Organic Acid Derivatives Research Articles

Revealing the effects and mechanism of wine processing on Corni Fructus using chemical characterization integrated with multi-dimensional analyses

Corni fructus (CF) is always subjected to wine processing before prescription in clinic, for an enhancing effect of nourishing liver and kidney. While, the underlying mechanism for this processing on CF remains obscure. In this study, a sensitive ultra-high-performance liquid chromatography mass spectrometry (UPLC-MS/MS) method combined multi-dimensional analyses was established to monitor chemical characterizations of raw and wine-processed CF (WCF) and hence reveal the effects and underlying mechanism of wine processing on CF. As indicated, a total of 216 compounds were tentatively identified, including 98 structurally complex and variable home/hetero-polymers, that were composed of iridoid glucosides, gallic acids, caffeic acid and/or 5-HMF. Interestingly, 53 of these compounds probably characterized potential novel, including 35 iridoid glucosides or their dimers, 9 iridoid glucoside-gallic acid dimers, 7 gallic acids derivatives and 2 gallic acid-caffeic acid dimers, which provides ideas for natural product researchers. Meanwhile, the multi-dimensional analyses including principal component analysis (PCA), partial least squares discriminant analysis (PLS-DA) and linear regression analysis were used to explore the differences between CF and WCF. The results showed that 23 compounds as chemical markers greatly contributing to the distinction were screened out, and 3 of which (7α/β-O-ethyl-morroniside, gallic acid and 5-HMF) in WCF indicated an increasing trend in intensities in relative to those in CF. Additionally, linear regression analysis showed that in WCF 53 compounds exhibited an increasing in intensities, while 132 ones did a decreasing trend, compared with those in CF. As our investigation demonstrated, acetal reaction of morroniside, ester hydrolysis in different organic acid derivatives as well as glycoside bond cleavage during wine processing probably resulted in the distinctions. The findings of this study provide a further understanding of the effect and mechanism of wine processing on CF.

Molecular Modeling, Synthesis, and Antihyperglycemic Activity of the New Benzimidazole Derivatives - Imidazoline Receptor Agonists.

The paper presents the results of a study on the first synthesized benzimidazole derivatives obtained from labile nature carboxylic acids. The synthesis conditions of these substances were studied, their structure was proved, and some components were found to have sugar-reducing activity on the model of alloxan diabetes in rats. The study used molecular modeling methods such as docking based on the evolutionary model (igemdock), RP_HPLC method to monitor the synthesis reaction, and 1H NMR and 13C NMR, and other methods of organic chemistry to confirm the structures of synthesized substances. The docking showed that the ursodeoxycholic acid benzimidazole derivatives have high tropics to all imidazoline receptor carriers (PDB ID: 2XCG, 2bk3, 3p0c, 1QH4). The ursodeoxycholic acid benzimidazole derivative and arginine and histidine benzimidazole derivatives showed the highest sugar-lowering activity in the experiment on alloxan-diabetic rats. For these derivatives, the difference in glucose levels of treated rats was significant against untreated control. Therefore, the new derivatives of benzimidazole and labile natural organic acids can be used to create new classes of imidazoline receptor inhibitors for the treatment of diabetes mellitus and hypertension.

Introduction of CdSe/ZnS Quantum Dots into Liquid Crystalline Matrix

An important aspect of modern materials science, namely the possibility of combining inorganic nanoparticles and liquid crystals in composite materials is discussed. These systems make it possible to combine liquid crystal properties of matrix and luminescent properties of quantum dots. A five-component mixture consisting mainly of 4-cyanobiphenyl derivatives used as a matrix. The substitution of ligands formed during the synthesis of quantum dots with derivatives of organic acids is shown. Using two new optically active ligands, the chiralization of the nematic matrix was demonstrated by introducing quantum dots into it.

Magnesium Nutrient Application Induces Metabolomics and Physiological Responses in Mulberry (Morus alba) Plants.

