[Germacranolides, Guaianolides, and Xanthanolides from the Flowers of Arnica mollis and an X-Ray Structure Analysis of Baileyin Acetate].

Abstract:

: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.

journal_name

Planta Med

journal_title

Planta medica

authors

Marcinek-Hüpen-Bestendonk C,Willuhn G,Steigel A,Wendisch D,Middelhauve B,Wiebcke M,Mootz D

doi

10.1055/s-2006-960898

subject

Has Abstract

pub_date

1990-02-01 00:00:00

pages

104-10

issue

1

eissn

0032-0943

issn

1439-0221

journal_volume

56

pub_type

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