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Supercritical CO2 extraction, chemical composition, and antioxidant effects of Coreopsis tinctoria Nutt. oleoresin

  • Yiyi Qiu and Hui Ruan EMAIL logo
Published/Copyright: August 8, 2022
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Open Life Sciences
From the journal Open Life Sciences Volume 17 Issue 1

Abstract

Coreopsis tinctoria Nutt. was used to extract oleoresin through supercritical CO2 extraction technology. The extraction conditions were optimized using response surface methodology, and the chemical composition of C. tinctoria Nutt. oleoresin (CTO) was analyzed. Under the optimal conditions, the antioxidant activity of oleoresin was determined using 1,1-diphenyl-2-picrylhydrazyl (DPPH˙) and 2,2′-azino-bis-(3-ethylbenzo-thiazoline-6-sulphonic acid)diammonium salt (ABTS˙+) free radical scavenging assays. The optimal extraction conditions were a 27.5 MPa extraction pressure, a 45°C extraction temperature, and a 3 h extraction time. Under these extraction conditions, oleoresin yield was up to 3.163%. Compared to steam distillation extraction, the CTO extracted using supercritical CO2 had more abundant components. The EC50 of CTO for DPPH˙ and ABTS˙+ free radical scavengers was 1.54 and 1.07 mg/mL, respectively.

Keywords: Coreopsis tinctoria Nutt.; oleoresin; supercritical fluid extraction; response surface methodology; antioxidant activities

1 Introduction

Coreopsis tinctoria Nutt., an annual herb widely distributed in North America, Central Asia, the Middle East, and Eastern Europe [1], grows in plateau areas in Xinjiang province, China. It is commonly known as Kunlun Snow Chrysanthemum because it grows all year in the snow-covered northern foothills of the Kunlun Mountains. Local Uyghurs refer to it as “Gulqai,” and it is used as a traditional medicine to prevent and treat hypertension and hyperlipidemia. Recent studies have reported that C. tinctoria has various biological activities, including hypoglycemic, hypotensive, anti-inflammatory, antioxidant, anticancer, antiaging, and antibacterial activities [2,3,4].

Oleoresin is a generic term for a kind of substance obtained from plants through oil dissolution, organic solvent extraction [5], three-phase partitioning [6], and supercritical fluid extraction (SFE) [7], which is composed of both volatile essential oils and nonvolatile compounds, such as pigments and fatty acids. Since oleoresin contains some natural antioxidants in the corresponding plants, it is more stable than essential oils [8]. According to literature reports, the supercritical extraction of oleoresin focused largely on spices like garlic, pepper (jalapeno) [9], and onion [10], among others. For spices, oleoresin better reflects flavor characteristics than essential oils obtained through hydrodistillation [11]. Furthermore, some studies have reported that oleoresin has stronger antioxidant and antimicrobial effects than essential oils [12,13,14]. While many studies are currently focusing on the flavonoids and polysaccharides of C. tinctoria, there are few studies devoted to C. tinctoria oleoresin (CTO), and challenges such as low extraction efficiency and poor application are common in research and development. Thus, it is important to optimize the extraction method and investigate its chemical composition for future studies.

The relative abundance of bioactive compounds in extracts from plant-derived sources depends on the extraction technique implemented [15]. Conventional organic solvent extraction, such as the Soxhlet extraction of oleoresins, has been widely adopted for its simplicity and economy. However, when compared to other extraction techniques, it is limited by its low efficiency and the large volume of solvents. Besides, its high operating temperatures are a major limitation, resulting in the formation of artifacts and the degradation of temperature-sensitive natural products [16].

Contrary to conventional extraction, supercritical CO2 extraction technology has a low extraction temperature, no toxic residue, and selective separation ability [17]. Therefore, it is particularly suitable for separating and extracting bioactive compounds with low concentration or low stability. The supercritical CO2 extraction technique was widely used for extra caffeine or decaffeination of tea at the industrial level [18,19], bringing high economic and medical value. Certainly, various researchers have produced plant oleoresin using supercritical CO2 extraction technology. Shukla et al. reported the supercritical CO2 extraction and online fractionation of dry ginger for the production of high-quality volatile oil and gingerol-enriched oleoresin, and the scale-up validation of this process has been achieved [20], revealing the potential of this technology. However, the insufficiencies caused by carbon dioxide emissions in this extraction process should be noted. It is a little contrary to the “low-carbon” concept. Thus, supercritical CO2 recycling is predicted to be a focus of studies.

In this study, the SFE of the CTO was optimized using the response surface methodology. Notably, we did not use co-solvents to accelerate extraction in this study, thereby substantially retaining the flavonoids and polysaccharides. The chemical composition of CTO was analyzed and compared with that of C. tinctoria essential oils (CTEOs). Furthermore, the antioxidant effects of CTO were determined through 1,1-diphenyl-2-picrylhydrazyl (DPPH˙) and 2,2′-azino-bis-(3-ethylbenzo-thiazoline-6-sulphonic acid)diammonium salt (ABTS˙+) free radical scavenging assays. We hope that this study provides basic data for high-value processing and utilization of C. tinctoria.

2 Materials and methods

2.1 Materials

Coreopsis tinctoria Nutt. (originated from Hetian, Xinjiang, batch number: 20190617-KLXJ) was purchased from Tongxiang Haitai Juye Co., Ltd. The DPPH kit was purchased from Sangon Biotech (Shanghai) Co., Ltd. The ABTS kit was bought from Beyotime Institute of Biotechnology, China. Dichloromethane and ethanol (analytical grade) were purchased from Sinopharm Chemical Reagent Co., Ltd, China.

2.2 Hydrodistillation extraction of CTEOs

The flowers of C. tinctoria Nutt. were dried in an oven at 60°C to a constant weight. Subsequently, they were hydrodistilled at a solid–liquid ratio of 1:10 for essential oil extraction.

