The structural investigation of synthesized compounds can be carried out by various spectroscopic techniques. It is an important prospect in order to elucidate the structure of the desired products before being further utilized. The preparation of new p-nitro stilbene Schiff base derivatives as an electrochemical DNA potential spacer was synthesized using (E)-4-(4-nitrostyryl)aniline from Heck reaction with aldehydes in ethanolic solution. The data presented here in this article contains FTIR, UV-Vis and 1H and 13C NMR of (E)-4-(4-nitrostyryl)aniline and nitrostyryl aniline derivatives.
Vinegars are liquid products produced from the alcoholic and subsequent acetous fermentation of carbohydrate sources. They have been used as remedies in many cultures and have been reported to provide beneficial health effects when consumed regularly. Such benefits are due to various types of polyphenols, micronutrients and other bioactive compounds found in vinegars that contribute to their pharmacological effects, among them, antimicrobial, antidiabetic, antioxidative, antiobesity and antihypertensive effects. There are many types of vinegars worldwide, including black vinegar, rice vinegar, balsamic vinegar and white wine vinegar. All these vinegars are produced using different raw materials, yeast strains and fermentation procedures, thus giving them their own unique tastes and flavours. The main volatile compound in vinegar is acetic acid, which gives vinegar its strong, sour aroma and flavour. Other volatile compounds present in vinegars are mainly alcohols, acids, esters, aldehydes and ketones. The diversity of vinegars allows extensive applications in food.
The re-proliferation of quiescent cancer cells is considered to be the primary contributor to prostate cancer (Pca) recurrence and progression. In this study, we investigated the inhibitory effect of safranal, a monoterpene aldehyde isolated from Crocus sativus (saffron), on the re-proliferation of quiescent Pca cells in vitro and in vivo. The results showed that safranal efficiently blocked the re-activation of quiescent Pca cells by downregulating the G0/G1 cell cycle regulatory proteins CDK2, CDK4, CDK6, and phospho-Rb at Ser807/811 and elevating the levels of cyclin-dependent kinase inhibitors, p21 and p27. Further investigation on the underlying mechanisms revealed that safranal suppressed the mRNA and protein expression levels of Skp2, possibly through the deregulation of the transcriptional activity of two major transcriptional factors, E2F1 and NF-κB subunits. Moreover, safranal inhibited AKT phosphorylation at Ser473 and deregulated both canonical and non-canonical NF-κB signaling pathways. Safranal suppressed the tumor growth of quiescent Pca cell xenografts in vivo. Furthermore, safranal-treated tumor tissues exhibited a reduction in Skp2, E2F1, NF-κB p65, p-IκBα (Ser32), c-MYC, p-Rb (Ser807), CDK4, CDK6, and CDK2 and an elevation of p27 and p21 protein levels. Therefore, our findings demonstrate that safranal suppresses cell cycle re-entry of quiescent Pca cells in vitro and in vivo plausibly by repressing the transcriptional activity of two major transcriptional activators of Skp2, namely, E2F1 and NF-κB, through the downregulation of AKT phosphorylation and NF-κB signaling pathways, respectively.
The present study was to evaluate the toxicity of damnacanthal, nordamnacanthal, betulinic acid and zerumbone isolated from local medicinal plants towards leukemia cell lines and immune cells by using MTT assay and flow cytometry cell cycle analysis. The results showed that damnacanthal significantly inhibited HL-60 cells, CEM-SS and WEHI-3B with the IC50 value of 4.0 µg/mL, 8.0 µg/mL and 3.3 µg/mL, respectively. Nordamnacanthal and betulinic acid showed stronger inhibition towards CEM-SS and HL-60 cells with the IC50 value of 5.7 µg/mL and 5.0 µg/mL, respectively. In contrast, Zerumbone was demonstrated to be more toxic towards those leukemia cells with the IC50 value less than 10 µg/mL. Damnacanthal, nordamnacanthal and betulinic acid were not toxic towards 3T3 and PBMC compared to doxorubicin which showed toxicity effects towards 3T3 and PBMC with the IC50 value of 3.0 µg/mL and 28.0 µg/mL, respectively. The cell cycle analysis exhibited that damnacanthal exerted its toxicity effect towards HL-60 cells by inducing apoptosis with value of 25% after 72 hours treatment. Thus, these compounds could be the potential anticancer drug with less toxic side effect.
