title: Ethynylbenzenoid metabolites of Antrodia camphorata: synthesis and inhibition of TNF expression.
abstract: An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro-Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-metabolite antrodioxolanone (4) were unsuccessful, but a samarium diiodide-mediated pinacol coupling of antrocamphin B did provide the chiral epimers (51). Antrocamphin A (2) inhibits Tumour Necrosis Factor (TNF) reporter gene expression, but its development as an anti-inflammatory agent may be limited by cytotoxicity.
authors.affiliation: School of Chemistry and Biochemistry, The University of Western Australia, Perth, WA, Australia. matthew.piggott@uwa.edu.au.
authors.forename: Marco
authors.initials: M
authors.lastname: Buccini
authors.forename: Kathryn A
authors.initials: KA
authors.lastname: Punch
authors.forename: Belinda
authors.initials: B
authors.lastname: Kaskow
authors.forename: Gavin R
authors.initials: GR
authors.lastname: Flematti
authors.forename: Brian W
authors.initials: BW
authors.lastname: Skelton
authors.forename: Lawrence J
authors.initials: LJ
authors.lastname: Abraham
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Piggott
mesh_terms: D000480:Alkynes / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000840:Anisoles / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D055491:Antrodia / Q000737:chemistry* / Q000378:metabolism; D001688:Biological Products / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D016923:Cell Death / Q000187:drug effects; D002460:Cell Line; D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure; D018124:Receptors, Tumor Necrosis Factor / Q000037:antagonists & inhibitors* / Q000235:genetics; D013329:Structure-Activity Relationship
chemical_list: D000480:Alkynes; D000840:Anisoles; D001688:Biological Products; D018124:Receptors, Tumor Necrosis Factor; C550852:antrocamphin A