scholarly journals Microbiological degradation of bile acids. The preparation of hexahydroindane derivatives as substrates for studying cholic acid degradation

1977 ◽  
Vol 164 (3) ◽  
pp. 709-714 ◽  
Author(s):  
S Hayakawa ◽  
T Takata ◽  
T Fujiwara ◽  
S Hashimoto
Keyword(s):  
Carboxylic Acid ◽  
Cholic Acid ◽  
Propionic Acid ◽  
Good Yield ◽  
Degradation Products ◽  
Chemical Oxidation ◽  
Compound Iiib ◽  
Partial Synthesis ◽  
Arthrobacter Simplex ◽  
Simple Method

Relatively large amounts of 3-(3aalpha-hexahydro-7abeta-methyl-1,5-dioxoindan-4alpha-yl)propionic acid (IIb), which is believed to be one of the intermediates involved in the degradation of cholic acid (I), were needed to identify is further degradation products. A simple method for the preparation of this compound was then investigated. Arthrobacter simplex could degrade-3-oxoandrost-4-ene-17beta-carboxylic acid (IIIa) to 3-(1beta-carboxy-3aalpha-hexahydro-7abeta-methyl-5-oxoindan-4alpha-yl)propionic acid (IVa) in good yield, the structure of which was established by partial synthesis. It was therefore expected that, if a similar degradation by this organism occurred with 17alpha-hydroxy-3-oxoandrost-4-ene-17beta-carboxylic acid (IIIb), which is easily obtained by chemical oxidation of commercially availabe 17alpha-hydroxydeoxycorticosterone, the resulting product, 3-(1beta-carboxy-3aalpha-hexahydro-1alpha-hydroxy-7abeta-methyl-5-oxoindan-4alpha-yl)propionic acid (IVb), could be readily converted chemically into the required dioxocarboxylic acid, (IIb). Exposure of compound (IIIb) to A. simplex produced, as expected, compound (IVb) which was then oxidized with NaBiO3 to give a reasonable yield of compound (IIb).

scholarly journals Microbiological degradation of bile acids. The preparation of some hypothetical metabolites involved in cholic acid degradation

1976 ◽  
Vol 154 (3) ◽  
pp. 577-587 ◽  
Author(s):  
S Hayakawa ◽  
Y Kanematsu ◽  
T Fujiwara ◽  
H Kako
Keyword(s):  
Fatty Acid ◽  
Carboxylic Acid ◽  
Bile Acids ◽  
Cholic Acid ◽  
Valeric Acid ◽  
Side Chain ◽  
Partial Synthesis ◽  
Arthrobacter Simplex ◽  
Acid Degradation ◽  
Oxidation Mechanisms

1. To identify the intermediates involved in the degradation of cholic acid, the further degradation of (4R)-4-[4a-(2-carboxyethyl)-3aa-hexahydro-7ab-methyl-5-oxoindan-1β-yl]valeric acid (IVa) by Arthrobacter simplex was attempted. The organism could not utilize this acid but some hypothetical intermediate metabolities of compound (IVa) were prepared for later use as reference compounds. 2. The nor homologue (IIIa) and the dinor homologue (IIIb) of compound (IVa) were prepared by exposure of 3-oxo-24-nor-5β-cholan-23-oic acid (I) and (20S)-3b-hydroxy-5-pregnene-20-carboxylic acid (II) to A. simplex respectively. These compounds correspond to the respective metabolites produced by the shortening of the valeric acid side chain of compound (IVa) in a manner analogous to the conventional fatty acid a- and b-oxidation mechanisms. Their structures were confirmed by partial synthesis. 3. The following authentic samples of reduction products of the oxodicarboxylic acids (IIIa), (IIIb) and (IVa) were also synthesized as hypothetical metabolities: (4R)-4-[3aa-hexahydro-5a-hydroxy-4a-(3-hydroxypropyl)-7ab-methylindan-1b-yl]valeric acid (Vb) and its nor homologue (VIIa) and dinor homologue (IXa);(4R)-4-[3Aaa-hexahydro-5a-hydroxy-4a-(3-hydroxypropyl)-7ab-methylindan-1b-yl]-pentan-1-ol (Vc); and their respective 5β epimers (Ve), (VIIc), (IXc) and (Vf). 4. In connexion with the non-utilization of compound (IVa) by A. simplex, the possibility that not all the metabolites formed from cholic acid by a certain micro-organism can be utilized by the same organism is considered.

