ACS Sustainable Chemistry & Engineering
·
2020
·
IF 7.632
Deqing Wang,Pu Zheng,Pengcheng Chen,Dan Wu
Deep eutectic solvents (DESs), considered to be “green media”, have recently been employed in multiple applications including biotransformations. Here, a DES was used in the production of isoquercitrin and l-rhamnose from rutin by enzymatic transformation with recombinant α-l-rhamnosidase from Aspergillus niger. A solution synthesized from choline chloride and urea (ChCl-U) performed best in the conversion of rutin among 24 kinds of DESs. When 130 g/L rutin was used as the substrate, the conversion rate was 100% and the productivity of l-rhamnose and isoquercitrin was 208.68 mM/h under optimized conditions in ChCl-U solution, which was 1.12 times higher than that in buffer (186.92 mM/h). The recycling of ChCl-U solution was also investigated by aqueous two-phase system extraction of l-rhamnose, and ChCl-U/K2HPO4 was screened as the suitable extraction solvent. When the ChCl-U content was 34%, the extraction efficiency of l-rhamnose was 79.06% with a purity and primary crystallization yield of 96.28 and 66.49%, respectively. After five cycles of ChCl-U solution, the average enzymatic conversion rate of recycling was 95.63% with an average purity of 94.22% of the isoquercitrin prepared. After 10 cycles of reuse, the residual conversion rate was 61.14%. The results indicate that the DES has obvious advantages in biocatalytic processes involving flavonoid conversion.
研究领域:
生物化学
·
绿色化学
·
酶工程
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DOI
高影响因子
GREEN CHEMISTRY
·
2020
·Vol. 22
·期 18
·5984-5988
·
IF 9.48
Yunchao Feng,Zheng Li,Sishi Long,Yong Sun,Xing Tang,Xianhai Zeng,Lu Lin
We report here that L-rhamnose, a less popular renewable and commercially available carbohydrate, can be used as a potential raw material to generate 5-methylfurfural (MF). In particular, nearly 100% yield of MF was achieved over 7 consecutive cycles in NaCl solution containing AlCl3 within 30 min, thus providing an alternative and industrializable way for the production of the potential bio-platform compound MF.
研究领域:
生物化学
·
可再生能源化学
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DOI
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2025
·
IF 8.5
Qihui Lu,Hui Liao,Zedong Jiang,Yanbing Zhu,Yijuan Han,Lijun Li,Hui Ni,Qingbiao Li
Glycosylation plays a critical role in regulating activity, stability, and correct folding of enzymes. In this study, recombinant Aspergillus niger α-L-rhamnosidase (r-Rha1) was employed to explore the impact of glycosylation in Pichia pastoris on the enzymatic properties and protein folding . β-elimination reaction and deglycosylase treatment assays demonstrated that r-Rha1 undergoes primarily N-glycosylation. The deglycosylated r-Rha1 was prepared in two ways: treating with Endoglycosidase F 1 after expression (referred to as r-Rha1- vitro ), or inhibiting intracellular glycosylation using tunicamycin (referred to as r-Rha1- vivo ). Deglycosylation resulted in a 0.22-fold decrease in activity for r-Rha1- vitro and due to its slower turnover rate, r-Rha1- vivo showed a 0.73-fold decrease in activity. r-Rha1- vitro maintained the similar optimal temperature as r-Rha1, r-Rha1- vivo displayed a 10 °C lower optimal temperature. Compared to the decreased extent of r-Rha1- vitro in t 1/2 at 55 °C, 60 °C, and 65 °C and T m , chemical interferent deglycosylation in vivo showed a more profound impact on r-Rha1. Analyses based on circular dichroism, fluorescence spectroscopy, and differential scanning calorimetry revealed significant changes in the structure and thermodynamic stability of r-Rha1- vivo , accounting for its marked decline in activity and stability. The significant and unpredictable structure changes of r-Rha1- vivo proved the essential role of glycosylation for appropriate folding in P. pastoris .
