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

Molecules

Atsuhito Kuboki¹  Kei Shimoda²  Takafumi Iwaki³  Hiroki Hamada⁴  Daisuke Uesugi⁴  Yuya Fujitaka⁴  Tomohiro Saikawa⁵  Yuya Kiriake⁶ 

[1] Department of Biochemistry, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan;Department of Biomedical Chemistry, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan;Department of Biophysics, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan;Department of Life Science, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan;Department of Nursing, Junshin Gakuen University, 1-1-1 Tikushigaoka, Fukuoka-shi, Minami-ku, Fukuoka 815-8510, Japan;Faculty of Medicine and Health Sciences, Yamaguchi University, 1-1-1 Minamikogushi, Ube-shi, Yamaguchi 755-8505, Japan;

关键词: daidzein;    α-tocopherol;    hesperetin;    β-glycoside;    anti-allergic activity;    tyrosinase inhibitory activity;   

DOI  :  10.3390/molecules24162975

来源: DOAJ

【 摘 要 】

Daidzein is a common isoflavone, having multiple biological 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, physicochemical stability, intestinal absorption, and biological half-life, and improve their bio- and pharmacological properties. They were transformed by cultured Nicotiana tabacum cells to 7-β-glucoside and 7-β-gentiobioside of daidzein, and 3′- and 7-β-glucosides, 3′,7-β-diglucoside, and 7-β-gentiobioside of hesperetin. Daidzein and α-tocopherol were glycosylated by galactosylation with β-glucosidase to give 4′- and 7-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 respective aglycones. In addition, these glycosides showed higher tyrosinase inhibitory activity than the corresponding aglycones. Glycosylation of daidzein, α-tocopherol, and hesperetin greatly improved their biological activities.

【 授权许可】

Unknown