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

Title
Svalbamides A and B, pyrrolidinone-bearing lipodipeptides from arctic paenibacillus sp.
Authors
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
남상집
SCOPUS Author ID
남상집scopusscopus
Issue Date
2021
Journal Title
Marine Drugs
ISSN
1660-3397JCR Link
Citation
Marine Drugs vol. 19, no. 4
Keywords
3-amino-2-pyrrolidinoneArcticDP4 calculationLipopeptideMarfey’s methodPaenibacillusQuinone reductaseSvalbard
Publisher
MDPI AG
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
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. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
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DOI
10.3390/MD19040229
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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