Microbial-Driven Synthesis and Hydrolysis of Neohesperidin Dihydrochalcone: Biotransformation Process and Feasibility Investigation

J Agric Food Chem. 2024 Feb 28;72(8):4246-4256. doi: 10.1021/acs.jafc.3c08339. Epub 2024 Feb 5.

Abstract

A novel yeast-mediated hydrogenation was developed for the synthesis of neohesperidin dihydrochalcone (NHDC) in high yields (over 83%). Moreover, whole-cell catalytic hydrolysis was also designed to hydrolyze NHDC into potential sweeteners, hesperetin dihydrochalcone-7-O-glucoside (HDC-G) and hesperetin dihydrochalcone (HDC). The biohydrogenation was further combined with whole-cell hydrolysis to achieve a one-pot two-step biosynthesis, utilizing yeast to hydrogenate C═C in the structure, while Aspergillus niger cells hydrolyze glycosides. The conversion of NHDC and the proportion of hydrolysis products could be controlled by adjusting the catalysts, the components of the reaction system, and the addition of glucose. Furthermore, yeast-mediated biotransformation demonstrated superior reaction stability and enhanced safety and employed more cost-effective catalysts compared to the traditional chemical hydrogenation of NHDC synthesis. This research not only provides a new route for NHDC production but also offers a safe and flexible one-pot cascade biosynthetic platform for the production of high-value compounds from citrus processing wastes.

Keywords: feasibility; neohesperidin dihydrochalcone; novel sweeteners; whole-cell catalytic hydrolysis; yeast-mediated hydrogenation.

MeSH terms

  • Biotransformation
  • Chalcones*
  • Feasibility Studies
  • Hesperidin* / analogs & derivatives*
  • Hesperidin* / chemistry
  • Hydrolysis
  • Saccharomyces cerevisiae* / metabolism

Substances

  • neohesperidin dihydrochalcone
  • dihydrochalcone
  • Hesperidin
  • Chalcones