Food Chemistry 270 (2019) 149–155

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Food Chemistry
journal homepage: www.elsevier.com/locate/foodchem

Conversion of 6-gingerol to 6-shogaol in ginger (Zingiber officinale) pulp and T

peel during subcritical water extraction
⁎
Min-Jung Ko1, Hwa-Hyun Nam1, Myong-Soo Chung
Department of Food Science and Engineering, Ewha Womans University, Seoul 120-750, South Korea

A R T I C LE I N FO A B S T R A C T

Chemical compounds studied in this article: Subcritical water extraction is an eco-friendly method for the extraction of less polar compounds without the use
6-Gingerol (PubChem CID: 442793) of organic solvents. This study determined the extraction conditions that maximize the contents of 6-gingerol
6-Shogaol (PubChem CID: 5281794) and 6-shogaol obtained from ginger pulp and peel. The highest yields of 6-gingerol (0.68 ± 0.08 mg/g), and 6-
Trolox (PubChem CID: 40634) shogaol (0.39 ± 0.03 mg/g) were obtained from ginger pulp at the extraction conditions of 130 °C/25 min, and
Keywords: 190 °C/15 min. 6-Shogaol content increased with the increasing extraction temperature and extraction time due
Ginger pulp to the conversion of 6-gingerol to 6-shogaol by thermal cracking. The antioxidant activity of ginger extracts were
Ginger peel increased depending on the increasing of 6-shogaol content.
6-Gingerol
6-Shogaol
Subcritical water extraction
Conversion

1. Introduction demonstrated that 6-shogaol rather than 6-gingerol inhibited the

Ginger is a rhizome of the plant Zingiber officinale Roscoe in the fa-
mily Zingiberaceae (Sharma, Vijayvergia, & Singh, 2010). It has been
used worldwide as an herb and spice due to its medical and culinary
characteristics. Ginger has been shown to be effective for treatment of
arthritis, fever, vomiting, migraine, hypercholesterolemia and ulcer
(Ali, Blunden, Tanira, & Nemmar, 2008). It is known to contain active
compounds such as gingerol, shogaol, paradol and zingerone (Shukla &
Singh, 2007). These compounds have antioxidant and anti-in-
flammatory activities (Kikuzaki & Nakatani, 1993; Li et al., 2012;
Masuda, Kikuzaki, Hisamoto, & Nakatani, 2004; Shakya, 2015). Among
the active compounds in ginger, 6-gingerol is the most abundant in
fresh ginger (Gopi, Varma, & Jude, 2016). Shogaol, the predominant
pungent compound of ginger, is the dehydrated form of the gingerols
(Connell & Sutherland, 1969). It is well-known that 6-shogaol has su-
perior anti-inflammatory and antioxidant properties compared to 6-
gingerol. The 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity
of 6-shogaol is higher than that of 6-gingerol. 6-shogaol has higher
antioxidant activity than 6-gingerol and was found to inhibit nitrite
production (Dugasani et al., 2010). 6-shogaol inhibits cancer cell
growth to greater extent than 6-gingerol (Cheng, Liu, Peng, Qi, & Li,
2011; Weng, Wu, Huang, Ho, & Yen, 2010). Sang et al. (2009)
growth of cancer cells.
Conventional extraction of ginger is performed from ginger using
organic solvents such as ethanol, ethylene dichloride and acetate, fol-
lowed by the removal of the solvent (Manasa, Srinivas, & Sowbhagya,
2013). However, subcritical water can be an alternative excellent
medium for the extraction of less polar compounds selectively by
varying the temperature (Ko, Cheigh, & Chung, 2014a, 2014b). Sub-
critical water is liquid at the temperatures between 100 °C and 374 °C
under pressure. As the temperature increases, the hydrogen bonding
interactions of water are weakened. Therefore, the dielectric constant
(ε) of subcritical water decreases (Teo, Tan, Yong, Hew, & Ong, 2010).
The dielectric constant of water is 80 at 25 °C but decreases to 27 at
225 °C, similar to the polarity of methanol (ε = 33) or ethanol (ε = 24)
at room temperature (Miller, Hawthorne, Gizir, & Clifford, 1998). Our
previous studies reported that selective extraction of flavonoids could
be achieved by changing the temperature of subcritical water (Ko et al.,
2014a, 2014b).
The aim of this study was to find the optimal conditions for the
extraction of 6-gingerol and 6-shogaol from ginger pulp, and peel using
subcritical water, and then compare the obtained results with the re-
sults obtained using organic solvents used in other extraction methods.
The extracts were evaluated for their antioxidant activity by ferric

