title: Anti-inflammatory and antimalarial meroterpenoids from the New Zealand ascidian Aplidium scabellum.
abstract: Bioassay-directed fractionation of an extract of the New Zealand ascidian Aplidium scabellum has afforded the anti-inflammatory secondary metabolite 2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate (1) and a family of pseudodimeric meroterpenoids scabellones A (2)-D (5). The benzo[c]chromene-7,10-dione scaffold contained within scabellones A-D is particularly rare among natural products. The structures were elucidated by interpretation of NMR data. Scabellone B was also identified as a moderately potent, nontoxic inhibitor of Plasmodium falciparum.
authors.affiliation: School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand.
authors.forename: Susanna T S
authors.initials: ST
authors.lastname: Chan
authors.forename: A Norrie
authors.initials: AN
authors.lastname: Pearce
authors.forename: Ana H
authors.initials: AH
authors.lastname: Januario
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Page
authors.forename: Marcel
authors.initials: M
authors.lastname: Kaiser
authors.forename: Rene J
authors.initials: RJ
authors.lastname: McLaughlin
authors.forename: Jacquie L
authors.initials: JL
authors.lastname: Harper
authors.forename: Victoria L
authors.initials: VL
authors.lastname: Webb
authors.forename: David
authors.initials: D
authors.lastname: Barker
authors.forename: Brent R
authors.initials: BR
authors.lastname: Copp
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology*; D000962:Antimalarials / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology*; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D009520:New Zealand; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000737:chemistry / Q000187:drug effects*; D011809:Quinones / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology*; D014561:Urochordata / Q000737:chemistry*
chemical_list: C570520:2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate; D000893:Anti-Inflammatory Agents; D000962:Antimalarials; D001578:Benzopyrans; D011809:Quinones; D013729:Terpenes; C570521:azo(c)chromene-7,10-dione