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WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY · 2025 ·Vol. 41 ·期 5 ·1-10 · IF 4.2

Bioconversion of sterol esters to steroid intermediates through Mycobacterium sp. fermentation

Bi Yingjing,Han Yun,Bi Yanlan,Zhang Linshang,Sun Shangde

Sterol esters are naturally present in the by-product of edible oil processing, which is generally converted to sterols through saponification. Steroid intermediates play a crucial role in the production of pharmaceuticals, and these intermediates are predominantly synthesized via fermentation of sterol. This research explored the direct conversion of sterol esters into steroid intermediates using Mycobacterium sp. as a fermentation agent. The results demonstrated the successful identification of four steroid intermediates: androstenedione, 1,4-androstadienedione, 22-hydroxy-23,24-bisnorchol-4-ene-3-one, and 22-hydroxy-23,24-bisnorchol-1,4-dien-3-one, their individual intermediate concentrations were as follows: 144.2, 176.2, 30.8, 53.6 mg/L, with a total yield of 404.8 mg/L and a conversion rate of 29.5%. The optimized fermentation conditions included soybean oil at 3%, an initial pH of 7.0, a nitrogen source of 4.5 g/L, and hydroxypropyl-β-cyclodextrin of 15.0 g/L. Proteomic analysis revealed that sterol esters conversion pathway mirrors that of sterol, with an additional hydrolysis process. This work significantly expands our understanding of steroid intermediates production and offers valuable insights for the bioproduction industry. Graphical

研究领域: 生物化学 · 制药工程 · 微生物学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2022 ·Vol. 102 ·期 15 ·7115-7125 · IF 4.125

Enhanced antioxidant capacity of lipoic acid in different food systems through lipase-mediated esterification with phytosterols

Wen-Sen He,Yuying Sun,Zhishuo Li,Haonan Yang,Junjie Li,Qingzhi Wang,Chen Tan,Bin Zou

BACKGROUND α-Lipoic acid has excellent antioxidant activity, but its poor lipid solubility greatly limits its practical application. This study was undertaken (i) to develop a novel and efficient enzymatic synthesis of lipophilic lipoic acid esters using Candida sp. 99-125 lipase as a catalyst; and (ii) to systematically evaluate their antioxidant potential against bulk oil, oil-in-water emulsion (O/W) and cooked ground meat. RESULTS Lipophilic lipoic acid esters were successfully and efficiently synthesized using phytosterols as acyl receptor in the presence of Candida sp . 99-125 lipase. The product was identified as phytosterol lipoate by mass spectrometry, Fourier transform infrared spectroscopy and nuclear magnetic resonance. The maximum conversion of phytosterol lipoate surpassed 90% within 12 h and its final yield exceeded 81%. Interestingly, the oil solubility of lipoic acid was increased at least 25-fold and other physicochemical properties were significantly improved. Most importantly, phytosterol lipoate exhibited higher antioxidant activity than lipoic acid in bulk oil, O/W emulsions and cooked ground meat. CONCLUSION The antioxidant capacity of lipoic acid can be significantly enhanced by esterification with phytosterols. Therefore, phytosterol lipoate could be further developed as a new antioxidant for use in oil- and fat-based foods. © 2022 Society of Chemical Industry.

研究领域: 食品科学 · 生物化学
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ACS Food Science & Technology · 2025 · IF 2.8

Fabrication of Plant Sterol Ester–Gelatin Bigels as Cocoa Butter Substitutes: A Strategy for Low-Calorie Chocolate Development

Min Pang,Lu Xu,Ying Qian,Mengke Li,Jianglin Chen,Jieshun Cheng,Lili Cao

Cocoa butter (CB) substitution remains challenging for low-calorie chocolates due to texture and stability compromises in conventional alternatives. This study developed bigels (oleogel/hydrogel ratios = 3:7, 5:5, 7:3 w/w) from phytosterol ester oleogel and gelatin hydrogel as CB substitutes. The optimal CB substitution was screened by characterizing the bigels’ physicochemical properties. Subsequently, compound chocolates were fabricated using the selected bigel system, with the optimal substitution ratio determined through the comprehensive evaluation of their micromorphology, thermal behavior, and sensory profiles. X-ray diffraction revealed peaks at 4.151 and 3.741 nm. At 70 wt % oleogel, the bigel exhibited the highest hardness (307.34 ± 30.66 g). Subsequently, compound chocolates were produced with bigels at substitution levels of 20–100 wt %, showing melting temperatures (42.66–75.30 °C) significantly higher than CB (41.51 °C). The L* (17.43 ± 0.64) and a* (2.13 ± 0.25) values of the CB group, along with its sensory evaluation score (83.50 ± 2.31), showed no statistically significant difference (p < 0.05) when compared to 20% (16.62 ± 0.41, 2.57 ± 0.12, 83.50 ± 1.97) and 40% samples (16.19 ± 0.58, 2.66 ± 0.14, 81.14 ± 2.35). Phytosterol ester–gelatin bigels successfully replicated CB’s functional properties, demonstrating feasibility as calorie-reduced alternatives. This work provides a novel strategy for designing structured lipid systems in confectionery applications, addressing both nutritional and sustainability demands in the food industry.

