The Encephalopathic Action of Five-carbon-atom Fatty Acids in the Rabbit

1976 ◽  
Vol 50 (6) ◽  
pp. 463-472 ◽  
Author(s):  
P. F. Teychenne ◽  
I. Walters ◽  
L. E. Claveria ◽  
D. B. Calne ◽  
Jane Price ◽  
...  
Keyword(s):  
Carbon Atom ◽  
Functional Group ◽  
Low Frequency ◽  
Isovaleric Acid ◽  
Valeric Acid ◽  
Inborn Errors ◽  
Pronounced Increase ◽  
Tiglic Acid ◽  
Ventriculocisternal Perfusion ◽  
Electroencephalographic Recording

1. Five-carbon-atom organic acids (C-5 acids) have been administered intravenously to rabbits with ventriculocisternal perfusion and continuous electroencephalographic recording (EEG). The concentration of the acids in the cerebrospinal fluid (CSF) perfusate have been compared with changes in integrated low-frequency activity in the EEG. 2. The C-5 acids investigated were those accumulating in inborn errors of metabolism, i.e. isovaleric acid, β-methylcrotonic acid, tiglic acid and α-keto- and α-hydroxy-isovaleric acid. Their activity was compared with that of valeric acid. 3. Valeric acid and isovaleric acid produced coma and pronounced increase in slow-wave electrical activity and these changes paralleled the increase in concentration of the acids in the CSF perfusate. 4. The concentration of β-methylcrotonic acid and tiglic acid in the CSF perfusate reached values comparable with valeric acid and isovaleric acid but showed less encephalopathic activity. An interaction between β-methylcrotonic acid and isovaleric acid was observed. 5. Although the concentrations of α-ketoisovaleric acid and α-hydroxyisovaleric acid rose to the lesser extent in the CSF perfusate, changes in reusability of the animal and in the EEG recording were demonstrated. 6. It is concluded that all the C-5 acids tested have encephalopathic activity although this is lessened by the presence of either a double bond or an oxygenated functional group.

scholarly journals Ester Dance Reaction on the Aromatic Ring

2019 ◽  
Author(s):  
Kaoru Matsushita ◽  
Ryosuke Takise ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Carbon Atom ◽  
Aromatic Ring ◽  
Functional Group ◽  
State Of The Art ◽  
Palladium Catalysis ◽  
Ester Group ◽  
Halogen Atoms ◽  
Ester Moiety ◽  
Rearrangement Reactions ◽  
Halogen Dance Reaction

Aromatic rearrangement reactions are useful tools in the organic chemist’s toolbox when generating uncommon substitution patterns. However, it is difficult to precisely translocate a functional group in (hetero)arene systems, with the exception of halogen atoms in a halogen dance reaction. Herein, we describe an unprecedented “ester dance” reaction: a predictable translocation of an ester group from one carbon atom to another on an aromatic ring. Specifically, a phenyl carboxylate substituent can be shifted from one carbon to an adjacent carbon on a (hetero)aromatic ring under palladium catalysis to often give a thermodynamically favored, regioisomeric product with modest to good conversions. The obtained ester moiety can be further converted to various aromatic derivatives through the use of classic as well as state-of-the-art transformations including an amidation, acylations and decarbonylative couplings.

scholarly journals The multiple effects of fecal microbiota transplantation on diarrhea-predominant irritable bowel syndrome (IBS-D) patients with anxiety and depression behaviors

2021 ◽  
Vol 20 (1) ◽  
Author(s):  
Hao Lin ◽  
Qingqing Guo ◽  
Zhiyong Wen ◽  
Songlin Tan ◽  
Jie Chen ◽  
...  
Keyword(s):  
Quality Of Life ◽  
Irritable Bowel Syndrome ◽  
Rating Scale ◽  
Isovaleric Acid ◽  
Valeric Acid ◽  
Metagenomic Analysis ◽  
Anxiety And Depression ◽  
Bacterial Invasion ◽  
Irritable Bowel

