Flavonoids and coumarins from Hieracium pilosella L. (Asteraceae)

Typical chromatographic methods were successfully applied to isolate nine flavonoid compounds and two coumarin glycosides from the inflorescences and the herb of Hieracium pilosella 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- s-glucopyranoside, luteolin 4’-O-s-glucopyranoside, isoetin 7-O-s- -glucopyranoside, isoetin 4’-O-s-glucuronide and new for the species – kaempferol 3-methyl ether and apigenin 7-O-s-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-s-glucopyranoside (skimmin) and new for the genus Hieracium esculetin 7-O-s-glucopyranoside (cichoriin) were determined by NMR and MS methods.

[1]  M. Gawrońska-Grzywacz,et al.  Free and bound phenolic acids in inflorescences and rhizomes with roots of Hieracium pilosella L. (Asteraceae) , 2011 .

[2]  M. Gawrońska-Grzywacz,et al.  Sterol composition from inflorescences of Hieracium pilosella L. , 2011 .

[3]  Yu Zhao,et al.  Preparative isolation and purification of three flavonoid glycosides from Taraxacum mongolicum by high-speed counter-current chromatography. , 2008, Journal of separation science.

[4]  C. Kroner,et al.  Herbal medicines as diuretics: a review of the scientific evidence. , 2007, Journal of ethnopharmacology.

[5]  M. Gawrońska-Grzywacz,et al.  Identification and determination of triterpenoids in Hieracium pilosella L. , 2007, Journal of separation science.

[6]  S. Moon,et al.  Isoetin 5'-Methyl Ether, A Cytotoxic Flavone from Trichosanthes kirilowii , 2007 .

[7]  H. Stuppner,et al.  Altitudinal differences in the contents of phenolics in flowering heads of three members of the tribe Lactuceae (Asteraceae) occurring as introduced species in New Zealand , 2005 .

[8]  P. Vernet,et al.  Interference between Hieracium pilosella and Arrhenatherum elatius in colliery spoils of north of France , 1988, Oecologia.

[9]  J. Vallès,et al.  Studies on pharmaceutical ethnobotany in the region of Pallars (Pyrenees, Catalonia, Iberian Peninsula). Part II. New or very rare uses of previously known medicinal plants. , 2003, Journal of ethnopharmacology.

[10]  W. Kisiel,et al.  A new coumarin glucoside ester from Cichorium intybus. , 2002, Fitoterapia.

[11]  H. Stuppner,et al.  Chemosystematic investigations on phenolics from flowerheads of Central European taxa of Hieracium sensu lato (Asteraceae) , 2002, Plant Systematics and Evolution.

[12]  M. Gawrońska-Grzywacz,et al.  Sterols in the roots and herb from Hieracium pilosella L. , 2002 .

[13]  K. Shimoda,et al.  Biotransformation of hydroxycoumarins by the cultured cells of Nicotiana tabacum , 2000 .

[14]  J. Fleurentin,et al.  Effect of extracts of Orthosiphon stamineus benth, Hieracium pilosella L., Sambucus nigra L. and Arctostaphylos uva‐ursi (L.) spreng. in rats , 1998, Phytotherapy research : PTR.

[15]  C. A. Williams,et al.  Flavonoids, cinnamic acids and coumarins from the different tissues and medicinal preparations of Taraxacum officinale. , 1996, Phytochemistry.

[16]  A. Planas,et al.  Synthesis of 4-methylumbelliferyl-β-d-glucan oligosaccharides as specific chromophoric substrates of (1 → 3),(1 → 4)-β-d-glucan 4-glucanohydrolases , 1995 .

[17]  G. Pauli,et al.  Phenolic glycosides from Adonis aleppica , 1995 .

[18]  John R. L. Walker,et al.  Luteolin and 6-hydroxyluteolin glycosides from Hebe stricta , 1993 .

[19]  P. Bolle,et al.  Hieracium Pilosella L.: Pharmacological Effect of Ethanol Extract , 1993 .

[20]  Jeffrey B. Haborne.  Revised structures for three isoetin glycosides, yellow flower pigments in Heywoodiella oligocephala , 1991 .

[21]  J. Favre-Bonvin,et al.  Glycosides and acylated glycosides of isoetin from european species of Hypochoeris , 1991 .

[22]  K. Hostettmann,et al.  Antimicrobial flavonoids from Psiadia trinervia and their methylated and acetylated derivatives , 1989 .

[23]  J. Marco,et al.  Flavonoids and other phenolics from Artemisia hispanica , 1988 .

[24]  M. Arisawa,et al.  A chemotaxonomic study of flavonoids in the leaves of six Trichosanthes species , 1987 .

[25]  D. Pilbeam.  The Flavonoids: Advances in Research : Edited by J.B. Harborne and T.J. Mabry Chapman and Hall; London, New York, 1982 744 pages. £ 49.50 , 1983 .

[26]  J. Harborne.  The rare flavone isoetin as a yellow flower pigment in Heywoodiella oligocephala and in other Cichorieae , 1978 .

[27]  T. Mabry,et al.  The flavonoids of tetragonotheca (compositae) , 1978 .

[28]  K. R. Markham.  Flavonoids and phylogeny of the ‘primitive’ New Zealand hepatic, Haplomitrium gibbsiae , 1977 .

[29]  K. R. Markham,et al.  Luteolin 3′,4′-di-O-β-d-glucuronide and luteolin 3′-O-β-d-glucuronide from Lunularia cruciata , 1974 .

[30]  T. Mabry,et al.  The Systematic Identification of Flavonoids , 1970, Springer Berlin Heidelberg.