MOLECULES
·
2017
·Vol. 22
·期 12
·2183
·
IF 2.861
Shujing Li,Li Yuan,Yong Chen,Wei Zhou,Xinrui Wang
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 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 β-CD, Me-β-CD and HP-β-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.Keywords:daidzein;cyclodextrin;inclusion complex;antioxidant activity
研究领域:
药学
·
化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CHINESE JOURNAL OF ANALYTICAL CHEMISTRY
·
2017
·
IF 0.795
Ying-Hui DENG,Li-Na SU,Yan-Hua PANG,Ya-Fei GUO,Fen WANG,Xia-Li LIAO,Bo YANG
To improve the water solubility of daidzein, solid inclusion complexes of daidzein with two amino-modified β -cyclodextrins (ACDs), i.e., mono-6-amino-6-deoxy- β -cyclodextrin (NCD) and mono-6-ethylenediamino-6-deoxy- β -cyclodextrin (ENCD), were prepared by the saturated solution method in water with yields of 83% and 67%, respectively, under the optimized conditions including the ratio of daidzein/ACD of 3:1 and the stirring time of 72 h. The formation of the two inclusion complexes was confirmed by X-ray diffractometry (XRD) and thermo gravimetric (TG) analysis. The inclusion stoichiometry of the inclusion complexes was 1:1 from the Job plot and their complexation stability constants ( K S ) were 899.2 and 203.8 M −1 from fluorescence titration, respectively. After formation of inclusion complexes with NCD and ENCD, the water solubility of daidzein was dramatically raised to 15.2 and 13.2 mg mL −1 at 25 °C, increasing by 1800 and 1500-fold compared to native daidzein (8.31 μg mL −1 ).
研究领域:
药物化学
·
材料科学
·
生物化学
✓ 已验证
产品关联
DOI
高影响因子
FLUID PHASE EQUILIBRIA
·
2014
·
IF 2.241
Ai-Guo Zeng,Xin-Li Pang,Na Wu,Duan Wang,Guan-Jun Nan,Guang-De Yang,Xiao-Li Bian
The solubility of daidzein in propylene glycol + water cosolvent mixtures was determined by UV spectrophotometry, and predicted using the Jouyban–Acree model and the mathematical model based on the algebraic rule of mixing. The thermodynamic functions, such as Gibbs energy, enthalpy, and entropy of solution and of mixing and so on, were obtained from these solubility data by using the van’t Hoff and Gibbs equations. The results show that the daidzein solubility increases as propylene glycol proportion increases in the mixtures and the solution temperature increases. The Jouyban–Acree model can be used to predict the solubility of daidzein in propylene glycol + water cosolvent mixtures at different temperatures. The driving mechanism for daidzein solubility in water-rich mixtures is the entropy, probably due to water-structure loss around the drug non-polar moieties by effect of propylene glycol, whereas the driving mechanism is the enthalpy above 0.20 mass fraction of propylene glycol, probably due to daidzein solvation increase by the cosolvent molecules. Non linear enthalpy–entropy compensation with negative slope from water up to 0.20 mass fraction of propylene glycol and positive slope beyond this composition up to pure propylene glycol is found.
研究领域:
药学
·
物理化学
✓ 已验证
产品关联
DOI
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2024
·
IF 13.3
Yongxian Niu,Xi zhang,Wenbing Yu,Han Yin,Rui Lu,Zhenggang Liu,Fang Lu
Herein, a renewable system consisted of tartaric acid and isopropanol was developed to produce diosgenin efficiently from Dioscorea zingiberensis rhizomes. The yield of diosgenin reached 4.15% comparable to the highest value reported in previous researches. The combination of experiment and DFT calculation revealed that the acid-alcohol system could regulate the hydrogen bond interaction of each component in the rhizomes to disassemble the connection network and promote the release of saponin. Meanwhile, the intramolecular hydrogen bond of tartaric acid and the steric hindrance effect of isopropanol could prevent the esterification reaction and maintain the strong acidity of the system for the high yield of diosgenin. The scale-up experiment with a 100-fold feeding capacity was also conducted successfully. Furthermore, the technological process integrated with purification of diosgenin, recovery of organic acid and solvent and upgrading of residual solid to porous carbon materials has been established systematically to verify the prospective of industrialization.
