Microorganisms
·
2021
·Vol. 9
·期 7
·1511
·
IF 4.128
Jia Yin,Yujie Song,Yaozhong Hu,Yuanyifei Wang,Bowei Zhang,Jin Wang,Xuemeng Ji,Shuo Wang
Akkermansia muciniphila, a potential probiotic, has been proven to lessen the effects of several diseases. As established, the relative abundance ofAkkermansiais positively correlated with tryptophan metabolism. However, the reciprocal interaction between tryptophan andAkkemansiais still unclear. Herein, for the first time, the possible effects of tryptophan and its derived metabolites onA. muciniphilawere preliminarily investigated, including growth, physiological function, and metabolism. Obtained results suggested that 0.4 g/L of tryptophan treatment could significantly promote the growth ofA. muciniphila. Notably, when grown in BHI with 0.8 g/L of tryptophan, the hydrophobicity and adhesion ofA. muciniphilawere significantly improved, potentially due to the increase in the rate of cell division. Furthermore,A. muciniphilametabolized tryptophan to indole, indole-3-acetic acid, indole-3-carboxaldehyde, and indole-3-lactic acid. Indoles produced by gut microbiota could significantly promote the growth ofA. muciniphila. These results could provide a valuable reference for future research on the relationship between tryptophan metabolism andA. muciniphila.Keywords:Akkermansia;tryptophan metabolites;indole;indole derivates
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JOURNAL OF CHROMATOGRAPHY A
·
2021
·
IF 4.759
Shaoping Ma,Fenfang Li,Zhijian Tan
The hydrophobic organic solvents/water biphasic system had been always used in the traditional enantioselective liquid-liquid extraction (ELLE). In recent years, aqueous biphasic systems (ABSs) are considered as a promising method used in the ELLE. In the present work, a recyclable ABS composed of a temperature-responsive polymer poly(MAH- β -CD- co -NIPAAm) (P N-CD ) and a pH-responsive polymer poly(AA-DMAEMA-BMA) (P ADB ) was employed in the enantioseparation of tryptophan enantiomers . The polymer P N-CD acted as not only the phase-forming component but also the chiral selector, which can be recycled by changing the temperature. The polymer P ADB can be used as the phase-forming component, which can also be recycled by adjusting the pH. The phase behaviors of this P N-CD /P ADB ABS had been studied. The influencing parameters were studied for this chiral separation process, including the polymer concentration, initial tryptophan concentration, extraction temperature, and system pH. The maximum separation factor ( α ) of 1.42 was obtained by one-step extraction under the optimal conditions. Meanwhile, the distribution coefficients of L -tryptophan ( L -Trp) and D -tryptophan ( D -Trp) were 2.79 and 1.96, respectively. This study develops a green and sustainable strategy for enantioseparation by using the ELLE.
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ACS Applied Bio Materials
·
2018
·
IF 0
Xiao-Rong Yang,Xiao-Dong Song,Han-Yan Zhu,Chang-Jing Cheng,Hai-Rong Yu,Huai-Hao Zhang
Multifunctional graphene oxide nanocomposites simultaneously possessing high enantioselectivity, excellent thermosensitivity, and magnetism demonstrate great application potentials in direct enantioseparation. We herein report one novel smart graphene oxide nanocomposite (MGO@PNG-CD) with high enantioselectivity, excellent thermosensitivity, and magnetism for highly efficient chiral identification and enantioseparation of tryptophan enantiomers. The MGO@PNG-CD is composed of graphene oxide nanosheets with immobilized superparamagnetic Fe3O4 nanoparticles and grafted PNG-CD smart polymer brushes. The PNG-CD is made up of poly(N-isopropylacrylamide-co-glycidyl methacrylate) (PNG) chains with numerous appended β-cyclodextrin (β-CD) units, which play a significant role in effective chiral discrimination and resolution of DL-tryptophan (DL-Trp). The β-CD units serve as chiral selectors capable of selectively recognizing and binding L-tryptophan (L-Trp) into their cavities to form stable host–guest inclusion complexes of β-CD/L-Trp. The PNIPAM chains in PNG act as a microenvironmental adjustor for the inclusion constants of β-CD/L-Trp complexes. The resulted MGO@PNG-CD demonstrates high thermosensitive enantioselectivity toward L-Trp over D-Trp based on the chiral discrimination ability of β-CD toward L-Trp and the thermosensitive volume phase transition of PNIPAM chains. Operating temperature and initial concentrations of DL-Trp are two significant factors affecting the separation efficiency of DL-Trp enantiomers. Moreover, the MGO@PNG-CD also displays satisfactory recycling and convenient magnetic separability from enantiomeric solution. Such a multifunctional graphene oxide nanocomposite developed in this study can serve as a high-performance nanoselector for highly efficient chiral recognition and enantioseparation of various chiral compounds.
