New Crystalline Salts of Nicotinamide Riboside as Food Additives.

NR+ is a highly effective vitamin B3 type supplement due to its unique ability to replenish NAD+ levels. While NR+ chloride is already on the market as a nutritional supplement, its synthesis is challenging, expensive, and low yielding, making it cumbersome for large-scale industrial production. Here we report the novel crystalline NR+ salts, d/l/dl-hydrogen tartrate and d/l/dl-hydrogen malate. Their high-yielding, one-pot manufacture does not require specific equipment and is suitable for multi-ton scale production. These new NR+ salts seem ideal for nutritional applications due to their bio-equivalence compared to the approved NR+ chloride. In addition, the crystal structures of all stereoisomers of NR+ hydrogen tartrate and NR+ hydrogen malate and a comparison to the known NR+ halogenides are presented.

Generation of High Dose Inhalable Effervescent Dispersions against Pseudomonas aeruginosa Biofilms.

PURPOSE: Novel particle engineering approach was used in this study to generate high dose inhalable effervescent particles with synergistic effects against Pseudomonas aeruginosa biofilms. METHODS: Spray dried co-amorphous salt of ciprofloxacin (CFX) and tartaric acid (TA) was prepared and coated with external layer of sodium bicarbonate and silica coated silver nanobeads. Design of experiments (DOE) was used to optimize physicochemical properties of particles for enhanced lung deposition. RESULTS: Generated particles were co-amorphous CFX/TA showing that CFX lost its zwitterionic form and exhibiting distinct properties to CFX/HCl as assessed by FTIR and thermal analysis. Particles exhibited mass mean aerodynamic diameter (MMAD) of 3.3 µm, emitted dose of 78% and fine particle dose of 85%. Particles were further evaluated via antimicrobial assessment of minimum inhibitory concentrations (MIC) and minimum biofilm eradication concentration (MBEC). MIC and MBEC results showed that the hybrid particles were around 3-5 times more effective when compared to CFX signifying that synergistic effect was achieved. Diffusing wave spectroscopy results showed that the silver containing particles had a disruptive effect on rheological properties as opposed to silver free particles. CONCLUSIONS: Overall, these results showed the potential to use particle engineering to generate particles that are highly disruptive of bacterial biofilms.

Synthesis and Therapeutic Applications of Iminosugars in Cystic Fibrosis.

Iminosugars are sugar analogues endowed with a high pharmacological potential. The wide range of biological activities exhibited by these glycomimetics associated with their excellent drug profile make them attractive therapeutic candidates for several medical interventions. The ability of iminosugars to act as inhibitors or enhancers of carbohydrate-processing enzymes suggests their potential use as therapeutics for the treatment of cystic fibrosis (CF). Herein we review the most relevant advances in the field, paying attention to both the chemical synthesis of the iminosugars and their biological evaluations, resulting from in vitro and in vivo assays. Starting from the example of the marketed drug NBDNJ (N-butyl deoxynojirimycin), a variety of iminosugars have exhibited the capacity to rescue the trafficking of F508del-CFTR (deletion of F508 residue in the CF transmembrane conductance regulator), either alone or in combination with other correctors. Interesting results have also been obtained when iminosugars were considered as anti-inflammatory agents in CF lung disease. The data herein reported demonstrate that iminosugars hold considerable potential to be applied for both therapeutic purposes.

[Electrochemical fingerprint of traditional Chinese medicines based on BrO⁻3-Ce4⁺-H⁺-malonic acid/tartaric acid chemical oscillating system].

A new composite organic oscillating reaction system based on BrO3-Ce(SO4)2-H2SO4-malonic acid/tartaric acid was proposed in this paper. On the basis of the influence of the concentration of each component on the stability and characteristic parameters of the blank system, the electrochemical fingerprints of 30 kinds of traditional Chinese medicines (TCM) were obtained. The results showed that the electrochemical fingerprint can be used for the identification of TCMs, the distinguishment of different parts and the appraisal of genuineness, which is fast, sensitive and accurate. At the same time, we explored and verified the mechanism of oscillation and the formation mechanism of TCM fingerprint.

