Abstract
The biotransformation of dehydroepiandrosterone, progesterone and pregnenolone by Aspergillus candidus MRC 200634 for 5 days is reported. Dehydroepiandrosterone was hydroxylated at C-6β, C-7β, C-7α, C-11α and C-15α. The 17-ketone was reduced to the 17β-alcohol whilst ring A of dehydroepiandrosterone was oxidised to a 4-en-3-one moiety. Progesterone was mainly hydroxylated at C-11α and C-15β and to a lesser extent at C-14α. Pregnenolone gave the same metabolites.
References
1.
Nassiri-Koopaei N.
, and
Faramarzi M. A.
, Biocatal. Biotransform. , 2015 , 33 , 1 .
2.
Samson R.A.
,
Hong S. B.
, and
Frisvad J. C.
, Med. Mycol. , 2006 , 44 , 133 .
3.
Lee S.K.
,
Kang H. G.
,
Na K. J.
, and
Han J. I.
, Equine Vet. Sci. , 2012 , 32 , 835 .
4.
Varga J.
,
Frisvad J. C.
, and
Samson R. A.
, Stud. Mycol. , 2007 , 59 , 75 .
5.
Kirk D.N.
,
Toms H. C.
,
Douglas C.
,
White K. A.
,
Smith K. E.
,
Latif S.
, and
Hubbard R. W. P.
, J. Chem. Soc. Perkin Trans. 2 , 1990 , 1567 .
6.
Blunt J.W.
, and
Stothers J. B.
, Org. Magn. Reson. , 1977 , 9 , 439 .
7.
Peart P.C.
,
McCook K. P.
,
Russell F. A.
,
Reynolds W. F.
, and
Reese P. B.
, Steroids , 2011 , 76 , 1317 .
8.
Janeczko T.
,
Świzdor A.
,
Dmochowska-Gładysz J.
,
Białońska A.
,
Ciunik Z.
, and
Kostrzewa-Susłow E.
, J. Mol. Catal. B-Enzym. , 2012 , 82 , 24 .
9.
Hanson J.R.
,
Nasir H.
, and
Parvez A.
, Phytochemistry , 1996 , 42 , 411 .
10.
Bensasson C.M.
,
Hanson J. R.
, and
Hunter A. C.
, Phytochemistry , 1998 , 49 , 2355 .
11.
Yousefi M.
,
Mohammadi M.
,
Habibi Z.
, and
Shafiee A.
, Biocatal. Biotransform. , 2010 , 28 , 254 .
12.
Herzog H.L.
,
Gentles M. J.
,
Charney W.
,
Sutter D.
,
Townley E.
,
Yudis M.
,
Kabasakalian P.
, and
Hershberg E. B.
, J. Org. Chem. , 1959 , 24 , 691 .
13.
Peterson D.H.
, and
Murray H. C.
, J. Am. Chem. Soc. , 1952 , 74 , 1871 .
14.
Schubert A.
,
Langbein G.
, and
Siebert R.
, Chem. Ber. , 1957 , 90 , 2576 .