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The medium-chain fatty acids octanoic acid (C8) and decanoic acid (C10) are gaining attention as beneficial brain fuels in several neurological disorders. The protective effects of C8 and C10 have been proposed to be driven by hepatic production of ketone bodies. However, plasma ketone levels correlates poorly with the cerebral effects of C8 and C10, suggesting that additional mechanism are in place. Here we investigated cellular C8 and C10 metabolism in the brain and explored how the protective effects of C8 and C10 may be linked to cellular metabolism. Using dynamic isotope labeling, with [U-13C]C8 and [U-13C]C10 as metabolic substrates, we show that both C8 and C10 are oxidatively metabolized in mouse brain slices. The 13C enrichment from metabolism of [U-13C]C8 and [U-13C]C10 was particularly prominent in glutamine, suggesting that C8 and C10 metabolism primarily occurs in astrocytes. This finding was corroborated in cultured astrocytes in which C8 increased the respiration linked to ATP production, whereas C10 elevated the mitochondrial proton leak. When C8 and C10 were provided together as metabolic substrates in brain slices, metabolism of C10 was predominant over that of C8. Furthermore, metabolism of both [U-13C]C8 and [U-13C]C10 was unaffected by etomoxir indicating that it is independent of carnitine palmitoyltransferase I (CPT-1). Finally, we show that inhibition of glutamine synthesis selectively reduced 13C accumulation in GABA from [U-13C]C8 and [U-13C]C10 metabolism in brain slices, demonstrating that the glutamine generated from astrocyte C8 and C10 metabolism is utilized for neuronal GABA synthesis. Collectively, the results show that cerebral C8 and C10 metabolism is linked to the metabolic coupling of neurons and astrocytes, which may serve as a protective metabolic mechanism of C8 and C10 supplementation in neurological disorders.

It was aimed at investigating the effect of co-cultivating Torulaspora delbrueckii (hereinafter abbreviated as T. delbrueckii) CCTCC M2019523 with Saccharomyces cerevisiae (hereinafter abbreviated as S. cerevisiae) on the quality of greengage wine and the diversity of the microbial community in the mash, including the ratio and sequence of cultivation. Among samples, it shows high quality of the fresh wine when sequential inoculated at the ratio of 1.2:1 and co-cultured. The content of the sugar and succinic acid decreased, while that of alcohol increased. Of them, the content of phenylethyl alcohol and capric aldehyde enhanced, while decanoic acid decreased, so that the intensity of rose and plant aroma was enhanced, the rare delicacy of spoilage and sourness was reduced. The acidity of the fresh wine was also significantly reduced by fed-batch culture and its plant aroma was also enhanced. It provides a new avenue to improve the flavor and quality of wine brewed by a featuring characteristic fruit.

Alteration in metabolite levels in response to heavy metal exposure plays an important role in sustaining metal stress in plants. The objective of the present study was to examine the change in metabolite profile of medicinal plant- Catharanthus roseus in response to heavy metal cadmium (Cd), using gas chromatography mass spectrometry (GC–MS). A total of 78 Cd responsive metabolites were identified in control and cadmium treated samples. These included fatty acids, alkaloids, terpenoids, phytosterols and other miscellaneous compounds. An increase in saturated fatty acids such as myristic acid, palmitic acid, adipic acid, stearic acid, decanoic acid, tridecanoic acid, pentadecanoic acid, octadecanoic acid and decrease in unsaturated fatty acids such as linoleic acid, 9-hexadecenoic acid and 9, 12-octadecadienoic acid indicated lipid peroxidation in treated plants. Higher malondialdehyde content and ultrastructural changes in chloroplasts in treated plants confirmed these results. Elevated levels of alkaloids vindolinine, catharanthine, vindoline, tabersonine, nicotine, coronaridine, vidorosine indicated effect on metabolic pathways including the monoterpenoid indole alkaloids pathway. Other responsive metabolites included terpenes like caryophyllene, campestrin, phytol, neophytadiene, cedrol and silicone oil in addition to isoprenoids and polyamines. These metabolites have known antioxidant properties and are employed by plants to overcome oxidative stress and maintain membrane integrity. Overall, metabolite profiling demonstrated that the Cd tolerance can be attributed to the differential accumulation of the secondary metabolites in C. roseus.

Several studies in hepatocyte cell lines reported that medium-chain fatty acids (MCFAs) with 6-12 carbons showed different metabolic properties from long-chain fatty acids (LCFAs). However, these studies reported unclear effects of different fatty acid molecules on hepatocyte metabolism. This study is aimed to capture the metabolic kinetics of MCFA assimilation in AML12 cells treated with octanoic acid (FA 8:0), decanoic acid (FA 10:0), or lauric acid (FA12:0) [LCFA; oleic acid (FA 18:1)] via metabolic profiling and dynamic metabolome analysis with 13C-labeling. The concentrations of total ketone bodies in the media of cells treated with FA 8:0 or FA 10:0 were 3.22- or 3.69-fold higher than those obtained with FA 18:1 treatment, respectively. FA 12:0 treatment did not significantly increase ketone body levels compared to DMSO treatment (control), whereas FA 12:0 treatment increased intracellular triacylglycerol (TG) levels 15.4 times compared to the control. Metabolic profiles of FA 12:0-treated samples differed from those of the FA 8:0-treated and FA 10:0-treated samples, suggesting that metabolic assimilation of MCFAs differed significantly depending on the MCFA type. Furthermore, the dynamic metabolome analysis clearly revealed that FA 8:0 was rapidly and quantitatively oxidized to acetyl-CoA and assimilated into ketone bodies, citrate cycle intermediates, and glucogenic amino acids but not readily into TGs.

The signal molecules in root exudates that are sensed by plant growth–promoting rhizobacteria (PGPR) are critical to regulate their root colonization. Phosphorylated Spo0A is an important global transcriptional regulator that controls colonization and sporulation in Bacillus species. In this study, we found that deletion of kinD from PGPR strain Bacillus amyloliquefaciens SQR9, encoding an original phosphate donor of Spo0A, resulted in reduced biofilm formation in root exudates compared with the wild-type strain, indicating that KinD is responsible for sensing root exudates. Ligands of B. amyloliquefaciens SQR9 KinD in cucumber root exudates were determined by both the nontargeted ligand fishing method and the targeted surface plasmon resonance detection method. In total, we screened 80 compounds in root exudates for binding to KinD and found that spermine and guanosine could bind to KinD with dissociation constant values of 213 and 51 μΜ, respectively. In addition, calcium l-threonate, N-acetyl-l-aspartic acid, sodium decanoic acid, and parabanic acid could also bind weakly to KinD. The three-dimensional binding models were then constructed to demonstrate the interactions between the root-secreted signals and KinD. It was observed that exogenous spermine reduced the wrinkles of biofilm when kinD was deleted, indicating that KinD might be involved in sensing root-secreted spermine and stabilizing biofilm in response to this negative effector. This study provided a new insight of interaction between a rhizobacterial sensor and root-secreted signals.

Alzheimer’s disease (AD), the most common cause of dementia in the elderly population, is closely linked to a dysregulated cerebral lipid homeostasis and particular changes in brain fatty acid (FA) composition. The abnormal extracellular accumulation and deposition of the peptide amyloid-β (Aβ) is considered as an early toxic event in AD pathogenesis, which initiates a series of events leading to neuronal dysfunction and death. These include the induction of neuroinflammation and oxidative stress, the disruption of calcium homeostasis and membrane integrity, an impairment of cerebral energy metabolism, as well as synaptic and mitochondrial dysfunction. Dietary medium chain fatty acids (MCFAs) and polyunsaturated ω-3-fatty acids (ω-3-PUFAs) seem to be valuable for disease modification. Both classes of FAs have neuronal health-promoting and cognition-enhancing properties and might be of benefit for patients suffering from mild cognitive impairment (MCI) and AD. This review summarizes the current knowledge about the molecular mechanisms by which MCFAs and ω-3-PUFAs reduce the cerebral Aβ deposition, improve brain energy metabolism, and lessen oxidative stress levels.

