Heterogeneously elevated branched-chain/aromatic amino acids among new-onset type-2 diabetes mellitus patients are potentially skewed diabetes predictors

BACKGROUND The lack of specific predictors for type-2 diabetes mellitus(T2DM)severely impacts early intervention/prevention efforts.Elevated branched-chain amino acids(BCAAs:Isoleucine,leucine,valine)and aromatic amino acids(AAAs:Tyrosine,tryptophan,phenylalanine)show high sensitivity and specificity in predicting diabetes in animals and predict T2DM 10-19 years before T2DM onset in clinical studies.However,improvement is needed to support its clinical utility.AIM To evaluate the effects of body mass index(BMI)and sex on BCAAs/AAAs in new-onset T2DM individuals with varying body weight.METHODS Ninety-seven new-onset T2DM patients(<12 mo)differing in BMI[normal weight(NW),n=33,BMI=22.23±1.60;overweight,n=42,BMI=25.9±1.07;obesity(OB),n=22,BMI=31.23±2.31]from the First People’s Hospital of Yunnan Province,Kunming,China,were studied.One-way and 2-way ANOVAs were conducted to determine the effects of BMI and sex on BCAAs/AAAs.RESULTS Fasting serum AAAs,BCAAs,glutamate,and alanine were greater and high-density lipoprotein(HDL)was lower(P<0.05,each)in OB-T2DM patients than in NW-T2DM patients,especially in male OB-T2DM patients.Arginine,histidine,leucine,methionine,and lysine were greater in male patients than in female patients.Moreover,histidine,alanine,glutamate,lysine,valine,methionine,leucine,isoleucine,tyrosine,phenylalanine,and tryptophan were significantly correlated with abdominal adiposity,body weight and BMI,whereas isoleucine,leucine and phenylalanine were negatively correlated with HDL.CONCLUSION Heterogeneously elevated amino acids,especially BCAAs/AAAs,across new-onset T2DM patients in differing BMI categories revealed a potentially skewed prediction of T2DM development.The higher BCAA/AAA levels in obese T2DM patients would support T2DM prediction in obese individuals,whereas the lower levels of BCAAs/AAAs in NW-T2DM individuals may underestimate T2DM risk in NW individuals.This potentially skewed T2DM prediction should be considered when BCAAs/AAAs are to be used as the T2DM predictor.

THERMODYNAMIC STUDY ON ADSORPTION OF AROMATIC SULFONIC ACIDS ONTO MACROPOROUS WEAK BASE ANION EXCHANGER FROM AQUEOUS SOLUTIONS

The adsorption equilibrium isotherms of three aromatic sulfonic acid compounds, 2-naphthalenesulfonic acid, p-toluenesulfonic acid and p-chlorobenzenesulfonic acid, from aqueous solutions by macroporous weak base anion exchanger within the temperature range of 293 K-313 K were obtained. Several isotherm equations were correlated with the equilibrium data, and the experimental data was found to fit the three-parameter Redlich-Peterson equation best within the entire range of concentrations. The study showed that the hydrophobicity of solute has distinct influence on adsorption capacity of the anion exchanger for the aromatic sulfonic acid. Moreover, estimations of the isosteric enthalpy, free energy, and entropy change of adsorption were also reported. The positive isosteric enthalpy and entropy change for adsorption indicate an endothermic and entropy driven process in the present study.

Separation of Aromatic Carboxylic Acids in IC and the Study on the Relationship Between Retention Behavior and Electrostatic Potential

A method has been developed for separation of 20 kinds of aromatic carboxylic acid using anion-exchange chromatography. A Dionex IonPac AS9-HC guard column （250mm×2mm） was used with a 9mmol/L sodium carbonate solution containing 50% （v/v） acetonitrile as eluent. A set of retention time data has been obtained using a conductivity detector DS6. Furthermore, geometrical optimization and electrostatic potential calculation of 20 kinds of aromatic carboxylic acid have been performed at the HF/6-31G＊ level of theory. A number of statistically-based parameters derived from molecular surface electrostatic potential have been obtained. Linear relationship between retention time and structural parameters has been established by multiple regression method. The result shows that parameters derived from electrostatic potential Vs ＋, Vs -, П together with the dipole moment μ can be well used to express the quantitative structure-retention time of this kind of aromatic carboxylic acid. Good predictive capability has also been demonstrated. The result has provided a framework which further proves the general applicability of this electrostatic potential parameter set to a great extent,and with which the ion chromatographic adsorption mechanism can be investigated.

