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ACS Applied Materials & Interfaces · 2024 · IF 8.3

Changing Cinnamaldehyde Skeleton Achieves Antibacterial Nanoswitch

Xiaoying Zhao,Ruoyan Miao,Tianze Xu,Xiaolong Du,Xueyan Zhang,Wanyu Zhao,Huidong Xie,Liang Zhang,Jianzheng He,Zhenhui Ma,Hu Liu

Changeable substituent groups of organic molecules can provide an opportunity to clarify the antibacterial mechanism of organic molecules by tuning the electron cloud density of their skeleton. However, understanding the antibacterial mechanism of organic molecules is challenging. Herein, we reported a molecular view strategy for clarifying the antibacterial switch mechanism by tuning electron cloud density of cinnamaldehyde molecule skeleton. The cinnamaldehyde and its derivatives were self-assembled into nanosheets with excellent water solubility, respectively. The experimental results show that α-bromocinnamaldehyde (BCA) nanosheets exhibits unprecedented antibacterial activity, but there is no antibacterial activity for α-methylcinnamaldehyde nanosheets. Therefore, the BCA nanosheets and α-methylcinnamaldehyde nanosheets achieve an antibacterial switch. Theoretical calculations further confirmed that the electron-withdrawing substituent of the bromine atom leads to a lower electron cloud density of the aldehyde group than that of the electron-donor substituent of the methyl group at the α-position of the cinnamaldehyde skeleton, which is a key point in elucidating the antimicrobial switch mechanism. The excellent biocompatibility of BCA nanosheets was confirmed by CCK-8. The mouse wound infection model, H&E staining, and the crawling ability of drosophila larvae show that as-prepared BCA nanosheets are safe and promising for wound healing. This study provides a new strategy for the synthesis of low-cost organic nanomaterials with good biocompatibility. It is expected to expand the application of natural organic small molecule materials in antimicrobial agents.

研究领域: 有机化学 · 纳米技术 · 生物医学工程 · 材料科学 · 药学
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JOURNAL OF MATERIALS SCIENCE · 2022 ·Vol. 57 ·期 5 ·3168-3182 · IF 4.682

Porous carbon-encapsulated Ni nanocatalysts for selective catalytic hydrogenation of cinnamaldehyde to hydrocinnamaldehyde

Tian Fuping,Zhang Mengjie,Zhang Xinchi,Chen Xiao,Wang Jinliang,Zhang Yifu,Meng Changgong,Liang Changhai

Hydrogenation of cinnamaldehyde (CAL) to cinnamyl alcohol (COL) or hydrocinnamaldehyde (HCAL) with high selectivity has important industrial value. Previous studies have shown that nickel-based catalysts are highly active and favor the selectivity to HCAL. However, Ni in metallic state is so active that most of nickel-based catalysts need to be pre-reduced before use. In this paper, a stable Ni–C catalyst was prepared by simple pyrolysis of Ni-BTC and systematically characterized. The results showed that metallic Ni nanoparticles were uniformly dispersed and encapsulated in the carbon layer, which protects the metallic Ni from oxidation. Therefore, the Ni–C catalyst can be directly used in CAL hydrogenation without pre-reduction. The catalyst Ni-C-600 achieved 92.5% selectivity to HCAL at 96.2% conversion of CAL at 120 °C under 2 MPa H 2 for 6 h with a poor reusability in isopropanol (IPA), while the catalytic performance and reusability were evidently enhanced (HCAL selectivity ~ 94%, CAL conversion ~ 99% in five consecutive runs for 4 h) in a solvent containing water and IPA. This study provides a facile and low-cost method to prepare effective Ni-based catalysts displaying excellent catalytic activity with high HCAL selectivity and stable reusability in CAL hydrogenation. Graphical abstract

研究领域: 催化化学 · 材料科学
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CHEMICAL ENGINEERING JOURNAL · 2018 · IF 6.735

Selective hydrogenation of the CC bond in cinnamaldehyde over an ultra-small Pd-Ag alloy catalyst

Rongrong Li,Wubing Yao,Yanxian Jin,Wenping Jia,Xiaoying Chen,Jingjing Chen,Jianli Zheng,Yuan Hu,Deman Han,Jia Zhao

