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GENETICA · 2024 ·Vol. 153 ·期 1 ·1-11 · IF 1.3

Glutathione S-transferase TcGSTu1 contributes to defense against eucalyptol in Tribolium castaneum

Gao Shanshan,Cao Yizhuo,Miao Wenbo,Li Dongyu,Zhou Can,Zhang Kunpeng

Eucalyptol is one of the major insecticidal active ingredients in a variety of plant essential oils, and has good killing and avoidance effects on Tribolium castaneum . The presence of detoxifying enzymes glutathione S-transferase (GST) in T. castaneum makes it resistant to a variety of insecticides. However, whether GST is involved in regulating the sensitivity of eucalyptol by T. castaneum is not well understood. In our previous study, a glutathione S-transferase, TcGSTu1 , was significantly up-regulated in RNA sequencing data when T. castaneum was exposed to eucalyptol. Therefore, in this study, the role of TcGSTu1 in the regulating the sensitivity of T. castaneum to eucalyptol was studied. The enzyme activities of GST and the transcription levels of TcGSTu1 were significantly increased following stimulation with eucalyptol. When using RNA interference technology knockdown TcGSTu1 heightens the sensitivity of T. castaneum to eucalyptol, demonstrating a link between TcGSTu1 and eucalyptol detoxification metabolism. Furthermore, TcGSTu1 is expressed in all developmental stages of T. castaneum , with higher expression levels observed particularly in the late egg stage. There was significant expression of TcGSTu1 in various tissues of different organisms, including larval head, fat body, and adult head. This observation indicated a possible connection between high TcGSTu1 expression and eucalyptol detoxification. The present findings suggest that TcGSTu1 may be involved in regulating the sensitivity and response of T. castaneum to treatment with eucalyptol, providing new research insight into pest control.

CAS / MDL: 470-82-6
研究领域: 昆虫学 · 分子生物学 · 害虫防治
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2016 · IF 2.196

(Liquid + liquid) extraction of phenols from aqueous solutions with cineole

Hengde Li,Li Wan,Guoqiang Chu,Wei Tan,Baoyu Liu,Yanlin Qin,Yuqing Feng,Dalei Sun,Yanxiong Fang

As an eco-friendly compound and good solvent, cineole (1,8-cineole, eucalyptol) has been evaluated for the extraction property of phenols (phenol or p-cresol) from aqueous solutions. This paper presents experimental (liquid   +   liquid) equilibrium (LLE) data for the ternary (water   +   phenol   +   cineole) and (water   +   p-cresol   +   cineole) mixtures from high concentration to low concentration of phenols-water solution. The mutual solubility of the binary (water   +   cineole) and (water   +   phenol or p-cresol) systems, and the LLE results for the ternary systems were determined with a tie-line method at T   =   (283.15, 298.15, and 313.15)   K under atmospheric pressure. The experiment LLE results showed that cineole as a good extractant exhibited high extraction   ability for phenol or p-cresol from aqueous solutions. The influence of temperature on the (liquid   +   liquid) phase equilibria was studied.   The well-known Hand and Bachman equations were used to test the reliability of the experimental values. Moreover, the experimental LLE results were satisfactorily correlated by the NRTL and UNIQUAC models.

研究领域: 化学工程 · 环境科学
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JOURNAL OF ENTOMOLOGICAL SCIENCE · 2024 · IF 0.7

An Epsilon Class Glutathione S-Transferase Gene Contributes to the Phytochemical Susceptibility of Tribolium castaneum (Coleoptera: Tenebrionidae)1

Gao Shanshan,Li Dongyu,Zhou Can,Zhu Min,Zhang Yonglei,Li Ruimin,Zhang Kunpeng

Evidence is accumulating that insect epsilon class glutathione S-transferases (GSTs) play an important role in the resistance to xenobiotics such as insecticides. A Tribolium castaneum (Herbst) (Coleoptera: Tenebrionidae) epsilon class GST gene, TcGSTe17 , was previously found to be significantly induced following exposure to the plant derivative eucalyptol. However, whether TcGSTe17 is involved in resistance to eucalyptol remains unclear. In this study, TcGSTe17 was cloned from the T. castaneum . Development stage expression profiling revealed that TcGSTe17 was expressed at all development stages of T. castaneum but was highly expressed in late-stage larvae. Subsequent expression profiling of tissues showed that TcGSTe17 was highly expressed in the gut of larvae and the fat body of adults, and also revealed gender-specific expression patterns. In addition, the transcripts of TcGSTe17 were significantly increased following exposure to eucalyptol, and RNAi increased the susceptibility of the beetles to eucalyptol. Collectively, these results suggest that TcGSTe17 contributes to the susceptibility of T. castaneum to eucalyptol. These findings provide new data for the prevention of pest resistance.

