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Planta Med 2005; 71(3): 254-260
DOI: 10.1055/s-2005-837841
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

New Cytotoxic Prenylated Isoflavonoids from Bituminaria morisiana

Filippo Cottiglia1 , Laura Casu1 , Leonardo Bonsignore1 , Mariano Casu2 , Costantino Floris2 , Marco Leonti3 , Jürg Gertsch3 , Jörg Heilmann3
  • 1Dipartimento Farmaco Chimico Tecnologico, University of Cagliari, Cagliari, Italy
  • 2Dipartimento di Scienze Chimiche, University of Cagliari, Cagliari, Italy
  • 3Department of Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology Zurich (ETH), Zurich, Switzerland
Further Information

Publication History

Received: May 13, 2004

Accepted: October 24, 2004

Publication Date:
15 March 2005 (online)

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Abstract

Using cytotoxicity against KB cancer cells as a lead, bioguided-fractionation of the petroleum ether and ethyl acetate extracts of Bituminaria morisiana leaves led to the isolation of two new pterocarpans, namely 3,9-dihydroxy-4-(3,3-dimethylallyl) [6aR, 11aR]-pterocarpan, 3-hydroxy-4-(3,3-dimethylallyl)-4′′,5′′-dehydropyrano[8,9:2′′,3′′][6aR,11aR]-pterocarpan and one new isoflavone identified as 4′,5′′-dihydroxy-6′′-methoxy-4′′,4′′-dimethyl-4′′,5′′-dihydro-6′′H-pyrano[2′′,3′′:7,8]-isoflavone. Moreover, two known pterocarpans, erybraedin C and bitucarpin A, three known isoflavones, daidzein, 8-prenyldaidzein and bidwillon C, one known furocoumarin, pseudoisopsoralen and one known coumestan, coumestrol were isolated. The structures of the isolated compounds were established by means of 1D and 2D NMR spectroscopy, as well as mass spectrometry. Further cytotoxicity tests against cells related to the immune system (Jurkat T, Mono-Mac-6 and polymorphonuclear cells) showed a moderate activity of the known pterocarpan erybraedin C against all cell lines used (IC50 values between 17.6 - 28.8 μM). In addition, erybraedin C was found to induce necrosis in leukaemia Jurkat T cells.

Key words

Bituminaria morisiana - Fabaceae - pterocarpans - isoflavones - cytotoxicity - necrosis

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Dr. Filippo Cottiglia

Dipartimento Farmaco Chimico Tecnologico

Faculty of Pharmacy

Via Ospedale 72

09124 Cagliari

Italy

Phone: +39-70-675-8679

Fax: +39-70-675-8553

Email: cottiglf@unica.it