Saccharomyces cerevisiae is an attractive chassis for the production of medium-chain fatty acids, but the toxic effect of these compounds often prevents further improvements in titer, yield, and productivity. To address this issue, Lem3 and Sfk1 were identified from adaptive laboratory evolution mutant strains as membrane asymmetry regulators. Co-overexpression of Lem3 and Sfk1 [Lem3(M)-Sfk1(H) strain] through promoter engineering remodeled the membrane phospholipid distribution, leading to an increased accumulation of phosphatidylethanolamine in the inner leaflet of the plasma membrane. As a result, membrane potential and integrity were increased by 131.5% and 29.2%, respectively; meanwhile, the final OD600 in the presence of hexanoic acid, octanoic acid, and decanoic acid was improved by 79.6%, 73.4%, and 57.7%, respectively. In summary, this study shows that membrane asymmetry engineering offers an efficient strategy to enhance medium-chain fatty acids tolerance in S. cerevisiae, thus generating a robust industrial strain for producing high-value biofuels.

Ketogenic diets have been utilized for many years to improve health, and as a dietary approach for the treatment of a range of diseases, where the mechanism of these low carbohydrate and high fat diets is widely considered to be through the production of metabolic products of fat breakdown, called ketones. One of these diets, the medium chain triglyceride ketogenic diet, involves high fat dietary intake in the form of medium chain fatty acids (MCFAs), decanoic and octanoic acid, and is commonly used in endurance and high intensity exercises but has also demonstrated beneficial effects in the treatment of numerous pathologies including drug resistant epilepsy, cancer, and diabetes. Recent advances, using Dictyostelium discoideum as a model, have controversially proposed several direct molecular mechanisms for decanoic acid in this diet, independent of ketone generation. Studies in this model have identified that decanoic acid reduces phosphoinositide turnover, diacylglycerol kinase (DGK) activity, and also inhibits the mechanistic target of rapamycin complex 1 (mTORC1). These discoveries could potentially impact the treatment of a range of disorders including epilepsy, cancer and bipolar disorder. In this review, we summarize the newly proposed mechanisms for decanoic acid, identified using D. discoideum, and highlight potential roles in health and disease treatment.

Perfluorodecanoic acid (C10F) is a persistent organic pollutant that bioaccumulates. This study investigated the cytotoxicity and cellular uptake of C10F. When compared with the non-fluorinated counterpart, decanoic acid (C10H), results showed that C10F was more toxic to mouse melanoma B16 cells. Whereas a viability of 97% has been observed even up to 800 μM in the presence of C10H, cytotoxicity was already detected at 100 μM (54% viability) in the presence of C10F. Significantly, cellular uptake of C10F was 32-fold higher than that of C10H. Time course analysis showed a correlation between cellular uptake of C10F and cell behavior. After 1 h of incubation in 50 μM C10F, results confirmed that cellular uptake of C10F already occurred concurrent to loss of cell spreading. This was accompanied by secretion of the black pigment melanin commensurate to the level of stress inflicted on the cells caused by the influx of C10F. When the amount of uptake reached a plateau, no significant change in cell behavior was likewise observed up to 24 h. The effect of C10F was also investigated in various human and animal cell lines. The results confirmed the detrimental effect that C10F has on morphology of different cells in culture, and the differences in cellular uptake. In Madin Darby canine kidney MDCK cells and human fetal lung fibroblast TIG cells, 3.75 and 3.42 pg/cell of C10F were detected, respectively. Comparing the human carcinoma cell lines used, 1.1 pg/cell of C10F was detected in hepatocellular (HepG2) and in renal (RCC) cells while 0.87 pg/cell in cervical (HeLa) cells.

Fatty acids are derived from diet and fermentative processes by the intestinal flora. Two to five carbon chain fatty acids, termed short chain fatty acids (SCFA) are increasingly recognized to play a role in intestinal homeostasis. However, the characteristics of slightly longer 6 to 10 carbon, medium chain fatty acids (MCFA), derived primarily from diet, are less understood. Here, we demonstrated that SCFA and MCFA have divergent immunomodulatory propensities. SCFA down-attenuated host pro-inflammatory IL-1β, IL-6, and TNFα response predominantly through the TLR4 pathway, whereas MCFA augmented inflammation through TLR2. Butyric (C4) and decanoic (C10) acid displayed most potent modulatory effects within the SCFA and MCFA, respectively. Reduction in TRAF3, IRF3 and TRAF6 expression were observed with butyric acid. Decanoic acid induced up-regulation of GPR84 and PPARγ and altered HIF-1α/HIF-2α ratio. These variant immune characteristics of the fatty acids which differ by just several carbon atoms may be attributable to their origins, with SCFA being primarily endogenous and playing a physiological role, and MCFA exogenously from the diet.

In recent years, there has been a growing interest in the screening of natural active ingredients from Eucalyptus essential oils because of their evident importance in practical utility and their undeniable therapeutic properties. Based on this, the aim of the present study was to investigate the chemical profile of the essential oils of the trunk bark of Eucalyptus torquata Luehm. (ETEO), and E. salmonophloia F. Muell. (ESEO), growing in Tunisia. The in vitro cytotoxic properties of the extracted EOs were also evaluated against two human cancer cell lines: breast carcinoma cell lines MDA-MB-231 and colorectal cancer cell lines SW620. The analysis by gas chromatography coupled with mass spectrometry (GC/MS) led to the identification of 32 compounds from the ETEO, with the dominant constituents being the monoterpenes trans-myrtanol (73.4 %) and myrtenol (4.7 %), and the apocarotene (E)-β-ionone (3.9 %). In the case of ESEO, 29 compounds were identified with trans-myrtanol (25.0 %), decanoic acid (22.1 %), nonanoic acid (9.8 %), γ-elemene (6.5 %), γ-maaliene (5.5 %), and α-terpineol (5.3 %) as the main components. The cytotoxicity of EOs against the two chosen cell lines was tested using Crystal Violet Staining (CVS) assay and 5-fluorouracil as a reference drug. The two EOs exhibited a significant dose-dependent inhibition against the viability of the used cell lines. Their inhibitory effects were particularly observed towards SW620 colon carcinoma cells with IC50 values of 26.71±1.22 and 22.21±0.85 μg/mL, respectively, indicating that both oils were more cytotoxic for SW620 cells compared to MDA-MB-231 one.

The subject of this study is the synthesis and biological evaluation of anoplin-based (Gly-Leu-Leu3 -Lys-Arg5 -Ile-Lys-Thr8 -Leu-Leu-NH2 )-designed (lipo)-peptides, aiming at the development of new antibiotic substances. The design of synthetic compounds based on natural bioactive molecules is an optimistic strategy for the development of new pharmaceutics. Antimicrobial peptides (AMPs) and (lipo)-peptides are two classes of promising compounds, with characteristics that allow them to express their activity by differentiated mechanisms of action. On this basis, anoplin, a natural AMP, was used as a scaffold to design five peptides and seven lipopeptide analogs of them. Substitutions were made on residues Leu3 and Arg5 of the interphase and on Thr8 of the polar phase, as well as N-terminus conjunctions with octanoic and decanoic acid. The outcome of the biological evaluation revealed that some analogs might have substantial clinical potential. Specifically, Ano 1-F, Ano 3-F, Ano 4-C10 , and Ano 5-F are strongly active against Gram-negative bacteria at minimum inhibitory concentration (MIC) values of 3 μg/ml, while Ano 4-F is active against Gram-positive bacteria at 1 μg/ml. Ano 2-C10 , C10 -Gly-Leu-Lys3 -Lys-Ile5 -Ile-Lys-Lys8 -Leu-Leu-NH2 , is the most promising compound (MIC = 0.5 μg/ml) for the development of new pharmaceutics. The conformational features of the synthetic peptides were investigated by circular dichroism spectroscopy, and their physicochemical parameters were calculated. Our study shows that appropriate substitutions in the anoplin sequence in combination with Nα -acylation may lead to new effective AMPs.

