JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2019
·
IF 3.571
Shanshan Wang,Kai Ye,Tong Shu,Xiuwen Tang,Xiu Jun Wang,Songbai Liu
In this study, incorporation of gallic acid into typical phytosterols (β-sitosterol and stigmasterol) through Steglich esterification was optimized employing the protection and deprotection strategy. A novel mechanism leading to side esterification was discovered. Complication of the phenolic hydroxyl groups and side reactions were successfully reduced under the optimized conditions. The structural identity and purity of galloyl stigmasterol and galloyl β-sitosterol were confirmed by NMR, FT-IR, and HPLC-MS. Evaluation of galloyl β-sitosterol and galloyl stigmasterol revealed their excellent antioxidant and cholesterol-reducing activities. Significant enhancement of cholesterol-reducing activity by galloylation was unveiled especially for β-sitosterol. Galloyl β-sitosterol had slightly better antioxidant activity at ambient temperature and better cholesterol-reducing activity. Molecular modeling suggested that a subtle difference of galloyl β-sitosterol and galloyl stigmasterol in activities could be attributed to variation of molecular rigidity and conformation. The excellent properties of galloyl β-sitosterol and galloyl stigmasterol suggested their great potential application in the food industry.
研究领域:
有机化学
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药学
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食品科学
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生物化学
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DOI
PubMed
高影响因子
MICROCHIMICA ACTA
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2024
·Vol. 191
·期 6
·1-14
·
IF 5.3
Guo Qi,Wang Du,Ma Fei,Fang Mengxue,Zhang Liangxiao,Li Peiwu,Yu Li
Phytosterols (PSs), a class of naturally occurring bioactive lipid compounds, have been found to possess a significant cholesterol-lowering effect. In developing countries, the consumption of rapeseed oil is the primary pathway of PS intake for the general population. However, developing low-cost, real-time, and high-throughput screening techniques for PSs remains a challenge. Here, a Cu-based nanocomposite CuOx@C was synthesized via a simple method of the calcination of HKUST-1 and systematically characterized by scanning electron microscopy, transmission electron microscopy, X-ray diffraction, and X-ray photoelectron spectroscopy. The CuOx@C demonstrated excellent peroxidase-like (POD-like) activity, functioning as a peroxidase mimic to facilitate the catalysis of 3,3′,5,5′-tetramethylbenzidine (TMB) into its oxidized form (oxTMB), thereby initiating a discernible color response. On the basis of this discovery, a CuOx@C-based colorimetric method for detecting total sterols in rapeseed was successfully constructed via cascade reactions. After optimizing the conditions, the high-throughput screening of total sterols in rapeseed could be completed in only 21 min, which significantly facilitated the sensing of PSs. A linear range of 0.6–6 mg/g was achieved for the detection of total sterols in rapeseed samples, thereby satisfying the requirements for detection. In addition, due to the high stability of CuOx@C and the specificity of cholesterol oxidase, the developed method had excellent stability and selectivity toward PSs, indicating that this work has huge prospects for commercial application. This innovative work overcomes the limitation of the instrumental method and provides a portable and reliable tool for total sterols detection. It can also facilitate the development of oilseeds with a high content of PSs. Graphical abstract
研究领域:
生物化学
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食品科学
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分析化学
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PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2025
·
IF 6.2
Zixing Chen,Chi Ho Jacky Chau,Andrew Erickson,Huafang Ding,Shouhe Huang,Wen-Sen He,Hanyue Zhu,Zhen-Yu Chen
Phytosterols have long been used to prevent hypercholesterolemia-related diseases, although their effects on intestinal cholesterol metabolism remain elusive. This study applied comparative proteomics to investigate the effects of various sterols on proteomic changes in differentiated Caco-2 cells. A total of 206, 231, 180, and 197 differentially expressed proteins were identified following treatment with cholesterol, β-sitosterol, stigmasterol, and campesterol, respectively. Functional enrichment analysis revealed that phytosterols significantly altered the proteome of Caco-2 cells, though their effect on cholesterol transport protein expression was negligible. Notably, while phytosterols did not regulate the expression of acyl-CoA:cholesterol acyltransferase 2 (ACAT2), β-sitosterol and stigmasterol significantly lowered the level of cholesterol oleate in Caco-2 cells by 57.1 ± 0.8% and 51.4 ± 3.9%, respectively, demonstrating that they inhibited ACAT2-catalyzed cholesteryl esterification activity. In view of the fact that cholesterol needs to be converted to cholesteryl esters before incorporation into chylomicrons, it was concluded that phytosterols primarily reduce intestinal cholesterol absorption by inhibiting ACAT2 enzyme activity rather than its gene expression. This study provides new insights into the regulation of cholesterol homeostasis by phytosterols in the small intestine.
