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daidzein
POLYMER BULLETIN · 2025 · IF 4

Preparation of daidzein-based bio-benzoxazine/novolac thermosetting blends with low curing temperature and high thermal stability

Jing Yichen,Lu Yin,Zhang Kan

It is well-established that the oxazine ring in benzoxazine resin generally exhibits good stability at ambient temperature, but undergoes ring-opening polymerization reactions at relatively higher temperatures. To make benzoxazine resin more practical for application, it is crucial to lower its curing temperature. In this study, novel thermosetting systems were prepared by using bio-based benzoxazine derived from daidzein (Dz-fa) blending with commercialized novolac resin. Novolac resin, which contains rich phenolic hydroxyl groups, was utilized as the curing accelerator for Dz-fa. The curing behavior of the thermosetting blends as well as the properties of the resulting thermosets was systematically investigated. The curing kinetics of the bio-based benzoxazine with novolac resin were monitored using differential scanning calorimetry and in situ FTIR spectroscopy. The thermal properties of the cured resins were assessed by thermogravimetric analysis and dynamic mechanical analysis. The flexural strength of materials is tested by universal material testing machine. These results demonstrated that employing the novolac resin effectively reduced the curing temperature of the bio-based benzoxazine without sacrificing too much in terms of the thermal stability and mechanical property. Specifically, the char yield of cured resin (Yc), the glass transition temperature ( T g ) and flexural strength of Dz-fa and novolac resin blends in the ratio of 9:1 were found to be 65.0%, 314 °C and 84.05 MPa, respectively. This study provides a practical approach to lowering the curing temperature of benzoxazine resins. The thermosets with relatively high thermal stability can be achieved through implementable process, thereby potentially reducing overall costs during the production of benzoxazine-based materials.

CAS / MDL: 30525-89-4 617-89-0
研究领域: 材料科学 · 化学工程
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ONCOLOGY REPORTS · 2015 ·Vol. 34 ·期 3 ·1115-1120 · IF 2.301

Effects of daidzein in regards to cytotoxicity in vitro, apoptosis, reactive oxygen species level, cell cycle arrest and the expression of caspase and Bcl-2 family proteins

Bing-Jie Han,Wei Li,Guang-Bin Jiang,Shang-Hai Lai,Cheng Zhang,Chuan-Chuan Zeng,Yun-Jun Liu

In the present study, the in vitro cytotoxicity of daidzein was evaluated in human BEL-7402, A549, HeLa, HepG-2 and MG-63 cancer cell lines. BEL-7402 cells were sensitive to daidzein treatment, with an IC50 value of 59.7±8.1 µM. Daidzein showed no cytotoxic activity toward A549, HeLa, HepG-2 and MG-63 cells. Daidzein increased the levels of reactive oxygen species (ROS) and induced a decrease in mitochondrial membrane potential. Morphological and comet assays showed that daidzein effectively induced apoptosis in BEL-7402 cells. Additionally, daidzein caused cell cycle arrest at the G2/M phase in the BEL-7402 cell line. Daidzein downregulated the expression of Bcl-2, Bcl-x and Baid proteins and upregulated the levels of Bim protein in the BEL-7402 cells. The results demonstrated that daidzein induced BEL-7402 cell apoptosis through an ROS-mediated mitochondrial dysfunction pathway.

研究领域: 肿瘤学 · 细胞生物学 · 药理学
✓ 已验证 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2020 · IF 6.306

Interaction among protein, daidzein and surfactants in the WPI-based daidzein self-microemulsifying delivery system

Huimin Chen,Fujia Yang,Liang Lv,Caili Fu,Xixi Cai,Shaoyun Wang

The self-microemulsifying delivery system was fabricated by whey protein isolate (WPI), daidzein (Dai) and surfactants, the interaction of WPI, Dai and D-α-Tocopherol polyethylene glycol succinate (TPGS) was hereby studied in the absence or presence of Tween 20. The increase of surfactant concentration led to the decrease of the modulus and changes of protein interfacial conformation, which allowed the formation of a strong intermolecular network. The environment and structure of WPI and daidzein could be changed by TPGS , and the addition of Tween 20 could further enhance the interaction between the components by changing TPGS structure. With the increase of surfactants and oil phase, Ksv and Ka values of WPI-Dai increased first and then decreased. Therefore, the interaction between the components was also dependent on the WPI-surfactant ration. These findings provide a potential strategy for designing microemulsion food system based on the understanding of the interactions among individual composition of microemulsions.

