Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase.
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.
Gray
Christopher A
CA
Department of Chemistry, University of British Columbia, Vancouver, British Columbia, V6T 1Z1 Canada.
de Lira
Simone P
SP
Silva
Marcio
M
Pimenta
Eli F
EF
Thiemann
Otavio H
OH
Oliva
Glaucius
G
Hajdu
Eduardo
E
Andersen
Raymond J
RJ
Berlinck
Roberto G S
RG
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
D004791:Enzyme Inhibitors; D013729:Terpenes; C522011:ilhabelanol; C522012:ilhabrene; C522013:isoakaterpin; D000228:Adenine Phosphoribosyltransferase