研究领域:
植物化学
·
药物化学
✓ 已验证
产品关联
DOI
高影响因子
ChemSusChem
·
2018
·Vol. 11
·期 18
·3175-3183
·
IF 7.411
Jinyue Dai,Na Teng,Yunyan Peng,Yuan Liu,Lijun Cao,Jin Zhu,Xiaoqing Liu
Graphical Renewable polymers : A biobased benzoxazine resin (Dz-f) with excellent thermal properties was synthesized from daidzein and furfurylamine by using a microwave heating method. It was then cured and its thermal properties evaluated by differential scanning calorimetry (DSC), TGA, and dynamic mechanical analysis (DMA; see figure). A biobased benzoxazine resin (Dz-f) demonstrating excellent thermal properties was synthesized from daidzein and furfurylamine by using a microwave heating method. The chemical structure of synthesized benzoxazine monomer was identified by FTIR and NMR ( 1 H and 13 C NMR) before it was cured and its thermal properties evaluated by differential scanning calorimetry (DSC), TGA, and dynamic mechanical analysis (DMA). The cured resin p(Dz-f) exhibited a glass transition temperature ( T g ) of 391 °C, a very high char yield of 68.7 %, and outstanding thermal stability; the T g value obtained was the highest thermal stability value ever reported for polybenzoxazine with a high biobased content. Moreover, Dz-f demonstrated a satisfying processability, which was rare for the high-performance thermosetting resins. This work provided us with a new strategy for the preparation of high biocontent resins with excellent thermal properties. In addition, the combination of biobased feedstocks with a microwave-assisted heating method as well as the potential application of this approach in high-end fields might perpetuate remarkable progress towards the sustainable development of the polymeric industry.
研究领域:
材料科学
·
有机化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Food & Function
·
2016
·Vol. 7
·期 11
·4683-4692
·
IF 2.686
Fan Yuan-jing,Wei Wei,Luo Jian-ping,Jin Yu-xia,Dai Zi-ling
This study aimed to explore the effects of genistein on regulating the activation of UGTs via the Nrf2/Keap1 pathway and to elucidate the underlying mechanisms of detoxification and hepatic protection. Experiments monitoring genistein-induced protection against acetaminophen-induced cell damage were performed in L-02, HepG2 and Hep3b cells. The results of the MTT, AST, ALT, LDH, GSH and GSSG assays showed that genistein evidently protected the cells from acetaminophen-induced injury in a dose-dependent manner. The control cells were treated with 10 mM acetaminophen without genistein to compare with the effects of the combination of acetaminophen and genistein on the expression of UGT1A1, 1A6 and 1A9, Nrf2 and Keap1 mRNAs, as well as the expression of Nrf2 and Keap1 proteins, which were tested by western blotting. The results showed that the expression of the Nrf2 mRNA and protein increased; in contrast, the expression levels of the Keap1 mRNA and protein were obviously reduced by genistein in a dose-dependent manner. Meanwhile, the expression of the UGT mRNA was increased, and UGT1A9 exhibited the highest expression among the three UGTs. Accordingly, the residual acetaminophen content was obviously reduced and acetaminophen glucuronidation increased after 24 hours of treatment with genistein in a dose-dependent manner.