研究领域: 昆虫学 · 分子生物学 · 害虫防治
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2023 · IF 4.7

Eucalyptol ameliorates chlorpyrifos-induced necroptosis in grass carp liver cells by down-regulating ROS/NF-κB pathway

Naixi Yang,Jinming Guo,Hao Wu,Meichen Gao,Shiwen Xu

Chlorpyrifos (Diethoxy-sulfanylidene-(3,5,6-trichloropyridin-2-yl) oxy-λ 5 -phosphane, CPF) was extensively used organophosphorus pesticide , extensively deteriorating public problem with the enrichment in the water bodies. Eucalyptol (1,3,3-Trimethyl-2-oxabicyclo[2.2.2] octane, EUC), a colorless cyclic monoterpene oxide, has shown anti-inflammatory and anti-oxidation properties. To explore the effect of EUC on CPF-induced necroptosis in the grass carp liver cells (L8824 cells), we treated L8824 cells with 60 mM CPF and 5 μM EUC for 24 h. The results showed that CPF exposed lead to excessive accumulation of reactive oxygen species (ROS) and oxidative stress , activating the NF-κB and RIPK1 pathway, increasing the level of cell necroptosis. However, EUC treatment attenuated the toxic effects of CPF treatment on L8824 cells. In summary, the study demonstrated that CPF induced necroptosis and inflammation, and EUC treatment could decrease CPF-caused cell injury.

CAS / MDL: 2921-88-2 5895-48-7
研究领域: 环境毒理学 · 细胞生物学 · 药理学
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Processes · 2024 ·Vol. 12 ·期 3 ·498 · IF 2.8

Determination of 24 Trace Aromatic Substances in Rosemary Hydrosol by Dispersed Liquid–Liquid Microextraction–Gas Chromatography

Xiaoming Zeng,Hao He,Liejiang Yuan,Haizhi Wu,Cong Zhou

A combined dispersed liquid–liquid microextraction (DLLME) and chromatography (GC) method was developed for the determination of 24 aromatic substances in rosemary hydrosol in this work. The pretreatment method of DLLME was optimized by carefully selecting the appropriate extraction agents, dispersants, and their respective amounts. With carbon tetrachloride as the extractant and acetone as the dispersant, the enrichment factor of DLLME is 13.3, and the 24 target substances such as eucalyptol, camphor and verbenone can be separated within 31 min and quantified by an external standard method using gas chromatography (GC). The correlation coefficient r2of the linear regression equation is within the range of 0.9983 to 0.9991. The detection limit of the method was 0.02 mg/L, the recovery rate of the spiked solution was 76.4–118.4%, the relative standard deviation was 0.4–6.9% and the method was used to detect the semi-finished products of rosemary hydrosol and the finished rosemary hydrosol sold on the market. This method also provides a reference for the qualitative and quantitative determination of aromatic substances in other hydrosols.

研究领域: 分析化学 · 环境科学 · 植物化学 · 食品科学
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Journal of Essential Oil Bearing Plants · 2022 · IF 1.971

Isolation, Antibacterial, Nematicidal and Anxiolytic Activities of Essential Oil from Cinnamomum longepaniculatum (Gamble) N. Chao ex H. W. Li Leaves

