Plant drug analysis : a thin layer chromatography atlas

368 Pages·1996·17.58 MB·English

by  Hildebert Wagner

PLANT
,
HeW agner
"SIS
A Thin Layer
I
Chromatography
Atlas
.
Photographs
by V. Rick1
Second Edition
-
Preface to the Second Edition
More than 12 years have passed since the first and very successf~a~tlt empt was made to
reproduce the thin layer chro~natography(T LC) separation of 170 medicinal plant drugs
in the form of color TLC fingerprints in a book. The reproduction of natural color
photographs in UV 365 nm was a difficult undertaking at that time due to the relatively
unsophisticated film and filter technology. The first German edition of this book with its
appended English translation met with worldwide acceptance in the field of natural
product chemistry and has remained an indispensable aid in the laboratory a~lalysiso f
nledicinal drugs.
Due to the higher demands now placed on plant drug quality, the introduction of herbal
preparations with medicinal significance, and the increasing number of yhytochemical
preparations, the analytical and standardization procedures of the plants have gained
even greater importance. We have tried to do justice to this development in this second
edition.
This TLC atlas now includes about 230 medicinal plants of worldwide interest. The
photographs of the TLC fingerprints and the descriptions of the characteristic com-
pounds of each plant extract are a quick and reliable source for the identification and
purity check of plant material and phytopreparations.
Most of the TLC systems are standard systems and have been optimized when necessary.
In spite of other available analytic techniques, such as gas chromatography and high
performance liquid chromatography, TLC still remains a most useful, quick, effective,
and low-cost method for the separation and identification of complex mixtures ofherbal
drug preparations and plant constituents.
The authors are most gratef~11to Ms. Ute Redl for her comprehensive technical assis-
tance. We also thank Ms. Veronika Rick1 not only for the excellent quality of the photo-
graphs, but also for the layout of the TLC fingerprint pages in the book and For [be
drawing of the chemical formulae.
Munich, March 1996
Hildebert Wagner Sabine Bladt
Plant Drug Analysis
A Thin Layer Chromatography Atlas
Second Edition
With 184 Colored Photographs
by Veronilca Rickl
Springer
Professor Dr. h.c. HII.DEBERW.~A GNER
Universiriit Miinchen
Institut fiir I'liarmazeutische Bjologie
KarlsstaRe 29
D-80333 Miinchen
Germany
Dr. rer, nat. SA~INBLEA DT
Urliversitat Miinchen
lnstitut fiir Pharmazeu~iscl~Beio logie
KarlsstraRe 29
D-80333 Mlinchen
Germany
lSRN 3-540-58676-82 nd ed. Springer-Verlag Berlin Heidelberg New Yorlc
ISRN 3-540-13195-71 st ed. Springer-Verlag Berlin Heidelberg New York
Library of Congress Crtaloging-in-Publica~loDn am
Wi~p,ner,H iltleberl, 1929-
[Drugenanalysc. English1
I'lanl drug analysis: e lliin layer cliro~natogrnpl~ayll ;~s/
Iiildcbcrl Wagner, Sabille Bld1.-2ntl cd.
p. 0111.
Inclucl~.sb ibliogr~phicr~elr ercncas s ~in~dedx.
ISBN 3-540-58676-8 (elk. paper)
I. Matc~.ian lnlict, Vegclablc-Analysis. 2. Thin layer
cliro~na~i>gr;~pl~I,y .D ladl, S. (Sabi~~e1),9 45- . 11. Tillc.
RS190.1'55W3313 1995
615'.32-rlc20
Tllc material L co~vcrned,s pecilically ~hrcig hls of lransla~iun,r eprinting reuse ol' illl~atralio~r~csc,il alion, bruadcz~sling,
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purtnlued o~llyu nder ll~epr ovisio~rso r tlie Gerninn Copyright Law oiSeptcr11ber 9, 1965, in its currelll vcrsio~i,a nd ~rern~is-
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n IIIFIIII%FI>I Uerte Ixmi~nnSpringcrS cic~,ce-kRl~si~M~ecrsl~ir ~C ilribH
Product Linbilily: The pulrlislicr can give nu guaralilcc for informnlinn about drug dosage :~ndn yplication tliereofcontaincd
in this book. Ine vury iodivitlr~ocla se Ihe respcctivc user must check ils accuracy by cunsi~lli~ot~hger plinrrnaceu.lical lircraturc.
