Journal of Chemistry

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The Development of Novel Biologically Active Small Molecules

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Research Article | Open Access

Volume 2021 |Article ID 5580756 | https://doi.org/10.1155/2021/5580756

Liangyu Li, Cheng Luo, Xiqun Zheng, "Purification of Anthocyanins Derived from Black Kidney Bean (Phaseolus vulgaris L.) by a Simulated Moving Bed", Journal of Chemistry, vol. 2021, Article ID 5580756, 12 pages, 2021. https://doi.org/10.1155/2021/5580756

Purification of Anthocyanins Derived from Black Kidney Bean (Phaseolus vulgaris L.) by a Simulated Moving Bed

Academic Editor: Wagdy Eldehna
Received26 Jan 2021
Revised26 Mar 2021
Accepted31 May 2021
Published16 Jun 2021

Abstract

Purification of anthocyanins derived from black kidney bean (Phaseolus vulgaris L.) by column chromatography and simulated moving bed (SMB) methods was investigated, and the anthocyanins of black kidney bean were identified. The SMB had advantages over column chromatography in processing efficiency, operation cost, and automation degree in contrast testing. The best SMB conditions resulted in purity and yield of black kidney bean anthocyanins of 24.61 ± 0.21% and 87.85 ± 0.32%, respectively. The half maximal inhibitory concentration (IC50) of 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging activity and 2,2ʹ-azinobis-(3-ethylbenzthiazoline-6-sulphonate) radical (ABTS+∙) scavenging activity was 0.95 and 2.14 of refined anthocyanins, respectively, indicating strong antioxidant capacity. Three anthocyanins were detected and identified by UPLC-Triple-TOF/MS from black kidney bean skins: delphinidin-3-O-glucoside, petunidin-3-O-glucoside, and malvidin-3-O-glucoside. The experimental results suggested that SMB may help promote industrialization and purification of anthocyanins from colored kidney beans as well as from other plant materials.

1. Introduction

Kidney bean (Phaseolus vulgaris L.) is a widely cultivated legume crop in China and has important nutritional and medicinal value. In recent years, the proteins [1, 2], oils [3], lectins [4], peptides [5], starch [68], polyphenols [9, 10], and flavonoids [11] of kidney bean have been researched, representing a great achievement. The utilization of kidney beans will increase with the development of these studies and result in discarding a lot of skin. The skin of colored kidney beans possesses superior antioxidative activity compared with white kidney beans because it contains anthocyanins [12, 13]. Most studies have focused on the antioxidant characteristics [14, 15] and the effect of processing methods on the bioactivity of anthocyanins of kidney beans [16], but research is rare on the purification method of anthocyanins derived from colored kidney beans. Studies on colored kidney beans have focused on red and Swedish brown kidney beans, with few on black kidney beans.

The methods for purifying anthocyanins include adsorption on macroporous resins [1719], liquid and subcritical carbon dioxide [20], membrane separation [21], preparative high-performance liquid chromatography [22], aqueous two-phase extraction [23, 24], ionic liquid solutions [25], high-speed countercurrent chromatography [26], high voltage paper electrophoresis [27], and column chromatography [28]. These methods can achieve high purity, but many are laboratory-level and cannot be industrialized. Some integration and combination technologies have been used to purify anthocyanins, and the process efficiency has been improved, but there is still some gap before industrialization [2931]. The continuous chromatography system is a type of simulated moving bed (SMB) chromatography and is an efficient and advanced purification technology. Compared with traditional column chromatography, the SMB method has a short processing time and good productivity and requires less buffer and volume of resin [32]. The SMB system has been used in many fields of protein separation [33], Ginkgo biloba enrichment [34], and heparin purification [35]. The use of the SMB system in purifying anthocyanins has not been reported. The objective of this study was to purify the anthocyanins derived from black kidney bean using the SMB system and investigate the in vitro antioxidant properties of black kidney bean anthocyanins (BKBA). The principal components of BKBA were also discussed. This will provide useful information for developing a new industrialization purification method for anthocyanins (see Figure 1).

2. Experimental

2.1. Methods
2.1.1. Black Kidney Bean Collection

Black kidney bean grown in Baiquan, Heilongjiang Province, was collected during autumn 2017. The beans were stored at −20°C within 2 h of collection.

2.1.2. BKBA Extraction

Before extraction, black kidney beans (cv. LongYun no. 4) were soaked at 30°C for 8 h, and the skin was obtained. The BKBA was extracted by the method of Li et al. [36]: the bran was extracted by an ultrasonic processor (JinBaiTe, China) twice with 70% (v/v) ethanol and 0.6% hydrochloric acid was added for 20 min. Operation parameters were set as follows: the liquid material ratio 20 mL/g, ultrasonic frequency 24 kHz, ultrasonic power 300 W, extraction temperature 30°C, and it was evaporated to dryness using a rotary evaporator (Buchi, Switzerland) at 50°C. The content of BKBA anthocyanin is about 40 mg/g [37]; the amount (21.5 mg/g) obtained by this method was consistent with previous studies [38].

