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INTERNATIONAL JOURNAL OF PHARMACEUTICS · 2018 · IF 3.862

Therapeutic efficacy of lipid emulsions of docetaxel-linoleic acid conjugate in breast cancer

Tao Zhang,Meng Li,Ruyi Yang,Dong Zhang,Jibin Guan,Jiang Yu,Bin Yang,Huicong Zhang,Shenwu Zhang,Dan Liu,Yongjun Wang

Docetaxel (DTX) solution is among the most widely-used parenteral formulations used in advanced breast cancer therapy. However, severe side effects have been observed due to the use of ethanol and polysorbate 80 . Herein, a novel DTX-based prodrug , docetaxel-linoleic acid conjugate (DTX-LA) was successfully synthesized. The high lipid solubility of DTX and DTX-LA resulted in a tendency for them to become entrapped in the oil core of the emulsions. As anticipated, nano-sized, sterically stabilized oil-in-water lipid emulsions (LMs) of DTX-LA LMs and DTX LMs were successfully constructed. Unlike DTX solution, LMs exhibited high colloidal stability and sustained-release behavior, having a narrow size distribution that was ∼220  nm in diameter. Compared with DTX LMs, DTX-LA LMs had a greater drug-loading capacity. Although the cytotoxicity of DTX-LA LMs was reduced in comparison with DTX solution, the pharmacokinetic study demonstrated increased bioavailability (p < 0.001) and half-life (p < 0.01). Finally, DTX-LA LMs displayed significant antitumor efficacy with reduced side effects in a 4T1 breast cancer xenograft model. Thus, the novel lipid emulsion-based docetaxel prodrug delivery system may be a promising strategy for improving intravenous administration for breast cancer treatment.

研究领域: 药学 · 肿瘤学
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Journal of Physical Chemistry C · 2016 · IF 4.509

Facile Synthesis of Water-Soluble WS2 Quantum Dots for Turn-On Fluorescent Measurement of Lipoic Acid

Yinghan Yan,Cuiling Zhang,Wei Gu,Caiping Ding,Xinchang Li,Yuezhong Xian

A facile and eco-friendly approach for the synthesis of water-soluble WS2 quantum dots (QDs) was developed via ultrasonication and a hydrothermal process from bulk WS2. In this strategy, the dispersity of bulk WS2 in aqueous phase was improved with the aid of a surfactant (hexadecyltrimethylammonium bromide, CTAB), which could shorten the exfoliation time and improve the exfoliation efficiency to form layered WS2 nanosheets. Through hydrothermal treatment, the nanosheets were further scissored into QDs with high quality. The QDs show excellent features with narrow size distribution, good water solubility, and stable fluorescence. We find that the fluorescence of WS2 QDs can be quenched by Fe3+ through photoinduced electron transfer, and a wide detection linear range for Fe3+ is acquired. It indicates that WS2 QD can be used as a “turn-off” probe for Fe3+. In the presence of lipoic acid (LA), the fluorescence was recovered due to the stronger interaction between LA and Fe3+ than WS2 QDs. A “turn-on” sensor for LA was developed with a linear range from 1 to 10 μM and a detection limit of 0.59 μM. The strategy might be suitable for the facile synthesis of other water-soluble transition metal dichalcogenide QDs. It is expected that the water-soluble QDs have great potential applications in biological system.

研究领域: 材料科学 · 分析化学 · 生物医学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2022 ·Vol. 103 ·期 1 ·108-117 · IF 4.125

Structure-guided preparation of fuctional oil rich in 1,3-diacylglycerols and linoleic acid from Camellia oil by combi-lipase

Chuanqing Huang,Zepeng Lin,Yunlong Zhang,Zeyu Liu,Xiaoyue Tang,Changzhu Li,Lin Lin,Wenqian Huang,Yong Ye

