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

Li Ming Yang, Shwu Fen Chang, Wen Kuang Lin, Bo Hon Chou, Li Hsuan Wang, Pan Chun Liu, Shwu Jiuan Lin

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)90-98
Number of pages9
JournalPhytochemistry
Volume75
DOIs
Publication statusPublished - Mar 2012

Fingerprint

Bioconversion
prostaglandin synthase
dexamethasone
biotransformation
metabolites
Metabolites
Mortierella
Bacillus megaterium
Messenger RNA
Dexamethasone
acids
Aspergillus niger
anti-inflammatory activity
X-ray diffraction
lipopolysaccharides
nuclear magnetic resonance spectroscopy
macrophages
Macrophages
Aspergillus
reverse transcriptase polymerase chain reaction

Keywords

  • COX-2
  • Diterpenoid
  • Isostevic acid
  • Microbial transformation
  • TNF-α

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Horticulture

Cite this

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. / Yang, Li Ming; Chang, Shwu Fen; Lin, Wen Kuang; Chou, Bo Hon; Wang, Li Hsuan; Liu, Pan Chun; Lin, Shwu Jiuan.

In: Phytochemistry, Vol. 75, 03.2012, p. 90-98.

Research output: Contribution to journalArticle

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