Journal of Ethnopharmacology,
Elsevier Scientific Publishers
233
24 zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJI
(1988) 233-246
Ireland Ltd.
WHEAT ROOTLET GROWTH INHIBITION TEST OF RWANDESE
MEDICINAL PLANTS: ACTIVE PRINCIPLES OF zyxwvutsrqponmlkjihgfedcbaZ
TETRADENIA
RIPARIA AND DIPLOLOPHIUM AFRICANUM
LUC VAN PUYVELDE”, NORBERT DE KIMPE’,
JEAN COSTAb, PROSPER NSHIMYUMUKIZAb,
HAKIZAMUNGU”
and NICEAS SCHAMP’
F’RANCOIS-XAVIER
AYOBANGIRA”
YVES BOILY”, ETIENNE
“Centre Universitaire
de Recherche SW la Pharmacopke
et la Mkdecine Tmditionnelle
CURPHAMETRA,
Universite’ Nationale
du Rwanda,
B.P. 117 Butare, bDt!partement
de
Chimie, Faculti des Sciences, Universiti
Nationab
du Rwanda,
B.P. 117 Butare (Rwanda) and
‘Laboratoy
of Organic Chemistry,
Faculty of Agricultural
Sciences, State University
of Gent,
Coupure Links 653, B-9000 Gent (Belgium)
(Accepted
July ZOth, 1988) zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDC
Summary
A series of 50 medicinal plants of Rwanda (121 plant samples) has been
screened for wheat rootlets inhibition activity. The minimum inhibitory
concentration
(MIC) of the active principle of Tetradenia riparia, i.e.
8( 14), 15sandaracopimaradiene-7
cy, l&diol (7.81 pglml), and of the active
principle of Diplolophium africanum, i.e. scoparone (62.5 pg/ml), in this
test was determined.
Introduction
In order to find Rwandese medicinal plants with antimitotic activity we
used a preliminary test inspired by the method of Ceriotti (1965), i.e. the
inhibition of the growth of the rootlets of wheat (Boily and Harelimana,
1979).
A series of 50 plants (121 plant samples) were screened in this test.
Plants were chosen among well known medicinal plants of the Rwandese
native medicine (Table 1) (Van Puyvelde et al., 1975, 1977a, 1977b, 1982).
The plant powders were first tested at a concentration
of 100 mglml. Afterwards, tests at a concentration
of the plant powders of 10, 5 and 1 mg/ml
were performed with the plants showing an inhibition of the growth of the
rootlets of 90% or more at the concentration
of 100 mg/ml.
0378-8741/88/$05.25
@ 1988 El sevier Scientific
Published and Printed in Ireland
Publishers
Ireland Ltd
234
TABLE
1
MEDICINAL
PLANTS
Family, botanical
ACANTHACEAE
USED IN THE RWANDESE
name
Folk name
NATIVE
MEDICINE
Plant
Disease, use
parts” zyxwvutsrqponmlkjihgfedcbaZYXW
zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
Igihapfu
Ikirogora
Magaru
L
L
Leprosy, vermifuge, emetic,
eczema, snakebite, lactogen
Jaundice
Ijojwe
L
Skin diseases
Gutwikumwe
Agaso
W.PL.
PL
Surgery
Poison
Igihondogoro
L
To favor&
placenta
Aspilia africana (Pers.)
C Adams
Icyumwa
L
Car&us lepthucanthus
Fresen.
Crassocephulum nwntuosum
@Moore)
Milne-Redh.
Elephantopus plurisetus
(0. Hoffm.) Clonts
Senecio mnmglrensis
0. Hoffm.
Vernonia hochstetteri A. Rich
Mugabudasumirwa
Igifuraninda
W.PL.
Anthrax, gonorrhea, syphilis,
yaws, pneumonia, leprosy,
malaria, epilepsy, antiseptic
Snakebite
L
Leprosy,
Igisharakisi
Igihuna
Imbatura
PL
Gastroenteritis
L
Yaws,
Ikonambogo
L
Anthrepsis
Indondoli
L
To benefit the uterine
contractions
Yaws
Brillantnisia cicatricosa
Lindau
Hypoestes trifkv-a (Forssk.)
Roem. et Schultes
Justicia flaua (Vahl)Vahl
APIACEAE
Centellu asiatica (L.) Urb.
Diplolophium africanum
Turcz.
ARALIACEAE
Cussonia arborea Hochst.