We demonstrate that medium‐chain fatty acids mimic the quorum‐sensing molecule farnesol. Six sets of evidence, that is, (i) structural similarities, (ii) inhibition of hyphal growth, (iii) inhibition of biofilm formation, (iv) inhibition of farnesol production, (v) inhibition of sterol production, and (vi) effects on gene expressions, which showed medium‐chain fatty acids interfere with farnesol signaling and that their antibiofilm and antivirulence activities are superior to that of farnesol. Our findings show that fatty acids found in prokaryotes and eukaryotes might interfere with fungal communication and that medium‐chain fatty acids might be used as developmental starting points for the design of potent antibiofilm and antifungal agents against fungal Candida species., Summary Candida biofilms are tolerant to conventional antifungal therapeutics and the host immune system. The transition of yeast cells to hyphae is considered a key step in C. albicans biofilm development, and this transition is inhibited by the quorum‐sensing molecule farnesol. We hypothesized that fatty acids mimicking farnesol might influence hyphal and biofilm formation by C. albicans. Among 31 saturated and unsaturated fatty acids, six medium‐chain saturated fatty acids, that is, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid and lauric acid, effectively inhibited C. albicans biofilm formation by more than 75% at 2 µg ml−1 with MICs in the range 100–200 µg ml−1. These six fatty acids at 2 µg ml−1 and farnesol at 100 µg ml−1 inhibited hyphal growth and cell aggregation. The addition of fatty acids to C. albicans cultures decreased the productions of farnesol and sterols. Furthermore, down‐regulation of several hyphal and biofilm‐related genes caused by heptanoic or nonanoic acid closely resembled the changes caused by farnesol. In addition, nonanoic acid, the most effective compound diminished C. albicans virulence in a Caenorhabditis elegans model. Our results suggest that medium‐chain fatty acids inhibit more effectively hyphal growth and biofilm formation than farnesol.

Medium-chain fatty acids (MCFA) are dietary components with a chain length ranging from 6 to 12 carbon atoms. MCFA can cross the blood-brain barrier and in the brain can be oxidized through mitochondrial β-oxidation. As components of ketogenic diets, MCFA have demonstrated beneficial effects on different brain diseases, such as traumatic brain injury, Alzheimer's disease, drug-resistant epilepsy, diabetes, and cancer. Despite the interest in MCFA effects, not much information is available about MCFA metabolism in the brain. In this study, with a gas chromatography-mass spectrometry (GC-MS)-based metabolomics approach, coupled with multivariate data analyses, we followed the metabolic changes of U87MG glioblastoma cells after the addition of octanoic (C8), or decanoic (C10) acids for 24 h. Our analysis highlighted significant differences in the metabolism of U87MG cells after the addition of C8 or C10 and identified several metabolites whose amount changed between the two groups of treated cells. Overall, metabolic pathway analyses suggested the citric acid cycle, Warburg effect, glutamine/glutamate metabolism, and ketone body metabolism as pathways influenced by C8 or C10 addition to U87MG cells. Our data demonstrated that, while C8 affected mitochondrial metabolism resulting in increased ketone body production, C10 mainly influenced cytosolic pathways by stimulating fatty acid synthesis. Moreover, glutamine might be the main substrate to support fatty acids synthesis in C10-treated cells. In conclusion, we identified a metabolic signature associated with C8 or C10 addition to U87MG cells that can be used to decipher metabolic responses of glioblastoma cells to MCFA treatment.

A major challenge in understanding how biological cells arose on the early Earth is explaining how RNA and membranes originally co-localized. We propose that the building blocks of RNA (nucleobases and ribose) bound to self-assembled prebiotic membranes. We have previously demonstrated that the bases bind to membranes composed of a prebiotic fatty acid, but evidence for the binding of sugars has remained a technical challenge. Here, we use pulsed field gradient nuclear magnetic resonance to demonstrate that ribose and other sugars bind to membranes of decanoic acid. Moreover, binding of some bases is strongly enhanced when they are linked to ribose to form a nucleoside or—with the addition of phosphate—a nucleotide. This enhanced binding could have played a role in the molecular evolution leading to the production of RNA.

The chemical composition of Anacyclus valentinus essential oil from Algeria was determined and its antifungal effect in vitro toward 7 toxigenic fungal strains was evaluated. Essential oil yield of 0.13% (v/w) was obtained from the aerial parts of A. valentinus using hydrodistillation. The GC/MS analysis identified 29 components of which ?-3-carene (31%), spathulenol (14.2%), decanoic acid (5.5%), ?-cadinene (4.4%), anethole (3.4%) and aromadendrene (3.3%) were the major compounds of this oil. The results of the antifungal activity showed that the most sensitive fungal strains to A. valentinus oil were Fusarium graminearum, Aspergillus parasiticus, and Penicillium expansum with lower minimal fungicidal concentration (MFC) of 1.25 µl/ml (v/v). The oil also had a strong fungicidal effect against A. flavus and F. moniliforme at a MFC value of 2.5 µl/ml, while the oil concentration of 10 µl/ml was needed to show a fungicidal activity against A. ochraceus and P. citrinum. This study suggested that A. valentinus oil is a potential candidate to be used as a safe biocontrol agent to prevent food crops from fungal diseases and improve product quality and safety. © 2018 Elsevier Ltd

Decanoic acid is a valuable compound used as precursor for industrial chemicals, pharmaceuticals, and biofuels. Despite efforts to produce it from renewables, only limited achievements have been reported. Here, we report an engineered cell factory able to produce decanoic acid as a major product from glycerol, and abundant and renewable feedstock. We exploit the overlapping chain-length specificity of β-oxidation reversal (r-BOX) and thioesterase enzymes to selectively generate decanoic acid. This was achieved by selecting r-BOX enzymes that support the synthesis of acyl-CoA of up to 10 carbons (thiolase BktB and enoyl-CoA reductase EgTER) and a thioesterase that exhibited high activity toward decanoyl-CoA and longer-chain acyl-CoAs (FadM). Combined chromosomal and episomal expression of r-BOX core enzymes such as enoyl-CoA reductase and thiolase (in the presence of E. coli thioesterase FadM) increased titer and yield of decanoic acid, respectively. The carbon flux toward decanoic acid was substantially increased by the use of an organic overlay, which decreased its intracellular accumulation and presumably increased its concentration gradient across cell membrane, suggesting that decanoic acid transport to the extracellular medium might be a major bottleneck. When cultivated in the presence of a n-dodecane overlay, the final engineered strain produced 2.1 g/L of decanoic acid with a yield of 0.1 g/g glycerol. Collectively, our data suggests that r-BOX can be used as a platform to selectively produce decanoic acid and its derivatives at high yield, titer and productivity.

Ketogenic diets, used in epilepsy treatment, are considered to work through reduced glucose and ketone generation to regulate a range of cellular process including autophagy induction. Recent studies into the medium-chain triglyceride (MCT) ketogenic diet have suggested that medium-chain fatty acids (MCFAs) provided in the diet, decanoic acid and octanoic acid, cause specific therapeutic effects independent of glucose reduction, although a role in autophagy has not been investigated. Both autophagy and MCFAs have been widely studied in Dictyostelium, with findings providing important advances in the study of autophagy-related pathologies such as neurodegenerative diseases. Here, we utilize this model to analyze a role for MCFAs in regulating autophagy. We show that treatment with decanoic acid but not octanoic acid induces autophagosome formation and modulates autophagic flux in high glucose conditions. To investigate this effect, decanoic acid, but not octanoic acid, was found to induce the expression of autophagy-inducing proteins (Atg1 and Atg8), providing a mechanism for this effect. Finally, we demonstrate a range of related fatty acid derivatives with seizure control activity, 4BCCA, 4EOA, and Epilim (valproic acid), also function to induce autophagosome formation in this model. Thus, our data suggest that decanoic acid and related compounds may provide a less-restrictive therapeutic approach to activate autophagy.