2.1.3. Effects of Separation Conditions on the Purification of BKBA by AB-8 Resin

The pretreated AB-8 resin (the macroporous slightly polar adsorbent resin of polystyrene, pore size 13-14 nm, specific surface area 450–530 m2/g, water content 65–75%, bulk density 0.62–0.72 g/mL, particle size 0.315–1.25 mm, porosity 42–46%, white opaque spherical particles) was put into a chromatography column (15 × 500 mm) (constructed by the National Coarse Cereal Engineering Technology Research Center). The AB-8 absorbs BKBA through surface adsorption and hydrogen bonds, forming a relatively stable structure and completing the adsorption process. Then, the BKBA is desorbed from the resin by washing with different polar solvents and constantly destroying the formed hydrogen bonds. Anthocyanins are compounds with a 2-phenyl chromogenic ketone structure; in addition to a keto carbonyl group, they often contain alcohol hydroxyl and phenol hydroxyl groups. Different anthocyanins have different polarities. Therefore, the molecular structure of anthocyanins contains both hydrogen-bonded donor and hydrogen-bonded receptor groups, so polar and nonpolar resins can be used for adsorption and desorption. The operation parameters were set as follows: column temperature of 30°C; BKBA concentrations of 100, 150, 200, 250, and 300 mg/mL (desorption flow rate: 2.0 mL/min); desorption flow rates of 1.0, 1.5, 2.0, 2.5, and 3.0 mL/min (BKBA concentration: 200 mg/mL). After saturated feed, the chromatography column was washed by deionized water (3 BV) and desorbed by 60% ethanol (3 BV). The lyophilized product was collected, and the purity and yield were calculated to study the effect of concentration on the purification of BKBA by the AB-8 resin.

2.1.4. Purification of BKBA by Column Chromatography

The column chromatography was a fixed mode and a true moving bed (TMB). The AB-8 resin was put into preparative chromatography column (15 × 500 mm). The operation parameters were set as follows: column temperature of 30°C, concentration of 200 mg/mL, and desorption flow rate of 2.0 mL/min. After saturating the feed, the chromatography column was washed by deionized water (3 BV) and desorbed by 20%, 40%, and 60% ethanol (3 BV), respectively. The eluent was, respectively, collected, and finally, the samples were analyzed by an ultraviolet spectrophotometer, and the antioxidant activities were determined, to study the purification of BKBA by column chromatography.

2.1.5. Purification of BKBA by SMB

The SMB (20 columns of 25 mm × 500 mm, National Coarse Cereal Engineering Technology Research Center) was used in this experiment. Using the SMB technology, the traditional SMB was improved according to the technical requirements. The whole process cycle consisted of a disk with a plurality of resin columns (20 columns) and a porous distribution valve. Through the rotation of the disk and the conversion of the valve mouth, the separation column completed the whole process of adsorption, purification, desorption, and regeneration in a process cycle. In the continuous separation system, the process steps were carried out simultaneously. Twenty chromatography columns (25 mm × 500 mm) were used in this study for the separation process.

Studies suggest that anthocyanins mainly exist in the 40% ethanol solution of black kidney bean. Accordingly, the chromatographic separation system of SMB separation for BKBA was divided into five parts: adsorption zone, refined zone, desorbing zone, regenerative zone, and water washing zone. The raw material was added to the system at the adsorption zone, where the anthocyanins were absorbed by the resin. The regenerative zone can also be regarded as the impurity removal region. The 20% ethanol was applied to remove proteins, polysaccharides, and other impurities. The desorption zone was eluted with 40% ethanol to obtain high purity BKBA products. In the regenerated zone, 80% ethanol was used to rinse the chromatographic column, and other impurities in the column were completely removed. In the wash zone, deionized water was used to remove ethanol from the chromatographic column and prepare for the feeding zone. The system had 20 chromatographic columns. When the system was running, the resin column and supporting chassis were in the fixed positions. The rotary valve rotated at a regular rate, and consequently, 20 chromatographic columns were used during the operation of five procedures, including continuous adsorption, purification, elution, regeneration, and water washing. Twenty slots were matched with the stiff end of the 20 columns. When the system was running, the liquid flow into or out of the fixed slot was constant and uninterrupted. When the rotating valves rotated in a circle, each column of resin underwent a complete process of adsorption, refining, desorption, regeneration, and water washing. On the basis of single column experiment, the equivalence and conversion relation between the SMB and TMB is linked by the following equations [39].

The conversion relationship between solid state flow and switching time of SMB is as follows:

Flow ratio formula of TMB is as follows:

The conversion relationship between the flow ratio of SMB and the flow ratio of TMB is as follows:

The conversion relationship between the flow rate ratio and the flow ratio of TMB is as follows:where QS is the solid state flow, Qj is the mobile state flow of zone j, ɛ is the porosity, t is the retention time, mj is the flow ratio of zone j at TMB, uj is the flow rate ratio of zone j, us is the flow rate ratio of solid state, and Dj is the axial diffusion coefficient.

