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Steroids

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https://www.readbyqxmd.com/read/30326212/study-on-the-reaction-of-diosgenin-acetate-with-trimethylsilylazide-catalyzed-by-lewis-acids
#1
Agnieszka Wojtkielewicz, Urszula Kiełczewska, Beata Banel, Jacek W Morzycki
The ring opening reaction of diosgenin acetate in presence of Lewis acids and trimethylsilyl azide was explored as a facile approach to the synthesis of an open chain derivative with a nitrogen-containing substituent at C26. The reaction, under optimal conditions (TMSOTf, 1 equiv.; TMSN3 , 1.1 equiv.; DCM; 48 h; rt), provided satisfactory yield (40%) of furostane-26-nitrile in a single step.
October 13, 2018: Steroids
https://www.readbyqxmd.com/read/30326211/highly-oxygenated-isoprenoid-lipids-derived-from-fungi-and-fungal-endophytes-origin-and-biological-activities
#2
REVIEW
Nick Savidov, Tatyana A Gloriozova, Vladimir V Poroikov, Valery M Dembitsky
This mini review is devoted to highly oxygenated isoprenoid lipids (HOIL) that are produced by fungi and fungal endophytes from various ecological niches, both terrestrial and aquatic. Steroids were distributed as from edible cultivated fungi, as well as fungi collected in forests. Fungal endophytes were generally isolated from plants and cultured to obtain sufficient biomass. Marine fungi were obtained from marine brown and red algae and marine invertebrates such as sponges, corals, worms, crustacea or from marine sediments...
October 13, 2018: Steroids
https://www.readbyqxmd.com/read/30315840/synthesis-cytotoxic-evaluation-and-molecular-docking-studies-of-the-semi-synthetic-triterpenoid-steroid-hybrids
#3
Irina A Tolmacheva, Alexey V Nazarov, Daria V Eroshenko, Victoria V Grishko
Synthetic transformations of steroids for drug discovery and improvement of drug effectiveness have been an important part of modern medicinal chemistry and pharmaceutical sciences. Pentacyclic triterpenoids, being represented in the nature by various structures and biogenetically related to steroids, can largely expand the spectrum of biologically active steroidal agents via synthesis of the so-called "triterpenoid-steroid" hybrids. In the presented work, the nitrile anion cyclizations of 3,4-secolupane and 3,4-seco-oleanane nitriles and follow-up synthetic transformations of the cyclized products with formation of the gemm-dimethyl-free A ring "triterpenoid-steroid" hybrids were studied...
October 10, 2018: Steroids
https://www.readbyqxmd.com/read/30296544/steroids-specific-target-library-for-steroids-target-prediction
#4
Xiaoxue Dang, Zheng Liu, Yanzhuo Zhou, Peizi Chen, Jiyuan Liu, Xiaojun Yao, Beilei Lei
Steroids exist universally and play critical roles in various biological processes. Identifying potential targets of steroids is of great significance in studying their physiological and biochemical activities, the side effects and for drug repurposing. Herein, aiming at more precise steroids targets prediction, a steroids-specific target library integrating 3325 PDB or homology modeling structures categorized into 196 proteins was built by considering chemical similarity from DrugBank and biological processes from KEGG...
October 6, 2018: Steroids
https://www.readbyqxmd.com/read/30296550/synthesis-and-antiproliferativeactivity-of-17-1-2-3-selenadiazolylpregnenolone-compounds
#5
Jianguo Cui, Liping Pang, Meizhen Wei, Chunfang Gan, Dandan Liu, Haiyan Yuan, Yanmin Huang
Using pregnenolone as a starting material, some 3-substituted 17-[1',2',3']-selenadiazolylpregnenolone derivatives were synthesized, and their structures were characterized by IR, NMR and HRMS. The in vitro antitumor activity of the compounds was assayed against PC-3、SKOV3、T47D、MCF-7 and HEK293T cell lines. The results show that some compounds display selective antiproliferative activity against PC-3 and SKOV3 cells lines and are almost inactive to normal kidney epithelial cells (HEK293T). The IC50 value are much better than that of abiraterone (positive control)...
October 5, 2018: Steroids
https://www.readbyqxmd.com/read/30296549/fluorine-containing-lupane-triterpenoid-acid-derivatives-design-synthesis-and-biological-evaluation-as-potential-anti-inflammatory-agents
#6
Tatyana S Khlebnicova, Yuri A Piven, Alexander V Baranovsky, Fedor A Lakhvich, Iryna V Sorokina, Tatyana G Tolstikova
A series of novel fluorine-containing lupane triterpenoid acid derivatives with fluoroaromatic amide moieties at the C-28 position (1-8) or with 2-(fluoroacyl)cyclopentane-1,3-dione fragments at the C-3 position (9-18) of lupane skeleton was synthesized. A simple synthesis of novel lupane triterpenoid hybrids with 2-(fluoroacyl)-2-cyclopenten-1-one moieties was developed. An interaction of 2-acyl-3-chlorocyclopent-2-en-1-ones, obtained from corresponding cyclic β-triketones, with methyl 3-amino-3-deoxybetulinate gave 3β-isomers (9-13) and 3α-isomers (14-18) of target hybrids, which were isolated as individual compounds...
