SEPARATION AND PURIFICATION TECHNOLOGY
·
2023
·
IF 8.6
Yulin Zhang,Shuo Cheng,Guozhao Ji,Aimin Li
The light fractions of tire pyrolysis oil (TPO) are rich in valuable chemicals, such as limonene, but the utilization of TPO-derived limonene or limonene derivatives was limited by the difficulties to separate limonene from the rest compounds, especially p -cymene which has a similar molecular structure and physical properties (molecular size, melting point and boiling point) as limonene. In order to utilize limonene and separate p -cymene, this study took advantage of the difference in oxidizability between limonene and p -cymene, and proposed a method of epoxidizing TPO before the separation. After epoxidation, limonene was successfully converted into limonene epoxides, while aromatic compounds in TPO such as p -cymene were inert and non-oxidizable. Limonene epoxides have a higher boiling point than p -cymene, so the limonene epoxides can be easily refined by distillation. In order to accelerate the oxidation of limonene, a peroxophosphotungstate catalyst was used as a sustainable solvent-free process. The fraction of TPO between 160 and 190 °C which has 298 g/L limonene was tested in this study. The epoxidation of the TPO 160-190 could reach complete conversion to limonene 1,2-oxides and diepoxide limonene. The resulting oil could be divided into p -cymene enriched fraction and limonene epoxides enriched fraction by simple distillation, and the limonene epoxides enriched fraction contained more than 80% of limonene epoxides. The catalytic mechanism was proposed with the assistance of FT-IR, GC–MS, and 31 P NMR analysis. This work presents a novel strategy of epoxidizing limonene for limonene epoxide and p -cymene separation, which could bring a breakthrough for limonene epoxide and p -cymene production from waste-derived oils.
研究领域:
化学工程
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环境科学
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DOI
高影响因子
JOURNAL OF FOOD SCIENCE
·
2025
·Vol. 90
·期 6
·e70310
·
IF 3.4
Arooj Rehman Sheikh,Miral Javed,Hao Zhang,Qiaojun Jia,Zisheng Luo
Camellia oleifera shells, waste material obtained after oil extraction, contain a significant number of terpenes. This study introduces a novel, eco-friendly, and sustainable method to combine N 2 -NBs with limonene and ultrasound to enhance terpene extraction from food waste. N 2 -NBs suspension stabilized by Tween 80, resulting in 255 nm size with reduced surface tension. Raman spectroscopy indicates strong hydrogen bonding at 1646 cm⁻¹, suggesting that the enhanced release of compounds and micelle formation improved the solubility of terpenes. Meanwhile, SEM demonstrated that the collapse of N 2 -NBs effectively disrupted cell walls. Together, these mechanisms significantly enhanced terpene compounds' release, solubility, and overall yield. Combining Tween 80 and N 2 -NBs with ultrasound achieved a terpene yield of 42.88 ± 1.87 mg/g DW, significantly higher than the 10.96 ± 2.87 mg/g DW from ethanol extraction. These findings highlight the novel eco-friendly approach to effectively extract terpenes, which can be useful for industrial applications. Practical applications The novel, eco-friendly extraction method can be used to reuse food waste. High-yielding extraction method can be used to extract pharmaceutical compounds. Extracted terpenes can be used for various food industry applications.
