Planta Med 2002; 68(1): 88-91
DOI: 10.1055/s-2002-20053
Letter

© Georg Thieme Verlag Stuttgart · New York

Phenolic Compounds from Hypericum perforatum

Guido Jürgenliemk1, 2 , Adolf Nahrstedt1
  • 11 Institute of Pharmaceutical Biology and Phytochemistry, Westfälische Wilhelms-University of Münster, Germany
  • 22 Part of the PhD thesis of G. Jürgenliemk
Further Information

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