Development of Biopolymer Composite Films Using a Microfluidization Technique for Carboxymethylcellulose and Apple Skin Particles.

Biopolymer films based on apple skin powder (ASP) and carboxymethylcellulose (CMC) were developed with the addition of apple skin extract (ASE) and tartaric acid (TA). ASP/CMC composite films were prepared by mixing CMC with ASP solution using a microfluidization technique to reduce particle size. Then, various concentrations of ASE and TA were incorporated into the film solution as an antioxidant and an antimicrobial agent, respectively. Fourier transform infrared (FTIR), optical, mechanical, water barrier, and solubility properties of the developed films were then evaluated to determine the effects of ASE and TA on physicochemical properties. The films were also analyzed for antioxidant effect on 2,2-diphenyl-1-picrylhydrazyl radical scavenging activity and antimicrobial activities against Listeria monocytogenes, Staphylococcus aureus, Salmonella enterica, and Shigella flexneri. From the results, the ASP/CMC film containing ASE and TA was revealed to enhance the mechanical, water barrier, and solubility properties. Moreover, it showed the additional antioxidant and antimicrobial properties for application as an active packaging film.

Tartaric acid induced conversion of protopanaxadiol to ginsenosides Rg3 and Rg5 and their in situ recoveries by integrated expanded bed adsorption chromatography.

Panax ginseng has been applied in traditional Chinese medicine for over 2000 years. It is still one of the most popular herbs in recent decades. The prescribed ginseng-containing medicines consist of protopanaxadiol and protopanaxatriol ginsenosides, which are the major constituents of the herb. Minor ginsenosides at low levels in the herb, such as Rg3 and Rg5 , have attracted more rising attention than the major ones. The existing approaches to prepare Rg3 and Rg5 usually rely on either steamed red ginseng as the source or chemical/enzymatic conversion of protopanaxadiol to the targets. It is still highly desirable to effectively achieve such minor components. In this paper, a method integrated extraction of protopanaxadiol and conversion of it to Rg3 and Rg5 has been proposed. Protopanaxadiol was extracted and simultaneously converted to Rg3 and Rg5 by d,l-tartaric acid. The targets were absorbed by resins on expanded bed adsorption chromatography and were then separated from other ginsenosides in different stages. Compared with conventional methods, the developed process has advantages in shortening time consumption and improving the conversion ratio of protopanaxadiol, which is promising in directly achieving Rg3 and Rg5 from P. ginseng.

[Effect of Low Molecular Weight Organic Acids on the Chemical Speciation and Activity of Mercury in the Soils of the Water-Level-Fluctuating Zone of the Three Gorges Reservoir].

To investigate the effect of low molecular weight organic acids ( LMWOA) on the ability of migration and the species of mercury in the soil of the Water-Level-Fluctuating Zone of the Three Gorges Reservoir, citric acid, tartaric acid and oxalic acid were dded into the soil to conduct simulation experiments. The results showed that the percentage of exchangeable mercury increased with the increase of the concentration of citric acid, but the value declined slightly as the concentration of tartaric acid and oxalic acid increased. While all three acids elevated the bioavailability of mercury, which increased with the increase of the concentration of acids. Vhen the concentration of citric acid reached 15 mmol x L(-1), the activation effect was the best. But for oxalic acid and citric acid, 10 mmol x L(-1) was the optimal concentration. In general, the effect of three organic acids on the activation of mercury in the soil followed the trend of citric acid > tartaric acid > oxalic acid. In the soil supplemented with 15 mmol x L(-1) citric acid, the change of mercury pecies was more and more striking with the prolonged incubation, and the conversion did not stop until 14 d, at that time the stomach cid dissolved mercury increased obviously, which was mainly converted from elemental mercury.

Perennial peanut (Arachis glabrata Benth.) leaves contain hydroxycinnamoyl-CoA:tartaric acid hydroxycinnamoyl transferase activity and accumulate hydroxycinnamoyl-tartaric acid esters.