A.Rich.
ex.
the delivery of the
ASTEXACEAE
malaria
syphilis
BALSAMINACEAE
Zmpatiens burtonii Hook. f.
R
BASELLACFXE
Basella
alba L.
Indarama
W.PL.
Snakebite, to facilitate
childbirth
Umukoli
L
Jaundice
Umukubagwa
R
Umushishi
R
Scabies, eczema, asthma,
leprosy, gastroenteritis
Cosmetic
Umurama
L
Snakebite,
BIGNONIACEAE
Markhnmia obtusifolia
(Baker) Sprague
CLUSIACEAE
Psorospermum febrifugum
Spach
Symphonia globulifem L.f.
COMBRETACRAE
Combreturn nude R.Br.
ex G. Don
cough
235 zyxwvut
TABLE
1 (Continaecf)
Family, botanical
name
Folk name
Plant
Disease, use
parts” zyxwvutsrqponmlkjihgfedcbaZYXW
Mugogutarengwa
PL
Snakebite
Ikiduha
LA
Gonorrhea, dysentery,
angina, vermifuge, tonicum
Umuhashya
Igitembatembe
Amakubwe
L+s
L
FR
R
Rectal prolapse, abcess
To benefit the uterine
contractions
Malnutrition
Female frigidity
W.PL.
Jaundice,
CYATHEACEAE
Cyathea monniana
Hook
EUPHORBIACEAE
Euphorbia
candelabrum
Welw.
FABACFAE
Dalbergia la&tea Vatke
Neorautanenia mitis
(A. Rich.) Verde.
HYDNORACEAE
Hydnora johanis Beccari
Umutima
w’isi
cardiotonicum
LAMIACEAE
Plectranthus
lariflorus Benth.
Pycnostnchys erici-rosenii
Rwagara
Cough, wounds,
abscess
Cough
Umutsinduka
breast
R.E. Fries
Angina, yaws, gastroenteritis,
Umuravumba
antiseptic, phagedenic
Codd zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
ulcer, toothache, malaria,
female sterility,
conservation of the
foodstuff
R
Gonorrhea
BR
Bronchitis, diarrhea
‘Z’etradenia riparia (Hochst.)
LAURACEXE
Ocotea michekonii
Rob. et
Umuganza
BS
Whipworm
Umushabishabi
L,R
Vermifuge
Intomvu
W.PL.
R
Cardiotonicum
Counterpoison
Umunyu
w’intama
L
Herpes, yaws, wounds,
epilepsy
Sprague
Umus hwati
L
Wounds
Fresen.
Umukaka
L
Whipworm,
Mumeya
BR
Ifumbib
Wilcz.
LILIACRAE
Asparagus falcatus L.
LOBELIACEAE
Lobelia petiolcrta Hauman
MELASTOMATACEAE
Dissotis b llzzzne cogn.
MELIACEAE
Campa gmndifkva
MELIANTHACRAE
Bersama abyssinica
MENISPERMACEAE
Albertisia
Forman
exelliana (Troupin)
ascaris,
diarrhea
236
TABLE
1 (Continued)
Family, botanical
MIMOSACEAE
name
Folk name
Disease, use
Plant
parts” zyxwvutsrqponmlkjihgfedcbaZYXW
zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
Acacida mearnsii De Wild.
Albizia adianthifolia @chum.)
W.F. Wight
Barakatsi
L
Umusebeya
Leprosy
Cough, jaundice,
ozena
anthrax,
MYRICACEAE
Myrica knndtiana Engl.
Isubyu
Umusengesi
PI,
Anal and vaginal prolapse,
anthrax, smallpox, counterpoison
Umugote
L,BS
Cough
Umubanga
L
Cough
Ikibundi
L
Poliomyelitis
Umunyagasozi
Umukuyu
L
Abortifacient,
snakebite
Rheumatism, toothache,
malnutrition, ifumbi”
MYRTACEAE
Syzygium cordatum Hochst.
ex Sonder
OLEACEAE
,Schrebera alata (Hochst.)
Welw.
PIPERACEAE
Piper capense L. f
POLYGALACEAE
Securiahca longepedunculata
Fresen.
R
POLYGONACEAE
Umulyanyoni
PL
Wounds,
Umugeshi
1,
Vermifuge,
Umutanoga
Umushabarara
L
BS
Cough, ascaris
Ascaris
Umutana
L
Pneumonia,
Solanum anguivii Lam.
Igitagarasolyo
FR
Solanum indicum L.