October 5, 2018: Steroids
https://www.readbyqxmd.com/read/30296548/separation-and-identification-of-the-epimeric-doping-agents-dexamethasone-and-betamethasone-in-equine-urine-and-plasma-a-reversed-phase-chiral-chromatographic-approach
#7
Tajudheen K Karatt, Ramy Sayed, Jahfar Nalakath, Zubair Perwad, Peter H Albert, K K Abdul Khader
Chirality is one of the most important considerations when controlling doping. The epimeric corticosteroids dexamethasone and betamethasone are significantly potent and long-acting, and they are highly abused in equestrian sports. The scope of this study was to develop a simple and reliable analytical method for simultaneously identifying and separating regularly abused co-eluting corticosteroids in equine urine and plasma. In this paper, we present a simple and rapid method for the chiral separation and identification of epimeric mixtures of dexamethasone and betamethasone using a Thermo Q Exactive high resolution accurate mass spectrometer...
October 5, 2018: Steroids
https://www.readbyqxmd.com/read/30296547/steroid-profiling-in-nails-using-liquid-chromatography-tandem-mass-spectrometry
#8
Clarissa Daniela Voegel, Pearl La Marca-Ghaemmaghami, Ulrike Ehlert, Markus R Baumgartner, Thomas Kraemer, Tina Maria Binz
The retrospective analysis of endogenous steroid hormones in nails can be used to elucidate endocrine diseases and thus help with their diagnosis and treatment. A liquid chromatography-tandem mass spectrometry (LC-MS/MS) based method was developed for the simultaneous identification and quantification of 12 steroid hormones (aldosterone, cortisone, cortisol, corticosterone, 11-deoxycortisol, androstenedione, 11-deoxycorticosterone, testosterone, dehydroepiandrosterone (DHEA), 17α-hydroxyprogesterone (17-OHP), dihydrotestosterone (DHT) and progesterone) in human fingernails...
October 5, 2018: Steroids
https://www.readbyqxmd.com/read/30296546/pregn-5-en-3%C3%AE-ol-and-androst-5-en-3%C3%AE-ol-dicarboxylic-acid-esters-as-potential-therapeutics-for-nmda-hypofunction-in-vitro-safety-assessment-and-plasma-stability
#9
Marika Matousova, Radko Soucek, Eva Tloustova, Barbora Slavikova, Hana Chodounska, Helena Mertlikova-Kaiserova, Eva Kudova
Neurosteroids are endogenous steroidal compounds that can modulate neuronal receptors. N-Methyl-D-aspartate receptors (NMDARs) are glutamate-gated, calcium-permeable ion channels that are of particular interest, as they participate in synaptic transmission and are implicated in various processes, such as learning, memory, or long-term neuronal potentiation. Positive allosteric modulators that increase the activity of NMDARs may provide a therapeutic aid for patients suffering from neuropsychiatric disorders where NMDAR hypofunction is thought to be involved, such as intellectual disability, autism spectrum disorder, or schizophrenia...
October 5, 2018: Steroids
https://www.readbyqxmd.com/read/30296545/timosaponin-aiii-a-novel-potential-anti-tumor-compound-from-anemarrhena-asphodeloides
#10
REVIEW
Feng-Ying Han, Xiao-Yu Song, Jing-Jie Chen, Guo-Dong Yao, Shao-Jiang Song
Timosaponin AIII, a major steroidal saponin found in Anemarrhena asphodeloides Bge., which has been widely used as anti-pyretic, anti-diabetic, anti-inflammatory, anti-platelet aggregator and anti-depressant agents in traditional Chinese medicine. Recent pharmacological study showed that timosaponin AIII had potent cytotoxicity, which was potential to be developed as an anticancer agent, however the molecular mechanism underlying the anticancer activity has not been fully elucidated. This review aims to give a systematic summary of the study of timosaponin AIII to reveal its anti-tumor activities by investigating invasion and migration, apoptosis, autophagy and reversing multi-drug resistance...
