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https://www.readbyqxmd.com/read/28533033/screening-for-strains-with-11%C3%AE-hydroxylase-activity-for-17%C3%AE-hydroxy-progesterone-biotransformation
#1
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
https://www.readbyqxmd.com/read/28502863/synthesis-of-16%C3%AE-amino-pregnenolone-derivatives-via-ionic-liquid-catalyzed-aza-michael-addition-and-their-evaluation-as-c17-20-lyase-inhibitors
#2
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
https://www.readbyqxmd.com/read/28502862/11-beta-hydroxysteroid-dehydrogenase-2-promoter-methylation-is-associated-with-placental-protein-expression-in-small-for-gestational-age-newborns
#3
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
https://www.readbyqxmd.com/read/28502861/analysis-of-testosterone-fatty-acid-esters-in-the-digestive-gland-of-mussels-by-liquid-chromatography-high-resolution-mass-spectrometry
#4
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
https://www.readbyqxmd.com/read/28502860/structure-activity-relationship-of-brassinosteroids-and-their-agricultural-practical-usages
#5
REVIEW
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 brassinosteriods 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
https://www.readbyqxmd.com/read/28502859/the-significance-of-estradiol-metabolites-in-human-corpus-luteum-physiology
#6
REVIEW
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
https://www.readbyqxmd.com/read/28502858/absolute-quantification-of-cholesteryl-esters-using-liquid-chromatography-tandem-mass-spectrometry-uncovers-novel-diagnostic-potential-of-urinary-sediment
#7
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
https://www.readbyqxmd.com/read/28502857/spirostanol-saponins-from-ypsilandra-parviflora-induce-platelet-aggregation
#8
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
https://www.readbyqxmd.com/read/28483508/synthesis-of-novel-4-acylamino-modified-21e-benzylidene-steroidal-derivatives-and-their-cytotoxic-activities
#9
Ning-Juan Fan, Yang-Yang Han, Yuan-Feng Li, Jin-Ming Gao, Jiang-Jiang Tang
A series of 4'-acylamino modified Δ(1,4)-pregnadien-21E-benzylidene-3,20-dione derivatives (6a-v) was synthesized from the commercially available progesterone (1). These title compounds were evaluated for their toxicity against brine shrimp (Artemia salina) and cytotoxic activities against two human cancer cell lines (HeLa and MCF-7). The results revealed that compound 6f exhibited promising in vitro cytotoxic activity to the two cancer cell lines and the nature of acylamino functional group in the benzylidene moiety had a significant influence on cytotoxicity...
May 5, 2017: Steroids
https://www.readbyqxmd.com/read/28483507/synthesis-and-spectral-properties-of-estrogen-and-androgen-bodipy-conjugates
#10
Samira Osati, Hasrat Ali, Brigitte Guerin, Johan E van Lier
To develop receptor based fluorescence ligands for imaging breast and prostate cancer, a series of estrogen-, testosterone- and 19-nortestosterone conjugates linked to BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) or aza-BODIPY, were prepared. Their synthesis involves attachment of iodo derivatives of differently substituted BODIPY and aza-BODIPY analogs to the C17α-position of the steroid moieties using either the Sonogashira coupling or Click reaction. The UV-Vis absorption spectra of the conjugates range from 500 to 710nm with fluorescence emission properties ranging from 520 to 700nm, facilitating observations in living cells and tissues...
May 5, 2017: Steroids
https://www.readbyqxmd.com/read/28456451/high-sensitivity-determination-of-estrogens-in-fish-plasma-using-chemical-derivatization-upstream-uhplc-msms
#11
Ugo Bussy, Yu-Wen Chung-Davidson, Tyler J Buchinger, Ke Li, Weiming Li
This article describes the development and validation of a sensitive LC-MSMS method for determination of estrogen in fish plasma. Dansyl chloride derivatization of the phenol functional group in estrogen was used to enhance the response to atmospheric pressure ionization leading to improve the sensitivity. Individual (13)C internal standards were selected after comparison with deuterated standards. Liquid-liquid extraction (ethyl acetate or methyl tert-butyl ether) and protein precipitation (acetonitrile, methanol or acetone) were compared for the extraction and clean-up of estrogens from fish plasma...