⁎
Corresponding author.
E-mail addresses: lucky0617@naver.com (M.-J. Ko), hwahyun4643@naver.com (H.-H. Nam), mschung@ewha.ac.kr (M.-S. Chung).
1
These authors contributed equally to this work.

https://doi.org/10.1016/j.foodchem.2018.07.078
Received 2 April 2018; Received in revised form 21 June 2018; Accepted 11 July 2018
0308-8146/ © 2018 Elsevier Ltd. All rights reserved.
M.-J. Ko et al.
reducing antioxidant power assay. The physicochemical properties af-
fecting the extraction of the active compounds in SWE were assessed
involving the conversion of 6-gingerol to 6-shogaol, and to deliver
practical applications to related industries for the effective extraction
using pilot-scale SWE plant. These results could offer valuable in-
formation on the selectivity of the extraction mechanisms for active
compounds in food industry.
2. Materials and methods
2.1. Sample preparation
The sample was purchased in South Korea at a local market. The
ginger was divided into pulp and peel, and then the pulp was cut into
pieces with the dimensions of 5 mm × 5 mm × 5 mm. All samples were
stored at 4 °C and were used within 4 days after the cutting. The
moisture contents of the ginger pulp and peel were 83.7 ± 1.2%, and
89.6 ± 0.3%, respectively.
2.2. Subcritical water extraction
The laboratory-scale SWE was performed using an accelerated sol-
vent extractor (ASE 350, DIONEX Co.) with purified water (MR-RO800,
Mirae ST, Anyang, Korea), according to the following procedures. Each
1 g of ginger pulp and peel was extracted with water in a stainless-steel
extraction cell with the volume of 22 ml containing a cellulose filter
(Whatman, Maidstone, UK) on the bottom. The extraction cell was
placed in an oven and filled with water for 30 s and was then heated
under high pressure (≈10 MPa) for the required extraction time. Then,
the extract was purged for 1 min, often with nitrogen gas, and the re-
sidual pressure was released from the extraction cell. The final extract
was collected in a collection bottle. The experiment was performed for
40 conditions of the ginger using combinations of the extraction tem-
peratures of 110, 130, 150, 170, and 190 °C, and extraction times of 5,
10, 15, 20, 25, 30, 35, and 40 min. SWE samples were diluted with an
equal volume of methanol. Then, all samples were filtered through a
0.45 μm PVDF 13 mm filter (Whatman, Maidstone, UK) for high-per-
formance liquid chromatography, and micro-spectrophotometer ana-
lysis.
The pilot-scale subcritical water extraction plant was used by the
following our previous study procedure (Ko, Kwon, & Chung, 2016).
Charge the stainless-steel extraction cell containing a cellulose filter on
the bottom with ginger pulp 50 g, and then put it into the extractor.
Turn the agitator preheater on, and automatically transfer the necessary
amount of solvent water 1.1 L. Turn the agitator extractor on, and heat
the extractor to the temperature 170 °C, and 190 °C. Keep operating the
extractor at the desired operating conditions for the extraction time 10,
15, and 20 min. After the extraction time elapsed, automatically
transfer the extract from the extractor to the collector about 1 L extract.
2.3. Conventional extractions
Conventional extraction was conducted using 99.8% methanol
(Duksan Pure Chemicala, Ansan, Korea) and hot water as the solvent.
Each 1 g of ginger pulp, and peel was mixed with 22 ml of methanol and
extracted in the water bath (C-WBI, Chanshin Scientific, Seoul, Korea)
at 60 °C and 25 °C for 2 h, respectively. Hot water extraction was also
carried out at 90 °C for 2 h in the water bath. All experiments were
conducted in triplicate.
Samples of hot water were diluted with an equal volume of me-
thanol. Samples of methanol extraction were diluted with an equal
