ABSTRACT
Octacosanol has various biological effects such as antioxidant, hypolipidemic and anti-fatigue. However, poor solubility has limited the application of octacosanol in food. The aim of this study was to prepare octacosanol nanoemulsions with better solubility, stability and safety and to investigate in vivo anti-fatigue effect. The food-grade formulation of the octacosanol nanoemulsions consisted of octacosanol, olive oil, Tween 80, glycerol and water with 0.1â¯%, 1.67â¯%, 23.75â¯%, 7.92â¯% and 66.65â¯% (w/w), respectively. The nanoemulsions had an average particle size of 12.26 ± 0.76â¯nm and polydispersity index of 0.164 ± 0.12, and showed good stability under different pH, cold, heat, ionic stress and long-term storage conditions. The results of animal experiments showed that the octacosanol nanoemulsions significantly prolonged the fatigue tolerance time, alleviated the fatigue-related biochemical indicators, and weakened the oxidative stress. Meanwhile, octacosanol nanoemulsions upregulated hepatic glycogen levels. Taken together, these findings suggested that octacosanol nanoemulsions have promising applications as anti-fatigue functional foods.
Subject(s)
Emulsions , Fatigue , Fatty Alcohols , Emulsions/chemistry , Animals , Fatty Alcohols/chemistry , Fatty Alcohols/pharmacology , Fatigue/drug therapy , Particle Size , Male , Water/chemistry , Oxidative Stress/drug effects , Rats , Antioxidants/pharmacology , Antioxidants/chemistry , Rats, Sprague-Dawley , Solubility , Liver/drug effects , Liver/metabolism , Glycogen/metabolism , Glycogen/chemistry , Polysorbates/chemistry , Polysorbates/pharmacology , Nanoparticles/chemistryABSTRACT
Human lysozyme undergoes a phase-separation process to form insoluble amyloid-architects that cause several pathologies including systemic amyloidosis. Here we have tailored 6-gingerol by extending its molecular framework with active functional groups to specifically target lysozyme phase-transition events. Aggregation assay revealed that tailored 6-gingerol with 4-aromatic moieties (MTV4) substantially suppressed the conversion of the lysozyme low-density liquid phase (LDLP) to solid-phase structured amyloids. The data obtained from biophysical, computational, and microscopic imaging tools suggest direct intervention of MTV4 with the liquid-liquid phase separation. The CD data suggest that MTV4 was able to retain the native conformation of lysozyme. Both biomolecular and computational data reveal the interference of MTV4 with the aggregation-prone hydrophobic stretches within the lysozyme, thereby retaining the native structure and reversing the misfolded intermediates to active monomers. Also, MTV4 was able to induce rapid dissolution of preformed-toxic amyloid fibrils. These results reinforce the importance of the aromatic-aromatic interaction in preventing human lysozyme phase separation.
Subject(s)
Amyloid , Catechols , Fatty Alcohols , Muramidase , Muramidase/chemistry , Muramidase/metabolism , Fatty Alcohols/chemistry , Humans , Catechols/chemistry , Amyloid/chemistry , Amyloid/metabolism , Hydrophobic and Hydrophilic Interactions , Molecular Structure , Phase Transition , Protein Aggregates , Phase SeparationABSTRACT
Slow-digesting starch with bioactive functionality has been attracting much interest with the increasing incidence of type-2 diabetes and other diet-related illnesses. The present study demonstrates a simple method for preparing a starch inclusion complex with reduced enzymic digestion and enhanced antioxidant activities using debranched pea starch (PS) and 10-gingerol (10G). Enzymically debranched starch complexed more 10G and formed more structurally ordered starch-10G complexes compared to PS that had not been debranched. Debranching for 6 h resulted in starch with better complexing ability for 10G than starches debranched for longer times. The debranched starch-10G complexes had higher antioxidant activities and a much slower in vitro enzymic digestion profile (rate and hydrolysis extent) than the 10G complex prepared with starch that was not debranched. Our study demonstrates that debranched pea starch-10G complexes with slow-digesting and antioxidant properties are likely to be of interest for developing ingredients for healthier food choices.
