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H. Wagner S. Bladt E.M.

Zgainski

Plant Drug
Analysis

A Thin Layer Chromatography Atlas


Translated by Th.A. Scott

With 170 Colored Photographs

Springer-Verlag Berlin Heidelberg GmbH 1984

Professor Dr. Hildebert Wagner


Dr. Sabine Bladt
Eva Maria Zgainski (Fachphotographin)
Institut fr Pharmazeutische Biologie
der Universitt Mnchen,
Karlstrae 29,
D-8000 Mnchen 2
Translator:
Dr. Thomas A. Scott
Department of Biochemistry
University of Leeds
GB-Leeds LS2 9JT

Translation of the German edition' Drogenanalyse '


Springer-Verlag Berlin Heide1berg 1983
ISBN 978-3-662-02400-3
ISBN 978-3-662-02398-3 (eBook)
DOI 10.1007/978-3-662-02398-3
Library of Congress Cataloging in Publication Data
Wagner, H. (Hildebert), 1929Plant drug analysis.
Includes bibliographical references and index.
1. Materia medica, Vegetable-Analysis. 2. Drugs-Analysis. 3. Thin layer chromatography. I.
Bladt, S. (Sabine), 1945. H. Zgainski, E.M. (Eva Maria), 1928. III. Title.
RS190.P55W3313 1984 615'.32 84-5348
This work is subject to copyright. All rights are reserved, whether the whole or part of the
material is concerned specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machine or similar means, and storage in data banks.
Under 54 of the German Copyright Law where copies are made for other than private
use, a fee is payable to "Verwertungsgesellschaft Wort", Munich.
by Springer-Verlag Berlin Heidelberg 1984
Originally published by Springer-Verlag Berlin Heidelberg New York in 1984.

Softcover reprint of the hardcover 1st edition 1984


The use of registered names, trademarks, etc. in this publication does not imply, even in
the absence of a specific statement, that such names are exempt from the relevant protective
laws and regulations and therefore for general use.
Product Liability: The publisher can give no guarantee for information ab out drug dosage
and application thereof contained in this book. In every individual case the respective user
must check its accuracy by consulting other pharmaceuticalliterature.
Reproduction of the figures : Gebrder Czech, D-8000 Mnchen
2131/3130-543210

Preface

Thin layer chromatography is the most widely used of all the simple chromatographie
methods for the analysis of mixtures. On account of its extreme rapidity and ease
of visual evaluation, thin layer chromatography has become the most ideal analytical
method for plant drugs and for preparations that contain drug extracts or pure
drug constituents.
One disadvantage of the technique was the lack of a satisfactory method for
the permanent recording of results. Analyses were recorded simply by verbal description of the chromatogram (e.g., in the pharmacopoeias), by schematic drawings,
or by idealized colored diagrams. All these methods are c1early makeshift solutions
to the problem of documentation. In order to make the documentation as realistic
as possible, we have therefore attempted to make faithful photographic reproductions of thin layer chromatographie separations of drugs in visible and UV-light.
The chief difficulty that we encountered in the preparation of this TLC atlas was
knowing how to take into account the natural qualitative and quantitative variations
that occur in the composition of individual drugs. We believe we have solved this
problem by selecting, from more than 10 years of photo graphie recording, those
pictures that are the most representative and are photographically the best reproductions of chromatograms of standard drugs. In choosing solvent systems, we have
relied primarilyon the pharmacopoeias, but we have also made proposals for improvements and for future standardization. In view of the extent of the present-day
world drug market, analyses of many commercial, non-official drugs have also been
documented. Emphasis was placed primarily on commercial European drugs.
We hope that this chromatographie drug atlas will help those who are learning
the technique, and serve as an aid for the evaluation of thin layer chromatograms.
Furthermore, we believe that this thin layer chromatographie drug atlas represents
an aid to the standardization of industrial plant drug preparations. It will enable
the systematization of the identification and purity control of plant drugs.
The authors are especially grateful to Mrs. J. DUFOSSE of Agfa photographie
services, Munieh, for the painstaking and faithful reproduction of the color pictures.
We thank Miss MAHN and Miss SCHUCKER for technical assistance, and Mrs.
ANDRAE for drawing the formulae. Thanks are due to Springer-Verlag, and especially
to Mrs. DEIGMLLER, for their helpful co operation to our wishes with regard to
the reproduction of the chromatograms and the overall layout of the book.
HILDEBER T WAGNER
SABINE BLADT
EVA MARIA ZGAINSKI

