134407-68-4Relevant academic research and scientific papers
Synthesis and comparative structure-activity study of carbohydrate-based phenolic compounds as α-glucosidase inhibitors and antioxidants
MacHida, Shota,Mukai, Saki,Kono, Rina,Funato, Megumi,Saito, Hiroaki,Uchiyama, Taketo
, (2019/12/04)
Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure-activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro -D-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.
Dual action of acertannins as potential regulators of intracellular ceramide levels
Kamori, Akiko,Kato, Atsushi,Miyawaki, Shota,Koyama, Junna,Nash, Robert J.,Fleet, George W.J.,Miura, Daisuke,Ishikawa, Fumihiro,Adachi, Isao
, p. 1177 - 1185 (2016/11/04)
Derived from the genus maple (Acer), acertannins are a group of gallotannins which have a characteristic 1,5-anhydro-D-glucitol (1,5-AG) occupying the central core position in the tannic acid structure whose hydroxyl groups have one or more galloyl residues. We have synthesized all ten naturally-occurring acertannins and seven new acertannin derivatives from 1,5-AG. Side-by-side comparisons revealed that 2,4,6-tri-O-galloyl-1,5-AG 21 (maplexin E) and maplexin F 22 (2,3,6-tri-O-galloyl-1,5-AG) were good inhibitors of ceramidase (CDase). In contrast, the core anhydrosugar 1,5-AG 12 itself and 3′,4′,5′-trimethoxy benzoyl derivatives 23–25 did not show CDase inhibition. Metabolic labelling experiments using NBD-hexanoic acid revealed that 50?μM of 6-O-galloyl-1,5-AG 16 (Ginnalin B), 2,6-di-O-galloyl-1,5-AG 19 (Ginnalin A), and 4,6-di-O-galloyl-1,5-AG 4 increased intracellular NBD-labeled ceramide, by 2.3, 2.2, and 2.1-fold, respectively. It is noteworthy that these acertannins 16, 19, and 4 promoted ceramide synthase 3 (CERS3) gene expression. Acertannins, therefore, represent a new class of potential intracellular ceramide regulators exhibiting both CDase inhibition and ceramide synthase promotion.
Synthesis and mass spectra of 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-(methoxycarbonylmethyl)-D-glucitol and the positional isomers of 4-O-acetyl-1,5-anhydro-di-O-(methoxycarbonylmethyl)-O-methyl-D-glucitol and 4-O-acetyl-1,5-anhydro-O-(methoxycarbonylmethyl)-
Zeller, Samuel G.,Griesgraber, George W.,Gray, Gary R.
, p. 47 - 57 (2007/10/02)
Reductive cleavage of fully methylated, partially O-carboxymethylated cellulose had previously been shown to produce 4-O-acetyl-1,5-anhydro-2,3,6-tri-O-methyl-, -2-O-(methoxycarbonylmethyl)-3,6-di-O-methyl-, -3-O-(methoxycarbonylmethyl)-2,6-di-O-methyl-,
