New Constituents of Leontopodium alpinum and their in vitro Leukotriene Biosynthesis Inhibitory Activity
2004; Thieme Medical Publishers (Germany); Volume: 70; Issue: 10 Linguagem: Inglês
10.1055/s-2004-832625
ISSN1439-0221
AutoresStefan Schwaiger, Michael Adams, Christoph Seger, Ernst P. Ellmerer, Rudolf Bauer, Hermann Stuppner,
Tópico(s)Natural product bioactivities and synthesis
ResumoPhytochemical 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).
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