Phenolic Alcohols Research Articles

Fourier Transform Infrared Spectroscopy (FTIR) Spectral evaluation in Chrysanthemum flower species

The current study's goal was to identify the various functional groups found in chrysanthemums using FTIR Spectroscopy. The FTIR spectrometer identifies 4000 series, with a scan range of 4,000–400 cm-1, was used to perform the FTIR analysis. The presence of distinct peak values with various useful mixtures of functional groups, including hydroxy groups (̶ OH), aliphatic, metal carbonyl, alcohols (̶ OH), nitrile (̶ C≡N), phenols, alkynes (CnH2n-2), ketones (C=O), carboxylic acids (R−COOH), amides (̶ CONH2), and aromatics, was revealed by FTIR spectroscopy analysis. The FTIR investigation showed that there were 17 functional groups in the chrysanthemum flowers. The FTIR spectra showed an intense peak that correlated to the hydroxyl groups, phenol alcohol, and aromatic compounds, respectively, at 3348.42 cm-1, 1380.02 cm-1, and 1480.33 cm-1 in various flower species. In light of this, the current investigation found that, in contrast to the extracts of Chrysanthemum flowers' leaves and bark, the flower extract had robust functional groups. FTIR spectroscopy was used to quantitatively analyse the flavonoids, phenolic acids, anthocyanins, and carotenoids present in the nine chrysanthemum cultivars' flowers.

Interaction Between Nonionic Surfactants and Alkyl Amidoamine Cationic Collector in the Reverse Flotation of Iron Ore

This paper evaluates the performance of four ethoxylated nonionic surfactants (nonyl phenol vs. C13 alcohols) to act as ancillary collectors with Alkyl Amidoamine (AAA) in the reverse flotation of quartz at pH8 to concentrate iron ores. Compared to 100% AAA, the blend composed of 80% AAA (Flotinor®5530) plus 20% of isotridecyl alcohol ethoxylated with five groups of ethylene oxide (DP-210 RO) improved quartz recovery (from 54% to 63%, p < 0.05) by increasing contact angle (from 55° to 56°, p < 0.05) and decreasing induction time (26 ms to 23 ms, p < 0.05). Compared to 100% AAA (200 g/t), the blend (160 g/t of AAA + 40 g/t of DP-210 RO) improved the flotation performance of iron ore, yielding richer hematite concentrate (65.3% Fe × 61.4% Fe) and less contaminated with quartz (4% SiO2 × 10.2% SiO2), coupled with an increase in Fe recovery from 79.8% × 81.6% in the sunken product as well as SiO2 recovery from 91.7% to 96.9% in the froth. Results from zeta potential, the hydrodynamic diameter of reagent droplets, and the surface tension of the solution provide insights into the synergism between AAA and DP-210 RO.

Selective Lipophilization of Natural Phenolic Alcohols Induced by In Situ Choline Chloride-Based Natural Deep Eutectic Solvents.

In this scientific work, a novel and green method for selective lipophilization of EVOO's bioactive phenolic alcohols (PAs), namely, tyrosol, hydroxytyrosol, and its metabolite homovanillyl alcohol as fatty acid esters, is elucidated. The PAs have been employed as hydrogen bond donors in the formation of natural deep eutectic solvents (NADES) with choline chloride (ChCl). The fast and cheap esterification method by in situ formation of choline chloride-based deep eutectic solvents promotes the derivatization of PAs with various fatty acids as acylating agents in the absence of organic solvents and catalysts. Furthermore, given the growing interest in the application of NADES formed by bioactive molecules in the pharmacological and cosmetic fields, we analyzed the activity of antioxidant enzymes, superoxide dismutase, and glutathione S-transferase of three chemical formulations obtained after the formation of PA-oleate in the H2O2-treated HaCat human keratinocytes cell line, assessing also their toxicity via the MTT assay.

Chemical Composition and Analgesic and Antidiabetic Activity of Chenopodium ambrosioides L.

