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Planta Med 1990; 56(1): 104-110
DOI: 10.1055/s-2006-960898
Paper

© Georg Thieme Verlag Stuttgart · New York

Germacranolide, Guaianolide und Xanthanolide aus Blüten von Arnica mollis und Röntgenstrukturanalyse von Baileyinacetat1

Germacranolides, Guaianolides, and Xanthanolides from the Flowers of Arnica mollis and an X-Ray Structure Analysis of Baileyin Acetate1 Christoph Marcinek-Hüpen-Bestendonk2 , Günter Willuhn2 , Alois Steigel3 , Detlef Wendisch4 , Birgit Middelhauve5 , Michael Wiebcke5 , Dietrich Mootz5
  • 1Postervortrag, 35. Vortragstagung der Gesellschaft für Arzneipnanzenforschung in Leiden, 20.-24.9.1987, s. Ref. (23)
  • 2Institut für Pharmazeutische Biologie der Heinrich-Heine-Universität Düsseldorf, Geb. 26.23, Universitätsstr.1, D-4000 Düsseldorf 1, Federal Republic of Germany
  • 3Institut für Organische Chemie und Makromolekulare Chemie der Heinrich-Heine-Universität Düsseldorf, D-4000 Düsseldorf 1, Federal Republic of Germany
  • 4Zentralbereich Forschung und Entwicklung der Bayer AG, D-5090 Leverkusen-Bayerwerk, Federal Republic of Germany
  • 5Institut für Anorganische Chemie und Strukturchemie der Heinrich-Heine-Universität Düsseldorf, D-4000 Düsseldorf 1, Federal Republic of Germany
Further Information

Publication History

1989

Publication Date:
05 January 2007 (online)

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Abstract

The flowers of Arnica mollis afforded, in addition to baileyin (1a), baileyin acetate (1b), xanthalongin (3), and 2-deacetoxy-11α,13-dihydroxanthuminol (6), the new 1,5-cis-guaianolides arnimollin acetate (2a) and arnimollin tiglinate (2a) and the new xanthanolides 11β3,13-dihydroxanthalongin (4) and 11α,13-dihydroxanthalongin (5). No traces of helenanolides were discernible. The structures were elucidated mainly by high-field NMR spectroscopy. The stereochemistry of 1b has been revised on the basis of an X-ray crystallographic study to be a 4α,5β-epoxygermacrolide instead of a 4α,5β-epoxymelampolide. The implications for the biosynthesis of cis- and trans-fused guaianolides are discussed. The co-occurrence of 1a with cis-fused guaianolides and xanthanolides (no helenanolides) in A. mollis and with trans-fused guaianolides and helenanolides (no xanthanolides) in A. acaulis supports the hypothesis that germacrolides represent the biogenetic precursors for cis- and trans- fused guaianolides.

Key words

Arnica mollis - Asteraceae - sesquiterpene lactones - germacrolides - 1,5-cis-guaianolides - xanthanolides - biosynthetic implications