Yuanyuan Zhang,Lin Zhang,Yongbin Meng,Yuangang Zu,Feng Han,Xiuhua Zhao

The utilization of natural product resources is significant for economic growth and health care. Herein, Cinnamomum longepaniculatum essential oil (CLEO) was isolated by microwave-assisted hydrodistillation (MAH). The composition of CLEO was determined by gas chromatography/mass spectrometry (GC/MS), and the antibacterial, nematicidal and anxiolytic activities of CLEO were evaluated. GC/MS results revealed that 33 compounds were identified, accounting for 99.87% of the total identified compounds. The major components of CLEO were monoterpenes, including β-myrcene (22.55%), eucalyptol (11.59%), α-pinene (11.56%), terpinen-4-ol (8.63%). Further research found that CLEO can inhibit the growth of Staphylococcus aureus (MIC 7.13 mg/mL, MBC 14.25 mg/mL), Escherichia coli (MIC 14.25 mg/mL, MBC 57 mg/mL), and Pseudomonas aeruginosa (MIC 14.25 mg/mL, MBC 28.50 mg/mL), the zone of inhibition were 17.49 ± 0.51 mm, 13.35 ± 0.27 mm and 15.15 ± 0.31 mm, respectively. CLEO could increase cell membrane permeability and make β-galactosidase, protein and other substances leak from the cell. Importantly, CLEO was first used to kill pine wood nematodes (PWN, Bursaphelenchus xylophilus). It was found that CLEO was toxic to B. xylophilus (LC50=30.81 mg/mL), and PWN treated with CLEO rapidly died and extended. Furthermore, CLEO was used in anxiolytic for the first time. CLEO inhalation can effectively relieve anxiety-like behaviors in open-field test (OFT) and elevated plus-maze test (EPT), and restore neurotransmitters (5-HT, NE, GABA) in brain tissue to normal levels. This study provides a strategy for the industrial production of CLEO and discovers its potential role in food transportation and preservation, forest pest control, and relief of emotional disorders such as anxiety and stress, which are beneficial to health care and economic development and provides a basis for broader application of CLEO.

CAS / MDL: 9048-46-8 369-07-3
研究领域: 药理学 · 植物科学 · 微生物学 · 神经科学
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Arabian Journal of Chemistry · 2023 · IF 6

Chemical characterization, antioxidant, antimicrobial, enzyme inhibitory and cytotoxic activities of Illicium lanceolatum essential oils

Tianming Zhao,Guang Fan,You Tai,Xinhe Shu,Fu Tian,Shuliang Zou,Qin Wu

Illicium lanceolatum is a medicinal and aromatic plant widely distributed in the south of China. The reports on chemical composition and biological activities of its essential oils (EOs) were very limited. In this study, Illicium lanceolatum EOs were extracted by hydro distillation, and analyzed by GC–MS and GC-FID. DPPH radical scavenging assay, ABTS cation radical scavenging assay and ferric reducing/antioxidant power (FRAP) assay were used for antioxidant activity evaluation. Minimum inhibitory concentrations (MICs) and minimum microbiocidal concentrations (MMCs) against 9 microorganisms were determined. The inhibitory effects on tyrosinase, α -glucosidase and cholinesterases were evaluated and cytotoxic activities were evaluated using MTT assay. The results revealed 110 identified compounds, with asaricin, eucalyptol, linalool and caryophyllene oxide as major compounds. Eucalyptol was the most abundant compound in the stem, leaf and fruit EOs while asaricin accounted for 50.52 ± 0.33 % in the root EO. Very weak radical scavenging capacities were noticed for all EOs, but the root EO showed moderate antioxidant activity (176.33 ± 4.52 mg TE/g of EO) in the FRAP assay, which could be attributed to asaricin. The root EO displayed better antimicrobial activities than other three EOs, with MIC values as 3.13 mg/mL against three bacteria including Staphylococcus aureus BNCC 186335, Bacillus cereus BNCC 103930 and Listeria monocytogenes BNCC 336877. Camphor and borneol were found to be important antimicrobial compounds. No inhibitory effect on α -glucosidase was found. The leaf EO displayed better acetylcholinesterase inhibitory activity (17.79 ± 0.32 mg GE/g of EO) while the root EO showed better tyrosinase (30.34 ± 0.40 mg KAE/g of EO) and butyrylcholinesterase (43.25 ± 1.50 mg GE/g of EO) inhibitory activities. Molecular docking between active compounds and enzymes revealed the main interactions as hydrophobic interaction, hydrogen bond and π -stacking. All EOs displayed weak cytotoxicity to HK-2 cells of normal kidney at six tested concentrations. The leaf EO showed strong anticancer activities to HepG2 cells at the concentration of 500 μg/mL. I. lanceolatum EOs showed promising prospects with possible applications in pharmaceutical and cosmetic industries.

