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Magnolol
POLYMER · 2021 · IF 4.43

Natural magnolol derivatives as platform chemicals for bio-based phthalonitrile thermoset: Achieving high performances without an external curing agent

Zhihuan Weng,Lequn Song,Yu Qi,Jiahui Li,Qi Cao,Cheng Liu,Shouhai Zhang,Jinyan Wang,Xigao Jian

Bio-based polymers with better comprehensive properties, showing more competitiveness than their petroleum-based counterparts in high-tech fields is an increasingly trend but also a formidable challenge. In the study, bio-based phthalonitrile precursors were synthesized from natural occurring magnolol derivatives through a highly efficient one step process. Self-curing reactions can be proceeded with allyl groups in the resultant precursors without sacrificing the thermal stabilities of the thermoset resins. The curing behavior, mechanism and processability of the phthalonitrile precursors were studied, and the thermal stabilities of cured polymers were evaluated. Of the two bio-based precursors, the honokiol derivate exhibited a wide processing window of 163 °C with a melting point lower than 70 °C. After curing, both the magnolol- and honokiol-based resins showed glass transition temperature higher than 500 °C and 5% weight loss temperature as high as 527 °C. These properties were superior to those of the petroleum-based reference without allyl group. A model reaction, showed that the curing mechanism of allyl/phthalonitrile system here was considered to be free radical polymerization . The results demonstrate that sustainable magnolol derivatives can be employed as platform chemicals to impart excellent performances to the bio-based polymers for great promise in cutting-edge applications.

研究领域: 材料科学 · 化学工程 · 有机化学
✓ 已验证 DOI 高影响因子
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IONICS · 2015 ·Vol. 21 ·期 9 ·2567-2574 · IF 1.754

Synthesis of 1-[3-(N-pyrrole)propyl]-3-[1-tert-butoxycarbonylamino-propyl]-imidazolium tetrafluoroborate ionic liquid for application in electrochemical sensing of magnolol

Liu Guishen,Ma Yanhui,Hou Xiaodong,huang Yina,Chen Jianpeng,Zhan Guoqing,Li Chunya

1-[3-(N-Pyrrole)propyl]-3-[1-tert-butoxy-carbonylamino-propyl]imidazolium tetrafluoroborate ionic liquid was successfully synthesized and characterized. The ionic liquid was electrochemically polymerized onto a glassy carbon electrode surface using a multi-potential step technique. Morphology and electrochemical properties of the polymerized ionic liquid film electrode were studied with scanning electronic microscopy and electrochemical impedance spectroscopy. Using the polymerized ionic liquid film as a sensing platform, electrochemical behaviors of magnolol were investigated by voltammetry. Under optimal experimental conditions, the oxidation peak currents were linearly related to magnolol concentrations in the range from 5.0 × 10 −8 to 1.0 × 10 −5  mol L −1 . The detection limit calculated from the standard deviation of the intercept was 2.3 × 10 −7  mol L −1 . Practical application of the polymerized ionic liquid film electrode was demonstrated by determining magnolol in the traditional Chinese medicine. The result is consistent with that obtained using high performance liquid chromatography. Polymerized ionic liquid film electrode fabricated with potential step technique and application in voltammetric sensing of magnolol

研究领域: 分析化学 · 电化学
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JOURNAL OF CHROMATOGRAPHY A · 2020 · IF 4.049

Preparation of restricted access monolithic tip via unidirectional freezing and atom transfer radical polymerization for directly extracting magnolol and honokiol from rat plasma followed by liquid chromatography analysis

