Comparative Physicochemical and Biochemical Characterization of Small-Molecule Glucosides

Fong Chin Huang, Isabelle Effenberger, Thilo Fischer, Isabella Louisa Hahn, Thomas Hoffmann, Wilfried Schwab

Research output: Contribution to journalArticlepeer-review

Abstract

Glycosylation of small molecules can significantly improve their physicochemical and biological properties. Only recently, decisive improvements in the biotechnological production of small-molecule glucosides (SMGs) have resulted in a large number of these compounds now being commercially available. In this study, we have analyzed a number of physical, chemical, and biological parameters of 31 SMGs, including solubility, stability, melting and pyrolysis points, partition coefficient log P, minimum inhibitory concentration against Escherichia coli (MIC), and enzymatic degradability. The properties such as water solubility, pH stability, and MICs of the glycosides were strongly dependent on the structures of the respective aglycones, which is why the SMG clustered according to their aglycones in most cases. Phenolic and furanone glucosides were readily hydrolyzed by saliva and skin microflora, whereas monoterpenol glycosides were poorer substrates for the enzymes involved. The results of this comparative analysis of SMGs provide valuable information for elucidating the biological functions of SMGs and the future technological applications of these useful natural products.

Original languageEnglish
Pages (from-to)15972-15980
Number of pages9
JournalJournal of agricultural and food chemistry
Volume70
Issue number50
DOIs
StatePublished - 21 Dec 2022

Keywords

  • comparative analysis
  • hydrolysis
  • physicochemical properties
  • small-molecule glucosides
  • stability

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