CAS / MDL: 140-67-0
研究领域: 药理学 · 生物化学 · 微生物学 · 植物科学 · 药物化学
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JOURNAL OF CHROMATOGRAPHY A · 2025 · IF 4

An unconventional separation method of α-Terpineol from its isomer 1,8-Cineole via in situ-association formation of deep eutectic solvent and machine learning

Yingjie Luo,Junjie Qiu,Qiwei Xu,Jing Wei,Hang Song,Beibei Guo,Xuesong Liu,Yong Chen,Tengfei Xu

α-Terpineol and 1,8-cineole are two important compounds in essential oils. This study developed an efficient method to recover α-terpineol from model oil (MO) based on association extraction by in situ formations of deep eutectic solvent (DES) between α-terpineol and some quaternary ammonium salts (QASs) by hydrogen-bond (HB) interaction. Such interaction could be broken almost completely by the introduction of water, due to the stronger HB interaction between water and QASs, which could release α-terpineol by liquid-liquid separation and save the organic solvents consumption. QASs were screened by gaussian energy calculation and experimental verification. Subsequently, the effect of physicochemical properties of the quaternary ammonium salts on the weak interaction between QASs and α-Terpineol was also screened using random forests model. Tetrabutylammonium chloride (TBAC) was proved to form DES with α-terpineol but not with 1,8-cineole, which was proved by FT-IR and 1 H nuclear magnetic resonance ( 1 H NMR) spectroscopy. After response surface methodology (RSM) and Genetic Algorithm-Back Propagation (GA-BP) neural network optimization, the distribution ratio and selectivity of α-terpineol to 1,8-cineole could reach a high value of 29.6 and 42.2. The α-terpineol could achieve a purity up to 99.6% with a recovery of 88.8% by the two-step back-extractions using n -hexane and water. Furthermore, camphor leaf essential oil was used to demonstrate the reliability of the method for further application. In this separation process, all reagents including organic salt, n -hexane and water could be recovered and reused. It provides an alternative and promising method for the economical and green treatment of essential oils.

研究领域: 化学工程 · 分析化学 · 人工智能
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2024 · IF 1.3

Allelopathic Influence of Artemisia lancea Essential Oil on Selected Broad and Narrow Weeds

Shan Zixiang,Zhou Shixing,Arafat Yasir,Shi Kai,Shao Hua

The present study analyzed the chemical composition and phytotoxic activity of Artemisia lancea essential oil (EO). Gas chromatography-mass spectrometry (GC-MS) results showed the presence of 55 compounds, representing 82.36% of the entire EO, with eucalyptol (18.7%) being the most abundant constituent. Phytotoxic bioassay results indicated that the EO (concentration ranging from 0.25-5 mg mL−1) inhibited the growth of Amaranthus retroflexus and Setaria viridis. Root length of A. retroflexus and S. viridis were reduced with the increasing concentration of the EO, especially when the EO was applied at 1-5 mg mL−1. When treated with 1-5 mg mL−1 EO, shoot length of A. retroflexus and S. viridis were also significantly suppressed. The half maximal inhibitory concentration (IC50) values for inhibiting root and shoot growth of A. retroflexus by the EO were 0.284 and 0.246 mg mL−1; for S. viridis, the EO showed IC50 values of 0.44 and 0.262 mg mL−1 for root and shoot inhibition, respectively. The most promising findings were observed when A. lancea EO concentration reached 1 mg mL−1 and higher, which completely inhibited seed germination of A. retroflexus and S. viridis. These findings suggest A. lancea EO has potential as an eco-friendly bioherbicide for agricultural weed control.

CAS / MDL: 470-82-6
研究领域: 植物学 · 农业科学 · 生态学
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FOOD CHEMISTRY · 2024 · IF 8.5

Comprehensive foodomics analysis reveals key lipids affect aroma generation in beef

Longzhu Zhou,Yimeng Ren,Yujie Shi,Shijie Fan,Liyuan Zhao,Miaomiao Dong,Jing Li,Youyou Yang,Yanan Yu,Qingyu Zhao,Junmin Zhang,Chaohua Tang

Lipids are vital precursors to beef aroma compounds, but the exact lipid molecules influencing aroma generation remain unconfirmed. This study employs gas chromatography–olfactometry–mass spectrometry and absolute quantitative lipidomics to identify beef's aroma and lipid profiles and to examine lipid alterations post-thermal processing. The aim is to understand the role of lipids in aroma generation during beef's raw-to-cooked transition. Eighteen key aroma compounds were identified as significant contributors to the aroma of beef. 265 lipid molecules were quantified accurately, and we found that triglycerides containing C18:1 or C18:2 chains, such as TG(16:0_18:1_18:1), TG(16:0_18:1_18:2), TG(16:0_16:1_18:1), as well as phosphatidylcholine and phosphatidylethanolamine containing PC(16:1e_20:4), PC(16:0e_20:4), PC(18:2e_18:2), and PE(16:1e_20:4), played important roles in the generation of key aroma compounds in beef. C18:1, C18:2, C18:3, and C20:4 were key substrates for the formation of aroma compounds. In addition, lysophosphatidylcholine and lysophosphatidylethanolamine containing unsaturated fatty acid chains may serve as important aroma retainers.