2.3 SFE of CTO

The SFE was conducted on a laboratory-scale supercritical system (SFE-2; Applied Separations Inc., Pennsylvania, USA). The flowers of C. tinctoria Nutt. were dried in the oven at 60°C to a constant weight, and a certain amount of flower powder was pressed into the extraction vessel with degreasing cotton at both ends. The flow rate of carbon dioxide was fixed at 20 L/h. Different extraction pressures, temperatures, and times were chosen for single-factor experiments (Table 1). The oleoresin yield (Y) was calculated using the following equation:

(1) Y = m 1 / m 2 × 100 % ,

where m 1 (g) is the weight of the extracted oleoresin and m 2 (g) is the weight of the sample C. tinctoria used.

Table 1

Factors and levels in single factor experiment

Level Time (h) Pressure (MPa) Temperature (°C)
1 0.5 15 35
2 1 20 40
3 1.5 25 45
4 2 30 50
5 2.5 35 55
6 3 — —

2.4 Response surface methodology experimental design

Based on the results of the single-factor experiment, a three-variable Box–Behnken design with three coded levels was implemented to rapidly determine the optimal conditions for supercritical extraction. Scientific software Design-Expert (version 10.0.8.0; Stat-Ease Inc., Minneapolis, MN, USA) was employed for the experimental design. Three independent variables, extraction time (X 1), extraction pressure (X 2), and temperature (X 3), were modified. The experimental range and the coded values of the three independent variables are listed in Table 2. The quadratic polynomial model proposed by the response surface methodology analysis for predicting the optimal combination can be expressed as the following equation:

(2) Y = β 0 + ∑ β i X i + ∑ β i i X i 2 + ∑ β i j X i X j ,

where Y is the yield of CTO; β 0, β i , β ii , and β ij are the regression coefficients for the intercept, linear, quadratic, and interaction terms, respectively; and X i and X j are the independent variables – time, temperature, and pressure. The significance of the model was evaluated, and the regression coefficient (R 2) was obtained.

Table 2

Factors and levers in the Box–Behnken experimental design

Level X 1 (time, h) X 2 (pressure, MPa) X 3 (temperature, °C)
−1 1 20 35
0 2 25 45
1 3 30 55

2.5 Chemical composition of CTEOs and CTO

GC-MS (7890B/7000C; Agilent Technologies, Palo Alto, PA, USA) was employed for the chemical composition analysis of CTO and CTEO, and an Agilent silica capillary column HP-5MS (30 m × 0.25 mm × 0.25 µm) was also used. For the chromatographic conditions, we followed the study by Wu et al. [21]. For the heating program, the initial temperature was set at 80°C and held for 3 min. Subsequently, the column was heated to 200°C at an 8°C/min rate and held for 5 min before being programmed to 260°C at an 8°C/min rate and held for 2 min. The sample solution was injected under a nitrogen atmosphere with a 10 mL/min flow rate. The sample dilution solution was prepared by dissolving a certain amount of CTO or CTEO in dichloromethane and then filtering it using a 0.22 µm membrane. An aliquot (1 µL) of sample dilution solution was injected under a helium carrier gas with a 1 mL/min flow rate, and the split ratio was fixed at 10:1. For the mass spectrometry conditions, the electron impact ion source energy was set as 70 eV, the ion source temperature was fixed at 250°C, and the mass scan range was m/z 30–600. Mass Hunter software (Agilent Technologies, Palo Alto, USA) was used for data analysis.

2.6 Antioxidant capability assay

2.6.1 DPPH˙ free radical scavenging rate

The DPPH˙ free radical scavenging rate assay of CTO was conducted following Wu et al.’s [22] method, with minor modifications. CTO dissolved in dichloromethane was diluted to 0.15, 0.3, 0.6, 3, 6, 9, 12, and 18 mg/mL and mixed with equal volumes of DPPH˙ solution (0.1 mmol/L). The mixture was incubated in the dark for 30 min, and the absorbance at 519 nm was assayed. Dichloromethane was used as a control. Each measurement was conducted in triplicate. The DPPH˙ scavenging rates of the samples were calculated using the following equation:

(3) DPPH ˙ scavenging rate ( % ) = ( A 0 − A 1 ) / A 0 × 100 % ,

where A 0 and A 1 represent the absorbance of the control and the sample, respectively.

2.6.2 ABTS˙+ free radical scavenging rate

The ABTS˙+ free radical scavenging rate was determined using a rapid assay kit (Sangon Biotech, Shanghai, China) following Luo et al. [23]. First, the ABTS˙+ solution was mixed with an oxidant solution at equal volume to prepare the working stock solution. Second, the stock solution was incubated at 20–25°C in the dark for 12–16 h and then diluted with dichloromethane solution to 0.7 absorbance at 734 nm before use. Third, 10 µL of the diluted working solution was added to the sample solution to achieve final concentrations of 0.15, 0.3, 0.6, 3, 6, 9, 12, and 18 mg/mL and then incubated at 20–25°C for 4 min. Finally, the absorbance at 734 nm was determined. Each measurement was conducted in triplicate. The ABTS˙+ antioxidant effects can be calculated using the following equation:

(4) ABTS ˙ + free radical scavenging rate ( % ) = ( A 0 − A 1 ) / A 0 × 100 % ,

where A 0 and A 1 represent the absorbance of the control and the sample, respectively.

2.6.3 EC50 estimation of antioxidant activity

EC50 estimation of antioxidant activity in DPPH˙ and ABTS˙+ assays using statistical programs based on Origin Pro 9.1 [24].

2.7 Statistical analysis

All experiments were implemented in triplicate. The differences between the mean values were analyzed by the Duncan test using SPSS Statistics 20 (IBM, Armonk, NY, USA). P < 0.05 was considered a statistically significant difference.

