1108-03-8Relevant articles and documents
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Stansbury
, p. 1243 (1943)
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Phycomysterols and other sterols from the Fungus phycomyces blakesleeanus
Barrero,Enrique Oltra,Poyatos,Jimenez,Oliver
, p. 1491 - 1496 (1998)
In the search for novel bioactive products from filamentous fungi, sterols and triterpenoids found in Phycomyces blakesleeanus were analyzed using semipreparative HPLC, GC-MS, and NMR techniques. Structures proposed for the three new compounds identified, phycomysterol A (1), phycomysterol B (2), and neoergosterol (3), were confirmed by chemical synthesis. Phycomysterols possess a new natural 19-norergostane skeleton with an aromatic B ring. Phycomysterol A showed anti-HIV activity.
Starratt,A.N.
, p. 2002 - 2003 (1976)
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
, p. 1437 - 1442 (2011)
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.
Selective acylation of hydroxy steroids with acyl cyanides
Havel,Velek,Pospisek,Soucek
, p. 2443 - 2446 (1979)
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Castells,J. et al.
, p. 2627 - 2639 (1960)
Yanotovskii et al.
, (1969)
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 (2014/07/08)
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.
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.
