Scientific Reports
·
2016
·Vol. 6
·期 1
·1-15
·
IF 5.228
Zhang Tingjing,Liang Jianqiang,Wang Panxue,Xu Ying,Wang Yutang,Wei Xinyuan,Fan Mingtao
Phloretin-2′- O -glycosyltransferase (P2′GT) catalyzes the last glycosylation step in the biosynthesis of phloridzin that contributes to the flavor, color and health benefits of apples and processed apple products. In this work, a novel P2′GT of Malus x domestica (Md P2′GT) with a specific activity of 46.82 μkat/Kg protein toward phloretin and uridine diphosphate glucose (UDPG) at an optimal temperature of 30 °C and pH 8.0 was purified from the engineered Pichia pastoris broth to homogeneity by anion exchange chromatography, His-Trap affinity chromatography and gel filtration. The purified Md P2′GT was low N -glycosylated and secreted as a stable dimer with a molecular mass of 70.7 kDa in its native form. Importantly, Md P2′GT also exhibited activity towards quercetin and adenosine diphosphate glucose (ADPG), kaempferol and UDPG, quercetin and UDP-galactose, isoliquiritigenin and UDPG, and luteolin and UDPG, producing only one isoquercitrin, astragalin, hyperoside, isoliquiritin, or cynaroside, respectively. This broad spectrum of activities make Md P2′GT a promising biocatalyst for the industrial preparation of the corresponding polyphenol glycosides, preferably for their subsequent isolation and purification. Besides, Md P2′GT displayed the lowest K m and the highest k cat /K m for phloretin and UDPG compared to all previously reported P2′GTs, making Md P2′GT favor phloridzin synthesis the most.
研究领域:
植物学
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生物化学
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食品科学
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DOI
PubMed
高影响因子
PLANT JOURNAL
·
2025
·Vol. 121
·期 3
·e17248
·
IF 5.7
Xiaomeng Zhang,Xinquan Tian,Junyu Luo,Xiaoyang Wang,Shoupu He,Gaofei Sun,Ruidan Dong,Panhong Dai,Xiao Wang,Zhaoe Pan,Baojun Chen,Daowu Hu,Liru Wang,Baoyin Pang,Aishuang Xing,Guoyong Fu,Baoquan Wang,Jinjie Cui,Lei Ma,Xiongming Du
SUMMARY Phloridzin has various functions, including antioxidant properties and the treatment of diabetes, and has long been used in pharmaceutical and physiological research. The glycosylation of phloretin is a key step in the biosynthesis of phloridzin. In this study, a genome-wide association study (GWAS) based on phloridzin content was applied, and the key gene GhUGT88F3 for phloridzin-specific biosynthesis was identified in cotton. A single-base deletion in GhUGT88F3 in haplotype I caused a frameshift mutation, leading to premature translation termination and a significant reduction in phloridzin content. Molecular docking revealed important amino acid residues for GhUGT88F3's UDP-glucose transfer activity. Additionally, the transcription factor GhMYB330 was found to positively regulate GhUGT88F3 expression through population transcriptome analysis and LUC experiment. Moreover, phloridzin content was significantly elevated in both GhUGT88F3 and GhMYB330 overexpression transgenic plants. This study expands the diversity of UDP-glucosyltransferases in plants and offers a potential strategy for the sustainable production of bioactive compounds with therapeutic potential.
研究领域:
植物学
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遗传学
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生物化学
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DOI
PubMed
高影响因子
FOOD CHEMISTRY
·
2018
·
IF 4.946
Yongsheng Chen,Jiangwei Liu,Sheng Geng,Yonglan Liu,Hanjun Ma,Jie Zheng,Benguo Liu,Guizhao Liang
Herein, we perform the regioselective acetylation of phloridzin catalyzed by immobilized Candida antarctica lipase B (CALB). We show that the enzyme amount and reaction time can significantly influence the composition of mono-, di- and tri-acetylated phloridzin in the product. The last acetylated derivative of phloridzin is isolated and identified as 4, 3″, 6″-3-O-acetyl-phloridzin by HPLC, UV, IR, MS and NMR. Molecular docking suggests that the first acetylation of phloridzin catalyzed by CALB occurs in 6″-OH, followed by 3″-OH, then 4-OH. During this process, hydrogen bond and hydrophobic forces play an important role in maintaining the binding interaction of CALB with phloridzin or its acetylated derivatives. Although, tri-acetylated phloridzin has moderate to minimal adverse-effects on LO-2, its anti-proliferative activity against human HepG2 cancer cells is superior to that of phloridzin, which attributes to its high capacity of inducing cell apoptosis, retarding cell cycle, lowering mitochondrial membrane potential and scavenging intracellular ROS.
