scholarly journals Chemical and biochemical studies on 18-hydroxyoestrone

1974 ◽  
Vol 137 (2) ◽  
pp. 263-272 ◽  
Author(s):  
John K. Findlay ◽  
Lothar Siekmann ◽  
Heinz Breuer
Keyword(s):  
Mass Spectra ◽  
Strong Acid ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
No Formation ◽  
Polar Metabolites ◽  
Characteristic Fragmentation ◽  
Liquid Chromatographic

1. 18-Hydroxyoestrone was reduced by NaBH4 in methanol, giving 18-hydroxyoestradiol-17α and 18-hydroxyoestradiol-17β in the ratio 3:7. 2. Treatment of 18-hydroxyoestrone with a strong alkali yielded 18-noroestrone; however, the 18-hydroxyoestradiols did not undergo transformation to their respective 18-nor derivatives. 3. All the 18-hydroxylated oestrogens were stable under acid conditions. They formed Kober chromogens: the chromogenicity of 18-hydroxyoestrone was only one-third that of the 18-hydroxyoestradiols and oestriol. 4. Paper-, thin-layer- and gas–liquid-chromatographic systems for the characterization of these compounds are described. 5. An examination of the mass spectra revealed peaks characteristic of the substituted carbon atoms. Definite assignment of the 17α- and 17β-hydroxyl groups of the epimeric 18-hydroxyoestrogens was possible by characteristic fragmentation of the free steroids. Further, the configuration of 18-hydroxyoestradiol-17β was confirmed by the formation of the dimethylsildioxy derivative of the 3-methylether of the steroid. 6. Both rat and rabbit liver slices reduced 18-hydroxyoestrone to 18-hydroxyoestradiol-17β and some other labile, polar metabolites with properties similar to 2-hydroxylated oestrogens. No formation of 18-hydroxyoestradiol-17α in vitro was observed. 7. The results are discussed with respect to the possible influence of the 18-hydroxyl group on reactions at C-17, as well as the reactions of 18-hydroxylated oestrogens with strong acid (Kober reactions) and alkali.

scholarly journals Enhancement of Antioxidant and Hydrophobic Properties of Alginate via Aromatic Derivatization: Preparation, Characterization, and Evaluation

Polymers ◽  
2021 ◽  
Vol 13 (15) ◽  
pp. 2575
Author(s):  
Smaher M. Elbayomi ◽  
Haili Wang ◽  
Tamer M. Tamer ◽  
Yezi You
Keyword(s):  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Gravimetric Analysis ◽  
Scanning Calorimetry ◽  
Benzoyl Group ◽  
Antioxidant Evaluation ◽  
Thermo Stability

The preparation of bioactive polymeric molecules requires the attention of scientists as it has a potential function in biomedical applications. In the current study, functional substitution of alginate with a benzoyl group was prepared via coupling its hydroxyl group with benzoyl chloride. Fourier transform infrared spectroscopy indicated the characteristic peaks of aromatic C=C in alginate derivative at 1431 cm−1. HNMR analysis demonstrated the aromatic protons at 7.5 ppm assigned to benzoyl groups attached to alginate hydroxyl groups. Wetting analysis showed a decrease in hydrophilicity in the new alginate derivative. Differential scanning calorimetry and thermal gravimetric analysis showed that the designed aromatic alginate derivative demonstrated higher thermo-stability than alginates. The aromatic alginate derivative displayed high anti-inflammatory properties compared to alginate. Finally, the in vitro antioxidant evaluation of the aromatic alginate derivative showed a significant increase in free radical scavenging activity compared to neat alginate against DPPH (2,2-diphenyll-picrylhydrazyl) and ABTS free radicals. The obtained results proposed that the new alginate derivative could be employed for gene and drug delivery applications.

scholarly journals Synthesis and Characterizations of Dipeptide Derivative of Gentamicin

2019 ◽  
Vol 28 (2) ◽  
pp. 73-82
Author(s):  
Oun D. Khudair ◽  
Diar A. Fatih
Keyword(s):  
Acid Chloride ◽  
Solution Method ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Free Hydroxyl ◽  
Ester Linkage ◽  
Amine Groups ◽  
Conventional Solution ◽  
Dipeptide Derivative

