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steroid synthesis

Luis Almagro, Manuel Nogueras, Margarita Suárez, Justo Cobo, Christopher Glidewell
Two new functionalized steroids containing both chloro and formyl substituents in ring A, and intended as precursors for the synthesis of hybrid systems, have been synthesized from ketosteroid precursors. 3-Chloro-2-formyl-17,17-dimethyl-18-nor-5α-androstane-2,13-diene, (I), and methyl 3-chloro-4-formyl-12-oxo-5β-cholan-3-ene-24-oate, C26 H37 ClO4 , (IV), have been synthesized using Vilsmeier reactions with 17β-hydroxy-17α-methyl-5α-androstan-3-one and methyl 3,13-dioxo-5β-cholan-24-oate, respectively...
December 1, 2018: Acta Crystallographica. Section C, Structural Chemistry
Samira Asghari, Amir Valizadeh Dizajeykan, Majid Ahmadi, Abolfazl Barzegari, Reza Rikhtegar, Sanam Dolati, Shahla Danaii, Sedigheh Abdollahi-Fard, Mohammad Nouri, Mahdi Mahdipour, Mehdi Yousefi
BACKGROUND: Despite at the beginning known as a benign disease, endometriosis is defined as a risk factor for developing ovarian carcinoma. The effect of endometriosis on ovarian malignancy is known but its role in granulosa cell tumor is still unclear. METHODS AND MATERIALS: In this study, serum samples were collected from patients with endometriosis and divided into whole and steroid-depleted groups. Desertification was performed according to the charcoal-dextran protocol and sera were added to the culture media of granulosa cells retrieved from tubal or male factor infertile women...
December 4, 2018: Journal of Cellular Physiology
Andy Pranata, Christopher C Fitzgerald, Olha Khymenets, Erin Westley, Natasha J Anderson, Paul Ma, Oscar J Pozo, Malcolm D McLeod
Doubly or bisconjugated steroid metabolites have long been known as minor components of the steroid profile that have traditionally been studied by laborious and indirect fractionation, hydrolysis and gas chromatography-mass spectrometry (GC-MS) analysis. Recently, the synthesis and characterisation of steroid bis(sulfate) (aka disulfate or bis-sulfate) reference materials enabled the liquid chromatography-tandem mass spectrometry (LC-MS/MS) study of this metabolite class and the development of a constant ion loss (CIL) scan method for the direct and untargeted detection of steroid bis(sulfate) metabolites...
December 1, 2018: Steroids
Ming Liu, Jian-Qiang Kong
Herein we describe the discovery and functional characterization of a steroidal glycosyltransferase (SGT) from Ornithogalum saundersiae and a steroidal glycoside acyltransferase (SGA) from Escherichia coli and their application in the biosynthesis of acylated steroidal glycosides (ASGs). Initially, an SGT gene, designated as OsSGT1, was isolated from O. saundersiae . OsSGT1-containing cell free extract was then used as the biocatalyst to react with 49 structurally diverse drug-like compounds. The recombinant OsSGT1 was shown to be active against both 3 β - and 17 β -hydroxyl steroids...
October 2018: Acta Pharmaceutica Sinica. B
Jin Yan, Wentao Zhu, Dezhen Wang, Miaomiao Teng, Sen Yan, Zhiqiang Zhou
In the environment, endosulfan persists in forms of two isomers (α and β) and a toxic metabolite, endosulfan sulfate. The toxicity of endosulfan on various mammalian tissues has been investigated, but whether the different isomers and metabolites of endosulfans affect mammalian reproductive function remains unclear. This study is aimed to elucidate the different toxicological effects of α-endosulfan, β-endosulfan, and endosulfan sulfate on adult mice testes. We found that the three endosulfans (α endosulfan, β endosulfan and endosulfan sulfate) altered serum sex steroid hormone levels, and changed expression of steroidogenesis genes...
November 20, 2018: Environmental Research
Shaoyong Ke, Ni Li, Ting Ke, Liqiao Shi, Zhigang Zhang, Wei Fang, Ya-Ni Zhang, Kaimei Wang, Ronghua Zhou, Zhongyi Wan, Ziwen Yang, Guangyang Zhang, Yanhong Wei
AIM: Many heterocyclic compounds derived from natural steroids exhibited broad activities, so this work focused on the investigations on a series of steroidal thiazoline conjugates as antiviral agents. MATERIALS & METHODS:  A series of steroid derivatives containing thiazoline heterocycles were designed and synthesized via a convenient condensation procedure. The compounds were screened for their potential antivirus activities against Enterovirus 71 (EV71) and Coxsackie Virus Type B (CVB3)...
November 30, 2018: Future Medicinal Chemistry
Heather K Knych, Rick M Arthur, Dan S McKemie, Kelsey Seminoff, Briana Hamamoto-Hardman, Philip H Kass
Phenylbutazone (PBZ) is a potent Non-Steroidal Anti-Inflammatory drug used commonly in performance horses. The objectives of the current study were to describe blood and urine concentrations and the pharmacokinetics of PBZ and its metabolites following IV and oral administration and to describe the duration of pharmacodynamic effect. To that end, 17 horses received an intravenous (IV) administration and 18 horses an oral administration of 2-grams of PBZ. Blood and urine samples were collected prior to and for up to 96 hours post drug administration...
