Biotransformation of dehydroepiandrosterone (DHEA) by environmental strains of filamentous fungi

作者: Ewa Kozłowska , Monika Urbaniak , Anna Kancelista , Monika Dymarska , Edyta Kostrzewa-Susłow

DOI: 10.1039/C7RA04608A

关键词: DehydroepiandrosteroneBiotransformationChemistryAspergillus versicolorPenicilliumStereochemistryMucor hiemalisSteroidBiochemistryHydroxylationStrain (chemistry)

摘要: Microbial transformations of steroids are an important method obtaining new steroid derivatives potential pharmaceutical activity, which follows the principles green chemistry. We studied ability selected filamentous fungus species to transform dehydroepiandrosterone (DHEA) and interesting DHEA were obtained. Twenty-five strains fungi isolated from soil air in Wroclaw they used as biocatalysts. Strains genus Penicillium transformed substrate into products Baeyer–Villiger lactonization D ring. Biotransformation by Fusarium acuminatum KCh S1 strain led a stereoselective hydroxylation at 7α (the product was obtained with 97% conversion). Androst-5-ene-3β,7α,17α-triol, compound high anticancer activity towards glioblastoma lymphoma cell lines 65% yield culture Mucor hiemalis W2 strain. In Aspergillus versicolor TJ1 strain, androst-1,4-diene-3,17-dione (ADD) yield.

参考文章(60)
Lorena Butinar, Martina Mohorčič, Valérie Deyris, Katia Duquesne, Gilles Iacazio, Magalie Claeys-Bruno, Josepha Friedrich, Véronique Alphand, Prevalence and specificity of Baeyer-Villiger monooxygenases in fungi. Phytochemistry. ,vol. 117, pp. 144- 153 ,(2015) , 10.1016/J.PHYTOCHEM.2015.06.009
Mange Ram Yadav, Mahesh A Barmade, Riyaj S Tamboli, Prashant R Murumkar, None, Developing steroidal aromatase inhibitors-an effective armament to win the battle against breast cancer. European Journal of Medicinal Chemistry. ,vol. 105, pp. 1- 38 ,(2015) , 10.1016/J.EJMECH.2015.09.038
Laura Fernández de las Heras, Robert van der Geize, Oliver Drzyzga, Julián Perera, Juana María Navarro Llorens, Molecular characterization of three 3-ketosteroid-Delta(1)-dehydrogenase isoenzynnes of Rhodococcus ruber strain Chol-4 The Journal of Steroid Biochemistry and Molecular Biology. ,vol. 132, pp. 271- 281 ,(2012) , 10.1016/J.JSBMB.2012.06.005
Elisa Beneventi, Gianluca Ottolina, Giacomo Carrea, Walter Panzeri, Giovanni Fronza, Peter C.K. Lau, Enzymatic Baeyer-Villiger oxidation of steroids with cyclopentadecanone monooxygenase Journal of Molecular Catalysis B-enzymatic. ,vol. 58, pp. 164- 168 ,(2009) , 10.1016/J.MOLCATB.2008.12.009
Olivier Hennebert, Marie-Agnès Pelissier, Sandrine Le Mee, Ernst Wülfert, Robert Morfin, Anti-inflammatory effects and changes in prostaglandin patterns induced by 7β-hydroxy-epiandrosterone in rats with colitis The Journal of Steroid Biochemistry and Molecular Biology. ,vol. 110, pp. 255- 262 ,(2008) , 10.1016/J.JSBMB.2007.12.014
Marcello Maggio, Francesca De Vita, Alberto Fisichella, Elena Colizzi, Sandra Provenzano, Fulvio Lauretani, Michele Luci, Graziano Ceresini, Elisabetta Dall’Aglio, Paolo Caffarra, Giorgio Valenti, Gian Paolo Ceda, DHEA and cognitive function in the elderly The Journal of Steroid Biochemistry and Molecular Biology. ,vol. 145, pp. 281- 292 ,(2015) , 10.1016/J.JSBMB.2014.03.014
R. MORFIN, P. LAFAYE, A. C. COTILLON, F. NATO, V. CHMIELEWSKI, D. POMPON, 7α-Hydroxy-Dehydroepiandrosterone and Immune Response Annals of the New York Academy of Sciences. ,vol. 917, pp. 971- 982 ,(2006) , 10.1111/J.1749-6632.2000.TB05464.X
Leslie Lehman, Jon Stewart, Filamentous Fungi Potentially Useful Catalysts for the Biohydroxylations of Non-Activated Carbon Centers Current Organic Chemistry. ,vol. 5, pp. 439- 470 ,(2001) , 10.2174/1385272013375490