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DOI: 10.1055/s-2002-20053
© Georg Thieme Verlag Stuttgart · New York
Phenolic Compounds from Hypericum perforatum
Publication History
February 1, 2001
May 27, 2001
Publication Date:
31 January 2002 (online)
Abstract
During a re-investigation of phenolic compounds from the dried crude drug material of St. John’s wort (Hypericum perforatum L.) 22 phenolic compounds were detected by HPLC; 14 of them were quantified using the same system. Twelve phenolic compounds were isolated from the plant material and their structures identified mainly by spectroscopic methods, among them quercetin-3-O-(2″-O-acetyl)-β-D-galactoside as a new natural product. Cryptochlorogenic acid, protocatechuic acid, 3-O-[Z]-p-coumaroylquinic acid, isoorientin, cyanidin-3-O-α-L-rhamnoside, and astilbin were obtained for the first time from this source; the earlier suspected neochlorogenic acid, 3-O-[E]-p-coumaroylquinic acid, mangiferin, miquelianin and guaijaverin were confirmed.
References
-
1 Nahrstedt A. Antidepressant constituents of Hypericum perforatum
. In : Chrubasik S, Roufogalis BD, editors
Herbal Medicinal Products for the Treatment of Pain . Southern Cross Univ. Press Lismore Australia; 2000: 144-53 - 2 Chatterjee S S, Bhattacharyra S K, Wonnemann M, Singer A, Müller W E. Hyperforin as a possible antidepressant compound of Hypericum extracts. Life Sci. 1998; 63 499-510
- 3 Butterweck V, Petereit F, Winterhoff H, Nahrstedt A. Solubilized hypericin and pseudohypericin from Hypericum perforatum exert antidepressant activity in the Forced Swimming Test. Planta Med. 1998; 64 291-4
- 4 Butterweck V, Jürgenliemk G, Nahrstedt A, Winterhoff H. Flavonoids from Hypericum perforatum show antidepressant activity in the Forced Swimming Test. Planta Med. 2000; 66 3-6
- 5 Mabry T J, Markham K R, Thomas M B. The Systematic Identification of Flavonoids. Springer-Verlag Berlin, Heidelberg, New York; 1970
- 6 Noe C R., Freissmuth J. Capillary zone electrophoresis of aldose enantiomers: separation after derivatization with S-(-)-1-phenylethylamine. J Chromatogr A. 1995; 704 503-12
- 7 Kuczkowiak U. Hydroxyzimtsäurederivate und Flavonoide in offizinellen Crataegus Arten. PhD Thesis 2000 Münster, Germany;
- 8 Wada H, Shimizu Y, Tanaka N, Cambie R C, Braggins J E. Chemical and chemotaxonomical studies of ferns. LXXXVII. Chem Pharm Bull. 1995; 43 461-5
- 9 Prox A. Massenspektroskopische Untersuchung einiger natürlicher C-Glucosyl-Verbindungen. Tetrahedron. 1968; 24 3697-715
- 10 Torskangerpoll K, Fossen T, Andersen M. Anthocyanin pigments of tulips. Phytochemistry. 1999; 52 1687-92
- 11 Merfort I, Wendisch W. Flavonolglucuronide aus den Blüten von Arnica montana . Planta Med. 1988; 54 247-50
- 12 De Britto J, Manickam V S, Gopalakrishnan S, Ushioda T, Tanaka N. Determination of aglycone chirality in dihydroflavonol 3-O-α-L-rhamnosides by 1H-NMR spectroscopy. Chem Pharm Bull. 1995; 43 338-9
- 13 Pachaly P, Klein M. Inhaltsstoffe von Andromeda polifolia . Planta Med. 1987; 53 442-4
- 14 Becchi M, Fraisse D. Fast atom bombardment and fast atom bombardment collision activated dissociation/mass analysed ion kinetic energy analysis of C-glycosidic flavonoids. Biomed Environ Mass Spectr. 1989; 18 122-30
- 15 Strack D, Wray V. In Dey PM, Harborne JB Methods in Plant Biochemistry. Vol. 1 Academic Press Limited London, San Diego, New York, Berkeley, Boston, Sydney; Tokyo, Toronto; 1989
- 16 Pedersen A T, Andersen M, Aksnes D W, Nerdal W. NMR of anthocyanins: assignments and effects of exchanging aromatic protons. Magn Res Chem. 1993; 31 972-6
- 17 He X G. On-line identification of phytochemical constituents in botanical extracts by high-performance liquid chromatographic-diode array detection-mass spectrometric techniques. J Chromatogr A. 2000; 880 203-32
- 18 Hansen S H, Jensen A G, Cornett C, Björnsdottir I, Taylor S, Wright B, Wilson I D. High-performance liquid chromatography on-line coupled to high-field NMR and mass spectrometry for structure elucidation of constituents of Hypericum perforatum L. Anal Chem. 1999; 71 5235-41
- 19 Seabra R M, Vasconcelos M H, Cruz Costa M A, Alves A C. Phenolic compounds from Hypericum perforatum and H. undulatum . Fitoterapia. 1992; 63 473-4
- 20 Hölzl J, Ostrowski E. Johanniskraut. Analyse der wichtigen Inhaltsstoffe und deren Variabilität in einer Population. Dtsch Apoth Ztg. 1987; 127 1227-30
- 21 Dias A CP, Seabra R M, Andrade P B, Fernandes-Ferreira M. The development and evaluation of an HPLC-DAD method for the analysis of the phenolic fractions from in vivo and in vitro biomass of Hypericum species. J. Liq. Chrom. & Rel. Technol.. 1999; 22 215-27
Prof. Dr. Adolf Nahrstedt
Institute for Pharmaceutical Biology and Phytochemistry
Westfälische Wilhelms-University of Münster
Hittorfstr. 56
48149 Münster
Germany
Phone: +49-251-8333-380
Email: nahrste@uni-muenster.de