Subject(s)
Antioxidants , Catechols , Pisum sativum , Starch , Antioxidants/chemistry , Antioxidants/pharmacology , Starch/chemistry , Catechols/chemistry , Pisum sativum/chemistry , Fatty Alcohols/chemistry , Hydrolysis , Amylose/chemistryABSTRACT
Gingerols are phenolic biomedical compounds found in ginger (Zingiber officinale) whose low aqueous solubility limits their medical application. To improve their solubility and produce novel glucosides, an α-glucosidase (glycoside hydrolase) from Agrobacterium radiobacter DSM 30147 (ArG) was subcloned, expressed, purified, and then confirmed to have additional α-glycosyltransferase activity. After optimization, the ArG could glycosylate gingerols into three mono-glucosides based on the length of their acyl side chains. Compound 1 yielded 63.0 %, compound 2 yielded 26.9 %, and compound 3 yielded 4.37 %. The production yield of the gingerol glucosides optimally increased in 50 mM phosphate buffer (pH 6) with 50 % (w/v) maltose and 1000 mM Li+ at 40 °C for an 24-h incubation. The structures of purified compound 1 and compound 2 were determined as 6-gingerol-5-O-α-glucoside (1) and novel 8-gingerol-5-O-α-glucoside (2), respectively, using nucleic magnetic resonance and mass spectral analyses. The aqueous solubility of the gingerol glucosides was greatly improved. Further assays showed that, unusually, 6-gingerol-5-O-α-glucoside had 10-fold higher anti-inflammatory activity (IC50 value of 15.3 ± 0.5 µM) than 6-gingerol, while the novel 8-gingerol-5-O-α-glucoside retained 42.7 % activity (IC50 value of 106 ± 4 µM) compared with 8-gingerol. The new α-glucosidase (ArG) was confirmed to have acidic α-glycosyltransferase activity and could be applied in the production of α-glycosyl derivatives. The 6-gingerol-5-O-α-glucoside can be applied as a clinical drug for anti-inflammatory activity.
Subject(s)
Agrobacterium tumefaciens , Anti-Inflammatory Agents , Catechols , Fatty Alcohols , Glucosides , alpha-Glucosidases , Fatty Alcohols/chemistry , Fatty Alcohols/pharmacology , Fatty Alcohols/metabolism , alpha-Glucosidases/metabolism , alpha-Glucosidases/chemistry , Catechols/chemistry , Catechols/pharmacology , Catechols/metabolism , Glucosides/chemistry , Glucosides/pharmacology , Glucosides/metabolism , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/chemistry , Solubility , Zingiber officinale/chemistryABSTRACT
Zhenwu Decoction (ZWD), a classic formula from Zhang Zhongjing's "Treatise on Typhoid Fever" in the Han Dynasty, consists of five traditional Chinese medicines: Aconiti Lateralis Radix Praeparata (ALRP), Paeoniae Radix Alba, Poria Cocos, Ginger, and Rhizoma Atractylodis Macrocephalae. To evaluate the chemical constituent consistency of ZWD before and after compatibility, an ultra-performance liquid chromatography-electrospray ionization-quadrupole time-of-flight mass spectrometry was established to comprehensively study the constituents of ZWD. By normalizing the peak area, the pairwise compatibility of ALRP and the other four medicinal herbs, as well as the compatibility of the entire formula were studied, respectively. Multivariate statistical analysis was used to identify the differences. The processed data were analyzed by principal component analysis and supervised orthogonal partial least squared discriminant analysis, and an S-plot was generated to compare the differences in the chemical composition of the two types of decoction samples. The results showed that during the decoction process of ZWD, a total of seven components were recognized as differential compounds before and after compatibility of ZWD, namely 6-gingerol, zingerone, benzoylhypaconine, hypaconitine, benzoylaconine, paeoniflorin and fuziline. The results of this study provide basic data reference for understanding the law of ZWD compatibility and are valuable for the compatibility study of other herbal medicines.
