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Hyphenation of solid-phase extraction with liquid chromatography and nuclear magnetic resonance: application of HPLC-DAD-SPE-NMR to identification of constituents of Kanahia laniflora.
Anal Chem. 2005 Jun 01; 77(11):3547-53.AC

Abstract

The introduction of on-line solid-phase extraction (SPE) in HPLC-NMR has dramatically enhanced the sensitivity of this technique by concentration of the analytes in a small-volume NMR flow cell and by increasing the amount of the analyte by multiple peak trapping. In this study, the potential of HPLC-DAD-SPE-NMR hyphenation was demonstrated by structure determination of complex constituents of flower, leaf, root, and stem extracts of an African medicinal plant Kanahia laniflora. The technique was shown to allow acquisition of high-quality homo- and heteronuclear 2D NMR data following analytical-scale HPLC separation of extract constituents. Four flavonol glycosides [kaempferol 3-O-(6-O-alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside; kaempferol 3-O-(2,6-di-O-alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside; quercetin 3-O-(2,6-di-O-alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside (rutin); and isorhamnetin, 3-O-(6-O-alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside] and three 5alpha-cardenolides [coroglaucigenin 3-O-6-deoxy-beta-d-allopyranoside; coroglaucigenin 3-O-(4-O-beta-d-glucopyranosyl)-6-deoxy-beta-d-glucopyranoside; 3'-O-acetyl-3'-epiafroside] were identified, with complete assignments of 1H and 13C resonances based on HSQC and HMBC spectra whenever required. Confirmation of the structures was provided by HPLC-MS data. The HPLC-DAD-SPE-NMR technique therefore speeds up the dereplication of complex mixtures of natural origin significantly, by characterization of individual extract components prior to preparative isolation work.

Authors+Show Affiliations

Department of Medicinal Chemistry, Danish University of Pharmaceutical Sciences, Universitetsparken 2, DK-2100 Copenhagen, Denmark.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

15924388

Citation

Clarkson, Cailean, et al. "Hyphenation of Solid-phase Extraction With Liquid Chromatography and Nuclear Magnetic Resonance: Application of HPLC-DAD-SPE-NMR to Identification of Constituents of Kanahia Laniflora." Analytical Chemistry, vol. 77, no. 11, 2005, pp. 3547-53.
Clarkson C, Staerk D, Hansen SH, et al. Hyphenation of solid-phase extraction with liquid chromatography and nuclear magnetic resonance: application of HPLC-DAD-SPE-NMR to identification of constituents of Kanahia laniflora. Anal Chem. 2005;77(11):3547-53.
Clarkson, C., Staerk, D., Hansen, S. H., & Jaroszewski, J. W. (2005). Hyphenation of solid-phase extraction with liquid chromatography and nuclear magnetic resonance: application of HPLC-DAD-SPE-NMR to identification of constituents of Kanahia laniflora. Analytical Chemistry, 77(11), 3547-53.
Clarkson C, et al. Hyphenation of Solid-phase Extraction With Liquid Chromatography and Nuclear Magnetic Resonance: Application of HPLC-DAD-SPE-NMR to Identification of Constituents of Kanahia Laniflora. Anal Chem. 2005 Jun 1;77(11):3547-53. PubMed PMID: 15924388.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hyphenation of solid-phase extraction with liquid chromatography and nuclear magnetic resonance: application of HPLC-DAD-SPE-NMR to identification of constituents of Kanahia laniflora. AU - Clarkson,Cailean, AU - Staerk,Dan, AU - Hansen,Steen Honoré, AU - Jaroszewski,Jerzy W, PY - 2005/6/1/pubmed PY - 2007/4/3/medline PY - 2005/6/1/entrez SP - 3547 EP - 53 JF - Analytical chemistry JO - Anal Chem VL - 77 IS - 11 N2 - The introduction of on-line solid-phase extraction (SPE) in HPLC-NMR has dramatically enhanced the sensitivity of this technique by concentration of the analytes in a small-volume NMR flow cell and by increasing the amount of the analyte by multiple peak trapping. In this study, the potential of HPLC-DAD-SPE-NMR hyphenation was demonstrated by structure determination of complex constituents of flower, leaf, root, and stem extracts of an African medicinal plant Kanahia laniflora. The technique was shown to allow acquisition of high-quality homo- and heteronuclear 2D NMR data following analytical-scale HPLC separation of extract constituents. Four flavonol glycosides [kaempferol 3-O-(6-O-alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside; kaempferol 3-O-(2,6-di-O-alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside; quercetin 3-O-(2,6-di-O-alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside (rutin); and isorhamnetin, 3-O-(6-O-alpha-l-rhamnopyranosyl)-beta-d-glucopyranoside] and three 5alpha-cardenolides [coroglaucigenin 3-O-6-deoxy-beta-d-allopyranoside; coroglaucigenin 3-O-(4-O-beta-d-glucopyranosyl)-6-deoxy-beta-d-glucopyranoside; 3'-O-acetyl-3'-epiafroside] were identified, with complete assignments of 1H and 13C resonances based on HSQC and HMBC spectra whenever required. Confirmation of the structures was provided by HPLC-MS data. The HPLC-DAD-SPE-NMR technique therefore speeds up the dereplication of complex mixtures of natural origin significantly, by characterization of individual extract components prior to preparative isolation work. SN - 0003-2700 UR - https://www.unboundmedicine.com/medline/citation/15924388/Hyphenation_of_solid_phase_extraction_with_liquid_chromatography_and_nuclear_magnetic_resonance:_application_of_HPLC_DAD_SPE_NMR_to_identification_of_constituents_of_Kanahia_laniflora_ L2 - https://doi.org/10.1021/ac050212k DB - PRIME DP - Unbound Medicine ER -