INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2018
·
IF 3.141
Feng Zhou,Hongchen Liu,Zhenghui Wen,Boyu Zhang,Guangwen Chen
Pseudoionone (PI) is a well-known and widely used precursor for ionones, which have been substantially applied in flavor, fragrance and pharmaceutical industry. The phase behavior in respect to the synthesis of PI was investigated through the combination of simulation and experiment to better understand the reaction process. A continuous-flow microreactor for efficient synthesis of PI was introduced. Various conditions (temperature, molar ratio of acetone to citral, citral concentration, NaOH concentration, residence time, and volume ratio of ethanol to water) were investigated to improve the synthesis process of PI. The condensation reaction preformed in the tubular and packed-bed microreactor under continuous-flow conditions was compared. Using a continuous-flow microreactor, PI could be efficiently synthesized from citral and a high PI yield of 93.8% could be achieved under the optimized conditions. Furthermore, a simplified kinetic model was developed to provide guidance for the synthesis of PI.
研究领域:
化学工程
·
香料与制药工业
✓ 已验证
产品关联
DOI
高影响因子
Polymers
·
2021
·Vol. 13
·期 19
·3314
·
IF 4.329
Rui Peng,Jingjing Zhang,Chungui Du,Qi Li,Ailian Hu,Chunlin Liu,Shiqin Chen,Yingying Shan,Wenxiu Yin
In the present study, the sustained-release system loading citral was synthesised by using PNIPAm nanohydrogel as a carrier and analysed its drug-release kinetics and mechanism. Four release models, namely zero-order, first-order, Higuchi, and Peppas, were employed to fit the experimental data, and the underlying action mechanism was analysed. The optimised system was applied to treat a bamboo mould, followed by assessment of the mould-proof performance. Our experimental results revealed that the release kinetics equation of the system conformed to the first order; the higher the external temperature, the better the match was. In the release process, PNIPAm demonstrated a good protection and sustained-release effect on citral. Under the pressure of 0.5 MPa, immersion time of 120 min, and the system concentration ratio of 1, the optimal drug-loading parameters were obtained using the slow-release system with the best release parameters. Compared to the other conditions, bamboos treated with pressure impregnation demonstrated a better control effect on bamboo mould, while the control effect onPenicillium citrinum,Trichoderma viride,Aspergillus niger, and mixed mould was 100% after 28 days. Moreover, the structure and colour of bamboo remained unchanged during the entire process of mould control.Keywords:nanohydrogels;citral;sustained-release;mechanism;bamboo;anti-mould
研究领域:
材料科学
·
微生物学
·
林业科学
✓ 已验证
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
·
药理学
·
天然产物研究
✓ 已验证
产品关联
DOI
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
·
2014
·
IF 2.009
Rong-Yu Li,Xiao-Mao Wu,Xian-Hui Yin,You-Hua Long,Ming Li
Given the importance of finding alternatives to synthetic fungicides, the antifungal effects of natural product citral on six plant pathogenic fungi ( Magnaporthe grisea, Gibberella zeae, Fusarium oxysporum, Valsa mali, Botrytis cinerea , and Rhizoctonia solani ) were determined. Mycelial growth rate results showed that citral possessed high antifungal activities on those test fungi with EC 50 values ranging from 39.52 to 193.00 µg/mL, which had the highest inhibition rates against M. grisea . Further action mechanism of citral on M. grisea was carried out. Citral treatment was found to alter the morphology of M. grisea hyphae by causing a loss of cytoplasm and distortion of mycelia. Moreover, citral was able to induce an increase in chitinase activity in M. grisea , indicating disruption of the cell wall. These results indicate that citral may act by disrupting cell wall integrity and membrane permeability, thus resulting in physiology changes and causing cytotoxicity. Importantly, the inhibitory effect of citral on M. grisea appears to be associated with its effects on mycelia reducing sugar, soluble protein, chitinase activity, pyruvate content, and malondialdehyde content.
