ACS Sustainable Chemistry & Engineering
·
2024
·
IF 7.1
Na Wang,Xiang Zhou,Youming Dong,Ying Zhang,Rong Liu,Haijiao Kang,Kaili Wang,Jianzhang Li
Natural mildew preventives, like citral, have great potential to protect bamboo from mildew, while their long-lasting antimildew performance is yet to be challenged owing to their oxidability and volatility. Inspired by biomimetic mineralization, in this work, citral@ZIF-67 particles were synthesized by encapsulating citral into a zeolite imidazolate framework-67 (ZIF-67) cage and introduced into a bamboo structure. Benefiting from the unique cage structure and large surface area of ZIF-67, it can encapsulate sufficient citral molecules. The encapsulation reduced the particle size of ZIF-67 due to the nucleation of citral. Furthermore, the surface area, pore size, and volume of citral@ZIF-67 particles gradually decreased with the increase in loading amounts of citral. ZIF-67 exhibited a certain antibacterial ability against E. coli and S. aureus. The encapsulation of citral can further enhance the antibacterial activity of ZIF-67. In addition, the citral@ZIF-67 showed slow-release performance that followed the Fickian diffusion mechanism. After the citral@ZIF-67 treatment, bamboo showed no mold spots on the surface with an infection grade of 0, which was retained, even though bamboo was conditioned at 50 °C and 85% relative humidity for 10 days. This proposed method can effectively improve the stability of natural mildew preventives and endow bamboo with long-term antimildew properties with low cost and minimized environmental impacts.
研究领域:
材料科学
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生物学
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林业科学
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产品关联
DOI
高影响因子
Food Bioscience
·
2025
·
IF 5.9
Jinming Dai,Mei Bai,Houzhi Fang,Tariq Aziz,Ashwag Shami,Fahad Al-Asmari,Fakhria A. Al-Joufi,Maher S. Alwethaynani,Haiying Cui
Citral is widely recognized as a membrane-targeting antimicrobial, with its bactericidal activity primarily dependent on the degree of membrane damage. This study reveals its dual mechanism involving oxidative assault against Listeria monocytogenes ( L. monocytogenes ). The induced cytotoxic effects appear closely associated with citral's interaction with bacterial cell membrane components and the resultant sustained membrane dysfunction. Our results showed that sublethal concentrations of citral induced rapid depolarization in L. monocytogenes while progressively increasing membrane permeability. Following 1 h of citral exposure, the intracellular generation of reactive oxygen species peaked. Further investigations indicated that citral could directly interact with and alter the chemical structure of reduced glutathione (GSH). Notably, exogenous GSH supplementation significantly attenuated citral's antimicrobial efficacy, suggesting that its biochemical reactivity targeting glutathione and related thiol-containing proteins plays a critical role in the antibacterial action against L. monocytogenes . Importantly, regardless of growth inhibition, all tested concentrations of citral significantly suppressed the hemolytic activity of L. monocytogenes . Overall, this study provides valuable insights into the antimicrobial mechanisms of citral, particularly at low concentrations.
