Microginins from a Microcystis sp. Bloom Material Collected from the Kishon Reservoir, Israel
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Abstract
During blooms, cyanobacteria produce diverse modified peptides. Among these are the microginins, which inhibit zinc-containing metalloproteases. Ten microginins, microginins KR767 (1), KR801(2), KR835 (3), KR785 (4), KR604 (5), KR638 (6), KR781 (7), KR815 (8), FR3 (9), and FR4 (10), were isolated from the extract of a bloom material of Microcystis sp. (IL-405) collected from the Kishon Reservoir, Israel in the fall of 2009. The structures of the pure compounds were elucidated using 1D and 2D NMR techniques and high-resolution mass spectrometry. The absolute configuration of the chiral centers of the amino acids were determined by Marfey’s and advance Marfey’s methods and by comparison of 1H and 13C NMR chemical shifts of the Ahda derivatives with those of known microginins. These microginins differ in sequence and absolute configuration of the chiral centers of the Ahda moieties and by N-methylation of the Ahda amine group and extent of chlorination of the Ahda terminal methyl group. The compounds were evaluated for inhibition of the zinc metalloprotease, aminopeptidase M, and exhibited low- to sub-nanomolar half maximal inhibitory concentration (IC50) values.
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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 [37]
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- Authors
- Lodin-Friedman, A., & Carmeli, S.
- Affiliations
- Tel Aviv University (IL)
- Corresponding author
- Carmeli, Shmuel
- ORCID
- Carmeli, Shmuel
- Venue
- Marine Drugs
- Publisher
- MDPI AG
- Published
- 2018-03-02
- Volume
- 16
- Issue
- 3
- Pages
- 78
- ISSN
- 1660-3397 (ISSN-L)
- PMC
- PMC5867622
- OpenAlex
- W2781542404
- Cited by
- 36
- References
- 22
- Citations by year
- 2026: 3 · 2025: 5 · 2024: 6 · 2023: 4 · 2022: 5 · 2021: 4 · 2020: 3 · 2019: 4 · 2018: 2
- FWCI
- 2.10
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Marine Drugs (publishedVersion, cc-by)
- Preprints.org (acceptedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- Israel Science Foundation (1298/13)
- Tel Aviv University
- Topics
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Physical Sciences › Environmental Science › Environmental Chemistry › Aquatic Ecosystems and Phytoplankton Dynamics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Marine Sponges and Natural Products
- Keywords
- microginins, Microcystis, cyanobacterial blooms, aminopeptidase M, absolute configuration, N-methylation, chlorination, structure elucidation
- MeSH terms
- Chromatography, High Pressure Liquid, Eutrophication, Israel, Peptides, Cyclic, Mass Spectrometry, Molecular Structure, Biomass, CD13 Antigens, Nuclear Magnetic Resonance, Biomolecular, Rivers, Microcystis, Enzyme Assays, Aquatic Organisms
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