Green-Efficient Enzymatic Synthesis and Characterization of Liposoluble 6′/6"-O-Lauryl Phenolic Glycosides with Enhanced Intestinal Permeability

作者：Xu, Zhengming; Liu, Shuang; Lai, Huining; You, Lijun; Zhao, Zhengang^*

来源：Journal of Agricultural and Food Chemistry, 2023, 71(20): 7689-7702.

DOI：10.1021/acs.jafc.3c00527

• phenolic glycoside esters
• lipase
• catalysis
• lipophilicity
• carboxylesterase
• transport

Arbutin, salidroside, polydatin, and phlorizin are typicallynaturalbioactive phenolic glycosides. To improve the liposolubility and bioavailability,highly liposoluble derivatives including 6 '-O-lauryl arbutin, 6 '-O-lauryl salidroside,6 ''-O-lauryl polydatin, and 6 ''-O-lauryl phlorizin were efficiently synthesized by enzymaticacylation in a green solvent 2-MeTHF. Their reaction conversions reached84.4, 99.5, 99.8, and 89.1%, respectively, when catalyzed by Lipozyme435 at 20 mg/mL at 50 degrees C. As expected, the derivatives had highlog P (1.66-2.37) and retained goodantioxidant activity, making them potential alternatives to butylatedhydroxytoluene (BHT) and tert-butyl-hydroquinone(TBHQ) in lipid systems. Then, the intestinal permeability characteristicsand metabolism of phenolic glycosides and their derivatives were investigatedbased on Caco-2 monolayers. The permeability of polydatin and phlorizinwas mainly through active transport, but that of arbutin and salidrosideinvolved both passive diffusion and active uptake. The acylated derivativessuffered from severe CES-mediated hydrolysis but exhibited a largertransported amount than phenolic glycosides.