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Oxygenated compounds from the bioconversion of isostevic acid and their inhibition of TNF-α and COX-2 expressions in LPS-stimulated RAW 264.7 cells.
- Source :
-
Phytochemistry [Phytochemistry] 2012 Mar; Vol. 75, pp. 90-8. Date of Electronic Publication: 2012 Jan 05. - Publication Year :
- 2012
-
Abstract
- Fourteen oxygenated compounds were isolated from the preparative-scale biotransformation of isostevic acid (ent-beyeran-19-oic acid). Incubation of it with Aspergillus niger BCRC 32720 produced eight metabolites, four with Bacillus megaterium ATCC 14581, and another four with Mortierella isabellina ATCC 38063. In addition to their structural elucidation by NMR spectroscopy and HRMS, structures of four of these were further confirmed by X-ray diffraction studies. Real-time reverse transcription PCR analysis found that 15 of these compounds displayed significant in vitro anti-inflammatory activity in lipopolysaccharide-stimulated RAW 264.7 macrophages by reducing the levels of both TNF-α and COX-2 mRNA relative to control cells stimulated by LPS alone. The activity of one metabolite was similar to that of dexamethasone in inhibiting the expression of TNF-α mRNA, while all test compounds except two of them were more potent than dexamethasone in inhibiting the expression of the COX-2 mRNA.<br /> (Copyright © 2011 Elsevier Ltd. All rights reserved.)
- Subjects :
- Animals
Anti-Inflammatory Agents, Non-Steroidal chemistry
Anti-Inflammatory Agents, Non-Steroidal metabolism
Crystallography, X-Ray
Cyclooxygenase 2 genetics
Cyclooxygenase 2 Inhibitors chemistry
Cyclooxygenase 2 Inhibitors metabolism
Diterpenes chemistry
Diterpenes metabolism
Drug Evaluation, Preclinical
Lipopolysaccharides pharmacology
Macrophages drug effects
Mice
Models, Molecular
Molecular Structure
RNA, Messenger drug effects
RNA, Messenger genetics
RNA, Messenger metabolism
Reverse Transcriptase Polymerase Chain Reaction
Stereoisomerism
Structure-Activity Relationship
Tumor Necrosis Factor-alpha genetics
Anti-Inflammatory Agents, Non-Steroidal pharmacology
Cyclooxygenase 2 metabolism
Cyclooxygenase 2 Inhibitors pharmacology
Diterpenes pharmacology
Macrophages metabolism
Tumor Necrosis Factor-alpha antagonists & inhibitors
Subjects
Details
- Language :
- English
- ISSN :
- 1873-3700
- Volume :
- 75
- Database :
- MEDLINE
- Journal :
- Phytochemistry
- Publication Type :
- Academic Journal
- Accession number :
- 22226038
- Full Text :
- https://doi.org/10.1016/j.phytochem.2011.12.006