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Published on: May 22, 2014
19-nor-Clerodane Diterpenoid Dimers from Croton euryphyllus and Their NLRP3 Inflammasome Inhibitory Activity
Xi-Hong Liu1,2, Bi-Xi Tang3,4, Cheng-Yu Zheng2
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China.
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Guided by LC-MS profiling and polarity-based fractionation, four novel 19-nor-clerodane diterpenoid dimers, euryproids A-D (1-4), were isolated from Croton euryphyllus, employing crotoeurin A (5) as a reference. Compound 1 possesses an architecturally novel 6/6/6/6/6 carbocyclic framework through an intermolecular Diels-Alder cycloaddition, while 2-4 feature a rare cyclobutane-bridged skeleton constructed via a [2 + 2] cycloaddition. Compound 4 exhibited potent NLRP3 inflammasome inhibition, significantly suppressing LDH release, IL-1β secretion, and ASC speck formation with minimal cytotoxicity.