Mulberry (Morus alba) is a significant plant with numerous economic benefits; however, its growth and development are affected by nutrient levels. A high level of magnesium (Mg) or magnesium nutrient starvation are two of the significant Mg factors affecting plant growth and development. Nevertheless, M. alba's metabolic response to different Mg concentrations is unclear. In this study, different Mg concentrations, optimal (3 mmol/L), high (6 mmol/L and 9 mmol/L), or low (1 and 2 mmol/L) and deficient (0 mmol/L), were applied to M. alba for three weeks to evaluate their effects via physiological and metabolomics (untargeted; liquid chromatography-mass spectrometry (LC-MS)) studies. Several measured physiological traits revealed that Mg deficiency and excess Mg altered net photosynthesis, chlorophyll content, leaf Mg content and fresh weight, leading to remarkable reductions in the photosynthetic efficiency and biomass of mulberry plants. Our study reveals that an adequate supply of the nutrient Mg promoted the mulberry's physiological response parameters (net photosynthesis, chlorophyll content, leaf and root Mg content and biomass). The metabolomics data show that different Mg concentrations affect several differential metabolite expressions (DEMs), particularly fatty acyls, flavonoids, amino acids, organic acid, organooxygen compounds, prenol lipids, coumarins, steroids and steroid derivatives, cinnamic acids and derivatives. An excessive supply of Mg produced more DEMs, but negatively affected biomass production compared to low and optimum supplies of Mg. The significant DEMs correlated positively with mulberry's net photosynthesis, chlorophyll content, leaf Mg content and fresh weight. The mulberry plant's response to the application of Mg used metabolites, mainly amino acids, organic acids, fatty acyls, flavonoids and prenol lipids, in the KEGG (Kyoto Encyclopedia of Genes and Genomes) pathways. These classes of compounds were mainly involved in lipid metabolism, amino acid metabolism, energy metabolism, the biosynthesis of other secondary metabolites, the biosynthesis of other amino acids, the metabolism of cofactors and vitamin pathways, indicating that mulberry plants respond to Mg concentrations by producing a divergent metabolism. The supply of Mg nutrition was an important factor influencing the induction of DEMs, and these metabolites were critical in several metabolic pathways related to magnesium nutrition. This study provides a fundamental understanding of DEMs in M. alba's response to Mg nutrition and the metabolic mechanisms involved, which may be critical to the mulberry genetic breeding program.

Uncovering the Nutritive Profiles of Adult Male Chinese Mitten Crab (E. sinensis) Harvested from the Pond and Natural Water Area of Qin Lake Based on Metabolomics.

E. sinensis, normally harvested in October and November, is an economic aquatic product in China. Pond culture has been widely applied for the production of E. sinensis, wherein a stable food supply for crabs is provided. In order to improve the nutritional quality of E. sinensis products, this study evaluated the effect of the local pond culture on the nutritive profiles of E. sinensis and screened out the best harvest time for the nutrient-rich crabs, thereby guiding the local crab industry to improve its aquaculture mode and harvest strategy. The results indicated that pond culture enhanced the levels of protein, amino acids, and specific organic acid derivatives, and reduced the levels of peptides and polyunsaturated fatty acids (PUFAs). Compared with E. sinensis harvested in October, peptide levels were significantly increased, whereas sugar, phenolic acid, and nucleotide levels were decreased in those harvested in November. Overall, the study revealed that the nutritive profile of the pond-reared E. sinensis was significantly modulated by a high-protein diet, thus lacking the diversity of metabolites. Additionally, October could be more appropriate for harvesting E. sinensis than November.

Evaluation of GC/MS-Based 13C-Positional Approaches for TMS Derivatives of Organic and Amino Acids and Application to Plant 13C-Labeled Experiments.

Analysis of plant metabolite 13C-enrichments with gas-chromatography mass spectrometry (GC/MS) has gained interest recently. By combining multiple fragments of a trimethylsilyl (TMS) derivative, 13C-positional enrichments can be calculated. However, this new approach may suffer from analytical biases depending on the fragments selected for calculation leading to significant errors in the final results. The goal of this study was to provide a framework for the validation of 13C-positional approaches and their application to plants based on some key metabolites (glycine, serine, glutamate, proline, α-alanine and malate). For this purpose, we used tailor-made 13C-PT standards, harboring known carbon isotopologue distributions and 13C-positional enrichments, to evaluate the reliability of GC-MS measurements and positional calculations. Overall, we showed that some mass fragments of proline_2TMS, glutamate_3TMS, malate_3TMS and α-alanine_2TMS had important biases for 13C measurements resulting in significant errors in the computational estimation of 13C-positional enrichments. Nevertheless, we validated a GC/MS-based 13C-positional approach for the following atomic positions: (i) C1 and C2 of glycine_3TMS, (ii) C1, C2 and C3 of serine_3TMS, and (iii) C1 of malate_3TMS and glutamate_3TMS. We successfully applied this approach to plant 13C-labeled experiments for investigating key metabolic fluxes of plant primary metabolism (photorespiration, tricarboxylic acid cycle and phosphoenolpyruvate carboxylase activity).

