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A novel chemo-enzymatic synthesis of hydrophilic phytosterol derivatives by Dr. Wen-Sen He

Phytosterols and phytosterol esters have similar biological activities, while phytosterol esters are advantageous since this compound has better solubility than the free phytosterols, which contribute to the practical application in foods. In our recent work, a novel method was developed for chemo-enzymatic synthesis of hydrophilic phytosterol derivatives, phytosteryl polyethylene glycol succinate (PPGS), through an intermediate phytosteryl hemisuccinate (PSHS), which was first chemically prepared and subsequently coupled with polyethylene glycol 1000 (PEG 1000) through lipase-catalyzed esterification (Fig. 1). The chemical structure of intermediate product and hydrophilic derivatives were finally confirmed to be PSHS and PPGS by fourier transform infrared spectroscopy (Fig. 2), mass spectroscopy  (Fig. 3) and nuclear magnetic spectroscopy (Fig. 3), suggesting that hydrophilic phytosterol derivatives were successfully synthesized. The effects of various parameters on the lipase-catalyzed conversion of PSHS to PPGS were investigated and the highest conversion (>78%) was obtained under the selected conditions: 75 mmol/L PSHS, 1: 2 molar ratio of PSHS to PEG 1000, 50 g/L Novozym 435, 120 g/L 3 Å molecular sieves in tert-butanol, 55 oC, 96 h and 200 rpm. The solubility of phytosterols in water was significantly improved by coupling with PEG 1000, facilitating the incorporation into a variety of foods containing water.



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