13-Docosenamide
(Synonyms: 芥酸酰胺) 目录号 : GC41910The amide of docosenoic acid
Cas No.:112-84-5
Sample solution is provided at 25 µL, 10mM.
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- Purity: >98.00%
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13-Docosenamide is the amide of docosenoic acid. It was first identified in the cerebrospinal fluid of sleep-deprived cats. It has also been detected in the cerebrospinal fluid of rats and humans. 13-Docosenamide causes reduced mobility and slightly lessened awareness in rats, whereas 9-octadecenamide induces physiological sleep.
Cas No. | 112-84-5 | SDF | |
别名 | 芥酸酰胺 | ||
Canonical SMILES | CCCCCCCC/C=C\CCCCCCCCCCCC(N)=O | ||
分子式 | C22H43NO | 分子量 | 337.6 |
溶解度 | acidic PBS: <50 µ g/ml,basic PBS: <50 µ g/ml,DMF: >14 mg/ml,DMSO: >20 mg/ml,Ethanol: >22 mg/ml,PBS pH 7.2: <50 µ g/ml | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 2.9621 mL | 14.8104 mL | 29.6209 mL |
5 mM | 0.5924 mL | 2.9621 mL | 5.9242 mL |
10 mM | 0.2962 mL | 1.481 mL | 2.9621 mL |
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2.
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13-Docosenamide release by bacteria in response to glucose during growth-fluorescein quenching and clinical application
Appl Microbiol Biotechnol 2018 Aug;102(15):6673-6685.PMID:29860593DOI:10.1007/s00253-018-9127-x.
Our investigations on extracellular biochemical events to find readily and sensitively detectable/measurable molecular targets for developing easier, simpler, and quicker diagnostic methods and tools for bacterial pathogens led to the observation that bacteria grown in the presence of glucose produced a compound capable of quenching fluorescein. Under the experimental conditions, among various sugars, glucose was found to induce maximum amount of the quencher when Escherichia coli was grown in presence of 50 mM glucose in rarified LB. The release of quencher closely following bacterial growth significantly from fourth hour after moderate inoculation. This fluorescein-quencher was purified using TLC and HPLC and identified using GC-MS as 13-Docosenamide or erucamide, originally known as plant lipid, is a neuroactive compound in human and animals. Fluorescence and UV-absorption spectral analysis showed that the compound formed stable adduct with fluorescein in the ground state. Commercial 13-docosonamide enabled quantitation of the compound produced in micromolar quantities during glucose utilization from the medium. Twenty-seven different commonly encountered bacteria, pathogens or otherwise, could produce the quencher. A simple microplate-based growth monitoring method was developed exploiting quenching as an easily and readily measurable signal, either using a reader or an imager. While 13-Docosenamide release by bacteria may be relevant in host-bacteria interactions, especially when growing under conditions that provide glucose, the new approach with inexpensive reagents can provide a new antibiogram technique.
A new pyrimidine alkaloid from the roots of Tadehagi triquetrum (L.) H.Ohashi
Nat Prod Res 2021 Feb;35(3):413-420.PMID:31311318DOI:10.1080/14786419.2019.1634716.
Tadehagi triquetrum (L.) H.Ohashi, also known as Desmodium triquetrum (Fabaceae) is the most important plant in the herbal remedies. The present study focus on the isolation, in-silico and in-vitro studies of the two alkaloids C1 (5-(4-[(methylcarbamoyl) amino]-2-oxopyrimidin-1(2H)-yl) tetrahydrofuran-2-yl) methyl methyl carbamate is novel alkaloid and C2 13-Docosenamide is a known alkaloid. The chemical structures of compounds have been elucidated based on comprehensive techniques like GCMS, IR and NMR. In order to know the molecular mechanisms for the two compounds, in silico molecular docking study has been performed. Both compounds have shown perfect binding affinity to the enzymes TNF α, IL-4, IL-13 and 5 LOX Enzyme. The compounds also exhibited comparable G-scores and Glide energy values in comparison with the standard dexamethasone. In addition both the compounds have been tested for in vitro antioxidant assay by using ABTS and DPPH method and the results were compared with standard ascorbic acid.
Phytochemical analysis and mode of action against Candida glabrata of Paeonia emodi extracts
J Mycol Med 2018 Sep;28(3):443-451.PMID:29803699DOI:10.1016/j.mycmed.2018.04.008.
