title: Indoleamine 2,3-dioxygenase inhibitors isolated from the sponge Xestospongia vansoesti: structure elucidation, analogue synthesis, and biological activity.
abstract: Two new IDO inhibitory meroterpenoids, xestolactone A (1) and xestosaprol O (2), have been isolated from the sponge Xestospongia vansoesti. Xestolactone A (1) has an unprecedented degraded meroterpenoid carbon skeleton. A short synthesis of the xestosaprol O (2) analogues 3 and 4 features the application of a rarely used photochemical coupling reaction. Synthetic analogue 3 is ∼40 times more potent than the inspirational natural product 2.
authors.affiliation: Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia , 2036 Main Mall, Vancouver V6T 1Z1, British Columbia, Canada.
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Centko
authors.forename: Anne
authors.initials: A
authors.lastname: Steinø
authors.forename: Federico I
authors.initials: FI
authors.lastname: Rosell
authors.forename: Brian O
authors.initials: BO
authors.lastname: Patrick
authors.forename: Nicole
authors.initials: N
authors.lastname: de Voogd
authors.forename: A Grant
authors.initials: AG
authors.lastname: Mauk
authors.forename: Raymond J
authors.initials: RJ
authors.lastname: Andersen
mesh_terms: D000818:Animals; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013329:Structure-Activity Relationship; D047131:Xestospongia / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D006576:Heterocyclic Compounds, 4 or More Rings; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase; D007783:Lactones; C000600291:xestolactone A; C000600290:xestosaprol O