title: Synthesis of glycosyl ferulate derivatives by amine-promoted glycosylation with regioselective hydrolysis using Novozym 435 and evaluation of their antioxidant properties.
abstract: Various glycosyl ferulates were efficiently synthesized from 2,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (TAGB) with amine by amine-promoted glycosylation without using heavy metal. The resulted acetylated glycosyl ferulates with acetoxyl groups at C-2, C-3 and C-4 were regioselectively deacetylated at C-4 and C-6 positions with Novozym 435. Antioxidant abilities of free ferulic acids and its synthetic glycosyl ferulates were evaluated by inhibitory effect on autoxidation of bulk methyl linoleate as well as their radical scavenging activity. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH·) decreased in the order ferulic acid>sinapinic acid ≈ glycosyl sinapinates ≈ glycosyl ferulates>p-coumaric acid>glycosyl p-coumarates. In bulk methyl linoleate, the antioxidant activity order against autoxidation was very consistent with the scavenging activity order. The results showed that glycosyl ferulates and sinapinates were effective as well as free carboxylic acid forms.
authors.affiliation: Department of Biotechnology and Environmental Chemistry, National University Corporation Kitami Institute of Technology, Kitami, Hokkaido, Japan. yasu@mail.kitami-it.ac.jp
authors.forename: Yasutaka
authors.initials: Y
authors.lastname: Shimotori
authors.forename: Kyohei
authors.initials: K
authors.lastname: Tsutano
authors.forename: Kouji
authors.initials: K
authors.lastname: Soga
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Osawa
authors.forename: Masakazu
authors.initials: M
authors.lastname: Aoyama
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Miyakoshi
mesh_terms: D000107:Acetylation; D000588:Amines / Q000737:chemistry*; D055162:Biocatalysis; D001713:Biphenyl Compounds / Q000737:chemistry; D002175:Candida / Q000201:enzymology; D060326:Chemistry Techniques, Synthetic; D003373:Coumaric Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D004800:Enzymes, Immobilized; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry*; D005656:Fungal Proteins; D006031:Glycosylation; D006868:Hydrolysis; D008041:Linoleic Acids / Q000737:chemistry; D008049:Lipase / Q000378:metabolism*; D010084:Oxidation-Reduction; D010851:Picrates / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000588:Amines; D001713:Biphenyl Compounds; D003373:Coumaric Acids; D004800:Enzymes, Immobilized; D016166:Free Radical Scavengers; D005656:Fungal Proteins; D008041:Linoleic Acids; D010851:Picrates; C005575:methyl linoleate; C004999:ferulic acid; C004931:1,1-diphenyl-2-picrylhydrazyl; C093667:Novozyme 435; D008049:Lipase