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

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

doi:10.3390/MD19040229

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

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

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

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.

Original language	English
Article number	229
Journal	Marine Drugs
Volume	19
Issue number	4
DOIs	https://doi.org/10.3390/MD19040229
State	Published - Apr 2021

Bibliographical note

Funding Information:
Funding: This work was supported by the Collaborative Genome Program of the Korea Institute of Marine Science and Technology Promotion (KIMST) funded by the Ministry of Oceans and Fisheries (MOF) (No. 20180430) and the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT) (2021R1A4A2001251) and partly by the Basic Core Technology Development Program for the Oceans and the Polar Regions (NRF-2015M1A5A1037243).

Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

3-amino-2-pyrrolidinone
Arctic
DP4 calculation
Lipopeptide
Marfey’s method
Paenibacillus
Quinone reductase
Svalbard

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title = "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{\textquoteright}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.",

keywords = "3-amino-2-pyrrolidinone, Arctic, DP4 calculation, Lipopeptide, Marfey{\textquoteright}s method, Paenibacillus, Quinone reductase, Svalbard",

author = "Du, {Young Eun} and Bae, {Eun Seo} and Yeonjung Lim and Cho, {Jang Cheon} and Nam, {Sang Jip} and Jongheon Shin and Lee, {Sang Kook} and Nam, {Seung Il} and Oh, {Dong Chan}",

note = "Funding Information: Funding: This work was supported by the Collaborative Genome Program of the Korea Institute of Marine Science and Technology Promotion (KIMST) funded by the Ministry of Oceans and Fisheries (MOF) (No. 20180430) and the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT) (2021R1A4A2001251) and partly by the Basic Core Technology Development Program for the Oceans and the Polar Regions (NRF-2015M1A5A1037243). Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2021",

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doi = "10.3390/MD19040229",

language = "English",

volume = "19",

journal = "Marine Drugs",

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AU - Bae, Eun Seo

AU - Lim, Yeonjung

AU - Cho, Jang Cheon

AU - Nam, Sang Jip

AU - Shin, Jongheon

AU - Lee, Sang Kook

AU - Nam, Seung Il

AU - Oh, Dong Chan

N1 - Funding Information: Funding: This work was supported by the Collaborative Genome Program of the Korea Institute of Marine Science and Technology Promotion (KIMST) funded by the Ministry of Oceans and Fisheries (MOF) (No. 20180430) and the National Research Foundation of Korea (NRF) grants funded by the Ministry of Science and ICT (MSIT) (2021R1A4A2001251) and partly by the Basic Core Technology Development Program for the Oceans and the Polar Regions (NRF-2015M1A5A1037243). Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2021/4

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N2 - 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.

AB - 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.

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KW - DP4 calculation

KW - Lipopeptide

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KW - Paenibacillus

KW - Quinone reductase

KW - Svalbard

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DO - 10.3390/MD19040229

M3 - Article

C2 - 33920625

AN - SCOPUS:85105237700

SN - 1660-3397

VL - 19

JO - Marine Drugs

JF - Marine Drugs

IS - 4

M1 - 229

ER -

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

Abstract

Bibliographical note

Keywords

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