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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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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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container_issue	13
container_start_page	2775
container_title	Organic letters
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creator	Pan, Li Zhou, Ping Zhang, Xiaofeng Peng, Shulin Ding, Lisheng Qiu, Samuel X
description	[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.
doi_str_mv	10.1021/ol0608552
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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
title	Skeleton-rearranged pentacyclic diterpenoids possessing a cyclobutane ring from Euphorbia wallichii
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