Aqueous and methanol extracts of the flowers of Clitoria ternatea (CT), a popularly
plant consumed for blue colour in Nasi Kerabu was selected to explore its cytotoxic
effect on six types of normal and cancer-origin cell lines. These included the hormone-dependent breast cancer cell line (MCF-7), non-hormone-dependent breast cancer cell
line (MDA-MB-231), human ovary cancer cell line (Caov-3), human cervical cancer cell line (Hela), human liver cancer cell line (HepG2) and human foreskin fibroblast cell line (Hs27). The anti-proliferation activities of the extracts were examined by employing colorimetric MTT (3-(4,5-dimethylthiazol-2-yl) 2,5 diphenyltetrazolium bromide) assay through time periods of 24, 48 and 72 hours. Preliminary results showed that the water extracted of CT had significant effects (p < 0.05) against MCF-7 with an IC50 value of 175.35 µg/ml. Furthermore, the aqueous and methanolic extracts were investigated by Gas Chromatogram-Mass spectrometry (GC-MS). The GC-MS chromatogram analysis of the water extracted had shown five peaks that represented components in the water extract namely mome inositol (38.7%) and pentanal (14.3%). Fifteen chemical constituents were identified in the methanol extract and the major chemical constituents were mome inositol (33.6%), cyclohexen, 1-methyl-4-(1-methylethylideme)- (7.1%), acetic acid, cyano- (6.5%) and hirsutene (5.7%). Heavy metals tested were at very low levels. The analysis conducted on the flowers provides a strong basis for emphasizing the medicinal and nutritional value of CT.
Biocatalysts have been gaining extra attention in recent decades due to their industrial-relevance properties, which may hasten the transition to a cleaner environment. Carboxylic acid reductases (CARs) are large, multi-domain proteins that can catalyze the reduction of carboxylic acids to corresponding aldehydes, with the presence of adenosine triphosphate (ATP) and nicotinamide adenine dinucleotide phosphate (NADPH). This biocatalytic reaction is of great interest due to the abundance of carboxylic acids in nature and the ability of CAR to convert carboxylic acids to a wide range of aldehydes essentially needed as end products such as vanillin or reaction intermediates for several compounds production such as alcohols, alkanes, and amines. This modular enzyme, found in bacteria and fungi, demands an activation via post-translational modification by the phosphopantetheinyl transferase (PPTase). Recent advances in the characterization and structural studies of CARs revealed valuable information about the dynamics, mechanisms, and unique features of the enzymes. In this comprehensive review, we summarize the previous findings on the phylogeny, structural and mechanistic insight of the domains, post-translational modification requirement, strategies for the cofactors regeneration, the extensively broad aldehyde-related industrial application properties of CARs, as well as their recent immobilization approaches.
A composite of chitosan biopolymer with microalgae and commercial carbon-doped titanium dioxide (kronos) was modified by grafting an aromatic aldehyde (salicylaldehyde) in a hydrothermal process for the removal of brilliant green (BG) dye. The resulting Schiff's base Chitosan-Microalgae-TiO2 kronos/Salicylaldehyde (CsMaTk/S) material was characterised using various analytical methods (conclusive of physical properties using BET surface analysis method, elemental analysis, FTIR, SEM-EDX, XRD, XPS and point of zero charge). Box Behnken Design was utilised for the optimisation of the three input variables, i.e., adsorbent dose, pH of the media and contact time. The optimum conditions appointed by the optimisation process were further affirmed by the desirability test and employed in the equilibrium studies in batch mode and the results exhibited a better fit towards the pseudo-second-order kinetic model as well as Freundlich and Langmuir isotherm models, with a maximum adsorption capacity of 957.0 mg/g. Furthermore, the reusability study displayed the adsorptive performance of CsMaTk/S remains effective throughout five adsorption cycles. The possible interactions between the dye molecules and the surface of the adsorbent were derived based on the analyses performed and the electrostatic attractions, H-bonding, Yoshida-H bonding, π-π and n-π interactions are concluded to be the responsible forces in this adsorption process.
