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Open AccessArticle

Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from Lunaria annua L. and Their Cytotoxic Activity

1
Department of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, Ruđera Boškovića 35, 21000 Split, Croatia
2
School of Medicine, University of Split, Šoltanska 2, 21000 Split, Croatia
3
Laboulet Ets, 81500 Lavaur, France
4
Department of Analytical Chemistry, Faculty of Chemistry and Technology, University of Split, Ruđera Boškovića 35, 21000 Split, Croatia
5
Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans et CNRS, UMR 7311, BP 6759, F-45067 Orléans, France
*
Author to whom correspondence should be addressed.
Biomolecules 2020, 10(2), 215; https://doi.org/10.3390/biom10020215
Received: 28 November 2019 / Revised: 29 January 2020 / Accepted: 30 January 2020 / Published: 1 February 2020
(This article belongs to the Section Natural and Bio-inspired Molecules)
Glucosinolates (GSLs) from Lunaria annua 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), CH2Cl2 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 (1), sec-butyl GSL (2), 5-(methylsulfinyl)pentyl GSL (3), 6-(methylsulfinyl)hexyl GSL (4), 5-(methylsulfanyl)pentyl GSL (5), 6-(methylsulfanyl)hexyl GSL (6), and benzyl GSL (7). 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 (IC50 18.8, and 33.5 μg/mL, respectively), and against breast cancer cell line MDA-MB-231 after 48 h (IC50 6.0 and 11.8 μg/mL, respectively). These activities can be attributed to the ITCs originating from 3 and 4. View Full-Text
Keywords: Lunaria annua; glucosinolates; isothiocyanates; microwave-assisted isolation; cytotoxic activity; human lung cancer cell line A549; breast cancer cell line MDA-MB-231 Lunaria annua; glucosinolates; isothiocyanates; microwave-assisted isolation; cytotoxic activity; human lung cancer cell line A549; breast cancer cell line MDA-MB-231
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Blažević, I.; Đulović, A.; Čikeš Čulić, V.; Popović, M.; Guillot, X.; Burčul, F.; Rollin, P. Microwave-Assisted versus Conventional Isolation of Glucosinolate Degradation Products from Lunaria annua L. and Their Cytotoxic Activity. Biomolecules 2020, 10, 215.

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