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Horticulture Research · 2022 · IF 7.291

Identification of UDP-rhamnosyltransferases and UDP-galactosyltransferase involved in flavonol glycosylation in Morella rubra

Ren Chuanhong,Guo Yan,Xie Linfeng,Zhao Zhikang,Xing Mengyun,Cao Yunlin,Liu Yilong,Lin Jing,Grierson Donald,Zhang Bo,Xu Changjie,Chen Kunsong,Li Xian

Flavonol glycosides are health-promoting phytochemicals important for human nutrition and plant defense against environmental stresses. Glycosylation modification greatly enriches the diversity of flavonols. Morella rubra, a member of the Myricaceae, contains high amounts of myricetin 3-O-rhamnoside (M3Rha), quercetin 3-O-rhamnoside (Q3Rha), and quercetin 3-O-galactoside (Q3Gal). In the present study, MrUGT78R1 and MrUGT78R2 were identified as two functional UDP-rhamnosyltransferases, while MrUGT78W1 was identified as a UDP-galactosyltransferase. Site-directed mutagenesis identified Pro143 and Asn386 as important residues for rhamnosyl transfer activity of MrUGT78R1, while the two corresponding positions in MrUGT78W1 (i.e. Ser147 and Asn370) also play important roles in galactosyl transfer activity. Transient expression data for these three MrUGTs in Nicotiana benthamiana tested the function of MrUGT78R1 and MrUGT78R2 as rhamnosyltransferases and MrUGT78W1 as a galactosyltransferase in glycosylation of flavonols. This work enriches knowledge of the diversity of UDP-rhamnosyltransferase in planta and identifies two amino acid positions important for both rhamnosyltransferase and galactosyltransferase.

研究领域: 植物科学 · 生物化学 · 分子生物学
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International Journal of Environmental Research and Public Health · 2022 ·Vol. 19 ·期 18 ·11518 · IF 4.614

Rhamnolipid-Enhanced ZVI-Activated Sodium Persulfate Remediation of Pyrene-Contaminated Soil

Wenyang Wang,Xiyuan Wang,Hao Zhang,Qingdong Shi,Huapeng Liu

In soil, polycyclic aromatic hydrocarbons (PAHs) are tightly bound to organic components, but surfactants can effectively transform them from a solid to a liquid phase. In this study, the biosurfactant rhamnolipid (RL) was selected as the eluent; shaking elution in a thermostatic oscillator improved the elution rate of pyrene, and the effects of RL concentration, temperature, and elution time on the elution effect were compared. After four repeated washings, the maximum elution rate was 75.6% at a rhamnolipid concentration of 20 g/L and a temperature of 45 °C. We found that 38 μm Zero-Valent Iron (ZVI) had a higher primary reaction rate (0.042 h−1), with a degradation rate of 94.5% when 3 g/L ZVI was added to 21 mM Na2S2O8at 60 °C. Finally, electron paramagnetic resonance (EPR) detected DMPO-OH and DMPO-SO4signals, which played a major role in the degradation of pyrene. Overall, these results show that the combination of rhamnolipid elution and persulfate oxidation system effectively remediated pyrene-contaminated soil and provides some implications for the combined remediation with biosurfactants and chemical oxidation.Keywords:soil washing;persulfate;ZVI;rhamnolipid;pyrene

研究领域: 环境科学 · 生物修复
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SCIENCE OF THE TOTAL ENVIRONMENT · 2023 · IF 9.8

A novel eco-friendly strategy for removing phenanthrene from groundwater: Synergism of nanobubbles and rhamnolipid

Wang Kai Tong,Chaomeng Dai,Jiajun Hu,Jixiang Li,Min-tian Gao,Xueji You,Xin Ru Feng,Zhi Li,Lang Zhou,Yalei Zhang,Xiaoying Lai,Long Kahon,Rongbing Fu

Nanobubbles (NBs), given their unique properties, could theoretically be paired with rhamnolipids (RL) to tackle polycyclic aromatic hydrocarbon contamination in groundwater. This approach may overcome the limitations of traditional surfactants, such as high toxicity and low efficiency. In this study, the remediation efficiency of RL, with or without NBs, was assessed through soil column experiments (soil contaminated with phenanthrene). Through the analysis of the two-site non-equilibrium diffusion model, there was a synergistic effect between NBs and RL. The introduction of NBs led to a reduction of up to 24.3 % in the total removal time of phenanthrene . The direct reason for this was that with NBs, the retardation factor of RL was reduced by 1.9 % to 15.4 %, which accelerated the solute replacement of RL. The reasons for this synergy were multifaceted. Detailed analysis reveals that NBs improve RL's colloidal stability, increase its absolute zeta potential , and reduce its soil adsorption capacity by 13.3 %–19.9 %. Furthermore, NBs and their interaction with RL substantially diminish the surface tension, contact angle, and dynamic viscosity of the leaching solution. These changes in surface thermodynamic and rheological properties significantly enhance the migration efficiency of the eluent. The research outcomes facilitate a thorough comprehension of NBs' attributes and their relevant applications, and propose an eco-friendly method to improve the efficiency of surfactant remediation.

