Biosynthesis of steroids from squalene

When the squalene molecule is represented as in Figure 20-35, the relationship of its linear structure to the cyclic structure of the sterols is apparent. All of the sterols have four fused rings (the steroid nucleus) and all are alcohols, with a hydroxyl group at C-3; thus the name "sterol." The action of squalene monooxygenase adds one oxygen atom from O 2 to the end of the squalene chain, forming an epoxide. This enzyme is another mixed-function oxidase (Box 20-1); NADPH reduces the other oxygen atom of O 2 to H 2 O. The double bonds of the product, squalene2,3-epoxide , are positioned so that a remarkable concerted reaction can convert the linear squalene epoxide into a cyclic structure. In animal cells, this cyclization results in the formation of lanosterol , which contains the four rings characteristic of the steroid nucleus. Lanosterol is finally converted into cholesterol in a series of about 20 reactions, including the migration of some methyl groups and the removal of others. Elucidation of this extraordinary biosynthetic pathway, one of the most complex known, was accomplished by Konrad Bloch, Feodor Lynen, John Cornforth, and George Popjak in the late 1950s.

1. Metabolism
     Global/overview    Carbohydrate    Energy    Lipid    Nucleotide    Amino acid    Other amino    Glycan
     Cofactor/vitamin    Terpenoid/PK    Other secondary metabolite    Xenobiotics    Chemical structure
2. Genetic Information Processing
3. Environmental Information Processing
4. Cellular Processes
5. Organismal Systems
6. Human Diseases
7. Drug Development

Anabolic steroids are synthetic substances related to male sex hormones (androgens). Although it is illegal in the United States to possess or distribute anabolic steroids for nonmedical use, a "black market" for them exists, and many amateur and professional athletes take them to enhance performance. In many cases, the athletes take doses that are extremely high—perhaps 100 times the doses that might be prescribed for medical use. As a result, they put themselves in real danger of short-term and long-term health problems. Blood testing, as has been used in the Olympic Games, can detect, identify, and quantify the presence of anabolic steroids in the blood of athletes, which can lead to the disqualification of an athlete.

The early steps in the biosynthesis of steroids of both plants and animals are the same, except that in plants lanosterol is replaced by the related compound cycloartenol, which contains a three-membered ring (C9, C10, C19) in lieu of the nuclear double bond of lanosterol. The side chains of the phytosterols, such as stigmasterol, and of the sterol ergosterol of yeasts and other fungi contain extra carbon atoms that are incorporated in reactions involving S -adenosylmethionine, which donates methyl groups in numerous biological processes. Although most plant tissues contain only traces of cholesterol, this sterol is the biogenetic precursor of such important plant steroids as the sapogenins , glycosides , and alkaloids . Because pregnane derivatives are intermediates in some of these transformations, plants and animals appear to have important features of steroid metabolism in common.

Biosynthesis of steroids from squalene

biosynthesis of steroids from squalene

The early steps in the biosynthesis of steroids of both plants and animals are the same, except that in plants lanosterol is replaced by the related compound cycloartenol, which contains a three-membered ring (C9, C10, C19) in lieu of the nuclear double bond of lanosterol. The side chains of the phytosterols, such as stigmasterol, and of the sterol ergosterol of yeasts and other fungi contain extra carbon atoms that are incorporated in reactions involving S -adenosylmethionine, which donates methyl groups in numerous biological processes. Although most plant tissues contain only traces of cholesterol, this sterol is the biogenetic precursor of such important plant steroids as the sapogenins , glycosides , and alkaloids . Because pregnane derivatives are intermediates in some of these transformations, plants and animals appear to have important features of steroid metabolism in common.

Media:

biosynthesis of steroids from squalenebiosynthesis of steroids from squalenebiosynthesis of steroids from squalenebiosynthesis of steroids from squalenebiosynthesis of steroids from squalene

http://buy-steroids.org