Jingwei Zhou,Yaoyao Hu,Peichun Chen,Hongwu Zhang

In the present study, a novel strategy based on unidirectional freezing and atom transfer radical polymerization combined with activator regenerated by electron transfer (ARGET-ATRP) was applied to synthesizing orderly macroporous monolithic column with restricted-access (RA) property in a 1000μL pipette tip. The RA column was composed of hydrophobic inner column (poly(styrene- co -ethylene glycol dimethacrylate) and hydrophilic outer layer (poly-hydroxyethyl methacrylate chain) which was grafted on the hydrophobic surface by means of the second ARGET-ATRP reaction. The as-prepared RA monolithic tip was connected to a 2mL syringe for directly extracting magnolol and honokiol from rat plasma just by manually pushing operation. The surface morphology and chemical composition of the column were characterized by scanning electronic microscope, infrared spectroscopy and X-ray photoelectron spectroscopy respectively. The determined results of evaluation experiments based on the optimized solid phase extraction conditions showed that the RA column possessed good protein exclusion power, extraction recovery and reusability. The constructed RA-SPE-HPLC/UV method for simultaneously analyzing magnolol and honokiol in rat plasma was validated with quality control (QC) samples at four concentration levels. Good precision (RSDs, 3.39~11.16%) and acceptable accuracy (relative recoveries, 89.52%~108.42%) were obtained for intra- and inter-day assays. The determined results of real rat plasma as well as the standard-addition samples demonstrated the developed method with good accuracy and precision. It can be extrapolated from the experimental results that this simple and cost-efficient RA-SPE method is also suitable for directly extracting other hydrophobic constituents in biological body fluid for therapeutic drug monitoring or pharmacokinetic study.

研究领域: 分析化学 · 药物分析 · 生物医学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CARBOHYDRATE POLYMERS · 2022 · IF 10.723

pH-responsive magnolol nanocapsule-embedded magnolol-grafted-chitosan hydrochloride hydrogels for promoting wound healing

Meng Wang,Huihua Huang,Chaokang Huang,Shujun Liu,Xiaohong Peng

Bacterial infection and oxidative stress seriously delay wound healing. Here, magnolol-grafted-chitosan hydrochloride (CSCl-MAG) was synthesized and crosslinked with genipin to form hydrogel (CSM H). By embedding magnolol-loaded chitosan nanocapsules (MCNGs) into CSM H, we designed a novel nanocapsule- embedded hydrogel dressing (MCNG-H) with sustained antibacterial and antioxidant properties. The swelling, rheology , cytotoxicity, antibacterial and antioxidant properties of MCNG-H were studied. MCNG-H exhibited good swelling properties and biocompatibility. The antibacterial and antioxidant assays in vitro demonstrated the corporative effect of CSM-H and MCNGs in inhibiting bacteria and eliminating reactive oxygen species (ROS). Moreover, MCNG-H revealed the pH-responsive release profiles of loaded MAG, and ensured sustained release of MAG with the dual protective effects of MCNG and CSM H, which helped to maintain long-term antibacterial and antioxidant activities. Finally, MCNG-H significantly accelerated wound healing in a splinted excisional dermal wound model, promising a competitive dressing for the treatment of infected wounds.

CAS / MDL: 6902-77-8 1338-43-8
研究领域: 生物材料学 · 药剂学 · 医学
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POLYMER · 2023 · IF 4.6

Enhancing the comprehensive performance of bisphenol A epoxy resin via blending with a bio-based counterpart

Hongwei Gu,Qi Cao,Jiahui Li,Jing Zhao,Shouhai Zhang,Xigao Jian,Zhihuan Weng

Modification of epoxy resins has emerged as a growing trend but also presents significant challenges, as it is difficult to trade off various properties, for example, improving the toughness of the resin often sacrifices its thermal stability and flame retardancy. In this study, a bio-based tetra-functional epoxy precursor (MTEP) derived from magnolol was blended to comprehensively improve the performances of the commonly used petroleum-based bisphenol A epoxy precursor (E51) with 4,4′-diaminodiphenyl sulfone (DDS) as curing agent , and the thermal stability, mechanical properties and flame retardancy of the blended systems were evaluated. The results showed that the MTEP/E51/DDS blend resin exhibited maximum impact strength (37.8 MPa), representing a 54.3% improvement over E51/DDS (24.5 MPa). The addition of 50 wt% of MTEP into E51/DDS increased the flexural modulus up to 3281 MPa (by ∼23.6%), in combination with appreciable increases in the glass transition temperature (by 50 °C) and intrinsically flame retardancy in UL-94 test (from NR to V-0). The above results prove that it is feasible to improve the performances of petroleum-based epoxy resin with high-performance bio-based counterpart, which is often the opposite before, which also provides a novel approach for the modification of epoxy resin.

