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naringenin
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2024 · IF 3.8

Nanomaterials Based on Magnetic Surface Molecularly Imprinted Polymers for Specific Recognition of Naringenin

Qingqing Rao,Wenwen Zhang,Xiaodong Ma,Yunlong Zhang,Yuanlian Li,Yi Kuang,Shengxiang Yang

Naringenin (Nar), a dihydroflavone, is widely used in medicine, food industry, and other fields. In this study, naringenin magnetic surface molecularly imprinted polymers (Nar/SMIPs) were prepared by etching nanomagnetic carriers and using computer-aided material design for highly selective adsorption of naringenin. The Nar/SMIPs exhibited a high adsorption capacity of 37.64 mg·g–1 in 30 min. They also showed excellent selectivity for naringenin, with an imprinting factor of 2.48, and the selection coefficients (K) for structurally similar compounds, diosmetin, chrysin, and alizarin, were 3.27, 2.82, and 3.07, respectively. Furthermore, they demonstrated high recoveries (89.47–95.95%) and precisions (relative standard deviation: 1.38–1.90%) in grapefruit peel extract. Thus, Nar/SMIPs hold tremendous potential for the selective extraction of naringenin.

CAS / MDL: 10025-77-1
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POLYMER SCIENCE SERIES A · 2023 ·Vol. 65 ·期 1 ·72-81 · IF 1

Surface Molecularly Imprinted Polymer Based on ZIF-8 for selective Adsorption of Naringenin

Ting Pu,Yang Qin,Xu Nan,Chen Fubin,Zhang Gui,Yang Chunyan

Abstract Naringenin, an herbal ingredient possesses a diversity of pharmacological action and bioactive functions. In this study, surface molecularly imprinted polymers named as Zeolite imidazolate framework-8 were successfully synthesized and applied in the selective adsorption of naringenin. A series of adsorption experiments evaluated the adsorption properties of polymers. The results showed that the molecularly imprinted polymers had a higher adsorption capacity than non-imprinted polymers. In addition, they have good selectivity for Naringenin compared with other flavonoid compounds, and its imprinting factor for naringenin is as high as 3 in single solutions. The Scatchard plots showed two distinct linear portions, indicating that two kinds of binding sites exist in the molecularly imprinted polymers. After eight cycles, the adsorption capacity of polymers did not decrease significantly in the initial affinity. These results demonstrated that prepared molecularly imprinted polymers could be promising functional materials for the selective adsorption of naringenin.

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Current Drug Delivery · 2023 ·Vol. 21 ·期 8 ·1142-1150 · IF 2.4

Chitosan Oligosaccharide Modified Bovine Serum Albumin Nanoparticles for Improving Oral Bioavailability of Naringenin

Fang Ruiyue,Liao Yiqi,Qiu Huishuang,Liu Yuxin,Lin Shiyuan,Chen Hui

Introduction: With the rapid development of nanotechnology, the research and development of nano-drugs have become one of the development directions of drug innovation. The encapsulation of the nanoparticles can change the biological distribution of the drug in vivo and improve the bioavailability of the drug in vivo. Naringenin is poorly soluble in water and has a low bioavailability, thus limiting its clinical application. The main purpose of this study was to develop a nano-sized preparation that could improve the oral bioavailability of naringenin. Methods: Chitosan oligosaccharide modified naringenin-loaded bovine serum albumin nanoparticles (BSA-COS@Nar NPs) were prepared by emulsification solvent evaporation and electrostatic interaction. The nanoparticles were characterized by HPLC, laser particle size analyzer, transmission electron microscope and X-ray diffraction analysis. The release in vitro was investigated, and the behavior of nanoparticles in rats was also studied. The caco-2 cell model was established in vitro to investigate the cytotoxicity and cellular uptake of nanoparticles. Results: BSA-COS@Nar NPs were successfully prepared, and the first-order release model was confirmed in vitro release. In vivo pharmacokinetic results indicated that the area under the drug concentration- time curve (AUC) of BSA-COS@Nar NPs was 2.37 times more than free naringenin. Cytotoxicity and cellular uptake results showed that BSA-COS@Nar NPs had no significant cytotoxic effect on Caco- 2 cells and promoted cellular uptake of the drug. Conclusion: BSA-COS@Nar NPs could improve the in vivo bioavailability of naringenin.

