Hindawi

Journal of Food Quality

Volume 2020, Article ID 8862020, 7 pages
https://doi.org/10.1155/2020/8862020

Research Article
The Effect of Thermal Processing on the Saponin Profiles of
Momordica charantia L.

Yi-Jui Liu,1 Yun-Ju Lai ,1 Reuben Wang,2,3 Yi-Chen Lo ,1 and Chun-Hui Chiu 4,5

1
Graduate Institute of Food Science and Technology, National Taiwan University, No. 1 Section 4 Roosevelt Road,
Taipei City, Taiwan
2
Institute of Food Safety and Health, College of Public Health, National Taiwan University, Taipei City, Taiwan
3
Master of Public Health Degree Program, College of Public Health, National Taiwan University, Taipei City, Taiwan
4
Graduate Institute of Health-Industry Technology, Research Center for Food and Cosmetic Safety, College of Human Ecology,
Chang Gung University of Science and Technology, No. 261 Wenhua 1st Rd., Guishan Dist., Taoyuan City, Taiwan
5
Department of Traditional Chinese Medicine, Chang Gung Memorial Hospital, Keelung City, Taiwan

Correspondence should be addressed to Yi-Chen Lo; [email protected] and Chun-Hui Chiu; [email protected]

Received 12 June 2020; Revised 12 August 2020; Accepted 14 August 2020; Published 22 September 2020

Academic Editor: Antimo Di Maro

Copyright © 2020 Yi-Jui Liu et al. This is an open access article distributed under the Creative Commons Attribution License,
which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Saponins from Momordica charantia L. are a class of triterpenoid glucoside molecules that contribute to the bitter flavour of the
plant and possess pharmacological properties. However, little is known about how the bioactivity and bitter flavour of saponins
are affected by thermal processing. We established saponin profiles in bitter gourd extracts using a UPLC-ESI-MS/MS method.
Seven saponins including momordicoside F1, momordicoside F2, momordicoside I, momordicoside K, momordicoside L,
3β,7β,25-trihydroxycucurbita-5, 23(E)-dien-19-al, and momordicine I were monitored for the effects of thermal processing on
their stabilities. The results showed that both 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al and momordicoside L were
extremely sensitive to heat treatment, particularly when they were heated at 100°C for more than 10 mins and under 121°C for
20 mins. Other saponins were reduced significantly by autoclaving, but they remained unchanged at lower temperatures. In
conclusion, specific bitter gourd saponins are affected by thermal treatment, which may modify the bioactive components or bitter
flavour of the bitter gourd extracts.

1. Introduction tannin content, carotenoid content, and antioxidant activity

measurements, when compared to microwave cooking
Bitter gourd (Momordica charantia L.) is a member of the [8, 9].
cucurbitaceae family. The most well-known functional Interestingly, the major active components of the
properties of M. charantia L. are the hypoglycaemic effects Momordica charantia L. extracts are cucurbitane-type tri-
and antidiabetic activities [1–5]. In Asian countries, bitter terpenes and related glycosides, also known as bitter gourd
gourds are usually cooked by steaming, microwave, or saponins [10–13]. Currently, more than 100 bitter gourd
boiling, while studies have shown these various preparation saponins have been isolated and identified from different
and cooking processes can affect the nutritional quality of parts of this plant, including the fruit, stems, or leaves. It is
the bitter gourd [6–8]. Shreds of evidence also shown that reported that the bitter gourd fruit is rich in momordicoside
thermal treatment can alter the nutritional profiles by I, momordicoside F2, and momordicoside F1 [14]. The
changing the stability and functionality of the ingredients in antidiabetic component, 3β,7β,25-trihydroxycucurbita-
vegetables [6, 9]. However, pressure cooking and frying were 5,23(E)-dien-19-al [15], has been used as the functional
reported to retain the maximum antioxidant potential of ingredient for dietary supplements extracted from the bitter
M. charantia L. fruit in total phenol content, total flavonoids, gourd [16]. However, only some bitter gourd saponins,
2 Journal of Food Quality

