title: New synthetic method of 8-oxocoptisine starting from natural quaternary coptisine as anti-ulcerative colitis agent.
abstract: Quaternary coptisine (1), a natural bioactive quaternary protoberberine alkaloid (QPA), was treated with potassium ferricyanide in aqueous solution of 5 N sodium hydroxide leading to the acquisition of 8-oxocoptisine (2) with much higher yield than reported in the literature. This is the first report of the oxidation of a natural QPA by applying potassium ferricyanide as an oxidant. 8-Oxocoptisine showed significant anti-ulcerative colitis efficacy in vitro with EC50 value being 8.12 × 10(- 8) M.
authors.affiliation: a State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , China.
authors.forename: Zhi-Hui
authors.initials: ZH
authors.lastname: Zhang
authors.forename: Lian-Qiu
authors.initials: LQ
authors.lastname: Wu
authors.forename: An-Jun
authors.initials: AJ
authors.lastname: Deng
authors.forename: Jin-Qian
authors.initials: JQ
authors.lastname: Yu
authors.forename: Zhi-Hong
authors.initials: ZH
authors.lastname: Li
authors.forename: Hai-Jing
authors.initials: HJ
authors.lastname: Zhang
authors.forename: Wen-Jie
authors.initials: WJ
authors.lastname: Wang
authors.forename: Hai-Lin
authors.initials: HL
authors.lastname: Qin
mesh_terms: D001599:Berberine / Q000031:analogs & derivatives; D001600:Berberine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003093:Colitis, Ulcerative / Q000188:drug therapy*; D005292:Ferricyanides / Q000494:pharmacology; D015394:Molecular Structure
chemical_list: C000592718:8-oxocoptisine; D001600:Berberine Alkaloids; D005292:Ferricyanides; C034384:coptisine; D001599:Berberine; C009090:protoberberine; C028033:potassium ferricyanide
keywords: 8-oxocoptisine; anti-ulcerative colitis; potassium ferricyanide; quaternary coptisine