Hydrocinnamaldehyde (HCAL) is a crucial intermediate in the manufacture of perfumes and pharmaceuticals, but highly selective hydrogenation of cinnamaldehyde (CALD) to hydrocinnamaldehyde with a good conversion rate is a challenging. We report that the incorporation of Ag into Pd-based catalysts promotes their catalytic activity and HCAL selectivity (HCAL selectivity of 98.6% with >99.9% CALD conversion for Pd-0.3Ag/MCM-41) for CALD hydrogenation compared to those of catalysts with no Ag, e.g., HCAL selectivity of 84.5% for Pd/MCM-41and 77.3% for Pd/AC (activated carbon). The Pd-0.3Ag/MCM-41 catalyst shows an outstanding stability during five cycles of use. The excellent performance of the Pd-0.3Ag/MCM-41 catalyst in CALD hydrogenation is due to the ultra-small size of the Pd nanoparticles (Pd-Ag alloy, a geometric and electronic modification of Pd).

研究领域: 化学工程 · 催化科学
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Catalysts · 2018 ·Vol. 8 ·期 5 ·200 · IF 3.465

Improvement Effect of Ni to Pd-Ni/SBA-15 Catalyst for Selective Hydrogenation of Cinnamaldehyde to Hydrocinnamaldehyde

Shiying Han,Yunfei Liu,Jiang Li,Rui Li,Fulong Yuan,Yujun Zhu

A series of Pd-Ni bimetallic catalysts supported on SBA-15 (0.2%Pd-x%Ni/SBA-15, x = 0.4, 0.7, and 1.2) were prepared through the impregnation method combined with the NaBH4reduction method. X-ray diffraction (XRD), N2adsorption-desorption, X-ray photoemission spectroscopy (XPS) and transmission electron microscope (TEM) were used to characterize the prepared catalysts. All the synthesized catalysts were evaluated for the liquid-phase hydrogenation of cinnamaldehyde (CAL). The addition of Ni obviously enhanced the CAL conversion and selectivity of C=C hydrogenation to hydrocinnamaldehyde (HALD) over the 0.2%Pd-x%Ni/SBA-15 catalysts. Meanwhile, 0.2%Pd-1.2%Ni/SBA-15 showed the best performance with 96.3% conversion and 87.8% selectivity toward HALD. This improvement was attributed to the synergistic effect between the Pd and Ni nanoparticles, enhancing the dispersion of Pd metal particles and increasing the content of surface Pd0species. In addition, the influences of a few reaction factors including H2pressure, reaction temperature, and reaction time were studied over 0.2%Pd-1.2%Ni/SBA-15.Keywords:selective hydrogenation;cinnamaldehyde;hydrocinnamaldehyde;synergistic effect;Pd-Ni/SBA-15

CAS / MDL: 7758-87-4 35947-07-0
研究领域: 催化化学 · 材料科学
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Processes · 2020 ·Vol. 8 ·期 8 ·897 · IF 2.753

Preparation of Long-Term Antibacterial SiO2-Cinnamaldehyde Microcapsule via Sol-Gel Approach as a Functional Additive for PBAT Film

Yangfan Xu,Chongxing Huang,Xiujie Dang,Muhammad Rafiullah Khan,Haohe Huang,Yuan Zhao,Shuangfei Wang

The mesoporous silica wall materials can achieve controlled load and sustained-release of active agents. An antimicrobial nanoscale silica microcapsule containing cinnamaldehyde (CA) was prepared by the sol-gel method and applied in poly (butyleneadipate-co-terephthalate) (PBAT) film. The surface morphology, physical and chemical properties, and antibacterial properties of microcapsules and films were studied. The effects of different temperatures and humidities on the release behavior of microcapsules were also evaluated. Results showed that CA was successfully encapsulated in silica microcapsule which had a diameter of 450–700 nm. The antibacterial CA agent had a long-lasting release time under lower temperature and relative humidity (RH) environment. At low temperature (4 °C), the microcapsules released CA 32.35% in the first 18 h, and then slowly released to 56.08% in 216 h; however, the microcapsules released more than 70% in 18 h at 40 °C. At low humidity (50%RH), the release rates of microcapsules at the 18th h and 9th d were 43.04% and 78.01%, respectively, while it reached to equilibrium state at 72 h under 90% RH. The sustained release process of CA in SiO2-CA microcapsules follows a first-order kinetic model. Physicochemical properties of PBAT films loaded with different amounts of microcapsules were also characterized. Results showed that the tensile strength and water vapor transmission rate (WVTR) of the composite film containing 2.5% microcapsules were increased by 26.98% and 14.61%, respectively, compared to the raw film, while the light transmittance was slightly reduced. The crystallinity of the film was improved and can be kept stable up to 384.1 °C. Furthermore, microcapsules and composite film both exhibited distinctive antibacterial effect onEscherichia coliandListeria monocytogenes. Therefore, SiO2-CA microcapsules and composite films could be a promising material for the active packaging.Keywords:cinnamaldehyde;PBAT;antibacterial materials;composite film

