Methylsteroids. III. Reduction of ketones derived from lanosterol

1957 ◽  
Vol 10 (3) ◽  
pp. 334 ◽  
Author(s):  
CS Barnes ◽  
A Palmer

The base catalysed hydrogen transfer from solvent alcohol to carbonyl groups is studied with 7,ll-dioxolanostan-3β-yl acetate (I ; R=Ac) and shown to give almost entirely 3β,7β,llβ-trihydroxylanostane (V ; R=R'=H) and the epimeric 3β,7-di-hydroxylanostan-11-ones (VI and VIII ; R=H). Generalizations are made to account for their formation and stereochemistry. The four 3β,7,11-trihydrosylanostanes are prepared.

1998 ◽  
Vol 136 (2) ◽  
pp. 147-151 ◽  
Author(s):  
David Dolmazon ◽  
Raluca Aldea ◽  
Howard Alper

2020 ◽  
Vol 21 (17) ◽  
pp. 6015
Author(s):  
Zhengwen Li ◽  
Mohamed Moalin ◽  
Ming Zhang ◽  
Lily Vervoort ◽  
Erik Hursel ◽  
...  

Most studies on the antioxidant activity of flavonoids like Quercetin (Q) do not consider that it comprises a series of sequential reactions. Therefore, the present study examines how the redox energy flows through the molecule during Q’s antioxidant activity, by combining experimental data with quantum calculations. It appears that several main pathways are possible. Pivotal are subsequently: deprotonation of the 7-OH group; intramolecular hydrogen transfer from the 3-OH group to the 4-Oxygen atom; electron transfer leading to two conformers of the Q radical; deprotonation of the OH groups in the B-ring, leading to three different deprotonated Q radicals; and finally electron transfer of each deprotonated Q radical to form the corresponding quercetin quinones. The quinone in which the carbonyl groups are the most separated has the lowest energy content, and is the most abundant quinone. The pathways are also intertwined. The calculations show that Q can pick up redox energy at various sites of the molecule which explains Q’s ability to scavenge all sorts of reactive oxidizing species. In the described pathways, Q picked up, e.g., two hydroxyl radicals, which can be processed and softened by forming quercetin quinone.


2005 ◽  
Vol 117 (38) ◽  
pp. 6370-6375 ◽  
Author(s):  
Walter Baratta ◽  
Giorgio Chelucci ◽  
Serafino Gladiali ◽  
Katia Siega ◽  
Micaela Toniutti ◽  
...  

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