including momordicoside K, momordicoside L, momordi- (Taipei, Taiwan) with purities of 94.3%, 95.6%, 92.3%,
cine I, and momordicine II are related to the bitter taste or 95.2%, 98.1%, 95.3%, and 92.2%, respectively.
bitterness of the bitter gourd [17]. The presence of these
bitter taste-related saponins may limit the consumption of
bitter gourds. Thus, potential food processing methods that 2.2. Sample Preparation. Bitter gourd powders (0.5 g) were
could remove some of the bitter taste-related saponins while sonicated in 40 mL of 100% methanol for 30 min, followed
retaining the functional component could make the bitter by centrifugation for 15 min at 4000 rpm. The supernatant
gourd acceptable to consumers. was transferred to a flask. This procedure was repeated five
Although saponins are considered the iconic com- more times. The combined supernatants were evaporated in
pounds of M. charantia L., little is known about the effects a Rotavapor (BÜCHI Labortechnik AG, Flawil, Switzerland)
of cooking methods on changes in the saponins of the until dry.
bitter gourd. Tan et al. discussed the effect of food pro-
cessing, including temperature, time, and water-to-sam-
ple ratio, on the stability of saponins in bitter gourds. The 2.3. Standard Preparation. Stock solutions of each standard
results indicated that the total saponin content of the saponin (1.0 mg/mL) were prepared in methanol and stored
bitter gourd is affected by temperature [18]. Donya et al. at –30°C. Different calibration levels were prepared by di-
specifically explored the effects of six treatments, in- luting the stock solutions with methanol. Seven stock so-
cluding frying, blanching, sun drying, oven drying, and lutions were mixed with methanol to prepare a working
freeze-drying on the proximate compositions and con- solution (1 μg/mL each). The working solution was further
tents of momordicoside K and momordicoside L. It was diluted to six concentration levels for the calibration curve
reported that momordicosides K and momordicosides L within the range of 20–200 μg/mL.
were not detected by HPLC–ESI/MS in the blanched
samples [19]. In addition, momordicoside L, but not
2.4. Thermal Stability Test. Methanol extracts of bitter
momordicoside K, was retained in the hot water (98°C ± 2,
gourds were dissolved in 40 mL of water and were used as a
3 min).
background control. The aqueous solution (5 ml) was
Due to the complexity of the saponin structure in
placed in a 50 ml test tube and boiled in a water bath at
M. charantia L. fruit, the detection of individual cucurbi-
various temperatures, including 30°C, 60°C, and 100°C for
tane-type triterpene glycoside in M. charantia fruit is
periods of 5, 10, and 20 mins, respectively. Samples were
challenging. Recently, Hu et al. developed a method for the
also autoclaved at 121°C for 20 minutes. After heating,
