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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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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 |
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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 |
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