研究领域:
微生物学
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食品科学
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生物化学
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产品关联
DOI
高影响因子
Bioresources and Bioprocessing
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2018
·Vol. 5
·期 1
·1-12
·
IF 0
Zheng Liandan,Lin Jinping,Zhang Baoqi,Kuang Yuyao,Wei Dongzhi
A NAD(P)H-dependent enoate reductase (OYE2p) from Saccharomyces cerevisiae YJM1341 was discovered by genome data mining for asymmetric reduction of (E/Z)-citral to (R)-citronellal with high enantioselectivity.This enzyme was heterologously expressed in E. coli and characterized for its biocatalytic properties. OYE2p was identified with reduction activities toward a diverse range of ɑ,β-unsaturated compounds bearing conjugated aldehyde, ketone, imide, carboxylic acid and ester.OYE2p showed the highest specific activity at 40 °C and a pH optimum at 7.0–8.0. The stability of OYE2p was rather pH-independent, and the half-life time values of the enzyme at pH 6.0–8.0 were more than 257 h. With regard to the reduction of (E)-citral and (Z)-citral, OYE2p exhibited different selectivity patterns. (E)-citral was exclusively reduced to (R)-citronellal by OYE2p in ≥ 99% ee, which was independent on pH. OYE2p produced both enantiomers of citronellal from (Z)-citral, but showed (R)-citronellal formation tendency, and the ee value of (R)-citronellal was affected by pH in the reaction system. Accordingly, the ee values for (R)-citronellal formation increased with the increasing levels of E-isomer in the (E/Z)-citral mixture as well as the increase of pH. Under the reaction conditions (30 °C and pH 8.6), using purified OYE2p as catalyst, 200 mM (E/Z)-citral (an approximately 10:9 mixture of geometric E-isomer and Z-isomer) was efficiently converted to (R)-citronellal with 88.8% ee and 87.2% yield.All these positive features demonstrate high potential of OYE2p for practical synthesis of (R)-citronellal and in asymmetric reduction of activated alkenes.
研究领域:
生物化学
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酶工程
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合成生物学
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产品关联
DOI
MOLECULAR PLANT PATHOLOGY
·
2023
·
IF 4.9
Wen Song,Zhiyuan Yin,Xinyu Lu,Danyu Shen,Daolong Dou
Phytophthora capsici is a notorious pathogen that infects various economically important plants and causes serious threats to agriculture worldwide. Plants deploy a variety of plant secondary metabolites to fend off pathogen attacks, but the molecular mechanisms are largely unknown. In this study, we screened 11 plant secondary metabolites to evaluate their biofumigation effects against P. capsici , and found that citral, carvacrol, and trans -2-decenal exhibited strong antimicrobial effects. Intriguingly, a low concentration of citral was effective in restricting P. capsici infection in Nicotiana benthamiana , but it was unable to inhibit the mycelial growth. A high concentration of citral affected the mycelial growth and morphology, zoospore germination, and cell membrane permeability of P. capsici. Further investigations showed that citral did not induce expression of tested plant immunity-related genes and reactive oxygen species (ROS) production, suggesting that a low concentration of citral could not trigger plant immunity. Moreover, RNA-Seq analysis showed that citral treatment regulated the expression of some P. capsici effector genes such as RxLR genes and P. cactorum - fragaria (PCF)/small cysteine-rich (SCR)74-like genes during the infection process, which was also verified by reverse transcription-quantitative PCR assay. Five candidate effector genes suppressed by citral significantly facilitated P. capsici infection in N. benthamiana or inhibited ROS triggered by flg22, suggesting that they were virulence factors of P. capsici . Together, our results revealed that plant-derived citral exhibited excellent inhibitory efficacy against P. capsici by suppressing vegetative growth and manipulating expression of effector genes, which provides a promising application of citral for controlling Phytophthora blight.
研究领域:
植物病理学
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分子生物学
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产品关联
DOI
PubMed
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
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2025
·
IF 6.6
Min Wen,Ran Tao,Jianchun Jiang,Yicun Chen,Yangdong Wang
Natural citral has attracted widespread attention for its antibacterial properties, but its instability during processing and in biological systems, such as the gastrointestinal tract, limits its application as an antibiotic alternative. This study aims to enhance the stability and antibacterial efficacy of citral by formulating it into a sustained-release system using Schiff base reaction and metal complexation with chitosan (CS), tannic acid (TA), and zinc (Zn). Characterization of the CS-CT-TA-Schiff base/OH-TA-Zn (CS-CT-TA-Zn) complex revealed a porous, rough morphology with an average particle size of 366.97 ± 48.02 nm. The composite exhibited a citral loading capacity of 57.78 ± 1.33%, with pH-responsive sustained release behavior observed within the pH range of 1.5–2.0. Tannic acid's antioxidant properties helped maintain the formulation’s stability. Antimicrobial testing showed that the citral loading in the composite at the Minimum Inhibitory Concentration (MIC) against Vibrio parahaemolyticus was 20 μg/mL, effectively disrupting the bacterial cell membrane and inhibiting biofilm formation. The CS-CT-TA-Zn complex significantly enhances the stability and antibacterial activity of citral, providing new insights into its application as an antimicrobial agent targeted for delivery to the human stomach, and increasing its potential as a more effective food additive.
