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Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms

Recently the number of studies investigating triterpenoid saponins has drastically increased due to their diverse and potentially attractive biological activities. Currently the literature contains chemical structures of few hundreds of triterpenoid saponins of plant and animal origin. Triterpenoid...

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Autores principales: Khakimov, Bekzod, Tseng, Li Hong, Godejohann, Markus, Bak, Søren, Engelsen, Søren Balling
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273444/
https://www.ncbi.nlm.nih.gov/pubmed/27886152
http://dx.doi.org/10.3390/molecules21121614
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author Khakimov, Bekzod
Tseng, Li Hong
Godejohann, Markus
Bak, Søren
Engelsen, Søren Balling
author_facet Khakimov, Bekzod
Tseng, Li Hong
Godejohann, Markus
Bak, Søren
Engelsen, Søren Balling
author_sort Khakimov, Bekzod
collection PubMed
description Recently the number of studies investigating triterpenoid saponins has drastically increased due to their diverse and potentially attractive biological activities. Currently the literature contains chemical structures of few hundreds of triterpenoid saponins of plant and animal origin. Triterpenoid saponins consist of a triterpene aglycone with one or more sugar moieties attached to it. However, due to similar physico-chemical properties, isolation and identification of a large diversity of triterpenoid saponins remain challenging. This study demonstrates a methodology to screen saponins using hyphenated analytical platforms, GC-MS, LC-MS/MS, and LC-SPE-NMR/MS, in the example of two different phenotypes of the model plant Barbarea vulgaris (winter cress), glabrous (G) and pubescent (P) type that are known to differ by their insect resistance. The proposed methodology allows for detailed comparison of saponin profiles from intact plant extracts as well as saponin aglycone profiles from hydrolysed samples. Continuously measured 1D proton NMR data during LC separation along with mass spectrometry data revealed significant differences, including contents of saponins, types of aglycones and numbers of sugar moieties attached to the aglycone. A total of 49 peaks were tentatively identified as saponins from both plants; they are derived from eight types of aglycones and with 2–5 sugar moieties. Identification of two previously known insect-deterrent saponins, hederagenin cellobioside and oleanolic acid cellobioside, demonstrated the applicability of the methodology for relatively rapid screening of bioactive compounds.
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spelling pubmed-62734442018-12-28 Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms Khakimov, Bekzod Tseng, Li Hong Godejohann, Markus Bak, Søren Engelsen, Søren Balling Molecules Article Recently the number of studies investigating triterpenoid saponins has drastically increased due to their diverse and potentially attractive biological activities. Currently the literature contains chemical structures of few hundreds of triterpenoid saponins of plant and animal origin. Triterpenoid saponins consist of a triterpene aglycone with one or more sugar moieties attached to it. However, due to similar physico-chemical properties, isolation and identification of a large diversity of triterpenoid saponins remain challenging. This study demonstrates a methodology to screen saponins using hyphenated analytical platforms, GC-MS, LC-MS/MS, and LC-SPE-NMR/MS, in the example of two different phenotypes of the model plant Barbarea vulgaris (winter cress), glabrous (G) and pubescent (P) type that are known to differ by their insect resistance. The proposed methodology allows for detailed comparison of saponin profiles from intact plant extracts as well as saponin aglycone profiles from hydrolysed samples. Continuously measured 1D proton NMR data during LC separation along with mass spectrometry data revealed significant differences, including contents of saponins, types of aglycones and numbers of sugar moieties attached to the aglycone. A total of 49 peaks were tentatively identified as saponins from both plants; they are derived from eight types of aglycones and with 2–5 sugar moieties. Identification of two previously known insect-deterrent saponins, hederagenin cellobioside and oleanolic acid cellobioside, demonstrated the applicability of the methodology for relatively rapid screening of bioactive compounds. MDPI 2016-11-24 /pmc/articles/PMC6273444/ /pubmed/27886152 http://dx.doi.org/10.3390/molecules21121614 Text en © 2016 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
Khakimov, Bekzod
Tseng, Li Hong
Godejohann, Markus
Bak, Søren
Engelsen, Søren Balling
Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms
title Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms
title_full Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms
title_fullStr Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms
title_full_unstemmed Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms
title_short Screening for Triterpenoid Saponins in Plants Using Hyphenated Analytical Platforms
title_sort screening for triterpenoid saponins in plants using hyphenated analytical platforms
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273444/
https://www.ncbi.nlm.nih.gov/pubmed/27886152
http://dx.doi.org/10.3390/molecules21121614
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