Abstract       The target derivative are gentamicin linked with L-Val- L-Ala by an ester linkage. These were synthesized by esterification method, which included the reaction of -OH hydroxyl group on (carbon No.5) of gentamicin with the acid chloride of the corresponding dipeptide, The preparation of new derivative of gentamicin involved protected the primary & secondary amine groups of Gentamicin, by Ethylchloroformate (ECF) to give N-carbomethoxy Gentamicin which was used for further chemical synthesis involving the free hydroxyl groups. Then prepared dipeptide (L-Val- L-Ala) by conventional solution method in present DCC & HoBt then reacted with thionyl chloride to prepared acid chloride of dipeptides, then after, linked by ester linkage to N-protection gentamicin in present pyridine as base, finally deportation the amino group of synthesized compound by using TFAA in present anisole. The characterization of the titled compounds were performed utilizing FTIR spectroscopy, CHNS elemental analysis, and by measurements of their physical properties.  

scholarly journals Characterization of the Urease Operon of Brucella abortus and Assessment of Its Role in Virulence of the Bacterium

2006 ◽  
Vol 75 (2) ◽  
pp. 774-780 ◽  
Author(s):  
Félix J. Sangari ◽  
Asunción Seoane ◽  
María Cruz Rodríguez ◽  
Jesús Agüero ◽  
Juan M. García Lobo
Keyword(s):  
Brucella Abortus ◽  
Urease Activity ◽  
Strong Acid ◽  
Oral Route ◽  
Open Reading Frames ◽  
Human Brucellosis ◽  
Major Route

ABSTRACT Most members of the genus Brucella show strong urease activity. However, the role of this enzyme in the pathogenesis of Brucella infections is poorly understood. We isolated several Tn5 insertion mutants deficient in urease activity from Brucella abortus strain 2308. The mutations of most of these mutants mapped to a 5.7-kbp DNA region essential for urease activity. Sequencing of this region, designated ure1, revealed the presence of seven open reading frames corresponding to the urease structural proteins (UreA, UreB, and UreC) and the accessory proteins (UreD, UreE, UreF, and UreG). In addition to the urease genes, another gene (cobT) was identified, and inactivation of this gene affected urease activity in Brucella. Subsequent analysis of the previously described sequences of the genomes of Brucella spp. revealed the presence of a second urease cluster, ure2, in all them. The ure2 locus was apparently inactive in B. abortus 2308. Urease-deficient mutants were used to evaluate the role of urease in Brucella pathogenesis. The urease-producing strains were found to be resistant in vitro to strong acid conditions in the presence of urea, while urease-negative mutants were susceptible to acid treatment. Similarly, the urease-negative mutants were killed more efficiently than the urease-producing strains during transit through the stomach. These results suggested that urease protects brucellae during their passage through the stomach when the bacteria are acquired by the oral route, which is the major route of infection in human brucellosis.

scholarly journals Characterization of a New Chitosanase from a Marine Bacillus sp. and the Anti-Oxidant Activity of Its Hydrolysate

Marine Drugs ◽  
2020 ◽  
Vol 18 (2) ◽  
pp. 126
Author(s):  
Chunrui Ma ◽  
Xiao Li ◽  
Kun Yang ◽  
Shangyong Li
Keyword(s):  
Radical Scavenging ◽  
Maximal Activity ◽  
Hydroxyl Groups ◽  
Bacillus Sp ◽  
Low Molecular Weight Chitosan ◽  
Anti Oxidant

Chitooligosaccharide (COS) has been recognized to exhibit efficient anti-oxidant activity. Enzymatic hydrolysis using chitosanases can retain all the amino and hydroxyl groups of chitosan, which are necessary for its activity. In this study, a new chitosanase encoding gene, csnQ, was cloned from the marine Bacillus sp. Q1098 and expressed in Escherichia coli. The recombinant chitosanase, CsnQ, showed maximal activity at pH 5.31 and 60 °C. Determination of CsnQ pH-stability showed that CsnQ could retain more than 50% of its activity over a wide pH, from 3.60 to 9.80. CsnQ is an endo-type chitosanase, yielding chitodisaccharide as the main product. Additionally, in vitro and in vivo analyses indicated that chitodisaccharide possesses much more effective anti-oxidant activity than glucosamine and low molecular weight chitosan (LMW-CS) (~5 kDa). Notably, to our knowledge, this is the first evidence that chitodisaccharide is the minimal COS fragment required for free radical scavenging.

scholarly journals Synthesis and Biological Evaluation of Novel 1,3-Benzoxathiol-2-one Sulfonamides against Toxic Activities of the Venom of Bothrops jararaca and B. jararacussu Snakes

2021 ◽  
Author(s):  
Eliza Chazin ◽  
Leonardo Martins ◽  
Marcus Vinícius de Souza ◽  
Claudia Regina Gomes ◽  
Ana Cláudia da Silva ◽  
...  
Keyword(s):  
Mass Spectra ◽  
Biological Evaluation ◽  
Ionization Mass ◽  
Bothrops Jararaca ◽  
Biological Potential ◽  
Serum Therapy ◽  
Synthesis And Biological Evaluation