Background Diacylglycerol (DAG)-enriched oil has been attracting attention because of its nutritional benefits and biological functions, although the composition of its various free fatty acids (FFAs) and an unclear relationship between substrate and yield make it difficult to be identified and qualified with respect to its production. In the present study, linoleic acid-enriched diacylglycerol (LA-DAG) was synthesized and enriched from Camellia oil by the esterification process using the combi-lipase Lipozyme TL IM/RM IM system. Results The relationship between FFA composition and DAG species productivity was revealed. The results showed that heterogeneous FFA with a major constituent (more than 50%) exhibited higher DAG productivity and inhibited triacylglycerol productivity compared to homogeneous constituents. Joint characterization by high-performance liquid chromatography-evaporative light scattering detection, gas chromatography-mass spectrometry and ultra-performance liquid chromatography-heated electrospray ionization-tandem mass spectrometry identified that DAG components contained dilinoleic acid acyl glyceride, linoleyl-oleyl glyceride and dioleic acid acyl glyceride in esterification products. Under the optimum conditions, 60.4% 1,3-DAG and 61.3% LA-DAG in the crude product at 1 h reaction were obtained, and further purified to 81.7% LA-DAG and 94.7% DAG via silica column chromatography. Conclusion The present study provides a guideline for the identification of DAG species, as well as a structure-guided preparation method of DAG-enriched oils via the cost-effective combi-lipase. © 2022 Society of Chemical Industry.

CAS / MDL: 1312-81-8 112-80-1
研究领域: 食品科学 · 生物化学
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RSC Advances · 2015 ·Vol. 5 ·期 26 ·20248-20255 · IF 3.84

Synergetic effect of ruthenium and basicity sites in the Ru–MgAl catalyst for hydrogen-free production of conjugated linoleic acids

Jiebo Chen,Xinxiang Chen,Ying Zheng,Qinglu Li

A series of Ru–MgAl composite oxide catalysts prepared by calcining the ruthenium grafted hydrotalcite-like precursor at various temperatures were used in the hydrogen-free production of conjugated linoleic acid. The effect of calcination temperature on the textural, base and catalytic properties of the materials was investigated. Results indicated that the Ru–MgAl composite oxides calcined at 450 °C showed high activity, namely, CLA productivity, CLA production rate and TOF up to 1.52 g CLA g (CLA) L−1 (solvent) min−1, 284 g (CLA) g−1 (Ru) h−1 and 102.6 mol (LA converted) mol−1 (Ru) h−1. Moreover, the biologically active CLA isomers, cis-9, trans-11, trans-10, cis-12 and trans-9, trans-11-CLA, were the main products, while almost no hydrogenated products were formed. Meanwhile, the role of ruthenium and basicity sites in the catalytic reaction has been studied. It was found that the basicity sites of the Ru–MgAl catalyst and the ruthenium activity sites seem to have a synergic effect on the catalytic reaction. The possible reaction mechanism for the isomerization was also proposed.

研究领域: 催化化学 · 食品科学 · 生物化学
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Frontiers in Oncology · 2025 · IF 3.3

Elucidating the role of fatty acid reprogramming in ovarian cancer: insights cross-talk between blood, subcutaneous fat, and ovarian cancer tissues

Xiaocui Zhong,Mamona Bilal,Yanqiu Zhou,Xiaojia Yang,Zuchao Qin,Qibing Li,Yang Yang,Ting-Li Han,Min Li

Introduction Aberrant fatty acid (FA) metabolism is increasingly recognized as a significant factor in ovarian cancer (OC) progression, although the comprehensive metabolic alterations across different body tissues remain unclear. Methods In this study, sixteen OC patients and twenty-nine non-cancer (NC) patients were recruited for metabolic profiling using a global and targeted metabolomic strategy based on a gas chromatography-hydrogen flame ionization detector (GC-FID). The patient survival was followed up to 3 years, and PFS was calculated. Results Our findings revealed distinct metabolite profiles that differentiate OC from NC groups across all sample types. We found seven, nine, and thirteen significant metabolites in subcutaneous fat, plasma, and ovarian tissue respectively. In particular, docosahexaenoic acid (DHA) and arachidonic acid (AA) levels were notably elevated in all sample types of OC patients. Furthermore, receiver operating characteristic (ROC) analysis highlight that three plasma FA showed the best specificity and sensitivity in differentiating the OC group from the NC group (Area Under The Curve, AUC > 0.89), including caprylic acid, myristoleic acid, and tetracosaenoic acid. Most of the significant FA in subcutaneous fat and ovarian tissue showed a high risk of OC. However, caprylic acid and tetracosanoic acid were identified as protective factors in the plasma sample. We also found that high levels of linoelaidic acid in subcutaneous fat and palmitelaidic acid in ovarian tissue were associated with poor prognosis. Pathway analysis indicated upregulation of fatty acid synthesis, inflammatory signaling, and ferroptosis pathways in OC patients. Discussion This study reveals a coordinated reprogramming of FA metabolism across multiple biospecimens in OC patients. Our results suggest that specific fatty acids may contribute to OC progression through dysregulation of fatty acid synthesis, inflammatory signaling, and ferroptosis. These findings offer mechanistic insights into OC progression and highlighting potential biomarkers and targeted therapeutic interventions.