This work employed the model protein β-lactoglobulin (BLG) to investigate the contribution of microstructural changes to regulating the interaction patterns between protein and flavor compounds through employing computer simulation and multi-spectroscopic techniques. The formation of molten globule (MG) state-like protein during the conformational evolution of BLG, in response to ultrasonic (UC) and heat (HT) treatments, was revealed through multi-spectroscopic characterization. Differential MG structures were distinguished by variations in surface hydrophobicity and the microenvironment of tryptophan residues. Fluorescence quenching measurements indicated that the formation of MG enhanced the binding affinity of heptanal to protein. LC-MS/MS and NMR revealed the covalent bonding between heptanal and BLG formed by Michael addition and Schiff-base reactions, and MG-like BLG exhibited fewer chemical shift residues. Molecular docking and molecular dynamics simulation confirmed the synergistic involvement of hydrophobic interactions and hydrogen bonds in shaping BLG-heptanal complexes thus promoting the stability of BLG structures. These findings indicated that the production of BLG-heptanal complexes was driven synergistically by non-covalent and covalent bonds, and their interaction processes were influenced by processes-induced formation of MG potentially tuning the release and retention behaviors of flavor compounds.
This paper deals with a review of the inhibition activity of a Schiff bases on the deterioration of mild steel in hydrochloric acid media. Two Schiff base ligands namely N,N’- Bis(salicylidene) ethylenediamine (Sadimine) and N,N’-Bis(bromosalicylidene)- ethylenediamine (Brosadimine) were synthesized from the condensation reactions of salicylaldehyde or 5-bromosalicylaldehyde with ethylenediamine respectively and evaluated as corrosion inhibitor for mild steel in 1 M HCl solution using weight loss method. The use of inhibitors is one of the most practical methods for protection of mild steel against corrosion in acidic media. Schiff bases are widely being employed in such applications. This paper highlights the influence of structure–inhibition activity relationship of Schiff base compounds
on their performance as corrosion inhibitors of mild steel in acid media. Sadimine and
Brosadimine show appreciable corrosion inhibition efficiency against the corrosion of mild
steel in 1 M HCl solution at room temperature. It has been found that Brosadimine shows
greater corrosion inhibition efficiency than Sadimine due to extra halogen group presence in
the structure. As the concentration of studied inhibitors increases, the corrosion inhibition
efficiency of the prepared compounds also increases. This study demonstrated that corrosion
inhibitors for metals and alloys can preserve the quality and life of metals from corrosion.
A series of ten 5-arylidene Meldrum’s acid derivatives had been synthesised in excellent yield via Knoevenagel condensation. This method does not require catalyst, or any further purification. Isopropylidene malonate (2,2-dimethyl-1,3-dioxane-4,6-dione), also known as Meldrum’s acid, is utilised as a core skeleton for various kind of reactions. Meldrum’s acid has features of a peculiar ring- opening sequences based on nucleophile-sensitive carbonyl functional groups at C-4 and C-6, which has made it possible for useful synthetic transformations, as well as its high acidity of methylene hydrogen at carbon position C-5. Hence, it allows the compound to be a flexible reagent for further reaction to prepare other derivatives. Therefore, Meldrum’s acid derivatives showed high potential of biological functions, such as antibacterial, antimalarial and antioxidant activities due to the olefinic linkage which played an important role in the enhancement of antimalarial activity. Furthermore, when arylidene Meldrum’s acid transformed to epoxide, the compound showed losses of antimalarial behaviour. Additionally, this compound has unique molecules due to the high acidity of methylene hydrogen at the carbon-5 position to initiate various reactions with different functional groups. In this research, Meldrum’s acid, 3 and ten its 5-arylidene derivatives (4a-e) and (5a-e) were synthesised by using two short and efficient reaction steps. The first step involved the condensation of malonic acid, 1 with acetone, 2 in acetic anhydride and acid via one-pot reaction to give Meldrum’s acid, 3 in 50% overall yield. Having Meldrum’s acid in hand, the reaction was proceeded with the Knoevenagel condensation reaction by using various functional groups, such as aryl aldehydes and aryl amines. All the synthesised compounds were characterised by using 1H and 13C spectroscopy.
