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

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

doi:10.1016/j.ijpharm.2016.07.018

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

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

Pharmaceutics

Research output: Contribution to journal › Article › peer-review

40 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 language	English (US)
Pages (from-to)	245-252
Number of pages	8
Journal	International journal of pharmaceutics
Volume	511
Issue number	1
DOIs	https://doi.org/10.1016/j.ijpharm.2016.07.018
State	Published - 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.

Keywords

Chirality
Dihydromyricetin molecular configuration
Enantiomer
Extraction
Solid-state characterization

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.ijpharm.2016.07.018

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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).",

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author = "Chenguang Wang and Wei Xiong and {Reddy Perumalla}, Sathyanarayana and Jianguo Fang and {Calvin Sun}, Changquan",

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: {\textcopyright} 2016 Elsevier B.V.",

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doi = "10.1016/j.ijpharm.2016.07.018",

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AU - Xiong, Wei

AU - Reddy Perumalla, Sathyanarayana

AU - Fang, Jianguo

AU - Calvin Sun, Changquan

N1 - 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.

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N2 - 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).

AB - 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).

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KW - Dihydromyricetin molecular configuration

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KW - Extraction

KW - Solid-state characterization

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

Abstract

Bibliographical note

Keywords

UN SDGs

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