研究领域:
营养生物化学
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分子生物学
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细胞生物学
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脂质代谢
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药理学
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蛋白质组学
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DOI
PubMed
高影响因子
BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY
·
2016
·Vol. 64
·期 6
·843-850
·
IF 1.429
Jianbin Ye,Zhan Zhang,Ji Yan,Hui Hao,Xiangzhen Liu,Zongcan Yang,Ke Ma,Xuepeng Yang,Duobin Mao,Hao Zhou
Phytosterols have been demonstrated to be precursors of polycyclic aromatic hydrocarbons (PAHs) formed during biomass pyrolysis. Here, a novel Paenibacillus sp. was evaluated for its ability to degrade phytosterols in tobacco waste extract (TWE). The optimal conditions for cell growth and stigmasterol (a representative of phytosterols) degradation were 37 °C, pH 7.0, 1.0 g/L yeast extract, and 6.0 g/L glucose. Paenibacillus sp. could degrade stigmasterol under high concentrations of glucose (up to 130 g/L) and tolerate wide pH (5.0–9.0) and temperature (25–42 °C) ranges. The new strain could degrade stigmasterol completely into CO 2 and H 2 O, and no intermediate steroids were detected during the degradation process. Phytosterol degradation in TWE was demonstrated by high-performance liquid chromatography–tandem mass spectrometry. Under optimal conditions (37 °C, pH 7.0, with the exponential-phase cells), the total degradation ratio of phytosterols reached 38.5% in TWE, including 45.2% of stigmasterol, 37.4% of β-sitosterol, 27.3% of campesterol, and 28.7% of cholesterol. These results showed that Paenibacillus sp. is a candidate for phytosterol degradation in TWE and other biomass and is potentially useful in reducing the PAHs generated from biomass pyrolysis.
研究领域:
环境微生物学
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生物降解
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生物质处理
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PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY A
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2011
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IF 4.194
Zhuomin Zhang,Wei Tan,Yuling Hu,Gongke Li
In this paper, an efficient and sensitive analytical method for the simultaneous determination of three trace sterols including ergosterol , stigmasterol and β-sitosterol in complicated biological samples was developed by gas chromatography–mass spectrometry (GC–MS) coupled with extraction using novel β-sitosterol magnetic molecularly imprinted polymer (mag-MIP) beads. Physical tests suggested that β-sitosterol mag-MIP beads prepared by a rapid microwave synthesis method possessed the porous morphology, narrow size distribution, stable chemical and thermal property. Due to the greatly enlarging surface area and the strong recognition to the target molecules, β-sitosterol mag-MIP beads have a higher enrichment factor for β-sitosterol (∼20-fold) and the higher selectivity for β-sitosterol and its analogs than that of β-sitosterol magnetic nonimprinted polymer (mag-NIP) beads. Under the optimum analytical conditions, all the target compounds achieved good chromatographic separation and sensitive detection without matrix interference. It was interesting that three target sterols were actually found in mushroom samples, and stigmasterol and β-sitosterol were actually found in serum and watermelon samples. The recoveries of spiked sample tests were in range of 71.6–88.2% with RSDs of 2.4–10.0% ( n = 3). This method is reliable and applicable for the simultaneous determination of trace sterols in real biological samples based on the β-sitosterol mag-MIP bead extraction.
研究领域:
分析化学
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生物化学
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PubMed
高影响因子
BIOCHEMICAL SYSTEMATICS AND ECOLOGY
·
2023
·
IF 1.6
Dongyu Gu,Chen Fang,Jing Liu,Zhongai Jiang,Gang Li,Minjing Li,Min Zhang,Yun Huang
Salicornia europaea L. is an economic plant which can grow in saline-alkali land, beach and other heavy saline soil . In this study, the inhibitory activities of S. europaea extracts against tumor cell growth including human non-small cell lung cancer cell A549 , human liver cancer cell HepG2, and brain glioma cell U251 were screened. The results showed that the ethanol extract of S. europaea had an inhibitory effect on the proliferation of A549 cells, and the inhibition of tumor cells showed time-dose relationship. Moreover, the ethanol extract of S. europaea was extracted and fractionated with different organic solvents and the activity results indicated that the petroleum ether fraction with IC 50 of 96.5 μg mL −1 possessed the best activity against A549 cells. Then seven compounds, including 30-norhederagenin ( 1 ), 24-methylenecycoartanol ( 2 ), pheophorbide A ( 3 ), stigmasterol ( 4 ), β -sitosterol ( 5 ), α-spinasterol ( 6 ), phytol ( 7 ) were isolated and identified from the petroleum ether fraction of S. europaea . Besides, the oil obtained from the petroleum ether fraction was analyzed by GC-MS, and fourteen compounds were identified. The compounds identified from the petroleum ether fraction mainly consisted of triterpenes , sterols, fatty acids, and their lipids .
