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Bisphenol A, an environmental compound with estrogenic activity, has been shown to bind human sex steroid hormone-binding globulin (hSHBG), the main plasma transport protein which regulates the metabolism of androgens and estrogens and limits their access to target organs. The present study was conducted to determine whether physiologically relevant concentrations of hSHBG can influence the blood...
A group of biologically active 4-azasteroids was studied by 13 C-NMR spectroscopy in solution and in the solid phase. A full assignment of signals in the spectra of samples in chloroform was performed for thirteen 4-azasteroids using two-dimensional techniques. Substituent and steric effects of a nitrogen atom, and their influence on chemical shifts of the neighboring carbon atoms are...
We investigated the effect of interleukin 1β (IL-1β) on steroid sulfatase (STS) activity and the expression of STS mRNA in human endometrial stromal cells. Endometrial tissue samples were obtained from patients undergoing hysterectomy to remove uterine fibroids. Stromal cells were isolated from the tissue preparation and cultured. IL-lβ (1~100 ng/ml) was added into the culture medium and incubated...
Pregnancy-induced hypertension (PIH) is a frequent cause of maternal and neonatal morbidity and mortality. 19-Noraldosterone, which was shown to be synthesized in the human adrenal gland, exhibits potent mineralocorticoid and hypertensive activity. To examine the role of mineralocorticoids in the pathophysiology of PIH, we studied urinary 19-noraldosterone, tetrahydroaldosterone, free cortisol, and...
Chemical investigation of methanol extract of the leaves of Diploclisia glaucescens of the family Menispermaceae furnished a new ecdysteroid, 3-deoxy-1β,20-dihydroxyecdysone. The structure of the new ecdysteroid was established on detailed analysis of spectral data. The 3-deoxy ecdysteroid showed 40% potency of 20-hydroxyecdysone in the spiracle index assay using the fourth instar larvae of the silkworm...
This article describes the oxidation of cholesta-5,7-dien-3β-yl acetate (4) with the urea-hydrogen peroxide adduct (UHP) using methyltrioxorhenium (MTO) as catalyst, under various conditions. Specifically, the effects of using different solvents (CHCl 3 and ethers) and additives (EtOH and pyridine) on the course of the MTO-catalyzed oxidation of 4 were investigated. Some new steroids (6, 9,...
The four 16-hydroxymethylestra-1,3,5(10)-triene-3,17-diol isomers were synthesized and tested in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities are lower than 2.0% relative to that of the reference molecule estra-1,3,5(10)-triene-3,17β-diol. The affinities of the tested compounds for the androgen and progesterone receptors are very...
An association between a gene polymorphism of the human glucocorticoid receptor (hGR) gene and rheumatoid arthritis has recently been suggested. This polymorphism contains an A to G mutation in the 3'UTR of exon 9β, which encodes the 3'UTR of the mRNA of the hGRβ isoform. The hGRβ isoform can act as a dominant negative inhibitor of hGRα, and therefore may contribute to glucocorticoid resistance. The...
This paper elaborates an improved synthesis of crinosterol and campesterol starting from stigmasterol. The proposed approach is based on Claisen rearrangement of Δ 23 -22-allylic alcohols with various configurations of the 22-hydroxy group and geometry of the Δ 23 -double bond. It allows complete use of the starting steroid for preparing 24α-methyl derivatives. It was possibe...
A series of progesterone-4-ovalbumin (OVA) conjugates with different length linkers (4-, 11-, and 18-atoms long) were synthesized by successive aminocaproic acid homologation of 3-(pregn-4-ene-3,20-dione-4-yl)thiopropanoic acid (1) before conjugation to ovalbumin. The performance studies of these progesterone-4-ovalbumin conjugates showed that the effects of the length of linker on the antibody binding...
Homogeneous catalytic hydrazinocarbonylation of some steroid derivatives possessing iodo-alkenyl moiety (17-iodo-androst-16-ene 1, 17-iodo-3-methoxy-estra-1,3,5(10),16-tetraene 2, 17-iodo-4-aza-4-methyl-androst-16-en-3-one 3 and 17-iodo-6β-hydroxy-3α,5α-cycloandrost-16-ene 4) were carried out in the presence of a palladium catalyst, a base and acetic or benzoic hydrazide as the nucleophilic reagent...
Increasing evidence indicates the existence of membrane receptors for testosterone (mAR) and estradiol (mER) on the surface of cells, besides the classic intracellular androgen receptor (iAR) and estrogen receptors (iER). Here, we investigate the occurrence of sex steroid receptors in B cells isolated from the spleen of C57BL/10 mice using magnetic cell sorting. RT-PCR reveals the presence of iAR,...
Androstenedione is a steroid hormone sold over-the-counter to individuals who expect that it will enhance strength and athletic performance. Endogenous androstenedione is the immediate precursor of testosterone. To evaluate the metabolism of oral androstenedione, we randomly assigned 37 healthy men to receive 0 (group 1), 100 mg (group 2), or 300 mg (group 3) of androstenedione in a single daily dose...
A number of [26- 2 H 3 ]brassinosteroids were prepared for biochemical studies. The parent, nondeuterated compounds were considered to be biosynthetic intermediates in brassinosteroid biosynthesis. Claisen rearrangement was used to construct the steroidal side chain. Deuterium was introduced by reducing the corresponding intermediates with lithium aluminium deuteride.
Though sex steroids are found to influence thyroid pathogenesis in human and in animals, their role in normal thyroid growth and thyrocyte proliferation is not yet understood fully. The present study is addressed to know the effect of testosterone and estradiol on the basal and TSH-induced thyrocyte proliferation in immature and adult rats in vitro. The male and female Wistar rats were gonadectomized...
Two new C-nor/D-homo corticosteroids were isolated from the filtrate of the triene carbonate intermediate during the production of betamethasone. Their structures were elucidated based on NMR spectroscopic studies and mass spectral analyses. The mechanism of formation of each of these two steroids was postulated as a Wagner-Meerwein rearrangement of the corresponding 12β-hydroxy steroid. The new 12β-hydroxy...
The incidence of cardiovascular disease is greater in men than in premenopausal women. Testosterone has been considered a significant risk factor for cardiovascular disease, but testosterone's mechanism of action and its cellular site of action are still not clear. However, it is likely that non-genomic extracellular effects of the hormone are involved. With the aim of providing further information...
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