Tl~lcts eiiigeneral descriptive eanles, rcgistcrerl names. Iradcmorks,rtc. in tliis p~rl~licaldiooe~s ~no 1 imply, cvcn in Ihenbse~lce
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Contents
....
Introduction
Alkaloid Drugs ..............................
........................
Preparation of Extracts
..................
Thin-Layer Chromatography
.................
Detection
..........................
Formulae
TLC Synopsis of Important Alkaloids .....
Chromatograrns .................. ................ 24
Rauvolfiae radix. Yohimbe cortex.
Quebracho coxtex. Catharanthi foiium .... .....F ig.3.4 ........ 24
Vincae minoris folium
Secale cornutum .................. .... Fig . 5. 6 ........ 26
Strychni and Ignatii semen
Gelsemii radix ................. .... Pig .7 . 8 ........ 28
Harrnalae semen
Justiciae-adhatodae foliurn. Uncariae radix . . . . . . . .Fi g . 9. I0 ....... 30
Ipecacuanhae radix
Chinae cortex ...................................F ig . 11. 12 ...... 32
Opium ........................................F.ig . 13. 14 ...... 34
............... . ......
Corydalidis rhizoma. Fumariae herba Fig 15. 16 36
Spartii flos. Sarothamni herba
Genist~eb erba ................ .... Fig . 17. 18 ...... 38
Chelidonii herba
....................... .... ......
Colchici semen Fig.19.20 40
Berberidis cortex. Colombo radix.
tIydrastis rhizoma. Mahoniae radixlcortex ... ....F ig . 21. 22 ...... 42
Boldo folium
Nicotiarlae folium ................................F ig. 23. 24 ...... 44
Aconiti tuber. Sabadillae semen
Lobeliae herba. Ephedrae herba ....................F ig. 25. 26 ...... 46
Solanaceae drugs ................................F ig. 27. 28 ...... 48
Purine drugs ....................................F ig. 29. 30 ...... 50
Drugs Containing Anthracene Derivatives ...
Preparation of Extracts .................
......................................
Thin-Layer Chromatography 53
Detection ...................................................... 54
......................
Circular TLC in Addition to the Ascending TLC 55
Chromatogra~ns. ............................................... 62
Aloes ...........................................Fi g . 1. 2 ........ 62
Rhamnus species .................................F ig . 3.4 ........ 64
.
Rhei radix .......................................F ig 5. 6 ........ 66
Sennae foliurn. fructus ............................F ig . 7.8 ........ 68
Circular TLC (CTLC) in comparison to ascending
TLC of Senna extracts
Hyperici herba .................................. Fig . 9. 10 ....... 70
Preparation of Extracts .......................................... 73
Thin-Layer Chromatography ..................................... 73
Detection ...................................................... 74
Drug List ...................................................... 75
Formulae ...................................................... 79
TLC Synopsis of Bitter Drugs ......................F.i g . 1.2 ........ 84
Chromatograms ................................................ 86
Gentianae radix. Centaurii herba. Menyanthidis
......................................... ........
folium .Fig. 3.4 86
TLC Syliopsis. Drugs with Iridoid Glycosides ..........F ig . 5.6 ........ 88
Absinthii herba
Cnici herba .....................................F ig . 7.8 ........ 90
Qleae folium. Marrubii herba
Quassiae lignum ................................. Fig . 9. 10 ....... 92
TLC Synopsis. Drgus with Cucurbitacins ............. Fig . 11. 12 ...... 94
Cynarae herba
I-lumuli lupuli strobulus ...........................F ig . 13. 14 ...... 96
Preparation of Extracts .......................................... 99
Thin-Layer Chromatography ..................................... 99
Detection ......................................................1 00
Drug List ......................................................1 02
Formulae and Tables ............................................ 104
TLC Synopsis of Cardiac Glycosides .................F ig . 1.2 ........ 110
................................................
Chromatograms 112
a
<:-
- ~ -~~~ --. -- . ~ ~ ~~ ~ --~ --
.....