This work describes the synthesis of new 1,3-benzoxathiol-2-one sulfonamides and evaluation of their ability to inhibit some in vitro (coagulant, proteolytic and hemolytic) and in vivo (hemorrhagic, edematogenic and lethality) toxic activities of Bothrops jararaca and B. jararacussu venoms. Compounds have been synthesized from the coupling of intermediate 5-amino-6‑methoxybenzo[d] [1,3]oxathiol-2-one 4 with benzenesulfonyl chlorides. Characterization of the products was achieved by nuclear magnetic resonance (NMR) and electrospray ionization mass spectra (ESI-MS) techniques. Biological assay results have shown that most of compounds inhibited the main toxic activities of the venom of the two snake species. Compound 5b (N-(6‑methoxy-2‑oxobenzo[d] [1,3]oxathiol-5-yl)-4-nitrobenzenesulfonamide) was the most efficient in inhibiting hemolysis of B. jararaca, and coagulation and proteolysis induced by both venoms. For in vivo activities, all compounds inhibited the edema, from 35 to 72%, and most of them exhibited antihemorrhagic and antilethality activities. Thus, the results pointed to the biological potential of these compounds, being promising molecules to treat envenomation by these snakes as well as to aid the current antivenom serum therapy.

Isolation and preliminary characterization of a fraction of bilirubin in serum that is firmly bound to protein.

1982 ◽  
Vol 28 (4) ◽  
pp. 629-637 ◽  
Author(s):  
J J Lauff ◽  
M E Kasper ◽  
T W Wu ◽  
R T Ambrose
Keyword(s):  
Azo Dyes ◽  
Diazonium Salt ◽  
Visible Spectrum ◽  
Strong Acid ◽  
The Other ◽  
Direct Reaction ◽  
Fraction Absorbed ◽  
Chromatographic Peaks ◽  
Liquid Chromatographic

Abstract We have isolated from pathological sera a bilirubin fraction (delta) that is very tightly, if not covalently, bound to protein, most likely albumin. This delta fraction absorbed at a lambda max of 433 nm in the visible spectrum, between the lambda max of unconjugated (alpha) and that of conjugated (Bc) bilirubin when measured in solutions containing albumin. However, unlike the other bilirubin species, this fraction could not be separated from the proteins in serum by exhaustive ultrafiltration in the presence of caffeine/benzoate solution. In the Jendrassik-Grof diazo procedure for bilirubin analysis, the delta fraction gave a large direct reaction (76-89% of the total reaction). Yet, when relatively hydrophobic azo dyes were formed by reaction of the delta fraction with the diazonium salt of dichloroaniline, only 50% of the dyes were extractable from aqueous solution. On chromatography the rest remained associated with protein. Of the extractable dye, more than 70% was accounted for by two liquid-chromatographic peaks with retentions identical with those of azo dyes formed from unconjugated bilirubin. This delta fraction was not appreciably separated from protein by treatment with strong acid or base, or by prolonged digestion with various enzymes. Finally, in a highly denaturing solvent (urea/mercaptoethanol), this fraction was not dialyzable through a membrane with a 12 000-dalton cutoff.

scholarly journals Bioapplications of Bacterial Cellulose Polymers Conjugated with Resveratrol for Epithelial Defect Regeneration

Polymers ◽  
2019 ◽  
Vol 11 (6) ◽  
pp. 1048 ◽  
Author(s):  
En Meng ◽  
Chin-Li Chen ◽  
Chuan-Chieh Liu ◽  
Cheng-Che Liu ◽  
Shu-Jen Chang ◽  
...  
Keyword(s):  
Mechanical Strength ◽  
Bacterial Cellulose ◽  
Wound Repair ◽  
Cell Attachment ◽  
Skin Irritation ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Skin Substitutes ◽  
Epithelial Regeneration

Excellent wound dressing is essential for effective wound repair and regeneration. However, natural polymeric skin substitutes often lack mechanical strength and hydrophilicity. One way to overcome this limitation is to use biodegradable polymers with high mechanical strength and low skin-irritation induction in wet environments. Bacterial cellulose (BC) is an attractive polymer for medical applications; unlike synthetic polymers, it is biodegradable and renewable and has a strong affinity for materials containing hydroxyl groups. Therefore, we conjugated it with resveratrol (RSV), which has a 4′-hydroxyl group and exhibits good biocompatibility and no cytotoxicity. We synthesized BC scaffolds with immobilized RSV and characterized the resulting BC/RSV scaffold with scanning electron microscopy and Fourier-transform infrared spectroscopy. We found that RSV was released from the BC in vitro after ~10 min, and immunofluorescence staining showed that BC was highly biocompatible and regenerated epithelia. Additionally, Masson’s trichrome staining showed that the scaffolds preserved the normal collagen-bundling pattern and induced re-epithelialization in defective rat epidermis. These results indicated that RSV-conjugated BC created a biocompatible environment for stem cell attachment and growth and promoted epithelial regeneration during wound healing.

scholarly journals Functional characterization of synthetic leukotriene B and its stereochemical isomers.

