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

Sojeong Kim, Chang Wook Lee, So Yeon Park, Ratnakar N. Asolkar, Haerin Kim, Geum Jin Kim, Song Jin Oh, Youngbae Kim, Eun Young Lee, Dong Chan Oh, Inho Yang, Man Jeong Paik, Hyukjae Choi, Hangun Kim, Sang Jip Nam, William Fenical

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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.

Original languageEnglish
Pages (from-to)2249-2255
Number of pages7
JournalJournal of Natural Products
Volume84
Issue number8
DOIs
StatePublished - 27 Aug 2021

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