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

Hsin Wei Fang, Yu Ren Liao, Tsong Long Hwang, Po Chuen Shieh, Kuo Hsiung Lee, Hsin Yi Hung, Tian Shung Wu

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

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).

Original languageEnglish
Article number22963
Pages (from-to)3822-3824
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number18
DOIs
Publication statusPublished - 2015 Aug 17

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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