Matrix Effects in GC–MS Profiling of Common Metabolites after Trimethylsilyl Derivatization

Metabolite profiling using gas chromatography coupled to mass spectrometry (GC-MS) is one of the most frequently applied and standardized methods in research projects using metabolomics to analyze complex samples. However, more than 20 years after the introduction of non-targeted approaches using GC-MS, there are still unsolved challenges to accurate quantification in such investigations. One particularly difficult aspect in this respect is the occurrence of sample-dependent matrix effects. In this project, we used model compound mixtures of different compositions to simplify the study of the complex interactions between common constituents of biological samples in more detail and subjected those to a frequently applied derivatization protocol for GC-MS analysis, namely trimethylsilylation. We found matrix effects as signal suppression and enhancement of carbohydrates and organic acids not to exceed a factor of ~2, while amino acids can be more affected. Our results suggest that the main reason for our observations may be an incomplete transfer of carbohydrate and organic acid derivatives during the injection process and compound interaction at the start of the separation process. The observed effects were reduced at higher target compound concentrations and by using a more suitable injection-liner geometry.

Chemical characterization and antioxidant potential of ecuadorian propolis

The chemical composition and the antioxidant potential of Ecuadorian propolis samples (n = 19) collected in different provinces were investigated. HPLC-DAD-ESI/MSn and GC-EI-MS analysis of the methanol extracts enabled us to define six types of Ecuadorian propolis based on their secondary metabolite composition. 68 compounds were identified, 59 of which are reported for the first time in Ecuadorian propolis. The detected compounds include flavonoids, diterpenes, triterpenes, organic acid derivatives, alkylresorcinol derivatives and nemorosone. Plants belonging to genera Populus, Mangifera and Clusia seemed to be vegetable sources employed by bees to produce Ecuadorian propolis. Total phenolic content and antioxidant activity of propolis extracts were determined by the Folin-Ciocalteu assay and 2,2-diphenyl-1-picrylhydrazyl and ferric reducing/antioxidant potential assays, respectively. As expected, the variable chemical composition affected the differences in terms of antioxidant potential.

Investigation of Enzyme Inhibitory Activities, Antioxidant Activities, and Chemical Properties of Pistacia vera Leaves Using LC-QTOF-MS and RP-HPLC.

Since the leaves of some Pistacia species are used in traditional folk medicine for diabetes, this study investigated the in vitro antidiabetic effect (α-glucosidase and α-amylase) of Pistacia vera leaves. Additionally, the current study investigated the antihypercholesterolemic (cholesterol esterase), antiobesity (pancreatic lipase), and antioxidant activities (i.e., total antioxidant capacity, DPPH (2,2-Diphenyl-1-picrylhydrazyl) radical scavenging activity, metal chelating activity, and ferric-reducing antioxidant power) of P. vera leaves. The aqueous-alcoholic leaf extract inhibited α-amylase, α-glucosidase, and pancreatic lipase with the half-maximal inhibitory concentration values of 7.74 ± 0.72, 11.08 ± 3.96, and 168.43 ± 26.10 µg/mL, respectively. It was determined that the crude extract had high DPPH radical scavenging activity, ferric-reducing power, and moderate metal chelating activity. The ethyl acetate (EtOAc) subextract obtained by the liquid-liquid fractionation of the crude extract showed potent α-amylase and α-glucosidase inhibitory activities. The EtOAc subextract (5.794 ± 0.027 g/100 g subextract) was standardized by reversed-phase high-performance liquid chromatography based on β-pentagalloyl glucose, which showed inhibitory effects on both amylase and glucosidase enzymes. Fifteen compounds, seven of which are organic acid derivatives and eight of which are flavonoids, were identified by liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF-MS) analysis in the crude extract of P. vera leaves. Seven of the fifteen phenolic compounds detected in the crude extract by LC-QTOF-MS have both glucosidase and amylase inhibitory effects. As a result, P. vera leaves can be a potential source for compounds with high antioxidant effects that show inhibitory effects on enzymes involved in carbohydrate digestion in the prevention and treatment of diabetes or can be evaluated as a standardized extract.

