|Year : 2023 | Volume
| Issue : 1 | Page : 43-52
Developing a novel single-marker-based method for the quantitative evaluation of the multiple active components in Corydalis yanhusuo W. T. Wang
Xin-Rong Yang1, Shuang Jiang1, Chun-Li Gan2, Jing Huang2, Fan-Shu Wei1, Zheng-Yang Wang1, He-Song Peng1, Jing Yang3, Chun-Juan Yang1
1 Department of Pharmaceutical Analysis and Analytical Chemistry, College of Pharmacy, Harbin Medical University, Harbin, China
2 Department of Medicinal Chemistry and Natural Medicine Chemistry, College of Pharmacy, Harbin Medical University, Harbin, China
3 Analytical Department, Johnson and Johnson, 199 Grandview Road, Skillman, NJ, USA
|Date of Submission||24-Jul-2021|
|Date of Acceptance||09-Oct-2021|
|Date of Web Publication||21-Dec-2022|
Prof. Chun-Juan Yang
Department of Pharmaceutical Analysis and Analytical Chemistry, College of Pharmacy, Harbin Medical University, 157 Baojian Road, Nangang District, Harbin 150081
Source of Support: None, Conflict of Interest: None
Objective: This study was designed to develop a method for detecting differences in the chemical composition of Corydalis yanhusuo W. T. Wang using high-performance liquid chromatography with a diode array detector technology. Materials and Methods: We established a novel quantitative evaluation method for identifying multiple components in natural extracts using a single-marker method quantitative analysis of multi-components by single marker (QAMS). This method was then validated using eight alkaloid phytochemical markers designed to evaluate C. yanhusuo quality. Results: Our evaluations revealed good linearity (R2 ≥ 0.9991) within the range of tested concentrations for all eight alkaloids, with recovery ranging from 95.5% to 101.5%. The evaluations also returned stability results that fell within the acceptable range. Cluster analysis and Heatmap analyses were applied to classify and evaluate alkaloids across 21 different production areas. These results revealed a significant difference in the component profiles between samples from different origins. Conclusions: Thus, these data suggest that in the absence of a material reference, QAMS may help facilitate the stable production of C. yanhusuo. In addition, our data suggest that this method may have value as a promising alternative to common quality evaluations for controlling C. yanhusuo composition.
Keywords: Corydalis yanhusuo W. T. Wang, high-performance liquid chromatography with a diode array detector, QAMS, quality evaluation
|How to cite this article:|
Yang XR, Jiang S, Gan CL, Huang J, Wei FS, Wang ZY, Peng HS, Yang J, Yang CJ. Developing a novel single-marker-based method for the quantitative evaluation of the multiple active components in Corydalis yanhusuo W. T. Wang. World J Tradit Chin Med 2023;9:43-52
|How to cite this URL:|
Yang XR, Jiang S, Gan CL, Huang J, Wei FS, Wang ZY, Peng HS, Yang J, Yang CJ. Developing a novel single-marker-based method for the quantitative evaluation of the multiple active components in Corydalis yanhusuo W. T. Wang. World J Tradit Chin Med [serial online] 2023 [cited 2023 Mar 28];9:43-52. Available from: https://www.wjtcm.net/text.asp?2023/9/1/43/364415
| Introduction|| |
Traditional Chinese medicine (TCM) is a distinctive healthcare system that has been successfully applied for thousands of years, accumulating a long history of clinical application, reliable therapeutic effect, and low toxicity. However, quality control (QC) over various products used in TCM remains difficult, creating a significant barrier to its application and development. This is because the efficacy of any specific TCM is likely the result of the synergistic effects of multiple components. This means that more conventional QC methods are not always sufficient to reflect the actual quality of these products. Therefore, it is important to develop methods that allow us to evaluate the quality of the various synergistic components of each TCM.
