An attempt was made to clarify how
Pellicularia filamentosa f. sp.
microsclerotia IFO 6298 capable of hydroxylating C
21-steroids at the C-19 position converts C
19-steroids, especially monohydroxyderivatives of androst-4-ene-3, 17-dione. Such substrates as 11β-hydroxyandrost-4-ene-3, 17-dione (I), androst-4-ene-3, 11, 17-trione (II), androsta-l, 4-diene-3, 17-dione (III), 11β-hydroxy-androsta-l, 4-diene-3, 17-dione (IV), 14α-hydroxyandrost-4-ene-3, 17-dione (V), 15α-hydroxyand-rost-4-ene-3, 17-dione (VI) and 9α-hydroxyandrost-4-ene-3, 17-dione (VII) were converted by the organism. All the main and several minor products were then isolated and identified. As a result it is concluded that this organism converts I and II into 14α-hydroxyandrost-4-ene-3, 11, 17-trione, III and IV into 14α-hydroxyandrosta-1, 4-diene-3, 11, 17-trione, V into llβ, l4α-dihydroxyandrost-4-ene-3, 17-dione (main) and 11β, 14α-dihydroxyandrost-4-ene-3, 17-dione (minor, a tentative structure), VI into 11β, 15α-dihydroxyandrost-4-ene-3, 17-dione (main) and 15α-hydroxyandrost-4-ene-3, 11, 17-trione (minor, a tentative structure) and VII into 9α, 14α-dihydroxyandrost-4-ene-3, 17-dione (main) and 6β, 9α-dihydroxyandrost-4-ene-3, 17-dione (minor).
In addition, the structural requirement of substrate for the 19-hydroxylation catalyzed by the organism and the influence of a hydroxyl group on steroid nucleus upon the 11β- and 14α-hydroxylations and the 11β-OH-dehydrogenation was discussed.
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