Subject(s)
Drugs, Chinese Herbal , Metabolomics , Spectrometry, Mass, Electrospray Ionization , Tandem Mass Spectrometry , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/analysis , Spectrometry, Mass, Electrospray Ionization/methods , Chromatography, High Pressure Liquid/methods , Tandem Mass Spectrometry/methods , Metabolomics/methods , Fatty Alcohols/analysis , Fatty Alcohols/chemistry , Principal Component Analysis , Catechols/analysis , Catechols/chemistry , Zingiber officinale/chemistry , Glucosides/analysis , Glucosides/chemistry , Monoterpenes/analysis , Monoterpenes/chemistry , Benzoates/analysis , Benzoates/chemistry , Bridged-Ring Compounds/analysis , Bridged-Ring Compounds/chemistry , Multivariate Analysis , Paeonia/chemistry , Aconitum/chemistry , Aconitine/analogs & derivativesABSTRACT
Effect of puffing on conversion of gingerols to shogaols, physicochemical properties as well as antioxidant and anti-inflammatory activities of puffed ginger was investigated. Puffing significantly increased extraction yield and the highest value was 12.52% at 980 kPa. The significant decrease in gingerols and increase in shogaols were occurred after puffing, respectively. Especially, 6-shogaol was dramatically increased from 4.84 to 99.10 mg/g dried ginger. Puffed ginger exhibited the higher antioxidant activities (analyzed by DPPH, ABTS, TPC, and TFC) than those of control, and they were significantly increased with increasing puffing pressure. In case of anti-inflammatory activity, puffed ginger did not inhibit NO production, but significantly inhibited TNF-α and IL-6 productions. Among gingerols and shogaols, 6-shogaol showed significantly strong correlations with both antioxidant and anti-inflammatory activities. Consequently, puffed ginger can be applied to functional food industry, which dramatically increased the contents of 6, 8, 10-shogaols, the main bioactive compounds in ginger.
Subject(s)
Anti-Inflammatory Agents , Antioxidants , Catechols , Fatty Alcohols , Plant Extracts , Zingiber officinale , Zingiber officinale/chemistry , Catechols/chemistry , Catechols/analysis , Antioxidants/chemistry , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Fatty Alcohols/chemistry , Fatty Alcohols/analysis , Fatty Alcohols/pharmacology , Plant Extracts/chemistry , Plant Extracts/pharmacology , Animals , MiceABSTRACT
Nanoliposomes (NLs) are ideal carriers for delivering complex molecules and phytochemical products, but ginger by-products, despite their therapeutic benefits, have poor bioavailability due to their low water solubility and stability. Crude ginger extracts (CGEs) and 6-gingerol were individually encapsulated within NLs for in vitro activity assessment. In vitro evaluation of anti-proliferative and anti-inflammatory properties of encapsulated 6-gingerol and CGE was performed on healthy human periodontal ligament (PDL) fibroblasts and MDA-MB-231 breast cancer cells. Encapsulation efficiency and loading capacity of 6-gingerol reached 25.23% and 2.5%, respectively. NLs were found stable for up to 30 days at 4°C with a gradual load loss of up to 20%. In vitro cytotoxic effect of encapsulated 6-gingerol exceeded 70% in the MDA-MB-231 cell line, in a comparable manner with non-encapsulated 6-gingerol and CGE. The effect of CGE with an IC50 of 3.11 ± 0.39, 7.14 ± 0.80, and 0.82 ± 0.55 µM and encapsulated 6-gingerol on inhibiting IL-8 was evident, indicating its potential anti-inflammatory activity. Encapsulating 6-gingerol within NLs enhanced its stability and facilitated its biological activity. All compounds, including vitamin C, were equivalent at concentrations below 2 mg/mL, with a slight difference in antioxidant activity. The concentrations capable of inhibiting 50% of 2,2-diphenyl-1-picrylhydrazyl (DPPH) substrate were comparable.
