Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from <i>Lunaria annua</i> L. and Their Cytotoxic Activity
Glucosinolates (GSLs) from <i>Lunaria annua</i> L. seeds were analyzed qualitatively and quantitatively by their desulfo counterparts using UHPLC-DAD-MS/MS technique and by their volatile breakdown products, isothiocyanates (ITCs), using GC-MS technique. GSL breakdown products were obtai...
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doaj-e1c446257aac490cb198db0498409c812020-11-25T01:42:25ZengMDPI AGBiomolecules2218-273X2020-02-0110221510.3390/biom10020215biom10020215Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from <i>Lunaria annua</i> L. and Their Cytotoxic ActivityIvica Blažević0Azra Đulović1Vedrana Čikeš Čulić2Marijana Popović3Xavier Guillot4Franko Burčul5Patrick Rollin6Department of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, Ruđera Boškovića 35, 21000 Split, CroatiaDepartment of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, Ruđera Boškovića 35, 21000 Split, CroatiaSchool of Medicine, University of Split, Šoltanska 2, 21000 Split, CroatiaDepartment of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, Ruđera Boškovića 35, 21000 Split, CroatiaLaboulet Ets, 81500 Lavaur, FranceDepartment of Analytical Chemistry, Faculty of Chemistry and Technology, University of Split, Ruđera Boškovića 35, 21000 Split, CroatiaInstitut de Chimie Organique et Analytique (ICOA), Université d’Orléans et CNRS, UMR 7311, BP 6759, F-45067 Orléans, FranceGlucosinolates (GSLs) from <i>Lunaria annua</i> L. seeds were analyzed qualitatively and quantitatively by their desulfo counterparts using UHPLC-DAD-MS/MS technique and by their volatile breakdown products, isothiocyanates (ITCs), using GC-MS technique. GSL breakdown products were obtained by conventional techniques (hydrodistillation in a Clevenger type apparatus (HD), CH<sub>2</sub>Cl<sub>2</sub> extraction after myrosinase hydrolysis (EXT) for 24 h) as well as by modern techniques, microwave-assisted distillation (MAD) and microwave hydrodiffusion and gravity (MHG). Seven GSLs were identified as follows: isopropyl GSL (<b>1</b>), <i>sec</i>-butyl GSL (<b>2</b>), 5-(methylsulfinyl)pentyl GSL (<b>3</b>), 6-(methylsulfinyl)hexyl GSL (<b>4</b>), 5-(methylsulfanyl)pentyl GSL (<b>5</b>), 6-(methylsulfanyl)hexyl GSL (<b>6</b>), and benzyl GSL (<b>7</b>). Additionally, pent-4-enyl- and hex-5-enyl ITCs were detected in the volatile extracts. However, their corresponding GSLs were not detected using UHPLC-DAD-MS/MS. Thus, they are suggested to be formed during GC-MS analysis via thermolysis of 5-(methylsulfinyl)pentyl- and 6-(methylsulfinyl)hexyl ITCs, respectively. Volatile isolates were tested for their cytotoxic activity using MTT assay. EXT and MHG showed the best cytotoxic activity against human lung cancer cell line A549 during an incubation time of 72 h (IC<sub>50</sub> 18.8, and 33.5 μg/mL, respectively), and against breast cancer cell line MDA-MB-231 after 48 h (IC<sub>50</sub> 6.0 and 11.8 μg/mL, respectively). These activities can be attributed to the ITCs originating from <b>3</b> and <b>4</b>.https://www.mdpi.com/2218-273X/10/2/215<i>lunaria annua</i>glucosinolatesisothiocyanatesmicrowave-assisted isolationcytotoxic activityhuman lung cancer cell line a549breast cancer cell line mda-mb-231 |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Ivica Blažević Azra Đulović Vedrana Čikeš Čulić Marijana Popović Xavier Guillot Franko Burčul Patrick Rollin |
spellingShingle |
Ivica Blažević Azra Đulović Vedrana Čikeš Čulić Marijana Popović Xavier Guillot Franko Burčul Patrick Rollin Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from <i>Lunaria annua</i> L. and Their Cytotoxic Activity Biomolecules <i>lunaria annua</i> glucosinolates isothiocyanates microwave-assisted isolation cytotoxic activity human lung cancer cell line a549 breast cancer cell line mda-mb-231 |
author_facet |
Ivica Blažević Azra Đulović Vedrana Čikeš Čulić Marijana Popović Xavier Guillot Franko Burčul Patrick Rollin |
author_sort |
Ivica Blažević |
title |
Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from <i>Lunaria annua</i> L. and Their Cytotoxic Activity |
title_short |
Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from <i>Lunaria annua</i> L. and Their Cytotoxic Activity |
title_full |
Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from <i>Lunaria annua</i> L. and Their Cytotoxic Activity |
title_fullStr |
Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from <i>Lunaria annua</i> L. and Their Cytotoxic Activity |
title_full_unstemmed |
Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from <i>Lunaria annua</i> L. and Their Cytotoxic Activity |
title_sort |
microwave-assisted versus conventional isolation of glucosinolate degradation products from <i>lunaria annua</i> l. and their cytotoxic activity |
publisher |
MDPI AG |
series |
Biomolecules |
issn |
2218-273X |
publishDate |
2020-02-01 |
description |
Glucosinolates (GSLs) from <i>Lunaria annua</i> L. seeds were analyzed qualitatively and quantitatively by their desulfo counterparts using UHPLC-DAD-MS/MS technique and by their volatile breakdown products, isothiocyanates (ITCs), using GC-MS technique. GSL breakdown products were obtained by conventional techniques (hydrodistillation in a Clevenger type apparatus (HD), CH<sub>2</sub>Cl<sub>2</sub> extraction after myrosinase hydrolysis (EXT) for 24 h) as well as by modern techniques, microwave-assisted distillation (MAD) and microwave hydrodiffusion and gravity (MHG). Seven GSLs were identified as follows: isopropyl GSL (<b>1</b>), <i>sec</i>-butyl GSL (<b>2</b>), 5-(methylsulfinyl)pentyl GSL (<b>3</b>), 6-(methylsulfinyl)hexyl GSL (<b>4</b>), 5-(methylsulfanyl)pentyl GSL (<b>5</b>), 6-(methylsulfanyl)hexyl GSL (<b>6</b>), and benzyl GSL (<b>7</b>). Additionally, pent-4-enyl- and hex-5-enyl ITCs were detected in the volatile extracts. However, their corresponding GSLs were not detected using UHPLC-DAD-MS/MS. Thus, they are suggested to be formed during GC-MS analysis via thermolysis of 5-(methylsulfinyl)pentyl- and 6-(methylsulfinyl)hexyl ITCs, respectively. Volatile isolates were tested for their cytotoxic activity using MTT assay. EXT and MHG showed the best cytotoxic activity against human lung cancer cell line A549 during an incubation time of 72 h (IC<sub>50</sub> 18.8, and 33.5 μg/mL, respectively), and against breast cancer cell line MDA-MB-231 after 48 h (IC<sub>50</sub> 6.0 and 11.8 μg/mL, respectively). These activities can be attributed to the ITCs originating from <b>3</b> and <b>4</b>. |
topic |
<i>lunaria annua</i> glucosinolates isothiocyanates microwave-assisted isolation cytotoxic activity human lung cancer cell line a549 breast cancer cell line mda-mb-231 |
url |
https://www.mdpi.com/2218-273X/10/2/215 |
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