研究领域:
植物病理学
·
真菌学
·
天然产物化学
·
农业科学
✓ 已验证
DOI
PubMed
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
·
食品科学
·
生物化学
✓ 已验证
产品关联
DOI
高影响因子
INDUSTRIAL CROPS AND PRODUCTS
·
2022
·
IF 6.449
Yue Jiang,Xiaolan Ji,Yueyang Zhang,Xiaoyu Pan,Yizhou Yang,Yiming Li,Wenhui Guo,Yong Wang,Zhiqing Ma,Bin Lei,He Yan,Xili Liu
Litsea cubeba essential oil (LCO) has a wide range of industrial uses. This study found that LCO has significant anti-TMV activity and that its active components are monoterpenoids. Citral , the main active component of the oil, showed outstanding anti-TMV activity. The protective, inactive, and curative efficacies of citral (500 μg/mL) against TMV were 76.27%, 55.14%, and 50.42%, respectively, which were significantly better than those of the positive control agent, chitosan oligosaccharide . Citral showed no direct effect on TMV particles but did induce hypersensitive response (HR). Bioassay results showed that citral induced significant plant disease resistance activity (68.20% at a concentration of 500 μg/mL). The results of physiological and biochemical experiments showed that citral induced the overexpression of defense enzymes such as SOD , CAT , POD , and PAL in tobacco (which increased by 5.3, 1.9, 3.0, and 4.0 times at a concentration of 500 μg/mL, respectively) as well as induced the overexpression of PR proteins, including NPR1 , PR1 , PR2 , and PR5 (which increased by 23.49, 39.27, 34.47, and 52.07 times at a concentration of 500 μg/mL, respectively). These results suggest that citral could induce systemic acquired resistance (SAR) in tobacco. Further mechanism studies conducted suggest that citral induces the overexpression of genes related to salicylic acid (SA) biosynthesis, including PAL , ICS , and PBS3 (50.74, 30.41, and 31.95 times higher than the control at a concentration of 500 μg/mL, respectively) and the accumulation of SA (5.1 times higher than the control at a concentration of 500 μg/mL). These results suggest that citral activates SAR through the SA pathway. The control efficacies induced by citral (500 μg/mL) on Erysiphe cucurbitacearum , Botrytis cinerea , and Sclerotinia sclerotiorum reached 67.39%, 59.61%, and 63.81%, respectively, indicating that citral can induce plant resistance against fungal diseases. The induced plant disease resistance activity of citral is prominent, with a long duration and a broad spectrum, performing better than the commercial agent chitosan oligosaccharide. Citral thus has the potential to be developed into a new botanical-derived anti-virus agent and plant immunity activator.
研究领域:
植物病理学
·
植物化学
·
分子生物学
·
农业科学
✓ 已验证
产品关联
DOI
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
·
2025
·
IF 4
Xuemei Lu,Ke Hu,Minggui Ou,Min Li,Xinchun Zhang,Xingyu Zhan,Xun Liao,Ming Li,Rongyu Li
The soft rot disease caused by Fusarium oxysporum leads to a significant reduction in the yield of Dendrobium officinale . However, research into the synergistic inhibitory effect of essential oils in D. officinale is extremely limited. In this study, we systematically investigated the direct and indirect inhibitory activity of carvacrol, citral and their combination against F. oxysporum , and their synergistic inhibitory mechanism. Carvacrol and citral exhibited significant direct and indirect inhibitory activity against F. oxysporum with EC 50 values of 54.37 mg/L and 119.32 mg/L (direct), 18.01 μL/(L•air) and 48.70 μL/(L•air) (indirect). Synergistic analysis revealed that the optimal synergistic toxicity of carvacrol and citral combination (Ca•Ci) against F. oxysporum was 10:1, with co-toxicity coefficient (CTC) of 131.57 and EC 50 value of 44.24 mg/L. Microscopy confirmed that the Ca•Ci led to more significant tip constriction, uneven surfaces and serious rupture of F. oxysporum mycelia than single compound. Transmission electron microscopy (TEM) showed that Ca•Ci also caused significant ultrastructural alterations to F. oxysporum , manifesting as cytoplasmic disorganization and partial organellar disintegration. Moreover, Ca•Ci dramatically increased the sensitivity of F. oxysporum to calcofluor white compared with a single compound. Ca•Ci also considerably upregulated the expression of chitinase-related gene ( FOXG _12882) and β -1,3-glucanase-related gene ( FOXG _10637) in F. oxysporum , resulting in higher chitinase and β -1,3-glucanase activity. However, it should be noted that carvacrol exerted a greater contribution than citral. In conclusion, the combination of carvacrol and citral greatly disrupted the cell wall integrity of F. oxysporum , thereby exhibiting a synergistic effect.
