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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

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
› Author Affiliations
Further Information

Publication History

received 05 March 2013
revised 04 July 2013

accepted 07 August 2013

Publication Date:
17 September 2013 (online)

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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 (1–9), together with a known compound (10). Mainly by NMR and HRESIMS experiments, eight compounds were identified as A1-barrigenol glycosides (1–7, 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 (1–4 and 10) showed antiproliferative effects with IC50 values of 4.1, 5.2, 2.1, 17.9, and 2.4 µM, respectively.

Key words

Pittosporum angustifolium - Pittosporaceae - A1-barrigenol - seco-glycosides - pittangretosides

Supporting Information

 

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