57760-54-0Relevant academic research and scientific papers
Marine and semi-synthetic hydroxysteroids as new scaffolds for pregnane X receptor modulation
Sepe, Valentina,Di Leva, Francesco Saverio,D'Amore, Claudio,Festa, Carmen,De Marino, Simona,Renga, Barbara,D'Auria, Maria Valeria,Novellino, Ettore,Limongelli, Vittorio,D'Souza, Lisette,Majik, Mahesh,Zampella, Angela,Fiorucci, Stefano
, p. 3091 - 3115 (2014)
In recent years many sterols with unusual structures and promising biological profiles have been identified from marine sources. Here we report the isolation of a series of 24-alkylated-hydroxysteroids from the soft coral Sinularia kavarattiensis, acting as pregnane X receptor (PXR) modulators. Starting from this scaffold a number of derivatives were prepared and evaluated for their ability to activate the PXR by assessing transactivation and quantifying gene expression. Our study reveals that ergost-5-en-3β-ol (4) induces PXR transactivation in HepG2 cells and stimulates the expression of the PXR target gene CYP3A4. To shed light on the molecular basis of the interaction between these ligands and PXR, we investigated, through docking simulations, the binding mechanism of the most potent compound of the series, 4, to the PXR. Our findings provide useful functional and structural information to guide further investigations and drug design.
Synthesis of a New Vitamin D3 Hapten and Its Protein Conjugates
Litvinovskaya,Savachka,Sauchuk,Pradko,Mirantsova,Khripach
, p. 778 - 786 (2019/02/26)
The synthesis of 25-(1-carboxymethoxy)-imino-3(S)-hydroxy-9,10-seco-27-norcholesta-5(Z),7(E),10(19)-triene, a new hapten of vitamin D3, has been carried out in ten steps from ergosterol. The hapten was conjugated to horseradish peroxidase and bovine serum albumin. Antibodies to 25-hydroxyvitamin D3 were obtained using the synthesized conjugates. An immunochemical system was developed for the quantitative determination of 25-hydroxyvitamin D3.
Steroid from the seeds of artabotrys odoratissimus
Prasad, Subedar,Gupta, Chitrasen
, p. 353 - 356 (2015/06/30)
A steroid has been isolated from the seeds of Artabotrys odoratissimus (Annonaceae) and its structure has been established as (3β, 22E)-ergosta-5,7,22-trien-3-ol by spectroscopic and chemical studies. By chemical correlations, it has been identified as a known compound ergosterol. This is the first report of isolation of ergosterol from this plant.
STEROL DERIVATIVE
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Page/Page column 49, (2012/06/05)
The present invention provides a sterol derivative or a pharmaceutically acceptable salt thereof having an activity to promote proliferation of neural stem cells. Namely, the present invention provides a sterol derivative represented by the general formula (I) (wherein Y represents optionally substituted lower alkyl or the like; Xa and Xb are the same or different, and represent a bond or the like; R1, R2, R3, R4, R7 and R8 are the same or different, and represent a hydrogen atom or the like; R5 and R6 are the same or different, and represent a hydrogen atom or the like; R9 represents a hydrogen atom or the like; R10 and R11 together represent a bond or the like; and R12 represents a hydrogen atom or the like) or a pharmaceutically acceptable salt thereof.
Synthetic routes to campesterol and dihydrobrassicasterol: A first reported synthesis of the key phytosterol dihydrobrassicasterol
O'Connell,O'Callaghan,O'Brien,Maguire,McCarthy
experimental part, p. 4995 - 5004 (2012/08/28)
Phytosterols are increasingly used as health supplements in functional foods and are associated with having both positive and negative effects on health. Given this disparity, an investigation of their full individual biological profile is imperative in order to assure food safety. This paper describes the de novo synthesis of pure phytosterols in multigram scale and we report the first synthesis of the key phytosterol dihydrobrassicasterol along with a comparison of routes to campesterol. A detailed spectroscopic analysis is included with full assignment of the 13C NMR spectroscopic data of both compounds, mixtures and their precursors leading to the potential use of NMR spectroscopy as a tool for analysis of these sterol mixtures.