Solanum nigrum L
Igitagarasolyo
Isogo
PL
L
Abcess, anthrax, amebic
dysentery
Taenifuge, toothpaste
Lactogen
Umugosora
L
Ascaris,
Polygonum setosulum Hochst
ex A. Rich
burns, snakebite
ROSACEAE
Hagenia abyssinica (Bruce)
J.F. Gmelin
cosmetic
RUBIACEAE
Fadogia ancylanth Hiern.
Rytigynia beniensis (De
Wild.) Robyns
RUTACEAE
Clausena anisata (Willd.)
Hoof. f. ex Benth.
sterility
30LANACEAE
JFXBENACEAE
Verbena ofiinalis
L.
leprosy
237
TABLE 1 (Continued)
Family, botanical name
VI’I‘ACEAE
Folk name
Plant
Disease, use
parts” zyxwvutsrqponmlkjihgfedcbaZYXW
zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
Rhoicissus tridentata (L.f .)
Igitongoro
BS
Gastro-intestinal
pain
Wild. et Drum.
“L, leaf; S, stem; R, root; FR, fruit; LA, latex; BR, bark of the root; RB, root without bark;
BS, bark of the stem; PL, plant without roots; W.PL., whole plant.
“Ifumbi: illnesses not identified by the traditional healer. This illness can attack each part of
the body and causes neuralgia, headache, imaginary pregnancy, abortion and deficient milk
production. Some traditional healers think it is a hereditary illness. zyxwvutsrqponmlkjihgfedcba
The leaves of ~etr~nia
riparia and the roots of D~p~~~phium africhosen for further investigation. Bioactivity-guided fractionation and chromatography has led to the isolation of the active principles.
Tetradenia riparia (Hochst) Codd. (Lamiaceae) is an important medicinal
plant in the native medicine of Rwanda, where it is known under the name
of umuravumba. The plant is used as a remedy against a wide range of
diseases including malaria, angina, yaws, anthelmin~s-induced diseases,
gastroen~ritis, gonorrhea, diarrhea, dental abcesses, headache and several
kinds of fevers and aches (Van Puyvelde et al., 1975, 1976).
Diplolophium africanum Turcz. (Apiaceae) is named agaso in Rwanda
while the plant is known in East Africa to be toxic for cattle (Watt and
Breyer-Brandwi j k, 1962).
cunum were
Material and methods
Plant ~teria~
Plants were collected and identified by one of the authors (F.X. Ayobangira). Voucher herbarium species are preserved in the herbarium of the
Department of Botany (CURPHAMEI’RA). Plant parts were air-dried and
afterwards powdered mechanically.
Biological utility
Grains of wheat were preliminary germinated in tape water during 24 h in
the dark. Afterwards, 10 grains were put on a filter-paper (Whatman no. 1,
diameter 9 cm) in a Petri dish (diameter 10 cm) containing 10 ml of tap
water and 1000 mg of the plant powder (concentration 100 mglml). The Petri
238 zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
dishes were then kept in the dark at ambiant temperature and the growth of
the rootlets was evaluated after 6 days. The inhibition of the growth of the
rootlets is given in per cent compared with the growth of the rootlets of
non-treated grains under the same conditions (expressed as the mean of 10
grains). For the plant powders which showed an inhibition of 90% or more
on the growth of the rootlets, further dilutions were tested at 10, 5 and
1 mglml.
The biological test was used during the whole isolation procedure of the
active principles of 2’. riparia and D. africanurn. The fractions were dissolved in acetone at a concentration
of 50 mg/ml. This acetone solution
(0.2 ml) was mixed with 9.8 ml of tap water in a Petri dish to obtain a final
concentration
of 1 mglml (2% acetone in water showed no effect on the
growth of the rootlets). For the active principles, the minimum inhibitory
concentration
(MIC) values were determined as the lowest concentration
of
the compound which completely inhibited (100%) the rootlets of wheat. zyxwvutsrqp
Isolation of active principles
T. riparia: a sample of 1000 g of the powder of the leaves was extracted
in a percolator with 151 chloroform.
The chloroform
extract was concentrated under reduced pressure (40°C) yielding a green residue (135 g). The
extract (18 g) was chromatographed
over a silica gel column (600 g; Merck,
230-400
mesh) using a benzene/chloroform/methanol
gradient 8(14),151) was
isolated
with
chloroSandaracopimaradiene-7
(Y,18-diol
(Fig.
form/methanol
(97:3) to afford 1.2 g (0.9% of dry plant) and was recrystallized from benzene giving colourless crystals (m.p. 86-87°C) (De Kimpe et
al., 1982).
