Fatty Esters Research Articles

Does Microbiome Matter in Chronic Intestinal Failure Due to Type 1 Short Bowel Syndrome in Adults?

The exact microbiome composition and function of patients with Short Bowel Syndrome (SBS) and Chronic Intestinal Failure (CIF) are still unknown. Patients with type I SBS-CIF (end-jejunostomy/ileostomy) are little represented in available studies. The aim of this study is to evaluate the microbiome characteristics of adult type 1 SBS-CIF patients according to their clinical features. Fecal microbiota was studied by amplicon-based sequencing and volatile organic compounds (VOCs) were assessed by solid-phase microextraction and gas chromatography-mass spectrometry. A total of 44 adult type 1 SBS-CIF patients were enrolled. At the family level, Lactobacillaceae (38% of the relative frequency) and Streptococcaceae (24%) were predominant; at the genus level, Streptococcus (38% of the relative frequency) and Lactobacillus (24%) were the dominant amplicon sequence variants (ASVs). Patients with increased stomal output showed higher ASVs for Lactobacillus (Rho = +0.38; p = 0.010), which was confirmed after adjusting for small bowel length (OR = 1.04; 95% CI 1.01-1.07, p = 0.023). Hyperphagia was associated with higher concentrations of short-chain fatty acid (SCFA) esters, such as butanoic acid ethyl ester (p = 0.005) and hexanoic acid ethyl ester (p = 0.004). Dietary fiber intake was directly correlated with most VOCs. Hyperphagia was associated with dietary fiber, after adjusting for small bowel length (OR = 1.35; 95% CI 1.01-1.81; p = 0.040). In type 1 SBS-CIF patients, a greater frequency of Lactobacilli was associated with increased stomal outputs, while increased fiber intake and concentrations of SCFA esters were associated with hyperphagia. These results might have implications for clinical practice.

Characterization and Antioxidant Activity Assay of Essential Oil Parts of Rosella (Hibiscus sabdariffa L.)

Rosella (Hibiscus sabdariffa L.) is known as a plant whose calyx contain high levels of antioxidant bioactive compounds and good inhibitory power against free radicals. However, other parts of the rosella plant have not yet been utilized for their antioxidant content and activity. The aim of this research is to compare the profiles of essential oils of parts of the rosella plant (seeds, leaves and flower petals) and their antioxidant activity. This research method begins with the process of extracting essential oils using the water-steam distillation method. Furthermore, the profile of the essential oil is known from the results of yield calculations and characterization using the GC-MS instrument. The antioxidant activity was tested using the DPPH method. The yield of essential oils obtained was 0.0107% for seeds, 0.0087% for leaves and 0.0136% for flower petals. GC-MS characterization shows that the most abundant chemical components contained in the essential oils of seeds, leaves, and flower petals are fatty acid compounds (2-propanoic acid, butanoic acid, hexanoic acid) and esters (neopentyl isobutyrate). The results of the antioxidant activity test showed the IC50 value for each essential oil, namely, seeds: 30.15 μg/ml, leaves: 171.27 μg/ml and flower petals: 126.58 μg/ml. The compound characteristics obtained showed the best results for rosella seed essential oil, this was supported by the fairly high antioxidant activity test results IC50 <50 μg/ml. Keywords: Antioxidant activity, Characterization, Essential oils, IC50, Yield.

Cerium(III)phosphotungstate: an efficient catalyst in esterification of fatty acids

In this report, a known heteropolyacid salt (HPAs) cerium (Ⅲ) phosphotungstate was synthesized in a volume ratio of 2:1:2 with a molar ratio of 1:1:1 of each ingredient. These HPAs are further utilized in form of a catalyst to generate biodiesel through the esterification of variable carbon chain length alcohols (methanol, ethanol, n-propanol, isopropanol, n-butanol) and stearic acid at different conditions of reaction. FTIR of the produced biodiesel was also done for the assurance of ester peaks in it. Analysis of some important biodiesel properties (density, dynamic viscosity, acid value, aniline point, boiling point, cloud and pour point, and flash and fire point) etc., to differentiate and validate the results. A large surface area of the catalyst i.e. 121.427 m2/g determined using the BET surface area analyser, supports the fact of outrageous catalytic action in the esterification reaction. The effect of additives was also studied on the properties of resultant biodiesel. The calorific value of the samples was measured at 7320 Kcal/kg without additive and 7512 Kcal/kg after adding toluene (as an additive) in the biodiesel generated in the study. The pour point temperature of the biodiesel with additives was observed even < 20℃.