Identification of Potential Anti-tooth-decay Compounds From Organic Cinnamic Acid Derivatives by Inhibiting Matrix Metalloproteinase-8: An In Silico Study

Background: Matrix metalloproteinase-8 (MMP-8) is the most abundant member of the MMP family in human dentin. It takes a part in the normal physiology of tissue remodeling and wound healing, while the overexpression/hyperactivity of this protein leads to several oral disorders, including dental caries and peri-implant inflammation/diseases, and therefore, MMP-8 inhibition may have therapeutic effects. Accordingly, the current study aimed to identify potential MMP-8 inhibitors from cinnamic acid derivatives. Methods: The binding affinity of cinnamic acid and its several derivatives to the MMP-8 active site were estimated using the AutoDock 4.0 software. The pharmacokinetics, toxicity, and bioavailability of top-ranked MMP-8 inhibitors were also predicted by utilizing bioinformatics web tools. Results: Five of the studied components, including chlorogenic acid (CGA), caffeic acid 3-glucoside, rosmarinic acid, N-p-Coumaroyltyramine, and caffeic acid phenethyl ester (CAPE) demonstrated a salient affinity of binding to the MMP-8 catalytic site (∆Gbinding<-10 kcal/mol). It was estimated that these compounds can inhibit the MMP-8 at the nanomolar concentration, and therefore, were considered as top-ranked MMP-8 inhibitors. Finally, none of the top-ranked components revealed a considerable side effect and thus were found to be suitable for oral use. Conclusions: The results of the present study suggested that CGA, caffeic acid 3-glucoside, rosmarinic acid, N-p-coumaroyltyramine, and CAPE might have protective effects on tooth decay and peri-implant inflammation/diseases.

Metabolomic analysis of photosynthetic biofilms on building façades in temperate climate zones

The aim of the study was to incorporate a multidimensional approach to the biodeteriorative influence of aerophytic algal biofilms colonising building materials, such as bricks and plasters in temperature climate zones. Stichococcus sp., Klebsormidium sp., Chlorococcum infusionum, Chlorella vulgaris and Pseudochlorella signiensis were detected in green biofilms covering internal and external walls of buildings in Poland. Their growth led to changes in the material's colour in the range of ΔE = 10.82–37.67, as well high water retention and absorptivity. The moisture content of analysed materials ranged from 9.00 to 14.59%. Further, the direct influence of algal growth on the mechanical properties of the analysed materials was not found. For metabolome analysis laser desorption/ionisation time-of-flight mass spectrometry with silver-109 and gold nanoparticles was used. Derivatives of sulfuric compounds and organic acids were detected but this was not the case for metabolites with well-documented biodeteriorative potential. 109AgNPET LDI MS allowed for the detection of 43 different metabolic pathways, using AuNPET LDI MS 25 pathways. In total, 110 metabolites were found. Although the spectrum of metabolites detected using 109AgNPET LDI MS was broader, AuNPET LDI MS allowed for the detection of pathways that were not found by 109AgNPET LDI MS. The combination of both methods allowed for the widest range of results.

A New Organic Acid Derivative from the Fruits of Rosa roxburghii

A New Organic Acid Derivative from the Fruits of Rosa roxburghii

Quantum Chemical Prediction of Electron Ionization Mass Spectra of Trimethylsilylated Metabolites.

Chemical derivatization, especially silylation, is widely used in gas chromatography coupled to mass spectrometry (GC-MS). By introducing the trimethylsilyl (TMS) group to substitute active hydrogens in the molecule, thermostable volatile compounds are created that can be easily analyzed. While large GC-MS libraries are available, the number of spectra for TMS-derivatized compounds is comparatively small. In addition, many metabolites cannot be purchased to produce authentic library spectra. Therefore, computationally generated in silico mass spectral databases need to take TMS derivatizations into account for metabolomics. The quantum chemistry method QCEIMS is an automatic method to generate electron ionization (EI) mass spectra directly from compound structures. To evaluate the performance of the QCEIMS method for TMS-derivatized compounds, we chose 816 trimethylsilyl derivatives of organic acids, alcohols, amides, amines, and thiols to compare in silico-generated spectra against the experimental EI mass spectra from the NIST17 library. Overall, in silico spectra showed a weighted dot score similarity (1000 is maximum) of 635 compared to the NIST17 experimental spectra. Aromatic compounds yielded a better prediction accuracy with an average similarity score of 808, while oxygen-containing molecules showed lower accuracy with only an average score of 609. Such similarity scores are useful for annotation of small molecules in untargeted GC-MS-based metabolomics, suggesting that QCEIMS methods can be extended to compounds that are not present in experimental databases. Despite this overall success, 37% of all experimentally observed ions were not found in QCEIMS predictions. We investigated QCEIMS trajectories in detail and found missed fragmentations in specific rearrangement reactions. Such findings open the way forward for future improvements to the QCEIMS software.

