Quantitative Analysis and Differential Evaluation of Radix Bupleuri Cultivated in Different Regions Based on HPLC-MS and GC-MS Combined with Multivariate Statistical Analysis
Abstract
:1. Introduction
2. Results and Discussion
2.1. Differential Analysis of Five Saikosaponins in Radix Bupleuri Samples Cultivated in Different Regions
2.1.1. Identification of Five Saikosaponins in Radix Bupleuri
2.1.2. Validation of Quantitative Method
2.1.3. Quantitative Analysis of Five Saikosaponins in Radix Bupleuri Cultivated in Different Regions
2.2. Differential Analysis of Radix Bupleuri from Different Cultivation Regions Based on HPLC-MS and GC-MS Analysis
2.2.1. Principal Component Analysis
2.2.2. Hierarchical Cluster Analysis
2.2.3. Partial Least Squares-Discriminate Analysis
3. Materials and Methods
3.1. Materials and Chemicals
3.2. Preparation of Sample and Standard Solutions
3.2.1. Extraction of Saikosaponins from Radix Bupleuri
3.2.2. Extraction of Volatile Compounds from Radix Bupleuri
3.2.3. Preparation of Standard Solutions
3.3. Chromatography-Based MS Conditions
3.3.1. HPLC-MS Conditions
3.3.2. GC-MS Conditions
3.4. Validation of Methodology
3.5. Data Processing and Statistical Analysis
3.6. General Process of Compound Identification
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Peak | tR (min) | Identification | Measured Mass | Molecular Formula | Product Ions |
---|---|---|---|---|---|
1 | 6.83 | SSc | 926.5 | C48H78O17 | 925.5 [M-H]−, 779.5 [M-Rha-H]−, 763.5 [M-Glc-H]−, 617.4 [M-Rha-Glc-H]−, 455.6 [M-Rha-2Glc-H]− |
2 | 7.69 | SSf | 928.5 | C48H80O17 | 927.5 [M-H]−, 781.5 [M-Fuc-H]−, 619.4 [M-Fuc-Glc-H]−, 457.4 [M-Fuc-2Glc-H]− |
3 | 10.39 | SSa | 780.5 | C42H68O13 | 779.5 [M-H]−, 617.4 [M-Glc-H]−, 471.4 [M-Glc-Fuc-H]− |
4 | 12.81 | SSe | 764.5 | C42H68O12 | 763.5 [M-H]−, 601.4 [M-Glc-H]−, 455.4 [M-Rha-2Glc-H]− |
5 | 14.22 | SSd | 780.5 | C42H68O13 | 779.5 [M-H]−, 617.4 [M-Glc-H]−, 471.6 [M-Glc-Fuc-H]− |
Saikosaponin | Calibration Curve | R2 | Linear Range (μg/mL) | LOD (μg/mL) | LOQ (μg/mL) |
---|---|---|---|---|---|
SSa | y = 13,888.3 + 92,655.3x | 0.9986 | 0.1–100.0 | 0.009 | 0.030 |
SSc | y = 64,383 + 755,798x | 0.9974 | 0.05–10.0 | 0.006 | 0.020 |
SSd | y = 36,478.4 + 89,231.8x | 0.9953 | 0.1–100.0 | 0.015 | 0.050 |
SSe | y = 133,789 + 313,062x | 0.9949 | 0.03–3.0 | 0.009 | 0.030 |
SSf | y = 46,408.3 + 909,911x | 0.9966 | 0.05–10.0 | 0.005 | 0.017 |
Saikosaponin | Intraday Precision RSD (n = 9, %) | Interday Precision RSD (n = 6, %) | Repeatability RSD (n = 6, %) | Stability RSD (n = 7, %) | Recovery (%)/RSD (n = 3, %) | ||