Corydalis yanhusuo, also known as YuanHu, YanHu, or XuanHu, is a key ingredient in Yuanhu Zhitong tablets, a well-known TCM prepared from the dried tubers of C. yanhusuo (Y. H. Chou and Chun C. Hsu) W. T. Wang ex Z. Y. Su and C. Y. Wu (Papaveraceae). C. yanhusuo is included in the Chinese Pharmacopoeia and Chinese National Essential Medicine List as one of the most significant crude extracts in TCM., These compounds have been widely used as an analgesic agent for treating spasticity, stomach ache, menstrual pains, and various injuries.,, Recent reports have identified several unique components in C. yanhusuo, which are likely to have some therapeutic effects. These include various alkaloids, aliphatic acid, and ecdysterone, among others. Of these, tetrahydropalmatine is the most well-established and regarded as the key phytochemical marker for evaluating the quality of C. yanhusuo as described by the Chinese Pharmacopoeia. In addition, alkaloids and coumarins have been shown to induce a variety of pharmacological effects, such as analgesia, spasmolysis, anti-inflammatory, antianxiety, and vasodilatation effects.,,
Many scholars have focused on the quantitative analysis of alkaloids, with the majority of these using high-performance liquid chromatography (HPLC) with an ultraviolet detector, or HPLC with a diode array detector (HPLC-DAD) as their base. Several of these methods were designed to facilitate the quantitative analysis of various alkaloids including fumaricine, dehydrocorydaline, canadine, palmatine, tetrahydroprotopapaverine, 13-methyl-dehydrocorydalmine, coptisine, demethylcorydalmine, columbamine, tetrahydrocolumbamine, 13-methylpalmatrubine, protopine, d-glaucine, dehydrocorybulbine, tetrahydropalmatine, and d, l-tetrahydrocoptisine. From the research status of C. yanhusuo, it could be found that there are many kinds of research on tetrahydropalmatine and its tertiary amine alkaloid derivatives, but the research on its raw materials was less and the research progress was limited. This means that the current status quo is not capable to perform an in-depth and thorough evaluation of C. yanhusuo for clinical therapy, suggesting an immediate need for further investigation. This gap may potentially be addressed by the application of a single standard to determine multiple components, also known as the quantitative analysis of multicomponents by single-related products (QAMS).,, QAMS is a novel method designed to facilitate the evaluation of herbal medicines and their related products, which means that QAMS can be applied for the evaluation of TCM, and it may allow for improved product detection accuracy, while reducing both analysis time and cost. The external standard method (EMS) can be used for the quantitative evaluation of various components whether there are other analytical peaks within the sample. EMS is also simple and does not require the use of a correction factor. However, the accuracy of this method is affected by the repeatability of injection and the stability of the experimental conditions. Given this, we designed this study to develop a novel QAMS-based method for evaluating C. yanhusuo products. To this end, we quantified the levels of corydaline, dehydrocorydaline, tetrahydropalmatine, protopine, palmatine, berberine, tetrahydroberberine, and coptisine in various C. yanhusuo products from 21 production areas using QAMS in an effort to determine its utility in the evaluation of C. yanhusuo quality. The reliability and accuracy of this method were then compared using a combination of hierarchical cluster-and-thermogram analysis across the 21 batches of C. yanhusuo.
| Experimental Procedure|| |
Instrumentation and reagents
Corydaline (151118), dehydrocorydaline (16051707), tetrahydropalmatine (151123), protopine (17062106), palmatine (140821), tetrahydroberberine (151111), berberine (141128), and coptisine (140430), all produced at over 98% purity, were purchased from Chengdu Pufei De Biotech Co., Ltd. (Chengdu, Sichuan province, China). HPLC-grade methanol and acetonitrile were purchased from Dikma Technologies Inc. (Beijing, China), while all other reagents were purchased at analytical grade. Ultra-pure water was prepared using a Milli-Q Water Purification System (Millipore, Molsheim, France). C. yanhusuo was collected from various TCM markets across different regions of China [Table 1] with each site identified by Prof. Zhenyue Wang from the Heilongjiang University of Chinese Medicine. All samples were bought in May 2017.
Apparatus and chromatographic conditions
Analyses of all eight alkaloids were performed using an Agilent 1260 HPLC-DAD (Agilent Technologies, USA). Detection wavelengths were set at 280 nm for each of the eight alkaloids, and samples were prepared using a Phenomenex Gemini C18 110A column (5 μm, 250 mm × 4.6 mm). Injected sample volume was 10 μL and the column was maintained at 30°C. The mobile phase consisted of (A) 0.2% acetic acid set to a pH of 5 using triethylamine (B) acetonitrile at the flow rate of 1.0 mL/min [Table 2].
|Table 2: Gradient elution program of mobile phase in quantitative analysis|
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The Chinese Pharmacopoeia stipulates a specific method for extracting components from C. yanhusuo. Briefly, each of the 21 batches of dried C. yanhusuo, each from different production areas, was crushed using a high-speed Chinese medicine shredder, then powdered and sieved through a 40-mesh sieve, before being weighed (0.5 g), and immersed in 60% ethanol (1:4, w/v) for 24 h. These samples were then extracted at 75°C for 2–3 h and then again at 75°C for another 2 h. The products were then filtered and dissolved in 10 mL of methanol before being filtered again and used in our HPLC analysis.
