APPLIED BIOCHEMISTRY AND MICROBIOLOGY
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2017
·Vol. 53
·期 1
·85-93
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IF 0.659
Fan N.,Du C. H.,Xu J. Q.,Xu Y. X.,Yu B. Y.,Zhang J.
The aim of the study was to expand the substrate scope of Gliocladium deliquescens NRRL 1086 and generate coumarin glycosides using 4-methylumbelliferone (4-MU) as a substrate. The obtained results indicated that 4-MU can be metabolized to its glucoside (M1) and sulfate conjugate (M2), and the structures of the metabolites were elucidated by spectroscopic or enzymatic methods. Time course experiments detected that nearly 90% of 4-MU could be metabolized within 24 h, and the maximum yield of M1 could reach as high as 32%. Further tests revealed that the glucose concentration in the medium had little effect on the yield of M1 but time of 4-MU-adding could markedly affect the glycosylation procedure, and the favorable time to accumulate M1 was in the 12 or 24 h-old stage II culture, while in the 36 h-old or even older stage II culture, the substrate was almost metabolized to M2. The attempts to alter the ratio between M1 and M2 were performed by addition of quercetin and S-tetrahydroberberrubine or reduction of the sulfate concentration in the culture medium. Herein we describe, to the best of our knowledge, the first example of simultaneously microbial glycosylation and sulfation of coumarins.
研究领域:
微生物学
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有机化学
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药理学
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DOI
高影响因子
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
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2013
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IF 2.823
Chen Hui Du,Jian Zhang,Shao Hua Xu,Xu Dong Wang,Jun Ping Kou,Bo Yang Yu
This study explored the substrate scope and regio-selectivity of Gliocladium deliquescens NRRL 1086 on hydroxylated benzophenones (HBPs), which was the follow-up investigation on the glycosylation of phenolic hydroxyl compounds by this unique microbe. Five HBPs substrates were used and three glycosylated metabolites, iriflophenone 2- O - β - d -glycopyranoside ( 6 , 40%), riflophenone 4- O - β - d -glycopyranoside( 7 , 21%) and 2,6,4′-trihydroxy-4-methoxybenzophenone-2- O - β - d -glycopyranoside ( 8 , 65%) were isolated and structurally identified unambiguously by ESI-MS, 1 H NMR, 13 C NMR, and 2D NMR spectroscopy. The versatile glycosylation ability of G. deliquescens NRRL 1086 on phenolic hydroxyl compounds may provide an alternative and convenient method to enable high-efficiency synthesis of various HBPs glycosides.
研究领域:
微生物学
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天然产物化学
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生物合成
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产品关联
DOI
高影响因子
CHEMISTRY & BIODIVERSITY
·
2021
·Vol. 18
·期 10
·e2100403
·
IF 2.408
Jie Yan,Wenxiu Guo,Lanyu Zhou,Dale Guo,Jin Pei,Yun Deng,Haoyuan Zheng,Ding Liu,Xiaofang Xie,Cheng Peng
Three previously undescribed chlorophenyl glycosides, (2,4,6-trichloro-3-hydroxy-5-methoxyphenyl)methyl β-D-glucopyranoside ( 1 ), (2,4-dichloro-3,5-dimethoxyphenyl)methyl 6- O -β-D-glucopyranosyl-β-D-glucopyranoside ( 2 ) and 4-chloro-3-methoxy-5-methylphenyl 6- O -(6-deoxy-β-L-mannopyranosyl)-β-D-glucopyranoside ( 3 ) were obtained from Lilium regale . The absolute configurations of these new finds were elucidated by comprehensive analyses of spectroscopic data combined with acid hydrolysis derivatization. (2,4-dichloro-3,5-dimethoxyphenyl)methyl 6- O -β-D-glucopyranosyl-β-D-glucopyranoside ( 2 ) can inhibit the proliferation of lung carcinoma A549 cells with an IC 50 value of 29 μΜ. Graphical