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PubMed
高影响因子
Life-Basel
·
2024
·Vol. 14
·期 6
·713
·
IF 3.2
Leyuan Liu,Lang Yang,Jinxi Yuan,Jie Zhang,Chenhao Liu,Hongxu Zhou,Wei Liu,Guirong Wang
The oriental fruit fly,Bactrocera dorsalis(Hendel), poses a significant threat to the global fruit industry, causing damage to diverse fruits like citrus, mango, and guava. Chemical pesticides have limited effectiveness, and pesticide residues and pesticide resistance are pressing issues. Therefore, it is essential to develop environmentally friendly pest control methods to address this problem. Behavior-modifying chemicals, including male attractants and intersex protein baits, play a critical role in the control ofB. dorsalis. The mature host fruit serves as both an oviposition site and food source under natural conditions, making it a potential attraction source for oriental fruit flies. Orange,Citrus sinensis, is a main host ofB. dorsalis, and commercial orange juice is a common attractant for the egg laying ofB. dorsalis. Although it can both attract and elicit oviposition behaviors inB. dorsalisadults, its active components are still unclear. This study utilized analytical chemistry, behavioral tests, and electrophysiology to identify the active components of commercial orange juice that attractB. dorsalis, with the aim of providing a reference for the development of behavior-modifying chemical-based techniques to controlB. dorsalis.Five compounds with a high abundance were identified via a GC-MS, including D-Limonene, butanoic acid ethyl ester, β-myrcene, linalool, and α-terpineol. Behavioral and electrophysiological experiments uncovered that D-Limonene was the active substance that was the main attractant in the mixture of these five substances, evoking a strong electrophysiological response in adultB. dorsalis. D-Limonene strongly attracts adultB. dorsalisonly when they are sexually mature, and the attraction is not rhythmic. Olfaction plays a leading role in the attraction of D-Limonene to adultB. dorsalis, andOrco−/−mediates the perception of D-Limonene byB. dorsalis. Overall, D-Limonene is one of the key attractant compounds forB. dorsalisin the volatile compounds of commercial orange juice, offering possible support for the development of behavior-modifying chemical-based technology to controlB. dorsalisin the future.
研究领域:
昆虫学
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化学生态学
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害虫防治
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PubMed
高影响因子
PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY
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2025
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IF 1.9
Zehao Li,Zixuan Wang,Lulu Zhang,Feng Yingjie,Jinchu Yang,Haoliang Li,Weimin Song,Qiuling Wang,Yongfeng Yang,Zhenzhen Huang,Yongming Xu,Yufeng Fu,Meizhou Ding,Gang Fan,Jingnan Ren,Aiqun Yu,Jian Feng,Guijie Li,Linhua Huang,Yujiao Cheng
α-Terpineol, an abundant oxygenated monoterpene compound, shows a varied range of beneficial bioactivities. This study focused on the efficient extraction and purification of α-terpineol from the biotransformation of limonene using Penicillium digitatum DSM 62840 mutant (PdTP1-overexpressed OE2 strain). The α-terpineol was primarily distributed in the supernatant, with minimal association with the biomass. And the optimal extraction was achieved using ethyl acetate as the extractant, which can directly obtain the highest recovery of α-terpineol without sequential extractions. The equilibrium of mass transfer was quickly reached (≤20 s in vortex). Additionally, the purification method of α-terpineol using column chromatography was described, further improving the purity of product to 96.86% in gas chromatography. Structural identification of purified α-terpineol was confirmed using gas chromatography-mass spectrometry, Fourier-transform infrared spectroscopy, and nuclear magnetic resonance. This simplified and efficient strategy for the extraction and purification of α-terpineol not only provides a solid theoretical basis for the final step in the relevant study of microbial synthesis of α-terpineol but also is of great significance for its industrial application.
