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JOURNAL OF ETHNOPHARMACOLOGY · 2025 · IF 5.4

Bio-affinity ultrafiltration combined with UPLC Q-Exactive Plus Orbitrap HRMS to screen potential COX-2 and 5-LOX inhibitors in mulberry (Morus alba L.) leaf

Yan Du,Yu-lang Chen,Ying Zhang,Yan-lin Zhao,Zhong Huang,Peng Jin,Shuai Ji,Dao-Quan Tang

Ethnopharmacological relevance Mulberry ( Morus alba L.) leaf is a well-known herbal medicine in China for thousands of years. Mulberry leaf can regulate arachidonic acid (ARA) metabolism disorder in obesity and type 2 diabetes mellitus. However, the active ingredients involved in this process are still unclear. Aim of study To explore the potential active ingredients in mulberry leaf against ARA metabolism disorder. Materials and methods In this research, an efficient method combining affinity ultrafiltration, molecular docking, and network pharmacology was developed and applied to explore cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) inhibitors from mulberry leaf. Results A total 17 potential inhibitors were screened by affinity ultrafiltration assay and identified by high resolution mass spectrometry. In addition, 8 bioactive ingredients were obtained after re-evaluated by molecular docking and network pharmacology, and their inhibitory activities on COX-2 and 5-LOX were confirmed by in vitro inhibitory assays. The results of cell experiments showed that the expressions of COX-2 and 5-LOX were significantly suppressed by neochlorogenic acid, rutin, isoquercetin, and (−)-syringaresinol-4-O-glucoside. Conclusion Neochlorogenic acid, rutin, isoquercetin, and (−)-syringaresinol-4-O-glucoside may be the potential material basis of mulberry leaf in the regulation of ARA metabolism of obesity and type 2 diabetes mellitus.

研究领域: 药理学 · 分析化学 · 中药学
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FOOD SCIENCE AND BIOTECHNOLOGY · 2015 ·Vol. 24 ·期 4 ·1257-1263 · IF 0.653

Examination of the effects of temperature and pressure on lipoxygenase activities in pork using response surface methodology

Huang Yechuan,Wu Zhaomin,Wang Yanrong,Li Feng

To investigate the effects of pressure and temperature on lipoxygenase (LOX) in meat, changes in LOX activities in minced pork and in crude enzyme extracts under different conditions of pressure (131.82–468.18 MPa), temperature (23.18–56.82°C), and duration (6.59–23.41 min) were evaluated using response surface methodology. LOX activities in extracts exhibited a decrease with an increasing treatment temperature, pressure, or duration. Each of these factors alone had a significant ( p <0.05) effect on LOX activities. Activation of LOX in most minced pork treated at less than 400 MPa was observed. Treatment pressure and temperature, and interactions between pressure and temperature and between duration and pressure, significantly ( p <0.05) affected LOX activities. LOX showed higher stability in muscles than in extracts during combined pressure-heat treatments. The most important factor affecting LOX was treatment temperature for extracts and treatment pressure for muscles.

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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FOOD SCIENCE AND BIOTECHNOLOGY · 2015 ·Vol. 24 ·期 3 ·867-873 · IF 0.653

Comparison of lipoxygenase activity characteristics in aqueous extracts from milk-stage sweet corn and waxy corn

Niu Liying,Li Dajing,Liu Chunquan,Liu Fuguo

Lipoxygenases (LOX) in milk-stage sweet corn and waxy corn were extracted using a phosphate buffer (pH 7.0) and enzyme activities were determined using linoleic acid as a substrate. Michaelis constant ( K m) values, decimal reduction times (D value), temperature sensitivity parameters (Z value), and activation energies ( E a) were calculated. Enzymes from both corn types followed first-order inactivation kinetics within 0–25 min and 50–70°C. However, enzymes exhibited different pH profiles and affinities toward linoleic acid. Km values (4.34 and 1.40 mM for sweet corn and waxy corn, respectively), heat stability values, and Ea values (116.81 and 246.82 kJ/mol) were different. Waxy corn LOX was more heat stable below 65–C with a higher D value, but was more temperature sensitive with a lower Z value. The different characteristics suggested the presence of different isoenzymes and necessitated the use of different parameters for blanching.

