Published January 31, 2020
| Version v1
Journal article
Restricted
Biotransformation of androstenedione and androstadienedione by selected Ascomycota and Zygomycota fungal strains
Authors/Creators
- 1. ∗ & Federal Research Center «Pushchino Center for Biological Research of the Russian Academy of Sciences», G.K. Skryabin Institute of Biochemistry and Physiology of & ∗ & Pharmins Ltd., Institutskaya ul, 4, 142290, Pushchino, Moscow Region, Russia
Description
Kollerov, Vyacheslav, Shutov, Andrei, Kazantsev, Alexey, Donova, Marina (2020): Biotransformation of androstenedione and androstadienedione by selected Ascomycota and Zygomycota fungal strains. Phytochemistry (112160) 169: 1-9, DOI: 10.1016/j.phytochem.2019.112160, URL: http://dx.doi.org/10.1016/j.phytochem.2019.112160
Files
Restricted
The record is publicly accessible, but files are restricted to users with access.
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:FFD3FFF17B3F8823FFC7FF8E036EFFDA
References
- Andryushina, V.A., Voishvillo, N.E., Druzhinina, A.V., Stytsenko, T.S., Yaderets, V.V., Petrosyan, M.A., Zeinalov, O.A., 2013. 14α- Hydroxylation of steroids by mycelium of the mold fungus Curvularia lunata (VKPM F-981) to produce precursors for synthesizing new steroidal drugs. Pharm. Chem. J. 47, 103-108. https://doi.org/10.1007/ s11094-013-0905-6.
- Arabia, H., Yazdia, M.T., Faramarzi, M.A., 2010. Influence of whole microalgal cell immobilization and organic solvent on the bioconversion of androst-4-en-3,17-dione to testosterone by Nostoc muscorum. J. Mol. Catal. B Enzym. 62, 213-217. https://doi. org/10.1016/j.molcatb.2009.10.006.
- Bolten, S.L., Clayton, R.A., Easton, A.M., Engel, L.C., Messing, D.M., Reitz, B., Walker, M. C., Wang, T. 2007. Aspergillus ochraceus 11alpha-Hydroxylase and Oxidoreductase. US Patent 7238507 B2.
- Choudhary, M.I., Musharraf, S.G., Shaheen, F., Rahman, A., 2002. Microbial transformation of (+)-androsta-1,4-diene-3,17-dione by Cephalosporium aphidicola. Nat.
- Choudhary, M.I., Sultan, S., Khan, M.T., Yasin, A., Shaheen, F., Rahman, A., 2004.
- Donova, M.V., Egorova, O.V., 2012. Microbial steroid transformations: current state and prospects. Appl. Microbiol. Biotechnol. 94, 1423-1447. https://doi.org/10.1007/
- Dovbnya, D., Khomutov, S., Kollerov, V., Donova, M.V., 2017. Obtaining of 11α- Hydroxyandrost-4-ene-3,17-dione from natural sterols. Methods Mol. Biol. 1645, 259-269. https://doi.org/10.1007/978-1-4939-7183-1_18.
- Durairaj, P., Hur, J., Yun, H., 2016. Versatile biocatalysis of fungal cytochrome P450 monooxygenases. Microb. Cell Factories 15, 125. https://doi.org/10.1186/s12934- 016-0523-6.
- Faramarzi, M., Yazdi, M.T., Mohseni, F.A., Amani, G.Z., Shafiee, A., 2004. Microbial production of testosterone and testololactone in the culture of Aspergillus terreus. World J. Microbiol. Biotechnol. 20, 657-660. https://doi.org/10.1007/s11274-004- 1003-4.
- Eshrat F., G., Aroona, C., 2011. Biotransformation of Progesterone by Penicillium aurantiogriseum. Research Journal of Microbiology 6, 98-104. https://doi.org/10.3923/ jm.2011.98.104.
- Faramarzi, M.A., Hajarolasvadi, N., Yazdi, M.T., Amini, M., Aghelnejad, M., 2007. Microbiological hydroxylation of androst-1,4-dien-3,17-dione by Neurospora crassa. Biocatal. Biotransform. 25, 72-78. https://doi.org/10.1080/10242420600893850.
- Felpeto-Santero, C., Galan, B., Luengo, J.M., Fernandez-Canon, J.M., Del Cerro, C., Medrano, F.J., Garcia, J.L., 2019. Identification and expression of the 11β- steroid hydroxylase from Cochliobolus lunatus in Corynebacterium glutamicum. Microb Biotechnol 12, 856-868. https://doi.org/10.1111/1751-7915.13428.
- Fernandez-Cabezon, L., Galan, B., Garcia, J.L., 2018. New insights on steroid biotechnology. Front. Microbiol. 9, 958. https://doi.org/10.3389/fmicb.2018.00958.
- Gao, X.Q., Feng, J.X., Wang, X.D., Hu, Q., Wei, D.Z., 2015. Enhanced steroid metabolites production by resting cell phytosterol bioconversion. Chem. Biochem. Eng. Q. 29, 567-573. https://doi.org/10.15255/CABEQ.2014.2098.