3 Results and discussion

3.1 Effects of variables on supercritical carbon dioxide extraction

The effects of each variable on the supercritical CO2 extraction of CTO were investigated using single-factor experiments. The results are shown in Figure 1. The effects of extraction time on the yield of CTO were studied under the following conditions: 45°C extraction temperature, 35 MPa extraction pressure, and 20 L/h CO2 flow rate. As shown in Figure 1a, the yield of CTO increased, but the extraction speed decreased with the extension of the extraction time. During the experiment, we also noticed that the color of CTO became darker as time increased. Although we set the experiment as a dynamic extraction, there was still some time before the temperature and the pressure were processed to the set value. This extended the extraction time and created a static extraction period; thus, the yield reached 50% of the total yield before 0.5 h. Barjaktarović et al. [25] studied the impact of time and pressure on the supercritical CO2 extracts of Juniperus communis L. fruits and proposed that 0–0.5 h is the “initial fast extraction period.” This is consistent with this study. Apart from the oleoresin yield, the extraction time can also affect the composition of oleoresins. Therefore, cost, efficiency, and component requirements should be considered when determining the extraction time. In this study, we chose 3 h for further investigation.

The impact of temperature is displayed in Figure 1c. Clearly, the yield reaches its maximum, and higher or lower temperatures result in lower yields. When the extraction temperature is lower than 45°C, a higher temperature means accelerated molecular thermal motion, increased coefficient of mass transfer, and greater volatility and diffusion speed, which induce a higher CTO yield. However, temperatures higher than 45°C will lower the solubility of CO2 by decreasing its density. Furthermore, excessively high temperatures will destroy CTO, which is highly volatile and heat sensitive. Thus, 45oC was selected as the center point in the response surface methodology.

After the time and temperature of the center point had been chosen, the effect of extraction pressure was investigated. The pressure was fixed at 10, 15, 20, 25, and 30 MPa when the time, temperature, and CO2 flow rate were set at 3 h, 45°C, and 20 L/h. The results are shown in Figure 1b. When the extraction pressure was between 10 and 25 MPa, a higher pressure would increase the density of supercritical CO2, which has greater solubility for oleoresins. In addition, high pressure acting on materials in the vessel may accelerate the dissolution of the CTO. When pressure is higher than 25 MPa, the yield of CTO shows a downward trend. This may be due to the decrease in CO2 fluid mobility caused by high pressure over a certain value [26]. In addition, the color of the CTO becomes darker with the increased pressure, indicating that the pressure also influences the components of the CTO. Gaspar [27] discovered that as the pressure increases, more phytowax would be extracted and cause the deterioration of plant oil. Consequently, we chose 20, 25, and 30 MPa for the response surface methodology.

Figure 1 Effects of extraction time, extraction pressure, and extraction temperature on the yield of CTO.
Figure 1

Effects of extraction time, extraction pressure, and extraction temperature on the yield of CTO.

3.2 Optimization of CTO SFE using response surface methodology

A three-level Box–Behnken design with three variances was constructed, setting extraction time (X 1), extraction temperature (X 2), and extraction pressure (X 3) as the variances and the CTO yield as the response value (Y), leading to 17 sets of experiments with five replicates at the center point. The results are listed in Table 3. We used Design-Expert to process the data by polynomial regression and generated the following polynomial quadratic equation:

(5) Y = 3.11 + 0.21 X 1 + 0.26 X 2 + 0.15 X 3 − 0.025 X 1 X 2 − 0.027 X 1 X 3 − 0.15 X 2 X 3 − 0.2 X 1 2 − 0.31 X 2 2 − 0.25 X 3 2 .

Table 3

Design and its results for the surface methodology experiment

Runs X 1 X 2 X 3 Y (yield, %)
1 0 1 1 2.81
2 0 −1 −1 1.97
3 0 1 −1 2.74
4 0 −1 1 2.64
5 1 0 1 2.99
6 −1 0 −1 2.27
7 1 0 −1 2.80
8 −1 0 1 2.57
9 1 1 0 3.04
10 −1 −1 0 2.10
11 1 −1 0 2.53
12 −1 1 0 2.71
13 0 0 0 3.03
14 0 0 0 3.07
15 0 0 0 3.13
16 0 0 0 3.14
17 0 0 0 3.16

Table 4 demonstrates the results of the analysis of variance. The p-value of this model is lower than 0.0001, indicating that the polynomial quadratic equation constructed by this model is extremely significant. The coefficient of determination (R 2) is 0.9869, which indicates a good fit, and 98.69% of the variability in the response originates from the selected variances [28]. The adjusted coefficient of determination (R 2 adj) is 0.9701, suggesting that 2.99% of the total variation could not be explained by the model. The lack of fit is not significant at α = 0.05, indicating that the residual is caused by errors, and the model can be used for result prediction. The visualization of the generated equation is displayed by response surfaces in Figure 2.

Table 4

Results of the response surface methodology regression analysis for CTO yield

Source Sum of squares df Mean square F-value p-value Significance
Model 2.12 9 0.24 58.71 <0.0001 Significant
X 1 0.37 1 0.37 91.07 <0.0001 ***
X 2 0.53 1 0.53 132.16 <0.0001 ***
X 3 0.19 1 0.19 47.12 0.0002 ***
X 1 X 2 2.500 × 10−3 1 2.500 × 10−3 0.62 0.4559
X 1 X 3 3.025 × 10−3 1 3.025 × 10−3 0.75 0.4141
X 2 X 3 0.090 1 0.090 22.42 0.0021 **
X 1 2 0.16 1 0.16 40.61 0.0004 **
X 2 2 0.42 1 0.42 103.60 <0.0001 ***
X 3 2 0.27 1 0.27 66.49 <0.0001 ***
Residual 0.028 7 4.014 × 10−3
Lack of fit 0.016 3 5.458 × 10−3 1.86 0.2766 Not significant
Pure error 0.012 4 2.930 × 10−3
Cor total 2.15 16
R 2 0.9869
R 2 Adj 0.9701

Notes: ***extremely significant (p < 0.0001); **highly significant (p < 0.01); *significant (p < 0.05).

