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2 Milestones in Drug Therapy MDT Series Editors Prof. Michael J. Parnham, PhD Prof. Dr. J. Bruinvels Senior Scientific Advisor Sweelincklaan 75 PLIVA Research Institute Ltd NL-3723 JC Bilthoven Prilaz baruna Filipovića 29 The Netherlands HR Zagreb Croatia

3 St. John s Wort and its Active Principles in Depression and Anxiety Edited by W. E. Müller Birkhäuser Verlag Basel Boston Berlin

4 Editor Walter E. Müller Pharmakologisches Institut für Naturwissenschaftler Biozentrum Universität Frankfurt Marie-Curie-Str Frankfurt Germany Advisory Board J.C. Buckingham (Imperial College School of Medicine, London, UK) R.J. Flower (The William Harvey Research Institute, London, UK) G. Lambrecht (J.W. Goethe Universität, Frankfurt, Germany) Library of Congress Cataloging-in-Publication Data St. John s Wort and its active principles in depression and anxiety / W.E. Müller, editor. p. ; cm.-- (Milestones in drug therapy) Includes bibliographical references and index. ISBN (alk. paper) 1. Hypericum perforatum--therapeutic use. 2. Affective disorders--treatment. I. Müller, Walter E. (Walter Erhard), II. Series. [DNLM: 1. Hypericum. 2. Phytotherapy. 3. Anxiety Disorders--drug therapy. 4. Depressive Disorder--drug therapy. QV 766 S ] RS165.H95S dc Bibliographic information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data is available in the Internet at < ISBN 10: Birkhäuser Verlag, Basel - Boston - Berlin ISBN 13: The publisher and editor can give no guarantee for the information on drug dosage and administration contained in this publication. The respective user must check its accuracy by consulting other sources of reference in each individual case. The use of registered names, trademarks etc. in this publication, even if not identified as such, does not imply that they are exempt from the relevant protective laws and regulations or free for general use. This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, re-use of illustrations, recitation, broadcasting, reproduction on microfilms or in other ways, and storage in data banks. For any kind of use, permission of the copyright owner must be obtained Birkhäuser Verlag, P.O. Box 133, CH-4010 Basel, Switzerland Part of Springer Science+Business Media Printed on acid-free paper produced from chlorine-free pulp. TCF Printed in Germany ISBN 10: ISBN 13: www. birkhauser.ch

5 Contents List of contributors VII Walter E. Müller Introduction and historical outline Kurt Hostettmann and Jean-Luc Wolfender Phytochemistry Marco Gobbi and Tiziana Mennini St. John s Wort and its active principles in depression and anxiety A critical analysis of receptor binding studies Kristina Treiber and Walter E. Müller Effects on transmitter uptake and their cellular and molecular basis.. 31 Jan Kehr, Sven Ove Ögren and Takashi Yoshitake Modulation of neurotransmitter release and metabolism Carla Gambarana and Daniela Giachetti Efficacy in behavioural models of antidepressant activity Michael Nöldner Comparative preclinical antidepressant activity of isolated constituents Shyam S. Chatterjee Hyperforin and efficacy in animal models for anxiety and cognition.. 85 Mario Wurglics and Manfred Schubert-Zsilavecz Pharmacokinetics and biopharmaceuticals Siegfried Kasper Clinical efficacy in depression Hans-Peter Volz Clinical efficacy of St. John s Wort in psychiatric disorders other than depression

6 VI Contents Volker Schulz and Andreas Johne Side effects and drug interactions Michael Franklin Endocrinology of St. John s Wort extract Index

7 VII List of contributors Shyam S. Chatterjee, Pharmacology Laboratories, Research and Development Department, Dr. Willmar Schwabe GmbH&Co KG, Willmar-Schwabe- Straße 4, Karlsruhe, Germany; Michael Franklin, University of Oxford Department of Psychiatry, Warneford Hospital, Oxford OX3 7JX, United Kingdom; and School of Biological and Molecular Sciences, Oxford Brookes University, Oxford OX3 0BP, United Kingdom; Carla Gambarana, Department of Neuroscience, Pharmacology Unit, University of Siena, Via Moro 4, Siena, Italy; unisi.it Daniela Giachetti, Department of Environmental Sciences, University of Siena, Via T. Pendola 62, Siena, Italy; Marco Gobbi, Istituto di Ricerche Farmacologiche Mario Negri, Via Eritrea 62, Milano, Italy; Kurt Hostettmann, Laboratoire de Pharmacognosie et Phytochimie, Section des Sciences Pharmaceutiques, Université de Genève, Quai Ernest Ansermet 30, CH-1211 Genève 4, Switzerland; Andreas Johne, Institut für Klinische Pharmakologie, Universitätsklinikum Charité, Schumannstraße 20, Berlin, Germany; Siegfried Kasper, Klinische Abteilung für Allgemeine Psychiatrie, Universitätsklinik für Psychiatrie, Medizinische Universität Wien, Währinger Gürtel 18 20, 1090 Wien, Austria; Jan Kehr, Department of Neuroscience, Karolinska Institutet, Retzius väg 8, Stockholm, Sweden; Tiziana Mennini, Istituto di Ricerche Farmacologiche Mario Negri, Via Eritrea 62, Milano, Italy; Walter E. Müller, Pharmakologisches Institut für Naturwissenschaftler, Biozentrum Universität Frankfurt, Marie-Curie-Str.9, Frankfurt, Germany; Michael Nöldner, Dr. Willmar Schwabe GmbH & Co KG, Willmar-Schwabe- Straße 4, Karlsruhe, Germany; schwabe.de Sven Ove Ögren, Department of Neuroscience, Karolinska Institutet, Retzius väg 8, Stockholm, Sweden; Manfred Schubert-Zsilavecz, Institute of Pharmaceutical Chemistry, Johann Wolfgang Goethe University Frankfurt/Main, Marie-Curie-Str. 9, 60439

8 VIII List of contributors Frankfurt/Main, Germany; Volker Schulz, Oranienburger Chaussee 25, Berlin, Germany; Kristina Treiber, Pharmakologisches Institut für Naturwissenschaftler, Biozentrum Universität Frankfurt, Marie-Curie-Str.9, Frankfurt, Germany; Hans-Peter Volz, Krankenhaus für Psychiatrie und Psychotherapie Schloss Werneck, Balthasar-Neumann-Platz 1, Werneck, Germany; Jean-Luc Wolfender, Laboratoire de Pharmacognosie et Phytochimie, Section des Sciences Pharmaceutiques, Université de Genève, Quai Ernest Ansermet 30, CH-1211 Genève 4, Switzerland; pharm.unige.ch Mario Wurglics, Institute of Pharmaceutical Chemistry, Johann Wolfgang Goethe University Frankfurt/Main, Marie-Curie-Str. 9, Frankfurt/Main, Germany; Takashi Yoshitake, Department of Neuroscience, Karolinska Institutet, Retzius väg 8, Stockholm, Sweden;