Abstract
Typical chromatographic methods were successfully applied to isolate nine flavonoid compounds and two coumarin glycosides from the inflorescences and the herb of <em>Hieracium pilosella</em> L. Repeated column chromatography, occasionally paper chromatography and recrystallization made the separation of three flavonoid aglycones and six glycosides - possible. Coumarin glycosides were isolated by preparative thin layer chromatography. Subsequent UV, NMR and MS analyses have led to identification of the following flavonoid derivatives: known for the species - apigenin, luteolin, luteolin 7-O- ß-glucopyranoside, luteolin 4’-O-ß-glucopyranoside, isoetin 7-O-ß- -glucopyranoside, isoetin 4’-O-ß-glucuronide and new for the species – kaempferol 3-methyl ether and apigenin 7-O-ß-glucopyranoside. Third isoetin glycoside contained two different sugar moieties: xylose and glucose, probably attached to the hydroxyl groups at C-4’ or C-4’ and C-2’(or 5’) of an aglycone. Umbelliferone 7-O-ß-glucopyranoside (skimmin) and new for the genus Hieracium esculetin 7-O-ß-glucopyranoside (cichoriin) were determined by NMR and MS methods.
Highlights
Hieracium pilosella L. is a common plant and a very invasive weed, native to Eurasia, but it has been introduced into North America and into New Zealand
Untill eleven different glycosides of isoetin have been identified in some species from the family Asteraceae mostly, in representatives of the genus Hieracium (GluchoffFiasson et al 1991; Harborne 1978, 1991; Marco et al 1988; Pauli and Junior 1995; Shi et al 2008; Zidorn et al 2002, 2005)
The knowledge of benzo-a-pirone and benzo-g-pirone derivatives present in this species is still incomplete and undoubtedly many therapeutic values of this plant may be attributed to these constituents
Summary
Hieracium pilosella L. (mouse-ear hawkweed) is a common plant and a very invasive weed, native to Eurasia, but it has been introduced into North America and into New Zealand. Some articles have reported the presence of coumarins or flavonoids in mouse-ear hawkweed, but none of them has concerned possibly the most complete isolation and full spectral identification of these polyphenolic biologically active components (Bate-Smith et al 1968; Haag-Berrurier and Duquénois 1962, 1963; Harborne 1978; Henn et al 1988; Sheluyto et al 1977; Zidorn et al 2002, 2005). Untill eleven different glycosides of isoetin have been identified in some species from the family Asteraceae mostly, in representatives of the genus Hieracium (GluchoffFiasson et al 1991; Harborne 1978, 1991; Marco et al 1988; Pauli and Junior 1995; Shi et al 2008; Zidorn et al 2002, 2005). The knowledge of benzo-a-pirone (e.g. coumarins) and benzo-g-pirone (flavonoids) derivatives present in this species is still incomplete and undoubtedly many therapeutic values of this plant may be attributed to these constituents. ISOLATION AND IDENTIFICATION OF FLAVONOIDS AND COUMARINS Gawroñska-Grzywacz M. et al
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