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Glucosinolate degradation products and other bound and free volatiles in the leaves and roots of radish (Raphanus sativus L.)

The volatile constituents from the leaves and roots of Raphanus sativus var. black, white and red were isolated by hydrodistillation in Clevenger-type apparatus and were analyzed by gas chromatography and gas chromatography – mass spectrometry (GC, GC-MS). The major components found in the oil of all leaves were: phytol (65.3 – 69.7 %), hexadecanoic acid (2.5 – 14.3 %), methyl linolenate (2.1 – 11.1 %), (Z)-3-hexene-1-ol (0.7 – 6.9 %). Corresponding aliphatic or aromatic glucosinolates compounds identified in the leaves constituted only 0.3 – 5.7 % of the isolated volatiles. They were: 5-methylthio-4-pentenenitrile (0.3 - 2.2 %), 4-methylthiobutyl isothiocyanate (0.3 - 1.7 %), 2-phenylethyl isothiocyanate (0.4 %), 4-methylthio-3-butenyl isothiocyanate, 4-methylpentyl isothiocyanate, benzyl isothiocyanate and benzenepropanenitrile. The major components in the oil of all roots were: hexadecanoic acid (30.3 – 49.9 %), 4-methylthiobutyl isothiocyanate (17.9 - 25.7 %), methyl linolenate (8.5 – 21.7 %), 5-methylthio-4-pentenenitrile (1.5 – 6.9 %), dimethyltrisulfide (1.1 - 3.8 %), 5-methylthiopentyl isothiocyanate (0.5 - 2.0 %), 4-methylthio-3-butenyl isothiocyanate (0.2 - 1.8 %) and 2-phenylethyl isothiocyanate (0.1 - 1.5 %). O-Glycosidically bound volatiles were isolated and hydrolyzed by  -glucosidase from almonds, nineteen volatile aglycons were identified for the first time in all the leaves of radish. The main aglycones were: eugenol (29.2 – 37.1 %), 2-phenylethanol (2.0 - 23.5 %), 4-vinyl-2-methoxyphenol (2.4 – 12.4 %), (Z)-3-hexen-1-ol (2.6 – 10.4 %), methyl vanillate (6.3 – 10.0 %), 1H-indole (0.7 – 6.8 %), benzyl alcohol (1.4 – 4.2 %), vanillin (3.5 – 6.3 %) and methyl salicylate (0.8 – 3.4 %). However, no volatile aglycons were detected after isolation in different varieties of radish roots.

Raphanus sativus L.; radish; Brassicaceae; glucosinolates; O-glycosides; volatile aglycones; isothiocyanates; nitriles; GC-MS

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