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Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis

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journal contribution
posted on 2016-04-01, 19:18 authored by 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
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.