Magnetic ligand fishing as a targeting tool for HPLC-HRMS-SPE-NMR: α-glucosidase inhibitory ligands and alkylresorcinol glycosides from Eugenia catharinae.

Publikation: Bidrag til tidsskriftTidsskriftartikelfagfællebedømt

  • Sileshi Gizachew Wubshet
  • Inês M. C. Brighente
  • Ruin Moaddel
  • Stærk, Dan
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.
OriginalsprogEngelsk
TidsskriftJournal of Natural Products
Vol/bind78
Udgave nummer11
Sider (fra-til)2657-2665
Antal sider9
ISSN0163-3864
DOI
StatusUdgivet - 2015

ID: 144151718