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Protective effect of total flavonoid C-glycosides from Abrus mollis extract on lipopolysaccharide-induced lipotoxicity in mice 被引量:8
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作者 WANG Yun JIANG Zhen-Zhou +7 位作者 CHEN Mi WU Mei-Juan GUO Hong-Li SUN Li-Xin WANG Hao ZHANG Shuang WANG Tao ZHANG Lu-Yong 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2014年第6期461-468,共8页
Abrus mollis is a widely used traditional Chinese medicine for treating acute and chronic hepatitis, steatosis, and fibrosis. It was found that the total flavonoid C-glycosides from Abrus mollis extract(AME) showed po... Abrus mollis is a widely used traditional Chinese medicine for treating acute and chronic hepatitis, steatosis, and fibrosis. It was found that the total flavonoid C-glycosides from Abrus mollis extract(AME) showed potent antioxidant, anti-inflammatory, and hepatoprotective activities. To further investigate the hepatoprotective effect of AME and its possible mechanisms, lipopolysaccharide(LPS)-induced liver injury models were applied in the current study. The results indicated that AME significantly attenuated LPS-induced lipid accumulation in mouse primary hepatocytes as measured by triglyceride(TG) and total cholesterol(TC) assays and Oil Red O staining. Meanwhile, AME exerted a protective effect on LPS-induced liver injury as shown by decreased liver index, serum aminotransferase levels, and hepatic lipid accumulation. Real-time PCR and immunoblot data suggested that AME reversed the LPS-mediated lipid metabolism gene expression, such as sterol regulatory element-binding protein-1(SREBP-1), fatty acid synthase(FAS), and acetyl-CoA carboxylase 1(ACC1). In addition, LPS-induced overexpression of activating transcription factor 4(ATF4), X-box-binding protein-1(XBP-1), and C/EBP homologous protein(CHOP) were dramatically reversed by AME. Furthermore, AME also decreased the expression of LPS-enhanced interleukin-6(IL-6) and cyclooxygenase-2(COX-2). Here, it is demonstrated for the first time that AME ameliorated LPS-induced hepatic lipid accumulation and that this effect of AME can be attributed to its modulation of hepatic de novo fatty acid synthesis. This study also suggested that the hepatoprotective effect of AME may be related to its down-regulation of unfolded protein response(UPR) activation. 展开更多
关键词 Flavonoid c-glycosides ENDOTOXIN Unfolded protein response Lipid metabolism Inflammation
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Anti-inflammatory and hepatoprotective effects of total flavonoid C-glycosides from Abrus mollis extracts 被引量:9
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作者 CHEN Mi WANG Tao +6 位作者 JIANG Zhen-Zhou SHAN Chun WANG Hao WU Mei-Juan ZHANG Shuang ZHANG Yun ZHANG Lu-Yong 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2014年第8期590-598,共9页
The aim of this study was to evaluate the anti-inflammatory and hepatoprotective effects of the total flavonoid C-glycosides isolated from Abrus mollis extracts(AME). In the anti-inflammatory tests, xylene-induced ear... The aim of this study was to evaluate the anti-inflammatory and hepatoprotective effects of the total flavonoid C-glycosides isolated from Abrus mollis extracts(AME). In the anti-inflammatory tests, xylene-induced ear edema model in mice and carrageenan-induced paw edema model in rats were applied. The hepatoprotective effects of AME were evaluated with various in vivo models of acute and chronic liver injury, including carbon tetrachloride(CCl4)-induced hepatitis in mice, D-galactosamine(D-GalN)-induced hepatitis in rats, as well as CCl4-induced hepatic fibrosis in rats. In the acute