Peroxide Index, Trans Fatty Acids, Acrylamide and Polycyclic Aromatic Hydrocarbons (Pah) Contents in Frying Oils and Fried Tuna Fish Involved in “Garba” Production in Côte d’Ivoire

This current study aims at determining the profile and contents of degradation compounds produced during the interaction between the frying oils and tuna fish involved in the cooking of “Garba”, a street food largely consumed in C&#244;te d’Ivoire. For this purpose, the peroxide index and the neoformed compounds, especially trans fatty acids, acrylamid, polycyclic aromatic hydrocarbons were determined. This trial was carried out on 90 samples of frying oils and fried tuna fish collected from restaurant owners of “Garba” food in three locations in Abidjan. The samples were divided into three groups (G1, G2, and G3) according to the similarity of the practices adopted by the restorers. The results show that the peroxide values (14.95;15.01 and 11.97 meqO2/kg) of the oils respectively for G2, G3, and G1 are higher than the values fixed by the Codex Alimentarius. The trans fatty acid contents of the frying oils were 56.80%;61.01% and 55.18% respectively for G3, G2 and G1. The average acrylamide content of fried Tuna (69.43 μg/kg) is higher than the value recorded in the cooking oil (19.99 μg/kg). The average contents of the eleven HAPs determined in the oils are higher than those of the Tuna. The Benzo (a) pyrene contents of both matrices are lower than the EU standard 1881/2011 except for the G2 oil (2.66 μg/kg). Increased consumption of “Garba” may pose health risks to consumers as practices of frying Tuna generate compounds that are harmful to human health.

Aromatic L-amino acid decarboxylase cells in the spinal cord:a potential origin of monoamines

Monoamine neurotransmitters include catecholamines and indoleamines. The most common catecholamines are do- pamine （DA）, noradrenaline （NA） and adrenaline, which are produced from phenylalanine and tyrosine; whereas the most common indoleamine is serotonin （5-hydroxytrypta mine, 5-HT）, which is produced from 5-hydroxytryptophan （5-HTP）.

Branched-chain/aromatic amino acids as integrated biomarker of type 2 diabetes mellitus: a systematic review and meta-analysis

Background:As type 2 diabetes mellitus(T2DM)biomarkers,branched-chain amino acids(BCAAs:valine,leucine and isoleucine)and aromatic amino acids(AAAs:phenylalanine,tryptophan and tyrosine)may be correlated with the occurrence and development of T2DM.However,there is still no consensus on the disperse and isolated biomarkers of T2DM.Purpose:To explore the correlation between amino acids and T2DM based on integrated biomarker approach revealed.Methods:PubMed,Web of Science and CNKI were selected to search the literature published until August 31,2019.The included studies described the association between BCAAs,AAAs and T2DM.Random effect model and fixed effect model were adopted in pooled analysis to determine mean difference and 95 percent confidence interval of metabolites.Integrated biomarker was constructed in form of concentration change ratios or risk ratio(RR),relative risk(HR)and odds ratio(OR)of BCAAs and AAAs to reflect the integrated change information of amino acids.Results:The selected 20 studies contained 14942 healthy individuals and 3615 T2DM patients.The levels of BCAAs,phenylalanine and tyrosine both in plasma and serum samples were increased among all T2DM patients compared with those of the healthy control subjects(P<0.00001).However,the mean difference of tryptophan concentration was not statistically significant(P=0.60).The concentration change ratios or HR/RR/OR of BCAAs and AAAs were connected to form integrated biomarker.Conclusion:The integrated biomarker including BCAAs and AAAs could reflect the basic characteristics of T2DM,which has the potential clinical value on comprehensive diagnosis of T2DM.