Many plants accumulate hydroxycinnamoyl esters to protect against abiotic and biotic stresses. Caffeoyl esters in particular can be substrates for endogenous polyphenol oxidases (PPOs). Recently, we showed that perennial peanut (Arachis glabrata Benth.) leaves contain PPO and identified one PPO substrate, caftaric acid (trans-caffeoyl-tartaric acid). Additional compounds were believed to be cis- and trans-p-coumaroyl tartaric acid and cis- and trans-feruloyl-tartaric acid, but lack of standards prevented definitive identifications. Here we characterize enzymatic activities in peanut leaves to understand how caftaric acid and related hydroxycinnamoyl esters are made in this species. We show that peanut leaves contain a hydroxycinnamoyl-CoA:tartaric acid hydroxycinnamoyl transferase (HTT) activity capable of transferring p-coumaroyl, caffeoyl, and feruloyl moieties from CoA to tartaric acid (specific activities of 11 ± 2.8, 8 ± 1.8, 4 ± 0.8 pkat mg(-1) crude protein, respectively). The HTT activity was used to make cis- and trans-p-coumaroyl- and -feruloyl-tartaric acid in vitro. These products allowed definitive identification of the corresponding cis- and trans-hydroxycinnamoyl esters extracted from leaves. We tentatively identified sinapoyl-tartaric acid as another major phenolic compound in peanut leaves that likely participates in secondary reactions with PPO-generated quinones. These results suggest hydroxycinnamoyl-tartaric acid esters are made by an acyltransferase, possibly a BAHD family member, in perennial peanut. Identification of a gene encoding HTT and further characterization of the enzyme will aid in identifying determinants of donor and acceptor substrate specificity for this important class of biosynthetic enzymes. An HTT gene could also provide a means by genetic engineering for producing caffeoyl- and other hydroxycinnamoyl-tartaric acid esters in forage crops that lack them.

Discovery of novel insomnia leads from screening traditional Chinese medicine database.

Insomnia is a prominent modern disease that affects an increasing population. Undesirable side effects of commercial drugs highlight the need to develop novel insomnia drugs. Virtual screening of traditional chinese medicine Database@Taiwan (TCM Database@Taiwan) identified 2-O-Caffeoyl tartaric acid (1), 2-O-Feruloyl tartaric acid (2), and Mumefural (3) as potential agonists for both gamma-amino butyric acid (GABA) or benzodiazepine (BZ) binding sites. The TCM candidates exhibited higher affinity than GABA and Zolpidem, a phenomenon that could be attributed to higher quantity of stabilizing H-bonds. Efficacy profiles using support vector machines and pharmacophore contour also suggest drug potential of the TCM candidates. Fragments added to the de novo derivatives 3a, 3b, 3c for GABA binding site, and 1a, 2a, and 3d for BZ binding site contributed to new binding sites and structural stability, further optimizing binding to GABA or BZ binding sites. Increased opening of the ion channel by candidate ligands provide strong support for their potential biological functions. The dual binding properties of the TCM candidates present a unique opportunity to develop twin-targeting drugs with less side effects. Derivative structures can be used as starting points for developing high affinity GABAA receptor agonists with specificity towards GABA binding site and BZ binding site.

Enantioseparation of tartaric acid by ligand-exchange capillary electrophoresis using contactless conductivity detection.

A method for the determination of tartaric acid enantiomers using CE with contactless conductivity detection has been developed. Cu(II) as a central metal ion together with L-hydroxyproline were used as a chiral selector, the BGE was composed of 7 mM CuCl2, 14 mM trans-4-hydroxy-L-proline, and 100 mM ε-aminocaproic acid; the pH was adjusted to 5 by hydrochloric acid. Separation with a resolution of 1.9 was achieved in 9 min in a polyacrylamide-coated capillary to suppress the EOF. Various counterions of the BGE were studied, and migration order reversal was achieved when switching from ε-aminocaproic acid to L-histidine. With detection limits of about 20 µM, the method was applied to the analysis of wine and grape samples; only L-tartaric acid was found.

Optimization of biodiesel production process from soybean oil using the sodium potassium tartrate doped zirconia catalyst under Microwave Chemical Reactor.