CAS / MDL: 9000-70-8
研究领域: 食品科学 · 营养学
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ACS Sustainable Chemistry & Engineering · 2021 · IF 8.198

Magnetic Switchable Pickering Interfacial Biocatalysis: One-Pot Cascade Synthesis of Phytosterol Esters from High-Acid Value Oil

Tao Yang,Yufei Zhang,Jing Wang,Fenghong Huang,Mingming Zheng

The traditional reutilization of high-acid value oil resources causes pollution, suffers from high energy consumption, and brings relatively low economic value. In this study, high-acid value oil was converted into high-value product phytosterol esters (PEs) using a “one-pot” enzymatic cascade reaction strategy including the hydrolysis of high-acid value oils into free fatty acids (FFAs) and followed by its esterification of phytosterols. Lipase AYS was immobilized on magnetic hollow mesoporous carbon nanospheres to obtain AYS@MHMCS, forming a sustainable and solvent-free Pickering interfacial biocatalysis platform. Each droplet in the emulsion system served as a microreactor with the reactants in the oil phase; the byproduct glycerol was spontaneously excreted to the aqueous phase which would “push” the hydrolysis reaction forward. The products of hydrolysis (fatty acids) remained in the oil phase, continuing the next esterification reaction with phytosterols, which ensured the efficient and continuous operation of the tandem reaction. Benefiting from the interfacial activation effect of lipase, the catalytic efficiency of the emulsion system was 30 times that of the single-phase system. The yield of PEs was up to 90%, while the highest in the single-phase was only 30%. Additionally, the magnetic-responsive Pickering emulsion could recover AYS@MHMCS intactly in 15 min, and there would be no significant loss of catalytic activity even after continuous reuse for 15 cycles. This method not only provides a robust biocatalysis technique with a sustainable interface but also paves the way to high-value utilization of high-acid value oil resources.

研究领域: 生物催化 · 环境科学 · 材料科学
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INTERNATIONAL JOURNAL OF DAIRY TECHNOLOGY · 2024 ·Vol. 77 ·期 3 ·961-972 · IF 2.5

A shelf life prediction method for butter based on the effects of β-carotene on colour and oxidative stability

Shujie Cheng,Shimin Wu

This study aimed to examine the impact of β-carotene, astaxanthin and phytosterol esters on the colour and oxidative stability of butter, as well as to explore a shelf life prediction method based on colour analysis. The results of correlation analysis indicated a significant linear correlation between acidity and whiteness index and yellowness index, with a linear fit coefficient ( r 2 ) exceeding 0.9796. In comparison with traditional shelf life prediction models, this method exhibited an average deviation of only 6.9% in its predicted results. The findings may contribute to the rapid evaluation of the shelf lives of commercial butter products.

CAS / MDL: 472-61-7 110-54-3
研究领域: 食品科学 · 生物学
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MATERIALS RESEARCH BULLETIN · 2015 · IF 2.288

Immobilization of Candida rugosa lipase on ZnO nanowires/macroporous silica composites for biocatalytic synthesis of phytosterol esters

Chuan-Yang Shang,Wei-Xun Li,Rui-Feng Zhang

ZnO nanowires were successfully introduced into a macroporous SiO 2 by in-situ hydrothermal growth in 3D pores. The obtained composites were characterized by SEM and XRD, and used as supports to immobilize Candida rugosa lipase (CRL) through adsorption. The high specific surface area (233   m 2 /g) and strong electrostatic interaction resulted that the average loading amount of the composite supports reached 287.2   mg/g. Both adsorption capacity and the activity of the CRL immobilized on the composite supports almost kept unchanged as the samples were soaked in buffer solution for 48   h. The immobilized CRL exhibited better thermal stability, reusability and pH adaptability in comparison to free CRL. The immobilized CRL was used as biocatalyst for the preparation of phytosterol esters by the esterification of phytosterol and oleic acid. A maximum molar conversion of 96.5% was achieved under the optimal condition. After twelve recycles the immobilized lipase could retain 89.9% of its initial activity.

