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Food Biophysics · 2026 ·Vol. 21 ·期 1 ·17 · IF 3.2

Enzymatic Synthesis, Characterization, Antioxidant Activity, and Density Functional Theory Calculation of Novel 1-O-alkylglyceryl Ferulate

Zhang Xinyu,Li Yijie,Lin Hong,He Junbo,Feng Jiangtao,Cai Meng

To improve the lipophilicity and antioxidant potential of ferulic acid (FA), four novel 1- O -alkylglyceryl ferulates (C 8 Gly 1 F, C 12 Gly 1 F, C 16 Gly 1 F, and C 18:1 Gly 1 F) were synthesized via Novozym 435-catalyzed transesterification in n -hexane at 65 °C, achieving high conversion rates and good enzyme reusability. Crystallinity and thermal properties, analyzed by polarized light microscopy and DSC, revealed that C 12 Gly 1 F exhibited optimal crystallinity, while C 18:1 Gly 1 F, due to its unsaturated alkyl chain, was predominantly amorphous, suggesting enhanced solubility. Antioxidant assays (DPPH and ABTS) demonstrated higher radical scavenging activity compared to ethyl ferulate, with C 18:1 Gly 1 F showing the best performance. Density functional theory calculations revealed its high electron affinity, electrophilicity, and a delocalized HOMO–LUMO distribution, supporting its proposed antioxidant mechanism. These findings highlight the potential of 1- O -alkylglyceryl ferulates as effective lipophilic antioxidants for use in functional foods and lipid-based delivery systems.

CAS / MDL: 4046-02-0
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FOOD RESEARCH INTERNATIONAL · 2026 · IF 8

Screening of a feruloyl esterase-producing lactobacillus strain and its application in citrus whole-fruit pulp fermentation: organic acids, volatile compounds, and sensory evaluation

Tian Tian,Yu Peng,Shuangyang Chen,Yue Zhang,Yi Li,Aonan Xia,Erhu Li,Xuedan Cao

Feruloyl esterase (FAE)-producing lactobacillus strains were selected from the citrus whole-fruit pulp after 48 h of fermentation. Among them, Lactiplantibacillus plantarum K33 showed the highest ferulic acid (FA) producing ability. Using citrus whole-fruit pulp as the fermentation matrix, physicochemical, compositional, and sensory outcomes were compared between pulps fermented by K33 and by the commercial strain L. plantarum N13 (Lp-N13). After fermentation, K33 increased total acidity, lowered pH, and markedly raised FA concentration and total phenolic content (TPC). Fermentation also altered other organic acids and volatile profiles: L-malic acid decreased significantly, whereas lactic and succinic acids increased. Terpenes remained predominant, with a significant rise in the relative proportion of alcohols. KEGG analysis showed that the differential of organic acids was mainly associated with arginine biosynthesis and other pathways. Sensory evaluation indicated enhanced lactic acid flavor and reduced citrus-peel aroma. Overall, K33 shows promise for fermentation of functional plant-based beverages.

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BIOCATALYSIS AND BIOTRANSFORMATION · 2022 · IF 2.325

A chlorogenic acid esterase from a metagenomic library with unique substrate specificity and its application in caffeic and ferulic acid production from agricultural byproducts

Jian Yao,Lun Gui,Qizhang Long

Soil microbes are an abundant source of enzymes with unique properties that may be useful for industrial applications. As most wild-type strains show low chlorogenic acid esterase expression and activity, and most microbes cannot be cultured in the laboratory, a metagenomic approach provides methods of identifying new enzymes. In this study, a gene encoding a chlorogenic acid esterase, named Tan410, was isolated from a soil metagenomic library and overexpressed in Escherichia coli BL21 (DE3). The recombinant enzyme, with a predicted molecular weight of 54.88 kDa, was purified to homogeneity. The Km and Vmax values for Tan410 were 1.26 mM and 0.33 mM min–1, respectively, with chlorogenic acid as the substrate. Its optimum temperature and pH for reaction were 30 °C and 7.5, respectively. The enzyme exhibited moderate thermostability and broad pH stability (3.0–10.0). Tan410 was also able to hydrolyse ethyl ferulate, methyl caffeate, propyl gallate, ethyl gallate, methyl vanillate, methyl benzoate, ethyl benzoate, methyl 2,5-dihydroxybenzoate, and methyl 3,5-dihydroxybenzoate, and it released caffeic and ferulic acids from agricultural byproducts (destarched wheat bran and coffee pulp). Tan140 has potential for industrial application in biomass valorization.