D. africanum: a sample of 180 g of the power of the roots was first
extracted in a percolator with petroleum ether (40”-6o”C) (0.81) and then
with chloroform
(41). The chloroform
extract was concentrated
under
reduced pressure yielding a yellow residue (15.5 g). The residue was dissolved again in chloroform
and extracted with methanol-water
(1: 0.75).
Fig. 1. Structure
of 8(14),15-sandaracopimaradiene-7u,l8-diol.
239 zyxwvu
Fig. 2. Structure of scoparone.
Both phases were concentrated to dryness under reduced pressure yielding a
chloroform residue (14.7 g) and a methanol/water residue (0.8 g). The
chloroform residue (14.7 g), absorbed on 75g silica gel, was chromatographed over a silica gel column (525g; Merck 230400mesh)
using a
petroleum/ether (40”-6O”C), benzene, chloroform, methanol gradient.
Scoparone (Fig. 2) was isolated with CHCl,-MeOH (97 : 3) to afford 4.31 g
(2.4% of dry plant) and was recrystallized from acetone giving white crystals, m.p. 145”-146°C (lit. m.p. 144”-146°C; Murray, 1978).
IR (KBr): 1700 cm-’ (broad, strong; vc-);
1610 cm ’ (medium vc&.
‘H-NMR (CDC13: 3.91 and 3.93 (each 3 H; each s, 2 x OMe); 6.25 (1 H, d,
J =9.4Hz, =CH(3)); 7.60 (lH, d, J=9.4Hz, = CH(4)); 6.80 and 6.85 (each
1 H, each s, = CH(5) and = CH(6)).
13C-NMR (CDC13): 56.35 (q; both methoxy signals at C(6) and C(7) overlap
completely); 161.3 (s, C = 0); 113.4 (d, = CH(3)); 114.4 (s, = C(4a)); 143.3
(d, = CH (4)); 99.9 (d, = CH (8)); 108.2 (d, = CH(5)); 146.3 (s, = C(6)); 150.0
(s, = C(8a)); 152.9 (s, = C(7)).
These 13C-NMR values fit very well with the 13C-NMR values of the
6,7-dihydro analogue, i.e. 6,7-dihydroxycoumarine (Chang and Floss, 1977)
and agree with data reported for 6-methoxycoumarine and 7-methoxycoumarine (Gottlieb et al., 1979).
Mass spectrum (70 eV): m/e 206 (M+, 100%). UV (MeOH): A,,, 268 nm. zyxwvuts
Results
and discussion
Of 121 plant samples tested (50 plants), 23 showed an inhibitory effect of
90% or more on the rootlets of wheat (Table 2) at a concentration of
100 mg/ml. zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
Tetradenia riparia and Diplolophium africanum were chosen for further
investigation as they showed the greatest inhibitory effect.
Tetradenia riparia
Besides the rootlets inhibitory activity, a substantial antimicrobial (Boily
and Van Puyvelde, 1986; Van Puyvelde et al., 1986) and antispasmodic
activity (Chagnon, 1985; Van Puyvelde et al., 1984, 1987) was found in the
leaves. This led to the isolation of a diterpenediol (Fig. l), i.e. 8(14),15sandaracopimaradiene_7a, 18-diol (De Kimpe et al., 1982). Several other
240
TABLE 2
INHIBITION
MEDICINAL
OF THE GROWTH
PLANTS
Family, botanical
OF THE ROOTLETS
name
Coil. no.
OF WHEAT
Plant
parts”
BY RWANDESE
% inhibition at concentration
of plant powder (mg/ml)
100
10
1 zyxwvutsr
5
ACANTHACRAE
Brillantaisia
cicatricosa
183
Lindau
Hypoestes triflora (Forssk.)
305
Roem. et Schultes
Justicia /lava (Vahl) Vahl
164
L
S
R
L
S
L
S
FR
97
64
14
100
52
91
93
84
W.PL
S
R
75
68
-
50
43
-
30
-
40
33
-
22
15
-
-
71
33
100
-
-
-
100
96
86
L
S
FL
51
57
81
-
-
-
S
R
L
S
R
L
S
FR
PL
R
L
S
L
S
R
33
45
86
82
55
95
67
49
63
98
73
17
100
13
16
-
-
-
-
3
APIACEAE
Centelhz asiatica (L.) Urb.
Diplolophium africanurn Turcz.
