Barrettides: A Peptide Family Specifically Produced by the Deep-Sea Sponge Geodia barretti
[Image: see text] 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 alt...
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ftpubmed:oai:pubmedcentral.nih.gov:8713285 2023-05-15T17:33:03+02:00 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, Ana Göransson, Ulf Cárdenas, Paco 2021-12-07 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8713285/ http://www.ncbi.nlm.nih.gov/pubmed/34874154 https://doi.org/10.1021/acs.jnatprod.1c00938 en eng American Chemical Society and American Society of Pharmacognosy http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8713285/ http://www.ncbi.nlm.nih.gov/pubmed/34874154 http://dx.doi.org/10.1021/acs.jnatprod.1c00938 © 2021 The Authors. Published by American Chemical Society and American Society of Pharmacognosy https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). CC-BY J Nat Prod Text 2021 ftpubmed https://doi.org/10.1021/acs.jnatprod.1c00938 2022-01-02T01:40:29Z [Image: see text] 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 C (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 (IC(50) 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. Text North Atlantic PubMed Central (PMC) Journal of Natural Products 84 12 3138 3146 |
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[Image: see text] 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 C (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 (IC(50) 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. |
format |
Text |
author |
Steffen, Karin Laborde, Quentin Gunasekera, Sunithi Payne, Colton D. Rosengren, K. Johan Riesgo, Ana Göransson, Ulf Cárdenas, Paco |
spellingShingle |
Steffen, Karin Laborde, Quentin Gunasekera, Sunithi Payne, Colton D. Rosengren, K. Johan Riesgo, 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, 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 |
American Chemical Society and American Society of Pharmacognosy |
publishDate |
2021 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8713285/ http://www.ncbi.nlm.nih.gov/pubmed/34874154 https://doi.org/10.1021/acs.jnatprod.1c00938 |
genre |
North Atlantic |
genre_facet |
North Atlantic |
op_source |
J Nat Prod |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8713285/ http://www.ncbi.nlm.nih.gov/pubmed/34874154 http://dx.doi.org/10.1021/acs.jnatprod.1c00938 |
op_rights |
© 2021 The Authors. Published by American Chemical Society and American Society of Pharmacognosy https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
op_rightsnorm |
CC-BY |
op_doi |
https://doi.org/10.1021/acs.jnatprod.1c00938 |
container_title |
Journal of Natural Products |
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84 |
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12 |
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3138 |
op_container_end_page |
3146 |
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1766131420668887040 |