In the model, X 1, X 2, and X 3 are all extremely significant, and the order ranked according to their p-value is as follows: X 2 (extraction pressure) > X 1 (extraction time) > X 3 (extraction temperature). The influence of variances can also be interpreted by the response surface and the contour plots. Each response surface and its corresponding contour plots represent the effect and mutual interaction of two variances against the response. From Figure 2a and b, with the increase of time or pressure, the yield of CTO first increased and then diminished. The change resulting from a pressure boost is more powerful than that of the time, suggesting that the extraction pressure has a more significant impact on the CTO yield. Figure 2c and d illustrates the effects of time and temperature. Clearly, time is slightly stronger than temperature. Figure 2e and f advocates that the pressure is a much more effective variance than the temperature. A high temperature would lead to a greater Brownian motion, beneficial to oleoresin extraction. Similarly, high pressure will enhance the solvation effect of CO2 fluid and further boost the CTO yield. However, excessively high temperature and pressure would hinder the dissolution of the CTO.

For the quadratic model generated by the response surface methodology, the first derivate of the equation can be applied to access the optimal conditions [29]. In this study, we employed Design-Expert for the calculation. The optimal condition was as follows: 27.5 MPa extraction pressure, 45.69°C extraction temperature, and 3 h extraction time. The predicted highest CTO yield was 3.163%. Considering the limitations in practice, we fixed the conditions at 27.5 MPa extraction pressure, 46°C extraction temperature, and 3 h extraction time. Under these conditions, we performed the extraction in triplicate, and the average value was 3.165%, which is consistent with the predicted value. In conclusion, the conditions optimized by the response surface methodology have good reliability and application value.

Liu et al. [30] extracted CTO under 60°C, 25 MPa, and 45 L/h CO2 flow rate for 1 h, and the yield was 11. 59% ± 0. 37%. The absolute value of the olefin content in the report was similar to that of this study, implying that Liu et al. might obtain more vegetable wax under a higher temperature. In addition, high temperature has negative effects on the quality of olefins. Thus, the CTO extracted by the present study may have higher olefin content and more potent antioxidant or antibacterial activities.

Figure 2 Response surface and contour line for predicted equation: (a and b) time and pressure (c and d) time and temperature, and (e and f) pressure and temperature.
Figure 2

Response surface and contour line for predicted equation: (a and b) time and pressure (c and d) time and temperature, and (e and f) pressure and temperature.

3.3 Chemical composition comparison between CTO and CTEOs

GC-MS was implemented for the chemical composition analysis of CTO and CTEO. Data were processed by the normalization method in Mass Hunter loaded with the NIST 11.L library. The main components detected by the GC-MS of CTO and CTEO are shown in Table 5. CTO and CTEO have a significant difference in their chemical compositions – 49 compounds were detected in CTO, whereas only 32 compounds were distinguished in CTEO. In addition, SEF extraction obtained more alkenes than steam distillation extraction (calculated by the alkenes yield per unit material mass). However, CTEO has more kinds of alkenes than CTO. Those alkenes not detected in CTO are also relatively low in CTEO; hence, they may exist in CTO but become undetectable by GC–MS.

Table 5

Main chemical components of Coreopsis tinctoria Nutt. extracted by SFE

No. Compound CTO (%) CTEO (%)
1 γ-Terpinene 7.47
2 Camphene 0.13
3 3-Carene 0.16
4 (+)-3-Carene 1.11
5 o-Cymene 1.88 16.54
6 p-Cymene 0.43
7 d-Limonene 8.21 40.69
8 Acetophenone 0.86
9 γ-Terpinene 0.29
10 Carveol 2.55 5.71
11 (−)-Carvone 1.15 3.23
12 2,4,6-Trimethylbenzyl alcohol 0.45
13 Tricyclo[5.2.1.0(1,5)]decane 0.17
14 Cyclohexane, 2-ethenyl-1,1-dimethyl-3-methylene- 0.13
15 Bicyclo[3.1.0]hexan-3-ol, 4-methylene-1-(1-methylethyl)-, [1S-(1α,3β,5α)]- 0.69
16 1,2-Dimethyl- 1.24
17 α-Campholenal 0.46
18 1,3,8-p-Menthatriene 1.17
19 4-Terpinenyl acetate 0.45
20 2,4-Dimethylstyrene 0.44
21 β-Humulene 0.18
22 1,2-Cyclohexanediol, 1-methyl-4-(1-methylethenyl)- 2.35
23 Epiglobulol 0.14
24 Lanceol 0.18
25 (−)-β-Chamigrene 0.12
26 Di-epi-α-cedrene 0.26
27 γ-Himachalene 0.19 3.75
28 Caryophyllene 0.21
29 δ-Selinene 0.21
30 Cis-sesquisabinene hydrate 0.14
31 Ascaridole epoxide 0.18
32 1,5,5-Trimethyl-6-methylene-cyclohexene 0.25
33 1,4-Cyclohexadiene, 3-ethenyl-1,2-dimethyl- 1.24
34 Thymol 0.28
35 Bicyclo[5.2.0]nonane, 2-methylene-4,8,8-trimethyl-4-vinyl- 0.15
36 Bicyclo[3.1.1]hept-2-ene, 2,6-dimethyl-6-(4-methyl-3pentenyl) 2.39
37 Naphthalene 0.16
38 3-Cyclohexene-1-acetaldehyde, α,4-dimethyl- 0.33
39 Benzene, 1-(1,5-dimethyl-4-hexenyl)-4-methyl 0.31 0.69
40 γ-Muurolene 1.64
41 Dodecanoic acid 0.12
42 Trans-Z-α-bisabolene epoxide 0.06
43 Trans-longipinocarveol 0.10
44 (−)-Spathulenol 0.27
45 Alloaromadendrene oxide 0.59
46 Aromadendrene oxide 0.08
47 Aromadendrene, dehydro- 0.18
48 Isoaromadendrene epoxide 0.07
49 Tricyclo[6.3.0.0(1,5)]undec-2en-4-one, 2,3,5,9-tetramethyl- 0.58
50 Fluorene 3.89 4.95
51 Trans-longipinocarveol 0.22
52 Ledene oxide-(II) 0.15
53 Berkheyaradulene 0.24
59 Phytol, acetate 0.45
60 9,12-Octadecadienoic acid (Z, Z) 4.01
61 9,12,15-Octadecatrienoic acid, (Z, Z, Z) 2.04
62 Eicosane 1.88
63 Behenic alcohol 5.03
64 Heneicosane 5.94 0.72
65 1-Dodecanol, 2-octyl 16.21
66 Squalene 1.88
67 Acetic acid, chloro-, octadecyl ester 2.15
68 Pentacosane 14.07
69 Tetradecane, 2,6,10-trimethyl 1.59
70 Tetracosane 5.28
71 Phytol 0.94 0.24
Total 91.67 93.22

