studied with the right tools.https://www.mdpi.com/1660-3397/18/9/443cyclic peptidesdereplicationfeature-based molecular networkingmarine spongesmetabolomicsmolecular networking |
| spellingShingle | Silvia Scarpato Roberta Teta Gerardo Della Sala Joseph R. Pawlik Valeria Costantino Alfonso Mangoni New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from <i>Stylissa caribica</i> Marine Drugs cyclic peptides dereplication feature-based molecular networking marine sponges metabolomics molecular networking |
| title | New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from <i>Stylissa caribica</i> |
| title_full | New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from <i>Stylissa caribica</i> |
| title_fullStr | New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from <i>Stylissa caribica</i> |
| title_full_unstemmed | New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from <i>Stylissa caribica</i> |
| title_short | New Tricks with an Old Sponge: Feature-Based Molecular Networking Led to Fast Identification of New Stylissamide L from <i>Stylissa caribica</i> |
| title_sort | new tricks with an old sponge feature based molecular networking led to fast identification of new stylissamide l from i stylissa caribica i |
| topic | cyclic peptides dereplication feature-based molecular networking marine sponges metabolomics molecular networking |
| url | https://www.mdpi.com/1660-3397/18/9/443 |
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