inflammation experiment, AME significantly suppressed xylene-induced ear edema and carrageenan-induced paw edema, respectively. In the acute hepatitis tests, AME significantly attenuated the excessive release of ALT and AST induced by CCl4 and D-GalN. In CCl4-induced hepatic fibrosis model, AME alleviated liver injury induced by CCl4 shown by histopathological sections of livers and improved liver function as indicated by decreased liver index, serum ALT, AST, TBIL, and ALP levels and hydroxyproline contents in liver tissues, and increased serum ALB and GLU levels. These results indicated that AME possesses potent anti-inflammatory activity in acute inflammation models and hepatoprotective activity in both acute and chronic liver injury models. In conclusion, AME is a potential anti-inflammatory and hepatoprotective agent and a viable candidate for treating inflammation, hepatitis, and hepatic fibrosis. 展开更多
关键词 Abrus mollis Flavonoid c-glycosides INFLAMMATION Liver injury
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Flavonoid C-glycosides from the seeds of Hovenia dulcis Thunb. 被引量:3
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作者 Fangfang Xu Biao Sun +1 位作者 Xiaoqi Zhang Bo Liu 《Journal of Chinese Pharmaceutical Sciences》 CAS CSCD 2020年第11期813-818,共6页
Ten known flavonoid C-glycosides identified as 2′′-O-β-D-glucopyranosyl isovitexin(1),spinosin(2),6′′′-acetyl spinosin(3),6′′′-p-hydroxycinnamoyl-2′′O-β-D-glucopyranosyl isovitexin(4),6′′′-p-hydroxy-cin... Ten known flavonoid C-glycosides identified as 2′′-O-β-D-glucopyranosyl isovitexin(1),spinosin(2),6′′′-acetyl spinosin(3),6′′′-p-hydroxycinnamoyl-2′′O-β-D-glucopyranosyl isovitexin(4),6′′′-p-hydroxy-cinnamoyl spinosin(5),6′′′-(E)-feruloyl O-β-Dglucopyranosyl isovitexin(6),isospinosin(7),isovitexin(8),swertisin(9),swertiajaponin(10)were purified from the seeds of Hovenia dulcis Thunb.Their structures were confirmed by spectroscopic data analysis and comparison with previous literature.All compounds were obtained from H.dulcis for the first time. 展开更多
关键词 Hovenia dulcis Thunb Chemical constituents Flavonoid c-glycosides
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Studies on C-glycosides——XII. Stereoselective synthesis of C-aryl glucosides
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作者 CAI Meng-Shen QIU Dong-Xu 《Acta Chimica Sinica English Edition》 SCIE CAS CSCD 1989年第4期372-375,共1页
2,3,4,6-Tetra-O-benzyl-D-glucopyranose l-a-(p-nitrobenzoate)reacted with aryl ethers in the presence of Lewis acid to give β-anomers stereoselectively in high yield, but reaction with 1,3- ditrimethylsilyloxybenzene ... 2,3,4,6-Tetra-O-benzyl-D-glucopyranose l-a-(p-nitrobenzoate)reacted with aryl ethers in the presence of Lewis acid to give β-anomers stereoselectively in high yield, but reaction with 1,3- ditrimethylsilyloxybenzene gave a-anomer using BF_3.Et_2O and β-anomer using anhydrous AICl_3 as catalyst. 展开更多
关键词 Stereoselective synthesis of C-aryl glucosides Studies on c-glycosides XII
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Synthesis of non-classical heteroaryl C-glycosides via Minisci-type alkylation of N‑heteroarenes with 4-glycosyl-dihydropyridines 被引量:1
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作者 Qingbing Wang Juan Duan +2 位作者 Pingping Tang Gong Chen Gang He 《Science China Chemistry》 SCIE EI CAS CSCD 2020年第11期1613-1618,共6页
A radical-mediated method was reported for diastereoselective synthesis of non-classical heteroaryl C-glycosides via Minisci-type alkylation of N-heteroarenes with 4-glycosyl-1,4-dihydropyridine(DHP)reagents.These DHP... A radical-mediated method was reported for diastereoselective synthesis of non-classical heteroaryl C-glycosides via Minisci-type alkylation of N-heteroarenes with 4-glycosyl-1,4-dihydropyridine(DHP)reagents.These DHP reagents serve as convenient precursors for various glycosyl radicals under the activation of single electron transfer(SET)oxidation by persulfate and visible light irradiation with or without photocatalyst. 展开更多