研究领域: 食品科学 · 分析化学 · 生物化学
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AICHE JOURNAL · 2024 ·Vol. 70 ·期 9 ·e18495 · IF 3.5

Biobutanol extraction and dehydration with eucalyptus oil yielding linear and cyclic biofuel blends

Jialin Tan,Hao Huang,Hengde Li,Xiaolan Cai,Guangping Zhou,Boxi Zeng,Jinrui He,Xiang Wang,Shaoqu Xie

The biobutanol-based biofuel fermentation is hindered by the challenge of inadequate fermentation broth concentration and the azeotropic systems of water. The application of eucalyptus oil in diesel fuel makes it a promising extractant for biobutanol extraction and dehydration, thus resulting in product recovery and the development of fuel blend technology. Eucalyptus oil-derived 1,8-cineole was applied to acetone-butanol-ethanol (ABE) and isobutanol systems to enhance the butanol recovery and dehydration. The recovery of n-butanol and isobutanol reached 92% and 95%, respectively, while the water removal in a 2% butanol system exceeded 99%. These results demonstrated that 1,8-cineole exhibited a high selectivity toward butanol, thus providing a robust theoretical foundation for the fermentation-based biofuel recovery and the elimination of azeotropic systems. The introduction of high-density diesel-fuel-like eucalyptus oil into low-energy-density biobutanol will increase the energy density of fermentation-based alcohols, yielding linear and cyclic biofuel blends.

CAS / MDL: 470-82-6
研究领域: 生物化学 · 能源生物学
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PEST MANAGEMENT SCIENCE · 2024 · IF 3.8

Enhancing agrochemical delivery in citrus leaves with geraniol: a promising strategy for controlling huanglongbing (HLB)

Shuning Chen,Ao Yuan,Huafeng Wang,Daibin Yang,Li Cui,Fengjiao Hao,Xiaojing Yan,Huizhu Yuan

BACKGROUND Citrus huanglongbing (HLB) is a devastating disease in citrus, caused by Candidatus Liberibacter asiaticus (CLas), which primarily resides in the phloem where chemicals cannot effectively reach, posing a significant challenge in controlling HLB. To address these challenges, plant essential oils (EOs), widely used as transdermal enhancers and known for their benefits for plant tissues, were investigated for their potential to enhance chemical permeation. RESULTS In this study, seven EOs – eugenol, carvacrol, eucalyptol, geraniol, linalool, cinnamaldehyde, and d -limonene – were evaluated for their potential to enhance chemical penetration into citrus leaves. Preliminary screening with tracer methods revealed that geraniol provided the greatest enhancement of permeation, achieving the deepest and broadest distribution into the spongy tissue of the citrus leaf. The permeation levels of rhodamine B and crystal violet through the cuticular layer were elevated from 0.55 mg L −1 and 0.11 mg L −1 to 20.04 mg L −1 and 7.14 mg L −1 , respectively, by the addition of geraniol. Further validation through high-performance liquid chromatography–mass spectrometry (HPLC–MS) confirmed that the penetration of fludioxonil and tetracycline into citrus leaf tissues was enhanced by 15.07-fold and 20.43-fold, respectively. In planta experiments confirmed that adding geraniol to tetracycline and oxytetracycline via foliar application eliminated CLas bacteria in HLB-affected citrus more efficiently than controls. CONCLUSION Our study underscores the potential of geraniol as an effective EO-based permeation enhancer for combating HLB. By significantly improving the delivery and efficacy of bactericidal treatments, geraniol offers a promising strategy for managing this catastrophic citrus disease, potentially transforming the approach to controlling HLB. © 2024 Society of Chemical Industry.

研究领域: 植物病理学 · 农业化学 · 植物化学
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