A solid base catalyst was prepared by the sodium potassium tartrate doped zirconia and microwave assisted transesterification of soybean oil was carried out for the production of biodiesel. It was found that the catalyst of 2.0(n(Na)/n(Zr)) and calcined at 600°C showed the optimum activity. The base strength of the catalysts was tested by the Hammett indicator method, and the results showed that the fatty acid methyl ester (FAME) yield was related to their total basicity. The catalyst was also characterized by FTIR, TGA, XRD and TEM. The experimental results showed that a 2.0:1 volume ratio of methanol to oil, 65°C reaction temperature, 30 min reaction time and 10 wt.% catalyst amount gave the highest the yield of biodiesel. Compared to conventional method, the reaction time of the way of microwave assisted transesterification was shorter. The catalyst had longer lifetime and maintained sustained activity after being used for four cycles.

Optimization of the selective preparation of 20(R)-ginsenoside Rg3 catalyzed by d, l-tartaric acid using response surface methodology.

The optimization of the selective preparation of 20(R)-ginsenoside Rg3 converting protopanaxadiol type saponins (PPD saponins) by the commercially available d, l-tartaric acid was carried out using response surface methodology (RSM) based on a three-factor and six-level central composite design. The optimal 20(R)-ginsenoside Rg3 de% was predicted to be 94.52% in the combination of the factors (d, l-tartaric acid concentration 1.19mol/L, temperature 107.9°C and time 2.79h) through the canonical analysis with maximum responses. Under the optimum reaction conditions, the actual 20(R)-ginsenoside Rg3 de% was 96.49%. 20(R)-ginsenoside Rg3 (1) and 20(S)-ginsenoside Rg3 (2) were separated and identified by (1)H-NMR and (13)C-NMR. Therefore, the RSM was effective to optimize the preparation of 20(R)-ginsenoside Rg3 by converting PPD saponins using d, l-tartaric acid.

New starch preparations resistant to enzymatic digestion.

BACKGROUND: New starch preparations were produced by thermolysis of potato starch in the presence of inorganic (hydrochloric) and organic (citric and tartaric) acids under controlled conditions. The starch preparations were physicochemically and structurally characterised and analysed for their resistance to enzymatic digestion in vitro. RESULTS: The content of resistant fraction in dextrin D1, obtained by heating starch acidified with hydrochloric and citric acids, determined by the AOAC 2001.03 and pancreatin-gravimetric methods was similar (~200 g kg⁻¹). In the case of dextrin D3, obtained by heating starch acidified with hydrochloric and tartaric acids, the result of determination by the pancreatin-gravimetric method was almost four times higher than that obtained with the AOAC 2001.03 method. The enzymatic tests revealed that dextrin D3 obtained with excess tartaric acid can be classified as RS4, which can only be partially determined by enzymatic-gravimetric methods. Tartaric acid at high concentration had a significantly stronger influence on starch hydrolysis than citric acid. This was confirmed by chromatographic analysis of dextrins and chemical investigation of the reducing power. CONCLUSION: The results confirmed the possibility of applying dextrins, prepared under specific conditions, as soluble dietary fibre.

[Optimization of the matrix formulation of compound Die Da Zhen Tong cataplasm by uniform design].

OBJECTIVE: To optimize the matrix formulation of compound Die Da Zhen Tong cataplasm. METHODS: The optimal preparation was selected by U17 (17(16)) uniform design, independent variables were the percentage ratio of the matrix formulation component part in compound Die Da Zhen Tong cataplasm,and the viscosity, continued viscosity and overall desirability used as indexes were dependent variables. RESULTS: The percentage of the matrix formulation component part in compound Die Da Zhen Tong cataplasm was, NP-700: carbomer 980: PVP K-90: dihydroxy aluminum: tartaric: kaolinite: sorbitol: glycerin = 5: 1. 2: 2.5: 0.25: 0.15:4: 12: 5. CONCLUSION: The optimized cataplasm has good viscosity, continued viscosity and high overall desirability.

Chemistry and pharmacological action of caffeoylquinic acid derivatives and pharmaceutical utilization of chwinamul (Korean Mountainous vegetable).

