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Reyna Zeferino-Diaz, J Ciciolil Hilario-Martinez, Maricela Rodriguez-Acosta, Alan Carrasco-Carballo, Maria Guadalupe Hernandez-Linares, Jesus Sandoval-Ramirez, Maria A Fernandez-Herrera
26-Hydroxycholestan-22-one derivatives with oxygenated functions in the rings A and/or B were successfully synthesized from diosgenin. After the modifications of rings A and B, the spiroketal side chain was selectively opened through a Lewis acid mediated acetolysis to afford the cholestane derivatives. These compounds incorporate pharmacophores, which mimic the activity of natural phytohormones and show high growth promoting activity in Mexican rice cultivars using the rice lamina inclination test.
June 18, 2017: Steroids
YoungAh Youn, Cheong-Jun Moon, In Kyung Sung
We examined whether hydrocortisone exposure ≤ 1week in very low birth weight infants (VLBWI) was associated with poor neurodevelopmental outcomes at corrected 18 months. Further, the clinical factors associated with worse long term outcome were also evaluated. Of a total of 191 VLBWI, the clinical data for these infants relating were retrospectively collected for analysis. Among the 191 VLBWI, 115 (60.2%) infants were exposed to early postnatal hydrocortisone ≤ 1 week of life in our NICU of Seoul St. Mary's Hospital, The Catholic University of Korea between December 2012 and December 2014...
June 18, 2017: Steroids
Michail Tsoukalas, Arianna Psichas, Frank Reimann, Fiona M Gribble, Annelise Lobstein, Aurélie Urbain
Five new pregnane-type steroidal glycosides, named menarandrosides A-E (1-2, 5-7) were isolated from the aerial parts of Cynanchum menarandrense, together with three known compounds, carumbelloside I (3), carumbelloside II (4), and pregnenolone-3-O-gentiobioside (8). Their structures were determined on the basis of spectroscopic analyses including NMR and mass spectrometry, reporting C-21 steroids glycosylated only by one or two glucose moieties. Compounds were then investigated for their potential to stimulate glucagon-like peptide-1 (GLP-1) secretion in intestinal cells; although none of the pure compounds had any influence, the fraction enriched in pregnanes exhibited a significant activity, suggesting a possible synergistic effect...
June 18, 2017: Steroids
Ahmed A Zaki, Zulfiqar Ali, Yan-Hong Wang, Yasser A El-Amier, Shabana I Khan, Ikhlas A Khan
Three new bidesmosidic cholestane-type steroidal glycosides,16-O-β-D-glucopyranosyl-cholest-5-en-3β,16β-diol-22-one-3-O-α-L-rhamnopyranosyl-(1→2)-O-[(β-D-glucopyranosyl(1→4)]-O-β-D-glucopyranoside (1), 16-O-β-D-glucopyranosylcholest-5-en-3β,16β-diol-22-one-3-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside (2), and 16-O-β-D-glucopyranosylcholestan-3β,16β-diol-6,22-dione-3-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranoside(3) were isolated from a methanolic extract of Panicum turgidum...
June 16, 2017: Steroids
David J Morris, Jason M Ridlon
A new concept is emerging in biomedical sciences: the gut microbiota is a virtual 'organ' with endocrine function. Here, we explore the literature pertaining to the role of gut microbial metabolism of endogenous adrenocorticosteroids as a contributing factor in the etiology of essential hypertension. A body of literature demonstrates that bacterial products of glucocorticoid metabolism are absorbed into the portal circulation, and pass through the kidney before excretion into urine. Apparent Mineralocorticoid Excess (AME) syndrome patients were found to have congenital mutations resulting in non-functional renal 11β-hydroxysteroid dehydrogenase-2 (11β-HSD2) and severe hypertension often lethal in childhood...
June 14, 2017: Steroids
Koen Van Gansbeke, Eirik Johansson Solum, Sandra Liekens, Anders Vik, Trond Vidar Hansen
The regioselective synthesis of estrogens and their derivatives continues to be of interest. Most reported syntheses require multistep protocols associated with poor overall yield and lack of regioselectivity. New preparative protocols are still desired. Herein, 11 2-alkylated 17β -estradiol analogs were synthesized in a highly regioselective manner. The products were obtained using a convenient, one pot and high-yielding protocol. The anti-proliferative activity of the compounds was tested in human T-cell leukemia (CEM), human cervix carcinoma (HeLa) and human dermal microvascular endothelial (HMEC-1) cells...