Stability and characteristics of kerosene-in-water emulsions with xanthate surfactants: Influence of hydrophilic-lipophilic balance and molecular weight

The understanding of emulsion stability is important for several industrial applications including foods, pharmaceuticals, petroleum, personal care products, and in our case mineral processing. Xanthate functional surfactants may be useful to improve mineral recovery through froth flotation by delivering oil to valuable mineral surfaces as they may be used to stabilize kerosene-in-water emulsions. The eco-friendly nature of naturally derived reagents such as vitamin E-based xanthates would be beneficial to the mineral processing industry. In this study, conventional (potassium amyl xanthate (PAX)) and novel xanthate functional surfactants such as α-tocopherol polyethylene glycol 400 succinate (TPGS) xanthates which we synthesized from Vitamin E were investigated as emulsifiers. The creaming and oil phase separation of the kerosene-in-water emulsions produced with the xanthate surfactants were studied. The influence of hydrophilic-lipophilic balances (HLBs) and molecular weights (MWs) of the water-soluble xanthates and other commercial surfactants including polyoxyethylene fatty acid esters (Tweens), sorbitan fatty acid esters (Spans), and polyoxyethylene fatty ethers (Brijs) on the characteristics of the kerosene-in-water emulsions was examined. The experimental results showed that the TPGS xanthate formed the most stable emulsion among the xanthate surfactants considered. The results indicated that HLB is not the only factor influencing the emulsifying properties of surfactants. The chemical structure, particularly the molecular weight of the surfactant has a significant impact on its emulsifying properties. Thus, an emulsion stability chart incorporating the HLB and molecular weight of surfactants is proposed. This stability chart can be used for a better classification of the emulsifying properties of commercially available surfactants and novel reagents.

Design, Synthesis, Bioactivity, and Tentative Exploration of Action Mode for Benzyl Ester-Containing Derivatives.

The active splicing strategy has witnessed improvement in bioactivity and antifungal spectra in pesticide discovery. Herein, a series of simple-structured molecules (Y1-Y53) containing chloro-substituted benzyl esters were designed using the above strategy. The structure-activity relationship (SAR) analysis demonstrated that the fatty acid fragment-structured esters were more effective than those containing an aromatic acid moiety or naphthenic acid part. Compounds Y36 and Y41, which featured a thiazole-4-acid moiety and trifluoromethyl aliphatic acid part, respectively, exhibited excellent in vivo curative activity (89.4%, 100 mg/L Y36) and in vitro fungicidal activity (EC50 = 0.708 mg/L, Y41) against Botrytis cinerea. Determination of antifungal spectra and analysis of scanning electron microscopy (SEM), membrane permeability, cell peroxidation, ergosterol content, oxalic acid pathways, and enzymatic assays were performed separately here. Compound Y41 is cost effective due to its simple structure and shows promise as a disease control candidate. In addition, Y41 might act on a novel target through a new pathway that disrupts the cell membrane integrity by inducing cell peroxidation.

A Facile LC-MS Method for Profiling Cholesterol and Cholesteryl Esters in Mammalian Cells and Tissues.

Cholesterol is central to mammalian lipid metabolism and serves many critical functions in the regulation of diverse physiological processes. Dysregulation in cholesterol metabolism is causally linked to numerous human diseases, and therefore, in vivo, the concentrations and flux of cholesterol and cholesteryl esters (fatty acid esters of cholesterol) are tightly regulated. While mass spectrometry has been an analytical method of choice for detecting cholesterol and cholesteryl esters in biological samples, the hydrophobicity, chemically inert nature, and poor ionization of these neutral lipids have often proved a challenge in developing lipidomics compatible liquid chromatography-mass spectrometry (LC-MS) methods to study them. To overcome this problem, here, we report a reverse-phase LC-MS method that is compatible with existing high-throughput lipidomics strategies and capable of identifying and quantifying cholesterol and cholesteryl esters from mammalian cells and tissues. Using this sensitive yet robust LC-MS method, we profiled different mammalian cell lines and tissues and provide a comprehensive picture of cholesterol and cholesteryl esters content in them. Specifically, among cholesteryl esters, we find that mammalian cells and tissues largely possess monounsaturated and polyunsaturated variants. Taken together, our lipidomics compatible LC-MS method to study this lipid class opens new avenues in understanding systemic and tissue-level cholesterol metabolism under various physiological conditions.