研究领域:
植物病理学
·
微生物学
·
植物化学
·
真菌学
·
农业科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
POSTHARVEST BIOLOGY AND TECHNOLOGY
·
2025
·
IF 6.8
Yuanyuan Chen,Yigui Zeng,Yi Li,Zimao Ye,Liulin Li,Zhiqin Zhou
Spot disease caused by Alternaria alternata ( A. alternata ) commonly occurs in postharvest pears, often resulting in severe rot and considerable economic losses. Here, citral, a natural compound, was found to exhibit potential inhibitory effects against A. alternata . The compound could markedly suppress mycelia growth, with a minimum inhibitory concentration of 0.156 g/L, and simultaneously reduce pear fruit decay. Further analysis revealed that citral altered the hyphal morphology of A. alternata and damaged the integrity of cellular membranes, leading to the release of nucleic acids and proteins. In addition, citral treatment was found to inhibit antioxidant enzyme activity, induce the accumulation of reactive oxygen species, and elevated the malondialdehyde level. It also resulted in a dose-dependent reduction in total cellular lipids, proteins, and sugars. Transcriptomic analysis revealed 1658 upregulated and 2741 downregulated genes in the citral treatment group. Among them, genes related to cell membrane lipids, such as those involved in lipid metabolism, glycerolipid metabolism, steroid biosynthesis, and sphingolipid biosynthesis, were notably enriched. Citral also disturbed fungal energy metabolism by affecting glycolysis/gluconeogenesis, the TCA cycle, and galactose metabolism pathways, which was also confirmed by metabolomic analysis. The results suggest that citral can effectively inhibit A. alternata growth by damaging membrane integrity, activating oxidative stress, and disturbing energy metabolism. Our findings provide new insights into understanding citral as a natural antifungal agent for controlling postharvest black spot disease in pears.
研究领域:
植物学
·
真菌学
·
植物病理学
·
食品科学
·
分子生物学
✓ 已验证
产品关联
DOI
高影响因子
CROP PROTECTION
·
2021
·
IF 2.571
Feng Zheng,Tiantian Li,Hanhong Xu,Pengtong Hu,Ruifei Wang,Zhixiang Zhang,Jinliang Jia
Using plant essential oil instead of chemical pesticides to control melon fly ( Bactrocera cucurbitae (Coquillett)) is still a great challenge in agricultural practices, which must effectively slow down the volatility rate of plant essential oil. In this study, citral as a natural plant essential oil was blended with environmentally friendly castor oil based waterborne polyurethane (PU). The interaction, chemical resistance, adhesion property and sustained release behavior of the composites with different citral content were clarified, and the efficacies against the melon fly under field conditions were explored. The results indicated that the composites prepared exhibited excellent adhesion behavior on bitter gourds ( Momordica charantia L.) even under rainfall washing, meanwhile the chemical resistance of composites could be tailored via controlling citral content. Low citral content composite films could be washed off by alcohol without worrying about the safety of that on crops. The composite prepared exhibited long-lasting repellent behavior against melon fly. The composite can be prepared via a simple technology and low cost, which has great value for plant essential oil applied in agriculture and can provide a new approach for melon fly control.
研究领域:
农业科学
·
昆虫学
·
材料科学
✓ 已验证
产品关联
DOI
高影响因子
JOURNAL OF FOOD SCIENCE
·
2021
·Vol. 86
·期 10
·4554-4565
·
IF 3.167
Wen Wang,Zhihui Ren,Li Wang,Ying Cai,Hang Ma,Liming Fang,Jianyu Su
Combinations of phytochemical(s) and engineered nanoparticles have attracted immense research interest due to their superior antimicrobial effects against contaminations. Herein, a Pickering emulsion is developed with capsulized phytochemicals including borneol and citral (BC–Cap) stabilized by hydrophilic amine-functionalized silica nanoparticles (SiO 2 ─NH 2 NPs). The droplet sizes of Pickering emulsion were 5.2 ± 1.4 µm under the condition that the concentrations of SiO 2 ─NH 2 NPs ranged from 0.6 to 1.2 wt.%, and the emulsion showed desirable stability during storage at 40°C for 365 days. In addition, the antibacterial and antibiofilm activities of the Pickering emulsion were investigated. The antibacterial effect of BC–Cap increased by two- to fourfold compared with citral or borneol alone. Treatment of BC/BC–Cap for 4 h eliminated the formation of biofilms generated by Listeria monocytogenes (at 5/1.25 mg/ml; 2 × MIC concentration) and Pseudomonas aeruginosa (at 5/2.5 mg/ml; 2 × MIC concentration). Further mechanistic studies revealed that the antibiofilm effects of BC–Cap were attributed to its ability to increase the porosity and lytic effects on the cell membrane of bacteria. Findings from the current study support the antibacterial and antibiofilm effects of BC–Cap Pickering emulsion as a promising food additive. Practical Application The Pickering emulsion has potential applications as bacteriostatic agent in packaging materials and general surface disinfectant. The combination of borneol and citral is stabilized by hydrophilic amine-functionalized silica nanoparticles (SiO 2 ─NH 2 NPs). With the synergistic effects of borneol and citral, the Pickering emulsion shows a promising elimination effect against the formation of biofilms produced by Listeria monocytogenes and Pseudomonas aeruginosa .