- Girvan, H.M., Munro, A.W., 2016. Applications of microbial cytochrome P450 enzymes in biotechnology and synthetic biology. Curr. Opin. Chem. Biol. 31, 136-145. https:// doi.org/10.1016/j.cbpa.2016.02.018.
- Guevara, G., Fernandez de las Heras, L., Perera, J., Navarro LIorens, J.M., 2017. Functional differentiation of 3-ketosteroid Δ1-dehydrogenase isozymes in Rhodococcus ruber strain Chol-4. Microb. Cell Factories 42, 1-16. https://doi.org/10. 1186/s12934-017-0657-1.
- Hawksworth, D.L., Lucking, R., 2017. Fungal diversity revisited: 2.2 to 3.8 million species. Microbiol. Spectr. 5, 1-17. https://doi.org/10.1128/microbiolspec.FUNK-0052- 2016.
- Heidary, M., Habibi, Z., 2016. Microbial transformation of androst-4-ene-3,17-dione by three fungal species Absidia griseolla var. igachii, Circinella muscae and Trichoderma virens. J. Mol. Catal. B Enzym. 126, 32-36. https://doi.org/10.1016/j.molcatb.2016. 01.007.
- Hosseinabadi, T., Vahidi, H., Nickavar, B., Kobarfard, F., 2014. Fungal transformation of androsta-1,4-diene-3,17-dione by Aspergillus brasiliensis. J Pharm Sci. 22, 1-5. https://doi.org/10.1186/s40199-014-0071-8.
- Hu, S., Genain, G., Azerad, R., 1995. Microbial transformation of steroids: contribution to 14α- hydroxylations. Steroids 60, 337-352. https://doi.org/10.1016/0039-128X(95) 00006-C.
- Huszcza, E., Dmochowska-Gladysz, J., 2003. Transformations of testosterone and related steroids in Absidia glauca culture. J. Basic Microbiol. 43, 113-120. https://doi.org/ 10.1002/jobm.200390011.
- Ikegami, C.I., Matsusaki, Y., 2008. Ursodeoxycholic acid. Mechanism of action and novel clinical applications. Hepatol. Res. 38, 123-131. https://doi.org/10.1111/j.1872- 034X.2007.00297.x.
- Janeczko, T., Dmochowska-G l adysza, J., Kostrzewa-Sus l owa, E., Bia l onska, A., Ciunik, Z., 2009. Biotransformations of steroid compounds by Chaetomium sp. KCH 6651. Steroids 74, 657-661. https://doi.org/10.1016/j.steroids.2009.02.006.
- Janeczko, T., Swizdor, A., Dmochowska-G l adysz, J., Bia l onska, A., Ciunik, Z., Kostrzewa-Sus l ow, E., 2012. Novel metabolites of dehydroepiandrosterone and progesterone obtained in Didymosphearia igniaria KCH 6670 culture. J. Mol. Catal. B Enzym. 82, 24-31. https://doi.org/10.1016/j.molcatb.2012.05.009.
- Kollerov, V.V., Shutov, A.A., Fokina, V.V., Sukhodol' skaya, G.V., Donova, M.V., 2008. Biotransformation of 3-keto-androstanes by the strain of Gongronella butleri VKM F-1033. J. Mol. Catal. B Enzym. 55, 61-68. https://doi.org/10.1016/j.molcatb.2008. 01.009.
- Kollerov, V.V., Shutov, A.A., Fokina, V.V., Sukhodolskaya, G.V., Gulevskaya, S.A., Donova, M.V., 2010. Bioconversion of C19- and C21- steroids with parent and mutant strains of Curvularia lunata. Appl. Biochem. Microbiol. 46, 198-205. https://doi.org/ 10.1134/S0003683810020122.
- Kollerov, V.V., Monti, D., Deshcherevskaya, N.O., Lobastova, T.G., Ferrandi, E.E., Larovere, A., Gulevskaya, S.A., Riva, S., Donova, M.V., 2013. Hydroxylation of lithocholic acid by selected actinobacteria and filamentous fungi. Steroids 78, 370-378. https://doi.org/10.1016/j.steroids.2012.12.010.
- Kollerov, V.V., Lobastova, T.G., Monti, D., Deshcherevskaya, N.O., Ferrandi, E.E., Fronza, G., Riva, S., Donova, M.V., 2016. Deoxycholic acid transformations catalyzed by selected filamentous fungi. Steroids 107, 20-29. https://doi.org/10.1016/j.steroids. 2015.12.015.
- Kollerov, V.V., Fokina, V.V., Sukhodolskaya, G.V., Shutovl, A.A., Donova, M.V., 2015. 11β- Hydroxylation of 6α- aluoro-16α- methyl-deoxycorticosterone 21-acetate by filamentous fungi. Appl. Biochem. Microbiol. 51, 169-179. https://doi.org/10.1134/ s0003683815020106.
- Koz l owska, E., Urbaniak, M., Kancelista, A., Dymarska, M., Kostrzewa-Sus l ow, E., Stepie n, L., Janeczko, T., 2017. Biotransformation of dehydroepiandrosterone (DHEA) by environmental strains of filamentous fungi. RSC Adv. 7, 31493-31501. https://doi.org/10.1039/C7RA04608A.