173
281
ARALIACEAE
Cussonia arborea Hochst - ex
219
A. Rich.
ASTERACEAE
Aspilia africana (Pers.) C. Adams
210
Carduus Leptacanthus Fresen.
257
Crassocephalum
nwntuosum
(S. Moore)
177
Milne - Redh.
Elephuntopus
plurisetus
(0. Hoffm.)
250
Clonts
Senecio maranguznsis
0. Hoff m.
172
Vernonia hochstetteri
A. Rich.
243
6
11
2
-
-
46
-
-
-
20
-
-
-
-
-
4
63
43
-
-
49
38
6
4
BALSAMINACEAE
Zmpatiens burtonii
Hook.
f.
128
L
S
30
54
180
L
S
100
93
L
S
58
71
BASELLACEAE
Base& alba L.
91
77
-
BIGNONIACEAE
Markhnmia obtusifolia
Sprague
(Baker)
248
-
241 zyxwvut
TABLE 2 (Continued)
Coll. no.
Family, botanical name
Plant
parts”
% inhibition at concentration
of plant powder (mglml)
106
CLUSIACEAE
Sprach
Psorospermum febrifugum
Symphonia
globulifera
L.f.
1 zyxwvutsr
5
10
L
S
L
S
BR
RB
71
66
82
0
79
32
-
-
-
227
L
83
75
-
-
-
174
L
S
67
73
-
-
-
134
PL
65
-
-
-
L
S
L
S
R
69
56
92
69
99
-
-
-
37
48
25
36
270
W.PL
76
-
-
-
198
L
S
L
S
L
S
R
100
79
76
18
100
33
75
100
100
-
41
97
-
7
95
-
311
I,
S
R
89
32
69
-
-
-
185
L
S
60
51
-
-
-
269
L
S
81
92
-
39
38
237
211
COMBRLWACRAE
Combreturn malls R.Br. ex G. Don
CYATHEACEAE
Cyntheu ~nn~ana
Hook
EUI’HORBIACEAE
Eupharbia candelabrum
Welw
FABACEAE
Vatke
Dalbergia &tea
mitis (A. Rich.)
Neorautanenia
Verde.
92
223
51
57
HYDNORACEAE
Hydnora johannis
Beccari
LAMIACEAE
Plectmnthus
laxiflorus Benth.
Pycnostachys erici-rosenii R.E.
Fries
Tetma!enia riparia (Hochst.) Codd
151
1
LAURACEAE
Ocotea micheLsonii Robyns
et Wilczek
LILIACEAE
Asparagus fa~at~
L.
LOBELIACEAE
Lobelia petiolata
Hauman
49
242
TABLE 2 (Continued)
Family, botanical
Cell. no.
name
Plant
parts”
Q inhibition at concentration
of plant powder (mglml)
100
10
1 zyxwvutsrq
5
MELASTOMATACEAE
196
L
S
75
71
-
-
-
Sprague
203
L
S
79
69
-
-
-
Fresen.
233
L
S
61
71
-
-
-
300
L
s
74
36
-
-
-
Acacia mearnsii De Wild.
149
Albizia adianthifolia
273
L
S
R
L
SB
BS
a2
82
83
68
98
30
-
-
-
-
52
-
-
131
S
R
BS
SB
71
81
80
29
-
-
-
216
L
S
80
78
-
-
-
249
L
S
R
89
32
69
-
-
-
294
S
R
81
96
-
-
-
84
87
100
67
-
-
-
100
-
96
-
82
-
brazzae Cogn
Ihsotis
MELIACEAE
&nqm
grandifha
MXLIANTHACEAE
Bersama
abyssinica
MENISPERMACEAE
Albertisia
exefliana (Troupin)
Forman
MIMOSACEAE
@chum.)
W.F. Wight
84
3
MYRICACEAE
Myricu kandtiana
Engl
MYRTACEAE
Syzygium
cord&urn Hochst.
ex Sonder
OLEXCEAE
Schreberu al&a (Hochst.)
Welw
PIPERACEAE
Piper capense L.f
54
21
0
POLYGALACEAE
Securidaca ~gepe~u~cu~~
Fresen.
240
L
S
BR
RB
243
TABLE 2 (Continued)
Family, botanical
Coil. no.
name
Plant
partsa
5%inhibition at concentration
of plant powder (mglml)
100
POLYGONACEAE
10
1 zyxwvutsrq
5
195
L
s
81
75
-
-
-
(Bruce)
150
L
S
R
61
67
66
-
-
-
Hiern
214
(De Wild.)