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iScience · 2025 · IF 4.1

Synergistic Immunomodulatory Effects of Naringenin and Photothermal Therapy in Triple-Negative Breast Cancer

Chunyu Lei,Yu Yao,Qian Xie,Na Li,Chenghao Zhu,Haomiao Lan,Sisi Yang,Gang Wang,Xianfeng Peng,Duwen Zheng,Haili Wang,Ke Zhu,Ziyang Zhu,Fuqiang Shao

Triple-negative breast cancer (TNBC) represents a highly aggressive subtype with limited treatment options, primarily relying on chemotherapy. Emerging therapies, including photothermal therapy (PTT) and related combination therapies, are considered highly promising. Naringenin is a flavonoid glycoside with diverse biological activities can enhance immune responses as well as inhibit cancer cell proliferation. We developed photothermal bovine serum albumin (BSA)-biomineralized MnO 2 nanoparticles (MnO 2 @BSA) by directly reducing KMnO 4 with BSA, which were then combined with naringenin to achieve immuno-enhanced PTT for TNBC. The results show that MnO 2 @BSA exhibits strong light absorption and tumor-targeting capabilities. Naringenin and PTT together significantly suppress TNBC cell proliferation and migration while enhancing antitumor immune responses. In vivo experiments confirm that the combined therapy reduces tumor growth and metastatic risk compared to monotherapy. Additionally, the treatment exhibits a favorable safety profile, offering potential for improved clinical outcomes in breast cancer treatment.

CAS / MDL: 7722-64-7
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CRYSTAL GROWTH & DESIGN · 2024 · IF 3.2

Cocrystal of Naringenin and Norfloxacin: Crystal Transformation, Solubility, and Antibacterial and Anticancer Activities

Xin Zeng,Chupei Zheng,Shouliang Qiu,Xin Jiang,Xiaoye Wang,Kun Qian,Rongbin Pan,Jie Yang,Yuexing Ma

Drug cocrystals can modulate the physical and chemical properties of drugs, even complement each other’s strengths, and have a synergistic enhancement effect. Here, we reported a drug cocrystal prepared by norfloxacin (NOR) and naringenin (NAR), comprising an antibacterial drug and an antitumor active pharmaceutical ingredient. The cocrystal hydrate obtained by crystal transformation methods enhanced the antibacterial activity of NOR against one Gram-positive bacterium (Staphylococcus aureus), three Gram-negative bacteria (Escherichia coli, Dysentery bacillus, Pseudomonas aeruginosa), and one fungus (Candida albicans), improved the solubility of NAR, reduced the hygroscopicity of NOR, and enhanced the anticancer activity of NAR against human breast cancer cells MDA-MB-231. This combination has potential therapeutic synergy in clinical terms.

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Integrative Biology · 2017 ·Vol. 9 ·期 10 ·820-829 · IF 3.252

Membrane and genomic DNA dual-targeting of citrus flavonoid naringenin against Staphylococcus aureus

Wang Lang-Hong,Wang Man-Sheng,Zeng Xin-An,Xu Xi-Ming,Brennan Charles S.

The antimicrobial mechanism of naringenin, one of the citrus antibacterial flavonoids against food-borne Staphylococcus aureus ATCC 6538, was investigated in this study. Analysis of gas chromatography-mass spectrometry (GC-MS) and fluorescence showed that relatively low concentrations of naringenin caused perturbations in the membrane fatty acid composition and the conformation of membrane proteins through changing the microenvironment of phenylalanine, tyrosine, and tryptophan residues. Exposure of naringenin at higher levels significantly increased membrane permeability and changed the morphology of S. aureus cells. The genomic DNA-binding of naringenin was also quantitatively monitored using UV-vis spectra in combination with multivariate curve resolution-alternating least squares (MCR-ALS) analysis, and the concentration and pure spectra profiles for the three reaction species (DNA, naringenin, and DNA–naringenin) were obtained. Moreover, the thermal behavior of DNA and docking studies revealed that naringenin preferentially bound to the A–T base pair regions of genomic DNA via groove binding, and atomic force microscopy and circular dichroism showed that naringenin induced mild secondary structure and obvious morphological variations of this biomacromolecule. These results suggested that naringenin exerting its antibacterial effects might be connected with disruption of the cytoplasmic membrane and DNA targeting effects in Staphylococcus aureus.

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CHEMICAL PAPERS · 2026 · IF 2.7

Preparation and characterization of naringenin/methyl-beta-cyclodextrin inclusion complex nanofibers for drug delivery