研究领域:
药理学
·
毒理学
·
细胞生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2023
·Vol. 28
·期 13
·5077
·
IF 4.6
Zhenhao Yao,Yin Lu,Jianan Song,Kan Zhang
In this work, a novel bio-based high-performance bisbenzoxazine resin was synthesized from daidzein, 2-thiophenemethylamine and paraformaldehyde. The chemical structure was confirmed using nuclear magnetic resonance spectroscopy (NMR) and Fourier-transform infrared spectroscopy (FT-IR). The polymerization process was systematically studied using differential scanning calorimetry (DSC) and in situ FT-IR spectra. It can be polymerized through multiple polymerization behaviors under the synergistic reaction of thiophene rings with benzopyrone rather than a single polymerization mechanism of traditional benzoxazines, as reported. In addition, thermogravimetric analysis (TGA) and a microscale combustion calorimeter (MCC) were used to study the thermal stability and flame retardancy of the resulting polybenzoxazine. The thermosetting material showed a high carbon residue rate of 62.8% and a low heat release capacity (HRC) value of 33 J/gK without adding any flame retardants. Based on its outstanding capability of carbon formation, this newly obtained benzoxazine resin was carbonized and activated to obtain a porous carbon material doped with both sulfur and nitrogen. The CO2absorption of the carbon material at 0 °C and 25 °C at 1 bar was 3.64 mmol/g and 3.26 mmol/g, respectively. The above excellent comprehensive properties prove its potential applications in many advanced fields.Keywords:benzoxazine;daidzein;thiophene;CO2absorption;thermal stability
研究领域:
材料科学
·
化学工程
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Tiefeng Yuan,Liping Wang,Linzhou Chen,Jinjian Zhong,Yuyang Lin,Yihan Wang,Chen Lin,Huajun Fan
In this study, an efficient approach to preparation of different anthocyanins from Purple-heart Radish was developed by combining microwave-assisted extraction (MAE), macroporous resin purification (MRP) and ultrasound-assisted acid hydrolysis (UAAH) for evaluation of physicochemical stability and pancreatic lipase (PL) inhibitory activity. By optimization of MAE, MRP and UAAH processes, the anthocyanins reached the yield of 6.081 ± 0.106 mg/g, the purity of 78.54 ± 0.62 % (w/w) and the content of 76.29 ± 1.31 % (w/w), respectively. With high-resolution UHPLC-Q-Orbitrap/MS, 15 anthocyanins were identified as pelargonins with diverse glucosides and confirmed by pelargonidin standard. By glycosylation, pelargonins exhibited higher stability in different pH, temperature, light, metal ions environments than that of pelargonidin. However, PL inhibitory assay, kinetic analysis and molecular docking demonstrated that pelargonidin had higher PL inhibitory activity than pelargonins even though with similar binding sites and a dose–effect relationship. The above results revealed that the effect of glycosylation and deglycosylation on PL inhibitory activity and physicochemical stability.
研究领域:
食品科学
·
药理学
·
化学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2022
·
IF 9.231
Yejun Zhong,Lei Yang,Taotao Dai,Ziyi Zhu,Hongyu Chen,Jianyong Wu,Er Sheng Gong
The effect of ovalbumin-flavonoids (naringenin, genistein, naringin, puerarin, and daidzein) interactions on the formation and properties of ovalbumin hydrogels was investigated. The results suggested that flavonoids were able to promote the gelation of low concentration ovalbumin solution, which was not able to form hydrogel upon heating. All hydrogels formed by flavonoids and ovalbumin were more elastic than viscous. The hydrogels formed by naringenin and ovalbumin showed the strongest gel hardness, springiness, and water holding capacity. Fluorescence spectroscopy and molecular docking analysis revealed that the main interactions between ovalbumin and naringenin, genistein, puerarin, naringin were hydrogen bond, while the main interaction between ovalbumin and daidzein was hydrophobic force. Flavonoids, which have a structure with more phenolic hydroxyl groups, a C2 = C3 double bond and dehydrogenated glycosides, possessed higher affinity to ovalbumin. This research provides new insights into mechanism of ovalbumin-flavonoids interactions and its influence on the formation and property of hydrogel.
研究领域:
食品科学
·
生物物理学
·
化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Yingchao Li,Xiaoyu Liu,Farong Lu,Huichao Li,Jiaming Zhang,Yawei Zhang,Wenchao Li,Weiping Wang,Miaomiao Yang,Zhining Ma,Hui Zhang,Xiaomian Zhou,Youjun Xu,Zhonggui He,Jin Sun,Tianhong Zhang,Qikun Jiang
Daidzein (DAN) is an isoflavone, and it is often found in its natural form in soybean and food supplements. DAN has poor bioavailability owing to its extremely low water solubility and first-pass metabolism. Herein, we hypothesized that a bioactivatable natural amino acid-bearing carbamate prodrug strategy could increase the water solubility and metabolic stability of DAN. To test our hypothesis, nine amino acid prodrugs of DAN were designed and synthesized. Compared with DAN, the optimal prodrug (daidzein-4′-O-CO-N-isoleucine, D-4′-I) demonstrated enhanced water solubility and improved phase II metabolic stability and activation to DAN in plasma. In addition, unlike the passive transport of DAN, D-4′-I maintained high permeability via organic anion-transporting polypeptide 2B1 (OATP2B1)-mediated transport. Importantly, D-4′-I increased the oral bioavailability by 15.5-fold, reduced the gender difference, and extended the linear absorption capacity in the pharmacokinetics of DAN in rats. Furthermore, D-4′-I exhibited dose-dependent protection against liver injury. Thus, the natural amino acid-bearing carbamate prodrug strategy shows potential in increasing water solubility and improving phase II metabolic stability to enhance the oral bioavailability of DAN.