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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2022 · IF 8.025

Deciphering the linkage type and structural characteristics of the p-hydroxyphenyl unit in Pinus massoniana Lamb compressed wood lignin

Xiaoxiao Wei,Yuanyuan Yu,Zheng Shen,Yi Liu,Xi Liu,Shuangfei Wang,Liming Zhang,Douyong Min

To reveal the existence of p -hydroxyphenyl (H) units in compressed wood lignin, four different milled wood lignins were extracted using Pinus massoniana Lamb compressed wood, Pinus massoniana Lamb normal wood, and sugarcane bagasse as raw materials. Then, three dehydrogenation polymers (DHPs) were synthesized using coniferyl/ p -coumaryl alcohol as raw materials to reveal the interunit linkages of H units. The lignin and DHP samples were systematically characterized by 1 H, 13 C, 2D HSQC, and 31 P NMR techniques. Compared with the opposite wood milled wood lignin (OW-MWL) and the normal wood milled wood lignin (NW-MWL), the compressed wood milled wood lignin (CW-MWL) contained a large amount of H units, and the H/G ratio and the p -hydroxyphenyl OH group contents were 0.15 and 1.09 mmol/g, respectively. Through the characterization of CW-MWL and DHPs, it was revealed that p -hydroxyphenyl units mainly coupled with other units by β-O-4, β-β, and β-5 linkages. Compared to the sugarcane bagasse milled wood lignin, it was clearly demonstrated that the H unit rather than p -coumarate ester occurred in CW-MWL. This study comprehensively explored the structural characteristics and linkages of H units in compress wood lignin, and provided useful information for revealing the participation of H units in the construction of lignin macromolecules .

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FOOD CHEMISTRY · 2023 · IF 8.8

Fermentation of Lactobacillus fermentum NB02 with feruloyl esterase production increases the phenolic compounds content and antioxidant properties of oat bran

Yueqin Li,Yunzhen Zhang,Lezhen Dong,Ying Li,Yahui Liu,Yang Liu,Lingyi Liu,Lianliang Liu

In this study, strains producing feruloyl esterase were screened by Oxford Cup clear zones method and by evaluating the ability to decompose hydroxycinnamoyl esters. The strain was identified by 16S rDNA molecular biology. The contents of dietary fiber, reducing sugar, water-extractable arabinoxylans, phytic acid, total phenolics, total flavonoid, phenolic compounds composition, microstructure and antioxidant activity in bran before and after fermentation were studied. Eight strains producing feruloyl esterase were screened, among which strain P 1 had the strongest ability to decompose hydroxycinnamoyl esters. The strain was identified and named L. fermentum NB02. Compared with unfermented bran, fermented bran exhibited higher contents of soluble dietary fiber, reducing sugar, water-extractable arabinoxylans, total phenolics, total flavonoid, and lower insoluble dietary fiber and phytic acid content. The dense surface structure of bran was destroyed, forming a porous structure. The release of phenolic compounds increased significantly. L. fermentum NB02 fermentation improved the antioxidant capacity of bran.

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CELLULOSE · 2021 ·Vol. 28 ·期 7 ·4397-4409 · IF 5.044

Laccase mediated phenol/chitosan treatment to improve the hydrophobicity of Kraft pulp

