Svalbamides A and B, pyrrolidinone-bearing lipodipeptides from arctic paenibacillus sp.

Young Eun Du, Eun Seo Bae, Yeonjung Lim, Jang Cheon Cho, Sang Jip Nam, Jongheon Shin, Sang Kook Lee, Seung Il Nam, Dong Chan Oh

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Two new secondary metabolites, svalbamides A (1) and B (2), were isolated from a culture extract of Paenibacillus sp. SVB7 that was isolated from surface sediment from a core (HH17-1085) taken in the Svalbard archipelago in the Arctic Ocean. The combinational analysis of HR-MS and NMR spectroscopic data revealed the structures of 1 and 2 as being lipopeptides bearing 3-amino-2-pyrrolidinone, D-valine, and 3-hydroxy-8-methyldecanoic acid. The absolute configurations of the amino acid residues in svalbamides A and B were determined using the advanced Marfey’s method, in which the hydrolysates of 1 and 2 were derivatized with L-and D-forms of 1-fluoro-2,4-dinitrophenyl-5-alanine amide (FDAA). The absolute configurations of 1 and 2 were completely assigned by deducing the stereochemistry of 3-hydroxy-8-methyldecanoic acid based on DP4 calcu-lations. Svalbamides A and B induced quinone reductase activity in Hepa1c1c7 murine hepatoma cells, indicating that they represent chemotypes with a potential for functioning as chemopreventive agents.

Original languageEnglish
Article number229
JournalMarine Drugs
Volume19
Issue number4
DOIs
StatePublished - Apr 2021

Keywords

  • 3-amino-2-pyrrolidinone
  • Arctic
  • DP4 calculation
  • Lipopeptide
  • Marfey’s method
  • Paenibacillus
  • Quinone reductase
  • Svalbard

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