Citation: ZHOU Kai, WENG Ying, HOU Qingqing, LOU Benyong. Preparation, Crystal Structure and Solubility of Organic Salt Hydrate of Berberine-Genistein[J]. Chinese Journal of Applied Chemistry, ;2019, 36(2): 230-235. doi: 10.11944/j.issn.1000-0518.2019.02.180163 shu

Preparation, Crystal Structure and Solubility of Organic Salt Hydrate of Berberine-Genistein

  • Corresponding author: LOU Benyong, lby@mju.edu.cn
  • Received Date: 9 May 2018
    Revised Date: 20 June 2018
    Accepted Date: 14 August 2018

    Fund Project: the National Undergraduate Innovative Training Program 201610395010Supported by the National Undergraduate Innovative Training Program(No.201610395010), the Natural Science Foundation of Fujian Province(No.2015J01599)the Natural Science Foundation of Fujian Province 2015J01599

Figures(6)

  • The organic salt hydrate of berberine with genistein, [C20H18NO4]+·[C15H9O5]-·2.5H2O·0.5(C2H5OH), was prepared and its crystal structure was determined. The result showed that the organic salt hydrate crystallized in monoclinic crystal system and P21/c space group. The 7-substituted hydroxyl of genistein lost its proton and turned to be anion. The resulting hydroxyl anion was involved in O—H····O- hydrogen bonding with 4'-substituted hydroxyl, which gave rise to an one-dimensional hydrogen-bonded chain-like structure. Two water molecules formed a chain-like structure through hydrogen-bonding interactions and further connected the 1D chain of genistein into a 2D hydrogen-bonded network. The hydrate turned to be amorphous form after losing water molecules by heating. The amorphous form could transform into crystalline organic salt hydrate after suspending in ethanol-water for 24 h. After forming berberine-genistein salt hydrate, the solubility of genistein in water increased slightly.
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    1. [1]

      Stahl P H, Wermuth C G. Handbook of Pharmaceutical Salts:Properties, Selection and Use[M]. Wiley-VCH, Chichester, 2002.

    2. [2]

      Sanphui P, Tothadi S, Ganguly S. Salt and Cocrystals of Sildenafil with Dicarboxylic Acids:Solubility and Pharmacokinetic Advantage of the Glutarate Salt[J]. Mol Pharm, 2013,10(12):4687-4697. doi: 10.1021/mp400516b

    3. [3]

      Black S N, Collier E, Davey R J. Structure, Solubility, Screening and Synthesis of Molecular Salts[J]. J Pharm Sci, 2007,96(5):1053-1068. doi: 10.1002/jps.20927

    4. [4]

      Thorat S H, Sahu S K, Patwadkar M V. Drug-Drug Molecular Salt Hydrate of an Anticancer Drug Gefitinib and a Loop Diuretic Drug Furosemide:An Alternative for Multidrug Treatment[J]. J Pharm Sci, 2015,104(12):4207-4216. doi: 10.1002/jps.24651

    5. [5]

      Bag P P, Ghosh S, Khan H. Drug-Drug Salt Forms of Ciprofloxacin with Diflunisal and Indoprofen[J]. CrystEngComm, 2014,16(32):7393-7396. doi: 10.1039/C4CE00631C

    6. [6]

      Gopi S P, Ganguly S, Desiraju G R. A Drug-Drug Salt Hydrate of Norfloxacin and Sulfathiazole:Enhancement of in Vitro Biological Properties via Improved Physicochemical Properties[J]. Mol Pharm, 2016,13(10):3590-3594. doi: 10.1021/acs.molpharmaceut.6b00320

    7. [7]

      Crozier A, Jaganath I B, Clifford M N. Dietary Phenolics:Chemistry, Bioavailability and Effects on Health[J]. Nat Prod Rep, 2009,26(8):1001-1043. doi: 10.1039/b802662a

    8. [8]

      LIN Fangxia, QIU Bingqing, LOU Benyong. Preparation, Crystal Structure and Solubility of Triethylamine Salt Monohydrate of Naringenin[J]. Chinese J Appl Chem, 2017,34(4):481-485.  

    9. [9]

      Baird A W, Taylor C T, Brayden D J. Non-Antibiotic Anti-Diarrhoeal Drugs:Factors Affecting Oral Bioavailability of Berberine and Loperamide in Intestinal Tissue[J]. Adv Drug Delivery Rev, 1997,23(1/2/3):111-120.  

    10. [10]

      Habtemariam S. Berberine and Inflammatory Bowel Disease:A Concise Review[J]. Pharmacol Res, 2016,113(partA):592-599.  

    11. [11]

      Jin Y, Khadka D B, Cho W J. Pharmacological Effects of Berberine and Its Derivatives:A Patent Update[J]. Expert Opin Ther Pat, 2016,26(2):229-243. doi: 10.1517/13543776.2016.1118060

    12. [12]

      Sun Y Y, Xu K L, Wang Y T. A Systematic Review of the Anticancer Properties of Berberine, A Natural Product from Chinese Herbs[J]. Anti-Cancer Drug, 2009,20(9):757-769. doi: 10.1097/CAD.0b013e328330d95b

    13. [13]

      Wang C, Perumalla SR, Lu R. Sweet Berberine[J]. Cryst Growth Des, 2016,16(2):933-939. doi: 10.1021/acs.cgd.5b01484

    14. [14]

      Zhang Y J, Lou B Y, Huang Y L. Crystal Structure, Stability and Dissolution of a Drug-Drug Molecular Salt Hydrate of Berberine with Protocatechuic Acid[J]. Chinese J Struct Chem, 2018,37(3):400-406.  

    15. [15]

      Zhou R J, Yang X Q, Wang D. Anti-Tumor Effects of All-Trans Retinoic Acid Are Enhenced by Genistein[J]. Cell Biochem Biophys, 2012,62(1):177-184. doi: 10.1007/s12013-011-9279-0

    16. [16]

      Rigaku. Crystal Clear Programs for Data Collection, Cell Refinement and Structure Solution[CP]. Japan: Rigaku Corp, 2000.

    17. [17]

      Sheldrick G M. A Short History of SHELX[J]. Acta Cryst Sect A, 2008,64(1):112-122. doi: 10.1107/S0108767307043930

    18. [18]

      Sheldrick G M. Crystal Structure Refinement with SHELXL[J]. Acta Cryst Sect C, 2015,71(1):3-8. doi: 10.1107/S2053229614024218

  • 加载中
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