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Synthesis of Daidzein Glycosides, α-Tocopherol Glycosides, Hesperetin Glycosides by Bioconversion and Their Potential for Anti-Allergic Functional-Foods and Cosmetics.
- Source :
-
Molecules (Basel, Switzerland) [Molecules] 2019 Aug 16; Vol. 24 (16). Date of Electronic Publication: 2019 Aug 16. - Publication Year :
- 2019
-
Abstract
- 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.
- Subjects :
- Animals
Anti-Allergic Agents metabolism
Biocatalysis
Cell Culture Techniques
Cosmetics metabolism
Functional Food analysis
Glycosides metabolism
Glycosylation
Hesperidin metabolism
Humans
Isoflavones metabolism
Male
Mast Cells cytology
Mast Cells drug effects
Mast Cells metabolism
Monophenol Monooxygenase antagonists & inhibitors
Monophenol Monooxygenase metabolism
Plant Cells metabolism
Primary Cell Culture
Rats
Rats, Wistar
Solubility
Nicotiana cytology
Nicotiana metabolism
alpha-Tocopherol metabolism
Anti-Allergic Agents chemical synthesis
Cosmetics chemical synthesis
Glycosides chemical synthesis
Hesperidin chemical synthesis
Isoflavones chemical synthesis
alpha-Tocopherol chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1420-3049
- Volume :
- 24
- Issue :
- 16
- Database :
- MEDLINE
- Journal :
- Molecules (Basel, Switzerland)
- Publication Type :
- Academic Journal
- Accession number :
- 31426346
- Full Text :
- https://doi.org/10.3390/molecules24162975