Biotransformation of dehydroepiandrosterone by Penicillium olsonii

Natural products not actively involved in creating and developing living things for the organisms they contain usually provide significantly better living conditions. Natural products are receiving increased attention because of their effects on other living things. Despite the fact that these compounds are numerous and have very different structures, due to some similarities in their biosynthesis, they are usually classified as terpenes, alkaloids, steroids, phenolic compounds, specialized carbohydrates, specialized peptides, polyketides, fatty acids, and fatty acid derivatives. One significant category of natural compounds is steroids. One of the most significant and well-known steroids is the cholesterol molecule that controls the fluidity of membranes in both humans and animals. Some substances with crucial roles, like vitamin D3, bile acids, and steroids, are biosynthesized from cholesterol. Cholesterol-derived steroid hormones are classified into five groups: progestogens (progestins), estrogens, androgens, androgens, mineralocorticoids, and glucocorticoids. The main circulating steroid usually classified as androgen is androgen, which encourages secondary sexual characteristics in males, such as dehydroepiandrosterone (DHEA). Biotransformations are chemical reactions when enzymes operate on materials that are not their typical substrates. The biotransformation-related enzymes can function in various biological systems or as free, fixed molecules. The most often utilized biological systems for biotransformations include bacteria, yeasts, and molds. These microbes can be used for microbial biotransformations, which have numerous benefits over current chemical synthesis techniques. These microorganisms can be immobilized on appropriate surfaces or employed freely to carry out microbial biotransformations. Due to the high regioselectivity and stereoselectivity of mold enzymes, microbial steroid biotransformations by molds are widely used to obtain many more important and functional compounds. The aim of this study was to investigate how dehydroepiandrosterone 9, also known as DHEA, is metabolized in Penicillium olsonii MRC 500780 isolate. For this purpose, fresh subcultures were periodically prepared for Penicillium olsonii MRC 500780 mold before the biotransformation experiment. Afterwards, the medium for the mold was prepared and distributed to the flasks and sterilized in an autoclave. The mold in the freshest subculture was inoculated into these flasks under sterile conditions, and the flasks were left to incubate for 3 days. DHEA 9 was added under sterile conditions to these flasks where enough mold grew and incubated for 5 days. After incubation, the medium was filtered, and possible metabolites were extracted to the organic phase by ethyl acetate extraction. The metabolites in the residue obtained by evaporation of the ethyl acetate extracts were separated by column chromatography. Structure determination of the metabolites was carried out by melting point determination, NMR and IR spectroscopy. Structure determinations revealed that biotransformation of DHEA 9 by Penicillium olsonii MRC 500780 resulted in the compounds androst-4-ene-3,17-dione 5 (8%), 15α-hydroxyandrost-4-ene-3,17-dione 15 (21%), 3β,7β-dihydroxyandrost-5-ene-17-one 21 (8%), 3β,7α-dihydroxyandrost-5-ene-17-one 22 (29%) and 15α,17β-dihydroxyandrost-4-ene-3-one 23 (6%).