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[Studies on chemical constituents from Euphorbia fischeriana Steud].

OBJECTIVE: To study the chemical constituents of ethanol extract from dried roots of Euphorbia fischeriana. METHOD: Compounds were separated by column chromatography with silca gel and elucidated by chemical evidence and spectral analysis. RESULT: Isobauerenyl acetate, beta-amyrin acetate, 24-methylenecycloartenone,octacosyl ferulate and 2,4-dihydroxy-6-methoxy-3-methyl acetophenone were isolated and elucidated. CONCLUSION: All the compounds were isolated from the plant for the first time.

Acetates↗

[LDH and structural analogues of pyruvate (author's transl)].

Pyruvate related compounds have been tested for their active or inhibitory properties on LDH. Special structure features were needed for compounds to be bound to the enzyme active site. Pyruvate and the LDH molecule were bound by the interaction of the carboxyl group or its ester derivative, with the enzyme. Ethyl pyruvate seemed to behave as a substrate of the enzyme whereas acetophenone, ethyl acetoacetate and beta-oxoglutarate did not act as substrates or inhibitors of LDH. Phenyl pyruvate, alpha-oxoglutarate and L-mandelate are not substrates but inhibitors of the LDH. It seems that a structure having a carbonyl group in the alpha-position to the carboxyl is required for the binding of a compound to the LDH molecule. Glyoxylate alpha-oxobutyrate and alpha-oxovalerianate appear to be worse LDH substrates than pyruvate itself. This seems to suggest that the shortening or the extension of the pyruvate aliphatic chain induces a decrease of the affinity of the enzyme towards their substrate homologues.

Animals↗

Fragments formed by the side chain cleavage of a 20-aryl analog of 20alpha-hydroxycholesterol by adrenal mitochondria.

An analog of 20alpha-hydroxycholesterol, (20R)-20-phenyl-5-pregnene-3beta,20-diol, which is completely substituted at C-22 was prepared with radioisotopes at various positions. The analog labeled with 3H at C-M and 14C at C-4 and C-IU was converted into radioactive pregnenolone by an enzyme preparation derived from adrenal mitochondria. Cleavage of the phenyl analog labeled with 3H in the aromatic ring by the same enzyme preparation led to the formation of [3H]phenol. Using the substrate doubly labeled with 14C at C-4 and 3H in the aromatic ring, it appeared that the products of the reactions, pregnenolone and phenol, were formed in equal amounts. During incubation of the side chain labeled substrate, another labeled fragment was formed. It was identified as acetophenone, a product resulting from cleavage of the C17,20 bond. The steroidal fragment corresponding to this C8 ketone was traced using nuclear label analog. From its nonpolar chromatographic properties it appears to be a C-17-deoxy-C19 steroid.

Adrenal Medulla↗

[Application of high resolution mass spectra to the analysis of alpha-thiocarbonylthioformamides].

Acetophenone and its derivatives reacted on thionyl chloride to form an intermediate, which can react on the secondary aminnes to form alpha-carbonylthioformamides (1a-1f), followed by sulfurization with lawesson reagent to give target compounds alpha-thiocarbonylthioformamides (2a-2f). Compounds 2a-2f are the deep-red or deep-green crystals because there are two thiocarbonyl groups in the molecule, and they can be used as far-infraed adsorbent dyes, laser-Q switch and organic conductors. Moreover, they are very important intermediates, can react on reagents with amino or diamino groups to produce a variety of acyclic or heterocyclic compounds, which can be used as pesticides and medicines. Therefore, it is necessary to develop a new method for the analysis of alpha-thiocarbonylthioformamides (2a-2f). OA-TOF high resolution mass spectrometer is suitable to do this because of its small volume, high speed and giving elemental composition of ions. In this paper, the mass fragmentation pattern of alpha-thiocarbonylthioformamides was studied in detail using OA-TOF high resolution mass spectrometer of Micromass. The results showed that the molecular ions appeared, then, a neutral molecule S2 was lost easily from the molecular ion of alpha-thiocarbonylthioformamides, forming a particular ion M-S2 (base peak). This provides an effective method for the analysis of these compounds.

English Abstract↗

[Schiff base type onno spectrophotometric determination of magnesium].

By condensing hydrazide salicylic acid with o-hydroxy carbonilic compounds it was obtained 2--hydroxy acetophenon--salicyl hidrazina, Schiff base--type ONNO. These Schiff bis bases present a good capacity of complexing the Mg (II) ions. The above mentioned Schiff base forms complex with Mg (II) cation, with maximum absorbance at 386 nm, and molar absorbtivity (epsilon) = 6.27 x 10(4) mol-1.L.cm-1. The complex with Mg (II) presents a maximum stability at pH = 9.6 - 10.0. The calculated apparent stability constant is K = 3.18 x 10(3). The absorbance is proportional to Mg (II) concentration in the range of 10-60 mg/mL. In this range, the Lambert--Beer law is respected, the linearity coefficient being 0.9818, SD = 0.83, RSD = 0.84 (n = 6). The results obtained for spectrophotometric determination of Mg (II) using this Schiff base as reagent were successfully applied to pharmaceutical products containing Mg (II) cation.