This study focuses on identifying active compounds within Chenopodium ambrosioides extracts and fractions, with a specific emphasis on their potential analgesic and antidiabetic properties. The motivation arises from the reported therapeutic effects of the plant and the desire to pinpoint the compounds responsible for these benefits. Gas chromatography-mass spectrometry spectrophotometric analysis was employed to characterize chemical constituents in the aqueous extracts (infused aqueous extract and macerated aqueous extract) and fractions (cyclohexane fraction, ethyl acetate fraction, butanol fraction, remaining aqueous fraction) of C. ambrosioides. Animal models were used to examine the analgesic activity, while α-glucosidase and α-amylase enzyme assays were used to investigate the antidiabetic effect. Throughout the investigation, several chemical families were found, including phenolic compounds, alcohols, acids, terpenes, steroids, and others. Trans-ascaridol glycol, palmitic acid, phenol, octadecadienoic acid, isoascaridol, eicosanoic acid, 2-methoxy-4-vinyl phenol, mexiletine, and thymol were among the significant chemicals found. At a dose of 500 mg/m, starting with α-amylase inhibition, among the extracts, EAF (59 ± 0.7 μg/mL) showed the highest potency, followed by FA (129 ± 0.22 μg/mL), FB (140 ± 0.9 μg/mL), and EAM (178 ± 0.9 μg/mL). Interestingly, EAI demonstrated a relatively weak inhibition (430 ± 0.2 μg/mL), and no result was reported for FCH in this category. Regarding α-glucosidase inhibition, the most potent activity was observed with EAM (1.4 ± 0.7 μg/mL), The other extracts demonstrated varying levels of inhibition, with EAI (4.4 ± 0.5 μg/mL) and EAF (140 ± 1.9 μg/mL) showing moderate activity. FA (25 ± 0.9 μg/mL) and FB (34 ± 0.3 μg/mL) exhibited lower inhibition compared to EAM but still outperformed acarbose in this test. The observed synergistic effects of phenolic compounds in Chenopodium ambrosioides provide insights into the biological properties contributing to its reported analgesic and antidiabetic effects. The study underscores the potential of natural plant products for pharmaceutical applications, especially in enzymatic inhibition. All things considered, these results add to the expanding corpus of information about substances originating from plants and their uses in industry and health.

Development and Validation of a Headspace GC-MS Method for Simultaneous Quantification of Antimicrobial Preservatives in Biopharmaceutical Peptide Formulations.

The four most used antimicrobial preservatives in biopharmaceutical parenteral formulations are phenol, meta-cresol, chlorobutanol, and benzyl alcohol. Preservatives are included in various combinations in biopharmaceuticals highlighting the importance of an analytical method to quantify the four preservatives simultaneously. A headspace GC-MS method was developed to quantify phenol, chlorobutanol, meta-cresol, and benzyl alcohol. The method was validated according to USP <1225>. System suitability <USP 621> was conducted daily for retention time (%RSD < 2.0%), peak area (%RSD < 5.0%), USP tailing factor (< 2.0 and %RSD < 10.0%), and peak resolution (> 2.0). Analytical ranges were 1.5-90 μg/mL for phenol and meta-cresol, 30-240 μg/mL for benzyl alcohol, and 30-300 μg/mL for chlorobutanol. Method accuracy ranged from 94% to 108% and precision from 4% to 15 %RSD for all the tested preservatives. The method was applied to three marketed teriparatide drug products selected as a model. Preservative concentrations of the biopharmaceutical marketed products were determined and were found to be comparable with the labeled concentrations, except for an expired product with 2.5% of the label claim. The developed headspace GC-MS method can be used to evaluate the drug quality of the parenteral formulations and to support the assessment of biopharmaceutical peptide drug products.