236
75
48
63
21
33
-
-
-
100
18
88
-
85
-
77
-
80
15
-
-
83
-
71
17
-
Hochst.
Polygonum
setosulum
ex A. Rich.
ROSACEAE
Hagenia abyssinica
J.F. Gmel.
RUBIACEAE
Fadogia
ancylan
Rytigynia
Robyns
th
beniensis
RUTACEAE
Clausena anisata (Willd.)
Hook. f. ex Benth.
218
L
S
SOLANACEAE
Solanum
anguivii
Solanum
indicum
Solnnum
nigrum
Lam.
L
S
FR
L
S
FR
L
S
98
37
93
40
60
91
97
35
-
76
80
-
274
L
BS
SB
85
65
75
-
-
-
234
L
S
R
57
63
61
-
-
-
346
L
324
L.
163
92
82
93
3
6
VEZRBENACEAE
Verbena
ofiinalis
L.
VITACEAE
Rhoicissus
trident&n
Wild et Drummond
(L.f.)
“L, leaf; S, stem; R, root; FR, fruit; PL, plant without root; BR, bark of the root; RB, root
without bark; BS, bark of the stem; SB, stem without bark.
244 zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
compounds
were isolated from the leaves, including ibozol, 7 cy-hydroxyroyleanone (Zelnik et al., 1978), umuravumbolide,
deacetylumuravumbolide,
deacetylboronolide
(Van Puyvelde et al., 1979), 1’,2’-dideacetylboronolide
(Van Puyvelde et al., 198 1) and 8( 14), 15-sandaracopimaradiene-2
a, 18-diol
(Van Puyvelde et al., 1987).
The inhibitory effect of the diterpenediol, 8(14),15sandaracopimaradiene7(r, 18-diol on the growth of the rootlets of wheat was determined. A MIC
value (minimum inhibitory concentration)
of 7.81 pg/ml was found. zyxwvutsrqpon
Diplolophium africanurn
The compound responsible for the inhibitory effect on the growth of the
rootlets of wheat was isolated from the chloroform extract of the roots after
column chromatography
on silica gel. The structure of the active principle
was determined by spectrometric
methods, including ‘H-NMR, 13C-NMR, IR
and MS and identified as scoparone (Fig. 2). The inhibitory effect on the
growth of the rootlets of wheat for scoparone
was determined
and a
MIC-value of 62.5 Kg/ml was found.
This is the first time that scoparone
was isolated from Diplolophium
africanum and that the inhibitory effect on the growth of the rootlets was
determined. The occurrence of coumarins in plant sources is widespread as
evidenced from a recent coverage of the literature in this area (Murray et
al., 1982).
Scoparone (6,7-dimethoxycoumarine
or 6,7-dimethoxy-2Ij-l-benzopyran‘L-one), also named escoparone,
is a frequently occurring coumarin derivative in plant sources. Some of the natural sources from which scoparone
was isolated include Artemisia scoparia (Ban’kovskaya
and Ban’kovskii,
1959; Nesmelova
and Sidyakin,
1971), Ferula oopoda (Kir’yalov
and
Serkerov,
1965), Custanea crenata (Kurogi and Uritani,
1965), Afraegle
paniculata (Adesogan,
1973), Achilles filipendulina (Sham’yanov
et al.
1974), Angelica pachycarpa (Mendez and Rubido, 1979), Angelica dahurica
(Kozawa et al., 1981), Zanthoxylum coreanum (Kim and Huh, 1981) and
Zanthoxylum William&i (Stermitz et al., 1980).
The biological activity of scoparone has been studied several times and
for instance this dimethoxylated
coumarine was found to display hypotensive and tranquilizing activity in laboratory animals and to cause peripheral
vasodilation,
antispasmodic
and relaxant action on the smooth muscle
(Jamwal et al., 1972, Thakur et al., 1978). In addition a pharmacokinetic
study was undertaken recently (Yamahara et al., 1981).
The MIC-values of the reference compounds in this test were 125 pglml
for colchicine and 500 pg/ml for podophylline.
It seems, that substances with antimitotic activity in animal cells do not
always have a similar activity in vegetal cells; thus the conclusion for our
two active principles to have antimitotic activity is irrelevant.
Nevertheless,
t,his simple biological test, can be used for isolating active
245 zyxwvu
principles:
the diterpenediol
which was also responsible
for the antispasmodic and antimicrobial
activity of T. riparia and the coumarine isolated
from D. africunum which was found to display several biological activities. zyxwvuts
Acknowledgement
The authors are indebted to the Belgian Administration
and Cooperation for financial support.
for Development
References
Adesogan, E.K. (1973) Coumarins and other components of Afmegle paniculata. Phytochemistry 12(g), 2310-2312.