quantitative determination of cucurbitane-type triterpenes
samples were immediately placed in an ice box to cool
and triterpene glycosides in bitter gourd juices using
down.
UHPLC [20]. Apart from momordicoside K and momor-
dicoside L, there is no literature available regarding the
thermal stability of the bitter saponins in M. charantia
2.5. UPLC-ESI-MS/MS Analysis. Methanol extracts of the
L. Thus, the objective of this study was to establish a UPLC-
bitter gourds and the aqueous solution were purified by
ESI-MS/MS method to simultaneously determine seven
reversed-phase C-18 solid-phase-extraction cartridges
bitter gourd saponins and to evaluate the profile changes of
(Agela, China) using 10–100% methanol as the elution
these saponins in M. charantia L. var. Hualien No. 3 before
buffer. The total eluted solvent was evaporated until dry. The
and after thermal treatment.
residues were reconstituted to 1 mL with methanol and
filtered using a 0.22 μm nylon membrane filter before UPLC-
2. Materials and Methods ESI-MS/MS analysis. UPLC-ESI-MS/MS analysis was per-
formed using a Waters ACQUITY ultra performance LC
2.1. Materials and Reagents. Hualien No. 3 wild bitter system (Waters, Milford MA, USA) equipped with a TQS
gourd was bred through the Hualien District Agricultural triple quadrupole MS/MS system (Waters, Milford, MA,
Improvement Station, Taiwan. The whole wild bitter USA). The reversed-phase Waters BEH RP-18 column
gourd fruits purchased from a local farm were dried at (2.1 mm × 100 m i.d., particle size 1.7 μm) (Waters, USA)
45°C and ground into a fine powder. Bitter gourd powder was maintained at 35°C with the flow rate of 0.3 mL/min. The
was vacuum packaged and stored at 4 °C in the dark mobile phase consisted of (A) water and (B) methanol, both
before use. Methanol (LC-MS grade) was purchased from containing 0.01% formic acid. Gradient elution was per-
J. T. Baker (Mallinckrodt Baker, Phillipsburg, NJ, USA). formed as follows: 0–2 min, 20% B; 2–6 min, 70% B;
Methanol (HPLC grade) was purchased from Macron 6–15 min, 70% B; 15–19 min, 72% B; 19–22 min, 72% B;
Fine Chemicals (Center Valley, PA, USA). Formic acid, 22–25 min, 80% B; 25–28 min, 80%. Two microliters of the
analytical grade 99.7% purity, was purchased from Rie- sample were injected by an autosampler. The ESI parameters
del-de Haen (Seelze, Germany). Saponin standards, in- were set as follows: capillary voltage was 3.0 kV, cone voltage
cluding momordicoside L, 3β,7β,25-trihydroxycucurbita- was 39 V, desolvation temperature was 200°C, desolvation
5,23(E)-dien-19-al, momordicoside K, momordicine I, gas flow was 800 (L/hr), and cone gas flow was 150 (L/hr).
momordicoside I, momordicoside F2, and momordico- Data were acquired and processed using the Mass Lynx 4.1
side F1, were purchased from Starsci Biotech Co., Ltd. software (Waters, Milford, MA, USA).
Journal of Food Quality 3

