Svalbamides A and B,Pyrrolidinone-Bearing Lipodipeptides from Arctic Paenibacillus sp. |
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| Authors: | Young Eun Du Eun Seo Bae Yeonjung Lim Jang-Cheon Cho Sang-Jip Nam Jongheon Shin Sang Kook Lee Seung-Il Nam Dong-Chan Oh |
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| Affiliation: | 1.Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea; (Y.E.D.); (E.S.B.); (J.S.); (S.K.L.);2.Department of Biological Sciences, Inha University, Incheon 22212, Korea; (Y.L.); (J.-C.C.);3.Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Korea;4.Korea Polar Research Institute, Incheon 21990, Korea; |
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| 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 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. |
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| Keywords: | Paenibacillus, Arctic, Svalbard, Marfey’ s method, DP4 calculation, quinone reductase, lipopeptide, 3-amino-2-pyrrolidinone |
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