Tissue-Specific Metabolite Profiling on the Different Parts of Bolting and Unbolting Peucedanum praeruptorum Dunn (Qianhu) by Laser Microdissection Combined with UPLC-Q/TOF–MS and HPLC–DAD
Abstract
:1. Introduction
2. Results
2.1. The Characteristics and Microscopic Frameworks Between Ci Qianhu and Xiong Qianhu
2.1.1. Ci Qianhu
2.1.2. Xiong Qianhu
2.2. Separation of Different Cells and Tissues by Fluorescence Microscopy
2.3. Metabolite Profiling by UPLC-Q/TOF–MS
2.4. Tissue-Specific Chemical Profiling of the Ci Qianhu
2.5. Tissue-Specific Chemical Profiling of the Xiong Qianhu
2.6. Comparison Between Ci Qianhu and Xiong Qianhu
2.7. Quantitative Analysis Results by HPLC–DAD
3. Materials and Methods
3.1. Samples and Reagents
3.2. Microscopic Analysis
3.3. UPLC-Q/TOF–MS Analysis
3.3.1. Sample Preparation
3.3.2. UPLC-Q/TOF–MS method
3.4. HPLC–DAD Analysis
3.4.1. Standard Solutions Preparation
3.4.2. Sample Preparation
3.4.3. HPLC–DAD Method
3.4.4. Method Validation
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Peak Number | tR (min) | Molecular Formula | Measured Mass (m/z) | Mass Error (ppm) | MS/MS(m/z) | Identification | Existence in C/X |
---|---|---|---|---|---|---|---|
1 | 2.20 | C14H14O5 | 263.0918 | 1.6 | 149.0234; 191.0342; 245.0808; 263.0496 | Rutatin | C, X |
2 | 2.39 | C20H24O9 | 408.9195 | −0.6 | 169.9816; 199.1246; 243.1513; 263.1489; 301.1412 | Nodakenin | C, X |
3 | 2.42 | C10H8O4 | 193.0497 | 0.2 | 133.5869; 177.1078; 182.9506 | Scopolin | C, X |
4 | 2.52 | C14H14O5 | 263.0911 | 2.4 | 107.0324; 117.0908; 135.0892; 145.0079 | Khellactone | X |
5 | 4.99 | C16H16O6 | 305.1024 | −2.9 | 141.9585; 175.0385; 203.0709; 245.0804; 327.0830 | Qianhucoumarin B | C, X |
6 | 6.66 | C13H10O5 | 247.0607 | 2.4 | 189.0185; 217.0492; 232.0362; 247.0607 | Isopimpinellin | X |
7 | 6.99 | C21H22O9 | 436.1648 | 0.6 | 175.0392; 227.0697; 245.0810; 359.1180 | 3′-(dihydroxyl-angel/dihydroxyl-senecioyl/dihydroxyl-tigloyl)-4′-acetylkhellactone | C, X |
8 | 7.42 | C21H22O8 | 425.1180 | 1.1 | 227.0705; 245.0809; 271.0971; 343.1180; 436.1979 | 3′-(hydroxyl-angel/hydroxyl-senecioyl/hydroxyl-tigloyl)-4′-acetylkhellactone | C, X |
9 | 7.83 | C21H22O8 | 425.1655 | 0.9 | 175.0392; 227.0707; 245.0815; 343.1180; 436.1936; 441.0936 | 3′-(hydroxyl-angel/hydroxyl-senecioyl/hydroxyl-tigloyl)-4′-acetylkhellactone | C, X |
10 | 8.36 | C18H18O7 | 369.0942 | −0.7 | 175.0390; 227.0705; 245.0813; 287.0916; | Qianhucoumarin D or trans-3,4-diacetylkhellactone | X |