Synthesis of N-trifluoromethyl amides from carboxylic acids

Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.

Phytochemical Analysis of the Fruits of Sea Buckthorn (Hippophae rhamnoides): Identification of Organic Acid Derivatives.

Hippophae rhamnoides L. (Elaeagnaceae), commonly known as “Sea buckthorn” and “Vitamin tree”, is a spiny deciduous shrub whose fruit is known for its nutritional composition, such as vitamin C, and is consumed as a dietary supplement worldwide. As part of our ongoing efforts to identify structurally new and bioactive constituents from natural resources, the phytochemical investigation of the extract of H. rhamnoides fruits led to the isolation of one malate derivative (1), five citrate derivatives (2–6), and one quinate derivative (7). The structures of the isolated compounds were elucidated by analysis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization (HR-ESI) liquid chromatography–mass spectrometry (LC/MS) data. Three of the citrate derivatives were identified as new compounds: (S)-1-butyl-5-methyl citrate (3), (S)-1-butyl-1′-methyl citrate (4), and (S)-1-methyl-1′-butyl citrate (6), which turned out to be isolation artifacts. The absolute configurations of the new compounds were established by quantum chemical electronic circular dichroism (ECD) calculation, which is an informative tool for verifying the absolute configuration of organic acid derivatives. The isolated compounds 1–7 were evaluated for their stimulatory effects on osteogenesis. Compounds 1, 3, 4, 6, and 7 stimulated osteogenic differentiation up to 1.4 fold, compared to the negative control. These findings provide experimental evidence that active compounds 1, 3, 4, 6, and 7 induce the osteogenesis of mesenchymal stem cells and activate bone formation.

UPLC-ESI-MS/MS Profile of The Ethyl Acetate Fraction of Aerial Parts of Bougainvillea 'Scarlett O'Hara' Cultivated in Egypt

The ethyl acetate fraction of Bougainvillea 'Scarlett O'Hara' cultivated in Egypt did not receive enough attention in phytochemical and biological studies. This inspired the authors to investigate the phytochemicals of this fraction for the first time using UPLC-ESI-MS/MS in negative and positive ionization modes to understand the distribution of the major secondary metabolites. The analysis revealed the tentative identification of fifty-seven compounds. The detected metabolites belonged to numerous chemical classes including seven organic acids, fourteen phenolic compounds, one betacyanin, seven anthocyanins, ten flavonoids, three saponins, six tannins, four cyclic tetrapyrolic derivatives and five miscellaneous. The LC-ESI-MS methodology in negative ionization mode was the most appropriate to detect the group of saponins (22.17%), flavonoids (14.27%), free organic (12.35%) and phenolic acid derivatives (14%). It can be seen that the highest ionization rate produced for cyclic tetrapyrolic derivatives (56.41%), anthocyanins (18.8%) and tannins (3.2%) in the positive mode chromatogram.

Investigation of Organic Acids in Saffron Stigmas (Crocus sativus L.) Extract by Derivatization Method and Determination by GC/MS

The beneficial health properties of organic acids make them target compounds in multiple studies. This is the reason why developing a simple and sensitive determination and investigation method of organic acids is a priority. In this study, an effective method has been established for the determination of organic (lactic, glycolic, and malic) acids in saffron stigmas. N-(tert-butyldimethylsilyl)-N-methyltrifluoroacetamide (MTBSTFA) was used as a derivatization reagent in gas chromatography combined with mass spectrometric detection (GC/MS). The saffron stigmas extract was evaporated to dryness with a stream of nitrogen gas. The derivatization procedure: 0.1 g of dried extract was diluted into 0.1 mL of tetrahydrofuran, then 0.1 mL MTBSTFA was orderly and successively added into a vial. Two different techniques were used to obtain the highest amount of organic acid derivatives from saffron stigmas. To the best of our knowledge, this is the first report of the quantitative and qualitative GC/MS detection of organic acids in saffron stigmas using MTBSTFA reagent, also comparing different derivatization conditions, such as time, temperature and the effect of reagent amount on derivatization process. The identification of these derivatives was performed via GC-electron impact ionization mass spectrometry in positive-ion detection mode. Under optimal conditions, excellent linearity for all organic acids was obtained with determination coefficients of R2 > 0.9955. The detection limits (LODs) and quantitation limits (LOQs) ranged from 0.317 to 0.410 µg/mL and 0.085 to 1.53 µg/mL, respectively. The results showed that the highest yield of organic acids was conducted by using 0.1 mL of MTBSTFA and derivatization method with a conventional heating process at 130 °C for 90 min. This method has been successfully applied to the quantitative analysis of organic acids in saffron stigmas.