Biocatalytic sulfation of aromatic and aliphatic alcohols catalyzed by arylsulfate sulfotransferases

Many relevant metabolites, as well as chemical commodities, contain at least one sulfate ester group. Consequently, biocatalytic strategies to attach sulfate to a molecule under mild conditions are of high interest. In order to expand the enzymatic toolbox available, five new arylsulfate sulfotransferases (ASSTs) were identified in this study. Overexpression in Escherichia coli and enzyme purification resulted in soluble proteins which catalyzed the sulfate transfer to an acceptor substrate using p-nitrophenyl sulfate (pNPS) as sulfate donor. Optimal reaction conditions were established with respect to temperature and pH, as well as their tolerance to organic co-solvents and melting temperature. Additionally, the kinetic parameters (Vmax, KM, and kcat) were determined. The substrate scope for the acceptor showed that a structurally diverse spectrum of alcohols is accepted. The substrates included phenolic alcohols with one, two, and three hydroxy groups, linear and cyclic aliphatic alcohols, and amines. The phenolic substrates were accepted reaching activities of up to 154 U/mg purified enzyme. Additionally, also the aliphatic alcohols (both linear and cyclic) were accepted at reduced activity, showing that these enzymes are not limited to phenolic alcohols. Moreover, catalytic activity was detected when using aniline as an acceptor substrate implying their ability to sulfate also amino groups. Finally, the consecutive sulfation of di- and trihydroxy compounds was observed, resulting in the detection of the corresponding disulfated molecules.Key points• Five novel arylsulfate sulfotransferases were identified and characterized.• Accepted substrates included aromatic and aliphatic alcohols, as well as aniline.• Disulfation of di- and trihydroxy aromatic compounds was studied and confirmed.

Analysis on Degradation Mechanism and Product Recycle of Ex-service Wind Turbine Blades by Hydrothermal Liquefaction.

The recycling of ex-service wind turbine blades (EWTBs) presents a significant challenge for the future. Hydrothermal liquefaction (HTL) has emerged as a promising approach for the recovery of resins and glass fibers (GFs) from EWTBs. This study offers a comprehensive analysis of the separation mechanisms and product characteristics under the catalytic effect of an acidic medium during the HTL tests. The primary factors were identified as hydrothermal temperature and H2SO4 concentration. The acidic medium facilitated disruption of the resin's structure by supplying hydronium ions, while temperature played a crucial role in determining the yield of oil-phase products. Operating conditions of 280 °C and 0.6 mol/L H2SO4 resulted in an oil-phase yield of 98.2%. The cleavage of cross-linked C-N and C-O-C bonds reacted with hydrogen ions to produce stable compounds, primarily phenol and p-cumyl alcohol. Based on these findings, two distinct mechanisms of resin depolymerization were proposed, depending on the sequential cleavage of C-O-C and C(benzene ring)-C(isopropyl) bonds. Intermediates, including bisphenol A and 2-propanol,1,3-diphenoxy-, were generated. They further decomposed into smaller units, eventually forming phenol. Moreover, temperature was found to be a critical factor in determining the strength of recycled glass fibers (RGFs). The optimal conditions of 260 °C and 0.6 mol/L H2SO4 concentration were identified as being capable of achieving complete resin depolymerization while preserving high-strength RGFs. These innovative findings provide valuable insights into the development of low-temperature, high-efficiency methods for the full-component recovery of EWTBs, offering significant guidance for future recycling efforts.

Distinct effects of dilute acid prehydrolysate inhibitors on enzymatic hydrolysis and yeast fermentation.