关键词 non-classical c-glycoside Minisci reaction 4-gIycosyl-dihydropyridine
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Controlled acid hydrolysis and kinetics of flavone C-glycosides from trollflowers 被引量:3
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作者 Mian Dou Xi-Hui He +4 位作者 Yan Sun Fang Peng Jiang-Yun Liu Li-Li Hao Shi-Lin Yang 《Chinese Chemical Letters》 SCIE CAS CSCD 2015年第2期255-258,共4页
Acid hydrolysis mechanisms of orientin-2"-O-galactopyranoside(OGA),orientin and other flavone C-glycosides in the trollflowers[Trollius chinensis Bunge) were studied in this report for the first time.Hydrolysis pa... Acid hydrolysis mechanisms of orientin-2"-O-galactopyranoside(OGA),orientin and other flavone C-glycosides in the trollflowers[Trollius chinensis Bunge) were studied in this report for the first time.Hydrolysis parameters including temperature,acidity,solvent and reaction time were comprehensively investigated.OGA could be hydrolyzed to orientin,followed by an isomerization to isoorientin via a reversible Wessely-Moser rearrangement reaction under stronger acidic conditions.A first-order kinetic model fitted the hydrolysis process of OGA well.Under the optimal hydrolysis conditions of 80 ℃,1.0 mol/L H^+ and 7 h reaction time,about 77%OGA was transformed to orientin with no detectable isoorientin.These results could be helpful for better understanding of the acid hydrolysis kinetics of flavone C-glycosides,as well as the preparation of these valuable components under controlled acid hydrolysis conditions. 展开更多
关键词 Flavone c-glycoside Orientin Trollius chinensis Acid hydrolysis Kinetic
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Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents
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作者 RANOUX Adeline LEMIEGRE Loc BENVEGNU Thierry 《Science China Chemistry》 SCIE EI CAS 2010年第9期1957-1962,共6页
This work presents expeditious synthesis of C-glycoside amphiphiles in aqueous media from unprotected di-or mono-saccharides.A Horner-Wadsworth-Emmons/Michael addition/Barbier allylation sequence led to C-glycosides t... This work presents expeditious synthesis of C-glycoside amphiphiles in aqueous media from unprotected di-or mono-saccharides.A Horner-Wadsworth-Emmons/Michael addition/Barbier allylation sequence led to C-glycosides that exhibit hydrotropic properties.The hydrotropic and solubilizing properties of these homoallylic alcohols including a β-C-glycoside moiety as well as additional β-C-glycosidic ketones with a short(C7) alkyl chain are also described and compared with those of commercial O-glucoside references. 展开更多
关键词 c-glycosidE amphiphiles Horner-Wadsworth-Emmons reaction Barbier ALLYLATION green CHEMISTRY HYDROTROPES
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A New C-glycosidic Hydrolysable Tannin from Rhodomyrtus tomentosa
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作者 Yan Ze LIU Ai Jun HOU +1 位作者 Chun Ru JI Yang Jie WU(Department of Phytochemistry Henen College of Traditional Chinese Medicine Xhengzhou 450003Department of Oraganic Chemistry Zhengzhou University Zhengzhou 450052) 《Chinese Chemical Letters》 SCIE CAS CSCD 1997年第1期39-40,共2页
Tomentosin(1), a new C-glycosidic hydrolysable tannin, isolated from the leaves of Rhodomyrtus tomentosa. Its structure determined by chemical method and (1)HNMR spectroscopic analysis.
