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Cyclotheonellazoles A–C, Potent Protease Inhibitors from the Marine Sponge Theonella aff. swinhoei
Open accessAbstract
The extract of a sample of the sponge Theonella aff. swinhoei collected in Madagascar exhibited promising in vitro antiplasmodial activity. The antiplasmodial activity was ascribed in part to the known metabolite swinholide A. Further investigation of the extract afforded three unusual cyclic peptides, cyclotheonellazoles A-C (1-3), which contain six nonproteinogenic amino acids out of the eight acid units that compose these natural products. Among these acids the most novel were 4-propenoyl-2-tyrosylthiazole and 3-amino-4-methyl-2-oxohexanoic acid. The structure of the compounds was elucidated by interpretation of the 1D and 2D NMR data, HRESIMS, and advanced Merfay's techniques. The new compounds were found to be nanomolar inhibitors of chymotrypsin and sub-nanomolar inhibitors of elastase, but did not present antiplasmodial activity.
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Cyanobacteria are a rich source of highly bioactive natural products, and in particular, protease inhibitors from numerous chemical classes.
“Cyanobacteria are known to be a rich source of highly bioactive natural products32–35, and in particular, protease inhibitors from numerous chemical classes36–41.”
From Native metabolomics identifies the rivulariapeptolide family of protease inhibitors (2022) · cites this paper as [40]
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Self-citationBindingDB Entry 50001754: Swinhoeisterols from the South China Sea Sponge Theonella swinhoei.
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Metadata
- Authors
- Issac, M., Aknin, M., Gauvin-Bialecki, A., De Voogd, N., Ledoux, A., Frederich, M., Kashman, Y., & Carmeli, S.
- Affiliations
- Tel Aviv University (IL)
- University of Reunion Island (RE)
- Laboratoire de Chimie des Substances Naturelles et des Aliments, Faculté des Sciences et Technologies, Université de La Réunion, 15 Avenue René Cassin, CS 92 003, 97 744, Saint-Denis, Cedex 9, France
- Naturalis Biodiversity Center, P.O. Box 9517, 2300 RA, Leiden, The Netherlands
- University of Liège (BE)
- Laboratory of Pharmacognosy, Department of Pharmacy, CIRM, University of Liège, B36, 4000 Liège, Belgium
- Corresponding author
- Carmeli, Shmuel
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-02-16
- Volume
- 80
- Issue
- 4
- Pages
- 1110-1116
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W2588034608
- Cited by
- 39
- References
- 24
- Citations by year
- 2026: 2 · 2025: 7 · 2024: 7 · 2023: 4 · 2022: 6 · 2021: 3 · 2020: 2 · 2019: 3 · 2018: 3 · 2017: 2
- FWCI
- 2.21
- Type
- journal article
- Language
- en
- Open access
- Licence
- other-oa
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion, other-oa)
- ORBi (University of Liège) (submittedVersion)
- Funders
- European Commission
- European Regional Development Fund
- Tel Aviv University
- Conseil R?gional de La R?union
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Marine Sponges and Natural Products
- Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Microbial Natural Products and Biosynthesis
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Drug Discovery › Bioactive natural compounds
- Keywords
- marine sponge metabolites, cyclic peptides, unnatural amino acids, swinholide A, antiplasmodial activity, chymotrypsin inhibitor, elastase inhibitors, protease inhibitors, structure elucidation
- MeSH terms
- Animals, Chymotrypsin, Madagascar, Marine Biology, Marine Toxins, Pancreatic Elastase, Peptides, Cyclic, Porifera, Protease Inhibitors, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Theonella
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