Contents

Introduction

Essential Oil Drugs (Aetherolea)

Extraction and TLC . . . . . . . .


List of Essential Oil Drugs . . . . .
Formulae of Constituents of Essential Oils

5
9
19

Reference Compounds

Figs. 1, 2

22

Cinnamoni cortex
Calami rhizoma

Figs. 3, 4

24

. . . . . . . . . . . . . Figs. 5, 6

26

Petroselini fructus
Myristicae semen
Macis
Caryophylli flos . . . . . . . . . . . . . Figs. 7, 8

28

Carvi fructus
Coriandri fructus
Juniperi fructus
Rosmarini folium

Figs. 9,10

30

Matricariae flos
Anthemidis flos

. Figs. 11, 12

32

Lavandulae flos
Cinae flos . . .

Figs. 13, 14

34

Menthae piperitae folium


Menthae crispae folium

. Figs. 15, 16

36

Salviae officinalis folium


Salviae trilobae folium
Eucalypti folium
. . . . . . . . . . Figs. 17, 18

38

Anisi fructus
F oeniculi fructus
Sassafras lignum
Basilici herba

Thymi herba
Serpylli herba
Ajowani fructus
Melissae folium

. Figs. 19,20

Curcumae rhizoma

Figs. 21, 22

40
42
VII

Ci tri pericarpium
Aurantii pericarpium

. . . . . . . . . . . Figs. 23, 24

44

Terebinthinae aeth.
Pini aetherolea
Myrrha . . . . .

. . . . . . . . . . . Figs. 25, 26

46

. . . . . . . . . . Figs. 27, 28

48

Benzoin
Balsamum tolutanum
Balsamum peruvianum

Alkaloid Drugs

51

Extraction and TLC


List of Alkaloid Drugs
Formulae of Constituents of Alkaloid Drugs

51
55
61

Reference Compounds

Figs 1, 2

66

Y ohimbe cortex
Quebracho cortex

Figs. 3, 4

68

Rauwolfiae radix

Figs. 5, 6

70

Strychni semen
Ignatii semen

. Fig. 7

72

Secale cornutum

. Fig. 8

72

Chinae cortex

Figs. 9, 10

74

Ipecacuanhae radix

.Figs. 11, 12

76

Opium

Figs. 13, 14

78

Berberidis radix
Colombo radix
Hydrastis rhizoma

. Figs. 15, 16

80

Chelidonii herba
Colchici semen

Fig. 17
Fig. 18

82
82

Aconiti tuber (herba)


Sabadillae semen
Lobeliae herba
Jaborandi folium
Boldo folium

Figs. 19, 20

84

Cacao semen
Coffeae semen

Fig. 21

86

Nicotianae folium
Ephedrae herba
Spartii herba . .
Belladonnae folium
Hyoscyami folium
Stramonii folium .

VIII

. . . . . . . . . . . . Fig. 22

. . . . . . . . . .

86

. . . . . . Figs. 23, 24

88

Belladonnae folium/semen/radix
Hyoscyami mutici/nigri folium
Stramonii folium/semen
Scopoliae radix . . . . . . . . . . . . . . Figs. 25, 26

90

Drugs Containing Anthracene Derivatives

93

Extraction and TLC . . . . . . . . . . . . .


