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The interplay between mineralocorticoids (MCs) and glucocorticoids (GCs) in sodium transporting epithelia is complex and only partially understood. In seminal papers published in the years soon after the discovery of aldosterone, various investigators experimentally observed that mineralocorticoid-induced renal sodium retention could only be reliably measured in adrenalectomized animals. Addition...
A synthetic androgen 7α-Methyl-19-nortestosterone (MENT) has a potential for therapeutic use in ‘androgen replacement therapy’ for hypogonadal men or as a hormonal male-contraceptive in normal men. Its tissue distribution, excretion and metabolic enzyme(s) have not been reported. Therefore, the present study tested the distribution and excretion of MENT in Sprague-Dawley rats castrated 24h prior to...
Seven new stigmastane-type steroidal glycosides, vernocuminosides A–G (1–7), have been isolated from the stem barks of Vernonia cumingiana Benth. The structural elucidation and stereochemistry determination were achieved by spectroscopic and chemical methods including 1D and 2D NMR ( 1 H– 1 H COSY, HSQC, HMBC, and NOE) experiments, especially the employment of Snatzke’s method expressed...
Experiments were performed to compare the regioselective hydroxylation of the isopropyl C–H bond at C-25 in 5α-cholestan-3β-yl acetate by in situ generated dimethyldioxirane, methyl(trifluoromethyl)dioxirane, hexafluoro(dimethyl)dioxirane or ethyl(trifluoromethyl)dioxirane (ETDO). The dioxiranes were generated from the corresponding ketones and potassium peroxymonosulfate in aq. NaHCO 3 ,...
Two novel C-22 steroidal lactone saponins, namely solanolactosides A, B (1, 2) and two new spirostanol glycosides, namely torvosides M, N (3, 4) were isolated from ethanol extract of aerial parts of Solanum torvum. Their structures were characterized as solanolide 6-O-[α-l-rhamnopyranosyl-(1→3)-O-β-d-quinovopyranoside] (1), solanolide 6-O-[β-d-xylopyranosyl-(1→3)-O-β-d-quinovopyranoside] (2), yamogenin...
Four new steroidal saponins, smilacinoside A (1), B (2), C (3), and D (4), together with three known saponins, funkioside D (5), aspidistrin (6) and 26-O-β-d-glucopyranosyl-22-methoxyl-(25R)-furost-5-en-3β,26-diol 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)-β-d-galactopyranoside (7) were isolated from the dried tender aerial parts of Smilacina atropurpurea (Franch.) Wang et Tang. The structures...
New type of linear cholesterol-like molecules based on cholesterol extended by attachment of etienic acid derivatives was designed and oligosteroids with two to four units were synthesized. Amide bond was used for inter steroid connections and 1-hydroxybenzotriazole active ester method was adapted for their formations. Use of disteroids as larger building blocks was applied.
Enol aldehydes are one type of key degradation and metabolic intermediates from a group of corticosteroids containing the 1,3-dihydroxyacetone side chain on their D-rings, such as betamethasone, dexamethasone, beclomethasone, and related compounds. The formation of enol aldehydes from these corticosteroids is via acid-catalyzed β-elimination of water from the side chain, a process known as Mattox...
Mouse models of cystic fibrosis (CF) display increased sulfotransferase 1E1 (SULT1E1) activity in hepatocytes of cystic fibrosis transmembrane receptor (CFTR)-deficient animals. SULT1E1 is responsible for the sulfation and inactivation of β-estradiol (E2) at physiological concentrations. IGF-1 message levels in CFTR(−/−) mouse livers were positively correlated with body weight and negatively correlated...
The Beckmann rearrangement of the syn and anti isomers of the spirocyclic oxime derived from a 16β,23:23,26-diepoxy-5β-cholestan-22-one was studied. Whereas the anti isomer always follows the Beckmann fragmentation course, the syn isomer, depending on the reaction conditions, follows the normal Beckmann rearrangement course and/or the isomerization to the anti isomer followed by the fragmentation...
There is evidence to suppose that cholesterol-lowering medicine might confer protection against dementia, probably via modulation of cholesterol synthesis in the brain. The aim of the present study was to investigate the potential influence of statins and cholesterol diet on selected parameters relevant to Alzheimer’s disease pathophysiology.For 15 days, rats were orally administered simvastatin (10...
Diflorasone diacetate, a steroid anti-inflammatory drug (marketed as Diacort ® or Florone ® by Pfizer) and used in the treatment of skin disorders, can be prepared as anhydrous form, DD1 (as deposited in the US pharmacopoeia), or as a monohydrated phase, DDW. Heating the DDW form above 90°C, a mixture of DD1 and of a new anhydrous polymorph, DD2 is obtained. Further heating of this...
The 2-methoxy derivative of estradiol is currently in Phase II clinical trial as an anticancer agent while the 4-methyl derivative has been shown to interact with cytoplasmic and nuclear estrogen receptors in rat pituitary gland and hypothalamus. We hypothesize that the 16α- 18 F-analogs of these estrogens could be suitable radiotracers to evaluate action mechanisms of the parent compounds...
Three new (1, 4, 9) and nine previously reported (2, 3, 5–8, 10–12) 5α,8α-epidioxysterols were isolated from the organic extracts of the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum. The structures and relative configurations of 1–12 were established on the basis of detailed NMR spectroscopic analyses and comparison with the literature. The growth inhibitory effects of 1–12...
The side chain of a compound plays an important role in its biological function. In our studies, we have found that hydroximinosteroid derivatives with different side chains and position of hydroximino on ring A and B displayed remarkable distinct cytotoxicities against a diversity of cancer cell types. Presence of an oxime group on ring B and a hydroxy on ring A or B resulted in a higher cytotoxicity...
Boldenone is an androgenic anabolic steroid intensively used for growth promoting purposes in animals destined for meat production and as a performance enhancer in athletics. Therefore its use is officially banned either in animals intended for consumption or in humans. Because most anabolic steroids are completely metabolized and usually no parent steroid is excreted, metabolite identification is...
The synthesis of 3β-hydroxy-androsta-5,7-dien-17-one from 3β-hydroxy-androst-5-en-17-one (dehydroepiandrosterone, DHEA) via microbial 7α-hydroxylation has been accomplished. At the first stage, 3β,7α-dihydroxy-androst-5-en-17-one was obtained in high yield (71.2%) using a strain of Gibberella zeae VKM F-2600, which was first applied for DHEA conversion. The further route included the substitution...
The synthesis of several novel 5α- and 5β-20-oxo-pregnane derivatives substituted in the position 3 and 7 of the steroid skeleton is described. Activity of synthesized compounds was studied in voltage-clamped cultured rat hippocampal neurons. Substituted derivatives inhibited NMDA-elicited neuronal activity. The relationship between biological activity and structure is discussed.
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