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Chemistry Central Journal · 2017 ·Vol. 11 ·期 1 ·1-15 · IF 2.442

Hemostatic chemical constituents from natural medicine Toddalia asiatica root bark by LC-ESI Q-TOF MSE

Zhang Xiaoyan,Sun Wenbo,Yang Zhou,Liang Yan,Zhou Wei,Tang Lei

Background Toddalia asiatica root bark as an effective hemostatic natural medicine or Chinese materia medica was applied in China for long history, its complex drug action mechanisms and unclear substance basis have been constraining the development of this drug.Results An intelligentized strategy by LC-ESI Q-TOF MSE was presented in this study for rapid identification of hemostatic chemical constituents from this natural medicine. Chromatographic separation was performed on a C18 column (150 mm × 2.1 mm, 1.8 μm), the MSE data in both negative and positive ion modes were acquired to record the high-accuracy MS and MS/MS data of all precursor ions. To reduce the false positive identifications, structural confirmation was conducted by comparison with the isolated reference standards (tR and MS, MS/MS data) or matching with natural product databases. Bioassay-guided fractionation of the extract of T. asiatica root bark was also carried out.Conclusion sAs a consequence, 31 natural compounds in T. asiatica root bark got putatively characterized. There were four main coumarins, isopimpinellin (Cp.23), pimpinellin (Cp.24), coumurrayin (Cp.30) and phellopterin (Cp.34) isolated and identified from T. asiatica root bark. The present study provided candidate strategy that helps to effectively identify the primary natural compounds of TCM or other complex natural medicines, and then promote development and application of natural medicines and their medicinal resources.

CAS / MDL: 64-18-6
研究领域: 药理学 · 中药学 · 分析化学
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Layer-by-layer assembled cellulase-based bioreactor with dual functions: Targeted biotransformation performances and enhanced photothermal antibacterial capabilities

Lina Fu,Jiandong Wang,Xinlin Zhang,Xuanting Zhao,Qi Gu,Guosheng Liu,Litao Wang,Yujie Fu

In this work, a core–shell cellulase-based bioreactor with dual functions was constructed, which can not only fully utilize their transformation characteristics but also can be used as photothermal antibacterial material. First, cellulose microspheres with porous nano-structure were used to immobilize enzymes. Subsequently, a molecularly imprinted layer was coated around the immobilized enzyme using dopamine as functional monomer and crosslinker. Therefore, the bioreactor achieved recognition and enrichment of phlorizin through targeted recognition sites on the surface of the shell structure. The bioreactor can convert phlorizin into phloretin, which can increase the yield of phloretin in lithocarpus litseifolius leaves extract by 122 times, and its conversion efficiency still maintained more than 95 % after 10 times of reuse. The molecular imprinting layer on the surface prepared with dopamine also showed excellent photothermal conversion characteristics. It was found that the bioreactor possessed good photothermal antibacterial abilities on both P. aeruginosa (antibacterial rate was 96.19 %) and B. subtilis (antibacterial rate was 85.98 %) via near-infrared light irradiation (808 nm). Moreover, the bioreactor with photothermal antibacterial property can effectively protect C. elegans from bacterial infections, and reduce the colonization of P. aeruginosa and B. subtilis in the C. elegans , thereby enhancing their survival rate. Our study offers a promising strategy to design a dual-functional bioreactor for the biotransformation of phytochemicals and expands the application of photothermal conversion technology in antibacterial fields.

研究领域: 生物技术 · 酶工程 · 光热疗法 · 抗菌技术
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JOURNAL OF FOOD BIOCHEMISTRY · 2017 ·Vol. 42 ·期 2 ·e12475 · IF 1

Enzymatic preparation and antioxidant activity of the phloridzin oxidation product

