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Martin Litzenburger, Rita Bernhardt
Steroids and their oxyfunctionalized counterparts are valuable compounds for the pharmaceutical industry; however, the regio- and stereoselective introduction of oxygen is a challenging task for the synthetic chemistry. Thus, cytochromes P450 play an important role for the functionalization of steroidal compounds. In this study, we elucidated the main product of 11-deoxycorticosterone conversion formed by CYP260B1 from Sorangium cellulosum So ce56 as 9α-OH 11-deoxycorticosterone by NMR spectroscopy. This is, to the best of our knowledge, the first identification of a 9α-hydroxylase for this substrate...
August 18, 2017: Steroids
Alina Świzdor, Anna Panek, Natalia Milecka-Tronina
Aspergillus niger, one of fungal species most frequently used for experimental and industrial-scale biotransformations of various organic compounds, is generally known to transform steroids at 16β position. In this work, application of the strain A. niger KCH910 to bioconversion of dehydroepiandrosterone (DHEA), androstenediol and testosterone is described, with emphasis on the metabolic steps leading to the products. Evidence from this study indicated that incubated 5-ene steroids underwent bioconversion within two metabolic pathways: oxidation by the action of 3β-HSD (3β-hydroxysteroid dehydrogenase) to 4-ene steroids, and minor allylic hydroxylation to epimeric 7-alcohols...
August 18, 2017: Steroids
Delia Soto-Castro, Roberto Carlos Lara Contreras, María Del Socorro Pina-Canseco, Rosa Santillán, María Teresa Hernández-Huerta, Guillermo E Negrón Silva, Eduardo Pérez-Campos, Susana Rincón
In this paper is described a synthetic route to 6β-phenylamino-cholestan-3β,5α-diol and (25R)-6β-phenylaminospirostan-3β,5α-diol, starting from Cholesterol and Diosgenin, respectively. The products were obtained in two steps by epoxidation followed by aminolysis, through an environmentally friendly and solvent-free method mediated by SZ (sulfated zirconia) as catalyst. The use of SZ allows chemo- and regioselective ring opening of the 5,6α-epoxide during the aminolysis reaction eliminating the required separation of the epoxide mixture...
August 18, 2017: Steroids
Francisca Plaza-Parrochia, Carmen Romero, Luis Valladares, Margarita Vega
Normal endometrial function requires of cell proliferation and differentiation; therefore, disturbances in these processes could lead to pathological entities such as hyperplasia and endometrial adenocarcinoma, where cell proliferation is increased. The development of these pathologies is highly related to alterations in the levels and/or action of sexual steroids. In the present review, it has been analyzed how steroids, particularly estrogens, androgens and progestagens are involved in the etiopathogenesis of hyperplasia and endometrial endometrioid adenocarcinoma...
August 18, 2017: Steroids
Wei Yang, Xiaomin Kang, Na Qin, Feng Li, Xinxin Jin, Zhengmin Ma, Zhuang Qian, Shufang Wu
Intra-articular injection of glucocorticoids is used to relieve pain and inflammation in osteoarthritis patients, which is occasionally accompanied with the serious side effects of glucocorticoids in collagen-producing tissue. Melatonin is the major hormone released from the pineal gland and its beneficial effects on cartilage has been suggested. In the present study, we investigated the protective role of melatonin on matrix degeneration in chondrocytes induced by dexamethasone (Dex). The chondrocytes isolated from mice knee joint were treated with Dex, melatonin, EX527 and siRNA targeted for SIRT6, respectively...
August 10, 2017: Steroids
Ádám Baji, Ferenc Kovács, Gergő Mótyán, Gyula Schneider, János Wölfling, Izabella Sinka, István Zupkó, Imre Ocsovszki, Éva Frank
Novel androstanopyrazoles have been efficiently synthesized from steroidal β-ketoaldehydes with different arylhydrazine hydrochlorides both under acidic and basic conditions. Knorr-type transformations of 16-hydroxymethylene-dehydroepiandrosterone containing its 1,3-dicarbonyl moiety on ring D, proved to be regioselective in pyridine at room temperature, while mixtures of regioisomers were obtained in acidic EtOH under reflux. Contrarily, the cyclocondensation reactions of 2-hydroxymethylene-dihydrotestosterone bearing its reactive functionalities on ring A, led to a mixture of pyrazole regioisomers in varying ratio depending on the applied medium...
August 10, 2017: Steroids
Sukanya Phungphong, Anusak Kijtawornrat, Sirinut Chaiduang, Vitoon Saengsirisuwan, Tepmanas Bupha-Intr
BACKGROUND: Ecdysteroids, a group of steroid hormones found in insects and many plants, have been shown to prevent various changes in mammalian tissues after female sex hormone deprivation. PURPOSE: To examine whether an ecdysteroid, 20-hydroxyecdysone (20-HE), exhibits regulatory or protective roles in the cardiovascular system. STUDY DESIGN/METHOD: Blood pressure and cardiac function were evaluated in spontaneously hypertensive rats (SHR) during and after daily treatment with 20-HE for six weeks...
