Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti
Natural product discovery by isolation and structure elucidation is a laborious task often requiring ample quantities of biological starting material and frequently resulting in the rediscovery of previously known compounds. However, peptides are a compound class amenable to an alternative genomic,...
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ftcsic:oai:digital.csic.es:10261/257781 2024-02-11T10:06:29+01:00 Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti Steffen, Karin Laborde, Quentin Gunasekera, Sunithi Payne, Colton D. Rosengren, K. Johan Riesgo Gil, Ana Göransson, Ulf Cárdenas, Paco Swedish Pharmaceutical Society European Commission 2021-12-07 http://hdl.handle.net/10261/257781 https://doi.org/10.1021/acs.jnatprod.1c00938 https://doi.org/10.13039/501100000780 en eng ACS Publications #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/EC/H2020/679849 Publisher's version https://pubs.acs.org/doi/10.1021/acs.jnatprod.1c00938 Sí Journal of Natural Products 84: 3138-3146 (2021) http://hdl.handle.net/10261/257781 doi:10.1021/acs.jnatprod.1c00938 0974-5211 http://dx.doi.org/10.13039/501100000780 open artículo http://purl.org/coar/resource_type/c_6501 2021 ftcsic https://doi.org/10.1021/acs.jnatprod.1c0093810.13039/501100000780 2024-01-16T11:17:21Z Natural product discovery by isolation and structure elucidation is a laborious task often requiring ample quantities of biological starting material and frequently resulting in the rediscovery of previously known compounds. However, peptides are a compound class amenable to an alternative genomic, transcriptomic, and in silico discovery route by similarity searches of known peptide sequences against sequencing data. Based on the sequences of barrettides A and B, we identified five new barrettide sequences (barrettides C−G) predicted from the North Atlantic deep-sea demosponge Geodia barretti (Geodiidae). We synthesized, folded, and investigated one of the newly described barrettides, barrettide (NVVPCFCVEDETSGAKTCIPDNCDASRGTNP, disulfide connectivity I−IV, II−III). Co-elution experiments of synthetic and sponge-derived barrettide C confirmed its native conformation. NMR spectroscopy and the anti-biofouling activity on larval settlement of the bay barnacle Amphibalanus improvisus (IC50 0.64 μM) show that barrettide C is highly similar to barrettides A and B in both structure and function. Several lines of evidence suggest that barrettides are produced by the sponge itself and not one of its microbial symbionts. K.S. thanks the Swedish pharmaceutical society (Apotekarsocieteten) for funds provided to purchase reagents for SPPS. K.S., A.R., and P.C. acknowledge SponGES; SponGES has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement no. 679849. Peer reviewed Article in Journal/Newspaper North Atlantic Digital.CSIC (Spanish National Research Council) Journal of Natural Products 84 12 3138 3146 |
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Open Polar |
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Digital.CSIC (Spanish National Research Council) |
op_collection_id |
ftcsic |
language |
English |
description |
Natural product discovery by isolation and structure elucidation is a laborious task often requiring ample quantities of biological starting material and frequently resulting in the rediscovery of previously known compounds. However, peptides are a compound class amenable to an alternative genomic, transcriptomic, and in silico discovery route by similarity searches of known peptide sequences against sequencing data. Based on the sequences of barrettides A and B, we identified five new barrettide sequences (barrettides C−G) predicted from the North Atlantic deep-sea demosponge Geodia barretti (Geodiidae). We synthesized, folded, and investigated one of the newly described barrettides, barrettide (NVVPCFCVEDETSGAKTCIPDNCDASRGTNP, disulfide connectivity I−IV, II−III). Co-elution experiments of synthetic and sponge-derived barrettide C confirmed its native conformation. NMR spectroscopy and the anti-biofouling activity on larval settlement of the bay barnacle Amphibalanus improvisus (IC50 0.64 μM) show that barrettide C is highly similar to barrettides A and B in both structure and function. Several lines of evidence suggest that barrettides are produced by the sponge itself and not one of its microbial symbionts. K.S. thanks the Swedish pharmaceutical society (Apotekarsocieteten) for funds provided to purchase reagents for SPPS. K.S., A.R., and P.C. acknowledge SponGES; SponGES has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement no. 679849. Peer reviewed |
author2 |
Swedish Pharmaceutical Society European Commission |
format |
Article in Journal/Newspaper |
author |
Steffen, Karin Laborde, Quentin Gunasekera, Sunithi Payne, Colton D. Rosengren, K. Johan Riesgo Gil, Ana Göransson, Ulf Cárdenas, Paco |
spellingShingle |
Steffen, Karin Laborde, Quentin Gunasekera, Sunithi Payne, Colton D. Rosengren, K. Johan Riesgo Gil, Ana Göransson, Ulf Cárdenas, Paco Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti |
author_facet |
Steffen, Karin Laborde, Quentin Gunasekera, Sunithi Payne, Colton D. Rosengren, K. Johan Riesgo Gil, Ana Göransson, Ulf Cárdenas, Paco |
author_sort |
Steffen, Karin |
title |
Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti |
title_short |
Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti |
title_full |
Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti |
title_fullStr |
Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti |
title_full_unstemmed |
Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti |
title_sort |
barrettides: a peptide family specifically produced by the deep-sea sponge geodia barretti |
publisher |
ACS Publications |
publishDate |
2021 |
url |
http://hdl.handle.net/10261/257781 https://doi.org/10.1021/acs.jnatprod.1c00938 https://doi.org/10.13039/501100000780 |
genre |
North Atlantic |
genre_facet |
North Atlantic |
op_relation |
#PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/EC/H2020/679849 Publisher's version https://pubs.acs.org/doi/10.1021/acs.jnatprod.1c00938 Sí Journal of Natural Products 84: 3138-3146 (2021) http://hdl.handle.net/10261/257781 doi:10.1021/acs.jnatprod.1c00938 0974-5211 http://dx.doi.org/10.13039/501100000780 |
op_rights |
open |
op_doi |
https://doi.org/10.1021/acs.jnatprod.1c0093810.13039/501100000780 |
container_title |
Journal of Natural Products |
container_volume |
84 |
container_issue |
12 |
container_start_page |
3138 |
op_container_end_page |
3146 |
_version_ |
1790604249545048064 |