研究领域:
植物化学
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药理学
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天然产物研究
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产品关联
DOI
PubMed
高影响因子
ACS Sustainable Chemistry & Engineering
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2022
·
IF 9.224
Dawei Dong,Yafei Xiao,Minghua Zhang,Peixin Gong,Yingqing Ye,Shuhua Peng,Ke Wang,Minmin Fan
Polysaccharide is a kind of biological macromolecule with a complex structure, which plays an irreplaceable role in the organism. Due to the complex purification process of natural polysaccharide, chemical synthesis is an important means to obtain it. In this work, a green and efficient solid-phase polymerization method was used to synthesize glucan polysaccharide from unprotected glucose in one step under mild solid-phase conditions, using Hβ zeolites as acidic catalyst. The final polysaccharide product was characterized by high-performance liquid chromatography (HPLC) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) with a conversion of 35.0% and a maximum degree of polymerization of 26. More importantly, it was speculated that the glycosylation of unprotected glucose catalyzed by Hβ zeolites conforms to the Fischer glycosylation mechanism. In addition, the results of methylation analysis and one-dimensional, two-dimensional nuclear magnetic resonance (1D, 2D NMR) showed that the resulting polysaccharides were mainly linear, containing 10 different glycosidic linkages, and (1,6-Glcp), (1-Glcp), and (1,4-Glcp) were the most abundant linkage types among them.
研究领域:
有机化学
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生物化学
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DOI
高影响因子
JOURNAL OF MOLECULAR LIQUIDS
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2024
·
IF 5.3
Chuxin Qi,Lifang Chen,Zhiwen Qi
The heterogeneous liquid–liquid O-glycosidation is a crucial step in pharmaceutical synthesis. Herein, a theoretical methodology based on COSMO-RS, quantum chemical calculations combined with Transformer-CNN model was used to screen ionic liquids (ILs) as phase transfer catalysts (PTCs) to intensify O-glycosidation between 4-nitrophenol and 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide. The anions of ILs were screened by the evaluation of ILs hydrophilicity via infinite dilution selectivity of ILs and the molecular descriptor HB_acc3 of the anion using COSMO-RS, a predictive model for thermodynamic properties. Additionally, the binding energy between the phenoxide anion and IL cation was used to assess reaction extent in the aqueous phase through quantum chemical calculation. The cations of ILs were evaluated by the infinite dilution selectivity of the combination between phenoxide anion and IL cations, and physical properties including viscosity and melting point were also predicted using an advanced Transformer-CNN model. The screened IL 1-octyl-3-methylimidazolium acetate and 1-hexyl-3-methylimidazolium acetate were demonstrated its superior catalytic activity for the aromatic O-glycosidation of not only 4-nitrophenol, but also various phenols and thiophenols. Moreover, the presence of PTCs enhances the likelihood of the reactant migrating into another phase. This behavior is validated by COSMO-RS calculated liquid–liquid equilibrium (LLE) and interaction energy analysis. The method provides great potential for screening and designing ILs as phase transfer catalysts for heterogeneous liquid–liquid reactions.
