ACS Sustainable Chemistry & Engineering
·
2022
·
IF 9.224
Guoqiang Cui,Xinyu Yang,Zaizhi Liu,Mengxia Wei,Tingting Liu,Huiyan Gu,Lei Yang
Limonene was used as an extraction solvent to obtain gutta-percha from leaves, samara, and bark of Eucommia ulmoides. The extraction conditions for the gutta-percha of E. ulmoides were optimized using a set of optimization processes. The optimized conditions were a liquid–solid ratio (L/S ratio) of 19.7 mL/g, extraction temperature of 134 °C, and extraction time of 1.8 h for the bark; an extraction temperature of 128 °C, extraction time of 1.7 h, and L/S ratio of 14 mL/g for the samara; and an extraction time of 1.4 h, L/S ratio of 15 mL/g, and reaction temperature of 138 °C for the leaves. Under these optimized extraction conditions, the actual extraction yields of gutta-percha were 55.32 ± 2.53 mg/g (bark), 81.14 ± 3.84 mg/g (samara), and 22.15 ± 1.08 mg/g (leaves). The gutta-percha obtained by limonene extraction was evaluated by thermogravimetric and differential thermogravimetric tests, gel permeation chromatography, differential scanning calorimetry, and Fourier transform infrared spectroscopy. Limonene has promising potential to replace traditional petroleum-based solvents to isolate gutta-percha from E. ulmoides.
研究领域:
植物化学
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材料科学
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环境科学
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DOI
高影响因子
BIORESOURCE TECHNOLOGY
·
2024
·
IF 9.7
Lili Xu,Qingqing Zhao,Haibo Liu,Dankui Liao,Aixing Tang,Youyan Liu
Limonene dioxide (LDO) is essential for manufacturing bio-based polycarbonate and non-isocyanate polyurethanes. Herein, we report a strategy for the chemoenzymatic epoxidation of (R)-(+)-limonene to LDO with high selectivity using Rhizopus oryzae whole cells. The presence of sufficient excess acid in the system is essential, in addition to overcoming the hydrolysis of the intermediate product, 1,2-limonene oxide, to accomplish the double epoxidation of limonene. When using a high concentration of H 2 O 2 and trisodium citrate, the conditions were effectively established, even when Novozym 435 was substituted, which had previously been reported to be ineffective in achieving high-yield double epoxidation of limonene. The transfer of H 2 O 2 and peracids between the cell and solvent slowed production. The total amount of peracids generated remained constant, but their concentrations remained moderate, favoring the double epoxidation of limonene. An LDO yield of 93 % and no intermediate product, limonene oxide, were obtained under optimized conditions within 20 h.
研究领域:
生物化学
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有机合成
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酶工程
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2025
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IF 6.2
Qin Hong,Di Liu,Linbo Gou,Shengfang Wu,Xiuwen Zhou,Tai-Ping Fan,Long Wang,Yujie Cai
Limonene is a vital monoterpenoid with wide applications in food, medicine, cosmetics, and other fields. Microbial limonene production is a green and sustainable strategy, but its yield is limited by product toxicity and the low terpene synthase activity. In this study, using Serratia. marcescens HBQA7 ΔslaAB-pyc as the chassis strain, we first screened the most active (S)-limonene synthase from Mentha spicata among five plant-derived ones. Then, to further improve its activity, we rationally engineered its active site and enhanced its expression via a bicistronic structure. Finally, 4.5 g/L (S)-limonene was achieved in shake flasks with glycerol as the carbon source after 72 h. In a 5 L bioreactor, production reached 22.8 g/L within 100 h, representing the highest microbial (S)-limonene yield reported to date.
