CHEMICAL ENGINEERING SCIENCE
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2022
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IF 4.889
Jie Liu,Jianhao Cui,Lei Chen,Jingjing Chen,Huidong Zheng,S. Ted Oyama
The conversion of terpinolene epoxide to terpinen-4-ol is a desirable chemical transformation for the production of a valuable intermediate. This paper describes a one-pot, two-step system for the reaction that uses a bifunctional Ni/TiO 2 -SiO 2 catalyst with isomerization and hydrogenation capabilities. The TiO 2 -SiO 2 serves to isomerize the starting epoxide. The Ni component works to hydrogenate the allylic double bond. The tandem system achieves a high 64% yield of terpinen-4-ol. X-ray diffraction analysis showed that TiO 2 -SiO 2 was a mixed binary oxide, and Fourier transform infrared spectroscopy of adsorbed pyridine suggested that acid sites were mainly Lewis acid sites. Electron microscopy showed that the Ni/TiO 2 -SiO 2 catalyst consisted of spherical particles comprising a titanosilicate phase with highly dispersed zero-valent Ni or anatase on the surface. Additionally, there was strong interaction between Ni and the TiO 2 -SiO 2 mixed oxides. Control kinetic experiments demonstrated that the tandem use of the catalysts was more effective than simultaneous operation.
研究领域:
化学工程
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催化科学
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高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2025
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IF 6.2
Mengli Chen,Zhanyi Xu,Guoxing Chen,Peitong Chen,Chunxia Tian,Jiali Qian,Tiefeng Song,Yongfeng Jin,Guonian Zhu,Ru Yan
Numerous essential oils have been well acknowledged as eco-friendly alternatives to combat insect pests due to synthetic insecticide-induced pest resistance and environment pollution. As a highly commercial essential oil, tea tree oil exhibits excellent insecticidal and repellent activities. However, the molecular mechanism of the olfactory system mediating the tea tree oil-induced repellency against insect pests remains unknown. In our study, mosquito was used as a suitable model to examine the molecular mechanism of tea tree oil-induced repellency against insect pests. The results showed that tea tree oil exhibited excellent spatial and oviposition repellency against Aedes aegypti adults and outstanding repellency against larvae, which were conferred by the main constituent terpinen-4-ol. The reduced repellency in the Orco–/– mutant strain revealed that tea tree oil-induced repellency against mosquitoes was dependent on odorant receptor(s). Moreover, we identified one antenna-biased odorant receptor, AaOr96, that was involved in detecting constituents of tea tree oil to elicit repellency, and the predicted protein–ligand complex indicated that AaOr96 interacted with terpinen-4-ol via van der Waals forces from five key residues. Finally, knocking out AaOr96 resulted in a reduced spatial repellency against A. aegypti by tea tree oil and terpinen-4-ol, and a reduced oviposition repellency by terpinen-4-ol, but not by tea tree oil. Our study not only reveals that tea tree oil has great potential in pest management but also provides more insights into the molecular basis of repellency of essential oils.
研究领域:
昆虫学
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分子生物学
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害虫管理
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DOI
PubMed
高影响因子
JOURNAL OF ASIA-PACIFIC ENTOMOLOGY
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2022
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IF 1.58
Shan-shan Gao,Yong-lei Zhang,Kun-peng Zhang,Xing-yun Wang,Qing-bo Tang,Yuan-chen Zhang
The terpene, terpinen-4-ol (T4ol), exhibits contact toxicity in Tribolium castaneum . However, the molecular mechanisms underlying this toxicity have not been elucidated. This study examined changes in the expression of four classic enzymes after exposure of T. castaneum to T4ol. Acetylcholinesterase and glutathione S-transferase activities were markedly inhibited after exposure to T4ol, while that of the detoxifying enzyme cytochrome oxidase P450 increased markedly. Carboxylesterase activity did not show significant changes. Furthermore, RNA sequencing revealed 260 differentially expressed genes (DEG) between the T4ol-treated and control samples, and qRT-PCR was used to validate the RNA-Seq data. The Gene Ontology analysis classified the DEGs into 36 functional groups, including the immune system processes, response to stimulus, and developmental processes. T4ol altered the response to stimulus and the immune system process of beetles by inducing the expression of the genes Stabilin-1, Attacin 1, and Defensin 1. Furthermore, the DEGs receptor tyrosine kinase Torso-like protein ( RTKTsl ), Frizzled 4 ( Fz4 ), Protein Wnt-5b, Ecdysone-induced protein 78C ( E78 ), Zinc finger protein GLIS1 ( ZFPGLIS1 ) were classified as participating in beetle development, and Fz4 and Protein Wnt-5b also mapped to the Wnt signaling pathway. This indicated that pathways associated with development are inhibited after exposure to T4ol. T4ol also induced CYP9Z6 / GSTs7 overexpression, and RNAi targeting these genes significantly increased larvae mortality on T4ol exposure, supporting the participation of CYP9Z6 / GSTs7 in the response to T4ol in T. castaneum . The results of this study will facilitate understanding of the toxic mechanisms of T4ol and provide a basis for controlling the pests of stored products.