CAS / MDL: 104-55-2 67-68-5
研究领域: 材料科学 · 生物技术
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Unravelling the synergy of platinum-oxygen vacancy in CoOx for modulating hydrogenation performance

Hao Xu,Hongxia Zhang,Lin Cui,Xinshuo Zhao,Jiao Xiao,Jian Zhang,Yong Qin,Jiankang Zhang

Constructing high-efficiency catalysts with high activity and selectivity is the long-term pursuit in heterogeneous catalysis field. Metal–oxygen vacancy (Ov) synergy provides a promising route to realizing the goal. In this study, the Pt/CoO x catalysts with Pt–Ov dual sites are designed by atomic layer deposition (ALD) for selective hydrogenation of cinnamaldehyde, and the Ov property, Pt size and the spatial relationship of Pt and CoO x can be well modulated. Experimental and theoretical investigations indicate that the substrate and hydrogen can be activated on Ov and Pt nanoparticles, respectively. The Ov introduced by ALD not only preferentially activates C O bond of CALD to achieve high selectivity to CALA, but also enhances the ability to dissociate hydrogen on Pt nanoparticles through Pt-Ov electron transfer. Importantly, the optimized Pt40/CoO x -Ov catalysts with suitable Ov coordination and Pt sizes (2.5 nm) show lower adsorption energy for reactant molecules, obtaining significantly enhanced activity with a turnover frequency value of 202.5 mol CALD ·mol Pt -1 ·min −1 and obviously improved selectivity of desired products (93 %). This work offers a fundamental understanding of Pt–Ov synergy toward hydrogenation of unsaturated compounds.

研究领域: 催化化学 · 材料科学
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Coatings · 2018 ·Vol. 8 ·期 10 ·372 · IF 2.35

Effects of Chitosan-Based Coatings Enriched with Cinnamaldehyde on Mandarin Fruit cv. Ponkan during Room-Temperature Storage

Yang Gao,Chaonan Kan,Ming Chen,Chuying Chen,Yuhuan Chen,Yongqi Fu,Chunpeng Wan,Jinyin Chen

The current work aimed to evaluate the efficacy of four coating formulations—chitosan coating (CH), 0.5% cinnamaldehyde + chitosan (0.5% CI–CH), 1.0% cinnamaldehyde + chitosan (1.0% CI–CH), and 1.5% cinnamaldehyde + chitosan (1.5% CI–CH)—on fresh mandarin fruit cv. Ponkan quality maintenance (weight loss, decay rate, total soluble solids, titratable acidity, vitamin C, color index, malondialdehyde, and antioxidant activity) over 100 days of storage at 20 °C. Compared to the control, chitosan treatment effectively reduced the decay and weight loss rates of mandarin fruit cv. Ponkan during storage at room temperature, delayed the decline of nutritional quality in fruits, increased the antioxidant capacity, and inhibited the accumulation of malondialdehyde (MDA). In comparison to chitosan coating, 1.5% CI–CH did not improve the fruit storage effect, but inhibited the normal color change of fruits and increased the accumulation of MDA. Both 0.5% CI–CH and 1.0% CI–CH effectively reduced the rate of fruit decay, improved the quality of fruits after harvest, and delayed fruit aging. Our study suggests that 0.5% CI–CH and 1.0% CI–CH might be good formulations for maintaining the quality of mandarin fruit cv. Ponkan during room-temperature storage.Keywords:chitosan;coating;cinnamaldehyde;fruit;room temperature

