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Preparative isolation of novel antioxidant flavonoids of alfalfa by stop-and-go counter-current chromatography and following on-line liquid chromatography desalination.
J Chromatogr A. 2011 Sep 09; 1218(36):6191-9.JC

Abstract

In this work, we have established a new stop-and-go two-dimensional chromatography coupling of counter-current chromatography and liquid chromatography (2D CCC × LC) for the preparative separation of two novel antioxidant flavonoids from the extract of alfalfa (Medicago sativa L.). The CCC column has been used as the first dimension to purify the target flavonoids using a solvent system of isopropanol and 20% sodium chloride aqueous solution (1:1, v/v) with the stop-and-go flow technique, and the LC column packed with macroporous resin has been employed as the second dimension for on-line absorption, desalination and desorption of the targeting effluents purified from the first CCC dimension. As a result, two novel flavonoids, 6,8-dihydroxy-flavone-7-O-β-D-glucuronide (15.3 mg) and 6-methoxy-8-hydroxy-flavone-7-O-β-D-glucuronide (13.7 mg), have been isolated from 126.8 mg of crude sample pre-enriched by macroporous resin column. Their structures have been identified by electrospray ionization mass spectrometry (ESI-MS), electrospray ionization time-of-flight mass spectrometry (ESI-TOF-MS) and one- and two-dimensional nuclear magnetic resonance spectra (1D and 2D NMR). Further antioxidant assays showed that the first component possess a strong antioxidant activity. All the results demonstrated that the stop-and-go 2D CCC × LC method is very efficient for the separation of flavonoids of alfalfa and it can also be applied to isolate other comprehensive multi-component natural products.

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Authors+Show Affiliations

Liang J
Research Center of Siyuan Natural Pharmacy and Biotoxicology, College of Life Sciences, Zhejiang University, Hangzhou, Zhejiang Province 310058, China.
Yang Z
No affiliation info available
Cao X
No affiliation info available
Wu B
No affiliation info available
Wu S
No affiliation info available

MeSH

AntioxidantsChromatography, LiquidCountercurrent DistributionFlavonoidsMedicago sativaMolecular StructurePlant ExtractsSpectrometry, Mass, Electrospray Ionization

Pub Type(s)

Evaluation Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21092976

Citation

Liang, Junling, et al. "Preparative Isolation of Novel Antioxidant Flavonoids of Alfalfa By Stop-and-go Counter-current Chromatography and Following On-line Liquid Chromatography Desalination." Journal of Chromatography. A, vol. 1218, no. 36, 2011, pp. 6191-9.
Liang J, Yang Z, Cao X, et al. Preparative isolation of novel antioxidant flavonoids of alfalfa by stop-and-go counter-current chromatography and following on-line liquid chromatography desalination. J Chromatogr A. 2011;1218(36):6191-9.
Liang, J., Yang, Z., Cao, X., Wu, B., & Wu, S. (2011). Preparative isolation of novel antioxidant flavonoids of alfalfa by stop-and-go counter-current chromatography and following on-line liquid chromatography desalination. Journal of Chromatography. A, 1218(36), 6191-9. https://doi.org/10.1016/j.chroma.2010.10.092
Liang J, et al. Preparative Isolation of Novel Antioxidant Flavonoids of Alfalfa By Stop-and-go Counter-current Chromatography and Following On-line Liquid Chromatography Desalination. J Chromatogr A. 2011 Sep 9;1218(36):6191-9. PubMed PMID: 21092976.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Preparative isolation of novel antioxidant flavonoids of alfalfa by stop-and-go counter-current chromatography and following on-line liquid chromatography desalination. AU - Liang,Junling, AU - Yang,Zhi, AU - Cao,Xiaoji, AU - Wu,Bing, AU - Wu,Shihua, Y1 - 2010/10/30/ PY - 2010/07/26/received PY - 2010/10/17/revised PY - 2010/10/25/accepted PY - 2010/11/25/entrez PY - 2010/11/26/pubmed PY - 2011/10/22/medline SP - 6191 EP - 9 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1218 IS - 36 N2 - In this work, we have established a new stop-and-go two-dimensional chromatography coupling of counter-current chromatography and liquid chromatography (2D CCC × LC) for the preparative separation of two novel antioxidant flavonoids from the extract of alfalfa (Medicago sativa L.). The CCC column has been used as the first dimension to purify the target flavonoids using a solvent system of isopropanol and 20% sodium chloride aqueous solution (1:1, v/v) with the stop-and-go flow technique, and the LC column packed with macroporous resin has been employed as the second dimension for on-line absorption, desalination and desorption of the targeting effluents purified from the first CCC dimension. As a result, two novel flavonoids, 6,8-dihydroxy-flavone-7-O-β-D-glucuronide (15.3 mg) and 6-methoxy-8-hydroxy-flavone-7-O-β-D-glucuronide (13.7 mg), have been isolated from 126.8 mg of crude sample pre-enriched by macroporous resin column. Their structures have been identified by electrospray ionization mass spectrometry (ESI-MS), electrospray ionization time-of-flight mass spectrometry (ESI-TOF-MS) and one- and two-dimensional nuclear magnetic resonance spectra (1D and 2D NMR). Further antioxidant assays showed that the first component possess a strong antioxidant activity. All the results demonstrated that the stop-and-go 2D CCC × LC method is very efficient for the separation of flavonoids of alfalfa and it can also be applied to isolate other comprehensive multi-component natural products. SN - 1873-3778 UR - https://www.unboundmedicine.com/medline/citation/21092976/Preparative_isolation_of_novel_antioxidant_flavonoids_of_alfalfa_by_stop_and_go_counter_current_chromatography_and_following_on_line_liquid_chromatography_desalination_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0021-9673(10)01487-1 DB - PRIME DP - Unbound Medicine ER -
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