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CHINESE JOURNAL OF CHEMICAL ENGINEERING
·
2017
·
IF 1.174
Qici Wu,Qilei Zhang,Shiwen Xu,Chengtong Ge,Shanjing Yao,Dongqiang Lin
Five tryptophan analogues with a hydrophobic indole ring and an amino group on each molecule were used as functional ligands of mixed-mode resins for human serum albumin (HSA) purification. Their adsorption performance was evaluated and the effects of pH and salt addition on HSA adsorption were studied. The resins prepared showed typical pH-dependent adsorption and the highest adsorption capacity and affinity were found at pH 5.0 for all the resins tested. The saturated adsorption capacity was 138.02 mg·g − 1 with the tryptamine-functionalized resin, which significantly decreased at pH below 4.0 due to electrostatic repulsion between ligands and HSA. Moreover, the addition of NaCl or (NH 4 ) 2 SO 4 in media reduced HSA adsorption capacity, although the two salts showed different affecting profiles. The tryptamine-functionalized resin showed the best salt-tolerant performance, and its high adsorption capacity was maintained under high salt concentrations. In addition, the five resins prepared showed good adsorption selectivity for recombinant HSA from Pichia pastoris broth. Molecular docking results between tryptamine and HSA indicated that tryptamine was favorable to bind on Site II (indole-binding site) of HSA.
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
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2017
·
IF 2.536
Yusheng Yuan,Liu Yang,Shaopu Liu,Jidong Yang,Hui Zhang,Jingjing Yan,Xiaoli Hu
A sensitive fluorescence sensor for warfarin was proposed via quenching the fluorescence of l -tryptophan due to the interaction between warfarin and l -tryptophan. Warfarin, as one of the most effective anticoagulants , was designed and synthesized via lipase from porcine pancreas (PPL) as a biocatalyst to catalyze the Michael addition of 4-hydroxycoumarin to α, β-unsaturated enones in organic medium in the presence of water. Furthermore, the spectrofluorometry was used to detect the concentration of warfarin with a linear range and detection limit (3σ/k) of 0.04–12.0 μmol L − 1 (R 2 = 0.994) and 0.01 μmol L − 1 , respectively. Herein, this was the first application of bio-catalytic synthesis and fluorescence for the determination of warfarin. The proposed method was applied to determine warfarin of the drug in tablets with satisfactory results.
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iScience
·
2024
·
IF 4.6
Junyang Li,Bingjie Mei,Lu Feng,Xiaoxin Wang,Dengfeng Wang,Jianming Huang,Guonan Zhang
Reprogramming tryptophan metabolism (TRP) may be able to overcome immunosuppression and restore the immune checkpoint blockade (ICB) response in epithelial ovarian cancer (EOC) patients resistant to ICB therapy. Because TRP metabolism is involved in the kynurenine/indole and serotonin pathways of tryptophan metabolism. Herein, employing amitriptyline (AMI), an antagonist of TLR4 and serotonin transporter (SERT), we revealed that AMI remodels the immunological landscape of EOC. In particular, AMI lowered the expression of IDO1, IL-4I1 and PD-L1, the quantity of KYN and indoles, and the level of immunosuppressive immune cells MDSC, Tregs and CD8+CD39+/PD-1+ T cell. AMI boosted the killing potential of anti-PD-1-directed CD8+T cells and worked in concert with PD-1 inhibitor to suppress tumor growth and to prolong the survival of EOC-bearing mice. This work highlights AMI as an effective regulator of ICB response by manipulating EOC cell TRP metabolism, indicating it could be a potential strategy for improving EOC ICB therapy.
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FOOD CHEMISTRY
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2024
·
IF 8.5
Li Zhang,Chao Li,Yue Chen,Shaobin Li,Xue Wang,Fengbo Li
L-tryptophan (L-Trp) is crucial for human metabolism, and its imbalance or deficiency can lead to certain diseases, such as insomnia, depression, and heart disease. Since the body cannot synthesize L-Trp and must obtain it from external sources, accurately monitoring L-Trp levels in food is essential. Herein, a nanocomposite film based on polyoxometalate (P 2 Mo 17 V), Ti 3 C 2 T x MXene , and chitosan (Cs) was developed through a green electrostatically mediated layer-by-layer self-assembly strategy for electrochemical detection of L-Trp. The composite film exhibits fast electron transfer and remarkable electrocatalytic performance for L-Trp with a wide linear range (0.1–103 μM), low limit of detection (0.08 μM, S/N = 3), good selectivity, reproducibility, and repeatability. In milk sample, the recoveries of L-Trp were from 95.78% and 104.31%. The P 2 Mo 17 V/Cs-Ti 3 C 2 T x electrochemical sensor not only provides exceptional recognition and detection capabilities for L-Trp but also shows significant potential for practical applications, particularly in food safety and quality control .
