Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group.
The investigation of a dichloromethane extract of flower heads of a Hungarian taxon of the Achillea millefolium group led to the isolation of three flavonoid aglycones, one triterpene, one germacranolide and five guaianolides. Their structures were elucidated by UV-VIS, EI- and CI-MS, 1H NMR and 13C NMR spectroscopic methods as well as by 2D-NMR studies and by selective 1D-NOE experiments. Besides apigenin, luteolin and centaureidin, beta-sitosterol, 3beta-hydroxy-11alpha,13-dihydro-costunolide, desacetylmatricarin, leucodin, achillin, 8alpha-angeloxy-leucodin and 8alpha-angeloxy-achillin were isolated. Both latter substances are reported here for the first time. Their NMR data were compared with those of the other guaianolides. The stereochemistry of 3beta-hydroxy-11alpha,13-dihydro-costunolide was discussed and compared with data of the literature.
Glasl
Sabine
S
Institute of Pharmacognosy, University of Vienna, Pharma Center, Althanstrasse 14, A-1090 Vienna, Austria. sabine.glasl@univie.ac.at
Mucaji
Pavel
P
Werner
Ingrid
I
Presser
Armin
A
Jurenitsch
Johann
J
D031162:Achillea / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification; D015939:Kitasamycin / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D013055:Spectrophotometry, Infrared
D005419:Flavonoids; D010936:Plant Extracts; D012717:Sesquiterpenes; D015939:Kitasamycin