7,642 results on '"Glucoside"'
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2. 饲料中单宁、硫代葡萄糖苷和植酸 对畜禽的影响及其降解方法.
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赵一鸣, 徐 文, 安容容, 王 淼, 李沁泽, and 张颖超
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Plants always produce anti-nutritional factors to resist external hurt, and contains different anti-nutritional factors in a variety of plants. Low concentration of anti-nutritional factors is beneficial for animals, while high content of anti-nutritional factor will hinder the digestion, absorption, and utilization of nutrients, and inhibit the growth of animal. Therefore, in order to provide reference for forage utilization, this review summarized the content, elimination methods and threshold of tannin, glucoside and phytic acid in different animals. [ABSTRACT FROM AUTHOR]
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- 2024
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3. Macromolecules: Synthesis, antimicrobial, POM analysis and computational approaches of some glucoside derivatives bearing acyl moieties
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Mohammad R. Kayes, Supriyo Saha, Mohammed M. Alanazi, Yasuhiro Ozeki, Dilipkumar Pal, Taibi B. Hadda, Abdelkhaleq Legssyer, and Sarkar M.A. Kawsar
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Glucoside ,Antimicrobial ,Antiproliferative ,Molecular docking/dynamics ,Computational approaches, POM ,Therapeutics. Pharmacology ,RM1-950 - Abstract
Macromolecules i.e., carbohydrate derivatives are crucial to biochemical and medical research. Herein, we designed and synthesized eight methyl α-D-glucopyranoside (MGP) derivatives (2–8) in good yields following the regioselective direct acylation method. The structural configurations of the synthesized MGP derivatives were analyzed and verified using multiple physicochemical and spectroscopic techniques. Antimicrobial experiments revealed that almost all derivatives demonstrated noticeable antifungal and antibacterial efficacy. The synthesized derivatives showed minimum inhibitory concentration (MIC) values ranging from 0.75 µg/mL to 1.50 µg/mL and minimum bactericidal concentrations (MBCs) ranging from 8.00 µg/mL to 16.00 µg/mL. Compound 6 inhibited Ehrlich ascites carcinoma (EAC) cell proliferation by 10.36% with an IC50 of 2602.23 μg/mL in the MTT colorimetric assay. The obtained results were further rationalized by docking analysis of the synthesized derivatives against 4URO and 4XE3 receptors to explore the binding affinities and nonbonding interactions of MGP derivatives with target proteins. Compound 6 demonstrated the potential to bind with the target with the highest binding energy. In a stimulating environment, a molecular dynamics study showed that MGP derivatives have a stable conformation and binding pattern. The MGP derivatives were examined using POM (Petra/Osiris/Molinspiration) bioinformatics, and as a result, these derivatives showed good toxicity, bioavailability, and pharmacokinetics. Various antifungal/antiviral pharmacophore (Oδ−, O′δ−) sites were identified by using POM investigations, and compound 6 was further tested against other pathogenic fungi and viruses, such as Micron and Delta mutants of SARS-CoV-2.
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- 2023
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4. Temperature–air velocity association, experimental and modeling study of stevia leaves solar drying.
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Castillo-Téllez, Beatriz, Téllez, Margarita Castillo, López-Vidaña, Erick César, Domínguez Niño, Alfredo, Mejía-Pérez, Gerardo A, and Vega-Gómez, Carlos Jesahel
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Sugar is a natural high-calorie sweetener. Its excessive consumption is associated with health problems such as obesity, diabetes, heart disease, and degenerative issues. The stevia plant is a great natural substitute. It provides no calories and has medicinal properties such as oral antibacterial, hypoglycemic, and anti-hypertensive with a high nutritional value. In this work, the effects of temperature and air velocity in drying kinetics of stevia leaves were studied using a convective drier operating with air velocities (2, 3, and 4 m/s) and temperatures controlled (45 °C, 55 °C, and 65 °C). The highest drying rate was obtained at 65 °C and 4 m/s air velocity at 0.05 kg water/kg dry matter min. The experimental data were fitted to theoretical drying models to determine the best approach. It is found that the Page model gives a good fit for all experiments, with correlation coefficients (R
2 ) > 0.9994. The equations to correlate this model's variables with air and temperature were determined. The results show that Δ E and glucoside values increase when temperature and air velocity increase. [ABSTRACT FROM AUTHOR]- Published
- 2023
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5. Co‐reactivity of glucosides: Retrospective analysis of North American Contact Dermatitis Group Data 2019–2020.
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Warshaw, Erin M., Xiong, Michelle, DeKoven, Joel G., Taylor, James S., Belsito, Donald V., Reeder, Margo J., Adler, Brandon L., Pratt, Melanie D., Atwater, Amber R., Maibach, Howard I., Silverberg, Jonathan I., Yu, JiaDe, Botto, Nina, Fowler, Joseph F., Houle, Marie‐Claude, Mowad, Christen M., Dunnick, Cory A., and DeLeo, Vincent A.
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GLUCOSIDES , *CONTACT dermatitis , *RETROSPECTIVE studies , *ALLERGIC rhinitis - Abstract
Keywords: allergic contact dermatitis; cetearyl glucoside; coco glucoside; contact allergy; co-reactivity; decyl glucoside; glucoside; lauryl glucoside; patch testing EN allergic contact dermatitis cetearyl glucoside coco glucoside contact allergy co-reactivity decyl glucoside glucoside lauryl glucoside patch testing 153 156 4 01/13/23 20230201 NES 230201 INTRODUCTION Alkyl glucosides are surfactants used in a variety of personal and household products.[1] Screening patch test series may not include glucosides and studies on co-reactivity are limited. Odds of atopic dermatitis history was significantly higher in glucoside-positive patients compared to glucoside-negative patients (39.1% vs. 31.6%, I p i = 0.0043). Allergic contact dermatitis, coco glucoside, contact allergy, co-reactivity, cetearyl glucoside, glucoside, lauryl glucoside, decyl glucoside, patch testing. [Extracted from the article]
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- 2023
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6. Bioactive Alpha-Pyrone and Phenolic Glucosides from the Marine-Derived Metarhizium sp. P2100.
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Ma, Zhong-Lian, Yu, Zhi-Pu, Zheng, Yao-Yao, Han, Na, Zhang, Ya-Hui, Song, Shu-Yue, Mao, Jun-Qiu, Li, Jiao-Jiao, Yao, Guang-Shan, and Wang, Chang-Yun
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METARHIZIUM , *PYRANOSIDE , *CIRCULAR dichroism , *ANTI-inflammatory agents , *NEOLIGNANS , *GLYCOSIDES - Abstract
Glycoside compounds have attracted great interest due to their remarkable and multifarious bioactivities. In this study, four hitherto unknown 4-methoxy-β-D-glucosyl derivatives were obtained and identified from the marine-derived fungus Metarhizium sp. P2100, including three alpha-pyrone glycosides (1–3) and one phenolic glycoside (4). Their planar structures were elucidated by comprehensive spectroscopic analysis, including 1D/2D NMR and HRESIMS. The absolute configurations of 1–3 were determined by a single-crystal X-ray crystallographic experiment, a comparison of the experimental, and a calculated electronic circular dichroism (ECD) spectra, respectively. Compounds 2 and 3 are a pair of rare epimeric pyranoside glycosides at C-7 with a core of aglycone as 2H-pyrone. Compounds 1–4 exhibited weak anti-inflammatory activities. In particular, compounds 1–3 displayed inhibitory activities against α-amylase, showing a potential for the development of a new α-amylase inhibitor for controlling diabetes. [ABSTRACT FROM AUTHOR]
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- 2023
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7. Patch testing with glucosides: The North American Contact Dermatitis Group experience, 2009-2018.
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Warshaw, Erin M., Xiong, Michelle, Atwater, Amber R., DeKoven, Joel G., Pratt, Melanie D., Maibach, Howard I., Taylor, James S., Belsito, Donald V., Silverberg, Jonathan I., Reeder, Margo J., Zug, Kathryn A., Sasseville, Denis, Fowler, Joseph F., DeLeo, Vincent A., Houle, Marie-Claude, Dunnick, Cory A., and Fowler, Joseph F Jr
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Background: Alkyl glucosides are nonionic surfactants that are increasingly used in personal care products.Objective: To characterize positive patch test reactions to decyl glucoside (5% petrolatum, tested 2009-2018) and lauryl glucoside (3% petrolatum, tested 2017-2018).Methods: Retrospective analysis of patients tested by the North American Contact Dermatitis Group.Results: Of 24,097 patients patch tested to decyl and/or lauryl glucoside, 470 (2.0%) had positive reactions. Compared with glucoside-negative patients, glucoside-positive patients had higher odds of occupational skin disease (13.4% vs 10.1%; P = .0207), history of hay fever (38.5% vs 31.6%; P = .0014), atopic dermatitis (39.0% vs 28.6%; P < .0001), and/or asthma (21.8% vs 16.5%; P = .0023). Most glucoside reactions (83.9%) were currently relevant. The most common source was personal care products (63.0%), especially hair products (16.5%) and skin cleansers (15.2%). Of 4933 patients tested to decyl and lauryl glucoside, 134 (2.7%) were positive to 1 or both; 43.4% (43 of 99) of decyl-positive patients were also positive to lauryl glucoside and 55.1% (43/78) of lauryl glucoside patients were also positive to decyl glucoside.Limitations: The cohort predominantly reflects a referral population, and follow-up after testing was not captured.Conclusion: Glucoside positivity occurred in 2.0% of the tested patients. Reactions were often clinically relevant and linked to personal care products. Cross-reactivity was >40%. [ABSTRACT FROM AUTHOR]- Published
- 2022
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8. Enhancing the stability of zein pickering foams via hydrophilic reassembly with sugar alcohols and glycosides: A structural and molecular investigation.