Ni Shuzhen,Liu Na,Fu Yingjuan,Gao Hailong,Qin Menghua

Abstract Herein, a great potential approach initiated by laccase is applied to graft the biopolymers (chitosan and phenols) onto the unbleached Kraft pulp fibers to enhance the hydrophobicity and strength. The results showed that the chitosan and laccase/phenols exhibited a synergistic action on the significant improvement of the hydrophobicity of the KP pulp fibers. Compared with the base paper, a high sizing degree value (227.08 s) was achieved when the fibers were treated by the laccase/4-hexyloxyphenol/chitosan (Lac/HP/CTS) system. The water retention value of the corresponding KP fibers reduced from 176.8 to 171.3%, and the Kappa number of treated fibers increased from 26.8 to 29.3, confirming the successful graft of HP onto the fibers. The effect of the reaction parameters, including the temperature, pH, HP and chitosan dosage, reaction time and pulp suspension consistency on the strength and hydrophobicity was investigated. pH value was found as the most remarkable factor influencing the sizing degree and gave a highest sizing value (506.2 s) at pH 5.5. The strength performance presented an opposite trend against the hydrophobicity, since the number of formed hydrogen bonds is the least when the hydrophobicity is the best. This work is extremely significant for providing valuable reference on improving the hydrophobicity and strength performance of papers through a green and biological way. Graphic abstract

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RSC Advances · 2020 ·Vol. 10 ·期 19 ·11139-11147 · IF 3.119

Ultrasonic-promoted enzymatic preparation, identification and multi-active studies of nature-identical phenolic acid glycerol derivatives

Teng Sun,Haiping Zhang,Zhe Dong,Zengshe Liu,Mingming Zheng

Phenolic acid glycerols (PAGs) are a group of rare phytochemicals found from potato periderm, which show great potential in the food, cosmetic and pharmaceutical industries. In this study, seven PAGs were enzymatically synthesized via transesterification of ethyl phenates (EPs) with glycerol by ultrasonic promotion. The conversions of 88.1–98.5% could be obtained in 1–9 h. Compared with the conventional stirring methods, the catalytic efficiency was significantly increased 11.0–44.0 folds by ultrasound assistance. The lipid peroxidation inhibition activity increased 8.1-fold and 14.4-fold compared to the parent phenolic acids (PAs). Furthermore, caffeoyl glycerol and feruloyl glycerol exhibited excellent antimicrobial activity against Escherichia coli compared to the corresponding PAs with minimum inhibitory concentration (MIC) decreasing 4–16-fold. The PAGs can also absorb a much wider and higher amount of the harmful UV-B rays than the corresponding PAs. The present strategy for facile synthesis of multifunctional PAGs paves the way for the development and application of natural phytochemicals and novel ingredients.

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PROTEIN EXPRESSION AND PURIFICATION · 2015 · IF 1.695

A stereoselective esterase from Bacillus megaterium: Purification, gene cloning, expression and catalytic properties

Jian-yong Zheng,Jian Wang,Sha-sha Zhou,Xiao-jun Li,Xiang-xian Ying,Zhao Wang

Esterases (EC 3.1.1.X) have been used as biocatalysts due to their good stability, high chemo-, regio- and stereoselectivity. In our previous studies, Bacillus megaterium WZ009 harboring esterase displayed the unique capability to convert ( S )-4-Chloro-3-hydroxyethylbutyrate (CHBE) in the racemate to ( S )-3-hydroxy-γ-butyrolactone (HL) through stereoselective hydrolysis, dechlorination, and lactonization. The remaining ( R )-CHBE and formed ( S )-HL could be obtained in a one-pot enzymatic reaction. An esterase from B. megaterium WZ009 was purified and was found to have 466 encoded amino acids and an apparent molecular mass of 55 kDa. The purified esterase exhibited maximal activity at a temperature of 25 °C and at a pH of 11.5 towards 100 mM CHBE. When the stereoselective biocatalysis of rac -CHBE was performed using the recombinant Escherichia coli BL21 (DH3) cells harboring the esterase, the catalytic activity increased by 20-fold compared with the original strain B. megaterium WZ009. With the addition of activated carbon (62 g/L) in the reaction system, the conversion was increased from 39% to 45% at a substrate concentration of 750 mM. Another remarkable advantage is that both of the obtained residual ( R )-CHBE and the formed ( S )-HL had high optical purities ( e.e. s  > 99.9%, e.e. p  > 99.9%), thereby making this esterase a usable biocatalyst for industrial application.