2-Octyl-1-dodecanol, pentacosane, and d-limonene are the three most abundant compounds in CTO, accounting for 16.21, 14.07, and 8.21% of the total peak area. 2-Octyl-1-dodecanol and pentacosane are waxes of plant cuticles [31]. 2-Octyl-1-dodecanol can be used as an emulsifier, solvent, and thickening agent, indicating the further exploitation of C. tinctoria. Pentacosane is a kind of higher aliphatic hydrocarbon that is common in plant SFE extract. d-Limonene is the highest compound in CTO alkenes, accounting for 18.15% of the total peak area. It is a monoterpene with several biological activities, including antioxidant, anticancer, asthmatic, anti-inflammatory, and antimicrobial effects [32], and has been widely applied as a food preservative [33]. γ-Muurolene and o-cymene are also important contents in CTO, accounting for 1.88 and 1.64%, respectively. γ-Muurolene, a sesquiterpene that is rich in Cananga odorata (Lam.) Hook.f. & Thomson and birch bud essential oils, is famous for its special scent. o-Cymene and its isomer, p-cymene, are derivatives of α-pinene and play a synergistic role in the antibacterial process of Thymus mongolicus Ronn essential oils [34]. Free fatty acids and fatty acid esters are two other kinds of important compounds in CTO, accounting for 7.76% of the total peak area, including linoleic acid, linolenic acid, and lauric acid. Reportedly, these free fatty acids are bioactive compounds. For instance, linoleic acid has a potent antibacterial effect against Mycobacterium tuberculosis in the MGIT 960 system, and its minimum inhibitory concentration is 200 μg/mL [35]. It is noteworthy that acetic acid, chloro-, octadecyl ester is unlikely to be found naturally in C. tinctoria Nutt. This may be due to environmental contamination or a mismatch in the libraries. Further study is needed to confirm the origin of this substance.

3.4 Antioxidant activities

The DPPH˙ and ABTS˙+ free radical scavenging capabilities of CTO were assayed, and Trolox was used as the positive control. The results are displayed in Figure 3. Evidently, CTO has a strong free radical scavenging capacity, and its EC50 against DPPH˙ and ABTS˙+ is 1.54 and 1.07 mg/mL, respectively. In earlier reports, SFE extracts always exhibit high antioxidant effects due to their mild extraction conditions and protection by supercritical CO2 [36,37]. Teixeira et al. [38] tested 17 kinds of commercial essential oils and found that while seven essential oils had EC50 ranging from 0.04 mg/mL to 10.4 mg/mL, others had almost no antioxidant capacity. In contrast, CTO has a strong antioxidant capacity. However, several studies have reported that oleoresins from different plants have a much more potent DPPH˙ free radical scavenging ability than the CTO extracted in this study [5,39,40], which may be due to the differences in extraction methods. The solvent extraction they used could extract many nonvolatile antioxidant compounds, such as flavones, leading to high free radical scavenging rates. The relatively low scavenging rate of CTO suggests that the SFE conditions optimized in this study did not extract flavones and other similar compounds. Thus, the flowers that have been extracted by SFE to obtain oleoresin can be used for further flavonoid extraction.

Figure 3 DPPH˙ free radical scavenging rate (a) and ABTS˙+ free radical scavenging rate (b) of CTO.
Figure 3

DPPH˙ free radical scavenging rate (a) and ABTS˙+ free radical scavenging rate (b) of CTO.

4 Conclusion

In conclusion, this study constructed a CTO SFE extraction method with conditions optimized using response surface methodology. The optimal conditions were 27.5 MPa as the extraction pressure, 45.69°C as the extraction temperature, and 3 h as the extraction time. The maximum CTO yield was 3.163%. The chemical composition of CTO was analyzed and compared with that of CTEO. Furthermore, the antioxidant effects of CTO were determined through DPPH˙ and ABTS˙+ free radical scavenging assays. CTO had more abundant components than CTEO and had higher alkene content. The antioxidant activities of CTO were excellent, and its EC50 against DPPH˙ and ABTS˙+ was 1.54 and 1.07 mg/mL, respectively. We hope this study provides theoretical guidance for CTO extraction and new insights into the further exploitation and application of C. tinctoria.

  1. Funding information: This study was supported by the Zhejiang Provincial Public Welfare Technology Application Research Project (No. LGF18C200002) and the Scientific and Technology Project of Zhejiang Province, China (No. 2017C26004).

  2. Conflict of interest: Authors state no conflict of interest.

  3. Data availability statement: The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

Appendix

Figure A1 GC-MS chromatograms of CTO (a) and CTEO (b).
Figure A1

GC-MS chromatograms of CTO (a) and CTEO (b).