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Qu, Zihan, Chen, Guiyun, Yang, Tongliang, Niu, Fushen, Bian, Yaqing, Yang, Cheng, Chen, Ye, and Li, Shuhong
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SUGAR alcohols , *MANNITOL , *FOAM , *VAN der Waals forces , *GLYCOSIDES , *MOLECULAR shapes , *AIR-water interfaces , *SWEETENERS - Abstract
Sucralose (Suc), maltitol (Mal), mannitol (Man), and stevioside (Ste) — a group of alcohol-soluble sugar derivatives with different contents and molecular configurations of hydrophilic groups — were complexed with deaminated zein to significantly enhance the stability of zein-based Pickering foams and develop new composite coacervates to replace animal protein-based foams. Compared with Suc, Mal, and Man, Ste induced better hydrophilic reassembly in zein by forming stronger van der Waals forces and hydrogen bonds, leading to optimum foamability (+160.66%) and foam stability (+17.11%). Moreover, it increased the solubility (+0.07 mg/mL) and decreased the surface hydrophobicity index (−24.88) of zein. These enhancements could primarily be attributed to alterations in the aggregation conformation and hydrophobic interactions within Ste/ZN. Subsequently, SEM and CLSM confirmed that due to the amphiphilic structure of Ste, dispersed zein micelles could aggregate into complex stacking structures. The increase in random coils (+2.48%) and β-sheets (+2.93%) indicated the enhanced flexibility of the zein chain, thereby facilitating zein adsorption and unfolding at the air-water interface. Moreover, molecular simulation demonstrated that an average of 3.1 hydrogen bonds were formed between zein and Ste, and the average binding free energy was −14.20 kcal/mol. These findings provide novel evidence and theoretical guidance for the development of highly stable plant protein-based food foams. The enhancement of Pickering foam stability holds significant implications for the storage and development of high-performance food foams. [Display omitted] • The foam properties of zein were effectively improved following deamination and combination with mannitol and stevioside. • Sugar derivatives improved the flexibility and hydrophilic aggregation of zein, increasing its stability and solubility. • The optimum foamability of Ste/ZN was attributed to greater hydrogen bond formation and reduced hydrophobicity. • Ste/ZN is a promising sweetening agent for highly stable Pickering foamed foods. [ABSTRACT FROM AUTHOR]
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- 2024
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9. Potential inhibitory properties of structurally modified quercetin/isohamnetin glucosides against SARS-CoV-2 Mpro; molecular docking and dynamics simulation strategies
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Peter Ifeoluwa Adegbola, Olumide Samuel Fadahunsi, Oluwasayo Esther Ogunjinmi, Aanuoluwa Eunice Adegbola, Fiyinfoluwa Demilade Ojeniyi, Adetayo Adesanya, Emmanuel Olagoke, Ayobami Damilare Adisa, Adeola Folasade Ehigie, Adewale Adetutu, and Banjo Semire
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Glucoside ,Quercetin ,Isorhamnetin ,Main protease ,SARS-CoV-2 ,Binding energy ,Computer applications to medicine. Medical informatics ,R858-859.7 - Abstract
Concerned organizations and individuals are fully engaged in seeking appropriate measures towards managing Severe Acute Respiratory Syndrome Coronavirus 2 (SAR-CoV-2) infection because of the unprecedented economic and health impact. SAR-CoV-2 Main protease (SARS-CoV-2 Mpro) is unique to the survival and viability of the virus. Therefore, inhibition of Mpro can block the viral propagation.Thirty (30) derivatives were built by changing the glucosides in the Meta and para position of quercetin and isohamnetin. Molecular docking analysis was used for the screening of the compounds. Dynamics simulation was performed to assess the stability of the best pose docked complex. Molecular mechanics binding free energy calculation was done by Molecular Mechanics/Poisson-Boltzmann Surface Area (MMPBSA).Overall analysis showed that the compounds are allosteric inhibitors of SARS-CoV-2 Mpro. Dynamic simulation analysis established the stability of Mpro-ISM-1, Mpro-ISD-3, Mpro-IST-2, Mpro-QM-2, and Mpro-QD-6 complexes with a maximum of 7 hydrogen bonds involved in their interaction. The MMPBSA binding free energies for ISM-1, ISD-3, IST-2, QM-2, and QD-6 were −92.47 ± 9.06, −222.27 ± 32.5, 180.72 ± 47.92, 156.46 ± 49.88 and −93.52 ± 48.75 kcal/mol respectively. All the compounds showed good pharmacokinetic properties, while only ISM-1 inhibits hERG and might be cardio-toxic.Observations in this study established that the glucoside position indeed influenced the affinity for SARS-CoV-2 Mpro. The study also suggested the potentials of ISD-3, QM-2 and QD-6 as potent inhibitors of the main protease, further experimental and clinical studies are however necessary to validate and establish the need for further drug development processes. Therefore, future studies will be on the chemical synthesis of the compounds and investigation of the in-vitro inhibition of SARS-CoV-2.
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- 2023
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10. Glycoside-specific metabolomics combined with precursor isotopic labeling for characterizing plant glycosyltransferases.
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Wu, Jie, Zhu, Wentao, Shan, Xiaotong, Liu, Jinyue, Zhao, Lingling, and Zhao, Qiao
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Glycosylation by uridine diphosphate-dependent glycosyltransferases (UGTs) in plants contributes to the complexity and diversity of secondary metabolites. UGTs are generally promiscuous in their use of acceptors, making it challenging to reveal the function of UGTs in vivo. Here, we described an approach that combined glycoside-specific metabolomics and precursor isotopic labeling analysis to characterize UGTs in Arabidopsis. We revisited the UGT72E cluster, which has been reported to catalyze the glycosylation of monolignols. Glycoside-specific metabolomics analysis reduced the number of differentially accumulated metabolites in the ugt72e1e2e3 mutant by at least 90% compared with that from traditional untargeted metabolomics analysis. In addition to the two previously reported monolignol glycosides, a total of 62 glycosides showed reduced accumulation in the ugt72e1e2e3 mutant, 22 of which were phenylalanine-derived glycosides, including 5-OH coniferyl alcohol-derived and lignan-derived glycosides, as confirmed by isotopic tracing of [13C 6 ]-phenylalanine precursor. Our method revealed that UGT72Es could use coumarins as substrates, and genetic evidence showed that UGT72Es endowed plants with enhanced tolerance to low iron availability under alkaline conditions. Using the newly developed method, the function of UGT78D2 was also evaluated. These case studies suggest that this method can substantially contribute to the characterization of UGTs and efficiently investigate glycosylation processes, the complexity of which have been highly underestimated. Glycoside-specific metabolomics combined with precursor isotopic labeling method is developed to effectively characterizeuridine diphosphate-dependent glycosyltransferases in planta, providing us with new knowledge including unknown substrate/product scope and unknown physiological roles of uridine diphosphate-dependentglycosyltransferases. The combined approach enables comprehensive understanding of the glycosylation networks, which are far more complicated than previously thought. [ABSTRACT FROM AUTHOR]
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- 2022
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11. A novel monoclonal antibody associated with glucoside kills gastric adenocarcinoma AGS cells based on glycosylation target.
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Xu, Heng, Dun, Boying, Liu, Beiyi, Mysona, David, She, Jin‐Xiong, and Ma, Rong
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CELL death ,GLYCOSYLATION ,MONOCLONAL antibodies ,IMMUNE recognition ,CANCER cells ,DEATH receptors ,CELL membranes ,ADENOCARCINOMA - Abstract
Glycosylation results in the production of glycans which are required for certain proteins to function. These glycans are also present on cell surfaces where they help maintain cell membrane integrity and are a key component of immune recognition. As such, cancer has been shown to alter glycosylation to promote tumour proliferation, invasion, angiogenesis, and immune envasion. Currently, there are few therapeutic monoclonal antibodies (mAb) which target glycosylation alterations in cancer. Here, we report a novel mAb associated with a glucoside, mAb 201E4, which is able induce cancer cell death and apoptosis based on a specific glycosylation target. This mAb evokes cancer cell death in vitro via caspase, fas, and mitochondrial associated apoptotic pathways. The efficacy of this mAb was further confirmed in vivo as treatment of mice with mAb 201E4 resulted in potent tumour shrinkage. Finally, the antibody was proven to be specific to glycosylation alterations in cancer and have no binding to normal tissues. This data indicates that mAb 201E4 successfully targets glycosylation alterations in neoplasms to induce cancer cell death, which may provide a new strategy for therapy in cancer. [ABSTRACT FROM AUTHOR]
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- 2022
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12. Antitobacco Mosaic Virus Activity of a New Eremophilane Glucoside From the Leaves of Nicotiana tabacum L.
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Wang, Hui, Zhang, Li-li, Li, Yong-sheng, Li, Shi-tou, He, Wen-miao, Wu, Ji-zhong, Bi, Yi-ming, Dai, Lu, Shen, Meng-hao, Yang, Jing, and Tie, Jin-xin
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MOSAIC viruses ,ELECTROSPRAY ionization mass spectrometry ,NUCLEAR magnetic resonance ,NICOTIANA - Abstract
A new eremophilane-type sesquiterpene glucoside, 13-hydroxycapsidiol 3- O - β -D-glucoside (1), was isolated from the leaves of Nicotiana tabacum L. The structure of this new metabolite was determined by one-dimensional (1D) and 2D nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), and comparison with values reported in the literature. Compound 1 was the second glycosylated eremophilane sesquiterpenoid isolated from plants of the Solanaceae family and exhibited a more potent anti-tobacco mosaic virus (anti-TMV) activity, with an inhibition rate of 39.4% at 20 μM, than the positive control ningnanmycin (34.8%). [ABSTRACT FROM AUTHOR]
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- 2022
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13. Two new phenolic glucosides from marine-derived fungus Aspergillus sp.
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Wen, Huiling, Zang, Yi, Zhu, Qianheng, Ouyang, Sheng, Luo, Juanjuan, Luo, Nianhua, Zhu, Hucheng, and Zhang, Yonghui
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ELECTROSPRAY ionization mass spectrometry ,GLUCOSIDES ,ASPERGILLUS ,POLYKETIDES - Abstract
Two new phenolic glucosides, including a new O-glycoside (1) and a new C-glycoside (2), were isolated from a marine-derived fungus Aspergillus sp. The structures of new compounds were elucidated through interpretations of spectroscopic evidence and high-resolution electrospray ionization mass spectrometry. The hexose unit of 1 was identified as β-D-glucose by comparison with an authentic sample via HPLC after acid hydrolysis and derivatization. All compounds were evaluated for their ability to inhibit LPS-induced NO production in RAW264.7 macrophages, but none of them displayed significant activity. [ABSTRACT FROM AUTHOR]
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- 2022
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14. 不同干燥工艺对高 RA 型甜叶菊糖苷含量的 影响.
