title: Synthesis and biological evaluation of chalcone, dihydrochalcone, and 1,3-diarylpropane analogs as anti-inflammatory agents.
abstract: Twenty-one chalcones were prepared via aldol condensation and subsequent reduction of these compound led to the corresponding dihydrochalcone and 1,3-diphenylpropane derivatives. The synthetic products were examined for their effects on NO inhibition in LPS-activated mouse peritoneal macrophages. Among the tested compounds, a 1,3-diarylpropane analog, 2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol (3p), displayed the most significant inhibitory effects against NO production. To investigate the mechanism of action, the effects of 3p on iNOS and COX-2 protein expression were studied by immunoblot. The results concluded that 3p is capable of inhibiting iNOS expression in LPS-induced RAW264.7 cells via attenuation of NF-κB signaling by ERK, p38, and JNK.
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan.
authors.forename: Mopur
authors.initials: M
authors.lastname: Vijaya Bhaskar Reddy
authors.affiliation: School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan 701, Taiwan.
authors.forename: Hsin-Yi
authors.initials: HY
authors.lastname: Hung
authors.affiliation: School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan 701, Taiwan.
authors.forename: Ping-Chung
authors.initials: PC
authors.lastname: Kuo
authors.affiliation: School of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, College of Pharmacy, China Medical University, Taichung 404, Taiwan.
authors.forename: Guan-Jhong
authors.initials: GJ
authors.lastname: Huang
authors.affiliation: Department of Biotechnology, Southern Taiwan University of Science and Technology, Tainan 710, Taiwan.
authors.forename: Yu-Yi
authors.initials: YY
authors.lastname: Chan
authors.affiliation: Graduate Institute of Pharmaceutical Science, Chia-Nan University of Pharmacy and Science, Tainan 717, Taiwan.
authors.forename: Shiow-Chyn
authors.initials: SC
authors.lastname: Huang
authors.affiliation: Department of Medical Technology, Chung Hua University of Medical Technology, Tainan 717, Taiwan.
authors.forename: Shwu-Jen
authors.initials: SJ
authors.lastname: Wu
authors.affiliation: Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, United States.
authors.forename: Susan L
authors.initials: SL
authors.lastname: Morris-Natschke
authors.affiliation: Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, United States; Chinese Medicinal Research and Development Center, China Medical University Hospital, China Medical University, Taichung 404, Taiwan. Electronic address: khlee@unc.edu.
authors.forename: Kuo-Hsiung
authors.initials: KH
authors.lastname: Lee
authors.affiliation: School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, Tainan 701, Taiwan; Department of Pharmacy, College of Pharmacy and Health Care, Tajen University, Pingtung 907, Taiwan. Electronic address: tswu@mail.ncku.edu.tw.
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*; D002460:Cell Line; D047188:Chalcones / Q000138:chemical synthesis / Q000494:pharmacology*; D051546:Cyclooxygenase 2 / Q000378:metabolism; D048049:Extracellular Signal-Regulated MAP Kinases / Q000378:metabolism; D048031:JNK Mitogen-Activated Protein Kinases / Q000378:metabolism; D051379:Mice; D016328:NF-kappa B / Q000378:metabolism; D009569:Nitric Oxide / Q000378:metabolism; D052247:Nitric Oxide Synthase Type II / Q000378:metabolism; D010636:Phenols / Q000138:chemical synthesis / Q000494:pharmacology*; D010766:Phosphorylation; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D015398:Signal Transduction; D048051:p38 Mitogen-Activated Protein Kinases / Q000378:metabolism
chemical_list: C000621524:2-(3-(3,4-dimethoxyphenyl)propyl)-5-methoxyphenol; D000894:Anti-Inflammatory Agents, Non-Steroidal; D047188:Chalcones; D016328:NF-kappa B; D010636:Phenols; D009569:Nitric Oxide; D052247:Nitric Oxide Synthase Type II; C496317:Nos2 protein, mouse; C077623:Ptgs2 protein, mouse; D051546:Cyclooxygenase 2; D048049:Extracellular Signal-Regulated MAP Kinases; D048031:JNK Mitogen-Activated Protein Kinases; D048051:p38 Mitogen-Activated Protein Kinases; D011407:Propane
keywords: 1,3-Diarylpropane analogs; Anti-inflammatory agents; Chalcones; Dihydrochalcones