Synthesis and anti-inflammatory activity of indole glucosinolates

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• 作者：Quan V. Vo ; Craige Trenerry ; Simone Rochfort ; Jenny Wadeson ; Carolina Leyton ; Andrew B. Hughes
• 关键词：DBU ; 1 ; 5-diazabicyclo [5.4.0]undecene ; DCM ; dichloromethane ; DME ; 1 ; 2-dimethoxyethane ; DMF ; N ; N-dimethylformamide ; DMF.DMA ; dimethylformamide dimethyl acetal ; ELISA ; enzyme-linked immunosorbent assay ; ESI ; electrospray ionization ; FTMS ; Fourier transform mass spectrometry ; GB ; glucobrassicin ; GLs ; glucosinolates ; HESI ; heated electrospray ionization ; HRMS ; high resolution mass spectrometry ; IR ; infra-red ; LPS ; lipopolysaccharides ; MGB ; 4-methoxyglucobrassicin ; MS ; mass spectrometry ; NCS ; N-chlor
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：15 January, 2014
• 年：2014
• 卷：22
• 期：2
• 页码：856-864
• 全文大小：827 K

文摘

The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassicin (NGB) in moderate overall yield for the first time. The anti-inflammatory activity of the synthetic indole GLs was determined by inhibition of TNF-伪 secretion in LPS-stimulated THP-1 cells. The data showed that glucobrassicin (GB) exhibited higher activity than other synthetic indolyl GLs.