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陈竞天, 欧珠, 杨云舒, 杨文艺, 侯凯, 张慧慧, and 吴卫
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HIGH performance liquid chromatography ,DRYING ,STEVIA rebaudiana ,STEVIOSIDE ,RAW materials ,STEVIA - Abstract
Copyright of Food Research & Development is the property of Food Research & Development Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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- 2022
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15. Bioactive Alpha-Pyrone and Phenolic Glucosides from the Marine-Derived Metarhizium sp. P2100
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Zhong-Lian Ma, Zhi-Pu Yu, Yao-Yao Zheng, Na Han, Ya-Hui Zhang, Shu-Yue Song, Jun-Qiu Mao, Jiao-Jiao Li, Guang-Shan Yao, and Chang-Yun Wang
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marine-derived fungus ,Metarhizium ,glucoside ,4-O-methyl-β-D-glucose ,α-amylase inhibitor ,Biology (General) ,QH301-705.5 - Abstract
Glycoside compounds have attracted great interest due to their remarkable and multifarious bioactivities. In this study, four hitherto unknown 4-methoxy-β-D-glucosyl derivatives were obtained and identified from the marine-derived fungus Metarhizium sp. P2100, including three alpha-pyrone glycosides (1–3) and one phenolic glycoside (4). Their planar structures were elucidated by comprehensive spectroscopic analysis, including 1D/2D NMR and HRESIMS. The absolute configurations of 1–3 were determined by a single-crystal X-ray crystallographic experiment, a comparison of the experimental, and a calculated electronic circular dichroism (ECD) spectra, respectively. Compounds 2 and 3 are a pair of rare epimeric pyranoside glycosides at C-7 with a core of aglycone as 2H-pyrone. Compounds 1–4 exhibited weak anti-inflammatory activities. In particular, compounds 1–3 displayed inhibitory activities against α-amylase, showing a potential for the development of a new α-amylase inhibitor for controlling diabetes.
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- 2022
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16. Glucoside Derivatives Of Podophyllotoxin: Synthesis, Physicochemical Properties, And Cytotoxicity
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Zi CT, Yang L, Kong QH, Li HM, Yang XZ, Ding ZT, Jiang ZH, Hu JM, and Zhou J
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podophyllotoxin ,glucoside ,synthesis ,cytotoxicity ,physicochemical properties ,Therapeutics. Pharmacology ,RM1-950 - Abstract
Cheng-Ting Zi,1,2,* Liu Yang,2,* Qing-Hua Kong,2 Hong-Mei Li,2 Xing-Zhi Yang,2 Zhong-Tao Ding,3 Zi-Hua Jiang,4 Jiang-Miao Hu,2 Jun Zhou2 1Key Laboratory of Pu-Er Tea Science, Ministry of Education, College of Science, Yunnan Agricultural University, Kunming, 650201, People’s Republic of China; 2State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People’s Republic of China; 3Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People’s Republic of China; 4Department of Chemistry, Lakehead University, Thunder Bay ON P7B 5E1, Canada*These authors contributed equally to this workCorrespondence: Zi-Hua JiangDepartment of Chemistry, Lakehead University, 955 Oliver Road, Thunder Bay ON P7B 5EI, CanadaTel +1 807 766 7171Fax +1 807 346 7775Email zjiang@lakeheadu.caJiang-Miao HuState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, No. 132, Lanhei Road, Kunming 650201, People’s Republic of ChinaTel +86 871 6522 3264Fax +86 871 6522 3261Email hujiangmiao@mail.kib.ac.cnBackground: Widespread concern of the side effects and the broad-spectrum anticancer property of podophyllotoxin as an antitumor agent highlight the need for the development of new podophyllotoxin derivatives. Although some per-butyrylated glucosides of podophyllotoxin and 4β-triazolyl-podophyllotoxin glycosides show good anticancer activity, the per-acetylated/free of podophyllotoxin glucosides and their per-acetylated are not well studied.Methods: A few glucoside derivatives of PPT were synthesized and evaluated for their in vitro cytotoxic activities against five human cancer cell lines, HL-60 (leukemia), SMMC-7721 (hepatoma), A-549 (lung cancer), MCF-7 (breast cancer), and SW480 (colon cancer), as well as the normal human pulmonary epithelial cell line (BEAS-2B). In addition, we investigated the structure–activity relationship and the physicochemical property–anticancer activity relationship of these compounds.Results: Compound 6b shows the highest cytotoxic potency against all five cancer cell lines tested, with IC50 values ranging from 3.27±0.21 to 11.37±0.52 μM. We have also found that 6b displays higher selectivity than the etoposide except in the case of HL-60 cell line. The active compounds possess similar physicochemical properties: MSA > 900, %PSA < 20, ClogP > 2, MW > 700 Da, and RB > 10.Conclusion: We synthesized several glucoside derivatives of PPT and tested their cytotoxicity. Among them, compound 6b showed the highest cytotoxicity. Further studies including selectivity of active compounds have shown that the selectivity indexes of 6b are much greater than the etoposide except in the case of HL-60 cell line. The active compounds possessed similar physicochemical properties. This study indicates that active glucoside analogs of podophyllotoxin have potential as lead compounds for developing novel anticancer agents.Keywords: podophyllotoxin, glucoside, synthesis, cytotoxicity, physicochemical properties
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- 2019
17. Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides
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Meihang Chen, Xun Zhang, Daowang Lu, Hairong Luo, Zengyan Zhou, Xufeng Qin, Wenneng Wu, and Guoping Zhang
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thiadiazole ,amide ,glucoside ,synthesis ,bioactivity ,Chemistry ,QD1-999 - Abstract
A series of novel 1,3,4-thiadiazole derivatives of glucosides were synthesized by the starting materials d-glucose and 5-amino-1,3,4-thiadiazole-2-thiol in good yields with employing a convergent synthetic route. The results of bioactivities showed that some of the target compounds exhibited good antifungal activities. Especially, compounds 4i showed higher bioactivities against Phytophthora infestans (P. infestans), with the EC50 values of 3.43, than that of Dimethomorph (5.52 μg/ml). In addition, the target compounds exhibited moderate to poor antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas campestris pv. citri (Xcc).
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- 2021
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18. Effect of different planting times on the quantitative variation of total seed isoflavone content and composition in Korean soybean cultivars (Glycine max (L.) Merr.).
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Kim, Hong-Sik, Kang, Beom-Kyu, Seo, Jeong-Hyun, Kim, Hyun-Tae, Ha, Tae-Joung, Oh, Jae-Hyeon, Shin, Sang-Ouk, and Baek, In-Yeol
- Abstract
There is great interest in the enhancement of isoflavones as one of the functional ingredients in soybean. This study aimed to investigate the effects of changes in the ecological environment over different planting times on isoflavone content. A total of 28 Korean soybean cultivars were grown at different planting times in late May, mid-June, and early July and their isoflavone content was measured over 2 years (2017 and 2018). Analyses of variance revealed significant effects of genotypes, planting times, years, and their interactions on isoflavone content. The average content of total isoflavone, as well as its component groups of malonylglucoside and aglycon, increased significantly as the seed planting time was delayed from late May to early July. The accumulation of each isoflavone component varied with changes in the planting time. The isoflavone content of the soybean cultivars for soy-sprout and soy-paste and tofu were higher for plantings in early July than for those in late May and/or mid-June, except for the black soybean cultivars. Despite significant correlations of the isoflavone content of the 28 cultivars among the three planting times, the responses of individual cultivars varied in isoflavone content by planting time. When planting was delayed, the time to flowering and maturity was also delayed and the number of days of growth from planting or flowering to maturity decreased; however, this was not related to isoflavone content. When planting was delayed, the temperature during the ripening period from flowering to maturity was lower, which was inversely related to the isoflavone content. [ABSTRACT FROM AUTHOR]
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- 2021
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19. Improving Aqueous Solubility of Natural Antioxidant Mangiferin through Glycosylation by Maltogenic Amylase from Parageobacillus galactosidasius DSM 18751
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Jiumn-Yih Wu, Hsiou-Yu Ding, Tzi-Yuan Wang, Yu-Li Tsai, Huei-Ju Ting, and Te-Sheng Chang
- Subjects
mangiferin ,maltogenic amylase ,glycosylation ,glucoside ,Parageobacillus galactosidasius ,Therapeutics. Pharmacology ,RM1-950 - Abstract
Mangiferin is a natural antioxidant C-glucosidic xanthone originally isolated from the Mangifera indica (mango) plant. Mangiferin exhibits a wide range of pharmaceutical activities. However, mangiferin’s poor solubility limits its applications. To resolve this limitation of mangiferin, enzymatic glycosylation of mangiferin to produce more soluble mangiferin glucosides was evaluated. Herein, the recombinant maltogenic amylase (MA; E.C. 3.2.1.133) from a thermophile Parageobacillus galactosidasius DSM 18751T (PgMA) was cloned into Escherichia coli BL21 (DE3) via the expression plasmid pET-Duet-1. The recombinant PgMA was purified via Ni2+ affinity chromatography. To evaluate its transglycosylation activity, 17 molecules, including mangiferin (as sugar acceptors), belonging to triterpenoids, saponins, flavonoids, and polyphenol glycosides, were assayed with β-CD (as the sugar donor). The results showed that puerarin and mangiferin are suitable sugar acceptors in the transglycosylation reaction. The glycosylation products from mangiferin by PgMA were isolated using preparative high-performance liquid chromatography. Their chemical structures were glucosyl-α-(1→6)-mangiferin and maltosyl-α-(1→6)-mangiferin, determined by mass and nucleic magnetic resonance spectral analysis. The newly identified maltosyl-α-(1→6)-mangiferin showed 5500-fold higher aqueous solubility than that of mangiferin, and both mangiferin glucosides exhibited similar 1,1-diphenyl-2-picrylhydrazyl free radical scavenging activities compared to mangiferin. PgMA is the first MA with glycosylation activity toward mangiferin, meaning mangiferin glucosides have potential future applications.
- Published
- 2021
- Full Text
- View/download PDF
20. Bambusicolasides VII and VIII, Two New Glucosides from the Bamboo Aphid Pseudoregma bambusicola.
- Author
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Zhang, Puzhao, Feng, Shao, and Zhang, Yamei
- Subjects
- *
APHIDS , *NAPHTHOL , *GLUCOSIDES , *BAMBOO - Abstract
Two new glucosides, bambusicolasides VII (1) and VIII (2), were isolated from the ethanolic extract of the bamboo aphid Pseudoregma bambusicola. The structures of the two glucosides were identified as 7-O-[2-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl]-2,5-dimethylchromone (1) and 1,3-di-(O-β-D-glucopyranosyl)-6-methyl-7-nitro-8-naphthol (2) on the basis of spectral data as well as chemical methods. [ABSTRACT FROM AUTHOR]
- Published
- 2020
- Full Text
- View/download PDF
21. Simultaneous quantification and rat pharmacokinetics of formononetin‐7‐O‐β‐d‐glucoside and its metabolite formononetin by high‐performance liquid chromatography–tandem mass spectrometry.