The effects of dilute acid prehydrolysate from poplar were investigated and compared in the enzymatic hydrolysis, fermentation, and simultaneous saccharification fermentation (SSF) in this study. The improvement of enzymatic hydrolysis and fermentation with resin adsorption and surfactant addition has also been represented. A total of 16 phenolic alcohols, aldehydes, acids and 3 furan derivatives in the prehydrolysates were identified and quantified by gas chromatography/mass spectrometry (GC/MS). The degree of inhibition from the phenolic compounds (26.55%) in prehydrolysate on the enzymatic hydrolysis was much higher than carbohydrates-derived inhibitors (0.52-4.64%). Around 40% degree of inhibition was eliminated in Avicel enzymatic hydrolysis when 75% of prehydrolysates phenolic compounds were removed by resin adsorption. This showed distinguishing inhibition degrees of various prehydrolysate phenolic compounds. Inhibition of prehydrolysate on enzymatic hydrolysis was more dosage-dependent, while their suppression on the fermentation showed a more complicated mode: fermentation could be terminated by the untreated prehydrolysate, while a small number of prehydrolysate inhibitors even improved the glucose consumption and ethanol production in the fermentation. Correlated with this distinct inhibition modes of prehydrolysate, the improvement of Tween 80 addition in SSF was around 7.10% for the final ethanol yield when the glucose accumulation was promoted by 76.6%.

Phytochemical Characterization of Two New Olive Oil Genotypes Growing in Southern Tunisia.

This research can be considered as the first complete survey for the valorization of new olive genotypes cultivated in the South-East of Tunisia as well as their oils. The study aimed to characterize the phytochemical composition of virgin olive oil produced from two olive cultivars, namely Nourgou and Gousalani. The pomological characterization of fruits, the quality criteria and the phytochemical profile were quantified. Additionally, antioxidant activity was evaluated using Ferric reducing antioxidant power (FRAP) and Oxygen radical absorbance capacity (ORAC) tests to also obtain a bioactive characterization of these monovarietal olive oils. The obtained results revealed that the analyzed olive oils samples can be classified into Extra Virgin category (EVOO) according to the regulated physicochemical characteristics. Our findings showed a significant variability in the chemical parameters of the analyzed EVOO likely associated with the genetic potential, mainly for chlorophylls contents (1.37-1.64 mg/kg), in carotenoids pigments (3.97-10.86 mg/kg), in α-tocopherol (175.59-186.87 mg/kg), in sterols (1036.4-1931.4 mg/kg) in oleic acid (65.33-68.73%), in palmitic acid (C16:0) (13.32-17.48%), in linoleic acid (C18:2) (11.06-13.47%). Additionally, the HPLC-MS/MS analysis showed that the two EVOOs analyzed contained appreciable amounts of total polyphenols, ranging from 348.03 up to 516.16 mg/kg, in Nourgou and Gousalani oils, respectively. Regarding the individual phenolic compounds, the EVOO samples were mainly characterized by phenolic alcohols, phenolic acids, secoiridoids, verbascoside, flavonoids and phenolic aldehydes. The prevalent simple phenolics detected were secoiridoids with the dominance of the oleuropein aglycone in Gousalani oil. In addition, findings from in vitro antioxidant assays (FRAP and ORAC) revealed that the two studied oils possessed a powerful antiradical activity and a good reducing power capacity. In conclusion, these new EVOOs exhibited a superior quality compared to other Tunisian varieties, considering their antiradical activity and reducing power capacity.

An improved Trizol method for extracting total RNA from Eleutherococcus senticosus (Rupr. & Maxim.) Maxim leaves.