scholarly journals Microbiological degradation of bile acids. Ring a cleavage and 7α,12α-dehydroxylation of cholic acid by Arthrobacter simplex

1969 ◽  
Vol 115 (2) ◽  
pp. 249-256 ◽  
Author(s):  
Shohei Hayakawa ◽  
Yoshiko Kanematsu ◽  
Takashi Fujiwara
Keyword(s):  
Bile Acids ◽  
Cholic Acid ◽  
Valeric Acid ◽  
Hydroxyl Groups ◽  
Partial Synthesis ◽  
Arthrobacter Simplex ◽  
Degradative Pathway ◽  
Acid Degradation

The metabolism of cholic acid by Arthrobacter simplex was investigated. This organism effected both ring a cleavage and elimination of the hydroxyl groups at C-7 and C-12 and gave a new metabolite, (4R)-4-[4α-(2-carboxyethyl)-3aα-hexahydro-7aβ-methyl-5-oxoindan-1β-yl]valeric acid, which was isolated and identified through its partial synthesis. A degradative pathway of cholic acid into this metabolite is tentatively proposed, and the possibility that the proposed pathway could be extended to the cholic acid degradation by other microorganisms besides A. simplex is discussed. The possibility that the observed reactions in vitro could occur during the metabolism of bile acids in vivo is considered.

Esterification of Alkene with Cerium(IV) Sulfate in Carboxylic Acid

2003 ◽  
Vol 2003 (5) ◽  
pp. 270-272 ◽  
Author(s):  
C. Akira Horiuchi ◽  
Tomoaki Fukushima ◽  
Noriyuki Furuta ◽  
Wen Chai ◽  
Shun-Jun Ji ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Formic Acid ◽  
Carboxylic Acids ◽  
Propionic Acid ◽  
Addition Reaction ◽  
Simple Method ◽  
Markovnikov Rule ◽  
Carboxylic Esters

Reaction of alkenes [cyclohexene (1), cycloheptene (2), cyclooctene (3), 1-heptene (4), 1-octene (5), styrene (6), 1,7-octadiene (7), indene (8), and 1,2-dihydronaphthalene (9)] with cerium(IV) sulfate (CS) in carboxylic acids [formic acid, acetic acid, and propionic acid] readily yielded the corresponding carboxylic esters. This addition reaction follows the Markovnikov rule. This reaction provides a new simple method for preparing carboxylic esters from alkenes. It was also found that this method is useful for formylation.

scholarly journals Microbiological degradation of bile acids, further degradation of a cholic acid metabolite containing the hexahydroindane nucleus by Corynebacterium equi

1977 ◽  
Vol 162 (2) ◽  
pp. 387-397 ◽  
Author(s):  
S Hayakawa ◽  
T Fujiwara
Keyword(s):  
Cholic Acid ◽  
Propionic Acid ◽  
Metabolic Pathways ◽  
Ring Opening ◽  
Initial Step ◽  
Valeric Acid ◽  
Acid Metabolite ◽  
Partial Synthesis ◽  
Initial Oxidation ◽  
Dioic Acid