---|---|---|---|---|---|---|---|
80% | 100% | 120% | |||||
SSa | 2.93 | 1.78 | 2.04 | 1.98 | 101.32/1.57 | 101.96/2.03 | 99.63/2.19 |
SSc | 2.06 | 1.90 | 1.68 | 1.53 | 100.91/1.95 | 102.46/1.47 | 95.55/2.09 |
SSd | 1.53 | 2.23 | 1.46 | 1.46 | 101.13/1.32 | 102.45/1.22 | 98.10/1.82 |
SSe | 3.14 | 2.77 | 3.23 | 3.28 | 97.47/1.65 | 103.20/2.59 | 98.46/1.48 |
SSf | 3.45 | 3.23 | 3.18 | 2.89 | 98.83/2.61 | 102.05/1.78 | 96.12/2.57 |
No. | tR (min) | VIP | Compound Name | [M-H]− Ion (m/z) | Fragment Ions (m/z) | Molecular Formula | References |
---|---|---|---|---|---|---|---|
1 | 4.01 | 2.0 | 3′,4′-dimethoxy quercetin | 329 | 314, 299 | C18H34O5 | [30] |
2 | 4.17 | 1.3 | hydroxy-SSc or its isomer | 943 | 811, 649, 503, 471, 453 | C48H80O18 | [12] |
3 | 4.49 | 1.6 | rotundioside w | 941 | 795, 777 | C48H78O18 | [31] |
4 | 4.86 | 1.6 | hydroxy-SSa | 797 | 635, 559, 489 | C42H70O14 | [12] |
5 | 6.57 | 3.3 | SSi | 925 | 779, 763, 617 | C48H78O17 | [12] |
6 | 6.69 | 3.3 | SSc | 971 | 925, 779, 763, 617, 455 | C48H78O17 | [12] |
7 | 6.77 | 1.2 | rotundioside n | 941 | 779, 763, 618 | C48H78O18 | [31] |
8 | 7.14 | 1.7 | hydroxy-SSd | 797 | 635, 559, 489 | C42H70O14 | [12] |
9 | 7.56 | 5.2 | SSf | 973 | 927, 781, 765, 619, 457 | C48H80O17 | [12] |
10 | 8.72 | 1.3 | rotundioside p | 943 | 811, 649, 503, 471 | C48H80O18 | [12] |
11 | 9.36 | 4.2 | 2″-O-acetyl SSb3 | 853 | 811, 793, 649 | C45H74O15 | [32] |
12 | 10.33 | 2.5 | SSa | 825 | 779, 617, 541, 471 | C42H68O13 | [12] |
13 | 10.5 | 13.4 | SSb2 | 825 | 779, 617, 541, 471 | C42H68O13 | [12] |
14 | 11.11 | 5.2 | isomer of SSf | 927 | 781, 765, 619 | C48H80O17 | [12] |
15 | 11.28 | 1.6 | chinoposaponin XVIII | 941 | 779, 617 | C48H78O18 | [7] |
16 | 11.43 | 1.2 | 2″-O-acetyl SSa | 821 | 779, 761, 617 | C44H70O14 | [12] |
17 | 11.49 | 1.0 | diacetyl SSa | 863 | 821, 761 | C46H72O15 | [30] |
18 | 11.54 | 1.5 | 3″-O-acetyl SSa | 821 | 779, 761, 617, 541, 471 | C44H70O14 | [30] |
19 | 11.66 | 1.5 | malonyl-SSa | 865 | 821, 779, 761, 617 | C45H70O16 | [7] |
20 | 11.85 | 12.0 | SSb1 | 825 | 779, 617, 471 | C42H68O13 | [12] |
21 | 11.89 | 2.3 | 3β, 23, 28-trihydroxyolean-11, 13(18)-diene-16-one 3-O-β-D-glucopyranosyl-(1-3)-β-D-fucopyranoside | 777 | 615, 539, 469, 437 | C42H66O13 | [12] |
22 | 11.92 | 3.6 | acetyl SSa | 821 | 779, 617 | C44H70O14 | [31] |
23 | 12.75 | 3.9 | SSe | 809 | 763, 601, 455 | C42H68O12 | [12] |
24 | 13.84 | 1.2 | 3″-O-acetyl SSb2 | 821 | 779, 761, 617 | C44H70O14 | [12] |
25 | 14.14 | 2.4 | SSd | 825 | 779, 617 | C42H68O13 | [12] |