volume of distilled water. Then, all samples were filtered through a
0.45 μm PVDF 13 mm filter (Whatman, Maidstone, UK) for analysis.
150
Food Chemistry 270 (2019) 149–155
2.4. Analysis of 6-gingerol and 6-shogaol by high-performance liquid
chromatography
High-performance liquid chromatography (HPLC) solvents such as
water and acetronitrile of HPLC grade were obtained from J.T. Baker
(Philipaburg, NJ, USA). Standard compounds of 6-gingerol
(purity ≥ 98%) and 6-shogaol (purity ≥ 90%) were purchased from
Sigma-Aldrich (St. Louis, MO, USA). Quantitative analysis was per-
formed using HPLC (1200 series, Agilent Technologies, Santa Clara, CA,
USA) with a Zorbax C18 column (4.6 mm × 150 mm, 5 μm pore size).
The injection volume was 20 μl and the flow rate was 1 ml/min. The
mobile phase consisted of water (solvent A), and acetronitrile (solvent
B) and was pumped at room temperature. The gradient consisted of
solvent B in the following concentrations: 45% at 0 min, 65% for
0–12 min, 80% for 12–18 min, 80% for 18–20 min, and the post time
was 10 min. The ultraviolet spectrum was recorded at 225 nm. The
typical chromatogram of 6-gingerol and 6-shogaol of ginger extract
allowed us to confirm that the peak times were 5.751, and 11.123 min,
respectively.
2.5. Antioxidant activity by ferric reducing antioxidant power assay
Ferric reducing antioxidant power (FRAP) assay was performed
using the procedure of Benzie and Strain (1996) with some modifica-
tion. 300 mM acetate buffer was made using 3.1 g C2H3Na2 × 3H2O
and 16 ml C2H4O2. The fresh working FRAP reagent was made by
mixing an acetate buffer, 10 mM 2,4,6-tris(2-pyridyl)-s-triazine in
40 mM HCl and 20 mM FeCl3 × 6H2O solution at the ratio of 10:1:1.
The working FRAP reagent was preheated at 37 °C prior to use. 10 μl of
samples reacted with 300 μl of the working FRAP reagent on a 96-well
plate for 30 min in dark conditions at 37 °C. Readings of the colored
product were then taken at 593 nm using a micro-spectrophotometer
(BNR 05606, VersaMax, Sunnyvlae, CA). The standard curve was linear
between 0.000977, 0.001953, 0.003906, 0.007813, 0.015625, 0.3125,
0.0625, 0.125, 0.25, and 0.5 mg/ml Trolox. The results are expressed in
mg/ml trolox equivalent (TE)/g fresh weight.
2.6. Data analysis
The content (expressed in units of mg/g fresh weight) was calcu-
lated from the calibration curve of standard compounds such as 6-
gingerol, and 6-shogaol. The optimum SWE temperature and time from
ginger pulp, and peel were chosen based on the highest concentration
or activities. All data are given as the mean ± SD values of three
measurements. The statistical analysis was performed a one-way ana-
lysis of variance (ANOVA) with Spearman’s rho correlation coefficients
(r) at p < 0.01, and a significant variation at p < 0.05 in Duncan’s test
using SPSS statistical software (version 24.0, IMB, Chicago, IL, USA).
The recovery rate of 6-gingerol, and 6-shogaol using pilot-scale
subcritical water extraction was calculated as follows:
Recovery rate (%)
Compound yield
= × 100
The highest total yield of 6−gingerol, and 6−shogaol
A tendency of the conversion of 6-gingerol to 6-shogaol with
changing extraction temperature during SWE process was also analyzed
from the data for all extraction conditions.
3. Results and discussion
3.1. Effect of extraction temperature and time from ginger pulp
We analyzed the 6-gingerol and 6-shogaol contents of ginger pulp
extracts for the extraction times of 5, 10, 15, 20, 25, 30, 35, and 40 min
at the temperatures of 110, 130, 150, 170, and 190 °C of subcritical
M.-J. Ko et al. Food Chemistry 270 (2019) 149–155

Fig. 1. Effect of extraction temperature, and time the SWE of 6-gingerol (solid block), and 6-shogaol (slashed block) from ginger (A), and peel (B). The data are mean
and standard deviations (n = 3).

