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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Magnetic ligand fishing as a targeting tool for HPLC-HRMS-SPE-NMR: α-glucosidase inhibitory ligands and alkylresorcinol glycosides from Eugenia catharinae. / Wubshet, Sileshi Gizachew; Brighente, Inês M. C.; Moaddel, Ruin; Stærk, Dan.
I: Journal of Natural Products, Bind 78, Nr. 11, 2015, s. 2657-2665.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Magnetic ligand fishing as a targeting tool for HPLC-HRMS-SPE-NMR: α-glucosidase inhibitory ligands and alkylresorcinol glycosides from Eugenia catharinae.
AU - Wubshet, Sileshi Gizachew
AU - Brighente, Inês M. C.
AU - Moaddel, Ruin
AU - Stærk, Dan
PY - 2015
Y1 - 2015
N2 - 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 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-α-l-rhamnopyranoside, myricetin, quercetin, and kaempferol as α-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-β-d-glucopyranoside, 5-propylresorcinol 4-O-β-d-glucopyranoside, 5-pentylresorcinol 4-O-[α-d-apiofuranosyl-(1→6)]-β-d-glucopyranoside, 5-pentylresorcinol 4-O-β-d-glucopyranoside, 4-hydroxy-3-O-methyl-5-pentylresorcinol 1-O-β-d-glucopyranoside, and 3-O-methyl-5-pentylresorcinol 1-O-[β-d-glucopyranosyl-(1→6)]-β-d-glucopyranoside.
AB - 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 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-α-l-rhamnopyranoside, myricetin, quercetin, and kaempferol as α-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-β-d-glucopyranoside, 5-propylresorcinol 4-O-β-d-glucopyranoside, 5-pentylresorcinol 4-O-[α-d-apiofuranosyl-(1→6)]-β-d-glucopyranoside, 5-pentylresorcinol 4-O-β-d-glucopyranoside, 4-hydroxy-3-O-methyl-5-pentylresorcinol 1-O-β-d-glucopyranoside, and 3-O-methyl-5-pentylresorcinol 1-O-[β-d-glucopyranosyl-(1→6)]-β-d-glucopyranoside.
U2 - 10.1021/acs.jnatprod.5b00603
DO - 10.1021/acs.jnatprod.5b00603
M3 - Journal article
C2 - 26496505
VL - 78
SP - 2657
EP - 2665
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 11
ER -
ID: 144151718