26 | 15.51 | 1.5 | malonyl-SSd | 865 | 821, 779, 761, 617 | C45H70O16 | [32] |
27 | 16.07 | 1.0 | diacetyl SSd | 863 | 821, 779, 76 | C46H72O15 | [30] |
28 | 16.13 | 1.5 | 6″-O-acetyl SSd | 821 | 779, 761, 617 | C44H70O14 | [12] |
No. | tR (min) | VIP | Compound Name | M+• Ion (m/z) | Molecular Formula |
---|---|---|---|---|---|
1 | 2.02 | 1.4 | L-isoleucine | 130.1 | C6H13NO2 |
2 | 2.02 | 1.4 | 3, 4-dimethyl-1-hexene | 111.2 | C8H16 |
3 | 2.55 | 1.2 | cyclobutene, 2-propenylidene | 91.1 | C7H8 |
4 | 2.56 | 1.0 | n-hexane | 85.2 | C6H14C6H14 |
5 | 2.85 | 1.6 | 2, 2-dimethyl heptane | 127.3 | C9H20 |
6 | 2.88 | 1.6 | 2-(1-methylbutyl)-oxirane | 113.2 | C7H14O |
7 | 4.03 | 1.3 | chloromethyl 2-chloroundecanoate | 268.2 | C12H22Cl2O2 |
8 | 4.03 | 1.3 | 2, 4, 6-trimethyl-heptane | 141.3 | C10H22 |
9 | 4.07 | 1.1 | 2, 5, 6-trimethyl-decane | 183.4 | C13H28 |
10 | 4.07 | 1.1 | trimethylene oxide | 57.1 | C3H6O |
11 | 4.40 | 1.1 | hexyl-oxirane | 71.1 | C4H8O |
12 | 4.40 | 1.1 | D-sphingosine | 298.5 | C18H37NO2 |
13 | 4.40 | 1.1 | 1-methyl-4-(1-methylethenyl)- 2-cyclohexene | 135.2 | C10H16 |
14 | 4.8 | 1.2 | phenacyl thiocyanate | 176.2 | C9H7NOS |
15 | 4.95 | 1.6 | 2-butenoic acid, 3-methylbutyl ester | 155.2 | C9H16O2 |
16 | 4.95 | 1.5 | 5-methyl-2-hexanamine | 114.2 | C7H17N |
17 | 5.02 | 2.0 | α-pinene | 135.2 | C10H16 |
18 | 5.05 | 1.7 | 4-octyl acetate | 171.3 | C10H20O2 |
19 | 5.05 | 1.7 | 4, 4-dimethyl-1-hexene | 111.2 | C8H16 |
20 | 5.05 | 1.7 | ethyl-cyclohexane | 111.2 | C8H16 |
21 | 5.09 | 1.4 | di-t-butylacetylene | 137.3 | C10H18 |
22 | 5.24 | 1.4 | 4-methyl-cyclopentadecanone | 237.4 | C16H30O |
23 | 5.36 | 1.3 | trans-4, 5-epoxydecane | 155.3 | C10H20O |
24 | 5.81 | 1.7 | 7-methylene-tridecane | 195.4 | C14H28 |
25 | 5.81 | 1.7 | benzyl 2-chloroethyl sulfone | 217.7 | C9H11ClO2S |
26 | 5.87 | 1.7 | n-nonane | 267.5 | C19H40 |
27 | 6.10 | 1.0 | acetophenone | 119.2 | C8H8O |
28 | 6.16 | 2.0 | 1-nitro-2-octanone | 172.2 | C8H15NO3 |
29 | 6.17 | 2.1 | 1-heptadecyne | 235.4 | C17H32 |
30 | 6.19 | 1.1 | cis-linaloloxide | 169.3 | C10H18O2 |
31 | 6.31 | 1.6 | heptanoic acid | 128.2 | C7H13O2 |
32 | 6.35 | 1.6 | cyclopropylacetic acid | 99.1 | C5H8O2 |
33 | 6.86 | 1.2 | 1-(3, 7-dimethyl-1-octenyl)-cyclopropanol | 195.3 | C13H24O |
34 | 6.90 | 1.4 | benzyl nitrile | 116.2 | C8H7N |
35 | 7.31 | 1.1 | 1-(ethenylthio)-octane | 171.3 | C10H20S |
36 | 7.32 | 1.0 | 1, 2, 3, 4, 5-cyclopentanepentol | 149.1 | C5H10O5 |
37 | 7.61 | 1.1 | 1, 4-dimethyl-adamantane | 163.3 | C12H20 |
38 | 7.90 | 1.4 | 1-tridecanol | 199.4 | C13H28O |
39 | 8.03 | 1.1 | 1-pentanol | 87.2 | C5H12O |