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BIOORGANIC CHEMISTRY
·
2024
·
IF 4.5
Yi Chen,Shasha Song,Yongfang Wang,Lili Wu,Jianbing Wu,Zhengmeng Jiang,Xinyu Li
Psoriasis (PSO) is a common inflammatory skin disease caused by multiple factors. Magnolia officinalis is an important medicinal plant in China, with various values such as ecology, medicine, food, and daily chemicals. However, its diverse application potential has not been fully explored. Magnolol (MGO) is the main active compound of Magnolia officinalis with significant anti-inflammatory effect. To investigate the application potential of MGO in inflammatory skin disease, the effects and underlying mechanisms of topical MGO treating psoriasis were explored in this study. Network pharmacology and molecular docking firstly predicted that topical MGO may treat psoriasis by regulating pyroptosis pathway and acting on caspase-1 (CASP1). In vitro experiments then demonstrated that MGO could inhibit the level of inflammatory cytokines and the key protein expression of NOD-like receptor protein 3 (NLRP3)/Caspase-1 pathway in lipopolysaccharide (LPS)-stimulated phorbol 12-myristate 13-acetate (PMA)-differentiated THP-1 cells. Meanwhile, MGO could inhibit CuSO 4 -induced neutrophils migration in Tg (mpx:EGFP) zebrafish by suppressing inflammation and pyroptosis. This study further indicated that topical application of MGO ameliorated imiquimod (IMQ)-induced psoriasis-like dermatitis by reducing the release of inflammatory factors and decreasing the key protein expression of pyroptosis-related NLRP3/Caspase-1 pathway. Metabolomics analysis revealed that topical application of MGO could significantly regulate tryptophan metabolism and affect the level of tryptophan in skin lesions. Tryptophan could also regulate inflammation-related genes and inhibit pyroptosis-related NLRP3/Caspase-1 pathway in LPS-stimulated PMA-differentiated THP-1 cells. In conclusion, this study suggested that topical MGO may ameliorate psoriasis-like dermatitis by inhibiting NLRP3/Caspase-1 pathway and regulating tryptophan metabolism.
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Qianxu Wang,Jiarui Liang,Qianhui Zou,Wenxiu Wang,Guiming Yan,Rui Guo,Tian Yuan,Yutang Wang,Xuebo Liu,Zhigang Liu
The balance of gut microbiota affects uric acid synthesis and excretion, influencing the development of hyperuricemia. This study aimed to investigate the effects and mechanisms of probiotics on hyperuricemia and adenine- and potassium oxonate-induced colonic damage. After two months of gavage at 109 CFU/day, the probiotic strains Lactobacillus rhamnosus UA260 and Lactobacillus plantarum YU28, identified through in vitro screening, significantly reduced serum uric acid levels in hyperuricemia mice from 109.71 ± 56.33 to 38.76 ± 15.06 and 33.22 ± 6.91 μmol/L, respectively. These strains attenuated inflammatory, repaired gut barrier damage, and enhanced colonic uric acid transporter function, thereby promoting uric acid excretion. Furthermore, the probiotics significantly reshaped gut microbiota by increasing the abundance of beneficial bacteria, including Lactobacillus and Coprococcus, while modulating tryptophan, purine, and riboflavin metabolism. Changes in tryptophan metabolites, specifically indole-3-propionic acid and indole-3-acetic acid, were correlated with xanthine oxidase activity, colonic injury, and the expression of the uric acid transporter protein ABCG2 during treatment. Probiotics intervention activated aryl hydrocarbon receptor pathways. These findings suggest that probiotics alleviate hyperuricemia and colonic inflammatory by regulating gut microbiota composition and tryptophan microbial metabolite pathways. Probiotics that modulate tryptophan microbial metabolism may provide a potential strategy for treating or preventing hyperuricemia.