关键词 A New c-glycosidic Hydrolysable Tannin from Rhodomyrtus tomentosa
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C-Glycoside Synthesis Enabled by Nickel Catalysis 被引量:3
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作者 Weidong Shang Rong Shi Dawen Niu 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2023年第17期2217-2236,共20页
Comprehensive Summary,C-Glycosides are critical,naturally occurring products and medicinal candidates,and extensive efforts have been made to explore efficient approaches for creating C-glycosidic bonds.Transition-met... Comprehensive Summary,C-Glycosides are critical,naturally occurring products and medicinal candidates,and extensive efforts have been made to explore efficient approaches for creating C-glycosidic bonds.Transition-metal-catalysis,particularly nickel-catalyzed C-glycosylation reactions constitute a promising strategy.However,achieving a stereoselective synthesis ofα-andβ-C-glycosides has been a long-standing challenge.To address this problem,a variety of nickel-mediated strategies have been developed.This review highlights recent developments in the nickel-catalyzed diastereoselective C-glycosylation reactions and briefly summarizes the mechanistic understandings of these methods. 展开更多
关键词 c-glycosides NICKEL GLYCOSYLATION Glycosyl radical Carbohydrates
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Structural mechanism of a dual-functional enzyme Dgp A/B/C as both a C-glycoside cleaving enzyme and an O-to C-glycoside isomerase
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作者 Pengfei He Sha Wang +7 位作者 Sen Li Siqi Liu Shuqi Zhou Jing Wang Jiayue Tao Dongdong Wang Rufeng Wang Wenfu Ma 《Acta Pharmaceutica Sinica B》 SCIE CAS CSCD 2023年第1期246-255,共10页
The C-glycosidic bond that connects the sugar moiety with aglycone is difficult to be broken or made due to its inert nature.The knowledge of C-glycoside breakdown and synthesis is very limited.Recently,the enzyme Dgp... The C-glycosidic bond that connects the sugar moiety with aglycone is difficult to be broken or made due to its inert nature.The knowledge of C-glycoside breakdown and synthesis is very limited.Recently,the enzyme Dgp A/B/C cascade from a human intestinal bacterium PUE was identified to specifically cleave the C-glycosidic bond of puerarin(daidzein-8-C-glucoside).Here we investigated how puerarin is recognized and oxidized by Dgp A based on crystal structures of Dgp A with or without substrate and biochemical characterization.More strikingly,we found that apart from being a C-glycoside cleaving enzyme,Dgp A/B/C is capable of efficiently converting O-to C-glycoside showing the activity as a structure isomerase.A possible mechanistic model was proposed dependently of the simulated complex structure of Dgp B/C with 3’’-oxo-daidzin and structure-based mutagenesis.Our findings not only shed light on understanding the enzyme-mediated C-glycosidic bond breakage and formation,but also may help to facilitate stereospecific C-glycoside synthesis in pharmaceutical industry. 展开更多
关键词 c-glycosidE O-Glycoside c-glycoside cleaving enzyme ISOMERASE Gut microbiota Flavonoid Puerarin and oxidoreductase
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Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides
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作者 Chen Li Ziyuan Zhao Shouyun Yu 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第6期263-267,共5页
Glycosyl radicals,produced under mild photoredox conditions,show unique utility in the preparation of C-linked glycoconjugates.We herein report the construction of C-glycosidic bonds on α,β-dehydroalanine(DHA)of pep... Glycosyl radicals,produced under mild photoredox conditions,show unique utility in the preparation of C-linked glycoconjugates.We herein report the construction of C-glycosidic bonds on α,β-dehydroalanine(DHA)of peptides with easily available glycosyl bromides as glycosyl radical precursors under highly anomeric control,leading to C-glycosylation modifications of peptides.This method not only has outstanding functional group compatibility,but also is feasible in near-physiological conditions(pH~7 and temperature T≤37℃ in aqueous media). 展开更多