Evolution of Aroma Profiles in Vitis vinifera L. Marselan and Merlot from Grapes to Wines and Difference between Varieties.

The fermentation process has a significant impact on the aromatic profile of wines, particularly in relation to the difference in fermentation matrix caused by grape varieties. This study investigates the leaching and evolution patterns of aroma compounds in Vitis vinifera L. Marselan and Merlot during an industrial-scale vinification process, including the stages of cold soak, alcohol fermentation, malolactic fermentation, and one-year bottle storage. The emphasis is on the differences between the two varieties. The results indicated that most alcohols were rapidly leached during the cold soak stage. Certain C6 alcohols, terpenes, and norisoprenoids showed faster leaching rates in 'Marselan', compared to 'Merlot'. Some branched chain fatty-acid esters, such as ethyl 3-methylbutyrate, ethyl 2-methylbutyrate, and ethyl lactate, consistently increased during the fermentation and bottling stages, with faster accumulation observed in 'Marselan'. The study combines the Orthogonal Partial Least Squares-Discriminant Analysis (OPLS-DA) model based on odor activity values to elucidate the accumulation of these ethyl esters during bottle storage, compensating for the reduction in fruity aroma resulting from decreased levels of (E)-β-damascenone. The 'Marselan' wine exhibited a more pronounced floral aroma due to its higher level of linalool, compared to the 'Merlot' wine. The study unveils the distinctive variation patterns of aroma compounds from grapes to wine across grape varieties. This provides a theoretical framework for the precise regulation of wine aroma and flavor, and holds significant production value.

Liquid-Liquid Equilibrium of Sesame Fatty Acid (Ethyl and Methyl) Ester + Glycerol + Ethanol/Methanol Mixtures at Different Temperatures.

This study aimed to investigate the liquid-liquid equilibrium (LLE) behavior of sesame fatty acid ethyl ester (FAEE) and methyl ester (FAME) in combination with glycerol and the co-solvents ethanol and methanol. FAEE and FAME were produced through the transesterification of mechanically extracted and purified sesame oil, using potassium hydroxide (KOH) as a homogeneous base catalyst. The reactions were conducted in ethanol and methanol to produce FAEE and FAME, respectively. Post-reaction, the products were separated and purified, followed by an analysis of the LLE behavior at 313.15 K and 323.15 K under atmospheric pressure (101.3 kPa). The experimental process for the miscibility analysis utilized a jacketed glass cell adapted for this study. Miscibility limits or binodal curves were determined using the turbidity-point method. Tie lines were constructed by preparing mixtures of known concentrations within the two-phase region, which allowed the phases to separate after agitation. Samples from both phases were analyzed to determine their composition. This study revealed that higher temperatures promoted greater phase separation and enhanced the biodiesel purification process. The NRTL model effectively correlated the activity coefficients with the experimental data, showing good agreement, with a root-mean-square deviation of 3.5%. Additionally, the data quality was validated using Marcilla's method, which yielded an R2 value close to 1. Attraction factors and distribution coefficients were also calculated to evaluate the efficiency of the co-solvents as extraction agents. The findings indicated higher selectivity for methanol than for ethanol, with varying degrees of distribution among the co-solvents. These results offer significant insights into enhancing biodiesel production processes by considering the effects of co-solvents on the LLE properties of mixtures, ultimately contributing to more efficient and cost-effective biodiesel production.