Benguo Liu,Jiangwei Liu,Chunling Zhang,Jiechao Liu,Zhonggao Jiao

During apple processing, phloridzin, the main flavonoid in apples, can be oxidized to the yellow pigment, which contributes to the color of apple juice and ciders. However, there was no report about the bioactivities of this yellow pigment. In this study, the oxidation of phloridzin catalyzed by tyrosinase from mushroom was investigated. The main oxidation product with bright yellow color was purified and identified as the phloridzin oxidation product j (POPj) based on electrospray ionization mass spectrometry (ESI-MS) and 13 C nuclear magnetic resonance ( 13 C-NMR) spectroscopy. In the chemical and cellular system, POPj exhibited the higher peroxyl radical-scavenging activity than phloridzin. Our results suggested that POPj was a kind of potential food yellow pigment with antioxidant activity, which partly explained health-promoting functions of apple juices and ciders. Practical applications In view of the potential toxicity of the artificial food yellow pigment, the need for natural and safe yellow pigment is increasing. In this study, the enzymatic preparation of the yellow pigment derived from phloridzin was investigated. Its antioxidant activity was first reported. This study can prompt the application of this new yellow pigment in food industry.

CAS / MDL: 60-81-1
研究领域: 食品科学 · 生物化学 · 农业化学
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Food & Function · 2021 ·Vol. 12 ·期 5 ·2148-2160 · IF 5.396

Phlorizin exerts potent effects against aging induced by D-galactose in mice and PC12 cells

Yaojie Liu,Ying Liu,Yatu Guo,Lin Xu,Hao Wang

Phlorizin is the main active ingredient of apple peel and has potential utilization value. Some recent studies have suggested that phlorizin may have antioxidant capacity and protect the liver. The injection of a low dose of D-galactose can cause some changes that resemble accelerated aging in mice. This study explored the protective effects of phlorizin on D-galactose-induced mice and PC12 cells. In this study, ICR mice were divided into a normal group (NOR), a D-galactose model group (D-gal) and phlorizin treatment groups (100 mg kg−1, 200 mg kg−1 and 400 mg kg−1). In addition to the NOR group, four other groups were injected with D-galactose (120 mg kg−1) for 12 weeks. The results showed that phlorizin reduced the decline of strength, coordination and spatial memory caused by aging, increased the activity of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GSH-Px), increased total antioxidant capacity (T-AOC), and reduced the content of malondialdehyde (MDA). On the other hand, phlorizin increased the levels of interleukin-2 (IL-2) and acetylcholine (ACh), reduced the release of interleukin-6 (IL-6), aspartate aminotransferase (AST) and alanine aminotransferase (ALT), and decreased the activity of acetylcholinesterase (AChE) in the brain, improved the expression of antioxidant genes related to the nuclear factor E2-related factor 2 (Nrf2) pathway, and reduced the occurrence of morphological lesions in the hippocampus and liver. In addition, phlorizin improved cell viability and reduced the cytotoxicity of D-galactose-induced oxidative stress in PC12 cells. Meanwhile, the protective effect of phlorizin was abolished in Nrf2 gene knockdown PC12 cells. Furthermore, molecular docking showed that phlorizin could bind Keap1 protein, which can interact with Nrf2 protein. Therefore, these results suggest that phlorizin may delay senescence and enhance antioxidant capacity through the Nrf2 pathway.

研究领域: 老年学 · 药理学 · 分子生物学
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Heliyon · 2019 · IF 0

Antioxidant capacity and hepatoprotective activity of myristic acid acylated derivative of phloridzin

Chunli Liu,Chunlong Yuan,Hosahalli S. Ramaswamy,Yamei Ren,Xiaolin Ren

The antioxidant activities in vitro and hepatoprotective effects against carbon tetrachloride (CCl 4 ) induced acute liver injury in vivo of myristic acid acylated derivative of phloridzin (PZM) were investigated. The PZM was obtained by enzymatic acylation of myristic acid and phloridzin (PZ). The antioxidant capability of PZM in vitro was evaluated by the ferric reducing antioxidant power assay (FRAP), 2,2′-Azinobis- 3-ethylbenzthiazoline-6-sulphonate (ABTS + ·) and 2,2-diphenyl-1-picrylhydrazyl (DPPH·) radical scavenging assay. Mice were intragastrically treated with control or PZM (20, 40, and 80 mg/kg) for 5 days and intra-peritoneal injection with CCl 4 . The enzymatic acylated synthesis of myristic acid and phloridzin was region-selective taken place on 6″-OH of phloridzin glycoside moiety and achieved 93% yield. PZM had a significantly higher total antioxidant ability, same scavenging ABTS + · ability and weaker scavenging DPPH· ability when compared to the parent PZ. The of aminotransferase serum activity and malondialdehyde hepatic activity were elevated (P < 0.015) after treatment with CCl 4 , while the related liver enzymatic activities and glutathione concentration were lower. These changes were enhanced by PZM. Further studies showed that PZM reduced the interleukin-6 expression and stimulated liver regeneration caused by CCl 4 . PZM attained good antioxidant capacity in vitro and had excellent hepatoprotective effects in vivo and better bioactivity compared to the parent phloridzin. The significance of hepatoprotective effect of phloridzin derivative against CCl 4 -induced hepatotoxicity in mice is an important and new finding.

