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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2009 · IF 2.063

Solid−Liquid Equilibria in Binary Mixtures of 1,8-Cineole with p-Cymene, β-Pinene, and Camphene

Dongwei Wei,Lishuo Wang,Chao Zhang

Solid−liquid equilibria have been measured for binary mixtures of 1,8-cineole with p-cymene, β-pinene, and camphene, respectively, using differential scanning calorimetry (DSC) over the whole composition concentration range. All three are simple eutectic systems. The eutectic point of the (1,8-cineole (1) + p-cymene (2)) mixture is at 200.0 K and x1 = 0.124, the (1,8-cineole (1) + β-pinene (2)) mixture at 205.6 K and x1 = 0.154, and the (1,8-cineole (1) + camphene (2)) mixture at 251.8 K and x1 = 0.582. An empirical equation of Ott and Goates was used for correlating the experimental data.

研究领域: 物理化学 · 热力学
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FLUID PHASE EQUILIBRIA · 2023 · IF 2.6

Liquid–liquid equilibria of ternary water—ethyl acetate—1,8-cineole system at different temperatures

Hengde Li,Hongna Qin,Shan Jiang,Bao Wang,Jianjiang Zeng,Kaiming Chen,Hao Tang,Yanxiong Fang

To separate and purify ethyl acetate (EA) from water, the ternary (water + ethyl acetate + 1,8-cineole) liquid–liquid equilibria at T  = (283.15, 298.15 and 313.15) K under atmospheric pressure were studied. The extraction capacity of 1,8-cineole as an extractant in the separation of EA from aqueous solution was researched. The influence of temperature on the LLE was examined. High distribution ratio and selectivity coefficient obtained reveal the extraction ability and potential of 1,8-cineole as a green solvent . Additionally, the experimental LLE data were satisfactorily correlated by the NRTL and UNIQUAC models, and the binary interaction parameters were validated using a graphical user interface (GUI) by MATLAB.

CAS / MDL: 470-82-6 141-78-6
研究领域: 化学工程 · 环境科学
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JOURNAL OF MOLECULAR LIQUIDS · 2022 · IF 6.633

Separation of 1,8-Cineole and terpenes by Liquid-liquid extraction with green alkanediols

Ke Yuan,Fulin Li,Lincai Peng,Xiaomeng Zhao,Hang Song

The difficulty of high purification of 1,8-cineole was mainly attributed to terpenes in plant essential oils. Therefore, the separation of 1,8-cineole and terpenes is significant for the preparation of high-purity 1,8-cineole. In this work, liquid–liquid extraction for high-purity 1,8-cineole was investigated with a series of low toxicity alkanediol extractants and some influence factors to the extraction were explored. 1,3-propanediol among alkanediols exhibited satisfactory purification effect on 1,8-cineole in model oil with high selectivity (7.02). Then, the back-extraction of 1,8-cineole and the extractant recovery were investigated with satisfactory results. Furthermore, the mechanism between the extractant and the target molecule in the extraction was studied by the molecular level through quantum computational chemistry. Finally, the whole liquid–liquid process was verified using real oil, Cinnamomum longepaniculatum oil , as raw material for considering its application and the high-purity of 1,8-cineole (98.3%) was achieved.

研究领域: 植物化学 · 分离技术 · 理论化学
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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 APPLIED MICROBIOLOGY · 2015 ·Vol. 119 ·期 5 ·1253-1262 · IF 2.479

Antifungal modes of action of tea tree oil and its two characteristic components against Botrytis cinerea

Yu D.,Wang J.,Shao X.,Xu F.,Wang H.

AimsThe essential oil of Melaleuca alternifolia (tea tree) has been evaluated as a potential eco‐friendly antifungal agent against Botrytis cinerea. In this study, we investigated the antifungal activity and mode of action of tea tree oil (TTO) and its components against B. cinerea.Methods and ResultsOf the components we tested in contact phase, terpinen‐4‐ol had the highest antifungal activity, followed by TTO, α‐terpineol, terpinolene, then 1,8‐cineole. As one of characteristic components of TTO, terpinen‐4‐ol treatment led to pronounced alterations in mycelial morphology, cellular ultrastructure, membrane permeability under scanning electron microscope, transmission electron microscope and fluorescent microscope, and also reduced the ergosterol content of fungi. As another characteristic component, 1,8‐cineole caused serious intracellular damage but only slightly affected B. cinerea otherwise. When terpinen‐4‐ol and 1,8‐cineole were used together, the synergistic antifungal activity was significantly higher than either component by itself.ConclusionsThe results of our study confirmed that terpinen‐4‐ol and 1,8‐cineole act mainly on the cell membranes and organelles of B. cinerea, respectively, and when combined are similar to TTO in antifungal activity due to their differences.Significance and Impact of the StudyUnderstanding the mechanism of terpinen‐4‐ol and 1,8‐cineole antifungal action to B. cinerea is helpful for investigation on their synergistic effect and explaining antifungal action modes of TTO.