Hydrothermal Co-Liquefaction of Sugarcane Bagasse and Residual Cooking Soybean Oil for Bio-Crude Production

Hydrothermal co-liquefaction (co-HTL) is a process involving two sources of biomasses aiming at bio-crude production. Since there is a lack of studies performed with sugarcane bagasse and residual soybean oil, this study investigated different conditions for the co-HTL of these biomasses, with and without the presence of ethanol as a co-solvent to maximize the bio-crude yield. All co-HTL reactions were carried out in a 300 mL Parr® reactor at temperatures ranging from 200 to 300 °C. After the reaction, a vacuum filtration was performed to separate the bio-char, later washed with ethanol to extract heavy bio-crude, while the liquid-phase was mixed with dichloromethane to recover light bio-crude. Bio-crude yields of around 95 wt.% were obtained at 300 °C using ethanol and water as solvents. The highest bio-char yield (16.6 wt.%) was achieved when using only sugarcane bagasse as the substrate, without the presence of soybean oil. Bio-crude samples obtained at higher temperatures (280 °C and 300 °C) using ethanol as a hydrogen donor presented higher contents of both free fatty acids and fatty acid ethyl esters. This work presents a promising process to produce high-quality bio-crude using an abundant feedstock (sugarcane bagasse) in the presence of a lipid source which could cause environmental problems if poorly handled.

Density-Gibbs energy correlation models for binary biofuel mixtures

The density of binary biofuel mixtures significantly influences fuel properties, directly affecting internal combustion engine performance. This research aims to develop correlational models to calculate densities in binary biofuel mixtures, leveraging the Gibbs energy mixing rule. Two correlation models are proposed: the ideal Gibbs energy mixing rule and the Gibbs energy quadratic mixing rule. These models aim to enhance the cross-interaction of Gibbs energy of activation (ΔG12) to improve predictive performance. Importantly, the constants of the existing models are directly related to thermodynamic parameters. To assess the accuracy of the models, observed densities were collected from four different binary systems: biodiesel + diesel, pure fatty acid ethyl ester + alcohol, biodiesel + alcohol, and alcohol binary mixtures, amounting to 2242 data points obtained from the literature. Based on mole fractions, both models were compared to earlier approaches. The examination revealed that the equation formulated by the quadratic mixing rule exhibited heightened precision and efficacy. Our data demonstrate that the extended ΔG12 provided the most accurate results.

The effectiveness of semi-wild Sumatran mango (Mangifera spp.) leaves as a phytotherapy agent for breast cancer

Background Breast cancer ranks first in the world, standing at a mortality rate of 24.5% per year and is the leading cause of cancer death in Indonesia. The current management of breast cancer therapy is considered less effective because of its careful use due to side effects that are detrimental to the patient. The semi-wild species from Sumatra are neglected and underutilized species but have the potential as a therapeutic agent. Previous research has revealed that this species of mango is high in antioxidant compounds. Objective This study was carried out to discover the anticancer activities of the semi-wild mango species via inhibitory activities and morphological changes in Michigan Cancer Foundation-7 (MCF-7) cells. Materials and methods The IC50 value of Mangifera sumatrana, Mangifera foetida, and Mangifera laurina leaves in n-hexane, ethyl-acetate, and methanol extracts was determined using the reagent 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide (MTT). Data were analyzed by two-way analysis of variance using IBM SPSS Statistics 21. Results and conclusion M. laurina n-hexane extracts exhibited anticancer activity (IC50 13.25 ppm). Nonpolar solutions were chosen as the most effective extraction solvent in anticancer tests because lipids in nonpolar solvents can hit the lipid bilayer. A hexane fraction was created by separating the majority of nonpolar fatty acid esters, and this fraction had a considerable impact on cytotoxic and apoptotic effects on MCF-7 cells. Therefore, all treatments can transform MCF-7 cells’ morphology into blackened dead cells that are degraded into small parts, such as apoptotic bodies in cells undergoing apoptotic processes. MTT assays against MCF-7 on three species of semi-wild Sumatran mango in different extraction solvents showed that n-hexane extracts of M. laurina had stronger anticancer activity than other samples. This study provides new information to support the development of standardized herbal medicines and phytopharmaca in the future.

Study on the Reactivity of Mixed Carboxylic Palmitic Anhydrides via the Esterification Reaction Using Heterogeneous Catalyst

Abstract: of Organic Chemistry LR17ES08: Faculty of Sciences in Sfax, Route de Soukra Km 3,5 – BP 1171-3000, Sfax, Tunisia : The anhydrides were prepared in the presence of triethylamine in the organic solvent by a reaction between fatty acid and acid chloride. Mixed aromatic palmitic were more reactive and selective than the aliphatic anhydrides. The palmitic group was the most involved in acylation. Good yields of fatty esters were obtained with total conversion of mixed anhydrides.