关键词 Glycosylation c-glycosides GLYCOPEPTIDES DEHYDROALANINE Photoredox catalysis
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Pd-Catalyzed Stereospecific Glycosyl Cross-Coupling of Reversed Anomeric Stannanes for Modular Synthesis of Nonclassical C‑Glycosides
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作者 Guoqiang Cheng Bo Yang +6 位作者 Yang Han Wei Lin Siyuan Tao Yong Nian Yingzi Li Maciej A.Walczak Feng Zhu 《Precision Chemistry》 2024年第11期587-599,共13页
Nonclassical C-glycosides,distinguished by their unique glycosidic bond connection mode,represent a promising avenue for the development of carbohydrate-based drugs.However,the accessibility of nonclassical C-glycosid... Nonclassical C-glycosides,distinguished by their unique glycosidic bond connection mode,represent a promising avenue for the development of carbohydrate-based drugs.However,the accessibility of nonclassical C-glycosides hinders broader investigations into their structural features and modes of action.Herein,we present the first example of Pd-catalyzed stereospecific glycosylation of nonclassical anomeric stannanes with aryl or vinyl halides.This method furnishes desired nonclassical aryl and vinyl C-glycosides in good to excellent yields,while allowing for exclusive control of nonclassical anomeric configuration.Of significant note is the demonstration of the generality and practicality of this nonclassical C-glycosylation approach across more than 50 examples,encompassing various protected and unprotected saccharides,deoxy sugars,oligopeptides,and complex molecules.Furthermore,biological evaluation indicates that nonclassical C-glycosylation modifications of drug molecules can positively impact their biological activity.Additionally,extensive computational studies are conducted to elucidate the rationale behind differences in reaction reactivity,unveiling a transmetalation transition state containing silver(Ag)within a six-membered ring.Given its remarkable controllability,predictability,and consistently high chemical selectivity and stereospecificity regarding nonclassical anomeric carbon and Z/E configuration,the method outlined in this study offers a unique solution to the longstanding challenge of accessing nonclassical C-glycosides with exclusive stereocontrol. 展开更多
关键词 Glycosylation CROSS-COUPLING Nonclassical c-glycosides Reversed anomeric stannanes STEREOSPECIFICITY
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A new flavonol C-glycoside and a rare bioactive lignanamide from Piper wallichii Miq. Hand.-Mazz 被引量:4
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作者 WANG Pei-Pei ZHAO Guo-Wei +2 位作者 XIA Wen HAN En-Ji XIANG Lan 《Chinese Journal of Natural Medicines》 SCIE CAS CSCD 2014年第5期377-381,共5页
This study was conducted to investigate the chemical constituents of Piper wallichii (Miq.) Hand.-Mazz. and evaluate their biological activity. Compounds were isolated by various column chromatographic methods, and ... This study was conducted to investigate the chemical constituents of Piper wallichii (Miq.) Hand.-Mazz. and evaluate their biological activity. Compounds were isolated by various column chromatographic methods, and their structures were elucidated on the basis of physical characteristics and spectral data. The 1, 1-diphenyl-2-picrylhydrazyl (DPPH)-scavenging activity and acetylcholinesterase (AChE)-inhibitory activity of the compounds were evaluated. Five compounds were obtained and identified as 8-C-β-D-glucopyranosylkaempferol-3-O-β-D-glucopyranoside (1), 1, 2-dihydro-6,8-dimethoxy-7-hydroxy-l-(3, 5-dimethoxy-4-hydroxyphenyl)-N^1, N^2-bis-[2-(4-hydroxyphenyl)ethyl]-2, 3-naphthalene dicarboxamide (2), goniothalactam (3), aristololactam A IIla (4) and piperlonguminine (5). Compound 1 was a new flavonol C-glycoside, 2 was a rare lignanamide, which was isolated from the family Piperaceae for the first time, and compound 3 was isolated from this plant for the first time. Among them, 2 showed potent DPPH-scavenging activity, with IC50 of 31.38 ± 0.97 μmol·L^-1; Compounds 2, 3, and 4 showed AChE inhibitory activity at 100 μmol·L^-1, with inhibition rates of 28.57% ± 1.47%, 18.48% ± 2.41% and 17.4% ±3.03%, respectively. 展开更多