2.6. Statistical Analysis. The data were presented as the collected the samples at 5 min intervals for saponin
mean ± standard deviation (SD) from three independent analysis. It was surprising that the levels of momordi-
experiments. The data were analysed using one-way coside L, momordicoside K, momordicoside I, and
ANOVA followed by Tukey’s honest significant difference momordicoside F1 remained stable during the 20 mins of
(HSD) test. Statistical significance is determined by P < 0.05. treatment at different temperatures (Figures 2(a)–2(d).
However, heating at 100°C might change the levels of
3. Results momordicoside F2 (Figures 2(e)) compared to those at
lower temperatures. The bioactive component, 3β,7β,25-
3.1. Identification and Quantification of Cucurbitane trihydroxycucurbita-5,23(E)-dien-19-al and the bitter
Triterpenoids. We first established the platform to analyse taste compound, momordicine I, were less affected after
the specific saponins from the wild bitter gourd and in- 30°C and 60°C treatment for 20 mins. However, the levels
vestigated the effect of thermal processing on these func- of 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al were
tional or bitter taste-related compounds (Figure 1). significantly reduced after 5 mins at 100°C and almost
Individual saponins were detected using tandem mass eliminated after 20 mins of high-temperature treatment
spectrometry with the multiple reaction monitoring (MRM) (Figures 2(f )). Momordicine I was the most sensitive to
mode. For each compound, the strongest MRM transition high temperature. It was barely detected after 10 mins at
was selected as the quantification ion and the other tran- 100°C (Figures 2(g)).
sition was used for qualification. To distinguish compounds
with the same MRM transitions, such as 3β,7β,25-trihy- 4. Discussion
droxycucurbita-5,23(E)-dien-19-al and momordicine I, m/z
495 ([M + Na]+) > m/z 477 ([M + Na–H2O]+), or momor- In this study, we identified that specific triterpenoids, in-
dicoside I and momordicoside F2, m/z 641 ([M + Na]+) > m/ cluding the bioactive component, 3β,7β,25-trihydrox-
z 337 ([M + Na–hexose-side chain]+), the retention time of ycucurbita-5,23(E)-dien-19-al, and the bitter taste
the individual compound was determined according to the compound, momordicine I, in the methanol extracts of
corresponding standard (Table 1). These identification bitter gourd were extremely sensitive to high temperature
profiles of individual saponins helped quantify the bitter (100°C) treatment. Others, including momordicoside L,
gourd saponins. momordicoside K, momordicoside I, and momordicoside
F1, were relatively stable under the same conditions. We also
3.2. The Specific Saponin Content of the Bitter Gourd. observed that autoclaving had profound effects on the levels
Calibration curves were established by independently of all 7 saponins studied. Indeed, Tan et al. reported that
diluting individual stock standard solutions. The con- thermal treatment exceeding 40°C would decrease total
centrations (20–200 ng/mL) of the target saponins were saponin content in the bitter gourd [18], but no specific
tested. The results showed that linearity was obtained for components were identified. Interestingly, Donya et al.
all analytes throughout the concentration range, and the could not detect momordicoside K and momordicoside L
coefficient of correlation (r) was greater than 0.9970 from the blanched bitter gourds. It was speculated that
(Table 2). The specific triterpenoid contents in the momordicosides might increase the loss in the blanching
methanol extract of bitter gourd were analysed and water or be degraded at the high blanching temperatures
calculated based on the standard curves. The results [19]. Here, we demonstrated that momordicoside K and
revealed that the bitter gourd extracts contained high momordicoside L are less affected by heating at 100°C for
amounts of momordicoside L (420.94 ± 18.17 μg/g) and 20 mins, which was more stringent than the blanching in
momordicine I (458.78 ± 35.08 μg/g) compared to other other experimental conditions.
analysed saponins (Table 3). The bitter gourd extracts also It is known that the bitter gourd fruit is rich in
contained a high amount of momordicoside F2 bioactive and bitter flavour-related saponins [15, 16]. The
profiles of saponins may vary in different breeds of bitter
(218.28 ± 26.43 μg/g), momordicoside I
gourds. In this study, we determined the levels of specific
(200.45 ± 26.71 μg/g), and 3β,7β,25-trihydroxycucurbita-
saponins in a hybrid bitter gourd, Hualien No. 3, in
5,23(E)-dien-19-al (190.00 ± 9.63 μg/g) (Table 3).
Taiwan. Interestingly, we found that momordicoside I
Momordicoside K (5.23 ± 0.79 μg/g) and momordicoside
and momordicoside L were abundant in our sample.
F1 (1.91 ± 0.24 μg/g) were minor components in our ex-
Wang et al. indicated that the amount of momordicoside
tract (Table 3).
L was the highest in the Fujian bitter gourd, while
kuguaglycoside C and goyaglycoside D were higher in the
3.3. The Effect of Thermal Processing on the Saponin Content. Guangdong bitter gourd [2]. However, others showed
To study the effect of thermal processing on the stability that momordicoside L and momordicoside F2 were the
of the bitter gourd saponins, we treated the bitter gourd major components, compared to other saponins, in the
extracts with an extreme autoclaving condition at 121°C bitter gourd extracts [21]. Thus, the content of these
for 20 mins as a control. The results showed that this saponins in the bitter gourd samples may be related to
dramatically reduced the levels of all saponins (Figure 2). environmental regions, species [2], or the extraction
We also heated the bitter gourd extracts at various methods. Notably, 3β,7β,25-trihydroxycucurbita-
temperatures, including 30°C, 60°C, and 100°C, and 5,23(E)-dien-19-al, has been used as the functional
4 Journal of Food Quality

