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
  • 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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