Synthesis of new UV-B light absorbents: (Acetylphenyl)glycosides with antioxidant activities

Takashi Otani; Tetsu Tsubogo; Naoki Furukawa; Takao Saito; Katsumi Uchida; Kanako Iwama; Yuki Kanai; Hirofumi Yajima

doi:10.1016/j.bmcl.2008.05.006

Synthesis of new UV-B light absorbents: (Acetylphenyl)glycosides with antioxidant activities

Bioorg Med Chem Lett. 2008 Jun 15;18(12):3582-4. doi: 10.1016/j.bmcl.2008.05.006. Epub 2008 May 6.

Authors

Takashi Otani¹, Tetsu Tsubogo, Naoki Furukawa, Takao Saito, Katsumi Uchida, Kanako Iwama, Yuki Kanai, Hirofumi Yajima

Affiliation

¹ Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.

PMID: 18511279
DOI: 10.1016/j.bmcl.2008.05.006

Abstract

m-Acetylphenyl-beta-d-glucopyranosides and m-acetylphenyl-alpha/beta-d-mannopyranosides were synthesized by the Koenigs-Knorr, Mitsunobu, and Helferich reactions as key glycosylation reactions, respectively. Their spectroscopic properties and antioxidative activities were characterized as potential ultraviolet B-ray absorbents.

MeSH terms

Antioxidants / chemical synthesis*
Antioxidants / chemistry
Antioxidants / radiation effects
Glycosides / chemical synthesis*
Glycosides / chemistry
Glycosides / radiation effects
Glycosylation
Molecular Structure
Singlet Oxygen / chemistry
Singlet Oxygen / radiation effects
Spectrophotometry, Ultraviolet / methods
Stereoisomerism
Sunscreening Agents / chemical synthesis*
Sunscreening Agents / chemistry
Sunscreening Agents / radiation effects
Ultraviolet Rays*

Substances

Antioxidants
Glycosides
Sunscreening Agents
Singlet Oxygen