Feng Shimiao,Chai Hongliang,Zhang Zhe,Zhang Yu,Li Fengrui,Liu Yanyan,Gao Shuang

Naringenin (NAR), a natural flavonoid, possesses potent antibacterial and antioxidant properties. However, its therapeutic potential is severely limited by poor water solubility. Therefore, there is an urgent need to explore efficient drug delivery formulations to improve the physicochemical properties of NAR. In the present work, NAR was successfully encapsulated into methyl- β -cyclodextrin (M β CD) to form inclusion complex, which were further processed into nanofibers (NAR/M β CD-IC-NF) via electrospinning technology. SEM results indicated that the nanofibers were uniform and bead-free, with the NAR/M β CD-IC-NF displaying a remarkably large surface area per unit mass together with a highly developed porous framework. Multiple complementary characterization techniques including Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), proton nuclear magnetic resonance ( 1 H NMR), carbon nuclear magnetic resonance ( 13 C NMR), and X-ray diffraction (XRD) were adopted to verify the successful formation of NAR/M β CD inclusion complex within nanofibers. Molecular docking simulation was further performed to illuminate the host–guest interaction and binding conformation between NAR and M β CD at the molecular level. Additionally, there was a marked increase in the water solubility of NAR, with NAR/M β CD-IC-NF capable of complete dissolution in water within 3 s. Free radical scavenging and antibacterial assays confirmed that NAR/M β CD-IC-NF significantly enhanced the biological activity of NAR. In summary, NAR/M β CD-IC-NF served as an effective carrier system to significantly improve the solubility of NAR, thereby expanding its application prospects and bioavailability in biopharmaceuticals. Graphical abstract

CAS / MDL: 67604-48-2
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JOURNAL OF NUTRITIONAL BIOCHEMISTRY · 2026 · IF 5.2

Naringenin ameliorate heat stress induced hearts injury by regulating ferroptosis and ferritinophagy in chicken

Jiahao Fang,Zhenpeng Jiang,Jingyan Luo,Shuli Wang,Xiaoquan Guo,Ping Liu,Zhanhong Zheng,Gaofeng Cai,Xiaona Gao

Intensive farming and global warming exacerbate the impact of heat stress on the broiler industry, often causing significant heart damage to poultry and thus reducing production performance. Naringenin has garnered significant attention due to its potent antioxidant properties and cardioprotective characteristics. This article aims to explore the role of ferroptosis and ferritinophagy in heat stress-induced heart injury and evaluate the preventive effect of naringenin. The chickens were randomly allocated to four groups for the experiment. The experimental results indicate that heat stress can disrupt the homeostasis of heart antioxidant function and lead to the accumulation of free radicals in chickens. The accumulated reactive oxygen species result in heart damage. Moreover, heat stress upregulates the gene transcription and protein expression levels of ferroptosis-related indicators (GPX4, NRF2, ACSL4, TFR1) and ferritinophagy-related indicators (NCOA4, FTH1, P62, LC3B, BECN1). Meanwhile, naringenin intervention can effectively enhance heart antioxidant function and inhibit ferroptosis and ferritinophagy. It significantly reduces heat stress levels and alleviates heat-stress-induced damage to chicken hearts. Thus, it offers a new way to explore the prevention of heat stress in chickens.

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FOOD HYDROCOLLOIDS · 2023 · IF 10.7

pH-shifted quinoa protein isolate-based nanocarriers for naringenin: Structure characterization and stability evaluation

Ying-Ying Chen,Qiang-Ming Li,Li-Hua Pan,Jian-Ping Luo,Xue-Ying Li,Xue-Qiang Zha

Naringenin (Nar) is an important natural flavonoid compound with multiple health functions, but stability issues and poor solubility greatly limit its bioavailability. To enhance the water-solubility, chemical stability and bioavailability of Nar, quinoa protein isolate (QPI)-Nar and pH-shifted QPI (PQPI)-Nar nanoparticles were constructed in this study. The results of ultraviolet–visible and fluorescence spectra showed there existed the interactions between QPI or PQPI and Nar, with stronger interaction between PQPI and Nar. Thermodynamic analysis indicated the molecular interactions between QPI or PQPI and Nar were mainly driven by hydrogen bonds. Circular dichroism (CD) and surface hydrophobicity results revealed that the binding of Nar changed the secondary structures and reduced surface hydrophobicity of QPI and PQPI. The measured DLS, LC and EE results suggested that PQPI-Nar nanoparticles formed a more stable system with higher encapsulation capacity. Additionally, PQPI-Nar nanoparticles exhibited higher antioxidant activity , superior slow-release property and biocompatibility, as well as better thermal and ultraviolet stability than QPI-Nar nanoparticles. These results indicated that PQPI-Nar nanoparticles could effectively improve the bioavailability of Nar. This study may provide a theoretical basis for the promising application of PQPI-Nar nanoparticle delivery systems in the food industry.