研究领域:
食品科学
·
纳米技术
·
微生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2021
·Vol. 26
·期 14
·4263
·
IF 4.412
Yin Zheng,Yanhong Shang,Mengyun Li,Yunzhou Li,Wuqing Ouyang
Trichophyton rubrumcauses ringworm worldwide. Citral (CIT), extracted fromPectisplants, is a monoterpene and naturally composed of geometric isomers neral (cis-citral) and geranial (trans-citral). CIT has promising antifungal activities and ergosterol biosynthesis inhibition effects against several pathogenic fungi. However, no study has focused on neral and geranial againstT. rubrum, which hinders the clinical application of CIT. This study aimed to compare antifungal activities of neral and geranial and preliminarily elucidate their ergosterol biosynthesis inhibition mechanism againstT. rubrum. Herein, the disc diffusion assays, cellular leakage measurement, flow cytometry, SEM/TEM observation, sterol quantification, and sterol pattern change analyses were employed. The results showed geranial exhibited larger inhibition zones (p< 0.01 or 0.05), higher cellular leakage rates (p< 0.01), increased conidia with damaged membranes (p< 0.01) within 24 h, more distinct shriveled mycelium in SEM, prominent cellular material leakage, membrane damage, and morphological changes in TEM. Furthermore, geranial possessed more promising ergosterol biosynthesis inhibition effects than neral, and both induced the synthesis of 7-Dehydrodesmosterol and Cholesta-5,7,22,24-tetraen-3β-ol, which represented marker sterols when ERG6 was affected. These results suggest geranial is more potent than neral againstT. rubrum, and both inhibit ergosterol biosynthesis by affecting ERG6.Keywords:neral;geranial;Trichophyton rubrum;ergosterol biosynthesis;ERG6;citral;antifungal activity;dermatophytes
研究领域:
微生物学
·
药理学
·
真菌学
✓ 已验证
DOI
PubMed
高影响因子
CHEMOSPHERE
·
2023
·
IF 8.8
Lei Wu,Xiaolu Gong,Cong Ma,Lan Xu,Ming Li,Chen Lyu,Nan Sun
In this study, hydrogels generated by the Schiff base reaction between citral and chitosan (CS) were used for the first time to improve the anti-bacterial property of forward osmosis (FO) membranes. The composite membranes were characterized by scanning electron microscopy (SEM), Fourier transform infrared (FTIR), Water contact angle (WCA), Zeta potential and confocal laser scanning microscopic (CLSM). In the FO filtration experiment, the membrane performance of TFC-1 with 1 M sodium chloride solution as the draw solution and deionized water as the feed solution was the best, with the water flux of 25.54 ± 0.7 L m −2 h −1 and the reverse salt flux of 4.7 ± 0.4 g m −2 h −1 . Although the hydrogel coating produced a certain hydraulic resistance, the flux of the modified membrane was only reduced by about 8%, compared with the unmodified membrane. However, the anti-bacterial property ( Pseudomonas aeruginosa ) and anti-fouling properties (bovine serum protein and lysozyme protein) of the modified membranes were improved, showing good antibacterial properties (99%) and flux recovery rate (over 90%). The modified method has the advantages of easy access to raw materials, simple operation and no risk of secondary pollution, which can effectively reduce the cost of chemical cleaning and extend the service life of the membrane. The modification of membrane by chitosan-based hydrogel is a promising option in the field of membrane anti-bacteria.
研究领域:
材料科学
·
膜科学与技术
·
生物医学工程
·
环境功能材料
·
抗菌材料
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）