Absolute configuration of naturally occurring glabridin.

IF 0.8 4区 化学 Acta crystallographica. Section C, Crystal structure communications Pub Date : 2013-11-01 Epub Date: 2013-10-09 DOI:10.1107/S0108270113018842
Charlotte Simmler, Frank R Fronczek, Guido F Pauli, Bernard D Santarsiero
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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.

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天然草木犀的绝对构型。
标题化合物{系统名称:4-[(3R)-8,8-二甲基-3,4-二氢-2H-吡喃并[2,3-f]苯并吡喃-3-基]苯-1,3-二醇,通称格拉布丁},C20H20O4,是甘草(豆科,欧洲甘草)根中的一种物种特异性生物标志物。本研究以 HW-40F、Sephadex LH-20 和 LiChroCN 为吸附剂,采用三步中压液相色谱法(MPLC)从根提取物的 CHCl3 富集馏分中纯化了这种前酰异黄酮。从 MeOH-H2O 混合物(95:5 v/v)中结晶出纯净的格拉布丁,得到无色晶体,每个不对称单元含有一个分子(Z' = 1),空间群为 P212121。虽然该晶体结构之前已有报道,但绝对构型的确定仍不确定。立体化学分析(包括圆二色性分析、核磁共振数据和具有 Bijvoet 差异的 X 射线衍射数据集)证实,从天然来源中提纯的格拉布林仅呈 C3 R 构型。因此,这些结果可作为任何分离或合成的格拉布丁样品的构型和对映体纯度分配的参考。
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期刊介绍: Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.
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