title: Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase.
abstract: Three new disulfated meroterpenoids, ilhabelanol (1), ilhabrene (2), and isoakaterpin (3), have been isolated from extracts of the Brazilian marine sponge Callyspongia sp. Isoakaterpin (3) inhibits Leishmania spp. adenosine phosphoribosyl transferase with an IC50 of 1.05 microM. The structures of 1, 2, and 3 were elucidated by analysis of one- and two-dimensional NMR data. Ilhabelanol (1) and ilhabrene (2) both have unprecedented meroterpenoid carbon skeletons.
authors.affiliation: Department of Chemistry, University of British Columbia, Vancouver, British Columbia, V6T 1Z1 Canada.
authors.forename: Christopher A
authors.initials: CA
authors.lastname: Gray
authors.forename: Simone P
authors.initials: SP
authors.lastname: de Lira
authors.forename: Marcio
authors.initials: M
authors.lastname: Silva
authors.forename: Eli F
authors.initials: EF
authors.lastname: Pimenta
authors.forename: Otavio H
authors.initials: OH
authors.lastname: Thiemann
authors.forename: Glaucius
authors.initials: G
authors.lastname: Oliva
authors.forename: Eduardo
authors.initials: E
authors.lastname: Hajdu
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Andersen
authors.forename: Roberto G S
authors.initials: RG
authors.lastname: Berlinck
mesh_terms: D000228:Adenine Phosphoribosyltransferase / Q000037:antagonists & inhibitors*; D000818:Animals; D047128:Callyspongia / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D007891:Leishmania / Q000201:enzymology; D008968:Molecular Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D013729:Terpenes; C522011:ilhabelanol; C522012:ilhabrene; C522013:isoakaterpin; D000228:Adenine Phosphoribosyltransferase