Solvate Formation of Bis(demethoxy)curcumin: Crystal Structure Analyses and Stability Investigations

Yuan Lina; Horosanskaia Elena; Engelhardt Felix; Edelmann Frank T.; Couvrat Nicolas; Sanselme Morgane; Cartigny Yohann; Coquerel Gerard; Seidel-Morgenstern Andreas; Lorenz Heike

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Solvate Formation of Bis(demethoxy)curcumin: Crystal Structure Analyses and Stability Investigations

机译：溶剂化物形成双（脱乙氧基）姜黄素：晶体结构分析和稳定性研究

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Bis(demethoxy)curcumin (BDMC), extracted from rhizomes of the traditional herb Curcuma longa, has revealed a wide range of medicinal applications, such as antimicrobial and anticarcinogenic. Pure BDMC was obtained by recrystallization from ethanol and three BDMC solvates were identified with acetone, methanol, and isopropanol. The crystal structures of pure BDMC and the solvates were resolved by single crystal X-ray diffraction. Analyses of the crystal structures and calculations of crystal packing efficiencies revealed that pure BDMC is efficiently packed. The solvents involved are not utilized to fill the void spaces in the crystal structures, but to provide effective intermolecular interactions. The stoichiometry of the three solvates obtained from single crystal data is 1:1, which is in good agreement with the gravimetric analyses. Furthermore, the desolvation process and the stability of the solvates were investigated by various analytical techniques including X-ray diffraction, differential scanning calorimetry, thermogravimetric analyses, hot-stage microscopy, and dynamic vapor sorption. Results show that the methanol solvate is more stable compared to the acetone and isopropanol solvates attributed to the strong hydrogen bonding network. Moreover, the desolvation process of the three solvates proceeds through a destructive-reconstructive mechanism.

机译：从传统的草本植物莪术Longa的根茎中提取的BIS（脱氧基）姜黄素（BDMC）揭示了各种药用应用，例如抗菌和抗癌性。通过从乙醇中重结晶获得纯BDMC，用丙酮，甲醇和异丙醇鉴定三种BDMC溶剂化物。通过单晶X射线衍射解析纯BDMC和溶剂化物的晶体结构。晶体填料效率的晶体结构分析显示纯BDMC有效填充。所涉及的溶剂不用于填充晶体结构中的空隙空间，而是提供有效的分子间相互作用。从单晶数据获得的三种溶剂化物的化学计量为1：1，与重量分析很好。此外，通过包括X射线衍射，差示扫描量热法，热阶段显微镜和动态蒸汽吸附，通过各种分析技术研究了溶剂化方法和溶剂化物的稳定性。结果表明，与丙酮和异丙醇溶剂化物归因于强氢键网络相比，甲醇溶剂化物更稳定。此外，三种溶剂化物的脱溶解方法通过破坏性重建机制进行。

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《Crystal growth & design》 |2019年第2期|共14页
作者
Yuan Lina; Horosanskaia Elena; Engelhardt Felix; Edelmann Frank T.; Couvrat Nicolas; Sanselme Morgane; Cartigny Yohann; Coquerel Gerard; Seidel-Morgenstern Andreas; Lorenz Heike;
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Max Planck Inst Dynam Complex Tech Syst D-39106 Magdeburg Germany;

Max Planck Inst Dynam Complex Tech Syst D-39106 Magdeburg Germany;

Otto von Guericke Univ Chem Inst Univ Pl 2 D-39106 Magdeburg Germany;

Otto von Guericke Univ Chem Inst Univ Pl 2 D-39106 Magdeburg Germany;

UNIROUEN Normandie EA3233 Lab Sci &

Methodes Separat Normandie Univ F-76821 Mont St Aignan France;

UNIROUEN Normandie EA3233 Lab Sci &

Methodes Separat Normandie Univ F-76821 Mont St Aignan France;

UNIROUEN Normandie EA3233 Lab Sci &

Methodes Separat Normandie Univ F-76821 Mont St Aignan France;

UNIROUEN Normandie EA3233 Lab Sci &

Methodes Separat Normandie Univ F-76821 Mont St Aignan France;

Max Planck Inst Dynam Complex Tech Syst D-39106 Magdeburg Germany;

Max Planck Inst Dynam Complex Tech Syst D-39106 Magdeburg Germany;

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Solvate Formation of Bis(demethoxy)curcumin: Crystal Structure Analyses and Stability Investigations

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