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Molecules 2014, 19(6), 6975-6986; doi:10.3390/molecules19066975

Novel Gram-Scale Production of Enantiopure R-Sulforaphane from Tuscan Black Kale Seeds

1
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
2
Institut de Chimie Organique et Analytique-UMR 7311, Université d'Orléans, Rue de Chartres, BP 6759, Orléans Cedex 2 45067, France
3
IRCCS Centro Neurolesi "Bonino-Pulejo", Via Provinciale Palermo, S.S.113, Contrada Casazza, Messina 98124, Italy
*
Authors to whom correspondence should be addressed.
Received: 18 April 2014 / Revised: 22 May 2014 / Accepted: 23 May 2014 / Published: 27 May 2014
(This article belongs to the Section Natural Products)
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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. View Full-Text
Keywords: R-sulforaphane; Tuscan black kale; Brassica oleracea; glucoraphanin; glucosinolate; biphasic system R-sulforaphane; Tuscan black kale; Brassica oleracea; glucoraphanin; glucosinolate; biphasic system
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MDPI and ACS Style

De Nicola, G.R.; Rollin, P.; Mazzon, E.; Iori, R. Novel Gram-Scale Production of Enantiopure R-Sulforaphane from Tuscan Black Kale Seeds. Molecules 2014, 19, 6975-6986.

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