Synthesis and Properties of Ternary Europium Complexes with Aromatic Carboxylic Acid and Nitrogen-Containing Heterocyclic Ligand

Seven ternary Eu （m） complexes were synthesized with aromatic carboxylic acid （benzoic acid, phenylacetic acid, phenylpropionic acid and cinnamic acid） as the first ligand and 1,10-phenanthro- line or 2,2＇-dipyridyl as the second ligand. The ternary Eu（ Ⅲ ） complexes were characterized by elemental analysis, IR and TG-DTG methods. In these complexes, the Eu （Ⅲ） ions are bonded to the oxygen atoms of carboxylate and the nitrogen atoms of neutral ligands. Four complexes whose second ligand is 1,10- phenanthrolin have fine thermal stability. Excitation and luminescence spectra of the tide complexes reveal that the fluorescence of the complexes in which 1,10- phenanthrolin as the second ligand are more intensive than those complexes in which 2, 2＇-dipyridyl as the second ligand. The order of the strongest emission peak of seven ternary complexes is： Eu（β-PPA）3phen 〉 Eu（BA）3phen 〉 Eu（PLA）3phen 〉 Eu（BA）3bipy 〉 Eu （ PEA）3bipy 〉 Eu （ CA ）3phen · H2O 〉 Eu （ CA ）3bipy （BA ： benzoic ; PEA ： phenylacetic ; β-PPA ：

Abundance and sources of particulate polycyclic aromatic hydrocarbons and aromatic acids at an urban site in central China

We conducted a simultaneous field study of PM_(2.5)-bound particulate polycyclic aromatic hydrocarbons(PAHs)and aromatic acids(AAs)in a polluted city Zhengzhou to explore the concentration,sources and potential conversion pathways between PAHs and AAs in different seasons.The average concentrations of PM_(2.5),28PAHs and 8AAs during the sampling period were 77μg/m^(3),75 ng/m^(3),and 283 ng/m^(3),respectively.The concentration of both28PAHs and 8AAs were highest in winter and lowest in summer with ratios of 6.3 and 2.3,respectively.PAHs with 5-7 rings were the main components of PAHs(52%),followed by 4rings PAHs(30%)and 2-3 rings PAHs(18%).According to the source appointment results obtained by positive matrix factorization,the main sources of PAHs were combustion and vehicle emissions,which account for 37%and 34%,respectively.8AAs were divided into three groups,including four benzene dicarboxylic acids(B2CAs),three benzene tricarboxylic acids(B3CAs)and one benzene tetracarboxylic acid(B4CA).And interspecies correlation analysis with PM_(2.5)source markers were used to investigate potential sources.Phthalic acid(o-Ph)was the most abundant specie of 8AAs(157 ng/m^(3),55%of 8AAs),which was well correlated with sulfate.Meanwhile,B3CAs and B4CA were highly correlated with sulfate and weakly correlated with levoglucosan,suggesting that secondary formation was their main source.As logical oxidation products of PAHs,o-Ph and B3CAs showed good correlations with a number of PAHs,indicating possible photochemical oxidation pathway by PAHs.In addition,O_(3),NO_(2),temperature and relative humidity have positive effects on the secondary formation of B3CAs.

Electrochemical-Voltammetry Behavior of Several Aromatic Aldehydes in Acid Solution

The electrochemical-voltammetry behavior of vanillin, heliotropin, anisaldehyde on the surface of Pt, Au electrodes in acid solution has been studied by means of the electrochemical cyclic voltammetry method. It was found that the electrochemical processes of them are irreversible on both Pt and Au electrodes. The electrochemical activity of vanillin is stronger than heliotropin's and heliotropin's is stronger than anisaldehyde's on Pt electrode. While the electrochemical activity of anisaldehyde is stronger than heliotropin's and vanillin's is the weakest on Au. The results indicate that when they are used as additives for electroplating, they must be consumptive, and it will improve the leveling ability of plating solution and brightness of the deposition layer.