- Kristan, K., Ri˘zner, T.L., 2012. Steroid-transforming enzymes in fungi. J. Steroid Biochem. Mol. Biol. 129, 79-91. https://doi.org/10.1016/j.jsbmb.2011.08.012.
- Lobastova, T.G., Gulevskaya, S.A., Sukhodolskaya, G.V., Turchin, K.F., Donova, M.V., 2007. Screening of mycelial fungi for 7α- and 7β- hydroxylase activity towards dehydroepiandrosterone. Biocatal. Biotransform. 25, 434-442. https://doi.org/10. 1080/10242420701568492.
- Lobastova, T.G., Gulevskaya, S.A., Sukhodolskaya, G.V., Donova, M.V., 2009. Dihydroxylation of dehydroepiandrosterone in positions 7α and 15α by mycelial fungi. Appl. Biochem. Microbiol. 45, 617-622. https://doi.org/10.1134/ S0003683809060076.
- Milecka-Tronina, N., Ko l ek, T., S'wizdor, A., Panek, A., 2014. Hydroxylation of DHEA and its analogues by Absidia coerulea AM93, Can an inducible microbial hydroxylase catalyze 7α- and 7β- hydroxylation of 5-ene and 5α- dihydro C19-steroids? Bioorg. Med. Chem. 22, 883-891. https://doi.org/10.1016/j.bmc.2013.11.050.
- Moriarty, R.M., Shores, M., David, N.E., Mahmood, N.A. 2014. Synthetic Bile Acid Compositions and Methods. US Patent 0038932 A1.
- Nassiri-Koopaei, N., Faramarzi, M.A., 2015. Recent developments in the fungal transformation of steroids. Biocatal. Biotransform. 33, 1-28. https://doi.org/10.3109/ 10242422.2015.1022533.
- Philipp, B., 2011. Bacterial degradation of bile salts. Appl. Microbiol. Biotechnol. 89, 903-915. https://doi.org/10.1007/s00253-010-2998-0.
- Rohman, A., Dijkstra, B.W., 2019. The role and mechanism of microbial 3-ketosteroid 1- dehydrogenases in steroid breakdown. J. Steroid Biochem. Mol. Biol (in press). https://doi.org/10.1016/j.jsbmb.2019.04.015.
- Schmitz, D., Zapp, J., Bernhardt, R., 2014. Steroid conversion with CYP106A2 - production of pharmaceutically interesting DHEA metabolites. Microb. Cell Factories 81, 1-13. https://doi.org/10.1186/1475-2859-13-81.
- Sharma, R., Prichard, D., Majer, F., Byrne, A.M., Kelleher, D., Long, A., Gilmer, J.F., 2011. Ursodeoxycholic acid amides as novel glucocorticoid receptor modulators. J. Med. Chem. 54, 122-130. https://doi.org/10.1021/jm100860s.
- Shen, G.J., Zhou, B., Lai, T.C., Su, H.L., Yang, H.Y., 2013. Study on biotransformation products of androstenedione by Paecilomyces victoria. Adv. Mater. Res. 807, 414-417. https://doi.org/10.4028/www.scientific.net/AMR.807-809.414.
- Shen, Q.Y., Huang, W., Wang, Y., Ren, J., Xia, T., Wang, M., 2017. Biocatalyst-mediated production of 11,15-dihydroxy derivatives of androst-1,4-dien-3,17-dione. J. Biosci. Bioeng. 123, 692-697. https://doi.org/10.1016/j.jbiosc.2017.01.008.
- Srisilam, K., Veeresham, C., 2003. Biotransformation of drugs by microbial cultures for predicting mammalian drug metabolism. Biotechnol. Adv. 22, 617. https://doi.org/ 10.1016/j.biotechadv.2004.07.001.
- Wang, F., Yao, K., Wei, D., 2011. From soybean phytosterols to steroid hormones. In: El- Shemy, H. (Ed.), Soybean and Health. INTECH Open Access Publisher, pp. 231-252. https://doi.org/10.5772/18808.
- Wang, Y., Yue, Q., Zhao, Y., Qiu, S., Peng, Y., Li, J., Zhang, T., Hai, L., Guo, L., Wu, Y., 2016. First synthesis of 22-oxa-chenodeoxycholic acid analogue. Steroids 110, 70-76. https://doi.org/10.1016/j.steroids.2016.04.004.
- Williams, C.I., Shaffer, E.A., 2008. Gallstone disease: current therapeutic practice. Curr. Treat. Options Gastroenterol. 48, 692-694. https://doi.org/10.1007/s11938-008- 0018-6.
- Xiong, Z., Wei, Q., Chen, H., Chen, S., Xu, W., Qiu, G., Liang, S., Hu, X., 2006. Microbial transformation of androst-4-ene-3,17-dione by Beauveria bassiana. Steroids 71, 979-983. https://doi.org/10.1016/j.steroids.2006.07.007.