According to the adsorption experiments of AB-8 resin for BKBA, the parameters, including saturated adsorption capacity, saturation time, eluent, elution and regeneration agent and water flow rate, regeneration and washing effect, and the actual operation performance of resin and equipment, were determined. The types of distribution of IE-SMB chromatographic separation zones were defined. The initial process parameters were calculated according to the static and dynamic experiments of resin and the material balance equation of the TMB model. According to the basic parameters of the TMB experiment, the technological parameters of the separation and purification of BKBA by SMB were further optimized.

2.1.6. Determination of Anthocyanins

Two samples of anthocyanin solution were diluted with potassium chloride buffer (pH 1.0) and sodium acetate buffer (pH 4.5), the ratio of the two solutions was 1 : 15, using distilled water as a blank, and adsorption was measured by an ultraviolet spectrophotometer (Evolution 220, Thermo Fisher Scientific, USA) at 515 nm and 700 nm. The anthocyanin content was calculated by formula (5), with cyanidin-3-O-glucoside (C3G) as the standard:where ΔA is the difference of absorbance, ΔA = (A510nm − A700nm)pH1.0 − (A510nm − A700nm)pH 4.5, Mw is the molecular weight of C3G (449.2 g/mol), DF is the dilution multiple, ε = 26,900 is the molar extinction coefficient of C3G, and l is the optical distance of the cuvette (cm).

2.1.7. UPLC-Triple-TOF/MS Analysis for BKBA

The UPLC-Triple-TOF/MS was determined by the method reported by Wang et al. [40]. The UPLC-Triple-TOF/MS system was TOF 5600+ of Acquity™ ultra Triple (Waters Corporation, Milford, MA, USA) equipped with a ZORBAX-SB C18 (4.6 mm × 100 mm, 1.8 μm, Agilent Co. Ltd., Palo Alto, CA, USA). The wavelength of the UV detector was set at 520 nm. The injection volume was 5 μL and the column temperature was 30°C. Mobile phase A consisted of a water solution containing 0.1% (v/v) formic acid, while mobile phase B was an acetonitrile solution containing 0.1% (v/v) formic acid. The gradient program at a flow rate of 0.8 mL/min was as follows: 0–25 min: 5% B; 25–35 min: 25% B; 35–38 min: 95% B. It was equipped with an electrospray ionization source (AB Sciex Co. Ltd., USA) and positive ion mode monitoring, the atomizing gas GS1 was 50 psi, atomizing gas GS2 was 50 psi, and the air curtain gas (CUR) was 35 psi, the ion source temperature (TEM) was 600°C (positive), the ion source voltage (IS) was 5,500 V (positive), and the m/z setting range was 100–1,500. First level scan: cluster voltage (DP), 100 V, and focus voltage (CE), 10 V. Secondary scanning: mass spectrometry data were collected by TOF MS-Product Ion-IDA mode. CID energy was 20, 40, and 60 V. Before injection, the mass axis was corrected by CDS pump, so that the mass axis error was less than 2 ppm. Compounds were identified using the SciFinder and Reaxys databases [41].

2.1.8. Determination of DPPH Radical Scavenging Activity

The DPPH (Sigma, USA) free radical scavenging activity was determined by the method of Maeda et al. with slight modification [42]. To the samples (2 mL) at different concentrations (0–50 μg/mL) was added 2 mL of 0.4 mM DPPH radicals. The mixture was shaken vigorously and left to stand for 30 min in darkness before the absorbance was measured at 517 nm against a methanol blank. Ascorbic acid (Vc) was used as a positive control. The percent inhibition of DPPH was calculated according to the following equation:where A is the absorbance of DPPH radical + methanol and B is the absorbance of DPPH + test samples. All determinations were performed in triplicate. IC50 is the concentration of the sample needed to decrease 50% of the DPPH concentration relative to that of control.

2.1.9. Determination of ABTS+∙ Radical Scavenging Activity

The ABTS+∙ free radical scavenging activity was determined by the method of Arnao et al. and Zhang et al. with slight modification [43, 44]. The ABTS (Sigma-Aldrich) solution (7 mmol/L; 5 mL) and potassium persulfate solution (2.45 mmol/L; 5 mL) were mixed in darkness for 12 h, to produce ABTS+∙. The ABTS+∙ solution was diluted with water, and the absorbance was 0.70 ± 0.02 at 734 nm. The percentage inhibition of ABTS was calculated according to the following equation:

2.2. Statistical Analysis

The data are presented as means ± SD. Statistical analyses were done using the statistical SAS program, and the significance of each group was verified by one-way ANOVA followed by Duncan’s test at .

3. Results

3.1. The Result of Separation Conditions on the Purification of BKBA by AB-8 Resin

The results showed a significant effect of concentration on the purification of BKBA by AB-8 resin (Figure 2). There were few differences in BKBA purity and yield at low concentrations (100–200 mg/mL), and BKBA purity and yield suddenly declined when the concentrations were above 200 mg/mL. The high concentration led to inadequate contact between BKBA molecules and resin and a decline in adsorption capacity, which affected the BKBA purification by the AB-8 resin. The best concentration was 200 mg/mL.

The desorption flow rate of AB-8 resin significantly affected BKBA purification (Figure 3). There were few differences in BKBA purity and yield at a low desorption flow rate (1.0–2.0 mL/min) and the BKBA purity and yield suddenly decreased for a desorption flow rate above 2.0 mL/min. A higher adsorption flow rate of AB-8 resin led to insufficient adsorption and lowered the adsorption capacity. That may have affected the BKBA purification. The best desorption flow rate was 2.0 mL/min.

