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Ology Science Determination of 1,8 Cineole in Fresh Rosemary and Sage Leaves by Solid-phase Microextraction and Gas Chromatography/Mass Spectrometry

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Ology Science Determination of 1,8 Cineole in Fresh Rosemary and Sage Leaves by Solid-phase Microextraction and Gas Chromatography/Mass Spectrometry

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This paper focuses on the determination of 1,8 cineole in fresh Rosmarinus officinalis and Salvia officinalis leaves by gas chromatography with mass spectrometry combined with solid-phase microextraction. Rosmarinus officinalis is commonly known as rosemary; it has been reported that the performance on cognitive tasks was statistically significant related to the concentration of absorbed 1,8 cineole following exposure to rosemary. A series of experiments were performed to determine the 1,8 cineole concentration in rosemary and sage leaves before and after heating as these herbs are widely used in the culinary arts. The results indicate that 50.0 mg of fresh rosemary leaf contains 0.23 ± 0.01 µg (95% confidence interval) of 1,8 cineole, which is 4.6 ± 0.2 ppm. Besides fresh rosemary leaves, Salvia officinalis which is commonly referred to as sage exhibited a higher 1,8 cineole concentration than fresh rosemary leaf, 50.0 mg of fresh sage leaf contained 0.37 ± 0.02 µg of 1,8 cineole, which is 7.4 ± 0.4 ppm.
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Ology Science
91 J Res Anal. (2017) Volume 3 • Issue 3 ISSN : 2473-2230
Determination of 1,8 Cineole in Fresh Rosemary
and Sage Leaves by Solid-phase Microextraction
and Gas Chromatography/Mass Spectrometry
Abstract
This paper focuses on the determination of 1,8 cineole in fresh Rosmarinus officinalis and Salvia officinalis
leaves by gas chromatography with mass spectrometry combined with solid-phase microextraction. Rosmarinus
officinalis is commonly known as rosemary; it has been reported that the performance on cognitive tasks was
statistically significant related to the concentration of absorbed 1,8 cineole following exposure to rosemary.
A series of experiments were performed to determine the 1,8 cineole concentration in rosemary and sage leaves
before and after heating as these herbs are widely used in the culinary arts. The results indicate that 50.0 mg
of fresh rosemary leaf contains 0.23 ± 0.01 µg (95% confidence interval) of 1,8 cineole, which is 4.6 ± 0.2
ppm. Besides fresh rosemary leaves, Salvia officinalis which is commonly referred to as sage exhibited a higher
1,8 cineole concentration than fresh rosemary leaf, 50.0 mg of fresh sage leaf contained 0.37 ± 0.02 µg of 1,8
cineole, which is 7.4 ± 0.4 ppm.
Keywords: Rosemary; Sage; 1,8 Cineole; SPME; GC/MS
*Corresponding author: Edward P.C. Lai
E-mail: peter.harrington@ohio.edu (P.D.B.H)
Copyright: ©2017 OLOGY Group.
Xue Zhao and Peter de B. Harrington*
Center for Intelligent Chemical Instrumentation, Clippinger Laboratories, Department of Chemistry and
Biochemistry, Ohio University, USA
Journal of Research Analytica
Research Article
Ology Science
92 J Res Anal. (2017) Volume 3 • Issue 3
Citation: Zhao X, Harrington PDB. Determination of 1,8 Cineole in Fresh Rosemary and Sage Leaves by Solid-phase Microextraction and Gas
Chromatography/Mass Spectrometry. J Res Anal. 2017; 3(2): 91-95
ISSN : 2473-2230
Introduction
Putative eects of aromas on aspects of human behavior can be
tracked back to ancient Greece, extracts from the aromatic plants
can be used for cosmetic and medical purposes [1]. Nowadays,
aromas are popular for pleasure, relaxation, and therapeutics.
Rosemary is a small evergreen plant with needle like leaves, it
grows wild in most Mediterranean countries [2]. Rosemary
possesses some pharmacological properties [3] besides being very
popular for its cooking qualities [4]. ere are many applications
of rosemary in everyday life, for example, reducing pests in
gardens and its extracted oil may be used as fragrance [5]. Moss et
al. [6] have found that sning essential oil from herbs enhanced
human memories. To study the possible relationship between
the 1,8 cineole level in the plasma and cognitive performance and
mood, he and his co-workers designed a series of rosemary tests,
which showed for the rst time that performance on cognitive
tasks is statistically signicant related to the concentration of
absorbed 1,8 cineole following exposure to rosemary aroma,
with improved performance at higher concentrations. In this
research, 1,8 cineole concentrations in fresh rosemary and sage
leaves were determined.