研究领域: 食品科学 · 植物保护
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2023 · IF 9.9

Cinnamaldehyde grafted porous Aerogel-Organ gel liquid infused surface for achieving difunctional long-term dynamic antifouling

Yuhan Guo,Minglong Yan,Wenjie Zhao

Marine biofouling caused a number of questions about energy consumption and safety. While there were still some challenges in developing an environmentally friendly, non-toxic and long-term antifouling slippery liquid-infused porous surface (SLIPS). Here, we proposed a difunctional antifouling strategy via constructing porous polydimethylsiloxane (PDMS) surface with a layer of aerogel by sol-gel method and grafted cinnamaldehyde chemically. The improvement in structure enhanced the liquid storage stability of coating, which in turn increases its anti-bioadhesive ability. In addition, the grafted cinnamaldehyde could also be used to act as a chemical antibacterial and is intelligently released in the face of harsh fouling environments, which played a key role in prolonging the antibacterial lifespan of the coating. After the 120-hour anti-bacteria experiment and the 25-day anti-algae experiment, the anti- Escherichia coli (anti- E. coli ) rate and the anti-algae rate of the coating reached 99.6% and 99.9%, respectively, which was attributed to the excellent long-term antifouling properties of the coating. The combination of physical and chemical antifouling property made the coating achieve long-term fouling prevention for marine engineering equipment.

研究领域: 材料科学 · 海洋生物学 · 环境科学
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Fishes · 2023 ·Vol. 8 ·期 3 ·122 · IF 2.3

Cinnamaldehyde Decreases the Pathogenesis of Aeromonas hydrophila by Inhibiting Quorum Sensing and Biofilm Formation

Shengping Li,Shun Zhou,Qiuhong Yang,Yongtao Liu,Yibin Yang,Ning Xu,Xiaohui Ai,Jing Dong

Antibiotics were the main fishery drugs for treatingAeromonas hydrophila(A. hydrophila) infection, which would generate selective pressure and result in the appearance of antibiotic-resistant bacteria. The bacterial quorum sensing (QS) system provides a new alternative strategy againstA. hydrophilainfection. QS inhibitors can reduce bacterial virulence behaviors by disrupting QS, which has no effect on bacterial growth. Therefore, we studied the effect of cinnamaldehyde from a natural plant extract on the QS ofA. hydrophilaaiming to reduce its pathogenicity. The efficacy of cinnamaldehyde againstA. hydrophilawas evaluated from various aspects, including the effects on aerolysin, lipase, protease, swarming motility, biofilm formation, acyl-homoserine lactones (AHLs), and QS-related genes. Moreover, the therapeutic effect of cinnamaldehyde in vitro and in vivo was studied. The results showed that cinnamaldehyde could decrease the virulence phenotypes ofA. hydrophilaregulated by QS. Moreover, the transcriptions of related genes (aerA,ahyR, andahyI) were downregulated following the addition of cinnamaldehyde. The in vitro and in vivo therapeutic assays show that cinnamaldehyde could reduce the aerolysin-mediated A549 cell injury and increase the survival rate of crucian carp infected withA. hydrophila. These results indicate that cinnamaldehyde would be a candidate QS inhibitor againstA. hydrophilainfection.Keywords:Aeromonas hydrophila;quorum sensing;cinnamaldehyde;virulence;biofilm

CAS / MDL: 104-55-2
研究领域: 微生物学 · 水产养殖 · 感染生物学
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FOOD CHEMISTRY · 2025 · IF 9.8

Enhancement of oil-resistance and antibacterial property of cellulose paper by coated with natural compound for eco-friendly cake packaging

Fang Wang,Wenwen Liu,Yumeng Jin,Wenyu Zou,Shouyan Zhu,Hangyu Shen,Xiaoying Wang,Ziqiang Xu,Fangong Kong

