title: Solid-state characterization of optically pure (+)Dihydromyricetin extracted from Ampelopsis grossedentata leaves.
abstract: Dihydromyricetin (DMY) is a natural flavanol compound isolated from a traditional Chinese medicine, Ampelopsis grossedentata. Despite that optically pure (+)DMY is desired for treating chronic pharyngitis and alcohol use disorders, only DMY racemate is commercially available due to prolonged exposure time to high temperature and the presence of metal ions during industrial extraction, which cause racemization of the homochiral (+)DMY. We have developed an extraction method for successfully obtain optically pure (+)DMY. We have further assessed the physicochemical properties of the two phases using PXRD, DSC, TGA, FTIR, and moisture sorption. Among them, PXRD and FT-IR are suitable for quickly distinguishing homochiral (+)DMY from racemic (±)DMY. Lastly, with the aid of cocrystallization with theophylline, the absolute configuration of homochiral (+)DMY was identified to be (2R, 3R).
authors.affiliation: Department of Pharmacy, Tongji Hospital affiliated with Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, PR China; Pharmaceutical Materials Science and Engineering Laboratory, Department of Pharmaceutics, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA.
authors.forename: Chenguang
authors.initials: C
authors.lastname: Wang
authors.affiliation: Department of Pharmacy, Tongji Hospital affiliated with Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, PR China.
authors.forename: Wei
authors.initials: W
authors.lastname: Xiong
authors.affiliation: Pharmaceutical Materials Science and Engineering Laboratory, Department of Pharmaceutics, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA.
authors.forename: Sathyanarayana
authors.initials: S
authors.lastname: Reddy Perumalla
authors.affiliation: Department of Pharmacy, Tongji Hospital affiliated with Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, PR China. Electronic address: fjg3560@sina.com.
authors.forename: Jianguo
authors.initials: J
authors.lastname: Fang
authors.affiliation: Pharmaceutical Materials Science and Engineering Laboratory, Department of Pharmaceutics, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA. Electronic address: sunx0053@umn.edu.
authors.forename: Changquan
authors.initials: C
authors.lastname: Calvin Sun
mesh_terms: D032421:Ampelopsis; D002151:Calorimetry / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004365:Drugs, Chinese Herbal / Q000032:analysis* / Q000737:chemistry; D044948:Flavonols / Q000032:analysis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D018515:Plant Leaves; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D014961:X-Ray Diffraction / Q000379:methods*
chemical_list: D004365:Drugs, Chinese Herbal; D044948:Flavonols; C472036:dihydromyricetin
keywords: Chirality; Dihydromyricetin molecular configuration; Enantiomer; Extraction; Solid-state characterization