Biotechnological modification of steroidal structures

Erkılıç, Umut
Steroids are important biological regulators existing in hormones which are used to control metabolism of the body. There are widespread applications in the pharmaceutical industry. Drugs of steroid nature - anti-inflammatory and antiallergic corticosteroids, diuretics, anabolics, androgens, gestagens, contraceptives, antitumor medications, etc. - are now widely used in human and veterinary medicine. Nowadays, biotechnological modifications of steroids are preferred over chemical modifications as a green chemistry since they are more likely to be natural. In this work four different Fusarium species were screened for bioconversion of steroids into pharmaceutically important derivatives of steroids by reduction, dehydrogenation, side-chain degradation etc. on A and D-rings containing many active sites. Fusarium spp. used in this work, namely Fusarium roseum OUT 4019, Fusarium anguioides OUT 4017, Fusarium bulbigenum OUT 4115 and Fusarium solani OUT 4021 are filamentous fungi, which belong to the class of Deuteromyces. They can grow using simple carbohydrates and nitrogen sources. 4-androstene-3,17-dione conversion is used as a model system. Under same environmental conditions it is found that whole cells of Fusarium roseum OUT 4019 can dehydrogenate at C-1 and C-2 producing androsta-1,4-diene-3,17-dione and also reduce at C-17 in addition to dehydrogenate at C-1 and C-2 producing 17-hydroxyandrosta- 1,4-dien-3-one, Fusarium anguioides OUT 4017 can reduce at C-17 producing 17-hydroxy-androst-4-en-3-one, Fusarium solani OUT 4021 can reduce at C-3 and C-17 producing androst-4-ene-3,17-diol at 25 C° and 160 rpm with uncontrolled pH. In these conversions, androsta-1,4-diene-3,17-dione, 17-hydroxy-androsta-1,4-dien- 3-one, 17-hydroxy-androst-4-en-3-one, androst-4-ene-3,17-diol were isolated with 54 %, 22 %, 26 %, 90 % yields, respectively. In another study, bioconversion reactions of aromatic methyl ethers by Fusarium roseum OUT 4019 were investigated and for some compounds, cleavage of methyl ether was observed.
Citation Formats
U. Erkılıç, “Biotechnological modification of steroidal structures,” M.S. - Master of Science, Middle East Technical University, 2008.