title: Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis.
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.
authors.affiliation: Pharmacognosy Department, College of Pharmacy, King Saud University , P.O. Box 2457, Riyadh 11451, Saudi Arabia.|Pharmacognosy Department, Faculty of Pharmacy, Assiut University , Assiut 71526, Egypt.|Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences , Datun Road, Chaoyang District, Beijing 100080, China.
authors.forename: Wael M
authors.initials: WM
authors.lastname: Abdel-Mageed
authors.affiliation: Pharmacognosy Department, Faculty of Pharmacy, Assiut University , Assiut 71526, Egypt.
authors.forename: Soad A L
authors.initials: SA
authors.lastname: Bayoumi
authors.affiliation: Chemistry Department, Science College, Princess Noura bint Abdul Rahman University , Riyadh 11671, Saudi Arabia.
authors.forename: Lamya H
authors.initials: LH
authors.lastname: Al-Wahaibi
authors.affiliation: Department of Medicinal Chemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College , Beijing 100050, China.
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.affiliation: Pharmacognosy Department, Faculty of Pharmacy, Assiut University , Assiut 71526, Egypt.
authors.forename: Hanaa M
authors.initials: HM
authors.lastname: Sayed
authors.affiliation: Department of Pharmacognosy, Faculty of Pharmacy, Sohag University , Nasser City, 82524 Sohag, Egypt.
authors.forename: Mohamed S A
authors.initials: MS
authors.lastname: Abdelkader
authors.affiliation: Pharmacognosy Department, College of Pharmacy, King Saud University , P.O. Box 2457, Riyadh 11451, Saudi Arabia.
authors.forename: Ali A
authors.initials: AA
authors.lastname: El-Gamal
authors.affiliation: Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences , Datun Road, Chaoyang District, Beijing 100080, China.
authors.forename: Mei
authors.initials: M
authors.lastname: Liu
authors.affiliation: Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences , Datun Road, Chaoyang District, Beijing 100080, China.
authors.forename: Jingyu
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences , Datun Road, Chaoyang District, Beijing 100080, China.
authors.forename: Lixin
authors.initials: L
authors.lastname: Zhang
authors.affiliation: Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences , Datun Road, Chaoyang District, Beijing 100080, China.
authors.forename: Xueting
authors.initials: X
authors.lastname: Liu
mesh_terms: D002942:Circular Dichroism; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D005960:Glucosides / Q000737:chemistry* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D057888:Iridoid Glucosides / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry* / Q000494:pharmacology; D018515:Plant Leaves
chemical_list: D052246:Cyclooxygenase 2 Inhibitors; D005960:Glucosides; D057888:Iridoid Glucosides; D009570:Nitriles; C000610794:simmonoside A; C000610796:simmonoside B