Preparation of the standard solution
Each of the eight standard compounds was accurately weighed and then placed in a 25 mL volumetric flask to produce our mixed standard solution, with each compound represented as follows: 520.0 μg/mL corydaline, 321.0 μg/mL dehydrocorydaline, 4000.0 μg/mL tetrahydropalmatine, 500.2 μg/mL protopine, 2000.0 μg/mL palmatine, 355.0 μg/mL tetrahydroberberine, 560.0 μg/mL berberine, and 510.0 μg/mL coptisine. This solution was then diluted with methanol to produce a series of working solutions for calibration. All the solutions above were prepared in dark brown volumetric flasks and stored at 4°C. The chemical structures of each alkaloid are shown in [Figure 1].
|Figure 1: The chemical structures of corydaline (a), dehydrocorydaline (b), tetrahydropalmatine (c), protopine (d), palmatine (e), tetrahydroberberine (f), berberine (g), and coptisine (h)|
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Calculation of the correction factor (fk/s)
The relative correction factor for each evaluation was calculated using the results from several experimental standards, with the average fk/s value calculated as follows:
fk/s = (Cs × Ak)/(Ck × As)
Mass concentrations for each component were then determined using the following formula:
Ck′ = (Cs × Ak′)/(fk/s × As)
Where Cs is the mass concentration for each reference substance, As is the peak area of the reference substance, and Ck is the mass concentration of the other reference substances. In addition, Ak and Ak′ represent the peak area of the other reference compounds and the peak area of the components to be measured, respectively.
Calibration curves and linearity
The stock and calibration solutions were prepared as described above and the solutions containing different concentrations of each of the eight analytes were injected into the HPLC, as described. We then produced the calibration curves for each standard by plotting the peak area (Y) against the compound concentrations (X, mg/L) within the mixed standard solutions.
Precision, repeatability, and accuracy
Precision was determined by comparing the outcomes for each of the eight analytes across six replicates with the changes in the peak areas for each evaluation and then used to calculate relative standard deviation (RSD).
Repeatability was evaluated by comparing the outcomes for six duplicates of each C. yanhusuo sample versus the standard, and any changes in these concentrations were then used to calculate RSD.
Accuracy was determined using the recovery method. Accurate volumes of each standard compound solution were added to known amounts of C. yanhusuo and then extracted and analyzed as described above. We then used these evaluations to determine the recovery rate for each compound in each sample and then used the recovery rate, calculated as recovery rate (%) = (Found amount − Known amount) × 100%/Added amount, as the evaluation index.
Stability was evaluated by injecting the same sample solution into the HPLC at 0, 2, 4, 6, 8, and 12 h and then comparing the concentrations of all eight compounds at each time point versus 0 h to calculate RSD.
The mixed reference stock and test solutions were compared with each of the injected samples using the same chromatographic conditions to confirm their specificity.
| Results|| |
Selection of chromatographic conditions
Our first observation was that the use of methanol as the mobile phase reduced the resolution between the peaks. However, this resolution was significantly improved by switching from methanol to acetonitrile. Given this, we then added 0.2% (v/v) acetic acid to the triethylamine aqueous phase changing the pH to 5 and found that this also improved peak resolution and eliminated peak-tailing in each of the target compounds. The column temperature was maintained at 30°C with good resolution, satisfactory retention time, and satisfactory peak shape. Multicomponent evaluations were then completed using diode array detection at 280 nm, which ensured sufficient absorption for each of the compounds [Figure 2].
|Figure 2: The ultraviolet spectra for each of the eight alkaloids: (1) protopine, (2) corydaline, (3) berberine, (4) dehydrocorydaline, (5) coptisine, (6) palmatine, (7) tetrahydroberberine, (8) tetrahydropalmatine|
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Reproducibility of fk/s
We then went on to evaluate the impact of two different chromatographic systems (Agilent 1260, Agilent 1100) and a variety of different chromatographic columns on the reproducibility of our evaluations (fk/s) in different laboratories. These results are summarized in [Table 3].