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Received: 2022-02-16
Revised: 2022-04-30
Accepted: 2022-05-03
Published Online: 2022-08-08

© 2022 Yiyi Qiu and Hui Ruan, published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/biol-2022-0092
Keywords for this article
Coreopsis tinctoria Nutt.; oleoresin; supercritical fluid extraction; response surface methodology; antioxidant activities
Creative Commons
BY 4.0

Articles in the same Issue

  1. Biomedical Sciences
  2. Effects of direct oral anticoagulants dabigatran and rivaroxaban on the blood coagulation function in rabbits
  3. The mother of all battles: Viruses vs humans. Can humans avoid extinction in 50–100 years?
  4. Knockdown of G1P3 inhibits cell proliferation and enhances the cytotoxicity of dexamethasone in acute lymphoblastic leukemia
  5. LINC00665 regulates hepatocellular carcinoma by modulating mRNA via the m6A enzyme
  6. Association study of CLDN14 variations in patients with kidney stones
  7. Concanavalin A-induced autoimmune hepatitis model in mice: Mechanisms and future outlook
  8. Regulation of miR-30b in cancer development, apoptosis, and drug resistance
  9. Informatic analysis of the pulmonary microecology in non-cystic fibrosis bronchiectasis at three different stages
  10. Swimming attenuates tumor growth in CT-26 tumor-bearing mice and suppresses angiogenesis by mediating the HIF-1α/VEGFA pathway
  11. Characterization of intestinal microbiota and serum metabolites in patients with mild hepatic encephalopathy
  12. Functional conservation and divergence in plant-specific GRF gene family revealed by sequences and expression analysis
  13. Application of the FLP/LoxP-FRT recombination system to switch the eGFP expression in a model prokaryote
  14. Biomedical evaluation of antioxidant properties of lamb meat enriched with iodine and selenium
  15. Intravenous infusion of the exosomes derived from human umbilical cord mesenchymal stem cells enhance neurological recovery after traumatic brain injury via suppressing the NF-κB pathway
  16. Effect of dietary pattern on pregnant women with gestational diabetes mellitus and its clinical significance
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  18. Effect of the genetic mutant G71R in uridine diphosphate-glucuronosyltransferase 1A1 on the conjugation of bilirubin
  19. Quercetin inhibits cytotoxicity of PC12 cells induced by amyloid-beta 25–35 via stimulating estrogen receptor α, activating ERK1/2, and inhibiting apoptosis
  20. Nutrition intervention in the management of novel coronavirus pneumonia patients
  21. circ-CFH promotes the development of HCC by regulating cell proliferation, apoptosis, migration, invasion, and glycolysis through the miR-377-3p/RNF38 axis
  22. Bmi-1 directly upregulates glucose transporter 1 in human gastric adenocarcinoma
  23. Lacunar infarction aggravates the cognitive deficit in the elderly with white matter lesion
  24. Hydroxysafflor yellow A improved retinopathy via Nrf2/HO-1 pathway in rats
  25. Comparison of axon extension: PTFE versus PLA formed by a 3D printer
  26. Elevated IL-35 level and iTr35 subset increase the bacterial burden and lung lesions in Mycobacterium tuberculosis-infected mice
  27. A case report of CAT gene and HNF1β gene variations in a patient with early-onset diabetes
  28. Study on the mechanism of inhibiting patulin production by fengycin
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  30. Relationship between blood clots and COVID-19 vaccines: A literature review
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  32. Bioinformatics network analyses of growth differentiation factor 11
  33. NR4A1 inhibits the epithelial–mesenchymal transition of hepatic stellate cells: Involvement of TGF-β–Smad2/3/4–ZEB signaling
  34. Expression of Zeb1 in the differentiation of mouse embryonic stem cell
  35. Study on the genetic damage caused by cadmium sulfide quantum dots in human lymphocytes
  36. Association between single-nucleotide polymorphisms of NKX2.5 and congenital heart disease in Chinese population: A meta-analysis
  37. Assessment of the anesthetic effect of modified pentothal sodium solution on Sprague-Dawley rats
  38. Genetic susceptibility to high myopia in Han Chinese population
  39. Potential biomarkers and molecular mechanisms in preeclampsia progression
  40. Silencing circular RNA-friend leukemia virus integration 1 restrained malignancy of CC cells and oxaliplatin resistance by disturbing dyskeratosis congenita 1
  41. Endostar plus pembrolizumab combined with a platinum-based dual chemotherapy regime for advanced pulmonary large-cell neuroendocrine carcinoma as a first-line treatment: A case report
  42. The significance of PAK4 in signaling and clinicopathology: A review
  43. Sorafenib inhibits ovarian cancer cell proliferation and mobility and induces radiosensitivity by targeting the tumor cell epithelial–mesenchymal transition
  44. Characterization of rabbit polyclonal antibody against camel recombinant nanobodies
  45. Active legumain promotes invasion and migration of neuroblastoma by regulating epithelial-mesenchymal transition
  46. Effect of cell receptors in the pathogenesis of osteoarthritis: Current insights
  47. MT-12 inhibits the proliferation of bladder cells in vitro and in vivo by enhancing autophagy through mitochondrial dysfunction
  48. Study of hsa_circRNA_000121 and hsa_circRNA_004183 in papillary thyroid microcarcinoma
  49. BuyangHuanwu Decoction attenuates cerebral vasospasm caused by subarachnoid hemorrhage in rats via PI3K/AKT/eNOS axis
  50. Effects of the interaction of Notch and TLR4 pathways on inflammation and heart function in septic heart
  51. Monosodium iodoacetate-induced subchondral bone microstructure and inflammatory changes in an animal model of osteoarthritis
  52. A rare presentation of type II Abernethy malformation and nephrotic syndrome: Case report and review
  53. Rapid death due to pulmonary epithelioid haemangioendothelioma in several weeks: A case report
  54. Hepatoprotective role of peroxisome proliferator-activated receptor-α in non-cancerous hepatic tissues following transcatheter arterial embolization
  55. Correlation between peripheral blood lymphocyte subpopulations and primary systemic lupus erythematosus
  56. A novel SLC8A1-ALK fusion in lung adenocarcinoma confers sensitivity to alectinib: A case report