Sage is also an herb commonly used for its medical properties. Its
genus name means long life and good health. Sage extracts have
been reported to possess several health eects, like antioxidant
capacity and anti-inammatory properties [7]. Bigford et al. [8]
stated that sage has been investigated as a potential treatment for
Alzheimer’s disease. e result of this study showed that fresh
sage plant contains higher 1,8 cineole than fresh rosemary leaf,
but there is no publication explaining that the reason sage can
enhance memory is the compound 1,8 cineole in the plant.
As the most common usage of rosemary in our daily life is
in culinary art, an experiment of comparing the 1,8 cineole
concentrations before and after heating was also designed. e
1,8 cineole concentration was signicantly decreased after heating
to 100°C. ere is much news about the ability of rosemary
to help enhance memory. For example, on the ‘Body Ecology’
website [9], there is an article called ‘e herb rosemary: super
antioxidant powerhouse memory booster and more’, which
encouraged people to eat rosemary dishes and cook with rosemary.
In this study, the result showed that at high temperature, the
1,8 cineole concentration was signicantly decreased, some
websites posted articles about the top ten herbs to help boost
your brain power. As some of them are dicult to collect, only
ginseng, sage, and green tea were collected to determine the 1,8
cineole concentration. e result is that only sage plant contains
higher 1,8 cineole concentration than rosemary, while the other
herbs all have lower 1,8 cineole concentration. However, on
many websites, like Natural Society [10], it listed rosemary as
a better herb than sage to boost your brain power, which is also
misleading, as the result showed that fresh sage contained more
1,8 cineole than fresh rosemary.
e principles of solid-phase micro-extraction (SPME) were rst
demonstrated by Pawliszyn and co-worker in 1990 [11], and
it has been greatly developed and widely applied over the past
twenty years [12]. Sample preparation is very important, SPME
is a very simple, ecient and solventless sample preparation
method [13]. is method saves preparation time and can
improve detection limits [14]. e SPME ber is the key part
of the SPME apparatus. e ber is a thin fused-silica optical
ber, coated with a thin polymer lm [15]. e most used ber
coating is polydimethylsiloxane (PDMS), which is also used
as a coating material in chromatography. SPME method was
chosen to perform an experiment and collect the extraction of
fresh rosemary and sage data because of its advantages. Several
approaches have been developed for separation of rosemary and
sage plant. Gas chromatography coupled with mass spectrometry
is the most widely accepted and reliable technique for separation
of rosemary and sage plants [16].
In this study, the 1,8 cineole concentrations in fresh rosemary
leaves and sage leaves were determined and compared. In our
daily life, typically rosemary and other aromatic plants are
consumed cooked, so the eect of heat to 100°C, on 1,8 cineole
concentrations before and after heating were also compared.
Experimental Section
Material and reagents
A 1,8 cineole, 99% stock solution was obtained from Alfa
Aesar (Ward Hill, MA). Standard solutions of 1,8 cineole with
concentrations of 0.1, 0.2, 0.4, and 0.8 µg/mL were prepared
by dilutions of the stock solution with pentane. A 100 µm
polydimethylsiloxane (PDMS) ber, 10 mL headspace glass vials,
and crimp seals were purchased from Sigma-Aldrich (St. Louis,
MO). A stainless steel ne mesh strainer colander sieve with
7.9 cm diameter was purchased from the Kroger supermarket
(Athens, OH). e samples of fresh rosemary and fresh sage
leaves were collected from the Kroger supermarket (Athens,
OH). All the fresh rosemary and sage leaves were analyzed
within 10 days of the production date and they were stored at
room temperature.
Instrumentation
All the experimental data were collected on a ermo Finnigan
PolarisQ quadrupole ion trap mass spectrometer/Trace Gas
Chromatography (GC/MS) system with a Triplus AS2000 auto
sampler (San Francisco, CA, USA). e GC/MS system was
controlled by the XCalibur software version 2.0.7 provided by
ermo. Analytes were separated on a 30 m × 0.25 mm × 0.1 µm
5% diphenyl/95% dimethylpolysiloxane cross-linked capillary
column (SHRXI-5MS, Shimadzu Scientic Instruments Inc.
Columbia, MD).
