A-ring modified betulinic acid derivatives as potent cancer preventive agents

Hsin Yi Hung, Kyoko Nakagawa-Goto, Harukuni Tokuda, Akira Iida, Nobutaka Suzuki, Ibrahim D. Bori, Keduo Qian, Kuo Hsiung Lee

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)


Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol-13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1 × 103 mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5 × 102, 1 × 10 2, and 1 × 10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay.

Original languageEnglish
Pages (from-to)1005-1008
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Issue number3
Publication statusPublished - 2014 Feb 1

All Science Journal Classification (ASJC) codes

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


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