Antioxidant and Cytotoxic Potential of ICarlina vulgaris/I Extract and Bioactivity-Guided Isolation of Cytotoxic Components
Carlina vulgaris is a poorly understood plant in the context of biological activity, despite its widespread application in ethnomedicine in numerous European countries. The aim of this study was to assess the cytotoxic potential of the plant against human colorectal adenocarcinoma (HT29) and to isol...
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Veröffentlicht in: | Antioxidants 2023-09, Vol.12 (9) |
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creator | Sowa, Ireneusz Paduch, Roman Mołdoch, Jarosław Szczepanek, Dariusz Szkutnik, Jacek Sowa, Paweł Tyszczuk-Rotko, Katarzyna Blicharski, Tomasz Wójciak, Magdalena |
description | Carlina vulgaris is a poorly understood plant in the context of biological activity, despite its widespread application in ethnomedicine in numerous European countries. The aim of this study was to assess the cytotoxic potential of the plant against human colorectal adenocarcinoma (HT29) and to isolate the plant components linked to this effect. Ultra-high performance liquid chromatography with a high-resolution/quadrupole time-of-flight mass spectrometer (UHPLC–HR/QTOF/MS–PDA) was used for the phytochemical characterization of the extract. Liquid–liquid extraction and preparative chromatography were employed for fractionation purposes. Our investigation demonstrated that the ethyl acetate fraction from C. vulgaris showed significant cytotoxicity, and a bioactivity-guided approach led to the isolation of oxylipins, including traumatic acid, pinellic acid, and 9,10-dihydroxy-8-oxsooctadec-12-enic acid. The structures of the compounds were confirmed by nuclear magnetic resonance spectroscopy. Among these compounds, the last one exhibited significant cytotoxicity, though without selectivity, and traumatic acid was characterized by mild cytotoxicity. The cytotoxicity was linked to intracellular reactive oxygen species generation. |
doi_str_mv | 10.3390/antiox12091704 |
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The aim of this study was to assess the cytotoxic potential of the plant against human colorectal adenocarcinoma (HT29) and to isolate the plant components linked to this effect. Ultra-high performance liquid chromatography with a high-resolution/quadrupole time-of-flight mass spectrometer (UHPLC–HR/QTOF/MS–PDA) was used for the phytochemical characterization of the extract. Liquid–liquid extraction and preparative chromatography were employed for fractionation purposes. Our investigation demonstrated that the ethyl acetate fraction from C. vulgaris showed significant cytotoxicity, and a bioactivity-guided approach led to the isolation of oxylipins, including traumatic acid, pinellic acid, and 9,10-dihydroxy-8-oxsooctadec-12-enic acid. The structures of the compounds were confirmed by nuclear magnetic resonance spectroscopy. Among these compounds, the last one exhibited significant cytotoxicity, though without selectivity, and traumatic acid was characterized by mild cytotoxicity. The cytotoxicity was linked to intracellular reactive oxygen species generation.</description><identifier>ISSN: 2076-3921</identifier><identifier>EISSN: 2076-3921</identifier><identifier>DOI: 10.3390/antiox12091704</identifier><language>eng</language><publisher>MDPI AG</publisher><subject>Antioxidants ; Colorectal cancer ; Esters ; Genetic aspects ; High performance liquid chromatography ; Nuclear magnetic resonance spectroscopy</subject><ispartof>Antioxidants, 2023-09, Vol.12 (9)</ispartof><rights>COPYRIGHT 2023 MDPI AG</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,860,27903,27904</link.rule.ids></links><search><creatorcontrib>Sowa, Ireneusz</creatorcontrib><creatorcontrib>Paduch, Roman</creatorcontrib><creatorcontrib>Mołdoch, Jarosław</creatorcontrib><creatorcontrib>Szczepanek, Dariusz</creatorcontrib><creatorcontrib>Szkutnik, Jacek</creatorcontrib><creatorcontrib>Sowa, Paweł</creatorcontrib><creatorcontrib>Tyszczuk-Rotko, Katarzyna</creatorcontrib><creatorcontrib>Blicharski, Tomasz</creatorcontrib><creatorcontrib>Wójciak, Magdalena</creatorcontrib><title>Antioxidant and Cytotoxic Potential of ICarlina vulgaris/I Extract and Bioactivity-Guided Isolation of Cytotoxic Components</title><title>Antioxidants</title><description>Carlina vulgaris is a poorly understood plant in the context of biological activity, despite its widespread application in ethnomedicine in numerous European countries. The aim of this study was to assess the cytotoxic potential of the plant against human colorectal adenocarcinoma (HT29) and to isolate the plant components linked to this effect. Ultra-high performance liquid chromatography with a high-resolution/quadrupole time-of-flight mass spectrometer (UHPLC–HR/QTOF/MS–PDA) was used for the phytochemical characterization of the extract. Liquid–liquid extraction and preparative chromatography were employed for fractionation purposes. Our investigation demonstrated that the ethyl acetate fraction from C. vulgaris showed significant cytotoxicity, and a bioactivity-guided approach led to the isolation of oxylipins, including traumatic acid, pinellic acid, and 9,10-dihydroxy-8-oxsooctadec-12-enic acid. The structures of the compounds were confirmed by nuclear magnetic resonance spectroscopy. Among these compounds, the last one exhibited significant cytotoxicity, though without selectivity, and traumatic acid was characterized by mild cytotoxicity. The cytotoxicity was linked to intracellular reactive oxygen species generation.