Professional Documents
Culture Documents
1971, Vol
Pergamon
Press. Pnnted
in England.
SATIVA
HEZNDRIKS,
THEO M. MALINGR&,SIEBBAITERMAN and REIN BOS
Abstract-A
waxy fraction obtained by column chromatography of the essential oil of Cannabis sativa consists of
n-alkanes ranging from Cg to C,,, 2-methyl and 3-methyl alkanes and some dimethyl alkanes. The qualitative and
quantitative composition of this fraction has been compared with the alkane fraction obtained by extraction of the
herb.
INTRODUCTION
In previous
151.
RESULTS
EXPERIMENTAL
PIant ntatmial. A botanical description has already been given
[3]. Voucher specimens are available at our Laboratory.
119
H.
720
R. Ros
Table 1. n- and branched alkanes present in the alkane fraction of the essential oil and the
alkane fraction obtained by extraction of Cannabis satiua leaves
Compound
M+
Formula
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
128
142
156
170
184
212
198
226
212
226
254
240
268
268
254
282
268
282
296
310
310
324
338
338
352
352
366
366
380
380
394
394
408
422
436
450
450
464
464
478
492
506
520
534
548
Cd-b,
Go%
CI1%
Cd%,
Ad-b,
G&32
C,,H,o
CisH3.,
C,,Hs,
k&a
Identification
(GC-MS)
n.d
n.d
n-W&o
n-AoH,,
n-G%
-CJ-L
n-&H,,
3,6_dimethyl C,,H,,
a-Ci.~Hso
2,ddimethyl C,,H,s
7G4432
n-G,H,,
2,6-dimethyl C,,H3,
C,,H,,
n-Ci,Hs,
3,6dimethyl C,,Ho4
r&H40
C,QH~O 3,7-dimethyl C,,H,,
CisHss
n-G,J53,
3,6-; 3,7-dimethyl ClsH3st
Go%
C,~HW u-&H,,
C,oH.,,
n-&H,,
CziH.,4 a-C,,H,,
3-methyl C,,H,,
CzzH,,
C,,H,,
n-C,,H,,
C,,H,s
n-Cz3H4s
3-methyl C,,H,,
C,4H,o
%H,o
n-C,,H,o
2-methyl Cz4H4s
C,sH,,
n-C,,Hs,
C,,Hs,
3-methyl r&H,,
C,,Hs,
Cz6Hs4 n-Cz6Hs1
2-methyl C,,H,,
r&H56
C2,Hs6 n-Cz7Hss
CzsH5s 3-methyl C2,HSS
C,sH,s
n-C,sH,s
C,,H,,
n-C,,H,o
C3oH.z~ n-C30H62
C3iHs4 n-C31H64
3methyl C,,H,,
r&H,,
Cd38
C,,H,,
n-C3&,
C,,H,s
C34H70
C3,H,,
C36H74
2-methyl C,,H,,
n-C,,H,s
n-C3,H,o
a-Cs,H,,
n-C,,H,,
C3J-h
n-C3,h
C3db
n-C3J-b8
C39Hm
n-C34bo
C33Ha
Unidentified
1.12*
4.74
0.64
2.84
6.80
0.97
1.65
0.45
0.78
1.83
0.19
1.94
2.14
1.31
1.20
1.42
0.18
1.38
2.61
0.18
2.77
0.75
6.43
0.97
4.64
1.23
8.79
0.94
4.71
10.65
4.07
3.36
0.45
1.94
0.41
1.31
0.82
0.56
0.30
0.19
10.30%
0.36
0.57
0.07
0.62
0.69
0.74
0.36
0.45
0.17
0.33
0.32
0.36
0.22
0.22
0.22
0.17
0.33
0.28
0.12
1.65
0.45
0.49
0.05
11.72
0.23
2.08
55.80
3.09
9.94
0.67
t
0.48
0.24
0.09
0.05
6.30 %
% : Calculated by the normalization method. t : < 0.05 %. n.d : not detected. * :O.xxdoes
not express the accuracy of the method. t : the two GLC peaks partly overlap.
Alkanes of Cannabis
GLC. Alkane fractions were investigated, using n-alkanes as
reference substances on a packed OV-17 column (2 m x 2 mm,
3% OV-17 on Chromosorb W) temp. programmed 7&300 at
I/min: flow N, 30 ml/min and on a micronacked OV-1 column
(6m x .I mm, G/o OV-1 on Chrompack SA) temp. programmed
8&250 at 4/min; flow N, 2ml/min. Injector and detector
temp. 250. GC-MS was performed on a LKB 2191 computerized
system connected via a Becker-Ryhage separator using the
micropacked OV-1 column under the conditions mentioned
above and on a Varian MAT 112 instrument via a split senarator
under the following condition : column OV-1 (2 m x 2 mm,
3/, OV-1 on Chromosorb Wl tema nroarammed 70-250 at
S/min, tlow He 2 ml/min. In both &a
s&n speed of 3 set/scan
(65OO), an ion source temp. of 250 and an electron energy of
70 eV were used.
AcknowledgementsThe
authors thank Mr. J. F. Visser for the
cultivation ofC. satioa in our experimental garden at Buitenpost,
121
REFERENCES
1. Malingre, Th. M., Hendriks, H., Batterman, S. and Bos, R.
(1973) Pharm. Weekblad 108.549.
2. Hen&&s, II., Malingre, Th.M., Batterman, S. and Bos, R.
(1975) Phytochemistry 14,814.
3. Malingre, Th. M., Hendriks, H., Batterman, S., Bos, R. and
Visser, J. F. (1975) Planta Med. 28.56.
4. Stromberg L. (1971) J. Chromatog. 63,391.
5. De Zeeuw, R. A., Wijsbeek, J. and Malingrt, Th. M. (1973)
J. Phann. Pharmac. 25.21.
6. Harborne, J. B. (1973) Phytochemical Methods. Chapter 5,
p. 150. Chapman & Hall, London.
7. Herbin, G. A. and Robins, P. A. (1969) Phytochemistry 8,
1985.
8. Gtllz, P. G. (1968) Phytochemistry 7, 1009.
9. Hunter, G. L. K. and Brogden, Jr., W. B. (1966) Phytochemistry 5,807.