11 | 8.78 | C19H20O6 | 367.1161 | 2.3 | 147.0441; 175.0391; 203.0704; 245.0810; 345.1303 | Qianhucoumarin A | C |
12 | 9.11 | C19H20O6 | 367.1146 | 0.6 | 175.0390; 203.0705; 245.0811; 345.1338 | 3′-(angeloyl/senecioyl/tigloyl)-khellactone | C |
13 | 9.23 | C21H22O8 | 425.1645 | −0.7 | 203.1077; 245.0810; 327.1225; 343.1174 | 3′-(hydroxyl-angel/hydroxyl-senecioyl/hydroxyl-tigloyl)-4′-acetylkhellactone | C, X |
14 | 10.46 | C19H22O6 | 369.1307 | 0.4 | 175.0391; 203.0705; 245.0811; 329.1385; 347.1468 | 3′-(isovaleryl/2-methylbutyryl)- khellactone | C, X |
15 | 10.70 | C16H14O4 | 271.0912 | −1 | 119.0853; 203.0337; 271.0912; 391.2840 | Imperatorin | C, X |
16 | 10.92 | C19H18O6 | 365.0990 | 0 | 163.0388; 243.0655; 261.0763; 343.1176 | Qianhucoumarin E | C, X |
17 | 11.48 | C19H20O6 | 367.1257 | -0.1 | 149.0233; 243.0657; 261.0762; 345.1332 | 3′-(isovaleryl/2-methylbutyryl)-4′-oxo-3′,4′-dihydroseselin | C, X |
18 | 11.54 | C15H16O4 | 261.0762 | −1 | 93.0567; 149.0233; 193.0492 | 7-methoxy-5-prenyloxycoumarin | C, X |
19 | 11.67 | C20H22O7 | 397.1258 | 0 | 175.0389; 199.0760; 227.0706; 245.0812; 315.1231 | Hyuganin D | C, X |
20 | 12.09 | C21H22O7 | 409.1253 | −1.4 | 175.0391; 245.0811; 299.1292; 327.1231 | Qianhucoumarin I | C, X |
21 | 12.22 | C21H22O7 | 409.1258 | 0.1 | 83.0492; 175.0389; 227.0707; 327.1229 | 3′-(tigloyl/senecioy)-4′-acetykhellactone | C, X |
22 | 12.37 | C21H22O7 | 409.1257 | 0.5 | 227.0709; 245.0808; 327.1233; 404.1704; 425.0995 | cis-3′-acetyl-4′-angeloykhellactone | C, X |
23 | 12.62 | C21H22O7 | 409.1256 | −0.3 | 83.0498; 227.0805; 245.0808; 327.1227 | Praeruptorin A | C, X |
24 | 13.31 | C21H24O7 | 411.1411 | −0.8 | 175.0389; 227.0705; 245.0811; 329.1384; 411.1411 | Hyuganin C | C, X |
25 | 14.49 | C22H24O7 | 423.1405 | −2.2 | 175.0387; 227.0705; 245.0805; 327.1226 | Qianhucoumarin J | C, X |
26 | 15.05 | C22H26O7 | 420.2010 | −1.7 | 227.0705; 245.0810; 329.1384 | 3′-(isovaleryl/2-methylbutyryl)-4′-propionylkhellactone | C |
27 | 17.06 | C23H26O7 | 432.2013 | −0.7 | 83.04914; 149.0234; 227.0704; 245.0791; 327.1228; 465.1300 | 3′-(angeloyl/senecioyl/tigloyl)-4-isovalerylkhellactone | C, X |
28 | 17.48 | C24H26O7 | 449.1517 | −0.5 | 149.0233; 175.0387; 227.0710; 327.1226 | 3′-(angeloyl/senecioyl/tigloyl)-4′- (angeloyl/senecioyl/tigloyl)’-khellactone | C, X |
