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Journal of Essential Oil Research
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Study on Roman Chamomile
(Chamaemelum nobile L. All.) Oil
Andrea Antonelli a & Cristiano Fabbri a
a Istituto di Industrie Agrarie , Via S. Giacomo 7, 40126,
Bologna, Italy
Published online: 09 Dec 2011.
To cite this article: Andrea Antonelli & Cristiano Fabbri (1998) Study on Roman Chamomile
(Chamaemelum nobile L. All.) Oil, Journal of Essential Oil Research, 10:5, 571-574, DOI:
10.1080/10412905.1998.9700974
To link to this article: http://dx.doi.org/10.1080/10412905.1998.9700974
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J.
Essent.
Oil
Res.,
10,
571-574 (Sep/Oct
1998)
RESEARCH NOTE
Study
on Roman Chamomile
(Chamaemelum
nobile
L.
All.)
Oil
Andrea Antonem' and
Cristiano
Fabbri
Istittito
di
Industrie Agrurie, Viu
S.
Giucomo
7,
40126
Bologna,
Italy
Abstract
In this report the comparative chemical composition
of
the essential
oil
of
Chunzaenzelrim
nohilc>
from two different regions in Northern Italy was examined by
GC and
GUMS.
No
significant differences were found in the composition
of
the two
oils
which were characterized by a high content
of
isobutyl angelate (36.3-38.5%),
2-methylbutyl angelate (18.2-20.30/) and other angelate esters.
Key Word Index
Chainaenieltim
nohile,
Antheinis
nohilis,
ASterdcede, essential
oil
composition,
isohutyl angelate, 2-methylbutyl angelate.
Introduction
One
of
the first papers on the detailed cornposition
of
Roman chamomile
oil
was that
of
Ndno
et
al.
(1).
Later, these same authors studied the
oil
in more detail (2,3). More recently, several other investigations
have addressed this topic
(4-6).
The composition
of
this
oil
was characterized by a high content
of
angelic esters Some papers
of
the last decade
(7-10)
reported a detailed composition
of
Roman charnomile but sometimes indicated
isohutyl
ester
(11)
or
butyl ester (4) or isoamyl
ester
(1)
as the major constituent.
The lack
of
pure reference standards and the unspecificity
of
the mass fragmentation
of
angelic esters
make peak identification uncertain. This shortcoming may
be
overcome by a comparison
of
the retention
times. For these reasons angelic and tiglic acids were esterified with alcohols at
1
to
6
carbon atoms.
Some authors also examined the anti-inflammatory, antidiuretic and sedative properties
of
this
oil
(12).
Experimental
Two different Roman chamomile oils were obtained from Giardino Officinale in Casola Valsenio
(RA
-
Italy). One
oil
was distilled from chamomile plants grown in the Emilia-Romagna region
(E),
and
the other one came from the Piemonte region
(P)
in Northern Italy (whole phnt; 0.30% and
0.28%
oil
yield
respeczively). The samples were analyzed
by
GC
and GC/MS after dilution in t-butyl methyl ether
(10
mg/mL).
GC
analyses were performed hy injecting
1
pL
of
the
oil
solutions in the split mock (split ratio 1:45)
into a Carlo Erba Strumentazione gas chromatograph HRGC 5160 (Milan, Italy) equipped with a 25 m
x
0.25 mm, 0.25
pm
film thickness SE-52 capillary column (Mega
S.p.A
,
Legnano, Italy). The column
*Address for correspondence
Received: March
I997
Rwised:
,hiire
1997
1041-2905/98/00~l5-0571$04.00/0--81998
Allurcd Publishing Corp.
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572
ANTONELLl
AND
FALIBIU
Table
1.
Percentage composition
of
samples
of
Roman chamomile oil
Peak
No.
Compound
E
P
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
isoarnyl acetate*
propyl methacrylate"'
isobutyl isobutyrate
a-pinene
isobutyl methacrylate
carnphene
B-pinene
propyl angelate2
butyl butyrate
isobutyl isovalerate"
isoarnyl isobutyrate*
2-rnethylbutyl isobutyrate*
limonene
1,8-cineole
isoarnyl rnethacrylate
2-rnethylbutyl rnethacrylate
isobutyl angelate
2-butenyl angelate"
butyl angelate
isobutyl tiglate3
2-rnethylbutyl 2-methylbutyrate
trans-pinocarveol"
terpinen-4-01
isoarnyl angelate
2-rnethylbutyl angelate
pinocarvone"
isobutyl3-hydroxy-2-rnethylenebutyrate*
angelyl angelaten4
2-hydroxy-2-rnethyl-3-butenyl
angelate'
hexyl angelate
unidentified Deaks
0.1
0.1
3.9
1.2
1.4
0.8
0.1
1
.I
0.8
0.1
0.4
3.1
0.1
0.1
0.2
0.7
38.5
8.4
0.8
0.3
0.5
3.1
0.3
5.3
20.3
4.1
0.3
1.4
0.3
0.1
2.4
0.1
0.2
5.3
1.6
2.1
0.7
0.2
1.3
0.9
0.2
0.4
3.5
0.1
0.1
0.2
0.8
36.3
7.9
0.7
0.4
0.5
4.5
0.3
4.6
18.2
4.5
0.3
0.9
0.4
0.1
3.3
~
1
=
1.8.