1981 ◽  
Vol 154 (4) ◽  
pp. 1243-1248 ◽  
Author(s):  
R A Lewis ◽  
E J Goetzl ◽  
J M Drazen ◽  
N A Soter ◽  
K F Austen ◽  
...  
Keyword(s):  
Functional Characterization ◽  
Neutrophil Infiltration ◽  
Eicosatetraenoic Acid ◽  
Human Neutrophils ◽  
Racemic Mixture ◽  
Hydroxyl Groups ◽  
Biological Assays ◽  
Neutrophil Chemotactic Activity

Leukotriene B (LTB), a potent lipid chemotactic factor for neutrophils, is 5S,12R-dihydroxy-6,14-cis,8,10-trans-eicosatetraenoic acid (Fig 1), based upon direct comparison of natural LTB with synthetic 5S,12R-dihydroxy-6,8,10,14-eicosatetraenoic acid (5,12-di-HETE) stereoisomers in three biological assays. Of the six synthetic stereoisomers evaluated, only the 5S,12R,6,14-cis,8,10-trans compound had chemotactic potency for human neutrophils in vitro that was comparable to that of natural LTB, with a concentration of 3 X 10(9-9) M eliciting a one-half maximum response. In contrast, the racemic mixture of 5R,12R- and 5S,12S-6,10-trans,8,14-cis, the racemic mixture of 5S,12R- and 5R,12S-6,10-trans,8,14-cis, the 5S,12R-6,8-trans,10,14-cis, the 5S,12R-6,8,10-trans,14-cis, and the 5S,12S-6,8,10-trans,14-cis stereoisomers required concentrations of 3 X 10(-7) to 1 X 10(-6) M to elicit comparable responses. Only natural LTB and its synthetic counterpart elicited a local neutrophil infiltration when injected into the skin of the rhesus monkey at 10 ng and 100 ng per site. Natural and synthetic LTB at a concentration of 3 X 10(-8) M each provoked an EC25 contractile response of guinea pig pulmonary parenchymal strips in vitro, whereas the other four tested stereoisomers of 5,12-di-HETE were inactive at this concentration. Structure-function analyses suggest that the neutrophil chemotactic activity depends critically upon the C-1 to C-12 domain, including the stereochemistry of the 6-,8-,and 10-olefinic bonds and the presence of both hydroxyl groups.

scholarly journals Metabolism of apigenin and related compounds in the rat. Metabolite formation in vivo and by the intestinal microflora in vitro

1972 ◽  
Vol 128 (4) ◽  
pp. 901-911 ◽  
Author(s):  
L. A. Griffiths ◽  
G. E. Smith
Keyword(s):  
Oral Administration ◽  
Intestinal Microflora ◽  
Biochanin A ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Flavonoid Compounds ◽  
Ring Fission ◽  
Micro Organisms

1. The metabolism of a group of flavonoid compounds related in structure to apigenin (4′,5,7-trihydroxyflavone) and including apigenin, apiin, naringin, phlorrhizin, acacetin, kaempferol, robinin, chrysin, tectochrysin and 4′,7-dihydroxyflavone, was studied both in vivo after oral administration to the rat, and in vitro in cultures of micro-organisms derived from the intestine of the rat. 2. The rat intestinal microflora is capable of effecting degradation of flavonoid compounds to metabolites observed in the urine after oral administration of the specific flavonoid. 3. All compounds possessing free 5- and 7-hydroxyl groups in the A ring and a free 4′-hydroxyl group in the B ring gave rise to ring-fission products, which included 4′-hydroxyphenylacyl derivatives. 4. On anaerobic incubation in a thioglycollate medium, intestinal micro-organisms can effect flavonoid-ring fission, cleavage of glycosidic bonds and the reduction of double bonds in the side chains of certain metabolites. 5. Two flavonoids (chrysin and tectochrysin) undergo hydroxylation in the 4′-position in vivo but not during incubation with the intestinal microflora in vitro. 6. Observations on the metabolism of other compounds substituted in the 4′-position, e.g. epiafzelechin, pelargonin and the isoflavones, genistein, biochanin A, daidzein and formononetin, by the intestinal microflora of the rat are also reported.

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