研究领域: 材料科学 · 化学工程
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COMPOSITES PART B-ENGINEERING · 2021 · IF 9.078

Facile synthesis of bio-based tetra-functional epoxy resin and its potential application as high-performance composite resin matrix

Yu Qi,Zhihuan Weng,Yan Kou,Jiahui Li,Qi Cao,Jinyan Wang,Shouhai Zhang,Xigao Jian

In order to meet the increasing performance demands for resin matrix in aerospace industry and fulfill the sustainable development strategy, designment of bio-based epoxy resins with satisfactory comprehensive properties outperforming N,N,N′,N′-tetraglycidyl-4,4′-diaminodipehnylmethane (TGDDM) for high-end application is of paramount important but also a formidable challenge. Herein, a simple and high-efficient method was proposed to synthesize a bio-based tetra-functional epoxy resin (MTEP) from a sustainable biomass feedstock , magnolol. With 4,4′-diaminodiphenyl sulfone (DDS) as curing agent , the cured MTEP/DDS showed a record glass transition temperature of 326 °C and an ultrahigh char yield of 52.1%, which was 83 °C and 1.1 times higher than those of TGDDM/DDS, respectively. In addition, the cured MTEP/DDS also exhibited a high flexural modulus of 3991 MPa and storage modulus (at 25 °C) of 3705 MPa, which were all superior to those of TGDDM/DDS. More impressively, thanks to the unique structure of magnolol, the cured MTEP/DDS illustrated lower water absorption in comparison with TGDDM/DDS, and possessed outstanding intrinsic flame retardancy , attaining V-0 rating in UL-94 test. This work adds new members to the synthetic toolbox of high-performance bio-based polymers as composite resin matrix for potential aerospace applications .

CAS / MDL: 937-14-4 106-89-8
研究领域: 材料科学 · 化学工程 · 航空航天工程
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Biomaterials Science · 2024 · IF 5.8

Ultrasmall Magnolol/Ebselen Nanomicelles for Preventing Renal Ischemia/Reperfusion Injury

Chang Liu,Linhua Li,Li Li,Qingyin Li,Jing Liu,Chunle Zhang,Zhengjiang Cao,Liang Ma,Xiaoxi Zeng,Ping Fu

Renal ischemia/reperfusion injury (RIRI) is an inevitable complication following kidney transplantation surgery, accompanied by the generation of massive of free radicals. The cascade of events including oxidative stress, extreme inflammation, cellular apoptosis, thrombosis disrupts the microenvironment of renal cells and the hematological system, ultimately leading to the development of acute kidney injury/ failure. Current research primarily focuses on reducing inflammation and mitigating damage to renal cells through antioxidative approaches. However, studies on simultaneously modulating the renal hematologic system remain unreported. Herein, a potent and novel drug-loaded nanomicelles can be efficiently self-assembled with magnolol (MG) and ebselen (EBS) by the π-π conjugation, hydrophobic action and the surfactant properties of Tween-80. The ultrasmall MG/EBS nanomicelles (Average particle size: 10–25 nm) not only fully preserve the activity of both drugs but also greatly enhance drug utilization (encapsulation rates: MG-90.1%, EBS-49.3%) and reduce drug toxicity. Furthermore, EBS, as a glutathione peroxidase mimic and NO catalyst, synergistically collaborates with the multifunctional MG to scavenge free radicals, significantly inhibiting inflammation and thrombosis while effectively preventing apoptosis of vascular endothelial cells and renal tubular epithelial cells. This study provides a new strategy and theoretical foundation for the simultaneous regulation of kidney cells and blood microenvironment stability.

CAS / MDL: 9005-65-6 60940-34-3
研究领域: 药理学 · 肾脏病学 · 纳米医学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Scientific Reports · 2015 · IF 5.578

Inhibitory effects of magnolol and honokiol on human calcitonin aggregation.

Caiao Guo,Liang Ma,Yudan Zhao,Anlin Peng,Biao Cheng,Qiaoqiao Zhou,Ling Zheng,Kun Huang

