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Preparative isolation and purification of isobenzofuranone derivatives and saponins from seeds of Nigella glandulifera Freyn by high-speed counter-current chromatography combined with gel filtration.
J Chromatogr A. 2009 May 08; 1216(19):4258-62.JC

Abstract

Although the medicinal plant and food Nigella glandulifera Freyn has been researched for decades, isobenzofuranones have never been isolated before. Two isobenzofuranone derivatives and two saponins were successfully separated and purified from seeds of N. glandulifera Freyn by high-speed counter-current chromatography (HSCCC) with the optimized two-phase solvent system, n-hexane-ethyl acetate-methanol-water (7:3:5:5, v/v). Salfredin B(11) (22.1mg, HPLC purity 95.3%), 5, 7-dihydroxy-6-(3-methybut-2-enyl) isobenzofuran-1(3H)-one (18.9mg, HPLC purity 97.3%) and crude sample 2 (555mg) were separated from 600mg of ethyl acetate extract of N. glandulifera Freyn. Following a cleaning-up step by chromatography on Sephadex LH-20, hederagenin (12mg) and 3-O-[beta-d-xylopyranosyl-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl]-hederagenin (45mg) were separated from sample 2. All of the fractions before peak II were collected and subjected to a Sephadex LH-20 column and eluted by methanol, two of triterpene saponins (12mg of hederagenin and 45mg of 3-O-[beta-d-xylopyranosyl-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl]-hederagenin) were isolated. The structures of peak fractions were identified by IR, electron ionization MS, (1)H NMR and (13)C NMR. 5, 7-Dihydroxy-6-(3-methybut-2-enyl) isobenzofuran-1(3H)-one was isolated for the first time from higher plant and salfredin B11 was isolated for the first time in this plant.

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Authors+Show Affiliations

Xin X
Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urmuqi, China.
Yang Y
No affiliation info available
Zhong J
No affiliation info available
Aisa HA
No affiliation info available
Wang H
No affiliation info available

MeSH

BenzofuransChromatography, GelCountercurrent DistributionNigellaPlant ExtractsSaponinsSeedsSolventsTriterpenes

Pub Type(s)

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

Language

eng

PubMed ID

19344906

Citation

Xin, Xuelei, et al. "Preparative Isolation and Purification of Isobenzofuranone Derivatives and Saponins From Seeds of Nigella Glandulifera Freyn By High-speed Counter-current Chromatography Combined With Gel Filtration." Journal of Chromatography. A, vol. 1216, no. 19, 2009, pp. 4258-62.
Xin X, Yang Y, Zhong J, et al. Preparative isolation and purification of isobenzofuranone derivatives and saponins from seeds of Nigella glandulifera Freyn by high-speed counter-current chromatography combined with gel filtration. J Chromatogr A. 2009;1216(19):4258-62.
Xin, X., Yang, Y., Zhong, J., Aisa, H. A., & Wang, H. (2009). Preparative isolation and purification of isobenzofuranone derivatives and saponins from seeds of Nigella glandulifera Freyn by high-speed counter-current chromatography combined with gel filtration. Journal of Chromatography. A, 1216(19), 4258-62. https://doi.org/10.1016/j.chroma.2009.03.050
Xin X, et al. Preparative Isolation and Purification of Isobenzofuranone Derivatives and Saponins From Seeds of Nigella Glandulifera Freyn By High-speed Counter-current Chromatography Combined With Gel Filtration. J Chromatogr A. 2009 May 8;1216(19):4258-62. PubMed PMID: 19344906.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Preparative isolation and purification of isobenzofuranone derivatives and saponins from seeds of Nigella glandulifera Freyn by high-speed counter-current chromatography combined with gel filtration. AU - Xin,Xuelei, AU - Yang,Yi, AU - Zhong,Jie, AU - Aisa,Haji Akber, AU - Wang,Hanqing, Y1 - 2009/03/24/ PY - 2008/08/21/received PY - 2009/03/03/revised PY - 2009/03/03/accepted PY - 2009/4/7/entrez PY - 2009/4/7/pubmed PY - 2009/7/16/medline SP - 4258 EP - 62 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1216 IS - 19 N2 - Although the medicinal plant and food Nigella glandulifera Freyn has been researched for decades, isobenzofuranones have never been isolated before. Two isobenzofuranone derivatives and two saponins were successfully separated and purified from seeds of N. glandulifera Freyn by high-speed counter-current chromatography (HSCCC) with the optimized two-phase solvent system, n-hexane-ethyl acetate-methanol-water (7:3:5:5, v/v). Salfredin B(11) (22.1mg, HPLC purity 95.3%), 5, 7-dihydroxy-6-(3-methybut-2-enyl) isobenzofuran-1(3H)-one (18.9mg, HPLC purity 97.3%) and crude sample 2 (555mg) were separated from 600mg of ethyl acetate extract of N. glandulifera Freyn. Following a cleaning-up step by chromatography on Sephadex LH-20, hederagenin (12mg) and 3-O-[beta-d-xylopyranosyl-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl]-hederagenin (45mg) were separated from sample 2. All of the fractions before peak II were collected and subjected to a Sephadex LH-20 column and eluted by methanol, two of triterpene saponins (12mg of hederagenin and 45mg of 3-O-[beta-d-xylopyranosyl-(1-->3)-alpha-l-rhamnopyranosyl-(1-->2)-alpha-l-arabinopyranosyl]-hederagenin) were isolated. The structures of peak fractions were identified by IR, electron ionization MS, (1)H NMR and (13)C NMR. 5, 7-Dihydroxy-6-(3-methybut-2-enyl) isobenzofuran-1(3H)-one was isolated for the first time from higher plant and salfredin B11 was isolated for the first time in this plant. SN - 1873-3778 UR - https://www.unboundmedicine.com/medline/citation/19344906/Preparative_isolation_and_purification_of_isobenzofuranone_derivatives_and_saponins_from_seeds_of_Nigella_glandulifera_Freyn_by_high_speed_counter_current_chromatography_combined_with_gel_filtration_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0021-9673(09)00363-X DB - PRIME DP - Unbound Medicine ER -
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