Total Synthesis and Anticancer Activity of Novel Pulsatilla Saponin D Analogues

Chemical & Pharmaceutical Bulletin
Minkyu KimMankil Jung

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).

References

Jan 1, 1994·Advances in Carbohydrate Chemistry and Biochemistry·R R Schmidt, W Kinzy
Oct 11, 2005·Archives of Pharmacal Research·Tran Manh HungKiHwan Bae
Nov 8, 2005·Chemical & Pharmaceutical Bulletin·Seong-Cheol BangByung-Zun Ahn
Aug 1, 2006·Biochimica Et Biophysica Acta·Martin ChwalekLaurence Voutquenne-Nazabadioko

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