Instability and Structural Change of 4-Methylsulfinyl-3-butenyl Isothiocyanate in the Hydrolytic Process

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• 作者：Dan Song ; Hao Liang ; Pengqun Kuang ; Pingwah Tang ; Gaofei Hu ; Qipeng Yuan
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2013
• 出版时间：May 29, 2013
• 年：2013
• 卷：61
• 期：21
• 页码：5097-5102
• 全文大小：335K
• 年卷期：v.61,no.21(May 29, 2013)
• ISSN：1520-5118

文摘

Sulforaphene (4-methylsulfinyl-3-butenyl isothiocyanate), which has significant chemopreventive activities, is an important phytochemical ingredient produced by myrosinase hydrolysis of glucoraphenin (4-methylsulfinyl-3-butenyl glucosinolate) found in radish seeds. In this research, we found that sulforaphene was unstable and converted rapidly to a water-soluble degradation product in the hydrolytic process. The degradation product was successfully purified by preparative high-performance liquid chromatography on a C₁₈ column using 10% methanol in water as the mobile phase. On the basis of MS and NMR spectroscopy data, the degradation product was identified to be 6-[(methylsulfinyl)methyl]-1,3-thiazinan-2-thione. The degradation pathway of sulforaphene was proposed in our study. Furthermore, low pH and metal ions were also found to have an effective inhibition to the degradation reaction of sulforaphene. Through adjusting the pH value of the system or adding metal ions after the content of sulforaphene has reached its maximum, the yield of sulforaphene increased significantly compared with that of the control.

Keywords:

sulforaphene; glucoraphenin; radish seeds; degradation; 6-[(methylsulfinyl)methyl]-1,3-thiazinan-2-thione