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Svalbamides A and B, pyrrolidinone-bearing lipodipeptides from arctic paenibacillus sp.
- Svalbamides A and B, pyrrolidinone-bearing lipodipeptides from arctic paenibacillus sp.
- Du Y.E.; Bae E.S.; Lim Y.; Cho J.-C.; Nam S.-J.; Shin J.; Lee S.K.; Nam S.-I.; Oh D.-C.
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- Marine Drugs
- Marine Drugs vol. 19, no. 4
- 3-amino-2-pyrrolidinone; Arctic; DP4 calculation; Lipopeptide; Marfey’s method; Paenibacillus; Quinone reductase; Svalbard
- MDPI AG
- SCIE; SCOPUS
- Document Type
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- 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. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
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