研究领域: 肿瘤学 · 代谢组学 · 生物化学
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Foods · 2024 ·Vol. 13 ·期 24 ·4153 · IF 4.7

Effect of Boiling Treatment on Linoleic Acid-Induced Oxidation of Myofibrillar Protein in Grass Carp

Mengcong Liu,Fuhua Li,Yuan Tang,Jichun Zhao,Xiaojuan Lei,Jian Ming

The aim of this study was to investigate the promotion of linoleic acid (OLA)-induced myofibrillar protein (MP) oxidation by boiling treatment. The effect of the boiling treatment on grass carp MP oxidation induced by OLA was investigated. The total sulfhydryl content, fluorescence intensity, and amino acid content were reduced with the increasing OLA concentration after the boiling treatment, while the boiled oxidized MP’s carbonyl content (4.76 ± 0.14 nmol/mg) was 2.14 times higher than that of the native MP (2.22 ± 0.02 nmol/mg) at an OLA concentration of 10 mM. Additionally, the secondary structure of MP became more disordered, shifting from an α-helix to random coils and β-turns. When the concentration of OLA was higher than 5 mM, both the surface hydrophobicity and water holding capacity (WHC) decreased with the increasing OLA concentration. Furthermore, the boiling treatment led to a reduction in immobile water and an increase in free water content in the MP gel. These findings establish a theoretical basis for regulating MP oxidation to improve fish quality during boiling.

研究领域: 食品科学 · 生物化学
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Foods · 2022 ·Vol. 11 ·期 7 ·980 · IF 5.561

Recombinant Porcine 12-Lipoxygenase Catalytic Domain: Effect of Inhibitors, Selectivity of Substrates and Specificity of Oxidation Products of Linoleic Acid

Jiamei Xu,Yu Liu,Jingjing Ma,Pengpeng Li,Zhiming Geng,Daoying Wang,Muhan Zhang,Weimin Xu

Lipoxygenase (LOX)is a major endogenous enzyme for the enzymatic oxidation of lipids during meat storage and meat product manufacturing. In the present work, some characteristics, i.e., effects of inhibitors, selectivity of substrates and specificity of oxidation products, were studied using recombinant porcine 12-lipoxygenase catalytic domain(12-LOXcd). Several familiar inhibitors were found inhibit the activity of recombinant porcine 12-LOXcd;nordihydroguaiaretic acid demonstrated the strongest inhibitory effect. The enzyme could oxygenate common polyunsaturated fatty acids, and showed the highest affinity to linoleic acid (LA), followed by arachidonic acid (AA), linolenic acid (LN) and docosahexaenoic acid (DHA). Under the action of porcine 12-LOXcd, LA was oxidized into four hydroxyoctadecadienoic acid (HODE) isomers, i.e., 13-Z,E-HODE, 13-E,E-HODE, 9-Z,E-HODE and 9-E,E-HODE. Variation of pH not only affected the yield of LA oxidation products, but also the distribution of HODE isomers. These results indicated that endogenous LOX activity and LOX-catalyzed lipid oxidation can be regulated during meat storage and meat product manufacturing.Keywords:Lipoxygenase;inhibitors;substrates;oxidation products;linoleic acid;porcine

