structure and absolute configuration of 20β-hydroxyprednisolone, a biotransformed product of predinisolone by the marine endophytic fungus penicilium lapidosum

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ID: 178697
2014
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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.
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sultan2014moleculesstructure Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors ;Sadia Sultan;Muhammad Zaimi bin Mohd Noor;El Hassane Anouar;Syed Adnan Ali Shah;Fatimah Salim;Rohani Rahim;Zuhra Bashir Khalifa Al Trabolsy;Jean-Frédéric Faizal Weber
Journal Journal of ethnopharmacology
Year 2014
DOI
10.3390/molecules190913775
URL
http://www.mdpi.com/1420-3049/19/9/13775
Keywords
DFT endophytes

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