October 5, 2018: Steroids
https://www.readbyqxmd.com/read/30296543/c-21-steroids-from-streptocaulon-juventas-lour-merr-induce-apoptosis-in-hepg2
#11
Wanfang Zhu, Shengzhi Su, Yunhui Xu, Zijian Xie, Yidan Bai, Wenyuan Liu, Masahiko Abe, Toshihiro Akihisa, Feng Feng, Jie Zhang
Three new C21 steroids, i.e., (3β,17α,20S)-pregn-5(6)-ene-3, 17, 20-triol-3-O-β-D- digitalopyranosyl-(1→4)-β-D-digitalopyranoside (4), (3β,17α,20S)- pregn-5(6)-ene-3, 17, 20-triol-20-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→2)-β-D-digital- opyranoside (8), (3β, 20R)-pregn-14(15)-ene-3, 20, 21-triol-3-O-β-D-glucopy- ranoside (10), along with ten known C21 steroids were isolated from Streptocaulon juventas. Their structures were elucidated on the basis of 1D and 2D NMR spectroscopic techniques, mass spectrometry as well as comparison with the literature...
October 5, 2018: Steroids
https://www.readbyqxmd.com/read/30278183/expression-of-oestrogen-receptor-beta-was-negatively-correlated-with-disease-activity-in-patients-with-crohn-s-disease-involving-the-terminal-ileum
#12
Hongxia Li, Hong Chen, Lu Chen, Duo Shen, Xiaoxin Xu
Crohn's disease (CD) is a chronic inflammatory disease. The recurrence and remission of symptoms in CD patients are associated with changes in hormones, such as in puberty, pregnancy, postpartum and menopause, reflecting that oestrogen and its receptor might play an important role in CD. The study aimed to investigate the expression and clinical significance of oestrogen receptor in patients with CD involving the terminal ileum. Expression of oestrogen receptor alpha (ERα) and oestrogen receptor beta (ERβ) of 37 patients with CD involving the terminal ileum and 21 healthy controls was determined by immunohistochemistry...
September 29, 2018: Steroids
https://www.readbyqxmd.com/read/30273696/anti-inflammatory-furostanol-saponins-from-the-rhizomes-of-smilax-china-l
#13
Yang Xie, Deng Hu, Cheng Zhong, Kai-Fei Liu, En Fang, Ying-Jun Zhang, Chun Zhou, Li-Wen Tian
Seven new furostanol saponins (1-7), chongrenosides A-G, were isolated from the rhizomes of Smilax china L., together with nine known furostanol saponins (8-16). The structures of the new furostanol saponins (1-7) were elucidated by extensive spectroscopic data analyses (1D and 2D NMR, HRESIMS) and chemical evidence. Compounds 1-6 and 8-16 were evaluated for TNF-α mRNA expression inhibitory activity on LPS induced RAW264.7 cells. Of them, 1, 4, 6, and 11 inhibited the TNF-α mRNA expression by 88%, 87%, 67%, and 93%, respectively, at the concentration of 10 µM...
September 29, 2018: Steroids
https://www.readbyqxmd.com/read/30273694/crystal-structures-and-hirshfeld-surface-analyses-of-the-di-and-tri-hydrates-of-5%C3%AE-17e-17-hydrazonoandrostan-3-ol-significant-differences-in-the-hydrogen-bonding-patterns-and-supramolecular-arrangements
#14
Ligia R Gomes, John N Low, Alan B Turner, Thomas C Baddeley, James L Wardell
The crystal structures, Hirshfeld surface analyses and electrostatic potential surfaces of the di- and tri-hydrates of (5α,17E)-17-hydrazonoandrostan-3-ol, 3, namely [3·(H2 O)2 ] and [3·(H2 O)3 ], are reported. The trihydrate, isolated from a solution of 3 in moist methanol, recrystallizes in the orthorhombic space group, P21 21 21 , while that of the dihydrate, isolated from a 1:1 aqueous methanol solution, recrystallizes in the monoclinic space group, P21 . The asymmetric unit of the trihydrate involves one steroid and three water molecules, while that of the dihydrate has two similar but independent steroid molecules and four hydrate molecules...
September 29, 2018: Steroids
https://www.readbyqxmd.com/read/30273695/chemical-synthesis-of-c3-oxiranyl-oxiranylmethyl-estrane-derivatives-targeted-by-molecular-modeling-and-tested-as-potential-inhibitors-of-17%C3%AE-hydroxysteroid-dehydrogenase-type-1
#15
Maxime Lespérance, Xavier Barbeau, Jenny Roy, René Maltais, Patrick Lagüe, Donald Poirier
17β-Hydroxysteroid dehydrogenase type 1 (17β-HSD1) is a promising therapeutic target known to play a pivotal role in the progression of estrogen-dependent diseases such as breast cancer, and endometriosis. This enzyme is responsible for the last step in the biosynthesis of the most potent estrogen, estradiol (E2) and its inhibition would prevent the growth of estrogen-sensitive tumors. Based on molecular modeling with docking experiments, we identified two promising C3-oxiranyl/oxiranylmethyl-estrane derivatives that would bind competitively and irreversibly in the catalytic site of 17β-HSD1...