Algorithms↗

Phenolic sodium sulphates of Frankenia laevis L.

Four new phenolic anionic conjugates have been isolated from the whole plant aqueous alcohol extract of Frankenia laevis L. Their structures were established, mainly on the basis of ESI-MS, 1D and 2D NMR spectroscopic evidence, as gallic acid-3-methyl ether-5-sodium sulphate, acetophenone-4-methyl ether-2-sodium sulphate, ellagic acid-3,3'-dimethyl ether-4,4'-di-sodium sulphate and ellagic acid-3-methyl ether-4-sodium sulphate.

Chromatography, Paper↗

Further characterization of monoclonal antibody indicates specificity for (6-4)-dipyrimidine photoproducts.

Monoclonal antibody aUVssDNA-1 is produced by hybridoma cell line 25JF.C3B6 originally selected from cell fusions using spleen cells from mice immunized with UV-irradiated polydeoxynucleotides (Strickland and Boyle, Photochem. Photobiol. 34, 595-601, 1981). Original and subsequent studies of the binding characteristics of aUVssDNA-1 indicated that it was specific for cyclobuta-dithymidine photoproducts. Those investigations examined action spectrum, short-wavelength photo-reversal, nucleotide sequence effects, and photoreactivation using E. coli photolyase and incandescent light. However, the more recent studies reported here examined acetophenone-UV-B photosensitization, UV-B photoisomerization, and photoreactivation using cloned E. coli photolyase and filtered incandescent light. The results indicate that aUVssDNA-1 recognizes photoproducts with characteristics of (6-4)-dipyrimidines. Thus, previous studies in which relatively rapid repair of cyclobuta-dithymidine photoproducts was inferred using this antibody, require re-interpretation in light of these new findings.

Animals↗

[Studies on the chemical constituents from the aerial parts of Breynia fruticosa].

OBJECTIVE: To investigate the chemical constituents from the aerial parts of Breynia fruticosa. METHOD: Various chromatographic techniques were employed for isolation and purification of the constituents. The structures were elucidated by chemical evidence and spectral methods. RESULT: Seven compounds were obtained and identified by spectroscopic methods and compared with authentic samples as aviculin [(+)-isolariciresinol-9'-rhamno-pyranoside], friedelan-3beta-ol, friedelin, arborinone, isoarborinol, 5-hydroxy-7,8,4'-trimethoxy flavone, 2,4-dihydroxy-6-methoxy-3-methyl-acetophenone. CONCLUSION: All compounds were firstly isolated from B. genus, furthermore, aviculin was isolated from Euphorbiaceae for the first time.

Euphorbiaceae↗

[Synthesis and antitumor activity of arylsubstituted imidazolin-2-one derivatives].

AIM: To design and synthesize new arylsubstituted imidazolin-2-one analogues as antitumor compounds. METHODS: Arylsubstituted imidazolin-2-ones were prepared by condensation the appropriate omega-amino-acetophenone hydrochloride with arylisocyanate in toluene. The target compounds prepared in this study were tested for cytotoxicity against PC-3, A549, HO-8910, Hela, HL60, K562 and HL60R cancer cell lines, and mechanism of one of the products 4y was further evaluated with its mechanium. RESULTS: Thirty-six new compounds were synthesized and confirmed by 1H NMR, MS and elemental analysis. One of the synthesized products, compound 4y, displayed an encouraging selective activity against HL60 cells, and it was partlydue to the cell cycle arrest and cell apoptosis. CONCLUSION: Compound 4y is worthy to be intensively studied.

Amides↗

[Binding of aromatic compounds to cornstarch polysaccharides].

Sorption of aromatic compounds from aqueous solutions by cryotextures and suspensions of native cornstarches was studied by capillary gas chromatography. Acetophenone and benzyl alcohol were not sorbed by cryotropic-cornstarch gel and native-cornstarch suspension. A linear concentration dependence was found for aldehydes. Phenylethyl alcohol was characterized by a nonlinear concentration dependence. The presence of a benzene ring contributed to decreased binding (relative to the level characteristic of aliphatic compounds). The degree of binding depended considerably on the type of functional group in the aromatic compounds. Cryotextures were more potent than granules of native cornstarch in binding aromatic compounds.

Adsorption↗

[Comparative evaluation of health hazards associated with industrial chemicals and their derivates forming during water chlorination].

