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

Abstract

Acremonamide (<b>1</b>) was isolated from a marine-derived fungus belonging to the genus <i>Acremonium</i>. The chemical structure of <b>1</b> was established using MS, UV, and NMR spectroscopic data analyses. Acremonamide (<b>1</b>) was found to contain <i>N</i>-Me-Phe, <i>N</i>-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 <i>O</i>-pentafluoropropionylated derivative of the (-)-menthyl ester of 2-hydroxyisovaleric acid. As an intrinsic biological activity, acremonamide (<b>1</b>) 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 (<b>1</b>) were confirmed <i>in vitro</i> and <i>in vivo</i>.