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

• Published in: Marine Drugs
• Main Authors: Young-Eun Du, Eun-Seo Bae, Yeon-Jung Lim, Jang-Cheon Cho, Sang-Jip Nam, Jong-Heon Shin, Sang-Kook Lee, Seung-Il Nam, Dong-Chan Oh
• Format: Article in Journal/Newspaper
• Language: English
• Published: MDPI AG 2021
• Subjects: Paenibacillus; Arctic; Svalbard; Marfey’s method; DP4 calculation; quinone reductase; Biology (General); QH301-705.5; Arctic Ocean; Svalbard Archipelago
• Online Access: https://doi.org/10.3390/md19040229; https://doaj.org/article/a98ed642f7f04403aed6fdc962eda138

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.