Malaria is still a global health problem. Plasmodium is a single-cell protozoan parasite that causes malaria and is transmitted to humans through the female Anopheles mosquito. The previous study showed that Sonchus arvensis L. callus has antiplasmodial activity. Several treatments are needed for callus quality improvement for antimalarial compound production. This study aimed to examine the effect of dolomite [CaMg(CO3)2] on growth (morpho-anatomical structure and biomass), secondary metabolite production, and in vitro antiplasmodial activity of S. arvensis L. callus. In this study, leaf explants were grown in Murashige and Skoog medium with a combination of 2,4-dichlorophenoxyacetic acid (2,4-D, one mg/L) and 6-benzyl amino purine (BAP, 0.5 mg/L) with dolomite (50, 75, 100, 150, and 200 mg/L). The 21 days callus ethanolic and methanolic extract were analyzed by gas chromatography-mass spectrometry (GC-MS) and thin-layer chromatography (TLC). The antiplasmodial test was performed on a blood culture infected with Plasmodium falciparum strain 3D7 using the Rieckmann method. The results showed that dolomite significantly affected callus growth, metabolite profile, and in vitro antiplasmodial activity. Dolomite (150 mg/L) showed the highest biomass (0.590 ± 0.136 g fresh weight and 0.074 ± 0.008 g dry weight). GC-MS analysis detected four compounds from callus ethanolic extract. Pelargonic acid, decanoic acid, and hexadecanoic acid were major compounds. One new terpenoid compound is based on TLC analysis. S. arvensis L. callus has antiplasmodial activity with the IC50 value of 5.037 μg/mL. It was three times lower than leaf methanolic extract and five times lower than leaf ethanolic extract.

PA forms a biofilm resistant to antibiotics, hindering antibiotics efficacy and preventing the eradication of PA, has attracted much attention for its biofilm. In this study, we first established and validated an efficient and sensitive gas chromatography-mass spectrometry (GC–MS) method for the quantification of metabolites in biofilm. Decanoic acid was used as the internal standard. The separation of Palmitic acid, stearic acid and Decanoic acid was conducted on an Elite-5 MS column (30 m × 0.25 mm, 0.25 μm) using gradient elution condition at a flow rate of 1 mL/min. Palmitic acid, stearic acid and Decanoic acid were determined under the positive ionization mode, respectively. The calibration curve of Palmitic acid and stearic acid were established in the range of 4 to 128 μg/mL (r2 = 0.999). The recovery of palmitic acid and stearic acid were between 98.76% and 113.91%, RSD ＜ 5%. The well validated method was used to detect the metabolites of Pseudomonas aeruginosa biofilm. 54 metabolites were isolated and identified from biofilm samples, and 7 important signal pathways were identified by KEGG enrichment analysis. ABC transporters and bacterial chemotaxis signaling pathways have an important impact on the growth of PA biofilm among these metabolic pathways. This study provides valuable references for the further study of PA biofilm, especially the change of metabolite content and the search for biomarkers.

ObjectivesThis study was carried out to investigate the impact of various isolated phytochemical components present in the Wattakaka volubilis leaves for the growth and proliferation of human osteoblast like cells (MG63).Key findingsEthyl acetate was found to be the best solvent for potential extraction of phytocompounds. Further, the MTT assay was carried out to deduce the viability of 44 isolated phytochemicals. Ten phytochemical fractions found to increase the cell growth were subjected to statistical tool namely Plackett–Burman and Central composite design to screen the optimum phytochemical fraction and its dosage. The active phytochemical constituents were analysed and identified as hexadeconoic acid, octadeconoic acid, N,N-diisopropyl(2,2,3,3,3-pentafluoropropyl)amine using GC-MS and HPLC techniques. The impact of optimized concentration was assessed on osteoblast cells. The maximum % cell viability, % DNA and collagen content were found to be 164.44, 159.32 and 3.81, respectively.ConclusionsThe results confirmed that the optimized fraction containing decanoic acid and isopropyl amine at particular concentration stimulated the proliferation of human osteoblast (MG63) cells. Hence, the optimized concentration of this compound from W. volubilis may used for treatment of bone related injuries externally.

Seed oils of many Cuphea sp. contain >90% of medium-chain fatty acids, such as decanoic acid (10:0). These seed oils, which are among the most compositionally variant in the plant kingdom, arise from specialized fatty acid biosynthetic enzymes and specialized acyltransferases. These include lysophosphatidic acid acyltransferases (LPAT) and diacylglycerol acyltransferases (DGAT) that are required for successive acylation of medium-chain fatty acids in the sn-2 and sn-3 positions of seed triacylglycerols (TAGs). Here we report the identification of a cDNA for a DGAT1-type enzyme, designated CpuDGAT1, from the transcriptome of C. avigera var pulcherrima developing seeds. Microsomes of camelina (Camelina sativa) seeds engineered for CpuDGAT1 expression displayed DGAT activity with 10:0-CoA and the diacylglycerol didecanoyl, that was approximately 4-fold higher than that in camelina seed microsomes lacking CpuDGAT1. In addition, coexpression in camelina seeds of CpuDGAT1 with a C. viscosissima FatB thioesterase (CvFatB1) that generates 10:0 resulted in TAGs with nearly 15 mol % of 10:0. More strikingly, expression of CpuDGAT1 and CvFatB1 with the previously described CvLPAT2, a 10:0-CoA-specific Cuphea LPAT, increased 10:0 amounts to 25 mol % in camelina seed TAG. These TAGs contained up to 40 mol % 10:0 in the sn-2 position, nearly double the amounts obtained from coexpression of CvFatB1 and CvLPAT2 alone. Although enriched in diacylglycerol, 10:0 was not detected in phosphatidylcholine in these seeds. These findings are consistent with channeling of 10:0 into TAG through the combined activities of specialized LPAT and DGAT activities and demonstrate the biotechnological use of these enzymes to generate 10:0-rich seed oils.

The present study aimed to identify some metabolites products obtained from different jojoba callus tissue extracts using gas chromatography/mass spectrometry analysis (GC-MS). It is known that Jojoba, a medicinal and oil-yielding, has multi-purpose uses. In addition, it produces toxins, fatty acids, phenolic compounds and other secondary metabolites from callus identified using GC-MS. Despite the direct effect of 2,4-D on directing the explant towards callus induction, it has interaction effect with Kin and achieves hormonal balance inside the explant. There is a significant interaction effect between Kin and 2,4-D. The increased concentration of both Kin and 2,4-D raises the extent of nodal segments response towards proliferation, development, and callus induction. Our results showed that the interaction effect between Kin and 2,4-D is the best results for phytochemical active constituents formation achieved from callus cultured. Qualitative results revealed that increasing cytokinins Kin concentration leads to slightly double increase in active constituents from the explants for Triodecanoic and Methoxyacetic acids. While, the gradual increase of 2,4-D to 2.0 mg l-1 caused a single increase in active constituents for Triodecanoic, Methoxyacetic and Octadecanoic acid, respectively. On the other hand, Decanoic acid has no effect by adding both hormones (Kin and 2,4-D) and also Octadecanoic acid when kin is added. Also, there is a direct relation between the development of callus and reproduction of active phytochemical constituents, which increase qualitatively by increasing callus development and 2,4-D hormone concentration at 2 mg l-1 for 1-Hexadecanol, Nonadecatriene, Aristolene and Tricosene, respectively compared to free hormone treatment. Key words: Active constituents, callus, fatty acids, jojoba, Simmondsia chinensis.

