Research Article
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Year 2024, , 1261 - 1266, 31.12.2024
https://doi.org/10.16984/saufenbilder.1496783

Abstract

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.

Biotransformation of Dehydroepiandrosterone by Penicillium olsonii MRC500780

Year 2024, , 1261 - 1266, 31.12.2024
https://doi.org/10.16984/saufenbilder.1496783

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.

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.
There are 18 citations in total.

Details

Primary Language English
Subjects Organic Chemistry (Other)
Journal Section Research Articles
Authors

Ali Kuru 0000-0002-8300-1572

Mena Albayaty 0009-0009-6630-2902

Project Number 2022-7-24-160
Early Pub Date December 11, 2024
Publication Date December 31, 2024
Submission Date June 6, 2024
Acceptance Date December 7, 2024
Published in Issue Year 2024

Cite

APA Kuru, A., & Albayaty, M. (2024). Biotransformation of Dehydroepiandrosterone by Penicillium olsonii MRC500780. Sakarya University Journal of Science, 28(6), 1261-1266. https://doi.org/10.16984/saufenbilder.1496783
AMA Kuru A, Albayaty M. Biotransformation of Dehydroepiandrosterone by Penicillium olsonii MRC500780. SAUJS. December 2024;28(6):1261-1266. doi:10.16984/saufenbilder.1496783
Chicago Kuru, Ali, and Mena Albayaty. “Biotransformation of Dehydroepiandrosterone by Penicillium Olsonii MRC500780”. Sakarya University Journal of Science 28, no. 6 (December 2024): 1261-66. https://doi.org/10.16984/saufenbilder.1496783.
EndNote Kuru A, Albayaty M (December 1, 2024) Biotransformation of Dehydroepiandrosterone by Penicillium olsonii MRC500780. Sakarya University Journal of Science 28 6 1261–1266.
IEEE A. Kuru and M. Albayaty, “Biotransformation of Dehydroepiandrosterone by Penicillium olsonii MRC500780”, SAUJS, vol. 28, no. 6, pp. 1261–1266, 2024, doi: 10.16984/saufenbilder.1496783.
ISNAD Kuru, Ali - Albayaty, Mena. “Biotransformation of Dehydroepiandrosterone by Penicillium Olsonii MRC500780”. Sakarya University Journal of Science 28/6 (December 2024), 1261-1266. https://doi.org/10.16984/saufenbilder.1496783.
JAMA Kuru A, Albayaty M. Biotransformation of Dehydroepiandrosterone by Penicillium olsonii MRC500780. SAUJS. 2024;28:1261–1266.
MLA Kuru, Ali and Mena Albayaty. “Biotransformation of Dehydroepiandrosterone by Penicillium Olsonii MRC500780”. Sakarya University Journal of Science, vol. 28, no. 6, 2024, pp. 1261-6, doi:10.16984/saufenbilder.1496783.
Vancouver Kuru A, Albayaty M. Biotransformation of Dehydroepiandrosterone by Penicillium olsonii MRC500780. SAUJS. 2024;28(6):1261-6.