11 Drugs Containing 1,4-Naphthoquinones

Droserae herba, Dionaeae herba

11.I Preparation of Extract

1. Powdered drug (1 g) is extracted for 15 rnin with 10 rnl methanol on a water bath; 30 p1 Droserae
of the clear filtrate is used for TLC. herba
2. Powdered drug (1 g) is distilled with 10 ml water and 1m12 M H,PO, in a 50-ml flask
through a glass pipe into a cllilled glass tube until 3 ml distillate has been collected
(see microdistillation, Sect. 6.1). After cooling, the lipophilic compounds are ex-
tracted with 1 rnl pentane; 10 y.l of this solution is used for TLC.

The whole fresh plant is put through a tincture press until 1 ml plant juice has been Dionaeae
collected. The juice is diluted with 9 ml CHC1, and 20 pl is used for TLC investigations. herba

1 1.2 Thin-Layer Chromatography

10 mg plumbagin and juglone are dissolved in 1 ml methanol and lop1 are used for Reference
TLC investigation. solutions

Silica gel 60F,,,-precoated TLC plates (Merck, Germany) Adsorbent

Toluene-formic acid (99:l)+naphtoquinone aglycone Solvent

Ethyl acetate-formic acid-glacial acetic acid-water (100:11:11:26) + glycosides systefns

11.3 Detection

All naphthoquinones show quenching in W-254nm.

After spraying with 10% methanolic KOH reagent, naphtoquinones show red
fluorescence in UV-365 nm and red to red-brown colour (vis).
 11.4 Drug List

Druglplant source Main constituents

Familylpharmacopoeia

Fig. I Droserae rotundifoliae herba >0.5% 1,4-naphthoquinones,

Round-leafed sundew plumbagin, 7-methyl-juglone,
Drosera rotundifolia L. droserone
b protected plant

Fig. 1 Droserae longifoliae herba >0.25% l,4-naphrhoquinones,

Long-leafed sundew plumbagin, ramentaceon and its
from various Drosera species e.g.: glucoside rossoliside
Drosera ramentacea BURCH. ex
HARV. et SOND.
Drosera longifolia, D. anglica
D.intermedia, D. burmanii
Droseraceae
MD

Fig. 2 Dionaeac muscipulae herba >0.85% total 1,4-naphthoquinones,

Dionaea muscipula ELLIS pluinbagin (-0.2%),
(syn. Drosera sessiliflora RAF.) hydroplumbagin-4-0-b-glucoside
Droseraceae (-0.6%), 3-clloro-p1umbagi.n
(-0.01%), droserone (-0.002%)

11.5 Formulae

Plumbagin R H
= Juglone R=H
Droserone R = OH Methyljuglone R = CH,
 11.6 Chromatograms

Droserae herba, Dionaeae herba

Drug sample 1 Droserae rotundifoliae herba (MeOH extract, 30 p1)
2 Droserae rotundifoliae herba (distillate)
3 Droserae rainentaceae herba (distillate)
4 Dionaeae muscipulae herba (pressed juice, 20 pl)
Reference T1 plumbagin
con~pound T2 juglone
T3 rutin (R, - 0.35) b cl~lorogenicacid (R,- 0.45) b hyperoside (R, - 0.6)
Solvent system Fig. 1 A-D toluene-formic acid (99:l) + system I
Fig. 2 A + R toluene-formic acid (99:l) + system I
C ethyl acetate-glacial acetic acid-formic acid-water (100:11:11:26)
+ system I1
Detection Pig. 1A-D 10% methanolic potassium hydroxide
A,D +vis B,C +UV-365 nm
Fig. 2A,B 10% nlethanolic potassium hydroxide
A +vis B +UV-365 nm
Fig. 2C Natural products-polyethylene glycol reagent
(NPIPEG No. 28) + UV-365 nm

Fig. I All three Drosera samples show the violet-brown (vis) and brown-yellow (UV-365 nm)
A-D fluorescent plumbagin (Tl) as the main zone at R,-0.45.
Plumbagin is accompanied in salnpIe 1 by 7-methyljuglone (the same R,. vaIue as
--
plumbagin) and juglone (Rf 0.4). Juglone is more highly concerltrated in sample 3 (D.
ramentacea). Droserone (R, 0.35) can be detected in sample 1.
Fig. 2 Dionaea muscipula (4) shows the prominent blue (vis/A) and red-brown (UV-365 nmlB)
A,B zone of plumbagin (TI)at K,
glucoside r e ~ n a i ~at
-
l s the start.
0.5 in solvent system I. The hydroplumbagin-4-fi-D-

c (NPJPEG reagent, UV-365 nm):

In solvent system I1 hydroplumbagin glucoside migrates as a blue-green band in to the R,
range 0.85-0.9. Further blue to greenish-blue zones are found in low concentrations in
the R, range of hyperoside (T3).