1. The further degradation of a cholic acid (I) metabolite, (4R)-4-[4alpha-(2-carboxyethyl)-3aalpha-hexahydro-7abeta-methyl-5-oxoindan-1beta-yl]valeric acid (IIa), by Corynebacterium equi was investigated. This organism effected ring-opening and gave (4R)-4-[2alpha-(2-carboxyethyl)-3beta-(3-carboxypropionyl)-2beta-methylcyclopent-1beta-yl]valeric acid (VI). The new metabolite was isolated as its trimethyl ester and identified by partical synthesis. It was not utilized by C. equi. 2. (4R)-4[4alpha-(2-Carboxyethyl)-3aalpha-decahydro-8abeta-methyl5-oxa-6-oxoazulen-1beta-yl]valeric acid (IVa), which is a hypothetical initial oxidation product in the above degradation, was not converted by C. equi into the expected metabolite (VI), but into 3 - [2beta - [(2S) - tetrahydro - 5 - oxofur - 2 - yl] - 1beta - methyl - 5 - oxocyclopent - 1alpha - yl]-propionic acid (VIII), the structure of which was established by partial synthesis. 3. Both the possible precursors of the metabolite (VI), an isomer of the epsilon-lactone (IVa), the gamma-lactone (XIa), and the open form of these lactones, the hydroxytricarboxylic acid (V), were also not utilized by C. equi. 4. Under some incubation conditions, C. equi also converted compound (IIa) and 3-(3aalpha-hexahydro-7abeta-methyl-1,5-dioxoindan-4alpha-yl)propionic acid (IIb) into 5-methyl-4-oxo-octane-1,8-dioic acid (III), (4R)-4-(2,3,4,6,6abeta,7,8,9,9aalpha,9bbeta-decahydro-6abeta-methyl-3-oxo-1H-cyclopenta[f]quinolin-7beta-yl)valeric acid (VII) and probably a monohydroxy derivative of compound (IIa) and compound (III), respectively. 5. The possibility that an initial step in the degradation of compound (IIa) by C. equi is oxygenation of the Baeyer-Villiger type, yielding compound (IVa), is discussed. Metabolic pathways of compound (IIa) to compounds (III), (VI), (VII) and (VIII) are also considered.

Development and validation of a fast and simple HPLC method for the simultaneous determination of aniline and its degradation products in wastewater

2016 ◽  
Vol 8 (30) ◽  
pp. 5949-5956 ◽  
Author(s):  
Soumia Boulahlib ◽  
Ali Boudina ◽  
Kahina Si-Ahmed ◽  
Yassine Bessekhouad ◽  
Mohamed Trari
Keyword(s):  
High Performance ◽  
Degradation Products ◽  
Reversed Phase ◽  
Hplc Method ◽  
Array Detector ◽  
Simple Method ◽  
Photodiode Array Detector ◽  
Photodiode Array ◽  
Development And Validation

In this study, a rapid and simple method based on reversed-phase high performance liquid chromatography (RP-HPLC) using a photodiode array detector (PDA) for the simultaneous analysis of five pollutants including aniline and its degradation products, para-aminophenol, meta-aminophenol, ortho-aminophenol and phenol, was developed.

Novel, simple method for the preparation of 7-hydroxy-4-phenylquinoline-2-carboxylic acid

2010 ◽  
Vol 46 (3) ◽  
pp. 358-360 ◽  
Author(s):  
V. O. Kozminykh ◽  
E. A. Kirillova ◽  
I. N. Nozdrin ◽  
O. N. Dvorskaya ◽  
E. N. Kozminykh
Keyword(s):  
Carboxylic Acid ◽  
Simple Method

A Simple Synthesis of 4-Substituted 2-(3-Hydroxy-2-oxo-1-phenethylpropylcarbamoyl) pyrrolidine-1-carboxylic Acid Benzyl Esters as Novel Cysteine Protease Inhibitors

2008 ◽  
Vol 63 (2) ◽  
pp. 210-216 ◽  
Author(s):  
Seikwan Oh ◽  
Jae-Chul Jung ◽  
Mitchell A. Avery
Keyword(s):  
Carboxylic Acid ◽  
Protease Inhibitors ◽  
Cysteine Protease ◽  
Good Yield ◽  
Sodium Acetate ◽  
Simple Synthesis ◽  
Insertion Reaction ◽  
Cysteine Protease Inhibitors ◽  
Convenient Synthesis ◽  
Benzyl Esters

A convenient synthesis of 4-substituted 2-(3-hydroxy-2-oxo-1-phenethylpropylcarbamoyl)pyrrolidine- 1-carboxylic acid benzyl esters 17 and 18 as new cysteine protease inhibitors is described. The synthetic key strategies involve the diazocarbonyl insertion reaction of N-Boc-L-homophenylalanine (1) by diazomethane, acetylation of the bromoketone 2 with sodium acetate, and condensation of acids 12, 14 with (3S)-3-amino-2-oxo-5-phenyl-pentyl acetate monohydrochloride (4) in good yield

scholarly journals DEVELOPMENT AND VALIDATION OF STABILITY INDICATING RP-HPLC METHOD FOR DETERMINATION OF β-ACETYLDIGOXIN

