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

• Published in: Molecules (Basel, Switzerland) Switzerland), 2019-08, Vol.24 (16), p.2975
• Main Authors: Fujitaka, Yuya, Hamada, Hiroki, Uesugi, Daisuke, Kuboki, Atsuhito, Shimoda, Kei, Iwaki, Takafumi, Kiriake, Yuya, Saikawa, Tomohiro
• Format: Article
• Language: English
• Subjects: Absorption; Aging; Aglycones; alpha-Tocopherol - chemical synthesis; alpha-Tocopherol - metabolism; Animals; anti-allergic activity; Anti-Allergic Agents - chemical synthesis; Anti-Allergic Agents - metabolism; Antitumor activity; Bioactive compounds; Biocatalysis; Bioconversion; Biological effects; Cancer; Carbon; Cell Culture Techniques; Cellobiase; Cosmetics; Cosmetics - chemical synthesis; Cosmetics - metabolism; Daidzein; Enzymes; Flavonoids; Food allergies; Functional Food - analysis; Galactosides; Glucosidase; Glucosides; Glycosides; Glycosides - chemical synthesis; Glycosides - metabolism; Glycosylation; hesperetin; Hesperidin; Hesperidin - chemical synthesis; Hesperidin - metabolism; Histamine; Humans; Inflammation; Intestinal absorption; Isoflavones - chemical synthesis; Isoflavones - metabolism; Male; Mast cells; Mast Cells - cytology; Mast Cells - drug effects; Mast Cells - metabolism; Monophenol Monooxygenase - antagonists & inhibitors; Monophenol Monooxygenase - metabolism; Nicotiana - cytology; Nicotiana - metabolism; NMR; Nuclear magnetic resonance; Oral administration; Peritoneum; Physiology; Plant Cells - metabolism; Primary Cell Culture; Rats; Rats, Wistar; Signal transduction; Solubility; Tocopherol; Tyrosinase; tyrosinase inhibitory activity; Vitamin E; α-tocopherol; β-Glucosidase; β-glycoside
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules24162975

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 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.