关键词 Piper wallichii Flavonol c-glycoside Lignanamide DPPH scavenging activity AChE inhibitory activity
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Synthesis of Triazole-Linked Amino Acid-Aryl C-Glycoside Hybrids via Click Chemistry as Novel PTPIB Inhibitors
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作者 Wang, Jia He, Xiaopeng +4 位作者 Gao, Lixin Sheng, Li Shi, Xiaoxin Li, Jia Chen, Guorong 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2011年第6期1227-1232,共6页
Triazolyl phenylalanine and tyrosine-aryl C-glycoside hybrids were readily synthesized via microwave-assisted Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition in high yields. Successive enzymatic assay identif... Triazolyl phenylalanine and tyrosine-aryl C-glycoside hybrids were readily synthesized via microwave-assisted Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition in high yields. Successive enzymatic assay identified the synthesized glycoconjugates as novel PTPlB inhibitors with low micromole-ranged inhibitory activity and at least several-fold selectivity over other homologous PTPs tested found crucial toward PTP1 B inhibition. In addition, the benzyl groups on glucosyl moiety were 展开更多
关键词 click chemistry c-glycosidE triazolyl amino acid PTP INHIBITORS
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C-Aryl Glycosylation via Interrupted Pummerer Rearrangement
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作者 Jiagen Li Xuefeng Jiang 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2023年第21期2843-2847,共5页
C-aryl glycosides are an important kind of carbohydrate derivatives for drug discovery,due to their distinctive attributes of resistance to hydrolysis from enzymes.Herein,C-aryl glycosylation was established for the s... C-aryl glycosides are an important kind of carbohydrate derivatives for drug discovery,due to their distinctive attributes of resistance to hydrolysis from enzymes.Herein,C-aryl glycosylation was established for the synthesis of 2-sulfur C-aryl glycals and 1,2-dihydrobenzofuran-fused C-aryl glycosides via interrupted Pummerer process,featured with sulfonium-tethered[3,3]-sigmatropic rearrangement between sulfoxide glycals and phenols.This protocol offers a broad substrate scope with diverse glycosyl and phenols.Dapagliflozin,Empagliflozin,and Ipragliflozin analogs were straightforward achieved,respectively. 展开更多
关键词 GLYCAL GLYCOSYLATION Interrupted pummerer REARRANGEMENT SULFOXIDE Carbohydrates c-glycosides Drug discovery
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A highly selective C-rhamnosyltransferase from Viola tricolor and insights into its mechanisms 被引量:2
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作者 Bo-Yun Han Zi-Long Wang +7 位作者 Junhao Li Qing Jin Hao-Tian Wang Kuan Chen Yang Yi Hansgren Xue Qiao Min Ye 《Acta Pharmaceutica Sinica B》 SCIE CAS CSCD 2023年第8期3535-3544,共10页