CAS / MDL: 98-55-5 10482-56-1
研究领域: 植物学 · 真菌学 · 农业科学
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FOOD HYDROCOLLOIDS · 2020 · IF 7.053

Optimization and characterization of 1,8-cineole/hydroxypropyl-β-cyclodextrin inclusion complex and study of its release kinetics

Hao Yin,Chenxiao Wang,Jin Yue,Yun Deng,Shunshan Jiao,Yanyun Zhao,Jie Zhou,Ting Cao

Essential oils can be capsulated by cyclodextrin to enhance its thermal stability and preserve the bioactivity. In this study, 1,8-cineole was used as a guest molecule to prepare the cyclodextrin inclusion complexes (ICs). The formulation and processing parameters were optimized using the response surface methodology (RSM), and the optimal conditions were identified to be: 2.30 h of encapsulating time, 30.1 °C of encapsulating temperature and 0.99 of molar ratio of 1,8-cineole to HP-β-CD. The corresponding encapsulation efficiency and loading efficiency were 83.17% and 8.40%, respectively. The produced 1,8-cineole/HP-β-CD ICs was characterized by SEM, FTIR and TGA, and the results proved the enhanced thermal stability of IC. The release behavior and kinetics of IC was investigated and showed that at elevated temperature and relative humidity, the releasing rate of 1,8-cineole from the ICs increased and followed the Fick's law.

研究领域: 药剂学 · 食品科学 · 化学工程
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INSECT BIOCHEMISTRY AND MOLECULAR BIOLOGY · 2025 · IF 3.7

Odorant receptor CaspOR39 underpinned cineole-mediated oviposition repellency in the rape stem weevil Ceutorhynchus asper

Fuqiang Rao,Jie Yang,Danhao Peng,Xinghao Li,Zhaoqun Li,Deguang Liu

Herbivorous insects rely on olfactory cues to select oviposition sites on host plants, which is a process critical for their reproductive success. The rape stem weevil, Ceutorhynchus asper Roel. (Coleoptera: Curculionidae), is a major pest that causes significant damage to rapeseed and other cruciferous crop production, yet the chemical and molecular mechanisms underlying its oviposition preference remain unknown. Our behavioral assays revealed that C. asper females strongly avoided pre-infested rapeseed plants. Five monoterpenes (p-cymene, 1,8-cineole, ocimene, camphor, and α-pinene) were identified as herbivore-induced plant volatiles of C. asper -infested plants, with their emission levels significantly higher than those in healthy plants. Among these five compounds, subsequent electroantennogram (EAG) screening revealed that only 1,8-cineole triggered significant responses in C. asper and showed a concentration-dependent sensitivity. Behavioral assays showed that female C. asper exhibited significant behavioral and oviposition avoidance when exposed to 1,8-cineole. We identified CaspOR39 as the specific odorant receptor for 1,8-cineole, with molecular docking for prediction of the binding affinity and key residues. RNAi of CaspOR39 abolished female EAG responses, as well as behavioral and oviposition avoidance of 1,8-cineole. These results revealed a sex-specific chemical sensing mechanism: female C. asper can utilize CaspOR39 to detect 1,8-cineole as a key cue of plant infestation, driving adaptive oviposition behaviors of this beetle. Our results provide mechanistic and molecular insights into CaspOR39-mediated oviposition behaviors of C. asper , and a basis for the development of semiochemical-based strategies for management of this weevil.

