title: Halicloic acids A and B isolated from the marine sponge Haliclona sp. collected in the Philippines inhibit indoleamine 2,3-dioxygenase.
abstract: Two new merohexaprenoids, halicloic acids A (1) and B (2), have been isolated from the marine sponge Haliclona (Halichoclona) sp. collected in the Philippines. The glycolic acids 1 and 2 slowly decomposed during acquisition of NMR data to aldehydes 3 and 4, respectively, via an oxidative decarboxylation. Halicloic acid B (2) has the new rearranged "haliclane" meroterpenoid carbon skeleton. The halicloic acids 1 and 2 are indoleamine 2,3-dioxygenase inhibitors that are significantly more active than the decomposition products 3 and 4.
authors.affiliation: Department of Chemistry, University of British Columbia, Vancouver, B.C., Canada, V6T 1Z1.
authors.forename: David E
authors.initials: DE
authors.lastname: Williams
authors.forename: Anne
authors.initials: A
authors.lastname: Steinø
authors.forename: Nicole J
authors.initials: NJ
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; D047129:Haliclona / Q000737:chemistry*; D006801:Humans; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase / Q000037:antagonists & inhibitors*; D008386:Marine Biology; D015394:Molecular Structure; D010679:Philippines; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase; D013729:Terpenes; C576024:halicloic acid A; C576025:halicloic acid B