New monoterpenoid by biotransformation of thymoquinone using Aspergillus niger

Transformation of thymoquinone (1) by Aspergillus niger produced three metabolites 2–4. Metabolite 2 was found to be new. Compound 4 showed a significant antioxidant activity in DPPH radical scavenging assay. [Display omitted] •Biotransformation of thymoquinone (1) with A. niger yielded 3 metabolite...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic chemistry 2018-10, Vol.80, p.212-215
Main Authors: Mohammad, Mohammad Yasin, Shakya, Ashok, Al-Bakain, Ramia, Haroon, M.H., Choudhary, M. Iqbal
Format: Article
Language:English
Subjects:
Antioxidant activity
Aspergillus niger
Fungal transformation
Oxidation
Reduction
Thymoquinone
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Transformation of thymoquinone (1) by Aspergillus niger produced three metabolites 2–4. Metabolite 2 was found to be new. Compound 4 showed a significant antioxidant activity in DPPH radical scavenging assay. [Display omitted] •Biotransformation of thymoquinone (1) with A. niger yielded 3 metabolites.•Metabolite 2, a new compound, may arise from Baeyer–Villiger oxidation.•Metabolite 4 showed a potent antioxidant activity.•Oxidation, and reduction were key reactions observed during the biotransformation. Microbial transformation of thymoquinone (5-isopropyl-2-methyl-cyclohexa-2,5-diene-1,4-dione) (1) by suspended cell-cultures of the plant pathogenic fungus Aspergillus niger resulted in the production of three metabolites. These metabolites were identified as 5-isopropyl-2-methyloxepin-1-one (2), 3-hydroxy-5-isopropyl-2-methylcyclohexa-2,5-diene-1,4-dione (3), and 5-isopropyl-2-methylbenzene-1,4-diol (4) by different spectroscopic methods. Metabolite 2 was found to be a new compound. Compound 4 showed a potent antioxidant activity.
ISSN:0045-2068
1090-2120
DOI:10.1016/j.bioorg.2018.06.019