CAS / MDL: 110-54-3
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FOOD CHEMISTRY · 2023 · IF 8.8

Electrospun polyvinyl alcohol/chitosan nanofibers incorporated with 1,8-cineole/cyclodextrin inclusion complexes: Characterization, release kinetics and application in strawberry preservation

Chuanxiang Cheng,Tiantian Min,Yuwan Luo,Yushan Zhang,Jin Yue

Development of food packaging systems containing essential oils (EOs) has gained increased attention recently. However, the instability of EOs restricts their application. Therefore, effective encapsulation of EOs is demanded for their protection and controlled release. In this work, 1,8-cineole, the major component in Eucalyptus globulus essential oil, was encapsulated into hydroxypropyl-β-cyclodextrin to form an inclusion complex, which was then incorporated into polyvinyl alcohol and chitosan composite polymer to fabricate nanofibrous film via electrospinning. The film with 40% (w/w) of inclusion complexes showed enhanced barrier and mechanical properties, and the release of 1,8-cineole from the film was sustained and dominated by the non-Fick diffusion. Moreover, this film could extend the shelf life of strawberries to 6 days at 25 ℃. This work suggested dual encapsulation of EOs by cyclodextrin and electrospun nanofibers is an ideal strategy to improve the availability of EOs, and the produced film is promising for food preservation.

CAS / MDL: 9002-89-5
研究领域: 食品科学 · 材料科学
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BIOORGANIC CHEMISTRY · 2022 · IF 5.307

Combination of 1,8-cineole and beta-caryophyllene synergistically reverses cardiac hypertrophy in isoprenaline-induced mice and H9c2 cells

Chunmei Bai,Qianqian Ma,Qi Li,Lijun Yu,Dong Zhen,Mingjie Liu,Chengxi Wei

Combination drug therapy has become an effective strategy for chronic metabolic disease, especially cardiovascular disease. In the present study, possible drug combinations were screened and the mechanism of the combinations against cardiac hypertrophy was examined within 1,8-cineole, β -caryophyllene, linalool, and β -pinene.H9c2 cells were treatment with 1,8-cineole, β -caryophyllene, linalool, and β -pinene individually or in combination for 24 h after isoprenaline stimulation. Cell viability was detected by the MTT assay. Subsequently, bioinformatic analysis and network pharmacology were used to reveal the multi-targeted synergistic therapeutic effect of the combination treatment compounds on cardiac hypertrophy. Ultimately, western blot and elisa was performed to analyses the protein expression in vivo . MTT results found that 1,8-cineole and β -caryophyllene synergistically increased cell viability with CalcuSyn software analyses. Specifically, bioinformatic and network pharmacology analysis showed PTGS2, TNF, IL-6, AKT1, NOS2, and CAT were identified as the key targets. P13K-AKT signaling pathway was involved in the reversal of cardiac hypertrophy by the combination of 1,8-cineole and β -caryophyllene. The in vitro results indicated that the combination synergistically treated the isoprenaline-induced mice against structural and functional myocardial damage via the P13K-AKT signaling pathway. Collectively, the combined application of 1,8-cineole and β -caryophyllene synergistically reverses cardiac hypertrophy in isoprenaline-induced H9c2 cells and mice.

CAS / MDL: 470-82-6 78-70-6
研究领域: 药理学 · 心血管疾病 · 细胞生物学 · 网络药理学
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BIOMEDICINE & PHARMACOTHERAPY · 2023 · IF 7.5

1,8-Cineole ameliorates diabetic retinopathy by inhibiting retinal pigment epithelium ferroptosis via PPAR-γ/TXNIP pathways

Zhangnian Liu,Shiquan Gan,Lingyun Fu,Yini Xu,Shengquan Wang,Guangqiong Zhang,Di Pan,Ling Tao,Xiangchun Shen

1,8-Cineole, the main component of volatile oil in aromatic plants, has diverse pharmacological properties, including antioxidant, anti-inflammatory, and anti-cancer properties. Diabetic retinopathy (DR) is a common microvascular complication of diabetes mellitus (DM). Here, we investigated the protective effect of 1,8-cineole on DR and found that 1,8-cineole treatment could alter the expression of several genes in both high glucose (HG)-induced ARPE-19 cells and retinal tissues of DM mice, as well as inhibit ferroptosis. Subsequent investigations into the molecular mechanisms underlying this inhibition revealed that expression of thioredoxin-interacting protein (TXNIP) was significantly upregulated while that of peroxisome proliferator-activated receptor γ (PPAR-γ) was significantly downregulated in HG-induced ARPE-19 cells, and treatment with 1,8-cineole could effectively reverse these changes. Treatment with a PPAR-γ pharmacological agonist (rosiglitazone), alone or combined with 1,8-cineole, significantly inhibited the transcription of TXNIP and ferroptosis in HG-induced ARPE-19 cells. Conversely, pretreatment with GW9662, a PPAR-γ inhibitor, upregulated the transcription and expression of TXNIP in HG-induced ARPE-19 cells; 1,8-cineole failed to reverse this upregulated expression. To explore these relationships, we constructed a PPAR-γ adenovirus shRNA to elucidate the effect of 1,8-cineole on the negative regulation of TXNIP by PPAR-γ. Taken together, the present findings indicate that HG-induced ferroptosis in retinal tissue plays an essential role in the pathogenesis of DR, which can be ameliorated by 1,8-cineole.