November 29, 2018: Drug Testing and Analysis
Rebeka Jójárt, Szabolcs Pécsy, György Keglevich, Mihály Szécsi, Réka Rigó, Csilla Özvegy-Laczka, Gábor Kecskeméti, Erzsébet Mernyák
Novel 2- or 4-phosphonated 13α-estrone derivatives were synthesized via the Hirao reaction. Bromo regioisomers (2- or 4-) of 13α-estrone and its 3-benzyl or 3-methyl ether were reacted with diethyl phosphite or diphenylphosphine oxide using Pd(PPh3 )4 as catalyst under microwave irradiation. The influence of the new compounds on the transport function of the organic anion transporting polypeptide OATP2B1 was investigated by measuring Cascade Blue uptake. Derivatives bearing a 3-benzyl ether function displayed substantial submicromolar OATP2B1 inhibitory activity...
2018: Beilstein Journal of Organic Chemistry
Mohita Sharma, Ramanpreet Kaur, Kuldeep Kaushik, Naveen Kaushal
Ulcerative colitis (UC), a form of inflammatory bowel disease (IBD), is an immune-modulated disorder characterized by chronic and recurring inflammatory episodes. Oxidative stress and COX pathway of prostaglandin (PG) biosynthesis is indispensable to pathogenesis of UC. Any imbalance between PGs can compromise the mucosal homeostasis, leading to mucosal damage and chronic inflammation. However, blocking these PGs using classical Cox inhibitors such as Non-steroidal anti-inflammatory drugs (NSAIDs) can instead aggravate signs of IBD...
November 29, 2018: Toxicology Mechanisms and Methods
Santosh Kumar Adla, Barbora Slavikova, Hana Chodounska, Vojtech Vyklicky, Marek Ladislav, Pavla Hubalkova, Barbora Krausova, Tereza Smejkalova, Michaela Nekardova, Marketa Smidkova, Lenka Monincova, Radko Soucek, Ladislav Vyklicky, Eva Kudova
Herein, we report the synthesis, structure-activity relationship study, and biological evaluation of neurosteroid inhibitors of N -methyl-D-aspartate receptors (NMDARs) receptors that employ an amide structural motif, relative to pregnanolone glutamate (PAG) - a compound with neuroprotective properties. All compounds were found to be more potent NMDAR inhibitors (IC50 values varying from 1.4 to 21.7 μM) than PAG (IC50 = 51.7 μM). Selected compound 6 was evaluated for its NMDAR subtype selectivity and its ability to inhibit AMPAR/GABAR responses...
2018: Frontiers in Pharmacology
Magdalena Szymanska, Agnieszka Blitek
The prostacyclin (prostaglandin I2) signaling system is an essential regulator of vascular homeostasis. Since the corpus luteum is a highly vascularized gland, prostacyclin seems to be crucial for luteal development and function. Although progress has been made in understanding the luteotropic action of prostacyclin in mammals, its role in the porcine corpus luteum remains to be determined. Therefore, studies were conducted to (1) determine profiles of prostacyclin synthase expression and prostacyclin metabolite concentration, as well as prostacyclin G-protein-coupled receptor expression in porcine luteal tissue on days 2 to 16 of the estrous cycle and days 10 to 30 of pregnancy using real-time PCR, western blot, or enzyme immunoassay; and (2) examine the effect of prostacyclin on progesterone synthesis in vitro...
August 3, 2018: Biology of Reproduction
Sarada D Tetali
Role of terpenes and isoprenoids has been pivotal in the survival and evolution of higher plants in various ecoregions. These products find application in the pharmaceutical, flavor fragrance, and biofuel industries. Fitness of plants in a wide range of environmental conditions entailed (i) evolution of secondary metabolic pathways enabling utilization of photosynthate for the synthesis of a variety of biomolecules, thereby facilitating diverse eco-interactive functions, and (ii) evolution of structural features for the sequestration of such compounds away from the mainstream primary metabolism to prevent autotoxicity...
November 22, 2018: Planta
Josaphat Miguel Montero-Vargas, Kena Casarrubias-Castillo, Norma Martínez-Gallardo, José Juan Ordaz-Ortiz, John Paul Délano-Frier, Robert Winkler
Jasmonic acid (JA) is a phytohormone involved in plant development and defense. A major role of JA is the enhancement of secondary metabolite production, such as response to herbivory. Systemin is a bioactive plant peptide of 18 amino acids that contributes to the induction of local and systemic defense responses in tomato (Solanum lycopersicum) through JA biosynthesis. The overexpression of systemin (PS-OE) results in constitutive JA accumulation and enhances pest resistance in plants. Conversely, mutant plants affected in linolenic acid synthesis (spr2) are negatively compromised in the production of JA which favors damage and oviposition by insect herbivores...