Subject(s)
Anti-Inflammatory Agents , Catechols , Fatty Alcohols , Liposomes , Zingiber officinale , Fatty Alcohols/chemistry , Fatty Alcohols/pharmacology , Humans , Catechols/chemistry , Catechols/pharmacology , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/administration & dosage , Anti-Inflammatory Agents/pharmacokinetics , Liposomes/chemistry , Cell Line, Tumor , Zingiber officinale/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Antineoplastic Agents/pharmacokinetics , Cell Survival/drug effects , Nanoparticles/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Interleukin-8/metabolism , Cell Proliferation/drug effectsABSTRACT
With the increasing number of diabetic patients in the world, there is an urgent requirement to reduce the incidence of diabetes. It is considered that a viable prophylactic treatment for type 2 diabetes mellitus is to reduce starch digestibility and oxidative stress. In this study, a novel type of slowly digested starch [pea starch (PS)-gingerol complex] was fabricated to evaluate its in vitro enzymatic digestibility and antioxidant activities. Theoretical and experimental analyses showed that PS can encapsulate gingerols with long alkyl chains to form starch-gingerol complexes, which are further stacked into a mixture of V6- and V7-crystallites. These complexes, in particular the PS-10-gingerol complex, showed high resistance to amylolysis and good antioxidant activities. This study demonstrates that these novel starch-gingerol complexes have the potential to deliver antioxidants encapsulated in starch with slow-digesting properties and reduce oxidative stress. Moreover, this new type of slowly digested starch with antioxidant properties showed great potential in the prevention of type 2 diabetes.
Subject(s)
Antioxidants , Catechols , Diabetes Mellitus, Type 2 , Fatty Alcohols , Starch , Starch/chemistry , Antioxidants/chemistry , Fatty Alcohols/chemistry , Catechols/chemistry , Diabetes Mellitus, Type 2/prevention & control , Oxidative Stress/drug effects , HumansABSTRACT
Herbivorous insects utilize intricate olfactory mechanisms to locate food plants. The chemical communication of insect-plant in primitive lineage offers insights into evolutionary milestones of divergent olfactory modalities. Here, we focus on a system endemic to the Qinghai-Tibetan Plateau to unravel the chemical and molecular basis of food preference in ancestral Lepidoptera. We conducted volatile profiling, neural electrophysiology, and chemotaxis assays with a panel of host plant organs to identify attractants for Himalaya ghost moth Thitarodes xiaojinensis larvae, the primitive host of medicinal Ophiocordyceps sinensis fungus. Using a DREAM approach based on odorant induced transcriptomes and subsequent deorphanization tests, we elucidated the odorant receptors responsible for coding bioactive volatiles. Contrary to allocation signals in most plant-feeding insects, T. xiaojinensis larvae utilize tricosane from the bulbil as the main attractant for locating native host plant. We deorphanized a TxiaOR17b, an indispensable odorant receptor resulting from tandem duplication of OR17, for transducing olfactory signals in response to tricosane. The discovery of this ligand-receptor pair suggests a survival strategy based on food location via olfaction in ancestral Lepidoptera, which synchronizes both plant asexual reproduction and peak hatch periods of insect larvae.
Subject(s)
Larva , Moths , Receptors, Odorant , Animals , Moths/physiology , Receptors, Odorant/genetics , Receptors, Odorant/metabolism , Smell/physiology , Insect Proteins/genetics , Insect Proteins/metabolism , Insect Proteins/chemistry , Phylogeny , Chemotaxis , Fatty Alcohols/pharmacology , Fatty Alcohols/chemistryABSTRACT
Ginger has traditionally been used to treat and prevent nausea and vomiting; however, the results of clinical trials are ambiguous. The efficacy of ginger is attributed to gingerols and their metabolites, shogaols. Since these compounds have different pharmacological profiles, the clinical efficacy of ginger products is largely dependent on their chemical composition. The goal of our study was to examine the stability of ginger, determining the 6-gingerol contents in order to assess the effects of different storage conditions. We have performed a 6-month stability test with dry ginger rhizome samples stored in a constant climate chamber in three different storage containers (uncovered glass container, glass container sealed with rubber stopper, and plastic container). The 6-gingerol contents were measured by HPLC method. The concentration of 6-gingerol decreased in all samples. In the sealed glass container, the decrease in 6-gingerol content was significantly lower than in the unsealed glass container and in the plastic container. These results demonstrate that storage conditions have a significant impact on the quality of ginger, which may also affect efficacy.
