Total synthesis and anticancer activity of novel Pulsatilla saponin D analogues

Minkyu Kim, Yongseo Park, Won Yoon Chung, Kwang Kyun Park, Mankil Jung

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Novel saponins that retain a free carboxyl group at the C-17 position and various sugars linked at the C-3 position of hederagenin aglycone were synthesized via stereospecific glycosylation. Since these natural products represented by Pulsatilla saponin D (PSD) were obtained in very small amounts, the total synthesis developed in this paper will resolve this problem of scarcity. The two types of synthesized arabinose- and rhamnose-cored saponins showed potent anticancer activity against a human lung cancer cell line (A549), and most disaccharide moiety saponins possessed more potent anti-lung cancer activity. Among the novel PSD analogues containing disaccharide saponins, compound 10i showed anti-lung cancer activity (6.6 μM) that was four-fold more potent than the clinical agent Iressa® (26.08 μM).

Original languageEnglish
Article numberA3
Pages (from-to)669-677
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume63
Issue number9
DOIs
Publication statusPublished - 2015 Sep 1

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

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