Germacranolide, Guaianolide und Xanthanolide aus Blüten vonArnica mollisund Röntgenstrukturanalyse von Baileyinacetat1
| Autor: | Detlef Wendisch, Christoph Marcinek-Hüpen-Bestendonk, B. Middelhauve, Dietrich Mootz, Michael Wiebcke, Günter Willuhn, Alois Steigel |
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| Rok vydání: | 1990 |
| Předmět: |
Pharmacology
biology Structure analysis Stereochemistry Organic Chemistry Pharmaceutical Science Nuclear magnetic resonance spectroscopy Asteraceae Sesquiterpene biology.organism_classification Analytical Chemistry Rhizome chemistry.chemical_compound Complementary and alternative medicine chemistry Arnica mollis Drug Discovery Molecular Medicine Organic chemistry |
| Zdroj: | Planta Medica. 56:104-110 |
| ISSN: | 1439-0221 0032-0943 |
| Popis: | The flowers of ARNICA MOLLIS afforded, in addition to baileyin ( 1A), baileyin acetate ( 1B), xanthalongin ( 3), and 2-deacetoxy-11alpha,13-dihydroxanthuminol ( 6), the new 1,5- CIS-guaianolides arnimollin acetate ( 2A) and arnimollin tiglinate ( 2A) and the new xanthanolides 11beta3,13-dihydroxanthalongin ( 4) and 11alpha,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 4alpha,5beta-epoxygermacrolide instead of a 4alpha,5beta-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. |
| Databáze: | OpenAIRE |
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