Abstract Background Anxiety and depression are complications in Irritable bowel syndrome (IBS) patients. In this study, we recruited 18 IBS patients with mild-modest anxiety and depression behaviors, and after the screening, we defined the FMT treatment group (n = 9) and the control group (n = 9). The IBS symptom severity scale (IBS-SSS), Hamilton Anxiety Rating Scale (HAM-A), Hamilton Depression Rating Scale (HAM-D), Irritable Bowel Syndrome Quality of Life (IBS-QOL) and Bristol stool scale (BSS) were evaluated one week before FMT (baseline), one-week-, one-month-, two-month-, and three-month-following FMT. Meanwhile, we determined the SCFAs in the patient’s feces and serum and continued the metagenomic analysis of the microorganisms in the patient’s feces. Results The results showed that the patient’s anxiety and depression behavior gradually improved with FMT treatment. Moreover, the illness and quality of life had also been relieved significantly. The content of isovaleric acid and valeric acid was significantly reduced in the FMT group compared to the Col group. Metagenomic analysis showed that FMT treatment decreased the abundance of Faecalibacterium, Eubacterium and Escherichia. From KEGG functional analysis, we confirmed that the top five abundant pathways were “bacterial chemotaxis, “flagellar assembly”, “glycine, serine and threonine metabolism”, “apoptosis”, and “bacterial invasion of epithelial cells”. Conclusions FMT treatment can effectively alleviate the anxiety and depression behaviors of IBS-D patients and reduce the IBS-SSS score, indicating that FMT can improve patients’ symptoms. The high throughput sequencing results show that Bifidobacterium and Escherichia play the most critical role in the formation and recovery of IBS-D patients. The GC/MS data indicated that faeces isovaleric acid and valeric acid might be more suitable as a metabolic indicator of IBS-D remission. Trial registration ChiCTR, ChiCTR1900024924, Registered 3 August 2019, https://www.chictr.org.cn/showproj.aspx?proj=41676.

scholarly journals Quantitative Charge-Tags for Sterol and Oxysterol Analysis

2015 ◽  
Vol 61 (2) ◽  
pp. 400-411 ◽  
Author(s):  
Peter J Crick ◽  
T William Bentley ◽  
Jonas Abdel-Khalik ◽  
Ian Matthews ◽  
Peter T Clayton ◽  
...  
Keyword(s):  
Cholesterol Synthesis ◽  
Functional Group ◽  
Isotope Labeling ◽  
Jugular Vein ◽  
Solid Phase ◽  
Inborn Errors ◽  
Internal Standards ◽  
Ms Analysis ◽  
Charge Tags ◽  
Prior Oxidation

Abstract BACKGROUND Global sterol analysis is challenging owing to the extreme diversity of sterol natural products, the tendency of cholesterol to dominate in abundance over all other sterols, and the structural lack of a strong chromophore or readily ionized functional group. We developed a method to overcome these challenges by using different isotope-labeled versions of the Girard P reagent (GP) as quantitative charge-tags for the LC-MS analysis of sterols including oxysterols. METHODS Sterols/oxysterols in plasma were extracted in ethanol containing deuterated internal standards, separated by C18 solid-phase extraction, and derivatized with GP, with or without prior oxidation of 3β-hydroxy to 3-oxo groups. RESULTS By use of different isotope-labeled GPs, it was possible to analyze in a single LC-MS analysis both sterols/oxysterols that naturally possess a 3-oxo group and those with a 3β-hydroxy group. Intra- and interassay CVs were <15%, and recoveries for representative oxysterols and cholestenoic acids were 85%–108%. By adopting a multiplex approach to isotope labeling, we analyzed up to 4 different samples in a single run. Using plasma samples, we could demonstrate the diagnosis of inborn errors of metabolism and also the export of oxysterols from brain via the jugular vein. CONCLUSIONS This method allows the profiling of the widest range of sterols/oxysterols in a single analytical run and can be used to identify inborn errors of cholesterol synthesis and metabolism.

scholarly journals Evaluation of Aroma in Oriental Tobaccos as Based On Valeric Acid Gas Chromatography

2008 ◽  
Vol 23 (2) ◽  
pp. 115-120 ◽  
Author(s):  
S Dagnon ◽  
R Tasheva ◽  
A Stoilova ◽  
D Christeva ◽  
A Edreva
Keyword(s):  
Gas Chromatography ◽  
Acid Content ◽  
Regression Models ◽  
Isovaleric Acid ◽  
Valeric Acid ◽  
Ionization Detector ◽  
Chemical Marker ◽  
Acid Gas ◽  
Flame Ionization ◽  
Aroma Characteristics