C-Glycosides are important natural products with various bioactivities.In plant biosynthetic pathways,the C-glycosylation step is usually catalyzed by C-glycosyltransferases(CGTs),and most of them prefer to accept uri... C-Glycosides are important natural products with various bioactivities.In plant biosynthetic pathways,the C-glycosylation step is usually catalyzed by C-glycosyltransferases(CGTs),and most of them prefer to accept uridine 5’-diphosphate glucose(UDP-Glc)as sugar donor.No CGTs favoring UDP-rhamnose(UDP-Rha)as sugar donor has been reported,thus far.Herein,we report the first selective C-rhamnosyltransferase VtCGTc from the medicinal plant Viola tricolor.VtCGTc could efficiently catalyze C-rhamnosylation of 2-hydroxynaringenin 3-C-glucoside,and exhibited high selectivity towards UDP-Rha.Mechanisms for the sugar donor selectivity of VtCGTc were investigated by molecular dynamics(MD)simulations and molecular mechanics with generalized Born and surface area solvation(MM/GBSA)binding free energy calculations.Val144 played a vital role in recognizing UDP-Rha,and the V144T mutant could efficiently utilize UDP-Glc.This work provides a new and efficient approach to prepare flavonoid C-rhamnosides such as violanthin and iso-violanthin. 展开更多
关键词 Flavonoid c-glycoside C-rhamnosyltransferase BIOSYNTHESIS Catalytic mechanisms Sugardonorselectivity
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Rapid characterization of 96 chemical constituents in Citri Reticulatae Folium(leaves of ‘Fuju') using HPLC-DAD-ESI-MS^n 被引量:5
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作者 曹规划 付庆荣 +2 位作者 张藏曼 王弘 陈世忠 《Journal of Chinese Pharmaceutical Sciences》 CAS CSCD 2016年第2期91-110,共20页
In order to systematically investigate the chemical constituents of Citri Reticulatae Folium (leaves of 'Fuju'), an analytical method that included high-performance liquid chromatography, diode array detection, el... In order to systematically investigate the chemical constituents of Citri Reticulatae Folium (leaves of 'Fuju'), an analytical method that included high-performance liquid chromatography, diode array detection, electrospray ionization, and ion-trap time-of-flight mass spectrometry (HPLC-DAD-ESI-MSn) was used to separate and identify the individual chemical components of Citri Reticulatae Folium. As a result, 96 compounds were tentatively identified in this study: including 31 phenolic acids, 4 flavonoid aglycones, 6 flavonoid mono-O-glycosides, 10 flavonoid-O-diglycosides, 5 flavonoid mono-C-glycosides, 5 flavonoid di-C-glycosides, 6 flavonoid O,C-glycosides, 5 (3-hydroxy-3-methylglutaryl) glycosyl flavonoids, 1 flavan-3-ol, and 2 alkaloids. In addition, 21 polymethoxy flavonoids (PMFs) were identified in this paper. Among these compounds, 52 compounds, which were previously found in other Citrus plants, have been identified for the first time in Citri Reticulatae Folium. 15 compounds have not been previously found in the Citrus genus were identified. Moreover, 9 potentially new compounds have also been detected in this paper. This is the first report of the full characterization of chemical components of Citri Reticulatae Folium (leaves of'Fuju') by HPLC-DAD-ESI-MSn. 展开更多
关键词 Citri Reticulatae Folium (leaves of ‘Fuju') HPLC-DAD-ESI-MS^n Flavonoid O c-glycosides PMFs
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Exploring the catalytic function and active sites of a novel C-glycosyltransferase from Anemarrhena asphodeloides 被引量:1
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作者 Jia Huang Yaru She +11 位作者 Jingyang Yue Yidu Chen Yu Li Jing Li Yonger Hu Deying Yang Jiabo Chen Lu Yang Zhongqiu Liu Ruibo Wu Pengfei Jin Lixin Duan 《Synthetic and Systems Biotechnology》 SCIE 2022年第1期621-630,共10页
Anemarrhena asphodeloides is an immensely popular medicinal herb in China,which contains an abundant of mangiferin.As an important bioactive xanthone C-glycoside,mangiferin possesses a variety of pharmacological activ... Anemarrhena asphodeloides is an immensely popular medicinal herb in China,which contains an abundant of mangiferin.As an important bioactive xanthone C-glycoside,mangiferin possesses a variety of pharmacological activities and is derived from the cyclization reaction of a benzophenone C-glycoside(maclurin).Biosyntheti-cally,C-glycosyltransferases are critical for the formation of benzophenone C-glycosides.However,the benzo-phenone C-glycosyltransferases from Anemarrhena