December 2018: Plant Science: An International Journal of Experimental Plant Biology
Shuxiong Chen, Fengge Wang, Zhuo Liu, Yun Zhao, Yanwen Jiang, Lu Chen, Chunjin Li, Xu Zhou
Brain-derived neurotrophic factor (BDNF) is involved in regulating the growth of ovarian follicles, maturation of the oocyte, and development of the early embryo through its receptor, tyrosine kinase receptor B (TrkB). However, it is still unclear as to how BDNF influences proliferation and steroidogenesis of bovine granulosa cells (GCs). In this paper, we confirmed that BDNF and TrkB were expressed in bovine GCs, and that proliferation and steroidogenesis by bovine GCs were reduced by knockdown of BDNF or inhibition of TrkB...
November 19, 2018: Journal of Cellular Physiology
Ling Xiao, Dengdong Wang, Yin Guo, Zhujing Tang, Qiongyu Liu, Shuisheng Li, Yong Zhang, Haoran Lin
In our previous studies, diploid and triploid hybrids have been detected from the hybridization of Epinephelus coioides♀ × E. lanceolatus♂. The triploid groupers have been found to be delayed in gonadal development, but the mechanism remains poorly understood. In this study, we examined the gonadal development, assayed the serum steroid hormone levels, and compared the BP (brain and pituitary) and G (gonad) transcriptomes of 18-month-old diploid and triploid hybrids. The results showed that levels of serum estradiol-17β and testosterone were significantly higher in triploid groupers...
November 16, 2018: Genomics
Brandon L Adler, Catherine J Wang, Thanh-Lan Bui, Hannah M Schilperoort, April W Armstrong
BACKGROUND: Though anti-tumor necrosis factor agents (anti-TNFs) have been recommended as third-line therapy for sarcoidosis, an up-to-date systematic synthesis of their efficacy and safety is lacking. OBJECTIVES: To systematically review the literature to characterize the efficacy and safety of anti-TNFs in sarcoidosis. SETTINGS: All countries and treatment settings were included. METHODS: We searched MEDLINE, EMBASE, CINAHL, Web of Science, ClinicalTrials...
October 16, 2018: Seminars in Arthritis and Rheumatism
Sean Ting-Shyang Wei, Yu-Wei Wu, Tzong-Huei Lee, Yi-Shiang Huang, Cheng-Yu Yang, Yi-Lung Chen, Yin-Ru Chiang
The 2,3- seco pathway, the pathway for anaerobic cholesterol degradation, has been established in the denitrifying betaproteobacterium Sterolibacterium denitrificans. However, knowledge of how microorganisms respond to cholesterol at the community level is elusive. Here, we applied mesocosm incubation and 16S rRNA sequencing to reveal that, in denitrifying sludge communities, three betaproteobacterial operational taxonomic units (OTUs) with low (94% to 95%) 16S rRNA sequence similarity to Stl. denitrificans are cholesterol degraders and members of the rare biosphere...
September 2018: MSystems
Gergő Mótyán, László Mérai, Márton Attila Kiss, Zsuzsanna Schelz, Izabella Sinka, István Zupkó, Éva Frank
Multistep syntheses of novel 17β-pyrazol-5'-ones in the Δ5 -androstane series were efficiently carried out from pregnenolone acetate. A steroidal 17-carboxylic acid was first synthesized as a norpregnene precursor by the bromoform reaction and subsequent acetylation. Its CDI-activated acylimidazole derivative was then converted to a β-ketoester containing a two carbon atom-elongated side chain than that of the starting material. A Knorr cyclization of the bifunctional 1,3-dicarbonyl compound with hydrazine and its monosubstituted derivatives in AcOH under microwave heating conditions led to the regioselective formation of 17- exo -heterocycles in good to excellent yields...
2018: Beilstein Journal of Organic Chemistry
Xueting Wang, Zhiran Zou, Zhihui Yang, Shan Jiang, Yapeng Lu, Dan Wang, Zhangji Dong, Sha Xu, Li Zhu
Hypoxia-inducible factor-1 (HIF1) is a critical transcription factor involved in cell response to hypoxia. Under physiological conditions, its a subunit is rapidly degraded in most tissues except testes. HIF1 is stably expressed in Leydig cells, which are the main source of testosterone for male, and might bind to the promoter region of steroidogenic acute regulatory protein (Star), which is necessary for the testosterone synthesis, according to software analysis. This study aims to identify the binding sites of HIF1 on Star promoter and its transcriptional regulation of Star to affect testosterone synthesis...
October 1, 2018: Journal of Molecular Endocrinology
Samuel D Offei, Hadi D Arman, Mirza Oais Baig, Lazaro S Chavez, Carlos A Paladini, Francis K Yoshimoto
Cholic acid is the endogenous 12α-hydroxylated bile acid, which possesses enhanced cholesterol absorption properties compared to its 12-desoxy counterpart, chenodeoxycholic acid. The oxysterol 12α-hydroxylase enzyme is cytochrome P450 8B1 (P450 8B1), which regioselectively and stereoselectively incorporates the 12α-hydroxy group in 7α-hydroxycholest-4-en-3-one, the biosynthetic precursor of cholic acid. Despite the vital role of P450 8B1 activity in cardiovascular health, research studies of other 12α-hydroxy steroid derivatives are rare...
December 2018: Steroids
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