2-methyl-2-propenoate;
*
=
i.e.
2-methyl-(2Z)-butenoate;
=
1.e.
2-methyl-(2E)-butenoate;
'
=
i.e. 2-methyl-2-butenyl 2-methyl-
(2Z)-butenoate, tentatively identified by the
MS
library;
E
=from Emilia-Romagna region; P
=
from Piemonte region
was operated with hydrogen as carrier gas
(1
mumin) with an initial temperature
of
50°C then raised
at 4"C/min
to
70°C held for
8
min and then raised at 5'C/min
to
20OoC, holding this temperature
for
6
min, and then ballistically to 300°C. Injector was kept at 250"C, and flame ionisation detector was set
at 300°C. Chromatograms were displayed and integrated by Chrom-Card data handling (Fisons
Instruments, Milan, Italy).
For GC/MS, a QMI)
1000
(Fisons Instruments, Milan, Italy) instrument was used maintaining the same
GC condition just described and recording
mass
spectra from 33 to 350
tu/z
at 70
eV.
Chromatographic peaks were identified by retention times and mass spectrometry
of
authentic
compounds.
Angelic acid
was
prepared from tiglic acid in accordance with I3uckles and Mock
(13).
Angelic and
tiglic
esters were prepared using the following procedure. Stock solutions
of
the two acids
(100
mCr/mL)
were prepared in diethyl ether. The esters were synthesized as follows:
10
mg
of
each acid were
separately esterified with a large
excess
of
methanol, ethanol, propanol, 2-metliylpropanol, butanol,
2-methylbutanol, isoarnyl alcohol, amyl alcohol and hexanol; a small amount
of
Ilowex
50
W
8X
resin
was used as the acid catalyst. The resin was removed by filtration, and the crude reaction mixtures were
simply diluted in t-butyl methyl ether prior analyses.
The
esters isobutyl isobutyrate,
Iwtyl
methacrylate,
butyl butyrate and 2-metliyll~utyl 2-methylbutyrate were prepared in the same way.
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ROMAN
CHAMOMILE
(CHAMAEMELUM
NOBILE)
On.
55
573
100-
136
C
A
100-
m.
r/?"
T
B
179
119
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574
ANTONELU
AND
FABBRI
Table
II.
Mass spectral data
of
tentatively identified peaks.
Peak No.
1
2
10
11
12
22
26
27
m.w.
130
128
158
158
158
152
150
172
4.
(rel.
int.)
115 [M-15]+(<1), 87(18), 70(42), 71(17),
55(50),
43(100).
101 [M-27]+(<1), 85(1), 73(13), 70(39), 55(18), 43(100).
116 [M-42]+(3), 103(22), 87(10), 85(100), 60(15), 57(73), 56(51), 41(43).
115 [M-431+(4), 89(16), 71(54), 70(73), 55(28), 43(100), 41(29).
115 [M-43]+(<1), 101(6), 89(11), 71(87), 70(79), 55(22), 43(100), 41(39).
152 [MI+(<l), 119(32), 109(27), 92(99), 91 (73), 83(55), 81(31), 70(63), 69(36), 55(84),
43(42), 41(100), 39(51).
41(78), 39(44).
45(27), 43(49),
41
(69).
150 [MI+(9), 135(26), 108(69), 107(45), 81(77), 79(37), 77(18), 69(22), 53(100), 43(19),
172 [MI+(<l), 101 (85),99(100), 98(53), 97(22), 81 (42), 83(36), 73(31), 57(99), 55(45),
angelate respectively
The
related
mass
spectra
are
reported
in
Figure
1.
Spectral data
of
peak
28
and
29
were
reported
by
Lawrence
(14)
and
other authors
(51,
respectively.
The
other
MS
spectra
of
tentatively identified
compounds
are
summarized
in
Table
11.
trans-Pinocarveol
and
pinocarvone
(15,16)
were
the most important monoterpcnes
(7-10%).
Furthermore,
small
quantities
of
a-
and
P-pinene,
camphene,
1,8-cineole
(3)
limonene
(17)
and
terpinen-4-01
(9)
were
detected.
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