Potential enzyme inhibitory properties of extracts and fractions from fruit latex of Ficus carica-based on inhibition of α-amylase and α-glucosidase

Ficus L. is one of the widespread genera of the Moraceae family. We aimed to evaluate the inhibiting effect on digestive enzymes linked to diabetes, the antioxidant activity and the phytochemical composition of active extract/fraction of fruit latex of Ficus carica L. subsp. carica (All.) Schinz Et Thel. The inhibition effect of extracts and fractions tested with α-amylase and α-glucosidase methods and the antioxidant effect investigated with ABTS·+ and FRAP tests. The qualitative determination of compounds within the active extract/fraction was carried out by LC–MS/MS. In a result, the highest α-amylase and α-glucosidase activity found in F2 fraction of fruit latex (IC50 = 195.205 ± 0.015 µg/mL and 6.920 ± 0.026 µg/mL, respectively). Moreover, the highest total phenolic (26.816 ± 0.007 mgGAE/gextract) and total flavonoid content (8.615 ± 0.009 mgCA /gextract) was found in S1extract and this extract showed the highest antioxidant activity on FRAP (at a concentration of 1 mg/mL equivalent to 179.802 ± 2.201 mmol Fe2+) and ABTS+· (at a concentration of 1 mg/mL equivalent to 0.296 ± 0.055 µM Trolox) tests. Besides that, a preliminary examination of the mass spectrums of active F2 fraction and S1 extract revealed the presence of one xanthone, one organic acid derivative, one chromone derivative, one fatty acid and one phenolic acid. It is the first report on α-amylase, α-glucosidase and antioxidant activities, and phytochemical analysis of fruit latex of F. carica subsp. carica and these studies could contribute to the advanced pharmacological activity studies of this species.

Polyphenolic profiling of two Embelia spp. endemic to South Western Ghats of India by liquid chromatography coupled with tandem mass spectrometry analysis

This study for the first time illustrates a comprehensive picture of the phenolic composition of Embelia adnata and Embelia gardneriana by high-performance liquid chromatography coupled with mass spectrometry analysis with ESI in negative ionisation. The analysis was performed in the methanolic extracts of different parts of these two species separately and identifies 54 individual phenolic compounds present in them. Among this by individual 36 and 28 compounds were recorded from E. adnata and E. gardneriana, respectively, and in this, 10 compounds were common in both the two species. The detected compounds come under the classes flavonoids, flavonoid glycosides, isoflavonoids, benzenoids, coumarins, stilbens, chalcones, polyphenols, gallic acid derivatives, tannins and different derivatives of various organic acids.

Organic acid conjugated phenolic compounds of hardy kiwifruit (Actinidia arguta) and their NF-κB inhibitory activity

Nine new compounds, argutinosides A-I (1–9) together with 20 known compounds (10–29), were isolated from the fruits of Actinidia arguta. Using spectral analysis, the structures of the isolated compounds were identified as 10 succinic acid derivatives, 11 quinic acid derivatives, two shikimic acid derivatives and six citric acid derivatives. The NF-κB transcriptional inhibitory activity of the compounds was evaluated using RAW 264.7 macrophages cells induced by lipopolysaccharide. Among four groups of different organic acid derivatives, the quinic acid derivatives inhibited NF-κB transcriptional activity with an IC50 value of 4.0 μM. Fruit is rich in organic acid and secondary metabolites, which differ depending on the type of fruit. Our present study showed the presence of various organic acids conjugates including nine new 2-methylsuccinic acid phenolic conjugates in kiwiberry and compared their biological activities. This will contribute to application of kiwiberry and also the diversity of different fruits.