研究领域:
微生物学
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天然产物化学
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药理学
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DOI
PubMed
高影响因子
Frontiers in Microbiology
·
2020
·
IF 4.236
Zhang Lu-Lu,Huang Wen,Zhang Ying-Ying,Fan Gang,He Jin,Ren Jing-Nan,Li Zhi,Li Xiao,Pan Si-Yi
α-Terpineol has been widely used in daily chemical, pharmaceutical, food, and flavor industries due to its pleasant odor with high economic value and pharmacological action. Our previous study showed that Penicillium digitatum DSM 62840 was an efficient biocatalyst for the transformation of limonene to α-terpineol. Thus, it was meaningful to explore the genome features and the gene expression differences of strain DSM 62840 during limonene biotransformation, and the detailed bioconversion pathways. In this study, the functional genes related to limonene bioconversion were investigated using genome and transcriptome sequences analysis. The results showed that the P. digitatum DSM 62840 genome was estimated to be 29.09 Mb and it encoded 9,086 protein-encoding genes. The most annotated genes were associated to some protein metabolism and energy metabolism functions. When the threshold for differentially expressed genes (DEGs) was set at twofold ratio, a total of 4,128, and 4,148 DEGs were identified in P_L_12h (limonene-treated condition) compared with P_0h (blank) and P_12h (limonene-untreated blank), respectively. Among them, the expression levels of genes involved in the biosynthesis of secondary metabolites, energy metabolism and ATP-binding cassette (ABC) transporters were significantly altered during the biotransformation. And the reliability of these results was further confirmed by quantitative real-time polymerase chain reaction (RT-qPCR). Moreover, we found that the enzyme participated in limonene biotransformation was inducible. This enzyme was located in the microsome, and it was inhibited by cytochrome P450 inhibitors. This indicated that the cytochrome P450 may be responsible for the limonene bioconversion. Several differentially expressed cytochrome P450 genes were further identified, such as PDIDSM_85260 and PDIDSM_67430, which were significantly up-regulated with limonene treatment. These genes may be responsible for converting limonene to α-terpineol. Totally, the genomic and transcriptomic data could provide valuable information in the discovery of related-genes which was involved in limonene biotransformation, pathogenicity of fungi, and investigation of metabolites and biological pathways of strain DSM 62840.
研究领域:
微生物学
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基因组学
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分子生物学
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生物技术
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生物化学
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DOI
PubMed
高影响因子
ADVANCED FUNCTIONAL MATERIALS
·
2015
·Vol. 25
·期 18
·2754-2762
·
IF 11.805
Yujing Zuo,Jinfeng Cao,Shengyu Feng
The increasing pursuit of biocontained elastic materials led the investigation of the potential use of the monoterpene limonene in film synthesis via thiol–ene reaction. Poly[(mercaptopropyl)methylsiloxane] (PMMS) is first synthesized. By controlling the molar ratio of PMMS and functional monomers, such as polyethylene glycol allyl methyl ether or rhodamine-B, PMMS is partially functionalized while leaving spare mercapto groups that could be further used as cross-linking sites. On the basis of the functionalized PMMS, novel transparent silicone luminescent films with hydrophilic tunable properties are prepared by natural-sunlight-triggered thiol–ene “click” chemistry by using d -limonene as a cross-linker. Their structures and properties are thoroughly characterized. Transparent luminescent films are coated on commercially available UV-light emitting diode (LED) cell from solution medium followed by an in situ cross-linking step; a colorful LED cell is obtained through this facile and efficient method. The UV-LED coated by films show very intense photoluminescence under normal visible light or the light is on, and has very high coloric purity.
研究领域:
材料科学
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化学工程
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DOI
高影响因子
FOOD HYDROCOLLOIDS
·
2023
·
IF 10.7
Xin Wang,Jiayi Sun,Shenghan Zhao,Fang Zhang,Xianghong Meng,Bingjie Liu
The objective of this work was to develop nanostructured lipid carriers (NLCs) with preservation effect by using pea protein isolate (PPI) nanoparticles as emulsifiers, candelilla wax (CW) as organo-gelator and d -limonene (DL) as antifungal agent. The optimal formulation parameters of NLCs were firstly determined based on results of particle size, poly-dispersity index and zeta potential, and then NLCs prepared by optimal formulation were further characterized. The results showed that DL was successfully encapsulated inside NLCs. Moreover, the encapsulation of amorphous DL led to more disordered crystalline state of NLCs. In addition, in comparing the properties of NLCs and nanoemulsions (NEs) without CW, it was found that the addition of CW seemed to have several beneficial effects on NLCs: 1) NLC droplets were well dispersed, whereas NE droplets exhibited coalescence and flocculation; 2) compared with NEs, NLCs displayed excellent storage stability and inhibition ability of DL release. Furthermore, antifungal activity of NLCs was observed by in vitro and in vivo study. The acquired information in current research can provide novel insight into development of stable and antifungal nanocarriers that own a promising application in tomato preservation.