研究领域:
生物化学
·
分子生物学
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产品关联
DOI
PubMed
高影响因子
Catalysts
·
2025
·Vol. 15
·期 5
·465
·
IF 4
Zongke He,Pengfei Jiang,Qianqian Cui,Ziyue Wang,Yaozhong Wei,Chao Luo,Jichang Guo,Chang Liu,Wei Zhang
In this work, the method of highly efficient conversion ofl-rhamnose to 5-methylfurfural (MF) catalyzed by various catalysts in a biphasic system was developed. To enhance the MF yield, the effects of the catalyst species, reaction temperature (150–180 °C), extraction solvents and volume ratio of the extraction to the aqueous phase (0–5) on the conversion ofl-rhamnose to MF were systematically investigated. Under optimal conditions, a high MF yield of 94% was achieved in the biphasic “diisopropyl ether (DIPE) + H2O” system due to the fact that the extraction of MF to the DIPE phase significantly inhibits the condensation and degradation of MF in water. Finally, detailed reaction energetics and chemical structures of intermediates of thel-rhamnose dehydration to MF were investigated using the B3LYP level of theory and the SMD solvation model. It is evident that MF, which exhibits excellent chemical stability, harbors the potential to function as a bio-derived platform chemical within the domain of the green industry.
研究领域:
有机化学
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催化化学
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绿色化学
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DOI
高影响因子
INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY
·
2017
·Vol. 52
·期 12
·2596-2603
·
IF 1.64
Lin Ge,Jingcong Xie,Tao Wu,Shanshan Zhang,Linguo Zhao,Gang Ding,Zhenzhong Wang,Wei Xiao
Summary A novel α-L-rhamnosidase was isolated and purified from Aspergillus oryzae NL-1. The enzyme was purified 13.2-fold by ultrafiltration, ion exchange and gel filtration chromatography with an overall recovery of 6.4% and specific activity of 224.4 U/mg, and the molecular mass of its subunit was approximately 75 kDa. Its optimal temperature and pH were 65 °C and 4.5, respectively. The enzyme was stable in the pH range 3.5–7.0, and it showed good thermostability at higher temperatures. The K M , kcat and kcat/K M values were 5.2 m m , 1624 s −1 and 312 s −1 m m −1 using p NPR as substrates, respectively. Moreover, the enzyme exhibited transglycosylating activity, which could synthesise rhamnosyl mannitol through the reactions of transglycosylation with inexpensive rhamnose as the glycosyl donor. Our findings indicate that the enzyme has potential value for glycoside synthesis in the food industry.
研究领域:
生物化学
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食品科学
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产品关联
DOI
高影响因子
PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY
·
2020
·
IF 1.415
Li Jun Li,Xiao Qing Liu,Xi Ping Du,Ling Wu,Ze Dong Jiang,Hui Ni,Qing Biao Li,Feng Chen
Isoquercitrin is a flavonoid with important applications in the pharmaceutical and nutraceutical industries. However, a low yield and high production cost hinders the industrial preparation of isoquercitrin. In the present study, isoquercitrin was prepared by biotransformation of rutin using α-L-rhamnosidase from Aspergillus niger JMU-TS528 combined with high-speed countercurrent chromatography (HSCCC) purification. As a result, the optimum transformation pH, temperature, and time were pH 4.0, 60 °C, and 60 min, respectively. The Km and Vmax were 0.36 mM and 0.460 mmol/min, respectively. For isoquercitrin production, the optimal rutin concentration and transformation time were approximately 1000 mg/L and 60 min. The rutin transformation rate reached 96.44%. The isoquercitrin was purified to a purity of 97.83% using one-step purification with HSCCC. The isoquercitrin was identified using UPLC-Q-TOF-MS. The comprehensive results indicated that the biotransformation procedure using the α-L-rhamnosidase from A. niger JMU-TS528 combined with HSCCC was a simple and effective process to prepare isoquercitrin, which might facilitate the production of isoquercitrin for industrial use.
