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Molecules 2014, 19(9), 13775-13787; doi:10.3390/molecules190913775

Structure and Absolute Configuration of 20β-Hydroxyprednisolone, a Biotransformed Product of Predinisolone by the Marine Endophytic Fungus Penicilium lapidosum

1
Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
2
Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
*
Authors to whom correspondence should be addressed.
Received: 4 April 2014 / Revised: 22 July 2014 / Accepted: 11 August 2014 / Published: 3 September 2014
(This article belongs to the Section Natural Products)
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Abstract

The anti-inflammatory drug predinisolone (1) was reduced to 20β-hydroxyprednisolone (2) by the marine endophytic fungus Penicilium lapidosum isolated from an alga. The structural elucidation of 2 was achieved by 1D- and 2D-NMR, MS, IR data. Although, 2 is a known compound previously obtained through microbial transformation, the data provided failed to prove the C20 stereochemistry. To solve this issue, DFT and TD-DFT calculations have been carried out at the B3LYP/6–31+G (d,p) level of theory in gas and solvent phase. The absolute configuration of C20 was eventually assigned by combining experimental and calculated electronic circular dichroism spectra and 3JHH chemical coupling constants. View Full-Text
Keywords: 20β-hydroxyprednisolone; endophytes; Penicilium lapidosum; DFT; TD-DFT; ECD spectra 20β-hydroxyprednisolone; endophytes; Penicilium lapidosum; DFT; TD-DFT; ECD spectra
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MDPI and ACS Style

Sultan, S.; Noor, M.Z.M.; Anouar, E.H.; Shah, S.A.A.; Salim, F.; Rahim, R.; Trabolsy, Z.B.K.A.; Weber, J.-F.F. Structure and Absolute Configuration of 20β-Hydroxyprednisolone, a Biotransformed Product of Predinisolone by the Marine Endophytic Fungus Penicilium lapidosum. Molecules 2014, 19, 13775-13787.

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