asphodeloides have not been discovered.Herein,a promiscuous C-glycosyltransferase(AaCGT)was identified from Anemarrhena asphodeloides.It was able to catalyze efficiently mono-C-glycosylation of benzophenone,together with di-C-glycosylation of dihydrochalcone.It also exhibited the weak O-glycosylation or potent S-glycosylation capacities toward 12 other types of flavonoid scaffolds and a simple aromatic compound with–SH group.Homology modeling and mutagenesis experiments revealed that the glycosylation reaction of AaCGT was initiated by the conserved residue H23 as the catalytic base.Three critical residues H356,W359 and D380 were involved in the recognition of sugar donor through hydrogen-bonding interactions.In particular,the double mutant of F94W/L378M led to an unexpected enzy-matic conversion of mono-C-to di-C-glycosylation.This study highlights the important value of AaCGT as a potential biocatalyst for efficiently synthesizing high-value C-glycosides. 展开更多
关键词 c-glycosides Anemarrhena asphodeloides C-glycosyltransferases BENZOPHENONE Active sites
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Synthesis of alkynes and alkynyl iodides bearing a protected amino alcohol moiety as functionalized amino acids precursors 被引量:1
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作者 AYED Charfedinne PICARD Julien +2 位作者 LUBIN-GERMAIN Nadège UZIEL Jacques AUGE Jacques 《Science China Chemistry》 SCIE EI CAS 2010年第9期1921-1926,共6页
Amino acid precursors in protected amino alcohol form are important synthons that can be used as building-blocks for the hemisynthesis of non-natural amino acids.Serine can be used as a common starting material for th... Amino acid precursors in protected amino alcohol form are important synthons that can be used as building-blocks for the hemisynthesis of non-natural amino acids.Serine can be used as a common starting material for the synthesis of such compounds differently protected.Particularly,protected amino alcohols bearing an ethynyl and/or an iodoethynyl group can be used in cross-couplings,in 1,3-dipolar cycloadditions and/or in Nozaki-Hiyama-Kishi type reactions.We thus demonstrated that the efficiently protected amino alcohols derived from serine can be coupled to a sugar derivative by an indium mediated alkynylation reaction.The conditions of this coupling are compatible with such functionalized derivatives and allow envisaging an access to C-glycosylated amino acids. 展开更多
关键词 AMINO alcohols AMINO acids OXAZOLIDINES ALKYNYL IODIDES c-glycosidE indium ALKYNYLATION
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Total Synthesis of C-α-Mannosyl Tryptophan via Palladium-Catalyzed C-H Glycosylation 被引量:3
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作者 Quanquan Wang Yue Fu +6 位作者 Wanjun Zhu Shuang An Qianyi Zhou Shou-Fei Zhu Gang He Peng Liu Gong Chen 《CCS Chemistry》 CAS 2021年第6期1729-1736,共8页
The C2-α-mannosyl-tryptophan amino acid is produced by a unique posttranslational modification(PTM)of proteins and poses a significant synthetic challenge.A new strategy based on Pd-catalyzed auxiliary-directed remot... The C2-α-mannosyl-tryptophan amino acid is produced by a unique posttranslational modification(PTM)of proteins and poses a significant synthetic challenge.A new strategy based on Pd-catalyzed auxiliary-directed remote C-H glycosylation of tryptophan was developed,which generates the C2-α-mannopyranose(Man)-Trp unit in a highly efficient and stereoselective fashion.Density functional theory(DFT)computational studies support a concerted oxidative addition mechanism for the stereospecific functionalization of a Pd(II)palladacycle intermediate with anα-mannosyl chloride donor.The utility of this method was demonstrated in the first total synthesis of insect C-glycopeptide hormone Cam-HrTH-I. 展开更多
关键词 c-glycosidE C−H glycosylation PALLADIUM AUXILIARY adipokinetic hormone
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