Amino Acid Conjugated Anthraquinones from the Marine-Derived Fungus Penicillium sp. SCSIO sof101

J Nat Prod. 2017 May 26;80(5):1668-1673. doi: 10.1021/acs.jnatprod.7b00269. Epub 2017 May 16.

Abstract

Emodacidamides A-H (1-8), natural products featuring anthraquinone-amino acid conjugates, have been isolated from a marine-derived fungus, Penicillium sp. SCSIO sof101, together with known anthraquinones 9 and 10. The planar structures of 1-8 were elucidated using a combination of NMR spectroscopy and mass spectrometry. The absolute configurations of the amino acid residues were confirmed using Marfey's method and chiral-phase HPLC analyses. Additionally, isolates were evaluated for possible immunomodulatory and cytotoxic activities. Emodacidamides A (1), C (3), D (4), and E (5) inhibited interleukin-2 secretion from Jurkat cells with IC50 values of 4.1, 5.1, 12, and 5.4 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry
  • Amino Acids / immunology
  • Amino Acids / isolation & purification*
  • Amino Acids / pharmacology*
  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology*
  • Chromatography, High Pressure Liquid
  • Fungi / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Interleukin-2 / agonists*
  • Interleukin-2 / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Penicillium / chemistry*

Substances

  • Amino Acids
  • Anthraquinones
  • Interleukin-2
  • emodacidamide A
  • emodacidamide C
  • emodacidamide D
  • emodacidamide E