研究领域:
昆虫学
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毒理学
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分子生物学
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基因组学
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DOI
高影响因子
FLAVOUR AND FRAGRANCE JOURNAL
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2014
·Vol. 30
·期 2
·179-187
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IF 1.761
Zujin Yang,Zuobing Xiao,Hongbing Ji
Terpinen-4-ol has several biological properties, but its low stability and water-solubility limit its use. This study reports the formation of a solid terpinen-4-ol/ β -cyclodextrin ( β -CD) inclusion complex via lyophilization. Release experiments were performed at various temperatures (40, 60, 80, and 100°C) with humidity of 70%. The release of terpinen-4-ol was significantly increased with rising temperature. Avrami's equation was used to analyse release kinetics and a good fit was observed for terpinen-4-ol release. In addition, the complex enhanced antibacterial activity against Staphylococcus aurueus, Pseudomonas aeruginosa and Escherichia coli , with concentration ranging from 1.25 mg/ml to 5 mg/ml. To explain the experimental data, physico-chemical techniques have been utilized to investigate the inclusion complex of terpinen-4-ol with β -CD. Finally, the possible structure of the complex was proposed by quantum chemical calculations. The results indicated that enhanced thermal stability and antibacterial activity of terpinen-4-ol could be attributed to the weak interactions of hydrogen bonds between terpinen-4-ol and β -CD. Copyright © 2014 John Wiley & Sons, Ltd.
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高影响因子
JOURNAL OF MOLECULAR STRUCTURE
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2026
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IF 4.9
Zhaomei Huo,Zhixia Wang,Fulin Li,Hang Song
Artificial formulation has higher antibacterial activity than tea tree oil (TTO). • The formation and physical properties of nanoemulsions is studied systematically. • Nanoemulsions exhibit superior antibacterial efficacy than reported nano-TTO. • Chitosan and the essential oil components exhibit a synergistic antibacterial effect. The volatility and instability of essential oil components often limit their practical application in antibacterial materials. In this study, a chitosan-based nanoemulsion (NE) loaded with an artificially designed synergistic formulation of two key components from tea tree oil (TTO) was developed to achieve enhanced and sustained antibacterial activity. The optimal 9:1 (v/v) ratio of terpinen-4-ol to 1,8-cineole, produced inhibition zones of 25.8 mm against S. aureus and 22.8 mm against E. coli , thereby outperforming commercial TTO (14.5 mm and 12.5 mm). Guided by pseudo-ternary phase diagrams, the formation of NE was determined. A 3:1 mass ratio of surfactant Tween 80 to co-surfactant ethanol yielded the largest nanoemulsifying region (38.33%), whereas 0.1% chitosan aqueous solution provided optimal antibacterial efficacy, uniform particle size (Z-Ave: 16.89 nm; PDI: 0.26), and good stability. Conductivity and viscosity changes were conducted to analysis the critical transition points of NEs, and NEs transitioned to the oil in water (O/W) phase when chitosan aqueous content exceeded 60% by mass. Interestingly, unlike the essential oil, the nanoemulsion exhibited higher antibacterial activity against E. coli than S. aureus , with minimum inhibition concentration of 3.91 μL·mL -1 and 7.81 μL·mL -1 , respectively. Chitosan rendered the nanoemulsion positively charged, facilitating easier interaction with the negatively charged cell walls of gram-negative bacteria. SEM revealed that NEs disrupted bacterial cell wall and membrane structures, leading to cell death and antibacterial activity. Additionally, the NEs demonstrated notable long-lasting effects. Overall, these eco-friendly NEs offer a promising alternative to antibiotics, especially for gram-negative bacteria inhibition. We designed chitosan-based nanoemulsion (NE) loaded with an artificially designed synergistic formulation of two key components from tea tree oil (TTO), achieving enhanced and sustained antibacterial activity. Guided by pseudo-ternary phase diagrams, the formulation of NE was determined. Moreover, conductivity and viscosity changes were conducted to analysis the critical transition points of NEs. Notably, the nanoemulsion exhibited minimum inhibition concentration of 3.91 μL·mL -1 and 7.81 μL·mL -1 against Escherichia coli and Staphylococcus aureus , respectively, which outperformed reported nano-TTO of 48.8 μL·mL -1 . Additionally, the NEs demonstrated notable long-lasting effects. Overall, these eco-friendly NEs offer a promising alternative to antibiotics. Download: Download high-res image (263KB) Download: Download full-size image
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高影响因子
FOOD CONTROL
·
2023
·
IF 6
Lingling Yu,Xingxing Wang,Yingying Wei,Shu Jiang,Jianfen Ye,Yi Chen,Feng Xu,Hongfei Wang,Xingfeng Shao
Terpinen-4-ol has potent antifungal activity and controls decay in postharvest strawberry fruit. In order to overcome the unstable and volatile characteristics of terpinen-4-ol, a γ-cyclodextrin (γ-CD) metal-organic framework (MOF) with high porosity and large specific surface area was synthesized by vapor diffusion and ultrasonic mixing. Terpinen-4-ol-loaded γ-CD-MOF (γ-CD-MOF/Ter) was then prepared using physical adsorption. Scanning electron microscopy, X-ray diffraction, Fourier transform infrared spectroscopy analysis, and nitrogen adsorption-desorption showed that terpinen-4-ol was successfully loaded into the center of the γ-CD-MOF structure, and that encapsulation efficiency and drug loading reached 53.61% and 9.31%, respectively. γ-CD-MOF/Ter reduced the release rate of terpinene-4-ol, and exhibited the higher antifungal effect against B. cinerea in vitro test. Meanwhile, it was effective in controlling gray mold and maintaining the quality of strawberry fruit. We conclude that γ-CD-MOF loads terpinen-4-ol and reduces its volatilization and has potential application in the preservation of strawberry fruit.