UV-induced photocleavage of unsaturated fatty esters in cod liver oil: Impact on iodine value and stability

UV-induced photocleavage of unsaturated fatty esters in cod liver oil: Impact on iodine value and stability

Network pharmacology-guided therapeutic exploration of a new trihydroxy fatty ester isolated from rhizomes of Trillium govanianum

One new previously undescribed trihydroxy fatty ester (1) and three known aliphatic alkenes (2–4) have been isolated from the rhizomes of Trillium govanianum Wall. ex D.Don. The structures of isolated molecules were elucidated using extensive spectroscopic techniques including NMR, HR-ESI-MS, and FT-IR, respectively. This is the first report on the isolation of compounds 3 and 4 from the Trillium genus. Moreover, through a network pharmacology approach, the therapeutic potential of the isolated molecules was investigated. This analysis revealed that these fatty alkenes can be utilised for managing health conditions such as pneumonitis, inflammatory pain, and endothelial dysfunction.

Phloridzin Docosahexaenoate, an Omega-3 Fatty Acid Ester of a Flavonoid Precursor, Inhibits Angiogenesis by Suppressing Endothelial Cell Proliferation, Migration, and Differentiation.

Angiogenesis is a normal physiological process that also contributes to diabetic retinopathy-related complications and facilitates tumor metastasis by promoting the hematogenic dissemination of malignant cells from solid tumors. Here, we investigated the in vitro, ex vivo, and in vivo anti-angiogenic activity of phloridzin docosahexaenoate (PZ-DHA), a novel ω-3 fatty acid ester of a flavonoid precursor. Human umbilical vein endothelial cells (HUVEC) and human dermal microvascular endothelial cells (HMVEC) treated with a sub-cytotoxic concentration of PZ-DHA to assess in vitro anti-angiogenic activity showed impaired tubule formation on a Matrigel matrix. Ex vivo angiogenesis was measured using rat thoracic aortas, which exhibited reduced vessel sprouting and tubule formation in the presence of PZ-DHA. Female BALB/c mice bearing VEGF165- and basic fibroblast growth factor-containing Matrigel plugs showed a significant reduction in blood vessel development following PZ-DHA treatment. PZ-DHA inhibited HUVEC and HMVEC proliferation, as well as the migration of HUVECs in gap closure and trans-well cell migration assays. PZ-DHA inhibited upstream and downstream components of the Akt pathway and vascular endothelial growth factor (VEGF165)-induced overexpression of small molecular Rho GTPases in HUVECs, suggesting a decrease in actin cytoskeletal-mediated stress fiber formation and migration. Taken together, these findings reveal the potential of combined food biomolecules in PZ-DHA to inhibit angiogenesis.

Antimicrobial, Cytotoxic and Phytochemical Analysis of Chloroform Extracts of Andrographis paniculata Root (Burm.F) and Parquetina nigrescens (Afzel) Aerial Part

The menace of antibiotic resistance especially multi-drug resistant bacteria is increasing in the clinical setting. Therefore, the study investigated antimicrobial activity and phytochemical constituents of chloroform extracts of Andrographis paniculata root (Burm.F.) and Parquetina nigrescens (Afzel) aerial part. The extracts were screened for cytotoxic activity using brine shrimp (Artemia salina) lethality bioassay. The antimicrobial activity of the extracts was tested against Citrobacter diversus, Klebsiella pneumoniae, Proteus vulgaris and Shigella sonnei using tetrazolium microtitre-plate method. Analysis of chemical components of the extracts was done on Agilent Technologies 7890A gas chromatograph system s. GC-MS analysis of A. paniculata root extract and P. nigrescens aerial part extracts revealed a total of 32 and 22 compounds, respectively. The major components identified in these two extracts were fatty acid esters, alkaloids and terpenes. The lowest MIC observed with A. paniculata extract was 6.25 μg/ml for Citrobacter diversus and 12.5 μg/ml for Klebsiella pneumoniae. The lowest MIC recorded for Parquetina nigrescens extract was 3.125 μg/ml for Citrobacter diversus, Shigella sonnei and Proteus vulgaris while it was 12.5 μg/ml for Klebsiella pneumoniae. The susceptibility was compared with a clinical antibiotic (0.02 μg/ml) which served as the positive control. P. nigrescens with LC50 of 89.75 ± 0.18 μg/ml showed higher lethal toxicity than A. paniculata with LC50 of 167.5 ± 0.21 μg/ml. The observed toxicity might be due to presence of fatty acids and alkaloids in the extracts. The extract of the plants investigated in our study showed promising antimicrobial activity. Dhaka Univ. J. Pharm. Sci. 23(1): 43-51, 2024 (June)