water conditions by laboratory-scale SWE. The contents obtained in water. Therefore, the higher temperature of the optimal conditions of 6-
these conditions are shown in Fig. 1(A), and 6-gingerol content in- shogaol compared to that of 6-gingerol is due to the presence of the
creased with increasing at the extraction temperature of 110 and double bond in 6-shogaol. Cheigh, Yoo, Ko, Chang and Chung (2015)
130 °C. However, it decreased gradually with increasing extraction time also reported that compounds bearing hydroxyl groups such as gingerol
in the 150–190 °C range. 6-shogaol was not extracted at 110 °C for up to were extracted at lower temperature, representing a higher dielectric
20 min and was extractable at the temperature greater than 130 °C. 6- constant of water polarity than 6-shogaol.
shogaol content was both time-dependent and temperature-dependent.
However, when the extraction time was too long at 170–190 °C, the 6-
3.2. Effect of extraction temperature and time for ginger peel
shogaol content decreased. Andersson, Hartonen, Hyötyläinen, and
Riekkola (2003) reported that polycyclic aromatic hydrocarbons were
We analyzed the 6-gingerol and 6-shogaol contents of ginger peel
degraded by heat at 200 °C. 6-shogaol would also be degraded by
extracts for the SWE times of 5, 10, 15, and 20 min at the temperatures
prolonged exposure to heat at high temperatures over 170–190 °C. This
of 110, 130, 150, 170, and 190 °C. The results are shown in Fig. 1(B).
is similar to the result of Sarip, Morad, Ali, Yusof, and Yunus (2014)
The highest yield of 6-gingerol (0.35 ± 0.10 mg/g) was obtained at
who studied the degradation of 6-shogaol at 170 °C for 50–60 min. The
130 °C for 10 min, decreasing gradually as the temperature increased
6-gingerol (0.68 ± 0.08 mg/g) content of ginger extracts was maximal
above 130 °C. 6-Shogaol was also extracted in the extracts of the ginger
for the extraction at 130 °C for 25 min, and the 6-shogaol
peel at the temperatures greater than 130 °C for 20 min. The content of
(0.39 ± 0.03 mg/g) content was maximal for the extraction at 190 °C
6-shogaol increased with increasing extraction time and temperature.
for 15 min. 6-Gingerol and 6-shogaol can be selectively extracted by
The optimum extraction of 6-shogaol (0.15 ± 0.03 mg/g) was
controlling the temperature and time of the treatment with subcritical
achieved at 190 °C and 15 min. The 6-gingerol and 6-shogaol contents
water. According to Ko, Cheigh, and Chung (2014) the double bond
obtained from ginger peel showed a similar trend to those from ginger
makes the compound more stable in high-temperature subcritical
pulp. SWE can selectively extract 6-gingerol and 6-shogaol from ginger

