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Study on Roman Chamomile (Chamaemelum nobile L. All.) Oil

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Abstract

In this report the comparative chemical composition of the essential oil of Chamaemelum nobile from two different regions in Northern Italy was examined by GC and GC/MS. 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 (18.2–20.3%) and other angelate esters.
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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.
Downloaded by [Univ Modena e Reggio Emilia BU] at 00:19 10 November 2014
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
Downloaded by [Univ Modena e Reggio Emilia BU] at 00:19 10 November 2014
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.
References
1.
2.
3.
4.
5.
6.
7.
8.
9.
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... Due to antimicrobial (Bail et al., 2009) and antioxidant properties (Piccaglia, Marotti, Giovanelli, Deans, & Eaglesham, 1993;Sharifzadeh, Jebeli Javan, Shokri, Abbaszadeh, & Keykhosravy, 2016), it has been used in medicinal, pharmaceutical and cosmetic products. Angelate, tiglate and butyrate esters, monoterpenes and sesquiterpenes and some other compounds were reported in C. nobile EO (Farkas et al. 2003;Antonelli & Fabbri, 1998;Hasebe & Oomura, 1989;Tognolini et al., 2006;Omidbaigi et al., 2004;Srivastava et al., 2010;Carnat, Carnat, Fraisse, Ricoux, & Lamaison, 2004;Bail et al., 2009;Umezu, Sano, Hayashi, Yoshikawa, & Shibata, 2017). ...
... C. nobile EOs were investigated considering various factors (Farkas et al., 2003;Antonelli & Fabbri, 1998;Tognolini et al., 2006;Omidbaigi et al., 2004;Srivastava et al., 2010;Hasebe & Oomura, 1989;Carnat et al., 2004;Povilaityte, Venskutonis, & Juknevičiene, 2001;Bail et al., 2009;Farhoudi, 2013;Wang et al., 2014), however the effects of such important factors as growing phase have not been reported previously. Percentage composition of 112 compounds, which were detected in Roman chamomile EO at 6 growth vegetation phases is presented in Table 3. ...
... isoamyl angelate (4.6-5.36%), and monoterpenes (E)pinocarveol (3.1-4.5%) and pinocarvone (4.1-4.5%) (Antonelli et al., 1998); isobutyl angelate (24.46%), 2-methylbutyl angelate (17.36%), isoamyl angelate (7.6%) and 2-butenyl angelate (7.34%) (Tognolini et al., 2006). Isobutyl angelate was a major EO constituent of C. nobile from France (Carnat et al., 2004;Bail et al., 2009) and Iran (Omidbaigi et al., 2004). ...
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Valorization of botanicals for the development of natural food-grade ingredients is an important task in terms of sustainability and processing waste reduction. In this study, Roman chamomile (Chamaemelum nobile L.) herb was collected at six different vegetation phases in the period 26 May – 23 August 2019 and subjected to biorefining into the several valuable fractions. The yield of hydro-distilled essential oil (EO) was in the range of 0.22% (intensive vegetative growth) to 0.80% (full flowering). Angelic, isobutyric, butyric and methacrylic acid esters and some monoterpene and sesquiterpene derivatives were the major EO constituents: 3-methylpentyl angelate (20.11-27.56%), methallyl angelate (7.28-10.33%), isoamyl angelate (5.57-9.02%), isobutyl angelate (4.84-6.79%), 2-methylbutyl angelate (3.11-6.32%), 3-methylamyl methacrylate (5.04-6.17%), 3-methylpentyl isobutyrate (4.29-6.64%), 3-methylamyl isobutyrate (4.29-6.64%), α-pinene (1.61-6.37%) and pinocarvone (1.46-4.67%). In order to valorize water soluble and solid EO distillation residues their antioxidant potential was evaluated by several in vitro assays: water extracts were considerably stronger antioxidants than acetone extracts isolated from the solid residues. Water extracts of the plants collected at flowering phases were the strongest antioxidants; their TPC, FRAP and ORAC values were up to 143.2 mg gallic acid equivalents/g, 650, and 5601 μmol TE/g dry extract, respectively, while effective concentrations (EC50) of DPPH• and ABTS•+ scavenging, were down to 0.59 and 0.49 mg/mL, respectively. Among 7 tentatively identified by UPLC/Q-TOF/MS phenolic constituents the intensity of molecular ion of 3,5-dicaffeoyl quinic acid was the largest. The results obtained may assist for developing flavorings, antioxidants and health beneficial preparations from C. nobile extracts.