研究领域:
合成生物学
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微生物生物技术
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代谢工程
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酶工程
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工业微生物学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF THE ENERGY INSTITUTE
·
2025
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IF 6.2
Yilun Shui,Huiyu Liu,Rui Shan,Min Hao,Chengyu Li,Jun Zhang,Haoran Yuan
The present study proposes a promising strategy for selective pyrolysis of waste tire rubber particles into high-value limonene under the dual action of chemical pretreatments and basic Ca x Mg 1-x Al oxides. The experimental results demonstrate that chemical pretreatments of rubber particles significantly enhance limonene selectivity in pyrolysis products while effectively suppressing the generation of sulfur-containing compounds. Among the various pretreatments, the rubber particles pretreated with 1 wt.% sulfuric acid exhibits optimal performance, which achieves a relative limonene content as high as 35%. The introduction of Ca 0.3 Mg 0.7 Al substantially promotes the selective production of limonene that gives a maximum relative content of 46% in pyrolysis oils. Kinetic analysis confirms that the application of as-prepared Ca 0.3 Mg 0.7 Al greatly lowered the average activation energy from 245.8 kJ/mol to 217.5 kJ/mol for waste tire rubber particles pyrolysis. Moreover, the plausible reaction pathway for waste tire rubber particles pyrolysis under the action of chemical pretreatments and composite metal oxides was proposed. This study, through experiments under ideal laboratory conditions, clarifies the core mechanism of the synergistic regulation of limonene selectivity by chemical pretreatments and basic Ca x Mg 1-x Al oxides, and provides basic research support and technical development directions for the subsequent targeted conversion of industrial-scale waste tire rubber into high-value limonene-rich pyrolysis oils.
研究领域:
环境科学
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材料化学
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能源工程
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绿色化学
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资源循环利用
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热解技术
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催化化学
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产品关联
DOI
高影响因子
JOURNAL OF FOOD SAFETY
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2021
·Vol. 41
·期 5
·e12918
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IF 1.953
Yingjie Han,Wenxue Chen,Zhichang Sun
In this study, inhibitory effect of limonene on Staphylococcus aureus ( S. aureus ) and its antibacterial mechanism was explored, respectively. The results showed that limonene effectively inhibited bacterial growth at a minimum inhibitory concentration (MIC) of 20 ml/L. Scanning electron microscopy (SEM), the reduction of AKP activity and fluorescence microscope observation confirmed that limonene caused the destruction of the cell morphology and cell wall integrity of S. aureus . The reduction of MFI in fluorescein diacetate staining experiment and leakage of biological macromolecules (nucleic acids and proteins) indicated that limonene damaged the cell membrane and increased membrane permeability. Besides, the reduction of membrane potential (MP) further confirmed that the damage to membrane and the reduction of respiratory metabolic activity. Furthermore, the respiratory depression test confirmed that the pathway of limonene affecting the respiratory metabolism of S. aureus is TCA pathway, followed by EMP. In addition, the disorder of succinate dehydrogenase (SDH), malate dehydrogenase (MDH), pyruvate kinase (PK), ATPase (T-ATPase, Na + -K + -ATPase, Ca 2+ -Mg 2+ -ATPase), and ATP concentration demonstrated that limonene could result in a slowdown of metabolism and metabolic dysfunction, thus inhibiting ATP synthesis.