Ban’kovskaya,
A.N. and Ban’kovskii,
A.I. (1959) Chemical study of Artemisia scoparia. Trudy
Vsesoyus, Nauch.-lssledovated. Inst. Lekarstv.i Aromat. Rast. 11, 177-9 (cited in Chemical
Abstracts 55 (1961) 17776~).
Boily, Y. and Harelimana, E. (1971), Des substances antimitotiques
et contre le cancer dans les
plantes medicinales du Rwanda. Etudes Rwandaises XIII, 1, 14-26.
Ceriotti, G. (1965), Studio di sostange anticrescita
di origine vegetale. Giornale Botanic0
Italian0 73, 139.
Chagnon, M. (1985), Inventaire Pharmacologique
General des PIantes Medicinales
Rwandaises. Journal of Ethnophurmucology 12, 239-251.
Chang, C., Floss, H.G. and S&k,
W. (1977), Carbon-13 Magnetic Resonance Spectroscopy of
Coumarins.
Carbon-13-Proton
Long-Range Couplings. Journal of Organic Chemistry 42,
1337.
De Kimpe, N., Schamp, N., Van Puyvelde, L., Dul&, S., Chagnon-Dub&, M., Borremans, F.,
Anteunis, M.J.O., Declercq, J.P., Germain, G. and Van Meerssche, M. (1982), Isolation and
structural identification
of 8(14),15-sandaracopimaradiene-7a,l&diol
from Zboza riparia.
Journal of Organic Chemistry 47, 3628.
Gottlieb, H.E., de Lima, R.A. and delle Monache, F. (1979), i3C Nuclear Magnetic Resonance
Spectroscopy
of 6- and 7-Substituted
Coumarins.
Correlation with Hammett Constants.
Journal of the Chemical Society, Perkin Transactions 11, 435.
Jamwal, K.S., Sharma, M.L., Chandhoke,
N. and Ghatak, B.J.R. (1972), Pharmacological
action of 6,7-dimethoxy
coumarin (scoparone)
isolated from Artemisia scoparia. Indian
Journal of Medical Research 60(5), 763-77 1.
Kim, C.M. and Huh, 1.0. (1981), A study of the chemical compounds
of Zanthoxylum
coreanum Nakai (Rutaceae), Saengyak Hakhoe Chi (Hanguk Saengyuk Hukhoe), 12(l), 5-11
(cited in Chemical Abstracts 95 (1981) 93843b).
Kir’yalov, N.P. and Serkerov, S.V. (1965). Scoparone in the root gum of Ferula oapoda. Zh.
Prikl. Khim., 38(l), 225-226 (cited in Chemical Abstracts 62 (1965) 13518h).
Kozawa, M., Baba, K., Okuda, K., Fukumoto, T. and Hata, K. (1981), Studies on chemical
components
of “Bai Zhi” (supplement 1). On coumarins from “Japanese Bai Zhi”. Shegakugaku Zasshi, 35(2), 90-95 (cited in Chemical Abstracts 95 (1981) 209449j).
Kurogi, M. and Utitani, I. (1965), Isolation and identification of two coumarin derivatives from
Japanese chestnuts. Agricultural and Biological Chemistry 30(l), 78-82.
Mendez, J. and Rubido, J. (1979), Coumarins of Angelica puchycccrpa fruits. Planta Medica
36(3), 219-220.
Murray, R.D.H. (1978), Naturally Occurring
Plant Coumarins.
Progress in Chemistry of
Organic Natural Products (Fortschr. Chem. Org. Naturstoffe), 35, 199.
Murray, R.D.H., Mendez, J. and Brown, S.A. (1982), The Natural C’uumarins. Occurrence,
Chemistry and Biochemistry, J. Wiley and Sons Ltd, Chichester. UK.
246 zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA
Nesmelova, E.F. and Sidyakin, G.P. (1971) Lactones of Artemisia scoparia. Khimiya zyxwvutsrqpo
Prirodnykh Soedinenii 7(3), 376-377 (cited in Chemical Abstracts 75 (1971) 115850t).
Sham’yanov,
L.D., Mallabaev, A. and Sidyakin, G.P. (1974) Components of Achilles filipendulina. Khimiya Prirodnykh Soedinenii 6, 784 (cited in Chemical Abstracts 82 (1975)
108838m).