CAS / MDL: 470-82-6
研究领域: 药理学 · 眼科学 · 分子生物学 · 糖尿病研究
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PHYTOMEDICINE · 2024 · IF 6.7

1,8-Cineole alleviates Nrf2-mediated redox imbalance and mitochondrial dysfunction in diabetes mellitus by targeting Sirt1

Hong Yang,Yong-xin Chen,Ke-gang Linghu,Peng-yan Ren,Yu-ting Yao,Feng Jiang,Guo-ping Wu,Ting-ting Chen,Ling Tao,Qian-yun Sun,Yue Li,Xiang-chun Shen

Background Type 2 diabetes mellitus (T2DM) is primarily attributed to impaired insulin secretion caused by β cell dysfunction. 1,8-Cineole is a key bioactive compound in the essential oil extracted from Fructus Alpiniae Zerumbet , which possesses anti-inflammatory and antioxidant properties. Nevertheless, it remains elusive about the protective effect and precise mechanisms of 1,8-Cineole against the β cell deterioration in DM. Purpose To investigate the effect of 1,8-Cineole on β cell dysfunction in T2DM and the potential mechanism of its action. Methods A mouse model of T2DM and a β cell model of high glucose induction were generated to analyze the pharmacological properties of 1,8-Cineole. Proteomic and network pharmacological analyses were conducted to identify the crucial pathways involved in T2DM. Resveratrol [a Sirtuin1 (Sirt1) agonist] and Sirt1 knockdown were used to ascertain the mechanism of 1,8-Cineole in T2DM. The binding affinity of 1,8-Cineole to Sirt1 was assessed with molecular docking, surface plasmon resonance, immunoprecipitation assay, and cellular thermal shift assay. Results First, dysregulated crucial pathways in T2DM were screened out, including redox imbalance and mitochondrial dysfunction. Subsequently, 1,8-Cineole was found to activate Sirt1 and nuclear factor E2-related factor 2 (Nrf2) to repress oxidative stress in both T2DM mice and high glucose-induced β cells, thereby relieving mitochondrial dysfunction and apoptosis. Furthermore, 1,8-Cineole specifically targeted Sirt1 and favored the direct interaction between Sirt1 and Nrf2, ultimately restoring β cell function. Conclusions Our findings provide the first evidence that 1,8-Cineole directly binds to Sirt1 protein and enhances its stability, therefore rectifying impaired oxidative homeostasis, and then suppressing mitochondrial dysfunction and apoptosis in T2DM, indicating that 1,8-Cineole may be a potential candidate drug for DM treatment.

CAS / MDL: 470-82-6
研究领域: 药理学 · 内分泌学 · 分子生物学
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INTERNATIONAL IMMUNOPHARMACOLOGY · 2025 · IF 4.7

1,8-Cineole alleviates spinal cord injury by inhibiting microglial pyroptosis via the P38 MAPK and PI3K/AKT/NLRP3 signaling pathways to protects neurons

Wenyang Zhou,Zhenhao Liu,Xichuan Qiu,Minghao Tian,Baoqiang He,Chao Tang,Qiang Tang,Rupei Ye,Dejun Zhong,Yehui Liao

Following spinal cord injury (SCI), pyroptosis plays a significant role in regulating neuroinflammation during the secondary phase of injury. Although 1,8-cineole possesses anti-inflammatory effects, its role in SCI and underlying molecular mechanisms remains unclear. This study revealed that 1,8-cineole promoted motor function recovery in spinal cord-injured rats, reduced NLRP3 inflammasome-mediated microglial pyroptosis and activation, enhanced neuronal regeneration, and suppressed neuronal apoptosis and glial scar formation. Network pharmacology analysis showed that 1,8-cineole targets the PI3K/AKT and P38 MAPK pathways to inhibit microglial activation and pyroptosis. Finally, using a conditional co-culture system, we demonstrated that 1,8-cineole-treated microglia facilitated neuronal regeneration while inhibiting apoptosis. These findings indicate that 1,8-cineole promotes functional recovery post-SCI by protecting neurons by suppressing microglial pyroptosis and activation through the PI3K/AKT and P38 MAPK axes.

CAS / MDL: 470-82-6
研究领域: 神经科学 · 药理学 · 细胞生物学 · 分子生物学 · 神经病学
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