CAS / MDL: 85-01-8 14808-60-7
研究领域: 环境科学 · 生态学
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ACS Sustainable Chemistry & Engineering · 2020 · IF 7.632

Highly Efficient Enzymatic Conversion of Rutin to Isoquercitrin and l-Rhamnose Using Deep Eutectic Solvents

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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COLLOIDS AND SURFACES B-BIOINTERFACES · 2019 · IF 3.973

Improvement on stability, loading capacity and sustained release of rhamnolipids modified curcumin liposomes

Ce Cheng,Zhihua Wu,David Julian McClements,Liqiang Zou,Shengfeng Peng,Wei Zhou,Wei Liu

A novel cholesterol-free curcumin delivery system was fabricated by rhamnolipids modified liposomes (RL-Lps). The incorporation of the rhamnolipids increased the sphericity, reduced the size, and decreased the polydispersity of the liposomes compared with pure liposomes (Lps). Analysis of the environmental stability of the RL-Lps showed they have good long-term stability over a wide range of pH (2–3 and 5–8), ionic strengths (0–200 mM), and accelerated centrifugal conditions. The curcumin-loaded rhamnolipids modified liposomes (Cur-RL-Lps) could be prepared with a relatively high loading efficiency (LE > 90%) and loading capacity (LC > 3.5%). The thermal and photochemical stability of the curcumin was improved after encapsulation in the Cur-RL-Lps. In vitro release studies indicated that the sustained release of the curcumin was prolonged when rhamnolipids were incorporated into the liposomes. This study shows that rhamnolipids have great potential for liposomal delivery system suitable for utilization in functional foods, dietary supplements, and pharmaceutical preparations.

CAS / MDL: 458-37-7
研究领域: 药学 · 药物递送系统 · 生物技术
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FUEL · 2023 · IF 7.4

Additions of esterase and rhamnolipid promote the degradation of Inner Mongolia coal by Pseudomonas japonica

Chen Shi,Xiangrong Liu,Shun-Sheng Zhao,Zaiwen Yang

The biodegradation of Inner Mongolia coal by Pseudomonas japonica ( P. japonica ) was investigated, showing that the biodegradability of P. japonica was related to its secretions: esterase (Es) and rhamnolipid (Rh). Therefore, the efficiencies of coal biodegradation were explored through additions of Es, Rh and the mixture of Es and Rh (Es-Rh) to the biodegradation system, respectively. It was found that the coal biodegradation rate all increased in the presence of Es-Rh, Es or Rh, among which Es-Rh significantly increased the coal biodegradation rate. When the ratio of Es-Rh was 150 mg/mL:1200 mg/mL, the coal biodegradation rate reached a maximum of 65.3% higher than the control group 18.8%, it was because the optical density and esterase activity of P. japonica were the highest, while the electronegativity and adsorption rate of coal samples were the optima. GC–MS of the degradation liquid products showed that the compositions of degradation liquid products in the presence of Es-Rh mainly contained long-chain alkanes, alcohols and ethers, of which the highest content of long-chain alkanes was 81.13%. FTIR analysis confirmed that the C H, C C and -COOR groups in Inner Mongolia coal were degraded in the presence of Es-Rh. XRD analysis demonstrated that the L c and N ave decreased in the presence of Es-Rh, indicating that the crystallization degree of Inner Mongolia coal decreased. This study indicated that the addition of mixture of Es and Rh could significantly promote the degradation of Inner Mongolia coal by P. japonica .

CAS / MDL: 94-75-7 7440-16-6
研究领域: 微生物学 · 环境科学
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GREEN CHEMISTRY · 2020 ·Vol. 22 ·期 18 ·5984-5988 · IF 9.48

Direct conversion of biomass derived L-rhamnose to 5-methylfurfural in water in high yield

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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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

Deglycosylation significantly affects the activity, stability and appropriate folding of recombinant Aspergillus niger α-L-rhamnosidase expressed in Pichia pastoris

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 .

CAS / MDL: 50-01-1
研究领域: 生物化学 · 分子生物学
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Catalysts · 2025 ·Vol. 15 ·期 5 ·465 · IF 4

Efficient Method for the Synthesis of 5-Methylfurfural from l-Rhamnose Using a Biphasic System

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 · 催化化学 · 绿色化学
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Environmental Pollutants and Bioavailability · 2022 · IF 2.828

Synchronously enhanced biofilm formation and m-dichlorobenzene removal in biotrickling filters by rhamnolipid chelating rare earth elements