研究领域: 食品科学 · 药学 · 胶体与界面化学
✓ 已验证 DOI PubMed 高影响因子
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FLUID PHASE EQUILIBRIA · 2014 · IF 2.241

Solubility of daidzein in propylene glycol plus water cosolvent mixtures

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.

CAS / MDL: 1344-28-1
研究领域: 药学 · 物理化学
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CHINESE JOURNAL OF POLYMER SCIENCE · 2026 · IF 4.6

Processable Main-chain Benzoxazine Resin Derived from Daidzein with Intrinsic Flame Retardancy

Hu Chao-Fan,Dai Jin-Yue,Liu Jing-Kai,Wang Shuai-Peng,Jia Li,Zhang Hui,Liu Xiao-Qing

The development of intrinsically flame-retardant, low-smoke, low-toxicity, and halogen-free polymers represents a critical challenge. In this study, bio-based daidzein was employed as a partial phenolic source, and a series of main-chain benzoxazine resins (Dz-Ph-ddm) was synthesized via Mannich condensation with phenol, 4,4′-diaminodiphenylmethane, and paraformaldehyde. The effects of daidzein content on the thermal stability, flame retardancy, mechanical properties, and char-forming behavior of cured resins were investigated. The results indicate that the rigid aromatic structure and benzopyranone unit of daidzein significantly promoted the formation of a dense and continuous char layer, achieving gas- and condensed-phase synergistic flame retardancy. With 20 mol% of daidzein addition, the resin exhibited a glass transition temperature ( T g ) of 259.6 °C, the char yield at 800 °C increased by 42.5% compared to the control group, a UL-94 V-0 rating, and a 30.9% reduction in total heat release (THR) in cone calorimetry tests. The glass fiber-reinforced composite prepared using this resin as the matrix showed a 100.6% improvement in impact strength, with flexural and compressive strengths reaching 748.4 and 340.8 MPa, respectively. Moreover, it demonstrated good fire safety performance even in an 80 kPa low-pressure combustion environment. This work provides a facile strategy for the preparation of high-performance eco-friendly flame-retardant composites. The alternative text for this image may have been generated using AI.

✓ 已验证 DOI 高影响因子
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Frontiers in Pharmacology · 2024 · IF 4.4

A new crystalline daidzein-piperazine salt with enhanced solubility, permeability, and bioavailability

Meng Jiacheng,Qiu Chenxu,Lu Chenyue,He Xin,Zhao Xinghua

To overcome the poor solubility, permeability, and bioavailability of the plant isoflavone daidzein (DAI), a novel salt of DAI with anhydrous piperazine (PIP) was obtained based on cocrystallization strategy. The new salt DAI-PIP was characterized by powder X-ray diffraction (PXRD), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), Fourier-transform infrared (FT-IR) spectroscopy, and optical microscopy. The results showed that the maximum apparent solubility (Smax) of DAI-PIP increased by 7.27-fold and 1000-fold compared to DAI in pH 6.8 buffer and water, respectively. The peak apparent permeability coefficient (Papp) of DAI-PIP in the Caco-2 cell model was 30.57 ± 1.08 × 10−6 cm/s, which was 34.08% higher than that of DAI. Additionally, compared to DAI, the maximum plasma concentration (Cmax) value of DAI-PIP in beagle dogs was approximately 4.3 times higher, and the area under the concentration-time curve (AUC0-24) was approximately 2.4 times higher. This study provides a new strategy to enhance the dissolution performance and bioavailability of flavonoid drugs, laying a foundation for expanding their clinical applications.