Stermitz, F.R., Caolo, M.A., Swinehart, J.A. (1980), Chemistry of Zanthoxylum.
Part 5.
Alkaloids and other constituents
of Zanthoxylum williamsii, Z. manophyllum and Z. fagam.
Phytochemistry, 19(7), 1469-1472.
Thakur, R.S., Bagadia, S.C. and Sharma, M.L. (1978), Hypotensive
activity of some dihydroxycoumarins
and their congeners. Erperientia, 34(2), 158-159.
Van Puyvelde, L., Pagezy, H. and Kayonga, A. (1975), Plantes medicinales et toxiques du
Rwanda (I). Afrique Medicate 14, 925-930.
Van Puyvelde, L. (1976), L’UMURAVUMBA
- Zboza riparia (Hochst) N.E.Br. (Lamiaceae), la
plante medicinale d’usage courant au Rwanda, Rapp. Deuxidme Colioq. CAMES 60.
Van Puyvelde, L., Mukarugambwa,
S., Rwangabo, P.C., Ngaboyisonga,
M. and RunyinyaBarabwiliza (1977a), Plantes mMicinaIes
et toxiques du Rwanda (II). Afrique Medicale 16,
531-534.
Van Puyvelde, L., Ngaboyisonga,
M., Rwangabo, P.C., Mukarugambwa,
S., Kayonga, A. and
Runyinya-Barabwiliza
(1977b),
Enqudtes
ethnobotaniques
sur la medecine traditionnelle
rwandaise. Tome 1: Prefecture de Kibuye, U.N.R., Butare.
Van Puyvelde, L., DuM, S., Uwimana, E., Uwera, C., Domisse, R.A., Esmans, E.L., Van
Schoor, 0. and Vhetinck, A.J. (1979) New a-Pyrones from Zbozo riparia. Phytochemistry 18,
1215-1218.
Van Puyvelde, L., De Kimpe, N., DuW, S., Chagnon-Dube,
M., Boily, Y., Borremans,
F.,
Schamp, N. and Anteunis, M.J.O. (1981), 1’,2’-Dideacetylboronolide,
a new n-Pyrone from
Zboza riparia. Phytochemistry 20, 2753-2755.
Van Puyvelde, L., Rwangabo, P.C., Barabwiliza-Runyinya,
Ayobangira, F.X. and Mungarulire,
J. (1982) Plantes medicinales et toxiques du Rwanda (III). Afrique Medicale 21, 401-404.
Van Puyvelde, L., De Kimpe, N., Schamp, N., Lefebvre, R. and Mugabo, P. (1984), Active
principles of Zbozo riparia. II. Antispasmodic
activity of 8( 14), 15-sandaracopimaraiene-7
cy,18diol. Farmaceutisch Tijfschrift VOOF Belgie 61, 317.
Van Puyvelde, L., Nyirankuliza,
S., Panebianco,
R., Boily, Y., Geizer, I., Sebikali, B., De
Kimpe, N. and Schamp, N. (1986a), Active principles of Tetradenia riparia. I. Antimicrobial
activity of 8(14),15-sandara-copimaradiene-7n,l&diol.
Journal of Ethnopharmacology 17, 269275.
F., Zhang, W. and Schamp, N., (1987b),
Van Puyvelde, L., De Kimpe, N., Borremans,
8(14),15-sandaracopimaradiene-2a,18diol,
a minor constituent
of the Rwandese medicinal
plant Tetmdenia riparia. Phytochemistry 26(2), 493-495.
Van Puyvelde, L., Lefebvre, R., Mugabo, P., De Kimpe, N. and Schamp, N. (1987). Active
principles of Tetradenia riparia, II. Antispasmodic
activity of 8(14),15-sandaracopimaradiene7a,l8-diol.
Planta Medica 2, 156-158.
Yamahara, J., Fukuda, Y., Sawada, T. and Fujimura, H. (1981). The effectiveness of Chinese
prescription.
The pharmacokinetic
study on the blood concentration
after administration
of
Capillaris fl&s and 6,7_dimethylesculetin.
Shoyokugoku Zasshi, 35(2), 108-114 (cited in Chemical Abstracts 95 (1981) 197103b).
Zelnik, R., Rabenhorst,
E., Matida, A.K., Gottlieb, H.F., Laire, D. and Panizza, S. (1978),
Ibozol, a new deterpenoid from Zbozo riparia. Phytochemistry 17, 1795-1997.