研究领域:
生物化学
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制药工程
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食品科学
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产品关联
DOI
PubMed
高影响因子
Food Bioscience
·
2025
·
IF 5.9
Cheng-Hai Yan,Ding Wang,Ruo-Xi Mei,Lu Tan,Yi-Jiang-Cheng Li,Richard Ansah Herman,Yan Xu,Lu-Chan Gong,Jun Wang
Natural flavonoids exhibit diverse physiological effects and are used as functional factors, antioxidants and pigments in food as well as pharmaceutical and cosmetic applications. However, their poor solubility and stability, result in low bioavailability. Biomodification through deglycosylation effectively enhances their bioactivity. This study developed two surface display strategies in Escherichia coli , anchoring α -L-rhamnosidase RhaB1-ΔN to the cell surface using the anchoring protein Lpp-OmpA. Immunofluorescence and proteinase K sensitivity tests confirmed the successful construction of surface-displaying strains E. coli Lpp-OmpA-RhaB1-ΔN and E. coli RhaB1-ΔN-SpyCatcher-SpyTag. Enzymatic property studies revealed improved temperature and pH stability of the whole-cell catalysts with surface compared to free enzymes. After 6 catalytic cycles, E. coli Lpp-OmpA-RhaB1-ΔN retained higher activity than E. coli RhaB1-ΔN. In flavonoid hydrolysis, E. coli Lpp-OmpA-RhaB1-ΔN increased yields of isoquercitrin and kaempferol-3- O -glucuronide by 20.25% and 10.99%, respectively, compared with that in whole-cell catalyst with intracellular enzyme ( p < 0.05). In addition, it should be noted that although the enzyme expression of E. coli RhaB1-ΔN-SpyCatcher-SpyTag is reduced, its hydrolysis ability of flavonoids is comparable to that of E. coli RhaB1-ΔN due to the efficient catalytic ability of extracellular enzymes. This study establishes reliable whole-cell catalysts with surface-displayed α -L-rhamnosidase for efficient natural flavonoid modification, with potential applications in the food and pharmaceutical industries.
研究领域:
生物化学
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食品科学
·
制药工程
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产品关联
DOI
高影响因子
COMBUSTION AND FLAME
·
2020
·
IF 4.57
Chuan Yuan,Ding Jiang,Shuang Wang,Bahram Barati,Xun Gong,Bin Cao,RuiPing Zhang,Chuang Zhang,Emmanuel A. Odey
In this study, L -rhamnose monohydrate (LRM) was used as a model compound of seaweed polysaccharide to study its pyrolysis and catalytic pyrolysis mechanism . Initially, the weight loss curve of LRM was obtained by thermogravimetric analysis. The main weight loss temperature was found to be at 350–550 °C. Then, the pyrolysis mechanism of LRM was analyzed and verified by macroscopic experiments and molecular simulations. Experiments showed that the bio-oil yield was highest when the temperature reached around 500 °C, and the bio-oil contained large amount of furan substances. Finally, the effects of different proportions of catalysts (Mg–Ce/ZSM-5) on bio-oil products were studied, and the catalytic reaction mechanism was discussed.
研究领域:
能源植物学
·
化学工程
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产品关联
DOI
高影响因子
Journal of Food Measurement and Characterization
·
2016
·Vol. 11
·期 2
·548-555
·
IF 0.521
Xiaohong Zhang,Zhidong Zhao,Xiongwei Lou,Jian Li,Guohua Hui
A maltose, L-rhamnose sensor based on porous Cu foam and electrochemical techniques was investigated in this paper. Cu foam material was prepared and characterized by scanning electron microscopy (SEM). The electro-oxidation reaction process of sweeteners occurred on Cu foam electrode was evaluated by cyclic voltammetry (CV) scanning. At an applied potential of 0.5 V, the linear range for maltose is 0.18–3.47 mM with sensitivity of 1.0492 mA cm −2 mM −1 . The limit of detection (LOD) was 15.86 μM (S/N = 3). The linear range for maltose is 0.18–3.47 mM with sensitivity of 0.6881 mA cm −2 mM −1 . The LOD was 24.18 μM (S/N = 3). Compared with Cu sheet electrode, Cu foam electrode showed higher current response towards maltose and L-rhamnose, leading to enhanced electrocatalytic activity, higher sensitivity, and lower LOD. Sweetener qualitative discrimination was carried out by stochastic resonance (SR) signal-to-noise ratio (SNR) spectrum eigen peak located noise intensities.
