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

Li Pan; Ping Zhou; Xiaofeng Zhang; Shulin Peng; Lisheng Ding; Samuel X. Qiu

doi:10.1021/ol0608552

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

Li Pan, Ping Zhou, Xiaofeng Zhang, Shulin Peng, Lisheng Ding, Samuel X. Qiu

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	2775-2778
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	13
DOIs	https://doi.org/10.1021/ol0608552
State	Published - Jun 22 2006
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "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.",

author = "Li Pan and Ping Zhou and Xiaofeng Zhang and Shulin Peng and Lisheng Ding and Qiu, {Samuel X.}",

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T1 - Skeleton-rearranged pentacyclic diterpenoids possessing a cyclobutane ring from Euphorbia wallichii

AU - Pan, Li

AU - Zhou, Ping

AU - Zhang, Xiaofeng

AU - Peng, Shulin

AU - Ding, Lisheng

AU - Qiu, Samuel X.

PY - 2006/6/22

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AB - 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.

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