Semi-Preparative Separation of 10 Caffeoylquinic Acid Derivatives Using High Speed Counter-Current Chromatogaphy Combined with Semi-Preparative HPLC from the Roots of Burdock (Arctium lappa L.)
Abstract
:1. Introduction
2. Results and Discussion
2.1. Optimization of HSCCC Conditions
2.1.1. Separation of Fr. 1 by HSCCC
2.1.2. Separation of Fr. 2 by HSCCC
2.1.3. Separation of Fr. 3 by HSCCC
2.2. Identification of Compounds
2.2.1. Identification of Known Compounds
2.2.2. Identification of New Compounds
3. Experimental
3.1. Material and Reagents
3.2. Apparatus
3.3. Pre-Processing of Crude Sample
3.4. Optimization of HPLC Conditions
3.5. Selection and Preparation of the Two-Phase Solvent System
3.6. Separation Procedure
3.7. Semi-Preparative HPLC Separations
3.8. Identification of Compounds
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Not available. |
Sample | Solvent System (Pet-EtOAc-MeOH-H2O, v/v) | KD | ||||||||
---|---|---|---|---|---|---|---|---|---|---|
A | B | C | D | E | F | G | H | I/J | ||
Fr. 1 | 0:5:0:5 | 0.55 | 0.58 | 4.82 | ||||||
0:5:0.5:5 | 0.47 | 0.52 | 2.21 | |||||||
Fr. 2 | 0:5:1:5 | 26.88 | ||||||||
1:5:1:5 | 4.00 | |||||||||
1:4:1:4 | 2.03 | |||||||||
Fr. 3 | 1:4:1:4 | 0.50 | 2.16 | 2.29 | 2.25 | 7.88 | ||||
1:4:2:3 | 0.19 | 0.29 | 0.39 | 0.41 | 0.76 |
Position | Compound I | Compound J | ||
---|---|---|---|---|
δH (ppm, Mult, J in Hz) | δC (ppm) | δH (ppm, Mult, J in Hz) | δC (ppm) | |
1 | 79.7 | 78.8 | ||
2 | 2.31–2.47 (m, overlap) | 32.3 | 2.34–2.58 (m, overlap) | 31.4 |
3 | 5.38 (d, 3.6) | 69.1 | 5.26 (m) | 69.5 |
4 | 4.88 (dd, 3.2, 8.8) | 74.7 | 3.85 (dd, 3.2, 8.8) | 71.3 |
5 | 4.14 (m) | 63.9 | 5.23 (m ) | 68.7 |
6 | 1.92 (m), 2.31–2.47 (m, overlap) | 39.4 (overlap) | 1.93 (m), 2.34–2.58 (m, overlap) | 35.9 |
7 | 172.6 | 172.0 | ||
1′ | 171.4 | 171.7 | ||
2′ | 2.31–2.47 (m, overlap) | 28.8 | 2.34–2.58 (m, overlap) | 28.3 |
3′ | 2.31–2.47 (m, overlap) | 29.3 | 2.34–2.58 (m, overlap) | 28.8 |
4′ | 172.4 | 171.2 | ||
-OCH3 | 3.48 (s) | 51.8 | 3.51 (s) | 51.3 |
1″ | 126.0 | 125.3 | ||
2″ | 7.07 (1H, br s) | 115.4 | 7. 07 (br s) | 114.7 |
3″ | 145.6 (overlap) | 145.8 | ||
4″ | 148.9 | 148.2 | ||
5″ | 6.78 (d, 8.4) | 116.3 | 6.79 (d, 8.0) | 115.7 |
6″ | 7.03 (d, 8.4) | 121.9 | 7. 03 (dd, 8.0) | 121.3 |
7″ | 7.50 (d, 15.6) | 146.1 | 7.51 (d, 16.0) | 145.2 |
8″ | 6.31 (d, 15.6) | 114.5 | 6.25 (d, 16.0) | 113.7 |
9″ | 166.5 | 165.1 | ||
1″′ | 125.9 | 125. 4 | ||
2′′′ | 7.06 (br s) | 115.3 | 7. 07(br s) | 114. 8 |
3′′′ | 145.6 (overlap) | 145.8 | ||
4′′′ | 149.0 | 148.3 | ||
5′′′ | 6.77 (d, 8.4) | 116.2 | 6.80 (d, 8.0) | 115.7 |
6′′′ | 7.00 (d, 8.4) | 121.8 | 7.05 (dd, 8.0) | 121.3 |
7′′′ | 7.47 (d, 15.6) | 146.1 | 7. 52 (d, 16.0) | 145.3 |
8′′′ | 6.23 (d, 15.6) | 114.5 | 6. 29 (d, 16.0) | 114.0 |
9′′′ | 165.8 | 165.9 |
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Zheng, Z.; Wang, X.; Liu, P.; Li, M.; Dong, H.; Qiao, X. Semi-Preparative Separation of 10 Caffeoylquinic Acid Derivatives Using High Speed Counter-Current Chromatogaphy Combined with Semi-Preparative HPLC from the Roots of Burdock (Arctium lappa L.). Molecules 2018, 23, 429. https://doi.org/10.3390/molecules23020429
Zheng Z, Wang X, Liu P, Li M, Dong H, Qiao X. Semi-Preparative Separation of 10 Caffeoylquinic Acid Derivatives Using High Speed Counter-Current Chromatogaphy Combined with Semi-Preparative HPLC from the Roots of Burdock (Arctium lappa L.). Molecules. 2018; 23(2):429. https://doi.org/10.3390/molecules23020429
Chicago/Turabian StyleZheng, Zhenjia, Xiao Wang, Pengli Liu, Meng Li, Hongjing Dong, and Xuguang Qiao. 2018. "Semi-Preparative Separation of 10 Caffeoylquinic Acid Derivatives Using High Speed Counter-Current Chromatogaphy Combined with Semi-Preparative HPLC from the Roots of Burdock (Arctium lappa L.)" Molecules 23, no. 2: 429. https://doi.org/10.3390/molecules23020429