- Author
-
Zhang, Peng, Ma, Han, Lin, Xiaolan, and Qiu, Feng
- Subjects
- *
LIQUID chromatography-mass spectrometry , *TANDEM mass spectrometry , *PHARMACOKINETICS , *METABOLITES , *FORMONONETIN , *ENTEROHEPATIC circulation , *RATS - Abstract
Formononetin‐7‐O‐β‐d‐glucoside has been proved to have significant anti‐inflammatory effect. To evaluate its rat pharmacokinetics, a rapid, sensitive, and specific liquid chromatography–tandem mass spectrometry method has been developed and validated for the quantification of formononetin‐7‐O‐β‐d‐glucoside and its main metabolite formononetin in rat plasma. Samples were pretreated using a simple protein precipitation and the chromatographic separation was performed on a C18 column by a gradient elution using a mobile phase consisting of water and acetonitrile both containing 0.1% formic acid. Both analytes were detected using a tandem mass spectrometer in positive multiple reaction monitoring mode. The assay showed wide linear dynamic ranges of both 0.10–100 ng/mL, with acceptable intra‐ and inter‐batch accuracy and precision. The lower limits of quantification were both 0.10 ng/mL using 50 μL of rat plasma for two analytes. The method has been successfully used to investigate the oral pharmacokinetic profiles of both analytes in rats. After oral administration of formononetin‐7‐O‐β‐d‐glucoside at the dose of 50 mg/kg, it was rapidly absorbed in vivo and metabolized to its metabolite formononetin. The plasma concentration‐time profiles both showed double‐peak phenomena, which would be attributed to the strong enterohepatic circulation of formononetin‐7‐O‐β‐d‐glucoside. [ABSTRACT FROM AUTHOR]
- Published
- 2020
- Full Text
- View/download PDF
22. 酸性条件下根皮苷对低酯果胶流变特性、 抗氧化活性及微观结构的影响.
- Author
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张舒翼, 丑述睿, 崔惠军, 王撼辰, 刘 璇, and 李 斌
- Subjects
SCANNING electron microscopy ,OXIDANT status ,PECTINS ,COLLOIDS ,MICROSTRUCTURE - Abstract
Copyright of Shipin Kexue/ Food Science is the property of Food Science Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
- Published
- 2020
- Full Text
- View/download PDF
23. Macromolecules: Synthesis, antimicrobial, POM analysis and computational approaches of some glucoside derivatives bearing acyl moieties.
- Author
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Kayes, Mohammad R., Saha, Supriyo, Alanazi, Mohammed M., Ozeki, Yasuhiro, Pal, Dilipkumar, Hadda, Taibi B., Legssyer, Abdelkhaleq, and Kawsar, Sarkar M.A.
- Abstract
Macromolecules i.e., carbohydrate derivatives are crucial to biochemical and medical research. Herein, we designed and synthesized eight methyl α-D-glucopyranoside (MGP) derivatives (2 – 8) in good yields following the regioselective direct acylation method. The structural configurations of the synthesized MGP derivatives were analyzed and verified using multiple physicochemical and spectroscopic techniques. Antimicrobial experiments revealed that almost all derivatives demonstrated noticeable antifungal and antibacterial efficacy. The synthesized derivatives showed minimum inhibitory concentration (MIC) values ranging from 0.75 µg/mL to 1.50 µg/mL and minimum bactericidal concentrations (MBCs) ranging from 8.00 µg/mL to 16.00 µg/mL. Compound 6 inhibited Ehrlich ascites carcinoma (EAC) cell proliferation by 10.36% with an IC50 of 2602.23 μg/mL in the MTT colorimetric assay. The obtained results were further rationalized by docking analysis of the synthesized derivatives against 4URO and 4XE3 receptors to explore the binding affinities and nonbonding interactions of MGP derivatives with target proteins. Compound 6 demonstrated the potential to bind with the target with the highest binding energy. In a stimulating environment, a molecular dynamics study showed that MGP derivatives have a stable conformation and binding pattern. The MGP derivatives were examined using POM (Petra/Osiris/Molinspiration) bioinformatics, and as a result, these derivatives showed good toxicity, bioavailability, and pharmacokinetics. Various antifungal/antiviral pharmacophore (O
δ− , O′δ− ) sites were identified by using POM investigations, and compound 6 was further tested against other pathogenic fungi and viruses, such as Micron and Delta mutants of SARS-CoV-2. [ABSTRACT FROM AUTHOR]- Published
- 2023
- Full Text
- View/download PDF
24. Enzymatic Synthesis of Novel Vitexin Glucosides
- Author
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Jiumn-Yih Wu, Tzi-Yuan Wang, Hsiou-Yu Ding, Yun-Rong Zhang, Shu-Yuan Lin, and Te-Sheng Chang
- Subjects
glycoside hydrolase ,glycosyltransferase ,glycosylation ,vitexin ,glucoside ,Organic chemistry ,QD241-441 - Abstract
Vitexin is a C-glucoside flavone that exhibits a wide range of pharmaceutical activities. However, the poor solubility of vitexin limits its applications. To resolve this limitation, two glycoside hydrolases (GHs) and four glycosyltransferases (GTs) were assayed for glycosylation activity toward vitexin. The results showed that BtGT_16345 from the Bacillus thuringiensis GA A07 strain possessed the highest glycosylation activity, catalyzing the conversion of vitexin into new compounds, vitexin-4′-O-β-glucoside (1) and vitexin-5-O-β-glucoside (2), which showed greater aqueous solubility than vitexin. To our knowledge, this is the first report of vitexin glycosylation. Based on the multiple bioactivities of vitexin, the two highly soluble vitexin derivatives might have high potential for pharmacological usage in the future.
- Published
- 2021
- Full Text
- View/download PDF
25. Enzymatic Production of 3-OH Phlorizin, a Possible Bioactive Polyphenol from Apples, by Bacillus megaterium CYP102A1 via Regioselective Hydroxylation
- Author
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Ngoc Anh Nguyen, Ngoc Tan Cao, Thi Huong Ha Nguyen, Jung-Hwan Ji, Gun Su Cha, Hyung-Sik Kang, and Chul-Ho Yun
- Subjects
bacterial CYP102A1 ,dihydrochalcone ,glucoside ,regioselective hydroxylation ,phloretin ,phlorizin ,Therapeutics. Pharmacology ,RM1-950 - Abstract
Phlorizin is the most abundant glucoside of phloretin from the apple tree and its products. Phlorizin and its aglycone phloretin are currently considered health-beneficial polyphenols from apples useful in treating hyperglycemia and obesity. Recently, we showed that phloretin could be regioselectively hydroxylated to make 3-OH phloretin by Bacillus megaterium CYP102A1 and human P450 enzymes. The 3-OH phloretin has a potent inhibitory effect on differentiating 3T3-L1 preadipocytes into adipocytes and lipid accumulation. The glucoside of 3-OH phloretin would be a promising agent with increased bioavailability and water solubility compared with its aglycone. However, procedures to make 3-OH phlorizin, a glucoside of 3-OH phloretin, using chemical methods, are not currently available. Here, a biocatalytic strategy for the efficient synthesis of a possibly valuable hydroxylated product, 3-OH phlorizin, was developed via CYP102A1-catalyzed regioselective hydroxylation. The production of 3-OH phlorizin by CYP102A1 was confirmed by HPLC and LC–MS spectroscopy in addition to enzymatic removal of its glucose moiety for comparison to 3-OH phloretin. Taken together, in this study, we found a panel of mutants from B. megaterium CYP102A1 could catalyze regioselective hydroxylation of phlorizin to produce 3-OH phlorizin, a catechol product.
- Published
- 2021
- Full Text
- View/download PDF
26. Identification of 24-O-β-d-Glycosides and 7-Deoxy-Analogues of Okadaic Acid and Dinophysistoxin-1 and -2 in Extracts from Dinophysis Blooms, Dinophysis and Prorocentrum Cultures, and Shellfish in Europe, North America and Australasia
- Author
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Alistair L. Wilkins, Thomas Rundberget, Morten Sandvik, Frode Rise, Brent K. Knudsen, Jane Kilcoyne, Beatriz Reguera, Pilar Rial, Elliott J. Wright, Sabrina D. Giddings, Michael J. Boundy, Cheryl Rafuse, and Christopher O. Miles
- Subjects
Dinophysis ,Prorocentrum ,okadaic acid ,dinophysistoxin ,glucoside ,7-deoxyokadaic acid ,Medicine - Abstract
Two high-mass polar compounds were observed in aqueous side-fractions from the purification of okadaic acid (1) and dinophysistoxin-2 (2) from Dinophysis blooms in Spain and Norway. These were isolated and shown to be 24-O-β-d-glucosides of 1 and 2 (4 and 5, respectively) by nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry, and enzymatic hydrolysis. These, together with standards of 1, 2, dinophysistoxin-1 (3), and a synthetic specimen of 7-deoxy-1 (7), combined with an understanding of their mass spectrometric fragmentation patterns, were then used to identify 1–5, the 24-O-β-d-glucoside of dinophysistoxin-1 (6), 7, 7-deoxy-2 (8), and 7-deoxy-3 (9) in a range of extracts from Dinophysis blooms, Dinophysis cultures, and contaminated shellfish from Spain, Norway, Ireland, Canada, and New Zealand. A range of Prorocentrum lima cultures was also examined by liquid chromatography–high resolution tandem mass spectrometry (LC–HRMS/MS) and was found to contain 1, 3, 7, and 9. However, although 4–6 were not detected in these cultures, low levels of putative glycosides with the same exact masses as 4 and 6 were present. The potential implications of these findings for the toxicology, metabolism, and biosynthesis of the okadaic acid group of marine biotoxins are briefly discussed.