29 | 17.93 | C24H26O7 | 449.1566 | −0.6 | 83.0493; 227.0705; 245.0806; 327.1230 | 3′-(angeloyl/senecioyl/tigloyl)-4′- (angeloyl/senecioyl/tigloyl)’-khellactone | C, X |
30 | 18.23 | C24H26O7 | 449.1563 | −0.9 | 227.0704; 245.0808; 327.1226 | Praeruptorin B | C, X |
31 | 19.37 | C24H28O7 | 451.1713 | 1.1 | 175.0385; 227.0706; 245.0807; 329.1386 | 3′-(isovaleryl/2-methylbutyryl)-4′-(tigloy/senecioyl/angeloyl)-khellactone | C, X |
32 | 19.64 | C24H28O7 | 451.1724 | −0.6 | 83.0487; 199.0753; 227.0703; 327.1226 | 3′-(isovaleryl/2-methylbutyryl)-4′-(tigloy/senecioyl/angeloyl)-khellactone | C, X |
33 | 20.12 | C24H28O7 | 451.1728 | 0.2 | 83.0491; 227.0706; 245.0810; 327.1230 | Praeruptorin E | C, X |
34 | 22.07 | C24H30O7 | 453.1886 | 1 | 175.0391; 227.2015; 245.0815; 329.1389 | cis-3′,4′-diisovalerylkhellactone | C, X |
Category | Tissue | The Content in Each Parts (mg/g) | Total | ||||||
---|---|---|---|---|---|---|---|---|---|
Peucedanol | Xanthotoxin | Bergapten | Imperatorin | Praeruptorin A | Praeruptorin B | Praeruptorin E | |||
Ci Qianhu | Bark | 0.38 ± 0.17 | 0.09 ± 0.10 | 0.43 ± 0.39 | 0.20 ± 0.08 | 12.56 ± 2.45 | 0.84 ± 0.36 | 2.85 ± 1.80 | 17.35 |
Middle part | 0.09 ± 0.02 | 0.03 ± 0.04 | 0.12 ± 0.08 | 0.18 ± 0.10 | 11.76 ± 4.01 | 1.11 ± 0.70 | 3.06 ± 2.10 | 16.35 | |
Inner part | 0.05 ± 0.05 | 0.01 ± 0.01 | 0.02 ± 0.01 | 0.10 ± 0.02 | 3.76 ± 3.42 | 0.29 ± 0.32 | 1.24 ± 1.46 | 5.46 | |
Whole root | 0.04 ± 0.20 | 0.15 ± 0.20 | 0.43 ± 0.52 | 0.23 ± 0.30 | 8.21 ± 3.30 | 2.12 ± 3.24 | 1.90 ± 0.99 | 13.09 | |
Xiong Qianhu | Bark | 0.68 ± 0.74 | 0.09 ± 0.10 | 0.39 ± 0.34 | 0.31 ± 0.27 | 20.13 ± 4.39 | 1.53 ± 1.29 | 6.53 ± 5.14 | 29.65 |
Middle part | 0.29 ± 0.18 | 0.09 ± 0.13 | 0.40 ± 0.43 | 0.35 ± 0.41 | 15.80 ± 9.44 | 1.06 ± 0.82 | 4.72 ± 4.43 | 22.70 | |
Inner part | 0.06 ± 0.00 | 0.02 ± 0.01 | 0.24 ± 0.23 | 0.03 ± 0.03 | 2.61 ± 1.52 | 0.21 ± 0.20 | 0.93 ± 0.89 | 4.10 | |
Whole root | 0.09 ± 0.05 | 0.17 ± 0.21 | 0.35 ± 0.20 | 0.25 ± 0.29 | 8.62 ± 3.29 | 1.25 ± 1.27 | 1.82 ± 0.755 | 12.55 |
Number | Collection Area | Collection Time | C/X (Ci Qianhu/Xiong Qianhu) | Latitude and Longitude |
---|---|---|---|---|
1 a | Gangkou, Ningguo, Anhui | 2016.12.20 | C | 30°41′42.28″ N, 118°54′51.06″ E |
2 a | Gangkou, Ningguo, Anhui | 2017.7.12 | X | 30°41′42.28″ N, 118°54′51.06″ E |
3 b | Gangkou, Ningguo, Anhui | 2016.11.16 | C | 30°41′42.28″ N, 118°54′51.06″ E |
4 b | Gangkou, Ningguo, Anhui | 2017.12.10 | X | 30°41′42.28″ N, 118°54′51.06″ E |