研究领域:
微生物学
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药理学
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细胞生物学
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生物化学
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产品关联
DOI
高影响因子
PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY
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2023
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IF 4.7
Wei Luo,Kaiyue Wang,Jingyi Luo,Yingchen Liu,Jiawen Tong,Mengting Qi,Yue Jiang,Yong Wang,Zhiqing Ma,Juntao Feng,Bin Lei,He Yan
The main component of orange peel essential oil is limonene . Limonene is a natural active monoterpene with multiple functions, such as antibacterial, antiseptic and antitumor activity, and has important development value in agriculture . This study found that limonene exhibited excellent anti-tobacco mosaic virus (TMV) bioactivity, with results showing that its protection activity, inactivation activity, and curative activity at 800 μg/mL were 84.93%, 59.28%, and 58.89%, respectively—significantly higher than those of chito-oligosaccharides. A direct effect of limonene on TMV particles was not observed, but limonene triggered the hypersensitive response (HR) in tobacco. Further determination of the induction activity of limonene against TMV demonstrated that it displayed good induction activity at 800 μg/mL, with a value of 60.59%. The results of physiological and biochemical experiments showed that at different treatment days, 800 μg/mL limonene induced the enhancement of defense enzymes activity in tobacco, including of SOD, CAT, POD, and PAL , which respectively increased by 3.2, 4.67, 4.12, and 2.33 times compared with the control (POD and SOD activities reached highest on the seventh day, and PAL and CAT activities reached highest on the fifth day). Limonene also enhanced the relative expression levels of pathogenesis related (PR) genes, including NPR1 , PR1 , and PR5 , which were upregulated 3.84-fold, 1.86-fold and 1.71-fold, respectively. Limonene induced the accumulation of salicylic acid (SA), and increased the relative expression levels of genes related to SA biosynthesis ( PAL ) and reactive oxygen species (ROS) burst ( RBOHB ), which respectively increased by 2.76 times and 4.23 times higher than the control. Systemic acquired resistance (SAR) is an important plant immune defense against pathogen infection. The observed accumulation of SA, the enhancement of defense enzymes activity and the high-level expression of defense-related genes suggested that limonene may induce resistance to TMV in tobacco by activating SAR mediated by the SA signaling pathway . Furthermore, the experimental results demonstrated that the expression level of the chlorophyll biosynthesis gene POR1 was increased 1.72-fold compared to the control in tobacco treated with 800 μg/mL limonene, indicating that limonene treatment may increase chlorophyll content in tobacco. The results of pot experiment showed that 800 μg/mL limonene induced plant resistance against Sclerotinia sclerotiorum (33.33%), Phytophthora capsici (54.55%), Botrytis cinerea (50.00%). The bioassay results indicated that limonene provided broad-spectrum and long-lasting resistance to pathogen infection. Therefore, limonene has good development and utilization value, and is expected to be developed into a new botanical-derived anti-virus agent and plant immunity activator in addition to insecticides and fungicides .
研究领域:
农业
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植物病理学
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植物化学
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分子生物学
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产品关联
DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2026
·
IF 8.7
Jingzhi Wu,Yaobin Huang,Xinming An,Yaqing Yin,Youyan Liu
Lignin-based nanoparticles enable covalent immobilization of lipase. • Biocatalytic nanoparticles stabilize Pickering emulsion interfaces. • Pickering emulsion biocatalysis epoxidizes limonene with stoichiometric H₂O₂. • Pickering emulsion interfacial system offers sustained catalyst recyclability. Chemoenzymatic epoxidation is a green route for terpene conversion but suffers from a fundamental trade-off. The high hydrogen peroxide (H₂O₂) loads required to overcome mass transfer paradoxically leads to severe enzyme inactivation. Herein, a lignin-based Pickering interfacial biocatalytic (PIB) system was constructed by covalently immobilizing Candida antarctica lipase B (CALB) onto functionalized lignin nanoparticles (CGPALPs). The resulting CGPALPs exhibit enhanced structural stability and oxidative resistance, retaining 71.4% of their activity after 12 h exposure to 1 M H₂O₂. Remarkably, this PIB system operates efficiently at a stoichiometric oxidant ratio (H₂O₂/limonene = 2:1). It achieves 92.97% limonene conversion and 92.23% total epoxide yield within 12 h. Most importantly, it delivers a 41.8% yield of limonene diepoxide without any excess H₂O₂, a result unattainable in chemoenzymatic biphasic systems. The system also demonstrates efficient H₂O₂ utilization (94.13%) and excellent reusability, maintaining over 80% activity after seven cycles. By integrating covalent enzyme immobilization with Pickering emulsion design, this work provides a sustainable and generalizable strategy to resolve the long-standing conflict between enzyme stability and mass transfer in chemoenzymatic epoxidation of hydrophobic substrates. Download: Download high-res image (138KB) Download: Download full-size image