3.2. Purification of BKBA by Column Chromatography

Scavenging capacity of BKBA and concentration of BKBA significantly differed with different EtOH concentrations (Figure 4). Most of the BKBA was concentrated in the 40% ethanol elution solution, and little was concentrated in deionized water or 20% ethanol or 60% ethanol elution solutions. In addition, the 40% ethanol had higher purity than the other eluents.

The results showed that the test samples and the positive control Vc had an inhibitory effect (Table 1), and the IC50 of DPPH and the IC50 of ABTS+∙ scavenging activity of 40% ethanol solution were 0.95 and 2.14 μg/mL, respectively. This was lower than in other samples, and scavenging activity was in the following order: 40% ethanol > 20% ethanol > Vc (positive control) > 60% ethanol > distilled water. Therefore, the best results for scavenging activity for BKBA were with 40% ethanol solution. The 40% ethanol elution solutions exhibited higher antioxidant activity than ascorbic acid. However, the IC50/DPPH of BKBA we obtained was slightly lower than the IC50/DPPH of the anthocyanins of the fruit of Berberis heteropoda Schrenk (2.25 μg/mL) reported by Sun et al. [45], and the IC50/ABTS+∙ of BKBA we obtained was slightly lower than the IC50/ABTS+∙ of the anthocyanins of blueberry (4.33 μg/mL) reported by Zhao et al. [46]. This was because we removed the 20% and 60% ethanol solution, and the 20% and 60% ethanol elution solutions had similar antioxidant activity to ascorbic acid, so the purity of BKBA was lower and may have contained proteins, polysaccharides, flavonoids, and other impurities.


SampleIC50 of DPPH scavenging activityIC50 of ABTS+∙ scavenging activity

Distilled water18.34 ± 0.36e35.21 ± 0.52e
20% ethanol4.86 ± 0.05b8.17 ± 0.13b
40% ethanol0.95 ± 0.03a2.14 ± 0.11a
60%7.79 ± 0.22d16.32 ± 0.35d
VC5.26 ± 0.08c9.69 ± 0.16c

Letters a–e indicate intergroup differences at .

Thus, we collected the 40% ethanol elution solution during the SMB.

3.3. SMB Purification for BKBA

Using the column chromatography results and free scavenging capacity research and correlation theory, we assigned the zoning mode of SMB and the primary parameters of SMB. The SMB had five zones: adsorption, refining, desorbing, regenerative, and water washing zones. These five zones had six (series connection), four (series connection), three (series connection), four (parallel countercurrent), and three columns (series connection), respectively. The primary parameters of SMB-IEC were adsorption zone flow rate of 12 mL/min, refined zone flow rate of 26 mL/min, desorbing zone flow rate of 24 mL/min, regenerative zone flow rate of 20 mL/min, water washing zone flow rate of 30 mL/min, and switching time of 1080 s. The results (Table 2) were obtained through experimental optimization.


No.Adsorption zone flow rate (mL/min)Refined zone flow rate (mL/min)Desorbing zone flow rate (mL/min)Regenerative zone flow rate (mL/min)Water washing zone flow rate (mL/min)Switching time (s)Purity (%)Yield (%)

111.027.523.523.532.0126023.22 ± 0.15c80.61 ± 0.22d
211.024.523.526.532.0126024.34 ± 0.18a84.92 ± 0.26c
312.529.524.522.037.5126020.28 ± 0.12f79.84 ± 0.19e
412.528.524.522.538.5108024.61 ± 0.21a87.85 ± 0.32b
514.536.524.528.542.0108022.19 ± 0.11d79.62 ± 0.28e
614.538.526.526.042.5108021.32 ± 0.09e90.91 ± 0.36a
716.042.530.029.545.5108023.78 ± 0.14b88.36 ± 0.35b

Letters a–f indicate intergroup differences ().

The SMB test results showed that the no. 4 test was better than the other six tests (Table 2), when we considered the quantity of treatment, ratio of material to water, purity, and yield. The best conditions were an adsorption zone flow rate of 12.5 mL/min, refined zone flow rate of 28.5 mL/min, desorbing zone flow rate of 24.5 mL/min, regenerative zone flow rate of 22.5 mL/min, water washing zone flow rate of 38.5 mL/min, and switching time of 1,080 s, which resulted in a purity and yield of BKBA of 24.61 ± 0.21% and 87.85 ± 0.32%, respectively.

3.4. UPLC-MS Analysis for 40% Ethanol Elution Components

Anthocyanins have a similar structure to flavonoids and they can easily be confused in routine mass spectrometry analysis, so we used positive ion detection, meaning that the main anthocyanins were concentrated within 7–15 min [45]. The UPLC-MS analysis for 40% ethanol elution indicated three compounds in the 40% ethanol elution of BKBA (Figure 5).

