Svalbamides A and B, pyrrolidinone-bearing lipodipeptides from arctic paenibacillus sp.
- 주제(키워드) 3-amino-2-pyrrolidinone , Arctic , DP4 calculation , Lipopeptide , Marfey’s method , Paenibacillus , Quinone reductase , Svalbard
- 후원정보 Oh, D.-C.; Natural Products Research Institute, South Korea; email: dongchanoh@snu.ac.kr
- 등재 SCIE, SCOPUS
- 발행기관 MDPI AG
- 발행년도 2021
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000181817
- 본문언어 영어
- Published As http://dx.doi.org/10.3390/MD19040229
초록/요약
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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