Amyloid formation is associated with multiple amyloidosis diseases. Human calcitonin (hCT) is a typical amyloidogenic peptide, its aggregation is associated with medullary carcinoma of the thyroid (MTC), and also limits its clinical application. Magnolia officinalis is a traditional Chinese herbal medicine; its two major polyphenol components, magnolol (Mag) and honokiol (Hon), have displayed multiple functions. Polyphenols like flavonoids and their derivatives have been extensively studied as amyloid inhibitors. However, the anti-amyloidogenic property of a biphenyl backbone containing polyphenols such as Mag and Hon has not been reported. In this study, these two compounds were tested for their effects on hCT aggregation. We found that Mag and Hon both inhibited the amyloid formation of hCT, whereas Mag showed a stronger inhibitory effect; moreover, they both dose-dependently disassembled preformed hCT aggregates. Further immuno-dot blot and dynamic light scattering studies suggested Mag and Hon suppressed the aggregation of hCT both at the oligomerization and the fibrillation stages, while MTT-based and dye-leakage assays demonstrated that Mag and Hon effectively reduced cytotoxicity caused by hCT aggregates. Furthermore, isothermal titration calorimetry indicated Mag and Hon both interact with hCT. Together, our study suggested a potential anti-amyloidogenic property of these two compounds and their structure related derivatives.

CAS / MDL: 7487-88-9 989-51-5
研究领域: 药理学 · 生物化学 · 分子生物学 · 中医药
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HIGH PERFORMANCE POLYMERS · 2024 · IF 1.8

Modification of bisphenol A type epoxy resin by biobased magnolol epoxy

Ming Yuan Wang,Shou Wu Yu,Chen Jing Zhao,Tian Yu Zhang,Gui Xiang Hou

Reducing the dependence of epoxy resin preparation on petroleum resources and developing thermosetting epoxy resins with excellent comprehensive performance are important directions for the current development of epoxy resins. This article uses biomass resource magnolol as the main raw material to prepare magnolol epoxy monomer (DGEM). Then, using 4,4-diaminodiphenylmethane (DDM) as the curing agent, the DGEM and bisphenol A epoxy resin (E44) were blended and cured. The results showed a dual modification effect of DGEM on the toughening and strengthening of E44 epoxy resin. When the mass ratio of DGEM to E44 is 30:70, the bending strength of the cured blended resin is 18.7% higher than that of the E44 system, and the tensile strength is 57.7% higher. When the mass ratio of DGEM to E44 is 5:95, the cured blended resin exhibits the optimal impact strength (5.10 kJ/mol), which is 22.9% higher than the pure E44 system. However, the addition of DGEM reduced the glass transition temperature and crosslinking degree of the blended resin system. The addition of DGEM improves the heat resistance and flame retardancy of the blended resin. When the mass ratio of DGEM: E44 was 50:50, the vertical combustion reached UL-94 V-0 level.

研究领域: 材料科学 · 生物质资源利用
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INTERNATIONAL JOURNAL OF PHARMACEUTICS · 2024 · IF 5.3

Pulmonary delivery of magnolol-loaded nanostructured lipid carriers for COPD treatment

Bei Jia,Jiachen He,Ying Zhang,Wenli Dang,Bin Xing,Mengru Yang,Haonan Xie,Jiawei Li,Zhidong Liu

Chronic obstructive pulmonary disease (COPD) is a prevalent lung condition characterized by airflow obstruction, disability, and high mortality rates. Magnolol (MA), known for its anti-inflammatory and antioxidant properties, holds the potential for alleviating COPD symptoms. However, MA faces challenges like poor aqueous solubility and low bioavailability. Herein MA-loaded nanostructured lipid carriers (MA-NLC) were prepared using emulsification and solvent evaporation. These carriers exhibited a particle size of (19.67 ± 0.36) nm, a polydispersity index of (0.21 ± 0.01), and a zeta potential of (−5.18 ± 0.69) mV. The fine particle fraction of MA-NLC was (68.90 ± 0.07)%, indicating minimal lung irritation and enhanced safety. Pulmonary delivery of MA-NLC via nebulizer actively targeted the diseased lung tissues, facilitated slow release, and overcame the challenges of low oral absorption and bioavailability associated with MA. This formulation prolonged the residence time of MA and optimized its therapeutic effect in pulmonary tissues. Upon pulmonary administration, MA-NLC effectively regulated inflammatory and oxidative stress markers in COPD models, demonstrating its potential as a promising therapeutic platform for COPD management.