研究领域:
食品科学
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微生物学
·
材料科学
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产品关联
DOI
高影响因子
PHYSIOLOGICAL AND MOLECULAR PLANT PATHOLOGY
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2021
·
IF 2.747
Ling Wei,Chuying Chen,Jinyin Chen,Liping Lin,Chunpeng Wan
The current study was conducted to evaluate the inhibitory effects of citral against various fungal pathogens viz: Botryosphaeria dothidea , Phomopsis macrospore , and Botrytis cinerea . The present study aimed to describe the antifungal mechanism of citral against B. dothidea , which is not fully elucidated yet. According to the results, citral showed potent inhibition on the hyphal growth of the three studied fungi with a minimum inhibitory concentration of 0.4 μL/mL. Citral changed the morphological characteristics of fungal hyphae of B. dothidea by resulting in the loss of cellular content and distortion of mycelia . Membrane permeability was increased by citral, as evidenced by increases in extracellular electrical conductivity and optical density (OD 260 ) and a decrease in soluble protein content in B. dothidea. A decline in the range of ergosterol levels proved that citral impaired the physiology of the cell membrane. Furthermore, the higher citral concentrations decrease the level of respiration-associated enzymes resulting in the disruption of energy metabolism. Importantly, citral also showed positive effects on fruit quality and reduced the decay rate of kiwifruit . These findings suggest that the antifungal activity of citral could be attributed to the increase in membrane permeability and the damage in the cell membrane. Citral can potentially be used as an alternative for kiwifruit storage.
研究领域:
植物病理学
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食品科学
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微生物学
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产品关联
DOI
高影响因子
Carbohydrate Polymer Technologies and Applications
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2025
·
IF 6.5
Jinhua Zhang,Jichen Su,Xinyi Liu,Min Chen,Baoqing Bai,Yukun Yang,Sanhong Fan,Tao Bo
s This study aimed to prepare a CS-TPP nanoparticle loaded with rosmarinic acid and citral and to evaluate the overall performance of the novel antimicrobial film prepared by the addition of the nanoparticles to the CMC film. The structure of the nanoparticles was determined by particle size potentiometry, SEM, and FTIR, and it was demonstrated that rosemarinic acid and citral were successfully combined with CS-TPP nanoparticles with a particle size of 446.2 nm. The surface morphology and mechanical properties of the films were determined by texture instrumentation, SEM, FTIR, and XRD.The CMC-XT showed a tensile strength of 9.30 N/mm² (49 % higher than the blank film, 6.23 N/mm²) and an elongation at break of 175 %, surpassing the CMC-RA (6.58 N/mm²). The antibacterial performance experiment showed that the inhibition rates of CMC-XT on E.coli and S.aureus were 69.4 % and 61.9 %, respectively, which were significantly better than the blank membrane (9.2 %).The experiment provides a new type of film that combines mechanical strength, antibacterial performance, and environmental friendliness for food preservation, solving the safety issues of traditional chemical preservatives and the cost limitations of physical preservation technology.As well as it utilizes natural antimicrobial agents and biodegradable polymers, reducing reliance on traditional chemical preservatives that may pose health risks or environmental concerns.