  57. β-Hydroxybutyrate upregulates FGF21 expression through inhibition of histone deacetylases in hepatocytes
  58. Identification of metabolic genes for the prediction of prognosis and tumor microenvironment infiltration in early-stage non-small cell lung cancer
  59. BTBD10 inhibits glioma tumorigenesis by downregulating cyclin D1 and p-Akt
  60. Mucormycosis co-infection in COVID-19 patients: An update
  61. Metagenomic next-generation sequencing in diagnosing Pneumocystis jirovecii pneumonia: A case report
  62. Long non-coding RNA HOXB-AS1 is a prognostic marker and promotes hepatocellular carcinoma cells’ proliferation and invasion
  63. Preparation and evaluation of LA-PEG-SPION, a targeted MRI contrast agent for liver cancer
  64. Proteomic analysis of the liver regulating lipid metabolism in Chaohu ducks using two-dimensional electrophoresis
  65. Nasopharyngeal tuberculosis: A case report
  66. Characterization and evaluation of anti-Salmonella enteritidis activity of indigenous probiotic lactobacilli in mice
  67. Aberrant pulmonary immune response of obese mice to periodontal infection
  68. Bacteriospermia – A formidable player in male subfertility
  69. In silico and in vivo analysis of TIPE1 expression in diffuse large B cell lymphoma
  70. Effects of KCa channels on biological behavior of trophoblasts
  71. Interleukin-17A influences the vulnerability rather than the size of established atherosclerotic plaques in apolipoprotein E-deficient mice
  72. Multiple organ failure and death caused by Staphylococcus aureus hip infection: A case report
  73. Prognostic signature related to the immune environment of oral squamous cell carcinoma
  74. Primary and metastatic squamous cell carcinoma of the thyroid gland: Two case reports
  75. Neuroprotective effects of crocin and crocin-loaded niosomes against the paraquat-induced oxidative brain damage in rats
  76. Role of MMP-2 and CD147 in kidney fibrosis
  77. Geometric basis of action potential of skeletal muscle cells and neurons
  78. Babesia microti-induced fulminant sepsis in an immunocompromised host: A case report and the case-specific literature review
  79. Role of cerebellar cortex in associative learning and memory in guinea pigs
  80. Application of metagenomic next-generation sequencing technique for diagnosing a specific case of necrotizing meningoencephalitis caused by human herpesvirus 2
  81. Case report: Quadruple primary malignant neoplasms including esophageal, ureteral, and lung in an elderly male
  82. Long non-coding RNA NEAT1 promotes angiogenesis in hepatoma carcinoma via the miR-125a-5p/VEGF pathway
  83. Osteogenic differentiation of periodontal membrane stem cells in inflammatory environments
  84. Knockdown of SHMT2 enhances the sensitivity of gastric cancer cells to radiotherapy through the Wnt/β-catenin pathway
  85. Continuous renal replacement therapy combined with double filtration plasmapheresis in the treatment of severe lupus complicated by serious bacterial infections in children: A case report
  86. Simultaneous triple primary malignancies, including bladder cancer, lymphoma, and lung cancer, in an elderly male: A case report
  87. Preclinical immunogenicity assessment of a cell-based inactivated whole-virion H5N1 influenza vaccine
  88. One case of iodine-125 therapy – A new minimally invasive treatment of intrahepatic cholangiocarcinoma
  89. S1P promotes corneal trigeminal neuron differentiation and corneal nerve repair via upregulating nerve growth factor expression in a mouse model
  90. Early cancer detection by a targeted methylation assay of circulating tumor DNA in plasma
  91. Calcifying nanoparticles initiate the calcification process of mesenchymal stem cells in vitro through the activation of the TGF-β1/Smad signaling pathway and promote the decay of echinococcosis
  92. Evaluation of prognostic markers in patients infected with SARS-CoV-2
  93. N6-Methyladenosine-related alternative splicing events play a role in bladder cancer
  94. Characterization of the structural, oxidative, and immunological features of testis tissue from Zucker diabetic fatty rats
  95. Effects of glucose and osmotic pressure on the proliferation and cell cycle of human chorionic trophoblast cells
  96. Investigation of genotype diversity of 7,804 norovirus sequences in humans and animals of China
  97. Characteristics and karyotype analysis of a patient with turner syndrome complicated with multiple-site tumors: A case report
  98. Aggravated renal fibrosis is positively associated with the activation of HMGB1-TLR2/4 signaling in STZ-induced diabetic mice
  99. Distribution characteristics of SARS-CoV-2 IgM/IgG in false-positive results detected by chemiluminescent immunoassay
  100. SRPX2 attenuated oxygen–glucose deprivation and reperfusion-induced injury in cardiomyocytes via alleviating endoplasmic reticulum stress-induced apoptosis through targeting PI3K/Akt/mTOR axis
  101. Aquaporin-8 overexpression is involved in vascular structure and function changes in placentas of gestational diabetes mellitus patients
  102. Relationship between CRP gene polymorphisms and ischemic stroke risk: A systematic review and meta-analysis
  103. Effects of growth hormone on lipid metabolism and sexual development in pubertal obese male rats
  104. Cloning and identification of the CTLA-4IgV gene and functional application of vaccine in Xinjiang sheep
  105. Antitumor activity of RUNX3: Upregulation of E-cadherin and downregulation of the epithelial–mesenchymal transition in clear-cell renal cell carcinoma
  106. PHF8 promotes osteogenic differentiation of BMSCs in old rat with osteoporosis by regulating Wnt/β-catenin pathway
  107. A review of the current state of the computer-aided diagnosis (CAD) systems for breast cancer diagnosis
  108. Bilateral dacryoadenitis in adult-onset Still’s disease: A case report
  109. A novel association between Bmi-1 protein expression and the SUVmax obtained by 18F-FDG PET/CT in patients with gastric adenocarcinoma
  110. The role of erythrocytes and erythroid progenitor cells in tumors
  111. Relationship between platelet activation markers and spontaneous abortion: A meta-analysis
  112. Abnormal methylation caused by folic acid deficiency in neural tube defects
  113. Silencing TLR4 using an ultrasound-targeted microbubble destruction-based shRNA system reduces ischemia-induced seizures in hyperglycemic rats
  114. Plant Sciences