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M.-J. Ko et al.
Fig. 2. Effect of extraction temperature, and time the SWE of FRAP antioxidant
activity from pulp (A), and peel (B) ginger for temperature of 110 °C (○), 130 °C
(□), 150 °C (♦), 170 °C (▴), and 190 °C (●). The data are mean and standard
deviations (n = 3).
peel by adjusting the extraction time and temperature. In this study, 6-
gingerol, and 6-shogaol were more than 2 times more plentiful in the
edible part than in the inedible part of the ginger. However, these
ginger peels could be used in the extraction of bioactive compounds
from agricultural by-product.
3.3. FRAP assay of antioxidant activity
The FRAP method was used to measure the antioxidant activities of
the extracts from the ginger pulp (Fig. 2(A)), and peel (Fig. 2(B)). The
antioxidant activity increased with increasing temperature in the short
extraction time range (5–20 min). The antioxidant activity of the ex-
tracts at 110–130 °C increased as the extraction time increased. The
antioxidant activity of the extracts extracted at 130 °C and 150 °C in-
creased until 20 min and then decreased. Extracts using subcritical
water at 190 °C showed the highest antioxidant activity. The anti-
oxidant activity extracted from ginger pulp increased with time up to
35 min (6.43 ± 0.11 mg TE/g). The highest antioxidant activity of
ginger peel extract was at 190 °C/15 min (4.11 ± 0.88 mg TE/g). An-
tioxidant activity results were similar to those for the 6-shogaol content.
6-shogaol has the greatest effect on the antioxidant activity in ginger
extracts. At relatively low temperatures of 110 °C and 130 °C, contents
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Food Chemistry 270 (2019) 149–155
Table 1
Spearman’s rho coefficients (r) for the correlation between FRAP assay of an-
tioxidant activity, 6-gingerol, 6-shogaol, and 6-gingerol + 6-shogaol contents
from ginger pulp, and peel.
6-gingerol 6-shogaol 6-gingerol + 6-shogaol
Ginger pulp FRAP assay −0257 0.838 **
0.146
Ginger peel −0.224 0.911** 0.298
** Indicates the significant level at < 0.01.
of 6-shogaol and 6-gingerol continuously increased and antioxidant
activity also increased. At 150 °C and 170 °C, the conversion of 6-gin-
gerol to 6-shogaol further increased and higher antioxidant activity was
also observed. However, the content of 6-shogaol and its antioxidant
activity started to reduce for the treatment of long extraction time
(40 min) at very high temperature (190 °C). As shown in Table 1, the
results of correlation analysis between antioxidant activity and contents
of 6-gingerol and 6-shogaol of SWE extracts also demonstrated that
there were significant correlations (r = 0.838 for ginger pulp and
r = 0.911 for ginger peel) at p < 0.01 between antioxidant activity
and 6-shogaol content.
The antioxidant activity of 6-shogaol is influenced by the α, β-un-
saturated ketone moiety and is higher than that of 6-gingerol (Dugasani
et al., 2010). Miller, Sampson, Candeias, Bramley, and Rice-Evans
(1996) showed that the conjugated double bond such as those of 6-
shogaol increase the antioxidant activity.
3.4. Comparison with conventional extractions
The extraction efficiency of SWE was evaluated by comparing the
contents of 6-gingerol, 6-shogarol, and the antioxidant activity of the
extracts obtained from ginger pulp, and peel using the conventional
extraction method (Table 2).
The contents of 6-gingerol and 6-shogaol were dependent on the
extraction solvent. The 6-shogaol contents of the extracts from ginger
pulp, and peel obtained using subcritical water at the optimal condi-
tions were higher than those of the conventional extraction methods
extracts. The antioxidant activities of ginger extract were strongly af-
fected by both the extraction conditions of the solvent and the 6-sho-
gaol content of extract. 6-shogaol was not extracted in the extracts
using both methanol at room temperature for 2 h, and hot water at
90 °C for 2 h. Antioxidant activity of FRAP assay was almost not de-
tected in the extracts in which no 6-shogaol content. In the case of
methanol extracts at 60 °C for 2 h, the content of 6-shogaol was much
smaller than that of 6-gingerol, but the antioxidant activity was greatly
increased. When extracted at 190 °C for a long time using subcritical
water from ginger pulp, the antioxidant activity was slightly different
from the 6-shogaol content, due to the effect of not only 6-shogaol
content but also other flavonoids. Ghasemzadeh, Jaafar, and Rahmat
(2010) identified flavonoids such as quercetin, catechin, epicatechin,
kaempferol, naringenin, and rutin in ginger. The flavonoids such as
quercetin, kaempferol and naringenin showed maximum yield when
extracted with subcritical water at 170 °C and 190 °C (Ko et al., 2014a,
2014b). Therefore, non-polar flavonoids, and 6-shogaol could not be
extracted in the high polarity hot water extract at 90 °C for 2 h, and thus
did not have FRAP antioxidant activity.
The results in this study demonstrate that SWE is a highly efficient
and rapid method for the extraction of active non polar 6-shogarol
compounds, and thus, subcritical water could be an excellent alter-
native medium replacing the use of organic solvents such as methanol
for the extraction of active compounds and providing an en-
vironmentally friendly process.
M.-J. Ko et al. Food Chemistry 270 (2019) 149–155

Table 2
Comparison of optimum SWE conditions and conventional extraction methods of 6-gingerol, 6-shogaol, and FRAP antioxidant activity from ginger pulp, and peel.
The data shown are the mean and standard deviations (n = 3).
Extraction solvent/extraction condition
Subcritical water/Optimum condition (°C, min) Methanol/25 °C, 2 h Methanol/60 °C, 2 h Hot water/90 °C, 2 h

Ginger pulp 6-gingerol (mg/g) 130, 25 0.68 ± 0.08b 0.04 ± 0.03a 0.84 ± 0.03c 0.74 ± 0.09bc
6-shogaol (mg/g) 190, 15 0.39 ± 0.03b N.D. 0.04 ± 0.01a N.D.
FRAP (mg TE/g) 190, 35 6.43 ± 0.11c 1.18 ± 0.10a 5.11 ± 0.09b N.D.