研究领域:
食品科学
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材料科学
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产品关联
DOI
高影响因子
PHARMACEUTICAL BIOLOGY
·
2018
·
IF 1.918
Huaqiao Tang,Nana Long,Min Dai,Lin Lin,Jianlong Li,Fenghui Sun,Lijuan Guo
Context: Citral is used as a potential natural treatment for various infectious diseases.Objective: To examine the effect of citral on the mRNA expression and activities of cytochrome P450 (CYP450) enzymes and establish the relationship between citral-induced liver injury and oxidative stress.Materials and methods: ICR mice were randomly divided into citral (20, 200, and 2000 mg/kglow), Tween-80, and control groups (0.9% saline), 10 mice in each group. The citral-treated groups were intragastrically administered citral for 3 d, control groups treated with 0.5% Tween-80 and 0.9% saline in the same way. Liver injury and CYP450 enzymes were analyzed by analyzing the histopathological changes and the changes of related enzymes.Results: Citral treatment (2000 mg/kg) for 3 d increased serum glutamic pyruvic transaminase and glutamic oxaloacetic transaminase levels, as well as glutathione, gydroxyl radicals, malonaldehyde and total superoxide dismutase contents, but decreased the content of total antioxidant capacity. In doses of 20 and 200 mg/kg groups mice, the contents of NO were decreased significantly and other changes were similar to the 2000 mg/kg group mice, but the liver damage was most severe in the 2000 mg/kg group. Citral induced the mRNA expression and activities of CYP450 1A2, 2D22, and 2E1 in the liver of mice at doses of 20 and 200 mg/kg. There were no changes in testing indexes in Tween-80 treated group mice. Due to its toxic effects, the CYP induction effect of citral negatively correlated with its dose. Although the mRNA expression of CYP450 3A11 was induced by citral, its activity was not affected by low and moderate doses of citral. CYP450 3A11 activity was significantly decreased by high-dose citral.Conclusions: Citral is hepatotoxic and induced oxidative stress in higher dose, which has a negative effect on CYP450 enzymes. These data suggest caution needs to be taken in order to avoid citral-drug interactions in human beings.
研究领域:
药理学
·
毒理学
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分子生物学
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产品关联
DOI
PubMed
高影响因子
Food Bioscience
·
2023
·
IF 5.2
Jinming Dai,Mei Bai,Changzhu Li,Wai San Cheang,Haiying Cui,Lin Lin
Citral, a natural antimicrobial agent, has been found to induce severe membrane damage resulting in bacterial death. Despite its effectiveness, there is a lack of in-depth research on its interaction with bacterial cells, especially at low concentrations. This work aimed to investigate the impact of citral concentration on its antibacterial effect against Staphylococcus aureus ( S. aureus ) and to analyze the relevance between membrane damage and cell death. In this study, the minimal inhibitory concentration of citral against S. aureus was measured at 0.25 mg/mL. At a concentration of 0.5 mg/mL, citral significantly disturbed the cell membrane fluidity and permeability, leading to the leakage of intracellular macromolecules and rapid cell death. However, when the concentration was decreased to 0.25 mg/mL, the membrane damage was greatly reduced, and a complex biological process between citral and membrane components was found. Under continuous drug exposure, the cell membrane underwent gradual rigidification, concomitant with the loss of membrane function, ultimately causing cell death. Despite the fact that no notable disturbance to membrane functions was discovered, the presence of 0.125 mg/mL citral could still weaken the metabolic vitality and growth of S. aureus . Therefore, it was suggested that there could be multiple mechanisms of citral action on S. aureus cells, with drug concentration being a critical factor affecting the mode of action. Overall, the findings of this study provide valuable insights into the antibacterial mechanisms of natural compounds and broaden the potential applications of citral as a natural antimicrobial.