A lysozyme-chitosan conjugate preparation (LYZOX), produced from egg white lysozyme and chitosan by Maillard reaction, is a commercial product developed as a cosmetic ingredient or food additive. Effects of LYZOX on in vitro growth of Candida albicans were examined. C. albicans cells were treated with LYZOX for 3 hrs, and then washed and cultured for an additional 16 hrs in modified RPMI1640 medium. Mycelial growth of C. albicans was clearly inhibited by more than 100 μg/ml of LYZOX in a concentration-dependent manner. On the other hand, corresponding concentration of chitosan or lysozyme or their mixture only scarcely showed clear inhibitory effect. Similarly, anti-Candida activity of the combination of LYZOX and decanoic acid, a middle-chain fatty acid, was also examined. Inhibitory activity of this combination against mycelial growth of C. albicans was very potent and appeared synergistic, since fractionated inhibitory concentration (FIC) index for 70% growth inhibition was calculated to be 0.20. Oral application of this combination improved the symptoms of Candida-infected-tongue in an experimental murine candidiasis model. On the basis of these results, the possible application of LYZOX as a new functional product with anti-candida activity was discussed.

Hydroxy fatty acids (HFAs) are valuable compounds that are widely used in medical, cosmetic and food fields. Production of ω-HFAs via bioconversion by engineered Escherichia coli has received lots of attention because this process is environmentally friendly. In this study, a whole-cell bio-catalysis strategy was established to synthesize medium-chain ω-HFAs based on the AlkBGT hydroxylation system from Pseudomonas putida GPo1. The effects of blocking the β-oxidation of fatty acids (FAs) and enhancing the transportation of FAs on ω-HFAs bio-production were also investigated. When fadE and fadD were deleted, the consumption of decanoic acid decreased, and the yield of ω-hydroxydecanoic acid was enhanced remarkably. Additionally, the co-expression of the FA transporter protein, FadL, played an important role in increasing the conversion rate of ω-hydroxydecanoic acid. As a result, the concentration and yield of ω-hydroxydecanoic acid in NH03(pBGT-fadL) increased to 309 mg/L and 0.86 mol/mol, respectively. This whole-cell bio-catalysis system was further applied to the biosynthesis of ω-hydroxyoctanoic acid and ω-hydroxydodecanoic acid using octanoic acid and dodecanoic acid as substrates, respectively. The concentrations of ω-hydroxyoctanoic acid and ω-hydroxydodecanoic acid reached 275.48 mg/L and 249.03 mg/L, with yields of 0.63 mol/mol and 0.56 mol/mol, respectively. This study demonstrated that the overexpression of AlkBGT coupled with native FadL is an efficient strategy to synthesize medium-chain ω-HFAs from medium-chain FAs in fadE and fadD mutant E. coli strains.

Macrosphyra longistyla has been used in many traditional systems of medicine for its anti-hemorrhagic, antidiabetic, anti-ulcer, and anti-diarrhea properties. The acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitions of the crude methanol extracts and its various partitioned fractions were determined by a modified method of Ellman. An evaluation of the antioxidant activity was carried out using 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging, ferric reducing power, and nitric oxide scavenging assays. The total flavonoids were estimated based on the aluminum chloride method, while the total tannins and phenolics were estimated based on the vanillin&ndash, HCl and Folin&ndash, Ciocalteu method, respectively. The ethyl acetate fraction had the highest DPPH radical scavenging activity, and the highest ferric reducing power with a concentration providing 50% inhibition (IC50) of 0.079 mg/mL and 0.078 mg/mL, respectively, while the crude methanol extract had the highest nitric oxide scavenging activity with an IC50 of 0.008 mg/mL. The methanol extract had the highest phenolics and flavonoids contents, while the aqueous fraction had the highest tannin content. The crude methanol extract had the best AChE and BuChE inhibitory action, with an IC50 of 0.556 &micro, g/mL and 5.541 &micro, g/mL, respectively, suggesting that the plant had a better AChE inhibiting potential. A moderate correlation was observed between the phenolic content and DPPH radical scavenging, NO radical scavenging, and AChE inhibitory activities (r2 = 0.439, 0.430, and 0.439, respectively), while a high correlation was seen between the flavonoid content and these activities (r2 = 0.695, 0.724, and 0.730, respectively), and the ferric reducing antioxidant power correlated highly with the proautocyanidin content (r2 = 0.801). Gas chromatography mass spectrometry (GCMS) revealed decanoic acid methyl ester (24.303%), 11,14-eicosadienoic acid methyl ester (16.788%), linoelaidic acid (10.444%), pentadecanoic acid (9.300%), and 2-methyl-hexadecanal (9.285%). Therefore, we suggest that M. longistyla contain bioactive chemicals, and could be a good alternative for the management of Alzheimer&rsquo, s and other neurodegenerative diseases.

The grape seed extract (GSE) hybridized with medium-chain saturated fatty acids (decanoic acid) exhibited higher lipophilicity, antioxidant activity, and anti-proliferative activity than its parents. The chemical structures of individual hybridized GSE derivatives were identified as 3′-O-decanoyl catechin, 3′-O-decanoyl epicatechin, 3′, 5′-2-O-decanoyl epigallocatechin, and 3′, 4′, 3″, 5″-4-O-decanoyl epicatechin gallate by HPLC-MS2 and 1H and 13C NMR. For growth inhibitory effect on HepG2 cells, hybridized GSE derivatives (EC50 = 44.38 μg/mL) were significantly (p

A simple and ecofriendly sample preparation method was developed for quantifying fluoroquinolone (FQ) antibiotics in surface water. Seventeen combinations of monoterpenes (menthol, thymol, and camphor), fatty acids (heptanoic, octanoic, nonanoic, and decanoic acids), and a benzoate ester (salol) were utilized for the in situ formation of hydrophobic deep eutectic solvents (hDESs) for liquid-liquid microextraction (LLME). The hDES comprising thymol and heptanoic acid (HA) exhibited the highest extraction efficiency for ofloxacin, norfloxacin, ciprofloxacin, and enrofloxacin. Optimization via the one-variable-at-a-time strategy revealed that a 2:1 ratio of thymol to HA yielded the highest efficiency for antibiotic extraction at pH 4-7. Further, response surface methodology-based optimization suggested that the optimal extraction conditions involved the use of appropriate amounts of thymol and HA to generate 100 μL of hDES in 10 mL of aqueous sample with incubation at 52 °C for 5 min, followed by automated shaking for 1 min. The collected hDES phase was diluted and subjected to liquid chromatography-ultraviolet detection analysis. The established method based on in situ formation of hDES coupled with shaker-assisted LLME (in situ hDES-SA-LLME) was validated. The method was specific and showed good linearity in the 15-3000 ng mL-1 concentration range (r2 ≥ 0.9997), with a limit of detection of 3.0 ng mL-1, limit of quantification of 9.0 ng mL-1, accuracy of 84.1-113.65%, and intra-day and inter-day precision of ≤7.78% RSD and ≤7.91% RSD, respectively. The method was successfully applied to three different types of real surface water samples. Without toxic volatile organic solvents, the developed method allows for safe and rapid, yet reliable, analysis of FQ antibiotics.

