2. Academic Validation
  3. Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis

Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis

  • Org Lett. 2016 Apr 15;18(8):1728-31. doi: 10.1021/acs.orglett.6b00206.
Wael M Abdel-Mageed 1 2 3,  Soad A L Bayoumi 2,  Lamya H Al-Wahaibi 4,  Li Li 5,  Hanaa M Sayed 2,  Mohamed S A Abdelkader 6,  Ali A El-Gamal 1,  Mei Liu 3,  Jingyu Zhang 3,  Lixin Zhang 3,  Xueting Liu 3
Affiliations

Affiliations

  • 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.
PMID: 27035218 DOI: 10.1021/acs.orglett.6b00206
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.

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