Physicochemical properties and mechanism of solubilised neohesperidin system based on inclusion complex of hydroxypropyl-β-cyclodextrin

被引:8
作者
Wang, Chunqing [1 ]
Xia, Na [1 ,2 ]
Yu, Ming [3 ]
Zhu, Siming [1 ]
机构
[1] South China Univ Technol, Sch Food Sci & Engn, Guangzhou, Peoples R China
[2] Kashi Univ, Coll Life & Geog Sci, Kashi, Peoples R China
[3] Tsinghua Univ Zhejiang, Inst Food & Hlth, Yangtze Delta Reg Inst, Jiaxing, Peoples R China
关键词
complex; HP-beta-CD; neohesperidin; solubility; SOLID DISPERSIONS; DISSOLUTION; DERIVATIVES; FLAVONOIDS; DRUG;
D O I
10.1111/ijfs.16167
中图分类号
TS2 [食品工业];
学科分类号
0832 ;
摘要
A solvent method was used to prepare the inclusion compound of neohesperidin (NH) and hydroxypropyl-beta-cyclodextrin (HP-beta-CD) to improve the water solubility and thermal stability of NH. The physical and chemical properties and supramolecular structure of the inclusion complex were investigated by UV-vis spectroscopy, FTIR, SEM, TG-DTG, PXRD, NMR and molecular docking techniques. The results showed that the C-ring of NH was embedded in the cavity of HP-beta-CD to form an inclusion complex. The phase has changed significantly, NH is completely dispersed in HP-beta-CD in an amorphous state, and the two are combined in the form of non-covalent bonds such as hydrogen bonds or van der Waals forces. Through inclusion of HP-beta-CD, the solubility of NH in water at 37 degrees C increased from 161.81 mu g ml(-1) to 1927.12 mu g ml(-1), and its stability was also significantly improved.
引用
收藏
页码:107 / 115
页数:9
相关论文
共 34 条
[1]   Characterization of thymoquinone/hydroxypropyl-β-cyclodextrin inclusion complex: Application to anti-allergy properties [J].
Al-Qubaisi, Mothanna Sadiq ;
Rasedee, Abdullah ;
Flaifel, Moayad Husein ;
Eid, Eltayeb E. M. ;
Hussein-Al-Ali, Samer ;
Alhassan, Fatah H. ;
Salih, Ashraf M. ;
Hussein, Mohd Zobir ;
Zainal, Zulkarnain ;
Sani, Dahiru ;
Aljumaily, Abdulmajeed Hammadi ;
Saeed, Mohammed Ibrahim .
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2019, 133 :167-182
[2]   Quercetin, Rutin And Quercetin-Rutin Incorporated Hydroxypropyl β-Cyclodextrin Inclusion Complexes [J].
Basaran, Ebru ;
Ozturk, A. Alper ;
Senel, Behiye ;
Demirel, Muzeyyen ;
Sarica, Senay .
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2022, 172
[3]   Influence of l-rhamnosyl-d-glucosyl derivatives on properties and biological interaction of flavonoids [J].
Bellocco, Ersilia ;
Barreca, Davide ;
Lagana, Giuseppina ;
Leuzzi, Ugo ;
Tellone, Ester ;
Ficarra, Silvana ;
Kotyk, Arnost ;
Galtieri, Antonio .
MOLECULAR AND CELLULAR BIOCHEMISTRY, 2009, 321 (1-2) :165-171
[4]   Study on the effect of solvent on the inclusion interaction of hydroxypropyl-β-cyclodextrin with three kinds of coumarins by phase solubility method [J].
Chen, Aiju ;
Liu, Min ;
Dong, Lina ;
Sun, Dezhi .
FLUID PHASE EQUILIBRIA, 2013, 341 :42-47
[5]   Naftopidil-fumaric acid interaction in a solid dispersion system: Improving the dissolution rate and oral absorption of naftopidil in rats [J].
Choi, Jin-Seok ;
Byeon, Jong Chan ;
Park, Jeong-Sook .
MATERIALS SCIENCE & ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS, 2019, 95 :264-274
[6]   Microfluidic reactor for lipase-catalyzed regioselective synthesis of neohesperidin ester derivatives and their antimicrobial activity research [J].
Du, Lihua ;
Jiang, Zhipeng ;
Xu, Liangliang ;
Zhou, Nani ;
Shen, Jiahong ;
Dong, Zhen ;
Shen, Le ;
Wang, Hong ;
Luo, Xiping .
CARBOHYDRATE RESEARCH, 2018, 455 :32-38
[7]   Water dispersibility of the β-carotene source and its effect on the physical, thermal, and in vitro release properties of an inclusion complex [J].
Flores, Floirendo P. ;
Kong, Fanbin .
INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY, 2021, 56 (07) :3618-3626
[8]   Enhanced dissolution and skin permeation profiles of epalrestat with β-cyclodextrin derivatives using a cogrinding method [J].
Furuishi, Takayuki ;
Takahashi, Shoma ;
Ogawa, Noriko ;
Gunji, Mihoko ;
Nagase, Hiromasa ;
Suzuki, Toyofumi ;
Endo, Tomohiro ;
Ueda, Haruhisa ;
Yonemochi, Etsuo ;
Tomono, Kazuo .
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2017, 106 :79-86
[9]   Preparation and Physical Characterization of a Diclofenac-Ranitidine Co-precipitate for Improving the Dissolution of Diclofenac [J].
Gaitano, Robertino O. ;
Calvo, Natalia L. ;
Narda, Griselda E. ;
Kaufman, Teodoro S. ;
Maggio, Ruben M. ;
Brusau, Elena V. .
JOURNAL OF PHARMACEUTICAL SCIENCES, 2016, 105 (03) :1258-1268
[10]   The kinetics of formation of resveratrol-β-cyclodextrin-NH2 and resveratrol analog-β-cyclodextrin-NH2 supramolecular complexes [J].
Hudson, Eliara Acipreste ;
de Paula, Hauster Maximiler Campos ;
Coelho, Yara Luiza ;
Glanzmann, Nicolas ;
da Silva, Adilson David ;
da Silva, Luis Henrique Mendes ;
Pires, Ana Clarissa dos Santos .
FOOD CHEMISTRY, 2022, 366