June 14, 2017: Steroids
Ming Bu, Tingting Cao, Hongxia Li, Mingzhou Guo, Burton B Yang, Yue Zhou, Na Zhang, Chengchu Zeng, Liming Hu
By inspiration of significant anti-cancer activity of our previously screened natural ergosterol peroxide (EP), a series of novel steroidal 5α,8α-endoperoxide derivatives 5a-d and 14a-f were designed, synthesized, and biologically evaluated for their in vitro anti-proliferative inhibitory and cytotoxic activity. The results revealed that most of these compounds showed moderate-to-excellent anti-proliferative effects against the tested cancer cell lines (i.e. HepG2, SK-Hep1, MDA-MB-231 and MCF-7). Among them, compound 5b and 14d exhibited preferable inhibitory activities (IC50 of 5b and 14d are 8...
June 9, 2017: Steroids
Marcin Górecki, Alicja Dziedzic, Roman Luboradzki, Anna Ostaszewska, Jadwiga Frelek, Wojciech J Szczepek
Four crystalline dutasteride hydrochloride hydrate solvates containing respectively methanol, ethanol, acetone and acetonitrile molecules were obtained. All samples were characterized by extensive spectroscopic analysis with infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC) and (1)H as well as (13)C NMR techniques. For three solvates, i.e. methanol, ethanol and acetone solvates, the single crystal X-ray diffraction (SCXRD) experiments were possible, and their respective crystal and molecular structures were determined...
June 8, 2017: Steroids
Lucía Pronsato, Lorena Milanesi, Andrea Vasconsuelo, Anabela La Colla
The loss of muscle mass and strength with aging, sarcopenia, is a prevalent condition among the elderly, associated with skeletal muscle dysfunction and enhanced muscle cell apoptosis. We have previously demonstrated that testosterone protects against H2O2-induced apoptosis in C2C12 muscle cells, at different levels: morphological, biochemical and molecular. Since we have observed that testosterone reduces p-p53 and maintains the inactive state of FoxO3a transcription factor, induced by H2O2, we analyzed if the hormone was exerting its antiapoptotic effect at transcriptional level, by modulating pro and antiapoptotic genes associated to them...
May 26, 2017: Steroids
Salman A Khan, Abdullah M Asiri
Ru(II) steroidal metal complexes were synthesized by the reaction of dichlorodicarbonyl ruthenium(II) [Ru(CO)2Cl2]n with Steroidal thiosemicarbazones. Coordination via the thionic sulfur and the azomethine nitrogen atom of the thiosemicarbazone to the Ru(II) metal. Steroidal thiosemicarbazone derivatives were obtained by the thiosemicarbazide with steroidal ketones. Structures of the steroidal thiosemicarbazone and their metal complexes were confirmed by the FT-IR, (1)H NMR, (13)C NMR, Fab-Mass spectroscopy and elemental analysis...
May 25, 2017: Steroids
Kejing Lao, Jie Sun, Chong Wang, Weiting Lyu, Boshen Zhou, Ruheng Zhao, Qian Xu, Qidong You, Hua Xiang
5α-Reductase is a key enzyme responsible for dihydrotestosterone biosynthesis and has been recognized as an important target for discovering new drugs against benign prostatic hyperplasia (BPH). In this study, a series of novel steroidal androst-3,5-diene-3-carboxylic acids have been designed and synthesized. Biological evaluations were performed on their 5α-reductase inhibitory activities by both in vitro enzyme inhibition assay and in vivo by prostate weighing method. Results showed that most of them displayed excellent 5α-reductase inhibitory potency...
May 24, 2017: Steroids
Marcus K Taylor, Genieleah A Padilla, Lisa M Hernández
We recently established stable daily profiles of the anabolic hormones dehydroepiandrosterone (DHEA) and testosterone in 57 elite military men. In this follow-on study, we explored associations of salivary anabolic hormone profiles with demographic (i.e., age, body mass index [BMI]) and biobehavioral health indices (i.e., blood pressure, sleep, perceived stress, fatigue) via correlational models. Next, nuanced patterns were constructed using quartile splits followed by one-way analysis of variance and post hoc subgroup comparisons...
May 21, 2017: Steroids
Qian Gao, Yuqian Qiao, Yanbing Shen, Min Wang, Xibo Wang, Yang Liu
Various corticosteroids are prepared by using 11α,17α-diOH-progesterone (11α,17α-diOH-PROG) as an important intermediate and raw material. Hence, strains that can improve the yields of 11α,17α-diOH-PROG should be screened. Cunninghamella elegans CICC40250 was singled out from five common 11α hydroxylation strains. The reaction parameters of 11α,17α-diOH-PROG production were also investigated. C. elegans CICC40250 could efficiently catalyze the hydroxylation of 17α-hydroxy progesterone (17α-OH-PROG) at C-11α position...