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DOI
高影响因子
Nanoscale
·
2022
·Vol. 14
·期 16
·6052-6065
·
IF 8.307
Ya Zou,Zishuo Zhou,Shanmei Yin,Chengyuan Huang,Hesong Tang,Zongning Yin
Gallbladder stones are a major pathogenic factor leading to cholecystitis, and it is increasingly important to explore innovative drug delivery methods for gallstones. In the present study, docosahexaenoic acid-coupled limonene bovine serum albumin nanoparticles (LIM-DHA-BSA-NPs) were constructed. The LIM-DHA-BSA-NPs are spherical structures, and the distribution was relatively uniform, and, more importantly, it has low cytotoxicity and good safety. The LIM-DHA-BSA-NPs solution shows higher uptake rates by RAW264.7 cells when compared with free limonene (LIM). The fluorescence intensity of FITC-modified BSA NPs was significantly higher than that of free FITC, which further indicated that the uptake of DHA-conjugated BSA NPs by RAW264.7 cells was stronger than that of the free drugs. Moreover, the in vivo distribution experiment showed that the enrichment of DiD-loaded BSA NPs in the gallbladder was significantly enhanced when compared with that of free DiD. The semi-quantitative fluorescence intensity results showed that the uptake of DiD-DHA-BSA-NPs was 4.5 times higher when compared with the free DiD. It is preliminarily shown that the DHA-conjugated BSA NPs that were constructed, have an ability to target the gallbladder. Furthermore, the Pearson colocalization coefficient Rcoloc from in vivo colocalization results indicates that the DHA-BSA-NPs had a good colocalization effect on the gallbladder epithelial cells (GBECs). In addition, the LIM-DHA-BSA-NPs solution not only significantly reduced the concentration of nitric oxide (NO) secreted by inflammatory model cells and the number of peripheral blood leukocytes in guinea pigs with cholecystitis, but also significantly decreased the activities of the aspartate transaminase (AST), alkaline phosphatase (ALP), alanine aminotransferase (ALT), glutamyl endopeptidase (GGT), total bile acid (TBA), and total bilirubin (TBIL) enzymes. Collectively, the LIM-DHA-BSA-NPs could be used as an effective anti-inflammatory agent at the cellular and animal levels. This experiment, for the first time, showed that DHA-conjugated BSA NPs could be absorbed into GBECs by megalin receptor-mediated endocytosis and then they exert an anti-cholecystitis effect because of the LIM. The active uptake of DHA-conjugated BSA NPs by the megalin receptors of the GBECs is expected to become an effective therapeutic strategy for cholecystolithiasis.
研究领域:
药剂学
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分子生物学
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医学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF CHEMICAL AND ENGINEERING DATA
·
2023
·
IF 2.6
Xuejuan Wei,Xiaopeng Chen,Linlin Wang,Xiaojie Wei,Jiaqi Liang,Zehui Xiong,Jiezhen Liang
For the isolation and purification of (−)-α-pinene and (−)-limonene from pine resin tapping by spraying ethephon solution on the cutting surface of pine tree, vapor–liquid equilibrium data for (−)-α-pinene and (−)-limonene with ethephon are indispensable. In this work, the isothermal vapor–liquid equilibria of binary system (−)-α-pinene + (−)-limonene and quaternary system (−)-α-pinene + (−)-limonene + water + ethephon were determined using headspace gas chromatography. The thermodynamic consistency of the experimental data was tested by the Van Ness point test and Redlich-Kister area test. The universal quasi-chemical (UNIQUAC) and nonrandom two-liquid (NRTL) models were applied to correlate the experimental data, and the absolute mean deviation of the vapor phase mole fraction and the relative mean deviation of the total system pressure were calculated. The results showed that the UNIQUAC model correlated the system more accurately than the NRTL model. The relative volatility of (−)-α-pinene to (−)-limonene was promoted by adding ethephon solution. In addition, the binding energies of (−)-α-pinene + water + ethephon and (−)-limonene + water + ethephon were calculated by DFT. The results showed that the intermolecular interaction between ethephon solutions with (−)-limonene was greater than that with (−)-α-pinene.