Subject(s)
Catechols , Fatty Alcohols , Zingiber officinale , Zingiber officinale/chemistry , Fatty Alcohols/chemistry , Fatty Alcohols/analysis , Fatty Alcohols/pharmacology , Catechols/chemistry , Catechols/analysis , Catechols/pharmacology , Chromatography, High Pressure Liquid , Rhizome/chemistry , Drug Stability , Drug Storage , Clinical Trials as Topic , Plant Extracts/chemistry , Plant Extracts/pharmacologyABSTRACT
BACKGROUND: Dietary supplements derived from botanicals are commonly consumed and investigated in biomedical studies for their potential health benefits. Accurate identification and quantification of key chemical constituents from botanical ingredients is necessary for consistent product preparations and reproducible research results. Manufacturers need quantitative reference materials of the chemical constituents of interest to verify the content of ingredients and products. The rigor and reproducibility of biomedical research is enhanced through thorough characterization of the interventions used in mechanistic, clinical, and safety investigations. Quantitative reference materials enable reliable product quality assessments and reproducible research results. OBJECTIVE: Solution-based certified reference material (CRM) mixes were developed as calibrants for phytochemicals in ginger and kava. The kava CRM contained yangonin, desmethoxyyangonin, dihydrokavain, DL-kavain, methysticin, dihydromethysticin, flavokawain A, flavokawain B, and flavokawain C. The ginger CRM contained 6-gingerol, 8-gingerol, 10-gingerol, 6-shogaol, 8-shogaol, and 10-shogaol. METHODS: Each phytochemical was sourced as an isolated compound and assigned a purity factor by a mass balance approach accounting for residual impurities. The solution standard mixes were formulated by gravimetric addition of each phytochemical incorporating the purity factor and diluting with acetonitrile to the target concentrations of 500 µg/mL for the gingerols and shogaols, 250 µg/mL for the kavalactones, and 25 µg/mL for the flavokawains. RESULTS: The concentration accuracy of each component in the solution mixes was analytically verified by ultra high performance liquid chromatography with ultraviolet detection (UHPLC-UV) assay comparison to an independently prepared calibration solution. Each component in the ginger and kava CRMs were within 5 and 7% of the target concentrations, respectively. CONCLUSION: Homogeneous kava and ginger phytochemical solution mixes were produced with accurate constituent concentrations and demonstrated good stability over 2 years. These solution mixes were launched as commercially available CRMs. HIGHLIGHTS: These mixes can be used as accurate concentration stock solutions to prepare calibrators and controls for botanical dietary supplement product testing and standardization.
Subject(s)
Fatty Alcohols , Kava , Phytochemicals , Reference Standards , Zingiber officinale , Zingiber officinale/chemistry , Kava/chemistry , Phytochemicals/analysis , Phytochemicals/standards , Phytochemicals/chemistry , Fatty Alcohols/analysis , Fatty Alcohols/chemistry , Catechols/analysis , Catechols/chemistry , Catechols/standards , Chromatography, High Pressure Liquid/methods , Dietary Supplements/analysis , Dietary Supplements/standardsABSTRACT
Self-assembled lipid nanoparticles (LNPs), serving as essential nanocarriers in recent COVID-19 mRNA vaccines, provide a stable and versatile platform for delivering a wide range of biological materials. Notably, LNPs with unique inverse mesostructures, such as cubosomes and hexosomes, are recognized as fusogenic nanocarriers in the drug delivery field. This study delves into the physicochemical properties, including size, lyotropic liquid crystalline mesophase, and apparent pKa of LNPs with various lipid components, consisting of two ionizable lipids (ALC-0315 and SM-102) used in commercial COVID-19 mRNA vaccines and a well-known inverse mesophase structure-forming helper lipid, phytantriol (PT). Two partial mesophase diagrams are generated for both ALC-0315/PT LNPs and SM-102/PT LNPs as a function of two factors, ionizable lipid ratio (α, 0-100 mol%) and pH condition (pH 3-11). Furthermore, the impact of different LNP stabilizers (Pluronic F127, Pluronic F108, and Tween 80) on their pH-dependent phase behavior is evaluated. The findings offer insights into the self-assembled mesostructure and ionization state of the studied LNPs with potentially enhanced endosomal escape ability. This research is relevant to developing innovative next-generation LNP systems for delivering various therapeutics.