April 27, 2017: Steroids
https://www.readbyqxmd.com/read/28450069/circulating-steroids-negatively-correlate-with-tinnitus
#12
Pavel Chrbolka, Zoltán Palúch, Martin Hill, Štefan Alušík
While not a disease entity in itself; symptoms of tinnitus (from Latin tinnio - clink) accompany a number of diseases. Tinnitus prevalence increases with age, deteriorates one's quality of life, and may even result in suicidal behavior. Tinnitus develops in response to a variety of risk factors, otoxic substances, noise exposure, hearing disorders, and psychological alterations. Tinnitus is closely related to mood, depression, and psychological state. In the present study, we focused on alterations of the steroid metabolome and particularly neuroactive, neuroprotective, and immunomodulatory steroids in patients with tinnitus...
April 25, 2017: Steroids
https://www.readbyqxmd.com/read/28450070/synthesis-of-androstene-oxime-nitrogen-mustard-bioconjugates-as-potent-antineoplastic-agents
#13
Pratap Chandra Acharya, Ranju Bansal
In the present study, synthesis and antineoplastic activity of phenylacetic acid and benzoic acid nitrogen mustard conjugates of various steroidal oximes are reported for the first time. The conjugation was achieved through a more stable oxime-ester linkage and the resulting newly synthesized conjugates were evaluated in vitro on various human cancer cell lines for cytotoxicity. The extent of their alkylating activity was investigated by the in vitro colorimetric 4-(p-nitrobenzyl)pyridine (NBP) assay. The 17E-steroidal oxime-benzoic acid mustard ester 3β-acetoxy-17E-[p-(N,N-bis(2-chloroethyl)amino)]benzoyloxyimino-androst-5-ene (8) emerged as the most potent conjugate having significant cytotoxicity on most of the NCI 60-cell lines...
April 24, 2017: Steroids
https://www.readbyqxmd.com/read/28435038/a-convergent-synthesis-of-novel-alkyne-azide-cycloaddition-congeners-of-betulinic-acid-as-potent-cytotoxic-agent
#14
Nisar A Dangroo, Jasvinder Singh, Santosh K Rath, Nidhi Gupta, Arem Qayum, Shashank Singh, Payare L Sangwan
In an endeavour to develop potent anti-tumor agents from betulinic acid (BA), a series of C-28 derived 1,2,3-triazolyl derivatives were designed and synthesized by employing Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. All the derivatives were evaluated for cytotoxic activity by MTT assay against five different human cancer cell lines: lung (A549), colon (HCT116), prostate (PC3), pancreatic (MIA PaCa-2) and breast (T47D). The data revealed that compounds 11c, 11d, 11g, 11h and 13a possess most promising cytotoxic potential...
April 21, 2017: Steroids
https://www.readbyqxmd.com/read/28404456/biotransformation-of-anabolic-compound-methasterone-with-macrophomina-phaseolina-cunninghamella-blakesleeana-and-fusarium-lini-and-tnf-%C3%AE-inhibitory-effect-of-transformed-products
#15
Malik Shoaib Ahmad, SammerYousuf, Atia-Tul-Wahab, Almas Jabeen, Atta-Ur-Rahman, M Iqbal Choudhary
Microbial transformation of methasterone (1) was investigated with Macrophomina phaseolina, Cunninghamella blakesleeana, and Fusarium lini. Biotransformation of 1 with M. phaseolina yielded metabolite 2, while metabolites 3-7 were obtained from the incubation of 1 with C. blakesleeana. Metabolites 8-13 were obtained through biotransformation with F. lini. All metabolites, except 13, were found to be new. Methasterone (1) and its metabolites 2-6, 9, 10, and 13 were then evaluated for their immunomodulatory effects against TNF-α, NO , and ROS production...
April 9, 2017: Steroids
https://www.readbyqxmd.com/read/28396219/novel-synthesis-of-steroidal-oximes-and-lactams-and-their-biological-evaluation-as-antiproliferative-agents
#16
Roxana Martínez-Pascual, Socorro Meza-Reyes, José Luis Vega-Baez, Penélope Merino-Montiel, José M Padrón, Ángel Mendoza, Sara Montiel-Smith
A novel three-step methodology to obtain 6a-aza-B-homo steroidal lactams has been developed starting from the easily available cholesterol and pregnenolone. In addition, a new procedure for the synthesis of a 6a-aza-B-homo steroidal lactam analog of vespertilin, starting from diosgenin has been established. In both synthetic pathways, the key intermediate is a hydroxyimino derivative obtained in a one- or two-step sequence from the starting materials. These methods avoid the use of hazardous oxidant agents in the process...