Ginger peel 6-gingerol (mg/g) 130, 10 0.35 ± 0.10b 0.01 ± 0.00a 0.53 ± 0.11c 0.27 ± 0.02b
6-shogaol (mg/g) 190, 15 0.15 ± 0.03b N.D. 0.04 ± 0.02a N.D.
FRAP (mg TE/g) 190, 15 4.11 ± 0.88b 0.55 ± 0.03a 3.30 ± 0.15b N.D.

N.D. is not detected.

Fig. 3. Conversion of 6-gingerol to 6-shogaol by temperature dependent thermal cracking (A). Effect of extraction temperature the SWE of 6-gingerol (○, and □), and
6-shogaol (●, and ■) from ginger pulp (solid line), and peel (dashed line) (B).

3.5. Conversion of 6-gingerol to 6-shogaol by subcritical water
The content of 6-gingerol was reduced and that of 6-shogaol was
increased in the extract with the increasing extraction temperature and
time for the extraction using subcritical water. This is due to the con-
version of 6-gingerol to 6-shogaol. The 6-gingerol can partially be
converted to 6-shogaol via thermal cracking at high temperature
(Fig. 3(A)). Thus, the conversion from 6-gingerol to 6-shogaol can occur
during high temperature processes such as subcritical water extraction
(Bhattarai, Tran, & Duke, 2001). Cheng et al. (2011) also suggested that
high temperatures are advantageous for the conversion of 6-gingerol to
6-shogaol.
Fig. 3(B) shows the effects of the extraction temperature on the
conversion of 6-gingerol to 6-shogaol in subcritical water. The con-
version occurred with increasing extraction temperature. Extraction
temperature was the major factor that affected the active compounds
amount of extracts. In other studies, Gopi et al. (2016) also reported
that the conversion of 6-gingerol was temperature-dependent. As in-
dicated by the results in Fig. 3(B), the conversion was accelerated over a
high extraction temperature, thus reducing the 6-gingerol content but
gradually increasing that of 6-shogarol. There was a significant increase
in efficiency of the 6-gingerol extraction from ginger peel at 130 °C
because of the optimum extraction conditions. Furthermore, an in-
crease in the extraction efficiency of 6-shogaol continued to 190 °C,
whereas that of 6-gingerol decreased. This means that the selectively
extraction of active compounds from ginger based on chemical