Subject(s)
Fatty Alcohols , Lipids , Liquid Crystals , Nanoparticles , Nanoparticles/chemistry , Fatty Alcohols/chemistry , Liquid Crystals/chemistry , Hydrogen-Ion Concentration , Lipids/chemistry , Ions/chemistry , LiposomesABSTRACT
Cubosomes are nanoparticles with bicontinuous cubic internal nanostructures that have been considered for use in drug delivery systems (DDS). However, their low structural stability is a crucial concern for medical applications. Herein, we investigated the use of a gemini surfactant, sodium dilauramidoglutamide lysine (DLGL), which is composed of two monomeric surfactants linked with a spacer to improve the structural stability of cubosomes prepared with phytantriol (PHY). Uniform nanosuspensions comprising a specific mixing ratio of DLGL and PHY in water prepared via ultrasonication were confirmed by using dynamic light scattering. Small-angle X-ray scattering and cryo-transmission electron microscopy revealed the formation of Pn3Ì m cubosomes in a range of DLGL/PHY solid ratios between 1 and 3% w/w. By contrast, cubosome formation was not observed at DLGL/PHY solid ratios of 5% w/w or higher, suggesting that excess DLGL interfered with cubosome formation and caused them to transform into small unilamellar vesicles. The addition of phosphate-buffered saline to the nanosuspension caused aggregation when the solid ratio of DLGL/PHY was less than 5% w/w. However, Im3Ì m cubosomes were obtained at solid ratios of DLGL/PHY of 6, 7.5, and 10% w/w. The lattice parameters of the Pn3Ì m and Im3Ì m cubosomes were approximately 7 and 11-13 nm, respectively. The lattice parameters of Im3Ì m cubosomes were affected by the concentration of DLGL. Pn3Ì m cubosomes were surprisingly stable for 4 weeks at both 25 and 5 °C. In conclusion, DLGL, a gemini surfactant, was found to act as a new stabilizer for PHY cubosomes at specific concentrations. Cubosomes composed of DLGL are stable under low-temperature storage conditions, such as in refrigerators, making them a viable option for heat-sensitive DDS.
Subject(s)
Drug Delivery Systems , Surface-Active Agents , Surface-Active Agents/chemistry , Fatty Alcohols/chemistry , Microscopy, Electron, Transmission , Particle SizeABSTRACT
This study presents an efficient strategy for large-scale preparation of low polarity gingerols directly from ginger crude extract by high-speed countercurrent chromatography with different rotation mode. The ultrasonic-assisted extraction conditions were optimized by response surface methodology and the results showed the major low polarity gingerols could be well enriched under the optimized extraction conditions. Then the crude extract without any pretreatment was directly separated by high-speed countercurrent chromatography with different rotation mode using n-hexane/ethyl acetate/methanol/water (6:4:6:4, v/v/v/v) as the solvent system. In about 400 min, five major gingerols including 150 mg of [6]-gingerol, 50 mg of [8]-gingerol, 20 mg of [6]-shogaol, 43 mg of [6]-dehydrogingerdione, and 40 mg of [10]-gingerol were obtained from 1.2 g of crude extract in a single run with repeated injection. Their structures were identified by 1 H-NMR spectroscopy.
Subject(s)
Countercurrent Distribution , Zingiber officinale , Countercurrent Distribution/methods , Zingiber officinale/chemistry , Rotation , Plant Extracts/chemistry , Fatty Alcohols/chemistryABSTRACT
Deep eutectic solvents (DES) are tailorable non-aqueous solvents with promising properties for a range of applications, from industrial dissolution of plant products to biomedicine. They are mixtures of hydrogen bond donors and acceptors with low melting points that can be tailored to specific applications, and many support the self-assembly of amphiphilic molecules into lyotropic liquid crystal phases. Self-assembled lipid structures have potential for numerous applications, including drug delivery. These ordered structures can act as carriers, slow-release vehicles, or microreactors. Lipid self-assembly in non-aqueous solvents, such as deep eutectic solvents, is important for applications at extreme temperatures, or involving water-insoluble or water sensitive components. However, lipid self-assembly in these solvents remains largely unexplored. In this paper, we have examined the self-assembly of phytantriol, a non-ionic lipid, at 10 and 30 wt% in the deep eutectic solvent choline chloride:urea, with and without water. Self-assembly was assessed using small angle X-ray scattering and cross polarised optical microscopy at temperatures from 25-66 °C. We found that pure choline chloride:urea supports a Pn3m cubic phase similar to that formed in water. However, mixtures of the DES with water resulted in phytantriol forming an inverse hexagonal phase and influenced the phase transition temperatures. These results demonstrate that choline chloride:urea can support diverse phase behaviour, and also provides a mechanism for tailoring the phase for particular applications simply by controlling the amount of water in the solvent. In the future this could lead to methods of triggered release of drugs and biomolecules by the simple addition of water which could be critical for drug delivery applications.
