Microbial conversion of pregna-4,9(11)-diene-17alpha,21-diol-3,20-dione acetates by Nocardioides simplex VKM Ac-2033D.
The conversion of pregna-4,9(11)-diene-17alpha,21-diol-3,20-dione 21-acetate (I) and 17,21-diacetate (VI) by Nocardioides simplex VKM Ac-2033D was studied. The major metabolites formed from I were identified as pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 21-acetate (II) and pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione (IV). Pregna-4,9(11)-diene-17alpha,21-diol-3,20-dione (III) and pregna-1,4,9(11)-triene-17alpha,20beta,21-triol-3-one (V) were formed in minorities. Biotransformation products formed from VI were pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 17,21-diacetate (VII), pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 21-acetate (II), pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione (IV), pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 17-acetate (VIII), pregna-1,4,9(11)-triene-17alpha,20beta,21-triol-3-one (V). The conversion pathways were proposed including 1(2)-dehydrogenation, deacetylation, 20beta-reduction and non-enzymatic migration of acyl group from position 17 to 21. The conditions providing predominant accumulation of pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 21-acetate (II) from I and pregna-1,4,9(11)-triene-17alpha,21-diol-3,20-dione 17-acetate (VIII) from VI in a short-term biotransformation were determined.
Fokina
Victoria V
VV
G.K. Skryabin Institute of Biochemistry and Physiology of Microorganisms, Russian Academy of Sciences, Pushchino, pr. Nauki 5, 142290 Moscow region, Russia. fokina@ibpm.serpukhov.su
Sukhodolskaya
Galina V
GV
Baskunov
Boris P
BP
Turchin
Konstantin F
KF
Grinenko
Galina S
GS
Donova
Marina V
MV
D001711:Biotransformation; D006863:Hydrogen-Ion Concentration; D006865:Hydrogenation; D009618:Nocardiaceae / Q000378:metabolism*; D011244:Pregnadienediols / Q000737:chemistry / Q000378:metabolism*; D013256:Steroids / Q000737:chemistry / Q000378:metabolism; D013329:Structure-Activity Relationship; D013997:Time Factors
D011244:Pregnadienediols; D013256:Steroids; C481864:pregna-4,9(11)-diene-17alpha,21-diol-3,20-dione acetates