Acremonamide, a Cyclic Pentadepsipeptide with Wound-Healing Properties Isolated from a Marine-Derived Fungus of the Genus Acremonium

J Nat Prod. 2021 Aug 27;84(8):2249-2255. doi: 10.1021/acs.jnatprod.1c00305. Epub 2021 Aug 13.

Abstract

Acremonamide (1) was isolated from a marine-derived fungus belonging to the genus Acremonium. The chemical structure of 1 was established using MS, UV, and NMR spectroscopic data analyses. Acremonamide (1) was found to contain N-Me-Phe, N-Me-Ala, Val, Phe, and 2-hydroxyisovaleric acid. The absolute configurations of the four aforementioned amino acids were determined through acid hydrolysis followed by the advanced Marfey's method, whereas the absolute configuration of 2-hydroxyisovaleric acid was determined through GC-MS analysis after formation of the O-pentafluoropropionylated derivative of the (-)-menthyl ester of 2-hydroxyisovaleric acid. As an intrinsic biological activity, acremonamide (1) did not exert cytotoxicity to cancer and noncancer cells and increased the migration and invasion. Based on these activities, the wound healing properties of acremonamide (1) were confirmed in vitro and in vivo.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acremonium / chemistry*
  • Animals
  • Aquatic Organisms / chemistry
  • Caco-2 Cells
  • HaCaT Cells
  • Humans
  • Male
  • Mice
  • Mice, Inbred BALB C
  • Molecular Structure
  • NIH 3T3 Cells
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / pharmacology*
  • Wound Healing / drug effects*

Substances

  • Peptides, Cyclic