研究领域:
药学
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食品科学
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材料科学
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微生物学
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DOI
高影响因子
Journal of Environmental Sciences
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2024
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IF 5.9
Yingqi Zhao,Zhaoyan Zhang,Ya Zhao,Chong Wang,Hua Xie,Jiayue Yang,Weiqing Zhang,Guorong Wu,Gang Li,Ling Jiang,Xueming Yang
It is highly challenging to precisely compare the impacts of anthropogenic pollutants on the photooxidation of isomeric volatile organic compounds with respect to molecular compositions and particle number/mass concentrations of secondary organic aerosols (SOAs). In this study, we conducted a series of well-defined indoor chamber experiments to compare the effects of NO x (NO and NO 2 ) on the photooxidation of isomeric monoterpenes of β -pinene and limonene. For the photooxidation of β -pinene with NO x , the increase of the initial concentrations of NO ([NO] 0 ) shows a monotonous suppression of the particle mass concentration, whereas the increase of [NO 2 ] 0 shows a monotonous enhancement of the particle mass concentration. For the photooxidation of limonene with NO x , the increase of [NO] 0 exhibits a monotonous suppression of the particle mass concentration, whereas the increase of [NO 2 ] 0 shows a parabolic trend of the particle mass concentration. Utilizing a newly developed vacuum ultraviolet free electron laser (VUV-FEL), the online threshold photoionization mass spectrometry reveals a series of novel compounds at molecular weight (MW) = 232 and 306 for the β -pinene + NO x system and MW = 187, 261, 280, and 306 for the limonene + NO x system. The molecular structures and formation pathways of these species were inferred, which led to the prediction of the diversity and difference of SOA products (i.e., ester and peroxide accretion products) formed from different monoterpene precursors. To improve the predictions of future air quality, it is recommended that climate models should incorporate the NO x -driven diurnal photooxidation of monoterpenes for SOA formation mechanisms.
研究领域:
大气化学
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环境科学
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DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
·
2024
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IF 5.3
Lei Xiao,Yuting Wei,Xin Liu,Bo Wang,Yueyuan Chen,Zhifang Cui
As an aldehyde derivative of monoterpene, citral is the main oxyterpene in various botanical essential oils which has been widely applied in food, cosmetics and medicines. The separation of oxyterpenes from terpenes (deterpenation) improves its stability and quality, which is an essential step for production of citral with high market value. Herein, the extractive separation of citral and limonene using deep eutectic solvents (DESs) of quaternary ammonium/alkanediol was explored. Influence of DESs components, including different quaternary ammonium salts as hydrogen bond acceptors (HBAs), various alkanediols as hydrogen bond donors (HBDs) and the changing of HBA to HBD ratios on citral extraction were studied. Distribution coefficient, selectivity and extraction yield of the citral of these DESs were experimentally evaluated. Among the HBAs investigated, tetrabutylammonium bromide (TBABr) was determined to be the suitable one, since halide Br - was better than Cl - , and quaternary ammonium cations with longer alkyl chain length was preferable. Meanwhile, 1,2-propanediol (1,2-PDO) outperformed other alkanediols, and higher HBD contents in DESs facilitated the separation. TBABr/1,2-PDO (molar ratio 1:10) exhibited the best performance, with citral distribution coefficient 1.28, selectivity 13.65 and extraction yield 64.26%. The type and strength of molecular interactions between citral solute and DESs were identified by employing quantum chemistry calculation and molecular dynamic simulations. The performance difference of these DESs can be ascribed to the difference of the direct hydrogen bond between the α-OH of alkanediols and the O from citral carbonyl group during extraction. The mechanisms exploration provides insights for rational fine-tuning the novel DESs with better deterpenation performance.