Synthesis of 6-F-ergosterol and its influence on membrane-permeabilization of amphotericin B and amphidinol 3
Kasai, Yusuke,Matsumori, Nobuaki,Ueno, Hiroyuki,Nonomura, Kenichi,Yano, Shinya,Michio, Murata,Oishi, Tohru
scheme or table, p. 1437 - 1442 (2011/04/22)
Two well-known antifungals, amphotericin B (AmB) and amphodinol 3 (AM3), are thought to exert antifungal activity by forming ion-permeable channels or pores together with sterol molecules. However, detailed molecular recognitions for AmB-sterol and AM3-sterol in lipid bilayers have yet to be determined. Toward 19F NMR-based investigation of the molecular recognition underlying their potent antifungal activity, we synthesized 6-fluoro-ergosterol in five steps via ring opening of (5α,6α)-epoxide of ergosterol acetate with using novel combination of TiF4 and n-Bu 4N+Ph3SiF2-. Then we evaluated its activity of promoting pore formation of AmB and AM3, and found that pore formation of AmB was barely promoted by 6-F-ergosterol in clear contrast to the dramatic promotion effect of unmodified ergosterol, whereas AM3 activity was markedly enhanced in the presence of 6-F-ergosterol, which was comparable to that of unmodified ergosterol. These results indicate that the introduction of an F atom at C6 position of ergosterol plays an inhibitory role in interacting with AmB, but it is not the case with AM3. The Royal Society of Chemistry 2011.
Syntheses and biological activity studies of novel sterol analogs from nitroso diels-alder reactions of ergosterol
Yang, Baiyuan,Miller, Patricia A.,Moellmann, Ute,Miller, Marvin J.
supporting information; experimental part, p. 2828 - 2831 (2009/12/06)
A serles of novel sterol analogs was prepared using nitroso Dlels-Alder reactions with ergosterol. Most cycloaddltlon reactions proceeded In an excellent reglo- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity In PC-3 and MCF-7 cancer cell lines
Side chain azasteroids and thiasteroids as sterol methyltransferase inhibitors in ergosterol biosynthesis
Renard, Delphine,Perruchon, Johann,Giera, Martin,Mueller, Joerg,Bracher, Franz
scheme or table, p. 8123 - 8137 (2010/03/30)
The synthesis of some novel azasteroids and thiasteroids based on a pregnan nucleus with a Δ7 double bond in two to five steps from the key aldehyde (3S,20S)-20-formylpregn-7-en-3-yl acetate has been disclosed herein. These compounds were evaluated as potential inhibitors of the enzyme Δ24-sterol methyltransferase (24-SMT), which is a key enzyme in the biosynthesis of ergosterol, and for their effects on the growth of the yeast Yarrowia lipolytica. Most of the side chain modified analogues were recognized as 24-SMT inhibitors, and in particular the 23-azasteroids 5f-5i and the 24-azasteroid 11 showed potent antifungal activity. The target enzyme could be identified unambiguously using an improved whole-cell assay combined with GC-MS analysis of the sterol pattern resulting upon incubation with the inhibitors.
Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2
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, (2008/06/13)
A method of inhibiting the hyperproliferation of malignant or neoplastic cells, comprising treating the cells with an antiproliferative amount of 1α,24(S)-dihydroxyvitamin D2. The method also includes the co-administration of cyotoxic agents with the 1α,24(S)-dihydroxyvitamin D2.
Methods for preparation and use of 1α,24(S)-dihydroxyvitamin D2
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, (2008/06/13)
A method of inhibiting the hyperproliferation of malignant or neoplastic cells, comprising treating the cells with an antiproliferative amount of 1α,24(S)-dihydroxyvitamin D2. The method also includes the co-administration of cyotoxic angents with the 1α,24(S)-dihydroxyvitamin D2.
