Dataset Information

Studies on the Inclusion Complexes of Daidzein with ?-Cyclodextrin and Derivatives.

ABSTRACT: The inclusion complexes between daidzein and three cyclodextrins (CDs), namely ?-cyclodextrin (?-CD), methyl-?-cyclodextrin (Me-?-CD, DS = 12.5) and (2-hydroxy)propyl-?-cyclodextrin (HP-?-CD, DS = 4.2) were prepared. The effects of the inclusion behavior of daidzein with three kinds of cyclodextrins were investigated in both solution and solid state by methods of phase-solubility, XRD, DSC, SEM, ¹H-NMR and 2D ROESY methods. Furthermore, the antioxidant activities of daidzein and daidzein-CDs inclusion complexes were determined by the 1,1-diphenyl-2-picryl-hydrazyl (DPPH) method. The results showed that daidzein formed a 1:1 stoichiometric inclusion complex with ?-CD, Me-?-CD and HP-?-CD. The results also showed that the solubility of daidzein was improved after encapsulating by CDs. ¹H-NMR and 2D ROESY analyses show that the B ring of daidzein was the part of the molecule that was most likely inserted into the cavity of CDs, thus forming an inclusion complex. Antioxidant activity studies showed that the antioxidant performance of the inclusion complexes was enhanced in comparison to the native daidzein. It could be a potentially promising way to develop a new formulation of daidzein for herbal medicine or healthcare products.

SUBMITTER: Li S

PROVIDER: S-EPMC6149782 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Studies on the Inclusion Complexes of Daidzein with β-Cyclodextrin and Derivatives.

Li Shujing S Yuan Li L Chen Yong Y Zhou Wei W Wang Xinrui X

Molecules (Basel, Switzerland) 20171208 12

The inclusion complexes between daidzein and three cyclodextrins (CDs), namely β-cyclodextrin (β-CD), methyl-β-cyclodextrin (Me-β-CD, DS = 12.5) and (2-hydroxy)propyl-β-cyclodextrin (HP-β-CD, DS = 4.2) were prepared. The effects of the inclusion behavior of daidzein with three kinds of cyclodextrins were investigated in both solution and solid state by methods of phase-solubility, XRD, DSC, SEM, ¹H-NMR and 2D ROESY methods. Furthermore, the antioxidant activities of daidzein and daidzein-CDs inc ...[more]

PMID: 29292784

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Project description:The study aimed to prepare inclusion complexes of 1,3-diphenylurea (DPU) with β-cyclodextrin (βCD) and 2-hydroxypropyl-β-cyclodextrin (HP-βCD) using a three-dimensional ground mixture (3DGM). Their physicochemical properties, intermolecular interactions, solubilities, and plant growth-promoting activities were investigated on broccoli sprouts. Phase-solubility diagrams indicated the stability constant (Ks) and complexation efficiency (CE) of βCD/DPU were found to be K1/1 = 250 M-1, CE = 2.48× 10-3. The Ks and CEs of HP-βCD/DPU were found to be K1/1 = 427 M-1, CE = 3.93 × 10-3 and K2/1 = 196 M-1, CE = 1.93 × 10-3 respectively. The powder X-ray diffraction results of 3DGM (βCD/DPU = 2/1, HP-βCD/DPU = 2/1) showed that the diffraction peaks originating from the DPU and βCD disappeared, indicating a halo pattern. Differential scanning calorimetry results showed an endothermic peak at 244 °C derived from the melting point of DPU, but the endothermic peak disappeared in the 3DGM (βCD/DPU = 2/1, HP-βCD/DPU = 2/1). Near-infrared absorption spectra showed peak shifts in 3DGM (βCD/DPU and HP-βCD/DPU) at the -CH and -NH groups of DPU and the -OH groups of βCDs and free water. In the dissolution test (after 5 min), the concentration of intact DPU was 0.083 μg/mL. However, the dissolution concentrations of DPU in the 3DGM (βCD/DPU = 1/1), 3DGM (βCD/DPU = 2/1), 3DGM (HP-βCD/DPU = 1/1), and 3DGM (HP-βCD/DPU = 2/1) were 3.27, 3.64, 5.70, and 7.03 μg/mL, respectively, indicating higher solubility than that of the intact DPU. Further, 1H-1H NOESY NMR spectroscopic measurements showed cross-peaks between H-A (7.32 ppm) and H-B (7.12 ppm) of DPU and H-6 (3.79 ppm) in the βCD cavity of the 3DGM (βCD/DPU = 2/1). A cross-peak was also observed among DPU H-A (7.32 ppm), H-B (7.11 ppm), and H-6 (3.78 ppm) in the βCD cavity. The results of the broccoli sprout cultivation experiment showed that 3DGM (βCD/DPU = 1/1), 3DGM (βCD/DPU = 2/1), 3DGM (HP-βCD/DPU = 1/1), and 3DGM (HP-βCD/DPU = 2/1) increased the stem thickness compared with that of the control group (DPU). These results indicated that the βCD/DPU and HP-βCD/DPU inclusion complexes were formed by the three-dimensional mixing and milling method, which enhanced the solubility and plant growth-promoting effects.

Dataset Information

Studies on the Inclusion Complexes of Daidzein with ?-Cyclodextrin and Derivatives.

Publications

Studies on the Inclusion Complexes of Daidzein with β-Cyclodextrin and Derivatives.

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