Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages

A madecassoside-rich fraction obtained from the industrial purification of Centella asiatica leaves afforded a new triterpene glycoside, named isomadecassoside (4), characterized by an ursane-type skeleton and migration of the double bond at Δ(20(21)) in ring E. The structure of isomadecassoside was...

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Autores principales: Chianese, Giuseppina, Masi, Francesca, Cicia, Donatella, Ciceri, Daniele, Arpini, Sabrina, Falzoni, Mario, Pagano, Ester, Taglialatela-Scafati, Orazio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8064468/
https://www.ncbi.nlm.nih.gov/pubmed/33806006
http://dx.doi.org/10.3390/biom11040494
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author Chianese, Giuseppina
Masi, Francesca
Cicia, Donatella
Ciceri, Daniele
Arpini, Sabrina
Falzoni, Mario
Pagano, Ester
Taglialatela-Scafati, Orazio
author_facet Chianese, Giuseppina
Masi, Francesca
Cicia, Donatella
Ciceri, Daniele
Arpini, Sabrina
Falzoni, Mario
Pagano, Ester
Taglialatela-Scafati, Orazio
author_sort Chianese, Giuseppina
collection PubMed
description A madecassoside-rich fraction obtained from the industrial purification of Centella asiatica leaves afforded a new triterpene glycoside, named isomadecassoside (4), characterized by an ursane-type skeleton and migration of the double bond at Δ(20(21)) in ring E. The structure of isomadecassoside was established by means of HR-ESIMS and detailed analysis of 1D and 2D NMR spectra, which allowed a complete NMR assignment. Studies on isolated J774A.1 macrophages stimulated by LPS revealed that isomadecassoside (4) inhibited nitrite production at non-cytotoxic concentrations, thus indicating an anti-inflammatory effect similar to that of madecassoside.
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spelling pubmed-80644682021-04-24 Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages Chianese, Giuseppina Masi, Francesca Cicia, Donatella Ciceri, Daniele Arpini, Sabrina Falzoni, Mario Pagano, Ester Taglialatela-Scafati, Orazio Biomolecules Article A madecassoside-rich fraction obtained from the industrial purification of Centella asiatica leaves afforded a new triterpene glycoside, named isomadecassoside (4), characterized by an ursane-type skeleton and migration of the double bond at Δ(20(21)) in ring E. The structure of isomadecassoside was established by means of HR-ESIMS and detailed analysis of 1D and 2D NMR spectra, which allowed a complete NMR assignment. Studies on isolated J774A.1 macrophages stimulated by LPS revealed that isomadecassoside (4) inhibited nitrite production at non-cytotoxic concentrations, thus indicating an anti-inflammatory effect similar to that of madecassoside. MDPI 2021-03-25 /pmc/articles/PMC8064468/ /pubmed/33806006 http://dx.doi.org/10.3390/biom11040494 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/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/ (https://creativecommons.org/licenses/by/4.0/) ).
spellingShingle Article
Chianese, Giuseppina
Masi, Francesca
Cicia, Donatella
Ciceri, Daniele
Arpini, Sabrina
Falzoni, Mario
Pagano, Ester
Taglialatela-Scafati, Orazio
Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages
title Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages
title_full Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages
title_fullStr Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages
title_full_unstemmed Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages
title_short Isomadecassoside, a New Ursane-Type Triterpene Glycoside from Centella asiatica Leaves, Reduces Nitrite Levels in LPS-Stimulated Macrophages
title_sort isomadecassoside, a new ursane-type triterpene glycoside from centella asiatica leaves, reduces nitrite levels in lps-stimulated macrophages
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8064468/
https://www.ncbi.nlm.nih.gov/pubmed/33806006
http://dx.doi.org/10.3390/biom11040494
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