研究领域:
材料科学
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食品科学
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植物病理学
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DOI
高影响因子
SEPARATION AND PURIFICATION TECHNOLOGY
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2025
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IF 9
Lijiao Yu,Lihong Deng,Jieyu Wu,Subhan Mahmood,Ke Yuan,Haoran Wu,Xiaodong Wang,Jing Zhang,Shun Yao
As a key component in tea tree oil (TTO), terpinen-4-ol exhibits ideal physiological activities. However, the high content of terpenes in crude TTO makes it challenging to enrich terpineol-4-ol. In this study, molecular simulations combined with experimental methods were used to select the optimal hydrogen bond acceptor (HBA), tetrabutylammonium chloride (TBAC), which forms a deep eutectic solvent (DES) with terpinen-4-ol in situ. Combined with necessary post-treatment process, it provided a feasible way for purification of TTO. Related DESs were prepared and characterized, and their main properties were also investigated. When the amount of TBAC was three times that of terpinen-4-ol, the formation of hydrogen bonds became more pronounced. At this point, the DES achieved its highest distribution coefficient for terpinen-4-ol (D t = 15.02), as well as superior selectivity for terpinen-4-ol (S t/c = 24.59, S t/γ = 57.69). Water as the back-extractant and n-hexane as the auxiliary extractant facilitated the deep purification of terpinen-4-ol. Response surface analysis and experimental results confirmed that the optimal enrichment conditions were 30 min of enrichment time, an enrichment temperature of 60℃, and 0.5 g/g of n-hexane dosage. The back-enrichment and recovery of TBAC also proved to be satisfactory, and when applied to real tea oil, the developed method achieved over 90 % enrichment efficiency for terpinen-4-ol.
研究领域:
化学工程
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植物化学
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DOI
高影响因子
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
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2025
·Vol. 26
·期 16
·7702
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IF 4.9
Xinyue Jiang,Liang Fei,Yayun Yang,Jiao Han,Zhaoxin Tang,Jianzhao Liao,Lianmei Hu,Ying Li,Jiaqiang Pan
Pulmonary hypertension syndrome (PHS), a metabolic disorder causing economic losses in broilers, arises from hypoxia-induced portal hypertension and liver cirrhosis, triggering mitochondrial oxidative damage, excessive ROS production, and altered mitochondrial biogenesis. This study explored terpinen-4-ol (T4O), known for antimicrobial and anti-inflammatory properties, in mitigating PHS. Broilers were divided into four groups, including PHS-affected birds with/without T4O supplementation. Analyses revealed that PHS birds exhibited reduced antioxidant capacity, elevated MDA and ROS levels, increased mitochondrial numbers, and upregulated expression of oxidative stress markers (Keap1, HO-1, Nrf-2) and mitochondrial biogenesis regulators (PGC-1α, Nrf-1, Tfam). T4O administration enhanced antioxidant activity, reduced ROS and MDA, suppressed compensatory mitochondrial proliferation, and downregulated Keap1/Nrf-2 and mitochondrial biogenesis pathways. These effects suggest that T4O alleviates hypoxia-driven oxidative stress and mitochondrial dysfunction in broilers. Findings highlight T4O’s potential as a therapeutic agent to mitigate PHS-related losses in poultry production.
研究领域:
兽医学
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动物营养
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分子生物学
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家禽科学
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药理学
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DOI
PubMed
高影响因子
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