title: Synthesis of hydroxycinnamoyl β-D-xylopyranosides and evaluation of their antioxidant properties.
abstract: Various hydroxycinnamoyl β-d-xylopyranosides were efficiently prepared from 2,3,4-tri-O-acetyl-α-d-xylopyranosyl bromide (TAXB) with amine by amine-promoted glycosylation. The resulted acetylated hydroxycinnamoyl β-d-xylopyranosides with acetoxy groups at C-2, C-3, and C-4 were regioselectively deacetylated at C-4 position with Novozym 435. Antioxidant activities of free hydroxycinnamic acids and the respective β-d-xylopyranosides were evaluated by DPPH radical scavenging activity as well as their inhibitory effect on autoxidation of bulk methyl linoleate. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) decreased in the order ferulic acid>caffeic acid≈caffeoyl β-d-xylopyranosides≈sinapinic acid>sinapoyl β-d-xylopyranosides≈feruloyl β-d-xylopyranosides>p-coumaric acid>p-coumaroyl β-d-xylopyranosides. In bulk methyl linoleate, the antioxidant activity order against autoxidation was almost consistent with the scavenging activity order. The results showed that caffeoyl β-d-xylopyranosides and sinapoyl β-d-xylopyranosides were as effective as free caffeic acid, sinapinic acid, and ferulic acid.
authors.affiliation: Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, Japan. Electronic address: yasu@mail.kitami-it.ac.jp.
authors.forename: Yasutaka
authors.initials: Y
authors.lastname: Shimotori
authors.affiliation: Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Hoshi
authors.affiliation: Department of Applied Chemistry, School of Science and Technology, Meiji University, 1-1-1 Higashi-mita, Tama-ku, Kawasaki, Japan.
authors.forename: Kouji
authors.initials: K
authors.lastname: Soga
authors.affiliation: Department of Applied Chemistry, School of Science and Technology, Meiji University, 1-1-1 Higashi-mita, Tama-ku, Kawasaki, Japan.
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Osawa
authors.affiliation: Department of Applied Chemistry, School of Science and Technology, Meiji University, 1-1-1 Higashi-mita, Tama-ku, Kawasaki, Japan.
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Miyakoshi
mesh_terms: D000107:Acetylation; D001713:Biphenyl Compounds / Q000037:antagonists & inhibitors; D002109:Caffeic Acids / Q000737:chemistry; D003373:Coumaric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004800:Enzymes, Immobilized; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry; D005656:Fungal Proteins; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D008041:Linoleic Acids / Q000737:chemistry; D008049:Lipase / Q000737:chemistry; D010084:Oxidation-Reduction; D010851:Picrates / Q000037:antagonists & inhibitors; D013237:Stereoisomerism; D014994:Xylose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001713:Biphenyl Compounds; D002109:Caffeic Acids; D003373:Coumaric Acids; D004800:Enzymes, Immobilized; D016166:Free Radical Scavengers; D005656:Fungal Proteins; D006027:Glycosides; D008041:Linoleic Acids; D010851:Picrates; C005575:methyl linoleate; C073734:sinapinic acid; D014994:Xylose; C004999:ferulic acid; C004931:1,1-diphenyl-2-picrylhydrazyl; C093667:Novozyme 435; D008049:Lipase; C040048:caffeic acid
keywords: Antioxidant properties; Hydroxycinnamic acids; Hydroxycinnamoyl β-d-xylopyranosides; Lipase; Regioselective transesterification