Publication
Bartolosides E–K from a Marine Coccoid Cyanobacterium
| dc.contributor.author | Afonso, Tiago B. | |
| dc.contributor.author | Costa, M. Sofia | |
| dc.contributor.author | Rezende de Castro, Roberta | |
| dc.contributor.author | Freitas, Sara | |
| dc.contributor.author | Silva, Artur | |
| dc.contributor.author | Schneider, Maria Paula Cruz | |
| dc.contributor.author | Martins, Rosario | |
| dc.contributor.author | Leão, Pedro N. | |
| dc.date.accessioned | 2017-01-16T10:50:30Z | |
| dc.date.available | 2017-01-16T10:50:30Z | |
| dc.date.issued | 2016 | |
| dc.description.abstract | The glycosylated and halogenated dialkylresorcinol (DAR) compounds bartolosides A-D (1-4) were recently discovered from marine cyanobacteria and represent a novel family of glycolipids, encoded by the brt biosynthetic gene cluster. Here, we report the isolation and NMR- and MS-based structure elucidation of monoglycosylated bartolosides E-K (5-11), obtained from Synechocystis salina LEGE 06099, a strain closely related to the cyanobacterium that produces the diglycosylated 2-4. In addition, a genome region containing orthologues of brt genes was identified in this cyanobacterium. Interestingly, the major bartoloside in S. salina LEGE 06099 was 1 (above 0.5% dry wt), originally isolated from the phylogenetically distant filamentous cyanobacterium Nodosilinea sp. LEGE 06102. Compounds 5-11 are analogues of 1, with different alkyl chain lengths or halogenation patterns. Their structures and the organization of the brt genes suggest that the DAR-forming ketosynthase BrtD can generate structural diversity by accepting fatty acyl-derived substrates of varying length. Compound 9 features a rare midchain gem-dichloro moiety, indicating that the putative halogenase BrtJ is able to act twice on the same midchain carbon. | pt_PT |
| dc.description.version | info:eu-repo/semantics/publishedVersion | pt_PT |
| dc.identifier.doi | 10.1021/acs.jnatprod.6b00351 | pt_PT |
| dc.identifier.issn | 0163-3864 | |
| dc.identifier.uri | http://hdl.handle.net/10400.22/9267 | |
| dc.language.iso | eng | pt_PT |
| dc.peerreviewed | yes | pt_PT |
| dc.publisher | American Chemical Society | pt_PT |
| dc.relation.publisherversion | http://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.6b00351 | pt_PT |
| dc.title | Bartolosides E–K from a Marine Coccoid Cyanobacterium | pt_PT |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.endPage | 2513 | pt_PT |
| oaire.citation.issue | 10 | pt_PT |
| oaire.citation.startPage | 2504 | pt_PT |
| oaire.citation.title | Journal of Natural Products | pt_PT |
| oaire.citation.volume | 79 | pt_PT |
| person.familyName | Martins | |
| person.givenName | Rosario | |
| person.identifier.ciencia-id | A919-DB40-EF10 | |
| person.identifier.orcid | 0000-0002-9882-4651 | |
| person.identifier.scopus-author-id | 21834368700 | |
| rcaap.rights | restrictedAccess | pt_PT |
| rcaap.type | article | pt_PT |
| relation.isAuthorOfPublication | 82a7c349-c88e-450f-adc7-3331d69149cf | |
| relation.isAuthorOfPublication.latestForDiscovery | 82a7c349-c88e-450f-adc7-3331d69149cf |