AbstractLevels of valeric acids (isovaleric and 3-methylvaleric) in leaves and smoke of different tobacco types were quantified by capillary gas chromatography (GC) using flame ionization detector (FID). The aroma characteristics of the smoke were scored by sensory evaluation. It was found that leaves of Oriental and burley tobaccos contain higher amounts of both valeric acid derivatives than Virginia tobaccos containing isovaleric acid but no 3-methylvaleric acid. Strong correlation between the aroma and pleasantness scores of smoke and the content of valeric acids in the leaves of Oriental tobaccos was observed, while it was not the case for leaves of Virginia and burley tobaccos. In all tobacco types no correlation between smoking characteristics and the content of valeric acids in the smoke was established. Regression models involving leaf isovaleric acid were developed that can be used to evaluate aroma and pleasantness of smoke in Oriental tobaccos. The data obtained allow the following conclusions to be drawn: a) 3-methylvaleric acid may be a chemical marker to distinguish Virginia tobaccos from Oriental and burley tobaccos; b) isovaleric acid content in leaves of Oriental tobaccos may be used for objective aroma evaluation that can be exploited for breeding and market purposes.

Le radical méthylènecyclopropyle: étude théorique. Chloration par t-BuOCl et réduction par (nBu)3SnH de dérivés cyclopropéniques

1985 ◽  
Vol 63 (9) ◽  
pp. 2511-2521 ◽  
Author(s):  
R. Arnaud ◽  
S. Choubani ◽  
R. Subra ◽  
M. Vidal ◽  
M. Vincens ◽  
...  
Keyword(s):  
Double Bond ◽  
Carbon Atom ◽  
Ring Opening ◽  
Functional Group ◽  
Theoretical Study ◽  
Reduction Process ◽  
Trans Position ◽  
Tertiary Alcohols ◽  
Abstraction Reaction ◽  
Allylic Radical

The allylic chlorination of ethyl 2,3-dialkyl 2-cyclopropenecarboxylate or primary and tertiary alcohols is highly regio- and stereoselective. The halogenated methylenecyclopropane derivative only is observed. In that compound, the halogen substituent and the functional group are in a trans position with respect to the ring. The halogenated allylic compounds of methylenecyclopropane and of cyclopropene undergo reduction by (nBu)3SnH with the same stereochemistry. Products arising from ring opening are also observed. The exocyclic migration of the double bond can be related to the formation of a transient allylic radical. A theoretical study performed within the MNDO (UHF and RHF) framework leads to a planar allylic radical, whatever the substituent. The radical abstraction reaction which takes place during the reduction process is easier for a cyclic carbon atom than for an exocyclic one. In the former case, the faster reaction is obtained for a chlorinated carbon atom.

One-pot Synthetic Approaches for the Construction of Isochroman-4-ones and Benzoxazin-3-ones Using O,P-Acetals

Synthesis ◽  
2021 ◽  
Author(s):  
Akira Nakamura ◽  
Kouhei Yamamoto ◽  
Ryo Murakami ◽  
Norihito Kawashita ◽  
Kouichi Matsumoto ◽  
...  
Keyword(s):  
Carbon Atom ◽  
Intramolecular Cyclization ◽  
Heterocyclic Compounds ◽  
Functional Group ◽  
Methylene Carbon ◽  
One Pot ◽  
Methylene Carbon Atom ◽  
Synthetic Approaches ◽  
Sequential Reactions

A method for synthesizing six-membered heterocyclic compounds was developed based on the features of O,P-acetals. Sequential reactions of intramolecular cyclization between the methylene carbon atom of O,P-acetal and its electrophilic functional group (ester or protected carbamate) was followed by Horner-Wadsworth-Emmons (HWE) olefination with various aldehydes. The developed one-pot method yielded isochroman-4-one and benzoxazin-3-one derivatives with an alkylidene moiety.

