title: Novel gram-scale production of enantiopure R-sulforaphane from Tuscan black kale seeds.
abstract: Dietary R-sulforaphane is a highly potent inducer of the Keap1/Nrf2/ARE pathway. Furthermore, sulforaphane is currently being used in clinical trials to assess its effects against different tumour processes. This study reports an efficient preparation of enantiopure R-sulforaphane based on the enzymatic hydrolysis of its natural precursor glucoraphanin. As an alternative to broccoli seeds, we have exploited Tuscan black kale seeds as a suitable source for gram-scale production of glucoraphanin. The defatted seed meal contained 5.1% (w/w) of glucoraphanin that was first isolated through an anion exchange chromatographic process, and then purified by gel filtration. The availability of glucoraphanin (purity≈95%, weight basis) has allowed us to develop a novel simple hydrolytic process involving myrosinase (EC 3.2.1.147) in a biphasic system to directly produce R-sulforaphane. In a typical experiment, 1.09 g of enantiopure R-sulforaphane was obtained from 150 g of defatted Tuscan black kale seed meal.
authors.affiliation: Consiglio per la Ricerca e la sperimentazione in Agricoltura, Centro di Ricerca per le Colture Industriali (CRA-CIN), Via Di Corticella 133, Bologna 40128, Italy. gina.denicola@cracin.it.
authors.forename: Gina Rosalinda
authors.initials: GR
authors.lastname: De Nicola
authors.affiliation: Institut de Chimie Organique et Analytique-UMR 7311, Université d'Orléans, Rue de Chartres, BP 6759, Orléans Cedex 2 45067, France. patrick.rollin@univ-orleans.fr.
authors.forename: Patrick
authors.initials: P
authors.lastname: Rollin
authors.affiliation: IRCCS Centro Neurolesi "Bonino-Pulejo", Via Provinciale Palermo, S.S.113, Contrada Casazza, Messina 98124, Italy. mazzon@irccsneurolesiboninopulejo.it.
authors.forename: Emanuela
authors.initials: E
authors.lastname: Mazzon
authors.affiliation: Consiglio per la Ricerca e la sperimentazione in Agricoltura, Centro di Ricerca per le Colture Industriali (CRA-CIN), Via Di Corticella 133, Bologna 40128, Italy. renato.iori@entecra.it.
authors.forename: Renato
authors.initials: R
authors.lastname: Iori
mesh_terms: D001937:Brassica / Q000378:metabolism*; D005961:Glucosinolates; D006026:Glycoside Hydrolases / Q000378:metabolism; D007096:Imidoesters; D017879:Isothiocyanates / Q000378:metabolism*; D010091:Oximes; D012639:Seeds / Q000378:metabolism*; D013454:Sulfoxides
chemical_list: D005961:Glucosinolates; D007096:Imidoesters; D017879:Isothiocyanates; D010091:Oximes; D013454:Sulfoxides; D006026:Glycoside Hydrolases; C022739:thioglucosidase; C016766:sulforaphane; C119494:glucoraphanin