Steroids? transformations in culture

Microbial Modifications of Androstane and Androstene Steroids by Penicillium vinaceum

“…Therefore we have included representatives of 19-OH steroids in our biotransformation experiments. Biosynthetic routes from 19-nortestosterone to 19-nortestololactone were established with the use of biocatalytic fungi Aspergillus tamarii [ 23 ] and Penicillium notatum [ 24 ], but we were able to obtain in the current study better final yields than those presented in the earlier reports.…”

“…Such an idea of configurational flexibility of steroid substrates was proposed already in 1967 on the basis of diverse metabolic fates of steroids biotransformed by Aspergillus tamarii cultures [ 28 ]. Some recent examples of the presence of steroidal BVMOs in fungal biotransformation pathways are: lactonization of progesterone and 5-ene steroids [ 29 , 30 ]; lactonization of dehydroepiandrosterone (DHEA), pregnenolone, and androstenedione by filamentous fungi of genus Penicillium [ 31 , 32 ]; lactonization of DHEA by Aspergillus parasiticus [ 33 ]; ring- d lactonization of steroidal C-17 ketones to 11α-hydroxy derivatives by Beauveria bassiana [ 34 ]; activity of Penicillium lanosocoeruleum in ring- d lactonization of C 19 -steroids [ 35 ] and pregnene-based steroids [ 36 ]; biotransformation of DHEA into hydroxylated steroid lactones Spicaria fumoso-rosea [ 37 ]; diverse biotransformation routes of steroids, including ring- d lactonization, in the cultures of Penicillium notatum [ 24 ] and Aspergillus terreus [ 38 ]; formation of testololactone from diverse steroidal substrates with the use of a multifunctional strain of Penicillium simplicissimum [ 39 ]; cascade of DHEA biotransformations by Beauveria species [ 40 ]; and the formation of new derivatives of 3β-acetyloxy-5α-chloro-6,19-oxidoandrostan-17-one [ 41 ]. This rich background of BVMO activity studies in fungal species, combined with the outlined above need for further research in the field of biotransformations, prompted us to investigate in detail metabolic fates of DHEA ( 1 ), epiandrosterone ( 2 ), androsterone ( 3 ), androstenedione ( 4 ), 19-OH-androstenedione ( 5 ), testosterone ( 6 ), 19-nortestosterone ( 7 ), progesterone ( 8 ), and pregnenolone ( 9 ) in the cultures of Penicillium vinaceum AM110.…”

Transformation of some 3α-substituted steroids by Aspergillus tamarii KITA reveals stereochemical restriction of steroid binding orientation in the minor hydroxylation pathway

“…Furthermore in both recorded cases the activity of this enzyme was observed post 48 h which suggests that the 1␤-hydroxylase responsible is induced. This also appears to be a highly unusual position of hydroxylation especially when compared to the wide range of fungi studied to date which can perform steroidal Baeyer-Villiger oxidation [15][16][17][18][19][20] including those of which can hydroxylate at C-11 [21][22][23] (Figs. 2 and 3).…”

Biotransformation of Steroids Using Different Microorganisms

“…Biotransformation of Steroids Using Different Microorganisms DOI: http://dx.doi.org/10.5772/intechopen.85849 6β,14α-dihydroxyandrost-4-en-3,17-dione (100), 11α-hydroxyandrost-4-en-3,17dione (101), androst-4-en-3,6,17-trione (102), and 5α-androst-3,6,17-trione (103) were produced as described by Schaaaf and Dettner [69].…”

“…The products 17β-hydroxy-17αmethyl-5α-androst-1,4-dien-3,6-dione (235), 7β-hydroxydianabol (236), 15β-hydroxydianabol (237), 17β-hydroxy-17α-methyl-5α-androst-1,4-dien-3,11-dione Biotransformation of Steroids Using Different Microorganisms DOI: http://dx.doi.org /10.5772/intechopen.85849 (238), and 11β-hydroxydianabol (239) were obtained from the biotransformation of 229 using Macrophomina phaseolina [101]. Biotransformation of 229 using several microorganisms has been reported, for example, Penicillium notatum [102] transformed 229 into 230 and 231, while Trichoderma hamatum produced 232 [103]. Similarly, B. bassiana, A. ochraceus, Colletotrichum lagenarium, and Sporotrichum sulfurreducens gave a biotransformed product 232 [104].…”