Novel Method for Selective Debenzylation Under Maintenance of Fluoro Atom Substituted on β-Amino Acids

tert-Butyl （R）-3-amino-3-（3-fluorophenyl）propanoate（5） was prepared with conventional debenzylation method. However, the tert-butyl （R）-3-[（S）-1-phenylethyl-amino]-3-（3-fluorophenyl） propanoate（6） and tert-butyl （R）-3-amino-3-phenylpropanoate（7） were generated as the byproducts under the general catalytic hydrogenation Pd（OH）2/C-H2 conditions. So a series of experiments was performed to optimize the reaction conditions so that product 5 could be obtained with high purity and yield. Finally an effective catalytic system, Pd/C-HCOOH-CH3OH, was discovered.

Effects of Exogenousα-Ketoglutaric Acid on 2-Acetyl-1-Pyrroline,Yield Formation and Grain Quality Characters of Aromatic Rice

The improvement of grain quality in aromatic rice is very important for farmer to increase their income.Present study was conducted with a two-year field experiment and three aromatic rice cultivars in order to study the effects of exogenousα-ketoglutaric acid on yield formation,grain quality characters and the biosynthesis of 2-acetyl-1-pyrroline(2-AP,key component of aromatic rice’s fragrance)in aromatic rice.At heading stage,0.50 mmol L^(-1)(T1)and 1.00 mmol L^(-1)(T2)α-ketoglutaric acid solutions were overhead sprinkle to aromatic rice plants,respectively while the treatment which was overhead sprinkled with distilled water was set as control(CK).The results showed that 17.34%-33.04%and 21.39%-34.74%higher grain 2-AP contents were recorded in T1 and T2 treatments,respectively.Compared with CK,T1 and T2 treatments significantly reduced the transcript level of gene BADH2 which is related to the 2-AP biosynthesis in aromatic rice.3.86%-7.51%higher grain protein contents and 1.15%-3.37%higher head rice rates were also recorded inα-ketoglutaric acid treatments than CK.Moreover,T1 and T2 treatments remarkably decreased the chalky rice rate,chalkiness and grain amylose content.However,there was no remarkable difference in grain yield and related trails(effective panicle number,grain number per panicle,seed-setting rate and 1000-grain weight)among CK,T1 and T2 treatments.In conclusion,application of exogenousα-ketoglutaric acid enhanced 2-AP biosynthesis and improved grain quality of aromatic rice.

Aromatic Bromination in Concentrated Nitric Acid

Action of bromine in concentrated nitric acid allows carrying out mono- and polybromination of moderately deactivated aromatic compounds. 4-Chloronitrobenzene and isophthalic acid turnes into 3-bromo-4-chloronitrobenzene and 5-bromoisophthalic acid at reaction with bromine in concentrated nitric acid at 20°C whereas in absence of bromine in the same conditions 4-chloro-1, 3-dinitrobenzene and 5-nitroisophthalic acid are formed accordingly. Presence of bromine in concentrated nitric acid changes nitrating capacity to brominating one. Terephthalic acid and phthalic anhydride at heating with bromine in concentrated nitric acid can be transformed to appropriating tetrabromo substituted compounds.

