Enzymatic Synthesis of α-Tocopherol Derivative Glycoside, Daidzein Glycoside, Daidzein Oligosaccharide, Resveratrol Oligosaccharide, and Curcumin Oligosaccharides and Their Anti-Allergic Activity and Neuroprotective Activity

• Published in: Natural product communications Vol. 16; no. 10
• Main Authors: Hamada, Hiroki, Hamada, Hatsuyuki, Ishihara, Kohji, Kuboki, Atsuhito, Iwaki, Takafumi, Kiriake, Yuya
• Format: Journal Article
• Language: English
• Published: Los Angeles, CA SAGE Publications 01.10.2021
• Subjects: daidzein; oligosaccharide; α-Tocopherol derivative; anti-allergic activity; glycoside; resveratrol; neuroprotective activity; curcumin
• ISSN: 1934-578X; 1555-9475
• DOI: 10.1177/1934578X211029095

Enzymatic glycosylations of an α-tocopherol derivative, daidzein, resveratrol, and curcumin were investigated. The plant polyphenol, resveratrol, was incubated with glucosyltransferase from Phytolacca americana. The resveratrol glycoside obtained was then incubated with cyclodextrin glucanotransferase to obtain resveratrol oligosaccharide. Daidzein and curcumin were also converted into daidzein glycoside, daidzein oligosaccharide, and curcumin oligosaccharides. Also, α-tocopherol derivative, that is, 2, 5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-ol, was glycosylated. The glycosides and oligosaccharides had strong anti-allergic activity such as suppression of IgE formation, inhibition of histamine release, and inhibition of O2 - generation. In addition, the glycosides and oligosaccharides showed efficient neuroprotective activity by inhibition of phosphodiesterase.