... Matricaria recutita commonly known as "German chamomile" (GC) and Chamaemelum nobile commonly known as Roman chamomile (RC) are the two major types of chamomile used for health conditions. They are believed to have similar effects on the body (16). Most research worked on GC but, studies on RC is limited and stronger evidence to support its use for inflammation is required. ...
... RC belongs to the family Asteraceae and is widely distributed in Asia, Europe, Africa and Northern America. RC is known as a medicinal plant since the middle age (16). However, the provided clinical and non-clinical data for RC do not fulfill the requirements of a well-established medicinal use with recognized efficacy (17,18). ...
... Table 1. Chemical composition of German [20] vs. Roman chamomile [21]. The values represent average amounts for the two species. ...
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Chamomile has a long history of traditional medicinal uses. The two commonly used varieties with therapeutic applications are German chamomile known as Matricaria chamomilla L. and Roman chamomile or Chamaemelum nobile L. The plant contains many components, namely, flavonoids, terpenoids, and coumarins, which are responsible for its medicinal properties. The review discusses recent developments that help in establishing its role as a therapeutic agent in various areas as an anti-inflammatory, antioxidant, analgesic, antimicrobial, hepatoprotective, anti-allergic, anticancer, and anti-hypertensive agent. Not much is known about its role in the treatment of CNS disorders and metabolic syndromes, which are also discussed. The chemical components responsible for the therapeutic activity and the respective mechanism of action are also elaborated.
... For instance, the composition of two oil samples from C. nobile grown in Northern Italy was dominated by isobutyl angelate (38.5/6.3%) and 2-methylbutyl angelate (20.3/18.2%) (29). The same esters were the main components (21.6% and 14.4%, respectively) of an oil sample isolated from plants cultivated in Slovak republic, accompanied by 3-methylamyl angelate (8.4%) (30). ...
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... Just as German chamomile essential oil possess blue color due to theterpenoidchamazulene. The major compounds were esters of angelic, tiglinic, isobutyric, butyric, methacrylic, acetic, crotonic, and valeric acids, as well as in less quantitychamazulene and α-bisabolol, as well as β-pinene, cine-1,8-ole, α-pinene, germacene D, α-cadinol, cedryl acetate, and (E,E)-farnesyl acetate (Antonelli and Fabbri 1998;Farhoudi 2013;Góra and Lis, 2017). The main chemical constituents are isobutyl angelate and 2- methylbutyl angelate. ...
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Roman chamomile (Chamaemelum nobile (L.) All.) is a perennial herbaceous medicinal plant species that has not yet been thoroughly researched in terms of the influence of growing conditions on its morphological characteristics, flower yield, and the content and quality of its essential oil (EO). The plant material was harvested in the subsequent two production years at three localities in Southeast Serbia, differing in soil type (Alluvial soil, Rendzina, and Calcomelanosol). Based on two-year average values, the best results were obtained from plants grown on Rendzina, including the yield of fresh flowers (1850.2 g/m2), the highest plant height (49.3 cm), the number of branches (4.1), leaves (11.6), and flower heads (3.6), the flower diameter (1.6 cm), and the essential oil content (1.6%). The major EO constituent obtained from the plants growing on Rendzina and Calcomelanosol was 3-methyl pentyl angelate (20.8% and 15.2%, respectively). In the EO obtained from the plants growing on Alluvial soil, the major EO constituent was isobutyl angelate (13.0%), while the content of 3-methyl pentyl angelate was close to it (12.2%). The outcomes of this study provide guidelines for further research related to the cultivation of a Roman chamomile genotype on various soil types in a hilly region of Southeast Serbia, where most cultivated plants cannot be grown.
