566-27-8Relevant articles and documents
Cholesterol degradation in archaeological pottery mediated by fired clay and fatty acid pro-oxidants
Hammann, Simon,Cramp, Lucy J.E.,Whittle, Mathilda,Evershed, Richard P.
, p. 4401 - 4404 (2018)
Cholesterol is generally absent in animal fat residues preserved in archaeological ceramic vessels. It is known from edible oil refining that during bleaching with activated clay sterols are degraded, largely via oxidation. Laboratory heating experiments
Metal-Free Allylic Oxidation of Steroids Using TBAI/TBHP Organocatalytic Protocol
Lam, Ying-Pong,Yeung, Ying-Yeung
supporting information, p. 2369 - 2372 (2018/04/19)
A mild, efficient and organocatalytic allylic oxidation of steroids using a TBAI/TBHP protocol has been developed. A range of bioactive Δ5-en-7-ones can be easily prepared from the corresponding Δ5-steroids. The methodology features several advantages, including readily available starting materials, environmentally benign oxidant, high functional group compatibility, and metal-free catalysis.
Oxyphytosterols as active ingredients in wheat bran suppress human colon cancer cell growth: Identification, chemical synthesis, and biological evaluation
Zhu, Yingdong,Soroka, Dominique,Sang, Shengmin
, p. 2267 - 2276 (2015/03/14)
Consumption of whole grains has been reported to be associated with a lower risk of colorectal cancer. Recent studies illustrated that phytochemicals in wheat bran (WB) may protect against colorectal cancer. There is a growing interest in the phytosterol contents of foods as either intrinsic or added components due to their beneficial health effects. However, little is known whether phytosterols in WB contribute the observed chemopreventative activity of the grain. In the present study, we directly purified and identified four oxyphytosterols 1-4 from sterol-enriched fraction of WB, and also successfully synthesized five sterol oxides 5-8 and 13. Using these nine compounds as references, we outlined a comprehensive profile of steroids in WB using tandem liquid chromatography mass spectrometry with electrospray ionization (LC-ESI/MSn, n = 2-3) techniques for the first time. Among them, three sterol oxides 13, 14, and 18 are novel compounds, and 14 compounds 3, 4, 6-11, 13, 14, 16, and 18-20 were reported in WB for the first time. Our results on the inhibitory effects of available sterol oxides 1-8 and 13 against the growth of human colon cancer cells HCT-116 and HT-29 showed that compounds 2-8 exerted significant antiproliferative effects, with oxysterol 8 being the most active one in both cells. We further demonstrated that four most active sterol oxides 5-8 could induce cell death through the apoptosis pathway. Our results showed that phytosterols, particularly oxyphytosterols, in WB possess significant antiproliferative properties, and thereby may greatly contribute the observed chemoprevention of the whole grain wheat.
