Preparative separation of isoquinoline alkaloids from Corydalis impatiens using middle chromatogram isolated gel column coupled with positively charged reversed-phase liquid chromatography.
isoquinoline alkaloids
positive charge
preparative separation
traditional Tibetan medicine
Journal
Journal of separation science
ISSN: 1615-9314
Titre abrégé: J Sep Sci
Pays: Germany
ID NLM: 101088554
Informations de publication
Date de publication:
Jul 2020
Jul 2020
Historique:
received:
14
11
2019
revised:
03
03
2020
accepted:
28
03
2020
pubmed:
3
4
2020
medline:
1
4
2021
entrez:
3
4
2020
Statut:
ppublish
Résumé
Positively charged reversed-phase liquid chromatography was employed for the efficient preparative separation of isoquinoline alkaloids from Corydalis impatiens. Ten commercially available columns were compared for isoquinoline alkaloids analysis. While tailing, overloading, lower resolution, and buffer salts limited the application in purification of isoquinoline compounds of many of these columns, one positively charged reversed-phase C18 column (XCharge C18) overcame these drawbacks, allowing for favorable separation resolution, even when loading isoquinoline compounds on a larger, preparative scale. The general separation process is as follows. First, isoquinoline alkaloids are enriched with Corydalis impatiens extract via a middle chromatogram isolated gel column. After column selection, separation is performed on an XCharge C18 analytical column, from which two evident chromatographic peaks are readily obtained. Finally, two isoquinoline alkaloids (protopine and corydamine) are selectively purified on the XCharge C18 preparative column. These results demonstrate that a middle chromatogram isolated gel column coupled with positively charged reversed-phase liquid chromatography is effective for the preparative separation of isoquinoline alkaloids from Corydalis impatiens.
Identifiants
pubmed: 32240569
doi: 10.1002/jssc.201901164
doi:
Substances chimiques
Alkaloids
0
Isoquinolines
0
isoquinoline
JGX76Y85M6
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2521-2528Subventions
Organisme : the Youth Innovation Promotion Association of the Chinese Academy of Sciences
ID : 2017471
Organisme : the Applied Basic Research Project of Qinghai Province
ID : 2016-ZJ-714
Organisme : the Innovation Platform for the Development and Construction of Special Project of Key Laboratory for Tibet Plateau Phytochemistry of Qinghai Province
ID : 2017-ZJ-Y19
Organisme : the International Cooperation Project of Qinghai Province
ID : 2019-HZ-805
Organisme : the Major New Drug Creation Special Projects
ID : 2019ZX09201001
Informations de copyright
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
Pan, G. Q., Shen, J. W., Ma, Y. H., He, Y. F., B, Y., Li, R. R., Wang, S. S., Wang, Q., Lin, P. C., Dang, J., Preparative separation of isoquinoline alkaloids from Corydalis impatiens using a middle-pressure chromatogram isolated gel column coupled with two-dimensional liquid chromatography. J. Sep. Sci. 2019, 42, 3182-3190.
Niu, X. F., Xu, H. B., Liu, X., Fan, T., Qi, L., Isoquinoline alkaloids from Corydalis impatiens. Chem. Nat. Compd. 2013, 49, 187-189.
Li, J. C., Dong, X. H., Deng, J. W., Dai, Y., Zhang, J. S., Li, G. P., Studies on the alkaloids from roots of Corydalis impatiens. J. Chin. Med. Mater. 2010, 33, 210-213.
Li, W. F., Huang, H. M., Zhang, Y. M., Fang, T., Liu, X., Xing, W., Niu, X. F., Anti-inflammatory effect of tetrahydrocoptisine from Corydalis impatiens is a function of possible inhibition of TNF-α, IL-6 and NO production in lipopolysaccharide-stimulated peritoneal macrophages through inhibiting NF-κB activation and MAPK pathway. Eur. J. Pharmacol. 2013, 715, 62-71.
Han, J. W., Shim, S. H., Jang, K. S., Choi, Y. H., Kim, H., Choi, G. J., In vivo disease control efficacy of isoquinoline alkaloids isolated from Corydalis ternata against wheat leaf rust and pepper anthracnose. J. Microbiol. Biotech. 2018, 28, 262-266.
Zhou, Y. F., Yu, Y. L., Gao, L. L., Fei, Y. F., Ye, T., Li, Q. S., Zhou, X. S., Gan, N., Shao, Y., Structuring polarity-inverted TBA to G-quadruplex for selective recognition of planarity of natural isoquinoline alkaloids. Analyst. 2018, 143, 4907-4914.
Niu, X. F., Li, W. F., Xu, H. B., Liu, X., Qi, L., Simultaneous quantification of 11 isoquinoline alkaloids in Corydalis impatiens (Pall.) Fisch by HPLC. J. Sep. Sci. 2013, 36, 2090-2095.
Resende, D. I. S. P., Papichaya, B., Sousa, E., Anake, K., Pinto, M. M. M., Chemistry of the fumiquinazolines and structurally related alkaloids. Nat. Prod. Rep. 2019, 36, 7-34.
Cordell, G. A., Quinn-Beattie, M. L., Farnsworth, N. R., The potential of alkaloids in drug discovery. Phytotherapy. 2010, 15, 183-205.
Zhang, Y. B., Li, M., Li, X. J., Zhang, T., Qin, M., Ren, L. Q., Isoquinoline alkaloids and indole alkaloids attenuate aortic atherosclerosis in apolipoprotein E deficient mice: A systematic review and meta-analysis. Front Pharmacol. 2018, 9, 602.
