{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T17:10:36Z","timestamp":1790356236206,"version":"4.1.0"},"reference-count":21,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2018,3,2]],"date-time":"2018-03-02T00:00:00Z","timestamp":1519948800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>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\u2019s and advance Marfey\u2019s 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.<\/jats:p>","DOI":"10.3390\/md16030078","type":"journal-article","created":{"date-parts":[[2018,3,2]],"date-time":"2018-03-02T11:53:40Z","timestamp":1519991620000},"page":"78","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":25,"title":["Microginins from a Microcystis sp. Bloom Material Collected from the Kishon Reservoir, Israel"],"prefix":"10.3390","volume":"16","author":[{"given":"Anat","family":"Lodin-Friedman","sequence":"first","affiliation":[{"name":"Raymond and Beverly Sackler School of Chemistry and Faculty of Exact Sciences, Tel Aviv University, Ramat-Aviv, Tel Aviv 69978, Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9641-9943","authenticated-orcid":false,"given":"Shmuel","family":"Carmeli","sequence":"additional","affiliation":[{"name":"Raymond and Beverly Sackler School of Chemistry and Faculty of Exact Sciences, Tel Aviv University, Ramat-Aviv, Tel Aviv 69978, Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,3,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1654","DOI":"10.2174\/138945011798109455","article-title":"Chemodiversity in freshwater and terrestrial cyanobacteria\u2014A source for drug discovery","volume":"12","author":"Chlipala","year":"2011","journal-title":"Curr. 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Stat."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"9347","DOI":"10.1016\/S0040-4020(01)00931-0","article-title":"Marine cyanobacteria\u2014A prolific source of natural products","volume":"57","author":"Burja","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"954","DOI":"10.1016\/j.phytochem.2007.01.012","article-title":"Bioactive natural products from marine cyanobacteria for drug discovery","volume":"68","author":"Tan","year":"2007","journal-title":"Phytochemistry"}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/16\/3\/78\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T14:57:14Z","timestamp":1760194634000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/16\/3\/78"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,3,2]]},"references-count":21,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2018,3]]}},"alternative-id":["md16030078"],"URL":"https:\/\/doi.org\/10.3390\/md16030078","relation":{"has-preprint":[{"id-type":"doi","id":"10.20944\/preprints201801.0027.v1","asserted-by":"object"}]},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,3,2]]}}}