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

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.

Taeanamides A and B, Nonribosomal Lipo-Decapeptides Isolated from an Intertidal-Mudflat-Derived Streptomyces sp.

“…Although the L-FDAA di-adduct of Dab eluted faster than its D-FDAA derivative, the absolute configuration of this unit could not be determined because predicting the elution order of the two advanced Marfey products (i.e., the L-and D-di-FDAA adducts) was not straightforward. We then derivatized authentic L-Dab with L-and D-FDAA [12], and analysis of the product retention times revealed the elution of L-to D-FDAA di-adducts (Table S3). Due to the fact that the Marfey adducts of the Dab unit from 1 eluted at retention times consistent with those of L-Dab, the absolute configuration of N-Ac-Dab was established to be L. Furthermore, the additional chiral center of the β-position in Thr was assigned as R based on the The geometric configuration of the C-41-C-42 double bond was determined to be 41E by the analysis of 3 J H41H42 coupling constant (15.0 Hz), while the absolute configurations of the amino acids present in 1 were determined by applying the advanced Marfey's method [11].…”

Marine natural products

“…20 Svalbamides A 61 and B 62, lipodipeptides possessing a pyrrolidinone moiety, were identied from a Paenibacillus sp. 21 Heterologous production using carotenoid biosynthetic genes obtained from Planococcus maritimus yielded C 30 -carotenoids 63, 64, 22 and a lipooligosaccharide 65 was identied from Pseudoalteromonas nigrifaciens. 23 Pseudoalteropeptide A 66, a new siderophoric lipopeptide, was puried from the fermentation broth of Pseudoalteromonas piscicida.…”

Beyond Soil-Dwelling Actinobacteria: Fantastic Antibiotics and Where to Find Them

“…Arctic isolates of Paenibacillus sp. are the source of svalbamides A and B ( Figure 20 ), lipodipeptides containing 3-amino-2-pyrrolidinone with potential chemopreventative activity [ 454 ].…”