研究领域:
化学工程
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植物化学
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热力学
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产品关联
DOI
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
·
2019
·
IF 3.714
Rui Cai,Miaomiao Hu,Yijun Zhang,Chen Niu,Tianli Yue,Yahong Yuan,Zhouli Wang
The aim of this study was to investigate the antifungal activity and mechanisms of citral, limonene and eugenol against Zygosaccharomyces rouxii . All the three essential oil ingredients presented strong antifungal activities against Z. rouxii . Minimum inhibitory concentrations of citral, limonene and eugenol were 0.188, 0.75 and 0.4 μL/mL, and the minimum fungicidal concentrations were 0.375, 3 and 0.8 μL/mL, respectively. Scanning electron microscopy showed that the tested essential oil compounds had destructive effects on the yeast cell surface. After treated by citral, limonene and eugenol, the relative electric conductivity and leakage of nucleic acid were increased significantly. SDS-PAGE analysis indicated that the essential oil components could result in the loss of soluble proteins and might also destroy the yeast protein or inhibit their expression. These results demonstrated that citral, limonene and eugenol exerted their antifungal action against Z. rouxii through cell membrane damage and destruction of cellular proteins. This study provided a theoretical possibility that citral, limonene and eugenol could be used as natural food preservatives for the control of Z. rouxii -related spoilage in the fruit juice industry.
研究领域:
食品科学
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微生物学
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药理学
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产品关联
DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2016
·
IF 3.138
Ping Shao,Huiling Ma,Qiang Qiu,Weiping Jing
The physical stability of R-(+)-Limonene emulsions stabilized by Ulva fasciata polysaccharide (UFP) was investigated in this study. Emulsion physical stability was evaluated under different polysaccharide concentrations (1%–5%, wt/wt) and pH values (3.0–11.0). The stability of R-(+)-Limonene emulsions was demonstrated by droplet size distribution, rheological properties, zeta potential and visual phase separation. R-(+)-Limonene emulsions displayed monomodal droplet size distributions, high absolute values of zeta potential and good storage stability when 3% (wt/wt) UFP was used. The rheological properties and stability of R-(+)-Limonene emulsions appeared to be dependent on polysaccharide concentration. The emulsion stability was impacted by pH. Higher zeta potential (−52.6 mV) and smaller mean droplet diameter (2.45 μm) were achieved in neutral liquid environment (pH 7.0). Extreme acidity caused the flocculation of emulsions, which was manifested as phase separation, while emulsions were quite stable in an alkaline environment. Through comparing the stabilities of emulsions stabilized by different emulsifiers (i.e. UFP, GA and Gelatin), the result suggested that UFP was the best emulsifying agent among them.
研究领域:
食品科学
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生物化学
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产品关联
DOI
PubMed
高影响因子
FOOD CONTROL
·
2014
·
IF 2.819
Mohamed Reda Zahi,Hao Liang,Qipeng Yuan
The purpose of this research was to develop a novel antimicrobial delivery system by encapsulating d -limonene into an organogel-based nanoemulsion and investigating its antimicrobial activity. The d -limonene organogel-based nanoemulsion was prepared by high pressure homogenization method. The surfactant concentration had a major impact on the droplets' formation and distribution. At the optimal condition (10% w/w Tween 80, 100 Mpa, and 10 Cycles) the smallest droplet size ( d ≈ 36 nm) could be obtained, which has shown a narrow structure and good stability. Results from the antimicrobial activity have shown the encapsulation of d -limonene (4% w/w) into the organogel-based nanoemulsion contributed to the increase of its antimicrobial activity. In addition, the mechanism of d -limonene organogel-based nanoemulsion against the tested microorganisms was studied by the electronic microscope observation and the cell constituent release. This research would have an important implication for the design of more efficient antimicrobial systems for food preservation and production.
研究领域:
食品科学
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微生物学
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材料科学
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DOI
高影响因子
危险品化学品经营许可证（带存储）