Medium-chain triglyceride (MCT) ketogenic diets increase ketone bodies, which are believed to act as alternative energy substrates in the injured brain. Octanoic (C8:0) and decanoic (C10:0) acids, which produce ketone bodies through β-oxidation, are used as part of MCT ketogenic diets. Although the ketogenic role of MCT is well-established, it remains unclear how the network metabolism underlying β-oxidation of these medium-chain fatty acids (MCFA) differ. We aim to elucidate basal β-oxidation of these commonly used MCFA at the cellular level. Human-induced pluripotent stem cell-derived (iPSC) astrocytes were incubated with [U-13C]-C8:0 or [U-13C]-C10:0, and the fractional enrichments (FE) of the derivatives were used for metabolic flux analysis. Data indicate higher extracellular concentrations and faster secretion rates of β-hydroxybutyrate (βHB) and acetoacetate (AcAc) with C8:0 than C10:0, and an important contribution from unlabeled substrates. Flux analysis indicates opposite direction of metabolic flux between the MCFA intermediates C6:0 and C8:0, with an important contribution of unlabeled sources to the elongation in the C10:0 condition, suggesting different β-oxidation pathways. Finally, larger intracellular glutathione concentrations and secretions of 3-OH-C10:0 and C6:0 were measured in C10:0-treated astrocytes. These findings reveal MCFA-specific ketogenic properties. Our results provide insights into designing different MCT-based ketogenic diets to target specific health benefits.

Skin wound dressing materials, which can accelerate wound healing and have the synthetic advantages of simplicity, environmental safety, and resource abundance, are becoming a hot topic of research now. Following such a research trend, we prepared novel decanoic acid functionalized chitosan (CSDA) with good solubility by acylation via a facile one-step method. FTIR, 1H NMR, and UV–Vis results demonstrated that alkyl chains were successfully grafted onto C2 positions of chitosan (CS) skeleton through acylation. XRD patterns implied that the crystallinity of CSDA greatly declined due to the introduction of alkyl moieties, favorable for improving water solubility. Conductometric titration results showed that the degrees of substitution of CSDA, CSDA1, and CSDA2 were 41.42, 26.12, and 23.17%, respectively. MTT assay and hemolysis experiments illustrated that all the CSDA samples tested in this work possessed good hemocompatibility (hemolysis rate 75%) toward L929 cells. Moreover, CSDA-soaked gauze dressings and full-thickness excisional wound models were employed to estimate the feasibility of CSDA as wound dressing material, and the results displayed that CSDA with the degree of substitution of 41.42% could enhance the wound healing rate to 100% on day 16. Altogether, CSDA might be potential material used as wound dressing.

Chloride and sodium constitute as the major ions in most saline soils, contributing to salt-induced damage in plants. Research on salt tolerance has mostly concentrated on the sodium toxicity; however, chloride toxicity also needs to be considered to understand the physiological, biochemical, and metabolite changes under individual and additive salts. In this study, we investigated the effect of individual Na(+) and/or Cl(−) ions (equimolar 100 mM NaCl, Na(+) and Cl(−) salts) using in vitro cultures of four soybean genotypes with contrasting salt tolerance. In general, all the treatments significantly induced antioxidant enzymes activities such as catalase, ascorbate peroxidase, glutathione reductase, guaiacol peroxidase, and superoxide dismutase and osmolytes including proline, glycine betaine, and total soluble sugar (TSS). Both individual (Na(+), Cl(−)) and additive (NaCl) stresses induced more pronounced activation of antioxidant enzyme machinery and osmolytes accumulation in the tolerant genotypes (MAUS-47 and Bragg). The sensitive genotypes (Gujosoya-2 and SL-295) showed higher accumulation of Na(+) and Cl(−), while the tolerant genotypes were found to maintain a low Na(+)/K(+) and high Ca(2+) level in combination with enhanced antioxidant defense and osmotic adjustment. Gas chromatography–mass spectrometry (GC–MS)-based metabolomic profiling depicted the association of certain metabolites under individualistic and additive salt effects. The genotype-specific metabolic changes indicated probable involvement of azetidine, 2-furanmethanol, 1,4-dioxin, 3-fluorothiophene, decanoic acid and 2-propenoic acid methyl ester in salt-tolerance mechanism of soybean. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s13205-019-1599-6) contains supplementary material, which is available to authorized users.

Halogen bonding (XB) was here proposed, for the first time, as a solubilization mechanism for increasing efficiency in the liquid-liquid microextraction of halogenated compounds. The approach was illustrated by the extraction of hexabromocyclododecane (HBCD) enantiomers in natural waters with a supramolecular solvent (SUPRAS) made up of inverted hexagonal aggregates of decanoic acid. The XB and dispersion interactions offered by the SUPRAS were able to extract the six HBCD enantiomers (i.e. (+)-α-, (-)-α- (+)-β-, (-)-β-, (+)-γ- and (-)-γ-) quantitatively (e.g. recoveries in the range 89–106%) and reach concentration factors as high as 720 without the need for solvent evaporation. HBCD enantiomers in the SUPRAS extract were directly analysed by chiral liquid chromatography coupled to tandem mass spectrometry (LC MS/MS). Quantitation limits of the method (0.09-0.9 ng L−1) were below the quality standard stablished by the European Union for HBCDs in inland surface water samples (1.6 ng L−1), and the precision, expressed as relative standard deviation (n = 6), was below 9% for all the HBCD enantiomers at concentrations within the range 50–500 ng L−1. The method was successfully applied to the enantioselective determination of HBCDs in the dissolved and the particle-bound fractions of river waters containing different concentration of suspended particles (10–57.8 mg L−1) that were spiked at two concentration levels (10 and 100 ng L−1). The results here obtained prove that XB is a valuable mechanism for the solubilisation of halogenated compounds that can effectively increase their recovery from liquid and solid samples.

Beef from Japanese Black cattle (Japanese Wagyu) is renowned for its flavor characteristics. To clarify the key metabolites contributing to this rich and sweet aroma of beef, an omics analysis combined with GC-olfactometry (GC-O) and metabolomics analysis with gas chromatography&ndash, mass spectrometry (GC-MS) were applied. GC-O analysis identified 39 odor-active odorants from the volatile fraction of boiled beef distilled by solvent-assisted flavor evaporation. Eight odorants predicted to contribute to Wagyu beef aroma were compared between Japanese Black cattle and Holstein cattle using a stable isotope dilution assay with GC&ndash, tandem quadrupole mass spectrometry. By correlating the sensory evaluation values of retronasal aroma, &gamma, hexalactone, &gamma, d2ecalactone, and &gamma, undecalactone showed a high correlation with the Wagyu beef aroma. Metabolomics data revealed a high correlation between the amounts of odorants and multiple metabolites, such as glutamine, decanoic acid, lactic acid, and phosphoric acid. These results provide useful information for assessing the aroma and quality of beef.

The chemical composition of the essential oil (EO) obtained from the aerial parts of Stachys benthamiana Boiss. was analyzed by GC and GC-MS. Thirty-four components were identified in the oil. Undecanoic acid (20.86%), dodecanoic acid (14.49%), dodecanal (11.07%), caryophyllene oxide (9.4%), spathulenol (8.6%), decanoic acid (6.84%) and β-eudesmol (4.94%), were the main compounds in the EOs. This is the first report of different chemical compositions of S. benthamiana EOs from the southern Zagros of Iran.

Conditions for the optimal production of polyhydroxyalkanoate (PHA) by Pseudomonas mendocina PSU using a biodiesel liquid waste (BLW) were determined by response surface methodology. These were an initial carbon to nitrogen ratio (C/N) of 40 (mole/mole), an initial pH of 7.0, and a temperature of 35 °C. A biomass and PHA concentration of 3.65 g/L and about 2.6 g/L (77% DCW), respectively, were achieved in a growth associated process using 20 g/L glycerol in the BLW after 36 h of exponential growth. The PHA monomer compositions were 3HB (3-hydroxybutyrate), a short-chain-length-PHA, and the medium-chain-length-PHA e.g. 3-hydroxyoctanoate and 3-hydroxydecanoate. Both the phbC and phaC genes were characterized. The phbC enzyme had not been previously detected in a Pseudomonas mendocina species. A 2.15 g/L of an exopolysaccharide, alginate, was also produced with a similar composition to that of other Pseudomonas species.