2016 ◽  
Vol 9 (1) ◽  
pp. 54
Author(s):  
Megha Sharma ◽  
Neeraj Mahindroo
Keyword(s):  
High Performance ◽  
Degradation Products ◽  
Hplc Method ◽  
Stability Study ◽  
Array Detector ◽  
Forced Degradation ◽  
Simple Method ◽  
Stability Indicating ◽  
Rp Hplc

Objective: The objective of the present study was to develop and validate a novel stability indicating reverse phase-high performance liquid chromatography (RP-HPLC) method for determination of β-acetyldigoxin, an active pharmaceutical ingredient (API).Methods: The chromatographic separation was carried out on Agilent Technologies 1200 series HPLC system equipped with photo diode array detector and C-18 (4.6x250 mm, 5 µ) column. The mobile phase consisted of water: acetonitrile (65:35 v/v), delivered at a flow rate of 1.5 ml/min and eluents were monitored at 225 nm.Results: The retention time of β-acetyldigoxin was 9.2 min. The method was found to be linear (R2= 0.9995) in the range of 31.25-500 µg/ml. The accuracy studies showed the mean percent recovery of 101.02%. LOD and LOQ were observed to be 0.289 µg/ml and 0.965 µg/ml, respectively. The method was found to be robust and system suitability testing was also performed. Forced degradation analysis was carried out under acidic, alkaline, oxidative and photolytic stress conditions. Significant degradation was observed under tested conditions, except for oxidative condition. The method was able to separate all the degradation products within runtime of 20 min and was able to determine β-acetyldigoxin unequivocally in presence of degradation products.Conclusion: The novel, economic, rapid and simple method for analysis of β-acetyldigoxin is reported. The developed method is suitable for routine quality control and its determination as API, and in pharmaceutical formulations and stability study samples.

scholarly journals Improved Method for the Determination of Anatoxin-a and Two of Its Metabolites in Blue-Green Algae Using Liquid Chromatography with Fluorescence Detection

2005 ◽  
Vol 88 (6) ◽  
pp. 1741-1747 ◽  
Author(s):  
Dorothea F K Rawn ◽  
Benjamin P-Y Lau ◽  
Barbara Niedzwiadek ◽  
James F Lawrence
Keyword(s):  
Liquid Chromatography ◽  
Green Algae ◽  
Fluorescence Detection ◽  
Background Noise ◽  
Degradation Products ◽  
Food Supplements ◽  
Primary Amines ◽  
Algal Toxins ◽  
Simple Method ◽  
Blue Green Algae

Abstract Anatoxin-a, a neurotoxin produced by blue-green algae (BGA) species, can cause death to exposed organisms. In North America, BGA are harvested and sold as food supplements, some of which contain elevated levels of other algal toxins, such as microcystins. Concern that elevated levels of anatoxin-a also may be present in BGA food supplements has led to the development of a simple method to determine the presence of anatoxin-a in BGA. Some researchers have successfully analyzed this compound using liquid chromatography with fluorescence detection by forming a fluorescent derivative with 4-fluoro-7-nitrobenzofurazan (NBD-F) in water and phytoplankton extracts. With this method, the background noise is high in BGA extracts due to the presence of co-extractives. Addition of o-phthaldialdehyde (OPA) and mercaptoethanol to the extract before addition of the NBD-F resulted in the successful removal of primary amines from the background noise when the NBD-F derivatives were detected with fluorescence. Improved chromatograms were obtained when extracts were cleaned up in this manner, leading to a lower detection limit (approximately 50 μg/kg) for anatoxin-a. The detection limits obtained for the 2 degradation products dihydroanatoxin-a and epoxyanatoxin-a in BGA extracts were similarly low (55 and 65 μg/kg, respectively).

ChemInform Abstract: Novel, Simple Method for the Preparation of 7-Hydroxy-4-phenylquinoline-2-carboxylic Acid.

ChemInform ◽  
2010 ◽  
Vol 42 (1) ◽  
pp. no-no
Author(s):  
V. O. Kozminykh ◽  
E. A. Kirillova ◽  
I. N. Nozdrin ◽  
O. N. Dvorskaya ◽  
E. N. Kozminykh
Keyword(s):  
Carboxylic Acid ◽  
Simple Method
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