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Planta Med 2014; 80(04): 297-305
DOI: 10.1055/s-0033-1360312
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Isolation, Characterization, and In Vitro Cytotoxicity of New Sesquiterpenoids from Achillea clavennae

Snežana Trifunović
1   Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
,
Anđelka M. Isaković
2   Institute of Medical and Clinical Biochemistry, School of Medicine, University of Belgrade, Belgrade, Serbia
,
Aleksandra Isaković
2   Institute of Medical and Clinical Biochemistry, School of Medicine, University of Belgrade, Belgrade, Serbia
,
Ivan Vučković
1   Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
,
Boris Mandić
1   Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
,
Miroslav Novaković
3   Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia
,
Vlatka Vajs
3   Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Belgrade, Serbia
,
Slobodan Milosavljević
1   Faculty of Chemistry, University of Belgrade, Belgrade, Serbia
,
Vladimir Trajković
4   Institute of Microbiology and Immunology, School of Medicine, University of Belgrade, Belgrade, Serbia
› Author Affiliations
Further Information

Publication History

received 16 May 2013
revised 29 December 2013

accepted 02 January 2014

Publication Date:
07 February 2014 (online)

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Abstract

Further phytochemical investigation of the aerial parts of Achillea clavennae has resulted in the isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and the iso-seco-guaianolide 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known compounds were also found, of which 9α-acetoxycanin (5), sintenin (6), and oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were elucidated by combined spectroscopic methods (1D and 2D NMR, HRESIMS, CIMS, and FTIR). While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines.

Key words

Achillea clavennae L. - Asteraceae - sesquiterpene lactones - iso-seco-guaianolide - NMR - cytotoxicity - apoptosis
 

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