研究领域: 药理学 · 生物化学
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FOOD RESEARCH INTERNATIONAL · 2021 · IF 6.475

pH-responsive antibacterial film based polyvinyl alcohol/poly (acrylic acid) incorporated with aminoethyl-phloretin and application to pork preservation

Zheng Hu,Hualin Wang,Linlin Li,Qian Wang,Suwei Jiang,Minmin Chen,Xingjiang Li,Jiang Shaotong

This study demonstrates a pH-responsive antibacterial film based on polyvinyl alcohol/poly (acrylic acid) incorporated with aminoethyl-phloretin (PVA/PAA-AEP) for intelligent food packaging. The thermal, mechanical, barrier and light transmittance properties of PVA/PAA are enhanced by PAA presence of ≤6%. The interactions between PVA and PAA were hydrogen and ester bonds. The pH-responsive characteristic is dependent on the protonation/deprotonation tendency of the carboxylic groups on PAA in acidic/alkaline environment. The PVA/PAA3 is selected for the incorporation of AEP and its pH-responsive swelling follows Ritger-Peppas and Schott second-order models. The AEP is hydrogen bonded with the matrix of PVA/PAA3 and the release of AEP is pH-responsive and a rate-limiting step following the First-order model. With pH decrease, the predominant release control was gradually changing from polymer relaxation to Fick diffusion. The PVA/PAA3-AEP films demonstrate AEP content dependent antioxidant and antimicrobial activities. Furthermore, the antibacterial efficiency against Listeria monocytogenes and Staphylococcus aureus is significantly better than Escherichia coli . The target film PVA/PAA3-AEP3 can effectively prolong the shelf-life of pork (TVB-N < 25 mg/100 g) by 4 days at 25 °C, suggesting its great potential in intelligent food packaging.

研究领域: 食品科学 · 材料科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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PHYTOMEDICINE · 2023 · IF 7.9

Phloretin alleviates doxorubicin-induced cardiotoxicity through regulating Hif3a transcription via targeting transcription factor Fos

Xiangyun Li,Taoli Sun,Jiaqin Liu,Shanshan Wei,Yuanying Yang,Jian Liu,Bikui Zhang,Wenqun Li

Background Doxorubicin (Dox), a chemotherapeutic agent known for its efficacy, has been associated with the development of severe cardiotoxicity, commonly referred to as doxorubicin-induced cardiotoxicity (DIC). The role and mechanism of action of phloretin (Phl) in cardiovascular diseases are well-established; however, its specific function and underlying mechanism in the context of DIC have yet to be fully elucidated. Objective This research aimed to uncover the protective effect of Phl against DIC in vivo and in vitro , while also providing a comprehensive understanding of the underlying mechanisms involved. Methods DIC cell and murine models were established. The action targets and mechanism of Phl against DIC were comprehensively examined by systematic network pharmacology, molecular docking, transcriptomics technologies, transcription factor (TF) prediction, and experimental validation. Results Phl relieved Dox-induced cell apoptosis in vitro and in vivo . Through network pharmacology analysis, a total of 554 co-targeted genes of Phl and Dox were identified. Enrichment analysis revealed several key pathways including the PI3K-Akt signaling pathway, Apoptosis, and the IL-17 signaling pathway. Protein-protein interaction (PPI) analysis identified 24 core co-targeted genes, such as Fos, Jun, Hif1a, which were predicted to bind well to Phl based on molecular docking. Transcriptomics analysis was performed to identify the top 20 differentially expressed genes (DEGs), and 202 transcription factors (TFs) were predicted for these DEGs. Among these TFs, 10 TFs (Fos, Jun, Hif1a, etc.) are also the co-targeted genes, and 3 TFs (Fos, Jun, Hif1a) are also the core co-targeted genes. Further experiments validated the finding that Phl reduced the elevated levels of Hif3a (one of the top 20 DEGs) and Fos (one of Hif3a's predicted TFs) induced by Dox. Moreover, the interaction between Fos protein and the Hif3a promoter was confirmed through luciferase reporter assays. Conclusion Phl actively targeted and down-regulated the Fos protein to inhibit its binding to the promoter region of Hif3a, thereby providing protection against DIC.