High-quality nucleic acids are the basis for molecular biology experiments. Traditional RNA extraction methods are not suitable for Eleutherococcus senticosus Maxim. To find a suitable method to improve the quality of RNA extracted, we modified the RNA extraction methods of Trizol. Based on the conventional Trizol method, the modified Trizol method 1 and modified Trizol method 2 were used as the control for extraction of RNA from E. senticosus Maxim leaves. The modified Trizol method 1 added β-mercaptoethanol on the conventional Trizol method. After RNA was dissolved, a mixed solution of phenol, chloroform, and isoamyl alcohol was added to denature protein and inhibit the degradation of RNA. The modified Trizol method 2 adds PVPP to grind on the basis of modified Trizol method 1, so as to better remove phenols from leaves, and eliminates the step of incubation at -20°C to reduce extraction time and RNA degradation. Chloroform, CTAB, and CH3COONa were used instead of a phenol, chloroform, and isoamyl alcohol mixed solution to ensure complete separation of nucleic acid from plant tissues and to obtain high-purity RNA. The research results showed that the quality of RNA extracted by conventional Trizol method, modified Trizol method 1, was incomplete, accompanied with different degrees of contamination of polysaccharides, polyphenols, and DNA. The modified Trizol method 2 could better extract RNA from E. senticosus Maxim leaves. The ratio of A260/A280 was in the range of 1.8-2.0, and the yield of RNA was the highest, which was 1.68 and 1.15 times compared with that by conventional Trizol method and modified Trizol method 1 extraction, respectively. The reverse transcription cDNA was further tested through PCR with the specific primers. The amplified fragments are displayed in clear and bright bands in accordance with the expected size. The modified Trizol method 2 could better extract RNA from E.senticosus Maxim leaves. High-quality RNA has more advantages in molecular biology study of E.senticosus Maxim.

Oxidative Stress as a Target for Non-Pharmacological Intervention in MAFLD: Could There Be a Role for EVOO?

Oxidative stress plays a central role in most chronic liver diseases and, in particular, in metabolic dysfunction-associated fatty liver disease (MAFLD), the new definition of an old condition known as non-alcoholic fatty liver disease (NAFLD). The mechanisms leading to hepatocellular fat accumulation in genetically predisposed individuals who adopt a sedentary lifestyle and consume an obesogenic diet progress through mitochondrial and endoplasmic reticulum dysfunction, which amplifies reactive oxygen species (ROS) production, lipid peroxidation, malondialdehyde (MDA) formation, and influence the release of chronic inflammation and liver damage biomarkers, such as pro-inflammatory cytokines. This close pathogenetic link has been a key stimulus in the search for therapeutic approaches targeting oxidative stress to treat steatosis, and a number of clinical trials have been conducted to date on subjects with NAFLD using drugs as well as supplements or nutraceutical products. Vitamin E, Vitamin D, and Silybin are the most studied substances, but several non-pharmacological approaches have also been explored, especially lifestyle and diet modifications. Among the dietary approaches, the Mediterranean Diet (MD) seems to be the most reliable for affecting liver steatosis, probably with the added value of the presence of extra virgin olive oil (EVOO), a healthy food with a high content of monounsaturated fatty acids, especially oleic acid, and variable concentrations of phenols (oleocanthal) and phenolic alcohols, such as hydroxytyrosol (HT) and tyrosol (Tyr). In this review, we focus on non-pharmacological interventions in MAFLD treatment that target oxidative stress and, in particular, on the role of EVOO as one of the main antioxidant components of the MD.

Monitoring the Phenolic and Terpenic Profile of Olives, Olive Oils and By-Products throughout the Production Process.

Olive oil is a food of great importance in the Mediterranean diet and culture. However, during its production, the olive oil industry generates a large amount of waste by-products that can be an important source of bioactive compounds, such as phenolic compounds and terpenes, revalorizing them in the context of the circular economy. Therefore, it is of great interest to study the distribution and abundance of these bioactive compounds in the different by-products. This research is a screening focused on phytochemical analysis, with particular emphasis on the identification and quantification of the phenolic and terpenic fractions. Both the main products of the olive industry (olives, olive paste and produced oil) and the by-products generated throughout the oil production process (leaf, "alpeorujo", liquid and solid residues generated during decanting commonly named "borras" and washing water) were analyzed. For this purpose, different optimized extraction procedures were performed for each matrix, followed by high-performance liquid chromatography coupled with electrospray time-of-flight mass spectrometry (HPLC-ESI-TOF/MS) analysis. Although no phenolic alcohols were quantified in the leaf and the presence of secoiridoids was low, this by-product was notable for its flavonoid (720 ± 20 µg/g) and terpene (5000 ± 300 µg/g) contents. "Alpeorujo" presented a complete profile of compounds of interest, being abundant in phenolic alcohols (900 ± 100 µg/g), secoiridoids (4500 ± 500 µg/g) and terpenes (1200 ± 100 µg/g), among others. On the other hand, while the solid residue of the borras was the most abundant in phenolic alcohols (3700 ± 200 µg/g) and secoiridoids (680 ± 20 µg/g), the liquid fraction of this waste was notable for its content of elenolic acid derivatives (1700 ± 100 µg/mL) and phenolic alcohols (3000 ± 300 µg/mL). Furthermore, to our knowledge, this is the first time that the terpene content of this by-product has been monitored, demonstrating that it is an important source of these compounds, especially maslinic acid (120 ± 20 µg/g). Finally, the phytochemical content in wash water was lower than expected, and only elenolic acid derivatives were detected (6 ± 1 µg/mL). The results highlighted the potential of the olive by-products as possible alternative sources of a wide variety of olive bioactive compounds for their revalorization into value-added products.