3.5. Component 1

The peak time of compound 1 was 9.26 min, [M]+m/z was 465.1019 Da, and the molecular formula was C21H21O12+. According to the secondary mass spectrometry, the parent nucleus of the compound was 303 Da, which indicated delphinidin. There was a six-carbon sugar structure in the compound. Searching the SciFinder and Reaxys database showed the compound to be delphinidin-3-O-glucoside. The mass and mass2 spectra and the possible structural formula of compound 1 are shown in Figure 6.

3.6. Component 2

The peak time of compound 2 was 11.67 min, [M]+m/z was 479.1173 Da, and the molecular formula was C22H23O12+, from the results of high resolution mass spectrometry. According to the second-order mass spectrometry, the parent nucleus of the compound was 317 Da, with one more methylene than the parent nucleus of component 1, indicating that it was petunidin. The m/z 317 [M-162] and m/z 302 [M-162-15] implied that there was a six-carbon structure in the compound. The structures of carbohydrate and methoxy groups were retrieved using the SciFinder and Reaxys databases and showed compound 2 to be petunidin-3-O-glucoside. The mass and mass2 spectra and the possible structure formula of the compound are shown in Figure 7.

3.7. Component 3

The peak time of compound 3 was 11.67 min, [M]+m/z was 493.1331 Da, and the fitting formula was C23H25O12+, using the results of high resolution mass spectrometry. According to the second-order mass spectrometry, the parent nucleus of the compound was 331 Da, with one more methylene than the parent nucleus of component 2, making it malvidin. The m/z 331 [M-162] indicated that it included a six-carbon sugar structure. Using the SciFinder and Reaxys databases, the structures of carbohydrate and methoxy groups were retrieved and showed compound 3 to be a malvidin-3-O-glucoside. The mass and mass2 spectra and the possible structure formula of the compound are shown in Figure 8.

4. Discussion

The procedures of SMB and TMB are quite different. The SMB feeding mode is continuous, and the TMB feeding mode is indirect. The SMB control mode is automatic, and the TMB control mode is manual (Table 3). Besides the differences in control devices, there are large differences in operation conditions. For the same resin, the treatment capacity of SMB is five times that of TMB. Under the same daily treatment capacity, the consumption of ethanol and water of SMB was only 0.48 and 0.63 times that of TMB, respectively. There were no significant differences in purity and yield between SMB and TMB separation methods (Table 3). The result was consistent with the principle of ion exchange separation. However, SMB had obvious advantages in industrial production compared with TMB. First, SMB is a continuous operation system of 20 separation columns. The resin in the SMB system had higher utilization rate and higher production efficiency. The TMB is a single column indirect operation system and its resin had a lower utilization rate and lower production efficiency. To achieve the same treatment capacity, SMB would require more than 20 separation columns in the TMB system. The volume of each TMB column was double that of SMB, and the floor area was increased accordingly. The SMB equipment is a well-knit structure, occupying less land, convenient for installation, and uses 1/2-1/3 of the amount of resin of TMB. Second, compared with TMB, the amount of eluent, regenerator, and water used in SMB was 40–60% lower. Finally, the SMB method used automatic control to adjust the parameters at any time according to the needs of the production process to reach an optimal economic state. Comparison of parameters showed that the SMB system had a larger operational capacity, lower solvent consumption, lower cost, higher production efficiency, and continuous production advantage. The SMB method was therefore very suitable for the industrial production of BKBA.


ItemsColumn chromatographySMB chromatography

Chromatographic columns numbers2020
Resin addition5 L5 L
Feeding modeIndirectContinuity
Control modeManualAutomatic
Processing quantity3.6 L/d18 L/d
Alcohol consumption: processing quantity6.4b3.04a
Water consumption: processing quantity9.6b6.08a
BKBA purity (%)24.35 ± 0.16%a24.61 ± 0.21%a
BKBA yield (%)86.76 ± 0.29%a87.85 ± 0.32%a

Letters a and b indicate intergroup differences .

To the best of our knowledge, this is the first report on the purification of BKBA by SMB. Moreover, the antioxidant activities were improved by SMB. This SMB method is of low cost; it is a simple process and a continuous operation, with obvious advantages compared with the combinatorial chromatography [47] and high-speed countercurrent chromatography aqueous two-phase system [48] in industrial production. These results are useful in guiding the industrial production of BKBA. They also provide evidence for the production and application of other agricultural byproducts. However, the results only represented the sample tested and might not be representative of the population of colored kidney beans. The separation and purification parameters of SMB in different cultivars should be tested in the future.

5. Conclusion

To the best of our knowledge, this is the first report on the purification of BKBA by SMB. Moreover, the antioxidant inhibition activities were improved by SMB. These results are useful as guidance for the industrial production of BKBA. It also provided evidence for the production and application of other agricultural byproducts. However, our results only represented the sample we tested and might not necessarily be representative of the population of black kidney bean. The separation and purification parameters of SMB in different cultivars should be tested in the future.

Data Availability

The data used to support the findings of this study are included within the article.

Conflicts of Interest

The authors declare that they have no conflicts of interest.