Calibration curves and linearity
Calibration curves were produced by plotting peak area (Y) against compound concentration (X, mg/L) within the mixed standard [Table 4] with each of the calibration curves being evaluated by HPLC. Analysis of these curves revealed good linearity (R2 ≥ 0.9991) within the range of tested concentrations, confirming the conditions for these assays.
|Table 4: The regression equations and linear ranges for the determination of the analytes|
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Precision, repeatability, and accuracy
Our evaluations of the RSD values for each of the eight peak areas associated with each of our analytes revealed that this method was extremely precise. This was then supported by the limited changes in RSD value for each compound even under varying concentrations, indicating that this method was highly reproducible. Finally, our accuracy evaluations revealed that the recovery rates for these compounds were between 95.5% and 98.5% and that their average RSD was ≤2.47% [Table 5].
Given that our previous assays showed that this method produced both reliable and accurate results, we then went on to determine the stability of these results. Our stability assay then revealed that all eight analytes were stable for over 12 h [Table 6].
Our final set of evaluations [Figure 3] was designed to evaluate the specificity of these assays. Here, we were able to show that the retention time of the sample was the same as that of the reference material, reproducibly producing the following chromatographic peaks: (1). protopine; (2) corydaline; (3) coptisine; (4) palmatine; (5) berberine; (6) dehydrocorydaline; (7) tetrahydroberberine; and (8) tetrahydropalmatine.
|Figure 3: Representative HPLC chromatograms for each of the eight reference solutions (a) and the Corydalis yanhusuo solution (b), HPLC: High-performance liquid chromatography|
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| Discussion|| |
Quantitative analysis of multicomponent products using QAMS
Our data revealed that we could successfully evaluate seven of the eight (all except tetrahydropalmatine) key alkaloids from the C. yanhusuo extracts collected from 21 different sources using QAMS [Table 7] and that these results were comparable to those of external standard method (ESM) [Table 8], QAMS and ESM were compared, confirming its potential as a quantitative evaluation method for complex products.
|Table 7: Content determination of the eight alkaloids from 21 different sources by quantitative analysis of multicomponents by single marker (n=3)|
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|Table 8: Content determination of eight alkaloids from 21 different sources by ESM (n=3)|
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Analysis of the results
Our data revealed that the alkaloid content of our C. yanhusuo samples was significantly affected by several factors, including geographical location, climate, and picking period. This was clearly visible in our thermogram analysis which allowed us to present these changes as progressive color differences, with each color change representing differences in the characteristics of a sample. Here, we used red to represent increased alkaloid content and purple to represent reduced alkaloid content [Figure 4]. Looking at this preliminary thermogram analysis, we were able to conclude that the alkaloid composition was significantly different across different areas when comparing our 21 C. yanhusuo samples, with tetrahydropalmatine presenting as the most abundant alkaloid in most samples. Tetrahydropalmatine was most enriched in the samples from Xiangyang, whereas palmatine was shown to be higher in samples from Xiangyang and Xuzhou. In addition, our evaluations revealed that tetrahydroberberine was most abundant in samples from Shijiazhuang. This is of interest as corydaline, dehydrocorydaline, and tetrahydropalmatine have been shown to exert the most significant analgesic effects,,, and all three were shown to be most heavily produced by samples from Xiangyang, Xi'an, and Hangzhou, suggesting that samples from these areas may be better for certain analgesic applications. It has also been reported that palmatine, berberine, tetrahydroberberine, and coptisine, have antimicrobial or anti-inflammatory properties,, and our data reveal the highest concentrations for these compounds in samples from Xuzhou, Chengdu, and Ningbo. Dehydrocorydaline, tetrahydroberberine, and coptisine have also been shown to exert a protective effect on the heart and cerebral vessels, and our data suggested that these alkaloids are most enriched in samples from Hanzhong, Xuzhou, and Huhehaote. Taken together, these data suggest that differences in geographical location and growth environments result in differences in the medicinal content of specific samples, which means that it is important to select samples from specific regions when using them as TCM for different diseases.
|Figure 4: Heatmap evaluation of the quality of Corydalis yanhusuo from each of the 21 production areas evaluated in this study. A-H represent eight alkaloids. (A) protopine, (B) corydaline, (C) coptisine, (D) palmatine, (E) berberine, (F) dehydrocorydaline; (G) tetrahydroberberine (H) tetrahydropalmatine|
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Xiangyang, Xuzhou, Datong, Hangzhou, Shijiazhuang were considered as category A, A could be also divided into A1 (Xiangyang) and A2 (Xuzhou, Datong, Hangzhou, Shijiazhuang). Samples of other producing areas were belonged to category B, which could be divided into B1 and B2. We then completed a cluster analysis on these products using the Euclidean distance method, with these evaluations producing a reasonably similar profile in sample grouping to the chemical analysis. This suggests that our HPLC approach is suitable for evaluating the quality of these medicinal materials and that the QAMS approach is a reliable predictor of product quality when applied using the proper marker components [Figure 5]. This analysis also allowed us to reveal that total alkaloid content was highest in samples from Shiyan and Xuzhou and that this increase may be related to their geographical location.