Characterization of Phenolic Compounds in Extra Virgin Olive Oil from Granada (Spain) and Evaluation of Its Neuroprotective Action.

The olive oil sector is a fundamental food in the Mediterranean diet. It has been demonstrated that the consumption of extra virgin olive oil (EVOO) with a high content of phenolic compounds is beneficial in the prevention and/or treatment of many diseases. The main objective of this work was to study the relationship between the content of phenolic compounds and the in vitro neuroprotective and anti-inflammatory activity of EVOOs from two PDOs in the province of Granada. To this purpose, the amounts of phenolic compounds were determined by liquid chromatography coupled to mass spectrometry (HPLC-MS) and the inhibitory activity of acetylcholinesterase (AChE) and cyclooxygenase-2 (COX-2) enzymes by spectrophotometric and fluorimetric assays. The main families identified were phenolic alcohols, secoiridoids, lignans, flavonoids, and phenolic acids. The EVOO samples with the highest total concentration of compounds and the highest inhibitory activity belonged to the Picual and Manzanillo varieties. Statistical analysis showed a positive correlation between identified compounds and AChE and COX-2 inhibitory activity, except for lignans. These results confirm EVOO's compounds possess neuroprotective potential.

Systematic evaluation of benzoylation for liquid chromatography-mass spectrometry analysis of different analyte classes

LC-MS is an indispensable tool for small molecule analysis in many fields; however, many small molecules require chemical derivatization to improve retention on commonly used reversed-phase columns and increase ionization. Benzoyl chloride (BzCl) derivatization is commonly used for derivatization of primary and secondary amines and phenolic alcohols, though evidence exists that with proper reaction conditions (i.e., specific bases), other hydroxyl groups may be derivatized too. Previous studies have examined BzCl concentration, reaction times, and reaction temperatures for derivatization of amines and phenols for LC-MS analysis; however, use of different bases, base concentration, and extending to conditions to hydroxyl groups for LC-MS analysis has not been well-studied. To address this understudied area and identify reaction conditions for both amino and hydroxyl groups, we performed a systematic study of reaction conditions on multiple classes of potential targets. For selected derivatization methods, detection limits and performance in a variety of biological matrices were assessed. Results highlight the importance of tailoring derivatization methods for a given application as they varied by molecule and/or molecule class. Compared to the standard BzCl method commonly used, alternative methods were identified to better derivatize challenging analytes (glucosamine, choline, cortisol, uridine, cytidine) with detection limits reaching 1100, 9, 38, 170, and 67 nM compared to undetectable, 170, 86, 1000, and 86 nM respectively. Sub-nanomolar detection limits were achieved for norepinephrine with alternative derivatization approaches. Improved derivatization methods for several classes and molecules including nucleosides, steroids, and molecules containing hydroxyl groups were also identified.