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FOOD HYDROCOLLOIDS · 2023 · IF 10.7

Obtention, interaction, and characterization of the soy protein isolate-glycyrrhizin nanocomplex for encapsulating naringenin

Qingchen Cui,Xixi Song,Mengshuang Li,Yanjun Wei,Juan Dong,Xianggen Wu

Naringenin (NAR) has several potential benefits as a bioactive nutrient, but its low water solubility and poor bioavailability have limited its application. Here, a soy protein isolate-naringenin complex (NAR@SPI) was prepared for NAR delivery. Furthermore, to improve the encapsulation capacity of SPI for hydrophobic bioactive nutrients and their complex physiochemical properties, dipotassium glycyrrhizinate (DG) was used to modify SPI with a simple stirring process to obtain the SPI-DG complex, and then this complex was used to load the NAR. The final obtained nanocomplex was named NAR@SPI-DG. This novel NAR@SPI-DG has shown higher encapsulation efficiency (93.20 ± 0.27% versus 62.09 ± 3.20%) and loading capacity (8.53 ± 0.02% versus 5.89 ± 0.30%) for NAR as compared to the NAR@SPI. Spectral evaluations and molecular simulations revealed that the SPI's and DG's interaction in SPI-DG involved the combination of a spontaneous exothermic reaction, and the mechanisms of interaction were dominated by a hydrogen bond and van der Waals forces. NAR@SPI-DG has demonstrated significant improvements in solubility, in vitro antioxidant activity, in vitro anti-diabetes activity, and in vitro bioaccessibility as compared with bare NAR and NAR@SPI. Consequently, the use of DG is promising in the modification of SPI protein to construct a nano-delivery system for hydrophobic bioactive nutrients, such as NAR, in functional foods.

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eFood · 2025 ·Vol. 6 ·期 1 ·e70032 · IF 5.7

Bioactive Evaluation of Naringenin in Ameliorating Hyperuricemia-Induced Liver Injury by Inhibiting Xanthine Oxidase

Xiaoyue Zhang,Linfeng Liu,Zhaosen Fan,Nilufar Mamadalieva,Chao Liu,Xu Guo,Shutao Sun,Hui Sun,Ningyang Li,Muxuan Wang

Hyperuricemia (HUA) is one of main risk factors for liver injury, and xanthine oxidase (XOD) is an important target for HUA-induced liver injury. As a typical natural active ingredient, naringenin (NAR) has been confirmed the good therapeutic effect on variety of diseases. However, studies of NAR ameliorating HUA-induced liver injury have not been reported. Therefore, we evaluated the bioactivity of NAR in ameliorating HUA-induced liver injury and investigated the related molecular mechanisms. The inhibitory activity and type of NAR on XOD was investigated by enzymatic reactions and kinetic analyses, and molecular docking showed that NAR was able to bind tightly to XOD. In vivo activity studies showed that NAR ameliorated liver function while being able to inhibit XOD activity. NAR alleviated oxidative stress in the liver caused by excess reactive oxygen species through antioxidant activity. At the same time, NAR exerted anti-inflammatory activity by regulating the levels of inflammatory factors. The molecular docking results suggested that NAR was able to interact with Keap1 and AMPK to exhibit antioxidant and anti-inflammatory effects. This work demonstrated the therapeutic effect of NAR on HUA-induced liver injury, which was valuable for the further development of related functional foods.

CAS / MDL: 315-30-0 67604-48-2
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Antioxidants · 2025 ·Vol. 14 ·期 8 ·914 · IF 6.6

Naringenin Inhibits Enterotoxigenic Escherichia coli-Induced Ferroptosis via Targeting HSP90 in IPEC-J2 Cells

Pengxin Jiang,Kangping Liu,Yanan Cui,Puyu Liu,Xutao Wang,Zijuan Hou,Jiamei Cui,Ning Chen,Jinghui Fan,Jianguo Li,Yuzhu Zuo,Yan Li

EnterotoxigenicEscherichia coli(ETEC) leads to severe diarrhea in piglets. Naringenin (Nar), a natural flavonoid compound, is known for its antibacterial and anti-antioxidant properties. However, the protective effects of Nar against ETEC-induced diarrhea have not been reported yet. This study investigated the protective mechanisms of Nar against ETEC infection in porcine intestinal epithelial cells (IPEC-J2). ETEC infection induced oxidative stress and ferroptosis in IPEC-J2 cells by elevating intracellular iron content and ROS accumulation, increasing MDA levels, downregulating SOD activity and GPX4 expression, and upregulating the transcription of CHAC1 and SLC7A11. In contrast, Nar suppressed ETEC-induced ferroptosis of IPEC-J2 cells by inhibiting the SLC7A11/GPX4 pathway. Specifically, Nar mitigated mitochondrial damage, reduced intracellular iron levels and ROS accumulation, and ultimately reversed the oxidative stress. Network pharmacology and molecular docking identified heat-shock protein 90 (HSP90) as a potential target of Nar. Overexpression and knockdown experiments revealed that ETEC-induced ferroptosis was mediated by upregulation of HSP90, while the protective effects of Nar against ETEC-induced ferroptosis were dependent on the downregulation of HSP90. In conclusion, Nar targets host HSP90 to protect IPEC-J2 cells from ferroptosis caused by ETEC infection. This study demonstrates that Nar is a potent antioxidant natural compound with potential for preventing ETEC-induced intestinal damage.

CAS / MDL: 67604-48-2
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