Decanoic acid is an ideal substrate for the synthesis of medium-chain-length poly-3-hydroxyalkanoate (MCL-PHA), but its use for this purpose has only previously been studied in shake-flasks likely due to its surfactant properties, low aqueous solubility and high melting temperature. A fed-batch fermentation process was developed for the production of MCL-PHA from decanoic acid using Pseudomonas putida KT2440. Decanoic acid was kept in liquid form by heating or by mixing with acetic acid to prevent crystallization. Different ratios of decanoic acid:acetic acid:glucose (DA:AA:G) were fed to produce a specific growth rate of 0.15 h(-1). This method produced a maximum of 39 g L(-1) dry biomass containing 67% MCL-PHA when the DA:AA:G ratio was 5:1:4. However, a declining growth rate occurred in the late stage of fermentation, resulting in decanoic acid accumulation in the bioreactor leading to foaming. The duration of MCL-PHA production was extended by shifting from exponential to linear feeding before accumulation of decanoic acid. This resulted in 75 g L(-1) biomass containing 74% PHA and an overall PHA productivity of 1.16 g L(-1)h(-1) with the production of each gram of PHA requiring only 1.16 g of decanoic acid. The final PHA composition (on a molar basis) was 78% 3-hydroxydecanoate, 11% 3-hydroxyoctanoate and 11% 3-hydroxyhexanoate.

Uncoupling protein 3 (UCP3) and pyruvate dehydrogenase kinase 4 (PDK4) in skeletal muscle are key regulators of the glucose and lipid metabolic processes that are involved in insulin resistance. Medium-chain fatty acids (MCFAs) have anti-obesogenic effects in rodents and humans, while long-chain fatty acids (LCFAs) cause increases in body weight and insulin resistance. To clarify the beneficial effects of MCFAs, we examined UCP3 and PDK4 expression in skeletal muscles of mice fed a MCFA- or LCFA-enriched high-fat diet (HFD). Five-week feeding of the LCFA-enriched HFD caused high body weight gain and induced glucose intolerance in mice, compared with those in mice fed the MCFA-enriched HFD. However, the amounts of UCP3 and PDK4 transcripts in the skeletal muscle of mice fed the MCFA- or LCFA-enriched HFD were similar. To further elucidate the specific effects of MCFAs, such as capric acid (C10:0), on lipid metabolism in skeletal muscles, we examined the effects of various FAs on expression of UCP3 and PDK4, in mouse C2C12 myocytes. Although palmitic acid (C16:0) and lauric acid (C12:0) significantly induced expression of both UCP3 and PDK4, capric acid (C10:0) upregulated only UCP3 expression via activation of peroxisome proliferator-activated receptor-δ. Furthermore, palmitic acid (C16:0) disturbed the insulin-induced phosphorylation of Akt, while MCFAs, including lauric (C12:0), capric (C10:0), and caprylic acid (C12:0), did not. These results suggest that capric acid (C10:0) increases the capacity for fatty acid oxidation without inhibiting glycolysis in skeletal muscle.

For a detailed examination of the interaction of rhamnose containing derivatives with recombinant horseshoe crab plasma lectin (rHPL), two di-rhamno-di-lipids (an α-1,2- and an α-1,3-linked) were synthesized via a new simple method. The N-iodosuccinimide/triflic acid mediated glycosylation of the methyl (R)-3-hydroxydecanoate with phenyl-1-thio-rhamnobioside donors afforded the mono-lipid disaccharides. Removal of the methyl ester group followed by esterification of the mono-lipids with a second (R)-3-hydroxydecanoate unit resulted in fully protected di-lipid derivatives, transformation of which into the target compounds was accomplished in two steps. This method allows the synthesis of both regioisomers in only 6 steps starting from the corresponding free disaccharides. Both synthetic di-rhamnolipids were biologically active for lectin binding differential binding preference between two isomeric di-rhamno-di-lipids. The rHPL lectin favours the α-1,3-linked di-rhamno-di-lipids over its α-1,2-linked regioisomer.

Deep eutectic solvents (DESs) were used as an extractant for the determination of pyrethroids in environmental water and tea beverage samples. Three different acids were chosen as hydrogen bond donors for preparation of DESs, and decanoic acid was optimal because of its high recovery. Factors affecting relative recovery were optimized individually, including salt addition, surfactant addition, extraction temperature, DES amount, and sample volume etc. Under the optimized experimental conditions, the relative recovery of pyrethroids was from 89.3% to 97.7%, with relative standard deviation (RSD) values ranging from 1.75% to 2.73%. The linear correlation coefficient ranged from 0.9981 to 0.9992, and the linear range was between 1.9 and 500 μg/L. Based on a signal-to-noise ratio (S/N) of 3:1, the limit of detection (LOD) values were 0.56 to 1.24 μg/L. The enrichment factor ranged from 92 to 105. In conclusion, good extraction efficiency was achieved in tea beverage samples under the optimized conditions.

Cyanobacteria can form extensive blooms in water with concurrent production and release of a large number of chemically diverse and bioactive metabolites, including hazardous toxins. Significant number of the metabolites belongs to non-ribosomal peptides, with unique residues, unusual structures and great potential for biotechnological application. The biosynthetic pathways of the peptides generate tens of variants, but only part of them has been identified. Microginins are an understudied class of cyanobacterial linear peptides with a characteristic decanoic acid derivative amino acid residue in their structure. In this study, cyanobacterial blooms and isolated strains from Greek lakes were analyzed for the presence of microginins by liquid chromatography coupled to hybrid triple quadrupole/linear ion trap mass spectrometer (LC-qTRAP MS/MS). Microginin structures were elucidated based on the obtained fragmentation spectra. A large number of microginins occurred in blooms of Greek freshwaters and the most frequently detected were Microginin FR1 (70% of samples), Microginin T1 (52%), Microginin 565B (52%), Microginin T2 (43%), and Microginin 565A (43%). Additionally, nine cyanobacterial strains i.e. Nostoc oryzae, Synechococcus sp., Microcystis aeruginosa, Microcystis viridis, and five Microcystis sp., were found to produce microginins. Thirty-six new microginin structures were characterized out of fifty-one totally detected variants. This is the first time that such a diversity of microginins is reported to be present in water bodies. Results clearly demonstrate the great metabolomic potential of cyanobacteria that inhabit Greek freshwaters and significantly expand the knowledge of cyanobacterial secondary metabolites with regards to the class of microginins.

Oxidative biocatalytic reactions performed by cytochrome P450 enzymes (P450s) are of high interest for the chemical and pharmaceutical industries. CYP267B1 is a P450 enzyme from myxobacterium Sorangium cellulosum So ce56 displaying a broad substrate scope. In this work, a search for new substrates was performed, combined with product characterization and a structural analysis of substrate-bound complexes using X-ray crystallography and computational docking. The results demonstrate the ability of CYP267B1 to perform in-chain hydroxylations of medium-chain saturated fatty acids (decanoic acid, dodecanoic acid and tetradecanoic acid) and a regioselective hydroxylation of flavanone. The fatty acids are mono-hydroxylated at different in-chain positions, with decanoic acid displaying the highest regioselectivity towards ω-3 hydroxylation. Flavanone is preferably oxidized to 3-hydroxyflavanone. High-resolution crystal structures of CYP267B1 revealed a very spacious active site pocket, similarly to other P450s capable of converting macrocyclic compounds. The pocket becomes more constricted near to the heme and is closed off from solvent by residues of the F and G helices and the B–C loop. The crystal structure of the tetradecanoic acid-bound complex displays the fatty acid bound near to the heme, but in a nonproductive conformation. Molecular docking allowed modeling of the productive binding modes for the four investigated fatty acids and flavanone, as well as of two substrates identified in a previous study (diclofenac and ibuprofen), explaining the observed product profiles. The obtained structures of CYP267B1 thus serve as a valuable prediction tool for substrate hydroxylations by this highly versatile enzyme and will encourage future selectivity changes by rational protein engineering.

