Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis

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 di...

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Bibliographic Details
Published in:Organic letters 2016-04, Vol.18 (8), p.1728-1731
Main Authors: Abdel-Mageed, Wael M, Bayoumi, Soad A. L, Al-wahaibi, Lamya H, Li, Li, Sayed, Hanaa M, Abdelkader, Mohamed S. A, El-Gamal, Ali A, Liu, Mei, Zhang, Jingyu, Zhang, Lixin, Liu, Xueting
Format: Article
Language:English
Subjects:
Circular Dichroism
Cyclooxygenase 2 Inhibitors - chemistry
Cyclooxygenase 2 Inhibitors - pharmacology
Glucosides - chemistry
Glucosides - pharmacology
Inhibitory Concentration 50
Iridoid Glucosides - chemistry
Iridoid Glucosides - pharmacology
Molecular Structure
Nitriles - chemistry
Nitriles - pharmacology
Plant Leaves
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00206