研究领域:
生物化学
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药物化学
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肿瘤学
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产品关联
DOI
PubMed
高影响因子
ANALYTICAL LETTERS
·
2021
·
IF 2.329
Zhiting Ma,Wenyan Du,Zhubing Yan,Xuesen Chen,Yanfang Wang,Zhiquan Mao
Phloridzin is a phenolic acid associated with the genus Malus (Mill.) that causes apple replant disease. The removal of phloridzin is of great significance to alleviate this condition, and hence biochar was investigated for this purpose. The goal of this study was to improve the adsorption capacity of biochar for phloridzin by chemical modification. Biochar from apple branches and biochar modified with chitosan to were characterized by elemental analysis, Brunauer Emmett Teller analysis, Fourier transform infrared spectroscopy, X-ray diffraction, and scanning electron microscopy. Batch adsorption experiments were employed to select the optimal biochar dosage and adsorption time. The results showed that biochar treated for 24 h at 6 g L−1 achieved best adsorption properties and that the chitosan-modified biochar provided a higher adsorption capacity than the unmodified material. The influence of pH upon the adsorption was studied and the results were fitted with isotherm and kinetic equations. The results showed that adsorption process corresponds to a Langmuir isotherm and pseudo-second-order kinetics. The qmax of the biochar was increased from 15.93 to 28.96 mg g−1 by modification with chitosan. The pH was shown to play an important role in the adsorption process. The adsorption of phloridzin to biochar was demonstrated to be a single-layer multiple component adsorption process based on chemisorption. This study provides a theoretical basis to alleviate apple replant disease.
研究领域:
植物学
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环境科学
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农业科学
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产品关联
DOI
高影响因子
TALANTA
·
2017
·
IF 4.162
Die Gao,Dan-Dan Wang,Qi-Feng Fu,Lu-Jun Wang,Kai-Lian Zhang,Feng-Qing Yang,Zhi-Ning Xia
In present study, magnetic molecularly imprinted polymers (MMIPs) were successfully prepared for specific recognition and selective enrichment of phloridzin from the leaves of Malus doumeri (Bois) A. Chev and rats' plasma. The magnetic Fe 3 O 4 were prepared by the solvothermal reaction method and followed by the modification of TEOS and functionalization with APTES . Using functionalized Fe 3 O 4 particles as the magnetic cores, phloridzin as template, ethylene glycol dimethacrylate (EGDMA) as cross-linker and 2,2-azobisisobutyonnitrile (AIBN) as initiator, the MMIPs were prepared through APTES to associate the template on the surface of the magnetic substrate. The structural features and morphological characterizations of MMIPs were performed by FT-IR, SEM, TEM, XRD, TGA and VSM . The adsorption experiments revealed that the MMIPs presented high selective recognition property to phloridzin. The selectivity experiment indicated that the adsorption capacity and selectivity of polymers to phloridzin was higher than that of baicalin and 2,3,5,4′-ttrahydroxy stilbene-2-O-β-D-glucoside. Furthermore, the MMIPs were employed as adsorbents for extraction and enrichment of phloridzin from the leaves of M. doumeri and rats' plasma. The recoveries of phloridzin in the leaves of M. doumeri ranged from 81.45% to 90.27%. The maximum concentration (C max ) of phloridzin in rats' plasma was detected as 12.19 ± 0.84 μg/mL at about 15 min after oral administration of phloridzin (200 mg/kg). These results demonstrate that the prepared MMIPs are suitable for the selective adsorption of phloridzin from complex samples such as natural medical plants and biological samples.
研究领域:
药学
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分析化学
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产品关联
DOI
PubMed
高影响因子
Natural Product Communications
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2021
·
IF 0.986
Haoyu Zhou,Changzhong Liu,Sheng Geng
Phloridzin is a naturally occurring dihydrochalcone with various therapeutic properties. However, its low aqueous solubility and poor enzyme inhibitory capacity have limited its application in functional foods and medicines. Inspections of the properties of natural polymeric flavonoids suggest that these limitations could be mitigated by the polymerization of phloridzin, although to date, no relevant studies have been conducted. Here, oxidative polymerization was used to prepare polymeric phloridzin using laccase as the catalyst, and its structure, antioxidant capacity and α-glucosidase inhibitory activity were characterized. The results showed that laccase catalyzed polymerization via oxidative generation of phenolic radicals in the B ring of phloridzin to achieve the polymerization. The 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) radical scavenging capacity of the polymer (IC50, 0.48 mg/mL) was inferior to that of phloridzin (IC50, 0.20 mg/mL), but the α-glucosidase inhibitory activity of the polymer (IC50, 0.12 mg/mL) was significantly higher than that of phloridzin (IC50, 0.21 mg/mL). These effects could be attributed to the reduction of available phenolic groups and binding of the polymer to the enzyme, respectively.
研究领域:
食品科学
·
生物化学
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产品关联
DOI
高影响因子
FOOD CHEMISTRY
·
2016
·
IF 4.052
Chun-Ling Zhang,Jie-Chao Liu,Wen-Bo Yang,Da-Lei Chen,Zhong-Gao Jiao
Phloridzin is a nutraceutical. Its use in food, medicine and cosmetics is limited because of its low aqueous solubility and stability limits, but it can be improved by complexing with cyclodextrins. In this study, we investigated the inclusion mechanism between phloridzin and hydroxylpropyl-β-cyclodextrin (HP-β-CD) using isothermal titration calorimetry (ITC), ultraviolet–visible spectrometry (UV), infrared spectrometry (IR), proton nuclear magnetic resonance spectroscopy ( 1 H NMR) and molecular docking simulations. The ITC results found that the equilibrium binding constant of HP-β-CD with phloridzin was higher than that of β-CD. Their inclusion was a spontaneous process with negative ΔG, ΔH and ΔS values. UV spectra showed that the aqueous solubility of phloridzin was enhanced by HP-β-CD. Our IR analysis verified the inclusion complexation of phloridzin into the HP-β-CD cavity. The Autodock determined that the substitution distribution of HP-β-CD influenced not only the orientation and depth degree of phloridzin within the cavity, but also the binding energies.