研究领域:
有机化学
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药物合成
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计算化学
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产品关联
DOI
高影响因子
Horticultural Plant Journal
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2023
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IF 5.7
Xiangmei Cao,Dan Jiang,Hanqing Wang,Boping Wu,Jianhui Cheng,Bo Zhang
Glycosylated volatiles are considered as hidden aroma precursors that affect fruit flavor and are involved in plant defense response. Several uridine-diphosphate (UDP)-glycosyltransferase (UGT) members related to the glycosylation of volatiles have been identified from grapevine berries. Although grapevine leaves produced much higher levels of glycosylated volatiles than berries, UGTs responsible for the production of glycosylated volatiles in leaves have not yet been identified. Here, eight novel UGT genes were cloned, among these four members that belong to UGT85A family (named UGT85A24, UGT85A25, UGT85A26, and UGT85A27) were localized in the cytoplasm and their recombinant proteins showed activity toward volatiles detected in grapevine, with geraniol as the preferred substrate in vitro . Two UGT genes with 98.1% homology differ in R/S -linalool selection. The UGT85A26-catalyzed substrate showed enrichment in S -linalool, whereas UGT85A27 showed a strong preference for R -linalool. UGT85A24 and UGT85A25 were expressed mainly in berries, and UGT85A26 and UGT85A27 were expressed predominantly in grapevine mature leaves and correlated with the highest content of glycosylated volatiles in the mature leaves. Methyl jasmonate (MeJA) induced the expression of UGT85A26 and UGT85A27 as well as the production of linalyl-β-glucoside, citronellyl-β-glucoside and phenethyl-β-glucoside. Transient overexpression of UGT85A26 and UGT85A27 in tobacco leaves led to the accumulation of linalyl-β-glucoside and an increase in citronellyl-β-glucoside in vivo . These results indicate that the expression of UGT85A26 and UGT85A27 is a major regulator affecting the content of glycosylated volatiles in grapevine.
研究领域:
植物学
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分子生物学
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DOI
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
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2019
·
IF 3.714
Meihui Fan,Huafang Ding,Guowen Zhang,Xing Hu,Deming Gong
Flavonoids possess the inhibition ability against tyrosinase. Here, the effects of flavonoids structure on inhibitory activity and binding affinity of tyrosinase were investigated. The results showed that the hydroxy groups of 5C−OH, 4′C−OH and 5′C−OH of flavonoids were in favor of forming hydrogen bond with the amino acid residues of tyrosinase, which played a crucial role in the binding and interaction between flavonoids and tyrosinase. Different groups of flavonoids exhibited different influences on tyrosinase inhibitory activity and binding affinity. The hydroxylation at C3′ position of flavonoids increased affinities for tyrosinase, whereas the inhibitory activities went downward and upward for flavone and flavonol, respectively. The hydrogenation of the C2 = C3 double bond of flavones weakened inhibitory activities and strengthened affinities, which increased affinities of flavonols with downward and upward inhibitions. The decreased inhibitory activities and affinities can be realized by the hydroxylation of the C4′ and C5′ of flavonoids. Methylation of flavonoids decreased the inhibition while methoxylation of 5′C increased affinity and methylation of 4’−OH led to an increase in affinity. Glycosylation mainly induced the decline in both inhibitory activities and affinities of flavonoids. These findings may provide useful information for the structural modification of flavonoids as effective tyrosinase inhibitors.
研究领域:
生物化学
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药理学
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产品关联
DOI
高影响因子
DRUG METABOLISM AND DISPOSITION
·
2018
·
IF 3.64
Danyi Lu,Dong Dong,Qian Xie,Zhijie Li,Baojian Wu
UDP-glucuronosyltransferases (UGTs) play an important role in metabolism and detoxification of amine-containing chemicals. However, the disposition mechanisms for amines via UGT metabolism are not fully clear. Here we aim to investigate a potential role of UGT2B10 in N-glucosidation, and to determine the transporters for excretion of N-glucosides. We first established a HEK293 cell line stably overexpressing UGT2B10. Incubation of mianserin or cyclizine with the cells generated one N-glucuronide and one N-glucoside. Chemical inhibition (using specific chemical inhibitor Ko143) and biological inhibition (using specific shRNA) of BCRP resulted in a significant reduction in efflux of N-glucuronide. Similar results were observed when MRP4 was inhibited. Furthermore, inhibition of BCRP led to increased intracellular N-glucoside, whereas inhibition of MRP4 caused no changes in disposition of N-glucosides. The data overall indicated that BCRP not MRP4 was responsible for excretion of N-glucosides, whereas both BCRP and MRP4 contributed to excretion of N-glucuronides. Interestingly, down-regulation of N-glucuronidation led to increased N-glucosidation in the cells, supporting the glucosidation as a potential complementary pathway for conventional glucuronidation. In conclusion, UGT2B10 was for the first time identified as a N-glucosidation enzyme. Generated N-glucosides were excreted primarily by the BCRP transporter.
