2874-25-1Relevant articles and documents
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.
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.