Synthetic Approach for Novel Fluorine Substituted <i>α</i>-Aminophosphonic Acids Containing 1,2,4-Triazin-5-One Moiety as Antioxidant Agents

Novel fluorine substituted α-amino phosphonic acids containing 1,2,4-triazin- 5-one (6a-f) have been obtained from fluoroacylation of 6-(2&prime;-amino-5&prime;-nitrophenyl)-3-thioxo-1,2,4-triazin-5(4H)-one (1) followed by ammonilysis to give the corresponding 3-amino-derivative 3. Condensation of compound 3 with nitro/halogenated aromatic aldehydes yielded the Schiff bases 4. The simple addition of diethyl phosphonate to compound 4 produced the α-amino phosphonates 5. Acidic hydrolysis of compound 5 produced the fluorine substituted α-amino acids derivatives 6. Structures of the new compounds have been established with the help of elemental analysis and spectral measurements. Also, the products evaluated as antioxidants, where the fluorinated α-amino phosphonic acids 6 are more active than the other synthesized systems.

Thermodynamic solvation of a series of homologous α-amino acids in non-aqueous mixture of ethylene-glycol and N,N-dimethyl formamide

Standard free energies (ΔG0t(i) ) and entropies (ΔS0t(i)) of transfer of some homologous α-amino acids viz. glycine (gly), dl-alanine (ala), dl-α-amino butyric acid (aba) and dl-nor-valine (nor-val) from protic ethylene glycol (EG) to dipolar aprotic N,N-dimethyl formamide (DMF) have been evaluated from solubility measure-ments at five equidistant temperatures i.e from 15 to 350C. The observed ΔG0t(i) and TΔS0t(i) Vs composition profiles are complicated because of the various interaction effects. The chemical effects of the transfer Gibbs energies (ΔG0t.ch(i)) and entropies of transfer (ΔS0t.ch(i)) have been obtained after elimination of cavity effect, estimated by the scaled particle theory and dipole-dipole interaction effects, estimated by the use of Keesom-orientation expression. The chemical contributions of transfer energetics of homologous α-amino acids are guided by the composite effects of increased dispersion interaction, basicity and decreased acidity, hydrogen bonding effects and solvophobic solvation of ethylene glycol and N, N-dimethyl formamide mixed solvent as compared to that of reference solvent (ethylene glycol).

Coking kinetics and influence of reaction-regeneration on acidity, activity and deactivation of Zn/HZSM-5 catalyst during methanol aromatization

The coking kinetics and reaction-regeneration on Zn/HZSM-5 （Zn/HZ） catalyst in the conversion of methanol to aromatics were investigated. The highest initial benzene, toluene and xylene （BTX） yield of ca. 67.7% was obtained on fresh Zn/HZ catalyst, which showed the worst catalytic stability. The cycle of reaction-regeneration significantly modified the texture and acidity of Zn/HZ catalyst, which in turn affected its catalytic performance and coking behavior in methanol conversion to BTX. The residual carbon located on the surface of Zn/HZ catalyst led to the decrease of acid sites and the change on the acid sites distribution, which played an important roles on its activity and deactivation. It was found that the high B/L ratio and the low total acid sites concentration of the Zn/HZ catalyst favored to the high BTX yield and good catalytic stability in methanol conversion.

Different characteristics of 40 kinds of free amino acids and 5-amino levulinic acid between wines and sakes(Japanese rice wines)

Based on a systemic analysis for the globa1 burden of disease study from 1990 to 2016,the Global Burden of Diseases(GBD)2016 Alcohol Collaborators reported that alcohol use was a 1eading nisk factor for globa1 disease burden and caused substantial health loss.However,alcoholic dnink(wines and sakes)contains abundant nutrients,particularly fermentable amino acids denived from grapes and rice.Amino acid nutrition and metabolism is strongly associated with health and preventiom against various diseases.The purpose of this study was to elucidate 40 kinds of free amino acid(FAA)profles in wines and sakes.In addition,the present study also provided the contents of 5-aminolevulinic acid(5-AI A)involved in the vital functionality of mitochondria.FAAs were detected and analyzed by use of an automatic amino acid analyzer.Aromatic amino acid,branched chain amino acid and Fischer ratio were calculated for each beverage.Individua1 FAAs showed significant differences between wines and sakes.Sakes abundantly contained almost all FAAs whereas wines had just a lttle content in some FAAs.Sakse were rich in arginine,glycine,alanine,valine,glutamic acid and leucine,while wines were remarkably nich in proline(Pro).Wines showed increased FAA levels in 6 kinds of variables(4-hydroxyproline,3-methy1 histidine,B-alanine,a-aminobutyric acid,Pro and a.-aminoadipic acid).In functionally characteristic FAAs,both wines and sakes were considerably abundant in y aminobutynic acid and 5-AI A The total amount of aromatic amino acid and branched chain amino acid were markedly higher in sakes than in wines.These results revealed that there were the apparent different characteristics in FAA profiles between wines and sakes.This difference resulted from fermentation process in wines(single fermentation)and sakes(paralle1 double fermentation).Forty kinds of FAA profiles are more usefu1 in investigating characteristics of the taste of wines and sakes.In future,detailed FAA analysis has the potential to find functional nutrients such as 5-AI A,whereas other foods generally contain ittle amount of these FAAs.