研究领域:
分析化学
·
生物传感技术
·
材料科学
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产品关联
DOI
高影响因子
MOLECULES
·
2025
·Vol. 30
·期 5
·980
·
IF 4.6
Bin-Chun Li,Bingbing Wu,Xueting Hou,Guo-Bin Ding
α-L-rhamnosidases play a key role in the metabolism and biodegradation of dietary flavonoid glycosides. We have developed a novel microplate spectrophotometric method to rapidly evaluate the conversion rates and substrate selectivities of mesophilic α-L-rhamnosidases towards citrus flavanone diglycosides by combining with a high-active and thermophilic β-D-glucosidase based on UV-visible spectral differences between citrus flavanone diglycosides and the corresponding aglycones under alkaline conditions. Furthermore, catalytic activities and enzyme kinetics of four α-L-rhamnosidases from human gut bacteria on various dietary flavonoid glycosides with different glycosidic bonds from various subclasses have been explored by HPLC. The α-L-rhamnosidase BtRha78A specifically removed the rhamnose group from the flavones, flavanones and flavonols diglycosides with the α-1,6 glycosidic bonds. Moreover, BtRha78A displayed higher catalytic activities on the rutinose group at 7-OH of the aglycones than at 3-OH. HFM-RhaA preferred to catalyze the flavones, flavanones and dihydrochalcones diglycosides with the α-1,2 glycosidic linkages at the 7-OH. However, this enzyme also showed high catalytic activity on the flavonol diglycoside rutin with the α-1,6 glycosidic bonds at the 3-OH. HFM-RhaC exhibited certain hydrolytic abilities towards all flavonoid diglycosides, and displayed higher activities on the flavonoid diglycosides with the α-1,6 glycosidic bonds. HFM-Rha78 weakly hydrolyzed the flavones, flavanones and dihydrochalcones diglycosides with the α-1,2 glycosidic bonds, and the flavonols diglycosides with α-1,6 glycosidic bonds. All four α-L-rhamnosidases from human gut bacteria did not exhibit catalytic activity towards the flavonoid glycosides with the α-1 glycosidic bonds. It was revealed that the α-L-rhamnosidases from human gut bacteria possessed diverse substrate selectivity on dietary flavonoid diglycosides. The structural basis for the specificity of BtRha78A on the flavonoid diglycosides with α-1,6 glycosidic bonds and the preference of HFM-RhaA on the flavonoid diglycosides with α-1,2 glycosidic bonds have been analyzed by molecular docking.
CAS / MDL:
研究领域:
生物化学
·
微生物学
·
营养学
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产品关联
DOI
PubMed
高影响因子
POLYHEDRON
·
2022
·
IF 2.975
Chunqing Wang,Na Xia,Siming Zhu,Lin Chen,Liang Chen,Zhendong Wang
In this study, α- l -rhamnosidase was immobilized on magnetic Fe 3 O 4 /MIL-101 (Cr) nanoparticles using MIL-101(Cr) as precursor by crosslinking method. The crosslinking agent concentration ratio and crosslinking time were EDC/NHS 1:1 and 2 h, respectively. The immobilized materials were characterized by FT-IR, XRD, SEM and VSM. The saturation magnetization of the prepared magnetic nanoparticles was 46.2 emu/g. The optimum pH and temperature of immobilized enzyme were 6 and 60 °C. The application of immobilized enzyme in the preparation of hesperidin dihydrochalcone glucoside (HMGDC) by hydrolysis of hesperidin dihydrochalcone (HSDDC) was studied. The results showed that immobilized enzyme had better temperature resistance, repeatability and stability than free enzyme. The immobilized enzyme activity was 293.55 U/g, and the recovery was 116.03%. After treatment at 60 °C for 4 days, the enzyme activity remained at 24.6%. The conversion rate of HSDDC reached 93.1%.
研究领域:
生物催化
·
食品科学
·
材料科学
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产品关联
DOI
高影响因子
FOOD CHEMISTRY
·
2014
·
IF 3.259
Chanjuan Xu,Bingxian Yang,Wei Zhu,Ximin Li,Jingkui Tian,Lin Zhang
The leaves of Linderae aggregate (LAL) has been used as a type of tea in China and other Southeast Asian countries. In this study, 11 polyphenols in LAL were clarified for the first time using multiple high-performance liquid chromatographic techniques. An optimal extracting method was developed through the comparison of the amount of quercetin-3- O -α- l -rhamnoside using a uniform design method. From the fingerprint liquid chromatography data, 11 common peaks in the 8 samples collected from April to November were semi-determined. The antioxidant capacities were examined using the 2,2-diphenyl-1-picrylhydrazyl free radical scavenging assay and the ferric reducing/antioxidant power assay. All 8 samples contained the same 11 polyphenols in similar ratios. Three samples, S2, S5 and S6 contained higher amount of quercetin-3- O -α- l -rhamnoside and were demonstrated to have stronger antioxidant capacities in both antioxidant assays. These results are critical in optimising harvest time and quality control of LAL.
研究领域:
植物化学
·
药理学
·
分析化学
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DOI
高影响因子
危险品化学品经营许可证（带存储）