Dataset Information

Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: ?-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae.

ABSTRACT: A bioanalytical platform combining magnetic ligand fishing for ?-glucosidase inhibition profiling and HPLC-HRMS-SPE-NMR for structural identification of ?-glucosidase inhibitory ligands, both directly from crude plant extracts, is presented. Magnetic beads with N-terminus-coupled ?-glucosidase were synthesized and characterized for their inherent catalytic activity. Ligand fishing with the immobilized enzyme was optimized using an artificial test mixture consisting of caffeine, ferulic acid, and luteolin before proof-of-concept with the crude extract of Eugenia catharinae. The combination of ligand fishing and HPLC-HRMS-SPE-NMR identified myricetin 3-O-?-L-rhamnopyranoside, myricetin, quercetin, and kaempferol as ?-glucosidase inhibitory ligands in E. catharinae. Furthermore, HPLC-HRMS-SPE-NMR analysis led to identification of six new alkylresorcinol glycosides, i.e., 5-(2-oxopentyl)resorcinol 4-O-?-D-glucopyranoside, 5-propylresorcinol 4-O-?-D-glucopyranoside, 5-pentylresorcinol 4-O-[?-D-apiofuranosyl-(1?6)]-?-D-glucopyranoside, 5-pentylresorcinol 4-O-?-D-glucopyranoside, 4-hydroxy-3-O-methyl-5-pentylresorcinol 1-O-?-D-glucopyranoside, and 3-O-methyl-5-pentylresorcinol 1-O-[?-D-glucopyranosyl-(1?6)]-?-D-glucopyranoside.

SUBMITTER: Wubshet SG

PROVIDER: S-EPMC5036580 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Publications

Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: α-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae.

Wubshet Sileshi G SG Brighente Inês M C IM Moaddel Ruin R Staerk Dan D

Journal of natural products 20151023 11

A bioanalytical platform combining magnetic ligand fishing for α-glucosidase inhibition profiling and HPLC-HRMS-SPE-NMR for structural identification of α-glucosidase inhibitory ligands, both directly from crude plant extracts, is presented. Magnetic beads with N-terminus-coupled α-glucosidase were synthesized and characterized for their inherent catalytic activity. Ligand fishing with the immobilized enzyme was optimized using an artificial test mixture consisting of caffeine, ferulic acid, and ...[more]

PMID: 26496505

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Project description:Commercial preparations of Ginkgo biloba are very complex mixtures prepared from raw leaf extracts by a series of extraction and prepurification steps. The pharmacological activity is attributed to a number of flavonoid glycosides and unique terpene trilactones (TTLs), with largely uncharacterized pharmacological profiles on targets involved in neurological disorders. It is therefore important to complement existing targeted analytical methods for analysis of Ginkgo biloba preparations with alternative technology platforms for their comprehensive and global characterization. In this work, (1)H NMR-based metabolomics and hyphenation of high-performance liquid chromatography, photo-diode array detection, mass spectrometry, solid-phase extraction, and nuclear magnetic resonance spectroscopy (HPLC-PDA-MS-SPE-NMR) were used for investigation of 16 commercially available preparations of Ginkgo biloba. The standardized extracts originated from Denmark, Italy, Sweden, and United Kingdom, and the results show that (1)H NMR spectra allow simultaneous assessment of the content as well as identity of flavonoid glycosides and TTLs based on a very simple sample-preparation procedure consisting of extraction, evaporation and reconstitution in acetone-d(6). Unexpected or unwanted extract constituents were also easily identified in the (1)H NMR spectra, which contrasts traditional methods that depend on UV absorption or MS ionizability and usually require availability of reference standards. Automated integration of (1)H NMR spectral segments (buckets or bins of 0.02 ppm width) provides relative distribution plots of TTLs based on their H-12 resonances. The present study shows that (1)H NMR-based metabolomics is an attractive method for non-selective and comprehensive analysis of Ginkgo extracts. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s11306-009-0195-x) contains supplementary material, which is available to authorized users.

Dataset Information

Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: ?-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae.

Publications

Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: α-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae.

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