Effect of surfactant addition on persulfate-assisted electrokinetic remediation of pyrene-spiked soil was studied. The influence of effective factors including voltage, surfactant addition, moisture content, and persulfate concentration on the removal of initial pyrene concentration of 200 mg kg–1 were investigated. A complete pyrene removal was observed for voltage of 1 V cm–1, saturated conditions, Tween 80 concentration of 20 mL kg–1, and persulfate concentration of 100 mg kg–1 after 24 h, corresponding to pyrene mineralization of 61 %, based on TPH analysis. The experimental results were best fitted with pseudo-first-order kinetic model with correlation coefficient of 0.968 and rate constant of 0.191 min−1. The main intermediates of pyrene degradation were benzene o-toluic acid, acetic, azulene, naphthalene and decanoic acid. Finally, an unwashed hydrocarbon- contaminated soil was subjected to persulfate-assisted electrokinetic remediation, and a TPH removal of 38 % was observed for the initial TPH content of 912 mg kg–1, under the selected conditions. This work is licensed under a Creative Commons Attribution 4.0 International License.

Medium chain fatty acids can activate the pro-inflammatory receptor GPR84 but so also can molecules related to 3,3′-diindolylmethane. 3,3′-Diindolylmethane and decanoic acid acted as strong positive allosteric modulators of the function of each other and analysis showed the affinity of 3,3′-diindolylmethane to be at least 100 fold higher. Methyl decanoate was not an agonist at GPR84. This implies a key role in binding for the carboxylic acid of the fatty acid. Via homology modelling we predicted and confirmed an integral role of arginine172, located in the 2nd extracellular loop, in the action of decanoic acid but not of 3,3′-diindolylmethane. Exemplars from a patented series of GPR84 antagonists were able to block agonist actions of both decanoic acid and 3,3′-diindolylmethane at GPR84. However, although a radiolabelled form of a related antagonist, [3H]G9543, was able to bind with high affinity to GPR84, this was not competed for by increasing concentrations of either decanoic acid or 3,3′-diindolylmethane and was not affected adversely by mutation of arginine172. These studies identify three separable ligand binding sites within GPR84 and suggest that if medium chain fatty acids are true endogenous regulators then co-binding with a positive allosteric modulator would greatly enhance their function in physiological settings.

A proteomic and exometabolomic study was conducted on Saccharomyces cerevisiae flor yeast strain growing under biofilm formation condition (BFC) with ethanol and glycerol as carbon sources and results were compared with those obtained under no biofilm formation condition (NBFC) containing glucose as carbon source. By using modern techniques, OFFGEL fractionator and LTQ-Orbitrap for proteome and SBSE-TD-GC-MS for metabolite analysis, we quantified 84 proteins including 33 directly involved in the metabolism of glycerol, ethanol and 17 aroma compounds. Contents in acetaldehyde, acetic acid, decanoic acid, 1,1-diethoxyethane, benzaldehyde and 2-phenethyl acetate, changed above their odor thresholds under BFC, and those of decanoic acid, ethyl octanoate, ethyl decanoate and isoamyl acetate under NBFC. Of the twenty proteins involved in the metabolism of ethanol, acetaldehyde, acetoin, 2,3-butanediol, 1,1-diethoxyethane, benzaldehyde, organic acids and ethyl esters, only Adh2p, Ald4p, Cys4p, Fas3p, Met2p and Plb1p were detected under BFC and as many Acs2p, Ald3p, Cem1p, Ilv2p, Ilv6p and Pox1p, only under NBFC. Of the eight proteins involved in glycerol metabolism, Gut2p was detected only under BFC while Pgs1p and Rhr2p were under NBFC. Finally, of the five proteins involved in the metabolism of higher alcohols, Thi3p was present under BFC, and Aro8p and Bat2p were under NBFC.

Objective It has been reported that administration of octanoic acid, one of medium-chain fatty acids (MCFAs), promoted leucine oxidation in vitro and in vivo, but it remained unclear how octanoic acid stimulated leucine oxidation. Therefore, the aim of this study was to elucidate the mechanism that octanoic acid facilitates branched-chain amino acid (BCAA) catabolism. Materials/Methods In in vivo experiments, male rats were orally administered MCFAs as free fatty acids or triacylglycerol (trioctanoin), and then activities of hepatic branched-chain α-ketoacid dehydrogenase (BCKDH) complex (BCKDC) and BCKDH kinase (BDK) and alterations in the concentration of blood components were analyzed. In in vitro experiments, purified BCKDC associated with BDK (BCKDH–BDK complex) was reacted with various concentrations of hexanoic, octanoic, and decanoic acids. Results Oral administration of trioctanoin in rats activated hepatic BCKDC via down-regulation of BDK activity in association with a decrease in plasma BCAA concentration and an increase in serum ketone body concentration. In vitro experiments using purified BCKDH–BDK complex showed that MCFAs (hexanoic, octanoic, and decanoic acids) inhibited BDK activity and that this inhibition was higher in hexanoic and octanoic acids than in decanoic acid. Oral administration of octanoic acid, but not decanoic acid, in rats activated hepatic BCKDC via down-regulation of BDK activity by decreasing the amount of BDK bound to the complex. The serum ketone body level was elevated by both administration of octanoic acid and decanoic acid. Conclusion These results suggest that octanoic acid promotes BCAA catabolism in vivo by activation of BCKDC via decreasing the bound form of BDK.

Alkyl carboxylic acid-based nanostructured solvents, synthesized in mixtures of tetrahydrofuran (THF) and water through self-assembly and coacervation, were proved to behave as restricted access liquids. Both physical and chemical mechanisms were found responsible for exclusion of macromolecules such as proteins and polysaccharides. The potential of these solvents for extracting small molecules from complex solid samples, without interference from large biomolecules, was here evaluated. For this purpose, they were applied to the extraction of 14 priority polycyclic aromatic hydrocarbons (PAHs) from mosses prior to their separation by liquid chromatography and fluorescence detection (LC-FLD). Sample treatment involved the vortex shaking of 200 mg of moss with 200 µL of decanoic acid-based solvent for 5 min, subsequent centrifugation for 8 min and analysis of the extract by LC-FLD using external calibration. Proteins precipitated during extraction because of both the decrease of the dielectric constant of the solution caused by THF and the formation of macromolecular complexes with decanoic acid. Polysaccharides were not solubilized in the aqueous cavities of the solvent because of their size exclusion. In-house method validation was performed according to the recommendations of the European Commission Decision 202/657/EC. Method detection and quantification limits for the different PAHs were in the ranges 0.04-0.24 and 0.14-0.80 µg kg-1, respectively. The method was applied to the determination of different moss species collected in both polluted and unpolluted sites in the South of Spain. Recoveries were within the range 71-110%. The results obtained show that solvents with restricted access properties have the potential to expand the scope of application of restricted access materials to areas other than biological fluids because of their suitability to combine analyte isolation and sample cleanup of solid samples in a single step. © 2015 Elsevier B.V., Council for Higher Education CTQ2014-53539-R Ministerio de Economía y Competitividad: BES-2012-052170, Authors gratefully acknowledge financial support from Spanish MINECO (Project CTQ2014-53539-R ). N. Caballero-Casero acknowledges the Spanish MINECO for the postgraduate fellowship (BES-2012-052170). H. Çabuk acknowledges the Higher Education Council of Turkey (YÖK) for the postdoctoral fellowship.