Sustainable bio-oil from banana peel waste biomass: Optimization study and effect of thermal drying

&lt;p&gt;Banana waste has a high level of volatile matter, making it a promising feedstock for pyrolysis in bio-oil generation. Thus, an oven drying method optimization study was conducted to find the drying process of Saba banana peel on flap opening and fan speed. Based on the ANOVA results, it was found that the drying process using 60% fan speed and 40% flap opening for 6 hours of drying time could remove 84.07% of the moisture content from the banana peel. Differential thermal analysis (DTA) was employed to characterize dried banana peels. The TGA study showed that the volatile matter concentration of the dried banana peels was 76.47% when using the ASTM drying method and 70.95% when using the improvement parameter optimization for the drying process. The bio-oil's high heating value (HHV) at 300 °C was 38.88 MJ/kg. The yields of bio-oil, biochar, and syngas obtained from the pyrolysis process were 16.6%, 36.45%, and 46.96%, respectively. The carbon hydrogen nitrogen sulfur (CHNS) ultimate analysis study showed a bio-oil elemental composition of 65.59% carbon, 8.27% hydrogen, 2.94% nitrogen, 0.93% sulfur, and 22.27% oxygen. Fourier transform infrared (FTIR) spectroscopy showed that functional groups including alcohol, alkane, phenol, and primary alcohol are present.&lt;/p&gt;&#x0D;

HS-SPME-GC–MS Profiling of Volatile Organic Compounds and Polar and Lipid Metabolites of the “Stendesto” Plum–Apricot Kernel with Reference to Its Parents

Plum–apricot hybrids are the successful backcrosses of plums and apricots. Plums and apricots are well-known and preferred by consumers because of their distinct sensory and beneficial health properties. However, kernel consumption remains limited even though kernels are easily accessible. The “Stendesto” hybrid originates from the “Modesto” apricot and the “Stanley” plum. Kernal metabolites exhibited quantitative differences in terms of metabolites identified by gas chromatography–mass spectrometry (GC–MS) analysis and HS-SPME technique profiling. The results revealed a total of 55 different compounds. Phenolic acids, hydrocarbons, organic acids, fatty acids, sugar acids and alcohols, mono- and disaccharides, as well as amino acids were identified in the studied kernels. The hybrid kernel generally inherited all the metabolites present in the parental kernels. Volatile organic compounds were also investigated. Thirty-five compounds identified as aldehydes, alcohols, ketones, furans, acids, esters, and alkanes were present in the studied samples. Considering volatile organic compounds (VOCs), the hybrid kernel had more resemblance to the plum one, bearing that alkanes were only identified in the apricot kernel. The objective of this study was to investigate the volatile composition and metabolic profile of the first Bulgarian plum–apricot hybrid kernels, and to provide comparable data relevant to both parents. With the aid of principal component analysis (PCA) and hierarchical cluster analysis (HCA), differentiation and clustering of the results occurred in terms of the metabolites present in the plum–apricot hybrid kernels with reference to their parental lines. This study is the first providing information about the metabolic profile of variety-defined kernels. It is also a pioneering study on the comprehensive evaluation of fruit hybrids.

Dihydro-10H-indeno[1,2-b]benzofurans and Tetrahydroindeno[1,2-c]isochromenes via Stereoselective Intramolecular Carbocation Cascade Cyclization.

Nazarov cyclization of the (E)-(2-stilbenyl)methanols under the catalysis of p-TsOH immobilized on silica (PTS-Si) proceeded to give the corresponding indanyl cation with the exclusive trans relationship at the two newly formed adjacent stereogenic centers. The ensuing intramolecular nucleophilic addition by the MOM-protected phenol (m = 0) or benzyl alcohol (m = 1) furnished the Indane-fused benzofuran [5/5] or isochroman [5/6] system, respectively, with the exclusive cis stereocontrol at the two-carbon ring junction. Thus, in a single step, from nonchiral starting materials, the intramolecular cascade carbocation cyclization (CCC) furnished the [5/5] or [5/6] oxygen-containing Indane fused-ring systems in moderate to good yields with excellent stereoselectivity on all three contiguous stereogenic centers.