研究领域: 药学 · 肺科学 · 纳米技术 · 药物递送系统
✓ 已验证 DOI PubMed 高影响因子
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Viruses-Basel · 2022 ·Vol. 14 ·期 7 ·1421 · IF 5.818

Synthesized Magnolol Derivatives Improve Anti-Micropterus salmoides Rhabdovirus (MSRV) Activity In Vivo

Yingjie Jin,Fei Yang,Gengrong Zhang,Qing Yu,Gaoxue Wang,Fei Ling,Tianqiang Liu

Micropterus salmoidesrhabdovirus (MSRV) is a primary viral pathogen in largemouth bass aquaculture, which leads to tremendous economic losses yearly. Currently, there are no approved drugs for the treatment and control of this virus. Our previous studies screened the herbMagnolia officinalisfrom many traditional Chinese medicines, and we isolated and identified magnolol as its main active compound against multiple rhabdoviruses, including MSRV. On the basis of the structure–activity relationship and pharmacophore model of magnolol, two new magnolol derivatives, namely, hydrogenated magnolol and 2,2′-dimethoxy-magnolol, were designed and synthesized. Their anti-MSRV activities were systematically investigated both in vitro and in vivo. By comparing the half-maximal inhibitory concentration (IC50), it was found that hydrogenated magnolol possessed a higher anti-MSRV activity than magnolol and 2,2′-dimethoxy-magnolol, with an IC50of 13.37 μM. Furthermore, hydrogenated magnolol exhibited a protective effect on the grass carp ovary (GCO) cell line by reducing the cytopathic effect induced by MSRV. Further studies revealed that hydrogenated magnolol did not directly impact virions or interfere with MSRV adsorption. It worked within the 6–8 h of the phase of virus replication. In vivo treatment of MSRV infection with magnolol and hydrogenated magnolol showed that they significantly improved the survival rate by 44.6% and 62.7%, respectively, compared to MSRV-infected groups. The viral load measured by the expression of viral glycoprotein in the organs including the liver, spleen, and kidney also significantly decreased when fish were intraperitoneally injected at a dose of 20 mg/kg. Altogether, the structural optimization of magnolol via hydrogenation of the propylene groups increased its anti-MSRV activity both in vitro and in vivo. These results may provide a valuable reference for anti-MSRV drug discovery and development in aquaculture.Keywords:Micropterus salmoidesrhabdovirus (MSRV);magnolol;largemouth bass;antiviral activity

研究领域: 水产养殖学 · 病毒学 · 药物化学
✓ 已验证 DOI PubMed 高影响因子
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ACS Applied Materials & Interfaces · 2026 · IF 8.2

Injectable Hydrogel Loaded with Magnolol and Nanohydroxyapatite for Treating Periodontitis in Diabetes

Sihui Li,Xiaofeng Ren,Yifan Pu,Aodi Li,Xiangrui Liu,Yuwen Huang,Ling Guo

Under the influence of diabetes, patients with periodontitis are not only prone to refractory infections, local oxygenation imbalances, and persistent inflammatory reactions in the periodontal tissues but also often suffer from insufficient neo-alveolar bone formation and secondary bone resorption, which makes the treatment of periodontitis with diabetes a major clinical challenge. In this study, a CMOC hydrogel was synthesized via the Schiff base reaction between carboxymethyl chitosan (CMCS) and oxidized carboxymethyl cellulose (OCMC), and subsequently, Magnolol nanoparticles (MAG-NCs) and nanohydroxyapatite (nHA) were encapsulated in it to construct the MAG/nHA/CMOC injectable hydrogel. The hydrogel exhibits good injectable and self-healing properties, which enable it to adapt to irregular alveolar bone absorption in deep periodontal pockets, and the MAG carried in it could achieve a continuous release of 95.51% within 72 h. In vitro experiments showed that the MAG/nHA/CMOC hydrogel has great antibacterial effects on Porphyromonas gingivalis (P. gingivalis), the key periodontal pathogenic bacteria, and it could effectively scavenge reactive oxygen species (ROS), inhibit the expression of M1-type macrophage markers and upregulate the expression of M2-type markers, and promote the differentiation of human periodontal membrane stem cells (hPDLSCs) into osteoblasts. In addition, the MAG/nHA/CMOC hydrogel still demonstrated outstanding anti-inflammatory and bone-promoting effects in the rat model of diabetic periodontitis, remarkably promoting periodontal repair and regeneration in diabetic periodontitis. In summary, the MAG/nHA/CMOC injectable hydrogel developed by this research provides a new personalized strategy for the treatment of diabetic periodontitis by combining the control of infection and inflammation, scavenging excessive ROS, and promoting periodontal tissue repair.

CAS / MDL: 5470-11-1
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