Synthesis of TMP Ester via Esterification of Corn Oil Fatty Acids and Trimethylolpropane as a Potential Biolubricant Base Stock

Synthesis of TMP Ester via Esterification of Corn Oil Fatty Acids and Trimethylolpropane as a Potential Biolubricant Base Stock

A Novel Data Fusion Strategy of GC-MS and 1H NMR Spectra for the Identification of Different Vintages of Maotai-flavor Baijiu.

Counterfeit Baijiu has been emerging because of the price variances of real-aged Chinese Baijiu. Accurate identification of different vintages is of great interest. In this study, the combination of gas chromatography-mass spectrometry (GC-MS) and proton nuclear magnetic resonance (1H NMR) spectroscopy was applied for the comprehensive analysis of chemical constituents for Maotai-flavor Baijiu. Furthermore, a novel data fusion strategy combined with machine learning algorithms has been established. The results showed that the midlevel data fusion combined with the random forest algorithm were the best and successfully applied for classification of different Baijiu vintages. A total of 14 differential compounds (belonging to fatty acid ethyl esters, alcohols, organic acids, and aldehydes) were identified, and used for evaluation of commercial Maotai-flavor Baijiu. Our results indicated that both volatiles and nonvolatiles contributed to the vintage differences. This study demonstrated that GC-MS and 1H NMR spectra combined with a data fusion strategy are practical for the classification of different vintages of Maotai-flavor Baijiu.

Insights into the mechanism of modification by self-assembling starch-based fatty acid esters that cause a pronounced time-dependent effect on asphalt hardness

Modifying and controlling the viscoelasticity of asphalt is a major challenge for maintaining and managing paved roads and extending their life. To date, asphalt has been modified with petroleum-based synthetic polymers, mainly to improve its resistance to permanent deformation. While, we are developing an asphalt modifier, 2,3,4,6-O-tetrapalmitoylated-1,5-anhydro-d-glucitol (C16AG), which is obtained from starch and fatty acids as raw materials. Here, we performed various experiments to obtain insights into the mechanism of asphalt modification by C16AG. The results showed that the hardness of C16AG-modified asphalt showed a time dependence: it remained softer than the original unmodified asphalt for several hours after the addition of C16AG and then hardened depending on the amount of C16AG added. The time dependence of the hardness of the C16AG-modified asphalt is related to the modification mechanism and it is proposed to include the following processes: (1) C16AG mixes with the resin and asphaltene that usually cause the hardening of asphalt and (2) prevents the ordering of these components; (3) then spontaneous fiber network is formed slowly by C16AG.

Common dietary emulsifiers promote metabolic disorders and intestinal microbiota dysbiosis in mice

Dietary emulsifiers are linked to various diseases. The recent discovery of the role of gut microbiota–host interactions on health and disease warrants the safety reassessment of dietary emulsifiers through the lens of gut microbiota. Lecithin, sucrose fatty acid esters, carboxymethylcellulose (CMC), and mono- and diglycerides (MDG) emulsifiers are common dietary emulsifiers with high exposure levels in the population. This study demonstrates that sucrose fatty acid esters and carboxymethylcellulose induce hyperglycemia and hyperinsulinemia in a mouse model. Lecithin, sucrose fatty acid esters, and CMC disrupt glucose homeostasis in the in vitro insulin-resistance model. MDG impairs circulating lipid and glucose metabolism. All emulsifiers change the intestinal microbiota diversity and induce gut microbiota dysbiosis. Lecithin, sucrose fatty acid esters, and CMC do not impact mucus–bacterial interactions, whereas MDG tends to cause bacterial encroachment into the inner mucus layer and enhance inflammation potential by raising circulating lipopolysaccharide. Our findings demonstrate the safety concerns associated with using dietary emulsifiers, suggesting that they could lead to metabolic syndromes.