Planta Med 2013; 79(15): 1461-1469
DOI: 10.1055/s-0033-1350806
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Triterpene Glycosides from the Leaves of Pittosporum angustifolium

Authors

  • Christian Bäcker

    1   Institute of Pharmacy, Department of Pharmaceutical Biology, Ernst Moritz Arndt University Greifswald, Greifswald, Germany
  • Kristina Jenett-Siems

    2   Institute of Pharmacy, Department of Pharmaceutical Biology, Free University of Berlin, Berlin, Germany
  • Karsten Siems

    3   AnalytiCon Discovery GmbH, Potsdam, Germany
  • Martina Wurster

    1   Institute of Pharmacy, Department of Pharmaceutical Biology, Ernst Moritz Arndt University Greifswald, Greifswald, Germany
  • Anja Bodtke

    4   Institute of Pharmacy, Department of Pharmaceutical/Medicinal Chemistry, Ernst Moritz Arndt University Greifswald, Greifswald, Germany
  • Chamseddin Chamseddin

    4   Institute of Pharmacy, Department of Pharmaceutical/Medicinal Chemistry, Ernst Moritz Arndt University Greifswald, Greifswald, Germany
  • Max Crüsemann

    1   Institute of Pharmacy, Department of Pharmaceutical Biology, Ernst Moritz Arndt University Greifswald, Greifswald, Germany
    5   Present address: Kekulé Institute of Organic Chemistry and Biochemistry, Rheinische Friedrich Wilhelms University Bonn, Bonn, Germany
  • Ulrike Lindequist

    1   Institute of Pharmacy, Department of Pharmaceutical Biology, Ernst Moritz Arndt University Greifswald, Greifswald, Germany
Further Information

Publication History

received 05 March 2013
revised 04 July 2013

accepted 07 August 2013

Publication Date:
17 September 2013 (online)

Abstract

Phytochemical investigation of the leaves of Pittosporum angustifolium resulted in the isolation and structural elucidation of nine new triterpene saponins, named pittangretosides A-I (19), together with a known compound (10). Mainly by NMR and HRESIMS experiments, eight compounds were identified as A1-barrigenol glycosides (17, 10), whereas two compounds exhibited an unusual 17,22-seco-backbone of oleanolic acid (8, 9). All compounds were evaluated for their in vitro cytotoxicities against human urinary bladder carcinoma cells (5637). Only compounds with an angeloyl-residue at C-22 of the aglycone (14 and 10) showed antiproliferative effects with IC50 values of 4.1, 5.2, 2.1, 17.9, and 2.4 µM, respectively.