Subject(s)
Choline , Urea , Urea/chemistry , Choline/chemistry , Deep Eutectic Solvents , Solvents/chemistry , Fatty Alcohols/chemistryABSTRACT
Indole-containing acyloins are either key intermediates of many antimicrobial/antiviral natural products or building blocks in the synthesis of biologically active molecules. As such, access to structurally diverse indole-containing acyloins has attracted considerable attention. In this report, we present a pilot study of using biotransformation to provide acyloins that contain various indole substituents. The biotransformation system contains the tryptophan synthase standalone ß-subunit variant, PfTrpB6, generated from directed evolution in the literature; a commercially available L-amino acid oxidase (LAAO); and the thiamine-diphosphate (ThDP)-dependent enzyme NzsH, encoded in the biosynthetic gene cluster (nzs) of the bacterial carbazole alkaloid natural product named neocarazostatin A. The utilization of the first two enzymes, the PfTrpB variant and LAAO, is designed to provide structurally diverse indole 3-pyruvate derivatives as donor substrates for NzsH-catalysed biotransformation to provide acyloin derivatives. Our results demonstrate that NzsH displays a considerable substrate profile toward donor substrates for production of acyloins with different indole ring systems, suggesting that NzsH could be further explored as a potential biocatalyst via directed evolution to improve the catalytic efficiency in the future.
Subject(s)
Fatty Alcohols , Indoles , Pilot Projects , Indoles/chemistry , Fatty Alcohols/chemistry , Pyruvic AcidABSTRACT
BACKGROUND: Ginger and its extracts have been frequently used in food processing and pharmaceuticals. However, the influence of ginger and its key compounds on benzo[a]pyrene (BaP) production in meat processing has not been investigated. The purpose of this study was to explore the effect of application of ginger and its important active ingredients on BaP formation and the mechanism of inhibiting BaP formation in charcoal-grilled pork sausages. RESULTS: The DPPH scavenging (23.59-59.67%) activity and the inhibition rate of BaP (42.1-68.9%) were significantly increased (P < 0.05) with increasing ginger addition. The active components extracted by supercritical carbon dioxide from ginger were identified by gas chromatography-mass spectrometry and 14 representative compounds (four terpenes, two alcohols, two aldehydes, four phenols and two other compounds, totaling 77.57% of the detected compounds) were selected. The phenolic compounds (eugenol, 6-gingerol, 6-paradol and 6-shogaol, accounting for 29.73% of the total composition) in ginger played a key role and had the strongest inhibitory effect on BaP (61.2-68.2%), whereas four other kinds of compound showed obviously feeble inhibitory activity (6.47-17.9%). Charcoal-grilled sausages with phenolic substances had lower values of thiobarbituric acid-reactive substances, carbonyl and diene (three classic indicators of lipid oxidation) (P < 0.05). CONCLUSION: Ginger and its key compounds could effectively inhibit the formation of BaP in charcoal-grilled pork sausages. Phenolic compounds make the strongest contribution to the inhibition of Bap formation, and the inhibitory mechanism was related to the inhibition of lipid oxidation. © 2023 Society of Chemical Industry.