Preparation of sample and calibration standards
To evaluate the cooking eect on rosemary, a 50.0 mg portion of
powdered rosemary was added to the SPME vial without crimp
seal and placed on the hotplate in the hood which was set at
75.0°C or 100.0°C for 15.00 min. Five replicates were collected
at each temperature.
e ber was thermally desorbed in the GC injector at 260.0°C
for 5.00 min. e temperature program was set to start at
50.0°C, hold for 1.00 min, ramp at 20.0°C min-1 to 110.0°C,
hold for 10.00 min, ramp at 20.0°C min-1 to 250.0°C, hold for
10.0 min. e carrier gas was helium with a constant ow rate
of 1 mL min-1. e transfer line temperature was maintained at
280.0°C. e inlet temperature was 260.0°C. Mass spectra were
93
Ology Science J Res Anal. (2017) Volume 3 • Issue 3 ISSN : 2473-2230
Citation: Zhao X, Harrington PDB. Determination of 1,8 Cineole in Fresh Rosemary and Sage Leaves by Solid-phase Microextraction and Gas
Chromatography/Mass Spectrometry. J Res Anal. 2017; 3(2): 91-95
obtained in electron ionization mode (70 eV) with the range
from mass-to-charge ratio (m/z) 40-550.
Rosemary and sage leaves were powdered instead of testing
individual leaves for better reproducibility. 1,8 Cineole standard
solutions with concentrations of 0.1, 0.2, 0.4, and 0.8 µg/mL
were prepared in pentane. Aliquots of 1.00 mL of each standard
solution were added to the SPME vial with 50.0 mg powdered
rosemary or sage. e SPME vials were left uncapped in the
hood at room temperature for 30.00 min to fully evaporate the
pentane. 1,8 Cineole has a boiling point 176.0°C so only an
insignicant loss was expected during this process. After 30.00
min of evaporation, the vials were placed into the auto sampler
tray for analysis. e sample vial was incubated at 55.0°C for 0.50
min. e SPME PDMS ber was then exposed to the headspace
for 30.00 min to achieve equilibrium [2]. e peak area of 50.0
mg rosemary or sage with each standard solution is listed in Table
1 and 2. e standard addition calibration curves are given in
Figures 1 and 2, the coecients of determination R2 were 0.9936
and 0.9938 that were calculated from the sample averages of a
random block design with ve replicates. A condence interval
of 95% is used for all measurements of precision. e 1,8 cineole
concentration in rosemary and sage were calculated from these
calibration curves. Each plant was analyzed by SPME-GC/MS
in ve replicates. ree days later, ve replicates were performed
on each plant.
e RAW les of GC/MS data were converted to the network
common documents format with Xcalibur Software ‘File Convert
Tool’. MATLAB R2015b (Math Works, Natick, MA) student
version was used to process the data.
Results and Discussion
A total-ion chromatogram of fresh rosemary leaves is in Figure 3.
e dierent peaks marked in the gures represent some typical
compounds in fresh rosemary leaves, peak 1 for α-pinene, peak
2 for 1,8 cineole, peak 3 for limonene, and peak 4 for camphor.
e peak for 1,8 cineole was identied from its mass spectrum,
which is given in Figure 4. e peaks of m/z 154, 139, 93, 81
and 67 are all characteristic peaks for 1,8 cineole. Figure 5 gives
6
5
4
3
2
1
0
-1
-0.6 -0.4 -0.2 0 0.2 0.4 0.6 0.8 1 1.2
Mass of 1,8 Cineole added (µg)
R2 = 0.9936
Peak Area
X 108
Figure 1: Rosemary 1,8 Cineole Calibraon Curve (95 % condence interval).
6
5
4
3
2
1
0
-1
X 108R2 = 0.9938
Peak Area
Mass of 1,8 Cineole added (µg)
-0.6 -0.4 -0.2 0 0.2 0.4 0.6 0.8 1 1.2
Figure 2: Sage 1,8 Cineole Calibraon Curve (95% condence interval).
Mass of 1,8 cineole added (µg) Peak Area (×108)
0.1 2.37
0.2 3.42
0.4 3.42
0.8 5.13
Table 1: Peak area for determinaon of 1,8-cineole in rosemary by standard
addion.
Mass of 1,8 cineole added (µg)Peak Area (×108)
0.1 2.62
0.2 3.28
0.4 3.59
0.8 5.23
Table 2: Peak area for determinaon of 1,8-cineole in sage by standard
addion.