September 28, 2018: Steroids
https://www.readbyqxmd.com/read/30244069/effects-of-glucocorticoid-on-the-eye-development-in-guinea-pigs
#16
Meihua Ding, Dadong Guo, Jianfeng Wu, Xiang Ye, Yueying Zhang, Fang Sha, Wenjun Jiang, Hongsheng Bi
Glucocorticoid (GC) has been widely used in clinic. However, the effect of GC on normal and myopic development of eyes is still unknown. In this study, 3-week-old guinea pigs were randomly divided into four groups: No-Lens (control), GC+No-Lens, negative lens-induced myopia (LIM), and GC+LIM. To induce myopia, right eyes were covered with a -10 D lens in GC+LIM and LIM groups. GC+No-Lens and GC+LIM groups received intraperitoneal injections of hydrocortisone (10 mg/kg) once daily for 2 weeks, and then received intragastric hydrocortisone (32...
September 20, 2018: Steroids
https://www.readbyqxmd.com/read/30236620/clickable-conjugates-of-bile-acids-and-nucleosides-synthesis-characterization-in-vitro-anticancer-and-antituberculosis-studies
#17
Devesh S Agarwal, Vagolu Siva Krishna, Dharmarajan Sriram, Perumal Yogeeswari, Rajeev Sakhuja
A series of clickable bile acid-nucleosides conjugates linked directly or via amino acid linker were synthesized, and characterized by spectroscopic techniques such as 1 H NMR, 13 C NMR, FT-IR, HRMS and HPLC. The synthesized compounds 6a-p were screened for their in vitro anticancer property against a panel of three cancer cell lines (PC-3, MCF-7, IMR-32). In addition, the synthesized derivatives were also tested for their antimycobacterial activity against Mycobacterium tuberculosis H37 Rv (ATCC 27294 strain)...
September 17, 2018: Steroids
https://www.readbyqxmd.com/read/30232035/correlation-between-chronological-and-physiological-age-of-males-from-their-multivariate-urinary-endogenous-steroid-profile-and-prostatic-carcinoma-induced-deviation
#18
Eleonora Amante, Eugenio Alladio, Alberto Salomone, Marco Vincenti, Federico Marini, Giorgio Alleva, Stefano De Luca, Francesco Porpiglia
The biosynthesis of endogenous androgenic anabolic steroids (EAAS) in males varies with age. Knowledge of the general urinary EAAS profile's dependence from aging - not reported up to now - may represents a prerequisite for its exploitation in the screening and diagnostic support for several pathologies. Extended urinary EAAS profiles were obtained from healthy and pathological individuals, using a GC-MS method which was fully validated by a stepwise, analyst-independent scheme. Seventeen EAAS and five of their concentration ratios were determined and investigated using multivariate statistical methods...
September 16, 2018: Steroids
https://www.readbyqxmd.com/read/30217788/ichnocarpus-frutescens-l-r-br-root-derived-phyto-steroids-defends-inflammation-and-algesia-by-pulling-down-the-pro-inflammatory-and-nociceptive-pain-mediators-an-in-vitro-and-in-vivo-appraisal
#19
Niranjan Das, Abhijit Bhattacharya, Sudip Kumar Mandal, Utsab Debnath, Biswanath Dinda, Subhash C Mandal, Prabir Kumar Sinhamahapatra, Amresh Kumar, M Dutta Choudhury, Sabyasachi Maiti, Partha Palit
Ichnocarpus frutescens, a climber plant, is distributed all over India. As its different parts are used as anti-inflammatory agent, so we re-investigated the roots to isolate compounds and evaluate its biological efficacy. Also, in-silico molecular docking was carried out to elucidate the structure activity relationship (SAR) of isolated compounds toward identifies the drug target enzyme with validation, which was further supported by anti-inflammatory in-vitro and in-vivo experimental models. The compounds have been undertaken mainly to investigate the anti-inflammatory and analgesic efficacy along with molecular docking investigation followed by anti-proteinase, anti-denaturation and cyclooxygenase (COX) inhibition studies...
September 12, 2018: Steroids
https://www.readbyqxmd.com/read/30217787/bile-acids-lipase-catalyzed-synthesis-of-new-hyodeoxycholic-acid-derivatives
#20
Santiago N Chanquia, Erika Ripani, Alicia Baldessari, Guadalupe García Liñares
In this work we present an efficient, environmentally friendly approach to the synthesis of a series of hyodeoxycholic acid derivatives applying Biocatalysis. Fifteen acetyl and ester derivatives, twelve of them new, were obtained through an enzymatic strategy in a fully regioselective way and in very good to excellent yield. In order to find the optimal reaction conditions, the influence of several parameters such as enzyme source, alcohol or acylating agent:substrate ratio, enzyme:substrate ratio, temperature and reaction solvent was considered...
September 12, 2018: Steroids
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