- Published
- 2021
- Full Text
- View/download PDF
27. Isoflavone, anthocyanin, and fatty acid contents of vegetable-type soybean grains at different maturity stages
- Author
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Mercedes Concórdia Carrão-Panizzi, Bruna dos Santos Silva, Rodrigo Santos Leite, Ronoel Luiz de Oliveira Godoy, Manuela Cristina Pessanha de Araujo Santiago, Ilana Felberg, and Maria Cristina Neves de Oliveira
- Subjects
Glycine max ,aglucone ,breeding line ,glucoside ,oil ,protein ,Agriculture (General) ,S1-972 - Abstract
Abstract: The objective of this work was to determine the oil, protein, fatty acid, isoflavone, and anthocyanin contents in soybean grains of different breeding lines and maturity stages. Evaluations were performed for the chemical profiles of black- (BRM09-50995) and of yellow-seed-coat (BRM11-51428 and BRM08-50643) breeding lines, harvested at the R6 (immature seeds), R7 (physiological maturity), and R8 (full maturity) maturity stages. Oil and protein contents increased from the R6 to the R8 stage, and BRM11-51428 showed the highest protein content. Palmitic, stearic, and linolenic fatty acids were higher at R6, and linoleic and oleic acids were higher at R7 and R8, respectively. At the R8 growth stage, BRM11-51428 and BRM 09-50995 showed the highest contents of oleic and linoleic acids, respectively, and the lowest content of linolenic acid. The amounts of isoflavone glucosides and aglucones were higher at R8, while malonyl forms were higher at R7. Total aglucones increased about three times from R6 to R8. BRM09-50995 showed the highest content of total isoflavones and anthocyanins, mainly at the R8 stage, which makes this lineage an option to process functional soybean food.
- Published
- 2019
- Full Text
- View/download PDF
28. A Synthetic, Small, Sulfated Agent Is a Promising Inhibitor of Chlamydia spp. Infection in vivo
- Author
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Karen M. Gallegos, Christopher R. Taylor, Daniel J. Rabulinski, Rosalinda Del Toro, Danielle E. Girgis, Dapinder Jourha, Vaibhav Tiwari, Umesh R. Desai, and Kyle H. Ramsey
- Subjects
Chlamydia trachomatis ,Chlamydia muridarum ,inhibition ,glucoside ,SPGG ,Microbiology ,QR1-502 - Abstract
Chlamydia is the most frequently reported sexually transmitted bacteria causing 2.9 million infections annually in the United States. Diagnosis, treatment, and sequelae of chlamydial disease cost billions of dollars each year in the United States alone. Considering that a heparin sulfate-like cell surface receptor is involved in Chlamydia infections, we reasoned that sulfated and sulfonated mimics of heparin sulfate would be useful in topical prophylactic prevention of Chlamydia. In this study, we tested a small, synthetic sulfated agent sulfated pentagalloyl glucoside (SPGG) and three synthetic sulfonated polymers PSS and SPS with average molecular weight in the range of 11 to 1000 kDa for inhibition against Chlamydia. Infection of HeLa cells with C. muridarum or C. trachomatis in the presence of increasing concentrations of SPGG or sulfonated polymers were quantified by immunofluorescence of Chlamydia inclusions. To determine whether in vitro pre-treatment of SPGG inhibits infection of C. muridarum, HeLa monolayers were incubated with SPGG-containing media, and then infected with Chlamydia. Our in vitro results show that SPGG pre-treatment inhibits Chlamydia infection in a dose-dependent manner. In addition, we further determined if SPGG treatment has an inhibitory effect during infection, therefore cell monolayers were infected with C. muridarum in the concurrent presence of SPGG. Our results show that SPGG inhibits C. muridarum infection with an IC50 at 10 μg/ml levels. We also tested the inhibitory effect of synthetic polymers PSS and SPS against Chlamydia and found inhibition of C. muridarum and C. trachomatis infections with IC50 ranging from 0.3 to 0.8 μg/ml. SPGG, PSS, and SPS inhibit formation of Chlamydia inclusions in a concentration-dependent manner. For evaluation of in vivo efficacy of the most effective agent in blocking C. muridarum, SPGG, we intravaginally pre-treated mice with SPGG before infection with C. muridarum. Cervical swabs were collected post-infection to quantify Chlamydia inclusions in vitro. Our in vivo data show that the SPGG-treated group has a statistically significant reduction of infection compared to the no-treatment control. Overall, our results show that SPGG could serve as a promising topical inhibitor for preventing Chlamydia infection.
- Published
- 2019
- Full Text
- View/download PDF
29. 利用密度泛函理论研究葡萄籽中甜味物质的性质.
- Author
-
齐于太, 张颖异, 侯英敏, 王 一, and 郁 玲
- Abstract
Copyright of Journal of Dalian Polytechnic University is the property of Journal of Dalian Polytechnic University Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
- Published
- 2019
- Full Text
- View/download PDF
30. Improved synthesis, X-ray structure, and antifungal activity of a sugar-psoralen conjugate: 4,4′-Dimethylxanthotoxol 2,3,4,6-tetra-O-Acetyl-β-D-glucoside.
- Author
-
Chen, Chao-Yue, Yang, Ting-Hai, Pan, Chang-Duo, and Wang, Xin
- Subjects
- *
PYRICULARIA grisea , *DIHEDRAL angles , *RHIZOCTONIA solani , *STERIC hindrance , *X-rays - Abstract
An improved synthesis for 4,4′-dimethylxanthotoxol 2,3,4,6-tetra-O-acetyl-β-D-glucoside (1) starting from resorcinol was developed. Crystallographic analysis of glucoside 1 indicated that the dihedral angles between the mean planes of the tricyclic ring system of adjacent molecules was 54.820(22)° probably due to the steric hindrance caused by the bulky O-glucoside moiety, which prevents the molecules from packing via π···π stacking between the tricyclic cores. The antifungal screening data revealed that glucoside 1 had higher inhibition than its parent compound 4,4′-dimethylxanthotoxol and azoxystrobin against Rhizoctonia solani, Pyricularia grisea, and Alternaria alternate Japanese pear pathotype, with the inhibitory rates of 75.4, 65.7 and 70.1%, respectively, at the 50 µg/mL concentration. [ABSTRACT FROM AUTHOR]
- Published
- 2019
- Full Text
- View/download PDF
31. A Synthetic, Small, Sulfated Agent Is a Promising Inhibitor of Chlamydia spp. Infection in vivo.
- Author
-
Gallegos, Karen M., Taylor, Christopher R., Rabulinski, Daniel J., Del Toro, Rosalinda, Girgis, Danielle E., Jourha, Dapinder, Tiwari, Vaibhav, Desai, Umesh R., and Ramsey, Kyle H.
- Subjects
CHLAMYDIA ,CHLAMYDIA infections ,SEXUALLY transmitted diseases ,PENTAGALLOYLGLUCOSE ,IMMUNOFLUORESCENCE - Abstract
Chlamydia is the most frequently reported sexually transmitted bacteria causing 2.9 million infections annually in the United States. Diagnosis, treatment, and sequelae of chlamydial disease cost billions of dollars each year in the United States alone. Considering that a heparin sulfate-like cell surface receptor is involved in Chlamydia infections, we reasoned that sulfated and sulfonated mimics of heparin sulfate would be useful in topical prophylactic prevention of Chlamydia. In this study, we tested a small, synthetic sulfated agent sulfated pentagalloyl glucoside (SPGG) and three synthetic sulfonated polymers PSS and SPS with average molecular weight in the range of 11 to 1000 kDa for inhibition against Chlamydia. Infection of HeLa cells with C. muridarum or C. trachomatis in the presence of increasing concentrations of SPGG or sulfonated polymers were quantified by immunofluorescence of Chlamydia inclusions. To determine whether in vitro pre-treatment of SPGG inhibits infection of C. muridarum , HeLa monolayers were incubated with SPGG-containing media, and then infected with Chlamydia. Our in vitro results show that SPGG pre-treatment inhibits Chlamydia infection in a dose-dependent manner. In addition, we further determined if SPGG treatment has an inhibitory effect during infection, therefore cell monolayers were infected with C. muridarum in the concurrent presence of SPGG. Our results show that SPGG inhibits C. muridarum infection with an IC
50 at 10 μg/ml levels. We also tested the inhibitory effect of synthetic polymers PSS and SPS against Chlamydia and found inhibition of C. muridarum and C. trachomatis infections with IC50 ranging from 0.3 to 0.8 μg/ml. SPGG, PSS, and SPS inhibit formation of Chlamydia inclusions in a concentration-dependent manner. For evaluation of in vivo efficacy of the most effective agent in blocking C. muridarum , SPGG, we intravaginally pre-treated mice with SPGG before infection with C. muridarum. Cervical swabs were collected post-infection to quantify Chlamydia inclusions in vitro. Our in vivo data show that the SPGG-treated group has a statistically significant reduction of infection compared to the no-treatment control. Overall, our results show that SPGG could serve as a promising topical inhibitor for preventing Chlamydia infection. [ABSTRACT FROM AUTHOR]- Published
- 2019
- Full Text
- View/download PDF
32. A New Isoflavan Glucoside from the Roots of Astragalus membranaceus var. mongholicus
- Author
-
Fenghuan Wang, Yuanhao Wang, Yadong Wang, Qing Hu, and Chao Wang
- Subjects
Pharmacology ,chemistry.chemical_compound ,Glucoside ,chemistry ,Traditional medicine ,Organic Chemistry ,Drug Discovery ,Plant Science ,Astragalus membranaceus var. mongholicus ,Biology - Published
- 2022
33. A New Iridoid Glucoside from the Stems of Myoporum bontioides (Sieb.et Zucc.) A. Gray
- Author
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Tran Thi Minh, Nguyen Thi Viet Thanh, and Vu Dinh Hoang
- Subjects
Pharmacology ,Iridoid ,biology ,medicine.drug_class ,Chemistry ,Myoporum ,Organic Chemistry ,Plant Science ,biology.organism_classification ,chemistry.chemical_compound ,Glucoside ,Drug Discovery ,Botany ,medicine - Published
- 2022
34. Separation of salidroside from the fermentation broth of engineered Escherichia coli using macroporous adsorbent resins
- Author
-
Xiaocui Sun, Xue Liu, and Guang-Rong Zhao
- Subjects
Environmental Engineering ,Chromatography ,General Chemical Engineering ,Salidroside ,Langmuir adsorption model ,General Chemistry ,Biochemistry ,Separation process ,Tyrosol ,chemistry.chemical_compound ,symbols.namesake ,Adsorption ,Glucoside ,chemistry ,Desorption ,symbols ,Fermentation - Abstract
Salidroside (8-O-β- d -glucoside of tyrosol), a plant-derived natural product, is used for treatment of hypoxia, fatigue and aging diseases. The availability of salidroside is restricted since it is extracted from 3-5 years old Rhodiola roots, which grow very slowly in the cold region of northern hemisphere of Earth. Our laboratory has constructed an engineered Escherichia coli and established a fermentation process to produce salidroside from glucose. In this article, nine macroporous resins from polarity to non-polarity, including NKA-9, S-8, AB-8, SP825, D101, LSA-8, LX-12, LX-18 and LX-68 resins, were tested to separate salidroside from fermentation broth. After static and dynamic experiments, the weakly polar SP825 resin had a better separation efficiency among nine resins. The adsorption kinetic and isotherm of salidroside on the SP825 resin were determined, and the pseudo-second-order kinetic model and Langmuir model could be fitted well. The effects of the pH on adsorption and ethanol concentration on desorption were investigated, and an optimal separation process was established. The adsorption for salidroside in the SP825 resin column was conducted with loading 150 ml at pH 7, and desorpted by washing 50 ml of 80% ethanol solution. Under the best process conditions, the purity and yield of salidroside in the final product were 91.6% and 74.0%, respectively. The results showed that the macroporous SP825 resin would be feasible and effective to prepare salidroside and has promising application in the downstream process of microbial fermentation. © 2020 The Chemical Industry and Engineering Society of China, and Chemical Industry Press Co., Ltd.. All rights reserved.