  115. Seasonal succession of bacterial communities in cultured Caulerpa lentillifera detected by high-throughput sequencing
  116. Cloning and prokaryotic expression of WRKY48 from Caragana intermedia
  117. Novel Brassica hybrids with different resistance to Leptosphaeria maculans reveal unbalanced rDNA signal patterns
  118. Application of exogenous auxin and gibberellin regulates the bolting of lettuce (Lactuca sativa L.)
  119. Phytoremediation of pollutants from wastewater: A concise review
  120. Genome-wide identification and characterization of NBS-encoding genes in the sweet potato wild ancestor Ipomoea trifida (H.B.K.)
  121. Alleviative effects of magnetic Fe3O4 nanoparticles on the physiological toxicity of 3-nitrophenol to rice (Oryza sativa L.) seedlings
  122. Selection and functional identification of Dof genes expressed in response to nitrogen in Populus simonii × Populus nigra
  123. Study on pecan seed germination influenced by seed endocarp
  124. Identification of active compounds in Ophiopogonis Radix from different geographical origins by UPLC-Q/TOF-MS combined with GC-MS approaches
  125. The entire chloroplast genome sequence of Asparagus cochinchinensis and genetic comparison to Asparagus species
  126. Genome-wide identification of MAPK family genes and their response to abiotic stresses in tea plant (Camellia sinensis)
  127. Selection and validation of reference genes for RT-qPCR analysis of different organs at various development stages in Caragana intermedia
  128. Cloning and expression analysis of SERK1 gene in Diospyros lotus
  129. Integrated metabolomic and transcriptomic profiling revealed coping mechanisms of the edible and medicinal homologous plant Plantago asiatica L. cadmium resistance
  130. A missense variant in NCF1 is associated with susceptibility to unexplained recurrent spontaneous abortion
  131. Assessment of drought tolerance indices in faba bean genotypes under different irrigation regimes
  132. The entire chloroplast genome sequence of Asparagus setaceus (Kunth) Jessop: Genome structure, gene composition, and phylogenetic analysis in Asparagaceae
  133. Food Science
  134. Dietary food additive monosodium glutamate with or without high-lipid diet induces spleen anomaly: A mechanistic approach on rat model
  135. Binge eating disorder during COVID-19
  136. Potential of honey against the onset of autoimmune diabetes and its associated nephropathy, pancreatitis, and retinopathy in type 1 diabetic animal model
  137. FTO gene expression in diet-induced obesity is downregulated by Solanum fruit supplementation
  138. Physical activity enhances fecal lactobacilli in rats chronically drinking sweetened cola beverage
  139. Supercritical CO2 extraction, chemical composition, and antioxidant effects of Coreopsis tinctoria Nutt. oleoresin
  140. Functional constituents of plant-based foods boost immunity against acute and chronic disorders
  141. Effect of selenium and methods of protein extraction on the proteomic profile of Saccharomyces yeast
  142. Microbial diversity of milk ghee in southern Gansu and its effect on the formation of ghee flavor compounds
  143. Ecology and Environmental Sciences
  144. Effects of heavy metals on bacterial community surrounding Bijiashan mining area located in northwest China
  145. Microorganism community composition analysis coupling with 15N tracer experiments reveals the nitrification rate and N2O emissions in low pH soils in Southern China
  146. Genetic diversity and population structure of Cinnamomum balansae Lecomte inferred by microsatellites
  147. Preliminary screening of microplastic contamination in different marine fish species of Taif market, Saudi Arabia
  148. Plant volatile organic compounds attractive to Lygus pratensis
  149. Effects of organic materials on soil bacterial community structure in long-term continuous cropping of tomato in greenhouse
  150. Effects of soil treated fungicide fluopimomide on tomato (Solanum lycopersicum L.) disease control and plant growth
  151. Prevalence of Yersinia pestis among rodents captured in a semi-arid tropical ecosystem of south-western Zimbabwe
  152. Effects of irrigation and nitrogen fertilization on mitigating salt-induced Na+ toxicity and sustaining sea rice growth
  153. Bioengineering and Biotechnology
  154. Poly-l-lysine-caused cell adhesion induces pyroptosis in THP-1 monocytes
  155. Development of alkaline phosphatase-scFv and its use for one-step enzyme-linked immunosorbent assay for His-tagged protein detection
  156. Development and validation of a predictive model for immune-related genes in patients with tongue squamous cell carcinoma
  157. Agriculture
  158. Effects of chemical-based fertilizer replacement with biochar-based fertilizer on albic soil nutrient content and maize yield
  159. Genome-wide identification and expression analysis of CPP-like gene family in Triticum aestivum L. under different hormone and stress conditions
  160. Agronomic and economic performance of mung bean (Vigna radiata L.) varieties in response to rates of blended NPS fertilizer in Kindo Koysha district, Southern Ethiopia
  161. Influence of furrow irrigation regime on the yield and water consumption indicators of winter wheat based on a multi-level fuzzy comprehensive evaluation
  162. Discovery of exercise-related genes and pathway analysis based on comparative genomes of Mongolian originated Abaga and Wushen horse
  163. Lessons from integrated seasonal forecast-crop modelling in Africa: A systematic review
  164. Evolution trend of soil fertility in tobacco-planting area of Chenzhou, Hunan Province, China
  165. Animal Sciences
  166. Morphological and molecular characterization of Tatera indica Hardwicke 1807 (Rodentia: Muridae) from Pothwar, Pakistan
  167. Research on meat quality of Qianhua Mutton Merino sheep and Small-tail Han sheep
  168. SI: A Scientific Memoir
  169. Suggestions on leading an academic research laboratory group
  170. My scientific genealogy and the Toronto ACDC Laboratory, 1988–2022
  171. Erratum
  172. Erratum to “Changes of immune cells in patients with hepatocellular carcinoma treated by radiofrequency ablation and hepatectomy, a pilot study”
  173. Erratum to “A two-microRNA signature predicts the progression of male thyroid cancer”
  174. Retraction
  175. Retraction of “Lidocaine has antitumor effect on hepatocellular carcinoma via the circ_DYNC1H1/miR-520a-3p/USP14 axis”
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