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M.-J. Ko et al.
Table 3
Extraction content and recovery of 6-gingerol, and 6-shogaol obtained by pilot-scale SWE at different SWE conditions from ginger pulp.
Extraction temperature Extraction time Content (mg/g)
6-gingerol
b b
170 10 0.15 ± 0.01
15 0.21 ± 0.01c
20 0.26 ± 0.01d
190 10 0.10 ± 0.14a
15 0.12 ± 0.01ab
20 0.13 ± 0.02ab
structure is adequate due to the conversion of 6-gingerol to 6-shogaol at
high temperature in subcritical water.
3.6. Pilot-scale subcritical water extraction from ginger pulp
We used a pilot-scale SWE plant for the scale up, and to deliver
practical applications to related industries for the extraction of 6-gin-
gerol, and 6-shogaol from ginger pulp. The highest yields 6-shogaol
(0.39 ± 0.03 mg/g) was obtained from ginger pulp at the extraction
conditions of 190 °C/15 min using laboratory-scale SWE. Table 3 lists
the effects of extraction time and temperature of 6-gingerol, and 6-
shogaol in pilot-scale SWE system from ginger pulp. The yield of 6-
shogaol (0.38 ± 0.01 mg/g) from the pilot-scale SWE was similar to
that obtained from laboratory-scale SWE.
The optimum pilot-scale SWE temperature/time condition for total
yield of 6-gingerol, and 6-shogaol was 190 °C/15 min. The total re-
covery rate of extract at 170 °C/15 min was similar to the 190 °C/
15 min, where the ratio of 6-gingerol to 6-shogaol was different. As
much as 6-gingerol at 170 °C/15, it was almost exactly converted to 6-
shogaol of the 190 °C/15 extract from ginger pulp. The SWE yields of
the 6-gingerol, and 6-shogaol were dependent upon both extraction
conditions such as temperature and time. The bioactive compounds
extraction from ginger via SWE was specifically more adequate for 6-
shogaol than 6-gingerol as the extraction temperature and time in-
creased. This means that 6-gingerol and 6-shogaol were selectively
extracted by control SWE conditions.
4. Conclusions
This study aimed to investigate the optimum extraction conditions
as well as antioxidant activities of 6-gingerol and 6-shogaol extracted
by SWE from ginger pulp, and peel using SWE. We observed the con-
version of 6-gingerol to 6-shogaol during the SWE process as the in-
creasing extraction temperature. It was found that the contents of 6-
gingerol and 6-shogaol from the peel were smaller than those from the
pulp but showed similar tendency with increasing temperature and
time on SWE. The FRAP assay of antioxidant activity of the extract
showed a similar tendency to that obtained for the 6-shogaol amount.
These results suggest that 6-shogaol has a great effect on the anti-
oxidant activity of ginger extract. The SWE selectivity of active com-
pounds could find practical application in the effective extraction from
foods and by-products.
Acknowledgement
This research was supported by the Basic Science Research Program
through the National Research Foundation of Korea (NRF) funded by
the Ministry of Education (2016R1D1A1B03930300), South Korea. This
work was supported by Korea Institute of Planning and Evaluation for
Technology in Food, Agriculture, Forestry and Fisheries (IPET) through
High Value-added Food Technology Development Program, funded by
Ministry of Agriculture, Food and Rural Affairs (MAFRA) (315063-3),
South Korea.
154
Food Chemistry 270 (2019) 149–155
Recovery rate (%)
6-shogaol 6-gingerol 6-shogaol Total recovery rate
b b
0.25 ± 0.01 29.54 49.05 78.60a
0.29 ± 0.01b 42.55c 56.92b 99.47b
0.12 ± 0.03a 52.20d 23.86a 76.06a
0.36 ± 0.01c 19.46a 70.82c 90.28ab
0.38 ± 0.01c 24.71ab 75.29c 100.00b
0.29 ± 0.07b 25.13ab 57.25b 82.38a
Appendix A. Supplementary data
Supplementary data associated with this article can be found, in the
online version, at https://doi.org/10.1016/j.foodchem.2018.07.078.
References
Ali, B. H., Blunden, G., Tanira, M. O., & Nemmar, A. (2008). Some phytochemical,
pharmacological and toxicological properties of ginger (Zingiber officinale Roscoe):
A review of recent research. Food and Chemical Toxicology, 46, 409–420.
Andersson, T., Hartonen, K., Hyötyläinen, T., & Riekkola, M. L. (2003). Stability of
polycyclic aromatic hydrocarbons in pressurised hot water. Analyst, 128, 150–155.
Benzie, I. F. F., & Strain, J. J. (1996). The ferric reducing ability of plasma (FRAP) as a
measure of “antioxidant power”: The FRAP assay. Analytical Biochemistry, 239,
70–76.
Bhattarai, S., Tran, V. H., & Duke, C. C. (2001). The stability of gingerol and shogaol in
aqueous solutions. Journal of Pharmaceutical Sciences, 90, 1658–1664.