研究领域: 食品科学 · 植物生理学
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FOOD RESEARCH INTERNATIONAL · 2023 · IF 8.1

The roles of lipoxygenases and autoxidation during mackerel (Scomberomorus niphonius) dry-cured processing

Qiaoyu Liu,Menglin Lei,Jianjun Lin,Wenhong Zhao,Xiaofang Zeng,Weidong Bai

The roles of enzymatic (Lipoxygenases, LOX) oxidation and autoxidation in the dry-cured processing of mackerel were investigated by adding exogenous substances in this study. Four groups, namely control, chlorogenic acid (inhibiting LOX activity), EDTA-2Na (inhibiting autoxidation), and exogenous LOX (adding eLOX), were assigned. The results showed that lipid oxidation of mackerel was reduced by inhibiting LOX activity and autoxidation, while adding eLOX promoted lipid oxidation. Inhibition of LOX activity and autoxidation suppressed fatty acid accumulation mainly in the air-drying and curing stage, respectively. The total contents of key flavors in the mackerel during dry-cured processing were decreased by inhibiting LOX activity and autoxidation, and the former inhibitory effect was stronger than autoxidation, while it was corresponding increased through adding eLOX, of particular in the later stage of air-drying. Collectively, LOX could promote the flavor formation of the mackerel in the dry-cured processing, which could be applied in the flavor adjustment of aquatic products or some similar fields.

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

Functional characterization of a novel lipoxygenase from Aliikangiella coralliicola for natural modification on gelation of soy protein isolate

Ang Yang,Huibing Chi,Zhaoxin Lu,Fengxia Lu,Ping Zhu

Lipoxygenase (LOX) can catalyze the production of hydroperoxides from polyunsaturated fatty acids, offering promising applications in the food industries with especial contribution of naturally modified function for food gelation. To date, commercially available LOXs primarily sourced from soybean meal, facing challenges such as containing isoenzymes and exhibiting low catalytic activity for broad utilization restrictions. Herein, a LOX was first derived from the marine microorganism Aliikangiella coralliicola (AcLOX) with a molecular weight of 80 kDa expressed in Escherichia coli . AcLOX exhibited good stability over a wide pH range of 4.0–9.0. Additionally, AcLOX displayed specific activity against α-Linolenic acid (ALA) of 6.67 × 10 4 U/mg, and kinetic parameters values for K m , k cat , and k cat / K m of 0.58 μM, 1.40 s −1 , and 2.42 μM −1  s −1 , respectively. Moreover, Ca 2+ and dimethyl sulfoxide (DMSO) activated the activity of AcLOX. To explore its gelation modification ability, AcLOX was applied to induce the cross-linking of soy protein isolate (SPI) subunits with increased particle size, potential, surface hydrophobicity (S o ), and as well as gel hardness at appropriate concentrations. This is the inaugural study to unveil the gelation modification ability of LOX from Aliikangiella coralliicola . These findings provide superior enzymatic performance and cross-linking potential of AcLOX for industrial applications.

研究领域: 食品科学 · 酶学 · 生物化学
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ULTRASONICS SONOCHEMISTRY · 2022 · IF 9.336

Inhibitory effects of ultrasonic and rosmarinic acid on lipid oxidation and lipoxygenase in large yellow croaker during cold storage

Ting-ting Chai,Yang-na Huang,Shao-tian Ren,Dan-li Jin,Jing-jing Fu,Jun-yan Guo,Yue-wen Chen

Lipid oxidation will lead to the deterioration of flavor, color and texture of aquatic products with high fatty acid content. The mechanism of ultrasound (US) combined with rosmarinic acid (RA) on lipid oxidation and endogenous enzyme activities of large yellow croaker during cold-storage (4 ℃) was investigated. The result showed that the US and RA have synergistic effects in delaying lipid oxidation and inhibiting endogenous lipase and lipoxygenase (LOX) activities related to oxidation. The inhibition of LOX activity by RA was dose-dependent, and US showed a negative effect on the inhibition of enzyme activity in the presence of low concentration RA. Moreover, RA changes the enzyme structure through static fluorescence quenching and interaction with enzyme molecules. Hydrogen bonding and hydrophobic interaction are the main interaction forces between RA and LOX. This study could provide basic mechanism of US treatment cooperating with polyphenols to inhibit lipid oxidation during food preservation.

