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- Title
Structure and Absolute Configuration of 20β-Hydroxyprednisolone, a Biotransformed Product of Predinisolone by the Marine Endophytic Fungus Penicilium lapidosum.
- Authors
Sultan, Sadia; bin Mohd Noor, Muhammad Zaimi; Anouar, El Hassane; Ali Shah, Syed Adnan; Salim, Fatimah; Rahim, Rohani; Khalifa Al Trabolsy, Zuhra Bashir; Faizal Weber, Jean-Frédéric
- 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.
- Subjects
ENDOPHYTIC fungi; GAS phase reactions; ENDOMYCORRHIZAS; CHEMICAL reactions; DICHROISM
- Publication
Molecules, 2014, Vol 19, Issue 9, p13775
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules190913775