- Published
- 2022
35. Whole-cell catalytic synthesis of 2-O-α-glucopyranosyl-l-ascorbic acid by sucrose phosphorylase from Bifidobacterium breve via a batch-feeding strategy
- Author
-
Yuele Lu, Gan Tian, Zhu Linjiang, Zhi Ma, Yaoyao Zhou, Xiaolong Chen, Ruini Jiang, and Hanchi Chen
- Subjects
Glycosylation ,Sucrose ,Chromatography ,Bifidobacterium breve ,ved/biology ,ved/biology.organism_classification_rank.species ,Bioengineering ,Fructose ,Sucrose phosphorylase ,Ascorbic acid ,Applied Microbiology and Biotechnology ,Biochemistry ,chemistry.chemical_compound ,chemistry ,Glucoside ,Glycosyl donor - Abstract
l -ascorbic acid 2-O-α- d -glucoside (AA-2G), a highly stabilized vitamin C derivative, has been widely applied in cosmetics, foods, and pharmaceuticals. Sucrose phosphorylase (SPase) was recently reported to be effective for producing AA-2G. In this study, SPase from Bifidobacterium breve (BbrSPase) was identified as a new AA-glycosylating tool with high activity and good thermostability. The optimal conditions for AA glycosylation are pH 5.5 and 55 °C. The K m and k c a t when sucrose was applied as a glycosyl donor were 2.72 ± 0.49 mM and 9.70 ± 0.10 s−1, respectively. The transglycosylation activity was seriously inhibited by fructose, which caused a sharp decline in the glycosylation rate but did not necessarily stop the yield of AA-2G due to the high affinity to sucrose. Therefore, to attenuate the inhibition of fructose, a new sucrose batch-feeding strategy was developed for the effective production of AA-2G. The maximum titer was 185 g/L within 72 h. The molar conversion rate of l -AA reached 50.2 %, which is the highest conversion rate to our knowledge.
- Published
- 2022
36. Estimation of some phytochemical materials and isolation of two flavonoids from pomegranate peel using different chromatographic techniques
- Author
-
Muhammad I Haggag and Mohammed H. Elhaw
- Subjects
chemistry.chemical_compound ,Chromatography ,chemistry ,Phytochemical ,Glucoside ,Target groups ,Ethyl acetate ,heterocyclic compounds ,General Medicine ,Isolation (microbiology) - Abstract
Recently, interest has increased in natural metabolites compounds from plants for industrial and pharmaceutical use rather than synthetic compounds. The pomegranate peels are one of the mostly thrown away in general and considered not so useful. Using different chromatographic techniques, extracted, separated, cleaned, and defined two flavonoids’ compounds as a result of these experiments were obtained the following compounds which are quercetin-3-methoxy glucoside and quercetin-3′-O-β-glucopyranoside. The structures of these compounds were identified by using, UV and NMR. The quantitative estimation of total flavonoids, total alkaloids, total saponins, and total tannins showed presence in a good amount in pomegranate peel. The phytochemical reactions of pure extract and the corresponding sub-fractions of pomegranate peel showed the presence of target groups of secondary metabolites in crude and ethyl acetate fractions.
- Published
- 2022
37. Enzymatic Synthesis of Resveratrol α-Glucoside by Amylosucrase of Deinococcus geothermalis
- Author
-
Hyunsu Park, Seola Lee, Jaeho Cha, and Keumok Moon
- Subjects
chemistry.chemical_classification ,Glycosylation ,Antioxidant ,endocrine system diseases ,biology ,organic chemicals ,medicine.medical_treatment ,food and beverages ,General Medicine ,Resveratrol ,biology.organism_classification ,Applied Microbiology and Biotechnology ,Bioavailability ,chemistry.chemical_compound ,Amylosucrase ,Enzyme ,chemistry ,Biochemistry ,Glucoside ,biology.protein ,medicine ,Deinococcus geothermalis ,Biotechnology - Abstract
Glycosylation of resveratrol was carried out by using the amylosucrase of Deinococcus geothermalis, and the glycosylated products were tested for their solubility, chemical stability, and biological activities. Two major glycosylated products were synthesized and identified as resveratrol-4'-O-α-glucoside and resveratrol-3-O-α-glucoside by nuclear magnetic resonance analysis with a ratio of 5:1. The water solubilities of two resveratrol-α-glucoside isomers (α-piceid isomers) were approximately 3.6 and 13.5 times higher than that of β-piceid and resveratrol, respectively, and highly stable in buffered solutions. The antioxidant activity of α-piceid isomers was examined by radical scavenging capability. The radical scavenging activity of α-piceid isomers was initially lower than that of resveratrol, but as time passed, the activity of α-piceid isomers became similar to that of reseveratrol. The α-piceid isomers also showed better tysoinase inhibitory activity and inhibition capability for melanin synthesis in B16F10 melanoma cells than β-piceid. The cellular uptake of α-piceid isomers, which was assessed by ultra-performance liquid chromatography analysis of the cell-free extracts of B16F10 melanoma cells, demonstrated that the glycosylated form of resveratrol was gradually converted to resveratrol inside the cells. These results indicate that the enzymatic glycosylation of resveratrol will be a useful method for the enhancement of the bioavailability of resveratrol.
- Published
- 2021
38. SGLT2 Inhibitors: Physiology and Pharmacology
- Author
-
Ernest M. Wright
- Subjects
biology ,Phlorizin ,business.industry ,Type 2 Diabetes Mellitus ,Renal function ,Physiology ,General Medicine ,Pharmacology ,Sodium-Glucose Transport Proteins ,Renal glucose reabsorption ,Excretion ,chemistry.chemical_compound ,Glucose ,Phlorhizin ,Diabetes Mellitus, Type 2 ,chemistry ,Glucoside ,Mole ,biology.protein ,Humans ,Medicine ,business ,Basic Science for Clinicians ,Sodium-Glucose Transporter 2 Inhibitors ,Sodium-glucose transport proteins - Abstract
SGLTs are sodium glucose transporters found on the luminal membrane of the proximal tubule, where they reabsorb some 180 grams (one mole) of glucose from the glomerular filtrate each day. The natural glucoside phlorizin completely blocks glucose reabsorption. Oral SGLT2 inhibitors are rapidly absorbed into the blood stream where they remain in in the circulation for hours. On glomerular filtration, they bind specifically to SGLT2 in the luminal membrane of the early proximal tubule to reduce glucose reabsorption by 50-60%. Because of glucose excretion, these drugs lower plasma glucose and glycosylated hemoglobin levels in patients with type 2 diabetes mellitus. The drugs also protect against heart and renal failure. The aim of this review is to summarize what is currently known about the physiology of renal SGLTs and the pharmacology of SGLT drugs.
- Published
- 2021
39. A Facile Method to Determine the Native Contents of 4′-O-Methylpyridoxine and 4′-O-Methylpyridoxine-5′-glucoside in Ginkgo biloba Seeds
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Fuliang Cao, Wen Zhang, Erzheng Su, Manman Shi, and Fang Zhang
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biology ,Ginkgo biloba ,food and beverages ,Water extraction ,General Chemistry ,biology.organism_classification ,Hydrolysis ,chemistry.chemical_compound ,Silver fluoride ,chemistry ,Glucoside ,Sample preparation ,Food science ,Cultivar ,General Agricultural and Biological Sciences ,Ginkgotoxin - Abstract
4'-O-Methylpyridoxine (MPN) and MPN-5'-glucoside (MPNG) are collectively known as ginkgotoxin, which are the main toxic ingredients of excessive consumption of Ginkgo biloba seeds. Water extraction is the generally adopted sample preparation method for high-performance liquid chromatography determination of ginkgotoxin. However, endogenous enzymes such as glycosidases in Ginkgo biloba seeds can hydrolyze MPNG to MPN in the process of water extraction, which will result in the measured contents of MPN and MPNG but not their natural contents in Ginkgo biloba seeds. In this work, inhibitors for the endogenous enzymes were first screened, and it was found that silver fluoride could effectively inhibit endogenous enzymes such as glucosidase and phosphatase. The optimized concentration of silver fluoride was 25 mmol/L, which could effectively inhibit the endogenous enzymes for more than 60 h. A new sample preparation method based on water extraction with 25 mmol/L silver fluoride addition was thus developed. This method was employed to determine the native contents of MPN and MPNG in the exotesta and kernel of five Ginkgo biloba seed cultivars. The result showed that the contents of MPNG in the exotesta and kernel of five cultivars were significantly higher than those of MPN. MPNG was present at high content in raw seeds, which was the main form of ginkgotoxin in seeds. The method established in this work is simple and effective and can be used to accurately quantify the native contents of MPN and MPNG.
