Planta Med 2003; 69(7): 623-627
DOI: 10.1055/s-2003-41115
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Antimicrobial Constituents from Goldenseal (the Rhizomes of Hydrastis canadensis) against Selected Oral Pathogens

Bang Yeon Hwang1 , Sara K. Roberts2 , Lucas R. Chadwick1 , Christine D. Wu2 , A. Douglas Kinghorn1
  • 1Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA
  • 2Department of Periodontics, College of Dentistry, University of Illinois at Chicago, Chicago, IL, USA
Further Information

Publication History

Received: November 12, 2002

Accepted: March 22, 2003

Publication Date:
04 August 2003 (online)

Abstract

Two new C-methyl flavonoids, 6,8-di-C-methylluteolin 7-methyl ether (1) and 6-C-methylluteolin 7-methyl ether (2), were isolated from a commercially available sample of the roots of Hydrastis canadensis, along with seven known compounds, berberine (3), β-hydrastine (4), canadine (5), canadaline (6), isocorypalmine (7), canadinic acid (8), and β-sitosterol 3-O-β-D-glucoside (9). The structures of the new compounds 1 and 2 were elucidated on the basis of their spectral data including 1D and 2D NMR techniques. Of these isolates, berberine (3) and, to a lesser extent, 1 and 2, showed antimicrobial activity when evaluated against the oral pathogens Streptococcus mutans and Fusobacterium nucleatum. Berberine (3) exhibited an additive antimicrobial effect when tested against S. mutans in combination with 1.

References

  • 1 Evans W C. Hydrastis.  In: Trease and Evans’ Pharmacognosy, 14th edn. London; WB Saunders Co. Ltd 1999: p. 374
  • 2 Mar C, Bent S. An evidence-based review of the 10 most commonly used herbs.  West J Med. 1999;  171 168-71
  • 3 Messana I, La Bua R, Galeffi C. The alkaloids of Hydrastis canadensis L. (Ranunculaceae). Two new alkaloids: Hydrastinine and isohydrastinine.  Gazz Chim Ital. 1980;  110 539-43
  • 4 Galeffi C, Cometa M F, Tomassini L, Nicoletti M. Canadinic acid: An alkaloid from Hydrastis canadensis .  Planta Med. 1997;  63 194
  • 5 Gentry E J, Jampani H B, Keshavarz-Shokri A, Morton M D, Vander Velde D, Telikepalli H, Mitscher L A. Antitubercular natural products: Berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, β-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2.  J Nat Prod. 1998;  61 1187-93
  • 6 Chadwick L R, Wu C D, Kinghorn A D. Isolation of alkaloids from goldenseal (Hydrastis canadensis rhizomes) using pH-zone refining countercurrent chromatography.  J Liq Chrom Rel Technol. 2001;  24 2445-53
  • 7 Scazzocchio F, Cometa M F, Tomassini L, Palmery M. Antibacterial activity of Hydrastis canadensis extract and its major isolated alkaloids.  Planta Med. 2001;  67 561-4
  • 8 Mills S, Bone K. Principles and practice of phytotherapy: Modern herbal medicine. London; Churchill Livingstone 2000: p. 286-96
  • 9 Roberts S K, Wei G -X, Wu C D. Evaluating biofilm growth of two oral pathogens.  Lett Appl Microbiol. 2002;  35 552-6
  • 10 Mabry T J, Markham K R, Thomas M B. The systematic identification of flavonoids. New York; Springer Verlag 1970: pp. 35-61
  • 11 Gupta D R, Ahmed B. A new C-methylflavone from Boerhaavia diffusa Linn. roots.  Indian J Chem. 1984;  23B 682-4
  • 12 Zheng S, Kang S, Shen Y, Sun L. Three new C-methylated flavones from Elsholtzia stauntonii .  Planta Med. 1999;  65 173-5
  • 13 Iwasa K, Nanba H, Lee D -U, Kang S I. Structure-activity relationships of protoberberines having antimicrobial activity.  Planta Med. 1998;  64 748-51
  • 14 Hu J P, Takahashi N, Yamada T. Coptidis Rhizoma inhibits growth and proteases of oral bacteria.  Oral Diseases. 2000;  6 297-302
  • 15 Stermitz F R, Tawara-Matsuda J, Lorenz P, Mueller P, Zenewicz L, Lewis K. 5-Methoxyhydnocarpin-D and pheophorbide A: Berberis species components that potentiate berberine growth inhibition of resistant Staphylococcus aureus .  J Nat Prod. 2000;  63 1146-9
  • 16 Stermitz F R, Lorenz P, Tawara J N, Zenewicz L A, Lewis K. Synergy in a medicinal plant: Antimicrobial action of berberine potentiated by 5-methoxyhydnocarpin, a multidrug pump inhibitor.  Proc Natl Acad Sci USA. 2000;  97 1433-7

Prof. A. Douglas Kinghorn

Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy

College of Pharmacy

University of Illinois at Chicago

Chicago

IL 60612

USA

Phone: +1-312-996-0914

Fax: +1-312-996-7107

Email: kinghorn@uic.edu

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