Chwinamul is a mountainous vegetable that refers to several species belonging to the family Compositae. Chwinamul has been used as a side dish or a medicinal herb to treat hypercholesterolemia, diabetes, common cold, atherosclerosis, and cardiovascular disease. Caffeoylquinic acids (CQs) are present in high levels in chwinamul, though caffeoyltartaric acids (CTs) are often occurred in the vegetables of Compositae. Here I review the chemical and pharmaceutical aspects of CQs and CTs. In particular, ¹³C-NMR data and CQ stereochemistry are discussed. CQ derivatives have antioxidative, peroxynitrite-scavenging, hepatoprotective, antiviral, antiobese, and antidiabetic activities.

Chemical composition and antidiabetic activity of Opuntia Milpa Alta extracts.

Three new compounds, 1-3, and 20 known compounds were isolated from the AcOEt and BuOH extract of edible Opuntia Milpa Alta. The petroleum ether extract was examined by GC and MS. A total of 26 compounds were identified, representing 95.6% of the total extract, phytosterol (36.03%) being the most abundant component, and polyunsaturated fatty acids (18.57%) represented the second largest group, followed by phytol (12.28%), palmitic acid, palmitate (13.54%), vitamin E (4.51%), and other compounds (7.47%). The effects of various extracts from edible Opuntia Milpa Alta (petroleum ether extract, AcOEt extract, BuOH extract, aqueous extract, H2O parts) and the positive control (received dimethylbiguanide) were tested on streptozotocin (STZ)-induced diabetic mice. The results indicated that all the treatment groups could significantly decrease blood glucose levels in STZ-induced diabetic mice compared to the model control group (P<0.01), except the aqueous extract group (P<0.05). Especially, the petroleum ether extract group and the positive control group showed remarkable decrease of blood glucose levels. Taken together, the results indicate that the petroleum ether extract is the major hypoglycemic part in edible Opuntia Milpa Alta, which may be developed to a potential natural hypoglycemic functional ingredient.

Spectroscopic and structural investigation of the confinement of D and L dimethyl tartrate in lecithin reverse micelles.

The confinement of D and L dimethyl tartrate in lecithin reverse micelles dispersed in cyclohexane has been investigated by FT-IR, polarimetry, electronic and vibrational circular dichroism (ECD and VCD), 1H NMR, and small-angle X-ray scattering (SAXS). Measurements have been performed at room temperature as a function of the solubilizate-to-surfactant molar ratio (R) at fixed lecithin concentration. The analysis of experimental data indicates that the dimethyl tartrate molecules are solubilized within reverse micelles in proximity to the surfactant head groups in the same way for the D and L forms. The encapsulation of dimethyl tatrate within lecithin reverse micelles involves changes in its H-bonds, from what is observed in the pure solid or in CCl4 solutions; this is a consequence of the establishment of specific solute-surfactant headgroup interactions and of confinement effects. In the 0 < or = R < or = 1.7 range, SAXS profiles of dimethyl tartrate/lecithin/ cyclohexane micellar solutions are well-described by a model of interacting polydisperse spherical micellar cores whose mean radius does not change appreciably with R (i.e., it changes from about 18 to 20 angstroms). 1H NMR diffusion measurements of both dimethyl tartrates and lecithin were rationalized in terms of collective translational motions of the entire micellar aggregate and of their molecular diffusion among clusters of reverse micelles. The association of optically active lecithin with D and L dimethyl tartrate leads to the formation of self-organized supramolecular aggregates whose interesting chiroptical features are evidenced by polarimetry and CD.

Kinetics of fluoride release from glass components of glass ionomers.

