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

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

doi:10.3390/molecules190913775

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

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

Universiti Teknologi MARA

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

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.

Original language	English
Pages (from-to)	13775-13787
Number of pages	13
Journal	Molecules
Volume	19
Issue number	9
DOIs	https://doi.org/10.3390/molecules190913775
State	Published - 3 Sep 2014
Externally published	Yes

Keywords

20β-hydroxyprednisolone
DFT
ECD spectra
endophytes
Penicilium lapidosum
TD-DFT

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10.3390/molecules190913775

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Sultan, S., Zaimi Bin Mohd Noor, M., Anouar, E. H., Shah, S. A. A., Salim, F., Rahim, R., Trabolsy, Z. B. K. A., & Weber, J. F. F. (2014). Structure and absolute configuration of 20β-hydroxyprednisolone, a biotransformed product of predinisolone by the marine endophytic fungus penicilium lapidosum. Molecules, 19(9), 13775-13787. https://doi.org/10.3390/molecules190913775

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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.",

keywords = "20β-hydroxyprednisolone, DFT, ECD spectra, endophytes, Penicilium lapidosum, TD-DFT",

author = "Sadia Sultan and \{Zaimi Bin Mohd Noor\}, Muhammad and Anouar, \{El Hassane\} and Shah, \{Syed Adnan Ali\} and Fatimah Salim and Rohani Rahim and Trabolsy, \{Zuhra Bashir Khalifa Al\} and Weber, \{Jean Fr{\'e}d{\'e}ric Faizal\}",

note = "Publisher Copyright: {\textcopyright} 2014 by the authors; licensee MDPI, Basel, Switzerland.",

year = "2014",

month = sep,

day = "3",

doi = "10.3390/molecules190913775",

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T1 - Structure and absolute configuration of 20β-hydroxyprednisolone, a biotransformed product of predinisolone by the marine endophytic fungus penicilium lapidosum

AU - Sultan, Sadia

AU - Zaimi Bin Mohd Noor, Muhammad

AU - Anouar, El Hassane

AU - Shah, Syed Adnan Ali

AU - Salim, Fatimah

AU - Rahim, Rohani

AU - Trabolsy, Zuhra Bashir Khalifa Al

AU - Weber, Jean Frédéric Faizal

PY - 2014/9/3

Y1 - 2014/9/3

N2 - 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.

AB - 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.

KW - 20β-hydroxyprednisolone

KW - DFT

KW - ECD spectra

KW - endophytes

KW - Penicilium lapidosum

KW - TD-DFT

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DO - 10.3390/molecules190913775

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SN - 1420-3049

VL - 19

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JO - Molecules

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ER -

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

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