Abstract
The incubations of androst-4-ene-3,17-dione with Aspergillus candidus MRC 200634, Aspergillus tamarii MRC 72400, Aspergillus wentii MRC 200316 and Mucor hiemalis MRC 70325 for 5 days are reported. A. candidus MRC 200634 mainly hydroxylated androst-4-ene-3,17-dione at C-11α, C-15α and C-15β whilst A. wentii MRC 200316 hydroxylated it mainly at C-6β. A. tamarii MRC 72400 showed predominately a Baeyer–Villiger monooxygenase activity. M. hiemalis MRC 70325 hydroxylated the substrate at C-14α and reduced most of it at C-17.
References
1.
Donova M.V.
, and
Egorova O.V.
, Appl. Microbiol. Biotechnol. , 2012 , 94 , 1423 .
2.
Malaviya A.
, and
Gomes J.
, Appl. Biochem. Biotechnol. , 2009 , 158 , 374 .
3.
Fernandes P.
,
Cruz A.
,
Angelova B.
,
Pinheiro H.M.
, and
Cabral J.M.S.
, Enzyme Microb. Tech. , 2003 , 32 , 688 .
4.
Heidary M.
, and
Habibi Z.
, J. Mol. Catal. B: Enzym. , 2016 , 126 , 32 .
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.
,
Reynolds W.F.
, and
Reese P.B.
, J. Mol. Catal. B: Enzym. , 2013 , 95 , 70 .
8.
Peart P.C.
,
McCook K.P.
,
Russell F.A.
,
Reynolds W.F.
, and
Reese P.B.
, Steroids , 2011 , 76 , 1317 .
9.
Yazdi M.T.
,
Arabi H.
,
Faramarzi M.A.
,
Gasemi Y.
,
Amini M.
,
Shokravi S.
, and
Mohseni F.A.
, Phytochemistry , 2006 , 65 , 2205 .
10.
Hanson J. R.
, and
Hunter A.C.
, Phytochemistry , 1998 , 49 , 2349 .
11.
Janeczko T.
,
Dmochowska-Gładysz J.
,
Kostrzewa-Susłow E.
,
Białońska A.
, and
Ciunik Z.
, Steroids , 2009 , 74 , 657 .
12.
Yildirim K.
, and
Kuru A.
, J. Chem. Res. , 2015 , 39 , 546 .
13.
Yildirim K.
,
Uzuner A.
, and
Gulcuoglu E.Y.
, Collect. Czech. Chem. Commun. , 2011 , 76 , 743 .
14.
Brannon D.R.
,
Martin J.
,
Oehlschlager A.C.
,
Durham N.N.
, and
Zalkow L.H.
, J. Org. Chem. , 1965 , 30 , 760 .
15.
Yildirim K.
,
Kupcu I.
, and
Gulsan F.
, Z. Naturforsch., C: J. Biosci. , 2010 , 65 , 688 .
16.
Yildirim K.
,
Saran H.
,
Dolu O.F.
, and
Kuru A.
, J. Chem. Res. , 2013 , 37 , 566 .
17.
Antoniou T.N.H.
,
Curran B.P.G.
, and
Smith K.E.
, Microbiol. , 1994 , 140 , 1633 .
18.
Mascotti M.L.
,
Orden A.A.
,
Bisogno F.B.
,
Gonzalo G.
, and
Kurina-Sanz M.
, J. Mol. Catal. B: Enzym. , 2012 , 82 , 32 .
19.
Miyazawa M.
,
Takahashi T.
,
Sakata K.
, and
Horibe I.
, J. Chem. Technol. Biotechnol. , 2008 , 83 , 1006 .
20.
Nagasawa M.
,
Hashiba H.
,
Watanabe N.
,
Bae M.
,
Tamura G.
, and
Arima K.
, Agr. Biol. Chem. , 1970 , 34 , 801 .
21.
Hanson J.R.
,
Nasir H.
, and
Parvez A.
, Phytochemistry , 1996 , 42 , 411 .
22.
Choudhary M.I.
,
Sultan S.
,
Khan M.T.H.
,
Yasin A.
,
Shaheen F.
, and
Rahman A.U.
, Nat. Prod. Res. , 2004 , 18 , 529 .
23.
Kołek T.
,
Szpineter A.
, and
Świzdor A.
, Steroids , 2008 , 73 , 1441 .