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

Chenguang Wang, Wei Xiong, Sathyanarayana Reddy Perumalla, Jianguo Fang, Changquan Calvin Sun

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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).

Original languageEnglish (US)
Pages (from-to)245-252
Number of pages8
JournalInternational journal of pharmaceutics
Volume511
Issue number1
DOIs
StatePublished - Sep 10 2016

Bibliographical note

Funding Information:
We are grateful for resources from the University of Minnesota through the Minnesota Supercomputing Institute and X-ray Crystallographic Facility in the Department of Chemistry. Some of the experiments were performed at the University of Minnesota I.T. Characterization Facility, which receives partial support from the NSF through the NNIN program.

Publisher Copyright:
© 2016 Elsevier B.V.

Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.

Keywords

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

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