An epigenetic modifier enhances the production of anti-diabetic and anti-inflammatory sesquiterpenoids from Aspergillus sydowii

Yu Ming Chung, Chien Kei Wei, Da Wei Chuang, Mohamed El-Shazly, Chi Ting Hsieh, Teigo Asai, Yoshiteru Oshima, Tusty Jiuan Hsieh, Tsong Long Hwang, Yang Chang Wu, Fang Rong Chang

Research output: Contribution to journalArticlepeer-review

65 Citations (Scopus)

Abstract

The addition of a DNA methyltransferase inhibitor, 5-azacytidine, to Aspergillus sydowii fungus culture broth changed its secondary metabolites profile. Analysis of the culture broth extract led to the isolation of three new bisabolane-type sesquiterpenoids: (7S)-(+)-7-O-methylsydonol (1), (7S,11S)-(+)-12-hydroxysydonic acid (2) and 7-deoxy-7,14-didehydrosydonol (3), along with eight known compounds. The isolated compounds were evaluated for their anti-diabetic and anti-inflammatory activities. Among the isolates, (S)-(+)-sydonol (4) did not only potentiate insulin-stimulated glucose consumption but also prevented lipid accumulation in 3T3-L1 adipocytes. Additionally, (S)-(+)-sydonol (4) exhibited significant anti-inflammatory activity through inhibiting superoxide anion generation and elastase release by fMLP/CB-induced human neutrophils. This is the first report on isolating a secondary metabolite with anti-diabetic and anti-inflammatory activities from microorganisms.

Original languageEnglish
Pages (from-to)3866-3872
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume21
Issue number13
DOIs
Publication statusPublished - 2013 Jul 1

Keywords

  • Anti-diabetic
  • Anti-inflammatory
  • Aspergillus sydowii
  • Bisabolane-type
  • Epigenetic

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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