Microbial Transformation of Epiandrosterone by Penicillium olsonii MRC500780

Year 2025, Volume: 36 Issue: 3, 194 - 198, 30.11.2025

Ali Kuru , Hümeyra Yılmaz

https://doi.org/10.36483/vanvetj.1722984

Abstract

Microbial fungal biotransformation refers to the ability of fungi to enzymatically modify organic compounds, often yielding structurally similar products with altered properties. This approach has gained considerable attention as a sustainable and selective alternative to conventional chemical synthesis, particularly in the context of complex molecules like steroids. Fungal species, especially filamentous types, are known for their rich enzymatic repertoire, which allows them to carry out site-specific modifications such as hydroxylation or oxidation. These transformations are not only efficient but also valuable for generating pharmacologically relevant derivatives. In the present study, we focused on the bioconversion of epiandrosterone 1 using Penicillium olsonii MRC500780. Through incubation under controlled conditions, we aimed to explore the metabolic capacity of this strain to produce new steroidal metabolites. The findings suggest that P. olsonii holds promise as a biocatalyst for steroid modification in pharmaceutical and biotechnological applications. Structure determinations showed that five-days biotransformation of epiandrosterone 1 by Penicillium olsonii MRC500780 afforded 4 metabolites. The four identified metabolites were as follows: 2, characterized by hydroxylation at the 15α-position of the 5α-androstane-3,17-dione scaffold; 3, bearing hydroxyl groups at both the 3β and 15α positions on the 5α-androstan-17-one backbone; 4, featuring hydroxylations at the 3β and 11α positions of 5α-androstan-17-one; 5, possessing hydroxyl groups at the 3β and 7α positions on the same steroidal framework.The biotransformation process revealed that P. olsonii MRC500780 catalyzed hydroxylation reactions at the C-7α, C-11α, and C-15α positions of epiandrosterone 1, along with an oxidative modification occurring at the C-3 site.

Keywords

Biocatalysis , Epiandrosterone , Penicillium

Ethical Statement

In accordance with the decision no. 16 taken during the 61st meeting of the Sakarya University Rectorate Ethics Committee held on 24 June 2025, it was concluded that ethics committee approval was not required for this study.

Epiandrosteronun Penicillium olsonii MRC500780 ile Mikrobiyal Transformasyonu

Abstract

Mikrobiyal fungal biyotransformasyon, küflerin organik bileşikleri enzimatik olarak değiştirme yeteneğini ifade eder; bu süreç genellikle yapısal olarak benzer, ancak özellikleri değiştirilmiş ürünler ortaya çıkarır. Bu yaklaşım, özellikle steroidler gibi karmaşık moleküller söz konusu olduğunda, geleneksel kimyasal senteze sürdürülebilir ve seçici bir alternatif olarak son yıllarda büyük ilgi görmektedir. Özellikle filamentöz türler olmak üzere birçok küf türü, hidroksilasyon veya oksidasyon gibi belirli konumlara özgü kimyasal değişiklikleri gerçekleştirebilen zengin bir enzim repertuarına sahiptir. Bu dönüşümler, yalnızca verimli olmakla kalmaz, aynı zamanda farmakolojik açıdan değerli türevlerin elde edilmesini de sağlar. Bu çalışmada, epiandrosteron 1’in Penicillium olsonii MRC500780 suşu tarafından biyotransformasyonuna odaklanılmıştır. Kontrollü koşullar altında yapılan inkübasyonlarla, bu suşun yeni steroidal metabolitler üretme potansiyeli araştırılmıştır. Elde edilen sonuçlar, P. olsonii’nin farmasötik ve biyoteknolojik uygulamalarda steroid modifikasyonu için umut vadeden bir biyokatalizör olduğunu göstermektedir. Yapı tayinleri, epiandrosteron 1’in Penicillium olsonii MRC500780 tarafından 5 gün süren biyotransformasyonu sonucunda dört metabolitin elde edildiğini ortaya koymuştur. Elde edilen dört metabolit sırasıyla; 15α-hidroksillenmiş 5α-androstan-3,17-dion 2, 3β ve 15α konumlarında hidroksil grupları taşıyan 5α-androstan-17-on 3, 3β ve 11α pozisyonlarında hidroksillenmiş 5α-androstan-17-on 4 ve son olarak 3β ile 7α hidroksilasyonuna uğramış 5α-androstan-17-on 5 olarak tanımlanmıştır.Yürütülen biyotransformasyon süreci sonucunda P. olsonii MRC500780 suşunun, epiandrosteron 1 üzerinde C-7α, C-11α ve C-15α karbonlarında hidroksilasyon reaksiyonları gerçekleştirdiği; buna ek olarak, C-3 konumunda oksidatif bir dönüşüm meydana getirdiği belirlenmiştir.

Keywords

Biyokataliz , Epiandrosteron , Penisilyum

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