5 b | Qimen, Huangshan, Anhui | 2016.12.20 | C | 29°59′11.78″ N, 117°20′50.28″ E |
6 b | Jixi, Xuancheng, Anhui | 2017.12.11 | C | 30°04′1.86″ N, 118°34′47.75″ E |
7 b | Qingyang, Chizhou, Anhui | 2018.9.18 | C | 30°38′24.72″ N, 117°50′50.96″ E |
8 b | Gangkou, Ningguo, Anhui | 2018.9.18 | C | 30°41′42.28″ N, 118°54′51.06″ E |
9 b | Gangkou, Ningguo, Anhui | 2018.9.18 | X | 30°41′42.28″ N, 118°54′51.06″ E |
10 b | Qingyang, Chizhou, Anhui | 2018.9.18 | X | 30°38′24.72″ N, 117°50′50.96″ E |
11 b | Jinde, Xuancheng, Anhui | 2018.9.3 | X | 30°17′14.03″ N,118°32′25.62″ E |
12 b | Modian, Hefei, Anhui | 2018.9.3 | X | 31°56′20.18″ N, 117°23′29.64″ E |
13 c | Huangdu, Ningguo, Anhui | 2017.12.10 | C | 30°43′14.70″ N, 118°51′6.95″ E |
14 c | Huangdu, Ningguo, Anhui | 2017.12.10 | C | 30°43′14.70″ N, 118°51′6.95″ E |
15 c | Huangdu, Ningguo, Anhui | 2017.12.10 | C | 30°43′14.70″ N, 118°51′6.95″ E |
16 c | Huangdu, Ningguo, Anhui | 2017.12.10 | C | 30°43′14.70″ N, 118°51′6.95″ E |
17 c | Huangdu, Ningguo, Anhui | 2017.12.10 | C | 30°43′14.70″ N, 118°51′6.95″ E |
18 c | Huangdu, Ningguo, Anhui | 2017.12.10 | C | 30°43′14.70″ N, 118°51′6.95″ E |
19 c | Gangkou, Ningguo, Anhui | 2017.12.10 | X | 30°41′42.28″ N, 118°54′51.06″ E |
20 c | Gangkou, Ningguo, Anhui | 2017.12.10 | X | 30°41′42.28″ N, 118°54′51.06″ E |
21 c | Gangkou, Ningguo, Anhui | 2017.12.10 | X | 30°41′42.28″ N, 118°54′51.06″ E |
22 c | Gangkou, Ningguo, Anhui | 2017.12.10 | X | 30°41′42.28″ N, 118°54′51.06″ E |
23 c | Gangkou, Ningguo, Anhui | 2017.12.10 | X | 30°41′42.28″ N, 118°54′51.06″ E |
24 c | Gangkou, Ningguo, Anhui | 2017.12.10 | X | 30°41′42.28″ N, 118°54′51.06″ E |
25 c | Xianyushan, Chizhou, Anhui | 2018.4.21 | C | 29°59′10.14″ N, 117°16′57.50″ E |
26 c | Xianyushan, Chizhou, Anhui | 2018.4.21 | C | 29°59′10.14″ N, 117°16′57.50″ E |
27 c | Xianyushan, Chizhou, Anhui | 2018.4.21 | C | 29°59′10.14″ N, 117°16′57.50″ E |
28 c | Xianyushan, Chizhou, Anhui | 2018.4.21 | C | 29°59′10.14″ N, 117°16′57.50″ E |
29 c | Xianyushan, Chizhou, Anhui | 2018.4.21 | C | 29°59′10.14″ N, 117°16′57.50″ E |
30 c | Xianyushan, Chizhou, Anhui | 2018.4.21 | C | 29°59′10.14″ N, 117°16′57.50″ E |
31 c | Xianyushan, Chizhou, Anhui | 2018.8.22 | X | 29°59′10.14″ N, 117°16′57.50″ E |
32 c | Xianyushan, Chizhou, Anhui | 2018.8.22 | X | 29°59′10.14″ N, 117°16′57.50″ E |