</description><subject>Antioxidants</subject><subject>Colorectal cancer</subject><subject>Esters</subject><subject>Genetic aspects</subject><subject>High performance liquid chromatography</subject><subject>Nuclear magnetic resonance spectroscopy</subject><issn>2076-3921</issn><issn>2076-3921</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNptjs1LAzEQxYMoWGqvngOet83XJptjXWpdKOih95LdJEtku5FmW1r8551awR6cOczjzbwfg9AjJVPONZmZfgjxSBnRVBFxg0aMKJlxzejtlb5Hk5Q-CJSmvCB6hL7mP8FgAYBNb3F5GuIARoPf4-BgaTocPa5Ks-tCb_Bh37VmF9KswovjsDPNJfYcIshwCMMpW-6DdRZXKXYG4P05_4ct4_Yz9kBOD-jOmy65ye8co_XLYl2-Zqu3ZVXOV1krlcg8L3zhBFfEUiqF1gqkryXLual5YT04MreNJYVshPK18NZJR7RnhlFt-Bg9XbCt6dwm9D6e396G1GzmSkrNcqUEXE3_uYK2bhsaeNgH8K8C37jecf4</recordid><startdate>20230901</startdate><enddate>20230901</enddate><creator>Sowa, Ireneusz</creator><creator>Paduch, Roman</creator><creator>Mołdoch, Jarosław</creator><creator>Szczepanek, Dariusz</creator><creator>Szkutnik, Jacek</creator><creator>Sowa, Paweł</creator><creator>Tyszczuk-Rotko, Katarzyna</creator><creator>Blicharski, Tomasz</creator><creator>Wójciak, Magdalena</creator><general>MDPI AG</general><scope/></search><sort><creationdate>20230901</creationdate><title>Antioxidant and Cytotoxic Potential of ICarlina vulgaris/I Extract and Bioactivity-Guided Isolation of Cytotoxic Components</title><author>Sowa, Ireneusz ; Paduch, Roman ; Mołdoch, Jarosław ; Szczepanek, Dariusz ; Szkutnik, Jacek ; Sowa, Paweł ; Tyszczuk-Rotko, Katarzyna ; Blicharski, Tomasz ; Wójciak, Magdalena</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g674-f38f8e4370d1164997370fb6253ab38df99765dcd086c47fb4fde6e09f2a219a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Antioxidants</topic><topic>Colorectal cancer</topic><topic>Esters</topic><topic>Genetic aspects</topic><topic>High performance liquid chromatography</topic><topic>Nuclear magnetic resonance spectroscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sowa, Ireneusz</creatorcontrib><creatorcontrib>Paduch, Roman</creatorcontrib><creatorcontrib>Mołdoch, Jarosław</creatorcontrib><creatorcontrib>Szczepanek, Dariusz</creatorcontrib><creatorcontrib>Szkutnik, Jacek</creatorcontrib><creatorcontrib>Sowa, Paweł</creatorcontrib><creatorcontrib>Tyszczuk-Rotko, Katarzyna</creatorcontrib><creatorcontrib>Blicharski, Tomasz</creatorcontrib><creatorcontrib>Wójciak, Magdalena</creatorcontrib><jtitle>Antioxidants</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sowa, Ireneusz</au><au>Paduch, Roman</au><au>Mołdoch, Jarosław</au><au>Szczepanek, Dariusz</au><au>Szkutnik, Jacek</au><au>Sowa, Paweł</au><au>Tyszczuk-Rotko, Katarzyna</au><au>Blicharski, Tomasz</au><au>Wójciak, Magdalena</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant and Cytotoxic Potential of ICarlina vulgaris/I Extract and Bioactivity-Guided Isolation of Cytotoxic Components</atitle><jtitle>Antioxidants</jtitle><date>2023-09-01</date><risdate>2023</risdate><volume>12</volume><issue>9</issue><issn>2076-3921</issn><eissn>2076-3921</eissn><abstract>Carlina vulgaris is a poorly understood plant in the context of biological activity, despite its widespread application in ethnomedicine in numerous European countries. The aim of this study was to assess the cytotoxic potential of the plant against human colorectal adenocarcinoma (HT29) and to isolate the plant components linked to this effect. Ultra-high performance liquid chromatography with a high-resolution/quadrupole time-of-flight mass spectrometer (UHPLC–HR/QTOF/MS–PDA) was used for the phytochemical characterization of the extract. Liquid–liquid extraction and preparative chromatography were employed for fractionation purposes. Our investigation demonstrated that the ethyl acetate fraction from C. vulgaris showed significant cytotoxicity, and a bioactivity-guided approach led to the isolation of oxylipins, including traumatic acid, pinellic acid, and 9,10-dihydroxy-8-oxsooctadec-12-enic acid. The structures of the compounds were confirmed by nuclear magnetic resonance spectroscopy. Among these compounds, the last one exhibited significant cytotoxicity, though without selectivity, and traumatic acid was characterized by mild cytotoxicity. The cytotoxicity was linked to intracellular reactive oxygen species generation.</abstract><pub>MDPI AG</pub><doi>10.3390/antiox12091704</doi></addata></record> |
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source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; MDPI - Multidisciplinary Digital Publishing Institute; EZB-FREE-00999 freely available EZB journals; PubMed Central |
subjects | Antioxidants Colorectal cancer Esters Genetic aspects High performance liquid chromatography Nuclear magnetic resonance spectroscopy |
title | Antioxidant and Cytotoxic Potential of ICarlina vulgaris/I Extract and Bioactivity-Guided Isolation of Cytotoxic Components |
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