Molecular origin for pH-responsive wormlike micelles of zwitterionic surfactants triggered by aromatic acid derivatives

Introduction of aromatic acid derivatives(AADs)into zwitterionic surfactants is an efficient method to prepare wormlike micelles with pH-controllable viscosity;however,the coincident molecular origin of AAD/zwitterionic surfactant binary mixtures remains unclear.Herein,the self-assembly of hydroxyl derivatives of benzoic acid(BA)and cetyldimethyl betaine(BS-16)mixtures in water was systematically assessed,and various factors,such as the molecular structure,molar ratio of AAD and BS-16,and solution pH,were investigated.The structure-property relationship of AAD/BS-16 binary mixtures was established,which provided the molecular origin for the effect of AAD on micellar microstructures and the pH-induced morphological transitions.The ortho-substituted hydroxyl moiety in the BA molecule facilitated the formation of larger wormlike micelles,whereas the effect of the meta-substituted moiety was less significant.The para-substituted hydroxyl moiety in BA did not favor micellar growth.This moiety exhibited similar characteristics to the increasing hydroxyl moiety number in the AAD molecules or solution pH where the negative effects of steric hindrance and electrostatic interactions of molecules in micelles aredominant.

Adsorption thermodynamics and kinetic investigation of aromatic amphoteric compounds onto different polymeric adsorbents

The adsorption behavior ofp-aminobenzoic acid and o-aminobenzoic acid onto the different polymeric adsorbents was systematically investigated as a function of the solution concentration and temperature. Experimental results indicated that the equilibrium adsorption data of the four polymeric adsorbents fitted well in the Freundlich isotherm. The adsorption capacity of multi-functional polymeric adsorbent NJ-99 was the highest, which might be attributed to the strong hydrogen-bonding interaction between the amino groups on the resin and the carboxyl group of aminobenzoic acid. The adsorption capacity of o-aminobenzoic acid onto any adsorbent was higher than p-aminobenzoic acid. Thermodynamic studies suggested the exothermic, spontaneous physical adsorption process. Adsorption kinetics results showed that the adsorption followed the pseudo-second-order kinetics model and the intraparticle mass transfer process was the rate-controlling step.

A practical synthesis of trifluorophenyl R-amino acid:The key precursor for the new anti-diabetic drug sitagliptin

Sitagliptin is the first new anti-diabetic drug in DPP-Ⅳ inhibitor class. The general synthesis of sitagliptin is by coupling of the β-amino acid fragment with the heterocycle fragment. Though the specific β-amino acid can be easily made from the corresponding R-amino acid by Arndt-Eistert hornologation, the optically pure precursor R-amino acid is difficult to prepare. We herein reported a practical protocol to make the trifluorophenyl substituted R-amino acid 4 in 〉99.9% ee and 40.3% yield by the enzymatic resolution employing enantioselective hydrolysis and a general separation procedure. This protocol requires only cheap starting materials and friendly reaction condition. The procedure not only allows people to prepare the drug substance, but also provides an alternative method for prepareing the rare α-amino acid and the subsequent β-amino acid.