研究领域: 食品科学 · 生物化学 · 酶学
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2024 ·Vol. 25 ·期 6 ·3194 · IF 4.9

NMR Study of Water-Soluble Carotenoid Crocin: Formation of Mixed Micelles, Interaction with Lipid Membrane and Antioxidant Activity

Wenjing Su,Anna V. Mastova,Maya A. Ul’yanova,Polina A. Kononova,Olga Yu. Selyutina,Veronika I. Evseenko,Elizaveta S. Meteleva,Alexander V. Dushkin,Weike Su,Nikolay E. Polyakov

Crocin is a unique water-soluble carotenoid found in crocus and gardenia flowers. Crocin has been shown to have a variety of pharmacological activities, such as antioxidant, anti-cancer, memory improvement, antidepressant, anti-ischemia, blood pressure lowering and aphrodisiac, gene protection and detoxification activities. Due to their amphiphilicity, crocin molecules form concentration-dependent self-associates (micelles) in a water solution. In the present study, using various NMR techniques (T2relaxation and selective gradient NOESY), we have demonstrated that crocin forms mixed micelles with water-soluble drug delivery system glycyrrhizin and linoleic acid molecules. Note, that the spin–spin T2relaxation time and NOESY spectroscopy are very sensitive to intermolecular interactions and molecular diffusion mobility. The second purpose of this work was the elucidation of the interaction of crocin with a model lipid membrane using NMR techniques and a molecular dynamics simulation and its effects on lipid oxidation. It was shown that the crocin molecule is located near the surface of the lipid bilayer and effectively protects lipids from oxidation by peroxyl radicals. The role of glycyrrhizin and vitamin C in metal-induced lipid oxidation was also elucidated. The results of this study may be useful for expanding the field of application of crocin in medicine and in the food industry.

CAS / MDL: 60-33-3
研究领域: 药理学 · 食品科学 · 生物化学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2024 ·Vol. 104 ·期 11 ·6787-6798 · IF 3.3

Influence mechanisms of linoleic acid and oleic acid on the gel properties of egg yolk protein

Xinyuan Huang,Xin Li,Yufeng Zhang,Xiefei Li,Pei Zhang,Hongbo Song,Qun Huang,Guiming Fu

BACKGROUND Gel property is among the crucial functional properties of egg yolk (EY), which determines the texture and flavor of EY products. In the present study, the effects of two unsaturated fatty acids [monounsaturated fatty acid oleic acid (OA) and diunsaturated fatty acid linoleic acid (LA)] on the gel properties of EY protein were investigated. RESULTS Compared with the blank group, the addition of LA and OA (10–50 g kg −1 ) improved the gel hardness (from 270.54 g to 385.85 g and 414.38 g, respectively) and viscosity coefficient (from 0.015 Pa.s n to 11.892 Pa.s n and 1.812 Pa.s n , respectively). The surface hydrophobicity of EY protein increased to a maximum value of 40 g kg −1 with the addition of both fatty acids (39.06 μg and 41.58 μg, respectively). However, excess unsaturated fatty acids (≥ 50 g kg −1 ) disrupted the completeness of the gel matrix and weakened the structural properties of the EY gel. CONCLUSION Both fatty acids improved the gel properties of EY protein. At the same addition level, OA was superior to LA in improving gel properties. The present study provides a theoretical underpinning for the sensible application of unsaturated fatty acids in improving EY gel properties. © 2024 Society of Chemical Industry.

CAS / MDL: 7439-91-0 112-80-1
研究领域: 食品科学 · 生物化学
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Antioxidants · 2022 ·Vol. 11 ·期 2 ·376 · IF 7.675

The Interplay of Ascorbic Acid with Quinones-Chelators—Influence on Lipid Peroxidation: Insight into Anticancer Activity

Olga Yu. Selyutina,Polina A. Kononova,Vladimir E. Koshman,Lidiya G. Fedenok,Nikolay E. Polyakov

