Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis

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• 作者：Wael M. Abdel-Mageed ; Soad A. L. Bayoumi ; Lamya H. Al-wahaibi ; Li Li ; Hanaa M. Sayed ; Mohamed S. A. Abdelkader ; Ali A. El-Gamal ; Mei Liu ; Jingyu Zhang ; Lixin Zhang ; Xueting Liu
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：18
• 期：8
• 页码：1728-1731
• 全文大小：299K
• 年卷期：0
• ISSN：1523-7052

文摘

Two new noncyanogenic cyanoglucoside dimers, simmonosides A and B (1 and 2), were identified from the aqueous extract of jojoba (Simmondsia chinensis) leaves. Compounds 1 and 2 are the first examples of noncyanogenic cyanoglucoside dimers containing a unique four-membered ring, representing novel dimerization patterns at α,β-unsaturated carbons of a nitrile group in 1 and γ,δ-unsaturated carbons in 2. Their structures were elucidated based on spectroscopic evidence and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 exhibit promising COX-2 inhibition activity, with IC₅₀ values of 13.5 and 11.4 μM, respectively.