CAS / MDL: 67-68-5
研究领域: 药理学 · 分子生物学 · 心血管疾病 · 肿瘤学
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CARBOHYDRATE POLYMERS · 2018 · IF 5.158

Structural characteristics and hepatoprotective potential of Aralia elata root bark polysaccharides and their effects on SCFAs produced by intestinal flora metabolism

Yong-Gang Xia,Tian-Long Wang,Si-Miao Yu,Jun Liang,Hai-Xue Kuang

The structural characteristics of the polysaccharides from Aralia elata root barks (AERP) were systematically investigated by FT-IR, HPSEC-ELSD and colorimetric methods as well as by GC MS based monosaccharide compositions, Smith degradations, and methylation analysis. The result showed average molecular weights of AERP were between 42.7 kDa and 93.9 kDa. AERP was composed of Ara, Rha, GlcA, Man, Glc, and Gal in a molar ratio of 22.2: 10.3: 8.1: 32.7: 5.7: 21.2 along with a small number of sulfate (3.38%) and acetyl (4.87%) groups. The abundant glycosidic linkages of Man, Ara, Gal, and Rha were observed as more than 90% of all the monosaccharides detected. Studies to evaluate hepatoprotective potentials of AERP showed that they had potent hepatoprotective effects in vivo in carbon tetrachloride-induced acute liver injury (CIALI) in mice by histopathological evaluation, biochemical examinations and ELISA assays. GC MS was further used to determine the effects of AERP on the chemical profiles of nine common short-chain fatty acids (SCFAs) produced by intestinal flora metabolism in CIALI mice. These findings not only provide novel insights into the pharmacological actions of AERP on the protection from CIALI in mice, but they also demonstrate that determining SCFA profiles by targeted GC–MS metabolomics is an effective technique to investigate the molecular mechanisms of the effects of plant polysaccharides on intestinal flora metabolism.

研究领域: 药理学 · 生物化学 · 代谢组学
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Foods · 2024 ·Vol. 13 ·期 22 ·3537 · IF 4.7

Antibacterial Activity of Phloretin Against Vibrio parahaemolyticus and Its Application in Seafood

Siyang Chen,Wenxiu Zhu,Yiqun Zhan,Xiaodong Xia

Although phloretin is widely utilized in the food industry as an additive, its effects on foodborne pathogens remain insufficiently investigated. This study aimed to evaluate the antimicrobial properties of phloretin (PHL) againstVibrio parahaemolyticus(V. parahaemolyticus) and to elucidate the potential mechanisms of action. After PHL treatment, alterations in the cell morphology, cell microstructure, and intracellular contents ofV. parahaemolyticuswere assessed. Scanning electron microscopy revealed substantial damage to cell integrity, subsequent to PHL treatment. A notable reduction in intracellular components, including proteins, ATP, and DNA, was observed in samples treated with PHL. PHL was shown to inhibit the activities ofATPase, β-galactosidase, and respiratory chain dehydrogenase inV. parahaemolyticus. Furthermore, it was demonstrated to elevate the intracellular levels of reactive oxygen species and promote cell death. After being applied to sea bass, shrimp, and oysters, PHL effectively inactivatedV. parahaemolyticusin these seafoods. These findings demonstrate that PHL has potential for application in seafood to controlV. parahaemolyticus.

