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 <i>Escherichia coli</i> by high-resolution magic angle spinning NMR spec...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/2/373 |
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| author | Valtteri Virtanen Susanna Räikkönen Elina Puljula Maarit Karonen |
| author_facet | Valtteri Virtanen Susanna Räikkönen Elina Puljula Maarit Karonen |
| author_sort | Valtteri Virtanen |
| collection | DOAJ |
| 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 <i>Escherichia coli</i> 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. |
| first_indexed | 2024-03-09T05:00:06Z |
| format | Article |
| id | doaj.art-71d7587c2ce6455aaf395583adb9f48c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T05:00:06Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-71d7587c2ce6455aaf395583adb9f48c2023-12-03T13:00:32ZengMDPI AGMolecules1420-30492021-01-0126237310.3390/molecules26020373Ellagitannin–Lipid Interaction by HR-MAS NMR SpectroscopyValtteri Virtanen0Susanna Räikkönen1Elina Puljula2Maarit Karonen3Natural Chemistry Research Group, Department of Chemistry, University of Turku, FI-20014 Turku, FinlandNatural Chemistry Research Group, Department of Chemistry, University of Turku, FI-20014 Turku, FinlandNatural Chemistry Research Group, Department of Chemistry, University of Turku, FI-20014 Turku, FinlandNatural Chemistry Research Group, Department of Chemistry, University of Turku, FI-20014 Turku, FinlandEllagitannins 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 <i>Escherichia coli</i> 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.https://www.mdpi.com/1420-3049/26/2/373<i>E. coli</i>HR-MAS-NMRinteractionlipid membranetanninsUPLC-DAD-MS |
| spellingShingle | Valtteri Virtanen Susanna Räikkönen Elina Puljula Maarit Karonen Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy Molecules <i>E. coli</i> HR-MAS-NMR interaction lipid membrane tannins UPLC-DAD-MS |
| 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 | <i>E. coli</i> HR-MAS-NMR interaction lipid membrane tannins UPLC-DAD-MS |
| url | https://www.mdpi.com/1420-3049/26/2/373 |
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