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Mechanism of Action of Antimicrobial and Antitumor Agents pp 577–584Cite as

Berberine

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Part of the book series: Antibiotics ((ANTIBIOTICS,volume 3))

Abstract

Berberine is a yellow alkaloid which occurs in numerous plants (Jeffs, 1967). It was first isolated from Xanthoxylon cava in 1826 by Chevallier and Pelletan. The chemical structure of berberine is shown in Fig. 1. The compound exists as an equilibrium mixture of three tautomeric forms (Gadamer, 1905). Structure la which contains a quarternary nitrogen, forms salts with mineral acids such as HCI and H2SO4 through elimination of one molecule of water; these salts are correctly designated as berberinium compounds. Berberinium nitrate is poorly soluble, and the addition of nitric acid to aqueous solutions of the alkaloid precipitates the nitrate. The quarternary base has an extraordinary high pKα of 15.23 in water (Shih-Chieh Ch’ou and Liang-Chun Ch’a, 1965).

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Authors
  1. Fred E. Hahn
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  2. Jennie Ciak
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Editor information

Editors and Affiliations

  1. Department of Biochemistry, The Medical and Dental Schools, Northwestern University, 303 E. Chicago Avenue, Chicago, Illinois, 60611, USA

    John W. Corcoran Ph.D.

  2. Department of the Army, Walter Reed Army Institute of Research, Walter Reed Army Medical Center, Washington, D.C., 20012, USA

    Fred E. Hahn Ph.D.

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© 1975 Springer-Verlag Berlin Heidelberg

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Hahn, F.E., Ciak, J. (1975). Berberine. In: Corcoran, J.W., Hahn, F.E., Snell, J.F., Arora, K.L. (eds) Mechanism of Action of Antimicrobial and Antitumor Agents. Antibiotics, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46304-4_38

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  • DOI: https://doi.org/10.1007/978-3-642-46304-4_38

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-46306-8

  • Online ISBN: 978-3-642-46304-4

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