研究领域:
药理学
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生物化学
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分子生物学
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DOI
PubMed
高影响因子
JOURNAL OF CHROMATOGRAPHY A
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2022
·
IF 4.601
Tao Chen,Qi Wang,Qiqi Wang,Mencuo La,Yulin Li,Liangliang He,Denglang Zou
In this study, a strategy based on COSMO-RS (Conductor-like Screening Model for Real Solvents) with a constrained optimization calculation was developed for ab initio calculation based solvent system selection in silico for counter-current chromatography. The separation of resibufogenin glycosylation products was selected as an example to show its practicability. The selected solvent system in silico gave the K values consistent with the experimentally measured data (RMSD=0.2861) and the glycosylation products, namely Resibufogenin-3-O- β -D-glucoside ( R-G ) and Resibufogenin-3-O- β -D-glucosyl (1→2)- β -D-glucoside ( R-2G ), were successfully separated by HSCCC.
研究领域:
分析化学
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计算化学
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药学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Current Research in Food Science
·
2023
·
IF 6.3
Shiye Lin,Jesus Simal-Gandara,Hui Cao,Jianbo Xiao
Polyhydroxy flavonols readily degraded during thermal processing. In this study, the UPLC-Q-tof-MS/MS was applied to explore the stability of dietary polyhydroxy flavonols, myricetin, kaempferol, galangin, fisetin, myricitrin, quercitrin and rutin, in boiling water. The decomposition of flavonols was mainly caused by the heterocyclic ring C opening to form simpler aromatic compounds. The degradation products mainly included 1,3,5-benzenetriol, 3,4,5-trihydroxybenzoic acid, 2,4,6-trihydroxybenzoic acid and 2,4,6-trihydroxybenzaldehyde, etc. Compared with myricetin with a pyrogallol-type structure on the ring B, the glycoside in myricitrin slightly affects the stability. However, the glycosides in rutin and quercitrin dramatically improved the stability in water. During the boiling process, flavonols underwent a series of chemical reactions, such as hydroxylation, dehydroxylation, deglycosidation, deprotonation, and C-ring cleavage.
研究领域:
食品科学
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分析化学
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植物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF FOOD COMPOSITION AND ANALYSIS
·
2022
·
IF 4.52
Shi Shen,Xi Chen,Qin Zhuo,Yan Ma,Jingbo Wang,Liyuan Wang,Zhaolong Gong,Junsheng Huo
To investigate the differences among kiwifruits from six different cultivars ( Actinidia chinensis , Actinidia delicosa and Actinidia arguta ), UPLC-QTOF-MS and UPLC-ESI-MS/MS coupled to multivariate statistical analysis were applied to untargeted metabolites and targeted analysis of kiwifruit samples for the first time. In untargeted analysis, the metabolome of kiwifruits was exhibited by principal component analysis (PCA), a total of 44 up-regulated feature compounds were screened based on the orthogonal partial least squares-discriminant analysis (OPLS-DA) and identified as glycosyl compounds , hydrocinnamic acids and various flavonoids . Furthermore, the contents of 27 targeted procyanidins , flavonoids and hydrocinnamic acids were analyzed by a UPLC-ESI-MS/MS method. It was indicated that phenol glycosides were much higher in A. arguta , responsible for the aroma of kiwifruits, various quercetin glycosides were higher in A. arguta , and much higher flavan-3-ols and hydrocinnamic acids were rich in A. Chinensis cv. Hongyang (red) kiwifruits. In addition, the results of chemometric analysis showed the untargeted metabolites and targeted compounds were responsible for the classification on the kiwifruits, which can benefit the scientific understanding of chemical diversity for kiwifruits, and improve the investigation of new wild kiwifruit cultivars, especially red kiwifruit and A. arguta .
研究领域:
植物科学
·
分析化学
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食品科学
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DOI
高影响因子
危险品化学品经营许可证（带存储）