Acknowledgments

This study was supported by the “Millions” Science and Technology Major Special Project (2019ZX06B02) of Heilongjiang Province, the Engineering Research Center of Processing and Utilization of Grain By-Products, Ministry of Education, Youth Science and Technology Innovation Talents Project (UNPYSCT-2017111) from the Heilongjiang Education Department, and the Key Technology of Corn Functional Sugar Production (2019ZX06B02-1) from the Department of Science and Technology of Heilongjiang.

References

  1. M. P. Hojilla-Evangelista, G. W. Selling, M. A. Berhow, and R. L. Evangelista, “Extraction, composition and functional properties of pennycress (Thlaspi arvense L.) press cake protein,” Journal of the American Oil Chemists’ Society, vol. 92, no. 6, pp. 905–914, 2015. View at: Publisher Site | Google Scholar
  2. Q. He, X. Sun, S. He et al., “PEGylation of black kidney bean (Phaseolus vulgaris L.) protein isolate with potential functional properties,” Colloids and Surfaces B: Biointerfaces, vol. 164, pp. 89–97, 2018. View at: Publisher Site | Google Scholar
  3. N. Sutivisedsak, B. R. Moser, B. K. Sharma et al., “Physical properties and fatty acid profiles of oils from black, kidney, great northern, and pinto beans,” Journal of the American Oil Chemists’ Society, vol. 88, no. 2, pp. 193–200, 2011. View at: Publisher Site | Google Scholar
  4. S. He, J. Shi, E. Walid, Y. Ma, and S. J. Xue, “Extraction and purification of a lectin from small black kidney bean (Phaseolus vulgaris) using a reversed micellar system,” Process Biochemistry, vol. 48, no. 4, pp. 746–752, 2013. View at: Publisher Site | Google Scholar
  5. S. Kumar, A. K. Verma, A. Misra et al., “Allergenic responses of red kidney bean (Phaseolus vulgaris cv chitra) polypeptides in BALB/C mice recognized by bronchial asthma and allergic rhinitis patients,” Food Research International, vol. 44, no. 9, pp. 2870–2879, 2011. View at: Publisher Site | Google Scholar
  6. M. Siddiq, R. Ravi, J. B. Harte, and K. D. Dolan, “Physical and functional characteristics of selected dry bean (Phaseolus vulgaris L.) flours,” LWT-Food Science and Technology, vol. 43, no. 2, pp. 230–237, 2010. View at: Publisher Site | Google Scholar
  7. S.-k. Du, H. Jiang, Y. Ai, and J.-l. Jane, “Physicochemical properties and digestibility of common bean (Phaseolus vulgaris L.) starches,” Carbohydrate Polymers, vol. 108, no. 1, pp. 200–205, 2014. View at: Publisher Site | Google Scholar
  8. S. Gupta, G. S. Chhabra, C. Liu, J. S. Bakshi, and S. K. Sathe, “Functional properties of select dry bean seeds and flours,” Journal of Food Science, vol. 83, no. 8, pp. 2052–2061, 2018. View at: Publisher Site | Google Scholar
  9. M. Dueñas, C. Martínez-Villaluenga, R. I. Limón, E. Peñas, and J. Frias, “Effect of germination and elicitation on phenolic composition and bioactivity of kidney beans,” Food Research International, vol. 70, pp. 55–63, 2015. View at: Publisher Site | Google Scholar
  10. P. X. Chen, H. Zhang, M. F. Marcone et al., “Anti-inflammatory effects of phenolic-rich cranberry bean (Phaseolus vulgaris L.) extracts and enhanced cellular antioxidant enzyme activities in Caco-2 cells,” Journal of Functional Foods, vol. 38, pp. 675–685, 2017. View at: Publisher Site | Google Scholar
  11. B. Xu and S. K. C. Chang, “Total phenolic, phenolic acid, anthocyanin, flavan-3-ol, and flavonol profiles and antioxidant properties of pinto and black beans (Phaseolus vulgaris L.) as affected by thermal processing,” Journal of Agricultural and Food Chemistry, vol. 57, no. 11, pp. 4754–4764, 2009. View at: Publisher Site | Google Scholar
  12. T. Madhujith and F. Hahidi Shahidi, “Antioxidant potential of pea beans (Phaseolus vulgaris L.),” Journal of Food Science, vol. 70, no. 1, pp. S85–S90, 2010. View at: Google Scholar
  13. T. J. Ha, M.-H. Lee, C.-H. Park et al., “Identification and characterization of anthocyanins in yard-long beans (Vigna unguiculata ssp. sesquipedalis L.) by high-performance liquid chromatography with diode array detection and electrospray ionization/mass spectrometry (HPLC-DAD-ESI/MS) analysis,” Journal of Agricultural and Food Chemistry, vol. 58, no. 4, pp. 2571–2576, 2010. View at: Publisher Site | Google Scholar
  14. B. D. Oomah, A. Cardador-Martínez, and G. Loarca-Piña, “Phenolics and antioxidative activities in common beans (Phaseolus vulgaris L.),” Journal of the Science of Food and Agriculture, vol. 85, no. 6, pp. 935–942, 2005. View at: Publisher Site | Google Scholar