4
3.5
3
2.5
2
1.5
1
0.5
0
x 107
0 5 10 15 20 25
Time (min)
Intensity
Rosemary Total-ion Chromatogram
Figure 3: Total-ion chromatogram of fresh rosemary leaf at room temperature
([1] α-pinene; [2] 1,8 cineole; [3] limonene; [4] camphor).
100
90
80
70
60
50
40
30
20
10
0
93
139
81
67
154
Relative Abundance
50 100 150
m/z
Figure 4: Mass spectrum of 1,8 cineole from fresh rosemary leaves.
Ology Science
94 J Res Anal. (2017) Volume 3 • Issue 3
Citation: Zhao X, Harrington PDB. Determination of 1,8 Cineole in Fresh Rosemary and Sage Leaves by Solid-phase Microextraction and Gas
Chromatography/Mass Spectrometry. J Res Anal. 2017; 3(2): 91-95
ISSN : 2473-2230
the fragmentation interpretation of 1,8 cineole. e molar mass
of 1,8 cineole is 154 g/mol. e fragment with m/z 139 is 1,8
cineole with a methyl group loss. Rosemary leaf contains 0.20
± 0.01 µg (95% condence interval) of 1,8 cineole, which gives
w/w concentration of 4.6 ± 0.2 ppm.
e most common use of rosemary is as a spice and in most cases
rosemary will be cooked at high temperature. An experiment
has been designed to compare the 1,8 cineole concentration in
rosemary at room temperature, 75.0°C and 100.0°C. e total-
ion chromatograms for the three temperatures are given in Figure
6. e intensities of many peaks at 100.0°C have decreased
compared with the peak intensities at 75.0°C. ere are several
peaks after a retention time of 20.00 min that are attenuated.
It can be explained that some compounds, for example,
α-humulene, has a boiling point that is 106.0°C, so was severely
attenuated when heated at 100.0°C. e boiling point of 1,8
cineole is 176.0°C and its peak has markedly decreased when the
rosemary was heated at 100.0°C. At 100.0°C, the concentration
of 1,8 cineole has signicantly decreased, so it can be concluded,
1,8 cineole cannot aect cognitive function after cooking at high
temperature.
e total-ion chromatogram of fresh sage is given in Figure 7.
e 1,8 cineole peak is marked in the chromatogram. e 1,8
cineole concentration in fresh sage leaves was calculated using the
sage 1,8 cineole standard addition calibration curve (Figure 2).
e result is that 50.0 mg fresh sage leaf contained 0.37 ± 0.02
µg of 1,8 cineole, which is 7.4 ± 0.4 ppm.
Conclusion
In this study, 1,8 cineole concentration in fresh rosemary and
sage leaves were determined. It is also demonstrated that, at
100.0°C, 1,8 cineole concentration is signicantly decreased
compared with room temperature rosemary. Besides rosemary,
1,8 cineole concentration in fresh sage leaves was also determined.
It contains higher 1,8 cineole concentration than rosemary. In
the future work, more herbs and their 1,8 cineole concentrations
will be determined and compared, as heating will decrease the
concentration of 1,8 cineole. Because chewing gum [17] also
has been reported to improve memory, it might be interesting
to produce some herbal gums [17] with fresh rosemary or sage.
In this way, the 1,8 cineole concentration can be kept at room
temperature, and people can enhance their memory eectively by
chewing rosemary gum.
Acknowledgement
Authors are thankful for Dr. Mengliang Zhang for his helpful
suggestions.
1,8 Cineole (C10H18O)
m/z 154
m/z 139
0
0
0
m/z 93 m/z 81
m/z 67
Figure 5: 1,8-Cineole mass spectrum interpretaon.
10
9
8
7
6
5
4
3
2
1
0
x 107
0.0 5.0 10.0 15.0 20.0 25.0 30.0
Room Tempeature Rosemary
75 °C Rosemary
100 °C Rosemary
Retention Time (min)
Intensity
Figure 6: Room temperature, 100 °C and 75 °C rosemary total-ion
chromatogram.
2.5
2
1.5
1
0.5
0
x 107Sage Total-ion Charomatogram
0 5 10 15 20 25
Retention Time (min)
Intensity
1,8-cineole
Figure 7: Fresh sage leaves total-ion chromatogram at room temperature.
9 5
Ology Science J Res Anal. (2017) Volume 3 • Issue 3 ISSN : 2473-2230
Citation: Zhao X, Harrington PDB. Determination of 1,8 Cineole in Fresh Rosemary and Sage Leaves by Solid-phase Microextraction and Gas
Chromatography/Mass Spectrometry. J Res Anal. 2017; 3(2): 91-95
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References
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