Polygonum odoratum Lour. has been reclassified as Persicaria odorata (Lour.) Soják [Wilson, K. L. Polygonum sensu lato (Polygonaceae) in Australia. Telopea 1988, 3, 177-182]; other synonyms currently used are Vietnamese mint or Vietnamese coriander and, in Malaysia, Daun Laksa or Laksa plant. The aerial parts of Laksa plant are highly aromatic, and they contain many organic compounds such as (Z)-3-hexenal, (Z)-3-hexenol, decanal, undecanal, and dodecanal that are typical for green, citrus, orange peel, and coriander odors. In addition to these aldehydes, 3-sulfanyl-hexanal and 3-sulfanyl-hexan-1-ol were discovered for the first time in this herb. The fresh leaves are pungent when they are chewed, although the active compound has never been identified. The pungency of Persicaria hydropiper (L.) Spach (formerly Polygonum hydropiper L., synonym water pepper) is produced by polygodial, a 1,4-dialdehyde derived from drimane terpenoids. We also identified polygodial as the active pungent compound in P. odorata (Lour.) Soják.
Carboxylic acid reductases (CARs) are attracting burgeoning attention as biocatalysts for organic synthesis of aldehydes and their follow-up products from economic carboxylic acid precursors. The CAR enzyme class as a whole, however, is still poorly understood. To date, relatively few CAR sequences have been reported, especially from fungal sources. Here, we sought to increase the diversity of the CAR enzyme class. Six new CAR sequences from the white-rot fungus Pycnoporus cinnabarinus were identified from genome-wide mining. Genome and gene clustering analysis suggests that these PcCAR enzymes play different natural roles in Basidiomycete systems, compared to their type II Ascomycete counterparts. The cDNA sequences of all six Pccar genes were deduced and analysis of their corresponding amino acid sequence showed that they encode for proteins of similar properties that possess a conserved modular functional tri-domain arrangement. Phylogenetic analyses showed that all PcCAR enzymes cluster together with the other type IV CARs. One candidate, PcCAR4, was cloned and over-expressed recombinantly in Escherichia coli. Subsequent biotransformation-based screening with a panel of structurally-diverse carboxylic acid substrates suggest that PcCAR4 possessed a more pronounced substrate specificity compared to previously reported CARs, preferring to reduce sterically-rigid carboxylic acids such as benzoic acid. These findings thus present a new functionally-distinct member of the CAR enzyme class.
Probiotics may be used to enhance the functionality and nutritional values of fermented sausages. This study aims to evaluate the physicochemical and sensory properties of beef sausages fermented by lactic acid bacteria of Lactobacillus plantarum IIA-2C12 and L. acidophilus IIA-2B4. These strains were isolated from beef cattle and have shown to display probiotic features. While the nutrient contents were not affected by the probiotics, the pH, texture, and color varied among the sausages. Further analysis on fatty acids showed different profiles of saturated (C14:0, C17:0, and C20:0) and unsaturated (C14:1, C18:1n9c, C18:2n6c, and C22:6n3) fatty acids in sausages with probiotics. Gas chromatography-mass spectrometry further revealed some flavor development compounds including acid, alcohols, aldehydes, aromatic, ketones, sulfur, hydrocarbons and terpenes, varied among the sausages. Hedonic test showed no difference in the preference toward aroma, texture, and color for untrained panelists.