August 9, 2017: Steroids
Shaymaa M M Yahya, Abdou O Abdelhamid, Mervat M Abd-Elhalim, Ghada H Elsayed, Emad F Eskander
Due to its high potency and selectivity, anticancer agents consisting of combined molecules have gained great interests. The current study introduces newly synthesized progesterone derivatives of promising anticancer effect. Moreover, the pro-apoptotic and anti-angiogenic effects of these compounds were studied extensively. Several thiazole, pyridine, pyrazole, thiazolopyridine and pyrazolopyridine progesterone derivatives were synthesized. The structure of the novel progesterone derivatives was elucidated and confirmed using the analytical and spectral data...
August 8, 2017: Steroids
Yoshajandith Aguirre-Vidal, Antonio Monroy-Noyola, Laura Anaya-Ramos, Marcela Arteaga-Silva, Marisela Mendez-Armenta, Pedro Ostoa-Saloma, Mariana Díaz-Zaragoza, Jorge Morales-Montor, Camilo Ríos, Sergio Montes
Estradiol (E2), in addition to its known hormone function, is a neuroactive steroid that has shown neuroprotective profile in several models of neurological diseases. The present study explores the antioxidant effect of β-estradiol-3-benzoate (EB) on the neurotoxicity elicited by MPP(+) in rat striatum. Male Wistar rats, that were gonadectomized 30days prior to EB, were given 100µgEB per rat every 48h for 11days and animals were infused with MPP(+) via intrastriatal at day six after beginning EB treatment...
August 4, 2017: Steroids
Rayala Naveen Kumar, Seongmin Lee
Cephalostatins, ritterazines and their hybrid bis-steroidal pyrazine analogs such as 25-epi-rittereostatin GN1N show unusually high potency against a wide range of cancer cell lines. Herein, we report the synthesis and bioactivity of 23-deoxy-25-epi ritterostatin GN1N, which lacks the 23-hydroxyl group of 25-epi rittereostatin GN1N. The less oxygenated bis-steroidal pyrazine was ∼50- to 1000-fold less potent than 25-epi ritterostatin GN1N, highlighting the importance of the 23-hydroxyl group for the antiproliferative activity of the cephalostatin/ritterazine class of drugs...
August 1, 2017: Steroids
Bingqing Yu, Zhaoxiang Liu, Jiangfeng Mao, Xi Wang, Junjie Zheng, Shuyu Xiong, Mingxuan Cui, Wanlu Ma, Qibin Huang, Hongli Xu, Bingkun Huang, Min Nie, Xueyan Wu
17β-Hydroxysteroid dehydrogenase type 3 (17β-HSD3) converts the inactive Δ4-androstenedione (A) to testosterone (T). Its deficiency is the most common testosterone biosynthesis defect that results in 46,XY Disorders Of Sex Development (DSD). However, the disease is difficult to distinguish from other 46,XY DSD for similar clinical phenotypes. Therefore, genetic testing provides good criteria for the diagnosis of the disease. In this study, HSD17B3 gene was examined in 3 unrelated Chinese patients with 46,XY DSD...
August 1, 2017: Steroids
Elias Baydoun, Atia-Tul-Wahab, Sheeza Iqbal, Colin Smith, M Iqbal Choudhary
Biotransformation of an orally active contraceptive drug, drospirenone (1), by Cunninghamella elegans ATCC 36114 yielded four new metabolites, 6β,7β,15β,16β-dimethylene-3-oxo-14α-hydroxy-17α-pregn-4-ene-21,17-carbolactone (2), 6β,7β,15β,16β-dimethylene-3,11-dioxo-17α-pregn-4-ene-21,17-carbolactone (3), 6β,7β,15β,16β-dimethylene-3,12-dioxo-17α-pregn-4-ene-21,17-carbolactone (4), and 6β,7β,15β,16β-dimethylene-3-oxo-11β,14α-dihydroxy-17α-pregn-4-ene-21,17-carbolactone (5), along with a known metabolite, 6β,7β,15β,16β-dimethylene-3-oxo-11α-dihydroxy-17α-pregn-4-ene-21,17-carbolactone (6)...
July 30, 2017: Steroids
Peter Ergang, Martin Vodička, Karla Vagnerová, Martin Moravec, Pavlína Kvapilová, Milan Kment, Jiří Pácha
The bioavailability of glucocorticoids is modulated by enzyme 11β-hydroxysteroid dehydrogenase type 1 (11HSD1), which catalyzes the conversion of inactive 11-oxo-glucocorticoids to active 11-hydroxy-glucocorticoids cortisol and corticosterone and is regulated by pro-inflammatory cytokines. Our aim was to assess the effect of colitis on the expression of 11HSD1 in specific microanatomical compartments of the mucosal immune system. Using qRT-PCR we quantified the expression of 11HSD1 and cytokines in the colon, mesenteric lymph nodes (MLN) and spleen of mice with colitis...
