Synthesis of Daidzein Glycosides, α-Tocopherol Glycosides, Hesperetin Glycosides by Bioconversi onand Their Potential for Anti-Allergic Functional-Foods and Cosmetics

Yuya Fujitaka, Hiroki Hamada, Daisuke Uesugi, Atsuhito Kuboki, Kei Shimoda, Takafumi Iwaki, Yuya Kiriake, Tomohiro Saikawa

Daidzein is a common isoflavone, having multiple biol. effects such as anti-inflammation, anti-allergy, and anti-aging. α-Tocopherol is the tocopherol isoform with the highest vitamin E activity including anti-allergic activity and anti-cancer activity. Hesperetin is a flavone, which shows potent anti-inflammatory effects. These compounds have shortcomings, i.e., water-insolubility and poor absorption after oral administration. The glycosylation of bioactive compounds can enhance their water-solubility, physicochem. stability, intestinal absorption, and biol. half-life, and improve their bio- and pharmacol. properties. They were transformed by cultured Nicotiana tabacum cells to β-glucoside and β-gentiobioside of daidzein, and 3'- and β-glucosides, 3',β-diglucoside, and β-gentiobioside of Hesperetin. Daidzein and α-tocopherol were glycosylated by galactosylation with β-glucosidase to give 4'- and β-galactosides of daidzein, which were new compounds, and α-tocopherol 6-β-galactoside. These nine glycosides showed higher anti-allergic activity, i.e., inhibitory activity toward histamine release from rat peritoneal mast cells, than their resp. aglycons. In addition, these glycosides showed higher tyrosinase inhibitory activity than the corresponding aglycons. Glycosylation of daidzein, α-tocopherol, and Hesperetin greatly improved their biol. activities. 

Molecules

MDPI

24

26

2975

2985