Stoffwechsel von steroidpharmaka

Schubert, K.; Schlegel, J.; Groh, H.; Rose, G.; Hörhold, C.

doi:10.1016/0022-4731(70)90019-1

Cited by 4 publications

(3 citation statements)

References 2 publications

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“…The 17α-methyl group did not inhibit hydroxylation in ring D. 1-Dehydro-17α-methyltestosterone was hydroxylated at the C-15. Similar results were obtained in the transformation of the same substrate by Aspergillus flavus (SCHUBERT et al 1972).…”

Section: Discussionsupporting

confidence: 90%

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Transformations of testosterone and related steroids in Absidia glauca culture

Huszcza

Dmochowska-Gładysz

2003

J. Basic Microbiol.

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In the following study, the course of transformations of testosterone and its derivatives with an additional C(1)-C(2) double bond and/or 17alpha-methyl group or without 19-methyl group in Absidia glauca culture was investigated. The fungi were observed to hydroxylate these compounds and to oxidise the 17beta-hydroxyl group. The products of 6beta, 7alpha, 7beta, 11alpha, 12beta or 15beta hydroxylation were obtained. 19-Nortestosterone was also hydroxylated at the 10beta position.The position and stereochemistry of the introduced hydroxyl group was dependent on the presence of the additional C(1)-C(2) double bond, while hydroxylation at the C-6beta was unaffected. The incubation of testosterone with Absidia glauca gave hydroxyderivatives of androstenedione: 7alpha-hydroxyandrostenedione and 6beta,11alpha-dihydroxyandrostenedione. When 1-dehydrotestosterone and 1-dehydro-17alpha-methyltestosterone were used, the products were hydroxylated at 6beta, 7beta or 15beta position while 17alpha-methyltestosterone and 19 nortestosterone products were hydroxylated at 6beta, 7alpha, 11alpha or 12beta position. Two metabolites: 6beta,11alpha-dihydroxyandrostenedione and 6beta,12beta-dihydroxy-17alpha-methyltestosterone were dihydroxylated. The presence of 17alpha-methyl group in 17alpha-methyltestosterone and 1-dehydro-17alpha-methyltestosterone did not influence the position of hydroxylation.

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Section: Discussionsupporting

confidence: 90%

“…In many cases, C-6β and C-10β hydroxylation are concurrent or occur with the same species and possibly are a function of the C-6β hydroxylating system (SCHUBERT et al 1972).…”

Section: Discussionmentioning

confidence: 99%

Transformations of testosterone and related steroids in Absidia glauca culture

Huszcza

Dmochowska-Gładysz

2003

J. Basic Microbiol.

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“…Fungal hydroxylations of 19-nortestosterone 1 in literature have often resulted in concurrent and independent C-10β and C-6β hydroxylations 15,16,20,21 as with A. wentii. It is thought that C-10β and C-6β hydroxylations probably are a function of the C-6β hydroxylating system 15,22 since these hydroxylations are concurrent and independent in many cases. It is also thought that hydroxylation of 1 at the C-10β position in some fungi 19,23 is highly induced by the absence of the 19-methyl group.…”

mentioning

confidence: 99%