Ghulam, H., Azhar, R., Haseeb, A., Nimra, A., Aroona, R., Wei, W., Muhammad, A., Li, J., Li, X. M., Role of plant derived alkaloids and their mechanism in neurodegenerative disorders. Int. J. Biol. Sci. 2018, 14, 341-357.
Bo, T., Zhong, L., Li, M., Luo, Y. Q., Li, K. A., Liu, H. W., Guo, D. A., Separation of isoquinoline alkaloids and saponins by microemulsion electrokinetic chromatography with anionic and cationic surfactants. Chromatographia. 2002, 56, 709-716.
Poole, C. F., Chromatographic test methods for characterizing alkylsiloxane-bonded silica columns for reversed-phase liquid chromatography. J. Chromatogr. B. 2018, 1092, 207-219.
Esmaiili, K., Shetab-Boushehri, S. V., Comparative verification study of silica gel-coated TLC and HPTLC plates’ performances in separation of opium alkaloids on the basis of their physicochemical properties. J. Anal. Sci. Technol. 2017, 8, 22.
Kim, K. H., Piao, C. J., Choi, S. U., Son, M. W., Lee, K. R., New cytotoxic tetrahydroprotoberberine-aporphine dimeric and aporphine alkaloids from Corydalis turtschaninovii. Planta Med. 2010, 76, 1732-1738.
Yang, J., Zhang, L. Y., Zhu, G. H., Li, L., Separation and enrichment of major quinolizidine type alkaloids from Sophora alopecuroides using macroporous resins. J. Chromatogr. B. 2014, 945-946, 17-22.
Niu, L. L., Xie, Z. S., Cai, T. X., Wu, P., Xue, P., Chen, X. L., Wu, Z. Y., Ito, Y., Li, F. M., Yang, F. Q., Preparative isolation of alkaloids from Corydalis bungeana Turcz. by high-speed counter-current chromatography using stepwise elution. J. Sep. Sci. 2011, 34, 987-994.
Feng, R. H., Hou, J. J., Zhang, Y. B., Pan, H. Q., Guo, D. A., Yang, W. Z., Qi, P., Yao, S., Cai, L. Y., Yang, M., Jiang, B. H., Liu, X., Wu, W. Y., Guo, D. A., An efficient and target-oriented sample enrichment method for preparative separation of minor alkaloids by pH-zone-refining counter-current chromatography. J. Chromatogr. A. 2015, 1409, 159-165
Jiao, L. J., Tao, Y. D., Wang, W. D., Shao, Y., Mei, L. J., Wang, Q. L., Dang, J. Preparative isolation of flavonoid glycosides from Sphaerophysa salsula using hydrophilic interaction solid-phase extraction coupled with two-dimensional preparative liquid chromatography. J. Sep. Sci. 2017, 40, 3808-3816.
Dang, J., Cui, Y. L., Pei, J. J., Yue, H. L., Liu, Z. G., Wang, W. D., Jiao, L. J., Mei, L. J., Wang, Q. L., Tao, Y. D., Shao, Y., Efficient separation of four antibacterial diterpenes from the roots of Salvia prattii using non-aqueous hydrophilic solid-phase extraction followed by preparative high-performance liquid chromatography. Molecules. 2018, 23, 1-12.
Li, S. L., Li, S. N., Huang, Y., Liu, C. M., Chen, L. N., Zhang, Y. C., Ionic-liquid-based ultrasound-assisted extraction of isoflavones from Belamcanda chinensis and subsequent screening and isolation of potential α-glucosidase inhibitors by ultrafiltration and semi-preparative high-performance liquid chromatography. J. Sep. Sci. 2017, 40, 2565-2574.
Chen, J. Y., He, L. H., Yang, T., Scale-up purification for rutin hyrdrolysates by high-performance counter-current chromatography coupled with semi-preparative high-performance liquid chromatography. J. Sep. Sci. 2016, 51, 1523-1530.
Gazic, I., Bosak, A., Sinko, G., Vinkovic, V., Kovarik, Z., Preparative HPLC separation of bambuterol enantiomers and stereoselective inhibition of human cholinesterases. Anal. Bioanal. Chem. 2006, 385, 1513-1519.
Mills, J. B., Mant, C. T., Hodges, R. S., One-step purification of a recombinant protein from a whole cell extract by reversed-phase high-performance liquid chromatography. J. Chromatogr. A. 2006, 1133, 248-253.
Wang, C. R., Guo, Z. M., Long, Z., Zhang, X. L., Liang, X. M., Overloading study of basic compounds with a positively charged C18 column in liquid chromatography. J. Chromatogr. A. 2013, 1281, 60-66.
Li, X. L., Guo, Z. M., Wang, C. R., Shen, A. J., Liu, Y. F., Zhang, X. L., Zhao, W. J., Liang, X. M., Purification of bufadienolides from the skin of Bufo bufo gargarizans cantor with positively charged C18 column. J. Pharmaceut. Biomed. Anal. 2014, 92, 105-113.
Qin, H. L., Wang, P., Li, Z. H., Liu, X., He, W. Y., The establishment of the control substance and 1H nuclear magnetic resonance fingerprint of Macleaya Microcarpa (Maxim.) Fedde. Chinese J. Anal. Chem. 2004, 32, 1165-1170.
Christoph, S., Sonja, S., Eva-Maria, S., Ernst, E., Hermann, S., 1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae). Magn. Reson. Chem. 2004, 42, 882-886.