Transformations of Steroids and Sterols,Glucocorticoids,Mineralocorticoids,Androgens,Estrogens,Progesterones,Molecular Skeleton

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Transformations of Steroids and Sterols
Most steroids have hormone properties and include glucocorticoids, mineralocorticoids, androgens, estrogens. progesterones. etc. All these steroids have a basic molecular skeleton, which is cyclopentano-perhydrophenanthrene or sterane nucleus.

Basic skelton sterane nucleus of a steroid molecules

Basic Skeleton Sterane Nucleus of a Steroid Molecule

One of the steroid hormone is progesterone, which is quite active during pregnancy. On industrial scale it acts as a precursor for producing atleast four other products, using micro-organisms. These conversions involve hydroxylation and dehydrogenation. The hydroxylated dehydro-genated products have better efficacy as hormone. For example, the oxygen at C – 11 is essential for the anti-inflammatory cortisone (another steroid hormone). The cortisone itself can be produced from progesterone and then modified.

Microbial Conversion of Progesterone

In 1949, 1.0g of cortisone was produced at a cost of about 200 US dollars, but as a result of introduction of the microbial process for the C-11 hydroxylation of progesterone, the cost had decreased to under 1 US dollar by 1979. Currently, almost all positions of the steroid molecules can be specifically hydroxylated by different micro-organisms.

Steroid hormones can also be produced from sterol precursors which are quite inexpensive. For instance, Diosgenin, β-sitosterol, cholesterol, etc. are often used as hormone precursors. These sterols have the same sterane nucleus and one or more side chains. The basic approach in their microbial bio-conversion is to remove the side chain. Production of some steroid hormones using cholesterol as primary molecule with the help of mycobacteria.

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Biotransformation of Cholestrol to androstadiendione by mycobacteria

Biotransformation of Cholesterol to Androstadiendione by Mycobacteria

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