NDeigriiit a(lOisl feoalniudmti) foliu,m,,... . ,.,.r&..w..i‘ ..iu Lrl;i~~.T.s~ A@~?i,~l~sm~~.~~~~~bd~~iIt~i~S&~U,;.Wi %~.n.%u~~%&~+, :~ ~"~h~b~b.b,bi. ~~.j~,;~
..I ..." qi&
... Uzarae (Xysmalobii) radix,:. Y. i.,. ..d.r*h~le.~\.~~~d,,r~i~>l$;,
, EStrryospimhai nhtehrib sae, mCehne iranthi h.erb.a .,..... ........(.,?..c.>...z.h,... i..r.. ;.u......t..).m . F ?igr:.l o7t, 8s s.d Gla;*n+tSv,::. ;.R... .J+&r ;
Adonidis herba, Convallariae herba. Fig. 9,10 ;arJ~%
. . . . .m
Helleborus spe.c.i.e.s. ..~..r.i. ....s .~. .s. .k.n.. ~..~ d.iurIid".b:or~. F3ig~, ~I 1~,l0t;~q~ J , ,
,,.~S.c illae bulbus ,irwdr?.- &r,q ;i Fig, 13,1411v~jii.,4~%.
.... C Orndg''*k ,.I;,..:,:..; ',.>. ,..:..;.. .,....., .:.. ,,, t.,t ... ,,,.,, . . ..;,f.n !:.i t1.,1.. ..I(; q; .v...r;.~\ i<..;,t,v;:,+k;k,,i ; mii ;i!b~f6tp~il Y2l',, ,. ':&~1<r,~;;f4fr ~s lLj~pF1', ;5 ?
Preparatio~m@.*,.. .... ........ ...+..r... + rwnig~i~~$6r :1su~ui3:..
.... T hin-&%+ .,u~cIl l$.m. ..+.t.~.p..i' .h.y..... . ,,. ..!.:. ...............I ..........I. ...... I.r... , nu U i~ un~t ~?'A @ , ~ ~ ~ ,
Detecff61T..: ..~~8,. r..:I. ... ........ .........c..:.~..!....i.t.~..~..b..s....s..~~.....u ... .:..S .,i@i.~.~.,~. u,~ .~L~.~@.;~.t~I...~ ,,.p i.&i,@$-~ i~.,
,D*cru: k,L,;is:tv . ,, ...:.. ;?@
~;doliial yhi;~yr iil:crl>oi hlo~vetrl'~
-. ~C<hr*o:m.sa:to.;g ram..slx .r. :.l...l.::....:. ..:.:.:.:. :...:..T ..:l.:, :.I .,:, ;.. ,::. .:.. v'.,$..,b.... '.i..7..f..* z '& $$& i'fi"l'I'iil.il.i'* . U&
Asperulae, Meliloti herba; ToncaS@&~~,:,..;,
..,
. mACiob uromtaanrciion hrset -erbx Ca, ,h Proamb.ia atnoig hreawrpi:bnh, a.i c..< "S.,. . .t.,a... n...d.. .,a...;...&.~ ,.l..,. , .: ,..:. ,~... .d,i , ( ...,n j ~J, .,...r..r.$,,<, $., v.; .*U .BiB~l&i&gr~ i:'l~Sto,3 : i@'i8(l),n n~: ?:a dr,,r. arl.7i~~. .1tu:.&..1i.i. L... . ..c~12$,m ,. .@q , b
Mandragorae radix
.........................
P,QBiMi B~W9*:19~&Xin%..%.,..E.?@ &lg&raysj3... &%&I
Imperatoriae, Angelicae and
.. p.@k$&&@e, ticih feErrbaiad@ .jj.,. +,:,,,.... ? ', :;,,@A ,,' ..>;+ ,,."$ ;,;:; ,..:e.;,,,; ,.$ , ! ; ;. &?,t:;?:r,' .?js.:,,< ,9.."i "., ..>." .‘E ^: . :r.r., r. ::.,, ,. $. . !.,i?-L~.., J n.EF?!digI&f.i $ 11~F32,$114'6 ~ ...~...~...~... ..~. . i,2.11I% $4~ 24
.....................,, .........,.;'i.,.. .7 .... n ! I ~ ~ l . ,
iDi -rugs .CIo$.n? t3a iin9in,g~ E~~ s..s-e~ ~.n ~.t i.a.l .O.i.ls. (.A..e.th.e.r.o.le.>a.~).c, .B~.~a.~ls.~a..m,.~.sl.I.,,a:,,;& ,, .,,tj. . .,,,. l,~,, ,,n , ,!,,I t,:.,(;7l , ,rfc,, . .
and Oleo-Gum-Resins ..
