Svalbamides A and B, Pyrrolidinone-Bearing Lipodipeptides from Arctic Paenibacillus sp.

• Published in: Marine Drugs
• Main Authors: 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
• Format: Text
• Language: English
• Published: Multidisciplinary Digital Publishing Institute 2021
• Subjects: Paenibacillus; Arctic; Svalbard; Marfey’s method; DP4 calculation; quinone reductase; lipopeptide; 3-amino-2-pyrrolidinone; Arctic Ocean; Svalbard Archipelago
• Online Access: https://doi.org/10.3390/md19040229

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 calculations. 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.