List of Drugs Containing Anthracene Glycosides
Formulae of Anthracene Derivatives Identified as Drug Constituents

93
97
100

Aloe resina

. Figs. 1,2

102

Rhamni purshiani cortex

. Fig. 3

104

TLC-Synopsis

. Fig. 4

104

Frangulae cortex
Oreoherzogiae cortex
Frangulae fructus
Rhamni cathartici fructus

Figs. 5, 6

" 106

Rhei radix . .

Figs. 7, 8

. 108

Sennae folium
Sennae fructus
Hyperici herba

. Figs. 9,10

110

Circular TLC
Sennae foliumjfructus
Rhei radix . . . . .

. Figs. 11, 12
Figs. 13, 14

112
114

Arbutin Drugs

117

Extraction and TLC


List of Drugs Containing Arbutin
...... .
Formulae

117
119

119

Uvae ursi folium


Vitis ideae folium
Myrtilli folium .

Figs. 1,2

120

Viburni prunifolii cortex


Viburni opuli cortex

Figs. 3,4

122

Bitter Principle Drugs


Extraction and TLC . . .
List of Bitter Principle Drugs
Formulae of Constituents
of Bitter Principle Drugs
Aurantii pericarpium
Harpagophythi radix
Gentianae radix
Centaurii herba
Condurango cortex
Menyanthidis folium
Cnici herba
Marrubii herba
Absinthii herba
Quassiae lignum

125
125

127
130

. . . . . . . . . . . Figs. 1,2

. . . . . . . . . 132

. . . . . . . . . . . . . Figs. 3, 4

. . . . . . . . . 134
IX

Gentianae radix
Plantaginis herba
Oleae folium/fructus

Figs. 5, 6

136

Bryoniae radix
Cucurbitae semen

Figs. 7, 8

138

Humuli strobuli

Figs. 9, 10

140

Salviae folium
Rosmarini folium
Cynarae herba .

Fig. 11
Fig. 12

142
142

Coumarin Drugs

145

Extraction and TLC


List of Coumarin Drugs
Formulae of Constituents of Coumarin Drugs

145
147
150

Reference compounds

. Fig. 1

152

Pimpinellae radix
Heraclei radix

. Fig. 2

152

Angelicae radix
Levistici radix
Imperatoriae radix
Scopoliae radix.

. . . . . . . . . . . . Figs. 3, 4

. . . . . . . . . 154

. . . . . . . . . . . . . Figs. 5, 6

. . . . . . . . . 156

Mezerei cortex
Fraxini cortex
Asa foetida

Figs. 7, 8

158

Ammi majoris fructus


Ammi visnagae fructus

Figs. 9, 10

160

Herniariae herba
Meliloti herba
Asperulae herba
Abrotani herba
Rutae herba.

Flavonoid Drugs

163

Extraction and TLC


List of Flavonoid Drugs
Formulae of Constituents of Flavonoid Drugs

163
165
170

Reference Compounds
. Figs. 1,2
TLC Synopsis (flos) . . . . . . . . . . . . Figs. 3, 4

172
174

Arnicae flos
Calendulae flos
Cacti flos
Farfarae flos
Primulae flos
Herniariae herba

. . . . . . . . Figs. 5, 6

. . . . . . . . . 176

Crataegi flos/folium/fructus
Sambuci flos
Stoechados flos
Verbasci flos . . . . . . . . . . . . . . . Figs. 7, 8

. . . . . . . . . 178

Acaciae flos
Pruni spinosae flos
Spireaae flos
Robiniae flos
Sambuci flos
Tiliae flos .
. . . . . . . . . . . . . Figs. 9, 10

. . . . . . . . 180

Betulae folium
Juglandis folium
Anthemidis flos

Figs. 11, 12

182

Matricariae flos

. Fig. 13

184

TLC Synopsis (Herba)

Fig. 14

184

Anserinae herba
Equiseti herba
Leonuri herba
Rutae herba
Sarothamni herba
Sophorae gemma
Veronicae herba
Violae tricoloris herba

. Figs. 15, 16

186

Citri pericarpium
Aurantii pericarpium

Fig. 17

188

Eriodictyonis herba
Orthosiphonis folium

Fig. 18

188

Cardui mariae (Silybi) fructus

Figs. 19,20

190

Farfarae folium
Petasites folium

Figs. 21, 22

192

Cardiac Glycoside Drugs

195

Extraction and TLC . . . .