Bairen Yang,Jiajie Wang,Qingqing Shang,Zhuqiu Sun,Yifan Wu

The effects of rhamnolipid chelating La (III) or Nd (III) on m-dichlorobenzene removal and biofilm growth were investigated. The rhamnolipid chelating La (III) or Nd (III) significantly increased the average m-dichlorobenzene elimination capacity by 24% and 29%, respectively, on day 70–130, and the average wet weights of biomass ranged from 11 kg/m3 to 15 kg/m3 in BTFs on day 100–180 at an inlet load of at 47–98 gm3/h and an EBRT of 60s-90s. Microbial community functional genes about biofilm growth and m-dichlorobenzene removal were also increased. In addition, the rhamnolipid chelating La (III) or Nd (III) can improve the membrane permeability, extracellular polymeric substance (EPS) production, catechol 2,3 dioxygenase (C23O) enzyme, and chlorobenzene dioxygenase activity. These results demonstrate that rhamnolipid chelating La (III) or Nd (III) have the potential to improve the performance of BTFs treating hydrophobic and highly toxic VOCs.

研究领域: 环境科学 · 微生物学
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PEDOSPHERE · 2022 · IF 5.514

Effects of rhamnolipids on bacterial communities in contaminated soil and earthworm guts

Bing XIA,Dan HUANG,Mao YE,Hao QIU,Hongfeng CHEN,Keqiang ZHAO,Rongliang QIU,Rongrong YING

Biosurfactant rhamnolipid and “soil ecosystem engineers” earthworms are often used to remediate contaminated soils. However, the effect of rhamnolipid on earthworm intestinal flora and microbial community in soil with earthworms is not understood. In our study, microcosm experiments were carried out to reveal the rhamnolipid on microbial abundance, composition, metabolism and contaminant degradation capacity. The results showed that both rhamnolipids and earthworms could have positive effects on soil bacteria. Bacteria in soil with rhamnosis have higher abundance and metabolic activity than in earthworm-only soils, while the improvement of rhamnolipid in bacterial composition and their contaminant degradation capacity were lower than earthworms. Notably, these changes were further amplified when rhamnolipids and earthworms coexisted. Specifically, the (log(copies/g) value increased from 9.50 (CK) to 10.25 (E), 10.50 (R) and 11.00 (RE). Comparing the soil with only earthworms (E), the relative abundance of dominant phyla Proteobacteria increased from 41.66% to 51.67% in the soil with both rhamnolipid and earthworms (RE), and more pollutant-degrading bacteria were also enriched in soil RE. Therefore, the increase in bacterial abundance and the enrichment of degrading bacteria lead that the removal rate of soil dioxins was earthworms + rhamnolipid (RE, 77.28%) > earthworms (E, 59.83%) > rhamnolipid (R, 24.65%) > control treatment (4.71%). Moreover, the addition of rhamnolipid enhanced the abundance of bacterial functional genes involved in “Metabolism” and “Environmental information processing”. In addition, the composition and diversity of bacteria in earthworms’ gut was conspicuously affected by rhamnolipid too, and the relative abundance of Microbacterium and Shewanella increased significantly (p<0.05). In conclusion, this study reveals that rhamnolipid will prominently influence the abundance, composition and metabolism of the microbial community in earthworms’ gut and soil, further promoting the degradation rate of dioxins. This study provides theoretical support for optimizing the combined application of rhamnolipid and earthworms in bioremediation engineering and the assessment of the ecological impacts of rhamnolipids.

研究领域: 环境科学 · 微生物学
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ACTA BIOCHIMICA ET BIOPHYSICA SINICA · 2025 ·Vol. 57 ·期 12 ·1983 · IF 3.4

Rhamnose alleviates the proinflammatory response during endotoxemia via the CEACAM1/LGALS9-p38 axis: Rhamnose alleviates the proinflammatory response

Rongjuan Wei,Tao Zhong,Ke Deng,Xianglong Zhang,Dongping Li,Meiling Chen,Ping Chang,Peng Wu,Zhanguo Liu

Gut microbiota plays an important role in orchestrating the host immune response. We previously reported that gut microbiota-derived rhamnose enhances the phagocytosis of macrophages, upon which we further asked whether rhamnose has modulatory effects on inflammation. Here, we show that, in an LPS-induced endotoxic mouse model, plasma rhamnose levels are increased. This bacteria-derived sugar alone does not impact inflammatory cytokine homeostasis or cause organ damage. In contrast, it is able to alleviate endotoxin-induced systemic inflammation and organ damage. Mechanistically, in macrophages in vitro , rhamnose binds to the V39, D40, and T101 sites of carcinoembryonic antigen-associated cell adhesion molecule 1 (CEACAM1), subsequently promoting the interaction between CEACAM1 and galectin 9 (LGALS9), which increases the protein level of dual-specificity protein phosphatase 1 (DUSP1). This inhibits p38 phosphorylation and thus attenuates the LPS-triggered expressions of proinflammatory factors. Collectively, our results suggest that rhamnose signals via the CEACAM1/LGALS9-p38 axis, which suppresses endotoxemia-associated inflammation, and that rhamnose is a candidate anti-inflammatory agent for the control of infection-induced organ damage.

CAS / MDL: 10030-85-0
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