title: Pycnalin, a new α-glucosidase inhibitor from Acer pycnanthum.
abstract: A new compound, pycnalin (1), together with four known compounds, ginnalins A (2), B (3), C (4), and 3,6-di-O-galloyl-1,5-anhydro-D-glucitol (3,6-di-GAG) (5), were isolated from Acer pycnanthum. The structure of 1 was determined on the basis of 2D-NMR spectral data and synthesis of 1. Pycnalin (1) is the first 1,5-anhydro-D-mannitol linked to a gallic acid, while compounds 2-5 were 1,5-anhydro-D-glucitol linked to gallic acids. All compounds were tested in vitro for α-glucosidase inhibitory and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities. Pycnalin (1) exhibited moderate α-glucosidase inhibitory activity as well as free radical scavenging activity. Ginnalin A (2) and 3,6-di-GAG (5), which have two galloyl groups, exhibited potent α-glucosidase inhibition, compared to those of other compounds 1, 3, and 4 containing a galloyl group. These results suggest that α-glucosidase inhibition is influenced by the number of galloyl groups.
authors.affiliation: Graduate School of Life and Environmental Sciences, University of Tsukuba, Japan.
authors.forename: Ai
authors.initials: A
authors.lastname: Ogawa
authors.forename: Yusaku
authors.initials: Y
authors.lastname: Miyamae
authors.forename: Atsushi
authors.initials: A
authors.lastname: Honma
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Koyama
authors.forename: Kazunaga
authors.initials: K
authors.lastname: Yazawa
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Shigemori
mesh_terms: D031002:Acer / Q000737:chemistry* / Q000378:metabolism; D001713:Biphenyl Compounds / Q000737:chemistry / Q000494:pharmacology; D003847:Deoxyglucose / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D005707:Gallic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D065089:Glycoside Hydrolase Inhibitors; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D007003:Hypoglycemia / Q000188:drug therapy / Q000378:metabolism / Q000473:pathology; D007004:Hypoglycemic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D010851:Picrates / Q000737:chemistry / Q000494:pharmacology; D010936:Plant Extracts / Q000737:chemistry / Q000378:metabolism; D013012:Sorbitol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: C559717:6-O-galloyl-1,5-anhydroglucitol; D001713:Biphenyl Compounds; D004791:Enzyme Inhibitors; D016166:Free Radical Scavengers; D065089:Glycoside Hydrolase Inhibitors; D006027:Glycosides; D007004:Hypoglycemic Agents; D010851:Picrates; D010936:Plant Extracts; C575803:ginnalin A; C560279:pycnalin; D013012:Sorbitol; C006584:1,5-anhydroglucitol; D005707:Gallic Acid; D003847:Deoxyglucose; C004931:1,1-diphenyl-2-picrylhydrazyl