Total synthesis and biological evaluation of viscolin, a 1,3-diphenylpropane as a novel potent anti-inflammatory agent.
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.
Su
Chung-Ren
CR
Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan.
Shen
Yuh-Chiang
YC
Kuo
Ping-Chung
PC
Leu
Yann-Lii
YL
Damu
Amooru G
AG
Wang
Yea-Hwey
YH
Wu
Tian-Shung
TS
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
D000894:Anti-Inflammatory Agents, Non-Steroidal; D001713:Biphenyl Compounds; D016207:Cytokines; C513809:viscolin; D011407:Propane; D019331:NG-Nitroarginine Methyl Ester