Preparation and biological activity of four epiprogoitrin myrosinase-derived products.
(5R)-5-Vinyl-1,3-oxazolidine-2-thione, (2S)-1-cyano-2-hydroxy-3-butene, and two diastereoisomeric erythro-(2S)- and threo-(2S)-1-cyano-2-hydroxy-3,4-epithiobutanes were prepared in pure form starting from (2S)-2-hydroxybut-3-enyl glucosinolate (epiprogoitrin). This glucosinolate was isolated in almost pure form using ripe seeds of Crambe abyssinica and then hydrolyzed under different conditions. The hydrolysis was carried out using either myrosinase immobilized on nylon, to produce (5R)-5-vinyl-1,3-oxazolidine-2-thione, or the endogenous myrosinase contained in defatted crambe meals, to produce the other epiprogoitrin-derived products. After purification and physicochemical characterization, all four myrosinase degradation products were tested for their biological activity. A bioassay on Lactuca sativa was chosen as a simple test to determine their apparent action on living tissues. (5R)-5-Vinyl-1,3-oxazolidine-2-thione negatively affected mainly root growth, whereas (2S)-1-cyano-2-hydroxy-3-butene affected the early phase of germination, and both (2S)-1-cyano-2-hydroxy-3,4-epithiobutane diastereoisomers appeared to negatively affect both germination and root growth at doses 5-10 times lower than those of (2S)-1-cyano-2-hydroxy-3-butene or (5R)-5-vinyl-1,3-oxazolidine-2-thione.
Galletti
S
S
Istituto Sperimentale per le Colture Industriali, Italian Ministry of Agricultural and Forestry Politics, Via di Corticella 133, I-40129 Bologna, Italy.
Bernardi
R
R
Leoni
O
O
Rollin
P
P
Palmieri
S
S
D019607:Brassicaceae / Q000737:chemistry* / Q000187:drug effects / Q000254:growth & development; D018525:Germination / Q000187:drug effects; D005961:Glucosinolates / Q000737:chemistry / Q000378:metabolism*; D006026:Glycoside Hydrolases / Q000737:chemistry / Q000378:metabolism*; D009570:Nitriles / Q000737:chemistry / Q000494:pharmacology; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D012639:Seeds / Q000737:chemistry; D013237:Stereoisomerism
D005961:Glucosinolates; D009570:Nitriles; C009048:progoitrin; D006026:Glycoside Hydrolases; C022739:thioglucosidase