The amphipathic property of paper inhibits its applications in cake packaging. Herein, sodium alginate, calcium chloride, and cinnamaldehyde were mixed, and the process was precisely controlled to maintain homogenously aqueous coating solution. Sodium alginate and Ca 2+ chelation is helpful to the intermolecular hydrogen bonding, which improves oil resistance of the coated papers. Kit number of the coated papers were 12 at 30, 45, 60, 75, 90, 105 and 120 °C, and soybean oil resistance time was over 24 h. The coated papers exhibited good biocompatibility, and the bacterial inhibition zones reached 28 ( Escherichia coli ) and 34 mm ( Staphylococcus aureus ). Additionally, the mechanical property, air permeability, ultraviolet and high-energy blue light blocking, and antioxidative property were all improved. Cake preservation results showed that the coated paper inhibited oil penetration and bacterial proliferation. This biomass-based coated papers can be an alternative for grease food packaging.

研究领域: 材料科学 · 食品科学 · 环境科学
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JOURNAL OF FOOD SCIENCE · 2020 ·Vol. 85 ·期 1 ·157-164 · IF 2.479

Investigating the antimicrobial and antibiofilm effects of cinnamaldehyde against Campylobacter spp. using cell surface characteristics

Hwan Hee Yu,Ye Ji Song,Hyung-Seok Yu,Na-Kyoung Lee,Hyun-Dong Paik

Campylobacter species are known as biofilm-forming bacteria in food systems. The aim of this study was to evaluate the antimicrobial and antibiofilm effects of cinnamaldehyde against Campylobacter jejuni and Campylobacter coli isolated from chicken meat. The biofilm-forming C. jejuni and C. coli strains from chicken meat were investigated using minimum inhibitory concentration (MIC) and Campylobacter spp. characteristics. The MIC value was 31.25 µg/mL for the Campylobacter strains tested. Cinnamaldehyde had an inhibition and degradation effect on Campylobacter biofilms at concentrations > 15.63 µg/mL. Campylobacter strains treated with 15.63 µg/mL CA exhibited significantly decreased autoaggregation, motility, exopolysaccharide production, and soluble protein. In addition, Campylobacter biofilms formed on stainless steel were degraded following cinnamaldehyde treatment, as determined by scanning electron microscopy. Taken together, these results suggest that cinnamaldehyde constitutes a potential natural preservative against Campylobacter and a nontoxic biofilm remover that could be applied to control food poisoning in the poultry manufacturing-related food industry. Practical Application Cinnamaldehyde was able to effectively remove the biofilm of Campylobacter in the small crack of stainless steel. Cinnamaldehyde has a potential to replace the synthetic antimicrobial and/or antibiofilm agent as well as has a positive influence on consumer concern for the food safety issues of the poultry industries.

CAS / MDL: 104-55-2
研究领域: 微生物学 · 食品安全 · 食品科学
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JOURNAL OF FOOD PROCESSING AND PRESERVATION · 2018 ·Vol. 42 ·期 8 ·e13696 · IF 1.51

Ethyl cellulose aqueous dispersions: A fascinating supporter for increasing the solubility and sustained-release of cinnamaldehyde

Xingzhong Zhang,Xia Wu,Wei Li,Xiaogang Luo,Yan Li,Bin Li,Shilin Liu

In order to increase the solubility, stability, and availability of cinnamaldehyde which was widely used in food industry, ethyl cellulose aqueous dispersions encapsulated cinnamaldehyde had been prepared by using an anti-solvent induced method. The particles size of the obtained aqueous dispersions was in the range of 150–200 nm, and it increased slightly with the increasing concentrations of the precursor solution. The prepared dispersions after being dried at ambient conditions had the ability to form a free-standing film, and the film had denser structure and smooth surface. Moreover, the ethyl cellulose dispersions had powerful encapsulation ability to cinnamaldehyde, and the encapsulated cinnamaldehyde could be sustained released, it could prolong the storage time of fresh pork samples for more than 6 days, and an excellent antimicrobial property for food spoilage was observed. It indicated that the prepared dispersions could be a fascinating supporter for increasing the stability and sustained-release of cinnamaldehyde. Practical applications In this work, the ethyl cellulose aqueous dispersions encapsulating with cinnamaldehyde had good stability, and the sustained released of cinnamaldehyde could effectively inhibit the growth of spoilage organism for a long time, which indicated that aqueous dispersions system had potential applications for food preservation.

研究领域: 食品科学 · 材料科学 · 生物学
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