Subject(s)
Pork Meat , Red Meat , Zingiber officinale , Animals , Swine , Benzo(a)pyrene/analysis , Zingiber officinale/chemistry , Charcoal , Red Meat/analysis , Pork Meat/analysis , Catechols/analysis , Phenols/chemistry , Fatty Alcohols/chemistry , Plant Extracts/chemistryABSTRACT
The rhizomes of ginger have been in use in many forms of traditional and alternative medicines. Besides being employed as condiment and flavoring agent, it is used in the treatment of nausea, osteoarthritis, muscle pain, menstrual pain, chronic indigestion, Alzheimer's disease, and cancer. Ginger rhizome contains volatile oils, phenolic compounds and resins, and characterization studies showed that [6]-gingerol, [6]-shogaol, and [6]-paradol are reported to be the pharmacologically active components. Gingerol is a major chemical constituent found as volatile oil in the rhizomes of ginger. It has several medicinal benefits and used for the treatment of rheumatoid arthritis, nausea, cancer, and diabetes. Many studies have been carried out in various parts of the world to isolate and standardize gingerol for their use as a complementary medicine. The present review summarizes wide range of research studies on gingerol and its pharmacological roles in various metabolic diseases.
Subject(s)
Catechols , Zingiber officinale , Catechols/pharmacology , Catechols/therapeutic use , Fatty Alcohols/pharmacology , Fatty Alcohols/therapeutic use , Fatty Alcohols/chemistry , Plant Extracts/chemistry , Zingiber officinale/chemistry , Zingiber officinale/metabolismABSTRACT
The present study investigated the cardioprotective properties of 6-gingerol against alcohol-induced ROS-mediated cardiac tissue damage in rats. Experiments were conducted on 4 groups of rats, orally treated with control, 6-gingerol (10 mg/kg body weight), alcohol (6 g/kg body weight) and combination of 6-gingerol plus alcohol for two-month. In the results, we found 6-ginger treatment to alcohol-fed rats substantially suppressed ROS production in cardiac tissue. Alcohol-induced elevated 8-OHDG and protein carbonyls which represent oxidative modification of DNA and proteins were completely reversed by 6-gingerol. This was further endorsed by restored superoxide dismutase and catalase activities with 6-gingerol against alcohol-induced loss. The elevated cardiac biomarkers (CK-MB, cTn-T, cTn-I) and dyslipidemia in alcohol-intoxicated rats was significantly reversed by 6-gingerol. Furthermore, alcohol-induced apoptosis characterized by overexpression of cytochrome C, caspase-8 and caspase-9 was diminished with 6-gingerol treatment. Transmission electron microscope images conferred the cardioprotective properties of 6-gingerol as we have seen less structural derangements in mitochondria and reappearance of myofilaments. Our findings conclude that 6-ginger effectively protect alcohol-induced ROS-mediated cardiac tissue damage, which may be due to its potent antioxidant efficacy. Therefore, 6-gingerol could be a potential therapeutic molecule that can be used in the treatment of alcohol-induced myocardial injury.
Subject(s)
Oxidative Stress , Zingiber officinale , Rats , Animals , Fatty Alcohols/pharmacology , Fatty Alcohols/chemistry , Catechols/pharmacology , Catechols/chemistry , Apoptosis , Zingiber officinale/chemistry , Antioxidants/pharmacology , Antioxidants/metabolism , Body WeightABSTRACT
Compared with polymers and nanoparticles, fatty alcohols can not only increase the stability of foam, but also maintain better foamability at pH < 2, which is beneficial to reduce waste liquid and increase decontamination efficiency for radioactive surface pollution. However, different fatty alcohols have different hydrophobic chain lengths. The effects of fatty alcohols with different chain lengths on the performance of decontamination foam were studied at pH < 2, to assist in the selection of suitable fatty alcohols as foam stabilizers. Combined with betaine surfactant and phytic acid, biomass-based foams were synthesized using fatty alcohols with different chain lengths. When the hydrophobic tail groups of the fatty alcohol and the surfactant were the same, the foam showed the best performance, including the lowest surface tension, the highest liquid film strength, the greatest sag-resistance and the best stability. However, when the hydrophobic tail groups were different, the space between adjacent surface active molecules was increased by thermal motion of the excess terminal tail segments (a tail-wagging effect), and the adsorption density reduced on the gas-liquid interface, leading to increased surface tension and decreased liquid film strength, sag-resistance and stability. The use of decontamination foam stabilized by fatty alcohols with the same hydrophobic group as the surfactant was found to increase the decontamination rate of radioactive uranium pollution from 64 to over 90% on a vertical surface.