研究领域:
药理学
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植物科学
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癌症研究
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生物化学
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DOI
高影响因子
METABOLIC ENGINEERING
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2019
·
IF 7.808
Wan-Ju Sun,Li Wang,Hao-Hao Liu,Yong-Jun Liu,Yu-Hong Ren,Feng-Qing Wang,Dong-Zhi Wei
The conversion of sterols to steroid synthons by engineered mycobacteria comprises one of the basic ways for the production of steroid medications in the pharmaceutical industry. Here, we revealed that high amounts of reactive oxygen species (ROS) generate during the conversion process of sterols, which impairs the cell viability of mycobacterial cells and thus hinders the conversion of sterols to steroid synthons. Accordingly, the endogenous antioxidants for detoxifying ROS in mycobacteria, ROS scavenging enzymes and low molecular weight thiols, were examined. The results revealed that three antioxidants, catalase (CAT), mycothiol (MSH), and ergothioneine (EGT), demonstrated efficacy toward neutralizing the excessive ROS produced during sterol metabolism . CAT overexpression or MSH or EGT augmentation enhanced the conversion of phytosterols to 22-hydroxy-23,24-bisnorchol-4-ene-3-one (4-HBC) by 18.9%, 23.8%, and 32.1%, respectively, and also enhanced the cell viability, indicating the benefits of these antioxidants in reducing ROS-induced stress. Further combinatorial augmentation of CAT, MSH, and EGT demonstrated enhanced effects toward intracellular ROS scavenging, resulting in 54.2% greater cell viability and 47.5% enhancement in 4-HBC production. These findings indicated that the excessive ROS induces cell stress, in turn limiting the conversion of sterols, whereas neutralization of the excessive ROS by combined control of CAT, MSH, and EGT serves as an effective strategy to boost the conversion productivity of sterols to steroid synthons.
研究领域:
药学
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微生物学
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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
LWT-FOOD SCIENCE AND TECHNOLOGY
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2022
·
IF 6.056
Fanfan Song,Jingnan Chen,Aoze Zheng,Shaojun Tian
The differences in sterol chemical structures influenced the membrane characteristics of liposomes, especially the physicochemical changes during storage. Therefore, the effects of sterols (cholesterol, β-sitosterol, and stigmasterol) on membrane characteristics were investigated and compared with liposomes without sterols. The incorporation of sterols increased the particle size of liposomes. Transmission electron microscopy images showed that sterols improved the rigidity and decreased the deformability of membranes. Cholesterol produced a more condensing effect on membranes, whereas stigmasterol reduced the effectiveness of lipid packing as shown by Raman spectroscopy. The addition of sterols provided good vesicle size stability during storage. Fluorescence probe analysis demonstrated decreased membrane hydrophobicity and micropolarity with prolonged storage. Phospholipid hydrolysis and oxidation played a major role in regulating membrane characteristics. Among the three sterols, β-sitosterol was the most effective for the inhibition of hydrolysis and oxidation.
研究领域:
药剂学
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生物物理学
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材料科学
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DOI
高影响因子
Food Quality and Safety
·
2023
·
IF 5.6
Li Yang,Wu Minyu,Zhai Liang,Zhang Hui,Shen Lirong
Camellia oil and olive oil with superior economic value are easily adulterated with other, cheaper oils. It is difficult to identify both oils by traditional methods because of their similar fatty acid profiles. In the present study, a novel method for qualitative and quantitative analysis of β-sitosterol using GC/MS and GC/FID was developed to identify camellia oil and olive oil. The method validation of β-sitosterol analysis showed good linearity and satisfactory values for recovery, accuracy, precision, and repeatability. The linear regression coefficient (R2) of the calibration curve was 0.9985. An acceptable limit of detection (0.36 mg/100 g) and limit of quantification (1.20 mg/100 g) were achieved. The spiked recoveries were 95.0% to 100.3%. The relative standard deviation (RSD) of within-day precision was less than 3.26%, and the RSD of retention times and peak areas for repeatability were within 0.03% and 1.08%, respectively. The contents of β-sitosterol in virgin camellia oil and virgin olive oil were in the range of 14.1–30.2 mg/100 g and 94.3–173.2 mg/100 g, respectively, indicating that the β-sitosterol content in the former is seven times that in the latter, and β-sitosterol could be a potential marker for the authentication and adulteration detection of both oils.
