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Org Lett. 2016 Apr 15;18(8):1728-31. doi: 10.1021/acs.orglett.6b00206. Epub 2016 Apr 1.

Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis.

Author information

1
Pharmacognosy Department, College of Pharmacy, King Saud University , P.O. Box 2457, Riyadh 11451, Saudi Arabia.
2
Pharmacognosy Department, Faculty of Pharmacy, Assiut University , Assiut 71526, Egypt.
3
Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences , Datun Road, Chaoyang District, Beijing 100080, China.
4
Chemistry Department, Science College, Princess Noura bint Abdul Rahman University , Riyadh 11671, Saudi Arabia.
5
Department of Medicinal Chemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050, China.
6
Department of Pharmacognosy, Faculty of Pharmacy, Sohag University , Nasser City, 82524 Sohag, Egypt.

Abstract

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.

PMID:
27035218
DOI:
10.1021/acs.orglett.6b00206
[Indexed for MEDLINE]

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