title: Total synthesis and biological evaluation of viscolin, a 1,3-diphenylpropane as a novel potent anti-inflammatory agent.
abstract: Total synthesis of viscolin, an anti-inflammatory 1,3-diphenylpropane isolated from Viscum coloratum, employing the Wittig reaction is reported. Key steps in the synthesis of viscolin depend on the selection of protecting groups to maintain the para hydroxyl group that is the most critical chemical structure influencing the biological activity of viscolin and the utilization of microwave-assisted Wittig olefination reaction. Anti-inflammatory potency of the synthetic viscolin, its precursor product 16, and its analogue 17, through their effects on reactive oxygen species (ROS), nitric oxide (NO), and pro-inflammatory cytokine production in leukocytes and microglial cells were evaluated. Excellent inhibition of ROS and NO production in inflammatory cells could confer the synthetic viscolin to be a potent anti-inflammatory agent for the treatment of oxidative stress-induced diseases.
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan.
authors.forename: Chung-Ren
authors.initials: CR
authors.lastname: Su
authors.forename: Yuh-Chiang
authors.initials: YC
authors.lastname: Shen
authors.forename: Ping-Chung
authors.initials: PC
authors.lastname: Kuo
authors.forename: Yann-Lii
authors.initials: YL
authors.lastname: Leu
authors.forename: Amooru G
authors.initials: AG
authors.lastname: Damu
authors.forename: Yea-Hwey
authors.initials: YH
authors.lastname: Wang
authors.forename: Tian-Shung
authors.initials: TS
authors.lastname: Wu
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D016207:Cytokines / Q000378:metabolism; D006801:Humans; D007962:Leukocytes / Q000187:drug effects / Q000502:physiology; D051379:Mice; D017628:Microglia / Q000187:drug effects / Q000502:physiology; D019331:NG-Nitroarginine Methyl Ester / Q000494:pharmacology; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology; D028181:Viscum
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D001713:Biphenyl Compounds; D016207:Cytokines; C513809:viscolin; D011407:Propane; D019331:NG-Nitroarginine Methyl Ester