title: Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursors.
abstract: In this study, cordatanine, with a canthin-6-one skeleton, was totally synthesized in four steps via a Pictet-Spengler reaction using tryptamine and methyl glyoxylate with a total yield of 8%. The NMR spectra of synthesized cordatanine compared well with those of drymaritin isolated by Hsieh et al., confirming the need to revise the original structural assignment. In addition, kumujian A, a synthetic intermediate, showed significant anti-inflammatory effects, inhibiting both superoxide anion generation (IC50 4.87 μg/mL) and elastase release (IC50 6.29 μg/mL).
authors.affiliation: School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, No. 1 University Road, Tainan 701, Taiwan.
authors.forename: Hsin Wei
authors.initials: HW
authors.lastname: Fang
authors.affiliation: School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, No. 1 University Road, Tainan 701, Taiwan.
authors.forename: Yu-Ren
authors.initials: YR
authors.lastname: Liao
authors.affiliation: Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Kweishan 333, Taoyuan, Taiwan.
authors.forename: Tsong-Long
authors.initials: TL
authors.lastname: Hwang
authors.affiliation: Department of Pharmacy, Tajen University, Pintung 907, Taiwan.
authors.forename: Po-Chuen
authors.initials: PC
authors.lastname: Shieh
authors.affiliation: Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA; Chinese Medicine and Development Center, China Medical University Hospital, Taichung 404, Taiwan.
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, No. 1 University Road, Tainan 701, Taiwan. Electronic address: z10308005@email.ncku.edu.tw.
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, No. 1 University Road, Tainan 701, Taiwan; Department of Pharmacy, Tajen University, Pintung 907, Taiwan. Electronic address: tswu@mail.ncku.edu.tw.
authors.forename: Tian-Shung
authors.initials: TS
authors.lastname: Wu
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D015394:Molecular Structure; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D002243:Carbolines; C489105:drymaritin; D013481:Superoxides; D010196:Pancreatic Elastase
keywords: Cordatanine; Drymaritin; Kumujian A