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ssential oils of pure lavender and lavender blends have been employed as potential anxiolytic aromas in aromatherapy, but a direct comparison of their effectiveness is lacking. The current study investigated the effects of aroma on induced anxiety in non-clinical adults, comparing pure lavender, a commercially available blend and a no aroma control. An experimental, quantitative, mixed factorial design with an opportunity sample of 60 participants was employed. Participants were randomly allocated to three equal groups, one tested in a room infused with lavender aroma, the second with the doTerra Peace® blend, and the third free from any aroma. Participants’ state anxiety scores were measured before and after a novel video-based anxiety induction procedure. Data analysis revealed that the anxiety induction was successful and that both aromas delivered small to medium-sized buffering effects compared to no aroma. The findings add to a small body of research in an area where the practice is global yet has limited scientific evaluation. Future studies utilising brain imaging and blood serum analysis to investigate the anxiolytic mechanism of aromas would be beneficial to further our understanding.
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A simple procedure, previously set up for the quick evaluation of aromatising herbs by direct headspace gas chromatographic analysis, was checked with regard to its application as a routine method. Many samples of herbs and drugs of various kinds and of different qualities were subjected to a sensory evaluation and to headspace analysis. There are significant analytical differences between herbs of good and inferior quality in agreement with the organoleptic evaluation of the same drugs, judged by an experienced panel of tasters. Some tests were performed to determine the exact content of each substance present in the headspace of the examined herbs: preliminary results are given. A suitable internal standard was used for quantitative purposes. The proposed technique is in accordance with the requirements of the Quality Control Service.
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Occurrence of New Bifunctional Esters In Roman Camomile Oil (Anthemis nobilisL.) Some novel aliphatic esters of the unusual 3-hydroxy-2-methylidenebutyric acid have been found in the commercially available essential oil. Additionally, esters of (Z)-2-methyl-2-butenoic acid of structurally similar diols or other bifunctional alcohols have also been identified. Spectral data as well as a synthetic approach to the new esters of 3-hydroxy-2-methylidenebutyric acid are given.
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1. Tiglic acid free of isomeric acids has been synthesized in 40-53% yields from 10 moles of 2-butanone. Angelic acid free of appreciable amounts of isomeric acids has been synthesized from tiglic acid in 33% yield by a three-step process. 2. Pure methyl and ethyl tiglate have been prepared by direct esterification of tiglic acid. Methyl angelate of confirmed identity has been prepared by a replacement reaction of angelate ion with methyl iodide.
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GC headspace analyses of various aromatizing herbs have been compared with those relating to the essential oils, obtained by steam distillation, of the same plants. In this way it was possible to establish the most significant differences between the composition of a herb flavor and that of its essential oil. In particular, we observed some very volatile compounds in the headspace samples which were absent from the essential oil; these components may make an important contribution to the herb flavor. The identification of these substances is still in progress.
Direct headspacegas chroniatographic aridysis zoirhglass capillarycolunzrrs i n quality control of aromatics herbs
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Aria(ysisofRoniu?i chanioniile. I'roceedings 1 lth Int'l Congress of Essent. Oils Fragrances and Flavors
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N. A. Shaath, S. Dedeian:lohnson and P. M. Griffin, Aria(ysisofRoniu?i chanioniile. I'roceedings 1 lth Int'l Congress of Essent. Oils Fragrances and Flavors. 4, 207-213, Oxford and IBH Publ. Co. 1% Ltd., New Iklhi (1989).
lJ?tsaturated coniporierits iii esseritia/ oil of Aiitbernis nobilis L. (Ronzan chanioniile)
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