研究领域:
药理学
·
药物化学
·
代谢组学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF BIOMEDICAL SCIENCE
·
2023
·Vol. 30
·期 1
·1-14
·
IF 11
Shen Weiyi,Shao Wentao,Wang Qihan,Wang Bo,Zhao Gang,Gu Aihua,Jiang Zhaoyan,Hu Hai
Background Cholesterol gallstone disease is a common disease. Reducing cholesterol burden is important to prevent/treat gallstone. In this study, we investigated the application of diosgenin (DG) to prevent the formation of gallstone in mice.Methods Adult male C57BL/6J mice were fed with the lithogenic diet (LD) only or LD supplemented with DG or ezetimibe for 8 weeks. Incidences of gallstone formation were documented. Intestine and liver tissues were collected to measure the lipid contents and expression of genes in cholesterol metabolism. Caco2 cells were treated with DG to monitor the regulation on cholesterol absorption and the transcriptional regulation of Npc1l1 gene. Changes of gut microbiota by DG was analyzed. Intraperitoneal injection of LPS on mice was performed to verify its effects on STAT3 activation and Npc1l1 expression in the small intestine.Results LD led to 100% formation of gallstones in mice. In comparison, dietary DG or ezetimibe supplementary completely prevents gallstones formation. DG inhibited intestinal cholesterol absorption in mice as well as in Caco2 cells by down-regulation of Npc1l1 expression. DG could directly inhibit phosphorylation of STAT3 and its transcriptional regulation of Npc1l1 expression. Furthermore, DG could modulate gut microbiota profiles and LPS mediated STAT3 activation and Npc1l1 expression.Conclusion Our results demonstrated that dietary DG could inhibit intestinal cholesterol absorption through decreasing NPC1L1 expression to prevent cholesterol gallstone formation.
研究领域:
药理学
·
胃肠病学
·
分子生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Food Bioscience
·
2025
·
IF 5.9
Yanling Sun,Shupeng Li,Rongxin Liu,Ning Ma,Xinghua Zhao,Xin He
Daidzein (DAI) and betaine (BTN) exhibit outstanding therapeutic effects on the treatment of obesity and lipid-related diseases. However, the low solubility and oral bioavailability of DAI, along with the poor stability of BTN, limit the clinical application of both compounds. Here, a novel 1:2 drug-drug cocrystal of daidzein and betaine (DAI-BTN) was successfully prepared using crystal engineering technology. Dynamic vapor sorption analysis showed that the mass change of DAI-BTN was reduced by 58% in a relatively humidity range of 0% to 95% compared to BTN. As compared to pure DAI, the intrinsic dissolution rate and the bioavailability of DAI-BTN were enhanced by 4.34-fold and 3.73-fold, respectively. Furthermore, the effect and mechanisms of DAI-BTN in a mouse model of diet-induced obesity were explored. The results showed that the DAI-BTN can reduce body weight and adipocyte area, which were negatively correlated with the levels of TG, TC, LDL-C, AST, ALT, TNF-α, IL-1β and IL-6. Particularly, DAI-BTN was associated with improving the diversity, structure, and composition of the gut microbiome, promoted the growth of beneficial bacteria (e.g., Proteobacteria and Akkermansia ) and inhibited the proliferation of harmful bacteria (e.g., Desulfovibrio and Flexispira ). Therefore, DAI-BTN hold great promise to be developed as an effective drug combination agent for the alleviation of obesity.
研究领域:
药理学
·
代谢生物学
·
微生物学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）