.. .?aa$ii?flb??.iiV4''
..~.(.1 ~S&l,~ll~ . dr'i ~..~..$.e..n..t ~i1a1lj~i,;~i? n~~;~fl~~c~.~ibI~i l!!~,x5:.:1q< ,~,!I i.LII~I~kII1~.UJ!I,~dI~ :~!iT~I,:&R~ .r,tb.7., M.~ .s1 i.11~2~~~~;i~!~~!,~4~~i?~
Layer :$&
+~~rr~~~r,~i'IItf:~tr.~l ,.
.. ,_ap.i@t,p,.f .b tip..a.. .....O..j...l.. P...g.::.. g @. ., 'AtL:.l;...l.: G um..s~a n..d~ R.es~in.$~.. ,~:,f. ,, ,.. l.,i.h~,n :,r,,., ,!., , 1-11.!'! .!~n!;~!u...;lr:~4~d[:n'r.u.!~Il.n1H tP?.Im.IbI S;+~T'i)* ~. P:;*~b$, ;a
.? ........,........... .. ,... ... . ncl'qrii. 3.&Il.l!.~.p*~!.i- ,,v.#
..........i,.,..'., .$.<P.. ....I.... ....... .1... ...,.. ,r:*$c, fidil~ d?:?. '
ReferencqW&p@*4)kaq& Uti~~z~wa:1d6h6
a ,
'ICA hnrisoim frautcotgursa,m Pso.e .n.i.cu..li. f.ru.c.t.u.s., .B.a.s. ic'.i..l4~i h1.e.1r.&.~.~...1,.u.h'.?.r' ."o~'.l:*te*r.: ~!..q ~'. fi.~'f.nl."e.b~I?.k~.'kl.a...k-.., !~,t : 1'IrTd .8~.. 0~1~~~i
SCainssnaafmraos mligi ncuomrte .x., .C.a.r.y.o.p.h.y..l..l..i. .R.....Q.....~.....,....., ..* ,..I] ..rn..,d.., y. ;.~,T t.,.T: t.i,.!ur.:j. Y.,1dI., .3&.F .i..e$o., dr5l. ,.(6 t...ae: .u m_I&>./.3I.~.~..!C..;;. .g.iJ -. . ':$.l&,t3m $ ~
Calami rhizoma, Asari radix ..'.'.'.'...L';...'e'..t.. Fig. 7,s ,c.,
.. %pi&~~~~~P.@~o~,eW&c...t...t..r l .8.. ?#..A,.+, ...... l-..;B$@Qh~kdi~il~.,$#r m
X Contents
Ajowani fructus. Thymi and Serpylli herba
Carvi. Coriandri. Cardamoni frucrus.
.
Menthae crispae folium ....................... Fig 11. 12 ....... 176
Menthae foliurn (Lamiaceae)
Rosmarini and Melissae folium (Larniaceae) ......... Fig. 13. 14 ....... 178
Melissae foliuln and substitutes (Lamiaceae)
Lavandulae flos and commercial oils (Larniaceae) .... Fig . 15. I6 ....... 180
Aurantii and Citri pericarpiurn .................... Fig . 17. 18 ....... 182
Salviae folium. Eucalypti folium ...................F ig. 19.2 0 ....... 184
Matricariae flos.
Anthemidis and Cinae flos ....... ... Fig . 21.22 ....... 186
Curcurnae rhizonla ............. ... Fig . 23.24 ....... 188
Juniper; aetherolea. Myrrha
Benzoin and balms .................... ... Fig . 25.26 ....... 190
Pini aetherolea. Terebinthinae aetherolea . . . . . . . . .F ig. 27. 28 ....... 192
Flavonoid Drugs Including Ginkgo Biloba
and Echinaceae Species ....................
Flavonoids ..................................
.......
Preparation of Extracts
Thin-Layer Chromatography. .....
Detection ..................
Drug List ..... ...
Formulae ..................
Reference Compounds .... ... Fig. 1. 2 ...