研究领域: 生物化学 · 纳米材料科学 · 酶工程
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ACS Food Science & Technology · 2025 · IF 2.8

Novel Phytosteryl-Ester-Based Mozafari Preparation of Liposomes and Layer-by-Layer Coating

Zhengyang Wu,Songbai Liu

In this study, a novel phytosteryl-ester (PSE)-based Mozafari preparation approach and subsequent LbL coating were successfully developed, employing tea polyphenol palmitate (TPP) as the key antioxidant component. Substantial lower temperature (50 °C) for phase transition was realized by employing PSE for liposome formation. Incorporation of PSE and TPP achieved optimal formation of liposomes. The prepared liposomes exhibited great stability and encapsulation efficiency for typical lipophilic curcumin (Cur) and hydrophilic anthocyanin (An) bioactives. Layer-by-layer (LbL) coating of the liposomes by alternate exposure to positively charged gelatin and negatively charged hyaluronic acid afforded extraordinary protection from oxidative degradation (Cur: 86%, An: 81% retention). Evaluation of ROS reduction capacity by the Escherichia coli Nissle 1917 probiotic model and release behavior in simulated digestion revealed exceptional antioxidant performance (Cur: 57%, An: 55% ROS reduction) and sustained release of liposomal bioactives. The developed approaches hold great promise in liposome bioactives delivery.

研究领域: 食品科学 · 生物化学 · 药物递送系统
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2024 · IF 6

Construction of Pickering emulsion and its application in enzymatic synthesis of phytosteryl oleate

Ning Wang,Donghua Wang,Dandan Wu,Liqi Wang,Xiuqing Zhu,Dianyu Yu

In this study, Janus nanoparticles were prepared and used to construct Pickering emulsion as an emulsifier in presence of lipase. The results showed that Janus nanoparticles could be used to stable water phase in emulsion and the average particle size of emulsion was 60 μm. Phytosterol ester was successfully synthesized in Pickering emulsion catalytic system by using oleic acid as acyl accepter, and the phytosterol conversion reached 91.65 ± 2.07% under the following conditions: emulsifier amount of 1.0 wt%, oil-water ratio of 6:1, phytosterol concentration of 110 mmol/L, lipase dosage of 20 g/L, reaction temperature of 45 °C. Compared with biphasic catalytic system, Pickering emulsion catalytic system could enhance the catalytic efficiency and shorten the reaction time due to large interface area and short molecule diffusion distance. At the end of reaction, Janus nanoparticles could be recovered by simple centrifugation, the relative activity of lipase remained 72.89 ± 1.83% after repeated use for 6 times. Overall, this paper provides a novel and high efficiency interfacial biocatalysis technique for the synthesis of phytosteryl oleate.

研究领域: 生物学 · 化学工程 · 食品科学
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JOURNAL OF FOOD COMPOSITION AND ANALYSIS · 2025 · IF 4.6

Comparative analysis of the characteristics and content of γ-oryzanol in 19 Chinese brown rice cultivars

Yongyao Lu,Yanlin Hou,Shutian Liu,Shugang Jia,Yanmei Zhu,Xuehong Zhang

The composition and content of γ-oryzanol significantly influenced its biological activity. The contents of γ-oryzanol in 19 Chinese brown rice ( Oryza sativa L.) cultivars were quantified and characterized using high-performance liquid chromatography/mass spectrometry . The total content of γ-oryzanol in these 19 Chinese brown rice cultivars ranged from 19.37 to 232.2 mg/100 g, with an average of 76.23 mg/100 g. Five specific steryl ferulates were identified. Cycloartenyl ferulate, 24-methylene cycloartanyl ferulate, and β-sitosteryl ferulate comprised approximately 82 % of the total γ-oryzanol content, while campesteryl ferulate and stigmastanyl ferulate constituted the remaining 18 %. Japonica and glutinous rice exhibited similar γ - oryzanol contents, which were significantly different from those of indica rice. No significant difference was observed in the total γ-oryzanol content between the short-grain and long-grain rice. However, there were significant differences in the steryl ferulates. Both latitude and longitude significantly influenced the γ-oryzanol content, and longitude had a more pronounced effect than latitude. Apart from the lack of correlation between cycloartenyl ferulate and β-sitosteryl ferulate, significant correlations were observed among the contents of the other steryl ferulates. This study offers valuable insights to scientifically assess the nutritional value of Chinese brown rice, guide the breeding of varieties and inform high-quality cultivation practices.