|Figure 5: Cluster analysis of the quality of the Corydalis yanhusuo from each of the 21 production areas. A, B respectively represent the two major categories of medicinal materials. A could be also divided into A1 and A2. Class B includes B1 and B2. B2 includes b1 and b2. The vertical column represents the origin of the medicinal materials|
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Comparing QAMS and ESM
The Chinese Pharmacopoeia uses tetrahydropalmatine as the standard for evaluating C. yanhusuo quality and alkaloid content. However, TCM is also reliant on several other alkaloids for its medicinal value. Thus, it is insufficient to control the quality of these products using only tetrahydropalmatine. However, in this experiment, only one reference standard was needed to evaluate the quality of all eight major alkaloids from C. yanhusuo, making these evaluations more comprehensive. The quantitative results of both methods were compared by bar graph [Figure 6], confirming its potential as a quantitative evaluation method for complex products. The quantitative results of both methods were compared by bar graph [Figure 6], confirming its potential as a quantitative evaluation method for complex products. Our data reveal that QAMS can be used to analyze complex TCM characterized by their diverse medicinal ingredients and applications. Given this, we went on to compare ESM, also known as the internal standard method, with QAMS and revealed that our method has several advantages including low operating costs and simple, fast synchronous detection of multiple components, which improves the overall efficiency of this approach. In addition, direct comparisons of the detection of seven of the eight key C. yanhusuo alkaloids by ESM and QAMS via hierarchical cluster-and-thermogram analysis [Figure 4] and [Figure 5] revealed that these methods were largely synonymous. Thus, we can conclude that QAMS is a feasible method for evaluating the alkaloid content of C. yanhusuo and that the application of this method might improve consistency in these products and support broad improvements in the quality evaluation of TCM materials.
|Figure 6: Comparison of the total content evaluations of the Corydalis yanhusuo samples as estimated by QAMS or ESM. (a) protopine, (b) corydaline, (d) palmatine, (e) berberine, (f) dehydrocorydaline; (g) tetrahydroberberine; (h) tetrahydropalmatine and total. QAMS: Quantitative analysis of multi-components by single marker, ESM: External standard method.|
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QAMS is also easily adapted to other sources which may help accelerate the internationalization of Chinese medicine. However, subsequent evaluations should combine chemical analysis, biological evaluation, pharmacological assays, and other methods to evaluate the quality of C. yanhusuo more fully which will facilitate better investigation of its clinical effect. QAMS is widely used in the QC of other TCM with similar composition, and it can be used to accurately and effectively evaluate the quality of various components in other TCM with similar ultraviolet absorption. Thus, our study verified that QAMS may be a suitable alternative for the comprehensive evaluation of C. yanhusuo quality.
| Conclusions|| |
Here, we describe the application of QAMS and ESM via HPLC-DAD to the evaluation of 21 samples of C. yanhusuo. Our results show that there are significant differences in the composition of these samples, with clear changes in the concentrations of each of the eight key alkaloid compounds across different regions. In addition, our evaluations revealed that while EMS-based evaluations might be slightly more accurate, and this advantage is lost in its more complex operation. Thus, we suggest that QAMS combined with HPLC might offer an improved quality analysis method for complex TCM and that this method might facilitate improved QC for C. yanhusuo. Taken together, our data suggest that this method has significant potential in the development of new quantitative QC techniques for QC evaluations and may aid in the development of a set of quality standards for C. yanhusuo. QAMS was shown to be a powerful and reliable technique providing quantitative data for comprehensive quality assessment of complex multicomponent systems. Thus, we conclude that QAMS may help improve the overall level of QC in TCM, making it an important developmental tool in establishing the protocols and standards needed to facilitate proper quality evaluations in TCM characterized by multicomponent profiles.
Financial support and sponsorship
This work was supported by The Scientific Research Project under the National Natural Science Foundation of China (No. 81872979 and 81603418).
Conflicts of interest
There are no conflicts of interest.
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[Figure 1], [Figure 2], [Figure 3], [Figure 4], [Figure 5], [Figure 6]
[Table 1], [Table 2], [Table 3], [Table 4], [Table 5], [Table 6], [Table 7], [Table 8]