...F ig. 3. 4 ...
Chromatograms ............ ....... . . 214
Arnicae flos and adulterants ...... ... Fig.5,G . . . . . 214
Calendulae, Cacti. Primulae flos ................ Fig. 7.8 . . . . . 216
Pruni spinosae. Robiniae.
Acaciae. Sambuci. Spiraeae and Tiliae flos ........... Fig . 9. 10 ....... 218
Farfarae folium; flos Petasitidis folium. radix ......... Fig. 11. 12 ...... 220
Betulae. Juglandis Rubi. and Ribis folium
Castaneae foliurn ................................F ig . 13. 14 ...... 222
Crataegi Eoliun~.f ructus flos. Lespedezae herba .......F ig . 15. 16 ...... 224
Equiseti herba ..................................F ig. 17. 18 ...... 226
Virgaureae herba
Violae herba ...................................F.i g. 19.2 0 . . . 2 28
Anserinae. Passiflorae herba. Sophorae gemmae
Flavon-C-glycosides as reference compounds ........ Fig . 21. 22 ...... 230
Citri. Aurantii pericarpium
Orthosiphonis. Eriodictyonis foli~lm. ........ ...F ig . 23. 24 ...... 232
Cardui mariae (Silybi) fructus
Viburni cortex ..................... ... Fig. 25. 26 ...... 234
Ginkgo biloba ..............
Contents
Preparation of Extracts ................................
....
Thin-Layer Chromatography
.................
Detection
.................
Drug Constituents
Formulae ...........................
Chro~natngram. ....... .......................
Ginkgo bilobae folium ...... ............... Fig .
Echinacea radix ............ ..........
......... ....
Preparation of Extracts
................
Solvent Systems and Detection
...............................
Drug List
Formulae ..................... ......................
Chromatogram ......................................
Echinaceae radix .................................F ig .
Drugs Containing Arbutin. Salicin and Salicoyl Derivatives .
Drugs with Arbutin (Hydroquinone derivatives) ..........
Preparation of Extracts ....................... . .
Thin-Layer Chromatography .... .......... . .
Detection ................. .... .....
Formulae ...........................................
Drugs Containing Salicin and its Derivatives ..............
........................
Preparation of Extracts for TLC
......................
Thin-Layer Chromatography
Detection .................
Drug List ... ....
Formulae .......
Chromatograms .... .............. .....
Arbutin drugs ...... ...................F ig .
Salicis cortex ....................................F ig .
Drugs Containing Cannabinoids and Kavapyrones ........
Cannabis Herba. Cannabis sativa var. indica L.,
............................
Cannabaceae
..........
Preparation of Drug Extracts
...........
Thin-Layer Chromatography
Contents
Detection ......................................................2 57
Formulae .......................................... . . 258
Kava.Kava. Piperis methystici rhizoma.
Piper methysticum G . FORST. Piperaceae (MD. DAC 86) .... .. 258
Preparation of Drug Extracts fox TLC ........................... 258
Thin-Layer Chromatography ......... ............ 258
Detection ..................... . . . . . . 259
Formulae .................. . . 259
...................................
Chromatograms
Cannabis herba. Hashish
Kava-Kava rhizoma. Piper methysticum ............F ig. 1.2
Drugs Containing Lignans ....................
Preparation of Extracts ......
Thin-Layer Chromatography .....
..................
Detection
........
Drug List
Formulae .....................
Chromatograms ................................................ 268
Eleutherococci radix (rhizoma) ....................F ig. 1. 2 ........ 268
Viscnm album ..................................F ig . 3. 4 ........ 270
Podophylli rhizo~na
Cubebae Fructus ...................... ....F ig . 5. 6 . . . . . 272
Drugs Containing 1.C Naphthoquinones
Droserae herba. Dionaeae herba ........
..................
Preparation of Extract
Thin-Layer Chrornatography ...................
...................................
Detection
................................
Drug List
Formulae ......................................................2 76
Chromatograms ................................................ 278
Droserae herba. Dionaeae herba ...................F ig . 1. 2 ........ 278
Drugs Containing Pigments ................... . . 281
Preparation of Extracts ................... ... . 281
Thin-Layer Chromatography ................................... 281
......................................................
Detection 282
DrugList ......................................................2 82