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Pseudoceramines A-D, new antibacterial bromotyrosine alkaloids from the marine sponge Pseudoceratina sp
Eskitis Institute, Griffith University, Brisbane, Australia.
Eskitis Institute, Griffith University, Brisbane, Australia.
Eskitis Institute, Griffith University, Brisbane, Australia.
Eskitis Institute, Griffith University, Brisbane, Australia.
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2011 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 9, 6755-6760 p.Article in journal (Refereed) Published
Description
Abstract [en]

Bioassay-guided fractionation of the CH(2)Cl(2)/MeOH extract of the Australian marine sponge Pseudoceratina sp. resulted in the purification of four new bromotyrosine alkaloids, pseudoceramines A-D (1-4), along with a known natural product, spermatinamine (5). The structures of 1-5 were determined by spectroscopic methods. Pseudoceramines A (1) and B (2) feature a rare bromotyrosyl-spermine-bromotyrosyl sequence, and pseudoceramine C (3) is the first example of bromotyrosine coupled with an N-methyl derivative of spermidine. Compounds 1-5 were screened for inhibition of toxin secretion by the type III secretion (T3S) pathway in Yersinia pseudotuberculosis. Compounds 2 and 5 inhibited secretion of the Yersinia outer protein YopE (IC(50) = 19 and 6 μM, respectively) and the enzyme activity of YopH (IC(50) = 33 and 6 μM, respectively).

Place, publisher, year, edition, pages
Royal Society of Chemistry , 2011. Vol. 9, 6755-6760 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-46062DOI: 10.1039/c1ob05581jPubMedID: 21850326OAI: oai:DiVA.org:umu-46062DiVA: diva2:436900
Available from: 2011-08-25 Created: 2011-08-25 Last updated: 2017-12-08Bibliographically approved

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