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Int J Pharm. 2016 Sep 10;511(1):245-252. doi: 10.1016/j.ijpharm.2016.07.018. Epub 2016 Jul 11.

Solid-state characterization of optically pure (+)Dihydromyricetin extracted from Ampelopsis grossedentata leaves.

Author information

1
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.
2
Department of Pharmacy, Tongji Hospital affiliated with Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, PR China.
3
Pharmaceutical Materials Science and Engineering Laboratory, Department of Pharmaceutics, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA.
4
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.
5
Pharmaceutical Materials Science and Engineering Laboratory, Department of Pharmaceutics, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA. Electronic address: sunx0053@umn.edu.

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).

KEYWORDS:

Chirality; Dihydromyricetin molecular configuration; Enantiomer; Extraction; Solid-state characterization

PMID:
27418561
DOI:
10.1016/j.ijpharm.2016.07.018
[Indexed for MEDLINE]

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