CAS / MDL: 90-30-2 60-82-2
研究领域: 食品科学 · 微生物学 · 食品安全
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PLANTA MEDICA · 2022 ·Vol. 88 ·期 13 ·1190-1198 · IF 3.007

Phloridzin Highly Accumulated in Malus rockii Rehder and Its Structure Revision and Hypolipidemic Activity

Li-Juan Lang,Min Wang,Chang Lei,Yi Shen,Qi-Jie Zhu,Hong-Mei Diao,Hao Chen,Lei Shen,Xiang Dong,Bei Jiang,Chao-Jiang Xiao

Phloridzin is a lead compound of the prestigious antidiabetic gliflozins. The present study found that phloridzin highly accumulated in Malus rockii Rehder. The content of phloridzin in M. rockii was the highest among wild plants, with the percentage of 15.54% in the dry leaves. The structure of phloridzin was revised by proton exchange experiments and extensive 2D NMR spectra. Phloridzin exhibited significant hypolipidemic activity in golden Syrian hamsters maybe by increasing the expression of CYP7A1, at the doses of 50 mg/kg and 200 mg/kg. The total performance of anti-hyperlipidemic effect of phloridzin may be superior to that of lovastatin, though lovastatin was more active than phloridzin. In addition, phloridzin exhibited moderate antimalarial activity with inhibition ratio of 31.3 ± 10.9% at a dose of 25 mg/kg/day, and showed moderate analgesic activity with 28.0% inhibition at a dose of 50 mg/kg.

CAS / MDL: 53-86-1
研究领域: 药理学 · 植物学 · 生物化学 · 药物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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TALANTA · 2017 · IF 4.162

A strategy for screening of α-glucosidase inhibitors from Morus alba root bark based on the ligand fishing combined with high-performance liquid chromatography mass spectrometer and molecular docking

Zhen Wang,Xiaoqing Li,Menghan Chen,Feiyan Liu,Chao Han,Lingyi Kong,Jianguang Luo

A new method based on ligand fishing combined with high-performance liquid chromatography quadrupole-time-of-flight mass spectrometer and molecular docking was established to screen α -glucosidase inhibitors from a traditional Chinese medicine Morus alba root bark. α -Glucosidase was immobilized on magnetic nanoparticles , used as a solid support to incubate with crude extract. After ligand fishing, the eluates were analyzed by high-performance liquid chromatography quadrupole-time-of-flight mass spectrometer, obtaining eleven ligands ( 1 – 4 , 6 – 12 ) eventually. In order to discriminate the non-specific binders and discover powerful enzyme inhibitors , molecular docking was further performed and three of the eleven ligands were optimized to be excellent α -glucosidase inhibitors by the confirmation of isolation and bioassay of individual compounds. These three ligands, sanggenons G ( 6 ), O ( 7 ) and sanggenol G ( 12 ) exhibited striking inhibitory activities with extremely low IC 50 values. The results suggest that established method will be applied to a wide range of target protein to screen potential bioactive constituents from herbal medicines.

研究领域: 中药学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MOLECULES · 2024 ·Vol. 29 ·期 2 ·315 · IF 4.2

Benzofuran Derivatives from Cortex Mori Radicis and Their Cholinesterase-Inhibitory Activity

Xiang Cui,Zehong Huang,Shanshan Deng,Yunxia Zhang,Guoyin Li,Lining Wang,Yanru Deng,Changjing Wu

The phytochemical investigation of Cortex Mori Radicis led to the isolation and identification of a new prenylated benzofuranone (1) and four ring-opening derivatives (2–5) named albaphenol A–E, as well as nigranol A (6), together with ten 2-arylbenzofuran derivatives (7–16). The characterization of the structures of the new compounds and the structural revision of nigranol A (6) were conducted using the comprehensive analysis of spectroscopic data (1D/2D NMR, HRESIMS, CD, and XRD). Compounds1–16were tested for their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Compounds1and4showed weak BChE-inhibitory activity (IC5045.5 and 61.0 μM); six 2-arylbenzofuran derivatives showed more-potent BChE-inhibitory activity (IC502.5–32.8 μM) than the positive control galantamine (IC5035.3 μM), while being inactive or weakly inhibitory toward AChE. Cathafuran C (14) exhibited the most potent and selective inhibitory activity against BChE in a competitive manner, with a Ki value of 1.7 μM. The structure–activity relationships of the benzofuran-type stilbenes were discussed. Furthermore, molecular docking and dynamic simulations were performed to clarify the interactions of the inhibitor–enzyme complex.

研究领域: 植物化学 · 药理学 · 神经科学
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