Many industrial chemicals found in waste waters are able to form organochlorine by-products during water disinfection. The transformation of seven model compounds, cyclohexene, n-butanol, diphenylmethane, acetophenone, aniline, 1-methylnaphthalene, and phenylxylylethane during a reaction with active chlorine was studied. Aqueous chlorine and sodium hypochlorite were used as chlorinating agents. The products of the reaction were analyzed by means of chromatomass-spectrometry. A schematic model of diphenylmethane transformation was proposed. Comparative evaluation of hazards associated with the model chemicals and their derivates confirmed that chlorination products can be more toxic and dangerous than the initial compounds, and may possess mutagenic and cancerigenic properties.

Aminophenols↗

Studies on breeding of antibiotic-producing strain 5102 by protoplast fusion. IV: Verification of fusant FR-008, and isolation and characterization of the new antimicrobial substance.

On the basis of the high performance liquid chromatography (HPLC) of Antibiotic 5102-1, the principal components of this antibiotic were isolated from the cultures of starting strain 10-22 and the fusant FR-008. The result further verified that FR-008 was a recombinant of intraspecific fusion of Streptomyces hygroscopicus subsp. yingchengensis. A new antimicrobial substance was isolated and purified from the fermented product of fusant FR-008, which could not be produced by the starting strain. The color reactions of the new substance with concentrated sulphuric acid or concentrated hydrochloric acid and the UV-VIS absorptions indicated that it was a haptene macrolide antibiotic. The liquid chromatography for aromatic moiety showed that this antibiotic contained p-amino-acetophenone moiety. The amino acid analysis of the antibiotic revealed that it contained an aminosugar moiety, which was different from that in any other haptene macrolide antibiotic. The detailed chemical structure of the aminosugar moiety has yet to be identified.

Anti-Bacterial Agents↗

[Epidemiological studies on the manufacture of cross-linked polyethylene].

In the production of cross-linked polyethylene in the air of the working environment above the norm concentrations of acetophenon, dicumyl peroxide and antioxidant are established, which create unfavourable working conditions. During clinical and laboratory examinations of 55 workers, engaged in the production of cross-linked polyethylene, are registered subjective complaints from the irritating effect of the chemical noxae on the mucous membranes and skin. Methaemoglobinaemia is found in 4 workers. There are deviations in the functional state of the liver (transaminase, APh, GGTP and triglycerides) in the group "maintaining staff". The same workers have also increased quantity of metabolite hippuric acid in the urine. On the grounds of the results, the group "maintaining staff" is determined as risk group. Recommendations are made for follow-up care and work in controlled parameters of the working environment.

Air Pollutants, Occupational↗

[Synthesis of the highly cardioselective beta-sympatholytic pacrinolol].

The synthesis is described of the enantiomerically pure (-)-3-(3,4-dimethoxyphenylethylamino)-2-hydroxypropoxy] phenyl]-cis-crotonic acid nitrile (13b) (free base) and its hydrochloride (13c) (pacrinolol, Hoe 224 A) starting from p-hydroxyacetophenone (1) and racemic epichlorohydrin (2). The p-(2,3-oxidopropoxy)acetophenone (2) resulting from this reaction is C-homologisized to (8); reactions of this with homoveratrylamine (9) leads to (10a), the racemic structural analog of (13b). Resolution of the racemate is achieved by fractional crystallisation of the diastereoisomeric mandelates (13a) and (14a) to afford the enantiomerically pure title compound (13c) and its dextrarotatory optical antipode (14c). Structural confirmation of (13b) and (13c) was achieved through physicochemical and spectroscopic data especially from the 1H-NMR- and MS-spectra. Pacrinolol (13c) is a highly cardioselective beta-sympathicolytic with significant and long acting blood pressure lowering properties (intravenous and oral in the dog).

Adrenergic beta-Antagonists↗

Synthesis of new quinoline derivatives as antimicrobial agents.

2-Hydroxyquinoline-4-hydrazide was condensed with some aromatic aldehydes and acetophenones to give the hydrazones 1a-h. It was also reacted with HCOOH, PhCOCl and p-CH3O-PhCOCl to afford 2a-c. Cyclization of 2b was completed by using PPA, POCl3 and/or P2S5, which gave compounds 3, 4, and 6 respectively. Reaction of 4 with some amines gave the corresponding derivatives 5a-f. The thiosemicarbazide 7 was cyclized under acid and basic condition to give the thiadiazolyl-8 and triazolyl-10 derivatives.

Anti-Bacterial Agents↗

Liquid chromatographic determination of carbofuran in technical and formulated products: collaborative study.

A liquid chromatographic (LC) method for the analysis of technical and formulated carbofuran samples was evaluated in a collaborative study. Carbofuran is determined by reverse phase LC, using a water-methanol mobile phase and acetophenone as internal standard, and detected at 280 nm. Twelve samples, 5 formulations and technical matched pairs, were analyzed by 17 collaborating laboratories. Accuracy and variability of results are typical of large LC data sets. The method has been adopted official first action.

Carbofuran↗