CAS / MDL: 1492-30-4
研究领域: 食品科学 · 生物化学
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Foods · 2023 ·Vol. 12 ·期 13 ·2504 · IF 5.2

Formation of Lipid-Derived Flavors in Dry-Cured Mackerel (Scomberomorus niphonius) via Simulation of Autoxidation and Lipoxygenase-Induced Fatty Acid Oxidation

Qiaoyu Liu,Menglin Lei,Wenhong Zhao,Xiangluan Li,Xiaofang Zeng,Weidong Bai

In this study, lipoxygenase (LOX) extracted from dry-cured mackerel was purified, resulting in a 4.1-fold purification factor with a specific activity of 493.60 U/min·g. LOX enzymatic properties were assessed, referring to its optimal storage time (1–2 days), temperature (30 °C), and pH value (7.0). The autoxidation and LOX-induced oxidation of palmitic acid (C16:0), stearic acid (C18:0), oleic acid (C18:2n9c), linoleic acid (C18:2n6c), arachidonic acid (C20:4), EPA (C20:5), and DHA (C22:6n3) were simulated to explore the main metabolic pathways of key flavors in dry-cured mackerel. The results showed that the highest LOX activity was observed when arachidonic acid was used as a substrate. Aldehydes obtained from LOX-treated C18:1n9c and C18:2n6c oxidation, which are important precursors of flavors, were the most abundant. The key flavors in dry-cured mackerel were found in the oxidative products of C16:0, C18:0, C18:1n9c, C18:2n6c, and C20:4. Heptanaldehyde could be produced from autoxidation or LOX-induced oxidation of C18:0 and C18:1n9c, while nonal could be produced from C18:1n9c and C18:2n6c oxidation. Metabolic pathway analysis revealed that C18:1n9c, C18:2n6c, EPA, and DHA made great contributions to the overall flavor of dry-cured mackerel. This study may provide a relevant theoretical basis for the scientific control of the overall taste and flavor of dry-cured mackerel and further standardize its production.Keywords:lipoxygenase;fatty acids;autoxidation;enzymatic oxidation;volatile compounds

研究领域: 食品科学 · 生物化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2020 · IF 4.192

Gel Properties of Soy Protein Isolate Modified by Lipoxygenase-Catalyzed Linoleic Acid Oxidation and Their Influence on Pepsin Diffusion and In Vitro Gastric Digestion

Jie Zhao,Jihong Wu,Yanni Chen,Mouming Zhao,Weizheng Sun

The model of lipoxygenase-catalyzed linoleic acid (LA) oxidation was selected as representative of a lipid peroxidation system to investigate the effects of oxidative modification on soybean protein isolate (SPI) gel properties and in vitro gastric digestion. Fluorescence recovery after the photobleaching (FRAP) technique was applied to evaluate pepsin diffusion in the gel. The results showed that oxidative modification increased the gel hardness as well as brought about a compact and three-dimensional network structure, which consequently decreased the water mobility as manifest by lowering the relaxation time of T2b and T21 from 0.55 and 3.22 ms for the control to 0.32 and 2.42 ms for 7LA+LOX (addition of 7 mL of LA and LOX), respectively. It was interesting to note that pepsin diffusion was significant correlated (p < 0.05) with T2b and DH (degree of hydrolysis), indicating that water mobility might be a factor related to FITC–pepsin diffusion, which would ultimately influence the gel gastric digestion. Compared with native SPI, moderate oxidation can improve the digestibility of SPI gel by the summed effects of pepsin diffusion limitation, microstructure variation, and hydrolysis degree.

