title: Euphomilones A and B, ent-Rosane Diterpenoids with 7/5/6 and 5/7/6 Skeletons from Euphorbia milii.
abstract: Three highly modified ent-rosane diterpenoids, euphomilones A (1) and B (2) and euphomianol A (3), were isolated from the aerial parts of Euphorbia milii. The structures were elucidated from physical, spectroscopic, and X-ray diffraction data, as well as experimental and calculated electronic circular dichroism (ECD) analysis. Plausible biogenetic pathways to 1-3 are proposed. Also, compound 1 exhibited inhibition of receptor activator of nuclear factor-kappaB ligand (RANKL)-induced osteoclast formation (IC50= 12.6 μM).
authors.affiliation: Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, People's Republic of China.
authors.forename: Shao-Nan
authors.initials: SN
authors.lastname: Liu
authors.affiliation: Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, People's Republic of China.
authors.forename: Dane
authors.initials: D
authors.lastname: Huang
authors.affiliation: Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina , Chapel Hill, North Carolina 27599, United States.
authors.forename: Susan L
authors.initials: SL
authors.lastname: Morris-Natschke
authors.affiliation: Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island , Kingston, Rhode Island 02881, United States.
authors.forename: Hang
authors.initials: H
authors.lastname: Ma
authors.affiliation: Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, People's Republic of China.
authors.forename: Zhi-Hong
authors.initials: ZH
authors.lastname: Liu
authors.affiliation: Bioactive Botanical Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island , Kingston, Rhode Island 02881, United States.
authors.forename: Navindra P
authors.initials: NP
authors.lastname: Seeram
authors.affiliation: Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, People's Republic of China.
authors.forename: Jun
authors.initials: J
authors.lastname: Xu
authors.affiliation: Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina , Chapel Hill, North Carolina 27599, United States.|Chinese Medicine Research and Development Center, China Medical University and Hospital , Taichung, Taiwan.
authors.forename: Kuo-Hsiung
authors.initials: KH
authors.lastname: Lee
authors.affiliation: Research Center for Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, People's Republic of China.
authors.forename: Qiong
authors.initials: Q
authors.lastname: Gu
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D028481:Euphorbia / Q000737:chemistry*; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D016328:NF-kappa B / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010010:Osteoclasts / Q000187:drug effects* / Q000378:metabolism; D010012:Osteogenesis / Q000187:drug effects*; D000067996:RAW 264.7 Cells; D013329:Structure-Activity Relationship
chemical_list: D004224:Diterpenes; D016328:NF-kappa B; C000627535:euphomilone A; C000627534:euphomilone B