In the present study, we have evaluated the antifungal activity of the seed, root and leaf of Paeonia emodi (commonly known as Himalayan peony) in four common solvents (acetone, chloroform, methanol and water) against six fungal strains. The methanolic seed extract (MSE) showed promising antifungal activity against Candida albicans (6.25mg/mL), Candida glabrata (3.12mg/mL) and Candida parapsilosis (12.50mg/mL) among all the fungal strains tested. Combination of the MSE with the well-known commercial antifungal drugs amphotericin B (Amp B), nystatin (NYS) and fluconazole (FLC) resulted in the killing of C. glabrata at non-inhibitory concentrations, i.e., 0.35μg/mL for Amp B, 0.55μg/mL for NYS and 1.19μg/mL for FLC. Notably, MSE caused cell wall damage of C. glabrata cells, as confirmed by confocal microscopy, flowcytometry and scanning electron microscopy (SEM). The MSE was fractionated by thin layer chromatography (TLC). TLC-bioautography was used to determine the active compounds present in the MSE. Column chromatography was used to separate the potential active compounds from the MSE. Furthermore, gas chromatography-mass spectrometry (GC-MS) andfourier-transform infrared spectroscopy (FTIR) were used to identify the phytocomponents of the MSE. These experiments revealed 13-Docosenamide/9-octadecenamide/trans-13-docosenamide (89.70%) as being the predominant compound using a chloroform/methanol solvent system for the separation. Interestingly, the MSE also exhibited less significant cytotoxicity at the minimum inhibitory concentration (MIC) against mammalian cells (HeLa and HEK293). This study suggests that the MSE of P. emodi can be used for the treatment of C. glabrata infection.
Plasma Metabolic Disturbances in Parkinson's Disease Patients
Biomedicines 2022 Nov 22;10(12):3005.PMID:36551761DOI:10.3390/biomedicines10123005.
Plasma from patients with Parkinson's disease (PD) is a valuable source of information indicating altered metabolites associated with the risk or progression of the disease. Neurotoxicity of dopaminergic neurons, which is triggered by aggregation of α-synuclein, is the main pathogenic feature of PD. However, a growing body of scientific reports indicates that metabolic changes may precede and directly contribute to neurodegeneration. Identification and characterization of the abnormal metabolic pattern in patients' plasma are therefore crucial for the search for potential PD biomarkers. The aims of the present study were (1) to identify metabolic alterations in plasma metabolome in subjects with PD as compared with the controls; (2) to find new potential markers, some correlations among them; (3) to identify metabolic pathways relevant to the pathophysiology of PD. Plasma samples from patients with PD (n = 25) and control group (n = 12) were collected and the gas chromatography-time-of-flight-mass spectrometry GC-TOFMS-based metabolomics approach was used to evaluate the metabolic changes based on the identified 14 metabolites with significantly altered levels using univariate and multivariate statistical analysis. The panel, including 6 metabolites (L-3-methoxytyrosine, aconitic acid, L-methionine, 13-Docosenamide, hippuric acid, 9,12-octadecadienoic acid), was identified to discriminate PD from controls with the area under the curve (AUC) of 0.975, with an accuracy of 92%. We also used statistical criteria to identify the significantly altered level of metabolites. The metabolic pathways involved were associated with linoleic acid metabolism, mitochondrial electron transport chain, glycerolipid metabolism, and bile acid biosynthesis. These abnormal metabolic changes in the plasma of patients with PD were mainly related to the amino acid metabolism, TCA cycle metabolism, and mitochondrial function.
High-throughput method for Antibiotic Susceptibility Testing based on Fluorescein Quenching by Bacteria: Application to Urinary Tract Infection
Sci Rep 2020 Mar 4;10(1):4058.PMID:32132575DOI:10.1038/s41598-020-60717-9.
We recently reported a sugar-induced bacterial release of 13-Docosenamide and its ability to quench fluorescein. This simple handle to monitor bacterial growth is readily applicable to develop a quicker antibiotic sensitivity testing method along with a low-cost field-use optical instrumentation. Conditions were standardized to perform this new procedure in the most preferred and CLSI-recommended microdilution format in 12-well strips. A simple and portable optoelectronic prototype was used to capture the image and read the fluorescence signal of the culture medium of the 12-well strips. This new Fluorescence Quenching Method along with the device enabled the choice of the right antibiotic within 8 h of sample collection from the patient. It was compliant to the Clinical Laboratory Standard Institute's quality control guidelines. Clinical assessment of the method using 440 urine samples from Urinary Tract Infection patients against 21 routinely used antibiotics showed a 94.3% match with the results of the Standard Disk Diffusion method. This new method saves the precious time taken for and the cost of antibiotic susceptibility testing for quicker and effective treatment with better compliance.