研究领域: 药学 · 药物递送 · 药理学 · 材料科学
✓ 已验证 DOI PubMed 高影响因子
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MOLECULES · 2017 ·Vol. 22 ·期 12 ·2183 · IF 2.861

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

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

CAS / MDL: 486-66-8
研究领域: 药学 · 化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2024 · IF 3.7

Study on trifluoromethanesulfonic acid-promoted synthesis of daidzein: process optimization and reaction mechanism

Hai Cao,Hai-Bin Yang,Yanxiong Fang,Yuandi Zeng,Xiaolan Cai,Jingjing Ma

Daidzein has been widely used in pharmaceuticals, nutraceuticals, cosmetics, feed additives, etc. Its preparation process and related reaction mechanism need to be further investigated. A cost-effective process for synthesizing daidzein was developed in this work. In this paper, a two-step synthesis of daidzein (Friedel-Craft acylation and [5+1] cyclization) was developed via the employment of trifluoromethanesulfonic acid (TfOH) as an effective promoting reagent. The effect of reaction conditions such as solvent, the amount of TfOH, reaction temperature, and reactant ratio on the conversion rate and the yield of the reaction, respectively, was systematically investigated, and daidzein was obtained in 74.0% isolated yield under optimal conditions. Due to the facilitating effect of TfOH, the Friedel-Craft acylation was completed within 10 min at 90 °C and the [5+1] cyclization was completed within 180 min at 25 °C. In addition, a possible reaction mechanism for this process was proposed. The results of the study may provide useful guidance for industrial production of daidzein on a large scale.

研究领域: 制药 · 营养补充品 · 化妆品 · 饲料添加剂 · 有机化学 · 工艺工程
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INTERNATIONAL IMMUNOPHARMACOLOGY · 2025 · IF 4.7

Targeting TBXAS1: a novel target of daidzein in alleviating APAP-induced hepatic injury

Lei Sun,Ziming Wu,Zhiwei Huang,Han Li,Pengru Wang,Jiatong Chen,Boyuan Gu,Shenglu Liu,Yu Jiang,Xiaolin Zhong,Yichao Du,Wenguang Fu

Background and Purpose Acetaminophen (APAP) overdose is a major cause of acute liver failure. TBXAS1, driving inflammation via processes like inflammatory cell aggregation, vasoconstriction, and thrombosis, was picked out as a crucial inflammatory regulator that catalyzes thromboxane A2 generation. This study was conducted to explore whether Daidzein (DAI), a bioactive compound, has hepatoprotective effects against APAP-induced liver injury by acting on TBXAS1. Methods and Results In vitro and in vivo experiments revealed that hepatic TBXAS1 levels increased following APAP induction. SiRNA-mediated TBXAS1 knockdown reduced APAP-induced inflammation and cytotoxicity. Network pharmacology and transcriptomic analysis identified TBXAS1 as a potential DAI target. In vivo, DAI pretreatment mitigated APAP-induced liver injury in mice and lowered TBXAS1 levels. In vitro, DAI pretreatment followed by APAP exposure in AML-12 cells resulted in reduced TBXAS1 expression and decreased inflammation, oxidative stress, and apoptosis. Mechanistic analysis showed that DAI regulates TBXAS1 expression both in vitro and in vivo. Specifically, DAI modulates the TLR4/NF-κB pathway by altering TXA2 levels mediated by TBXAS1, thereby protecting against APAP-induced injury. Conclusion TBXAS1 is identified as a novel target of DAI. By modulating TBXAS1, DAI can reduce APAP-induced liver damage, including hepatocyte injury, oxidative stress, apoptosis, and inflammation. This study provides a new therapeutic approach for managing APAP-induced liver damage.

CAS / MDL: 103-90-2
✓ 已验证 产品关联 DOI PubMed 高影响因子
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TALANTA · 2017 · IF 4.162

Facile synthesized SnO2 decorated functionalized graphene modified electrode for sensitive determination of daidzein

Yamin Fu,Lu Wang,Yinghao Duan,Lina Zou,Baoxian Ye

A one-step and facile method using SnCl 2 ·H 2 O as reducing agent to reduce graphene oxide (GO) was performed in the aid of poly(diallyldimethylammonium chloride) solution (PDDA). SnCl 2 ·H 2 O is not only a reducing agent for graphene oxide (GO), but also a precursor of SnO 2 . SnO 2 -PDDA-GR composite was characterized by various surface, structural and electrochemical analysis techniques, such as transmission electron microscopy (TEM), UV spectrum (UV–vis), Infrared Spectrum (IR), X-ray diffraction (XRD), Cyclic voltammograms (CV) and electrochemical impedance (EIS). The SnO 2 -PDDA-GR composite was used to constructed electrochemical sensor (SnO 2 -PDDA-GR/GCE) for the determination of daidzein . Under the optimized experimental condition, it was found that the response of peak current is linear to the concentration of daidzein in the ranges of 2.0×10 −8 −1.0×10 −6   mol   L −1 , and the detection limit was estimated to be 6.7×10 −9   mol L −1 (S/N=3). Furthermore, this sensor was successfully applied for the determination of daidzein in traditional Chinese medicine (pueraria lobata) and Daidzein tablets.

