Cargando…

Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy

Ellagitannins have antimicrobial activity, which might be related to their interactions with membrane lipids. We studied the interactions of 12 different ellagitannins and pentagalloylglucose with a lipid extract of Escherichia coli by high-resolution magic angle spinning NMR spectroscopy. The nucle...

Descripción completa

Detalles Bibliográficos
Autores principales: Virtanen, Valtteri, Räikkönen, Susanna, Puljula, Elina, Karonen, Maarit
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7828275/
https://www.ncbi.nlm.nih.gov/pubmed/33445813
http://dx.doi.org/10.3390/molecules26020373
_version_ 1783640971918966784
author Virtanen, Valtteri
Räikkönen, Susanna
Puljula, Elina
Karonen, Maarit
author_facet Virtanen, Valtteri
Räikkönen, Susanna
Puljula, Elina
Karonen, Maarit
author_sort Virtanen, Valtteri
collection PubMed
description Ellagitannins have antimicrobial activity, which might be related to their interactions with membrane lipids. We studied the interactions of 12 different ellagitannins and pentagalloylglucose with a lipid extract of Escherichia coli by high-resolution magic angle spinning NMR spectroscopy. The nuclear Overhauser effect was utilized to measure the cross relaxation rates between ellagitannin and lipid protons. The shifting of lipid signals in 1H NMR spectra of ellagitannin–lipid mixture due to ring current effect was also observed. The ellagitannins that showed interaction with lipids had clear structural similarities. All ellagitannins that had interactions with lipids had glucopyranose cores. In addition to the central polyol, the most important structural feature affecting the interaction seemed to be the structural flexibility of the ellagitannin. Even dimeric and trimeric ellagitannins could penetrate to the lipid bilayers if their structures were flexible with free galloyl and hexahydroxydiphenoyl groups.
format Online
Article
Text
id pubmed-7828275
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-78282752021-01-25 Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy Virtanen, Valtteri Räikkönen, Susanna Puljula, Elina Karonen, Maarit Molecules Article Ellagitannins have antimicrobial activity, which might be related to their interactions with membrane lipids. We studied the interactions of 12 different ellagitannins and pentagalloylglucose with a lipid extract of Escherichia coli by high-resolution magic angle spinning NMR spectroscopy. The nuclear Overhauser effect was utilized to measure the cross relaxation rates between ellagitannin and lipid protons. The shifting of lipid signals in 1H NMR spectra of ellagitannin–lipid mixture due to ring current effect was also observed. The ellagitannins that showed interaction with lipids had clear structural similarities. All ellagitannins that had interactions with lipids had glucopyranose cores. In addition to the central polyol, the most important structural feature affecting the interaction seemed to be the structural flexibility of the ellagitannin. Even dimeric and trimeric ellagitannins could penetrate to the lipid bilayers if their structures were flexible with free galloyl and hexahydroxydiphenoyl groups. MDPI 2021-01-12 /pmc/articles/PMC7828275/ /pubmed/33445813 http://dx.doi.org/10.3390/molecules26020373 Text en © 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Virtanen, Valtteri
Räikkönen, Susanna
Puljula, Elina
Karonen, Maarit
Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy
title Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy
title_full Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy
title_fullStr Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy
title_full_unstemmed Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy
title_short Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy
title_sort ellagitannin–lipid interaction by hr-mas nmr spectroscopy
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7828275/
https://www.ncbi.nlm.nih.gov/pubmed/33445813
http://dx.doi.org/10.3390/molecules26020373
work_keys_str_mv AT virtanenvaltteri ellagitanninlipidinteractionbyhrmasnmrspectroscopy
AT raikkonensusanna ellagitanninlipidinteractionbyhrmasnmrspectroscopy
AT puljulaelina ellagitanninlipidinteractionbyhrmasnmrspectroscopy
AT karonenmaarit ellagitanninlipidinteractionbyhrmasnmrspectroscopy