Skeleton Rearranged and Oxygenated ent-Rosane Diterpenoids with Antiadipogenic Activity from Euphorbia milii
Qin-Qin Song
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, 198 East Binhai Road, Yantai, Shandong, 264117 China
Search for more papers by this authorYue Guo
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, 198 East Binhai Road, Yantai, Shandong, 264117 China
University of Chinese Academy of Sciences, Beijing, 100049 China
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203 China
Search for more papers by this authorPeng Sun
CAS Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, No. 88, Xuefu Rd, Kunming, Yunnan, 650223 China
Search for more papers by this authorCorresponding Author
Yao-Yue Fan
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, 198 East Binhai Road, Yantai, Shandong, 264117 China
University of Chinese Academy of Sciences, Beijing, 100049 China
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Kai-Long Ji
CAS Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, No. 88, Xuefu Rd, Kunming, Yunnan, 650223 China
E-mail: [email protected]; [email protected]Search for more papers by this authorQin-Qin Song
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, 198 East Binhai Road, Yantai, Shandong, 264117 China
Search for more papers by this authorYue Guo
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, 198 East Binhai Road, Yantai, Shandong, 264117 China
University of Chinese Academy of Sciences, Beijing, 100049 China
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203 China
Search for more papers by this authorPeng Sun
CAS Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, No. 88, Xuefu Rd, Kunming, Yunnan, 650223 China
Search for more papers by this authorCorresponding Author
Yao-Yue Fan
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, 198 East Binhai Road, Yantai, Shandong, 264117 China
University of Chinese Academy of Sciences, Beijing, 100049 China
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai, 201203 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Kai-Long Ji
CAS Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, No. 88, Xuefu Rd, Kunming, Yunnan, 650223 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
Five unreported and oxygenated ent-rosane diterpenoids (ent-RDs), Euphomillanols A—E (1—5), were isolated from Euphorbia milii. Among them, compounds 1 and 2 are unprecedented 7/7/6-fused tricyclic 5,10-seco-ent-RDs and possess a unique 11-oxabicyclo[4.4.1]undeca-1(10),5-diene moiety, while 3 is characterized by a 1-methyl-6-oxabicyclo[3.2.1]oct-2-ene motif of ring A. Their structures with absolute configurations were unambiguously determined by the extensive spectroscopic methods, X-ray crystallography, and ECD calculation. Putative biosynthetic pathways for compounds 1—3 are proposed. All compounds exhibited antiadipogenic effects in 3T3-L1 adipocytes, and the most potent compound 4 showed an EC50 value of 3.92 μmol/L with low cytotoxicity (IC50 > 89.54 μmol/L).
Supporting Information
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