Selenoglucosinolates and their metabolites produced in Brassica spp. fertilised with sodium selenate |
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| Affiliation: | 1. Public Monitoring Center for Agro-Product, Guangdong Academy of Agricultural Sciences, Guangzhou 510640, China;2. Key Laboratory of Testing and Evaluation for Agro-product Safety and Quality, Ministry of Agriculture, Guangzhou 510640, China;3. Laboratory of Quality and Safety Risk Assessment for Agro-product (Guangzhou), Ministry, Guangzhou 510640, China;4. College of Resources and Environment, Huazhong Agricultural University, Wuhan 430070, China;1. College of Natural Resources and Environment, Northwest A&F University, Yangling, Shaanxi 712100, China;2. Key Laboratory of Plant Nutrition and the Agri-environment in Northwest China, Ministry of Agriculture, Yangling, Shaanxi 712100, China;1. Graduate School of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8572, Japan;2. Faculty of Life and Environmental Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8572, Japan;3. Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan;4. Microbiology Research Center for Sustainability (MiCS), University of Tsukuba, Tsukuba, Ibaraki 305-8572, Japan;1. Department of Food Chemistry and Nutrition, Faculty of Pharmacy, Medical College, Jagiellonian University, Medyczna 9, 30-688 Kraków, Poland;2. Instituto de Química Orgánica General (IQOG-CSIC), Consejo Superior de Investigaciones Científicas, Juan de la Cierva 3, 28006 Madrid, Spain;3. Department of Pharmaceutical Technology and Chemistry, School of Pharmacy and Nutrition, University of Navarra, Pamplona, Spain;4. Instituto de Investigaciones Sanitarias de Navarra (IdiSNA), Pamplona, Spain;5. Universite de Pau et des Pays de l''Adour, E2S UPPA, CNRS, IPREM UMR 5254, Hélioparc, 64053 Pau, France;6. IM Sechenov First Moscow State Medical University (Sechenov University), 119146 Moscow, Russia;7. Department of Technology and Biotechnology of Drugs, Medical College, Jagiellonian University, Medyczna, 9 30-688 Kraków, Poland;8. Division of Bioorganic Chemistry, School of Pharmacy, Saarland University, Campus B 2.1, D-66123 Saarbruecken, Germany;9. Department of Pharmacognosy, Faculty of Pharmacy, Medical College, Jagiellonian University Medyczna 9, 30-688 Kraków, Poland;10. Institute for Drug Research, School of Pharmacy, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem 9112001, Israel |
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| Abstract: | Glucosinolates are sulphur-containing glycosides found in many Brassica spp. that are important because their aglycone hydrolysis products protect the plant from herbivores and exhibit anti-cancer properties in humans. Recently, synthetically produced selenium analogues have been shown to be more effective at suppressing cancers than their sulphur counterparts. Although selenium is incorporated into a number of Brassica amino acids and peptides, firm evidence has yet to be presented for the presence of selenium in the glucosinolates and their aglycones in planta. In this study broccoli and cauliflower florets, and roots of forage rape, all obtained from plants treated with sodium selenate, were analysed for the presence of organoselenides. GC–MS analysis of pentane/ether extracts identified six organoselenium compounds including selenium analogues of known myrosinase-derived Brassica volatiles: 4-(methylseleno)butanenitrile, 5-(methylseleno)pentanenitrile, 3-(methylseleno)propylisothiocyanate, 4-(methylseleno)butylisothiocyanate, and 5-(methylseleno)pentylisothiocyanate. LC–MS analysis of ethanolic extracts identified three selenoglucosinolates: 3-(methylseleno)propylglucosinolate (glucoselenoiberverin), 4-(methylseleno)butylglucosinolate (glucoselenoerucin), and 5-(methylseleno)pentylglucosinolate (glucoselenoberteroin). LC–MS/MS analysis was used to locate the position of the selenium atom in the selenoglucosinolate and indicates preferential incorporation of selenium via selenomethionine into the methylselenyl moiety rather than into the sulphate or β-thioglucose groups. In forage rape, selenoglucosinolates and their aglycones (mainly isothiocyanates), occurred at concentrations up to 10% and 70%, respectively, of their sulphur analogues. In broccoli, concentrations of the selenoglucosinolates and their aglycones (mainly nitriles) were up to 60% and 1300%, respectively of their sulphur analogues. These findings indicate the potential for the incorporation of high levels of selenium into Brassica glucosinolates. |
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