研究领域:
微生物学
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药理学
·
天然产物研究
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产品关联
DOI
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
·
2024
·
IF 4.2
Jiying Zhang,Huifang Liu,Jianmei Yao,Chiyu Ma,Wen Yang,Zhiwei Lei,Rongyu Li
Anthracnose, a fungal disease, commonly infects tea plants and severely impacts the yield and quality of tea. One method for controlling anthracnose is the application of citronellol, a plant extract that exhibits broad-spectrum antimicrobial activity. Herein, the physiological and biochemical mechanism by which citronellol controls anthracnose caused by Colletotrichum camelliae was investigated. Citronellol exhibited excellent antifungal activity based on direct and indirect mycelial growth inhibition assays, with EC 50 values of 76.88 mg/L and 29.79 μL/L air, respectively. Citronellol also exhibited good control effects on C. camelliae in semi-isolated leaf experiments. Optical and scanning electron microscopy revealed that citronellol caused C. camelliae mycelia to thin, fracture, fold and deform. Transmission electron microscopy revealed that the mycelial cell walls collapsed inward and separated, and the organelles became blurred after treatment with citronellol. The sensitivity of C. camelliae to calcofluor white staining was significantly enhanced by citronellol, while PI staining showed minimal fluorescence, and the relative conductivity of mycelia were not significantly different. Under citronellol treatment, the expression levels of β -1,3-glucanase, chitin synthase, and chitin deacetylase-related genes were significantly decreased, while the expression levels of chitinase genes were increased, leading to lower chitinase activity and increased β -1,3-glucanase activity. Therefore, citronellol disrupted the cell wall integrity of C. camelliae and inhibited normal mycelial growth.
研究领域:
植物病理学
·
分子生物学
·
真菌学
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产品关联
DOI
PubMed
高影响因子
Molecular Catalysis
·
2021
·
IF 5.062
Jian He,Zhaozhuo Yu,Hongguo Wu,Hu Li,Song Yang
Effective synthesis of aromatic compounds from renewable biomass is highly important yet challenging. p -Cymene is an attractive aromatic compound with various promising applications in the manufacture of fine chemicals. In this study, a novel and effective catalytic system based on mesoporous tin phosphate (M-SnPO) with Lewis-Brønsted dual acidity was developed for the fast synthesis of p -cymene from the cyclodehydration of bio-based citral. Up to 78.5% yield of p -cymene was achieved from the cyclodehydration of citral at 180 °C within only 0.5 h, superior to the results reported for benchmark homogeneous acid catalysts. Characterization of as-prepared M-SnPO catalyst via various techniques indicates that the synergic effect of Lewis and Brønsted acidic sites, large pore-sized structure, and high surface area are responsible for its remarkable catalytic performance. In addition, the effectiveness of the M-SnPO catalyst could be almost sustained over multiple cycles without significant loss. The work herein is the first example of developing a Lewis-Brønsted dual acidic heterogeneous catalyst for the fast synthesis of p -cymene from the cyclodehydration of citral.
研究领域:
催化化学
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生物质转化
·
材料科学
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产品关联
DOI
高影响因子
PROGRESS IN ORGANIC COATINGS
·
2025
·
IF 7.3
Shuai He,Yun Zhao,Weiyu Liu,Zhenfeng Huang,Nanlan Shen,Chuanbai Yu,Wenhui Rao
Transparent flame-retardant epoxy coatings with high toughness and sustainability are of great interest for advanced protective and electronic applications. In this work, a bio-sourced flame-retardant toughening agent (CTDP) was synthesized using citral and a phosphorus-containing compound. The resulting molecule features dangling aliphatic chains and multiple reactive groups, enabling it to act not only as a flame-retardant toughening agent but also as a co-curing agent within the epoxy resin (EP). At a low loading of 0.5 wt%, the EP/CTDP-0.5 achieved a limiting oxygen index of 27.5 % and achieved the UL-94 V-1 rating, demonstrating significantly enhanced flame retardancy compared to neat EP. Cone calorimeter results further demonstrated a 14.9 % reduction in peak heat release rate and a 13.2 % decrease in total smoke production, highlighting the effective fire-safety performance of CTDP. Remarkably, the incorporation of only 0.5 wt% CTDP led to a significant 209.9 % increase in impact strength, highlighting its excellent toughening effect. This improvement is primarily attributed to the flexible dangling aliphatic chains in CTDP, which promote microphase separation and facilitate the formation of a hyperbranched-like crosslinked structure. Importantly, the EP/CTDP composites maintained excellent optical transparency, with visible-light transmittance remaining high even at increased CTDP content. These findings demonstrate that CTDP effectively integrates flame retardancy, mechanical toughness, and transparency within a single bio-based molecular framework, offering a promising and sustainable strategy toward the design of advanced multifunctional EPs.
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产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）