40 | 8.11 | 1.3 | methyl-cycloheptane | 111.2 | C8H16 |
41 | 8.11 | 1.3 | 1, 2-dimethyl-cyclohexane | 111.2 | C8H16 |
42 | 8.36 | 1.1 | 2, 4-bis(diazo)adamantane | 187.2 | C10H12N4 |
43 | 8.36 | 1.1 | isopulegol | 153.3 | C10H18O |
44 | 8.6 | 1.9 | cyclopentadecanol | 225.4 | C15H30O |
45 | 8.68 | 1.3 | 2, 5-diethylphenol | 149.2 | C10H14O |
46 | 8.69 | 1.1 | thymol | 149.2 | C10H14O |
47 | 8.70 | 1.0 | 3-methyl-5-(1-methylethyl)-phenol methylcarbamate | 206.3 | C12H17NO2 |
48 | 9.11 | 1.1 | 2-carbonitrile-cyclopentanone | 108.1 | C6H7NO |
49 | 9.18 | 1.5 | 2-undecenal | 167.3 | C11H20O |
50 | 9.68 | 1.3 | n-decanoic acid | 171.3 | C10H20O2 |
51 | 9.68 | 1.3 | cubenol | 221.4 | C15H26O |
52 | 9.70 | 1.1 | 3-methyl-heptanedioic acid dimethyl ester | 201.2 | C10H18O4 |
53 | 9.73 | 1.3 | chamigrene | 203.4 | C15H24 |
54 | 9.80 | 1.0 | cyclodecane | 139.3 | C10H20 |
55 | 9.94 | 1.4 | 15(S)-hydroxy-(5Z, 8Z, 11Z, 13E)- eicosatetraenoic acid | 319.5 | C20H32O3 |
56 | 9.95 | 1.0 | 1, 8-cyclopentadecadiyne | 201.3 | C15H22 |
57 | 23.2 | 2.9 | 12, 15-octadecadienoic acid, methyl ester | 293.5 | C19H34O2 |
58 | 24.06 | 3.1 | linoleic acid ethyl ester | 307.5 | C20H36O2 |
Saikosaponin | Precursor Ion (m/z) | Product Ion I (m/z)/Collision Energy (eV) | Product Ion II (m/z)/Collision Energy (eV) |
---|---|---|---|
SSa | 779.5 | 439.6/52.0 | 617.3/32.2 |
SSc | 971.5 | 779.3/38.9 | 925.4/23.7 |
SSd | 779.5 | 439.2/55.0 | 617.3/33.1 |
SSe | 809.5 | 601.3/33.0 | 763.3/21.3 |
SSf | 973.5 | 781.3/39.9 | 927.4/23.4 |
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Wang, Z.; Zhao, H.; Tian, L.; Zhao, M.; Xiao, Y.; Liu, S.; Xiu, Y. Quantitative Analysis and Differential Evaluation of Radix Bupleuri Cultivated in Different Regions Based on HPLC-MS and GC-MS Combined with Multivariate Statistical Analysis. Molecules 2022, 27, 4830. https://doi.org/10.3390/molecules27154830
Wang Z, Zhao H, Tian L, Zhao M, Xiao Y, Liu S, Xiu Y. Quantitative Analysis and Differential Evaluation of Radix Bupleuri Cultivated in Different Regions Based on HPLC-MS and GC-MS Combined with Multivariate Statistical Analysis. Molecules. 2022; 27(15):4830. https://doi.org/10.3390/molecules27154830
Chicago/Turabian StyleWang, Zhenhuan, Huanxi Zhao, Lu Tian, Mengya Zhao, Yusheng Xiao, Shuying Liu, and Yang Xiu. 2022. "Quantitative Analysis and Differential Evaluation of Radix Bupleuri Cultivated in Different Regions Based on HPLC-MS and GC-MS Combined with Multivariate Statistical Analysis" Molecules 27, no. 15: 4830. https://doi.org/10.3390/molecules27154830