研究领域:
食品科学
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药物化学
·
生物化学
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DOI
PubMed
高影响因子
Analytical Methods
·
2024
·Vol. 16
·期 16
·2513-2521
·
IF 2.7
Zhengming Qian,Qinggui Lei,Dan Tang,Guoying Tan,Qi Huang,Fucai Zhou,Wenhao Wang
Sweet tea is a functional herbal tea with anti-inflammatory, anti-diabetic, and other effects, in which phloridzin and trilobatin are two functional compounds. However, the current methods for their quantification are time-consuming, costly, and environmentally unfriendly. In this paper, we propose a rapid method that integrates online pressurized liquid extraction and high-performance liquid chromatography featuring a superficially porous column for fast separation. Moreover, we employ an equal absorption wavelength method to eliminate using multiple standard solutions and relative calibration factors. Our verification process corroborated the technique's selectivity, accuracy, precision, linearity, and detection limitations. Separately, our methodology demonstrated excellent analytical efficiency, cost-effectiveness, and environmental friendliness. Practical application using six distinct batches of sweet tea samples yielded results in congruence with the external standard method. The analytical rate of this technique is up to over 18 times faster than traditional methods, and organic solvent consumption has been reduced to less than 1.5 mL. Therefore, this method provides a valuable way to achieve quality control and green analysis of sweet tea and other herbal teas.
研究领域:
植物化学
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分析化学
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药学
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产品关联
DOI
PubMed
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
·
2023
·
IF 6
Fang Wei,Liyong Luo,Liang Zeng
Camellia nanchuanica gained attention for having original tea tree characteristics and producing black tea with appealing sweetness . To better study the sweet taste of Camellia nanchuanica black tea, 30 kinds of Camellia nanchuanica black tea (NCBT) samples were classified into three types (high, middle and low sweetness) according to the differences in sweetness. A total of 844 metabolites were detected in NCBT; among them, there were 155 differential metabolites. Four differential metabolites (phloridzin, dulcitol, l -alanine, and sucrose) positively correlated with sweetness and showed higher VIP (variable importance for the projection) values (>1), which made main contributions to the sweetness of NCBT. Phloridzin and l -alanine might be the key sweet compounds of NCBT due to higher DoT (dose-over-threshold) values. Addition experiments further verified that phloridzin was the key sweet taste compound because phloridzin significantly increased the sweet taste of low sweetness samples. Notably, although NCBT24, 26, and 28 belonged to high sweetness samples, phloridzin content was lower. Based on the interactions of binary mixture, hyper-addition effects of phloridzin, dulcitol, l -alanine, and sucrose existed in NCBT24, 26 and 28.
研究领域:
食品科学
·
植物化学
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产品关联
DOI
高影响因子
JOURNAL OF FOOD BIOCHEMISTRY
·
2017
·Vol. 42
·期 2
·e12475
·
IF 1
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.
研究领域:
食品科学
·
生物化学
·
农业化学
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产品关联
DOI
高影响因子
Heliyon
·
2019
·
IF 0
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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DOI
PubMed
TROPICAL JOURNAL OF PHARMACEUTICAL RESEARCH
·
2012
·Vol. 11
·期 4
·545-551
·
IF 0.82
E Yuan,B Liu,W Li,Q Li
Purpose: To improve the aqueous solubility of phloridzin by complexing it with hydroxypropyl-β-cyclodextrin (HP-β-CD).Methods: The complex of phloridzin with HP-β-CD was prepared by freeze-drying method. The physicochemical properties of the complex were investigated by ultraviolet-visible spectrometry (UV), infrared spectrometry (IR), differential scanning calorimetry (DSC) and x-ray diffractometry (XRD). The antioxidant activity was examined by DPPH and ABTS radical-scavenging activities.Results: Phloridzin in the complex was molecularly dispersed in HP-β-CD matrix. The complex was an effective scavenger of DPPH and ABTS radicals. At a concentration of 0.8 mg/mL and 30 μg/mL, DPPH and ABTS radical scavenging activities of the complex were 83.7 and 74.9 %, respectively.Conclusion: By forming inclusion complex with HP-β-CD, the solubility of phloridzin in water was significantly enhanced. The complex showed strong DPPH and ABTS radical scavenging activities.
研究领域:
药剂学
·
药物化学
·
分子药理学
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天然产物化学
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药物递送系统
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抗氧化研究
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DOI
高影响因子
危险品化学品经营许可证（带存储）