Biotransformation of Dehydroepiandrosterone by Penicillium olsonii MRC500780

Year 2024, Volume: 28 Issue: 6, 1261 - 1266, 31.12.2024

Ali Kuru , Mena Albayaty

https://doi.org/10.16984/saufenbilder.1496783

https://izlik.org/JA54HR57JX

Abstract

This work reported the biotransformation of dehydroepiandrosterone 1 with Penicillium olsonii MRC500780. Structure determinations revealed that biotransformation of 1 by Penicillium olsonii MRC500780 afforded androst-4-ene-3,17-dione 2, 15α-hydroxyandrost-4-ene-3,17-dione 3, 3β,7β-dihydroxyandrost-5-ene-17-one 4, 3β,7α-dihydroxyandrost-5-ene-17-one 5, and 15α,17β-dihydroxyandrost-4-ene-3-one 6. This fungus primarily isomerized the starting material in terms of the double bond and the hydroxyl group at 3β oxidised, then hydroxylated it at the C-15α position and reduced it at the C-17 position; also, hydroxylations at the C-7α position and C-7β position were observed.

Keywords

Penicillium olsonii , Dehydroepiandrosterone , Biotransformation

Supporting Institution

SAÜ BAPK

Project Number

2022-7-24-160

References

• M. S. Smitha, S. Singh, R. Singh, “Microbial biotransformation: A process for chemical alterations”, Journal of Bacteriology & Mycology: Open Access, vol. 4, no.2, p. 85, 2017.
• N. Nassiri-Koopaei, M. A. Faramarzi, “Recent developments in the fungal transformation of steroids”, Biocatalysis and Biotransformation, vol. 33, no.1, pp. 1-28, 2015.
• V. Dave, P. Khirwadkar, K. Dashora, “A review on biotransformation”, Indian Journal of Research in Pharmacy and Biotechnology, vol. 2, no. 2, p. 1136, 2014.
• S.S. Mohamed, A. A. El-Hadi, K. M. Abo-Zied, “Biotransformation of prednisolone to hydroxy derivatives by Penicillium aurantiacum”, Biocatalysis and Biotransformation, vol. 35, no.3, pp. 215-222, 2017.
• M. Panjari, S. R. Davis, “DHEA therapy for women: Effect on sexual function and wellbeing”, Human reproduction update, vol. 13, no. 3, pp. 239-248, 2007.
• L.H. Huang, J. Li, G. Xu, X. H. Zhang, Y. G. Wang, Y. L. Yin, H. M. Liu, “Biotransformation of dehydroepiandrosterone (DHEA) with Penicillium griseopurpureum Smith and Penicillium glabrum (Wehmer) Westling”, Steroids, vol. 75, no.13, pp. 1039-1046, 2010.
• A. Swizdor, “Baeyer-villager oxidation of some C19 steroids by penicillium lanosocoeruleum”, Molecules, vol. 18, no. 11, pp. 13812–13822, 2013.
• T. Kołek, A. Szpineter, A. Świzdor, “Baeyer-Villiger oxidation of DHEA, pregnenolone, and androstenedione by Penicillium lilacinum AM111”, Steroids, vol. 73, no. 14, pp. 1441–1445, 2008.
• A. Panek, P. Łyczko, A. Świzdor, “Microbial modifications of androstane and androstene steroids by Penicillium vinaceum”, Molecules, vol. 25, no. 18, p. 4226, 2020.
• E. Kozłowska, M. Urbaniak, A. Kancelista, M. Dymarska, E. Kostrzewa-Susłow, Ł. Stępień, T. Janeczko, “Biotransformation of dehydroepiandrosterone (DHEA) by environmental strains of filamentous fungi”, RSC advances, vol. 7, no. 50, pp. 31493-31501, 2017.
• H. M. Liu, H. Li, L. Shan, J. Wu, “Synthesis of steroidal lactone by penicillium citreo-viride”, Steroids, vol. 71, no. 11, pp. 931-934, 2006.‏
• B. Yang, Y. Wang, X. Chen, J. Feng, Q. Wu, D. Zhu, Y. Ma, “Biotransformations of steroids to testololactone by a multifunctional strain Penicillium simplicissimum WY134-2”, Tetrahedron, vol. 70, no. 1, pp. 41-46, 2014.
• T. Kołek, A. Szpineter, A. Świzdor, “Studies on Baeyer–Villiger oxidation of steroids: DHEA and pregnenolone d-lactonization pathways in Penicillium camemberti AM83”, Steroids, vol. 74, no. 10, pp. 859-862, 2009.
• T. Iida, K. Omura, R. Sakiyama, M. Kodomari, “Regioselective dehydrogenation of 3-keto-steroids to form conjugated enones using o-iodoxybenzoic acid and trifluoroacetic acid catalysis”, Chemistry and Physics of Lipids, vol. 178, pp. 45-51, 2014.
• P. C. Peart, K. P. McCook, F. A. Russell, W. F. Reynolds, P. B. Reese, “Hydroxylation of steroids by Fusarium oxysporum, Exophiala jeanselmei and Ceratocystis paradoxa”, Steroids, vol. 76, no.12, pp. 1317-1330, 2011.
• C. S. Bensasson, J. R. Hanson, Y. Le Huerou, “The microbiological hydroxylation of 3α, 5-cycloandrostanes by Cephalosporium aphidicola”, Phytochemistry, vol. 52, no. 7, pp. 1279-1282, 1999.
• D. N. Kirk, H. C. Toms, C. Douglas, K. A. White, K. E. Smith, S. Latif, R.W.P Hubbard, “A survey of the high-field 1H NMR spectra of the steroid hormones, their hydroxylated derivatives, and related compounds”, Journal of the Chemical Society, Perkin Transactions, vol. 2, pp. 1567-1594, 1990.
• J. W. Blunt, J. B. Stothers, “13C NMR spectra of steroids a survey and commentary”, Organic Magnetic Resonance, vol. 9, pp. 439-464, 1977.