Bioactive secondary metabolites from the marine-associated fungus Aspergillus terreus

Bioorg Chem. 2018 Oct:80:525-530. doi: 10.1016/j.bioorg.2018.06.029. Epub 2018 Jun 27.

Abstract

Three new compounds, including a prenylated tryptophan derivative, luteoride E (1), a butenolide derivative, versicolactone G (2), and a linear aliphatic alcohol, (3E,7E)-4,8-dimethyl-undecane-3,7-diene-1,11-diol (3), together with nine known compounds (4-12), were isolated and identified from a coral-associated fungus Aspergillus terreus. Their structures were elucidated by HRESIMS, one- and two-dimensional NMR analysis, and the absolute configuration of 2 was determined by comparison of its electronic circular dichroism (ECD) spectrum with the literature. Structurally, compound 1 featured an unusual (E)-oxime group, which occurred rarely in natural products. Compounds 1-3 were evaluated for the α-glucosidase inhibitory activity, and compound 2 showed potent inhibitory potency with IC50 value of 104.8 ± 9.5 μM, which was lower than the positive control acarbose (IC50 = 154.7 ± 8.1 µM). Additionally, all the isolated compounds were evaluated for the anti-inflammatory activity against NO production, and compounds 1-3, 5-7, and 10 showed significant inhibitory potency with IC50 values ranging from 5.48 to 29.34 μM.

Keywords: Anti-inflammatory; Antibacterial; Aspergillus terreus; Marine-associated fungus; Molecular docking; α-Glucosidase inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • Animals
  • Anthozoa / microbiology*
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / metabolism
  • Anti-Inflammatory Agents / pharmacology
  • Aspergillus / chemistry*
  • Aspergillus / metabolism
  • Bacteria / drug effects
  • Biological Products / chemistry*
  • Biological Products / isolation & purification
  • Biological Products / metabolism
  • Biological Products / pharmacology
  • Glycoside Hydrolase Inhibitors / chemistry*
  • Glycoside Hydrolase Inhibitors / isolation & purification
  • Glycoside Hydrolase Inhibitors / metabolism
  • Glycoside Hydrolase Inhibitors / pharmacology
  • Mice
  • Molecular Docking Simulation
  • Nitric Oxide / antagonists & inhibitors
  • RAW 264.7 Cells
  • Saccharomyces cerevisiae / enzymology
  • Secondary Metabolism
  • Sesquiterpenes

Substances

  • Anti-Inflammatory Agents
  • Biological Products
  • Glycoside Hydrolase Inhibitors
  • Sesquiterpenes
  • Nitric Oxide
  • butenolide
  • 4-Butyrolactone