July 25, 2017: Steroids
Ana Lúcia Bertarello Zeni, Anderson Camargo, Ana Paula Dalmagro
Corticosterone (CORT) treatment has been evidenced to develop a depression-like state in animals, that mimic hypothalamic-pituitary-adrenal (HPA)-axis dysregulation implicated in the development of depression. The present study aimed to examine the ferulic acid (FA), a natural phenolic compound, antidepressant and antioxidant activities on the CORT chronic model. Mice orally treated with 20mg/kg of CORT for 21days were connsidered control group, while mice treated with FA (1mg/kg) or fluoxetine (10mg/kg) for the last week of CORT treatment, as drug groups...
July 19, 2017: Steroids
Christoph Zutz, Karen Wagener, Desislava Yankova, Stefanie Eder, Erich Möstl, Marc Drillich, Kathrin Rychli, Martin Wagner, Joseph Strauss
Estrogenic active compounds are present in a variety of sources and may alter biological functions in vertebrates. Therefore, it is crucial to develop innovative analytical systems that allow us to screen a broad spectrum of matrices and deliver fast and reliable results. We present the adaptation and validation of a fungal biosensor for the detection of estrogen activity in cow derived samples and tested the clinical applicability for pregnancy diagnosis in 140 mares and 120 cows. As biosensor we used a previously engineered genetically modified strain of the filamentous fungus Aspergillus nidulans, which contains the human estrogen receptor alpha and a reporter construct, in which β-galactosidase gene expression is controlled by an estrogen-responsive-element...
July 14, 2017: Steroids
Mohammad Samadi, Thomas Nury, Ali Khalafi-Nezhad, Gérard Lizard
We report the first Barton radical decarboxylation of unprotected bile acids via in situ irradiation of their thiohydroxamic esters in the presence of citraconic anhydride and citracoimide, leading to the synthesis a series of steroidal maleic anhydrides and maleimides as novel hybrid bile acids. The cytotoxic activities were evaluated on C6 rat glioma cells.
July 13, 2017: Steroids
Himanshu Yadav, Bechan Lal
Considering the absence of information on testicular growth factors in fishes, present study was aimed to elucidate the existence of BMP15, an important member of TGF-β superfamily, in the testis of a seasonally breeding freshwater catfish, Clarias batrachus and its role in regulation of testicular activities. The study demonstrated the expression of BMP15 in the somatic cells (Sertoli and interstitial cells) in fish testis. The expression varied with changing testicular activity; the expression was very high in the quiescent and early recrudescing testis coinciding with the renewal of spermatogonial cells...
July 13, 2017: Steroids
Weronika Kozanecka-Okupnik, Beata Jasiewicz, Tomasz Pospieszny, Monika Matuszak, Lucyna Mrówczyńska
Bile acids (lithocholic: LCA, deoxycholic: DCA and cholic: CA) and their formyl- and acetyl- derivatives can be used as starting material in chemical synthesis of compounds with different biological activity strongly depended on their chemical structures. Our previous studies showed that biological activity of bile acids salts with gramine toward human erythrocytes was significantly different from the activity of bile acids alone. Moreover, gramine effectively modified the membrane perturbing activity of other steroids...
July 12, 2017: Steroids
Tatsuya Higashi, Shui Watanabe, Koki Tomaru, Wataru Yamazaki, Kazumi Yoshizawa, Shoujiro Ogawa, Hidenori Nagao, Kouichi Minato, Masamitsu Maekawa, Nariyasu Mano
Although some studies have revealed the implication of bile acids (BAs) and neurological diseases, the levels and origin of the BAs in the brain are not fully understood. In this study, we first developed and validated a sensitive and specific method for the determination of three unconjugated BAs [cholic acid (CA), chenodeoxycholic acid (CDCA) and deoxycholic acid (DCA)] in the rat brain by liquid chromatography/electrospray ionization-tandem mass spectrometry combined with chemical derivatization. The measured brain concentrations (mean±standard deviation, n=10) of normal rats were 58...
July 8, 2017: Steroids
Ze-Dan Wang, Guo-Dong Yao, Wei Wang, Wen-Bao Wang, Shao-Jie Wang, Shao-Jiang Song
Sarsasapogenin, extracted from Anemarrhena asphodeloides Bunge., has been reported to protect neurons from H2O2-induced damage. In the current study, four series of 26-amino acid methyl ester substituted sarsasapogenin derivatives (5a-5e, 5f-5j, 6a-6e and 7a-7e) were synthesized and tested for neuroprotective activity by evaluating their neuroprotective ratio against SH-SHY5Y cell lines. Studies showed that most of the target compounds displayed better neuroprotective effects than that of sarsasapogenin. Structure-activity relationship analysis suggested that 3-methoxy derivatives (5f-5j) were more potent than other series and the phenylalanine methyl ester moiety at C-26 was important for exhibiting apparent neuroprotective activity...
July 5, 2017: Steroids
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