Ascorbic acid is a multifaceted compound that can perform both antioxidant and pro-oxidant activities in the redox reactions induced by transition metal ions, so its role in nature and especially in the human body is still the subject of debate. In the present study, we have examined the influence of ascorbic acid on lipid peroxidation in a model system that mimics the cell membrane, namely micelles of linoleic acid (LA), induced by chelate complexes of iron and copper ions with quinone-chelator 2-phenyl-4-(butylamino)-naphtholquinoline-7,12-dione (Q1). This quinone effectively generates reactive oxygen species and semiquinone radicals inside cancer cells via a cycling redox reaction. Here it was demonstrated that in the absence of quinone-chelator ascorbic acid significantly accelerates the lipid peroxidation induced by both Fe(II) and Cu(II) ions. It has been shown also that Q1 chelate complexes with Fe(II) and Cu(II) ions are redox active in the LA micelles oxidation. No effect of ascorbate was detected on the reactivity of chelate complex with Fe(II) ions. On the other hand, ascorbate performs pro-oxidant activity in Q1-Cu(II) complex induced reaction. We can conclude that ascorbate-driven redox cycling of Q1 may promote its anti-tumor activity.Keywords:anthraquinones;ascorbic acid;lipid peroxidation;anticancer activity;linoleic acid;NMR

CAS / MDL: 60-33-3
研究领域: 生物化学 · 医学研究
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INDUSTRIAL CROPS AND PRODUCTS · 2025 · IF 6.2

Preparation and characteristics of dehydrated ricinoleic acid by ionic liquid catalysis

Panpan Xu,Fengdan Yan,Mengyang Liu,Yanlan Bi,Shangde Sun,Jun Li

Effects of N-methylimidazole hydrogen sulfate, 2-pyrrolidone hydrogen sulfate, N-methyl pyrrolidone hydrogen sulfate, and their -SO 3 H functionalized acidic ionic liquids were comparatively investigated on the dehydration degree of ricinoleic acid (RA) sample and conjugated linoleic acid (CLA) content in the resulting dehydrated ricinoleic acid (DRA) sample. Results showed the -SO 3 H functionalized N-methyl pyrrolidone hydrogen sulfate ([C 3 SO 3 Hnmp]HSO 4 ) had the strongest catalytic activity among the six ionic liquids. Under the optimal conditions (4 % [C 3 SO 3 Hnmp]HSO 4 , 250 °C, and 30 min), the dehydration degree of RA sample reached 98.69 % with 42.57 % of CLA in the resulting DRA sample. Results from nuclear magnetic resonance, Fourier transform infrared spectroscopy, and mass spectrometry indicated the hydroxyl group of RA underwent intramolecular dehydration to form new double bonds; RA sample was randomly dehydrated with both non-conjugated linoleic acid and CLA present in DRA sample. Rheological analysis showed that RA sample had a higher viscosity than DRA sample due to the presence of hydrogen bonds. Thermogravimetric analysis showed RA and DRA samples were thermally stable at up to 250 °C.

研究领域: 食品科学 · 化学工程
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Food Bioscience · 2024 · IF 4.8

Effects of pH, linoleic acid, and reheating on volatile compounds in glucose-lysine model system

Feng Du,Yiqun Huang,Zhijie Liu,Junjian Miao,Keqiang Lai

This study aimed to investigate the effects of pH (5.8, 7.0, and 10.0), linoleic acid , and reheating (heating: 180 °C, 30 min; reheating: 100 °C, 10 min) on the reactants, α-dicarbonyl compounds, and volatile compounds in the glucose-lysine model system, with a specific focus on exploring the influences of volatile compounds. The results showed that under three different pH glucose-lysine model system yielded the detection of 9, 15, and 29 volatile compounds, respectively. Notably, both the number and content of volatile compounds exhibited an upward trend as the pH increased. Reheating treatment led to changes in both the number and content of volatile compounds. The addition of linoleic acid affected the generation of heterocyclic compounds associated with the Maillard reaction . Volatile compounds such as aldehydes and alcohols were generated in systems containing linoleic acid, resulting in a higher number and content of volatile compounds compared to systems without linoleic acid.

CAS / MDL: 60-24-2 S294951
研究领域: 食品科学 · 化学
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