Total synthesis of cordatanine, structural reassignment of drymaritin, and anti-inflammatory activity of synthetic precursors

  • Bioorg Med Chem Lett. 2015 Sep 15;25(18):3822-4. doi: 10.1016/j.bmcl.2015.07.074.
Hsin Wei Fang  1 ,  Yu-Ren Liao  1 ,  Tsong-Long Hwang  2 ,  Po-Chuen Shieh  3 ,  Kuo-Hsiung Lee  4 ,  Hsin-Yi Hung  5 ,  Tian-Shung Wu  6
Affiliations
  • 1. School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, No. 1 University Road, Tainan 701, Taiwan.
  • 2. Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Kweishan 333, Taoyuan, Taiwan.
  • 3. Department of Pharmacy, Tajen University, Pintung 907, Taiwan.
  • 4. 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.
  • 5. School of Pharmacy, National Cheng Kung University Hospital, College of Medicine, National Cheng Kung University, No. 1 University Road, Tainan 701, Taiwan. Electronic address: [email protected].
  • 6. 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: [email protected].
PMID: 26248804 DOI: 10.1016/j.bmcl.2015.07.074
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).

Keywords
Cordatanine; Drymaritin; Kumujian A.
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