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dc.contributor.authorRudolph, Kathryn E
dc.contributor.authorLiberio, Michelle S
dc.contributor.authorDavis, Rohan A
dc.contributor.authorCarroll, Anthony R
dc.date.accessioned2021-06-18T03:35:13Z
dc.date.available2021-06-18T03:35:13Z
dc.date.issued2013
dc.date.modified2013-11-11T21:57:43Z
dc.identifier.issn1477-0520
dc.identifier.doi10.1039/c2ob26879e
dc.identifier.urihttp://hdl.handle.net/10072/54123
dc.description.abstractFour new acylated pteridine alkaloids, duramidines A-D, two new acylated thymidine alkaloids, leptoclinidines A and B, two new 1-acylglyceryl-3-(O-carboxyhydroxymethylcholine) alkaloids, durabetaines A and B, three new 1,3-dimethyl-5-methylsulfanylimidazole alkaloids, leptoclinidamines D-F, and the known alkaloids leptoclinidamines B and C and 6-bromo-1H-indolo-3-yl-oxoacetic acid methyl ester were isolated from the Australian ascidian Leptoclinides durus. The duramidines are the first pteridine alkaloids, possessing a three carbon side chain esterified at C-1' with a 4-hydroxy-2'-methoxycinnamic acid, and are either hydroxylated or sulfated at C-2'. The leptoclinidines are the first 3'-indole-3-carboxylic acid ester derivatives of thymidine to be reported in the literature. The durabetaines are the first glyceryl-3-(O-carboxyhydroxymethylcholine) alkaloids to be reported from an animal source and are also the only known derivatives from this class to be acylated with aromatic carboxylic acids. MS and NMR data analysis established the structures of the new compounds. All compounds were shown to be inactive when tested for cytotoxic activity against prostate (LNCaP) and breast (MDA-MB-231) cancer cell lines and antimicrobial activity against Pseudomonas aeruginosa and Staphylococcus aureus.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.publisher.placeUnited Kingdom
dc.relation.ispartofstudentpublicationY
dc.relation.ispartofpagefrom261
dc.relation.ispartofpageto270
dc.relation.ispartofissue2
dc.relation.ispartofjournalOrganic & Biomolecular Chemistry
dc.relation.ispartofvolume11
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchBiologically active molecules
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode340401
dc.subject.fieldofresearchcode3405
dc.titlePteridine-, thymidine-, choline- and imidazole-derived alkaloids from the Australian ascidian, Leptoclinides durus
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
dc.description.versionAccepted Manuscript (AM)
gro.facultyGriffith Sciences, Griffith School of Environment
gro.rights.copyright© 2013 Royal Society of Chemistry. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal website for access to the definitive, published version.
gro.date.issued2013
gro.hasfulltextFull Text
gro.griffith.authorDavis, Rohan A.
gro.griffith.authorCarroll, Anthony R.
gro.griffith.authorRudolph, Kathryn
gro.griffith.authorda Silva Liberio, Michelle


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