OBJECTIVES: To compare the F release from glass ionomer glasses (GICs) into water changed periodically with release into an unchanged "sink" [Williams JA, Billington RW, Pearson GJ. The glass ionomer cement: the sources of soluble fluoride. Biomaterials 2002;23:2191-200]. To evaluate the effect of replacing Ca wholly or partially by Sr. To compare two different methods of decomplexing F containing species. METHODS: All four glasses contained Al, Si, P, O and F. Glass AH2 (Advanced Healthcare Ltd.) had Na and Ca, LG26 (Advanced Healthcare Ltd.) had Ca, LG26Sr (ULTRASET project) had Ca and Sr, and LG125 (ULTRASET project) had Sr. Glasses were tested: after ball-milling, after washing in dilute acid, and W mixed with 35% acetic acid to form a "pseudo-cement". F(-) release was from 130mg samples into 10ml of deionised water changed at 1, 3, 7, 14, 21, 28, 35, and 42 days. Analysis was carried out: (a) using ISE without decomplexing, (b) using TISAB buffer, and (c) acid hydrolysis+TISAB (after Hattab). RESULT: The cumulative release rates from all glasses and treatments are linear with respect to t(1/2) with r=0.97 or greater (p=<0.001). F release into a "sink" showed no such correlation. The higher release rate from AH2 is more than accounted for by its higher F content. Most F release is not complexed except of AH2. AH2 has 20% of complex fluoride from raw glass, 44% from acid-washed glass and 51% from pseudo-cement. More fluoride is released after acid treatment from all 4 glasses, these are on average 4.4 times higher from acid-washed glass and 5.3 times higher from pseudo-cement. For TISAB fluoride release, LG26Sr is 26% more than LG26. Hattab fluoride>TISAB fluoride only for raw glasses. CONCLUSIONS: Changing water produces diffusion controlled kinetics. Acid treated will increase the complex fluoride from AH2. Replacing Ca by Sr enhances F release rate slightly.

Development of chitosan-coated liposomes for sustained delivery of tamarind fruit pulp's extract to the skin.

In this study, chitosan-coated liposomes were developed. To entrap lyophilized tamarind extract containing alpha-hydroxy acids (AHAs) together with tartaric acid, the reverse phase evaporation method was used to obtain well-formed liposomes loaded with the extract. The highest entrapment efficiency of 68.3 +/- 3.0% into the liposomes was obtained with liposomes consisting of phosphatidylcholine and cholesterol in a molar ratio of 2 : 1 after the extrusion process. The average particle size of the prepared liposomes was 158 +/- 26 nm showing a negative zeta potential of -6 mV. For the preparation of the chitosan-coated liposomes, two selected independent parameters were varied: chitosan concentrations of 0.1, 0.5 and 1.0% w/v and volumes of the chitosan solutions of 1, 2 and 3 mL, to study the effects of such parameters on the entrapment efficiency of the extract-loaded liposomes. Variation in the volumes of the chitosan solution did not affect the entrapment efficiency of the liposomes. However, the entrapment efficiency of the AHAs in the chitosan-coated liposomes significantly increased with increasing chitosan concentrations. The size of the chitosan-coated liposomes was in the range of 200-300 nm with a positive zeta potential in the range of 6-29 mV. An in vitro release study using dialysis technique was performed to evaluate the release profile of the tartaric acid from the chitosan-coated liposomes. The obtained results showed the effect of the chitosan-coated liposomes on the lower release rate and on the amount of tartaric acid in comparison with that of the uncoated liposomes. The study in an in vitro skin cell model indicated that the developed system could enhance the potential of tamarind's AHAs on the stimulation of human keratinocyte proliferation being two-fold higher than the solution of the tamarind extract.

Control of oenological products: discrimination between different botanical sources of L-tartaric acid by isotope ratio mass spectrometry.

Following previous studies on counterfeit of wines with synthetic ingredients, the possibility of frauds by natural external L-tartaric acid has also been investigated. The aim of this research was to map the stable isotope ratios of L-tartaric acid coming from botanical species containing large amounts of this compound: grape and tamarind. Samples of L-tartaric acid were extracted from the pulp of tamarind fruits originating from several countries and from grape must. delta(13)C and delta(18)O were measured for all samples. Additional delta(2)H measurements were performed as a complementary analysis to help discrimination of the botanical origin. Different isotopic patterns were observed for the different botanical origins. The multivariate statistical analysis of the data shows clear discrimination among the different botanical and synthetic sources. This approach could be a complementary tool for the control of L-tartaric acid used in oenology.