title: Asymmetric synthesis and biological activity of nor-α-tocopherol, a new vitamin E analogue.
abstract: The vitamin E analogues (2R,4'R,8'R)-nor-α-tocopherol (94 % de) and (2RS,4'R,8'R)-nor-α-tocopherol have been synthesized from (all R)-hexahydrofarnesol and phytol, respectively. According to in vitro experiments with murine macrophages nor-α-tocopherol is an anti-inflammatory compound more potent than α-tocopherol.
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns Ring 19, 4056 Basel, Switzerland.
authors.forename: Julien
authors.initials: J
authors.lastname: Chapelat
authors.forename: Urs
authors.initials: U
authors.lastname: Hengartner
authors.forename: Antoinette
authors.initials: A
authors.lastname: Chougnet
authors.forename: Kegang
authors.initials: K
authors.lastname: Liu
authors.forename: Patricia
authors.initials: P
authors.lastname: Huebbe
authors.forename: Gerald
authors.initials: G
authors.lastname: Rimbach
authors.forename: Wolf-D
authors.initials: WD
authors.lastname: Woggon
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D016207:Cytokines / Q000378:metabolism; D007249:Inflammation / Q000235:genetics; D008264:Macrophages / Q000187:drug effects / Q000201:enzymology / Q000378:metabolism; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D052247:Nitric Oxide Synthase Type II / Q000378:metabolism; D012333:RNA, Messenger / Q000235:genetics / Q000378:metabolism; D013237:Stereoisomerism; D024502:alpha-Tocopherol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D016207:Cytokines; D012333:RNA, Messenger; D052247:Nitric Oxide Synthase Type II; D024502:alpha-Tocopherol