{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,8]],"date-time":"2025-11-08T13:27:56Z","timestamp":1762608476460,"version":"build-2065373602"},"reference-count":20,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2021,10,19]],"date-time":"2021-10-19T00:00:00Z","timestamp":1634601600000},"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>The sponge metabolite ancorinoside B was prepared for the first time in 16 steps and 4% yield. It features a \u03b2-d-galactopyranosyl-(1\u21924)-\u03b2-d-glucuronic acid tethered to a d-aspartic acid-derived tetramic acid. Key steps were the synthesis of a fully protected d-lactose derived thioglycoside, its attachment to a C20-aldehyde spacer, functionalization of the latter with a terminal N-(\u03b2-ketoacyl)-d-aspartate, and a basic Dieckmann cyclization to close the pyrrolidin-2,4-dione ring with concomitant global deprotection. Ancorinoside B exhibited multiple biological effects of medicinal interest. It inhibited the secretion of the cancer metastasis-relevant matrix metalloproteinases MMP-2 and MMP-9, and also the growth of Staphylococcus aureus biofilms by ca 87% when applied at concentrations as low as 0.5 \u00b5g\/mL. This concentration is far below its MIC of ca 67 \u00b5g\/mL and thus unlikely to induce bacterial resistance. It also led to a 67% dispersion of preformed S. aureus biofilms when applied at a concentration of ca 2 \u00b5g\/mL. Ancorinoside B might thus be an interesting candidate for the control of the general hospital, catheter, or joint protheses infections.<\/jats:p>","DOI":"10.3390\/md19100583","type":"journal-article","created":{"date-parts":[[2021,10,20]],"date-time":"2021-10-20T03:01:13Z","timestamp":1634698873000},"page":"583","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis and Bioactivity of Ancorinoside B, a Marine Diglycosyl Tetramic Acid"],"prefix":"10.3390","volume":"19","author":[{"given":"Kevin J.","family":"Soliga","sequence":"first","affiliation":[{"name":"Department of Chemistry, University Bayreuth, Universitaetsstr. 30, D-95440 Bayreuth, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sofia I.","family":"B\u00e4r","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University Bayreuth, Universitaetsstr. 30, D-95440 Bayreuth, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Natalie","family":"Oberhuber","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University Bayreuth, Universitaetsstr. 30, D-95440 Bayreuth, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Haoxuan","family":"Zeng","sequence":"additional","affiliation":[{"name":"Department of Microbial Drugs, Helmholtz Centre for Infection Research GmbH, Inhoffenstrasse 7, 38124 Braunschweig, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hedda","family":"Schrey","sequence":"additional","affiliation":[{"name":"Department of Microbial Drugs, Helmholtz Centre for Infection Research GmbH, Inhoffenstrasse 7, 38124 Braunschweig, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8413-4342","authenticated-orcid":false,"given":"Rainer","family":"Schobert","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University Bayreuth, Universitaetsstr. 30, D-95440 Bayreuth, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,10,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1981","DOI":"10.1021\/cr00038a009","article-title":"Naturally occurring tetramic acids: Structure, isolation, and synthesis","volume":"95","author":"Royles","year":"1995","journal-title":"Chem. 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