A number of offensive odorants including volatile organic compounds (VOCs), reduced sulfur compounds (RSCs), carbonyls, and ammonia were measured along with several reference pollutants (like benzene (B), CS(2), SO(2), CO, and total hydrocarbon (THC)) from combusted fumes of barbecue charcoals produced from five different countries (Korea, China, Indonesia, Malaysia, and the US). Although the emission concentrations of most odorants were generally below the reference guideline set by the malodor prevention law in Korea, the mean concentration of some aldehydes (acetaldehyde, propionaldehyde, and isovaleraldehyde) and ammonia exceeded those guidelines. As such, aldehydes were the most dominant odorant released from charcoal combustion followed by VOC and ammonia. If odorant levels of charcoal products are compared, there are great distinctions between the products of different countries. If comparison is made using the concept of the sum of odor intensity (SOI), the magnitude of SOI for the charcoal products from the five different countries varied in the order of 4.30 (Korea), 3.10 (Indonesia), 2.97 (China), 2.76 (Malaysia), and 2.76 (the US).
This study was conducted to evaluate the oxidative damage in diabetic mellitus induced rats. The evaluation of DNA damage was carried out by the Alkaline Comet Assay using peripheral lymphocyte cells taken from streptozotocin-induced diabetic rats (50 mg/kg) and control rats. The levels of malondealdehyde (MDA), 4-hydroxynonenal (4-HNE), fasting blood glucose (FBG) and HbA1c were also measured. All the induced diabetic rats were hyperglycemic until the end of the study with significantly higher levels of FBG and HbA1c as compared to the control rats. The results showed the percentage of tail DNA and tail moment values were also significantly higher in the diabetic induced rats. The same observations were made on the levels of plasma MDA and 4-HNE. In conclusion, this study indicated that hyperglycemic condition in diabetic induced rats could generate oxidative DNA damage.
Physical training is associated with oxidative stress and improvement in blood antioxidant status. In this study, we investigated the effects of training on plasma malondialdehyde (MDA) and 4-hydroxynonenal (4-HNE) as markers of lipid peroxidation, superoxide dismutase (SOD) activity, and ascorbic acid (AA) after a single bout of acute exercise. Twelve healthy, untrained young adult men were recruited for 5 weeks of aerobic training period. They were subjected to a rope-skipping exercise for 20 minutes at the intensity of 65-80% of heart rate reserve, thrice weekly. They also had to perform a single, acute bout of the same exercise protocol prior to and after training period. Venous blood samples were collected at resting condition (BL), immediately (0 h) and 24 hours (24 h) post acute exercise on both single bout sessions. Results showed that the pattern changes of oxidative stress response are quite similar on both acute sessions. The acute bouts of rope-skipping is associated with a significant increased (p = 0.001) in lipid peroxidation markers immediately after cessation of exercise, with a concomitant increases in antioxidant levels, albeit higher when compared to pre-training values (p = 0.001). These changes were followed by a significant decreased (p = 0.001) in all parameters, toward resting values, 24 hours thereafter. The training program seemed to induce a significant increase in MDA and 4-1-INE but also enhanced the antioxidant defense system namely SOD and AA among the untrained subjects.
Three strains of the chain-forming diatom Skeletonema marinoi, differing in their production of polyunsaturated aldehydes (PUA) and nutritional food components, were used in experiments on feeding, egg production, hatching success, pellet production, and behavior of three common planktonic copepods: Acartia tonsa, Pseudocalanus elongatus, and Temora longicornis. The three different diatom strains (9B, 1G, and 7J) induced widely different effects on Acartia tonsa physiology, and the 9B strain induced different effects for the three copepods. In contrast, different strains induced no or small alterations in the distribution, swimming behavior, and turning frequency of the copepods. 22:6(n-3) fatty acid (DHA) and sterol content of the diet typically showed a positive effect on either egg production (A. tonsa) or hatching success (P. elongatus), while other measured compounds (PUA, other long-chain polyunsaturated fatty acids) of the algae had no obvious effects. Our results demonstrate that differences between strains of a given diatom species can generate effects on copepod physiology, which are as large as those induced by different algae species or groups. This emphasizes the need to identify the specific characteristics of local diatoms together with the interacting effects of different mineral, biochemical, and toxic compounds and their potential implications on different copepod species.