研究领域: 食品科学 · 生物化学
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STEROIDS · 2013 · IF 2.803

One-pot efficient synthesis of 13(R),14(R)-epoxy-17β-methyl-20(S)-hydroxyl-18-nor-pregna-4-en-3-one via a tandem epoxidation-rearrangement-epoxidation reaction sequence

Shu-Xiao Feng,Ya-Dong Zhang

One-pot synthesis of an 18-norsteroid compound, 13( R ),14( R )-epoxy-17β-methyl-20( S )-hydroxyl-18-nor-pregna-4-en-3-one has been achieved with peracetic acid/acetic acid under a mild condition, via a proved tandem epoxidation-rearrangement-epoxidation sequence. Its structure was designated on the basis of NMR and X-ray crystallography data.

研究领域: 有机化学 · 药物化学
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PLoS One · 2025 ·Vol. 20 ·期 4 ·e0320582 · IF 2.6

Extraction of total flavonoids from Chaenomeles speciosa (Sweet) Nakai and its antioxidant and lipoxygenase inhibition effects

Wenqing Pei,Yuting Sun,Juan Li,Yupei Zhang,Chenkang Jian,Feng Lu,Ali Tao,Qizhao Li

Ultrasound-assisted extraction technology was utilized to extract total flavonoids from Chaenomeles speciosa (Sweet) Nakai, and response surface methodology was employed to optimize the extraction process. The anti-oxidant and lipoxygenase inhibitory activities were evaluated, along with an analysis of the type of inhibition. The results revealed that the optimal extraction conditions for total flavonoids from Chaenomeles speciosa (Sweet) Nakai were as follows: an ethanol concentration of 62%, a liquid-to-solid ratio of 15:1 mL/g, an ultrasonic temperature of 68°C, and an ultrasonic time of 40 min, resulting in a total flavonoid extraction rate of 10.18%. Antioxidant assays demonstrated that the Chaenomeles speciosa (Sweet) Nakai extract exhibited significant radical scavenging activities against 1,1-diphenyl-2-picrylhydrazyl radicals, 2,2’-azinobis (3-ethylbenzothiazoline-6-sulfonic acid ammonium salt) radicals, and hydroxyl radicals, with IC 50 values of 582 µg/mL, 538 µg/mL, and 1709 µg/mL, respectively. Furthermore, enzyme inhibition assays indicated that the Chaenomeles speciosa (Sweet) Nakai extract possesses notable inhibitory activity against lipoxygenase, with an IC 50 value of 2658 µg/mL. This inhibition is mediated through a mixed reversible inhibition mechanism.

研究领域: 植物化学 · 药理学 · 食品科学
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FOOD SCIENCE AND BIOTECHNOLOGY · 2024 · IF 2.4

Enhancing emulsification and gelation properties of porcine myofibrillar protein under low NaCl by lipoxygenase from volvaria volvacea

Zhang Jinhua,Bi Penghui,Guo Jiamin,Zou Jinhao,Wang Xuping

The objective of this research was to present an alternate approach for enhancing the emulsification and gelation properties of porcine MP under low NaCl conditions (0.1 M). This was achieved by utilizing lipoxygenase from Volvaria volvacea ( vv LOX). Addition of vv LOX from 0 to 1000 U/mL, gradually decreased the protein particle size, polydispersity index, and zeta potential values at same time increased the emulsion activity and stability index of the MP emulsion. Additionally, the gel strength and water holding capability of the MP gel also increased. At a concentration of 0.1 M NaCl, the application of vv LOX treatment resulted in a compact gel matrix for the MP gel, as evidenced by measurements of dynamic viscoelasticity and microstructure. The mechanism of enhancing emulsification and gelation properties by vv LOX addition could attribute to decreasing the dispersion of particle sizes and increasing the repulsive forces between droplets.

研究领域: 食品科学 · 生物化学
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