List of Cardiac Glycoside Drugs
Formulae of Constituents
of Cardiac Glycoside Drugs

195

198
200

Reference compounds . .

Figs. 1,2
Figs. 3, 4

204
206

Digitalis lanatae folium


Digitalis purpureae folium

Figs. 5-8

208

Nerii (oleandri) folium

Figs. 9, 10

212

TLC Comparison
Strophanthi semen
Adonidis herba
Convallariae herba

Figs. 11, 12

214

Strophanthi grati semen


Strophanthi kombe semen

Figs. 13, 14

216

Adonidis herba
Convallariae herb'it

Figs. 15, 16

218
XI

Uzarae (Xysmalobii) radix


Helleborii radix

. Fig. 17
Fig. 18

220
220

Scillae bulbus
var. alba/var. rubra

Figs. 19,20

222

Saponin Drugs

225

Extraction and TLC


List of Saponin Drugs
Formulae of Constituents of Saponin Drugs

225
227
230

TLC Synopsis

Figs. 1, 2

234

Primulae radix
Saponariae radix

. Fig. 3
. Fig. 4

236
236

Ginseng radix
Eleutherococci radix

Figs. 5, 6

238

Liquiritiae radix

Figs. 7, 8

240

A venae herba
Hederae folium

. Fig. 9

242

Hippocastani semen

Fig. 10

242

TLC-Analysis of Saponins

. Figs. 11, 12

244

Drugs Containing Pungent Principles

247

Extraction and TLC . . . . . . . . . .


List of Drugs Containing Pungent Principles
........... .
Formulae

247
248
249

Capsici fructus
Cubebae fructus
Piperis fructus

XII

. . . . Figs. 1, 2

. . . . . . . . . 250

Mustard Oil Drugs and Allium

253

Extraction and TLC


List of Drugs . . .
Formulae

253
255
255

Sinapis albae (Erucae) semen


Sinapis nigri semen

. Fig. 3

256

Thiourea derivatives
Allium sativum . .

. Fig. 4

256

N arcotic Drugs .

259

Extraction and TLC


List of Drugs .
Formulae

259
259
260

Cannabis herba
Hashish . . . . . . . . . . . . . . . . . Figs. 1, 2

260

Drugs Containing Valepotriates

263

Extraction and TLC


List of Drugs .
Forrnulae

263
264
265

Valerianae radix

266

. . . . . . . . . . . . . Figs. 1, 2

Drugs Containing Pigments

269

Extraction and TLC


List of Drugs
Forrnulae

269
270
271

Cyani flos
Hibisci flos
Malvae flos

. . . . . . . . . . . . . . . Figs. 1, 2

. . . . . . . . . 272

Hibisci flos
Paeoniae flos
Croci stigma . . . . . . . . . . . . . . . Figs. 3, 4

. . . . . . . . . 274

Drugs with Miscellaneous Constituents

277

Extraction and TLC . . .


List of Miscellaneous Drugs
Forrnulae . . . . . . .

277
278
280

Salicis cortex . . . . . . . . . . . . . . . Fig. 1

282

Hamamelidis folium
Filicis rhizoma
Pyrethri flos . .

. Fig. 2

282

Lichen islandicus
Podophylli resina
Visci albi herba
Amino acids . .

. Fig. 3
. Fig. 4
. Figs. 5, 6
. Figs. 7, 8

284
284
286
288

TLC Screening of an Unknown Commercial Drug

291

Extraction and TLC . . . . . . . . .


Scheme of Separation and Identification

291
294

TLC Analysis of Herbai Drug Mixtures

296

Spray Reagents

. . . . . .

299

Abbreviations and Definitions

305

References

307

Subject Index

309

XIII