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- 2021
40. Ascorbic acid 2‐glucoside: An ascorbic acid pro‐drug with longer‐term antioxidant efficacy in skin
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Camille Genies, Anne Laure Gaudry, Hélène Duplan, Nathalie Borotra, Fabio Sanches, Fernanda Chaves, Sandrine Bessou-Touya, Amelie Tourette, Carine Jacques, and Daniel Bacqueville
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Aging ,Antioxidant ,medicine.medical_treatment ,Pharmaceutical Science ,Human skin ,Ascorbic Acid ,Dermatology ,Absorption (skin) ,Antioxidants ,Superoxide dismutase ,chemistry.chemical_compound ,Colloid and Surface Chemistry ,Glucoside ,Drug Discovery ,medicine ,Humans ,Prodrugs ,Food science ,Skin ,biology ,Vitamin C ,Chemistry ,Ascorbic acid ,Malondialdehyde ,Oxidative Stress ,Chemistry (miscellaneous) ,biology.protein - Abstract
Deleterious effects of pollutants and ultraviolet radiation on the skin can be attenuated using formulations containing antioxidants. However, these have disadvantages, including chemical instability, photodegradation, poor bioavailability or biological activity. Here, two commercial formulations were evaluated: one optimized to stabilize and deliver ascorbic acid (AA) at 15% and the other containing a glucoside form of AA, namely ascorbic acid 2-glucoside (AA2G), at 1.8% and at a physiological pH. We compared the skin delivery, antioxidative effects and chemical stability of AA2G with AA in their respective formulations.Skin delivery was measured using fresh viable human skin explants, and oxidative stress was measured using a human reconstructed epidermal (RHE) model according to levels of malondialdehyde (MDA), superoxide dismutase (SOD) and catalase.Ascorbic acid 2-glucoside was completely metabolized to AA by the skin before entering the receptor compartment. The skin contained parent and AA, indicating a reserve of AA2G was present for further metabolism. For AA2G and AA, maximum flux of AA-equivalents was at 12 h, with continued absorption over 24 h. The absolute amount in µg was higher in the skin after application of AA than after application of AA2G. This may suggest a greater antioxidative effect; however, according to all three measurements of oxidative stress, the protective effect of AA and AA2G was similar. Unlike AA, AA2G was chemically stable under storage conditions.A lower concentration of AA2G is as effective as the active metabolite, AA, in terms of antioxidant effects. AA2G was chemically stable and can be applied at a lower concentration than AA, thus avoiding the need for an acidic formulation with a pH below 3.5.Les effets délétères des polluants et des rayonnements ultraviolets au niveau cutané peau peuvent être atténués avec des formulations contenant des antioxydants. Cependant, ceux-ci peuvent présenter des inconvénients comme une instabilité chimique, une photodégradation, une faible biodisponibilité ou une faible activité biologique. Nous avons évalué deux formulations commerciales: l'une optimisée pour stabiliser et libérer de l'acide ascorbique (AA) à 15 % et l'autre contenant une forme conjugué de l'AA, à savoir l'acide ascorbique 2-glucoside (AA2G), à 1.8% et formulée à un pH physiologique. Nous avons comparé le passage percutané, les effets antioxydants et la stabilité chimique de l'AA2G avec l'AA dans leurs formulations respectives. MÉTHODES: Le passage percutané a été évalué avec des explants de peau humaine maintenus en survie et le stress oxydatif a été évalué à l'aide d'un modèle d'épiderme reconstruit humain (RHE) en mesurant les niveaux de malondialdéhyde (MDA), de superoxyde dismutase (SOD) et de catalase. RÉSULTATS: L'AA2G a été complètement métabolisé en AA par la peau avant d'atteintre le compartiment récepteur. Le composé parent et l’AA ont été retrouvé dans la peau, indiquant qu'une réserve d'AA2G était présente pour une libération prolongée. Pour l’AA2G et l’AA, le flux maximal d'équivalents AA était à 12 h, avec une absorption continue sur 24 h. La quantité absolue en µg était plus élevée dans la peau après application de la formulation contenant 15% d'AA qu'après application de la formule contenant 1.8% d'AA2G. Cela peut suggérer un effet antioxydant plus important ; cependant, selon les trois paramètres évalués pour le stress oxydatif, l'effet protecteur de l'AA et de l'AA2G était similaire. Contrairement à l'AA, l'AA2G est chimiquement plus stable dans des conditions de stockage.Une concentration plus faible d'AA2G est aussi efficace que le métabolite actif, l'AA, en termes d'effets antioxydants. L'AA2G est chimiquement plus stable et peut être appliqué à une concentration inférieure à l'AA, évitant ainsi le besoin d'une formulation acide avec un pH inférieur à 3.5.
- Published
- 2021
41. Naturally Occurring and Artificial N9-Cytokinin Conjugates: From Synthesis to Biological Activity and Back
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Hana Vylíčilová, Magdaléna Bryksová, Vlasta Matušková, Karel Doležal, Lucie Plíhalová, and Miroslav Strnad
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cytokinin sugar conjugates ,glucoside ,riboside ,D-arabinoside ,disaccharides ,cytokinin nucleosides ,Microbiology ,QR1-502 - Abstract
Cytokinins and their sugar or non-sugar conjugates are very active growth-promoting factors in plants, although they occur at very low concentrations. These compounds have been identified in numerous plant species. This review predominantly focuses on 9-substituted adenine-based cytokinin conjugates, both artificial and endogenous, sugar and non-sugar, and their roles in plants. Acquired information about their biological activities, interconversions, and metabolism improves understanding of their mechanisms of action and functions in planta. Although a number of 9-substituted cytokinins occur endogenously, many have also been prepared in laboratories to facilitate the clarification of their physiological roles and the determination of their biological properties. Here, we chart advances in knowledge of 9-substituted cytokinin conjugates from their discovery to current understanding and reciprocal interactions between biological properties and associated structural motifs. Current organic chemistry enables preparation of derivatives with better biological properties, such as improved anti-senescence, strong cell division stimulation, shoot forming, or more persistent stress tolerance compared to endogenous or canonical cytokinins. Many artificial cytokinin conjugates stimulate higher mass production than naturally occurring cytokinins, improve rooting, or simply have high stability or bioavailability. Thus, knowledge of the biosynthesis, metabolism, and activity of 9-substituted cytokinins in various plant species extends the scope for exploiting both natural and artificially prepared cytokinins in plant biotechnology, tissue culture, and agriculture.
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- 2020
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42. Comprehensive metabolic study of IOX4 in equine urine and plasma using liquid chromatography/electrospray ionization Q Exactive high‐resolution mass spectrometer for the purpose of doping control
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Jenny K.Y. Wong, Yat-Ming So, Kanichi Kusano, Yu Sone, Masayuki Yamada, Takahiro Kamiya, Emmie N.M. Ho, Hideaki Ishii, Ai Wakuno, Hideki Ito, Mariko Shibuya, Gary Ngai-Wa Leung, and Kenji Miyata
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Doping in Sports ,Spectrometry, Mass, Electrospray Ionization ,Chromatography ,Electrospray ionization ,Pharmaceutical Science ,Urine ,Plasma ,Mass spectrometry ,Analytical Chemistry ,chemistry.chemical_compound ,Glucuronides ,Glucoside ,chemistry ,In vivo ,Enzymatic hydrolysis ,Animals ,Environmental Chemistry ,Horses ,Glucuronide ,Spectroscopy ,Chromatography, Liquid - Abstract
IOX4 is a hypoxia-inducible factor prolyl hydroxylase (HIF-PHD) inhibitor, which was developed for the treatment of anemia by exerting hematopoietic effects. The administration of HIF-PHD inhibitors such as IOX4 to horses is strictly prohibited by the International Federation of Horseracing Authorities and the Fédération Équestre Internationale. To the best of our knowledge, this is the first comprehensive metabolic study of IOX4 in horse plasma and urine after a nasoesophageal administration of IOX4 (500 mg/day, 3 days). A total of four metabolites (three mono-hydroxylated IOX4 and one IOX4 glucuronide) were detected from the in vitro study using homogenized horse liver. As for the in vivo study, post-administration plasma and urine samples were comprehensively analyzed with liquid chromatography/electrospray ionization high-resolution mass spectrometry to identify potential metabolites and determine their corresponding detection times. A total of 10 metabolites (including IOX4 glucuronide, IOX4 glucoside, O-desbutyl IOX4, O-desbutyl IOX4 glucuronide, four mono-hydroxylated IOX4, N-oxidized IOX4, and N-oxidized IOX4 glucoside) were found in urine and three metabolites (glucuronide, glucoside, and O-desbutyl) in plasma. Thus, the respective quantification methods for the detection of free and conjugated IOX4 metabolites in urine and plasma with a biphase enzymatic hydrolysis were developed and applied to post-administration samples for the establishment of elimination profiles of IOX4. The detection times of total IOX4 in urine and plasma could be successfully prolonged to at least 312 h.
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- 2021
43. Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues
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Yujiao He, Hongbo Dong, Min Wu, Zheng Shi, Weihong Du, and Yingying Wang
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Lipopolysaccharides ,Pharmacology ,Phenylpropionates ,Traditional medicine ,medicine.drug_class ,Organic Chemistry ,Anti-Inflammatory Agents ,Pharmaceutical Science ,Nitric Oxide ,Syringaldehyde ,Anti-inflammatory ,Analytical Chemistry ,Syringin ,Mice ,chemistry.chemical_compound ,RAW 264.7 Cells ,Glucosides ,Complementary and alternative medicine ,chemistry ,Glucoside ,Drug Discovery ,medicine ,Animals ,Molecular Medicine ,No production - Abstract
Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.
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- 2021
44. Involvement of CYP347W1 in neurotoxin 3‐nitropropionic acid‐based chemical defense in mustard leaf beetle Phaedon cochleariae
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Tobias Becker, Wolfgang Brandt, Nanxia Fu, Antje Burse, Maritta Kunert, and Wilhelm Boland
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biology ,Neurotoxins ,Phaedon cochleariae ,Active site ,Cytochrome P450 ,Monooxygenase ,Nitro Compounds ,General Biochemistry, Genetics and Molecular Biology ,Enzyme assay ,Coleoptera ,chemistry.chemical_compound ,Glucoside ,chemistry ,Biochemistry ,Biosynthesis ,Insect Science ,Hemolymph ,biology.protein ,Animals ,Propionates ,Agronomy and Crop Science ,Ecology, Evolution, Behavior and Systematics ,Mustard Plant - Abstract
Chrysomelina beetlesstore 3-nitropropionic acid in form of a pretoxin, isoxazolin-5-one glucoside-conjugated ester, to protect themselves against predators. Here we identified a cytochrome P450 monooxygenase, CYP347W1, to be involved in the production of the 3-nitropropionic acid moiety of the isoxazolin-5-one glucoside ester. Knocking down CYP347W1 led to a significant depletion in the concentration of the isoxazolin-5-one glucoside ester and an increase in the concentration of the isoxazolin-5-one glucoside in the larval hemolymph. Enzyme assays with the heterologously expressed CYP347W1 showed free β-alanine was not the direct substrate. Homology modeling indicated that β-alanine-CoA ester can fit into CYP347W1's active site. Furthermore, we proved that Phaedon cochleariae eggs are not able to de novo synthesize 3-NPA, although both isoxazolin-5-one glucoside and its 3-NPA-conjugated ester are present in the eggs. These results provide direct evidence for the involvement of CYP347W1 in the biosynthesis of a P. cochleariae chemical defense compound.