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CELL
·
2025
·
IF 42.5
Jun Lin,Qixing Nie,Jie Cheng,Ya-Ni Zhong,Tianyao Zhang,Xiuying Zhang,Xiaoyan Ge,Yong Ding,Canyang Niu,Yuhua Gao,Kai Wang,Mingxin Gao,Xuemei Wang,Weixuan Chen,Chuyu Yun,Chuan Ye,Jinkun Xu,Weike Shaoyong,Lijun Zhang,Pan Shang,Xi Luo,Zhiwei Zhang,Xin Zheng,Xueying Sha,Jinxin Zhang,Shaoping Nie,Xuguang Zhang,Fazheng Ren,Huiying Liu,Erdan Dong,Xiao Yu,Linong Ji,Yanli Pang,Jin-Peng Sun,Changtao Jiang
Recently, microbial amino-acid-conjugated bile acids (MABAs) have been found to be prevalent in human samples. However, their physiological significance is still unclear. Here, we identify tryptophan-conjugated cholic acid (Trp-CA) as the most significantly decreased MABA in patients with type 2 diabetes (T2D), and its abundance is negatively correlated with clinical glycemic markers. We further demonstrate that Trp-CA improves glucose tolerance in diabetic mice. Mechanistically, we find that Trp-CA is a ligand of the orphan G protein-coupled receptor (GPCR) Mas-related G protein-coupled receptor family member E (MRGPRE) and determine the binding mode between the two. Both MRGPRE-Gs-cyclic AMP (cAMP) and MRGPRE-β-arrestin-1-aldolase A (ALDOA) signaling pathways contribute to the metabolic benefits of Trp-CA. Additionally, we find that the bacterial bile salt hydrolase/transferase of Bifidobacterium is responsible for the production of Trp-CA. Together, our findings pave the way for further research on MABAs and offer additional therapeutic targets for the treatment of T2D.
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BIOLOGICAL & PHARMACEUTICAL BULLETIN
·
2018
·Vol. 41
·期 8
·1243-1250
·
IF 1.694
Yunpeng Qi,Renping Wang,Liang Zhao,Lei Lv,Fan Zhou,Tian Zhang,Feng Lu,Hongli Yan,Gengli Duan
Celastrol is well known for its anti-cancer effects, yet its specific mechanisms against colon cancer are still not fully elucidated. In this study, cytotoxic effect of celastrol against HCT116 colon cancer cells was investigated based on cell viability assay and flow cytometry assay, and the possible mechanism was explored using a strategy combining metabolic profiling and targeted metabolite analysis based on ultra performance liquid chromatography (UPLC)/MS. Celastrol was found to inhibit the growth of colon cancer cells and induce apoptosis. Metabolomics analysis revealed characteristic changes in metabolic profiles of the colon cancer cells, revealing altered levels of amino acids, carnitine, and lipid markers. Most interestingly, with the assistance of targeted metabolite analysis, tryptophan (Trp) level was significantly increased whereas kynurenine (Kyn) level was decreased in colon cancer cells after celastrol treatment, together with markedly declined Kyn/Trp ratios. Western blot analysis revealed that expression of indoleamine 2,3-dioxygenase (IDO), the enzyme catalyzing Trp to generate Kyn, was dramatically inhibited in colon cancer cells after celastrol treatment, with a dose-dependent manner. These results suggest that suppression of IDO expression and tryptophan catabolism may be part of the mechanisms of celastrol in its cytotoxic effect against HCT116 colon cancer cells. This study provided scientific basis for further development of celastrol on treating colon cancer.
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ARCHIV DER PHARMAZIE
·
2024
·
IF 4.3
Xianghao Zeng,Shaobing Cheng,Huilan Li,Haiyang Yu,Yushun Cui,Yuanying Fang,Shilin Yang,Yulin Feng
Alzheimer's disease (AD) is a multifactorial neurological disease, and the multitarget directed ligand (MTDL) strategy may be an effective approach to delay its progression. Based on this strategy, 27 derivatives of l -tryptophan, 3a-1–3d-1 , were designed, synthesized, and evaluated for their biological activity. Among them, IC 50 (inhibitor concentration resulting in 50% inhibitory activity) values of compounds 3a-18 and 3b-1 were 0.58 and 0.44 μM for human serum butyrylcholinesterase ( h BuChE), respectively, and both of them exhibited more than 30-fold selectivity for human serum acetylcholinesterase. Enzyme kinetics studies showed that these two compounds were mixed inhibitors of h BuChE. In addition, these two derivatives possessed extraordinary antioxidant activity in OH radical scavenging and oxygen radical absorption capacity fluorescein assays. Meanwhile, these compounds could also prevent β-amyloid (Aβ) self-aggregation and possessed low toxicity on PC12 and AML12 cells. Molecular modeling studies revealed that these two compounds could interact with the choline binding site, acetyl binding site, and peripheral anionic site to exert submicromolar BuChE inhibitory activity. In the vitro blood–brain barrier permeation assay, compounds 3a-18 and 3b-1 showed enough blood–brain barrier permeability. In drug-likeness prediction, compounds 3a-18 and 3b-1 showed good gastrointestinal absorption and a low risk of human ether-a-go-go-related gene toxicity. Therefore, compounds 3a-18 and 3b-1 are potential multitarget anti-AD lead compounds, which could work as powerful antioxidants with submicromolar selective inhibitory activity for h BuChE as well as prevent Aβ self-aggregation.
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