  15. L. Mojica, M. Berhow, and E. Gonzalez de Mejia, “Black bean anthocyanin-rich extracts as food colorants: physicochemical stability and antidiabetes potential,” Food Chemistry, vol. 229, pp. 628–639, 2017. View at: Publisher Site | Google Scholar
  16. A. López, T. El-Naggar, M. Dueñas et al., “Effect of cooking and germination on phenolic composition and biological properties of dark beans (Phaseolus vulgaris L.),” Food Chemistry, vol. 138, no. 1, pp. 547–555, 2013. View at: Publisher Site | Google Scholar
  17. C. Jampani, A. Naik, and K. S. M. S. Raghavarao, “Purification of anthocyanins from jamun (Syzygium cumini L.) employing adsorption,” Separation and Purification Technology, vol. 125, no. 4, pp. 170–178, 2014. View at: Publisher Site | Google Scholar
  18. Y. Yang, X. Yuan, Y. Xu, and Z. Yu, “Purification of anthocyanins from extracts of red raspberry using macroporous resin,” International Journal of Food Properties, vol. 18, no. 5, pp. 1046–1058, 2015. View at: Publisher Site | Google Scholar
  19. J. Heinonen, H. Farahmandazad, A. Vuorinen, H. Kallio, B. Yang, and T. Sainio, “Extraction and purification of anthocyanins from purple-fleshed potato,” Food and Bioproducts Processing, vol. 99, no. 7, pp. 136–146, 2016. View at: Publisher Site | Google Scholar
  20. M. Bleve, L. Ciurlia, E. Erroi et al., “An innovative method for the purification of anthocyanins from grape skin extracts by using liquid and sub-critical carbon dioxide,” Separation and Purification Technology, vol. 64, no. 2, pp. 192–197, 2008. View at: Publisher Site | Google Scholar
  21. O. Acosta, F. Vaillant, A. M. Pérez, and M. Dornier, “Potential of ultrafiltration for separation and purification of ellagitannins in blackberry (Rubus adenotrichus Schltdl.) juice,” Separation and Purification Technology, vol. 125, no. 4, pp. 120–125, 2014. View at: Publisher Site | Google Scholar
  22. Y. Liu, N. Murakami, L. Wang, and S. Zhang, “Preparative high-performance liquid chromatography for the purification of natural acylated anthocyanins from red radish (Raphanus sativus L.),” Journal of Chromatographic Science, vol. 46, no. 8, pp. 743–746, 2008. View at: Publisher Site | Google Scholar
  23. X. Wu, L. Liang, Y. Zou et al., “Aqueous two-phase extraction, identification and antioxidant activity of anthocyanins from mulberry (Morus atropurpurea Roxb.),” Food Chemistry, vol. 129, no. 2, pp. 443–453, 2011. View at: Publisher Site | Google Scholar
  24. B. Qin, X. Liu, H. Cui, Y. Ma, Z. Wang, and J. Han, “Aqueous two-phase assisted by ultrasound for the extraction of anthocyanins from Lycium ruthenicum Murr,” Preparative Biochemistry & Biotechnology, vol. 47, no. 9, pp. 881–888, 2017. View at: Publisher Site | Google Scholar
  25. Á. S. Lima, C. M. F. Soares, R. Paltram, H. Halbwirth, and K. Bica, “Extraction and consecutive purification of anthocyanins from grape pomace using ionic liquid solutions,” Fluid Phase Equilibria, vol. 451, no. 11, pp. 68–78, 2017. View at: Publisher Site | Google Scholar
  26. A. Degenhardt, H. Knapp, and P. Winterhalter, “Separation and purification of anthocyanins by high-speed countercurrent chromatography and screening for antioxidant activity,” Journal of Agricultural and Food Chemistry, vol. 48, no. 2, pp. 338–343, 2000. View at: Publisher Site | Google Scholar
  27. R. E. Asenstorfer, A. L. Morgan, Y. Hayasaka, M. Sedgley, and G. P. Jones, “Purification of anthocyanins from species of Banksia and Acacia using high-voltage paper electrophoresis,” Phytochemical Analysis, vol. 14, no. 3, pp. 150–154, 2003. View at: Publisher Site | Google Scholar
  28. S.-q. Cao, S.-y. Pan, X.-l. Yao, and H.-f. Fu, “Isolation and purification of anthocyanins from blood oranges by column chromatography,” Agricultural Sciences in China, vol. 9, no. 2, pp. 207–215, 2010. View at: Publisher Site | Google Scholar
  29. L. G. D’Alessandro, P. Vauchel, R. Przybylski, G. Chataigné, L. Nikov, and K. Dimitrov, “Integrated process extraction adsorption for selective recovery of antioxidant phenolics from Aronia melanocarpa berries,” Separation and Purification Technology, vol. 120, no. 12, pp. 92–101, 2013. View at: Google Scholar
  30. C. Jampani and K. S. M. S. Raghavarao, “Process integration for purification and concentration of red cabbage (Brassica oleracea L.) anthocyanins,” Separation and Purification Technology, vol. 141, no. 2, pp. 10–16, 2015. View at: Publisher Site | Google Scholar