scholarly journals Ester dance reaction on the aromatic ring

2020 ◽  
Vol 6 (28) ◽  
pp. eaba7614
Author(s):  
Kaoru Matsushita ◽  
Ryosuke Takise ◽  
Kei Muto ◽  
Junichiro Yamaguchi
Keyword(s):  
Carbon Atom ◽  
Aromatic Ring ◽  
Functional Group ◽  
State Of The Art ◽  
Palladium Catalysis ◽  
Ester Group ◽  
Halogen Atoms ◽  
Ester Moiety ◽  
Rearrangement Reactions ◽  
Halogen Dance Reaction

Aromatic rearrangement reactions are useful tools in the organic chemist’s toolbox when generating uncommon substitution patterns. However, it is difficult to precisely translocate a functional group in (hetero) arene systems, with the exception of halogen atoms in a halogen dance reaction. Here, we describe an unprecedented “ester dance” reaction: a predictable translocation of an ester group from one carbon atom to another on an aromatic ring. Specifically, a phenyl carboxylate substituent can be shifted from one carbon to an adjacent carbon on a (hetero) aromatic ring under palladium catalysis to often give a thermodynamically favored, regioisomeric product with modest to good conversions. The obtained ester moiety can be further converted to various aromatic derivatives through the use of classic and state-of-the-art transformations including amidation, acylations, and decarbonylative couplings.

scholarly journals Long-Term Aerosol Trends and Variability over Central Saudi Arabia Using Optical Characteristics from Solar Village AERONET Measurements

Atmosphere ◽  
2019 ◽  
Vol 10 (12) ◽  
pp. 752 ◽  
Author(s):  
Mohammed Al Otaibi ◽  
Ashraf Farahat ◽  
Bassam Tawabini ◽  
M. Hafidz Omar ◽  
Emad Ramadan ◽  
...  
Keyword(s):  
Saudi Arabia ◽  
Low Frequency ◽  
Radiation Budget ◽  
Optical Parameters ◽  
Anthropogenic Aerosols ◽  
Hysplit Model ◽  
Pronounced Increase ◽  
Local Emissions ◽  
Network Station

Natural and anthropogenic aerosols over the Kingdom of Saudi Arabia (KSA) play a major role in affecting the regional radiation budget. The long-term variability of these aerosols’ physical and optical parameters, including aerosol optical depth (AOD) and Ångström exponent (α), were measured at a location near central KSA using the Solar Village (SV) AERONET (Aerosol Robotic Network) station during the period December 1999–January 2013. The AERONET measurements show an overall increase in AOD on an annual basis. This upward trend is mainly attributed to a prolonged increase in the monthly/seasonal mean AOD during March–June and during August–September. In contrast, lower AOD values were observed during November–December. This can be attributed to a low frequency of dust outbreaks and higher precipitation rates. An overall, weak declining trend in α was observed, except during the summer. The spring and summer seasons experienced a pronounced increase in the number of coarse particles (~2 µm) during April 2006–January 2013 as compared to December 1999–March 2006, suggesting an increase in natural aerosol loadings. Using the HYSPLIT model, it was found that the March 2009 dust storm contributed to the mixing of long-transported dust with anthropogenic local emissions near the SV. The results suggest that extensive industrial activity contributed to the increase of anthropogenic emissions over KSA during the period April 2006–January 2013.

A Brief Discussion on Nucleophilic Substitution Reaction on Saturated Carbon Atom

2013 ◽  
Vol 312 ◽  
pp. 433-437 ◽  
Author(s):  
Yan Ding
Keyword(s):  
Reaction Mechanism ◽  
Carbon Atom ◽  
Nucleophilic Substitution ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Substitution Reaction ◽  
Functional Group ◽  
Hydrolysis Reaction ◽  
Nucleophilic Substitution Reaction ◽  
Saturated Carbon Atom

Nucleophilic substitution reaction is an important reaction of haloalkane. By such a reaction, halogen functional group can turn into various other functional groups. Therefore, it is widely used in organic synthesis and there are many researches on its reaction mechanism. Hydrolysis reaction of bromoalkane is especially a nucleophilic substitution reaction that is studied quite fully. This paper mainly discusses the nucleophilic substitution reaction on saturated carbon atom.

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