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Planta Med 2004; 70(10): 978-985
DOI: 10.1055/s-2004-832625
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag KG Stuttgart · New York

New Constituents of Leontopodium alpinum and their in vitro Leukotriene Biosynthesis Inhibitory Activity

Stefan Schwaiger1 , Michael Adams2 , Christoph Seger1 , Ernst P. Ellmerer3 , Rudolf Bauer2 , Hermann Stuppner1
  • 1Institut für Pharmazie, Abteilung Pharmakognosie, Leopold-Franzens-Universität Innsbruck, Innsbruck, Austria
  • 2Institut für Pharmazeutische Wissenschaften, Abteilung Pharmakognosie, Karl-Franzens-Universität Graz, Graz, Austria
  • 3Institut für Organische Chemie, Leopold-Franzens-Universität Innsbruck, Innsbruck, Austria
Further Information

Publication History

Received: April 27, 2004

Accepted: July 12, 2004

Publication Date:
18 October 2004 (online)

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Abstract

Phytochemical investigations of the roots of Leontopodium alpinum Cass. resulted in the isolation and structure elucidation of six novel compounds and two known compounds. Novel constituents could be identified as the polyacetylenes 1-acetoxy-3-angeloyloxy-(4E,6E)-tetradeca-4,6-diene-8,10,12-triyne and its (6Z)-isomer, the kaurenic acid derivative methyl ent-7α,9α-dihydroxy-15β-[(2Z)-2-methyl-but-2-enoyloxy]kaur-16-en-19-oate, the bisabolane derivative (1R*,3S*,4R*,6S*)-9-(acetoxy)-4-hydroxy-1-[(2Z)-2-methylbut-2-enoyloxy]bisabol-10(11)-ene and the lignans [(2S,3R,4R)-4-(3,4-dimethoxybenzyl)-2-(3,4,5-trimethoxyphenyl)-tetrahydrofuran-3-yl]-methyl-(2Z)-2-methylbut-2-enoate and its 3,4,5-trimethoxybenzyl derivative. Known compounds, reported here for the first time for the genus Leontopodium, were identified as ent-kaur-16-en-19-oic acid and T-cadinol. The obtained compounds were tested together with 15 previously described compounds of L. alpinum in an ex vivo leukotriene biosynthesis inhibition assay. The highest activities were determined for the bisabolane derivates (IC50: 7.7 to 11.4 μM), one lignan (IC50 : 10.7 μM) and the ent-kaurenoate (IC50: 10.4 μM).

Key words

Leontopodium alpinum - leukotriene biosynthesis inhibition - lignan - bisabolane - polyacetylene - kaurenic acid

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Univ.-Prof. Dr. Hermann Stuppner

Institut für Pharmazie

Leopold-Franzens-Universität Innsbruck

Innrain 52

6020 Innsbruck

Austria

Phone: +43-512-507-5300

Fax: +43-512-507-2939

Email: Hermann.Stuppner@uibk.ac.at