CAS / MDL: 4046-02-0
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ULTRASONICS SONOCHEMISTRY · 2017 · IF 4.218

Ultrasound irradiation promoted enzymatic alcoholysis for synthesis of monoglyceryl phenolic acids in a solvent-free system

Chunfang Xu,Haiping Zhang,Jie Shi,Mingming Zheng,Xia Xiang,Fenghong Huang,Junyong Xiao

Monoglyceryl phenolic acids (MPAs) were known as the natural hydrophilic antioxidants which could be used in different fields such as food, pharmaceutical, cosmetic etc. A novel enzymatic route of MPAs synthesis by the alcoholysis of phenolic acid ethyl esters with glycerol under ultrasound irradiation in solvent free system was developed. Optimization of reaction parameters shows that a high conversion of above 97.4% can be obtained under the following conditions: phenolic acid ethyl esters to glycerol molar ratio of 1:10, with 6% catalyst (Novozym 435), at 60   °C and 200   rpm, with ultrasound input of 250   W, at 20   kHz frequency. Compared to the conventional stirring method, the activation energy for phenolic acid ethyl esters conversion was decreased from 65.0   kJ/mol to 32.1   kJ/mol under ultrasound promotion; the apparent kinetic constant (V m /K m ) increased above 1.2-folds; the lipase amount decreased to 50%; the time required for the maximum conversion reduced up to 3-folds without damaging the lipase activity, which is the fastest report for enzymatic synthesis of MPAs.

CAS / MDL: 102-37-4 4046-02-0
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FOOD CHEMISTRY · 2017 · IF 4.529

Enzymatic preparation of “functional oil” rich in feruloylated structured lipids with solvent-free ultrasound pretreatment

Haiping Zhang,Mingming Zheng,Jie shi,Hu Tang,Qianchun Deng,Fenghong Huang,Dan Luo

In this study, a series of functional oils rich in feruloylated structured lipids (FSLs) was prepared by enzymatic transesterification of ethyl ferulate (EF) with triglycerides under ultrasound pretreatment. A conversion of more than 92.7% and controllable FSLs (3.1%–26.3%) can be obtained under the following conditions: 16% enzyme, substrate ratio 1:5 (oil/EF, mol/mol), 85 °C, ultrasound 1 h, pulse mode 3 s/3s (working/waiting), and 17.0 W/mL. Compared to conventional mechanical stirring, the activation energy decreased from 50.0 kJ/mol to 40.7 kJ/mol. The apparent kinetic constant increased by more than 13 times, and the time required for the maximum conversion reduced sharply from 20–60 h to 4–6h, which was the fastest rate for enzymatic synthesis of FSLs. The antioxidant activities of the functional oil significantly increased 1.0- to 8.1-fold more than that of the raw oil. The functional oil could be widely applied in various fields of functional foods.

CAS / MDL: 4046-02-0
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2024 · IF 4.3

Characterization of the structural and molecular interactions of Ferulic acid ethyl ester with human serum albumin and Lysozyme through multi-methods

Wen-hua Tong,Shu-qin Wang,Guan-ying Chen,Dong-xu Li,Yan-sen Wang,Li-ming Zhao,Ying Yang

Ferulic acid ethyl ester (FAEE) is an essential raw material for the formulation of drugs for cardiovascular and cerebrovascular diseases and leukopenia. It is also used as a fixed aroma agent for food production due to its high pharmacological activity. In this study, the interaction of FAEE with Human serum albumin (HSA) and Lysozyme (LZM) was characterized by multi-spectrum and molecular dynamics simulations at four different temperatures. Additionally, the quenching mechanism of FAEE-HSA and FAEE-LZM were explored. Meanwhile, the binding constants, binding sites, thermodynamic parameters, molecular dynamics, molecular docking binding energy, and the influence of metal ions in the system were evaluated. The results of Synchronous fluorescence spectroscopy, UV–vis spectroscopy, CD, three-dimensional fluorescence spectrum, and resonance light scattering showed that the microenvironment of HSA and LZM and the protein conformation changed in the presence of FAEE. Furthermore, the effects of some common metal ions on the binding constants of FAEE-HSA and FAEE-LZM were investigated. Overall, the experimental results provide a theoretical basis for promoting the application of FAEE in the cosmetics, food, and pharmaceutical industries and significant guidance for food safety, drug design, and development.

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