研究领域:
化学
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分离科学
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材料科学
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DOI
高影响因子
INFLAMMOPHARMACOLOGY
·
2025
·
IF 5.3
Xu Wenxiu,Wang Hongbo,Sun Zhenyu,Zhang Hui,Zhang Zhijun,Sun Xiangrong,Gu Jiayu,Gong Yanling
Limonene, a monoterpene naturally abundant in various Citrus fruits, is widely used as a fragrance component and dietary supplement. Ulcerative colitis (UC), a representative inflammatory bowel disease, is characterized by an arising incidence and considerable impact on human health. Although several reports have demonstrated the beneficial effects of limonene on UC, detailed mechanisms remain incompletely understood. In this study, we employed a dextran sulfate sodium (DSS)-induced UC murine model and a lipopolysaccharide (LPS)-stimulated Caco-2 cell model to explore the mechanisms of limonene on UC. The results revealed that limonene significantly decreased disease activity index (DAI) score and alleviated pathological damage in UC mice, exhibiting therapeutic potential for UC. Limonene significantly inhibited interleukin-6 (IL-6), interleukin-1β (IL-1β), tumor necrosis factor-α (TNF-α) and malondialdehyde (MDA) while increased superoxide dismutase (SOD) in both DSS-induced UC mice and LPS-induced Caco-2 cells. Furthermore, limonene significantly increased expressions of Zonula occludens-1 (ZO-1), occludin, and claudin-1, thereby enhancing intestinal barrier integrity. Limonene mitigated UC-associated dysbiosis by shifting the gut microbial composition toward that of healthy controls. Specifically, it modulated the microbiota at the phylum, family, genus and species levels, increasing the abundance of anti-inflammatory bacteria while decreasing inflammatory related taxa. Collectively, our in vivo and in vitro results demonstrate that limonene alleviates UC involving in anti-inflammation, anti-oxidation, restoration of intestinal barrier integrity and regulation of the gut microbiota. Future studies are warranted to explore whether gut microbial metabolites contribute to the protective effects of limonene in UC. Graphical abstract
研究领域:
消化病学
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免疫学
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分子生物学
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药理学
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微生物组学
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氧化应激
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肠道屏障功能
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天然产物药理
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产品关联
DOI
PubMed
高影响因子
Journal of Functional Foods
·
2019
·
IF 3.197
Ze-hua Li,Ming Cai,Kai Yang,Pei-long Sun
Nanoemulsion loading finger citron essential oil (FCEO) can maintain bioactivities of FCEO and increase its water solubility. In this study, stability of FCEO nanoemulsions during digestion in vitro were evaluated and the release kinetics of d-limonene (the main component in the oil) were developed. Compared with free oil released to maximum for 6 min, all nanoemulsions kept sustainably releasing for 300 min or longer. Droplet size of the nanoemulsions increased from 10–18 nm of initial to 105–1106 nm after digestion, indicating coalescence or aggregation occurred. Zero-order, Hixcon-Crowell, Higuchi, Ritger-Peppas and Niebergull models were used to describe the release kinetics. The results showed zero-order and Ritger-Peppas models were the best fit models at mouth and intestinal stage, respectively. Both zero-order and Higuchi models were appropriate at gastric stage. This study could demonstrate the digestion mechanisms of FCEO loaded nanoemulsion and facilitate the design of hydrophobic nutraceuticals delivery systems in food industry.
研究领域:
食品科学
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药剂学
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化学工程
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产品关联
DOI
高影响因子
REACTIVE & FUNCTIONAL POLYMERS
·
2017
·
IF 3.151
Jingjing Liu,Yin Zhao,Hailing Chen,Zhengbiao Zhang,Wei Zhang,Xiulin Zhu
A novel circular dichroism (CD)-silent π -conjugated polyfluorene bearing the bulky crown ether pendant ( PF8C4 ) as the potassium ion binding site was successfully prepared by polymerization of the corresponding monomers with palladium catalyst. The polymer containing polar groups was found to form the eximious helical assembly by aggregating in chiral limonene at a lower temperature. The aggregates obtained from R - and S -limonene exhibited mirror-image CD peaks in the UV–vis region of polymer backbone. Therefore, the chirality of enantiopure limonene was successfully transferred to the optically inactive PF8C4 , and the relative P - and M -helical supramolecules were successfully prepared. Moreover, after appending K + ion to the helical supramolecules, the complexation between the K + ion and the crown ether pendant helped to strengthen the optical activity , and thus more stable optically active supramolecular structures were achieved.
研究领域:
材料科学
·
有机化学
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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）