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 journalArticle

26 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2775-2778
Number of pages4
JournalOrganic Letters
Volume8
Issue number13
DOIs
StatePublished - Jun 22 2006
Externally publishedYes

Fingerprint

Cyclobutanes
Euphorbia
osteoporosis
cyclobutane
Diterpenes
stereochemistry
musculoskeletal system
Skeleton
nuclear magnetic resonance
acids
Stereochemistry
rings
Osteogenesis
Osteoporosis
x rays
Nuclear magnetic resonance
X-Rays
X rays
Acids
Therapeutics

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Skeleton-rearranged pentacyclic diterpenoids possessing a cyclobutane ring from Euphorbia wallichii. / Pan, Li; Zhou, Ping; Zhang, Xiaofeng; Peng, Shulin; Ding, Lisheng; Qiu, Samuel X.

In: Organic Letters, Vol. 8, No. 13, 22.06.2006, p. 2775-2778.

Research output: Contribution to journalArticle

Pan, Li ; Zhou, Ping ; Zhang, Xiaofeng ; Peng, Shulin ; Ding, Lisheng ; Qiu, Samuel X. / Skeleton-rearranged pentacyclic diterpenoids possessing a cyclobutane ring from Euphorbia wallichii. In: Organic Letters. 2006 ; Vol. 8, No. 13. pp. 2775-2778.
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