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dc.contributor.authorYin, Sheng
dc.contributor.authorDavis, Rohan A
dc.contributor.authorShelper, Todd
dc.contributor.authorSykes, Melissa L
dc.contributor.authorAvery, Vicky M
dc.contributor.authorElofsson, Mikael
dc.contributor.authorSundin, Charlotta
dc.contributor.authorQuinn, Ronald J
dc.date.accessioned2017-05-03T13:12:11Z
dc.date.available2017-05-03T13:12:11Z
dc.date.issued2011
dc.date.modified2012-03-09T05:30:35Z
dc.identifier.issn1477-0520
dc.identifier.doi10.1039/C1OB05581J
dc.identifier.urihttp://hdl.handle.net/10072/43495
dc.description.abstractBioassay-guided fractionation of the CH2Cl2/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 (IC50 = 19 and 6 mM, respectively) and the enzyme activity of YopH (IC50 = 33 and 6 mM, respectively).
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.publisher.placeUnited Kingdom
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom6755
dc.relation.ispartofpageto6760
dc.relation.ispartofissue6755
dc.relation.ispartofjournalOrganic & Biomolecular Chemistry
dc.relation.ispartofvolume9
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchMedicinal and biomolecular chemistry not elsewhere classified
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode340499
dc.subject.fieldofresearchcode3405
dc.titlePseudoceramines A-D, new antibacterial bromotyrosine alkaloids from themarine sponge Pseudoceratina sp.
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.facultyGriffith Sciences, Griffith Institute for Drug Discovery
gro.date.issued2011
gro.hasfulltextNo Full Text
gro.griffith.authorQuinn, Ronald J.
gro.griffith.authorDavis, Rohan A.
gro.griffith.authorSykes, Melissa L.
gro.griffith.authorAvery, Vicky M.
gro.griffith.authorYin, Sheng
gro.griffith.authorShelper, Todd B.


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