CAS / MDL: 11042-64-1
研究领域: 食品科学 · 植物化学 · 营养学
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RSC Advances · 2021 ·Vol. 11 ·期 25 ·15204-15212 · IF 3.361

Enzymatic preparation of phytosterol esters with fatty acids from high-oleic sunflower seed oil using response surface methodology

Xiaoping Wang,Bing Xiao,Guolong Yang,Jingnan Chen,Wei Liu

Phytosterol esters are functional compounds that can effectively reduce plasma cholesterol concentration, and have wide applications in the food industry. In this study, a simple and efficient enzymatic method was successfully applied to synthesize phytosterol oleic acid esters with fatty acids from high-oleic sunflower seed oil. Among the tested lipases, Candida rugosa lipase (CRL) exhibited higher catalytic activity in the esterification of phytosterols with fatty acids (oleic acid 84%) from high-oleic sunflower seed oil. Box–Behnken design and response surface methodology were used to investigate the influence of reaction factors on the conversion of phytosterols. The maximum conversion of phytosterols (96.8%) and yield of phytosterol esters (92%) could be obtained under optimal conditions: reaction temperature 50 °C, a molar ratio of phytosterols to fatty acids at 1 : 2.3, enzyme loading of 5.8%, isooctane volume of 2 mL and reaction time of 2 h. It was noteworthy that this enzymatic esterification method indeed expended a much shorter reaction time (2 h) than that observed in previous reports. In general, the enzymatic preparation of phytosterol oleic acid esters with fatty acids from high-oleic sunflower seed oil will be a simple and rapid method for producing unsaturated fatty acid esters of phytosterol with both higher oil solubility and oxidative stability, which is beneficial as functional food ingredients.

CAS / MDL: 112-80-1
研究领域: 食品科学 · 生物化学
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Food & Function · 2019 ·Vol. 11 ·期 1 ·977-991 · IF 3.241

The regulatory effects of phytosterol esters (PSEs) on gut flora and faecal metabolites in rats with NAFLD

Lihua Song,Yating li,Dan Qu,Pengling Ouyang,Xinwen Ding,PeiYing Wu,Qi Guan,Li Yang

Recent studies have shown that the occurrence and progression of nonalcoholic fatty liver disease (NAFLD) can be aggravated by dysregulation of intestinal flora. We previously found that phytosterol esters (PSEs) could effectively prevent the progression of NAFLD. Here, we further investigated the regulatory effect that PSEs have on gut flora and faecal metabolites in rats with NAFLD. Adult SD (Sprague Dawley) rats were randomized into four groups: the normal chow diet (NC), high-fat diet (HFD), low-dose PSE (0.05 g per 100 g BW, PSEL) and high-dose PSE (0.10 g per 100 g BW, PSEH) groups. PSEs were intragastrically administered once a day for 12 consecutive weeks. Our work indicated that high-dose PSE treatment effectively inhibited the increase in liver and abdominal fat indexes (P < 0.01) and hepatic lipids (P < 0.01); a high dose PSE treatment effectively corrected the HFD-induced intestinal flora imbalance by changing the diversity. The relative abundances of the four phyla (Firmicutes, Proteobacteria, Actinobacteria and Verrucomicrobia) and partial bacteria at the genus level (Faecalibacterium, Akkermansia, etc.) in the PSEH group were closer to those in the NC group. High-dose PSE intervention significantly increased the relative abundance of Bacteroidetes and Anaerostipes. Compared with the HFD, PSEH treatment significantly decreased the ionic strengths of bile acid metabolism products (P < 0.05), which were positively correlated with hepatic steatosis. In conclusion, PSE treatment exerts a beneficial effect on NAFLD that is associated with its regulatory action on intestinal flora and faecal metabolites, which might present a new opportunity to develop effective and safe preventive strategies against NAFLD.

研究领域: 营养学 · 微生物学 · 肝病学
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JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC · 2015 · IF 2.128

Improved enzymatic properties of Candida rugosa lipase immobilized on ZnO nanowires/macroporous SiO2 microwave absorbing supports

Chuan-Yang Shang,Wei-Xun Li,Feng Jiang,Rui-Feng Zhang

ZnO nanowires/macroporous SiO 2 composites were used as a new type of microwave absorbing support to immobilize Candida rugosa lipase (CRL). Under microwave irradiation the immobilized lipase was used to catalyze esterification of phytosterol and oleic acid for the synthesis of phytosterol esters. A great improvement of the catalytic activity was found in the systems in which composited ZnO nanowires were present. The microwave absorbing properties of ZnO nanowires have been proved to be helpful for the synergistic effect between microwave irradiation and enzyme catalysis. The immobilized CRL showed higher thermal stability at 55   °C under microwave irradiation than conventional heating. A maximum molar conversion of 95.4% under microwave irradiation was achieved under the optimal condition: 0.1   M phytosterol, 0.2   M oleic acid, water activity ( a w ) of 0.11, reaction temperature at 50   °C and reaction time of 1   h.

研究领域: 生物化学 · 酶工程 · 纳米材料科学
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