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    Absolute configuration of naturally occurring glabridin

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    Date
    2013-11
    Author
    Simmler, Charlotte
    Fronczek, Frank R
    Pauli, Guido F
    Santarsiero, Bernard D
    Publisher
    International Union of Crystallography
    Metadata
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    Abstract
    The title compound {systematic name: 4-[(3R)-8,8-dimethyl-3,4-di­hydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol, commonly named glabridin}, C20H20O4, is a species-specific biomarker from the roots Glycyrrhiza glabra L. (European licorice, Fabaceae). In the present study, this prenylated isoflavan has been purified from an enriched CHCl3 fraction of the extract of the root, using three steps of medium-pressure liquid chromatography (MPLC) by employing HW-40F, Sephadex LH-20 and LiChroCN as adsorbents. Pure glabridin was crystallized from an MeOH-H2O mixture (95:5 v/v) to yield colorless crystals containing one mol­ecule per asymmetric unit (Z' = 1) in the space group P212121. Although the crystal structure has been reported before, the determination of the absolute configuration remained uncertain. Stereochemical analysis, including circular dichroism, NMR data and an X-ray diffraction data set with Bijvoet differences, confirms that glabridin, purified from its natural source, is found only in a C3 R configuration. These results can therefore be used as a reference for the assignment of the configuration and enantio­purity of any isolated or synthetic glabridin sample.
    Subject
    crystal structure; absolute configuration; glabridin; natural compounds
    Type
    Article
    Date available in INDIGO
    2016-04-26T21:02:18Z
    URI
    http://hdl.handle.net/10027/20448
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