- Published
- 2021
45. Antibacterial phytocomplexes and compounds from Psychotria sycophylla (Rubiaceae) against drug-resistant bacteria
- Author
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Paul Nayim, Olive Monique F Demgne, Véronique Penlap Beng, Armel Jackson Seukep, Michel-Gael F. Guefack, Mathieu Tene, Pierre Tane, Brice E. N. Wamba, Judith Flore Tchuissang Mbougnia, Victor Kuete, and Armelle T. Mbaveng
- Subjects
Chromatography ,biology ,Chemistry ,Ethyl acetate ,biology.organism_classification ,chemistry.chemical_compound ,Complementary and alternative medicine ,Glucoside ,Ursolic acid ,Betulinic acid ,Antibacterial activity ,Oleanolic acid ,Bacteria ,Lupeol - Abstract
In this study, we examined the antibacterial and antibiotic-resistance reversal properties of methanol (MeOH) and ethyl acetate (EtOAc) extracts and compounds from Psychotria sycophylla aerial parts against drug-resistant bacteria. The tests were performed using the microdilution method. The mechanisms of action were investigated on growth kinetic and proton pumps of Escherichia coli. The structures of isolated compounds including oleanolic acid (1), ursolic acid (2), lupeol (3), betulinic acid (4), β-sitosterol glucoside (5), and stigmasterol (6), were established based on nuclear magnetic resonance (NMR) and electrospray ionization-mass spectrometry (ESI–MS). The extracts displayed noteworthy antibacterial activities, with recorded minimal inhibitory concentrations (MIC) ranging from 4 to 1024 µg/mL. Significant activities (MIC
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- 2021
46. Salicylate Glucoside as a Nontoxic Plant Protectant Alternative to Salicylic Acid
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Girish Swayambhu, Baradwaj G. Ravi, Indu Raghavan, Zhen Q. Wang, and Blaine A. Pfeifer
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chemistry.chemical_compound ,Chromatography ,Glucoside ,chemistry ,Plant Science ,Agricultural and Biological Sciences (miscellaneous) ,Agronomy and Crop Science ,Salicylic acid ,Food Science - Published
- 2021
47. Flavonoid compounds of buah merah (Pandanus conoideus Lamk) as a potent SARS-CoV-2 main protease inhibitor: in silico approach
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Umar, Abd. Kakhar
- Subjects
Antiparasitic ,medicine.drug_class ,medicine.medical_treatment ,Quercetin 3′-glucoside ,Taxifolin 3-O-α-arabinopyranose ,Flavonoid ,RM1-950 ,chemistry.chemical_compound ,Pharmacy and materia medica ,Glucoside ,medicine ,Taxifolin ,chemistry.chemical_classification ,Protease ,Traditional medicine ,biology ,Chemistry ,Research ,COVID-19 ,Anti-SARS-CoV-2 agents ,Pandanus conoideus ,biology.organism_classification ,RS1-441 ,Docking (molecular) ,Therapeutics. Pharmacology ,Quercetin ,Quercetin 3-O-glucose - Abstract
Background COVID19 is a global pandemic that threatens all nations. As there is no effective antiviral drug for COVID19, we examined the potency of natural ingredients against the SARS-CoV-2 main protease (PDB ID 6YNQ). Buah merah is a typical fruit from Papua, Indonesia, which is known to contain high levels of carotenoids and flavonoids. The contents have been proven to be effective as antiparasitic and anti-HIV. An in silico approach to 16 metabolites of buah merah (Pandanus conoideus Lamk) was carried out using AutoDock Vina. Furthermore, the study of the dynamics of ligand–protein interactions was carried out using CABS Flex 2.0 server to determine the test ligand and receptor complexes' stability. ADMET prediction was also carried out to study the pharmacokinetic profile of potential antiviral candidates. Result The docking results showed that 3 of the 16 buah merah metabolites were potent inhibitors against the SARS-CoV-2 main protease. The flavonoid compounds are quercetin 3′-glucoside, quercetin 3-O-glucose, and taxifolin 3-O-α-arabinopyranose with a binding affinity of − 9.7, − 9.3, and − 8.8, respectively, with stable ligand–protein complex. ADMET study shows that the three compounds are easily dissolved, easily absorbed orally and topically, have a high unbound fraction, low toxicity, and non-irritant. Conclusion We conclude that quercetin 3′-glucoside, quercetin 3-O-glucose, and taxifolin 3-O-α-arabinopyranose can be used and improved as potential anti-SARS-CoV-2 agents in further study.
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- 2021
48. Characterization of β-glucosidase of Lactobacillus plantarum FSO1 and Candida pelliculosa L18 isolated from traditional fermented green olive
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Nabil Ghabbour, Yahya Rokni, Ismail Hasnaoui, Z. Lamzira, Houssam Abouloifa, Sara Gaamouche, Ennouamane Saalaoui, Reda Bellaouchi, Abdeslam Asehraou, and Riadh Ben Salah
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Antioxidant ,medicine.medical_treatment ,QH426-470 ,chemistry.chemical_compound ,Glucoside ,Oleuropein ,medicine ,Genetics ,Candida pelliculosa ,Food science ,biology ,Research ,Olive ,biology.organism_classification ,Ascorbic acid ,Enzyme assay ,β-Glucosidase ,chemistry ,biology.protein ,Hydroxytyrosol ,Fermentation ,Lactobacillus plantarum ,TP248.13-248.65 ,Biotechnology - Abstract
Background Oleuropein, the main bitter phenolic glucoside responsible for green olive bitterness, may be degraded by the β-glucosidase enzyme to release glucose and phenolic compounds. Results Lactobacillus plantarum FSO1 and Candida pelliculosa L18 strains, isolated from natural fermented green olives, were tested for their β-glucosidase production and activity at different initial pH, NaCl concentrations, and temperature. The results showed that strains produced extracellular and induced β-glucosidase, with a molecular weight of 60 kD. The strains demonstrated their biodegradation capacity of oleuropein, associated with the accumulation of hydroxytyrosol and other phenolic compounds, resulting in antioxidant activity values significantly higher than that of ascorbic acid. The highest production value of β-glucosidase was 0.91 U/ml obtained at pH 5 and pH 6, respectively for L. plantarum FSO1 and C. pelliculosa L18. The increase of NaCl concentration, from 0 to 10% (w/v), inhibited the production of β-glucosidase for both strains. However, the β-glucosidase was activated with an increase of NaCl concentration, with a maximum activity obtained at 8% NaCl (w/v). The enzyme activity was optimal at pH 5 for both strains, while the optimum temperature was 45 °C for L. plantarum FSO1 and 35 °C for C. pelliculosa L18. Conclusions L. plantarum FSO1 and C. pelliculosa L18 strains showed their ability to produce an extracellular and induced β-glucosidase enzyme with promising traits for application in the biological processing of table olives.
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- 2021
49. Recent progress on biological production of α-arbutin.
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Zhu, Xingtong, Tian, Yuqing, Zhang, Wenli, Zhang, Tao, Guang, Cuie, and Mu, Wanmeng
- Subjects
- *
ARBUTIN , *HYDROQUINONE , *GLYCOSYLTRANSFERASES , *ENZYMES , *CYCLODEXTRINS - Abstract
Arbutin, a glucoside of hydroquinone, is used as a powerful skin lightening agent in the cosmeceutical industry because of its strong inhibitory effect on the human tyrosinase activity. It is a natural compound occurring in a number of plants, with a β-anomeric form of the glycoside bond between glucose and hydroquinone. α-Arbutin, which glycoside bond is generated with α-anomeric form, is the isomer of natural arbutin. α-Arbutin is generally produced by transglucosylation of hydroquinone by microbial glycosyltransferases. It is interesting that α-arbutin is found to be over 10 times more effective than arbutin, and thus biological production of α-arbutin attracts increasing attention. Seven different microbial enzymes have been identified to be able to produce α-arbutin, including α-amylase, sucrose phosphorlase, cyclodextrin glycosyltransferase, α-glucosidase, dextransucrase, amylosucrase, and sucrose isomerase. In this work, enzymatic and microbial production of α-arbutin is reviewed in detail. [ABSTRACT FROM AUTHOR]
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- 2018
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50. Glucosylation of T-2 and HT-2 toxins using biotransformation and chemical synthesis: Preparation, stereochemistry, and stability.
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Schmidt, Henning Sören, Schulz, Mareike, Focke, Christine, Becker, Stefanie, Cramer, Benedikt, and Humpf, Hans-Ulrich
- Abstract
Plant-derived phase II metabolites of T-2 toxin (T2) and HT-2 toxin (HT2) were first described in 2011 and further characterized in the following years. Since then, some efforts have been made to understand their biosynthesis, occurrence, toxicity, toxicokinetics, and finally relevance for consumers. Thus, the probably most important question is whether and how these metabolites contribute to toxicity upon hydrolysis either during food processing or the gastrointestinal passage. To answer this question, firstly, knowledge on the correct stereochemistry of T2 and HT2 glucosides is important as this affects hydrolysis and chemical behavior. So far, contradictory results have been published concerning the number and anomericity of occurring glucosides. For this reason, we set up different strategies for the synthesis of mg-amounts of T2, HT2, and T2 triol glucosides in both α and ß configuration. All synthesized glucosides were fully characterized by NMR spectroscopy as well as mass spectrometry and used as references for the analysis of naturally contaminated food samples to validate or invalidate their natural occurrence. Generally, 3-O-glucosylation was observed with two anomers of HT2 glucoside being present in contaminated oats. In contrast, only one anomer of T2 glucoside was found. The second aspect of this study addresses the stability of the glucosides during thermal food processing. Oat flour was artificially contaminated with T2 and HT2 glucosides individually and extruded at varying initial moisture content and temperature. All four glucosides appear to be more stable during food extrusion than the parent compounds with the glucosidic bond not being hydrolyzed. [ABSTRACT FROM AUTHOR]
- Published
- 2018
- Full Text
- View/download PDF
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