17 - Drugs Containing Valepotriates

16 Drugs Containing Triterpenes
This drug group includes Cimicifugae rhizoma (Tetracyclic triterpene glycosides,

actein, cimifugoside) and Ononidis radix (Triterpene a->
16.1 Preparation of Extracts
Powdered drug (1 g) is extracted with I0 ml methanol for 15 min on a water bath; 30 PI of Ciicifugae
the fltrate is used for TLC. rhizoma
Powdered drug (1 g) is extracted with chloroform for 1 h under reflw; 20 ~1 of the filtrate Ononidis
is used for TLC of terpenes. radix
Powdered drug (1 g) is extracted with I0 mI methanol for 15 min on a water bath; 20 pl is
used for TLC of flavonoid glycosides and terpenes.
16.2 Thin-Layer Chromatography
Caffeic and ferulic acid; ononin, rutin, chlorogenic acid, hy-peroside as a 0.1% solution in Reference
methanol; 10 yl is used for TLC. solutions
Silica gel 60 I?,,,-precoated plates (Merck, Germany) Adsorbent
Ethyl formiate-toluene-formic acid (50:50: 15) + Cimicifugae rhizoms Chromatography

Toluene-chloroform-ethanol (40:40:10) -+ Ononidis radix solvents
Ethyl acetate-glacial acetic acid-formic acid-water + polar compounds
(100:11:11:26) -+ ononin (isoflavone)
16.3 Detection
UV-254 n ~ n calfeic acid, its derivatives and isoflavones show

quenching
UV-365 nm caffeic acid, its derivatives and isoflavones
fluoresce blue
Anisaldehyde-sulphuric Tile sprayed TLC is heated for 6 rnin at 100°C;
acid reagent (AS No. 3) evaluation in vis.: triterpenes blue-violet
(see Appendix A) (Cimicifugae rhizoma) and red to red-violet
(Ononidis radix)
16.4 Drug List
Druglpla Main cor

Familylpr~arrna~u,
Fig. 1 Cimicifugae rhizoma b Tetracyclic triterpene glycosides:

Cimicifuga, black cohosh actein (acetyl-acteol xyloside),
Cimicifuga racemosa (L.) NUTT cimicifugoside (cimicigenol xyloside)
(syn. Actaea racemosa L.) b Isoflavone: formononetin
Ranunculaceae , Caffeic and isoferulic acid
MD, Japan, China (other b 15%-20% resins (cimicifugin)
Cimicifuga species)
Pig. 2 Ononidis radix b Triterpenes: u-onocerin (= onocol)

Restharrow root b Isoflavones: ononin (= formononetin-
Ononis syinosa L. 7-glucoside), formononetin-7-(6"-
Fabaceae 0-maloy1)-glucoside, biochanin A-7-
OAB, MD glucoside
b 0.02%-1% essential oil: anethole, carvon,
menthol
16.5 Formulae
Cimifugoside R = Xylose
Cimicigenol R=H
16 Drugs Containing Triterpenes 337
Actein R = Xylose
Acetyl-acteol R = H
Ononin R = Glucose
Formononetin R = H
16.6 Chromatograms
Cimicifugae rhizoma
Drug sample 1 Cimicifugae rhizoma (methanolic extract, 10 y1)
Reference T1 caffeic acid (I- methylester of caffeic acid)
cornpoul~d T2 formononetin
Solvent system Fig, 1 ethyl formiate-toluene-formic acid (50:50:15)
Detection A UV-254nm
B Natural product polyethylene reagent (NSTIPEG No. 28) 4 UV-365 nm
C Anisaldehyde-sulphuric acid reagent (AS No. 3) + vis.
Fig. I A In UV-254nm Cimicifugae rhizoma (1) shows two prominent quenching zones at R,
0.55-0.65 due to caffeic acid (TI) and the isoflavone formononetin (T2). The zones a t
R, 0.05-0.1 are phenol carboxylic acids.
n After treatment with the NSTIPEG reagent, the main zones develop a bright blue
fluorescence in UV-365 nm.
C Treatment with AS reagent reveals the violet zones of the triterpene glycosides in the R,
range 0.3-0.55. The prominent zones are due to actein and cimifugoside.
Ononidis radix
Drug salllple I Ononidis radix (methanolic extract, 20 yl)
Reference TL ononin
compou~~d T2 rutin (R, - 0.4) F chlorogenic acid ( R ,- 0.5) b hyperoside (R,- 0.6)
Solvent system Fig. 2 A ethyl acetate-glacial acetic acid-formic
acid-water (100:ll:l l:26) 4 system 1
B + C toluene-chloroform-ethanol (40:40: 10) + system 2
Detection A UV-254nm
B UV-365 nm
C Anisaldehyde-sulph~~ric
acid reagent (AS No. 3) + vis
Fig. 2 A Ononidis radix (1). The characteristic isoflavone formononetin-7-0-glucoside (ononinl

T I ) and its -8"-rnalonate are found as quenching zones in the R, range 0.65-0.75 in
system 1. The terpenes move with the solvent front.
B In the lipophilic solvent system 2 the green-blue fluorescent ononin (T1)remains close
to the start; additional blue fluorescent zones are found in the R, range 0.2-0.45. The
terpenes migrate to the lower Rr range, detectable after treatment with the AS reagent.
c Treatment with AS reagent reveals five violet-red zones (R, 0.05-0.55) with onocerin as
-
the major terpene zone at R, 0.4 (vis).

17 - Drugs Containing Valepotriates

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16 Drugs Containing Triterpenes

This drug group includes Cimicifugae rhizoma (Tetracyclic triterpene glycosides,

16.1 Preparation of Extracts

16.2 Thin-Layer Chromatography

Silica gel 60 I?,,,-precoated plates (Merck, Germany) Adsorbent

Ethyl formiate-toluene-formic acid (50:50: 15) + Cimicifugae rhizoms Chromatography

UV-254 n ~ n calfeic acid, its derivatives and isoflavones show

Druglpla Main cor

Fig. 1 Cimicifugae rhizoma b Tetracyclic triterpene glycosides:

Pig. 2 Ononidis radix b Triterpenes: u-onocerin (= onocol)

Fig. 2 A Ononidis radix (1). The characteristic isoflavone formononetin-7-0-glucoside (ononinl

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