Structure and absolute configuration of 20β-Hydroxyprednisolone, a biotransformed product of predinisolone by the marine endophytic fungus Penicilium lapidosum

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...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2014-09, Vol.19 (9), p.13775-13787
Main Authors: Sultan, Sadia, Noor, Muhammad Zaimi Bin Mohd, Anouar, El Hassane, Shah, Syed Adnan Ali, Salim, Fatimah, Rahim, Rohani, Al Trabolsy, Zuhra Bashir Khalifa, Weber, Jean-Frédéric Faizal
Format: Article
Language:English
Subjects:
20β-hydroxyprednisolone
Base Sequence
DFT
DNA Primers
ECD spectra
endophytes
Magnetic Resonance Spectroscopy
Marine Biology
Penicilium lapidosum
Penicillium - metabolism
Prednisolone - analogs & derivatives
Prednisolone - chemistry
Prednisolone - metabolism
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
TD-DFT
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules190913775