Euphomilones A and B, ent-Rosane Diterpenoids with 7/5/6 and 5/7/6 Skeletons from Euphorbia milii

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 circul...

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Bibliographic Details
Published in:Organic letters 2016-12, Vol.18 (23), p.6132-6135
Main Authors: Liu, Shao-Nan, Huang, Dane, Morris-Natschke, Susan L, Ma, Hang, Liu, Zhi-hong, Seeram, Navindra P, Xu, Jun, Lee, Kuo-Hsiung, Gu, Qiong
Format: Article
Language:English
Subjects:
Animals
Crystallography, X-Ray
Dose-Response Relationship, Drug
Euphorbia - chemistry
Mice
Models, Molecular
Molecular Conformation
NF-kappa B - antagonists & inhibitors
NF-kappa B - metabolism
Osteoclasts - drug effects
Osteoclasts - metabolism
Osteogenesis - drug effects
RAW 264.7 Cells
Structure-Activity Relationship
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Summary: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).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03142