研究领域:
食品科学
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分析化学
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产品关联
DOI
高影响因子
PROSTAGLANDINS & OTHER LIPID MEDIATORS
·
2025
·
IF 2.5
Jindao Wang,Minghui Zhou,Qiuli Zhou,Guangyang Sun,Yu Zhang,Feng Tao,Minfeng Ye
Background Gastric cancer (GC) is the third leading culprit of cancer-related deaths around the world. Beta-sitosterol (BS) is an important phytosterol that has been proven to have anti-proliferative effects on GC and other tumors. However, mechanisms and targets of BS in cancer are rarely explored. Methods In this investigation, the targets of BS in the treatment of GC were analyzed by network pharmacology. Molecular docking and cellular thermal shift assay were introduced to validate the binding relationship between BS and PTGS1. The impacts of BS on GC cell viability, half maximal inhibitory concentration, proliferation ability, apoptosis level, and angiogenesis ability were detected by using Cell Counting Kit-8, clone formation assay, flow cytometry, and angiogenesis experiment, respectively. In addition, the expression levels of angiogenic factors (VEGF, FGF, PAI-1) were detected by using western blot. Results In this project, through cell experiments, PTGS1 was identified as a protein that directly binds to BS. In vitro cell experiments revealed that BS promoted apoptosis and inhibited GC cell proliferation and angiogenesis. Importantly, treatment with BS attenuated the promoting influence of PTGS1 overexpression on GC cell proliferation and angiogenesis. Conclusion This investigation highlighted PTGS1 as the target of BS in GC cells. BS can regulate PTGS1 to inhibit GC cell proliferation and angiogenesis, providing new evidence for the potential use of BS as a therapeutic agent for GC.
研究领域:
肿瘤学
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药理学
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分子生物学
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DOI
PubMed
高影响因子
Biotechnology Journal
·
2024
·Vol. 19
·期 11
·e202400489
·
IF 3.2
Bo Zhang,Sifang Zhu,Yi Zhu,Xin Sui,Junping Zhou,Zhiqiang Liu,Yuguo Zheng
Boldenone (BD), a protein anabolic hormone, is commonly used to treat muscle damage, osteoporosis, and off-season muscle building in athletes. Traditional BD synthesis methods rely on chemical processes, which are costly and environmentally impactful. Therefore, developing a more sustainable and economical biosynthetic pathway is crucial for BD production. This study aimed to achieve efficient production of BD. Firstly, the catalytic performance of 17β-hydroxysteroid dehydrogenase and 3-ketosteroid-Δ 1 -dehydrogenase was improved through enzyme engineering, and their expression in the new strain of Mycobacterium neoaurum was enhanced using metabolic engineering. These improvements significantly increased BD production to 4.05 g/L, with a significant decrease in by-product generation. To further increase the yield, a multi-enzyme fusion expression system was constructed, and a key cell wall gene kasB was knocked out, resulting in a spatial-time yield of BD reaching 1.02 g/(L·d). Subsequent optimization of the transformation system further increased the BD production to 5.56 g/L, with a spatiotemporal yield of 1.39 g/(L·d). The green biosynthetic route of phytosterol one-step conversion to BD developed in this study lays the foundation for industrial production.
研究领域:
生物化学
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微生物学
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合成生物学
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DOI
PubMed
高影响因子
FOOD HYDROCOLLOIDS
·
2023
·
IF 10.7
Bo-wen Yang,Sheng-yang Ji,Tian Zhao,Zhang-tie Wang,Yan-song Zhang,Qian-nan Pan,Wei-su Huang,Bai-yi Lu
Although phytosterols (PS) showed various excellent health functions, their applications in the food industry were limited by poor water solubility and high oxidation sensitivity. This study investigated the fabrication of phytosterol-enriched emulsions stabilized by different emulsifiers and evaluated the effect of different interfacial layers on the photooxidation of phytosterols and emulsions. The emulsions were prepared with Tween 20, whey protein isolate (WPI), and soy protein isolate (SPI) to achieve interfacial membranes with different properties. The SPI-dextran mixture or dextran-glycated SPI was adopted as the additional emulsifier. Compared with Tween 20, high molecular weight emulsifiers (proteins and their mixtures) exhibited stronger photooxidation stabilities and high viscosity and density of droplet interfacial membrane. The stability of PS emulsions that undergo photooxidation was impacted by the inclusion of these emulsifiers, whereas the extent of phytosterols photooxidation was, from highest to lowest, in the following order: SPI/dextran mixture > glycated SPI mixture > WPI > SPI > Tween 20. The proper SPI concentration (1.5 wt%) showed the highest interface pressure and viscosity and the higher PS stability. Moreover, the higher rheological properties and surface pressure of droplets reveal extra oxidative stability and lower oxidation rate of PS, as well as the formation of additional 7β-OH products. This work demonstrates that emulsions may be tuned toward better photooxidation oxidative stability by modifying interface composition and interfacial properties.
研究领域:
食品科学
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生物学
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DOI
高影响因子
危险品化学品经营许可证（带存储）