Skeleton-rearranged pentacyclic diterpenoids possessing a cyclobutane ring from Euphorbia wallichii

[structure: see text] Two novel rearranged trachylobane diterpenoids, designated as wallichanol A (2) and wallichanol B (3), consisting of an unprecedented pentacyclic skeleton named wallichane with a cyclobutane ring, and a new ent-trachylobane diterpenoid, 3-oxo-ent-trachyloban-17-oic acid (1), we...

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Bibliographic Details
Published in:Organic letters 2006-06, Vol.8 (13), p.2775-2778
Main Authors: Pan, Li, Zhou, Ping, Zhang, Xiaofeng, Peng, Shulin, Ding, Lisheng, Qiu, Samuel X
Format: Article
Language:English
Subjects:
Bone Resorption - prevention & control
Crystallography, X-Ray
Cyclobutanes - chemistry
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Euphorbia - chemistry
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Osteoclasts - drug effects
Osteoporosis - prevention & control
Plant Roots - chemistry
Plants, Medicinal - chemistry
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Summary:[structure: see text] Two novel rearranged trachylobane diterpenoids, designated as wallichanol A (2) and wallichanol B (3), consisting of an unprecedented pentacyclic skeleton named wallichane with a cyclobutane ring, and a new ent-trachylobane diterpenoid, 3-oxo-ent-trachyloban-17-oic acid (1), were isolated from the roots of Euphorbia wallichii. Their structures were elucidated by comprehensive analysis of 2D-NMR spectroscopic data, with the stereochemistry of 1 confirmed by X-ray crystallographic study. All of these compounds potently block osteoclastogenesis in vitro, suggesting a potential therapeutic application in prevention of osteoporosis.
ISSN:1523-7060
DOI:10.1021/ol0608552