May 19, 2017: Steroids
Eszter Szánti-Pintér, Lilla Maksó, Ágnes Gömöry, Johan Wouters, Bianka Edina Herman, Mihály Szécsi, Gábor Mikle, László Kollár, Rita Skoda-Földes
Aza-Michael addition of 16-dehydropregnenolone was studied in the presence of a basic ionic liquid, [DBU][OAc] as catalyst and solvent. The reaction was carried out using different primary and secondary amines as N-nucleophiles. The products were obtained in moderate to good yields and were characterized by (1)H and (13)C NMR, MS and IR. The ionic liquid was found to be an efficient and recyclable catalyst that was reused five times. The products were investigated for the inhibition of in vitro C17,20-lyase activity and displayed moderate inhibitory effect...
May 11, 2017: Steroids
Maria-Luisa Lazo-de-la-Vega-Monroy, Martha-Olivia Solís-Martínez, Gustavo Romero-Gutiérrez, Victor E Aguirre-Arzola, Katarzyna Wrobel, Kazimierz Wrobel, Silvio Zaina, Gloria Barbosa-Sabanero
Small for gestational age infants have greater risk of developing metabolic diseases in adult life. It has been suggested that low birth weight may result from glucocorticoid excess in utero, a key mechanism in fetal programming. The placental enzyme 11-beta hydroxysteroid dehydrogenase type 2 (11β-HSD2, HSD11B2 gene) acts as a barrier protecting the fetus from maternal corticosteroid deleterious effects. Low placental 11β-HSD2 transcription and activity have been associated with low birth weight, yet the mechanism regulating its protein expression is not fully understood...
May 11, 2017: Steroids
Cesare Guercia, Piergiorgio Cianciullo, Cinta Porte
Several studies have indicated that up to 70% of the total steroids detected in molluscs are in the esterified form and that pollutants, by modifying the esterification of steroids with fatty acids, might act as endocrine disrupters. However, despite the strong physiological significance of this process, there is almost no information on which fatty acids form the steroid esters and how this process is modulated. This study (a) investigates the formation of fatty acid esters of testosterone in digestive gland microsomal fractions of the mussel Mytilus galloprovincialis incubated with either palmitoly-CoA or CoA and ATP, and (b) assesses whether the endocrine disruptor tributyltin (TBT) interferes with the esterification of testosterone...
May 11, 2017: Steroids
Jinna Liu, Di Zhang, Xiaoyu Sun, Tingle Ding, Beilei Lei, Cunli Zhang
Brassinosteroids (BRs) control several important agronomic traits, such as strengthening resistance to diverse adversity, improving the quality, and increasing crop yield. Their chemical structures and varieties, specific methods for the evaluation of bioactivities, structure-activity relationships, potential novel compounds, and practical agricultural uses were summarized. The findings allow the examination of brassinosteroids in two important issues: 1) Do the results of different bioevaluation protocols provide similar activities for BRs? and 2) which bioevaluated compounds would proof to have a greater potential for application in agricultural usages?...
May 11, 2017: Steroids
Luigi Devoto, Soledad Henríquez, Paulina Kohen, Jerome F Strauss
The human corpus luteum (CL) is a temporary endocrine gland derived from the ovulated follicle. Its formation and limited lifespan is critical for steroid hormone production required to support menstrual cyclicity, endometrial receptivity for successful implantation, and the maintenance of early pregnancy. Endocrine and paracrine-autocrine molecular mechanisms associated with progesterone production throughout the luteal phase are critical for the development, maintenance, regression, and rescue by hCG which sustains CL function into early pregnancy...
May 11, 2017: Steroids
Yusuke Miura, Takayuki Furukawa, Miho Kobayashi, Rojeet Shrestha, Ryoji Takahashi, Chikara Shimizu, Hitoshi Chiba, Shu-Ping Hui
BACKGROUND: Urine has been utilized as a source of biomarkers in renal disease. However, urinary lipids have not attracted much attention so far. Here we studied urinary cholesteryl ester (CE) and its relevance in renal disease. METHODS: Quantitative analysis of CE molecular species in serum, urinary supernatant, and urinary sediment from patients with renal disease (N=64) and non-renal disease (N=23) was carried out using liquid chromatography-tandem mass spectrometry (LC-MS/MS) and deuterated CEs as internal standards...
May 11, 2017: Steroids
Ting-Xiang Lu, Tong Shu, Xu-Jie Qin, Wei Ni, Yun-Heng Ji, Qi-Run Chen, Afsar Khan, Qing Zhao, Hai-Yang Liu
Phytochemical investigation on the whole plants of Ypsilandra parviflora led to the isolation of seven new spirostanol saponins, named ypsiparosides A-G, together with 14 known saponins. Their structures were unambiguously established based on extensive spectroscopic evidence and chemical methods. The induced rabbit platelet aggregation activities of the isolates were tested. Compounds 4, 15, and 17 showed maximal platelet aggregation rates ranging from 43 to 55% at a concentration of 300μg/mL. Further experiments exhibited that compounds 4, 15, and 17 possessed EC50 values of 642...
May 11, 2017: Steroids
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