title: Structure and absolute configuration of 20β-Hydroxyprednisolone, a biotransformed product of predinisolone by the marine endophytic fungus Penicilium lapidosum.
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.
authors.affiliation: Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia. drsadia@puncakalam.uitm.edu.my.
authors.forename: Sadia
authors.initials: S
authors.lastname: Sultan
authors.affiliation: Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia.
authors.forename: Muhammad Zaimi Bin Mohd
authors.initials: MZ
authors.lastname: Noor
authors.affiliation: Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia. anouarelhassane@yahoo.fr.
authors.forename: El Hassane
authors.initials: el H
authors.lastname: Anouar
authors.affiliation: Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia. syedadnan@puncakalam.uitm.edu.my.
authors.forename: Syed Adnan Ali
authors.initials: SA
authors.lastname: Shah
authors.affiliation: Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia.
authors.forename: Fatimah
authors.initials: F
authors.lastname: Salim
authors.affiliation: Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia.
authors.forename: Rohani
authors.initials: R
authors.lastname: Rahim
authors.affiliation: Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia.
authors.forename: Zuhra Bashir Khalifa
authors.initials: ZB
authors.lastname: Al Trabolsy
authors.affiliation: Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia.
authors.forename: Jean-Frédéric Faizal
authors.initials: JF
authors.lastname: Weber
mesh_terms: D001483:Base Sequence; D017931:DNA Primers; D009682:Magnetic Resonance Spectroscopy; D008386:Marine Biology; D010407:Penicillium / Q000378:metabolism*; D011239:Prednisolone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
chemical_list: D017931:DNA Primers; D011239:Prednisolone