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

• Published in: Marine Drugs
• Main Authors: Du, Young Eun, Bae, Eun Seo, Lim, Yeonjung, Cho, Jang-Cheon, Nam, Sang-Jip, Shin, Jongheon, Lee, Sang Kook, Nam, Seung-Il, Oh, Dong-Chan
• Format: Article in Journal/Newspaper
• Language: unknown
• Published: Multidisciplinary Digital Publishing Institute (MDPI) 2021
• Subjects: Paenibacillus; Arctic; Svalbard; Marfey& #8217; s method; DP4 calculation; quinone reductase; lipopeptide; 3-amino-2-pyrrolidinone; Arctic Ocean; Svalbard Archipelago
• Online Access: https://hdl.handle.net/10371/205754; 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. Y 1