  31. E. Wang, Y. Yin, C. Xu, and J. Liu, “Isolation of high-purity anthocyanin mixtures and monomers from blueberries using combined chromatographic techniques,” Journal of Chromatography A, vol. 1327, no. 1, pp. 39–48, 2014. View at: Publisher Site | Google Scholar
  32. V. Girard, N.-J. Hilbold, C. K. S. Ng et al., “Large-scale monoclonal antibody purification by continuous chromatography, from process design to scale-up,” Journal of Biotechnology, vol. 213, pp. 65–73, 2015. View at: Publisher Site | Google Scholar
  33. G. Iberer, H. Schwinn, D. Josić, A. Jungbauer, and A. Buchacher, “Improved performance of protein separation by continuous annular chromatography in the size-exclusion mode,” Journal of Chromatography A, vol. 921, no. 1, pp. 15–24, 2001. View at: Publisher Site | Google Scholar
  34. J. Zhu, W. Cui, W. Xiao et al., “Isolation and enrichment of Ginkgo biloba extract by a continuous chromatography system,” Journal of Separation Science, vol. 41, no. 11, pp. 2432–2440, 2018. View at: Publisher Site | Google Scholar
  35. L. P. Zhang, Study on a Novel Extraction and Purification Technology of Heparin and Bioactivity of Degraded Heparin, Jilin University, Changchun, China, 2010.
  36. L. Y. Li, D. W. Song, J. J. Diao, P. Y. Jia, and L. P. Zhang, “Adsorption characteristics of AB-8 resin for anthocyanins from Lonicera edulis Turcz,” Natural Product Research and Development, vol. 28, no. 8, pp. 1289–1295, 2016. View at: Google Scholar
  37. H. Z. Wang, Y. Zhu, Y. Zhu et al., “Phenolic composition and antioxidant activity of seed coats of kidney beans with different colors,” Food Science, vol. 41, no. 12, pp. 204–210, 2020. View at: Google Scholar
  38. W. J. Zhao and Y. W. Zhao, “Optimization test on extraction process of anthocyanin pigment from black kidney bean,” Modern Agricultural Science and Technology, vol. 278, no. 16, pp. 244–247, 2016. View at: Google Scholar
  39. L. Li, W. Liu, D. Song, C. Li, P. Jia, and G. Niu, “Simulated moving bed purification for flavonoids from tartary buckwheat shell,” Journal of Chromatographic Science, vol. 58, no. 4, pp. 362–372, 2020. View at: Publisher Site | Google Scholar
  40. Y. Wang, G. Luan, W. Zhou et al., “Subcritical water extraction, UPLC-triple-TOF/MS analysis and antioxidant activity of anthocyanins from Lycium ruthenicum Murr,” Food Chemistry, vol. 249, no. 5, pp. 119–126, 2018. View at: Publisher Site | Google Scholar
  41. C. P. Nie, J. Yang, D. Wu, L. P. Wan, and G. P. Liang, “Inhibitory activities on α-glucosidase and composition analysis of different fractions of ethanol extraction from Actinidia chinensis radix,” Chemical Research in Chinese Universities, vol. 35, no. 10, pp. 823–829, 2019. View at: Publisher Site | Google Scholar
  42. G. Maeda, K. Takara, K. Wada et al., “Evaluation of antioxidant activity of vegetables from Okinawa prefecture and determination of some antioxidative compounds,” Food Science and Technology Research, vol. 12, no. 1, pp. 8–14, 2006. View at: Publisher Site | Google Scholar
  43. M. B. Arnao, A. Cano, and M. Acosta, “The hydrophilic and lipophilic contribution to total antioxidant activity,” Food Chemistry, vol. 73, no. 2, pp. 239–244, 2001. View at: Publisher Site | Google Scholar
  44. H. Zhang, Y.-f. Yang, and Z.-q. Zhou, “Phenolic and flavonoid contents of mandarin (Citrus reticulata Blanco) fruit tissues and their antioxidant capacity as evaluated by DPPH and ABTS methods,” Journal of Integrative Agriculture, vol. 17, no. 1, pp. 256–263, 2018. View at: Publisher Site | Google Scholar
  45. L.-L. Sun, W. Gao, M.-M. Zhang et al., “Composition and antioxidant activity of the anthocyanins of the fruit of Berberis heteropoda Schrenk,” Molecules, vol. 19, no. 11, pp. 19078–19096, 2014. View at: Publisher Site | Google Scholar
  46. H. F. Zhao, W. L. Wu, L. Ma, J. H. Teng, B. Yao, and W. L. Li, “Separation of polyphenols from blueberry based on antioxidative activities,” Science and Technology of Food Industry, vol. 36, no. 5, pp. 251–254, 2015. View at: Google Scholar
  47. N. Chorfa, S. Savard, and K. Belkacemi, “An efficient method for high-purity anthocyanin isomers isolation from wild blueberries and their radical scavenging activity,” Food Chemistry, vol. 197, pp. 1226–1234, 2016. View at: Publisher Site | Google Scholar
  48. Y. Wu, Y. Wang, W. Zhang et al., “Extraction and preliminary purification of anthocyanins from grape juice in aqueous two-phase system,” Separation and Purification Technology, vol. 124, no. 6, pp. 170–178, 2014. View at: Publisher Site | Google Scholar

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