CAS / MDL: 486-66-8 26062-79-3
研究领域: 材料科学 · 电化学 · 分析化学 · 药物分析
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Advanced Composites and Hybrid Materials · 2023 ·Vol. 6 ·期 6 ·1-15 · IF 20.1

Magnetic surface molecularly imprinted polymers for efficient selective recognition and targeted separation of daidzein

Wang Biao,Kuang Yi,Li Minghui,Wang Xing,Zhang Xiaotian,Rao Qingqing,Yuan Bingnan,Yang Shengxiang

Daidzein, a naturally occurring source of estrogenic isoflavones, holds significant promise for various applications in food and drug development. Therefore, to realize efficient and precise daidzein separation, we synthesized a magnetic surface molecularly imprinted polymer (Daidzein/SMIPs) via free radical-initiated polymerization via magnetic surface molecular imprinting technology. The adsorption capacity of the Daidzein/SMIPs for daidzein at an initial concentration of 300 µg·mL −1 reached 18.44 mg·g −1 within 20 min at 298 K. Even after nine adsorption-desorption cycles, the adsorption capacity remained high (81.42% of the initial adsorption capacity). Furthermore, the Daidzein/SMIPs exhibited exceptional selectivity for daidzein, with an imprinting factor of 1.83 and selection coefficients ( K ) of 1.94, 2.43, 2.63, and 1.66 for structurally similar competing molecules such as naringin, quercetin, diosmetin, and alizarin, respectively. In practical applications, isolating daidzein from real daidzein tablets using the Daidzein/SMIPs resulted in high recoveries of 88.09 to 98.12% with excellent precision (relative standard deviation of 1.51–1.02%). Therefore, the constructed Daidzein/SMIPs feature immense potential for targeted daidzein isolation applications.

研究领域: 分析化学 · 高分子科学 · 药学 · 食品科学 · 分离技术
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Cell Host & Microbe · 2023 ·Vol. 31 ·期 5 ·766-780 · IF 30.3

Liberation of daidzein by gut microbial β-galactosidase suppresses acetaminophen-induced hepatotoxicity in mice.

Zeng Y,Wu R,Wang F,Li S,Li L,Li Y,Qin P,Wei M,Yang J,Wu J,Chen A,Ke G,Yan Z,Yang H,Chen Z,Wang Z,Xiao W,Jiang Y,Chen X,Zeng Z,Zhao X,Chen P,Gong S

Acetaminophen (APAP) overdose is a leading cause of drug-induced liver injury (DILI). The impact of the gut microbiota and associated metabolites on APAP and liver function remains unclear. We show that APAP disturbance is associated with a distinct gut microbial community, with notable decreases in Lactobacillus vaginalis. Mice receiving L. vaginalis showed resistance to APAP hepatotoxicity due to the liberation of the isoflavone daidzein from the diet by bacterial β-galactosidase. The hepatoprotective effects of L. vaginalis in APAP-exposed germ-free mice were abolished with a β-galactosidase inhibitor. Similarly, β-galactosidase-deficient L. vaginalis produced poorer outcomes in APAP-treated mice than the wild-type strain, but these differences were overcome with daidzein administration. Mechanistically, daidzein prevented ferroptotic death, which was linked to decreased expression of farnesyl diphosphate synthase (Fdps) that activated a key ferroptosis pathway involving AKT-GSK3β-Nrf2. Thus, liberation of daidzein by L. vaginalis β-galactosidase inhibits Fdps-mediated hepatocyte ferroptosis, providing promising therapeutic approaches for DILI.

研究领域: 药理学 · 胃肠病学 · 微生物学 · 毒理学
✓ 已验证 DOI PubMed 高影响因子
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