33 c | Xianyushan, Chizhou, Anhui | 2018.8.22 | X | 29°59′10.14″ N, 117°16′57.50″ E |
34 c | Xianyushan, Chizhou, Anhui | 2018.8.22 | X | 29°59′10.14″ N, 117°16′57.50″ E |
35 c | Xianyushan, Chizhou, Anhui | 2018.8.22 | X | 29°59′10.14″ N, 117°16′57.50″ E |
36 c | Xianyushan, Chizhou, Anhui | 2018.8.22 | X | 29°59′10.14″ N, 117°16′57.50″ E |
Analytes. | Peucedanol | Xanthotoxin | Bergapten | Imperatorin | Praeruptorin A | Praeruptorin B | Praeruptorin E |
---|---|---|---|---|---|---|---|
Range (μg /mL) | 10–60 | 2–100 | 5.7–456 | 3.6–360 | 160–16,000 | 18–1800 | 9–1440 |
Regression equation | y = 11.29x − 0.2129 | y = 8.6057x + 5.4184 | y = 24.171x − 0.2627 | y = 4.9076x + 3.1037 | y = 404.9x − 9.8906 | y = 40.943x − 16.533 | y = 190.48x + 9.9344 |
LOD (μg/mL) | 0.10 | 0.02 | 0.03 | 0.02 | 0.01 | 0.02 | 0.08 |
LOQ (μg/ mL) | 0.22 | 0.04 | 0.07 | 0.06 | 0.75 | 0.72 | 0.12 |
R2 | 0.9998 | 0.9972 | 1.0000 | 0.9998 | 0.9999 | 0.9999 | 1.0000 |
Intra-precision (%RSD) | 1.85 | 1.67 | 1.04 | 1.46 | 0.95 | 1.29 | 1.14 |
Inter-precision (%RSD) | 4.71 | 1.71 | 0.70 | 1.25 | 0.78 | 0.98 | 0.77 |
Repeatability (%RSD) | 1.34 | 1.30 | 1.08 | 1.19 | 1.01 | 0.93 | 0.78 |
Stability (%RSD) | 4.01 | 0.50 | 2.99 | 2.92 | 0.55 | 0.60 | 0.55 |
Recovery (%) | 95.54 | 100.25 | 99.18 | 95.45 | 102.30 | 98.98 | 102.99 |
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Chen, L.L.; Chu, S.S.; Zhang, L.; Xie, J.; Dai, M.; Wu, X.; Peng, H.S. Tissue-Specific Metabolite Profiling on the Different Parts of Bolting and Unbolting Peucedanum praeruptorum Dunn (Qianhu) by Laser Microdissection Combined with UPLC-Q/TOF–MS and HPLC–DAD. Molecules 2019, 24, 1439. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24071439
Chen LL, Chu SS, Zhang L, Xie J, Dai M, Wu X, Peng HS. Tissue-Specific Metabolite Profiling on the Different Parts of Bolting and Unbolting Peucedanum praeruptorum Dunn (Qianhu) by Laser Microdissection Combined with UPLC-Q/TOF–MS and HPLC–DAD. Molecules. 2019; 24(7):1439. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24071439
Chicago/Turabian StyleChen, Ling Li, Shan Shan Chu, Ling Zhang, Jin Xie, Min Dai, Xin Wu, and Hua Sheng Peng. 2019. "Tissue-Specific Metabolite Profiling on the Different Parts of Bolting and Unbolting Peucedanum praeruptorum Dunn (Qianhu) by Laser Microdissection Combined with UPLC-Q/TOF–MS and HPLC–DAD" Molecules 24, no. 7: 1439. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24071439