Cheigh, C. I., Yoo, S. Y., Ko, M. J., Chang, P. S., & Chung, M. S. (2015). Extraction
characteristics of subcritical water depending on the number of hydroxyl group in
flavonols. Food Chemistry, 168, 21–26.
Cheng, X. L., Liu, Q., Peng, Y. B., Qi, L. W., & Li, P. (2011). Steamed ginger (Zingiber
officinale): Changed chemical profile and increased anticancer potential. Food
Chemistry, 129, 1785–1792.
Connell, D. W., & Sutherland, M. D. (1969). A re-examination of gingerol, shogaol, and
zingerone, the pungent principles of ginger (Zingiber officinale Roscoe). Australian
Journal of Chemistry, 22, 1033–1043.
Dugasani, S., Pichika, M. R., Nadarajah, V. D., Balijepalli, M. K., Tandra, S., & Korlakunta,
J. N. (2010). Comparative antioxidant and anti-inflammatory effects of [6]-gingerol,
[8]-gingerol, [10]-gingerol and [6]-shogaol. Journal of Ethnopharmacology, 127,
515–520.
Ghasemzadeh, A., Jaafar, H. Z., & Rahmat, A. (2010). Identification and concentration of
some flavonoid components in Malaysian young ginger (Zingiber officinale Roscoe)
varieties by a high performance liquid chromatography method. Molecules, 15,
6231–6243.
Gopi, S., Varma, K., & Jude, S. (2016). Study on temperature dependent conversion of
active components of ginger. International Journal of Pharma Sciences, 6, 1344–1347.
Kikuzaki, H., & Nakatani, N. (1993). Antioxidant effects of some ginger constituents.
Journal of Food Science, 58, 1407–1410.
Ko, M. J., Cheigh, C. I., & Chung, M. S. (2014a). Optimization of subcritical water ex-
traction of flavanols from green tea leaves. Journal of Agricultural and Food
Engineering, 62, 6828–6833.
Ko, M. J., Cheigh, C. I., & Chung, M. S. (2014b). Relationship analysis between flavonoids
structure and subcritical water extraction (SWE). Food Chemistry, 143, 147–155.
Ko, M. J., Kwon, H. L., & Chung, M. S. (2016). Pilot-scale subcritical water extraction of
flavonoids from satsuma mandarin (Citrus unshiu Markovich) peel. Innovative Food
Science and Emerging Technology, 38, 175–181.
Li, F., Nitteranon, V., Tang, X., Liang, J., Zhang, G., Parkin, K. L., et al. (2012). In vitro
antioxidant and anti-inflammatory activities of 1-dehydro-[6]-gingerdione, 6-sho-
gaol, 6-dehydroshogaol and hexahydrocurcumin. Food Chemistry, 135, 332–337.
Manasa, D., Srinivas, P., & Sowbhagya, H. B. (2013). Enzyme-assisted extraction of
bioactive compounds from ginger (Zingiber officinale Roscoe). Food Chemistry, 139,
509–514.
Masuda, Y., Kikuzaki, H., Hisamoto, M., & Nakatani, N. (2004). Antioxidant properties of
gingerol related compounds from ginger. BioFactors, 21, 293–296.
Miller, D. J., Hawthorne, S. B., Gizir, A. M., & Clifford, A. A. (1998). Solubility of poly-
cyclic aromatic hydrocarbons in subcritical water from 298 K to 498 K. Journal of
Chemical & Engineering Data, 43, 1043–1047.
Miller, N. J., Sampson, J., Candeias, L. P., Bramley, P. M., & Rice-Evans, C. A. (1996).
Antioxidant activities of carotenes and xanthophylls. Federation of European
Biochemical Societies Letters, 384, 240–242.
Sang, S., Hong, J., Wu, H., Liu, J., Yang, C. S., Pan, M. H., et al. (2009). Increased growth
inhibitory effects on human cancer cells and anti-inflammatory potency of shogaols
from Zingiber officinale relative to gingerols. Journal of Agricultural and Food
Chemistry, 57, 10645–10650.
Sarip, M. S. M., Morad, N. A., Ali, N. A. M., Yusof, Y. A. M., & Yunus, M. A. C. (2014). The
kinetics of extraction of the medicinal ginger bioactive compounds using hot com-
pressed water. Separation and Purification Technology, 124, 141–147.
M.-J. Ko et al.
Shakya, S. R. (2015). Medicinal uses of ginger (Zingiber officinale Roscoe) improves
growth and enhances immunity in aquaculture. International Journal of Chemical
Studies, 3, 83–87.
Sharma, S., Vijayvergia, R., & Singh, T. (2010). Evaluation of antimicrobial efficacy of
some medicinal plants. Journal of Chemical and Pharmaceutical Research, 2, 121–124.
Shukla, Y., & Singh, M. (2007). Cancer preventive properties of ginger: A brief review.
155
Food Chemistry 270 (2019) 149–155
Food and Chemical Toxicology, 45, 683–690.
Teo, C. C., Tan, S. N., Yong, J. W. H., Hew, C. S., & Ong, E. S. (2010). Pressurized hot
water extraction (PHWE). Journal of Chromatography A, 1217, 2484–2494.
Weng, C. J., Wu, C. F., Huang, H. W., Ho, C. T., & Yen, G. C. (2010). Anti-invasion effects
of 6-shogaol and 6-gingerol, two active components in ginger, on human hepato-
carcinoma cells. Molecular Nutrition & Food Research, 54, 1618–1627.