Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis

Wael M. Abdel-Mageed, Soad A.L. Bayoumi, Lamya H. Al-Wahaibi, Li Li, Hanaa M. Sayed, Mohamed S.A. Abdelkader, Ali A. El-Gamal, Mei Liu, Jingyu Zhang, Lixin Zhang, Xueting Liu

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8 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1728-1731
Number of pages4
JournalOrganic Letters
Volume18
Issue number8
DOIs
Publication statusPublished - 15 Apr 2016

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Cyclooxygenase Inhibitors
Dimers
inhibitors
Carbon
dimers
Nitriles
Dimerization
carbon
nitriles
dimerization
Circular Dichroism
leaves
Inhibitory Concentration 50
dichroism
rings
electronics
simmonoside B
simmonoside A

Cite this

Abdel-Mageed, W. M., Bayoumi, S. A. L., Al-Wahaibi, L. H., Li, L., Sayed, H. M., Abdelkader, M. S. A., ... Liu, X. (2016). Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis. Organic Letters, 18(8), 1728-1731. https://doi.org/10.1021/acs.orglett.6b00206
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. / Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis. In: Organic Letters. 2016 ; Vol. 18, No. 8. pp. 1728-1731.
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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.",
author = "Abdel-Mageed, {Wael M.} and Bayoumi, {Soad A.L.} and Al-Wahaibi, {Lamya H.} and Li Li and Sayed, {Hanaa M.} and Abdelkader, {Mohamed S.A.} and El-Gamal, {Ali A.} and Mei Liu and Jingyu Zhang and Lixin Zhang and Xueting Liu",
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Abdel-Mageed, WM, Bayoumi, SAL, Al-Wahaibi, LH, Li, L, Sayed, HM, Abdelkader, MSA, El-Gamal, AA, Liu, M, Zhang, J, Zhang, L & Liu, X 2016, 'Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis', Organic Letters, vol. 18, no. 8, pp. 1728-1731. https://doi.org/10.1021/acs.orglett.6b00206

Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis. / 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.

In: Organic Letters, Vol. 18, No. 8, 15.04.2016, p. 1728-1731.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Noncyanogenic Cyanoglucoside Cyclooxygenase Inhibitors from Simmondsia chinensis

AU - Abdel-Mageed, Wael M.

AU - Bayoumi, Soad A.L.

AU - Al-Wahaibi, Lamya H.

AU - Li, Li

AU - Sayed, Hanaa M.

AU - Abdelkader, Mohamed S.A.

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AU - Zhang, Jingyu

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AU - Liu, Xueting

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