April 7, 2017: Steroids
https://www.readbyqxmd.com/read/28377207/2-naphthoic-acid-ergosterol-ester-an-ergosterol-derivative-exhibits-anti-tumor-activity-by-promoting-apoptosis-and-inhibiting-angiogenesis
#17
Mingzhu Lin, Haijun Li, Yan Zhao, Enbo Cai, Hongyan Zhu, Yugang Gao, Shuangli Liu, He Yang, Lianxue Zhang, Guosheng Tang
Phytosterol is a natural component of vegetable oil and includes ergosterol (ER) and β-sitosterol. In this study, three new ergosterol monoester derivatives were obtained from the reflux reaction with ergosterol, organic acids (furoic acid, salicylic acid, and 2-naphthoic acid), EDCI, and DMAP in dichloromethane. The chemical structures were defined by IR and NMR. On the basis of the results, 2-naphthoic acid ergosterol ester (NE) had the highest tumor inhibition rate and was selected to study anti-tumor activity and its mechanism at doses of 0...
April 1, 2017: Steroids
https://www.readbyqxmd.com/read/28342744/synthesis-and-anti-cancer-activity-of-chiral-tetrahydropyrazolo-1-5-a-pyridine-fused-steroids
#18
Susana M M Lopes, Emanuel P Sousa, Luísa Barreira, Cátia Marques, Maria João Rodrigues, Teresa M V D Pinho E Melo
Regio- and stereoselective synthesis of novel chiral 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused steroids via [8π+2π] cycloaddition of diazafulvenium methides with steroidal scaffolds is reported. The biological evaluation of the new family of hexacyclic steroids as anti-cancer agents was also carried out. Hexacyclic steroids bearing a benzyl group at C-22, derived from 16-dehydropregnenolone and 16-dehydroprogesterone, show considerable cytotoxicity against EL4 (murine T-lymphoma) in contrast with the corresponding C-22-unsubstituted derivatives showing low cytotoxicity...
March 22, 2017: Steroids
https://www.readbyqxmd.com/read/28327355/cytotoxic-and-apoptosis-inducing-activity-of-c21-steroids-from-the-roots-of-cynanchum-atratum
#19
Jian Zhang, Lin Ma, Zheng-Feng Wu, Shu-Le Yu, Lei Wang, Wen-Cai Ye, Qing-Wen Zhang, Zhi-Qi Yin
Two new (1-2) and two known C21 steroids (3-4) were isolated from the roots of Cynanchum atratum. Their structures were elucidated by detailed 1D and 2D spectroscopic. The MTT assay showed that compounds 1-4 displayed obvious cytotoxic activities against HepG2 cells with IC50 values ranging from 10.19μM to 76.12μM. Compounds 1-3 also exhibited cytotoxic effects in A549 cells with IC50 values of 30.87-95.39μM. Compound 3 showed the antiproliferative activity via G0/G1 cell cycle arrest and proapoptosis in HepG2 cells by Flowcytometry analysis...
March 19, 2017: Steroids
https://www.readbyqxmd.com/read/28322864/water-soluble-derivatives-of-25-och3-ppd-and-their-anti-proliferative-activities
#20
Wu-Xi Zhou, Yuan-Yuan Sun, Wei-Hui Yuan, Yu-Qing Zhao
(20R)-25-Methoxyl-dammarane-3β,12β,20-triol (25-OCH3-PPD, AD-1) is a dammarane-type sapogenin showing anti-tumor potential. In the search for new anti-tumor agents with higher potency than our previously identified compound 25-OCH3-PPD, 11 novel sulfamic acid and diacid derivatives that could improve water solubility and contribute to good drug potency and pharmacokinetic profiles were designed and synthesized. Their in vitro anti-tumor activities in MCF-7, A-549, HCT-116, and BGC-823 cell lines and one normal cell line were tested by standard MTT assay...
March 18, 2017: Steroids
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