Curcumin (diferuloylmethane), a biologically active ingredient derived from rhizome of the plant Curcuma longa, has potent anticancer properties as demonstrated in a plethora of human cancer cell lines/animal carcinogenesis model and also acts as a biological response modifier in various disorders. We have reported previously that dietary supplementation of curcumin suppresses renal ornithine decarboxylase (Okazaki et al. Biochim Biophys Acta 1740:357-366, 2005) and enhances activities of antioxidant and phase II metabolizing enzymes in mice (Iqbal et al. Pharmacol Toxicol 92:33-38, 2003) and also inhibits Fe-NTA-induced oxidative injury of lipids and DNA in vitro (Iqbal et al. Teratog Carcinog Mutagen 1:151-160, 2003). This study was designed to examine whether curcumin possess the potential to suppress the oxidative damage caused by kidney-specific carcinogen, Fe-NTA, in animals. In accord with previous report, at 1 h after Fe-NTA treatment (9.0 mg Fe/kg body weight intraperitoneally), a substantial increased formation of 4-hydroxy-2-nonenal (HNE)-modified protein adducts in renal proximal tubules of animals was observed. Likewise, the levels of 8-hydroxy-2'-deoxyguanosine (8-OHdG) and protein reactive carbonyl, an indicator of protein oxidation, were also increased at 1 h after Fe-NTA treatment in the kidneys of animals. The prophylactic feeding of animals with 1.0% curcumin in diet for 4 weeks completely abolished the formation of (i) HNE-modified protein adducts, (ii) 8-OHdG, and (iii) protein reactive carbonyl in the kidneys of Fe-NTA-treated animals. Taken together, our results suggest that curcumin may afford substantial protection against oxidative damage caused by Fe-NTA, and these protective effects may be mediated via its antioxidant properties. These properties of curcumin strongly suggest that it could be used as a cancer chemopreventive agent.
A variety of dihydroquinazolin-4(1H)-one derivatives (1-37) were synthesized via "one-pot" three-component reaction scheme by treating aniline and different aromatic aldehydes with isatoic anhydride in the presence of acetic acid. Chemical structures of compounds were deduced by different spectroscopic techniques including EI-MS, HREI-MS, 1H-, and 13C-NMR. Compounds were subjected to α-amylase and α-glucosidase inhibitory activities. A number of derivatives exhibited significant to moderate inhibition potential against α-amylase (IC50 = 23.33 ± 0.02-88.65 ± 0.23 μM) and α-glucosidase (IC50 = 25.01 ± 0.12-89.99 ± 0.09 μM) enzymes, respectively. Results were compared with the standard acarbose (IC50 = 17.08 ± 0.07 μM for α-amylase and IC50 = 17.67 ± 0.09 μM for α-glucosidase). Structure-activity relationship (SAR) was rationalized by analyzing the substituents effects on inhibitory potential. Kinetic studies were implemented to find the mode of inhibition by compounds which revealed competitive inhibition for α-amylase and non-competitive inhibition for α-glucosidase. However, in silico study identified several important binding interactions of ligands (synthetic analogues) with the active site of both enzymes.
The influence of human salivary enzymes on palm wines' odorant concentrations were investigated by the application of aroma extracts dilution analysis (AEDA) and by the calculation of odour activity values (OAVs), respectively. The odorants were quantified by means of stable isotope dilution assays (SIDA), and the degradation profiles of odorants by human saliva were also studied. Results revealed 46 odour-active compounds in the flavour dilution (FD) factor range of 4-256, and all were subsequently identified. Of the 46 odorants, 41 were identified in the Elaeis guineensis wine, 36 in Raphia hookeri wine and 29 in Borassus flabellifer wine. Among the odorants, the highest FD-factors were obtained from acetoin, 2-acetyl-1-pyrroline and 3-isobutyl-2-methoxypyrazine. Among the 13 potent odorants identified, five aroma compounds are reported here as important contributors to palm wine aroma, namely 3-isobutyl-2-methoxy-pyrazine, acetoin, 2-acetyl-1-pyrroline, 3-methylbutylacetate and ethyl hexanoate. Meanwhile, salivary enzymic degradation of odorants was more pronounced among the aldehydes, esters and thiols.