Chisopanins A-K, 11 new protolimonoids from Chisocheton paniculatus and their anti-inflammatory activities

Bioorg Med Chem. 2011 Feb 15;19(4):1409-17. doi: 10.1016/j.bmc.2011.01.007.

Ming-Hua Yang ¹, Jun-Song Wang, Jian-Guang Luo, Xiao-Bing Wang, Ling-Yi Kong

Affiliations

Affiliation

1 Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, PR China.

PMID: 21288727 DOI: 10.1016/j.bmc.2011.01.007

Abstract

Eleven new protolimonoids, chisopanins A-K (1-11), were isolated from the twigs of Chisocheton paniculatus, as well as thirteen known (12-24) protolimonoids. The structures were elucidated on the basis of spectroscopic analysis, X-ray crystallographic analysis, and chemical methods. Chisopanins A and B (1 and 2) possessing uncommon hemiketal tetrahydropyran ring at C-17 showed the most potent inhibitory activities on lipopolysaccharide-stimulated inflammation factor-release with IC(50) values at 5.4 and 7.9 μM for NO, and at 26.9 and 30.7 μM for TNF-α, respectively. In addition, compounds 5-7, 9, 12, 13, and 20 were potent to inhibit NO production with IC(50) value lower than 10 μM.

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