H OH H OH

OHC H OHC H

H H

HO O-Glc HO OH

(a) (b)

H OCH3 H
OH
OHC H OHC H

H H

HO O-Glc HO OH

(c) (d)

H OH H OH

H H

H O H O

Glc-O All-O

(e) (f )

H OCH3

H O
Glc-O

(g)

Figure 1: Structures of specific bitter gourd saponins. (a) Momordicoside L, (b) 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al,
(c) momordicoside K, (d) momordicine I, (e) momordicoside I, (f ) momordicoside F2, and (g) momordicoside F1. Glc denotes a glucose
molecule. All denotes allose. Structures were drawn by MDL ISIS/Draw 2.5.

Table 1: Retention times and fragment ions of bitter gourd saponins.

Parent ion (m/z) > daughter
Bitter gourd saponins Retention time (min) MW ion (m/z)
Quality Quantity
Momordicoside L 9.52 634 657 > 203 657 > 477
3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al 11.51 472 495 > 477 495 > 495
Momordicoside K 14.55 648 671 > 203 671 > 491
Momordicine I 15.24 472 495 > 477 495 > 495
Momordicoside I 15.46 618 641 > 337 641 > 203
Momordicoside F2 15.80 618 641 > 337 641 > 203
Momordicoside F1 24.03 632 655 > 337 655 > 625
Journal of Food Quality 5

Table 2: Calibration curve for specific bitter gourd saponins by UPLC-ESI/MS/MS.

Bitter gourd saponins Linear range (ng/mL) Calibration curve r
Momordicoside L 20–200 y � 397.55x − 1373.1 0.9995
3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al 20–200 y � 8175.7x − 160.56 0.9997
Momordicoside K 20–200 y � 236.32x − 700.75 0.9991
Momordicine I 20–200 y � 1997x − 5541 0.9988
Momordicoside I 20–200 y � 27.691x − 149.9 0.9993
Momordicoside F2 20–200 y � 29.61x − 133 0.9970
Momordicoside F1 20–200 y � 122.42x − 272.49 0.9994

Table 3: Contents of specific bitter gourd saponins in bitter gourd extracts.

Bitter gourd saponins Bitter gourd methanol extracts (μg/g)
Momordicoside L 420.94 ± 18.17
3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al 190.00 ± 9.63
Momordicoside K 5.23 ± 0.79
Momordicine I 458.78 ± 35.08
Momordicoside I 200.45 ± 26.71
Momordicoside F2 218.28 ± 26.43
Momordicoside F1 1.91 ± 0.24

4000 150
Concentration (ng/mL)
Concentration (ng/mL)

3000
100
a
2000
a
50
1000 ab
b
b 0
0
0 5 10 15 20 25 0 5 10 15 20 25
Time (min) Time (min)

30°C 100°C 30°C 100°C

60°C 121°C 60°C 121°C
(a) (b)
1500 10
Concentration (ng/mL)

Concentration (ng/mL)

8
1000 a
a 6

4
500
b 2

0 0
0 5 10 15 20 25 0 5 10 15 20 25
Time (min) Time (min)
30°C 100°C 30°C 100°C
60°C 121°C 60°C 121°C
(c) (d)
Figure 2: Continued.
6 Journal of Food Quality

1000 600
a

Concentration (ng/mL)
Concentration (ng/mL)
800
a a
ab 400 ab a
600 a
b
a
400 b
c 200
b
200
b
0 0 b
0 5 10 15 20 25 0 5 10 15 20 25
Time (min) Time (min)
30°C 100°C 30°C 100°C
60°C 121°C 60°C 121°C
(e) (f )
150
Concentration (ng/mL)

100

a
a
a
50 a

b b
0
0 5 10 15 20 25
Time (min)

30°C 100°C
60°C 121°C
(g)

Figure 2: The effect of thermal processing on the contents of bitter gourd saponins. Bitter gourd extracts were treated at 30°C (filled circle),
60°C (filled square), 100°C (filled triangle), or 121°C (inverted triangle). (a) momordicoside L, (b) momordicoside K, (c) momordicoside I,
(d) momordicoside F1, (e) momordicoside F2, (f ) 3, 7, 25-trihydroxycucurbita-5,23(E)-dien-19-al, and (g) momordicine I were analysed by
UPLC-ESI-MS/MS. Different letters represent significant differences. The error bars represent the standard deviation (n � 3).

ingredient for dietary supplement extracted from the Conflicts of Interest

bitter gourd [16]. Our study revealed that 3β,7β,25-tri-
hydroxycucurbita-5,23(E)-dien-19-al is unstable after The authors declare that there are no conflicts of interest.
heating at high temperatures or autoclaving. Thus, this
compound could be a good indicator of functional in- Acknowledgments
gredients and a quality control for bitter gourd saponins
in the future. This research was financially supported by Ministry of Science
and Technology, Taiwan, ROC (NSC 102-2313-B-002-057-
MY3, MOST105-2320-B-002-026-MY3, and MOST 107-2320-
5. Conclusions
B-255-007).
In conclusion, our results demonstrate that cooking at high
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