Efficient polymalic acid production from corn straw hydrolysate by detoxification of phenolic inhibitors.

Inhibitory compounds generated from lignocellulose pretreatment would inhibit Poly (malic acid) (PMA) production by Aureobasidium pullulans, but the tolerance mechanism of A. pullulans to lignocellulosic inhibitor is poorly understood. In this study, the cellular response of A. pullulans to lignocellulosic inhibitor stress was studied. Among the three groups of inhibitors (furans, weak acids and phenolic aldehydes), phenolic aldehyde was the dominant inhibitor for PMA production. Phenolic aldehyde was mainly converted into phenolic alcohol by A. pullulans, and phenolic alcohol also exhibited severe inhibition on PMA production. Furthermore, the effect of detoxification methods on inhibitor-removal and PMA fermentation was investigated, both CaCO3 and overliming presented poor detoxification effect, whereas resin H103 could remove both furan derivatives and phenolic compounds efficiently, thereby producing 26.27g/L of PMA with a yield of 0.30g/g in batch fermentation. This study will be beneficial for the development of PMA production from lignocellulosic biomass.

One-pot solvent-free sequential synthesis of high-density polycycloalkanes fuels from lignin-derivatives over laminated NbOPO4 catalyst

Upgrading lignocellulose biomass to renewable fuels is essential to achieve carbon neutrality. However, the multiple synthetic, and purification steps as well as the employment of solvents in the production of renewable fuel inhibit the overall yields and cause the waste of energy and resources. Herein, a new catalytic strategy for one-pot solvent-free sequential synthesis (OSS) of perhydrofluorene and dicyclohexylmethane was developed from lignin-derivatives. A two-dimensional layered nanosheet niobium phosphate (NbOPO4-IB) catalyst was fabricated to efficiently integrate the alkylation of phenol and benzyl alcohol and sequential hydrodeoxygenation with a cocatalyst of Ru/C. The high crystalline NbOPO4 phase and the lamellar morphology contributes to the large specific surface area to expose more active sites, especially more Brønsted acid sites. The NbOPO4-IB catalyst with a suitable Brønsted/Lewis acid ratio of 1.49 favors the selectivity of fuel precursors benzyl phenol in the alkylation and also provides the appropriate acid strength to promote hydrodeoxygenation activity. NbOPO4-IB also shows good reusability. Excessive phenol plays a vital role in promoting the alkylation reaction by dissolving the intermediates, and then into cyclohexane to enhance the H2 dissolution in the hydrodeoxygenation. A possible mechanism of OSS from lignin-derivatives into polycycloalkanes over the cocatalysts was proposed.

The development of logic gate-based fluorescent probes that respond to intracellular hydrogen peroxide and pH in tandem

Logic gate-based fluorescent probes are powerful tools for the discriminative sensing of multiple signaling molecules that are expressed in concert during the progression of many diseases such as inflammation, cancer, aging, and other disorders. To achieve logical sensing, multiple functional groups are introduced to the different substitution sites of a single fluorescent dye, which increases the complexity of chemical synthesis. Herein, we report a simple strategy that incorporates just one responsive unit into a hemicyanine dye achieving the logic gate-based sensing of two independent analytes. We introduce boronic acid to hemicyanine to quench the fluorescence, and in the presence of hydrogen peroxide (H2O2), the fluorescence is recovered due to removal of the boronate. Interestingly, the subsequent decrease in pH turned the red fluorescence of hemicyanine to green emissive because of protonation of the phenolic alcohol. This unique feature of the probe enables us to construct “INHIBIT” and “AND” logical gates for the accurate measuring of intracellular H2O2 and acidic pH in tandem. This study offers insight into the simple construction of logic-gate based fluorescent probes for the tandem sensing of multiple analytes that are correlatively produced during disease progression.